Pyridone derivatives having a binding activity to the cannabinoid type 2 receptor

• US 20060052411A1
• Filed: 06/29/2005
• Published: 03/09/2006
• Est. Priority Date: 12/28/2000
• Status: Active Grant

• Current Assignee: Kohji Hanasaki, Yasuyoshi Iso, Yukio Tada
• Original Assignee: Kohji Hanasaki, Yasuyoshi Iso, Yukio Tada
• Inventors: Hanasaki, Kohji, Tada, Yukio, Iso, Yasuyoshi
• Granted Patent: US 7,652,141 B2
• Time in Patent Office: Days
• US Class Current: 514/300
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/04 Centrally acting analgesics, e.g. opioids
• 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 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 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 213/69 Two or more oxygen atoms
• CPC Class Codes: C07D 213/70 Sulfur atoms
• CPC Class Codes: C07D 213/75 Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• CPC Class Codes: C07D 213/82 in position 3
• CPC Class Codes: C07D 215/227 only one oxygen atom which is attached in position 2
• CPC Class Codes: C07D 215/38 Nitrogen atoms nitro radicals C07D215/18
• CPC Class Codes: C07D 215/54 attached in position 3
• CPC Class Codes: C07D 217/22 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
• CPC Class Codes: C07D 217/26 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 221/10 Aza-phenanthrenes
• CPC Class Codes: C07D 221/16 containing carbocyclic rings other than six-membered
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/56 : with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 : 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 401/04 : directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/06 : linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 401/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/06 : linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 405/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/14 : containing three or more hetero rings
• CPC Class Codes: C07D 413/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/14 : containing three or more hetero rings
• CPC Class Codes: C07D 417/12 : linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 455/02 : containing not further condensed quinolizine ring systems
• CPC Class Codes: C07D 455/06 : containing benzo [a] quinolizine ring systems
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems
• CPC Class Codes: C07D 491/04 : Ortho-condensed systems

Abstract

It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I):
wherein R¹ is a group represented by the formula: —Y¹—Y²—Y³—R^a wherein Y¹ is single bond or the like; Y² is —C(═O)—NH— or the like; Y³ is optionally substituted aryl or the like; R² is hydrogen or the like; R³ is alkyl or the like; R⁴ is alkyl or the like; R⁵ is optionally substituted alkyl or the like; or R³ and R⁴ taken together with the adjacent atom form cyclic group or the like.

Claims

1-18. -18. (canceled)

19. A library of compound of the formula (I):

20. The compound according to claim 19;

provided that the case wherein R³ and R⁴ taken together with adjacent atom form 6-membered carbocyclic group (provided that the bond between carbon atom substituted with R³ and carbon atom substituted R⁴ is the double bond, and the other bonds between carbon atoms are single bond), and R¹ is a group represented by the formula;

—

Y¹—

Y²—

Y³—

R^a wherein Y¹ and Y³ are single bond;

Y² is —

O—

;

R^a is phenyl is excluded;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

39. A pharmaceutical composition which contains as an active ingredient a compound of claim 20.

21. A library of compound of the formula (I):

22. The compound according to claim 21;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

40. A pharmaceutical composition which contains as an active ingredient a compound of claim 22.

23. A library of compound of the formula (I):

24. The compound according to claim 23;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

41. A pharmaceutical composition which contains as an active ingredient a compound of claim 24.

25. A compound of the formula:

26. The compound according to claim 25 wherein Y is —

(CH₂)₃—

;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

28. The compound according to claim 25 wherein Y³ is optionally substituted alkylene;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

37. The compound according to claim 26 wherein Y³ is optionally substituted alkylene;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

42. A pharmaceutical composition which contains as an active ingredient a compound of claim 25.

43. A pharmaceutical composition which contains as an active ingredient a compound of claim 26.

45. A pharmaceutical composition which contains as an active ingredient a compound of claim 28.

27. A compound of the formula:

38. The compound according to claim 27 wherein Y³ is optionally substituted alkylene;

a prodrug, a pharmaceutically acceptable salt or solvate thereof.

44. A pharmaceutical composition which contains as an active ingredient a compound of claim 27.

29-36. -36. (canceled)