Pyrrolo[1,2-a]imidazoles and imidazo[1,2-a]pyridines

• US 4,507,481 A
• Filed: 07/29/1983
• Issued: 03/26/1985
• Est. Priority Date: 07/29/1983
• Status: Expired due to Fees

• Current Assignee: Fisons Limited (Sanofi )
• Original Assignee: Pennwalt Corporation (Arkema)
• Inventors: Murray, Robert J., Davidson, Thomas A.
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Dentz, Bernard I.
• Application Number:
  US06/518,514
• Time in Patent Office: 606 Days
• Field of Search: 546/121, 548/324
• US Class Current: 546/121
• 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 37/06 Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems

Abstract

Novel 7-ether and 7-thioether derivatives of 2-aryl, 3-aryl, and 2,3-diaryl-2,5,6,7-tetrahydro-3H-pyrrolo[1,2-a]-imidazole and 8-ether and 8-thioether derivatives of 2-aryl, 3-aryl, and 2,3-diaryl-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]-pyridine, such as 2,3,5,6,7,8-hexahydro-2-phenyl-8,8-dimethoxy-imidazo[1,2-a]pyridine hydrochloride, useful as immunomodulators.

Claims

1. The compound selected from the group consisting of (a) a 2-phenyl, 3-phenyl and 2,3-diphenyl-2,5,6,7-tetrahydro-3H-pyrrolo[1,2-a]imidazole which is mono- or di-substituted at the 7-position with --XR₁ and a (b) 2-phenyl, 3-phenyl or 2,3-diphenyl-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine which is mono- or di-substituted at the 8-position with --XR₁, wherein X is 0 or S(0)n;

n is 0, 1 or 2;

R₁ is hydrogen, lower alkyl, phenyl, benzyl, or phenyl or benzyl substituted by lower alkyl, amino, lower alkylamino, nitro, halogen, hydroxy or lower alkoxy;

the 2,3-position of said compound has a single or a double bond;

the phenyl groups at the 2 and/or 3 positions are unsubstituted or substituted with lower alkyl, amino, lower alkylamino, nitro, hydroxy, lower alkoxy or halogen;

in the case where one of the 2 or 3 positions is substituted by a phenyl or substituted phenyl, then the other of said 2 and 3 positions may be substituted by a lower alkyl group; and

pharmaceutically acceptable salts thereof.

2. The compound of group (b) of claim 1 having a single bond at the 2,3-position.

3. The compound of claim 2 wherein the 8-position is disubstituted with XR₁, the 2-position has an unsubstituted phenyl substituent, and the 3-position is unsubstituted.

4. The compound of claim 3, 2,3,5,6,7,8-hexahydro-2-phenyl-8,8-dimethoxyimidazo[1,2-a]-pyridine hydrochloride.