IP Library Granted Patent US 8,273,770
Granted Patent B2
US 8,273,770 · App. 12/176,144 · Granted Sep 25, 2012

5-pyridinone substituted indazoles

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Quick Facts
Patent No.
US 8,273,770
App. No.
12/176,144
Granted
Sep 25, 2012
Kind
B2
Abstract

5-pyridinone substituted indazoles of the formula and methods of their use are presented.

Claims (33)

1. A compound of formula I:

wherein

n is 0 or 1;

R is an optionally substituted pyrrolidin-1-yl;

R 3 and R 4 are each independently H or alkyl;

B is selected from aryl, and cycloalkyl;

R 5 , R 6 , R 7 are each independently selected from H, —OH, —O-alkyl, alkyl, halo, —CF 3 , —CN, and —O-aryl; and

R 14 is H or —OH;

wherein optional substituents are selected from the group consisting of alkyl, halogen, haloalkyl, hydroxy, lower alkoxy, carboxy, carboalkoxy, carboxamido, cyano, carbonyl, nitro, amino, alkylamino, dialkylamino, mercapto, alkylthio, sulfoxide, sulfone, acylamino, amidino, phenyl, benzyl, heteroaryl, phenoxy, benzyloxy, and heteroaryloxy; and

provided that when n is 0, R 3 and R 4 are H and R is pyrrolidin-1-yl, then

when B is phenyl which is substituted at the 2-position by methoxy or at the 3-position by methyl, there is at least one additional substituent on the phenyl ring;

or pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 , wherein R is selected from the group consisting of pyrrolidin-1-yl, 3-hydroxypyrrolidin-1-yl, and 3-hydroxymethylpyrrolidin-1-yl.

3. A compound according to claim 1 , wherein R is selected from S-3-hydroxypyrrolidin-1-yl, R-3-hydroxypyrrolidin-1-yl, S-3-hydroxymethylpyrrolidin-1-yl, and R-3-hydroxymethylpyrrolidin-1-yl.

4. A compound according to claim 3 , wherein R 3 and R 4 are both H.

5. A compound according to claim 1 , wherein B, taken together with R 5 , R 6 and R 7 , is 4-trifluoromethylphenyl and n is 1.

6. A compound according to claim 5 , wherein R 14 is —OH.

7. A compound according to claim 1 , wherein n is 0.

8. A compound according to claim 1 , wherein n is 1.

9. A compound according to claim 1 , wherein B is phenyl.

10. A compound according to claim 9 , wherein B, taken together with R 5 , R 6 and R 7 , is selected from the group consisting of phenyl, 4-chlorophenyl, 4-fluorophenyl, 3-chlorophenyl, 3-phenoxyphenyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2,4-dichlorophenyl, 4-methylphenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 4-methoxyphenyl, 2-cyano-4-fluorophenyl, 2,4-dimethoxyphenyl, 2,4-difluorophenyl, 4-isopropoxyphenyl, 2,4-di-trifluoromethylphenyl, 4-n-butoxy-2-methylphenyl, 2-methylphenyl, 4-benzyloxy-2-methylphenyl, 4-chloro-2-methoxyphenyl, 4 methoxy-2-methylphenyl, 2-chloro-4-trifluoromethylphenyl, 4-chloro-2-fluorophenyl, 4-trifluoromethyl-2-fluorophenyl, 4-methoxy-2-fluorophenyl, 4-methoxy-2-chlorophenyl, 4-ethoxyphenyl, 4-trifluoromethoxy-2-fluorophenyl, and 4-trifluoromethoxy-2-methylphenyl.

11. A compound according to claim 1 , wherein B, taken together with R 5 , R 6 and R 7 , is selected from napthalen-1-yl and naphthalen-2-yl.

12. A compound according to claim 1 , wherein B, taken together with R 5 , R 6 and R 7 , is selected from 4-methylcyclohex-1-enyl.

13. A compound according to claim 1 , wherein B, taken together with R 5 , R 6 and R 7 , is selected from 4-methylcyclohex-1-yl.

14. A compound according to claim 1 , wherein the compound is selected from the group consisting of:

15. A compound according to claim 14 , which is a pharmaceutically acceptable salt thereof.

16. A compound according to claim 1 , wherein the compound is selected from the group consisting of:

17. A compound according to claim 16 , which is a pharmaceutically acceptable salt thereof.

18. A compound according to claim 1 , wherein the compound is selected from the group consisting of:

19. A compound according to claim 18 , which is a pharmaceutically acceptable salt thereof.

20. A compound according to claim 1 , wherein the compound is selected from the group consisting of:

21. A compound according to claim 20 , which is a pharmaceutically acceptable salt thereof.

22. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, excipient or diluent therefor.

Assignments (10)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT PATENT NO. 7541537 PREVIOUSLY RECORDED AT REEL: 034045 FRAME: 0951. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Aug 14, 2018
From: ALBANY MOLECULAR RESEARCH, INC.; ALO ACQUISITION LLC; AMRI BURLINGTON, INC.; AMRI RENSSELAER, INC.; CEDARBURG PHARMACEUTICALS, INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC
To: BARCLAYS BANK PLC, AS THE COLLATERAL AGENT
Reel/Frame 046796/0352 →
RELEASE OF SECURITY INTEREST Recorded Aug 31, 2017
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: ALBANY MOLECULAR RESEARCH, INC.; ALO ACQUISITION LLC; AMRI BURLINGTON, INC.; AMRI RENSSELAER, INC.; CEDARBURG PHARMACEUTICALS, INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC; AMRI SSCI, LLC; EUTICALS INC.
Reel/Frame 043742/0085 →
SECURITY INTEREST Recorded Oct 24, 2014
From: ALBANY MOLECULAR RESEARCH, INC.; ALO ACQUISITION LLC; AMRI BURLINGTON, INC.; AMRI RENSSELAER, INC.; CEDARBURG PHARMACEUTICALS, INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC
To: BARCLAYS BANK PLC, AS THE COLLATERAL AGENT
Reel/Frame 034045/0951 →
RELEASE OF SECURITY INTEREST Recorded Jul 9, 2014
From: WELLS FARGO
To: ALBANY MOLECULAR RESEARCH, INC.
Reel/Frame 033283/0357 →
SECURITY AGREEMENT Recorded Apr 20, 2012
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; AMRI BOTHELL RESEARCH CENTER, INC.; AMRI RENESSELAER, INC.
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 028078/0227 →
TERMINATION Recorded Apr 19, 2012
From: BANK OF AMERICA, N.A.
To: ALBANY MOLECULAR RESEARCH, INC.; AMRI BOTHELL RESEARCH CENTER, INC.; AMRI BURLINGTON, INC.; AMRI RENESSELAER, INC.
Reel/Frame 028072/0335 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jun 6, 2011
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI RENSSELAER, INC.; AMRI BOTHELL RESEARCH CENTER, INC.; AMRI BURLINGTON, INC.
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 026397/0001 →
MERGER Recorded Feb 8, 2010
From: AMR TECHNOLOGY, INC.
To: ALBANY MOLECULAR RESEARCH, INC.
Reel/Frame 023905/0317 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2009
From: AMR TECHNOLOGY, INC.
To: ALBANY MOLECULAR RESEARCH, INC.
Reel/Frame 023057/0995 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2008
From: GUZZO, PETER; SURMAN, MATTHEW DAVID; HENDERSON, ALAN JOHN; HADDEN, MARK
To: AMR TECHNOLOGY, INC.
Reel/Frame 021730/0155 →