IP Library Granted Patent US 8,101,632
Granted Patent B2
US 8,101,632 · App. 12/522,709 · Granted Jan 24, 2012

5-furopyridinone substituted indazoles

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Quick Facts
Patent No.
US 8,101,632
App. No.
12/522,709
Granted
Jan 24, 2012
Kind
B2
Abstract

Compounds are disclosed. The compounds act as MCH1 modulators. Other embodiments are also disclosed.

Claims (31)

1. A compound of formula I:

or a pharmaceutically acceptable salt form wherein

n is 1 or 2;

R is NR 1 R 2 , wherein R 1 and R 2 are each independently selected from H and optionally substituted alkyl, or R 1 and R 2 , together with the N atom to which they are attached, form a 4-7 membered optionally substituted heterocyclic ring which optionally contains 1 or 2 heteroatoms in addition to the N atom shown;

R 3 and R 4 are each independently selected from H and alkyl, or R, R 3 and R 4 may combine to form an optionally substituted imidazolin-2-yl;

B is aryl or heteroaryl; and

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

provided that the compound is not one of the following:

2. A compound according to claim 1 , wherein R is selected from the group consisting of pyrrolidin-1-yl, 2-hydroxymethylpyrrolidin-1-yl, 3-hydroxypyrrolidin-1-yl, and morpholin-4-yl and piperazin-1-yl.

3. A compound according to claim 1 , wherein R is selected from S-2-hydroxymethylpyrrolidin-1-yl, R-2-hydroxymethylpyrrolidin-1-yl, S-3-hydroxypyrrolidin-1-yl and R-3-hydroxypyrrolidin-1-yl.

4. A compound according to claim 1 , wherein R 3 and R 4 are both H.

5. A compound according claim 1 , wherein R, R 3 and R 4 combine to form an imidazolin-2-yl which is optionally independently substituted at each of the 1-, 4- and 5- positions with alkyl.

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

7. A compound according to claim 1 , wherein n is 2.

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

9. A compound according to claim 8 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, 2-chlorophenyl, 4-trifluoromethylphenyl, 2-cyano-4-fluorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 2-chloro-4-fluorophenyl, 4-chloro-2-methoxyphenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-4-methylphenyl and 4-methylphenyl.

10. A compound according to claim 1 , wherein B is pyridine.

11. A compound according to claim 10 wherein B, taken together with R 5 , R 6 and R 7 , is selected from the group consisting of 5-chloropyridin-2-yl, pyridin-3-yl, 5-fluoropyridin-2-yl, and pyridin-2-yl.

12. A compound according to claim 1 wherein B is pyridazine.

13. A compound according to claim 12 wherein B, taken together with R 5 , R 6 and R 7 , is 6-methylpyridazine-3-yl.

14. A compound according to claim 1 wherein B is pyrimidine.

15. A compound according to claim 14 wherein B, taken together with R 5 , R 6 and R 7 , is pyrimidin-2-yl.

16. A compound according to claim 1 , wherein R 5 , R 6 , R 7 are each independently selected from H, —O-alkyl, alkyl, halo, —CF 3 , and —CN.

17. A compound according claim 1 which is selected from the following:

18. A compound according to claim 1 which is in pharmaceutically acceptable salt form.

19. A compound according to claim 18 which is the HCl salt form.

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

21. A method of treating obesity, comprising administering to a patient in need of obesity reduction an obesity-reducing effective amount of a compound according to claim 1 , wherein treating does not include prevention.

22. A method of treating anxiety, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound according to claim 1 , wherein treating does not include prevention.

23. A method of treating depression, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound according to claim 1 , wherein treating does not include prevention.

24. A method of treating non-alcoholic fatty liver disease, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound according to claim 1 , wherein treating does not include prevention.

Assignments (6)
ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY, RECORDED ON SEPTEMBER 1, 2017, AT REEL/FRAME 043746/0621 Recorded Mar 17, 2025
From: BARCLAYS BANK PLC, AS EXISTING AGENT
To: APOLLO ADMINISTRATIVE AGENCY LLC, AS SUCCESSOR AGENT
Reel/Frame 070531/0279 →
RELEASE OF SECURITY INTEREST Recorded Oct 29, 2020
From: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
To: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC
Reel/Frame 054252/0687 →
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 →
FIRST LIEN SECURITY AGREEMENT Recorded Sep 1, 2017
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING, LLC-BY ITS SOLE MEMBER: ALO ACQUISITION LLC
To: BARCLAYS BANK, PLC AS COLLATERAL AGENT
Reel/Frame 043746/0621 →
SECOND LIEN SECURITY AGREEMENT Recorded Sep 1, 2017
From: ALBANY MOLECULAR RESEARCH, INC.; AMRI BURLINGTON, INC.; CEDARBURG PHARMACEUTICALS, INC.; EUTICALS INC.; OSO BIOPHARMACEUTICALS MANUFACTURING LLC-BY ITS SOLE MEMBER:ALO ACQUISITION LLC
To: MORGAN STANLEY SENIOR FUNDING, INC.
Reel/Frame 043746/0657 →
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 →