Cannabinoid receptor ligands

• US 7,507,767 B2
• Filed: 02/06/2002
• Issued: 03/24/2009
• Est. Priority Date: 02/08/2001
• Status: Expired due to Fees

• Current Assignee: Merck Sharp & Dohme Corporation (Merck & Co., Inc.)
• Original Assignee: Schering Corporation (Merck & Co., Inc.)
• Inventors: Shih, Neng-Yang, Lavey, Brian J., Tong, Ling, Shankar, Bandarpalle B., Kozlowski, Joseph A., Wolin, Ronald L., Wong, Michael K., Rizvi, Razia K., Spitler, James M.
• Primary Examiner(s): Saeed; Kamal A
• Assistant Examiner(s): Coppins; Janet L
• Application Number:
  US10/072,354
• Publication Number:
  US 20030096844A1
• Time in Patent Office: 2,603 Days
• Field of Search: 568/34, 568/30, 546/294, 546/192, 564/341, 564/161, 564/305, 548/560, 514/709, 514/315, 514/336, 514/422, 514/615, 514/646
• US Class Current: 514/615
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/02 Nasal agents, e.g. decongestants
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 11/08 Bronchodilators
• CPC Class Codes: A61P 11/16 Central respiratory analeptics
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 21/04 for myasthenia gravis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/06 Antiglaucoma agents or miotics
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 35/02 : specific for leukemia
• CPC Class Codes: A61P 37/00 : Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 37/06 : Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: A61P 37/08 : Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/14 : Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
• CPC Class Codes: C07C 2601/02 : with a three-membered ring
• CPC Class Codes: C07C 2601/08 : the ring being saturated
• CPC Class Codes: C07C 2601/14 : The ring being saturated
• CPC Class Codes: C07C 2603/74 : Adamantanes
• CPC Class Codes: C07C 31/24 : Tetrahydroxylic alcohols, e.g. pentaerythritol
• CPC Class Codes: C07C 317/22 : with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 317/32 : with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 317/36 : with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
• CPC Class Codes: C07C 317/44 : having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• CPC Class Codes: C07C 323/41 : Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07C 323/65 : containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
• CPC Class Codes: C07D 213/70 : Sulfur atoms
• CPC Class Codes: C07D 213/71 : to which a second hetero atom is attached
• CPC Class Codes: C07D 213/74 : Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• CPC Class Codes: C07D 213/89 : with hetero atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 215/36 : Sulfur atoms C07D215/24 takes precedence
• CPC Class Codes: C07D 233/42 : Sulfur atoms
• CPC Class Codes: C07D 233/84 : Sulfur atoms
• CPC Class Codes: C07D 239/38 : One sulfur atom
• CPC Class Codes: C07D 307/64 : Sulfur atoms
• CPC Class Codes: C07D 333/20 : by nitrogen atoms nitro, nitroso radicals C07D333/12
• CPC Class Codes: C07D 333/34 : Sulfur atoms
• CPC Class Codes: C07D 333/38 : Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

There are disclosed compounds of the formula

a prodrug thereof, or a pharmaceutically acceptable salt, solvate or stereoisomer of the compound or of said prodrug; which exhibit anti-inflammatory and immunodulatory activity. Also disclosed are pharmaceutical compositions containing said compounds and methods of using the compounds for the treatment of various diseases and conditions.

Claims

1. A compound of the formula

2. The compound according to claim 1 of the formula

3. The compound according to claim 1 of the formula

4. The compound according to claim 1 of the formula

5. The compound according to claim 1 of the formula

6. The compound according to claim 1 of the formula

7. The compound according to claim 1 of the formula

8. The compound according to claim 1 of the formula

9. The compound according to claim 1 of the formula

10. The compound according to claim 1 of the formula

11. The compound according to claim 1 of the formula

12. The compound according to claim 1 of the formula

13. The compound according to claim 1 of the formula

14. The compound according to claim 1 of the formula

15. The compound according to claim 1 of the formula

16. The compound according to claim 1 of the formula

17. The compound according to claim 1 of the formula

18. The compound according to claim 1 of the formula

19. The compound according to claim 1 of the formula

20. A pharmaceutical composition comprising an effective amount of a compound, a prodrug thereof, or a pharmaceutically acceptable salt, or stereoisomer of the compound or of said prodrug, according to claim 1 and a pharmaceutically acceptable carrier.

21. A pharmaceutical composition comprising an effective amount of a compound, a prodrug thereof, or a pharmaceutically acceptable salt, or stereoisomer of the compound or of said prodrug, according to claim 3 and a pharmaceutically acceptable carrier.

22. A pharmaceutical composition made by combining a compound, a prodrug thereof, or a pharmaceutically acceptable salt, or stereoisomer of a compound or of said prodrug, of claim 1 and a pharmaceutically acceptable carrier therefor.

23. The compound according to claim 1 of the formula

24. The compound according to claim 1 of the formula

25. The compound according to claim 1 of the formula

26. The compound according to claim 1 of the formula

27. The compound according to claim 1 of the formula

28. The compound according to claim 1 of the formula

29. The compound according to claim 1 of the formula

30. The compound according to claim 1 of the formula

31. The compound according to claim 1 of the formula

32. The compound according to claim 1 of the formula

33. The compound according to claim 1 of the formula

34. The compound according to claim 1 of the formula

35. The compound according to claim 1 of the formula

36. The compound according to claim 1 of the formula

37. The compound according to claim 1 of the formula