BACKGROUND OF THE INVENTION There are many compounds that contain amide groups which have desirable pharmacological activity. For example, oxazolidinone derivatives containing an amide group are known to exhibit a variety of biological activities.

Oxazolidinone derivatives have been shown to be inhibitors of monoamine oxidase-B, an enzyme implicated in Parkinson's disease. Ding et al., J. Med. Chem.

36: 3606-3610 (1993).

Scientists have reported that certain oxazolidinone derivatives exhibit beneficial antibacterial effects.

For instance, N- [3- [3-fluoro-4- (morpholin-4-yl) phenyl] 2- oxooxazolidin-5 (s)-ylmethyl] acetamide (below) has been reported to be useful for the treatment of bacterial infections. Lizondo et al., Drugs of the Future, 21 : 1116-1123 (1996).

A ten step synthesis of oxazolidinone antibiotics has been described in U. S. Patent No. 5,547, 950. A four step synthesis of the antibacterial compound U-100592 also has been reported. Schauss et al., Tetrahedron Letters, 37 : 7937-7940 (1996). A five step preparation of enantiomerically pure cis-and trans-N- (propionyl) hexahydrobenzoxazolidin-2-ones further was reported in De Parrodi et al., Tetrahedron : Asymmetry, 8 : 1075-1082 (1997).

The synthesis of the oxazolidinone antibacterial agent shown below has been reported. Wang et al., Tetrahedron, 45: 1323-1326 (1989). This oxazolidinone was made using a process that included the reaction of an aniline with glycidol to provide an amino alcohol, and the diethylcarbonate mediated cyclization of the amino alcohol to afford an oxazolidinone.

The synthesis of oxazolidinone antibacterial agents, including the compound shown below has been reported.

U. S. Pat. No. 4, 705, 799. The process used to make the compound shown below included a metal mediated reduction of a sulfonyl chloride to provide a sulfide.

The synthesis of oxazolidinone antibacterial agents, including the pyridyl compound shown below has been reported. U. S. Patent No. 4,948, 801. The process used included an organometallic mediated coupling of an organotin compound and an aryl iodide.

U. S. Patent 5,652, 238 discloses carboxylic and phosphate esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones.

U. S. Patent 5,688, 792 discloses substituted oxazine and thiazine oxazolidinone useful as antibacticals.

PCT International Publication WO 98/54161 discloses oxazolidinone antibacterial agents having a thiocarbonyl functionality.

U. S. Patent 5,968, 962 and PCT International Publication WO 99/29688 discloses phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings.

U. S. Patent 5,952, 324 discloses bicyclic oxazine and thiazine oxazolidinone useful as antibacticals.

PCT publications, WO 99/64416, WO 99/64417, and WO 00/21960 disclose oxazolidinone derivatives useful as antibacterial agents.

PCT Publication, WO 00/10566 discloses isoxazolinones useful as antibacterial agents.

U. S. Patent No. 5,880, 118 discloses substituted oxazine and thiazine oxazolidinone antimocrobials.

U. S. Patent No. 6,968, 962 discloses phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings.

U. S. Patent No. 5,981, 528 discloses antibiotic oxazolidinone derivatives.

U. S. Patent application Serial No. 60/236595 discloses N- ( { (5S)-3- [4- (l, l-dioxido-9-thiomorpholinyl)- 3, 5-difluorophenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide.

PCT publications, WO 99/64416, WO 99/64417, and WO 00/21960 disclose isoxazolinone derivatives useful as antibacterial agents.

PCT publication, WO 00/10566 discloses isoxazolinones useful as antibacterial agents.

U. S. Patent No. 5,164, 510 discloses 5'- indolinyloxazolidin-2-ones of formula XI which are useful as antibacterial agents.

U. S. Patent Nos. 5,036, 092; 5,036, 093; 5,039, 690; 5,032, 605 and 4,965, 268 disclose aminomethyl oxazolidinyl aza cycloalkylbenzene derivatives useful as antibacterial agents.

U. S. Patent Nos. 5,792, 765 and 5, 684,023 disclose substituted isoxazolinones useful as antibacterial agents.

International Publication No. WO 97/09328 discloses phenyloxazolidinones having a C-C bond to 4-8 membered heterocyclic rings useful as antimicrobial agents.

PCT International Publication WO 93/23384 discloses oxazolidinones containing a substituted diazine moiety and their use as antimicrobials.

PCT International Publication WO 95/07271 discloses substituted oxazine and thiazine oxazolidinones and their use as antimicrobials.

However, even though some amide-containing compounds have been shown to be extremely effective in the treatment of certain physiological disorders, some of these compounds have a low bioavailability due to their low water solubility and/or low permeability through biological barriers, such as the blood brain barrier and the intestinal barrier.

In order to increase the bioavailability of certain amines, peptides and peptidomimetics, prodrugs of these compounds, have been proposed. Zheng et al, Tetrahedron Letters, 55: 4237-4254 (1999), Wang et al, Journal of Controlled Release, 65: 245-251 (2000) and Wang et al, Bioorganic & Medicinal Chemistry, 6 : 417-426 (1998).

These prodrugs derivatize certain polar functional groups transiently and bioreversably to mask undesirable physical chemical characteristics of the groups without permanently altering the pharmacological properties of the molecules and have been used very successfully in cases where the prodrug derivatization involves converting a carboxyl or a hydroxyl functional group into an ester which can be readily hydrolyzed in vivo either chemically or enzymatically. However, this strategy has not been successfully used in the case of an amide group due to the chemical stability thereof.

As such, there is a need for amide-containing compounds having an improved water-solubility and bioavailability and for methods for synthesizing these compounds.

SUMMARY OF THE INVENTION The objects of the present invention are met by providing an oxazolidinone derivative of Formula (I) wherein J is 0 or S ; R3io/P4io and R5io each independently are a) H, b) C1-4 alkyl, c) halogen, d) C14 alkoxy, e) hydroxy, f) (CH2) cOP (0) (OH) 2, g) C14 acyloxy, or h) C1-4 alkyl substituted by halogen, hydroxy, acyloxy, NR1210R1310, or alkoxy; Rsio, Rpio and Rgio each independently are a) H, b) CH3, or c) C2H5 ; Rglo and Rlolo each independently are a) H, b) CH3, c) CZHS, or d) combine to form a C3-5 cycloalkyl ; Rlllo is H or C1-6 alkyl ; R1210 and R1310 each independently are a) H, b) C14 alkyl, or c) combine to form a heterocyclic ring; wherein a is 0 or 1, b is 0 or 1, and c is 0 or 1, with e R 710 810 the proviso that when Q'is, b is 0 and a+b is 0 or 1 ; R1 is a) C1-4 alkyl, b) C2-4 alkenyl, c) OC1-4 alkyl, d) C3-6 cycloalkyl, e) C1-4 alkyl substituted with 1-3F, 1-2C1, CN, -COOC1-4 alkyl or a C3-6 cycloalkyl ; or f) H R4 is a) C1-4 alkyl optionally substituted with one or more halos, OH, CN, NRl0Rll, or-CO2R13, b) C2-4 alkenyl, c)-NRl6Rl8, <BR> <BR> d)-N3,<BR> e) -NHC (=O) R7, f)-NR20C (=O) R7, <BR> <BR> g)-N (Rl) 2,<BR> h)-NRi6Rl9, or<BR> i)-NRlgR20, R5 and R6 at each occurrence are the same or different and are a) C1-2 alkyl, or b) R5 and R6 taken together are-(CH2)k-; R7 is C1-4 alkyl optionally substituted with one or more halos; Rlo and RI, at each occurrence are the same or different and are a) H, b) Cl-4 alkyl, or c) C3-8 cycloalkyl ; R13 is a) H, or b) C1-4 alkyl ; R14 and Ris at each occurrence are the same or different and are a) C14 alkyl, or b) R14 and R15 taken together are- (CH) i- ; R16 is a) H, b) C1-4 alkyl, or c) C3-8 cycloalkyl ; R17 is a) C14 alkyl, or b) C3-8 cycloalkyl ; R18 is a) H, b) C14 alkyl, c) C2-4 alkenyl, d) C3-4 cycloalkyl, e)-OR13 or f)-NR21R22 ; Rlg is a) Cl, b) Br, or c) I; R20 is a physiologically acceptable cation; R21 and R22 at each occurrence are the same or different and are a) H, b) C14 alkyl, or c)-NR2lR22 taken together are- (CH2) m- ; wherein R23 and R24 at each occurrence are the same or different and are a) H, b) F, c) Cl, d) C1_2 alkyl, e) CN f) OH, g) C1_2 alkoxy, h) nitro, or i) amino; m) a diazinyl group optionally substituted with X and Y, n) a triazinyl group optionally substituted with X and Y, o) a quinolinyl group optionally substituted with X and Y, p) a quinoxalinyl group optionally substituted with X and Y, q) a naphthyridinyl group optionally substituted with X and Y, Q and R24 taken together are wherein Z1 is a)-CH2-, b)-CH(Rl04)-CH2-, c)-C(O)-, or d)-CH2CH2CH2-; wherein Z2 is <BR> <BR> a)-02S-,<BR> b)-O-,<BR> c)-N(R107)-,<BR> d)-OS-,<BR> e) -S-, or<BR> f)S(O)(NR190); wherein Z3 is <BR> <BR> a)-02S-,<BR> b)-O-, c)-OS-, d) -S-, or e) S(O)(NR190) wherein A¹ is a) H-, or b) CH3 ; wherein A2 is a) H-, b) HO-, c) CH3-, d) CH30-, e) Rl02O-CH2-C(O)-NH- f) R1030-C (0)-NH-, g) (C1-C2) alkyl-0-C (0)-, h) HO-CH2-, i) CH30-NH-, j) (C1-C3) alkyl-02C- k) CH3-C (0)-, 1) CH3-C (0)-CH2-, m), or A1 and A2 taken together are: wherein R102 is a) H-, b) CH3-, c) phenyl-CH2-, or d) CH3C(O)-; wherein R103 is a) (Cl-C3) alkyl-, or b) phenyl- ; wherein R104 is a) H-, or b) HO- ; wherein R106 is a) CH3-C(O)-, b) H-C (O)-, c) Cl2CH-C(O)-, d) HOCH2-C(O)-, e) CH3S02-, 115 '-='°'-' g) F2CHC (O)-, h) N-N-C (O)- i) H3C-C (0)-0-CH2-C (0)-, j) H-C (0)-0-CH2-C (0)-, k) b C (O)-t 1) HC=C-CH2O-CH2-C(O)-, or m) phenyl-CH2-0-CH2-C (0)- ; wherein R107 is a) R102O-C(R110)(R111)-C(O)-, b) R103O-C(O)-, c) R108-C(O)-, 0 d) t^ H e)/--,. owny o f) H3C-C (0)- (CH2) 2-C (0)-, nl09 r.,-, g) R-SOz-, 0 o 0 i) HO-CH2-C (0)-, j) Rll6-(CH2)2-, k) Rll3-C(O)-O-CH2-C(O)-, 1) (CH3) 2N-CH2-C (0) -NH-, m) NC-CH2-, n) F2-CH-CH2-, or o) R150Rl51NSO2 p) C (O)CRl80Rl80Rl8lORl82, q) C (0) CH2S (0) iCH3, r) C (0) CH2S (0) (NR183) CH3, s) C (S)R184, t) C (0) CH20R185, u) C (0) (CH2) jC (0) CH3, v) C (O)(CH20H)2CH3, w) C (0) CH2CH2OR189, or x) -CN; wherein R108 is a) H-, b) (Cl-C4) alkyl, c) aryl-(CH2)p, d) ClH2C-, e) Cl2HC-, f) FH2C-, g) F2HC-, h) (C3-C6) cycloalkyl, or i) CNCH2-. wherein R109 is a) alkylCl-C4, b)-CH2Cl c)-CH2CH=CH2, d) aryl, or e)-CH2CN ; wherein Rll0 and R'll are independently a) H-, b) CH3- or wherein R112 is a) H-, b) CH30-CH20-CH2-, or c) HOCH2-; wherein Rll3 is a) CH3-, b) HOCH2-, c) (CH3) 2N-phenyl, or d) (CH3)2N-CH2-; wherein Rll4 is a) HO-, b) CH30-, c) H2N-, d) CH30-C (0)-0-, e) CH3-C (0)-0-CH2-C (0)-0-, f) phenyl-CH2-0-CH2-C (0)-0-, g) HO- (CH2) 2-0-, h) CH30-CH2-0- (CH2) 2-0-, or i) CH3O-CH2-O-; wherein R"5 is a) H-, or b) C1- ; wherein Rll6 is a) HO- b) CH30-, or c) F; wherein R 150 and R151 are each H or alkyl C1-C4 or R150 and Rl5l taken together with the nitrogen atom to which each is attached form a monocyclic heterocyclic ring having from 3 to 6 carbon atoms ; R152 is a) H, b) Cl4alkyl, c) Cl-4heteroalkyl, d) (CH2)iC(=O)OC1-4alkyl, e) (CH2)iC(=O)C1-4alkyl, f) aryl, or g) hetl ; R153 and R154 are independently a) H, b) F, c) Cl-4alkyl, d) C3-6cYcloalkyl, e) Cl4heteroalkyl, f) aryl, g) hetl, h) OC1-4alkyl, i) O(C=O)C1-4alkyl, j) (C=O) OCl4alkyl ; or k) R153 and R154 taken together are C36cycloalkyl ; R155 is a) H, b) F, c) Cl_4alkyl, d) OC1-4alkyl, e) SCl4alkyl, or f) NHCl-4alkyl; R156 is a) H, b) Cl_4alkyl, c) OC1-4alkyl, d) SCl-4alkyl, or e) NHC1-4alkyl; R157 is <BR> <BR> a)-H,<BR> b)-F, c)-Cl, <BR> <BR> d)-NH2,<BR> e)-OH,<BR> f)-CN, g)-Cl-4alkyl, h)-OC1-4alkyl, i)-C1-4alkyl-W-C1-4alkyl, j)-NHC1-4alkyl, k)-(CH2)iC3-6cycloalkyl,<BR> l)-C(=O)C1-4alkyl, m)-OC(=O)C1-4alkyl, n)-C(=O)OC1-4alkyl, o)-S(O)iC1-4alkyl, or p)-C(=O)NHC1-4alkyl; Rise is<BR> a)-H, b)-CH3, c)-F, or d) -OH; R159 is a)-H, b)-C1-4alkyl, c)-C (=O) Cl_4alkyl,<BR> d) -C (=O) NHC1_4alkyl,<BR> e)-OC(=O)C1-4alkyl, f)-C(=O)OCl-4alkyl, or g) -S (O) iCl-4alkyl, or h)-C1-4alkyl-W1-C1-4alkyl; R160 is H, C2-6 alkenyl, C2-7alkynyl, C1-6 alkyl substituted with one or two of the following: a) F, b) Cl, <BR> c) CF3,<BR> d)-OH, e) Cl_4alkoxy, f)-CH2C(=O)C1-4alkyl,<BR> g)-OC(=O)N(Rl6l)2, h) Cl 4alkyl S (0) n, (wherein n is 0,1 or 2), i)-CN, j) carboxy, k)-Cl4alkoxycarbonyl,<BR> 1) -C (=O) N (Rl6l) 2, m)-N(Rl6l)SO2C1-4 alkyl, n) -N (Rl6l)C(=O)C1-4 alkyl,<BR> o) -N (Ri6i) C (=O) N (R4) 2, p)-N (Rl6l) C (=O) Cl4 alkoxy, q) aryl, or r) Hetl ; Ri6i is a) H, or b) C1-3 alkyl ; R162 is a) H, b) C1-8 alkyl, optionally substituted with one to three F, Cl, OH, CN, NH2, OC (=O) Cl4alkyl, or OC1-4 alkyl, c) C3-8 alkene, or d) C(=O)NR163R164 ; R163 and R164 are independently a) H, or b) C1-8 alkyl, optionally substituted with one to three F, Cl, OH, CN, or NH2; R165 is C1-4 alkyl, optionally substituted with 1-3 R168 ; R166 is a) Ci-s alkyl, optionally substituted with 1-3 halo, CN, NO2, OH, SH or NH2, b) -C (=O) R167 or c) -C (=S) NHC1-4 alkyl ; R167 is a) H, b) C1-6 alkyl, optionally substituted with OH, C1-4 alkoxy, NH2, SH or halo, or c)-CH2OC(=O)C1-4 alkyl ; R168 is j) halo, k)-CN,<BR> 1)-OH, m)-SH, n)-NH2, o)-OR169, p)-NHR169, q)-N(R169)2, or r) -S (=O) iRl69 ; R169 iS g) C1-6 alkyl, h) -C (=O) C1_4 alkyl,<BR> i) -C (=O) O C1_4 alkyl,<BR> j) -C (=O) NH2, k)-C(=O)NHC1-4 alkyl, or l)-SO2 C1-4 alkyl ; with the proviso that where j is 0, Y2 is -CH2-.

R170 is a) H, b) Cl-12 alkyl, optionally substituted with phenyl or CN, or c) C2-12 alkyl substituted with OH, SH, NH2,-OCi-6 alkyl,-NHC16 alkyl,-NHCOC1-6 alkyl, -NHSO2C1-6 alkyl,-S(O)iC1-6 alkyl, or one to three halo; R172 is a) H, b) C1-8 alkyl, c) aryl, d) hetl, e) C(=W)R174, f) or g) S (=O) iRl76 ; R173 iS a) H, or b)C1-8 alkyl ; R174 is a) H, b) aryl, c) hetl, d) NR177Rl78, or e) C1-8 alkyl ; R175 is a) C1-8 alkyl, b) aryl, or c) hetl ; R176 is a) aryl, b) hetl, c) NR177Rl78, or d) Cl_s alkyl ; R177 and R178 are independently a) H, b) C1-8 alkyl, or c) aryl; Rise and R181 taken together form C3-5 cycloalkyl ; R182 is H, CH3 or C1-4 alkanoyl; R183 is H, C1-4 alkyl, C1-4 alkanoyl, -C(=O)NH-C1-4 alkyl or -CO2C1-4 alkyl ; R184 is C1-4 alkyl, CH2OR186, S-C1-4 alkyl, OC1-4 alkyl, or NR187R188 ; Roi85 is phenyl,-CO2-(CH2) 2-OCH3,-P (=O) (OH) 2, -C(=O)-NR187R186, or -C(=O)-(CH2)2-CO2H ; Ri86 is H, phenyl, benzyl, CH3 or C (=O) CH3; R187 and R188 are independently H or C1-3 alkyl ; or R187 and R188 taken together form a 5-or 6-membered saturated heterocycle, wherein said saturated heterocycle may further contain one or two additional hetero-atoms selected from a group consisting of O, S(O)n or NR182 ; R, 89 is H, CH3 or benzyl; Rise is a) H, b) C1-4 alkyl, c) C (=O) C1_4 alkyl, d) C(=O)OC1-4 alkyl, e) C (=O) NHRl9l, or f) C (=S)NHRl91; R191 is H, C1-4 alkyl, or phenyl; at each occurrence, alkyl in Rlgo and Rl9l is optionally substituted with one or more halo, CN, NO2, phenyl, C3-6 cycloalkyl, OR192, C (=O) R192, OC (=O) R192, C (=O) OR192, SC(=O)iRl92, s(=O)iNRl92Rl92, NRl92Rl92, NRl92SO2Rl92, NRl92SO2Rl92Rl92, NRl92C (=O) Rl92, C (=O)NRl92Rl92, NRl92Rl92, oxo or oxime ; R192 is H, C1-4 alkyl, or phenyl; at each occurrence, phenyl in Rl9l and R192 is optionally substituted with one or more halo, CN, NO2, phenyl, C3-6 cycloalkyl, OR192, C (=O) R192, OC (=O) Ri92, C (=O) OR, 92, S (=O) ira196, S (=O)iNR192Rl92, NR192SO2Rl92, NR192SO2NR192R192, NR192C(=O)R192, C (=O)NR192R192, or NR192Rl92; R193 is selected from the group consisting of null, H, Cl-C4alkyl, C3-C5Cycloalkyl, Cl-C4haloalkyl, and halophenyl; R194 is selected from the group consisting of H, alkyl, Cl-C2alkoxy, halo, and haloalkoxy, or R193 and R, 94 can be taken together to form a 5-or 6-membered, optionally substituted, heteroalkyl or heteroaryl ring ; Rl9s is H or F ; R196 is selected from the group consisting of H, methyl, amino, and F; R197 is H, CH3, or F; B is an unsaturated 4-atom linker having one nitrogen and three carbons; M is a) H, b) C1-8 alkyl, c) C3-8 cycloalkyl, d) - (CH2) mORl3, or e)- (CH2) h-NR2lR22 ; Z is a) 0, b) S, or c) NM; W is a) CH, b) N, or c) S or 0 when Z is NM; Y is a) H, b) F, c) Cl, d) Br, e) C1-3 alkyl, or f) N02 ; X is a) H, b)-CN, c) OR27, d) halo, e) NO2, f) tetrazoyl, <BR> g)-SH,<BR> h) -S (=O) iR4, i)-S(=O)2-N=S(O)jR5R6, j)-SC(=O)R7, k) -C (=0) RZS,<BR> 1)-C(=O)NR27R28,<BR> m)-C(=NR29)R25, n)-C(R25)(R28)-OR13, O)-C(R25)(R28)-OC(=O)R13, P)-C(R28)(OR13)-(CH2)h-NR27R28, q)-NR27R28, r) -N (R27) C (=O) R7,<BR> s) -N (R27)-S (=O) iR7, t)-C(OR14)(OR15)R28, u)-C(R25)(Rl6)-NR27R26, or v) C1-8 alkyl substituted with one or more halos, OH, =0 other than at alpha position,-S(=O)iR17, -NR27R28, C2-5 alkenyl, 2-5 alkynyl, or C3-8 cycloalkyl ; X1 is N or CRise ; Y1 is a) S(O)i, b) S (NRi59), or c) S (NR159)(O); Mi is O or S ; X2 is 0 or NRl62 ; X3 is S (0) i or NR, 66 ; Y2 is a) 0 b) NH, c) CH2, or d) S (O) i; X4 is a) O b) NR172, c) S (0) i, or d) S (0) (NR173) ; and Y3 is CH or N; R4, R5, R6, R7, R13, R14, R15, R16, and R17 are the same as defined above; R25 is a) H, b) C1-3 alkyl optionally substituted with one or more halos, C3-8 cycloalkyl, C1-4 alkyl substituted with one or more of-S (=O)iR17, -OR13, or OC (=O) R13, NR27R28, or c) C2-5 alkenyl optionally substituted with CHO, or C02R13 ; R26 is a) R28, or b) NR27NR28 ; R27 and R28 at each occurrence are the same or different and are a) H, b) Cl8 alkyl, c) C3-8 cycloalkyl, d) - (CH2) mORl3, e)- (CH2) h-NR2lR22, or f) R27 and R28 taken together are- (CH2) 20 (CH2) 2-, - (CH2)hCH(COR7)-, or-(CH2)2N(CH2)2(R7); R29 is a)-NR27R28, b)-OR27, or c) -NHC (=O) R28 ; wherein R30 is a) H, b) C1-8 alkyl optionally substituted with one or more halos, or c) C1-8 alkyl optionally substituted with one or more OH, or C1_6 alkoxy; wherein E is a) NR39, b)-S(=O)i, <BR> c) 0, or<BR> c) O, or d) S (0) (NRlso) R38 is a) H, b) C1_6 alkyl, c)- (CH2) q-aryl, or d) halo; R39 is a) H, b) C1_6 alkyl optionally substituted with one or more OH, halo, or-CN, c) - (CH2) q-aryl, d)-CO2R40, <BR> e)-COR41,<BR> f)-C(=O)-(CH2)q-C(=O)R40,<BR> g) -S (=O) 2-C1-6alkyl,<BR> h) -S (=O) 2- (CH2) q-aryl, or i)-(C=O)j-Het; R40 is a) H, b) Cl-6 alkyl optionally substituted with one or more OH, halo, or-CN, c)-(CH2)q-aryl, or d)- (CH2) q-OR42 ; R41 is a) C1-6 alkyl optionally substituted with one or more OH, halo, or-CN, b)- (CH2) q-aryl, or c)- (CH2) q-OR42 ; R42 is a) H, b) C1_6 alkyl, c)- (CH2) q-aryl, or d)-C(=O)-Cl-6 alkyl ; aryl is a) phenyl, b) pyridyl, or c) napthyl; a to c optionally substituted with one or more halo, -CN, OH, SH, C16 alkyl, C16 alkoxy, or Cl-6 alkylthio; h is 1,2, or 3; i is 0,1, or 2; j is 0 or 1, with the proviso that when j is O, Y2 is -CH2- ; k is 3,4, or 5; 1 is 2 or 3; m is 4 or 5 ; n is 0, 1, 2,3, 4, or 5; p is 0,1, 2,3, 4, or 5; with the proviso that n and p together are 1,2, 3,4, or 5; q is 1,2, 3, or 4; u is 1 or 2; w is 0, 1, 2, or 3; x is 0,1, 2,3 or 4; and y is 0,1, 2,3 or 4; with the proviso that x and y taken together are 3 or 4; z is 1,2, 3,4 or 5, provided that i and z taken together are 2,3, 4 or 5; and G is The present invention also provides an oxazolidinone derivative of Formula (II) wherein J, R1, G and A are as defined above.

The present invention also is directed to an oxazolidinone derivative of formula (VIII) having an improved solubility, wherein R is-CH2-G-A and R1, G and A are as defined above. The present invention also is directed to a method of improving the solubility of an amide of Formula (III) in which the compound of Formula (VIII) is prepared, wherein R is-CH2-G-A and R1, G and A are as defined above. The present invention also is directed to a method of improving the solubility of an amide of Formula (III) in which the compound of Formula (XII) is prepared, wherein R is-CH2-G-A, with G, A, Q; Rsio, R4i0f Rsio and Rgio being as defined above.

The present invention is also directed to an oxazolidinone derivative of formula (XIII) wherein R is-G-A; J, G and A being as defined above; Ri'is a) H, b) OH, c) alkyl, d) alkoxy, e) alkenyl, f) amino, g) substituted alkyl, h) substituted alkoxy, i) substituted alkenyl, or j) substituted amino, R310, R4io and R5, o each independently are a) H, b) C1-4 alkyl, c) halogen, d) C1-4 alkoxy, e) hydroxy, f) (CH2) cOP (0) (OH) 2, g) C1-4 acyloxy, or h) C1-4 alkyl substituted by halogen, hydroxy, acyloxy, NRi2ioRi3io, or alkoxy; and Reic is a) H, b) CH3, or c) C2H5- The present invention is also directed to a method of preparing an oxazolidinone derivative having an improved water solubility comprising the steps of providing an amide of formula (XVI) reacting the amide with a compound of formula (XIV) to form a compound of formula (XVII) and removing the protecting groups to form a compound of formula (XVIII) wherein R is-G-A and J, R'1, G, A and Pr are as described above.

DETAILED DESCRIPTION OF THE INVENTION For the purpose of the present invention, the carbon content of various hydrocarbon containing moieties is indicated by a prefix designating the minimum and maximum number of carbon atoms in the moiety, i. e. , the prefix Ci-j defines the number of carbon atoms present from the integer"i"to the integer"j", inclusive. Thus, 1-4 alkyl refers to alkyl of 1-4 carbon atoms, inclusive, or methyl, ethyl, propyl, butyl and isomeric forms thereof.

The terms"1-2 alkyl",''C13 alkyl","C1-4 alkyl", "Ci-5 alkyl","C16 alkyl","C1_8 alkyl", and"C1_16 alkyl" refer to an alkyl group having one to two, one to three, one to four, one to five, one to six, one to eight, or one to sixteen carbon atoms respectively such as, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and their isomeric forms thereof.

The terms"2-4 alkenyl","2-5 alkenyl","2-3 alkenyl","2-14 alkenyl"and"Cz-16 alkenyl"refer to at least one double bond alkenyl group having two to four, two to five, two to eight, two to fourteen, or two to sixteen carbon atoms, respectively such as, for example, ethenyl, propenyl, butenyl, pentenyl, pentdienyl, hexenyl, hexdienyl, heptenyl, heptdienyl, octenyl, octdienyl, octatrienyl, nonenyl, nonedienyl, nonatrienyl, undecenyl, undecdienyl, dodecenyl, tridecenyl, tetradecenyl and their isomeric forms thereof.

The terms"2-5 alkynyl","2-9 alkynyl", and"2-10 alkynyl"refer to at least one triple bond alkynyl group having two to five, two to eight, or two to ten carbon atoms respectively such as, for example, ethynyl, propynyl, butynyl, pentynyl, pentdiynyl, hexynyl, hexdiynyl, heptynyl, heptdiynyl, octynyl, octdiynyl, octatriynyl, nonynyl, nonediynyl, nonatriynyl and their isomeric forms thereof.

The terms"C3-4 cycloalkyl","C3-6 cycloalkyl","C5-6 cycloalkyl", and"3-8 cycloalkyl"refer to a cycloalkyl having three to four, three to six, five to six, or three to eight carbon atoms respectively such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and their isomeric forms thereof.

The terms"1-4 alkoxy",''C16 alkoxy", and''C18 alkoxy"refer to an alkyl group having one to four, one to six, or one to eight carbon atoms respectively attached to an oxygen atom such as, for example, methoxy, ethoxy, propyloxy, butyloxy, pentyloxy, hexyloxy, heptyloxy, or octyloxy and their isomeric forms thereof.

The terms''C16 alkylamino", and''C18 alkylamino" refer to an alkyl group having one to six, or one to eight carbon atoms respectively attached to an amino moiety such as, for example, methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, heptylamino, or octoylamino and their isomeric forms thereof.

The terms"C16 dialkylamino", and''C18 dialkylamino" refer to two alkyl groups having one to six, or one to eight carbon atoms respectively attached to an amino moiety such as, for example, dimethylamino, methylethylamino, diethylamino, dipropylamino, methypropylamino, ethylpropylamino, dibutylamino, dipentylamino, dihexylamino, methylhecylamino, diheptylamino, or dioctoylamino and their isomeric forms thereof.

The terms"1-3 acyl","C1-4 acyl","C1_5 acyl",''C16 acyl",''C18 acyl", and"2-3 acyl"refer to a carbonyl group having an alkyl group of one to three, one to four, one to five, one to six, one to eight, or two to eight carbon atoms.

The terms''C14 alkoxycarbonyl","C16 alkoxycarbonyl", and''C18 alkoxycarbonyl"refer to an ester group having an alkyl group of one to four, one to six, or one to eight carbon atoms.

The term''C18 alkyl phenyl"refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one phenyl radical.

The term"C2-8 alkenyl phenyl"refers to a at least one double bond alkenyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one phenyl radical.

The term''C1_8 alkyl pyridyl"refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one pyridyl radical.

The term''C18 hydroxyl"refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof attached to a hydroxy group.

The term''C1_8 alkylsulfonyl"refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof attached to a SO2 moiety.

The term"C16 alkylthio"refers to an alkyl group having one to six carbon atoms and isomeric forms thereof attached to a sulfur atom.

The term"Het"refers to 5 to 10 membered saturated, unsaturated or aromatic heterocyclic rings containing one or more oxygen, nitrogen, and sulfur forming such groups as, for example, pyridine, thiophene, furan, pyrazoline, pyrimidine, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2- pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 3-pyridazinyl, 4-pyridazinyl, 3-pyrazinyl, 2-quinolyl, 3-quinolyl, 1- isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 2- quinazolinyl, 4-quinazolinyl, 2-quinoxalinyl, 1- phthalazinyl, 4-oxo-2-imidazolyl, 2-imidazolyl, 4- imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- oxazolyl, 4-oxo-2-oxazolyl, 5-oxazolyl, 4,5,- dihydrooxazole, 1,2, 3-oxathiole, 1,2, 3-oxadiazole, 1,2, 4- oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 2- thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazole, 4- isothiazole, 5-isothiazole, 2-indolyl, 3-indolyl, 3- indazolyl, 2-benzoxazolyl, 2-benzothiazolyl, 2- benzimidazolyl, 2-benzofuranyl, 3-benzofuranyl, benzoisothiazole, benzisoxazole, 2-furanyl, 3-furanyl, 2- thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3- isopyrrolyl, 4-isopyrrolyl, 5-isopyrrolyl, 1,2, 3, - oxathiazole-1-oxide, 1, 2,4-oxadiazol-3-yl, 1,2, 4- oxadiazol-5-yl, 5-oxo-1, 2,4-oxadiazol-3-yl, 1,2, 4- thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl, 3-oxo-1, 2,4- thiadiazol-5-yl, 1, 3,4-thiadiazol-5-yl, 2-oxo-1, 3,4- thiadiazol-5-yl, 1, 2,4-triazol-3-yl, 1, 2,4-triazol-5-yl, 1, 2,3, 4-tetrazol-5-yl, 5-oxazolyl, 1-pyrrolyl, 1- pyrazolyl, 1,2, 3-triazol-1-yl, 1,2, 4-triazol-1-yl, 1- tetrazolyl, 1-indolyl, 1-indazolyl, 2-isoindolyl, 7-oxo- 2-isoindolyl, l-purinyl, 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, 1,3, 4, -oxadiazole, 4-oxo-2- thiazolinyl, or 5-methyl-1, 3,4-thiadiazol-2-yl, thiazoledione, 1,2, 3,4-thiatriazole, 1,2, 4-dithiazolone.

Each of these moieties may be substituted as appropriate.

The term hertz at each occurrence is independently a C-linked 5-or 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur within the ring.

The term het2 at each occurrence is independently a N-linked 5-or 6-membered heterocyclic ring having 1 to 4 nitrogen and optionally having one oxygen or sulfur within the ring.

The term Het, is a 5-or 6-membered heteroaromatic moiety having 1-3 N, 0 or S atoms, optionally substituted with the following: a) F, b) Cl, c) C1-3 alkoxy, d) C13 alkylthio, or e) CN.

The term het, is a C-linked 5-or 6-membered saturated or unsaturated heterocyclic ring having 1, 2, or 3 heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen, which is optionally fused to a benzene ring.

The term halo refers to fluoro, chloro, bromo, or iodo.

The term Pr refers to a suitable phosphate protecting group, such as benzyl, alkyl, tert-butyl, etc.

The compounds of the present invention can be converted to their salts, where appropriate, according to conventional methods.

The term"pharmaceutically acceptable salts"refers to acid addition salts useful for administering the compounds of this invention and include hydrochloride, hydrobromide, hydroiodide, sulfate, phosphate, acetate, propionate, lactate, mesylate, maleate, malate, succinate, tartrate, citric acid, 2-hydroxyethyl sulfonate, fumarate and the like. These salts may be in hydrated form.

When Q is the structure of the dotted line in the heterocyclic ring means that this bond can be either single or double. In the case where the dotted line is a double bond, the R39 group will not be present.

The compounds of this invention contain a chiral center at C5 of the isoxazoline ring, and as such there exist two enantiomers or a racemic mixture of both. This invention relates to both the enantiomers, as well as mixtures containing both the isomers. In addition, depending on substituents, additional chiral centers and other isomeric forms may be present in any of A or R group, and this invention embraces all possible stereoisomers and geometric forms in these groups.

The compounds of this invention are useful for treatment of microbial infections in humans and other warm blooded animals, under both parenteral and oral administration. The inventive compounds have antibacterial activity against a number of human and veterinary pathogens including Gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci, Gram-negative organisms such as H. influenzae and M. catarrhalis, anaerobic organisms such as Bacteroides spp. and Clostridasppa, Mycobacterium tuberculosis, M. avium and M. spp. and organisms such as Mycoplasma spp.

The pharmaceutical compositions of this invention may be prepared by combining the compounds of this invention with a solid or liquid pharmaceutically acceptable carrier and, optionally, with pharmaceutically acceptable adjuvants and excipients employing standard and conventional techniques. Solid form compositions include powders, tablets, dispersible granules, capsules, cachets and suppositories. A solid carrier can be at least one substance which may also function as a diluent, flavoring agent, solubilizer, lubricant, suspending agent, binder, tablet disintegrating agent, and encapsulating agent. Inert solid carriers include magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, cellulosic materials, low melting wax, cocoa butter, and the like.

Liquid form compositions include solutions, suspensions and emulsions. For example, there may be provided solutions of the compounds of this invention dissolved in water and water-propylene glycol and water-polyethylene glycol systems, optionally containing suitable conventional coloring agents, flavoring agents, stabilizers and thickening agents.

Preferably, the pharmaceutical composition is provided employing conventional techniques in unit dosage form containing effective or appropriate amounts of the active component, that is, the compound according to this invention.

The quantity of active component, that is the compound according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application, the potency of the particular compound, the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition.

In therapeutic use for treating, or combatting, bacterial infections in warm-blooded animals, the compounds or pharmaceutical compositions thereof will be administered orally, parenterally and/or topically at a dosage to obtain and maintain a concentration, that is, an amount, or blood-level of active component in the animal undergoing treatment which will be antibacterially effective. Generally, such antibacterially effective amount of dosage of active component will be in the range of about 0.1 to about 100, more preferably about 3.0 to about 50 mg/kg of body weight/day. It is to be understood that the dosages may vary depending upon the requirements of the patient, the severity of the bacterial infection being treated, and the particular compound being used. Also, it is to be understood that the initial dosage administered may be increased beyond the above upper level in order to rapidly achieve the desired blood-level or the initial dosage may be smaller than the optimum and the daily dosage may be progressively increased during the course of treatment depending on the particular situation. If desired, the daily dose may also be divided into multiple doses for administration, e. g. , 2-4 four times per day.

When the compounds according to this invention are administered parenterally, i. e. , by injection, for example, by intravenous injection or by other parenteral routes of administration. Pharmaceutical compositions for parenteral administration will generally contain a pharmaceutically acceptable amount of the compound or a soluble salt (acid addition salt or base salt) dissolved in a pharmaceutically acceptable liquid carrier such as, for example, water-for-injection and a buffer to provide a suitably buffered isotonic solution, for example, having a pH of about 3.5-6. Suitable buffering agents include, for example, trisodium orthophosphate, sodium bicarbonate, sodium citrate, N-methylglucamine, L (+)- <BR> <BR> lysine and L (+) -arginine to name but a few representative buffering agents. The compound of this invention gener- ally will be dissolved in the carrier in an amount sufficient to provide a pharmaceutically acceptable injectable concentration in the range of about 1 mg/mL to about 400 mg/mL of solution. The resulting liquid pharmaceutical composition will be administered so as to obtain the above-mentioned antibacterially effective amount of dosage. The compounds according to this invention are advantageously administered orally in solid and liquid dosage forms.

As a topical treatment an effective amount of Formula I is admixed in a pharmaceutically acceptable gel or cream vehicle that can be applied to the patient's skin at the area of treatment. Preparation of such creams and gels is well known in the art and can include penetration enhancers.

The present invention improves the solubility and bioavailability of an amide of Formula III by converting it into a prodrug of Formula (VIII). The general scheme for preparing the prodrug of Formula (VIII) is shown below in Schemes 1 and 2. O Scheme 1 (PhCH20) 2p b o + RNH2 Ste V IV O O ici (PhCH20) 2 p (PhCH20) 2 P O 0 ! vn R1 COCI < ! JX C : O vu 6 o vu O R vil (HO) 2P VII Õ O Step 3 N"'R Ri I R vm In the above reaction scheme, the carboxylic acid derivative of Formula IV is prepared as described in M. G.

Nicolaou, C. -S. Yuan and R. T. Borchardt, J. Med. Chem.

1996,61, 8636-8641. Condensation of the amine of Formula V with the carboxylic acid of IV is accomplished by methods known in the art for amide or peptide bond formation. Examples include 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride and 4- (dimethylamino)- pyridine and solvents such as methylene chloride at reaction temperatures of 0 to 24°C, 1- (3-dimethylamino- propyl) -3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole and solvents such as dimethylformamide at 0 to 24°C, and bis (2-oxo-3- oxazolidinyl) phosphinic chloride and triethylamine and solvents such as methylene chloride at 0 to 24°C.

In Step 2 of Scheme 1, the amide of VI undergoes an acylation reaction to give the compound of VII, wherein J is an oxygen atom. This reaction is conveniently carried out by allowing the compound of VI to react with an acid chloride in the presence of an efficient acid scavenger.

Solvents such as methylene chloride, ethylene chloride or carbon tetrachloride at a temperature of from 24°C to the reflux temperature of the solvent can be used. Acid scavengers such as 3 A units molecular sieves, propylene oxide, 1, 8-bis (dimethylamino) naphthalene and methyl trimethylsilylcarbamate are suitable for use in this reaction. In Step 3 of Scheme 1, the phosphate esters of Formula VII are deprotected. This can be carried out by hydrogenolysis at atmospheric pressure and ambient temperature with a palladium catalyst. Solvents such as tetrahydrofuran, diethylether, or 1,2-dimethoxyethane can be used for this reaction.

Alternatively, compounds of formula (VIII) can be prepared according to the following Scheme 2. In Scheme 2, Pr of formula (XIII) represents a suitable phosphate protecting group, such as benzyl, alkyl or tert-butyl.

Scheme 2 0 0 (PrO) 2 b (PrO P (COCI2/DMF O k k 2 2 Step 1 (XIV) (XIII) J O R-N ! C-R (PrO) 20 (III) R R Step 2 I N Step 3 (XV) 0 (HO) 2 P Õ O R C=J (VIII) In Step 1, the acid (XIII) is converted to the acid chloride (XIV) with, for example, oxalyl chloride and dimethylformamide in a solvent, such as methylene chloride, at temperatures of from 0 to 30°C. In Step 2, the compound of formula (XIV) is allowed to react with the compound of formula (III) in a solvent, such as methylene chloride, ethylene chloride or acetonitrile, in the presence of an efficient acid scavenger, such as methyl trimethylsilylcarbamate, at the reflux temperature of the solvent. In Step 3, the phosphate protecting groups of the compound of formula (XV) is removed by methods known in the art.

Examples of amides containing oxazolidinone groups that can be used in the present invention are shown below. The preparation of the following amides of Examples 1-434 are shown in United States Patent No.

6,362, 189 B1, the disclosure of which is herein incorporated by reference thereto.

TABLE A EXAMPLE 1: (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]- 2-oxo-5-oxazolidinyl] methyl] thioacetamide (I) EXAMPLE 2: (S)-N-[[3-[3-Fluoro-4-[4-(5-methyl-1,3,4- thiadiazol-2-yl)-1-piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] thioacetamide (2) EXAMPLE 3: (5)-N- [ [3- [3-Fluoro-4- [2', 5- dioxospiro [piperidine-4, 4'-imidazolidine]-1-yl] phenyl] - 2-oxo-5-oxazolidinyl] methyl] thioacetamide (3).

EXAMPLE 4 : (S)-N-[[3-[3-Fluoro-4-(4- morpholinyl) phenyl]-2-oxo-5- oxazolidinyl] methyl] thioacetamide (4).

EXAMPLE 5: (S)-cis-N-[[3-[3-Fluoro-4-(tetrahydro-1- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide EXAMPLE 6: (S) -trans-N- [ [3- [3-Fluoro-4- (tetrahydro-l- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide EXAMPLE 7: (S) -N- [ [3- [3-Fluoro-4- (tetrahydro-1, 1- dioxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide EXAMPLE 8: (S)-N- [ [3- [3-Fluoro-4- (4-morpholinyl) phenyl]- 2-oxo-5-oxazolidinyl] methyl] -thioformamide (7).<BR> <P>EXAMPLE 9: (S)-N- [ [3- [3-Fluoro-4- (4-morpholinyl) phenyl] - 2-oxo-5-oxazolidinyl] methyl] thiopropion-amide (9).

EXAMPLE 10: (S)-N-[[3-[3-Fluoro-4-(4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl] -2- chlorothioacetamide (11).

EXAMPLE 11: (S)-N- [ [3- [3-Fluoro-4- (4- moropholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a, a, a-trifluorothioacetamide (13).

EXAMPLE 12: (S)-N- [ [3- [3-Fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a- fluorothioacetamide (15).

EXAMPLE 13: (S)-N- [ [3- [3-Fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a, a- difluorothioacetamide (17).

EXAMPLE 14: (S)-N-[[3-[3-Fluoro-4-(4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a- cyanothioacetamide (19).

EXAMPLE 15: (S)-N- [ [3- [3-Fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a, a- dichlorothioacetamide (21).

EXAMPLE 16: (S)-N- [ [3- [3-Fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-a- (methoxycarbonyl) thioacetamide (23).

EXAMPLE 17: (S)-N-[[3-[4-[1-[1,2,4] Triazolyl] phenyl-2- oxo-5-oxazolidinyl] methyl] thioacetamide (25).

EXAMPLE 18: (S)-N-[[3-[4-[1-[1,2,4] Triazolyl] phenyl-2- oxo-5-oxazolidinyl] methyl] thioacetamide (25).

EXAMPLE 19: (S)-N- [ [3- [1- (Hydroxyacetyl)-5-indolinyl]-2- oxo-5-oxazolidinyl] methyl] thioacetamide (28).

EXAMPLE 20: (S)-N- [ [3- [3-Fluoro-4- [4- (hydroxyacetyl)-l- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] thioacetamide (30).

EXAMPLE 21: (S)-N- [ [3- [3-Fluoro-4- (4- <BR> thiomorpholinyl) phenyl] -2-oxo-5-oxazolidinyl] methyl] thio- acetamide (32).

EXAMPLE 22: (S)-N- [ [3- [3-Fluoro-4- (4- thiomorpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thio- acetamide, thiomorpholine S-oxide (34).

EXAMPLE 23: (S)-N-[[3-[3-Fluoro-4-(4- thiomorpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thio- acetamide, thiomorpholine S, S-dioxide (36).

EXAMPLE 24: (S)-N- [ [3- [3, 5-Difluoro-4- [4- (hydroxyacetyl)-1-piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] thioacetamide (38).

TABLE B Example Compound R, R' No.

25 (S)-N- [ [3- [3-Fluoro-4- (4-morp R = H, R'= holinyl)-CH (CH3) 2 <BR> <BR> phenyl]-2-oxo-5-oxazolidinyl]<BR> methyl]-2- methylpropanethioamide; mp 152-153 °C (dec. ); Anal. calcd for CieH24FN303S : C, 56. 67 ; H, 6. 34 ; N, 11. 02. Found : C, 56. 58 ; H, 6. 41 ; N, 10. 81 26 (S)-N- [ [3- [3-Fluoro-4- (4-morp holinyl)-R H, R'= phenyl]-2-oxo-5-oxazolidinyl] methyl- cyclopropane-carbothioamide ; mp 155-156 °C ; Anal. calcd for C18H22FN303S : C, 56. 98 ; H, 5. 84 ; N, 11. 07. Found : C, 56. 98 ; H, 5. 85 ; N, 10. 97 27 (S)-N- [ [3- [3, 5-Difluoro-4- (4- R F, R'CH3 morpholinyl)- phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide TABLE C Example Compound Amine Dithio No. Compound (from Preparation Z) 28 (S)-N- [ [3- [3-Fluo o Z (a) ro-4-O=SL2N>NS (4-thiomorpholiny F 2 1)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- propanethioamide, thiomorpholine S-oxide ; mp 196-197°C ; Anal. calcd for C17H22FN303S2 : C, 51. 11 ; H, 5. 55 ; N, 10. 52 ; S, 16. 05. Found : C, 50. 99 ; H, 5. 60 ; N, 10. 55 ; S, 15. 75 Example Compound Amine Dithio No. Compound (from Preparation Z) 29 S)-N-3- [3-Fluor Same as Z (b) <BR> o-4- (4- above<BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5 oxazolidinyl] meth yl]-2- methylpropanethio - amide, thiomorpholine S-oxide; mp 195-196°C ; Anal. calcd for Cl8H24FN303S2 : C, 52. 28 ; H, 5.85 ; N, 10.16 ; S, 15.51. Found: C, 52.24 ; H, 5.97 ; N, 10.16 ; S, 15.28 30 (S)-N-3- [3-Fluo Same as Z (c) ro-4-above (4-thiomorpholiny 1)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiomorpholine S-oxide; mp 109-110°C ; Anal. calcd for CisH22FN303S2 : C, 52. 54 ; H, 5.39 ; N, 10.21 ; S, 15.58. Found: C, 52.48 ; H, 5.51 ; N, 10.28 ; S, 15.29 Example Compound Amine Dithio No. Compound (from Preparation Z) 31 (S)-N- [ [3- [3-Fluo Same as Z (d) ro-4-above (4-thiomorpholiny<BR> 1) phenyl] -2-oxo-5 oxazolidinyl] meth yl] butanethioamide, thiomorpholine S-oxide 32 (S)-N-[[3-[3-Fluo Same as Z (e) ro-4-above (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth yl]-3 methylbutanethioa mide, thiomorpholine S-oxide 33 (S)-N-[[3-[3-Fluo Same as Z (f) ro-4-above (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth yl]-2 methylbutanethioa mide, thiomorpholine S-oxide 34 (S)-N-[[3-[3-Fluo Same as Z (g) ro-4-above (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth Example Compound Amine Dithio No. Compound (from Preparation Z) yl] 3,3-dimethylbutan ethio-amide, thiomorpholine S-oxide 35 (S)-N- [ [3- [3-Fluo Same as Z (h) ro-4-above (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth yl] cyclobutanecarbot hio-amide, thiomorpholine S-oxide 36 (S)-N-3- [3-Fluo Same as Z (i) ro-4-above (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth yl]-1- cyclopentanecarbo thio-amide, thiomorpholine S-oxide 37 (S)-N- [ [3- [3-Fluo Same as above Z (j) ro-4- (4-thiomorpholiny 1) phenyl]-2-oxo-5 oxazolidinyl] meth yl] cyclohexanecarbot hio- amide, thiomorpholine S-oxide Example Compound Amine Dithio No. Compound (from Preparation Z) 38 (S)-N- [ [3- [3-Fluo Same as above Z (k) ro-4- (4-thiomorpholiny 1)- phenyl]-2-oxo-5 oxazolidinyl] meth yl]-2- cyclopropylethane thio- amide, thiomorpholine S-oxide 39 (S)-N-3- [3-Fluo Same as above Z (1) ro-4- (4-thiomorpholiny 1)- phenyl]-2-oxo-5 oxazolidinyl] meth yl]-2- cyclobutylethanet hio- amide, thiomorpholine S-oxide 40 (S)-N- [ [3- [3-Fluo Same as above Z (m) ro-4- (4-thiomorpholiny 1)- phenyl]-2-oxo-5 oxazolidinyl] meth yl]-2- cyclopentylethane thio- amide, thiomorpholine S-oxide 41 (S)-N- [ [3- [3-Fluo F o Ethyl ro-4-O=SrENANAO dithioacetate (4-thiomorpholiny F-1-t-H NH2 Example Compound Amine Dithio No. Compound (from Preparation Z) 1)- phenyl]-2-oxo-5 oxazolidinyl] meth yl]- thioacetamide, thiomorpholine S-oxide 42 (S)-N-3- [3-Fluo Same as above Z (a) ro-4- (4-thiomorpholiny 1)- phenyl]-2-oxo-5 oxazolidinyl] meth yl]- propanethioamide, thiomorpholine S-oxide 43 (S)-N- [ [3- [3-Difl Same as Z (b) uoro-above 4- (4-thiomorpholiny <BR> <BR> 1)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiomorpholine S-oxide 44 (S)-N-[[3-[3-Difl Same as Z (c) uoro-above 4- (4-thiomorpholiny <BR> <BR> 1)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiomorpholine S-oxide (S)-N- [ [3- [4- (4 Ethyl thiomorpholinyl)- dithioacetate phenyl]-2-oxo-5-o=s NeNXO oxazolidinyl] meth" Y1 _ thioacetamide, thiomorpholine S-oxide (S)-N- [ [3- [4- (4 Same as Z (a) thiomorpholinyl)-above phenyl]-2-oxo-5- oxazolidinyl] meth yl]- propanethioamide, thiomorpholine S-oxide (S)-N- [ [3- [4- (4 Same as Z (b) thiomorpholinyl)-above phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiomorpholine S-oxide (S)-N- [ [3- [4- (4 Same as Z (c) thiomorpholinyl)-above phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiomorpholine S-oxide

(S)-N- [ [3- [3, 5- Z (a) Difluor- p F OII 4 HOCH2-C N hydroxyacetyl)-1- piperazinyl] pheny NH2 1]-2- oxo-5- oxazolidinyl]- methyl] propanethi o- amide (S)-N- [ [3- [3, 5- Same as Z (b) Difluoro-above 4- (4- hydroxyacetyl)-1- piperazinyl] pheny 1]-2- oxo-5- oxazolidinyl]- methyl]-2-methyl- propanethioamide (S)-N- [ [3- [3, 5- Same as Z (c) Difluoro-above 4- (4- hydroxyacetyl)-1- piperazinyl] pheny 1]-2- oxo-5- oxazolidinyl]- methyl] cyclopropa ne- thioamide (S)-N- [ [3- [3- [4 Z (a) (hydroxyacetyl)- 1-11/-\ HOCH-C-N N- -N0 piperazinyl] pheny =''--H 11-2- oxo-5- oxazolidinyl]- methyl] propanethi o- amide (S)-N- [ [3- [3- [4 Same as Z (b) (hydroxyacetyl)-above 1- piperazinyl] pheny 1]-2- oxo-5- oxazolidinyl]-<BR> methyl]-2-methyl- propanethioamide 54 (S)-N-[[3-[3-[4 Same as Z (c) <BR> <BR> (hydroxyacetyl)-above<BR> 1- piperazinyl] pheny 1]-2- oxo-5- oxazolidinyl]- methyl] cyclopropa ne- carbothioamide TABLE D Example Compound Amine Dithio No. Compound (from Preparation Z) 55 (S)-N- [ [3- [3- Z (a) Fluoro-4-o (4-A, HOCHZ-C-N N I N thiomorpholinyl)-V-H phenyl]-2-oxo-5-NHy oxazolidinyl] meth yl]- propanethioamide, thiomorpholine S, S- dioxide 56 (S)-N- [ [3- [3- Same as Z (b) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio Example Compound Amine Dithio No. Compound (from Preparation Z) amide, thiomorpholine S, S-dioxide 57 (S)-N- [ [3- [3- Same as Z (c) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiomorpholine S, S-dioxide 58 (S)-N- [ [3- [3, 5- Difluoro-ozs N<N O 4- (4- H NHZ thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]- methyl] thioacetam ide, thiomorpholine S, S- dioxide 59 (S)-N- [ [3- [3, 5-Same as Z (a) Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- propanethioamide, thiomorpholine S, S- dioxide Example Compound Amine Dithio No. Compound (from Preparation Z) 60 (S)-N- [ [3- [3, 5- Same as Z (b) Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiomorpholine S, S-dioxide 61 (S)-N- [ [3- [3, 5- Same as Z (c) Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl] cyclopropanecarbo thio- amide, thiomorpholine S, S-dioxide 62 (S)-N- [ [3- [4- (4- o Ethyl thio-o2s<N e N) (o dithioacetate morpholinyl) pheny-" l]-2-oxo-5-NHz oxazolidinyl]- methyl] thioacetam ide, thiomorpholine S, S-dioxide 63 (S)-N- [ [3- [4- (4- Same as Z (a) thio-above morpholinyl) pheny l]-2-oxo-5- oxazolidinyl]- methyl] propanethi Example Compound Amine Dithio No. Compound (from Preparation Z) o- amide, thiomorpholine S, S-dioxide 64 (S)-N- [ [3- [4- (4- Same as Z (b) thio-above morpholinyl) pheny <BR> <BR> 1)-2-oxo-5-<BR> oxazolidinyl]-<BR> methyl]-2-methyl- propanethioamide, thiomorpholine S, S-dioxide 65 (S)-N-[[3-[4-(4- Same as Z (c) thio-above morpholinyl) pheny <BR> <BR> l]-2-oxo-5-<BR> oxazolidinyl]- methyl] cyclopropa ne- carbothioamide, thiomorpholine S, S-dioxide TABLE E Example Compound Amine Dithio No. Compound (from Preparation Z) 0 66 (s)-N-[[3-[3-s N4N O Z (a) Fluoro-4-H (4-F-NH2 thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- propanethioamide 67 (S)-N-[[3-[3- Same as Z (b) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide 68 (S)-N-[[3-[3- Same as Z (c) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide 69 (S)-N-[[3-[3- Same as Z (d) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl] butanethioamide 70 (S)-N- [ [3- [3- Same as Z (e) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-3- methylbutanethioa mide 71 (S)-N-[[3-[3- Same as Z (f) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylbutanethioa mide 72 (S)-N-[[3-[3- Same as Z (g) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- 3,3- dimenthylbutaneth io- amide 73 (S)-N-[[3-[3- Same as Z (h) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclobutanecarbot hio- amide 74 (S)-N-[[3-[3- Same as Z (i) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopentanecarbo thio- amide 75 (S)-N-[[3-[3- Same as Z (j) Fluoro-4-above (4- <BR> <BR> thiomorpholinyl)-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclohexanecarbot hio- amide 76 (S)-N- [ [3- [3- Same as Z (k) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclopropylethane thio- amide 77 (S)-N- [ [3- [3- Same as Z (1) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclobutylethanet hio- amide 7 8 (S)-N- [ [3- [3-Same as Z (m) Fluoro-4-above (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclopentylethane thio- amide 7 9 (S)-N- [ [3- [3, 5-F o Ethyl Difluoro-s NN) 4O dithioacetate 4- (4--H thiomorpholinyl)-F NH2 phenyl]-2-oxo-5- oxazolidinyl] meth yl] thioacetamide 80 (S)-N- [3- [3, 5-Same as Z (a) .. _ t, ______ _, _ ____ Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl] propanethioamide 81 (S)-N- [ [3- [3, 5- Same as Z (b) Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide 82 (S)-N- [ [3- [3, 5- Same as Z (c) Difluoro-above 4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl] meth yl] cyclopropanecarbo thio-amide 83 (S)-N- [ [3- [4- (4- thio-s NoNto morpholinyl) pheny" l]-2-oxo-5-NH2 oxazolidinyl]- methyl] thioacetam ide 84 (S)-N- [ [3- [4- (4- Same as Z (a) thio-above morpholinyl) pheny l]-2-oxo-5- oxazolidinyl]- methyl] propanethi o amide 85 (S)-N- [ [3- [4- (4- Same as Z (b) thio-above morpholinyl) pheny <BR> <BR> l]-2-oxo-5-<BR> oxazolidinyl]-<BR> methyl]-2-methyl- propanethioamide 86 (S)-N- [ [3- [4- (4- Same as Z (c) thio-above morpholinyl) pheny <BR> <BR> l]-2-oxo-5-<BR> oxazolidinyl]- methyl] cyclopropa ne- carbothioamide EXAMPLE 87: (S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5- oxazolidinyl] methyl]-l-azetidinecarbothioamide, thiomorpholine S-oxide; Anal. Calcd for Cl8H23FNe03S2, C, 50.69 ; H, 5.43 ; N, 13.14. Found: C, 50.79 ; H, 5.45 ; N, 12.82 ; mp 213-214°C.

EXAMPLE 88: (S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5- oxazolidinyl] methyl]-1-azetidinecarbothioamide.

EXAMPLE 89: (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]ph enyl-2-oxo-5-oxazolidinyl] methyl] propanethioamide TABLE F Example No. Compound Example No. Compound 90 (S)-N- [ [3- [3-Fluoro-4- [4- (hy R CH (CH3) 2 droxy- acetyl)-1-piperazinyl] phenyl ]-2-oxo-5- oxazolidinyl] methyl]-2-methy lpropane-thioamide ; Anal. calcd for C2oH27FN404S : C, 54. 78 ; H, 6. 21 ; N, 12. 78 ; S, 7. 31. Found : C, 54. 67 ; H, 6. 34 ; N, 12. 41 ; S, 7. 15 91 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy-R =-a acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl] cyclop ropane-carbothioamide ; mp 179-181°C ; Anal. calcd for C2oH25FN404S : C, 55. 03 ; H, 5. 77 ; N, 12. 84 ; S, 7. 34. Found : C, 55. 15 ; H, 5. 72 ; N, 12. 76 ; S, 7. 09 92 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy- acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl] butane thioamide 93 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy- acetyl)-1-piperazinyl] phen R= CH2-CH-CH3 yl]-2-oxo-5- oxazolidinyl] methyl]-3-met hylbutane- thioamide 94 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy- acetyl)-1-piperazinyl] phen R=CH-CH2-CH3 yl]-2-oxo-5- oxazolidinyl] methyl]-2-met hylbutane- Example No. Compound thioamide 95 (S)-N- [ [3- [3-Fluoro-4- [4- ( R = CH2-C (CH3) 3 hydroxy acetyl)-1-piperazinyl] phen yl]-2-oxo-5-oxazolidinyl oxazolidinyl] methyl]-3, 3-d imethyl- butanethioamide 96 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy- acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl] cyclob utane-carbothioamide 97 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy- acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl] cyclop entane- carbothioamide 98 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy-R= acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl] cycloh exane- carbothioamide 99 (S)-N- [ [3- [3-Fluoro-4- [4- ( hydroxy-R=CH2-< acetyl)-1-piperazinyl] phen yl]-2-oxo-5- oxazolidinyl] methyl]-2-cyc lopropyl-ethanethioamide 100 (S)-N- [ [3- [3-Fluoro-4- [4- (hy droxy- acetyl)-1-piperazinyl] phenyl Example No. Compound ]-2-oxo-5- oxazolidinyl] methyl]-2-cyclo butyl ethanethioamide 101 (S)-N- [ [3- [3-Fluoro-4- [4- (hy droxy-R = CH24 acetyl)-1-piperazinyl] phenyl ]-2-oxo-5- oxazolidinyl] methyl]-2-cyclo pentylethanethioamide EXAMPLE 102: (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]ph enyl]-2oxo-5-oxazolidinyl] methyl]-l-azetidinecarbothio- amide.

EXAMPLE 103: (S)-N-[[3-Fluoro-4-(4-acetyl-l-piperazinyl)phenyl]-2-oxo- 5-oxazolidinyl] methyl] thioacetamide TABLE G Example Dithio No. Product Amine Compound 104 (S)-N- [[3-[3-Fluoro-4-(4-acetyl-l-pi P-90 Z (a) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] propanethioamide ; mp 161-162°C ; Anal. calcd for C19H25FN403S : C, 55.87 ; H, 6.17 ; N, 13.72 ; S, 7.85. Found: C, 55.79 ; H, 6.26 ; N, 13.60 ; S, 7.71 105 (S)-N- [ [3- [3-Fluoro-4- (4-acetyl-1-pi P-90 Z (b) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl]-2-methylpropane- thioamide Example Dithio No. Product Amine Compound 106 (S)-N- [ [3- [3-Fluoro-4- (4-acetyl-1-pi P-90 Z (c) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] cyclopropanecarbo- thioamide; mp 159-160°C ; Anal. calcd for C2oH25FN403S : C, 57.13 ; H, 5.99 ; N, 13.32 ; S, 7.62. Found: C, 57.05 ; H, 6.01 ; N, 13.15 ; S, 7.45.

107 (S)-N- [[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (d) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] butanethioamide 108 (S)-N- [[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (e) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl]-3-methylbutanethioamide 109 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (f) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl]-2-methylbutane-thioamide 110 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (g) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] -3, 3-dimethylbutane- thioamide 111 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (h) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] cyclobutanecarbo-thioamide 112 (S)-N- [ [3- [3-Fluoro-4- (4-acetyl-l-pi P-90 Z (i) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] cyclopentanecarbo- thioamide 113 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (j) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl] cyclohexanecarbo-thioamide 114 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (k) perazinyl) phenyl]-2-oxo-5-oxazolidin Example Dithio No. Product Amine Compound yl] methyl]-2-cyclopropylethane- thioamide 115 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-l-pi P-90 Z (1) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl]-2-cyclobutylethane- thioamide 116 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1-pi P-90 Z (m) perazinyl) phenyl]-2-oxo-5-oxazolidin yl] methyl]-2-cyclopentylethane- thioamide 117 (S)-N- [ [3- [3, 5-Difluoro-4- (4-acetyl- P-91 Ethyl 1-piperazinyl)-dithio- phenyl]-2-oxo-5-oxazolidinyl] methyl] acetate thioacetamide 118 (S)-N- [ [3- [3, 5-Difluoro-4- (4-acetyl- P-91 Z (a) 1-piperazinyl)- phenyl] -2-oxo-5-oxazolidinyl] methyls propane-thioamide 119 (S)-N- [ [3- [3, 5-Difluoro-4- (4-acetyl- P-91 Z (b) 1-piperazinyl)- phenyl] -2-oxo-5-oxazolidinyl] methyls - 2-methyl-propanethioamide 120 (S)-N- [ [3- [3, 5-Difluoro-4- (4-acetyl- P-91 Z (c) 1-piperazinyl)- phenyl]-2-oxo-5-oxazolidinyl] methyl] cycloproane- carbothioamide 121 (S)-N-[[3-[4-(4-Acetyl-1-piperazinyl P-92 Ethyl <BR> <BR> )-2-oxo-5-<BR> dithio- oxazolidinyl] methyl] thioacetamide acetate 122 (S)-N-[[3-[4-(4-Acetyl-1-piperazinyl P-92 Z (a) )-2-oxo-5- oxazolidinyl] methyl] propanethioamide Example Dithio No. Product Amine Compound 123 (S)-N-[[3-[4-(4-Acetyl-1-piperazinyl P-92 Z (b) )-2-oxo-5- oxazolidinyl] methyl]-2- methylpropanethioamide 124 (S)-N-[[3-[4-(4-Acetyl-l-piperazinyl P-92 Z (c) )-2-oxo-5- oxazolidinyl] methyl] cyclopropanecarb othioamide 125 (S)-N- [ [3- [3-Fluoro-4- [4- P-93 Ethyl <BR> <BR> (methoxyacetyl)-1-dithio-<BR> piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl]-thioacetamide 126 (S)-N-[[3-[3-Fluoro-4-[4-P-93 Z (a) (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]- propanethioamide 127 (S)-N- [ [3- [3-Fluoro-4- [4- P-93 Z (b) (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]- propanethioamide 128 (S)-N-[[3-[3-Fluoro-4-[4-P-93 Z (c) (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]- methylpropanethioamide 129 (S)-N-[[3-[3-Fluoro-4-[4-P-93 Z (d) (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]- butanethioamide 130 (S)-N-[[3-[3-Fluoro-4-[4-P-93 Z (e) (methoxyacetyl)-1- (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]-3- methylbutanethioamide 131 (S)-N- [ [3- [3-Fluoro-4- [4- P-93 Z (f) (methoxyacetyl)-1- piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl]-2- methylbutanethioamide 132 (S)-N-[[3-[3-Fluoro-4-[4-(methoxyace P-93 Z (g) tyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolid inyl] methyl]-3, 3- dimethylbutanethioamide 133 (S)-N-[[3-[3-Fluoro-4-[4-(methoxyace P-93 Z (h) <BR> <BR> tyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolid inyl] methyl- cyclobutanecarbothioamide 134 (S)-N-[[3-[3-Fluoro-4-[4-(methoxyace P-93 Z (i) <BR> <BR> tyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolid inyl] methyl]- cyclopentanecarbothioamide 135 (S)-N-[[3-[3-Fluoro-4-[4-(methoxyace P-93 Z (j) tyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolid inyl] methyl]- cyclohexanecarbothioamide 136 (S)-N-[[3-[3-Fluoro-4-[4-(methoxyace P-93 Z (k) <BR> <BR> tyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolid inyl] methyl]-2- cyclopropylethanethioamide 137 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxyace P-93 Z (1) tyl)-1-piperazinyl] phenyl]-2-oxo-5-o xazolidinyl] methyl]-2- cyclobutylethanethioamide 138 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxyacet P-93 Z (m) <BR> <BR> yl)-l-piperazinyl] phenyl]-2-oxo-5-oxa<BR> zolidinyl] methyl]-2- cyclopentylethanethioamide 139 (S)-N- [ [3- [3, 5-Difluoro- [4- [4- (methox P-94 Ethyl yacetyl)-1-dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 140 (S)-N- [ [3- [3, 5-Difluoro- [4- [4- (methox P-94 Z (a) <BR> <BR> yacetyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 141 (S)-N- [ [3- [3, 5-Difluoro- [4- [4- (methox P-94 Z (b) <BR> <BR> yacetyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 142 (S)-N-[[3-[3,5-Difluoro-[4-[4-(methox P-94 Z (c) <BR> <BR> yacetyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 143 (S)-N-[[3-[4-[4-(methoxyacetyl)-l-pip P-95 Ethyl erazinyl] phenyl]-2-oxo-5-oxazolidinyl dithio- ] methyl] thioacetamide acetate 144 (S)-N- [[3-[4-[4-(methoxyacetyl)-l-pip P-95 Z (a) erazinyl] phenyl]-2-oxo-5-oxazolidinyl ] methyl] propanethioamide 145 (S)-N- [[3-[4-[4-(methoxyacetyl)-l-pip P-95 Z (b) erazinyl] phenyl]-2-oxo-5-oxazolidinyl ] methyl]-2-methylpropane-thioamide 146 (S ?-N- ( [3- [9- [4- (methoxyacetyl)-1-pip P-95 Z (c) erazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] cyclopropanecarbothioamide 147 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanoacetyl P-96 Ethyl )-1-piperazinyl] dithio- -phenyl]-2-oxo-5-oxazolidinyl] methyl] acetate thioacetamide 148 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanoacetyl P-96 Z (a) )-1-piperazinyl]- phenyl]-2-oxo-5-oxazolidinyl] methyls propanethioamide 149 (S)-N-[[3-[3-Fluoro-4-[4-(cyanoacetyl P-96 Z (a) <BR> <BR> )-1-piperazinyl]-<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl] - 2-methyl-propanethioamide 150 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanoacetyl P-96 Z (b) )-1-piperazinyl]- phenyl]-2-oxo-5-oxazolidinyl] methyl] c yclopropane-carbothioamide 151 (S)-N-[[3-[3,5-Difluoro-4-[4-(cyanoac P-97 Ethyl etyl)-1-dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl]- methyl] thioacetamide 152 (S)-N-[[3-[3,5-Difluoro-4-[4-(cyanoac P-97 Z (a) etyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl]-methyl] propanethioamide 153 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (cyanoac P-97 Z (b) <BR> <BR> etyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 154 (S)-N- [ (3- [3, 5-Difluoro-4- [4- (cyanoac P-97 Z (c) <BR> <BR> etyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl]- methyl] cyclopropanecarbothioamide 155 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1-piper P-98 Ethyl azinyl] phenyl]-2-oxo-5-oxazolidinyl] m dithio- azinyl] phenyl]-2-oxo-5-oxazolidinyl] m dithio- ethyl] thioacetamide acetate 156 (S)-N-[[3-[4-[4-(Cyanoacetyl)-l-piper P-98 Z (a) azinyl] phenyl]-2-oxo-5-oxazolidinyl] m ethyl] propanethioamide 157 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1-piper P-98 Z (b) <BR> <BR> azinyl] phenyl]-2-oxo-5-oxazolidinyl] m<BR> ethyl]-2-methylpropanethioamide 158 (S)-N-[[3-[4-[4-(Cyanoacetyl)-l-piper P-98 Z (c) azinyl] phenyl]-2-oxo-5-oxazolidinyl] m ethyl] cycopropanecarbothioamide 159 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Ethyl yl)-1-dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 160 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (a) yl)-l- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 161 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (b) <BR> <BR> yl)-l-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 162 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (c) <BR> <BR> yl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 163 (S)-N-[[3-[3-Fluoro-4-[4-(acetoxyacet P-99 Z (d) <BR> <BR> yl)-l-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-butanethioamide 164 (S)-N-[[3-[3-Fluoro-4-[4-(acetoxyacet P-99 Z (e) yl)-1-piperazinyl] phenyl]-2-oxo-5-oxa zolidinyl] methyl]-3- methylbutanethioamide 165 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (f) yl)-1-piperazinyl] phenyl]-2-oxo-5-oxa<BR> zolidinyl] methyl]-2- methylbutanethioamide 166 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (g) yl)-l- piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl] -3, 3- dimethylbutanethioamide 167 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (h) <BR> <BR> yl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-cyclobutanecarbothioamide 168 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (i) yl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopentanecarbothioamide 169 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (j) yl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-cyclohexanecarbothioamide 170 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (k) yl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl] -2- cyclopropylethanethioamide 171 (S)-N-[[3-[3-Fluoro-4-[4-(acetoxyacet P-99 Z (1) yl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- cyclobutylethanethioamide 172 (S)-N- [ [3- [3-Fluoro-4- [4- (acetoxyacet P-99 Z (m) yl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl-2- cyclopentylethanethioamide 173 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (acetoxy P-Ethyl acetyl)-1-100 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl- thioacetamide 174 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (acetoxy P-Z (a) acetyl)-1-100 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 175 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (acetoxy P-Z (b) acetyl)-1-100 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- methylpropanethioamide 176 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (acetoxy P-Z (c) acetyl)-1-100 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 177 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1-pip P-Ethyl erazinyl] phenyl]-2-oxo-5-oxazolidinyl 100 dithio- ] methyl] thioacetamide acetate 178 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1-pip P-Z (a) erazinyl] phenyl]-2-oxo-5-oxazolidinyl 101 ] methyl] propanethioamide 179 (S)-N- [ [3- [4- [4- (Acetoxyacetyl)-l-pip P-Z (b) erazinyl] phenyl]-2-oxo-5-oxazolidinyl 101 ] methyl]-2-methylpropane-thioamide 180 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1-pip P-Z (c) erazinyl] phenyl]-2-oxo-5-oxazolidinyl 101 ] methyl] cyclopropanecarbo-thioamide 181 (S)-N- [ [3- [3-Fluoro-4- [4- (benzyloxyac P-Ethyl etyl)-1-102 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 182 (S)-N- [ [3- [3-Fluoro-4- [4- (benzyloxyac P-Z (a) etyl)-1-102 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 183 (S)-N- [ [3- [3-Fluoro-4- [4- (benzyloxyac P-Z (b) <BR> <BR> etyl)-1-102<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 184 (S)-N- [ [3- [3-Fluoro-4- [4- (benzyloxyac P-Z (c) etyl)-1-piperazinyl] phenyl]-2-oxo-5-o 102 xazolidinyl] methyl]- cyclopropanecarbothioamide 185 (S)-N-[[3-[3,5-Difluoro-4-[4-(benzylo P-Ethyl xyacetyl)-1-103 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 186 (S)-N-[[3-[3,5-Difluoro-4-[4-(benzylo P-Z (a) xyacetyl)-1-103 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 187 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (benzylo P-Z (b) <BR> <BR> xyacetyl)-1-103<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 188 (S)-N-[[3-[3,5-Difluoro-4-[4-(benzylo P-Z (c) <BR> <BR> xyacetyl)-l-103<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 189 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Ethyl onyl)-1-105 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 190 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Z (a) onyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 191 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Z (b) onyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- methylpropanethioamide 192 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Z (c) <BR> <BR> onyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 193 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarbo P-Z (d) nyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidin<BR> yl] methyl] -butanethioamide 194 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarbo P-Z (e) nyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidin yl] methyl]-3-methylbutanethioamide 195 (S)-N- [ [3- [3-Fluoro-4- (4- (methoxycarbo P-Z (f) nyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidin yl] methyl]-2- methylbutanethioamide 196 (S)-N-[[3-[3-Fluoro-4-[4-(methoxycarbo P-Z (g) nyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidin yl] methyl]-3, 3-dimethylbutanethioamide 197 (S)-N-[[3-[3-Fluoro-4-[4-(methoxycarbo P-Z (h) nyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidin yl] methyl]-cyclobutanecarbothioamide 198 (S)-N-[[3-[3-Fluoro-4-[4-(methoxycarbo P-Z (i) nyl)-1-105 piperazinyl] phenyl]-2-oxo-5-oxazolidin yl] methyl]-cyclopentanecarbothioamide 199 (S)-N-[[3-[3-Fluoro-4-[4-(methoxycarbo P-Z (j) nyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidin<BR> yl] methyl]-cyclohexanecarbothioamide 200 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Z (k) <BR> <BR> onyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2- cyclopropylethanethioamide 201 (S)-N-[[3-[3-Fluoro-4-[4-(methoxycarb P-Z (1) <BR> <BR> onyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2- cyclobutylethanethioamide 202 (S)-N- [ [3- [3-Fluoro-4- [4- (methoxycarb P-Z (m) <BR> <BR> onyl)-1-105<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- cyclopentylethanethioamide 203 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methoxy P-Ethyl carbonyl)-1-106 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 204 (S)-N-[[3-[3,5-Difluoro-4-[4-(methoxy P-Z (a) carbonyl)-1-106 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 205 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methoxy P-Z (b) carbonyl)-1-106 <BR> <BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 206 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methoxy P-Z (c) carbonyl)-1-106 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 207 (S)-N-[[3-[4-(4-(methoxycarbonyl)-1-P-Ethyl piperazinyl] phenyl] -2-oxo-5-oxazolidi 107 dithio- nyl] methyl]- acetate thioacetamide 208 (S)-N- [ [3- [4- [4- (methoxycarbonyl)-1- P-Z (a) piperazinyl] phenyl] -2-oxo-5-oxazolidi 107 nyl] methyl]-propanethioamide 209 (S)-N- [ [3- [4- [4- (methoxycarbonyl)-1- P-Z (b) piperazinyl] phenyl]-2-oxo-5-oxazolidi 107 nyl] methyl]-2-methylpropanethioamide 210 (S)-N-[[3-[4-[4-(methoxycarbonyl)-1-P-Z (c) piperazinyl] phenyl]-2-oxo-5-oxazolidi 107 nyl] methyl]- cyclopropanecarbothioamide 211 (S)-N-[[3-[3-Fluoro-4-[4-(methanesulf P-Ethyl onyl)-1-108 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide; mp 197-198°C ; Anal. calcd for C17H23FN404S2 : C, 47. 43 ; H, 5.39 ; N, 13. 01 ; S, 14. 89. Found: C, 47. 25 ; H, 5. 40 ; N, 12.82 ; S, 14.56.

212 (S)-N- [ [3- [3-Fluoro-4- [4- (methanesulf P-Z (a) onyl)-1-108<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide ; mp 207-208°C ; Anal. calcd for C18H25FN404S2 : C, 48. 63 ; H, 5.67 ; N, 12.60 ; S, 14.42. Found: C, 48.51 ; H, 5.59 ; N, 12.52 ; S, 14.09.

213 (S)-N-[[3-[3-Fluoro-4-[4-(methanesulf P-Z (b) onyl)-1-108<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl] -2-methylpropanethioamide ; mp 204-206°C ; Anal. calcd for Cl9H27FN4O4S2 : C, 49.76 ; H, 5.93 ; N, 12.22 ; S, 13.98. Found: C, 49.63 ; H, 5.92 ; N, 14.14 ; S, 13.91.

214 (S)-N- [ [3- [3-Fluoro-4- [4- (methanesulf P-Z (a) <BR> <BR> onyl)-1-108<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide; Anal. calcd for C1gH25FN404S2 : C, 49.98 ; H, 5. 52 ; N, 12. 27 ; S, 14.04. Found: C, 49.42 ; H, 5.50 ; N, 12.08 ; S, 13.80.

215 (S)-N-[[3-[3,5-Difluoro-4-[4-(methane P-Ethyl sulfonyl)-1-109 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 216 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methane sulfonyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 217 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methane sulfonyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 218 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (methane sulfonyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl- cyclopropanecarbothioamide 219 (S)-N-[[3-[4-[4-(methanesulfonyl)-l- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- thioacetamide 220 (S)-N-[[3-[4-[4-(methanesulfonyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 221 (S)-N-[[3-[4-[4-(methanesulfonyl)-l- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 222 (S)-N-[[3-[4-[4-(methanesulfonyl)-l- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 223 (S)-N- [ [3- [3-Fluoro-4- [4- (ethanesulfo nyl)-1- <BR> <BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl] - thioacetamide 224 (S)-N- [ [3- [3-Fluoro-4- [4- (ethanesulfo nyl)-1- piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 225 (S)-N-[[3-[3-Fluoro-4-[4-(ethanesulfo P- nyl)-1-111 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- methylpropanethioamide 226 (S)-N-[[3-[3-Fluoro-4-[4-(ethanesulfo P- nyl)-1-111 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 227 (S)-N-[[3-[3,5-Difluoro-4-[4-(ethanes P- ulfonyl)-1-112<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- thioacetamide 228 (S)-N-[[3-[3,5-Difluoro-4-[4-(ethanes P-11 <BR> <BR> ulfonyl)-1-2<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl] -propanethioamide 229 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (ethanes P- <BR> <BR> ulfonyl)-1-112<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 230 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (ethanes P- <BR> <BR> ulfonyl)-1-112<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl- cyclopropanecarbothioamide 231 (S)-N- [ [3- [4- [4- (ethanesulfonyl)-1-pi P- perazinyl] phenyl]-2-oxo-5-oxazolidiny 113 l] methyl] thioacetamide 232 (S)-N-[[3-[4-[4-(ethanesulfonyl)-l-pi P- perazinyl] phenyl]-2-oxo-5-oxazolidiny 113 l] methyl] propanethioamide 233 (S)-N- [ [3- [4- [4- (ethanesulfonyl)-1-pi P- perazinyl] phenyl]-2-oxo-5-oxazolidiny 113 l] methyl]-2-methylpropane-thioamide 234 (S)-N- [ [3- [4- [4- (ethanesulfonyl)-1-pi P-Z (c) perazinyl] phenyl]-2-oxo-5-oxazolidiny 113 l] methyl] cyclopropanecarbothioamide 235 (S)-N-[[3-[3-Fluoro-4-[4-(chlorometha P-Ethyl nesulfonyl)-1-114 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl] - thioacetamide 236 (S)-N- [ [3- [3-Fluoro-4- [4- (chlorometha P-Z (a) <BR> <BR> nesulfonyl)-1-114<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 237 (S)-N- [ [3- [3-Fluoro-4- [4- (chlorometha P-Z (b) <BR> <BR> nesulfonyl)-1-114<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 238 (S)-N-[[3-[3-Fluoro-4-[4-(chlorometha P-Z (c) <BR> <BR> nesulfonyl)-1-114<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 239 (S) -N- [ [3- [3, 5-Difluoro-4- [4- (chlorom P-Ethyl<BR> ethanesulfonyl) -115 dithio- 1-piperazinyl] phenyl]-2-oxo-5-oxazoli acetate dinyl] methyl]- thioacetamide 240 (S) -N- [ [3- [3, 5-Difluoro-4- [4- (chlorom P-Z (a)<BR> ethanesulfonyl)-115<BR> 1-piperazinyl] phenyl]-2-oxo-5-oxazoli dinyl] methyl] propanethioamide 241 (S) -N- [ [3- [3, 5-Difluoro-4- [4- (chlorom P-Z (b) ethanesulfonyl)-1-piperazinyl] phenyl] 115 - 2-oxo-5-oxazolidinyl] methyl] -2- methylpropanethioamide 242 (S) -N- [ [3- [3, 5-Difluoro-4- [4- (chlorom P-Z (c) ethanesulfonyl)-1-piperazinyl] phenyl] 115 -2-oxo-5-oxazolidinyl] methyl] - cyclopropanecarbothioamide 243 (S)-N- [ [3- [4- [4- (chloromethanesulfony P-Ethyl 1)-1-116 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl- thioacetamide 244 (S)-N- [ [3- [4- [4- (chloromethanesulfony P-Z (a) 1)-1-116 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 245 (S)-N- [ [3- [4- [4- (chloromethanesulfony P-Z (b) 1)-1-piperazinyl] phenyl]-2-oxo-5-oxaz 116 olidinyl] methyl]-2- methylpropanethioamide 246 (S)-N-[[3-[4-[4-(chloromethanesulfony P-Z (c) 1)-1-116<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 247 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethan P-Ethyl e-sulfonyl)-1-117 dithio- piperazinyl] phenyl]-2-oxo-5- acetate oxazolidinyl] methyl] thioacetamide 248 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethan P-Z (a) <BR> <BR> e-sulfonyl)-1-117<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 249 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethan P-Z (b) e-sulfonyl)-1-117<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 250 (S)-N-[[3-[3-Fluoro-4-[4-(cyanomethan P-Z (c) e-sulfonyl)-1-117<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 251 (S)-N-[[3-[3,5-Difluoro-4-[4-(cyanome Ethyl thane-sulfonyl)-1-piperazinyl] phenyl] dithio- -2-oxo-5-acetate oxazolidinyl] methyl] thioacetamide 252 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (cyanome P-Z (a) thane-sulfonyl)-1-piperazinyl] phenyl] 118 -2-oxo-5-oxazolidinyl]- methyl] propanethioamide 253 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (cyanome P-Z (b) thane-sulfonyl)-1-piperazinyl] phenyl] 118 -2-oxo-5-oxazolidinyl] methyl] -2- methylpropanethioamide 254 (S)-N-[[3-[3,5-Difluoro-4-[4-(cyanome P-Z (c) thane-sulfonyl)-1-piperazinyl] phenyl] 118 -2-oxo-5-oxazolidinyl] methyl]- cyclopropanecarbothioamide 255 (S)-N-[[3-[4-[4-(Cyanomethanesulfonyl P-Ethyl )-1-119 dithio- piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl] thioacetamide 256 (S)-N- [ [3- [4- [4- (Cyanomethanesulfonyl P-Z (a) )-1-119 piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] propanethioamide 257 (S)-N- [ [3- [4- [4- (Cyanomethanesulfonyl P-Z (b) <BR> <BR> )-1-119<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 258 (S)-N-[[3-[4-[4-(Cyanomethanesulfonyl P-Z (c) )-1-piperazinyl] phenyl]-2-oxo-5- 119 oxazolidinyl] methyl] cyclopropanecarbo thioamide 259 (S)-N- [ [3- [3-Fluoro-4- [4- (N-methylsul P-Ethyl famoyl)-1-120 dithio- piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl]-thioacetamide 260 (S)-N- [ [3- [3-Fluoro-4- [4- (N-methylsul P-Z (a) famoyl)-1-120<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 261 (S)-N- [ [3- [3-Fluoro-4- [4- (N-methylsul P-Z (b) famoyl)-1-120<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 262 (S)-N-[[3-[3-Fluoro-4-[4-(N-methylsul P-Z (c) <BR> <BR> famoyl)-1-120<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 263 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (N-methy P-Ethyl lsulfamoyl)-1-121 dithio- piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl] thioacetamide 264 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (N-methy P-Z (a) <BR> <BR> lsulfamoyl)-l-121<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 265 (S)-N-[[3-[3,5-Difluoro-4-[4-(N-methy P-Z (b) lsulfamoyl)-1-121<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 266 (S)-N-[[3-[3,5-Difluoro-4-[4-(N-methy P-Z (c) lsulfamoyl)-1-121<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 267 (S)-N-[[3-[4-[4-(N-methylsulfamoyl)-1 P-Ethyl 122 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 268 (S)-N-[[3-[4-[4-(N-methylsulfamoyl)-1 P-Z (a) <BR> <BR> 122<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 269 (S)-N-[[3-[4-[4-(N-methylsulfamoyl)-l P-Z (b) <BR> <BR> 122<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 270 (S)-N-[[3-[4-[4-(N-methylsulfamoyl)-l P-Z (c) <BR> <BR> 122<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 271 (S)-N- [ [3- [3-Fluoro-4- [4- (N, N-dimethy P-Ethyl lsulfamoyl)-1-123 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 272 (S)-N-[[3-[3-Fluoro-4-[4-(N,N-dimethy P-Z (a) <BR> <BR> lsulfamoyl)-1-123<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 273 (S)-N-[[3-[3-Fluoro-4-[4-(N,N-dimethy P-Z (b) <BR> <BR> lsulfamoyl)-1-. 123<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 274 (S)-N- [ [3- [3-Fluoro-4- [4- (N, N-dimethy P-Z (c) lsulfamoyl)-1-123<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 275 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (N, N-dim P-Ethyl ethylsulfamoyl)-1-piperazinyl] phenyl] 124 dithio- - 2-oxo-5-oxazolidinyl] methyl]- acetate thioacetamide 276 (S)-N-[[3-[3,5-Difluoro-4-[4-(N,N-dim P-Z (a) ethylsulfamoyl)-1-piperazinyl] phenyl] 124 -2-oxo-5-oxazolidinyl] methyl] - propanethioamide 277 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (N, N-dim P-Z (b) ethylsulfamoyl)-1-piperazinyl] phenyl] 124 - 2-oxo-5-oxazolidinyl] methyl]-2- methylpropanethioamide 278 (S)-N-[[3-[3,5-Difluoro-4-[4-(N,N-dim P-Z (c) ethylsulfamoyl)-1-piperazinyl] phenyl] 124 -2-oxo-5-oxazolidinyl] methyl] - cyclopropanecarbothioamide 279 (S)-N- [ [3- [9- [4- (N, N-dimethylsulfamoy P-Ethyl 1)-1-125 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 280 (S)-N-[[3-[4-[4-(N,N-dimethylsulfamoy P-Z (a) 1)-1-125 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 281 (S)-N- [ [3- [4- [4- (N, N-dimethylsulfamoy P-Z (b) 1)-1-125 piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 282 (S)-N- [ [3- [4- [4- (N, N-dimethylsulfamoy P-Z (c) <BR> <BR> 1)-1-125<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 283 (S)-N- [ [3- [3-Fluoro-4- [4- (ethoxycarbo P-Ethyl nyl)-1-126 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl- thioacetamide 284 (S)-N- [ [3- [3-Fluoro-4- [4- (ethoxycarbo P-Z (a) <BR> <BR> nyl)-1-126<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 285 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (b) nyl)-1-126 <BR> <BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 286 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (c) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 287 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (d) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-butanethioamide 288 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (e) nyl)-1-126 <BR> <BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-3-methylbutanethioamide 289 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (f) nyl)-1-126 <BR> <BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylbutanethioamide 290 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (g) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl] -3, 3- dimethylbutanethioamide 291 (S)-N- [ [3- [3-Fluoro-4- [4- (ethoxycarbo P-Z (h) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-cyclobutanecarbothioamide 292 (S)-N- [ [3- [3-Fluoro-4- [4- (ethoxycarbo P-Z (i) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopentanecarbothioamide 293 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (j) <BR> <BR> nyl)-l-126<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-cyclohexanecarbothioamide 294 (S)-N- [ [3- [3-Fluoro-4- [4- (ethoxycarbo P-Z (k) nyl)-1-126 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- cyclopropylethanethioamide 295 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (1) <BR> <BR> nyl)-l-126<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- cyclobutylethanethioamide 296 (S)-N-[[3-[3-Fluoro-4-[4-(ethoxycarbo P-Z (m) <BR> <BR> nyl)-l-126<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2- cyclopentylethanethioamide 297 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (ethoxyc P-Ethyl arbonyl)-1-127 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetmide 298 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (ethoxyc P-Z (a) <BR> <BR> arbonyl)-l-127<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-propanethioamide 299 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (ethoxyc P-Z (b) <BR> <BR> arbonyl)-l-127<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2-methylpropanethioamide 300 (S)-N-[[3-[3,5-Difluoro-4-[4-(ethoxyc P-Z (c) <BR> <BR> arbonyl)-1-127<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 301 (S)-N-[[3-[4-[4-(ethoxycarbonyl)-l-pi P-Ethyl perazinyl]-127 dithio- phenyl]-2-oxo-5-oxazolidinyl] methyl] t acetate hioacetamide 302 (S)-N-[[3-[4-[4-(ethoxycarbonyl)-l-pi P-Z (a) perazinyl]-128 phenyl]-2-oxo-5-oxazolidinyl] methyl- propanethioamide 303 (S)-N-[[3-[9-[4-(ethoxycarbonyl)-1-pi P-Z (b) perazinyl]-128<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl] - 2-methylpropanethioamide 304 (S)-N-[[3-[4-[4-(ethoxycarbonyl)-l-pi P-Z (c) perazinyl]-128 phenyl]-2-oxo-5-oxazolidinyl] methyl] c yclopropane-carbothioamide 305 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-l-P-Ethyl piperazinyl) -129 dithio- phenyl]-2-oxo-5-oxazolidinyl] methyl] t acetate hioacetamide 306 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (a) piperazinyl)-129<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl] - propanethioamide 307 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (b) piperazinyl)-129<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl] - 2-methylpropanethioamide 308 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (c) <BR> <BR> piperazinyl)-129<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl] - cyclopropanecarbothioamide 309 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-l-P-Z (d) piperazinyl)-phenyl]-2-oxo-5-129 oxazolidinyl] methyl] butanethioamide 310 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (e) <BR> <BR> piperazinyl) phenyl] -2-oxo-5-oxazolidi 129<BR> nyl] methyl]-3-methylbutanethioamide 311 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (f) piperazinyl) 129 phenyl]-2-oxo-5-oxazolidinyl] methyl] - 2-methylbutanethioamide 312 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (g) piperazinyl) phenyl]-2-oxo-5-oxazolidi 129 nyl] methyl]-3, 3- dimethylbutanethioamide 313 (5)-N- [ [3- [3-Fluoro-4- (4-sulfamoyl-l- P-Z (g) piperazinyl) phenyl]-2-oxo-5- 129 oxazolidinyl] methyl] cyclobutanecarbot hioamide 314 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1-P-Z (i) piperazinyl) phenyl]-2-oxo-5- 129 oxazolidinyl] methyl] cyclopentanecarbo thioamide 315 (5)-N- [ [3- [3-Fluoro-4- (4-sulfamoyl-l- P-Z (j) piperazinyl) phenyl]-2-oxo-5-129 oxazolidinyl] methyl] cyclohexanecarbot hioamide 316 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-l-P-Z (k) piperazinyl) phenyl]-2-oxo-5-oxazolidi 129 nyl] methyl]-2- cyclopropylethanethioamide 317 (S)-N-[[3-[3-Fluoro-9-(4-sulfamoyl-1-P-Z (1) piperazinyl) phenyl]-2-oxo-5-oxazolidi 129 nyl] methyl]-2- cyclobutylethanethioamide 318 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-l-P-Z (m) piperazinyl) phenyl] -2-oxo-5-oxazolidi 129 nyl] methyl]-2- cyclopentylethanethioamide 319 (S)-N- [ [3- [3, 5-Difluoro-4- (4-sulfamoy P-Ethyl 1-1-piperazinyl) phenyl]-2-oxo-5- 130 dithio- oxazolidinyl] methyl] thioacetamide acetate 320 (S)-N- [ [3- [3, 5-Difluoro-4- (4-sulfamoy P-Z (a) 1-1-piperazinyl) phenyl]-2-oxo-5- 130 oxazolidinyl] methyl] propanethioamide 321 (S)-N- [ [3- [3, 5-Difluoro-4- (4-sulfamoy P-Z (b) 1-1-130 piperazinyl) phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2- methylpropanethioamide 322 (S)-N-[[3-[3,5-Difluoro-4-(4-sulfamoy P-Z (c) 1-1-piperazinyl) phenyl]-2-oxo-5- 130 oxazolidinyl] methyl] cyclopropanecarbo thioamide 323 (S)-N-[[3-[4-(4-sulfamoyl-1-piperazin P-Ethyl yl) phenyl]-2-oxo-5-oxazolidinyl] methy 131 dithio- 1] thioacetamide acetate 324 (S)-N-[[3-[4-(4-sulfamoyl-l-piperazin P-Z (a) yl) phenyl]-2-oxo-5-oxazolidinyl] methy 131 l] propanethioamide 325 (5)-N-[[3-[4-(4-sulfamoyl-l-piperazin P-Z (b) yl) phenyl]-2-oxo-5-oxazolidinyl] methy yl) phenyl]-2-oxo-5-oxazolidinyl] methy 131 l]-2-methylpropanethioamide 326 (S)-N- [ [3- [4- (4-sulfamoyl-1-piperazin P-Z (c) yl) phenyl]-2-oxo-5-oxazolidinyl] methy 131 l] cyclopropanecarbothioamide 327 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethyl P-Ethyl )-1-132 dithio- piperazinyl] phenyl] -2-oxo-5-oxazolidi acetate nyl] methyl] thioacetamide 328 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethyl P-Z (a) <BR> <BR> )-1-132<BR> piperazinyl] phenyl]-2-oxo-5 oxazolidinyl] methyl] propanethioamide 329 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethyl P-Z (b) <BR> <BR> )-1-132<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 330 (S)-N- [ [3- [3-Fluoro-4- [4- (cyanomethyl P-Z (c) )-1-132 piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] cyclopropanecarbo thioamide 331 (S)-N-[[3-[3,5-Difluoro-4-[4-(P-Ethyl cyanomethyl)-1-133 dithio- piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl] thioacetamide 332 (S)-N-[[3-[3,5-Difluoro-4-[4-(P-Z (a) cyanomethyl)-1-133 piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] propanethioamide 333 (S)-N-[[3-[3,5-Difluoro-4-[4 P-Z (b) cyanomethyl)-1-133 piperazinyl] phenyl]-2-oxo-5-oxazolidi<BR> nyl] methyl]-2- methylpropanethioamide 334 (S)-N-[[3-[3,5-Difluoro-4-[4-(cyanome P-Z (c) thyl)-l-piperazinyl] phenyl]-2-oxo-5-o 133 xazolidinyl] methyl]- cyclopropanecarbothioamide 335 (S)-N-[[3-[4-[4-(cyanomethyl)-1-piper P-Ethyl azinyl] phenyl]-2-oxo-5-oxazolidinyl] m 134 dithio- ethyl] thioacetamide acetate 336 (S)-N-[[3-[4-[4-(cyanomethyl)-1-piper P-Z (a) azinyl] phenyl]-2-oxo-5-oxazolidinyl] m 134 ethyl] propanethioamide 337 (S)-N-[[3-[4-[4-(cyanomethyl)-1-piper P-Z (b) azinyl] phenyl]-2-oxo-5-oxazolidinyl] m 134 ethyl]-2-methylpropanethioamide 338 (S)-N-[[3-[4-[4-(cyanomethyl)-1- piperazinyl] phenyl] - 2-oxo-5-oxazolidinyl] methyl] cyclopro panecarbothioamide 339 (S)-N- [ [3- [3-Fluoro-4- [4- (2-fluoroeth P-Ethyl yl)-l-135 dithio- piperazinyl] phenyl]-2-oxo-5-acetate oxazolidinyl] methyl] thioacetamide 340 (S)-N- [ [3- [3-Fluoro-4- [4- (2-fluoroeth P-Z (a) <BR> <BR> yl)-l-135<BR> piperazinyl] phenyl]-2-oxo-5- oxazolidinyl] methyl] propanethioamide 341 (S)-N- [ [3- [3-Fluoro-4- [4- (2-fluoroeth P-Z (b) yl)-1-135 piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 342 (S)-N-[[3-[3-Fluoro-4-[4-(2-fluoroeth P-Z (c) <BR> <BR> yl)-l-135<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 343 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (2-fluor P-Ethyl oethyl)-l-136 dithio- piperazinyl] phenyl]-2-oxo-5-oxazolidi acetate nyl] methyl]- thioacetamide 344 (S)-N-[[3-[3,5-Difluoro-4-[4-(2-fluor P-Z (a) <BR> <BR> oethyl)-l-136<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyls propanethioamide 345 (S)-N- [ [3- [3, 5-Difluoro-4- [4- (2-fluor P-Z (b) oethyl)-l-136<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]-2-methylpropanethioamide 346 (S)-N-[[3-[3,5-Difluoro-4-[4-(2-fluor P-Z (c) <BR> <BR> oethyl)-1-136<BR> piperazinyl] phenyl]-2-oxo-5-oxazolidi nyl] methyl]- cyclopropanecarbothioamide 347 (S)-N-[[3-[4-[4-(2-fluoroethyl)-l-pip P-Ethyl erazinyl] phenyl]- 137 dithio- 2-oxo-5-oxazolidinyl] methyl] thioaceta acetate mide 348 (S)-N-[[3-[4-[4-(2-fluoroethyl)-l-pip P-Z (a) erazinyl] phenyl]-137 2-oxo-5-oxazolidinyl] methyl] propaneth ioamide 349 (S)-N-[[3-[4-[4-(2-fluoroethyl)-l-pip P-Z (b) <BR> <BR> erazinyl] phenyl]- 137<BR> 2-oxo-5-oxazolidinyl] methyl] -2- methylpropanethioamide 350 (S)-N- [ [3- [4- [4- (2-fluoroethyl)-1-pip P-Z (c) erazinyl] phenyl] 137 - 2-oxo-5-oxazolidinyl] methyl] cyclopro pane-carbothioamide 351 (S)-N-[[3-[3-Fluoro-4-(4-formyl-1-pip P-Ethyl erazinyl) phenyl]-2-oxo-5-oxazolidinyl 138 dithio- ] methyl] thioacetamide; Anal calcd for acetate C17H21FN403S : C, 53.67 ; H, 5.56 ; N, 14. 73 ; S, 8.43. Found: C, 53.14 ; H, 5.42 ; N, 14.25 ; S, 8.18.

352 (S)-N-[[3-[3-Fluoro-4-(4-formyl-1-pip P-Z (a) erazinyl) phenyl] -2-oxo-5-oxazolidinyl 138 ] methyl] propanethioamide ; mp 166-167°C ; Anal. calcd for C18H23FN403S : C, 54.81 ; H, 5.88 ; N, 14.20 ; S, 8.13. Found: C, 54.83 ; H, 6.00 ; N, 14.12 ; S, 7.96.

353 (S)-N-[[3-[3-Fluoro-4-(4-formyl-l-pip P-Z (b) <BR> <BR> erazinyl) phenyl] -2-oxo-5-oxazolidinyl 138<BR> ] methyl] -2-methylpropane-thioamide ; mp 157-158°C : Anal. calcd for C1gH25FN403S : C, 55.87, H, 6. 17 ; N, 13.72 ; S, 7.85. Found: C, 55.67 ; H, 6.19 ; N, 13.50 ; S, 7.70.

354 (S)-N- [ [3- [3-Fluoro-4- (4-formyl-1-pip P-Z (c) erazinyl) phenyl]-2-oxo-5-oxazolidinyl 138 ] methyl] cyclopropane-carbothioamide ; mp 178-179°C ; Anal. calcd for C19H23FN403S : C, 56.14 ; H, 5.70 ; N, 13.78 ; S, 7.89. Found: C, 56.13 ; H, 5.64 ; N, 13.64 ; S. 7.75.

355 (S)-N-[[3-[3,5-Difluro-4-(4-formyl-1-P-Ethyl piperazinyl) -139 dithio- phenyl]-2-oxo-5-oxazolidinyl] methyl] t acetate hioacetamide 356 (S)-N- [ [3- [3, 5-Difluro-4- (4-formyl-1- P-Z (a) <BR> <BR> piperazinyl)-139<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl]- propanethioamide 357 (S)-N-[[3-[3,5-Difluro-4-(4-formyl-1-P-Z (b) piperazinyl)-139<BR> phenyl]-2-oxo-5-oxazolidinyl] methyl]- 2-methyl-propanethioamide 358 (S)-N-[[3-[3,5-Difluro-4-(4-formyl-1-P-Z (c) piperazinyl)-139 phenyl]-2-oxo-5-oxazolidinyl] methyl] c yclo-propanecarbothioamide 359 (S)-N-[[3-[4-(4-formyl-l-piperazinyl) P-Ethyl phenyl]-2-oxo-5-140 dithio- oxazolidinyl] methyl] thioacetamide acetate 360 (S)-N-[[3-[4-(4-formyl-1-piperazinyl) P-Z (a) phenyl]-2-oxo-5-140 oxazolidinyl] methyl] propanethioamide 361 (S)-N-[[3-[4-(4-formyl-1-piperazinyl) P-Z (b) phenyl]-2-oxo-5-140 oxazolidinyl] methyl]-2-methylpropanet hioamide 362 (S)-N-[[3-[4-(4-formyl-1-piperazinyl) P-Z (c) phenyl]-2-oxo-5-140 oxazolidinyl] methyl] cyclopropane-carb othioamide Isothiocyanate Example Corresponding<BR> Example Product to Amine No. Amine No.

363 (S)-N- [ [3- [3-Fluoro-4- (4-acety 1-1- piperazinyl) phenyl]-2-oxo-5-ox azolidinyl]-<BR> methyl]-l-azetidinecarbothioam ide 364 (S)-N- [ [3- [3-Fluoro-4- [4- (meth oxyacetyl)-1-piperazinyl] pheny<BR> l]-2-oxo-5- oxazolidinyl] methyl]-l- azetidinecarbothioamide 365 (S)-N-[[3-[3-Fluoro-4-[4-(acet <BR> <BR> oxyacetyl)-1-<BR> piperazinyl] phenyl]-2-oxo-5-ox<BR> azolidinyl]-<BR> methyl]-l-azetidinecarbothioam ide 366 (S)-N- [ [3- [3-Fluoro-4- [4- (meth oxycarbonyl)-1-piperazinyl] phe nyl]-2-oxo-5-oxazolidinyl]-<BR> methyl]-1-azetidinecarbothioam ide 367 (S)-N-[[3-[3-Fluoro-4-[4-(etho xycarbonyl)-1-piperazinyl] phen<BR> yl]-2-oxo-5-oxazolidinyl]-<BR> methyl]-1-azetidinecarbothioam ide 368 (S)-N- [ (3- [3-Fluoro-4- (4-sulfa moyl-1- piperazinyl) phenyl]-2-oxo-5-ox azolidinyl]-<BR> methyl]-1-azetidinecarbothioam ide EXAMPLE 369.

(5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4 (5H) yl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide, thiazepine S-oxide TABLE H Example Compound Amine Dithioester No. (from Preparation Z) 370 (5S)-N- [ [3- [3- Z (a) Fluoro-4- (tetrahydro-1, 4- I O thiazepin-4 (5H)- N 0 yl)) FoN O phenyl]-2-oxo-5- oxazolidinyl] meth yl]- propanethioamide, thiazepine S- oxide 371 S)-N-[[3-[3-Same as above Z (b) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiazepine S- oxide.

372 (5S)-N- [ [3- [3- Same as above Z (c) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiazepine S- oxide.

373 (5S)-N-[[3-[3-Same as above Z (d) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- butanethioamide, thiazepine S- oxide 374 (5S)-N-[[3-[3-Same as above Z (e) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] methy 1]-3- methylbutanethioam ide, thiazepine S-oxide 375 (5S)-N-[[3-[3-Same as above Z (f) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] methy 1]-2- methylbutanethioam ide, thiazepine S-oxide 376 (5S)-N-[[3-[3-Same as above Z (g) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] methy 1]- 3,3- dimethylbutanethio amide, thiazepine S- oxide 377 (5S)-N- [ [3- [3- Same as above Z (h) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] methy 1]- cyclobutanecarboth io- amide, thiazepine S- oxide 378 (5S)-N- [ [3- [3- Same as above Z (i) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]-1- cyclopentanecarbot hio- amide, thiazepine S- oxide 379 (5S)-N- [ [3- [3- Same as above Z (j) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclohexanecarbot hio- amide, thiazepine S- oxide 380 (5S)-N-[[3-[3-Same as above Z (k) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclopropylethane thio- amide, thiazepine S- oxide 381 (5S)-N- [ [3- [3- Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclobutylethanet hio- amide, thiazepine S- oxide 382 (5S)-N- [ [3- [3- Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclopentylethane thio- amide, thiazepine S- oxide Example 383.

(5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H ) -yl) phenyl] -2-oxo-5-oxazolidinyl] methyl] thioacetamide, thiazepine S-oxide TABLE I Example Compound Amine Dithioester No. (from Preparation Z) 384 (5S)-N- [ [3- [3, 5- Z (a) Difluoro-4- (tetrahydro-F 1, 4-thiazepin- N 4 (5H)-yl))- phenyl]-2-oxo-5-F9W>N O oxazolidinyl] meth < NH2 yl]- propanethioamide, thiazepine S- oxide 385 (5S)-N-3- [3, 5-Same as above Z (b) Difluoro-4- (tetrahydro- 1, 4-thiazepin- 4 (5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiazepine S- oxide 386 (5S)-N- [ [3- [3, 5- Same as above Z (c) Difluoro-4- (tetrahydro- 1,4-thiazepin- 4 (5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiazepine S- oxide Example 387.

(5S)-N-[[3-[9-(Tetrahydro-1,4-thiazepin-4 (5H)-yl) phenyl- 2-oxo-5- oxazolidinyl] methyl] thioacetamide, thiazepine S-oxide.

TABLE J Example Compound Amine Dithioester No. (from Preparation Z 388 (5S)-N- [ [3- [4- 0 Z (a) (Tetrahydro-1, 4-fS) thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5-N O oxazolidinyl] meth < NH2 yl]- propanethioamide, thiazepine S- oxide 389 (5S)-N-[[3-[4-Same as above Z (b) (Tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide, thiazepine S- oxide 390 (5S)-N-[[3-[4-Same as above Z (c) (Tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide, thiazepine S- oxide Example 391.

(5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4 (5H) -yl ) phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide, thiazepine S, S-dioxide TABLE K Example Compound Amine Dithioester No. (from Preparation Z) 392 (5S)-N- [ [3- [3- O Z (a) Fluoro-4-°~S ors thiomorpholinyl] t2 NAO F, N 0 phenyl]-2-oxo-5- MHz oxazolidinyl] met hyl] propanethioamide r thiazepine S, S- dioxide 393 (5S)-N- [ [3- [3- Same as above Z (b) Fluoro-4- (4- thiomorpholinyl] phenyl]-2-oxo-5- oxazolidinyl] met hyl]-2- methylpropanethi o amide, thiazepine S, S- dioxide 394 (5S)-N- [ [3- [3- Same as above Z (c) Fluoro-4- (4- thiomorpholinyl] phenyl]-2-oxo-5- oxazolidinyl] met hyl]- cyclopropanecarb othio- amide, thiazepine S, S- dioxide Example 395.

(5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H ) yl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide, thiazepine S, S-dioxide TABLE L Example Compound Amine Dithioester No. (from Preparation Z) 396 (5S)-N- [ [3- [3, 5-0 Z (a) Difluoro-4- (4- thiomorpholinyl]-°--S 9 F phenyl]-2-oxo-5- oxazolidinyl] methy'k 1]-FNO propanethioamide, 1--lVNH2 2 thiazepine S, S- dioxide 397 (5S)-N- [ [3- [3, 5- Same as above Z (b) Difluoro-4- (4- thiomorpholinyl]- phenyl]-2-oxo-5- oxazolidinyl] methy 1]-2- methylpropanethio- amide, thiazepine S, S- dioxide 398 (5S)-N- [ [3- [3, 5- Same as above Z (c) Difluoro-4- (4- thiomorpholinyl]- phenyl]-2-oxo-5- oxazolidinyl] methy 1]- cyclopropanecarbot hio- amide, thiazepine S, S- dioxide Example 399.

(5S)-N-[[3-[4-(Tetrahydro-1,4-thiazepin-4 (5H)-yl) phenyl- 2-oxo-5- oxazolidinyl] methyl] thioacetamide, thiazepine S, S-dioxide TABLE M Example Compound Amine Dithioester No. (From Preparation Z) 400 (5S)-N- [ [3- [4- Z (a) (tetrahydro-1, 4- 0 thiazepin-4 (5H)-Og yl)) phenyl]-2-oxo- 5_ N i L ! l 1L oxazolidinyl]--aN A 0 methyl] propanethio < NH2 2 amide, thiazepine S, S- dioxide 401 (5S)-N- [ [3- [4- Same as above Z (b) (tetrahydro-1, 4- thiazepin-4 (5H)- yl)) phenyl]-2-oxo- 5- oxazolidinyl] methy 1]-2- methylpropanethio- amide, thiazepine S, S- dioxide 402 (5S)-N- [ [3- [4- Same as above Z (c) (tetrahydro-1, 4- thiazepin-4 (5H)- yl)) phenyl]-2- oxo-5- oxazolidinyl]- methyl] cyclopropa ne- carbothioamide, thiazepine S, S- dioxide EXAMPLE 403.

(5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4 (5H) - yl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide.

TABLE N Example Compound Amine Dithioester No. (From Preparation Z) 404 (5S)-N- [ [3- [3- S^ Z (a) Fluoro-4- (tetrahydro-N I O FNO phenyl]-4 (5H)-< NH2 y))- henYlJ-2-oxo-5- oxazolidinyl] me thyl]- propanethio- amide 405 (5S)-N- [ [3- [3- Same as above Z (b) Fluoro-4- (tetrahydro-1, 4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylpropanethio amide 406 (5S)-N- [ [3- [3- Same as above Z (c) Fluoro-4- (tetrahydro-1, 4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopropanecarbo thio- amide 407 (5S)-N- [ [3- [3- Same as above Z (d) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- butanethioamide 408 (5S)-N- [ [3- [3- Same as above Z (e) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]-3- methylbutanethioa mide 409 (5S)-N- [ [3- [3- Same as above Z (f) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- methylbutanethioa mide 410 (5S)-N- [ [3- [3- Same as above Z (g) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- 3,3- dimethylbutanethi o- amide 411 (5S)-N- [ [3- [3- Same as above Z (h) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclobutanecarbot hio- amide 412 (5S)-N- [ [3- [3- Same as above Z (i) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclopentanecarbo thio- amide 413 (5S)-N-[[3-[3-Same as above Z (j) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] meth yl]- cyclohexanecarbot hio- amide 414 (5S)-N- [ [3- [3-5 Same as above Z (k) Fluoro- 4- (tetrahydro- 1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclopropylethane thio- amide 415 (5S)-N- [ [3- [3- Same as above Z (1) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- <BR> <BR> yl))-<BR> phenyl]-2-oxo-5- oxazolidinyl] meth yl]-2- cyclobutylethanet hio- amide 416 (5S)-N- [ [3- [3- Same as above Z (m) Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]-2- cyclopentylethanet hioam ide EXAMPLE 417.

(5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H)-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl] thioacetamide TABLE O Example Compound Amine Dithio Compound No. (from Preparation Z) 418 (5S)-N- [ [3- [3, 5- S F Z (a) Difluoro-4- (tetrahydro- 1, 4-thiazepin-F N O 4 (5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]- propanethioamide 419 (5S)-N- [ [3- [3, 5- Same as above Z (b) Difluoro-4- (tetrahydro- 1, 4-thiazepin- 4 (5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]-2- methylpropanethioa mide 420 (5S)-N- [ [3- [3, 5- Same as above Z (c) Difluoro-4- (tetrahydro- 1, 4-thiazepin- 4 (5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]- cyclopropanecarbot hio- amide EXAMPLE 421.

(5S)-N-[[3-[4-(Tetrahydro-1,4-thiazepin-4 (5H)-yl) phenyl- 2-oxo-5-oxazolidinyl] methyl] thioacetamide TABLE P Example Compound Amine Dithio Compound No. (from Preparation Z) 422 (5S)-N- [ [3- [4- Z (a) (Tetrahydro-1, 4-S thiazepin-4 (5H)- y))- phenyl]-2-oxo-5-N O oxazolidinyl]- v methyl] propanethio amide 423 (5S)-N- [ [3- [4- Same as above Z (b) (Tetrahydro-1, 4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl] methy 1]-2- methylpropanethioa mide 424 (5S)-N- [ [3- [4- Same as above Z (c) (Tetrahydro-1, 4- thiazepin-4 (5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl]- methyl] cyclopropane- carbothioamide 425 (5S)-N- [ [3- [3-Fluo ro-4- (tetrahydro-1, 4- thiazepin-4 (5H)- yl) phenyl]-2-oxo-5 oxazolidinyl] methy 1]-1- azetidinecarbothio amide, thiazepine S-oxide 426 (5S)-N-[[3-[3-Fluo ro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl) phenyl]-2-oxo-5 oxazolidinyl] methy 1]-0- methylthiocarbamat e, thiazepine S-oxide 427 (5S)-N-[[3-[3,5- Difluoro-4- (tetrahydro- 1,4-thiazepin- 4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-l- azetidinecarbothi oamide, thiazepine S- oxide 428 (5S)-N-[[3-[4- (Tetrahydro-1,4- thiazepin-4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-1 azetidinecarbothi oamide, thiazepine S-oxide 429 (5S)-N-[[3-[3-Flu oro-4- (tetrahydro-1,4 thiazepin-4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth y 1] 1 azetidinecarbothi oamide, thiazepine S, S-dioxide 430 (5S)-N-[[3-[3,5- Difluoro-4- (tetrahydro- 1,4-thiazepin- 4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-1- azetidinecarbothi oamide, thiazepine S, S- dioxide 431 (5S)-N-[[3-[4- (Tetrahydro-1,4- thiazepin-4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-l- azetidinecarbothi oamide, thiazepine S, S- dioxide 432 (5S)-N- [ [3- [3- Fluoro-4- (tetrahydro-1,4- thiazepin-4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-1- azetidinecarbothi oamide 433 (5S)-N-[[3-[3,5- Difluoro-4- (tetrahydro- 1,4-thiazepin- 4 (5H)- yl) phenyl-2- oxo-5- oxazolidinyl] met hyl]-1- azetidinecarboth ioamide 434 (5S)-N-[[3-[4- (Tetrahydro-1,4- thiazepin-4 (5H)- yl) phenyl]-2-oxo- 5- oxazolidinyl] meth yl]-l- azetidinecarbothi oamide EXAMPLE 435 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide-Method A Step 1: Preparation of (5R)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxylic acid A solution of benzyl 3-fluoro-4- (4- morpholinyl) phenylcarbamate (J. Med. Chem. 1996, 39 (3), 673-679,2. 50 g, 7.57 mmol) in dry tetrahydrofuran (37.8 0 mL) at-78 C under nitrogen was treated with n- butyllithium (1.6M in hexanes, 4.82 mL, 7.72 mmol) o dropwise and stirred at-78 C for 30 minutes. The cooling bath was removed and the mixture was allowed to slowly 0 warm to-40 C, at which point potassium (2R)-glycidate (J.

Org. Chem. 1992, 57 (12), 3380-3387,974 mg, 7.72 mmol) was added. After subsequent warming to ambient temperature, the resulting mixture was vigorously stirred for 2.75 days and then quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 75 mL) to remove the remaining starting. The aqueous phase was adjusted to pH 2 with 1M aqueous hydrochloric acid, saturated with sodium chloride and extracted with methylene chloride (5 x 100 mL), and this combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The product mixture was then chromatographed on a Flash 40M silica gel (90 g, 32-63 Mm) cartridge, eluting with a gradient of acetonitrile/methylene chloride (10/90-40/60) containing 1 % formic acid, and those fractions with an Rf = 0.15 by TLC (acetonitrile/methylene chloride, 50/50 + 1% formic acid) are pooled and concentrated to give the title compound, 1H NMR (400 MHz, DMSO-d6) 6 13.7 (bs, 1H), 7.48 (dd, 1H), 7.23 (m, 1H), 7.05 (t, 1H), 5.17 (dd, 1H), 4.30 (t, 1H), 4.06 (dd, 1H), 3.73 (m, 4H), 2.96 (m, 4H) ; MS (ESI+) for C14Hl5FN205 m/z 311 (M+H) + ; [a] 2'D =-38° (c 0.94, DMSO).

Step 2: Preparation of (5R)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide To a flame-dried flask containing (5R)- (-)-3- [3- fluoro-4- (4-morpholinyl) phenyl]-2-oxo-5- oxazolidinecarboxylic acid (Step 1,250 mg, 0.806 mmol) under nitrogen was added oxalyl chloride (4 mL) with stirring. The flask was capped with a drying tube, and the mixture was stirred at ambient temperature for 15 hours and then concentrated under reduced pressure to give the acid chloride intermediate [MS (ESI+) m/z 325 (M+H) + observed for the methyl ester obtained by reaction of the acid chloride with methanol] which was used without further purification. This intermediate was then taken up in anhydrous tetrahydrofuran (8 mL) under 0 nitrogen, cooled to 0 C, and ammonia (g) was bubbled in for 5 minutes. The resulting mixture was capped with a drying tube, stirred at ambient temperature for 1 hour, and then diluted with water (20 mL) and extracted with methanol/chloroform (10/90,2 x 30 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the product mixture was recrystallized from ethyl acetate/hexane to 0 give the title compound, mp 185-187 C (decomp. ) ; MS (ESI+) for C14Hl6FN304 m/z 310 (M+H) + ; [a] 25D =-23° (c 0.89, DMSO).

EXAMPLE 436 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-N-methyl-2-oxo-5-oxazolidinecarboxamide Following the general procedure of EXAMPLE 435, Step 2, and making non-critical variations but substituting methylamine for ammonia, the title compound 0 was/obtained, mp 182-183 C (decomp. ); MS (ESI+) for C15Hl8FN304 m/z 324 (M+H) + ; [a] 250 =-39° (c 0.92, DMSO).

EXAMPLE 437 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-N-allyl-2-oxo-5-oxazolidinecarboxamide To a flame-dried flask under nitrogen was added allylamine (0.60 mL, 8.05 mmol). The flask was cooled in an ice bath, and a solution of (5R)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarbonyl chloride (EXAMPLE 435, Step 2,0. 805 mmol theory) in anhydrous tetrahydrofuran (8.0 mL) was added. The resulting mixture was stirred under nitrogen for 2 hours, allowing the cooling bath to slowly expire, and was then diluted with water (10 mL) and extracted with methylene chloride (20 mL). The organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 Am) cartridge, eluting with a gradient of methanol/methylene chloride (0.5/99. 5-2/98). Pooling and concentration of those fractions with an Rf = 0.44 by TLC (methanol/chloroform, 5/95) provides the title 0 compound, mp 167-169 C ; MS (ESI+) for C17H20FN304 m/z 350 (M+H) ; [a] D =-44° (c 0.94, DMSO).

EXAMPLE 438 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-N-propyl-2-oxo-5-oxazolidinecarboxamide Following the general procedure of EXAMPLE 437, and making non-critical variations but substituting propylamine for allylamine and triturating and filtering the final product from methanol/diethyl ether, the title 0 compound was obtained, mp 165-167 C; MS (ESI+) for C17H22FN304 m/z 352 (M+H) + ; [a] 25D =-43° (c 1.02, DMSO).

EXAMPLE 439 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-N-methoxy-2-oxo-5-oxazolidinecarboxamide A mixture of (5R)- (-)-3- [3-fluoro-4- (4-morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxylic acid (EXAMPLE 1, Step 1,150 mg, 0.483 mmol) and 0-methylhydroxylamine hydrochloride (61 mg, 0.724 mmol) in tetrahydrofuran/water (1/1, 4. 8 mL) was treated with 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (278 mg, 1.45 mmol), and the resulting mixture was stirred at ambient temperature for 30 minutes and was then diluted with water (10 mL) and extracted with ethyl acetate (2 x 20 mL). The combined organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 m) cartridge, eluting with methanol/methylene chloride (2.5/97. 5).

Pooling and concentration of those fractions with an Rf = 0.53 by TLC (methanol/chloroform, 10/90) gives the title 0 compound, mp 206-208 C (decomp.) ; MS (ESI+) for CisHiaFN30s m/z 340 (M+H) + ; [a] 25D =-56° (c 0.92, DMSO).

EXAMPLE 440 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl) phenyl]-N-hydroxy-2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of (5R)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-N-benzyloxy-2-oxo-5- oxazolidinecarboxamide Following the general procedure of EXAMPLE 439, and making non-critical variations but substituting O- benzylhydroxylamine hydrochloride for 0- methylhydroxylamine hydrochloride, the title compound was 0 obtained, mp 191-193 C (decomp.) ; MS (ESI+) for C21H22FN305 m/z 416 (M+H) + ; [a] 25D =-46° (c 0.93, DMSO).

Step 2: Preparation of (5R)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-N-hydroxy-2-oxo-5- oxazolidinecarboxamide To a mixture of (5R)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-N-benzyloxy-2-oxo-5- oxazolidinecarboxamide (Step 1, 300 mg, 0.722 mmol) in methanol (28.8 mL) was added 5% palladium-on-carbon (77 mg) under nitrogen. The resulting mixture was degassed and stirred under a hydrogen atmosphere (balloon) for 1 hour. The catalyst was then removed by filtration through Celite, rinsing with methanol (60 mL), and the filtrate was concentrated under reduced pressure.

Trituration of this residue with (5% methanol/methylene <BR> <BR> chloride) /diethyl ether gives the title compound, mp 141 - oc ; MS (ESI+) for C14Hl6FN305 m/z 326 (M+H) + ; [a] 25D = - 70° (c 0.99, DMSO).

EXAMPLE 441 (5R)- (-)-3- [4- (3-Pyridyl)-3-fluorophenyl]- 2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of (5R)- (-)-3- [3-fluoro-4- iodophenyl]-5-hydroxymethyl-2-oxazolidinone A solution of isobutyl 3-fluoro-4- iodophenylcarbamate (Org. Process Res. Dev. 2001, 5 (1), 80-83,5. 00 g, 14.83 mmol) in dry tetrahydrofuran (59 mL) 0 at-78 C under nitrogen was treated with lithium hexamethyldisilazide (1. OM in tetrahydrofuran, 15.6 mL, 0 15.57 mmol) dropwise and stirred at-78 C for 45 minutes.

Then, (R) -glycidyl butyrate (2.21 mL, 15.57 mmol) was added dropwise, and the resulting mixture was stirred at a - 78 C for 1 hour and at ambient temperature for 2.75 days.

The reaction mixture was then quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (20 mL) and the layers are separated. The aqueous phase was extracted with ethyl acetate (25 mL), and the combined organic phase was washed with water (25 mL) and saline (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product mixture was then chromatographed on a Flash 40M silica gel (90 g, 32-63 zm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98), and those fractions with an Rf= 0. 25 by TLC (methanol/chloroform, 5/95) are pooled and concentrated to give the title 0 compound, mp 116-117 C ; MS (ESI+) for CloH9FIN03 m/z 338 (M+H) + ; [OC315D =-41 (c 0.98, DMSO).

Step 2: Preparation of (-)-methyl (5R)-3- [3-fluoro-4- iodophenyl]-2-oxo-5-oxazolidinecarboxylate A solution of (5R)- (-)-3- [3-fluoro-4-iodophenyl]-5- hydroxymethyl-2-oxazolidinone (Step 1,7. 61 g, 22.58 0 mmol) in acetone (150 mL) at-10 C was treated with a mixture of Cr03 (6.21 g, 62.1 mmol) in sulfuric acid (6M, 16.9 mL, 101 mmol) dropwise over 15 minutes. The resulting mixture was allowed to slowly warm to ambient temperature with vigorous stirring (slight exotherm to 35°C) and was stirred for an additional 16 hours. The mixture was then treated with isopropanol (35 mL), diluted with saline (150 mL) and diethyl ether (150 mL), stirred until all solids are dissolved, and the layers are separated. The aqueous phase was extracted with diethyl ether (100 mL), and the combined organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the crude carboxylic acid intermediate which was taken up in methanol (225 mL) and treated with concentrated sulfuric acid (8 drops). The resulting homogeneous mixture was stirred at ambient temperature for 20 hours and was then concentrated under reduced pressure to give the crude methyl ester product which was chromatographed on two Flash 40M 90g silica gel (32-63 Um) cartridges, eluting with a gradient of ethyl acetate/heptane (20/80-40/60).

Pooling and concentration of those fractions with an Rf= 0.36 by TLC (ethyl acetate/hexane, 50/50) gives the title compound, mp 106-109OC ; MS (ESI+) for C11HgFIN09 m/z 366 (M+H) + ; [a] 25D =-30 (c 0.93, DMSO).

Step 3: Preparation of (5R)- (-)-3- [3-fluoro-4- iodophenyl]-2-oxo-5-oxazolidinecarboxamide A solution of (-)-methyl (5R)-3- [3-fluoro-4- iodophenyl]-2-oxo-5-oxazolidinecarboxylate (Step 2,6. 23 g, 17.1 mmol) in acetonitrile (85 mL) was treated with concentrated ammonium hydroxide (85 mL), and the resulting mixture was stirred at ambient temperature for 1 hour. The mixture was then diluted with saline (100 mL) and extracted with methylene chloride (3 x 100 mL), and the combined organic phase was washed with saline (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was diluted with hot ethyl acetate (200 mL) and filtered to remove inorganic residue, and the filtrate was diluted with hexanes (300 mL). The resulting precipitate was isolated by filtration to give the title compound, mp 176-178OC ; MS (ESI+) for C1oH8FIN203 m/z 351 (M+H) + ; [a] 25D = - 19 (c 0.97, DMSO).

Step 4: Preparation of 3- (trimethylstannyl) pyridine A mixture of hexamethylditin (654 mg, 1.99 mmol), 3- bromopyridine (300 mg, 1.90 mmol) and bis (triphenylphosphine) palladium (II) chloride (40 mg, 0.057 mmol) in 1,4-dioxane (9.5 ml) was degassed, heated up to 90°C under nitrogen, stirred at this temperature for 2.5 hours and at ambient temperature overnight, and was then concentrated under reduced pressure. The product mixture was chromatographed on a Flash 40S 40g silica gel (32-63 m) cartridge, eluting with ethyl acetate/heptane (20/80), and those fractions with an Rf= 0.47 by TLC (ethyl acetate/hexane, 50/50) are pooled and concentrated to give the title compound (see Chem. Pharm.

Bull. 1982, 30 (5), 1731-1737 for characterization).

Step 5: Preparation of (5R)- (-)-3- [4- (3-pyridyl)-3- fluorophenyl]-2-oxo-5-oxazolidinecarboxamide A mixture of (5R)- (-)-3- [3-fluoro-4-iodbphenyl]-2- oxo-5-oxazolidinecarboxamide (Step 3,422 mg, 1.21 mmol), 3- (trimethylstannyl) pyridine (Step 4,350 mg, 1.45 mmol), tris (dibenzylideneacetone) dipalladium (0) (22 mg, 0.0242 mmol), triphenylarsine (59 mg, 0.194 mmol) and copper (I) iodide (9 mg, 0.0484 mmol) in N-methyl-2-pyrrolidinone 0 (4.8 mL) under nitrogen was degassed, heated up to 50 C and stirred at this temperature for 2 days, during which additional tris (dibenzylideneacetone) dipalladium (0) (22 mg, 0.0242 mmol), triphenylarsine (59 mg, 0.194 mmol) and copper (I) iodide (9 mg, 0.0484 mmol) are added. The resulting mixture was diluted with water (15 mL) and extracted with methylene chloride (3 x 20 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oil was diluted with ethyl acetate (25 mL) and extracted with aqueous hydrochloric acid (1M, 25 mL), and the aqueous phase was neutralized with sodium hydroxide (s), saturated with sodium chloride and extracted with methylene chloride (3 x 25 mL) containing a small amount of methanol. This combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the title compound, mp 240-242 C <BR> <BR> (dec. ); MS (ESI+) for ClsHl2FN3o3 m/z 302 (M+H) + ; [a] 25D 25 (c 0.94, DMSO).

EXAMPLE 442 (5R)- (-)-3- [4- (4-Pyridyl)-3-fluorophenyl]- 2-oxo-5-oxazolidinecarboxamide Following the general procedure of EXAMPLE 441, Step 5, and making non-critical variations but substituting 4- (trimethylstannyl) pyridine (US 5,990, 136,23 November 1999) for 3- (trimethylstannyl) pyridine, the title 0 compound was obtained, mp 256-259 C (dec. ); MS (ESI+) for C15Hl2FN303 m/z 302 (M+H) +i [a] 25D =-27 (c 0.94, DMSO).

EXAMPLE 443 (5R)- (-)-3- [4- (3, 6-Dihydro-2H-pyran-4-yl) -<BR> 3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of (5R)-3- [4- (trimethylstannyl)-3- fluorophenyl]-2-oxo-5-oxazolidinecarboxamide A mixture of (5R)- (-)-3- [3-fluoro-4-iodophenyl]-2- oxo-5-oxazolidinecarboxamide (EXAMPLE 441, Step 3,3. 50 g, 10.0 mmol), hexamethylditin (3.44 g, 10.5 mmol) and bis (triphenylphosphine) palladium (II) chloride (140 mg, 0.200 mmol) in 1,4-dioxane (50 mL) under nitrogen was 0 0 degassed, heated up to 90 C and stirred at 90 C for 2 hours and at ambient temperature overnight. The resulting mixture was concentrated under reduced pressure to remove dioxane, diluted with methylene chloride (75 mL), washed with saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The residue was chromatographed on a Flash 40M 90g silica gel (32-63 tm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98), and those fractions with an Rf= 0.26 by TLC (methanol/chloroform, 5/95) are pooled and concentrated to give the title compound, 1H NMR (400 MHz, CDC13) 6 7. 38 (m, 2 H), 7.20 (m, 1 H), 6.65 (s, 1 H), 5.82 (s, 1 H), 5.00 (dd, 1 H), 4. 26 (m, 2 H), 0.35 (m, 9 H).

Step 2: Preparation of (5R)- (-)-3- [4- (3, 6-dihydro-2H- pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxamide A mixture of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonic acid ester (US 5,968, 962,19 October 1999,682 mg, 2.94 mmol), tris (dibenzylidene- acetone) dipalladium (0) (54 mg, 0.0588 mmol) and triphenylarsine (144 mg, 0.470 mmol) in N-methyl-2- pyrrolidinone (14.7 mL) was degassed and stirred under nitrogen for 5 minutes. (5R)-3- [4- (trimethylstannyl)-3- fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (Step 1, 1.14 g, 2.94 mmol) was then added, and the resulting mixture was stirred at ambient temperature for 5 days.

The reaction mixture was then diluted with water (25 mL) and extracted with ethyl acetate (3 x 30 mL), and the combined organic phase was washed with water (3 x 30 mL) and saline (20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product mixture was chromatographed on a Flash 40M 90g silica gel (32-63 pm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99- 2.5/97. 5), and those fractions with an Rf = 0.40 by TLC (methanol/chloroform, 2 x 5/95) are pooled and concentrated to give the title compound, mp 164-169 C ; MS (ESI-) for C15HlsN2o4F m/z 305 (M-H)- ; [a] 2SD =-23 (c 0.96, DMSO).

EXAMPLE 444 (5R)- (-)-3- [4- (Tetrahydro-2H-pyran-4-yl)- 3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide A mixture of (5R)- (-)-3- [4- (3, 6-dihydro-2H-pyran-4- yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 443, Step 2,200 mg, 0.653 mmol) and 10% palladium-on-carbon (139 mg, 0.131 mmol) in methanol (26 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 5 hours. The catalyst was then removed by filtration through a pad of Celite, and the filtrate was concentrated under reduced pressure and chromatographed on a Flash 40S 40g silica gel (32-63 h-n) cartridge, eluting with a gradient of methanol/methylene chloride (2/98-3/97). Pooling and concentration of those fractions with an Rf = 0.37 by TLC (methanol/chloroform, 2 x 5/95) gives the title compound, mp 153-156OC ; MS (ESI-) for C15Hl7N204F m/z 307 (M-H)- ; [a] 25D =-21 (c 0.87, DMSO).

EXAMPLE 445 (5R)-3- [4- (3, 6-Dihydro-2H-thiopyran-4-yl)- 3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide Step 1: Preparation of (-)-methyl (5R)-3- [4- (3, 6- dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oXo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 435, Step 1, and making non-critical variations but substituting isobutyl 4- (3, 6-dihydro-2H-thiopyran-4-yl) -3- fluorophenylcarbamate (WO 00/44741,3 August 2000) for benzyl 3-fluoro-4- (4-morpholinyl) phenylcarbamate, the crude (5R)-3- [4- (3, 6-dihydro-2H-thiopyran-4-yl)-3- fluorophenyl]-2-oxo-5-oxazolidinecarboxylic acid intermediate was obtained and was used without further purification. This intermediate (540 mg crude) was taken up in methanol (16 mL), a drop of concentrated sulfuric acid was added, and the mixture was stirred at ambient temperature for 21 hours. Then, the reaction mixture was concentrated under reduced pressure and chromatographed on a Flash 40S 40g silica gel (32-63 item) cartridge, eluting with ethyl acetate/heptane (25/75). Pooling and concentration of those fractions with an Rf = 0.25 by TLC (ethyl acetate/hexs, 50/50) give the title compound, mp 106-110OC ; MS (ESI+) for C16Hl6NO4FS m/z 338 (M+H) + ; [a] 25D = - 36 (c 0.99, DMSO).

Step 2: Preparation of (5R)- (-)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinecarboxamide Following the general procedure of EXAMPLE 441, Step 3, and making non-critical variations but substituting (-)-methyl (5R)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxylate (Step 1) for (-)-methyl (5R)-3- [3-fluoro-4- iodophenyl]-2-oxo-5-oxazolidinecarboxylate and purifying the product by recrystallization from methanol/diethyl 0 ether, the title compound was obtained, mp 182-184 C <BR> <BR> (dec. ) ; MS (ESI-) for Cl5H15FN203S m/z 321 (M-H)- ; [a] = - 24 (c 0.93, DMSO).

Step 3: Preparation of (5R)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxamide S-oxide A mixture of (5R)- (-)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinecarboxamide (Step 2,294 mg, 0.912 mmol) in methanol (18 mL) was treated with sodium periodate (205 mg, 0.958 mmol) in water (3.8 mL), and the mixture was stirred at ambient temperature for 44 hours. The resulting mixture was diluted with water (25 mL) and extracted with methylene chloride (5 x 30 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product mixture was triturated with acetone/diethyl ether and then filtered to give the title compound as a mixture of two diastereomers, 1H NMR (400 MHz, DMSO-d6) 7.87 (s, 1 H), 7.63 (s, 1 H), 7.52 (d, 1 H), 7.39 (m, 2 H), 5.83 (m, 1 H), 5.04 (dd, 1 H), 4.29 (t, 1 H), 4.02 (dd, 1 H), 3.65 (m, 1 H), 3.39 (m, 1 H), 3.10 (m, 1 H), 2.92 (m, 2 H), 2.54 (m, 1 H); MS (ESI+) for C15Hl5FN204S m/z 339 (M+H) +.

EXAMPLE 446 (5R)- (-)-3- [4- (3, 6-Dihydro-2H-thiopyran-4- yl) -3-fluorophenyl] -2-oxo-5-oxazolidinecarboxamide S, S- dioxide A solution of (5R)- (-)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxamide (EXAMPLE 445, Step 2,209 mg, 0.648 mmol) in water/acetone (25/75,13 mL) under nitrogen was treated with N-methylmorpholine N-oxide (190 mg, 1.62 mmol) and osmium tetroxide (2.5 wt% in tBuOH, 0.41 mL, 0.0324 mmol), and the mixture was stirred at ambient temperature for 43 hours. The reaction was then treated with - saturated aqueous sodium bisulfite (25 mL) and extracted with methylene chloride (3 x 25 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a Flash 40S 40g silica gel (32-63 m) cartridge, eluting with a gradient of methanol/methylene chloride (2.5/97. 5-4/96), and those fractions with an Rf= 0.48 by TLC (methanol/chloroform, 10/90) are pooled and concentrated to give the title compound, mp 206-208 ; MS (ESI-) for C15Hl5FN205S m/z 353 (M-H)-; [a] 25D =-20 (c 0.98, DMSO).

EXAMPLE 447 (5R)- (-)-3- [4- (Tetrahydro-2H-thiopyran-4- <BR> <BR> yl) -3-fluorophenyl] -2-oxo-5-oxazolidinecarboxamide S, S- dioxide A mixture of (5R)- (-)-3- [4- (3, 6-dihydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinecarboxamide S, S-dioxide (EXAMPLE 446,73 mg, 0.206 mmol) and 10% palladium-on-carbon (44 mg, 0.0412 mmol) in methanol (21 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 16 hours.

The catalyst was then removed by filtration through a pad of Celite, rinsing with methanol and tetrahydrofuran, and the filtrate was concentrated under reduced pressure and triturated with (5% methanol/methylene chloride)/diethyl ether. Filtration then provides the title compound, mp 229-231°C (dec. ); MS (ESI-) for C15HiiFN205S m/z 355 (M-H)-; [a] 25D =-20 (c 0.83, DMSO).

EXAMPLE 448 (5R)- (-)-3- [3-Fluoro-4- [4- (hydroxyacetyl)- 1-piperazinyl] phenyl]-2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of (-)-phenylmethyl 4- [4- [ (5R)-5- (aminocarbonyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1- piperazinecarboxylate Following the general procedure of EXAMPLE 435, Step 1, and making non-critical variations but substituting benzyl 4-(4-{[benzyloxycarbonyl] amino}-2-fluorophenyl)-1- piperazinecarboxylate (J. Med. Chem. 1996, 39 (3), 673- 679) for benzyl 3-fluoro-4- (4-morpholinyl) phenyl- carbamate, the crude 1- (phenylmethyl)-4- [4- [ (5R)-5- carboxy-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1- piperazinecarboxylate intermediate was obtained [MS (ESI-) for C22H22N306F m/z 442 (M-H)-] and was used without further purification. This intermediate (1.66g crude) was taken up in methanol (75 mL), 4 drops of concentrated sulfuric acid are added, and the mixture was stirred at ambient temperature for 19 hours. Then, the reaction mixture was concentrated under reduced pressure and chromatographed twice on a Flash 40M 90g silica gel (32- 63 pm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98). Pooling and concentration of those fractions with an Rf = 0. 64 by TLC (methanol/chloroform, 5/95) provides 740 mg of the phenylmethyl 4- [2-fluoro-4- [ (5R)-5- (methoxycarbonyl)-2- oxo-3-oxazolidinyl] phenyl]-l-piperazinecarboxylate intermediate [MS (ESI+) for C23H2qN306F m/z 458 (M+H) + ; 75- 80% purity] which was used without further purification.

This intermediate was taken up in 2M ammonia in methanol (13 mL), and the resulting mixture was stirred at ambient temperature for 3 hours and then concentrated under reduced pressure. The residue was chromatographed on a Flash 40M 90g silica gel (32-63 Um) cartridge, eluting with a gradient of methanol/methylene chloride (1/99- 3/97), and those fractions with an Rf = 0. 20 by TLC (methanol/chloroform, 5/95) are pooled and concentrated 0 to give the title compound, mp 172-175 C ; MS (ESI+) for C22H23N405F m/z 443 (M+H) + ; [a] 25 =-17 (c 1.04, DMSO).

Step 2: Preparation of (5R)-3- [3-fluoro-4- [4- [(phenylmethoxy) acetyl]-1-piperazinyl] phenyl]-2-oXo-5- oxazolidinecarboxamide A mixture of (-)-phenylmethyl 4- [4- [ (5R)-5- (aminocarbonyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1- piperazinecarboxylate (Step 1, 415 mg, 0.938 mmol) and 10% palladium-on-carbon (100 mg, 0.0938 mmol) in methanol (45 mL) was shaken under a 45 psi hydrogen atmosphere on a Parr apparatus for 4 hours. The catalyst was then removed by filtration through a pad of Celite, and the filtrate was concentrated under reduced pressure to give 290 mg (100%) of the (5R)-3- [ (3-fluoro-4-piperazinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide intermediate [MS (ESI+) for C14Hl7N403F m/z 309 (M+H) +] which was used without further purification. A mixture of this intermediate (240 mg, 0.778 mmol) in methylene chloride (7.8 mL) under nitrogen was treated with triethylamine (163 FL, 1.17 mmol) followed by benzyloxyacetyl chloride (135 IL, 0.856 mmol), and the resulting homogeneous mixture was stirred at ambient temperature for 3 hours.

The reaction mixture was then diluted with water (20 mL) and methylene chloride (20 mL), the layers are separated, and the organic phase was washed with saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which was then chromatographed on a Flash 40M 90g silica gel (32-63 m) cartridge, eluting with methanol/methylene chloride (2.5/97. 5). Pooling and concentration of those fractions with an Rf = 0.50 by TLC (methanol/chloroform, 10/90) provides the title compound, 1H NMR (400 MHz, DMSO- d6) b 7. 85 (s, 1 H), 7. 61 (s, 1 H), 7. 52 (dd, 1 H), 7. 36 (m, 4 H), 7.31 (m, 1 H), 7.24 (m, 1 H), 7.06 (m, 1 H), 5.01 (dd, 1 H), 4.53 (s, 2 H), 4.25 (m, 3 H), 3.97 (dd, 1 H), 3.58 (m, 4 H), 2.96 (m, 4 H); MS (ESI+) for C23H25FN405 m/z 457 (M+H) +.

Step 3: Preparation of (5R)- (-)-3- [3-fluoro-4- [4- (hydroxyacetyl)-1-piperazinyl] phenyl]-2-oxo-5- oxazolidinecarboxamide A mixture of (5R)-3- [3-fluoro-4- [4- [ (phenylmethoxy)- acetyl]-1-piperazinyl] phenyl]-2-oxo-5-oxazolidine- carboxamide (Step 2,260 mg, 0.570 mmol) and 10% palladium-on-carbon (61 mg, 0.0570 mmol) in a mixture of methanol (5 mL) and EtOH (23 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 22 hours.

The catalyst was then removed by filtration through a pad of Celite, rinsing with tetrahydrofuran (200 mL), and the filtrate was concentrated under reduced pressure and triturated with methanol/diethyl ether. Filtration then 0 provided the title compound, mp 232-235 C (dec. ) ; MS (ESI+) for C16H1gFN405 m/z 367 (M+H) + ; [a] 25D =-20 (c 0.98, DMSO).

EXAMPLE 449 (5R)- (-)-3- [4- (Thiomorpholin-4-yl)-3, 5- difluorophenyl]-2-oxo-5-oxazolidinecarboxamide S, S- dioxide Step 1: Preparation of 4- (2, 6-difluorophenyl) thio- morpholine 1, 1-dioxide Aluminum chloride (310 g, 2.3 mol) was added to chlorobenzene (2.5 L) to give a cloudy green suspension.

Vinyl sulfone (230 mL, 2.3 mol) was added via funnel, followed by 2,6-difluoroaniline (250 mL, 2.3 mol). The 0 light brown solution was heated to 110 C. Upon completion of the reaction, the heat was removed and the 0 black solution was self-cooled to 70 C. The reaction mixture was then quenched in methylene chloride (4 L) and ice water (5 L), the aqueous phase was extracted with methylene chloride (3 L, 2 L, 2 L, 2 L) and the combined organic layers are concentrated, rediluted with branched 0 octane (3 L), and then cooled to 0 C for 30 minutes. The solids are filtered and washed with branched octane (2 x 500 mL) and are then dissolved in methylene chloride (3 L) and loaded onto a Si02 plug (1.8 kg). The column was eluted with dichloromethane (16 L) until clear. The methylene chloride solution was concentrated, and the solids are dissolved in hot ethyl acetate (3 L) followed by the addition of hexanes (900 mL). The black solution was self-cooled to room temperature overnight, and the resulting light amber crystal needles are filtered and washed with hexanes (4 x 250 mL). The solids are dried 0 under reduced pressure at 50 C overnight to give the title compound, 1H NMR (CDC13) (5) : 7.08 (m, 1H), 6.91 (m, 2H), 3.67 (m, 4H), 3.18 (m, 4H).

Step 2: Preparation of 4- (2, 6-difluoro-4-nitro- phenyl) thiomorpholine 1,1-dioxide To a suspension of 4- (2, 6-difluorophenyl) thio- morpholine 1, 1-dioxide (Step 1,300 g, 1.21 mol) in 3 L of acetic acid, nitric acid (255 mL, ca. 6 mol, fuming, 90%) was added over 30 minutes at ambient temperature. A yellow precipitate forms within minutes and increases over time. The reaction was kept at room temperature for 18 hours and was then poured into 6 L of water. After stirring for 2 hours, the yellow suspension was filtered.

The precipitate was washed with water (1.5 L x 3) and ethanol (0.5 L 2) and dried at 50 C overnight to give the title compound, 1H NMR (DMSO-d6) (6) : 8.05 (m, 2H), 3.69 (m, 4H), 3.26 (m, 4H).

Step 3: Preparation of 4- (1, 1-dioxido-4-thio- morpholinyl) -3,5-difluoroaniline To an autoclave was added 4- (2, 6-difluoro-4- nitrophenyl) thiomorpholine 1,1-dioxide (Step 2,7. 0 kg, 24 moles, 1.0 eq). Raney Nickel (1.4 kg) was activated and suspended in tetrahydrofuran (4 L), and the slurry was added to the autoclave followed by additional tetrahydrofuran (66 L). The mixture was heated at 40 C under a 40 psi hydrogen atmosphere until the reaction was complete. The mixture was then filtered, and the filtrate was directly used in the next step. A small portion of the filtrate can be concentrated and recrystallized in isopropanol to give the title compound in pure form, 1H NMR (DMSO-d6) (5) : 6.17 (m, 2H), 5. 35 (s, 2H), 3. 32 (m, 4H), 3.15 (m, 4H).

Step 4: Preparation of isobutyl 4- (1, 1-dioxido-4- thiomorpholinyl) -3,5-difluorophenylcarbamate To a 400 L glass-lined reactor containing the 4- (1, 1-dioxido-4-thiomorpholinyl)-3, 5-difluoroaniline/ tetrahydrofuran solutions (Step 3,12. 6 kg, 48 moles, 1.0 eq) was added 47% potassium carbonate solution (14.1 kg, 48 moles, 1.0 eq). The mixture was heated to 0 approximately 45 C, and isobutyl chloroformate (7.2 kg, 53 moles, 1. 1 eq) was added while maintaining a reaction temperature between 45° C and 55 C. The reaction was stirred at 45°-55 C. Once deemed complete, the reaction was quenched by slowly adding water (45 L) over 15 0 minutes. The reaction mixture was cooled to 25 C and the phases are separated. The tetrahydrofuran solution was swapped to an isopropanol (150 L) /water (50 L) 0 suspension, and the slurry was slowly cooled to 5 C. The yellow slurry was then filtered and the cake washed with cold isopropanol (2 x 30 L). The yellow solids are dried with 60°C nitrogen to give the title compound, 1H NMR (CDC13) (5) : 7.02 (m, 2H), 6.81 (s, 1H), 3.95 (d, 2H), 3.60 (m, 4H), 3.17 (m, 4H), 1.97 (m, 1H), 0.94 (d, 6H).

Step 5: Preparation of (5R)- (-)-3- [4- (thiomorpholin-4- yl) -3, 5-difluorophenyl]-2-oxo-5-oxazolidinecarboxamide S, S-dioxide Following the general procedure of EXAMPLE 448, Step 1, and making non-critical variations but substituting isobutyl 4- (1, 1-dioxido-4-thiomorpholinyl)- 3,5-difluorophenylcarbamate (Step 4) for benzyl 4- (4- {[benzyloxycarbonyl] amino}-2-fluorophenyl)-1- piperazinecarboxylate and purifying the final product by trituration and filtration from (10% methanol/ chloroform) /diethyl ether, the title compound was 0 obtained, mp 245-248 C (dec.) ; MS (ESI+) for C14Hl5F2N305S m/z 376 (M+H) + ; [5] 25D =-22 (c 1.00, DMSO).

EXAMPLE 450 (5R)- (-)-3- [3-Fluoro-4- (4-morpholinyl)- phenyl]-2-oxo-5-oxazolidinecarboxamide-Method C Step 1 : Preparation of ethyl (5R)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxylate A solution of 3-fluoro-4-morpholinoaniline (J. Med.

Chem. 1996, 39 (3), 673-679,0. 796 g, 4.0 mmol), ethyl 2 (R) -epoxypropanoate (0.696 g, 6.0 mmol) and lithium triflate (0.97 g, 6.2 mmol) in acetonitrile (12 mL) was 0 stirred at 50-60 C overnight. Solvent and excess epoxide was removed under reduced pressure, and the crude amino alcohol was redissolved in dry acetonitrile (40 mL) and 1, 1'-carbonyldiimidazole (1.46 g, 9.0 mmol) was added. The mixture was stirred at ambient temperature overnight, and then the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (70 mL) and 3% aqueous citric acid (100 mL), the layers are separated, and the organic phase was washed with 3% aqueous citric acid (3 x 100 mL), water and saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product mixture was then purified by silica gel chromatography, eluting with ethanol/methylene chloride (2/98), and the appropriate fractions are pooled and concentrated to give the title compound, MS (ESI+) for C16HlgN205F m/z 339 (M+H) +.

Step 2: Preparation of (SR)- (-)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide A mixture of of ethyl (5R)-3- [3-fluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1,0. 22 g, 0.65 mmol) in 2M ammonia in methanol (5-6 0 mL) was heated in a closed vial at 60 C for approximately 1 hour. The resulting mixture was cooled to ambient temperature and concentrated under reduced pressure, and the crude product was recrystallized from methanol to give the title compound, MS (ESI+) for C14Hl6N304F m/z 310 (M+H) +.

EXAMPLE 451 (5R)- (-)-3- [3, 5-Difluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of butyl (5R)-3- [3, 5-difluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxylate A solution of 3, 5-difluoro-4- (4-morpholinyl) aniline (See US Patent No. 5,688, 792,2. 00 g, 9.34 mmol), butyl 2 (R) -glycidate (2.02 g, 14.0 mmol) and lithium triflate (2.18 g, 14.0 mmol) in acetonitrile (37 mL) was stirred 0 at 60 C under N2 for 48 hrs. Solvent was removed under reduced pressure, and the residue was taken up in MeOH/CH2Cl2 (5/95,100 mL), washed with water (2 x 25 mL) and saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was flushed through a Flash 40M 90 g silica gel cartridge with EtOAc/CH2Cl2 (10/90), and the appropriate fractions were pooled and concentrated to give the amino alcohol intermediate [Rf= 0.10 by TLC, EtOAc/hexanes (25/75)] which was contaminated with residual starting material.

This intermediate (2.5 g in two lots) was then dissolved in acetonitrile (total of 70 mL) and treated with 1, 1'- carbonyldiimidazole (total of 1.69 g, 10.4 mmol, 1.5 equiv. ), and the reaction mixtures were stirred at ambient temperature for 6 days and then concentrated under reduced pressure. The product mixtures were each taken up in CH2Cl2 (50 mL), washed with 0. 1M hydrochloric acid (2 x 20 mL) and saline (10 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/CH2Cl2 (5/95). Those fractions with an Rf= 0.16 by TLC (EtOAc/hexanes, 25/75) were pooled and 0 concentrated to give the title compound, mp 99-100 C; MS (ESI+) for C18H22N205F2 m/z 385 (M+H) +.

Step 2: Preparation of (5R)- (-)-3- [3, 5-difluoro-4- (4- morpholinyl) phenyl]-2-oxo-5-oxazolidinecarboxamide The butyl (5R)-3- [3, 5-difluoro-4- (4-morpholinyl)- phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1,350 mg, 0.910 mmol) was treated with 7N ammonia in methanol (9.1 mL) under N2, and the mixture was stirred at ambient temperature for 30 mins. The reaction mixture was then concentrated under reduced pressure, and the residue was recrystallized from EtOAc/hexanes to give the title 0 compound, mp 181-183 C ; MS (ESI+) for C14Hl5N304F2 m/z 328 (M+H) + ; [a] 25D-23 (c 0.94, DMSO). <BR> <BR> <P>EXAMPLE 452 (5R)- (-)-3- [4- (Thiomorpholin-4-yl) phenyl] - 2-oxo-5-oxazolidinecarboxamide S, S-dioxide Step 1: Preparation of butyl (5R)-3- [4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate A solution of 4- (4-thiomorpholinyl) aniline (See Med.

Chem. Res. 1999, 9 (3), 149-161,2. 60 g, 13.4 mmol), butyl 2 (R) -glycidate (2.89 g, 20.1 mmol) and lithium triflate (3.13 g, 20.1 mmol) in acetonitrile (54 mL) was stirred 0 at 60 C under N2 for 36 hrs. Solvent was removed under reduced pressure, and the residue was taken up in MeOH/CH2Cl2 (5/95,100 mL), washed with water (50 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was flushed through a Flash 40M 90 g silica gel cartridge with EtOAc/CH2Cl2 (15/85), and the appropriate fractions were pooled and concentrated to give the amino alcohol intermediate [Rf= 0.19 by TLC, EtOAc/hexanes (25/75)] which was contaminated with the dialkylated by-product.

This intermediate (4.25 g) was then dissolved in acetonitrile (125 mL) and treated with 1, 1'-carbonyl- diimidazole (3.05 g, 18.8 mmol, 1.5 equiv. ), and the reaction mixture was stirred at ambient temperature for approximately 3 days and then concentrated under reduced pressure. The product mixture was taken up in CH2Cl2 (100 mL), washed with 0. 1M hydrochloric acid (3 x 25 mL) and saline (25 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/CH2Cl2 (15/85). Those fractions with an Rf= 0.57 by TLC (EtOAc/hexanes, 50/50) were pooled and concentrated to 0 give the title compound, mp 95. 5-98 C ; MS (ESI+) for C18H24N204S m/z 365 (M+H) +.

Step 2: Preparation of butyl (5R)-3- [4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide A solution of butyl (5R)-3- [4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 600 mg, 1.65 mmol) in water/acetone (25/75,32 mL) under N2 was treated with N-methylmorpholine N-oxide (483 mg, 4.12 mmol) and osmium tetroxide (2.5 wt% in tBuOH, 1.03 mL, 0.0825 mmol), and the mixture was stirred at ambient temperature for 18 hrs. The reaction was then treated with h-saturated aqueous sodium bisulfite (20 mL), diluted with water (20 mL) and extracted with CH2Cl2 (2 x 50 mL). The combined organic phase was washed with saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the product mixture was chromatographed on a Flash 40S 40 g silica gel cartridge with MeOH/CH2Cl2 (1/99). Pooling and concentration of those fractions with an Rf= 0.5 by TLC (MeOH/CHCl3, 5/95) followed by recrystallization from EtOAc/hexanes gave the title compound, mp 100-102 C; MS (ESI+) for C18H24N206S m/z 397 (M+H) +.

Step 3: Preparation of (5R)- (-)-3- [4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S, S-dioxide The butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl] -2- oxo-5-oxazolidinecarboxylate S, S-dioxide (Step 2, 400 mg, 1.01 mmol) was treated with 7N ammonia in methanol (10.1 mL) under N2, and the mixture was stirred at ambient temperature for 25 mins. The resulting slurry was then diluted with diethyl ether (5 mL) and filtered to give 0 the title compound, mp 226-228 C ; MS (ESI-) for C14H17N305S m/z 338 (M-H)- ; [a] 25D-22 (c 0.94, DMSO).

EXAMPLE 453 (5R)- (-)-3- [3-Fluoro-4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S, S-dioxide Step 1: Preparation of butyl (5R)-3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3- fluoro-4- (4-thiomorpholinyl) aniline (See J. Med. Chem.

1996, 39 (3), 680-685) for 4- (4-thiomorpholinyl) aniline, 0 the title compound was obtained, mp 128-130 C; MS (ESI+) for C18H23N204FS m/z 383 (M+H) +.

Step 2: Preparation of butyl (5R)-3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate S, S-dioxide Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting butyl (5R)-3- [3-fluoro-4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl] -2-oxo-5- oxazolidinecarboxylate, the title compound was obtained, 0 mp 169-171 C (dec. MS (ESI+) for C18H23N206FS m/z 415 (M+H) + Step 3: Preparation of (5R)- (-)-3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide S, S-dioxide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations but substituting butyl (5R)-3- [3-fluoro-4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide (Step 2) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate S, S-dioxide, the title 0 compound was obtained, mp 245-247 C (dec.) ; MS (ESI+) for C14Hl6N305FS m/z 358 (M+H) + ; [a] 25D-22 (c 0.92, DMSO).

EXAMPLE 454 (5R)- (-)-3- [3-Fluoro-4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide Step 1: Preparation of butyl (5R)-3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate S-oxide A solution of sodium periodate (265 mg, 1.24 mmol) in water (5 mL) was treated with a slurry of butyl (5R)- 3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate (EXAMPLE 20, Step 1,450 mg, 1.18 mmol) in methanol (24 mL), and the mixture was stirred at ambient temperature for 23 hrs. The resulting mixture was diluted with water (20 mL) and saline (20 mL) and extracted with CH2C12 (2 x 40 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a Flash 40S 40 g silica gel cartridge, eluting with a gradient of MeOH/CH2Cl2 (1/99-2/98), and those fractions with an Rf = 0.37 by TLC (MeOH/CHC13, 5/95) were pooled and concentrated and the residue recrystallized from EtOAc/hexanes to give the title compound, mp 128-129°C ; MS (ESI+) for C18H23N205FS m/z 399 (M+H) +.

Step 2: Preparation of (5R)- (-)-3- [3-fluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide S-oxide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting (5R)-3- [3-fluoro-4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide (Step 1) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]-2-oxo- 5-oxazolidinecarboxylate S, S-dioxide and purifying the product by trituration and filtration from hot acetonitrile, the title compound was obtained, mp 264- 266 C (dec. ) ; MS (ESI+) for C14Hl6N304FS m/z 342 (M+H) + ; [a] 25D-22 (c 0.39, DMSO).

EXAMPLE 455 (5R)- (-)-3- [3, 5-Difluoro-4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide Step 1: Preparation of 4- (2, 6-Difluoro-4- nitrophenyl) thiomorpholine A solution of 3,4, 5-trifluoronitrobenzene (5.00 g, 0 28.24 mmol) in acetonitrile (60 mL) was cooled to 0 C and treated with N, N-diisopropylethylamine (7.38 mL, 42.35 mmol) followed by thiomorpholine (2.98 mL, 29.65 mmol).

The ice bath was removed and the reaction mixture stirred at room temperature under nitrogen for approximately 24 hrs, during which additional thiomorpholine (0.1 eq) was added. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid (until the washings were acidic), saturated aqueous sodium bicarbonate and saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound, mp 0 104-105 C.

Step 2: Preparation of 3, 5-difluoro-4- (4- morpholinyl) aniline A solution of 4- (2, 6-difluoro-4-nitrophenyl) thio- morpholine (3.00 g, 11.5 mmol) in tetrahydrofuran (60 mL) was added to a Parr bottle containing a mixture of Raney nickel (1 g) in water (15 mL) under N2, and the reaction mixture was shaken on a Parr apparatus under a hydrogen atmosphere at 40 psi for 24 hrs. The catalyst was removed by filtration through Celite, rinsing with tetrahydrofuran and water, the filtrate was diluted with water (50 mL) and EtOAc (50 mL), and the layers were separated. The organic phase was washed with saline (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting oil was chromatographed on a Flash 40M 90 g silica gel cartridge eluting with EtOAc/heptane (15/85). Pooling and concentration of those fractions with an Rf = 0. 19 by TLC (EtOAc/hexanes, 25/75) gave the title compound, mp 85-86 C; MS (ESI+) for C1oHl2N2F2S m/z 231 (M+H) +.

Step 3: Preparation of butyl (5R)-3- [3, 5-difluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3, 5-difluoro-4- (4-morpholinyl) aniline (Step 2) for 4- (4-thiomorpholinyl) aniline, the title 0 compound was obtained, mp 102-103 C; MS (ESI+) for C18H22N204F2S m/z 401 (M+H) +.

Step 4: Preparation of butyl (5R)-3- [3, 5-difluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate S-oxide Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3- [3, 5-difluoro-4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 3) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate, the title compound was obtained, mp 114-116°C ; MS (ESI+) for C18H22N205F2S m/z 417 (M+H) +.

Step 5: Preparation of (5R)- (-)-3- [3, 5-Difluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide S-oxide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting (5R)-3- [3, 5-difluoro-4- (thiomorpholin-4-yl) phenyl]-2-oxo- 5-oxazolidinecarboxamide S-oxide (Step 4) for butyl (5R)- 3- [4- (thiomorpholin-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate S, S-dioxide, the title compound was obtained, 0 mp 273-276 C (dec.) ; MS (ESI+) for C14Hl5N304F2S m/z 360 (M+H) + ; [a] 25D-24 (c 0.96, DMSO).

EXAMPLE 456 (5R)-3- [3-Fluoro-4- (cis-tetrahydro-1- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide Step 1: Preparation of 2-methylpropyl [3-fluoro-4- (tetrahydro-2H-thiopyran-4-yl) phenyl] carbamate A solution of 2-methylpropyl [3-fluoro-4- (tetrahydro-4-hydroxy-2H-thiopyran-4-yl) phenyl] carbamate (See Org. Proc. Res. Dev. 2001,5, 80-83,4. 00 g, 12.2 mmol) in trifluoroacetic acid (19 mL, 244 mmol) under N2 was treated with triethylsilane (5.85 mL, 36.6 mmol) dropwise, stirred for 1 hr, and then added dropwise to saturated aqueous potassium carbonate (250 mL) with vigorous stirring. The mixture was extracted with diethyl ether (200 mL), and the organic phase was washed with water (2 x 50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Trituration and filtration from diethyl ether/hexanes or ethyl acetate/hexanes gave the title compound, 1H NMR (CDC13, 400 MHz) S 7.26 (m, 1H), 7.11 (t, 1H), 6.97 (m, 1H), 6.59 (bs, 1H), 3.95 (d, 2H), 2.85 (m, 3H), 2.68 (m, 2H), 2.09 (m, 2H), 1.98 (m, 1H), 1. 84 (m, 2H), 0. 96 (d, 6H).

Step 2: Preparation of 3-fluoro-4- (tetrahydro-2H- thiopyran-4-yl) benzenamine A mixture of 2-methylpropyl [3-fluoro-4- (tetrahydro- 2H-thiopyran-4-yl) phenyl] carbamate (Step 1, 2. 12 g, 6.81 mmol) in ethylene glycol (25 mL) was treated with aqueous potassium hydroxide (45%, 25.5 g, 204 mmol) with vigorous 0 stirring, and the mixture was heated to 95 C and stirred at this temperature for 18 hrs. The reaction was then cooled to ambient temperature and diluted with water (50 mL) and CH2Cl2 (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was chromatographed on a Flash 40M 90 g silica gel cartridge with a gradient of EtOAc/heptane (15/85-25/75), and those fractions with an Rf = 0.32 by TLC (EtOAc/hexanes, 25/75) were pooled and concentrated to 0 give the title compound, mp 96-98 C; MS (ESI+) for C1lHl4NFS m/z 212 (M+H) +.

Step 3: Preparation of butyl (5R)-3- [3-fluoro-4- (tetrahydro-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3-fluoro-4- (tetrahydro-2H-thiopyran-4- yl) benzenamine (Step 2) for 4- (4-thiomorpholinyl) aniline, 0 the title compound was obtained, mp 98-100 C; MS (ESI+) for Cl9H24NO4FS m/z 382 (M+H) +.

Step 4: Preparation of butyl (5R)-3- [3-fluoro-4- (cis- tetrahydro-1-oxido-2H-thiopyran-4-yl) phenyl]-2-oXo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3- [3-fluoro-4- (tetrahydro-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 3) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2: 1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title 0 compound, mp 142-145 C; MS (ESI+) for C1gH24NO5FS m/z 398 (M+H) +.

Step 5: Preparation of (5R)-3- [3-fluoro-4- (cis- tetrahydro-1-oxido-2H-thiopyran-4-yl) phenyl]-2-oXo-5- oxazolidinecarboxamide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3- [3-fluoro-4- (cis-tetrahydro-1- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate (Step 4) for butyl (5R)-3- [4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide and purifying the product by trituration and filtration from hot methanol and acetonitrile, the title compound 0 was obtained, mp 279-281 C (dec. ); MS (ESI+) for C15Hl7N204FS m/z 341 (M+H) +.

EXAMPLE 457 (5R)-3- [3-Fluoro-4- (trans-tetrahydro-l- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide Step 1: Preparation of butyl (5R)-3- [3-fluoro-4- (trans- tetrahydro-1-oxido-2H-thiopyran-4-yl) phenyl]-2-oXo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3- [3-fluoro-4- (tetrahydro-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 23, Step 3) for butyl (5R)-3- [4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2: 1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided 0 the title compound, mp 133-136 C ; MS (ESI+) for ClsH24NO5FS m/z 398 (M+H) +.

Step 2: Preparation of (5R)-3- [3-fluoro-4- (trans- tetrahydro-1-oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxamide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3- [3-fluoro-4- (trans-tetrahydro- 1-oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxylate (Step 1) for butyl (5R)-3- [4- (thiomorpholin- 4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide, 0 the title compound was obtained, mp 201-203 C; MS (ESI+) for C15Hl7N204FS m/z 341 (M+H) +.

EXAMPLE 458 (5R)- (-)-3- [4- (tetrahydro-2H-thiopyran-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S, S-dioxide Step 1: Preparation of 2-methylpropyl 4- bromophenylcarbamate A solution of 4-bromoaniline (10.0 g, 58.1 mmol) in tetrahydrofuran (230 mL) was treated with sodium bicarbonate (9.77 g, 116.2 mmol) and water (100 mL) followed by isobutyl chloroformate (8.3 mL, 63.9 mmol), and the mixture was stirred at ambient temperature for 2 hrs. The mixture was then diluted with water (100 mL) and EtOAc (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Recrystallization of the resulting solid from EtOAc/hexanes provided the title compound, mp 95-96 C ; MS (ESI-) for CIIH14NO2Br m/z 270 (M-H)-.

Step 2: Preparation of 2-methylpropyl [4- (tetrahydro-4- hydroxy-2H-thiopyran-4-yl) phenyl] carbamate A solution of 2-methylpropyl 4-bromophenylcarbamate (Step 1,10. 0 g, 36.7 mmol) in anhydrous tetrahydrofuran 0 (184 mL) at-78 C under N2 was treated n-butyllithium (1.6M in hexanes, 48.2 mL, 77.1 mmol) dropwise over 20 0 mins, and the mixture was stirred at-78 C for 45 mins.

The resulting slurry was then treated with a solution of tetrahydro-2H-thiopyran-4-one (4.48 g, 38.5 mmol) in anhydrous tetrahydrofuran (38 mL) dropwise over 5 mins to give an opaque mixture which was allowed to slowly warm to 0 C with stirring over approximately 2.5 hrs. The mixture was then quenched by the slow addition of saturated aqueous ammonium chloride (75 mL), water (75 mL) was added, and the layers were separated. The organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the crude product was recrystallized from EtOAc/hexanes to give the 0 title compound, mp 150-151 C ; MS (ESI-) for C16H23NO3S m/z 308 (M-H)-.

Step 3: Preparation of 2-methylpropyl [4- (tetrahydro- 2H-thiopyran-4-yl) phenyl] carbamate Following the general procedure of EXAMPLE 456, Step 1, and making non-critical variations but substituting 2-methylpropyl [4- (tetrahydro-4-hydroxy-2H- thiopyran-4-yl) phenyl] carbamate (Step 2) for 2- methylpropyl [3-fluoro-4- (tetrahydro-4-hydroxy- 2H-thiopyran-4-yl) phenyl] carbamate and purifying the product by recrystallization from EtOAc/hexanes, the 0 title compound was obtained, mp 126-128 C; MS (ESI-) for C16H23NO2S m/z 292 (M-H)-.

Step 4: Preparation of 4- (tetrahydro-2H-thiopyran-4- yl) benzenamine Following the general procedure of EXAMPLE 456, Step 2, and making non-critical variations but substituting 2-methylpropyl [4- (tetrahydro-2H-thiopyran- 4-yl) phenyl] carbamate (Step 3) for 2-methylpropyl [3- fluoro-4- (tetrahydro-2H-thiopyran-4-yl) phenyl] carbamate, 0 the title compound was obtained, mp 103-106 C; MS (ESI+) for C1lHl5NS m/z 194 (M+H) +.

Step 5: Preparation of butyl (5R)-3- [4- (tetrahydro-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 4- (tetrahydro-2H-thiopyran-4-yl) benzenamine (Step 4) for 4- (4-thiomorpholinyl) aniline, the title 0 compound was obtained, mp 94-96 C; MS (ESI+) for C19H25NO4S m/z 364 (M+H) +.

Step 6: Preparation of butyl (5R)-3- [4- (tetrahydro-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting butyl (5R)-3- [4- (tetrahydro-2H-thiopyran-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 5) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate, the title compound was obtained, mp 176-179° C; MS (ESI+) for C19H25NO6S m/z 396 (M+H) +.

Step 7: Preparation of (5R)- (-)-3- [4- (tetrahydro-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxamide S, S-dioxide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3- [4- (tetrahydro-2H-thiopyran-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide (Step 6) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate S, S-dioxide, the title 0 compound was obtained, mp 211-212 C; MS (ESI-) for C15Hl8N205S m/z 337 (M-H)-i [O] 25D-19 (c 0.95, DMSO). EXAMPLE 459 (5R)-3- [4- (cis-tetrahydro-1-oxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxamide Step 1: Preparation of butyl (5R)-3- [4- (cis-tetrahydro- 1-oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 459, Step 1, and making non-critical variations but substituting butyl (5R)-3- [4- (tetrahydro-2H-thiopyran-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 458, <BR> <BR> Step 5) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl] - 2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2: 1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 127-130 C ; MS (ESI+) for C1gH25NO5S m/z 380 (M+H) +.

Step 2: Preparation of (5R)-3- [4- (cis-tetrahydro-l- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3- [4- (cis-tetrahydro-l-oxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate S, S-dioxide, the title 0 compound was obtained, mp 269-273 C (dec. ) ; MS (ESI-) for C15Hl8N204S m/z 321 (M-H)-.

EXAMPLE 460 (5R)-3- [4- (trans-tetrahydro-l-oxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxamide Step 1 : Preparation of butyl (5R)-3- [4- (trans- tetrahydro-1-oxido-2H-thiopyran-4-yl) phenyl]-2-oXo-5- oxazolidinecarboxylate Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3- [4- (tetrahydro-2H-thiopyran-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 458, Step 5) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2: 1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 115-117 C; MS (ESI+) for C1sH25NO5S m/z 380 (M+H) +.

Step 2: Preparation of (5R)-3- [4- (trans-tetrahydro-l- oxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidine- carboxamide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3- [4- (trans-tetrahydro-1-oxido- 2H-thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]- 2-oxo-5-oxazolidinecarboxylate S, S-dioxide, the title 0 compound was obtained, mp 174-175 C; MS (ESI-) for C15Hl8N204S m/z 321 (M-H)-.

EXAMPLE 461 (5R)-3- [4- (Tetrahydro-2H-thiopyran-4-yl)- 3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S, S- dioxide-Method B Step 1: Preparation of 2-methylpropyl [4- (tetrahydro- 1, 1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl] carbamate Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting 2-methylpropyl [4- (tetrahydro-2H-thiopyran- <BR> <BR> 4-yl) -3-fluorophenyl] carbamate (EXAMPLE 456, Step 1) for butyl (5R)-3- [4- (thiomorpholin-4-yl) phenyl]-2-oxo-5- oxazolidinecarboxylate, the title compound is obtained, 1H NMR (CDC13) (8) 7.36 (bd, 1H), 7.14 (t, 1H), 6.99 (m, 1H), 6.70 (bs, 1H), 3.95 (d, 2H), 3.14 (m, 4H), 3.07 (m, 1H), 2.38 (m, 2H), 2.18 (m, 2H), 1.95 (m, lH), 0.96 (d, 6H).

Step 2: Preparation of (5R)-3- [4- (tetrahydro-2H- thiopyran-4-yl)-3-fluorophenyl]-5-hydroxymethyl-2- oxazolidinone S, S-dioxide A solution of 2-methylpropyl [4-(tetrahydro-1, 1- dioxido-2H-thiopyran-4-yl)-3-fluorophenyl] carbamate (Step 1,2. 00 g, 5.82 mmol) in dry tetrahydrofuran at- 0 78 C under N2 was treated with n-butyllithium (1.6M in hexanes, 3.82 mL, 6.11 mmol) dropwise and stirred at- 0 78 C for 45 mins. Then, (R) -glycidyl butyrate (0.86 mL, 6.11 mmol) was added dropwise, and the resulting mixture 0 was stirred at-78 C for 30 mins and at ambient temperature for 2.75 days. The reaction mixture was then quenched with saturated aqueous ammonium chloride (15 mL), diluted with water (15 mL) and EtOAc (25 mL), and the layers were separated. The organic phase was diluted with small amounts of methylene chloride, methanol and tetrahydrofuran in an attempt to dissolve a precipitate that had formed and was then washed with water (20 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure.

The resulting solid was then diluted with hot methanol/EtOAc (1: 5,100 mL), followed by hexanes (150 mL), and filtered to give the title compound, 1H NMR (DMSO) (8) 7.51 (dd, 1H), 7.37 (t, 1H), 7.30 (m, 1H), 5.21 (t, 1H), 4.70 (m, 1H), 4. 07 (t, 1H), 3.81 (dd, 1H), 3.65 (m, 1H), 3.55 (m, 1H), 3.37 (m, 2H), 3.20 (m, 1H), 3.10 (m, 2H), 2.15 (m, 2H), 2.03 (m, 2H).

Step 3: Preparation of methyl (5R)-3- [4- (tetrahydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxylate S, S-dioxide A mixture of ruthenium (III) trichloride (29 mg, 0.139 mmol, 4 mol%), sodium periodate (3.21 g, 15.0 mmol), and sodium dihydrogen phosphate monohydrate (2.60 g, 18.8 mmol) in water/methylene chloride (10: 1, 21 mL) was treated with a suspension of (5R)-3- [4- (tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5- hydroxymethyl-2-oxazolidinone S, S-dioxide (Step 2, 1.20 g, 3.49 mmol) in acetonitrile (35 mL), and the resulting mixture was stirred at ambient temperature for 24 hrs and was then adjusted to pH 2 with aqueous hydrochloric acid (1M) and extracted with methylene chloride (3 x 100 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was flushed through a Flash 40M 90 g silica gel cartridge with a gradient of CH3CN/CH2Cl2 (20/80-40/60) containing 1% formic acid. Those fractions containing the carboxylic acid intermediate (920 mg total) were pooled and concentrated, and the white solid was dissolved in methanol (25 mL) and treated with 3 to 4 drops of concentrated sulfuric acid. The resulting mixture was stirred at ambient temperature for 4 hrs and was then concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel cartridge, eluting with a gradient of MeOH/CH2Cl2 (1/99-2/98). Pooling and concentration of those fractions with an Rf = 0.53 by TLC (MeOH/CH2Cl2, 5/95) provided the title compound as an amorphous solid, 1H NMR (CDC13) 8) 7.50 (dd, 1H), 7.25 (t, 1H), 7.15 (m, 1H), 5.09 (dd, 1H), 4.27 (t, 1H), 4.13 (dd, 1H), 3.88 (s, 3H), 3.15 (m, 4H), 3.11 (m, 1H), 2.40 (m, 2H), 2.19 (m, 2H).

Step 4: Preparation of (5R)-3- [4- (tetrahydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine- carboxamide S, S-dioxide Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations but substituting methyl (5R)-3- [4- (tetrahydro-2H-thiopyran-4- yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylate S, S- dioxide (Step 3) for butyl (5R)-3- [4- (thiomorpholin-4- yl) phenyl]-2-oxo-5-oxazolidinecarboxylate S, S-dioxide and purifying the product by trituration and filtration from (5% MeOH/CH2Cl2)/Et20, the title compound was obtained, mp 231-234°C (dec. ); MS (ESI-) for C15Hl7FN205S m/z 355 (M-H)-.

Additional Examples of amide-containing compounds that can be used in the present invention are disclosed below.

EXAMPLE 462: N- 3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- <BR> <BR> [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-acetamide,<BR> EXAMPLE 463: N- {3- [3-fluoro-4- (6 (S) -methyl-5-oxo-5,6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 464: N- {3- [3-fluoro-4- (6 (R) -methyl-5-oxo-5,6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 465: N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- <BR> <BR> [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-propionamide, EXAMPLE 466: cyclopropanecarboxylic acid {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2- oxo-oxazolidin-5 (S)-ylmethyl}-amide, EXAMPLE 467: N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- <BR> <BR> [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-thioacetamide, EXAMPLE 468: AT-f3- [3-fluoro-4- (S-thioxo-5, 6-dihydro-4H- <BR> <BR> [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-thioacetamide, EXAMPLE 469: N-f3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-acetamide, EXAMPLE 470: N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5- ylmethyl}-3- (4-hydroxy-phenyl)-acrylamide, EXAMPLE 471: N- {3- [4- (6, 6-dimethyl-5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-3-fluoro-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 472 : N- {3- [3-fluoro-4- (6-ethyl-5-oxo-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 473: N- {3- [3-fluoro-4- (9-oxo-5-thia-7, 8-diaza- spiro [3.5] non-6-en-6-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-acetamide, EXAMPLE 474: N- {3- [3-fluoro-4- (5-oxo-6-phenyl-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 475 : N-13- [3-fluoro-4- (5-oxo-5, 6-dihydro-4-H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-2-hydroxy-acetamide, EXAMPLE 476 : N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) -<BR> ylmethyl}-3-oxo-butyramide, EXAMPLE 477: N- 3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S) - ylmethyl}-3- (4-fluoro-phenyl)-3-oxo-propionamide, EXAMPLE 478: N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl) -phenyl] -2-oxo-oxazolidin-5 (S)-<BR> ylmethyl}-3- [4- (hydroxyimino-methyl)-phenyl]-acrylamide, EXAMPLE 479: N- {3- [3-fluoro-4- (5-oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl) -phenyl] -2-oxo-oxazolidin-5 (S)-<BR> ylmethyl}-3- [4- (methoxyimino-methyl)-phenyl]-acrylamide, EXAMPLE 480: N-f3- [4- (6, 6-dimethyl-1, 1, 5-trioxo-1, 4,5, 6- tetrahydro-186- [1, 3,4] thiadiazin-2-yl)-3-fluoro-phenyl]-2- oxo-oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 481: N- {3- [3-fluoro-4- (4-methyl-5-oxo-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 482: N- 3- [3-fluoro-4- (5-oxo-6-propyl-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 483: N-f3- [3-fluoro-4- (6-isopropyl-5-oxo-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 484: N- {3- [3-fluoro-4- (6-fluoro-5-oxo-5, 6- dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 485: N- {3- [3-fluoro-4- (6-hydroxymethyl-5-oxo- 5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 486: N- {3- [3-fluoro-4- (6- (2-hydroxy-ethyl)-5- oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl)-phenyl]-2-oxo- oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 487: N- (3-3-fluoro-4- (6- (4-hydroxy-phenyl)-5- oxo-5, 6-dihydro-4H- [1, 3,4] thiadiazin-2-yl]-phenyl}-2-oxo- oxazolidin-5 (S)-ylmethyl)-acetamide, EXAMPLE 488: N-13- [4- (6, 6-dimethyl-1, 5-dioxo-1, 4,5, 6- tetrahydro-184- [1, 3, 4]-thiadiazin-2-yl)-3-fluoro-phenyl]- 2-oxo-oxazolidin-5 (S)-ylmethyl}-acetamide, EXAMPLE 489: N- [ [ (5S)-3- [4- (3, 4-dihydro-2H-thiopyran-4- yl) -3-fluorophenyl] -2-oxo-5-oxazolidinyl] methyl] -2, 2,2- trifluoroacetamide, EXAMPLE 490: N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4- yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 491: N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4- yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 492: N- [ [ (5S)-3- [4- (3, 4-dihydro-l-oxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 493: N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 494: N- [ [ (5S)-3- [4- (3, 4-dihydro-l-oxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 495: N- [ [ (5S)-3- [4- (2, 3-dihydro-1, 1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 496: N- [ [ (5S)-3- [4- (2, 3-dihydro-l, l-dioxido-4H- 1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 497: N- [ [ (SS)-3- [4- (3, 4-dihydro-1, 1-dioxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl]-2, 2-difluoroacetamide, EXAMPLE 498: N-[[(5S)-3-[4-(3,4-dihydro-l,l-dioxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] -2, 2-difluoroethanethioamide,<BR> EXAMPLE 499: 2,2-Dichloro-N- [[(5S)-3-[4-(3,4-dihydro- 1, 1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 500: N- [ [ (5S)-3- [4- (3, 4-dihydro-4-hydroxy-1, 1- dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oXo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 501: N-[[(5S)-3-[3-Fluoro-4-(4-fluoro-3,4- dihydro-1, 1-dioxido-2H-thiopyran-4-yl) phenyl]-2-oXo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 502: N-[[5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 503: N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-2, 2- difluoroacetamide, EXAMPLE 504: 2,2-dichloro-N- [[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 505: [ [ (55)-3- [4- (3, 4-dihydro-l, l-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-2, 2- difluoroethanethioamide, EXAMPLE 506: N- [ [ (5S)-3- [4- (3, 4-dihydro-1, 1-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] propionamide, EXAMPLE 507: N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl) -3, 5-difluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 508: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] -2, 2-difluoroethanethioamide, EXAMPLE 509: 2, 2-dichloro-N- [ [ (5S)-3- [4- (2, 3-dihydro- 1, 1-dioxido-4H-1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 510: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] -2, 2-difluoroacetamide, EXAMPLE 511: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl- 2,2-difluoroethanethioamide, EXAMPLE 512: 2,2-dichloro-N- [[(5S)-3-[4-(2,3-dihydro- 1, 1-dioxido-4H-1, 4-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 513: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl] - 2,2-difluoroacetamide, EXAMPLE 514 : N-[[(5S)-3-[4-(2,3-Dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2-oxo-5-<BR> oxazolidinyl] methyl]-2, 2-difluoroethanethioamide, EXAMPLE 515: 2, 2-dichloro-N- [ [ (SS)-3- [4- (2, 3-dihydro- 1, 1-dioxido-4H-1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2- oxo-5-oxazolidinyl] methyl] acetamide, or EXAMPLE 516: N- [ [ (5S)-3- [4- (2, 3-dihydro-1, 1-dioxido-4H- 1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2-oxo-5- oxazolidinyl] methyl]-2, 2-difluoroacetamide.

EXAMPLE 517: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 518: 2,2-dichloro-N- [[(5S)-3-[4-(3,4-dihydro- 1, 1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oXo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 519: 2,2-dichloro-N- [[(5S)-3-[4-(3,4-dihydro- 1, 1-dioxido-2H-thiopyran-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 520: 2,2-dichloro-N- [[(5S)-3-[4-(2,3-dihydro- 1, 1-dioxido-4H-1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 521: 2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro- 1, 1-dioxido-4H-1, 4-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 522: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 523: N- [ [ (5S)-3- [4- (3, 4-dihydro-1, 1-dioxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] -2, 2-difluoroacetamide, EXAMPLE 524: N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl]-2, 2-difluoroethanethioamide, EXAMPLE 525: N- [ [ (SS)-3- [4- (3, 4-dihydro-1, 1-dioxido-2H- thiopyran-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-2, 2- difluoroacetamide, EXAMPLE 526: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl]-2, 2-difluoroethanethioamide, EXAMPLE 527: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl]-2, 2-difluoroacetamide, EXAMPLE 528: N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H- 1, 4-thiazin-4-yl) phenyl]-2-oxo-5-oxazolidinyl] methyl- 2,2-difluoroethanethioamide, or EXAMPLE 529: 2,2-dichloro-N- [[(5S)-3-[4-(2,3-dihydro-<BR> 1, 1-dioxido-4H-1, 4-thiazin-4-yl) -3, 5-difluorophenyl]-2- oxo-5-oxazolidinyl] methyl] acetamide, EXAMPLE 530: (S)-N- [ [3- [3-fluoro-4- (1, 2,3, 4,6, 7- hexahydro-5-oxo-1, 4-diazepin-1-yl) phenyl]-2- oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 531: (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7- hexahydro-5-oxo-1, 4-diazepin-1-yl) phenyl]-2- oxo-5- oxazolidinyl] methyl] thioacetamide, EXAMPLE 532: (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7- hexahydro-4-methyl-5-oxo-1, 4-diazepin-1-yl) phenyl]-2-oxo- 5-oxazolidinyl] methyl] acetamide, or EXAMPLE 533: (S)-N- [ [3- [3-fluoro-9- (1, 2,3, 4,6, 7- hexahydro-4-methyl-5-oxo-1, 4-diazepin-1-yl) phenyl]-2-oxo- 5-oxazolidinyl] methyl] thioacetamide, EXAMPLE 534: N-[[(5S)-3-[3-fluoro-4-[tetrahydro-1,1- dioxido-2- (2-propenyl)-2H-1, 2-thiazin-4-yl] phenyl]-2-oxo- 5-oxazolidinyl] methyl] acetamide, EXAMPLE 535: N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1- dioxido-2H-1, 2-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 536: N- [[(5S)-3-[3-fluoro-4-(tetrahydro-1,1- dioxido-2H-1, 2-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 537: N- [ [ (5S)-3- [-fluoro-4- (tetrahydro-2-methyl- 1, 1-dioxido-2H-1, 2-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 538: N-[[(5S)-3-[4-(2,2-dioxido-1,2-oxathian-5- yl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 539: N-[[(5S)-3-[4-(1,1-dioxido-4- isothiazolidinyl)-3-fluorophenyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, or EXAMPLE 540: N- [ [ (5 S)-3- [3-fluoro-4- (tetrahydro-2- methyl-1, 1-dioxido-2H-1, 2-thiazin-4-yl) phenyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 541: N- (5S)-3-[(2R)-1-(2-fluoroethyl)-2- methyl-2, 3-dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 542: N- ( [ (5S)-3- ( (2R)-l-glycoloyl-2-methyl-2, 3- dihydro-lH-indol-5-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl) acetamide, EXAMPLE 543: N-({(5S)-3-[(2R)-1-glycoloyl-2-methyl-2, 3- dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 544 : N-({(5S)-3-[(2R)-1-formyl-2-methyl-2, 3- dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 545: N-({(5S)-3-[(2R)-1-formyl-2-methyl-2,3- dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5- yl}methyl)propanamide, EXAMPLE 546: N-({(5S)-3-[(2R)-1-formyl-2-methyl-2, 3- dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5- yl} methyl) ethanethioamide, EXAMPLE 547: N-({(5S)-3-[(2R)-1-(2-methoxyacetyl)-2- methyl-2, 3-dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 548: N-({(5S)-3-[(2R)-1-acetyl-2-methyl-2, 3- dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 549: N-[((5S)-3-{(2R)-2-methyl-1- [ (methylamino) carbothioyl] -2, 3-dihydro-lH-indol-5-yl}-2- oxo-1,3-oxazolidin-5-yl) methyl] acetamide, EXAMPLE 550: N-({(5S)-3-[(2R)-1-glycoloyl-2-methyl-2, 3- dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) ethanethioamide, EXAMPLE 551: N-{[(5S)-3-[(2R)-1-formyl-2-methyl-1, 2,3, 4- tetrahydro-6-quinolinyl]-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 552: N-{[(5S)-3-[(2R)-1-glycoloyl-2-methyl- 1,2, 3, 4-tetrahydro-6-quinolinyl]-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 553: N-({(5S)-3-[(2R)-1-formyl-2-methyl-1, 2,3, 4- tetrahydro-6-quinolinyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 554: N-({(5S)-3-[(2R)-1-formyl-2-methyl-1, 2,3, 4- tetrahydro-6-quinolinyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) ethanethioamide, EXAMPLE 555: N-{[(5S)-3-[(3R) 4-Formyl-3-methyl-3,4- dihydro-2H-1, 4-benzoxazin-7-yl]-2-oxo-1, 3-oxazolidin-5- yl] methyl) acetamide, EXAMPLE 556: N-( {(5S) -3-[(3R)-4-Formyl-3-methyl-3,4- dihydro-2H-1, 4-benzoxazin-7-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 557: N-({(5S)-3-[(3R)-4-Formyl-3-methyl-3, 4- dihydro-2H-1, 4-benzoxazin-7-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) ethanethioamide, EXAMPLE 558: N-({(5S)-3-[(2R) 2-(fluoromethyl)-1-formyl- 2, 3-dihydro-lH-indol-5-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 559: N-f [ (5R)-3- (2 (+) -methyl-2, 3-dihydro-1- benzothien-5-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, or EXAMPLE 560: N-[[(5S)-3-[2-(1,1-dimethylethyl)-1-formyl- 2, 3-dihydro-lH-indol-5-yl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 561: N-f [ (5S)-3- (l-Methyl-2, 2-dioxo-2,3-dihydro- 1H-2,1-benzisothiazol-5-yl)-2-oxo-1,3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 562: N-({(5S)-3-[1-(2-Fluoroethyl)-2,2-dioxo- 2, 3-dihydro-lH-2, 1-benzisothiazol-5-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, EXAMPLE 563: N- ( { (5S)-3- [l- (2-Nitriloethyl)-2, 2-dioxo- 2, 3-dihydro-lH-2, 1-benzisothiazol-5-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, EXAMPLE 564: N-(((5S)-3-[1-(2-Methoxyethyl)-2,2-dioxo- 2, 3-dihydro-lH-2, 1-benzisothiazol-5-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, or EXAMPLE 565: N- ( { (5S)-3- [l- (2-Fluoroethyl)-2, 2-dioxo- 2, 3-dihydro-lH-2, 1-benzisothiazol-5-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) ethanethioamide, EXAMPLE 566: (-)-N-[[(5S)-3-[2-formyl-1,2,3,4- tetrahydro-6-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 567: (-)-N- [ [ (5S)-3- [2- [ (acetyloxy) acetyl] - 1,2, 3, 4-tetrahydro-6-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 568: (-)-N-[[(5S)-3-[2-[(hydroxy)acetyl]- 1,2, 3, 4-tetrahydro-6-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 569: (+)-N-[[(5S)-3-[2-formyl-1,2,3,4- tetrahydro-6-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, or EXAMPLE 570: (+)-N-[[(5S)-3-[2-[(hydroxy) acetyl]- 1,2, 3, 4-tetrahydro-6-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 571: (+)-N-[[(5S)-3-[2-formyl-1,2,3,4- tetrahydro-7-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, or EXAMPLE 572: (+)-N- [ [ (5S)-3- [2- [ (hydroxy) acetyl] - 1,2, 3, 4-tetrahydro-7-isoquinolinyl]-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 573: (-)-N- [ [ (5S)-3- (3, 4-dihydro-lH-2- benzopyran-6-yl)-2-oxo-5-oxazolidinyl] methyl] acetamide, EXAMPLE 574: (+)-N- [ [ (5S)-3- (3, 4-dihydro-lH-2- benzopyran-6-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 575: (-)-N-[[(5S)-3-(3,4-dihydro-1H-2- benzothiopyran-6-yl)-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 576: (+)-N-[[(5S)-3-(3,4-dihydro-1H-2- benzothiopyran-6-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, or EXAMPLE 577: (+)-N- [ [ (5S)-3- (3, 4-dihydro-2, 2-dioxido-lH- 2-benzothiopyran-6-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 578: (+)-N-[[(5S)-3-(3,4-dihydro-1H-2- benzopyran-7-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 579: (-)-N-[[(5S)-3-(3,4-dihydro-1H-2- benzothiopyran-7-yl)-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 580: (+)-N-[[(5S)-3-(3,4-dihydro-1H-2- benzothiopyran-7-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, EXAMPLE 581: (+)-N- [ [ (5S)-3- (3, 4-dihydro-2, 2-dioxido-lH- 2-benzothiopyran-7-yl)-2-oxo-5- oxazolidinyl] methyl] ethanethioamide, or EXAMPLE 582: N-[[(5S)-3-(3,4-dihydro-2-oxido-1H-2- benzothiopyran-7-yl)-2-oxo-5- oxazolidinyl] methyl] acetamide, EXAMPLE 583: N-I [ (5S)-3- (3-formyl-1, 2,4, 5-tetrahydro-lH- 3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 584: N-{[(5S)-3-(3-glycoloyl-1,2,4,5-tetrahydro- 1H-3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 585: N-{[(5S)-3-(3-glycoloyl-1,2,4,5-tetrahydro- 1H-3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} ethanethioamide, EXAMPLE 586: N-I [ (5S)-3- (3-acetyl-1, 2,4, 5-tetrahydro-lH- 3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl) acetamide, EXAMPLE 587: N-{[(5S)-3-(3-benzoyl-1,2,4,5-tetrahydro- 1H-3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 588: N- ( { (5S)-3- [3- (5-amino-1, 3,4-thiadiazol-2- yl) -1,2, 4, 5-tetrahydro-lH-3-benzazepin-7-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, EXAMPLE 589: N- ( { (5S)-3- [3- (methylsulfonyl)-1, 2,4, 5- tetrahydro-lH-3-benzazepin-7-yl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, EXAMPLE 590: N-({(5S)-3-[3-(5-methylthio-1,3,4- thiadiazol-2-yl) -1,2, 4, 5-tetrahydro-lH-3-benzazepin-7- yl]-2-oxo-1, 3-oxazolidin-5-yl} methyl) acetamide, EXAMPLE 591: N-({(5S)-3-[3-(5-methyl-1,3,4-thiadiazol-2- yl)-1, 2,4, 5-tetrahydro-lH-3-benzazepin-7-yl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, EXAMPLE 592: N- [ ( (5S)-3- {3- (phenyl) acetyl-1, 2,4, 5- tetrahydro-lH-3-benzazepin-7-yl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] acetamide, EXAMPLE 593: N- [ ( (5S)-3-13- [5- (formylamino)-1, 3,4- thiadiazol-2-yl] -1,2, 4, 5-tetrahydro-lH-3-benzazepin-7- yl}-2-oxo-1, 3-oxazolidin-5-yl) methyl] acetamide, EXAMPLE 594 : N- [5-(7-{(5S)-5-[(acetylamino) methyl]-2- oxo-1, 3-oxazolidin-3-yl}-1, 2,4, 5-tetrahydro-3H-3- benzazepin-3-yl)-1, 3,4-thiadiazol-2-yl]-2- hydroxyacetamide, EXAMPLE 595: N- [ ( (5S)-3- {3- [ (4-iodophenyl) acetyl]- 1, 2,4, 5-tetrahydro-lH-3-benzazepin-7-yl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] acetamide, EXAMPLE 596: N-[((5S)-3-{3-[(3- trifluoromethyl) phenyl) acetyl] -1, 2,4, 5-tetrahydro-lH-3- benzazepin-7-ylE-2-oxo-1, 3-oxazolidin-5- yl) methyl] acetamide, EXAMPLE 597: N-[((5S)-3-{3-[(4- trifluoromethyl) phenyl) acetyl] -1, 2,4, 5-tetrahydro-lH-3- benzazepin-7-yl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] acetamide, EXAMPLE 598: N- ( ( (5S)-2-oxo-3- [3- (5-oxopentanoyl)- 1, 2,4, 5-tetrahydro-lH-3-benzazepin-7-yl]-1, 3-oxazolidin- 5-yl} methyl) acetamide, EXAMPLE 599: N- ( ( (5S)-2-oxo-3- [3- (5-oxohexanoyl)- 1, 2,4, 5-tetrahydro-lH-3-benzazepin-7-yl]-1, 3-oxazolidin- 5-yl) methyl) acetamide, EXAMPLE 600: N-f [ (5S)-3- (2-formyl-1, 3,4, 5-tetrahydro-lH- 2-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 601: N-J [ (SS)-3- (2-glycoloyl-1, 3,4, 5-tetrahydro- 1H-3-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 602: N-{[(5S)-3-(2-acetyl-1,3,4,5-tetrahydro-1H- 2-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 603: 7-{(5S)-5-[(acetylamino) methyl]-2-oxo-1, 3- oxazolidin-3-yl}-N-phenyl-1, 3,4, 5-tetrahydro-2H-2- benzazepine-2-carboxamide, EXAMPLE 604: N-{[(5S)-3-(1-formyl-2,3,4,5-tetrahydro-1H- 1-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} acetamide, EXAMPLE 605: N- ( [ (5S)-3- (l-formyl-2, 3,4, 5-tetrahydro-lH- 1-benzazepin-7-yl)-2-oxo-1, 3-oxazolidin-5- yl] methyl} ethanethioamide, EXAMPLE 606: N- [ [ (5S)-2-oxo-3- (1, 2,4, 5-tetrahydro-3- benzothiepin-7-yl)- 5-oxazolidinyl] methyl] acetamide, EXAMPLE 607: N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3,3- dioxido-3-benzothiepin-7-yl)-5- oxazolidinyl] methyl] acetamide, EXAMPLE 608: N- [ [ (5S)-2-oxo-3- (1, 2,4, 5-tetrahydro-3- benzothiepin-7-yl)- 5-oxazolidinyl] methyl] ethanethioamide, EXAMPLE 609: N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3,3- dioxido-3-benzothiepin-7-yl)-5- oxazolidinyl] methyl] ethanethioamide EXAMPLE 610: N- ( { (55)-3- [3-fluoro-4- (l-imino-l-oxido-l, 4-thiazinan-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) ethanethioamide, EXAMPLE 611: N- (1 (5S)-3- [3-fluoro-4- (l-imino-l-oxido- 14, 4-thiazinan-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, EXAMPLE 612: N- ( (5S)-3- [3-fluoro-4- (l-imino-l-oxido-1 4-thiazinan-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl}methyl) cyclopropanecarbothioamide, EXAMPLE 613: N- ( { (5S)-3- [3-fluoro-4- (1-imino-1- oxidOhexahydro-1X4-thiopyran-4-yl) phenyl]-2-oXo-1, 3- oxazolidin-5-yl} methyl) acetamide (E)-isomer, EXAMPLE 614: N-({(5S)-3-[3-fluoro-4-(1-imino-1- oxidshexahydro-1X4-thiopyran-4-yl) phenyl]-2-oXo-1, 3- oxazolidin-5-yl} methyl) ethanethioamide (E)-isomer, EXAMPLE 615: N- ( { (5S)-3- [3-fluoro-4- (l-imino-l- oxidOhexahydro-1X4-thiopyran-4-yl) phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) propanethioamide (E)-isomer, EXAMPLE 616: N- ( { (5S)-3- [3-fluoro-4- (l-imino-l- oxidohexahydro-19-thiopyran-4-yl) phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) cyclopropanecarbothioamide (E)- isomer, EXAMPLE 617: N- ( ( (5S)-3- [3-fluoro-4- (l-imino-1- oxidohexahydro-1#4-thiopyran-4-yl)phenyl]-2-oxo-1,3- oxazolidin-5-yl} methyl) acetamide (Z)-isomer, EXAMPLE 618: N- ( { (5S)-3- [3-fluoro-4- (l-imino-l- oxidOhexahydro-1X4-thiopyran-4-yl) phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) ethanethioamide (Z)-isomer, EXAMPLE 619: N-(((5S)-3-[3-fluoro-4-(1-imino-1- oxidohexahydro-lX4-thiopyran-4-yl) phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) propanethioamide (Z)-isomer, EXAMPLE 620: N- ( { (5S)-3- [3-fluoro-4- (l-imino-l- oxidOhexahydro-1X4-thiopyran-4-yl) phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) cyclopropanethioamide (Z)-isomer, EXAMPLE 621: N-(((5S)-3-[3-fluoro-4-[1-(acetylimino)-1- oxidohexahydro-1X4-thiopyran-4-yl] phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) acetamide, Z-isomer EXAMPLE 622: N- (1 (5S)-3- [3-fluoro-4- [l- (methylimino)-l- oxidohexahydro-1#4-thiopyran-4-yl]phenyl]-2-oxo-1,3- oxazolidin-5-yl} methyl) propanethioamide, Z-isomer, EXAMPLE 623: N- ( { (5S)-3- [3-fluoro-4- [l- (acetylimino)-1- oxidohexahydro-1#4-thiopyran-4-yl]phenyl]-2-oxo-1,3- oxazolidin-5-yl} methyl) propanethioamide, Z-isomer, EXAMPLE 624: N-(((5S)-3-[3-fluoro-4-[1-(ethylimino)-1- oxidohexahydro-1#4-thiopyran-4-yl]phenyl]-2-oxo-1,3- oxazolidin-5-yl} methyl) propanethioamide, Z-isomer, EXAMPLE 625: N- (1 (5S)-3- [3-fluoro-4-fl- [(phenylmethyl) imino]-1-oxidohexahydro-1k4-thiopyran-4- yl] phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 626: N- (1 (5S)-3- [3-fluoro-4- [l- [ (3- phenylpropyl) imino]-1-oxidohexahydro-1X4-thiopyran-4- yl] phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 627: N- (1 (5S)-3- [3-fluoro-4- (l- {[(methylamino) carbonyl] imino}-1-oxidohexahydro-1X4- thiopyran-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 628: N- ( ( (55)-3- [3-fluoro-4- (l- [(methOxyCarbonyl) imino]-1-oxidohexahydro-1X4-thiopyran-4- yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 629: N- (1 (5S)-3- [3-fluoro-4- (l- [ [ (ethoxycarbonyl) methyl] imino]-1-oxidshexahydro-1X4- thiopyran-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 630: N-({(5S)-3-[3-fluoro-4-(1-{[[(4- nitrophenyl) amino] carbonyl] imino}-1-oxidohexahydro-1"- thiopyran-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 631: N- ( { (5S)-3- [3-fluoro-4- [1- [(aminocarbonyl) imino]-1-oxidohexahydro-1X4-thlopyran-4- yl] phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 632: N-({(5S)-3-[3-fluoro-9-[1- [ [ (aminocarbonyl) methyl] imino]-l-oxidohexahydro-l- thiopyran-4-yl] phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 633: N- (f (SS)-3- [3-fluoro-4- [l- [ (2- hydroxyethyl) imino]-l-oxidohexahydro-l-thiopyran-4- yl] phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, Z-isomer, EXAMPLE 634: N- [ ( (55)-3- {3-fluoro-4- [l- (methylimino)-l- oxido-1k4, 4-thiazinan-4-yl] phenyl}-2-oxo-1, 3-oxazolidin- 5-yl) methyl] propanethioamide, EXAMPLE 635: N- [ ( (5S)-3- {3-fluoro-4- [l- (methylimino)-l- oxido-1", 4-thiazinan-4-yl] phenyl}-2-oxo-l, 3-oxazolidin- 5-yl) methyl] cyclopropanecarbothioamide, EXAMPLE 636: N-[((5S)-3-{3-fluoro-4-(1- [(methoxycarbonyl) imino]-1-oxido-1k4, 4-thiazinan-4- yl) phenyl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] propanethioamide, EXAMPLE 637: N-[((5S)-3-{3-fluoro-4-(1- [(methoxyzarbonyl) imino]-1-oxido-1#4, 4-thiazinan-4- yl) phenyl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] cyclopropanecarbothioamide, EXAMPLE 638: N- (f (5S)-3- [3-fluoro-4- [l- (methylimino)-l- oxidohexahydro-1X4-thiopyran-4-yl] phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) cyclopropanecarbothioamide, Z- isomer, EXAMPLE 639: N- [ ( (5S)-3-13-fluoro-4- [l- <BR> <BR> [(methoxyCarbonyl) imino]-1-oxidohexahydro-1X4-thiopyran-4- yl] phenyl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] cyclopropanecarbothioamide, Z-isomer, EXAMPLE 640: N- [ ( (5S)-3- {3-fluoro-4- [1- (methylimino)-1- oxidOhexahydro-1x4-thiopyran-4-yl] phenyl}-2-oXo-1, 3- oxazolidin-5-yl) methyl] cyclopropanecarbothioamide, E- isomer, EXAMPLE 641: N- [ ( (5S)-3-13-fluoro-4- [l- (methylimino)-l- oxidohexahydro-lk4-thiopyran-4-yl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, E-isomer, EXAMPLE 642: N- [ ( (5S)-3-13-fluoro-4- [l- [[(phenylmethoxy) carbnonyl] imino]-1-oxidohexahydro-1X4- thiopyran-4-yl] phenyl}-2-oxo-1, 3-oxazolidin-5- yl) methyl] acetamide, Z-isomer, EXAMPLE 643: N- ( { (5S)-3- [3-Fluoro-4- (l- {[(benzylamino) carbonyl] imino}-1-oxidohexahydro-1X4- thiopyran-4-yl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) acetamide, Z-isomer, EXAMPLE 644 : N { [ (5S)-3- (3-fluoro-4- {4- [2- (methylsulfinyl) acetyl]-1-piperazinyl} phenyl)-2-oxo-1, 3- oxazolidin-5-yl] methyl} propanethioamide, EXAMPLE 645: N-{[(5S)-3-(3-fluoro-4-{4-[2- (methylsulfanyl) acetyl]-1-piperazinyl} phenyl)-2-oxo-1, 3- oxazolidin-5-yl] methyl} propanethioamide, EXAMPLE 646: N-{[(5S)-3-(3-fluoro-4-{4-[2- (methylsulfonyl) acetyl]-1-piperazinyl} phenyl]-2-oxo-1, 3- oxazolidin-5-yl] methyl} propanethioamide, EXAMPLE 647: N- ( ( (5S)-3- [4- (4-ethanethiolyl-1- piperazinyl)-3-fluorophenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, EXAMPLE 648: N- ( ( (5S)-3- [4- (4-cyano-l-piperazinyl)-3- fluorophenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, EXAMPLE 649: N-({(5S)-3-(3-fluoro-4-{4-[2- (methylaminocarbonyloxy) acetyl]-1-piperazinyl} phenyl)-2- oxo-1, 3-oxazolidin-5-yl} methyl) propanethioamide, EXAMPLE 650: N- ( { (5S)-3- (3-fluoro-4- {4- [2- [ (2- methoxyethoxy) carbonyloxy] acetyl]-1-piperazinyl} phenyl) - 2-oxo-1, 3-oxazolidin-5-yl} methyl) propanethioamide, EXAMPLE 651: N-[((5S)-3-{3-fluoro-4-[4-((2S)-2-hydroxy- 3-methoxypropanoyl)-1-piperazinyl] phenyl}-2-oXo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 652: N-[((5S)-3-{3-fluoro-4-[4-((2S)-2,3- dimethyoxypropanoyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 653: N-[((5S)-3-{3-fluoro-4-[4-((2S)-3-hydroxy- 2-methyoxypropanoyl)-1-piperazinyl] phenyl)-2-oxo-1, 3- oxazolidin-5-yl)methyl]propanethioamide, EXAMPLE 654: N-({(5S)-3-[3-fluoro-4-(4-acetoacetyl-1- piperazinyl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, EXAMPLE 655: N- ( { (5S)-3- [3-fluoro-4- (4-pyruvoyl-l- piperazinyl) phenyl]-2-oxo-1, 3-oxazolidin-5- yl} methyl) propanethioamide, EXAMPLE 656: N- ( { (5S)-3- [3-fluoro-4- [4- (3- hydroxypropanoyl)-1-piperazinyl] phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl] propanethioamide, EXAMPLE 657: N- { [ (5S)-3- (3-fluoro-4- {4- [ (1- hydroxycyclopropyl) carbonyl]-l-piperazinyl} phenyl)-2-oxo- 1, 3-oxazolidin-5-yl] methyl} propanethioamide, EXAMPLE 658: N- [ ( (5S)-3- (3-fluoro-4- [4- (2- phenoxyacetyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 659: N- ( { (5S)-3- [3-fluoro-4- [4- ( (2S)-2, 3- dihydroxypropanoyl)-1-piperazinyl] phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) propanethioamide, EXAMPLE 660: N- (f (5S)-3- [3-fluoro-4- [4- ( (2R)-2, 3- dihydroxypropanoyl)-1-piperazinyl] phenyl]-2-oxo-1, 3- oxazolidin-5-yl} methyl) propanethioamide, EXAMPLE 661: N-{[(5S)-3-(3-fluoro-4-{4-[3-hydroxy-2- (hydroxymethyl)-2-methylpropanoyl]-1-piperazinyl} phenyl)-<BR> 2-oxo-1, 3-oxazolidin-5-yl] methyl} propanethioamide, EXAMPLE 662: N- [ ( (5S)-3- {3-fluoro-4- [4- ( (2S)-2-hydroxy- 3-phenylpropanoyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 663: N- [ ( (5S)-3-i3-fluoro-4- [4- ( (2R)-2-hydroxy- 3-phenylpropanoyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 664: N- [ ( (5S)-3-f3-fluoro-4- [4- ( (2R)-2-hydroxy- 2-phenylacetyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide, EXAMPLE 665: N- [ ( (5S)-3-13-fluoro-4- [4- ( (2S)-2-acetoxy- 2-phenylacetyl)-1-piperazinyl] phenyl}-2-oxo-1, 3- oxazolidin-5-yl) methyl] propanethioamide.

In order to more fully illustrate the nature of the invention and the manner of practicing the same, the following synthesis Example is presented.

SYNTHESIS EXAMPLE 2- {3- [Acetyl ( { (5S)-3- [4- (l, l-dioxidotetrahydro-2H- thiopyran-4-yl)-3-fluorophenyl]-2-oxo-1, 3-oxazolidin 5- yl} methyl) amino]-1, 1-dimethyl-3-oxopropyl}-3t5- dimethylphenyl dihydrogen phosphate.

Step 1.

A stirred mixture of 2 (0.57 g, 1.18 mmol) (M. G.

Nicolaou, C. -S. Yuan and R. T. Borchardt, J. Org. Chem.

1996, 61, 8636-8641), 3 (0.45 g, 1.19 mmol) (Case 6118. N CN1, Example 11, Step 1) and triethylamine (0.8 ml) in CH2Cl2 (60 ml), under nitrogen was cooled in an ice bath and treated with bis (2-oxo-3-oxazolidinyl) phosphinic chloride (0.456 g, 1.79 mmol). It was kept in the ice 0 bath for 45 min and at ambient temperature (24 C) for 2 h 15 min and then concentrated in vacuo. The residue was mixed with EtOAc and washed with 5% aqueous citric acid and brine, dried (MgSO) and concentrated. Chromatography of the residue on silica gel with 2. 5% MeOH-CH2Clz gave 0.88 g of 4 : 1H NMR (300 MHz, CDC13) 8 1.61, 1.65 (s, s, 6H), 2.08 (s, 3H), 2.15 (m, 2H), 2.37 (m, 2H), 2.48 (s, 3H), 2.56 (m, 2H), 3.13 (m, 6H), 3.35 (m, 3H), 4.28 (m, 1H), 5.12 (m, 4H), 6.66 (s, 1H), 6.98 (s, 1H), 7.13 (m, 3H), 7.36 (m, 11H) ; MS (ESI) m/z 807 (M+H+), 829 (M+Na+).

Step 2.

A stirred solution of 4 (0.85 g, 1.05 mmol) in methyl trimethylsilylcarbamate (3 ml), under nitrogen was treated, dropwise with acetyl chloride (0.25 ml, 3.5 mmol) and kept at ambient temperature (24°C) for 3.5 h.

It was then diluted with pentane to give a gum. The liquid was decanted and the residue was trituratred twice with pentane and once with Et20 to give a semisolid material that was chromatographed on silica gel with 30% EtOAc-CH2Cl2. The product amounted to 0.62 g of 5 : 1H NMR (300 MHz, CDC13) b 1.55 (s, 3H), 1.62 (s, 3H), 2.16 (s, 3H), 2.20 (m, 1H), 2.23 (s, 3H), 2.42 (m, 2H), 2.57 (s, 3H), 3. 17 (m, 5H), 3.52 (m, 5H), 3.87 (m, 2H), 4.61 (m, 1H), 5.05 (m, 4H), 6.79 (s, 1H), 6.98 (s, 1H), 7.11 (dd, 1H), 7.28 (m, 11H), 7.42 (dd, 1H) ; HRMS (FAB) calcd for C44H51FN2OloPS (M+H+), 849.2986, found 849.2988.

Step 3.

A mixture of 5 (0.62 g), 10% palladium-on-carbon catalyst (0.16 g) and THF (20 ml) was hydrogenated at atmospheric pressure for 80 min, filtered through celite and concentrated in vacuo. The resulting foam was triturated with Et20 to give 0.419 g of 1, a white powder: mp 116- 124OC (dec) ; MS (ESI) m/z 627 (M+H+), 649 (M+Na+) ; HRMS (FAB) calcd for C28H37FN2OsPS (M+H+) 627.1941, found 627.1947.

Although the present invention has been exemplified using oxazolidinone compounds, it is understood that any amide-containing compound can be made more water-soluble using the present invention. Moreover, although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity and understanding, it would be apparent to those skilled in the art that certain changes and modifications could be made without departing from the scope and spirit of the present invention. As such, the description and example should not be construed as limiting the scope of the invention.