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Title:
DEFORMYLASE INHIBITOR, PROCESS FOR PREPARING THE SAME, AND ANTIBACTERIAL COMPOSITION COMPRISING THE SAME
Document Type and Number:
WIPO Patent Application WO/2004/087643
Kind Code:
A1
Abstract:
Provided are a novel compound useful for a deformylase inhibitor with excellent antibacterial activity or a pharmaceutically acceptable salt thereof, a process for preparing the same, and an antibacterial composition including the same as an active ingredient. The deformylase inhibitor effectively acts against a broad spectrum of bacteria, including bacteria with resistance to existing antibacterial agents.

Inventors:
LEE BONG-JIN (KR)
LEE SEUNG-KYU (KR)
CHOI KWANG-HYUN (KR)
LEE SANG-JAE (KR)
Application Number:
PCT/KR2004/000502
Publication Date:
October 14, 2004
Filing Date:
March 11, 2004
Export Citation:
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Assignee:
PROMEDITECH INC (KR)
LEE BONG-JIN (KR)
LEE SEUNG-KYU (KR)
CHOI KWANG-HYUN (KR)
LEE SANG-JAE (KR)
International Classes:
C07C239/16; C07C275/28; C07C275/30; C07C275/34; C07C275/38; C07C275/42; C07D295/135; C07K5/06; C07K5/062; (IPC1-7): C07C275/28
Domestic Patent References:
WO2001044178A12001-06-21
WO1999039704A11999-08-12
WO1994010990A11994-05-26
Foreign References:
Other References:
ZHENGYU YUAN ET AL.: "Deformylase as a novel antibacterial target", DRUG DISCOVERY TODAY, vol. 6, no. 18, 15 September 2001 (2001-09-15), pages 954 - 961, XP002904381
Attorney, Agent or Firm:
Lee, Young-pil (1571-18 Seocho-dong Seocho-gu, Seoul 137-874, KR)
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Claims:
Claims
1. A compound of formula (I) or a pharmaceutically acceptable salt thereof: Wherein, R¹ is a straight or branched C1 ~ C6 alkyl group; or a C1 ~ C2 alkyl substituted with a C3 ~ C6 cycloalkyl group, R2 is a straight or branched C1 ~ C6 alkyl group, X is a phenyl group; or a heteroaryl group selected from the group consisting of 1,4benzodioxolyl, pyridinyl, quinolinyl, and benzothiazolyl (wherein, the phenyl group or the heteroaryl group may be substituted with 1 to 3 substituent (s) selected from the group aDnsiting of C1 ~ C4 alkyl, C1 ~ C4 alkoxy, hydroxy, halogen, cyano, nitro, acetyl, phenyl, trifluoromethyl, trifluoromethoxy, methanesulfonyl, piperidinyl, morpholinyl, pyrrolidinyl, and benzoyl).
2. 5 A process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, which comprises reacting a compound of formula (II) with hydroxyl amine: [2] The compound of formula (I) or its pharmaceutically acceptable salt of claim 1, wherein X is a phenyl group substituted with 1 to 3 substituent (s) selected from the group consiting of C1 ~ C4 alkyl, C1 ~ C4 alkoxy, hydroxy, halogen, cyano, nitro, acetyl, phenyl, trifluoromethyl, trifluoromethoxy, methanesulfonyl, piperidinyl, morpholinyl, pyrrolidinyl, and benzoyl.
3. The compound of formula (I) or its pharmaceutically acceptable salt of claim 1, wherein X is a heteroaryl group selected from the group consisting of 1,4benzodioxolyl, pyridinyl, quinolinyl, and benzothiazolyl, which may be substituted with 1 or 2 substituent (s) selected from the group consiting of C ~ C alkyl, C ~ C alkoxy, and halogen.
4. 14 [4] The compound of formula (I) or its pharmaceutically acceptable salt of claim 1, which is selected from the group consisting of: 1((S)1(N((hydroxycarbamoyl) methyl) Nbutylcarbamoyl) 2, 2dimethylpropy 1)3(3chlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3(3chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3ptolylurea ; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3mtolylurea ; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (3methoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl) 3mtolylurea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclohexylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3chlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclohexylmethyl) carbamoyl) 2,2 dimethylpropyl) 3mtolylurea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclohexylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3methoxyphenyl) urea 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (biphenyl4yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(3syanophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3(3chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl) 3ptolylurea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl) 3mtolylurea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (3methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(4syanophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3fluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2fluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (4fluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2nitrophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3nitrophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 3dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3, 4dichlorophenyl) urea 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (4nitrophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (4acetylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (4 (trifluoromethoxy) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (benzo [d] [1, 3] dioxol5yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (2, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (3, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (2methoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (4 (trifluoromethyl) phenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2ethylphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2ethoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3, 4difluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3, 5difluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 5difluorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (3chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2fluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2, 4difluorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (3, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 5difluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (2, 5difluorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (3, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2, 5difluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(2methoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(2, 4dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(2, 5dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(2, 5difluorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(5chloro2methoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2 (trifluoromethoxy) phenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2 methylbutyl)3 (2, 5dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 3 methylbutyl)3 (2, 5dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 5dichlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 4dichlorophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (2chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2 methylpropyl)3(5chloro2methoxyphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 5dimethoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2methoxy5methylphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2methoxy5methylphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2, 4dimethoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (2, 4dimethoxyphenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2chloropyridin3yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2benzoyl3chlorophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (benzo [d] thiazol6yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(2(piperidin1yl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (5 (trifluoromethyl)2morpholinophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(3chloro4morpholinophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (quinolin5yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(2(pyrrolidin1yl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (5fluoro2 (pyrrolidinlyl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (5fluoro2 (piperidin1yl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (5fluoro2morpholinophenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3fluoro4 (pyrrolidinlyl) phenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3fluoro4 (piperidin1yl) phenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (3fluoro4morpholinophenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3(5chloroquinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2chloro4 (methylsulfonyl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (5fluoro2 (pyrrolidinlyl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3(4chloro2methoxy5meth6ylphenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl) 2, 2dimethylpr opyl)3 (quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3 (5fluoro2 (pyrrolidin1yl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2,2 dimethylpropyl)3(quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (5fluoro2 (pyrrolidinlyl) phenyl) urea 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (5fluoro2 (pyrrolidinlyl) phenyl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclopentylmethyl) carbamoyl) 2 methylpropyl)3 (quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl) methyl) Nisopentylcarbamoyl)2methylpropy 1)3(quinolin8yl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2 methylpropyl)3(4chloro2methoxy5methylphenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2 methylpropyl)3 (5fluoro2 (pyrrolidinlyl) phenyl) urea; 1((S)1(N((hydroxycarbamoyl)methyl)N(2cyclopentylethyl) carbamoyl) 2 methylpropyl)3 (quinolin8yl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (6methoxyquinolin8yl) urea; 1((S)l(N((hydroxyCarbamoyl) methyl)N(cyclobutylmethyl) carbamoyl) 2m ethylpropyl)3 (6methoxyquinolin8yl) urea; and 1((S)1(N((hydroxycarbamoyl)methyl)N(cyclobutylmethyl) carbamoyl) 2,2 dimethylpropyl)3 (2hydroxyphenyl) urea.
5. A process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, which comprises reacting a compound of formula (II) with hydroxyl amine: Wherein, R1, R2, and X are the same as defined in claim 1 and R3 is C # C 1 4 alkyl.
6. The process of claim 5, wherein the compound of formula (II) is obtained by reacting a compound of formula (III) or its salt with O=C=NX : wherein, R1, R2, and X are the same as defined in claim 1 and R3 is C # C alkyl.
7. 1 4 [7] The process of claim 5, wherein the compound of formula (II) is obtained by a process comprising reacting a compound of formula (III) or its salt with triphosgen or 1,1'carbonyldiimidazole to obtain a compound of formula (IV); and then reacting the a compound of formula (IV) with NHX: wherein, R1, R2, and X are the same as defined in claim 1, R3 is C1 # C4 alkyl, and R4 is chloro or imidazole.
8. The process of Claims 6 or 7, wherein the compound of formula (III) or its salt is obtained by a process comprising (a) reacting a compound of formula (V) with a compound of formula (VI); and then (b) deprotecting the product of Step (a): wherein, R and R are the same as defined in claim 1, R isCC alkyl, andR 1 4 is a amino protecting group.
9. The process of Claim 8, wherein the compound of formula (V) is obtained by reacting a compound of formula (VII) or its salt with a compound of formula (VIII) in the presence of a base: wherein, R is the same as defined in claim 1, R isCC alkyl, and Z is 1 4 chloro, ptolunesulfonyl, or methanesulfonyl.
10. An antibacterial composition comprising a therapeutically effective amount of the compound of formula (I) or its pharmaceutically acceptable salt of any one of claims 1 to 4 and a pharmaceutically acceptable carrier.
Description:
Description DEFORMYLASE INHIBITOR, PROCESS FOR PREPARING THE SAME, AND ANTIBACTERIAL COMPOSITION COMPRISING THE SAME Technical Field [1] The present invention relates to a novel compound useful for a deformylase inhibitor, and more particularly, to a novel compound useful for a deformylase inhibitor with excellent antibacterial activity or a pharmaceutically acceptable salt thereof, a process for preparing the same, and an antibacterial composition comprising the same as an active ingredient.

Background Art [2] Deformylase is metallopeptidase found in prokaryotes such as bacteria. In prokaryotes, protein synthesis is initiated with N-formyl methionine (fMet). The formyl group is removed by deformylase before a protein reaches its mature form.

Since such deformylation is a prerequisite for protein maturation, it is known that de- formylase is essential for bacterial growth (Chang et al., J. Bacteriol. 171 : 4071-4072 (1989); Meinnel T, Blanquet S, J. Bacteriol. 176 (23): 7387-90 (1994); Mazel D et. al., EMBO J. 13 (4): 914-23 (1994)). However, fMet is not a requisite for initiation of eukaryotic protein synthesis, and thus, deformylase inhibitors can be ef- fectively used as antibacterial agents with broad-spectrum.

[3] Deformylase inhibitors are disclosed in WO 02/102791 (pyrrolidine bicyclic derivatives), WO 02/102790 (N-formyl hydroxyl amine derivatives), WO 01/44179 (susdnate derivatives), WO 01/44178 (urea derivatives), and WO 01/85170 (petide derivatives).

[4] HDwever, development of novel deformylase inhibitors which are active against a broad spectrum of bacteria, including bacteria with resistance to existing antibacterial agents, is still required.

Disclosure of Invention [5] The present invention provides a novel compound useful for a deformylase inhibitor with multi-polypeptide bonds and a process for preparing the same. The present invention also provides an antibacterial composition comprising the compound as an active ingredient.

[6] In one aspect of the present invention, there is provided a compound of formula (I) or a pharmaceutically acceptable salt thereof: [7] wherein, R is a straight or branched C-C alkyl group; or a C-C alkyl 1 6 1 2 substituted with a C ~ C cycloalkyl group, 3 6 [8] R2 is a straight or branched C1 # C6 alkyl group, [9] X is a phenyl group; or a heteroaryl group selected from the group consisting of 1,4-benzodioxolyl, pyridinyl, quinolinyl, and benzothiazolyl (wherein, the phenyl group or the heteroaryl group may be substituted with 1 to 3 substituent (s) selected from the group aDnsiting of C C alkyl, C-C alkoxy, hydroxy, halogen, cyano, 4 1 4 nitro, acetyl, phenyl, trifluoromethyl, trifluoromethoxy, methanesulfonyl, piperidinyl, morpholinyl, pyrrolidinyl, and benzoyl).

[10] In another aspect of the present invention, there is provided a process for preparing a compound of formula (I) or a pharmaceutically acceptable salt thereof, which comprises reacting a compound of formula (II) with hydroxyl amine: [11] wherein, R1, R2, and X are the same as defined above and R3 is C # C alkyl.

1 4 [12] In still another aspect of the present invention, there is provided an antibacterial composition comprising a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

Best Mode for Carrying Out the Invention [13] In one aspect of the present invention, there is provided a compound of formula (I) or a pharmaceutically acceptable salt thereof: [14] wherein, R is a straight or branched C ~ C alkyl group ; or a C ~ C alkyl 1 6 1 2 substituted with a C3 ~ C6 cycloalkyl group, [15] R2 is a straight or branched C1 ~ C6 alkyl group, [16] X is a phenyl group; or a heteroaryl group selected from the group consisting of 1,4-benzodioxolyl, pyridinyl, quinolinyl, and benzothiazolyl (wherein, the phenyl group or the heteroaryl group may be substituted with 1 to 3 substituent (s) selected from the group aDnsiting of C # C alkyl, C # C alkoxy, hydroxy, halogen, cyano, 1 4 1 4 nitro, acetyl, phenyl, trifluoromethyl, trifluoromethoxy, methanesulfonyl, piperidinyl, morpholinyl, pyrrolidinyl, and benzoyl).

[17] Among the compounds of the present invention, preferably X is a phenyl group substituted with 1 to 3 substituent (s) selected from the group aDnsiting of C ~ C 1 4 alkyl, C-C alkoxy, hydroxy, halogen, cyano, nitro, acetyl, phenyl, trifluoromethyl, 1 4 trifluoromethoxy, methanesulfonyl, piperidinyl, morpholinyl, pyrrolidinyl, and benzoyl.

[18] Further, among the compounds of the present invention, preferably X is a heteroaryl group selected from the group consisting of 1,4-benzodioxolyl, pyridinyl, quinolinyl, and benzothiazolyl, which may be substituted with 1 or 2 substituent (s) selected from the group consiting of C ~ C alkyl, C ~ C alkoxy, and halogen.

1 4 1 4 [19] More preferably, the compounds of formula (1) are : [20] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-butylcarbamoyl) -2, 2-dimethylpropyl)- 3- (3-chlorophenyl) urea; [21] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-chlorophenyl) urea; [22] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-chlorophenyl) urea; [23] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl) -3-p-tolylurea; [24] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl) -3-m-tolylurea; [25] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-methoxyphenyl) urea; [26] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl) -3-m-tolylurea; [27] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-chlorophenyl) urea; [28] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-di methylpropyl) -3-m-tolylurea; [29] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-methoxyphenyl) urea [30] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (biphenyl-4-yl) urea; [31] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-methoxyphenyl) urea; [32] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-chlorophenyl) urea; [33] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(3syanophenyl) urea; [34] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3-(3-chlorophenyl) urea; [35] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl) -3-p-tolylurea; [36] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl) -3-m-tolylurea; [37] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (3-methoxyphenyl) urea; [38] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(4syanophenyl) urea; [39] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-fluorophenyl) urea; [40] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-fluorophenyl) urea; [41] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (4-fluorophenyl) urea; [42] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-nitrophenyl) urea; [43] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-nitrophenyl) urea; [44] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 3-dichlorophenyl) urea; [45] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 4-dichlorophenyl) urea; [46] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 5-dichlorophenyl) urea; [47] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3, 4-dichlorophenyl) urea [48] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3, 5-dichlorophenyl) urea; [49] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (4-nitrophenyl) urea; [50] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (4-acetylphenyl) urea; [51] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (4- (trifluoromethoxy) phenyl) urea; [52] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (benzo [d] [1, 3] dioxol-5-yl) urea; [53] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 4-dichlorophenyl) urea; [54] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 5-dichlorophenyl) urea; [55] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-methoxyphenyl) urea; [56] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (2, 4-dichlorophenyl) urea; [57] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (2, 5-dichlorophenyl) urea; [58] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (3, 4-dichlorophenyl) urea; [59] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (2-methoxyphenyl) urea; [60] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (4- (trifluoromethyl) phenyl) urea; [61] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-ethylphenyl) urea; [62] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-ethoxyphenyl) urea; [63] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3, 4-difluorophenyl) urea; [64] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3, 5-difluorophenyl) urea; [65] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2, 5-difluorophenyl) urea; [66] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (2-methoxyphenyl) urea; [67] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (2-chlorophenyl) urea; [68] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2-methoxyphenyl) urea; [69] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2-chlorophenyl) urea; [70] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2-methoxyphenyl) urea; [71] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2-chlorophenyl) urea; [72] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (3-chlorophenyl) urea; [73] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2, 4-dichlorophenyl) urea; [74] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2-fluorophenyl) urea; [75] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2, 4-difluorophenyl) urea; [76] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (2-methoxyphenyl) urea; [77] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (2-chlorophenyl) urea; [78] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (3, 4-dichlorophenyl) urea; [79] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (2, 4-dichlorophenyl) urea; [80] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (2, 5-dichlorophenyl) urea; [81] 1-((S)-l-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (2, 5-difluorophenyl) urea; [82] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (2, 4-dichlorophenyl) urea; [83] 1- ( (S)-l- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (2, 5-dichlorophenyl) urea; [84] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (2, 5-difluorophenyl) urea; [85] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (3, 4-dichlorophenyl) urea; [86] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2, 5-dichlorophenyl) urea; [87] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2, 5-difluorophenyl) urea; [88] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (2-methoxyphenyl) urea; [89] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (2-chlorophenyl) urea; [90] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (2, 4-dichlorophenyl) urea; [91] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (2, 5-dichlorophenyl) urea; [92] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (2, 5-difluorophenyl) urea; [93] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [94] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2- (trifluoromethoxy) phenyl) urea; [95] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylbutyl)-3- (2, 5-dichlorophenyl) urea; [96] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -3-met hylbutyl)-3- (2, 5-dichlorophenyl) urea; [97] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2, 5-dichlorophenyl) urea; [98] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2, 4-dichlorophenyl) urea; [99] 1-((S)-1-(N-((hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (2-chlorophenyl) urea; [100] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-chlorophenyl) urea; [101] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [102] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3-(5-chloro-2-methoxyphenyl) urea; <BR> <BR> <BR> <BR> [103] 1- ((S)-1- (N- ( droxycarbamoyl) methyl) -N- (2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [104] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [105] 1- ((S)-1- (N- ( droxycarbamoyl) methyl) -N- (cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [106] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3-(5-chloro-2-methoxyphenyl) urea; [107] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3-(5-chloro-2-methoxyphenyl) urea; [108] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2, 5-dimethoxyphenyl) urea; [109] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2-methoxy-5-methylphenyl) urea; [110] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2-methoxy-5-methylphenyl) urea; [111] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2, 4-dimethoxyphenyl) urea; [112] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (2, 4-dimethoxyphenyl) urea; [113] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-chloropyridin-3-yl) urea; [114] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [115] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-benzoyl-3-chlorophenyl) urea; [116] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (quinolin-8-yl) urea; [117] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (benzo [d] thiazol-6-yl) urea; [118] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(2-(piperidin-1-yl) phenyl) urea; [119] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (5- (trifluoromethyl)-2-morpholinophenyl) urea; [120] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(3-chloro-4-morpholinophenyl) urea; [121] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (quinolin-5-yl) urea; [122] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(2-(pyrrolidin-1-yl) phenyl) urea; [123] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(5-fluoro-2-(pyrrolidin-1-yl) phenyl) urea; [124] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (5-fluoro-2- (piperidin-1-yl) phenyl) urea; [125] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (5-fluoro-2-morpholinophenyl) urea; [126] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(3-fluoro-4-(pyrrolidin-1-yl) phenyl) urea; [127] 1- ((S)-1- (N- ( droxycarbamoyl) methyl) -N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-fluoro-4- (piperidin-1-yl) phenyl) urea; [128] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (3-fluoro-4-morpholinophenyl) urea; [129] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3-(5-chloroquinolin-8-yl) urea; [130] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl)-N- (cyclopentylmethyl) carbamoyl) -2,2-di methylpropyl)-3- (2-chloro-4- (methylsulfonyl) phenyl) urea; [131] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [132] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (5-fluoro-2- (pyrrolidin-l-yl) phenyl) urea; [133] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (quinolin-8-yl) urea; [134] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [135] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylprop yl)-3- (quinolin-8-yl) urea; [136] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [137] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3-(5-fluoro-2-(pyrrolidin-1-yl) phenyl) urea; [138] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2,2-di methylpropyl)-3- (quinolin-8-yl) urea; [139] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [140] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3-(5-fluoro-2-(pyrrolidin-1-yl) phenyl) urea [141] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (quinolin-8-yl) urea; [142] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea; [143] 1- ((S)-1- (N- ( droxycarbamoyl) methyl) -N- (cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (5-fluoro-2- (pyrrolidin-l-yl) phenyl) urea; [144] 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-met hylpropyl)-3- (quinolin-8-yl) urea; [145] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3-(4-chloro-2-methoxy-5-methylphenyl) urea; [146] 1- ( (S)-1- (N- ( (hydroxyrarbamoyl) methyl) -N-isopentylcarbamoyl)-2-methylpropyl)- 3- (quinolin-8-yl) urea; [147] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (4-chloro-2-methoxy-5-methylphenyl) urea; [148] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (5-fluoro-2- (pyrrolidin-l-yl) phenyl) urea; [149] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(2qclopentylethyl) carbamoyl) -2-met hylpropyl)-3- (quinolin-8-yl) urea; [150] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (6-methoxyquinolin-8-yl) urea; [151] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclobutylmethyl) carbamoyl) -2-meth ylpropyl)-3- (6-methoxyquinolin-8-yl) urea; and [152] 1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cwclobutylmethyl) carbamoyl) -2,2-dim ethylpropyl)-3- (2-hydroxyphenyl) urea.

[153] A compound of the present invention may be in the form of a pharmaceutically acceptable salt, hydrate (s), or solvate (s). The pharmaceutically acceptable salts which may be applied to a compound of the present invention include, but are not limited to, hydrochloride, hydrobromide, sulfate, methylsulfonate, p-tolunesulfonate, phosphate, acetate, citrate, sminate, lactate, tartarate, fumarate, malate, a sodium salt, a magnesium salt, and a calcium salt.

[154] A compound of the present invetnion may also be in the form of racemates or optical isomers due to presence of chiral centers. Therefore, a compound of the present invention includes both racemates and optical isomers.

[155] In accordance with another aspect of the present invention, there is provided a process for preparing the compound of formula (I) or its pharmaceutically acceptable salt. In other words, there is provided a process for preparing the compound of formula (I) or its pharmaceutically acceptable salt, which comprises reacting a compound of formula (II) with hydroxyl amine: [156] wherein, R, R, and X are the same as defined above and R is C-C alkyl.

1 4 [157] Reacting the compound of formula (II) with hydroxyl amine may be carried out in a lower alkanol solvent such as methanol and ethanol at room temperature for about 3 to 6 hours.

[158] The compound of formula (II) may be obtained by reacting a compound of formula (III) or its salt (e. g., HC1 salt) with O=C=N-X. And also, the compound of formula (II) may obtained by a process comprising reacting a compound of formula (III) or its salt with triphosgen or 1, l'-carbonyldiimidazole to obtain a compound of formula (IV); and then reacting the compound of formula (IV) with NH2-X.

[159] wherein, R1, R2, R3, and X are the same as defined above and R4 is chloro or imidazole.

[160] Preferably, reacting the compound of formula (III) or its salt with O=C=N-X may be carried out in an organic solvent such as dichloromethane, acetonitrile, tetrahydrofuran, dimethyl sulfoxide, and toluene in the presence of a base such as tri- ethylamine, N, N-diisopropylethylamine, and N-methylmorpholine.

[161] Reacting the compound of formula (IV) with NH2-X may be carried out in an organic solvent such as dichloromethane, acetonitrile, tetrahydrofuran, dimethyl sulfoxide, and toluene, with stirring under reflux.

[162] The compound of formula (III) or its salt may be obtained by a process comprising (a) reacting a compound of formula (V) with a compound of formula (VI); and then (b) deprotecting the product of Step (a): [163] wherein, R1, R2, and R3 are the same as defined above and R5 is a amino protecting group.

[164] The amino protecting group may be a commonly used protecting group, for example, t-butoxycarbonyl, benzyloxycarbonyl, or p-nitrobenzyloxycarbonyl.

[165] The compound of formula (V) may be obtained by reacting a compound of formula (VII) or its salt with a compound of formula (VIII) in the presence of a base: [166] wherein, R and R are the same as defined above and Z is chloro, p-tolunesulfonyl, or methanesulfonyl.

[167] The base that can be used in reacting the compound of formula (VII) or its salt with the compound of formula (VIII) may be an inorganic base such as potassium carbonate, sodium bicarbonate (NaHCO3), and cesium carbonate. Reacting the compound of formula (VII) or its salt with the compound of formula (VIII) may be carried out in a solvent such as acetonitrile, acetone, methanol, and ethanol.

[168] The present invention also provides an antibacterial composition comprising a ther- apeutically effective amount of the compound of formula (I) or its pharmaceutically acceptable salt and a pharmaceutically acceptable carrier. The composition of the present invetnion is useful for treating patients or animals with bacterial infections by administration or spreading over infected skins. The composition of the present invetion is also useful for antibacterial purification and disinfection.

[169] The composition of the present invetnion may be orally or parenterally ad- ministered. The composition of the present invention for oral administration may be in the form of tablet, capsule, powder, granule, solution, suspension, or gel, and may comprise common additives such as a diluent, a disintegrating agent, and a lubricant.

Examples of the additives include a diluent such as syrup, Arabic gum, gellatin, sortitol, lactose, suger, corn starch, calcium phosphate, glycine, magenesium stearate, talc, polyethylene glycol, silica, potato starch, and sodium lauryl sulfate, a flavorant, and a colorant. The composition (e. g. , injection) of the present invention for parenteral administration may be an isotonic solution or may be sterilized. In this case, the composition of the present invention may comprise common additives such as a preservative and a stabilizer.

[170] The antibacterial composition of the present invetnion may be administered in an average adult (about 70 kg) dosage of abut 7mg/day to 35 g/day for antibacterial treatment. An adequate dosage is determined depending on the type and the degree of severity of diseases. In this regard, an average adult dosage may comprise about 0.7 mg to 2.8 g of the compound of the present invention together with a pharmaceutically acceptable carrier.

[171] The following Examples are given for the purpose of illustration only, and are not intended to limit the scope of the invention.

[172] Example 1.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-butylcarbamoyl)-2, 2-dimethylpropyl)-3- ( 3-chlorophenyl) urea [173] The title compound was prepared according to the following Scheme 1: [174] Scheme 1 [175] Step 1: Butylaminoacetic add ethyl ester [176] An acetonitrile suspension (358 ml) of glycine ethyl ester hydrochloride (10 g, 71.6 mmol), 1-bromobutane (7.7 ml, 71.6 mmol), and potassium carbonate (9.9 g, 71.6 mmol) was heated at 60 °C and then stirred for 18 hours. The precipitate was removed by filtration of the reaction suspension and the filtrate was concentrated under vacuum.

The resultant concentrate was purified by silica gel chromatography to give 4 g (yield 35%) of the title compound.

[177] H-NMR (CDCI) o 0.91 (t, J=7.2Hz, 3H), 1.28 (t, J=7. 1Hz, 3H, ), 1.34 (m, 2H), 3 1.46 (m, 2H), 2.60 (t, J=7.1 Hz, 2H), 3.40 (s, 2H), 4.19 (q, J=14.3Hz, J=7.4Hz, 2H) [178] [179] Step 2: [ ( (S)-2-tert-butoxycarbonylamino-3, 3-dimethylbutyryl) butylamino] acetic add ethyl ester [180] 1-hydroxybenzotriazole (3.0 g, 22.1 mmol), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.2 g, 22.1 mmol), N, N-diisopropylethylamine (6.3 ml, 36.7 mmol), and L- N-t-butoxycarbonyl-t-butyl-leuane (3.4 g, 14.7 mmol) were added to a dichloromethane solution (73 ml) of butylaminoacetic acid ethyl ester (2.3 g, 14.7 mmol). The reaction mixture was stirred at room temperature for 18 hours and then washed with distilled water and a solution of IN HCl. The organic layer was dried on anhydrous sodium sulfate and concentrated under vacuum. The resultant concentrate was purified by silica gel chromatography to give 4.3 g (yield 78%) of the title compound.

[181] H-NMR (CDCI) o 1.02 (m, 12H), 1.24-1. 58 (m, 16H), 3.2 (m, 1H), 3.6 (m, 2H), 3 4.17 (m, 2. 5H), 4.54 (m, 1. 5H), 5.25 (m, 1H) [182] [183] Step 3: (S)-1-(butylethoxycarbonylmethylcarbamoyl)-2, 2-dimethylpropylamine hy- drochloride [184] A 1,4-dioxane solution (3.4 ml) of 4N HCl was added to [((S)-2-tert-butoxyCarbonylamino-3, 3-dimethylbutyryl) butylamino] acetic acid ethyl ester (4.2 g, 11.3 mmol). The reaction mixture was stirred at room temperature for 18 hours and then concentrated under vacuum. The resultant concentrate was used in the next step without further purification.

[185] <BR> <BR> <BR> <BR> <BR> [186] Step 4: (butyl- { (S) -2- [3-(3-chlorophenyl) ureido] -3, 3-dimethylbutyryl} amino) acetic add ethyl ester [187] Triethylamine (0.1 ml, 0.70 mmol) and 3-chlorophenylisocyanate (0.04 ml, 0.31 mmol) were added to a dichlorometane solution (0.9 ml) of (S)-l-(butylethoxyCarbonylmethylcarbamoyl)-2, 2-dimethylpropylamine hydrochloride (0.1 g, 0.35 mmol). The reaction mixture was stirred at room temperature for 18 hours and then washed with water. The organic layer was dried on anhydrous sodium sulfate and concentrated under vacuum. The resultant concentrate was purified by silica gel chromatography to give 0.05 g (yield 40%) of the title compound.

[188] H-NMR (CDCI) o 0.88-1. 04 (m, 12H), 1.26-1. 70 (m, 7H), 3.40-5. 25 (m, 7H), 3 6.87-7. 54 (m, 4H) [189] [190] Step 5: 1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-butylcarbamoyl)-2, 2-dimethylpropyl)-3- ( 3-chlorophenyl) urea [191] A methanol solution (0.5 ml) of 3 M KOH was dropwise added to a methanol solution (0.5 ml) of 2 M NH2OH HCl and stirred for 30 minutes. The precipitate was removed by filtration. Then, butyl-{(S)-2-[3-(3-chlorophenyl)ureido] - 3, 3-dimethylbutyryl}amino) acetic add ethyl ester (0.05 g, 0.12 mmol) was dissolved in the filtrate and stirred for 2 hours. After concentration and water addition, the reaction mixture was neutralized with a solution of 1 N HC1, extracted with dichloromethane, dried on anhydrous sodium sulfate, and concentrated under vacuum.

The resultant concentrate was purified by silica gel chromatography to give 0.032 g (yield 61%) of the title compound.

[192]'H-NMR (CDC1) 6 0.88-1. 04 (m, 12H), 1.26-1. 70 (m, 4H), 3.42-5. 32 (m, 5H), 3 6.87-7. 54 (m, 4H) [193] [194] The compounds of the following Examples were prepared in the same manner as in Example 1 except that bromomethylcyclohexane, p- tolunesulfonylmethylcyclopentane, 1-p-tolunesulfonyl-3-methylbutane, l-p-tolunesulfonyl-2qclopentylethane, or p-tolunesulfonylmethylcwclobutane was used instead of 1-bromobutane of Step 1, L-N-t-butoxycarbonyl-valine, L- N-t-butoxycarbonyl-leucine, or L-N-t-butoxycarbonyl-isoleudne was used instead of L-N-t-butoxycarbonyl-t-butyl-leudne of Step 2, or substituted isocyanate was used instead of 3-chlorophenylisocyanate of Step 4.

[195] [196] Example 2.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(3-chlorophenyl) urea [197] H-NMIWCDC1) b 1.03 (s, 9H), 1.22-1. 67 (m, 8H), 2.19 (m, 1H), 3.37-4. 64 (m, 3 5H), 6.92-7. 49 (m, 4H) [198] [199] Example 3.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3-(3-chlorophenyl) urea [200]'H-NMR (CDC1) 6 1.01-1. 11 (m, 13H), 1.44-1. 78 (m, 7H), 3.55-4. 79 (m, 5H), 3 6.92-7. 51 (m, 4H) [201] [202] Example 4.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3-p-tolylurea <BR> <BR> [203] 1H-NMR(CDCl3) # 1.00-1.11 (m, 13H), 1.51-1.77 (m, 7H), 1.28 (s, 3H), 3.41-4.51 (m, 5H), 7.06-7.25 (m, 4H) [204] [205] Example 5.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3-m-tolylurea <BR> <BR> [206] 1H-NMR(CDCl3) # 0.98-1.01 (m, 13H), 1.48-1.75 (m, 7H), 1.29 (s, 3H), 3.58-4.62 (m, 5H), 6.82-7.23(m, 4H) [207] [208] Example 6.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (3-methoxyphenyl) urea [209] 1H-NMR(CDCl ) # 0.92-1. 12 (m, 13H), 1.50-1. 75 (m, 7H), 3.58-4. 62 (m, 8H), 3 6.54-7. 23 (m, 4H), 7.63 (s, 1H) [210] [211] Example 7.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-m-tolylurea [212]'H-NMR (CDC1) 6 1.01 (s, 9H), 1.15-1. 67 (m, 8H), 2.17-2. 27 (m, 4H), 3.48-4. 73 3 (m, 5H), 6.79-7. 18 (m, 4H) [213] [214] Example 8.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(3-chlorophenyl) urea <BR> <BR> [215] 1H-NMR(CDCl3) # 1.00-1.28 (m, 15H), 1.63 (s, 5H), 3.42-4.73 (m, 5H), 6.69-7.41 (m, 4H) [216] [217] Example 9.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-m-tolylurea [218] 1H-NMR(CDCl ) # 1.00-1. 28 (m, 15H), 1.62 (s, 5H), 2.26 (s, 3H), 3.42-4. 73 (m, 3 5H), 6.79-7. 18 (m, 4H) [219] [220] Example 10.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclohexylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-methoxyphenyl) urea [221] H-NMR (CDCI) o 1.00-1. 28 (m, 15H), 1.63 (s, 5H), 3.41-4. 71 (m, 8H), 6.50-7. 12 3 (m, 4H) [222] [223] Example 11.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(biphenyl-4-yl) urea [224] 1H-NMR(CDCl ) # 1.02 (s, 9H), 1.48 (m, 8H), 2.17 (m, 1H), 4.02 (m, 3H), 4.64 3 (m, 1H), 6.26 (m, 1H), 7.42 (m, 10H), 7. 89 (m, 1H) [225] [226] Example 12.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-methoxyphenyl) urea [227] H-NMIWCDC1) b 1.04 (s, 9H), 1.48 (m, 8H), 2.18 (m, 1H), 3.57 (m, 1H), 3.81 (s, 3 3H), 4.10 (m, 3H), 4.64 (m, 1H), 6.28 (m, 1H), 6.85 (m, 3H), 7.45 (m, 1H), 8.00 (m, 1H) [228] [229] Example 13.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-chlorophenyl) urea [230] 1H-NMR(CDCl3) # 1.02 (s, 9H), 1.53 (m, 8H), 2.20 (m, 1H), 3.49 - 4.79 (m, 5H), 6.79 (m, 1H), 7.21 (m, 3H), 7.62 (m, 1H), 7.98 (m, 1H) [231] [232] Example 14.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(3syanophenyl) urea [233] H-NMIWCDC1) b 1.05 (s, 9H), 1.58 (m, 8H), 2.20 (m, 1H), 3.58-4. 70 (m, 5H), 3 7.12-7. 65 (m, 4H) [234] [235] Example 15.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl)-2, 2-dimethylpropyl) -3-(3-chlorophenyl) urea [236]'H-NMR (CDC1) 6 0.89-1. 05 (m, 15H), 1.42-1. 85 (m, 3H), 3.57-4. 61 (m, 5H), 3 6.87-7. 53 (m, 4H) [237] [238] Example 16.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3-p-tolylurea [239] 1H-NMR(CDCl3) # 0.85-1.04 (m, 15H), 1.30-1.65 (m, 3H), 2.27 (s, 3H), 3.57-4.61 (m, 5H), 6.87-7.53(m, 4H) [240] [241] Example 17.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3-m-tolylurea [242] 1H-NMR(CDCl ) # 0.85-1. 02 (m, 15H), 1.35-1. 59 (m, 3H), 2.28 (s, 3H), 3 3.58-4. 57 (m, 5H), 6.82-7. 20 (m, 4H) [243] [244] Example 18.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) - 3- (3-methoxyphenyl) urea [245] 1H-NMR(CDCl ) # 0.85-1. 02 (m, 15H), 1.37-1. 61 (m, 3H), 3.58-4. 57 (m, 8H), 3 6.54-7. 13 (m, 4H) [246] [247] Example 19.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(4syanophenyl) urea [248] H-NMIWCDC1) b 1.06 (s, 9H), 1.57 (m, 8H), 2.27 (m, 1H), 3.05-4. 11 (m, 5H), 3 6.15-7. 76 (m, 6H) [249] [250] Example 20.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-fluorophenyl) urea <BR> <BR> <BR> [251] 1H-NMR(CDCl3) # 1.05 (s, 9H), 1.53 (m, 8H), 2.24 (m, 1H), 3.51 - 4.80 (m, 5H), 6.61 - 8.09 (m, 6H) [252] [253] Example 21.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-fluorophenyl) urea [254]'H-NMR (CDC1) 6 1.01 (s, 9H), 1.52 (m, 8H), 2.23 (m, 1H), 3.45-4. 79 (m, 5H), 3 6.89-8. 09 (m, 6H) [255] [256] Example 22.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (4-fluorophenyl) urea [257] 1H-NMR(CDCl ) # 1.01 (s, 9H), 1.56 (m, 9H), 2.23 (m, 1H), 3.45-4. 79 (m, 5H), 3 6.89-8. 09 (m, 6H) [258] [259] Example 23.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-nitrophenyl) urea [260] 1H-NMR(CDCl3) # 1.02 (s, 9H), 1.54 (m, 8H), 2.20 (m, 1H), 3.50 - 4.88 (m, 5H), 6.97 - 8.49 (m, 4H) [261] [262] Example 24.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-nitrophenyl) urea [263] 1H-NMR(CDCl ) # 1.02 (s, 9H), 1.55 (m, 8H), 2.21 (m, 1H), 3.59-4. 88 (m, 5H), 3 6.74-8. 25 (m, 6H) [264] [265] Example 25.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 3-dichlorophenyl) urea [266] 1H-NMR(CDCl ) # 1.02 (s, 9H), 1.10-1. 74 (m, 8H), 2.19 (m, 1H), 3.48-4. 80 (m, 3 5H), 6.70-8. 28 (m, 4H) [267] [268] Example 26.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 4-dichlorophenyl) urea [269] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.05-1. 68 (m, 8H), 2.19 (m, 1H), 3.48-4. 84 (m, 3 5H), 6.75-8. 30 (m, 5H) [270] [271] Example 27.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 5-dichlorophenyl) urea [272] H-NMIWCDC1) b 1.03 (s, 9H), 1.10-1. 67 (m, 8H), 2.22 (m, 1H), 3.48-4. 81 (m, 3 5H), 6.70-8. 10 (m, 5H) [273] [274] Example 28.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3, 4-dichlorophenyl) urea [275] 1H-NMR(CDCl3) # 1.03 (s, 9H), 1.25-1.69 (m, 8H), 2.25 (m, 1H), 3.47-4.72 (m, 5H), 7.21-7.65 (m, 3H) [276] [277] Example 29.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3, 5-dichlorophenyl) urea [278] H-NMIWCDC1) b 1.02 (s, 9H), 1.23-1. 69 (m, 8H), 2.24 (m, 1H), 3.49-4. 74 (m, 3 5H), 6.51-7. 36 (m, 4H) [279] [280] Example 30.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (4-nitrophenyl) urea [281] 1H-NMR(CDCl ) # 1.05 (s, 9H), 1.23-1. 69 (m, 8H), 2.23 (m, 1H), 3.49-4. 72 (m, 3 5H), 7.29-8. 13 (m, 4H) [282] [283] Example 31.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (4-acetylphenyl) urea [284] H-NMIWCDC1) b 1.06 (s, 9H), 1.21-1. 77 (m, 8H), 2.26 (m, 4H), 3.55-4. 67 (m, 3 5H), 77.21-7. 52 (m, 4H) [285] [286] Example 32.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (4- (trifluoromethoxy) phenyl) urea [287] H-NMIWCDC1) b 1.05 (s, 9H), 1.21-1. 66 (m, 8H), 2.28 (m, 1H), 3.53-4. 70 (m, 3 5H), 7.07-7. 43 (m, 4H) [288] [289] Example 33.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (benzo [d] [1, 3] dioxol-5-yl) urea <BR> <BR> <BR> [290] 1H-NMR(CDCl3) # 0.99 (s, 9H), 1.60 (m, 8H), 2.24 (m, 1H), 3.54 - 3.91 (m, 3H), 4.25 (m, 1H), 4.52 (m, 1H), 5.92 (s, 2H), 6.72 - 6.95 (m, 3H) [291] [292] Example 34.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 4-dichlorophenyl) urea [293] 1H-NMR(CDCl3) # 1.02-1.11 (m, 13H), 1.45-1.76 (m, 7H), 3.48-4.69 (m, 5H), 6.81 (bs, 1H), 7.15-7.26 (m, 2H), 7.68 (s, 1H), 8,25 (m, 1H) [294] [295] Example 35.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 5-dichlorophenyl) urea [296] 1H-NMR(CDCl ) # 1.03-1. 12 (m, 13H), 1.41-1. 88 (m, 7H), 3.53-4. 75 (m, 5H), 3 6.84-7. 17 (m, 2H), 7.69 (bs, 1H), 8.32 (s, 1H) [297] [298] Example 36.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (2-methoxyphenyl) urea [299] H-NMIWCDC1) b 1.03 (m, 13H), 1.46-1. 77 (m, 7H), 3.60-4. 65 (m, 8H), 6.29 (bs, 3 1H), 6.82-6. 99 (m, 2H), 7.92 (s, 1H), 8.07 (m, 1H) [300] [301] Example 37.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) - 3- (2, 4-dichlorophenyl) urea [302] 1H-NMR(CDCl ) # 0.80-1. 03 (m, 15H), 1.51-1. 62 (m, 3H), 3.54-4. 67 (m, 5H), 6.85 3 (bs, 1H), 7.14-7. 26 (m, 2H), 7.70 (s, 1H), 7.14 (m, 1H) [303] [304] Example 38.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) - 3- (2, 5-dichlorophenyl) urea [305] 1H-NMR(CDCl ) # 0.80-1. 17 (m, 15H), 1.51-1. 62 (m, 3H), 3.56-4. 71 (m, 5H), 3 6.89-7. 18 (m, 2H), 7.67 (s, 1H), 8.32 (s, 1H) [306] [307] Example 39.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3-(3, 4-dichlorophenyl) urea <BR> <BR> <BR> [308] 1H-NMR(CDCl3) # 0.90-1.04 (m, 15H), 1.36-1.62 (m, 3H), 3.56-4.65 (m, 5H), 6.56 (bs, 1H), 7.16-7.33 (m, 2H), 7.68 (s, 1H), 8.62 (m, 1H) [309] [310] Example 40.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) - 3- (2-methoxyphenyl) urea [311] 1H-NMR(CDCL ) # 0.82-1. 04 (m, 15H), 1.28-1. 68 (m, 3H), 3.59-4. 63 (m, 8H), 6.24 3 (bs, 1H), 6. 83-1. 99 (m, 2H), 7.44 (m, 1H), 8.06 (m, 1H) [312] [313] Example 41.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (4- (trifluoromethyl) phenyl) urea [314] H-NMIWCDC1) b 1.10 (s, 9H), 1.28 (m, 2H), 1.63 (m, 6H), 2.30 (m, 1H), 3 3.61-4. 75 (m, 5H), 7.52 (m, 4H) [315] [316] Example 42.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-ethylphenyl) urea [317] 1H-NMR(CDCl ) # 0.99 (s, 9H), 1.22 (m, 5H), 1.61 (m, 6H), 2.22 (m, 1H), 2.65 3 (m, 2H), 3.53-4. 62 (m, 5H), 7.31 (m, 4H) [318] [319] Example 43.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-ethoxyphenyl) urea [320] 1H-NMR(CDCl3) # 1.04 (s, 9H), 1.20 (m, 2H), 1.40-1.70 (m, 9H), 2.24 (m, 1H), 3.45-4.76 (m, 7H), 5.90 (m, 1H), 6.85-7.16 (m, 4H) [321] [322] Example 44.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3, 4-difluorophenyl) urea [323] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.26 (m, 2H), 1.55-1. 76 (m, 6H), 2.25 (m, 1H), 3 3.40-4. 72 (m, 5H), 6.34 (m, 1H), 6.55 (m, 1H), 6.98 (m, 2H), 8.75 (m, 1H) [324] [325] Example 45.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3, 5-difluorophenyl) urea [326] 1H-NMR(CDCl ) # 1.04 (s, 9H), 1.24 (m, 2H), 1.54-1. 86 (m, 6H), 2.23 (m, 1H), 3 3.40-4. 70 (m, 5H), 6.48 (m, 1H), 6.98 (m, 2H), 7.51 (m, 1H), 8.60 (m, 2H) [327] [328] Example 46.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2, 5-difluorophenyl) urea [329] 1H-NMR(CDCl ) # 0.97 (s, 9H), 1.20 (m, 2H), 1.48-1. 62 (m, 6H), 2.18 (m, 1H), 3 3.15-4. 74 (m, 5H), 6.73 (m, 1H), 7.22 (m, 2H), 8.00 (m, 2H), 8.83 (m, 2H) [330] [331] Example 47.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (2-methoxyphenyl) urea [332] 1H-NMR(CDCl ) # 0.96-1. 28 (m, 8H), 1.53-2. 16 (m, 8H), 3.20-4. 52 (m, 8H), 3 6.71-6. 91 (m, 4H), 7.57-8. 11 (m, 2H) [333] [334] Example 48.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (2-chlorophenyl) urea [335] 1H-NMR(CDCl3) # 0.97-1.28 (m, 8H), 1.57-2.17 (m, 8H), 3.37-4.56 (m, 5H), 6.87-7.26 (m, 4H), 7.63 (m, 1H), 8.12 (m, 1H) [336] [337] Example 49.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2-methoxyphenyl) urea [338] 1H-NMR(CDCl ) # 1.04 (s, 9H), 1.75-2. 04 (m, 6H), 2.65 (m, 1H), 3.53-4. 70 (m, 3 8H), 6.15 (bs, 1H), 6.84-6. 98 (m, 3H), 7.51 (m, 1H), 8.07 (m, 1H) [339] [340] Example 50.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2-chlorophenyl) urea [341] H-NMIWCDC1) b 1.03 (s, 9H), 1.75-2. 05 (m, 6H), 2.65 (m, 1H), 3.72-4. 75 (m, 3 5H), 6.20 (bs, 1H), 6.90-7. 30 (m, 3H), 7.56 (m, 1H), 8.29 (m, 1H) [342] [343] Example 51.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2-methoxyphenyl) urea [344] 1H-NMR(CDCl ) # 0.94-0. 02 (m, 6H), 1.80-2. 08 (m, 7H), 2.60 (m, 1H), 3.52-4. 5 3 (m, 8H), 6.74-6. 93 (m, 4H), 7.63-8. 10 (m, 2H) [345] [346] Example 52.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2-chlorophenyl) urea [347] 1H-NMR(CDCl ) # 0.96-1. 02 (m, 6H), 1.74-1. 90 (m, 7H), 2.62 (m, 1H), 3.53-4. 54 3 (m, 8H), 6.87-7. 26 (m, 4H), 7.69-8. 65 (m, 2H) [348] [349] Example 53.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (3-chlorophenyl) urea <BR> <BR> <BR> [350] 1H-NMR(CDCl3) # 0.95-1.04 (m, 6H), 1.83-2.11 (m, 7H), 2.65 (m, 1H), 3.30-4.67 (m, 5H), 6.93-7.22(m, 3H), 7.54 (s, 1H) [351] [352] Example 54.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2, 4-dichlorophenyl) urea [353] 1H-NMR(CDCl ) # 0.96-1. 03 (m, 6H), 1.77-2. 09 (m, 7H), 2.57 (m, 1H), 3.53-4. 46 3 (m, 5H), 7.09-8. 11 (m, 3H) [354] [355] Example 55.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2-fluorophenyl) urea [356] 1H-NMR(CDCl ) # 0.94-1. 04 (m, 6H), 1.75-2. 04 (m, 7H), 2.62 (m, 1H), 3.52-4. 53 3 (m, 5H), 6.82-7. 05 (m, 4H), 7.75-8. 11 (m, 2H) [357] [358] Example 56.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2, 4-difluorophenyl) urea <BR> <BR> <BR> [359] 1H-NMR(CDCl3) # 0.94-1.05 (m, 6H), 1.73-2.05 (m, 7H), 2.62 (m, 1H), 3.52-4.51 (m, 5H), 6.53-6.99 (m, 3H), 7.66-7.99 (m, 2H) [360] [361] Example 57. l-((S)-l-(N-((h ydroxy- carbamoyl) methyl)-N-(2eclopentylethyl) carbamoyl)-2-methylpropyl)-3-(2-methoxy phenyl) urea [362]'H-NMR (CDC1) 6 0.96-1. 10 (m, 8H), 1.33-2. 05 (m, ICH), 3.10-4. 46 (m, 8H), 3 6.78-6. 93 (m, 4H), 7. 62-8. 10 (m, 2H) [363] [364] Example 58.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (2-chlorophenyl) urea [365] H-NMR (CDCI) o 0.95-1. 11 (m, 8H), 1.33-2. 05 (m, ICH), 3.19-4. 50 (m, 5H), 3 6. 85-7. 26 (m, 4H), 7. 74-8. 17 (m, 2H) [366] [367] Example 59.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (3, 4-dichlorophenyl) urea [368] H-NMR (CDCI) o 0.95-1. 15 (m, 8H), 1.53-2. 00 (m, ICH), 3.19-4. 41 (m, 5H), 3 7.11-7. 56 (m, 3H) [369] [370] Example 60.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (2, 4-dichlorophenyl) urea [371] H-NMR (CDCI) o 0.961. 15 (m, 8H), 1.51-2. 01 (m, ICH), 3.19-4. 41 (m, 5H), 3 7.07-8. 12 (m, 3H) [372] [373] Example 61.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (2, 5-dichlorophenyl) urea [374] 1H-NMR(CDCl ) # 0.95-1. 11 (m, 8H), 1.54-2. 05 (m, ICH), 3.19-4. 54 (m, 5H), 3 6.8-8. 29 (m, 5H) [375] [376] Example 62.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (2, 5-difluorophenyl) urea [377] 1H-NMR(CDCl ) # 0.92-1. 14 (m, 8H), 1.57-2. 05 (m, ICH), 3.19-4. 55 (m, 5H), 3 6.49-7. 92 (m, 5H) [378] [379] Example 63.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (2, 4-dichlorophenyl) urea [380]'H-NMR (CDC1) 6 1.04-1. 25 (m, 8H), 1.47-1. 81 (m, 6H), 2.17 (m, 2H), 3.55-4. 60 3 (m, 5H), 6.66-7. 05 (m, 2H), 7.62-8. 56 (m, 3H) [381] [382] Example 64.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (2, 5-dichlorophenyl) urea [383] 1H-NMR(CDCl ) # 0.99 (m, 6H), 1.23 (m, 2H), 1.58-2. 17 (m, 8H), 3.71-4. 60 (m, 3 5H), 6.82-7. 12 (m, 2H), 7.68-8. 31 (m, 2H) [384] [385] Example 65.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (2, 5-difluorophenyl) urea [386] 1H-NMR(CDCl ) # 0.92-1. 07 (m, 6H), 1.26 (m, 2H), 1.60-2. 16 (m, 8H), 3.35-4. 60 3 (m, 5H), 6.48 (m, 1H), 6.90 (m, 1H), 7.26-7. 92 (m, 3H) [387] [388] Example 66.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (3, 4-dichlorophenyl) urea [389] 1H-NMR(CDCl ) # 0.99 (m, 6H), 1.76-2. 11 (m, 7H), 2.61 (m, 1H), 3.20-4. 48 (m, 3 5H), 7.12-7. 61 (m, 3H) [390] [391] Example 67.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2, 5-dichlorophenyl) urea [392] 1H-NMR(CDCl ) # 0.99 (m, 6H), 1.78-2. 07 (m, 7H), 2.60 (m, 1H), 3.53-4. 58 (m, 3 5H), 6.82-6. 85 (m, 2H), 7.68-8. 29 (m, 2H) [393] [394] Example 68.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2, 5-difluorophenyl) urea [395] 1H-NMR(CDCl3) # 0.93-1.08 (m, 6H), 1.80-2.05 (m, 7H), 2.62 (m, 1H), 3.52-4.56 (m, 5H), 6.52 (m, 1H), 6.91 (m, 1H), 7.20-7.94 (m, 3H) [396] [397] Example 69.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-isopentylcarbamoyl)-2-methylpropyl)-3-( 2-methoxyphenyl) urea [398] 1H-NMR(CDCl3) # 0.79-1.03 (m, 12H), 1.25-2.05 (m, 4H), 3.15-4.47 (m, 8H), 6.75-6.92 (m, 4H), 7.59-8.10 (m, 2H) [399] [400] Example 70.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-isopentylcarbamoyl)-2-methylpropyl)-3-( 2-chlorophenyl) urea [401] 1H-NMR(CDCl ) # 0.82-1. 02 (m, 12H), 1.23-2. 05 (m, 4H), 3.66-4. 52 (m, 5H), 3 6.87-7. 26 (m, 4H), 7.67-8. 18 (m, 2H) [402] [403] Example 71.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( 2,4-dichlorophenyl) urea [404] H-NMIWCDC1) b 0.83-1. 02 (m, 12H), 1. 28--2. 02 (m, 4H), 3.40-4. 48 (m, 5H), 3 7.02-7. 22 (m, 3H), 7.66-8. 14 (m, 2H) [405] [406] Example 72.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( 2,5-dichlorophenyl) urea [407] 1H-NMR(CDCl ) # 0.83-1. 02 (m, 12H), 1.23-2. 00 (m, 4H), 3.41-4. 55 (m, 5H), 3 6.8-7. 26 (m, 3H), 7.76-8. 29 (m, 2H) [408] [409] Example 73.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( 2,5-difluorophenyl) urea [410] 1H-NMR(CDCl ) # 0.90-1. 07 (m, 12H), 1.39-1. 95 (m, 4H), 3.41-4. 54 (m, 5H), 6.50 3 (m, 1H), 6. 87 (m, 1H), 7. 23 (m, 1H), 7. 36-7. 92 (m, 2H) [411] [412] Example 74.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (5-chloro-2-methoxyphenyl) urea [413] H-NMR(CDCl ) # 1.03 (9H, s), 1.16 (m, 2H), 1.55-1. 68 (m, 6H), 2.17 (m, 1H), 3 3.50-4. 12 (m, 6H), 4.59 (m, 1H), 4.77 (m, 1H), 6.52 (m, 1H), 6.70 (m, 1H), 6.84 (m, 1H), 7.63 (d, 1H), 8.19 (d, 1H) [414] [415] Example 75.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2- (trifluoromethoxy) phenyl) urea [416] 1H-NMR(CDCl ) # 1.01 (s, 9H), 1.24 (m, 2H), 2.21 (m, 1H), 3.47-4. 80 (m, 5H), 3 6. 78-7. 24 (m, 3H), 7. 72-8. 20 (m, 2H) [417] [418] Example 76.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl butyl) -3- (2,5-dichlorophenyl) urea [419] 1H-NMR(CDCl ) # 0.90 (m, 6H), 1.22 (m, 4H), 1.66 (6H), 2.94-4. 63 (m, 6H), 3 6.82 (m, 1H), 7.10 (m, 1H), 7.42-7. 92 (m, 2H), 8.28 (d, 1H) [420] [421] Example 77.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -3-methyl butyl) -3- (2,5-dichlorophenyl) urea <BR> <BR> <BR> [422] 1H-NMR(CDCl3) # 0.93 (m, 6H), 1.26 (3H), 1.63 (m, 8H), 2.95 - 4.73 (5H), 6.79 (m, 1H), 7.09 (m, 1H), 7.45 - 8.18 (m, 3H) [423] [424] Example 78.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2, 5-dichlorophenyl) urea [425] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.71-2. 06 (m, 7H), 2.65 (m, 1H), 3.51-5. 29 (m, 3 4H), 6.84 (m, 2H), 7.12 (m, 1H), 7.70 (d, 1H), 8.30 (d, 1H) [426] [427] Example 79.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2, 4-dichlorophenyl) urea [428] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.70-1. 95 (m, 7H), 2.65 (m, 1H), 3.51-5. 29 (m, 3 4H), 6.84 (m, 1H), 7.14 (m, 1H), 7.25 (m, 1H), 7.70 (d, 1H), 8.11 (m 1H) [429] [430] Example 80.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3- (2-chlorophenyl) urea [431] 1H-NMR(CDCl ) # 0.94 (m, 15H), 1.62 (m, 3H), 3.00-4. 69 (m, 5H), 6.61 (m, 1H), 3 6.91 (m, 1H), 7.20 (m, 2H), 7.56 (s, 1H), 8.17 (d, 1H) [432] [433] Example 81.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (2-chlorophenyl) urea [434] 1H-NMR(CDCl ) # 1.03 (m, 11H), 1.50-1. 75 (m, 9H), 3.00-4. 70 (m, 5H), 6.77 3 (m, 1H), 6.90 (m, 1H), 7. 19 (m, 2H), 7. 65 (s, 1H), 8. 17 (m, 1H) [435] [436] Example 82.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3-(5-chloro-2-methoxyphenyl) urea [437] H-NMIWCDC1) b 1.03 (s, 9H), 1.75-2. 09 (m, 7H), 2.51-4. 74 (m, 8H), 6.27 (m, 3 1H), 6.72 (m, 1H), 6.87 (m, 1H), 7.49 (s, 1H), 8.20 (s, 1H) [438] [439] Example 83.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3-(5-chloro-2-methoxyphenyl) urea [440] 1H-NMR(CDCl ) # 0.81-1. 04 (m, 15H), 1.25-1. 82 (m, 3H), 3.00-4. 67 (m, 8H), 3 6.48 (m, 1H), 6.67 (m, 1H), 6.85 (m, 1H), 7.64 (s, 1H), 8.20 (s, 1H) [441] [442] Example 84.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3-(5-chloro-2-methoxyphenyl) urea [443] H-NMR (CDCI) o 1.04 (m, 11H), 1.43-1. 76 (m, 7H), 3.00-4. 69 (m, 8H), 6.57 3 (m, 2H), 6.84 (m, 1H), 7. 75 (m, 1H), 8.21 (m, 1H) [444] [445] Example 85.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3-(5-chloro-2-methoxyphenyl) urea [446] 1H-NMR(CDCl ) # 1.01 (m, 6H), 1.74-2. 08 (m, 8H), 2.61-4. 53 (m, 8H), 6.70 3 (m, 3H), 7. 51 (m, 1H), 8. 47 (m, 1H) [447] [448] Example 86.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3-(5-chloro-2-methoxyphenyl) urea [449] 1H-NMR(CDCl ) # 1.00 (m, 6H), 1.20 (m, 2H), 1.50 (m, 6H), 2.01 (m, 1H), 2.16 3 (m, 1H), 2.90-4. 56 (m, 8H), 6.70 (m, 3H), 7.55 (m, 1H), 8.22 (m, 1H) [450] [451] Example 87.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( 5-chloro-2-methoxyphenyl) urea <BR> <BR> <BR> [452] 1H-NMR(CDCl3) # 0.86-1.04 (m, 12H), 1.26-1.66 (m, 3H), 2.00 (m, 1H), 3.01-4.51 (m, 8H), 6.60-6.87 (m, 3H), 7.99 (m,1H), 8.20 (m, 1H) [453] [454] Example 88.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3-(5-chloro-2-methoxyphenyl) urea [455] 1H-NMR(CDCl ) # 0.97-1. 03 (m, 8H), 1.54-1. 77 (m, 9H), 2.00 (m, 1H), 3.05-4. 47 3 (m, 8H), 6.58-6. 94 (m, 3H), 7.69-8. 19 (m, 2 H) [456] [457] Example 89.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2, 5-dimethoxyphenyl) urea [458] H-NMIWCDC1) b 1.04 (s, 9H), 1.70-1. 89 (m, 6H), 2.60 (m, 1H), 3.50-4. 67 (m, 3 11H), 6.29-6. 72 (m, 3H), 7. 56-7. 84 (m, 2H) [459] [460] Example 90.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2-methoxy-5-methylphenyl) urea [461] H-NMIWCDC1) b 1.04 (s, 9H), 1.70-1. 93 (m, 6H), 2.51 (m, 1H), 2.27 (s, 3H), 3 3.55-4. 72 (m, 8H), 6.20 (m, 1H), 6.78 (m, 2H), 7.34-7. 92 (m, 2H) [462] [463] Example 91.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2-methoxy-5-methylphenyl) urea [464] 1H-NMR(CDCl ) # 0.96-1. 05 (m, 6H), 1.73-1. 90 (m, 6H), 2.24 (s, 3H), 2.55 (m, 3 1H), 3.51-4. 49 (m, 8H), 6.70 (m, 3H), 7.38-8. 35 (m, 2H) [465] [466] Example 92.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2, 4-dimethoxyphenyl) urea <BR> <BR> <BR> [467] 1H-NMR(CDCl3) # 1.00 (s, 9H), 1.69-2.07 (m, 6H), 2.60 (m, 1H), 3.50-4.66 (m, 11H), 6.00 (m, 1H), 6.44 (s, 2H), 7.02-7.78 (m, 2H) [468] [469] Example 93.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (2, 4-dimethoxyphenyl) urea [470]'H-NMR (CDC1) 6 0.98 (m, 6H), 1.71-1. 97 (m, 6H), 2.64 (m, 1H), 3.51-4. 45 (m, 3 11H), 6.28-6. 44 (m, 3H), 7.19-7. 80 (m, 2H) [471] [472] Example 94.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-chloropyridin-3-yl) urea [473] The title compound was prepared according to the following Scheme 2: [474] Scheme 2 [475] Step 1: C) clopentylmethylaminoacetic add ethyl ester [476] An acetonitrile suspension (84 ml) of glycine ethyl ester hydrochloride (5.8 g, 41.8 mmol), p-tolunesulfonylmethylcyclopentane (10.6 g, 41.8 mmol), and potassium carbonate (5.8 g, 41.8 mmol) was heated at 60 °C and then stirred for 18 hours. The precipitate was removed by filtration of the reaction suspension and the filtrate was concentrated under vacuum. The resultant concentrate was purified by silica gel chro- matography to give 1.3 g (yield 16.8%) of the title compound.

[477] H-NMR (CDCI) o 1.19 (m, 2H), 1.27 (t, J=7. 1Hz, 3H), 1.54 (m, 4H), 1.77 (m, 3 2H), 2.01 (m, 1H), 2.51 (d, J=7. 1Hz), 3.40 (s, 2H), 4.20 (q, J=7. 1Hz, J=14. 2Hz, 2H) [478] [479] Step 2: [(2S-t-butoxyCarbonylamino-3, 3-dimethylbutyryl) cyclopentylmethylamino] acetic acid ethyl ester [480] 1-hydroxybenzotriazole (0.44 g, 3.2 mmol), 1- (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.62 g, 3.2 mmol), N, N-diisopropylethylamine (0.93 ml, 5.4 mmol), and L- N-t-butoxycarbonyl-phenylalanine (0.5 g, 2.2 mmol) were added to a dichloromathane solution (4.3 ml) of cyclopentylmethylaminoacetic add ethyl ester (0.4 g, 2.2 mmol).

The reaction mixture was stirred at room temperature for 18 hours and washed with distilled water and a solution of 1 N HC1. The organc layer was dried on anhydrous sodium sulfate and concentrated under vacuum. The resultant concentrate was purified by silica gel chromatography to give 0.5 g (yield 57.4%) of the title compound.

[481] H-NMIWCDC1) b 1.02 (s, 9H), 1.25 (m, 5H), 1.29 (s, 9H), 1.44-1. 69 (m, 6H), 3 2.22 (m, 1H), 3.15 (m, 1H), 3.66 (m, 2H), 4.14-4. 63 (m, 4H), 5.32 (s, 1H) [482] [483] Step 3: [ (2S-amino-3, 3-dimethylbutyryl) c) clopentylamino] acetic add ethyl ester hydrochloride [484] A 1,4-dioxane solution (1.6 ml) of 4N HCl was added to [(2S-t-butoxyCarbonylamino-3, 3-dimethylbutyryl) cyclopentylmethylamino] acetic acid ethyl ester (0.5 g, 1.24 mmol). The reaction mixture was stirred at room temperature for 18 hours and concentrated under vacuum. The resultant concentrate was used in the next step without further purification.

[485] [486] Step 4: (cwclopentylmethyl- { (S)-2-[(imidazol-1-carbonyl) amino] - 3, 3-dimethylbutyryl}amino) acetic add ethyl ester [487] Carbonyldiimidazole (0.34 g, 2.11 mmol) was added to a dichloromethane solution (10 ml) of [ (2S-amino-3, 3-dimethylbutyryl) c) clopentylamino] acetic add ethyl ester hydrochloride (0.47 g, 1.41 mmol) and then N, N-diisopropylethylamine (0.24 ml, 1.41 mmol) was dropwise added thereto. The reaction mixture was stirred at room temperature for 4 hours and washed with water. The organic layer was dried on anhydrous sodium sulfate and concentrated under vacuum to give 0.49 g (yield 88%) of the title compound.

[488] H-NMIWCDC1) b 1.11 (s, 9H), 1.26 (m, 5H), 2.22 (m, 1H), 1.65 (m, 6H), 2.04 3 (m, 1H), 3.24 (m, 1H), 3.71 (m, 2H), 4.18 (m, 2H), 4.48 (m, 1H), 5.00 (m, 1H), 6.5 (m, 1H), 7.1 (s, 1H), 7.35 (s, 1H), 8.13 (s, 1H) [489] [490] Step 5: ({(S)-2-[3-(2-chloropyridin-3-yl) ureido] - 3, 3-dimethylbutyryl} cwclopentylmethylamino) acetic acid ethyl ester [491] 3-amino-2-chloropyridine (0.039 g, 0.3 mmol) was added to a toluene solution (1.5 ml) of (cyclopentylmethyl- { (S) -2- [(imindazol-1-carbonyl) amino] - 3, 3-dimethylbutyryl}amino) acetic add ethyl ester (0.12 g, 0.3 mmol) and stirred under reflux for 18 hours. The reaction mixture was concentrated under vacuum and purified by silica gel chromatography to give 0.014 g (yield 10%) of the title compound.

[492] H-NMIWCDC1) b 1.05 (s, 9H), 1.14-1. 74 (m, 11H), 2.22 (m, 1H), 3.47-4. 83 (m, 3 7H), 7.04-7. 83 (m, 3H) [493] [494] Step 6: 1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-chloropyridin-3-yl) urea [495] A methanol solution (0.3 ml) of 3 M KOH was dropwise added to a methanol solution (0.3 ml) of 2 M NH2OH HCl and then stirred for 30 minutes. The precipitate was removed by filtration. ({(S)-2-[3-(2-chloropyridin-3-yl)ureido] - 3, 3-dimethylbutyryl} cwclopentylmethylamino) acetic acid ethyl ester (0.014 g, 0.03 mmol) was dissolved in the resultant filtrate and stirred for 2 hours. The reaction mixture was neutralized with Dowex 50WX4-100. Dowex resin was removed by filtration and the filtrate was concentrated. The resultant concentrate was purified by silica gel chromatography to give 0.002 g (yield 14.3%) of the title compound.

[496] H-NMIWCDC1) b 1.03 (s, 9H), 1.14-1. 25 (m, 2H), 1.52-1. 74 (m, 6H), 2.22 (m, 3 1H), 3.47-4. 83 (m, 5H), 7.08 (m, 2H), 7.82-7. 91 (m, 2H), 8.52 (m, 1H) [497] [498] The comounds of the following Examples were prepared in the same manner as in Example 94 except that 1-p-toluenesulfonyl-3-methylbutane, l-p-toluenesulfonyl-2Mclopentylethane, or p-toluenesulfonylmethylcyclobutane was used instead of p-toluenesulfonylmethylcyclopentane of Step 1, L- N-t-butoxycarbonyl-valine was used instead of L-N-t-butoxycarlnyl-t-butyl-leudne of Step 2, or substituted amine was used instead of 3-amino-2-chloropyridine of Step 5.

[499] [500] Example 95.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea [501] H-NMIWCDC1) b 1.02 (s, 9H), 1.16 (m, 2H), 1.54-1. 68 (m, 6H), 2.17 (m, 4H), 3 3.52-4. 11 (m, 6H), 4. 58 (m, 1H), 4.75 (m, 1H), 6.46 (m, 1H), 6.76 (m, 1H), 7.50 (d, 1H), 7.98 (d, 1H) [502] [503] Example 96.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-benzoyl-3-chlorophenyl) urea [504] 1H-NMR(CDCl ) # 1.02 (s, 9H), 1.26 (m, 2H), 1.66 (m, 6H), 2.18 (m, 1H), 3.48- 3 4.09 (m, 3H), 4.52-4. 71 (m, 2H), 7.43 (m, 5H), 7.66 (m, 3H), 8.36 (m, 1H), 9.99 (d, 1H) [505] [506] Example 97.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (quinolin-8-yl) urea <BR> <BR> <BR> [507] 1H-NMR(CDCl3) # 1.06 (s, 9H), 1.63 (m, 8H), 2.17 (m, 1H), 3.63 - 4.29 (m, 3H), 4.65 (m, 1H), 4.84 (m, 1H), 6.87 - 7.03 (m, 1H), 7.34 (m, 3H), 8.04 - 8.62 (m, 3H), 9.26 (d, 1H) [508] [509] Example 98.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (benzo [d] thiazol-6-yl) urea [510] 1H-NMR(CDCl ) # 1.05 (s, 9H), 1.21 (m, 2H), 2.20 (m, 1H), 3.46-4. 66 (m, 5H), 3 7.13 (m, 1H), 7. 74-8. 88 (m, 3H) [511] [512] Example 99.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2- (piperidin-1-yl) phenyl) urea [513] H-NMIWCDC1) b 1.04 (s, 9H), 1.23 (m, 2H), 1.57-1. 72 (m, 10H), 2.21 (m, 1H), 3 2.80 (m, 4H), 3. 56-4. 75 (m, 5H), 7.05 (m, 3H), 7.61-7. 89 (m, 2H) [514] [515] Example 100.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (5- (trifluoromethyl)-2-morpholinophenyl) urea [516]'H-NMR (CDC1) 6 1.02 (s, 9H), 1.24 (m, 2H), 2.21 (m, 1H), 2.88 (m, 4H), 3 3.53-4. 76 (m, 9H), 6.67 (m, 1H), 7.10-7. 26 (m, 2H), 7.95-8. 49 (m, 2H) [517] [518] Example 101.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(3-chloro-4-morpholinophenyl) urea [519] H-NMIWCDC1) b 1.01 (s, 9H), 1.21 (m, 2H), 1.28-1. 64 (m, 6H), 2.18 (m, 1H), 3 2.98 (m, 4H), 3. 55-4. 70 (m, 9H), 6.20-7. 54 (m, 4H) [520] [521] Example 102.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (quinolin-5-yl) urea [522]'H-NMR (CDC1) 6 1.06 (s, 9H), 1.63 (m, 8H), 2.17 (m, 1H), 3.63-4. 29 (m, 3H), 3 4.65 (m, 1H), 4.84 (m, 1H), 6.60-8. 80 (m, 8H) [523] [524] Example 103.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2- (pyrrolidin-1-yl) phenyl) urea [525] H-NMR (CDCI) o 0.93 (s, 9H), 1.24 (m, 2H), 1.52-1. 65 (m, 6H), 1.90 (m, 4H), 3 2.17 (m, 1H), 3. 11-4. 61 (m, 9H), 6.07 (m, 1H), 6.85-7. 44 (m, 5H) [526] [527] Example 104.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(5-fluoro-2-(pyrrolidin-1-yl) phenyl) urea [528] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.23 (m, 2H), 1.56-1. 71 (m, ICH), 2.20 (m, 1H), 3 2.73 (m, 4H), 3. 64-4. 84 (m, 5H), 6.61 (m, 1H), 6.99 (m, 1H), 7.81-8. 07 (m, 2H) [529] [530] Example 105.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (5-fluoro-2- (piperidin-1-yl) phenyl) urea [531] H-NMIWCDC1) b 1.03 (s, 9H), 1.20 (m, 2H), 1.57-1. 68 (m, 6H), 2.17 (m, 1H), 3 3.42-4. 78 (m, 9H), 6.35-6. 66 (m, 2H), 7.04 (m, 1H), 7.89-8. 17 (m, 2H) [532] [533] Example 106.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (5-fluoro-2-morpholinophenyl) urea [534] H-NMIWCDC1) b 1.03 (s, 9H), 1.16 (m, 2H), 1.52-1. 70 (m, 6H), 2.17 (m, 1H), 3 2.90 (m, 4H), 3. 50-4. 72 (m, 9H), 6.30 (m, 1H), 6.80-7. 37 (m, 3H), 7.90 (m, 1H) [535] [536] Example 107.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-fluoro-4- (pyrrolidin-l-yl) phenyl) urea <BR> <BR> <BR> [537] 1H-NMR(CDCl3) # 0.99 (s, 9H), 1.15 (m, 2H), 1.49-1.69 (m, 6H), 1.91 (m, 4H), 2.17 (m, 1H), 3.27 (s, 4H), 3.86-4.70 (m, 5H), 6.09 (bs, 1H), 6.51-7.12 (m, 3H), 7.60 (s, 1H) [538] [539] Example 108.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-fluoro-4- (piperidin-1-yl) phenyl) urea [540]'H-NMR (CDC1) 6 1.00 (s, 9H), 1.21 (m, 2H), 1.52-1. 68 (m, 12H), 1.91 (m, 4H), 3 2.17 (m, 1H), 2. 90 (m, 4H), 3.50-4. 72 (m, 5H), 6.27 (bs, 1H), 6.76-7. 18 (m, 3H), 7.84 (s, 1H) [541] [542] Example 109.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (3-fluoro-4-morpholinophenyl) urea [543] H-NMIWCDC1) 6 1.01 (s, 9H), 1.21 (m, 2H), 1.28-1. 64 (m, 6H), 2.18 (m, 1H), 3 2.98 (m, 4H), 3. 55-4. 70 (m, 9H), 6.20 (m, 1H), 6.78-7. 54 (m, 3H) [544] [545] Example 110.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3-(5-chloroquinolin-8-yl) urea [546] 1H-NMR(CDCl ) # 1.04-1. 28 (m, 17H), 2.25 (m, 1H), 3.64-4. 81 (m, 5H), 6.8-9. 19 3 (m, 1H), 6.76-7. 18 (m, 7H) [547] [548] Example 111.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimet hylpropyl)-3- (2-chloro-4- (methylsulfonyl) phenyl) urea [549] H-NMIWCDC1) b 1.04 (s, 9H), 1.26 (m, 2H), 1.55-1. 68 (m, 6H), 2.18 (m, 1H), 3 3.43-4. 15 (m, 4H), 4.60-4. 80 (m, 1H), 7.74 (m, 2H), 8.03-8. 49 (m, 2H) [550] [551] Example 112.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea [552] 1H-NMR(CDCl ) # 1.03 (s, 9H), 1.68-2. 04 (m, 7H), 2.25 (s, 3H), 2.45-4. 67 (m, 3 8H), 6.50 (m, 1H), 6.76 (s, 1H), 7.57 (m, 1H), 7.98 (s, 1H) [553] [554] Example 113.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (5-fluoro-2- (pyrrolidin-1-yl) phenyl) urea [555] H-NMIWCDC1) b 1.02 (s, 9H), 1.72-2. 08 (m, 11H), 2.62 (m, 1H), 3.00 (m, 4H), 3 3.54-4. 66 (m, 4H), 6.31 (m, 1H), 6.66 (m, 1H), 6.94 (m, 1H), 7.38-7. 90 (m, 2H) [556] [557] Example 114. 1- ( (S)-l- (N- ( (hydroxycarbamoyl) methyl)-N- (cyclobutylmethyl ) carbamoyl)-2, 2-dimethylpropyl)-3- (quinolin-8-yl) urea [558] H-NMIWCDC1) b 1.08 (s, 9H), 1.70-2. 09 (m, 7H), 2.54-4. 81 (m, 5H), 6.65 (m, 3 1H), 7.34 (m, 2H), 7.47 (m, 1H), 8.05 (m, 1H), 8.45 (m, 1H), 8.64 (m, 1H), 9.15 (m, 1H) [559] [560] Example 115.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) -3-(4-chloro-2-methoxy-5-methylphenyl) urea [561] H-NMR (CDCI) o 0.83-1. 04 (m, 15H), 1.25-1. 65 (m, 3H), 2.27 (s, 3H), 3.00- 3 4.62 (m, 8H), 6.14 (m, 1H), 6.78 (s, 1H), 7.36 (m, 1H), 7.98 (m, 1H) [562] [563] Example 116.

1- ( (S)-1- (N- ( (hydroxycarbamoyl) methyl) -N-isopentylcarbamoyl) -2, 2-dimethylpropyl) - 3- (quinolin-8-yl) urea [564] 1H-NMR(CDCl ) # 0.80-1. 10 (m, 15H), 1.25-1. 69 (m, 3H), 3.00-4. 77 (m, 5H), 3 6.66 (m, 1H), 7. 31 (m, 3H), 8.04 (m, 1H), 8.47 (m, 1H), 8.63 (m, 1H), 9.15 (m, 1H) [565] [566] Example 117.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (4-chloro-2-methoxy-5-methylphenyl) urea [567] 1H-NMR(CDCl ) # 1.03 (m, 11H), 1.42-1. 75 (m, 7H), 2.21 (s, 3H), 3.00-4. 64 3 (m, 8H), 6.52 (m, 1H), 6.75 (m, 1H), 7.62 (s, 1H), 8.00 (s, 1H) [568] [569] Example 118.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3-(5-fluoro-2-(pyrrolidin-1-yl) phenyl) urea [570]'H-NMR (CDC1) 6 0.88-1. 13 (m, 11H), 1.53-1. 95 (m, 7H), 3.05 (m, 4H), 3.55- 3 4.60 (m, 5H), 6.13 (m, 1H), 6.68 (m, 1H), 6.98 (m, 1H), 7.46-7. 87 (m, 2H) [571] [572] Example 119.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2,2-dimet hylpropyl)-3- (quinolin-8-yl) urea <BR> <BR> <BR> [573] 1H-NMR(CDCl3) # 0.89 - 1.03 (m, 11H), 1.38 - 1.73 (m, 7H), 3.00 - 4.74 (m, 5H), 7.03 - 7.45 (m, 4H), 7.98 (m, 1H), 8.47 (m, 2H), 9.37 (m, 1H) [574] [575] Example 120.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea [576] 1H-NMR(CDCl ) # 1.01 (m, 6H), 1.67-2. 22 (m, 8H), 2.62-4. 44 (8H), 6.68 (m, 3 2H), 7.39 (m, 1H), 7.89 (m, 1H) [577] [578] Example 121.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (5-fluoro-2- (pyrrolidin-1-yl) phenyl) urea [579] H-NMR (CDCI) o 0.96 (m, 6H), 1.84 (m, 12H), 2.62-4. 47 (m, 9H), 6.46 (m, 1H), 3 6.65 (m, 1H), 6.99 (m, 1H), 7.70 (m, 1H), 7.94 (m, 1H) [580] [581] Example 122.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (quinolin-8-yl) urea [582] 1H-NMR(CDCl ) # 0.88 (m, 3H), 1.12 (m, 3H), 1.80-2. 16 (m, 7H), 2.62 (m, 1H), 3 3.61 (m, 2H), 4.09 (m, 1H), 4.80 (m, 2H), 7.43 (m, 2H), 7.56 (m, 1H), 8.02 (m, 1H), 8.19 (m, 1H), 8.54 (m, 1H), 8.71 (m, 2H) [583] [584] Example 123.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea [585] H-NMR (CDCI/CD OD) 6 1.00 (m, 6H), 1.22 (m, 2H), 1.55 (m, 6H), 2.01 (m, 3 3 1H), 2.14 (m, 4H), 3.05-4. 41 (m, 8H), 6.80 (s, 1H), 7.95 (s, 1H) [586] [587] Example 124.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (5-fluoro-2- (pyrrolidin-1-yl) phenyl) urea [588] H-NMR (CDCI) o 0.98 (m, 6H), 1.18 (m, 2H), 1.59 (m, 6H), 1.92 (m, 5H), 2.18 3 (m, 1H), 3.04 (m, 4H), 3.34-4. 49 (m, 5H), 6.55 (m, 1H), 6.65 (m, 1H), 6.98 (m, 1H), 7. 72 (m, 1H), 7. 96 (m, 1H) [589] [590] Example 125.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclopentylmethyl) carbamoyl) -2-methyl propyl)-3- (quinolin-8-yl) urea [591] 1H-NMR(CDCl ) # 0.88-1. 31 (m, 8H), 1.57-1. 80 (m, 6H), 2.18 (m, 2H), 3.44-3. 65 3 (m, 2H), 4.10 (m, 1H), 4.73-4. 87 (m, 2H), 7.43-7. 59 (m, 3H), 7.94-8. 22 (m, 2H), 8.56-8. 77 (m, 3H) [592] [593] Example 126.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( 4-chloro-2-methoxy-5-methylphenyl) urea <BR> <BR> <BR> [594] 1H-NMR(CDCl3) # 0.83-1.05 (m, 12H), 1.26-1.60 (m, 3H), 1.99 (m, 1H), 2.21 (s, 3H), 3.10-4.38 (m, 8H), 6.71-6.99 (m, 2H), 7.50-7.91 (m,2H) [595] [596] Example 127.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-isopentylcarbamoyl) -2-methylpropyl)-3-( quinolin-8-yl) urea [597] 1H-NMR(CDCl ) # 0.86-1. 14 (m, 12H), 1.40-1. 70 (m, 3H), 2.16 (m, 1H), 3.55 (m, 3 2H), 4.12 (m, 1H), 4.62-4. 87 (m, 2H), 7.43-7. 59 (m, 3H), 7.99-8. 23 (m, 2H), 8.55-8. 79 (m, 3H) [598] [599] Example 128.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3-(4-chloro-2-methoxy-5-methylphenyl) urea [600] 1H-NMR(CDCl ) # 0.96-1. 04 (m, 8H), 1.52-7. 79 (m, 9H), 1.98 (m, 1H), 2.21 (s, 3 3H), 3.03-4. 39 (m, 8H), 6.72-7. 00 (m, 2H), 7.53-7. 91 (m, 2 H) [601] [602] Example 129.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (5-fluoro-2- (pyrrolidin-1-yl) phenyl) urea [603] H-NMR (CDCI) o 0.96-1. 19 (m, 8H), 1.55-1. 96 (m, 14H), 2.99 (m, 4H), 3.38-4. 45 3 (m, 5H), 6.44-7. 00 (m, 3H), 7. 71-7. 85 (m, 2 H) [604] [605] Example 130.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(2-cyclopentylethyl ) carbamoyl) -2-methyl propyl)-3- (quinolin-8-yl) urea <BR> <BR> <BR> [606] 1H-NMR(CDCl3) # 0.88-1.14 (m, 8H), 1.51-1.82 (m, 9H), 2.15 (m, 1H), 3.53 (m, 2H), 4.11 (m, 1H), 4.64-4.46 (m, 2H), 7.43-7.59 (m, 3H), 7.99-8.21 (m, 2H), 8.55-8.79 (m, 3H) [607] [608] Example 131.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (6-methoxyquinolin-8-yl) urea [609] H-NMIWCDC1) b 1.09 (s, 9H), 1.75-1. 89 (m, 6H), 2.50 (m, 1H), 3.50-4. 80 (m, 3 8H), 6.58-6. 76 (m, 2H), 7.62-9. 18 (m, 5H) [610] [611] Example 132.

1-((S)-1-(N-((hydroxyCarbamoyl) methyl)-N-(cyclobutylmethyl) carbamoyl) -2-methylp ropyl)-3- (6-methoxyquinolin-8-yl) urea [612] 1H-NMR(CDCl ) # 0.92-1. 23 (m, 6H), 1.80-1. 93 (m, 6H), 2.63 (m, 1H), 3.57-4. 84 3 (m, 8H), 6.73 (s, 1H), 7.40 (m, 1H), 8.04-8. 76 (m, 5H) [613] [614] Example 133.

1-((S)-1-(N-((hydroxycarbamoyl)methyl)-N-(cyclobutylmethyl) carbamoyl) -2,2-dimeth ylpropyl)-3- (2-hydroxyphenyl) urea [615] 1H-NMR(CDCl ) # 0.99 (s, 9H), 1.63-2. 04 (m, 6H), 2.57 (m, 1H), 3.40-4. 70 (m, 3 5H), 6.74-7. 06 (m, 5H), 7.89 (bs, 1H) [616] [617] Experimental Example 1: Evaluation of deformylase inhibitory activity [618] (1) Production and purification of deformylase [619] Deformylase-produang bacteria strains (Novagen, America, cat. no. 69041) were inoculated into 50 °C LB media (tryptone 8g/1, yeast extract 5g/1, NaCl 5g/1, IN NaOH 2. 5ml) mntaining ampicillin and then cultured at 37 °C. The cultures were then inoculated into new LB media (3L) with the same composition as in the above- described LB media. When O. D (660 nm) reached 0.5, protein expression was induced by addition of 1 mM isopropyl-ß-D-thiogalactopyranoside to the LB media. Then, cell pellets were harvested by centrifugation, incubated at-80 °C for 30 minutes, re- suspended in a phosphate buffer, followed by lysis of bacteria cells by sonification with 8 seconds interval between each pulse (1 second). The supernatant was obtained by ultracentrifugation, loaded onto an affinity column, followed by elution with an elution buffer. The eluted fractions containing peptide deformylase were identified by SDS-PAGE, followed by elution by gel chromatography. At this time, a buffer containing 5 mM NiCl was used as a stabilizer for the enzyme source, and SDS- 2 PAGE and Dynamic Light Scattering were used to identify the purification of the enzyme source. The purified enzyme source was kept at-80 °C until use.

[620] (2) Deformylase inhibition test [621] Each of the compounds prepared in Examples was dissolved in dimethyl sulfoxide to a concentration of 2 mM. 7 (le of each of the reaction mixtures was loaded into each well of microtiter plates. The deformylase as prepared in section (1) was diluted with a buffer (50mM HEPES, pH7.0, 10mM NaCL, 5mM NiCl2, 0.1% Triton X-100) to a con- centration of 250 nM and then loaded into each well of the microtiter plates. Then, continuous dilution for each of the compounds of Examples was performed with a dilution ratio of 7: 2 to make a final volume of 50 0 for each well, followed by incubation at room temperature for 5 minutes. Then, 50 (le of 5 mM formyl- Met-Ala-Ser used as a substrate source was loaded into each well and incubated at 30 °C for 10 minutes to induce enzyme reaction. When the enzyme reaction was completed, the obtained samples were treated with 50 0 of fluorescamine and 50 (le of 50 mM borate-sodium hydroxide buffer (pH 9.5) to measure fluorescence at an excitation wavelength of 390 nm and an emission wavelength of 465 nm. Based on the fluorescence thus measured, the concentrations (IC50) of the samples that decrease enzyme activity by 50% were calculated and the results are presented in Table 1 below.

[622] Table 1 Samples IC50 (nM) Samples IC50 (nM) Example 1 28 Example 41 24 Example 2 25 Example 42 16 Example 3 75 Example 43 16 Example 4 61 Example 44 36 Example 5 63 Example 45 44 Example 6 48 Example 46 33 Example 7 38 Example 47 13 Example 8 52 Example 48 36 Example 9 21 Example 49 13 Example 10 20 Example 50 12 Example 11 224 Example 51 29 Example 12 29 Example 52 30 Example 13 52 Example 53 29 Example 14 54 Example 54 33 Example 15 30 Example 55 31 Example 16 32 Example 56 28 Example 17 38 Example 57 21 Example 18 27 Example 58 20 Example 19 60 Example 59 77 Example 20 31 Example 60 45 Example 21 43 Example 61 57 Example 22 26 Example 62 32 Example 23 51 Example 63 24 Example 24 12 Example 64 29 Example 25 60 Example 65 23 Example 26 52 Example 66 43 Example 27 46 Example 67 26 Example 28 35 Example 68 27 Example 29 68 Example 69 23 Example 30 19 Example 70 27 Example 31 23 Example 71 25 Example 32 20 Example 72 29 Example 33 19 Example 73 28 Example 34 50 Example 74 44 Example 35 62 Example 75 14 Example 36 31 Example 76 109 Example 37 20 Example 77 88 Example 38 24 Example 78 35 Example 39 22 Example 79 42 Example 40 21 Example 80 33 [623] Table 1 (Continued) Samples IC50 (nM) Samples IC50 (nM) Example 81 24 Example 111 66 Example 82 37 Example 112 34 Example 83 31 Example 113 26 Example 84 35 Example 114 27 Example 85 26 Example 115 24 Example 86 36 Example 116 31 Example 87 15 Example 117 32 Example 88 25 Example 118 38 Example 89 23 Example 119 30 Example 90 28 Example 120 31 Example 91 32 Example 121 29 Example 92 34 Example 122 16 Example 93 31 Example 123 35 Example 94 31 Example 124 27 Example 95 38 Example 125 29 Example 96 256 Example 126 25 Example 97 72 Example 127 17 Example 98 31 Example 128 15 Example 99 27 Example 129 28 Example 100 32 Example 130 21 Example 101 28 Example 131 23 Example 102 34 Example 132 37 Example 103 20 Example 133 31 Example 104 23 Example 105 24 Example 106 24 Example 107 29 Example 108 20 Example 109 34 Example 110 72 [624] [625] Experimental Example 2: Antibacterial effect test [626] Minimal inhibitory concentrations (MICs) of the compounds of Examples were determined for Hemophilus influenza (ATCC 51907), Streptococcus pneumoniae (ATCC 6305), and Moraxella cararrhalis (ATCC 43617).

[627] Each of the compounds of Examples was dissolved in dimethyl sulfoxide to a con- centration of 2 mg/ml. At this time, actinonin (Sigma, America) or ampiållin (Sigma, America) was used as standard antibiotic in a concentration of 2 mg/ml.

[628] For bacteria culture, Hemophilus influenza and Moraxella cararrhalis were inoculated into culture media such as brain heart infusion (37 g/1, Duoo, America) sup- plemented with NAD lOmg/1 and hemin 5mg/1 and then cultured for 24 and 48 hours, respectively. Streptococcus pneumoniae was inoculated into GC media containing 5% horse serum and cultured for 48 hours. The cultures were diluted to a concentration of 1 x 106CFU/ml and inoculated into wells of microtiter plates. After incubation at 37 °C , 5% CO for 24 hours for Hemophilus influenza and 48 hours for Moraxella 2 cararrhalis and Streptococcus pneumoniae, MICs, the lowest concentrations able to inhibit visual growth, were determined and the results are presented in Table 2 below.

[629] Table 2 Samples MIC (, ug/ml) Streptococcus Hemophilus Moraxella pneumoniae influenza cararrhalis Example 1 1.6 0.8 0.4 Example 2 0.8 0.2 0.1 Example 3 1.6 0.2 0.2 Example 4 1.6 0.4 0.1 Example 5 1.6 0.4 0.1 Example 6 1.6 0.4 0.1 Example 7 1.6 0.4 0.1 Example 8 1.6 0.4 0.1 Example 9 1.6 0.4 0.1 Example 10 1.6 0.4 0.1 Example 11 0.4 0.1 0.1 Example 12 0.2 0.2 0.1 Example 13 0.2 0.8 0.1 Example 14 0.8 0.4 0.1 Example 15 0.8 0.8 0.1 Example 16 1.6 1.6 0.1 Example 17 0.8 1.6 0.1 Example 18 0.4 1.6 0.1 Example 19 0.8 0.4 0.1 Example 20 0.8 0.2 0.1 Example 21 0.8 0.4 0.1 Example 22 0.8 0.4 0.1 Example 23 0.4 0.8 0.1 Example 24 0.8 0.2 0.1 Example 25 0.8 0.2 0.1 Example 26 0.1 0.1 0.1 Example 27 0.4 0.2 0.1 Example 28 0.4 0.1 0.1 Example 29 0.8 0.2 0.1 Example 30 1.6 0.2 0.1 Example 31 1.6 0.4 0.1 Example 32 1.6 0.2 0.1 Example 33 1.6 0.4 0.1 Example 34 0.4 0.2 0.1 Example 35 0.2 0.1 0.1 Example 36 0.4 0.8 0.1 Example 37 0.8 1.6 0.1 Example 38 0.2 0.8 0.1 Example 39 0.8 0.4 0.1 Example 40 0.8 0.8 0.1 Example 41 1.6 0.2 0.2 Example 42 0.8 1.6 0.1 Example 43 0.4 0.2 0.1 Example 44 1.6 0.2 0.1 Example 45 0.8 0.1 0.1 Example 46 0.4 0.1 0.2 Example 47 0.8 0.8 0.1 Example 48 0.8 0.8 0.1 Example 49 0.4 0.4 0.1 Example 50 0.4 0.4 0.1 Example 51 1.6 0.8 0.8 Example 52 0.8 0.8 0.4 Example 53 1.6 0.8 0.4 Example 54 0.4 0.4 0.1 Example 55 1.6 0.8 0.8 Example 56 1.6 0.8 0.4 Example 57 0.4 0.2 0.1 Example 58 0.4 0.2 0.1 Example 59 1.6 0.2 0.1 Example 60 0.4 0.2 0.1 Example 61 0.4 0.1 0.1 Example 62 0.8 0.2 0.1 Example 63 0.8 0.4 0.1 Example 64 0.4 0.2 0.1 Example 65 1.6 0.4 0.2 Example 66 0.8 0.4 0.1 Example 67 0.2 0.2 0.1 Example 68 0.8 0.8 0.8 Example 69 1.6 1.6 0.4 Example 70 1.6 1.6 0.4 Example 71 0.8 0.8 0.2 Example 72 0.8 0.4 0.2 Example 73 1.6 1.6 0.4 Example 74 0.2 0.1 0.1 Example 75 0.8 0.8 0.2 Example 76 1.6 0.4 0.1 Example 77 1.6 0.4 0.4 Example 78 0.1 0.1 0.1 Example 79 0.1 0.1 0.1 Example 80 0.8 1.6 0.1 Example 81 0.2 0.2 0.1 Example 82 0.1 0.1 0.1 Example 83 0.1 0.2 0.1 Example 84 0.1 0.1 0.1 Example 85 0.1 0.2 0.1 Example 86 0.4 0.2 0.1 Example 87 0.4 0.8 0.1 Example 88 0.2 0.1 0.1 Example 89 0.2 0.1 0.1 Example 90 0.1 0.1 0.2 Example 91 0.2 0.2 0.4 Example 92 0.4 0.4 0.1 Example 93 0.8 0.8 0.8 Example 94 0.8 0.4 0.1 Example 95 0.1 0.1 0.1 Example 96 1.6 0.1 0.1 Example 97 0.2 0.1 0.1 Example 98 1.6 0.4 0.2 Example 99 0.8 0.8 0.1 Example 100 0.1 1.6 0.1 Example 101 0.8 0.2 0.1 Example 102 0.8 0.4 0.1 Example 103 1.6 1.6 0.1 Example 104 0.1 0.2 0.1 Example 105 0.2 0.8 0.1 Example 106 0.4 0.1 0.1 Example 107 0.8 0.2 0.1 Example 108 0.8 0.1 0.1 Example 109 1.6 0.4 0.1 Example 110 0.1 0.1 0.1 Example 111 0. 1 0.8 0.4 Example 112 0.1 0.1 0.1 Example 113 0.1 0.8 0.2 Example 114 0.1 0.1 0.1 Example 115 0.1 0.2 0.1 Example 116 0.1 0.4 0.1 Example 117 0.1 0.1 0.1 Example 118 0.4 0.8 0.1 Example 119 0.1 0.1 0.1 Example 120 0.1 0.1 0.1 Example 121 0.8 1.6 0.2 Example 122 0.1 0.4 0.1 Example 123 0.1 0.2 0.1 Example 124 1.6 1.6 0.2 Example 125 0.1 0.2 0.1 Example 126 0.1 0.4 0.1 Example 127 0.1 0.8 0.1 Example 128 0.2 0.1 0.1 Example 129 1.6 1.6 0.1 Example 130 0.2 0.1 0.1 Example 131 0.1 0. 1 0. 4 Example 132 0.1 0.1 0.2 Example 133 1.6 0.8 0.1