Heterocyclic compounds and methods of making and using thereof

• US 7,456,288 B2
• Filed: 10/28/2004
• Issued: 11/25/2008
• Est. Priority Date: 10/28/2003
• Status: Expired due to Fees

• Current Assignee: Dr. Reddy's Laboratories Ltd.
• Original Assignee: Reddy US Therapeutics, Inc.
• Inventors: Pillarisetti, Ram, Pal, Manojit, Venkateswarlu, Akella, Sharma, Vedula Manohar, Rao, Yeleswarapu Koteswar, Padakanti, Srinivas, Rao, Kalleda Srinivasa
• Primary Examiner(s): SEAMAN, D MARGARET M
• Application Number:
  US10/976,284
• Publication Number:
  US 20050119269A1
• Time in Patent Office: 1,489 Days
• Field of Search: 546/158, 546/157
• US Class Current: 546/158
• CPC Class Codes: A61K 31/427 not condensed and containing further heterocyclic rings
• 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: C04B 35/632 Organic additives
• CPC Class Codes: C07D 215/56 with oxygen atoms in position 4
• CPC Class Codes: C07D 239/88 Oxygen atoms
• CPC Class Codes: C07D 239/90 with acyclic radicals attached in position 2 or 3
• CPC Class Codes: C07D 311/30 not hydrogenated in the hetero ring, e.g. flavones
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

Compounds of formula (I), and methods and/or compositions comprising compounds that are effective in modulating inflammatory responses, such as those resulting from AGE and glycated protein accumulation are provided. Methods and/or compositions comprising compounds that are effective in modulating smooth muscle cell proliferation and the diseases or conditions related thereto are also provided.

Claims

1. A compound of general formula (III)

3. The compound of claim 1, wherein any of R¹, R², R³ and R⁴ independently are substituted with hydrogen, a halogen, a nitro group, an amino group, a mono- or di-substituted amino group, a hydroxy group, an alkoxy group, a carboxy group, a cyano group, an oxo(O═

) group, a thio(S═

) group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, a cycloalkyl group, an aryl group, a benzyloxy group, an acyl group, an acyloxy group, an aroyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryl group, a heterocyclyl group, an aralkyl group, an alkylsulfonyl group, an alkylsulfinyl group, an arylsulfonyl group, an arylsulfinyl group, an alkylthio group, an arylthio group, a heteroarylthio group, an aralkylthio group, or a heterocyclyl sulfonyl group, which is optionally substituted with a halogen, a hydroxyl group, a nitro group, an amino group, an alkyloxy group, or any combination thereof, and wherein the heterocycle group is optionally a substituted morpholinyl group, a thiomorpholinyl group, or a piperzinyl group, wherein the substituent on the heterocyclyl group is a halogen, a nitro group, an amino group, an alkyl group, an alkoxy group, or an aryl group.

5. The compound of claim 1, wherein any of R¹, R², R³, and R⁴ independently are substituted with hydrogen, a halogen, a nitro group, an amino group, a mono- or di-subsituted amino group, a hydroxyl group, an alkoxy group, a carboxy group, a cyano group, an oxo(O═

) group, a thio(S═

) group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, a cycloalkyl group, an aryl group, a benzyloxy group, an acyl group, an acyloxy group, an aroyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryl group, a heterocyclyl group, an aralkyl group, an alkylsulfonyl group, an alkylsulfinyl group, an arylsulfonyl group, an arylsulfinyl group, an alkylthio group, an arylthio group, a heteroarylthio group, an aralkylthio group, or a heterocyclyl sulfonyl group, which is optionally substituted with a halogen, a hydroxyl group, a nitro group, an aminio group, an alkyloxy group, or any combination thereof, and wherein the heterocyclyl group is optionally a substituted morpholinyl group, a thiomorpholinyl group, or a piperzinyl group, wherein the substituent on the heterocyclyl group is a halogen, a nitro group, an amino group, an alkyl group, an alkoxy group, or an aryl group.

6. The compound of claim 1, wherein one or both of R′

and R″

independently are substituted with a halogen, a hydroxyl group, a nitro group, an amino group, or an alkyloxy group.

7. The compound of claim 1, wherein one or both of R′

or R″

independently are substituted with a heterocyclyl group comprising a morphonyl group, a thiomorphoine, or a piperzine.

8. The compound of formula (III) as claimed in claim 1, wherein the compound is:

2. A compound of general formula (II)

4. The compound of claim 2, wherein any of R¹, R², R³, and R⁴ independently are substituted with hydrogen, a halogen, a nitro group, an amino group, a mono- or di-substituted amino group, a hydroxy group, an alkoxy group, a carboxy group, a cyano group, an oxo(O═

) group, a thio(S═

) group, an alkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, a cycloalkyl group, an aryl group, a benzyloxy group, an acyl group, an acyloxy group, an aroyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryl group, a heterocyclyl group, an aralkyl group, an alkylsulfonyl group, an alkylsulfinyl group, an arylsulfonyl group, an arylsulfinyl group, an alkylthio group, an arylthio group, a heteroarylthio group, an aralkylthio group, or a heterocyclyl sulfonyl group, which is optionally substituted with a halogen, a hydroxyl group, a nitro group, an amino group, an alkyloxy group, or any combination thereof, and wherein the heterocycle group is optionally a substituted morpholinyl group, a thiomorpholinyl group, or a piperzinyl group, wherein the substituent on the heterocyclyl group is a halogen, a nitro group, an amino group, an alkyl group, an alkoxy group, or an aryl group.