IP Library › Granted Patent US 7,342,013
Granted Patent B2
US 7,342,013 · App. 11/442,060 · Granted Mar 11, 2008

Benzamides and related inhibitors of factor Xa

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Quick Facts
Patent No.
US 7,342,013
App. No.
11/442,060
Granted
Mar 11, 2008
Kind
B2
Abstract

Novel benzamide compounds including their pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives having activity against mammalian factor Xa are described. Compositions containing such compounds are also described. The compounds and compositions are useful in vitro or in vivo for preventing or treating coagulation disorders.

Claims (35)

1. A compound of the formula:

wherein:

A-Q is selected from the group consisting of:

R 1a is hydrogen or fluoro,

R 1d1 is selected from the group consisting of H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH 2 , —NMe 2 , —NHMe, —NHSO 2 Me, —NHCOMe, —CH 3 , —CF 3 , —OH, —OCH 3 , —SCH 3 , —OCF 3 , —OCH 2 F, —OCHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —NO 2 , —CN, —CO 2 H, —CO 2 Me, —CO 2 Et, —CONH 2 , —CONHMe, —CONMe 2 , —SO 2 NH 2 , —SO 2 CH 3 , —SO 2 NMe 2 , —CH 2 OH, —CH 2 NH 2 , —CH 2 NHMe, —CH 2 NMe 2 , —OCH 2 CO 2 H, —OCH 2 CO 2 Me, —OCH 2 CO 2 Et, —OCH 2 CONH 2 , —OCH 2 CONMe 2 , —OCH 2 CONHMe, —OCH 2 CH 2 OMe, —OCH 2 CH 2 OEt, —OCH 2 CH 2 NH 2 , —OCH 2 CH 2 NHMe, —OCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 OMe, —SCH 2 CH 2 OMe, —SO 2 CH 2 CH 2 OMe, —OCH 2 CH 2 SO 2 Me, —NHCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 NMe 2 , —N(CH 2 CH 2 OH) 2 ; —N(CH 2 CH 2 OMe) 2 , —NHCH 2 CO 2 H, —NHCH 2 CO 2 ,Et, —NHCH 2 CO 2 Et, —NHCH 2 CONH 2 , —NHCH 2 CONMe 2 , —NHCH 2 CONHMe, —N(CH 3 )CH 2 CO 2 H, —N(CH 3 )CH 2 CO 2 Et, —(NMe)CH 2 COOH, —N(Me)CH 2 CONH 2 , —N(Me)CH 2 CH 2 NMe 2 , —N(Me)CH 2 CH 2 OMe, —NHCH 2 CH 2 OMe,

or a pharmaceutically acceptable isomer, salt, hydrate, solvate or prodrug thereof.

2. The compound of claim 1 , wherein A-Q is

3. The compound of claim 2 , wherein R 1a is hydrogen.

4. The compound of claim 2 , wherein R 1d1 is hydroxy.

5. A compound of the formula:

wherein:

A-Q is a member selected from the group consisting of:

R 1a is hydrogen or fluoro;

R 1e is a member selected from the group consisting of hydrogen, —F, —SO 2 Me, —SO 2 NH 2 , —CN, —CONH 2 , —CH 2 NH 2 , and —CH 2 NMe 2

R 1d3 is selected from the group consisting of -Me, —F, chloro, bromo, aryl, heteroaryl, —NH 2 , —NMe 2 , —NHMe, —NHSO 2 Me, —NHCOMe, —CH 3 , —CF 3 , —OCH 3 , —SCH 3 , —OCF 3 , —OCH 2 F, —OCHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —NO 2 , —CN, —CO 2 H, —CO 2 Me, —CO 2 Et, —CONH 2 , —CONHMe, —CONMe 2 , —SO 2 NH 2 , —SO 2 CH 3 , —SO 2 NMe 2 , —CH 2 OH, —CH 2 NH 2 , —CH 2 NHMe, —CH 2 NMe 2 , —OCH 2 CO 2 H, —OCH 2 CO 2 Me, —OCH 2 CO 2 Et, —OCH 2 CONH 2 , —OCH 2 CONMe 2 , —OCH 2 CONHMe, —OCH 2 CH 2 OMe, —OCH 2 CH 2 OEt, —OCH 2 CH 2 NH 2 , —OCH 2 CH 2 NHMe, —OCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 OMe, —SCH 2 CH 2 OMe, —SO 2 CH 2 CH 2 OMe, —OCH 2 CH 2 SO 2 Me, —NHCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 NMe 2 , —N(CH 2 CH 2 OH) 2 ; —N(CH 2 CH 2 OMe) 2 , —NHCH 2 CO 2 H, —NHCH 2 CO 2 Et, —NHCH 2 CO 2 Et, —NHCH 2 CONH 2 , —NHCH 2 CONMe 2 , —NHCH 2 CONHMe, —N(CH 3 )CH 2 CO 2 H, —N(CH 3 )CH 2 CO 2 Et, —(NMe)CH 2 COOH, —N(Me)CH 2 CONH 2 , —N(Me)CH 2 CH 2 NMe 2 , —N(Me)CH 2 CH 2 OMe, —NHCH 2 CH 2 OMe,

or a pharmaceutically acceptable isomer, salt, hydrate, solvate or prodrug thereof.

6. The compound of claim 5 , wherein A-Q is

7. The compound of claim 6 , wherein R 1a is hydrogen.

8. The compound of claim 7 , wherein R 1d3 is chloro.

9. The compound of claim 8 , wherein R 1e is hydrogen.

10. A compound of the formula:

wherein:

R 1a is hydrogen or fluoro;

A-Q is a member selected from the group consisting of

R 1d1 is a member selected from the group consisting of —H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH 2 , —NMe 2 , —NHMe, —NHSO 2 Me, —NHCOMe, —CH 3 , —CF 3 , —OH, —OCH 3 , —SCH 3 , —OCF 3 , —OCH 2 F, —OCHF 2 , —OCH 2 CF 3 , —OCF 2 CF 3 , —NO 2 , —CN, —CO 2 H, —CO 2 Me, —CO 2 Et, —CONH 2 , —CONHMe, —CONMe 2 , —SO 2 NH 2 , —SO 2 CH 3 , —SO 2 NMe 2 , —CH 2 OH, —CH 2 NH 2 , —CH 2 NHMe, —CH 2 NMe 2 , —OCH 2 CO 2 H, —OCH 2 CO 2 Me, —OCH 2 CO 2 Et, —OCH 2 CONH 2 , —OCH 2 CONMe 2 , —OCH 2 CONHMe, —OCH 2 CH 2 OMe, —OCH 2 CH 2 OEt, —OCH 2 CH 2 NH 2 , —OCH 2 CH 2 NHMe, —OCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 OMe, —SCH 2 CH 2 OMe, —SO 2 CH 2 CH 2 OMe, —OCH 2 CH 2 SO 2 Me, —NHCH 2 CH 2 NMe 2 , —NHCH 2 CH 2 NMe 2 , —N(CH 2 CH 2 OH) 2 ; —N(CH 2 CH 2 OMe) 2 , —NHCH 2 CO 2 H, —NHCH 2 CO 2 Et, —NHCH 2 CO 2 Et, —NHCH 2 CONH 2 , —NHCH 2 CONMe 2 , —NHCH 2 CONHMe, —N(CH 3 )CH 2 CO 2 H, —N(CH 3 )CH 2 CO 2 Et, —(NMe)CH 2 COOH, —N(Me)CH 2 CONH 2 , —N(Me)CH 2 CH 2 NMe 2 , —N(Me)CH 2 CH 2 OMe, —NHCH 2 CH 2 OMe,

R 1d3 is a member selected from the group consisting of:

—F, —Cl, —Br, —OCH 3 , —OCF 3 , —OCH 2 F, —OCHF 2 , —OCH 2 CF 3 , OCF 2 CF 3 ; and

X is a member selected from the group consisting of

or a pharmaceutically acceptable isomer, salt, hydrate, solvate and prodrug derivatives thereof.

11. The compound of claim 10 , wherein A-Q is

12. The compound of claim 11 , wherein R 1a is hydrogen.

13. The compound of claim 12 , wherein R 1d1 is —OH.

14. The compound of claim 13 , wherein R 1d3 is —Cl or —Br.

15. The compound of claim 14 , wherein X is

16. A pharmaceutical composition for treating a condition in a mammal characterized by undesired thrombosis comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of one of claims 1 , 5 , or 10 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2012
From: ZHU, BING-YAN; ZHANG, PENGLIE; WANG, LINGYAN; HUANG, WENRONG; GOLDMAN, ERICK A.; LI, WENHAO; ZUCKETT, JINGMEI; SONG, YONGHONG; SCARBOROUGH, ROBERT M.
To: COR THERAPEUTICS, INC.
Reel/Frame 029502/0737 →
MERGER Recorded Dec 19, 2012
From: COR THERAPEUTICS, INC.
To: MILLENNIUM PHARMACEUTICALS, INC.
Reel/Frame 029504/0084 →