Title:
HSV PRIMASE INHIBITORS
Document Type and Number:
WIPO Patent Application WO/2000/058270
Kind Code:
A2
Abstract:
The invention provides compounds of formula (1) that are active against the HSV primase enzyme: wherein R¿1? is hydroxy or amino; R¿2? is hydrogen, halo, (C¿1-4?)alkyl or (C¿1-4?)alkoxy; R¿3? is hydrogen, halo, (C¿1-4?)alkyl, (C¿1-4?)alkoxy, amino or azido; R¿4? has the same significance as R¿2?; R¿5? is hydrogen or (C¿1-4?)alkyl; and R is (C¿1-7?)alkyl, (C¿3-6?)cycloalkyl, {phenyl(C¿1-7?)alkyl}, {phenyl(C¿1-7?)alkoxy}, {{(monocyclic heterocyclo)-{(C¿1-7?)alkoxy}}, CH(W)C(O){O-(C¿1-4?)alkyl} wherein W is hydrogen or (C¿1-7?)alkyl, or (a) wherein Y is hydrogen or (C¿1-7?)alkyl, and Z is (C¿1-7?)alkyl, (C¿3-6?) cycloalkyl, {(C¿3-6?)cycloalkyl}-{(C¿1-7?)alkyl}, phenyl(C¿1-7?)alkyl or {{(monocyclic heterocyclo)-{(C¿1-7?)alkyl}}, or Y and Z together with the nitrogen atom to which they are attached represent, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl or 1-(4-methylpiperazinyl); with the provisos that (1) when R is CH(W)C(O)-{O-(C¿1-4?)alkyl} as defined herein, then R¿5? is hydrogen; and (2) at least one of R¿2?, R¿3? and R¿4? is other than hydrogen.
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Inventors:
SIMONEAU BRUNO (CA)
LIUZZI MICHELE (CA)
MENTRUP ANTON (DE)
LIUZZI MICHELE (CA)
MENTRUP ANTON (DE)
Application Number:
PCT/CA2000/000324
Publication Date:
October 05, 2000
Filing Date:
March 23, 2000
Export Citation:
Assignee:
BOEHRINGER INGELHEIM CA LTD (CA)
SIMONEAU BRUNO (CA)
LIUZZI MICHELE (CA)
MENTRUP ANTON (DE)
SIMONEAU BRUNO (CA)
LIUZZI MICHELE (CA)
MENTRUP ANTON (DE)
International Classes:
A61K31/165; C07D295/18; A61K31/167; A61K31/4402; A61K31/4453; A61K31/52; A61K31/522; A61K31/535; A61K31/7068; A61K38/17; A61K45/06; A61K48/00; A61P31/22; C07C235/00; C07C235/60; C07C235/62; C07C235/64; C07C237/30; C07C237/38; C07C237/40; C07C237/42; C07C237/44; C07C247/18; C07D213/30; C07D213/40; C07D295/192; (IPC1-7): C07C235/00
Foreign References:
| EP0497816A1 | 1992-08-12 | |||
| US5258407A | 1993-11-02 |
Other References:
DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KONDRAT'EV, V. P. ET AL: "Effectiveness of novel salicylanilide derivatives for the treatment of fascioliasis in livestock" retrieved from STN Database accession no. 104:101982 CA XP002155157 & DOKL. VSES. AKAD. S-KH. NAUK IM. V. I. LENINA (1985), (9), 32-4 , 1985,
Attorney, Agent or Firm:
Bernier, Louise G. (Quebec H7S 2G5, CA)
Download PDF:
Claims:
What is claimed is:
| 1. | A compound of formula 1 wherein R, is hydroxy or amino; R2 is hydrogen, halo, (C14)alkyl or (Ci4) atkoxy; R3 is hydrogen, halo, (C14)alkyl, (C14)alkoxy, amino or azido; R4 has the same significance as R2; R5 is hydrogen or (Ct 4) alkyl; and R is (C36)cycloalkyl, {{(monocyclicheterocyclo){(C1{phenyl(C17)alkyl),{phenyl(C17)alkoxy}, 7) alkoxy}}, CH (W) C (O) {0 (Ci. 4) alkyl} wherein W is hydrogen or (C17) alkyl, or wherein Y in hydrogen or (C17) alkyl, and Z is (C1. 7) alkyl, (C3. 6)cycloalkyl, { (C3_6) cycloalkyl} or{{(monocyclicheterocyclo)((C17)alkyl}},or{(C17)alkyl},phenyl(C17)alkyl Y and Z together with the nitrogen atom to which they are attached represent, 1pyrrolidinyl, 1piperidinyl, 4morpholinyl or 1 (4 methylpiperazinyl); with the provisos that (1) when R is CH (W) C (O) {O(C14)alkyl} as defined herein, then R5 is hydrogen; and (2) at least one of R2, R3 and R4 is other than hydrogen; or a salt thereof. |
| 2. | A compound according to claim 1, wherein R, is hydroxy. |
| 3. | A compound according to claim 1, wherein R2 is hydrogen or halo. |
| 4. | A compound according to claim 1, wherein R2 is hydrogen or chloro. |
| 5. | A compound according to claim 1, wherein R2 is hydrogen. |
| 6. | A compound according to claim 1, wherein R3 is hydrogen, chloro, methyl, methoxy, amino or azido. |
| 7. | A compound according to claim 1, wherein R3 is methyl, methoxy, amino or azido. |
| 8. | A compound according to claim 1, wherein R4 is hydrogen or halo. |
| 9. | A compound according to claim 1, wherein R4 is hydrogen, chloro or iodo. |
| 10. | A compound according to claim 1, wherein R5 is hydrogen or methyl. |
| 11. | A compound according to claim 1, wherein R5 is hydrogen. |
| 12. | A compound according to claim 1, wherein R is methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopentyl, cyclohexyl, phenylmethyl, 2phenylethyl, phenylmethoxy, 2phenylethoxy, 2, 3or 4pyridinylmethoxy, 2 (2, 3 or 4 pyridinyl) ethoxy, CH2C (O) {O{(C1. 4) alkyl}}, cyclopentylamino,CH{(C17)alkyl}C(O){OC14)alkyl},(C17)alkylamino, cyclohexylamino, (cyclohexylmethyl) amino, (2cyclohexylethyl) amino, (phenylmethyl) amino, (2phenylethyl) amino, 2 (3 or (4pyridylmethyl) amino or 2 (2, (3or (4pyridylethyl) amino. |
| 13. | A compound according to claim 1 wherein R is pentyl, hexyl, cyclohexyl, phenylmethyl, 2phenylethyl, phenylmethoxy, 2, 3or 4 pyridinylmethoxy, CH2C (O) OCH2CH3, CH (CH2CH2CH2CH3) C (O) OCH2CH3, ethylamino, propylamino, butylamino, cyclohexylamino, (cyclohexylmethyl) amino, (2cyclohexylethyl) amino, (phenylmethyl) amino, (2 phenylethyl) amino, or (2, (3or (4pyridylmethyl) amino, or 2 (2, (3, or (4 pyridinylethyl) amino. |
| 14. | A pharmaceutical composition for the treatment or prevention of a disease or condition involving herpes virus, comprising an effective amount of a compound according to claim 1, and a pharmaceutically acceptable carrier or auxiliary agent. |
| 15. | Use of a compound according to claim 1, for the manufacture of a medicament for treating a herpes virus infection in a mammal. |
| 16. | The use of claim 15, wherein said medicament is administered to said mammal in conjunction with an additional antiviral agent. |
| 17. | The use of claim 16, wherein the addition antiviral agent is selected from acyclovir, pencyclovir, famciclovir, valaciclovir and ganciclovir. |
| 18. | A method for inhibiting herpes virus replication, comprising exposing cells infected with herpes virus to a compound according to claim 1. |
| 19. | A compound selected from: , and , or a salt thereof. |
Description:
INTERNATIONAL SEARCH REPORT Inten nal Application No PCT/CA 00/00324 C. (Continuation) DOCUMENTS CONSIDERED TO BE RELEVANT Category Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. A DATABASE CHEMABS'Online ! 1,14,15, CHEMICAL ABSTRACTS SERVICE, COLUMBUS, 18,19 OHIO,US; KONDRAT'EV, V. P. ET AL:"Effectiveness of novel salicylanilide derivatives for the treatment of fascioliasis in livestock" retrieved from STN Database accession no. 104: 101982 CA XP002155157 abstract &DOKL. VSES. AKAD. S-KH. NAUK IM. V. I. LENINA (1985), (9), 32-4, 1985, 2 INTERNATIONAL SEARCH RETORT Inten nal Application No informationon patent family members PCT/CA 00/00324 Patent document Publication Patent family Publication cited in search report date member (s) date EP 0497816 A 12-08-1992 US 5268389 A 07-12-1993 BR 9007758 A 11-08-1992 DE 69019533 D 22-06-1995 DE 69019533 T 26-10-1995 GR 3017128 T 30-11-1995 JP 6102641 B 14-12-1994 KR 222233 B 01-10-1999 RU 2108785 C 20-04-1998 AT 122654 T 15-06-1995 AU 636409 B 29-04-1993 AU 6603590 A 16-05-1991 CA 2067381 A 17-04-1991 CN 1051036 A 01-05-1991 DK 497816 T 09-10-1995 HU 60713 A 28-10-1992 IL 95956 A 31-03-1996 JP 4507422 T 24-12-1992 WO 9105761 A 02-05-1991 US 5693827 A 02-12-1997 ZA 9008094 A 28-08-1991 US 5258407 A 02-11-1993 US 5466715 A 14-11-1995
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