Claims
- 1. A compound represented by the formula ##STR8## and the 2,3-dihydro,5,6,7,8-tetrahydro and 2,3,5,6,7,8-hexahydro derivatives thereof, and the pharmaceutically acceptable salts thereof, wherein:
- R.sub.2 is hydrogen, lower alkyl or hydroxyloweralkyl;
- R.sub.3 is lower alkyl, --CH.sub.2 CN, hydroxyloweralkyl, --NO, --CH.sub.2 N.dbd.C or ##STR9## (wherein R.sub.6 and R.sub.7 are independently selected from the group consisting of hydrogen and lower alkyl) or hydrogen, provided R.sub.2 is not hydrogen;
- R.sub.4 is Z-T-W wherein Z represents --O--, --NH-- or a single bond; T represents a straight or branched chain lower alkylene group and when Z is a single bond, T also represents an ethenylene or a propenylene group wherein the unsaturated carbon is at the single bond and when Z is --O--, T also represents an allylene group wherein the saturated carbon is at the oxygen;
- W represents Ar and when T is allylene and Z is --O--, W represents hydrogen;
- Ar represents thienyl, pyridinyl, furanyl, phenyl and substituted phenyl wherein there are one or more substituents on the phenyl independently selected from halogen or lower alkyl; and
- R.sub.5 is hydrogen, halogen or lower alkyl.
- 2. A compound of claim 1 wherein R.sub.2 is methyl or ethyl;
- R.sub.3 is --NH.sub.2, --NHC.sub.2 H.sub.5, --CH.sub.2 CN, --CH.sub.3, --CH.sub.2 OH or --CH.sub.2 NC;
- R.sub.4 is --OCH.sub.2 Ar, --CH.dbd.CH--(CH.sub.2).sub.n Ar or --CH.sub.2 CH.sub.2 (CH.sub.2).sub.n Ar wherein n is zero or one and Ar is as defined in claim 1; and
- R.sub.5 is hydrogen, fluoro, chloro or methyl.
- 3. A compound of claim 1 wherein R.sub.4 is at the 8-position.
- 4. A compound of claim 3 wherein R.sub.4 is phenylmethoxy, phenylethyl, 3-phenyl-1-propenyl, phenylethenyl, benzylamino, 3-thienylmethoxy or 3-thienylmethanamino.
- 5. A compound of claim 4 wherein:
- R.sub.2 is methyl;
- R.sub.3 is amino, cyanomethyl or methyl;
- R.sub.5 is hydrogen or methyl.
- 6. A compound of claim 1 which is 2-methyl-6-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
- 7. A compound of claim 1 which is 2-methyl-6-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 8. A compound of claim 1 which is 2-methyl-5-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
- 9. A compound of claim 1 which is 2-methyl-5-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 10. A compound of claim 1 which is 2,3-dimethyl-5-benzyloxyimidazo[1,2-a]pyridine.
- 11. A compound of claim 1 which is 2-methyl-7-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 12. A compound of claim 1 which is 2-methyl-7-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
- 13. A compound of claim 3 which is 2-methyl-8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 14. A compound of claim 3 which is 2-methyl-8-phenylethoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 15. A compound of claim 3 which is 8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 16. A compound of claim 3 which is 2-methyl-8-(4-chlorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 17. A compound of claim 3 which is 2-hydroxymethyl-8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 18. A compound of claim 3, said compound being 2-methyl-8-(2-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 19. A compound of claim 3 which is 2-methyl-8-(4-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 20. A compound of claim 3 which is 2-methyl-8-(2-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-methanol.
- 21. A compound of claim 3 which is 2-methyl-8-(3-thienyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 22. A compound of claim 3 which is 2-methyl-8-(2-thienyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 23. A compound of claim 3 which is 8-benzyloxy-2,7-dimethylimidazo[1,2-a]pyridine-3-acetonitrile.
- 24. A compound of claim 3 which is 2-methyl-8-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
- 25. A compound according to claim 3 which is 2-methyl-8-(3-thienyl)methylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
- 26. A compound of claim 1 wherein R.sub.4 is allyloxy.
- 27. A compound of claim 26 which is 2-methyl-8-allyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
- 28. A compound of claim 3 which is 8-benzyloxy-2-ethylimidazo[1,2-a]pyridine-3-acetonitrile.
- 29. A compound of claim 3 which is 3-amino-2-methyl-8-benzyloxyimidazo[1,2-a]pyridine.
- 30. A compound of claim 3 which is 3-amino-2-methyl-8-phenylethylimidazo[1,2-a]pyridine.
- 31. A compound of claim 3 which is 3-nitroso-2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridine.
- 32. A compound of claim 4 which is 2,3-dimethyltrans(8-phenylethenyl)imidazo[1,2-a]pyridine.
- 33. A compound of claim 3 which is 2-methyl-8-(trans 3-phenyl-1-propenyl)-imidazo[1,2-a]pyridine-a-acetinitrile.
- 34. A compound of claim 3 which is 3-nitroso-2-methyl-8-phenylethylimidazo[1,2-a]pyridine.
- 35. A method for the treatment of the symptoms of peptic ulcer disease in mammals, which comprises administering to a mammal having peptic ulcer disease a therapeutically effective quantity of a compound of claim 1.
- 36. A method for the treatment of gastric ulcers in mammals which comprises administering to a mammal having gastric ulcers a therapeutically effective quantity of a compound of claim 1.
- 37. A method for the treatment of duodenal ulcers in mammals which comprises administering to a mammal having duodenal ulcers a therapeutically effective quantity of a compound of claim 1.
- 38. A method for inhibiting the formation of gastrointestinal irritation and damage in mammals due to drug-induced gastrointestional irritation and damage which comprises administering a therapeutically effective amount of a compound of claim 1 during the term said gastrointestinal irritating and damaging drug is administered for its therapeutic effect.
- 39. A method for the treatment of gastrointestinal damage due to stress which comprises administering to a mammal suffering from such damage a therapeutically effective quantity of a compound of claim 1.
- 40. A pharmaceutical formulation for use in the treatment of ulcers which comprises a compound of claim 1 in a therapeutically effective amount sufficient to alleviate the symptoms of peptic ulcer disease together with a non-toxic, pharmaceutically acceptable carrier.
- 41. A pharmaceutical formulation of claim 40 comprising a therapeutically effective amount of 2-methyl-8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile together with a non-toxic pharmaceutically acceptable carrier.
- 42. A pharmaceutical formulation of claim 40 comprising a therapeutically effect amount of 8-benzyloxy-2,7-dimethylimidazo[1,2-a]pyridine-3-acetonitrile.
Priority Claims (2)
Number |
Date |
Country |
Kind |
81/0219 |
Jan 1981 |
ZAX |
|
82105411.1 |
Jun 1981 |
EPX |
|
Parent Case Info
This application is a continuation-in-part of our copending application Ser. No. 277,576, filed June 26, 1981, now abandoned, which is a continuation-in-part of Ser. No. 114,473, filed Jan. 23, 1980 and now abandoned.
US Referenced Citations (4)
Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
277576 |
Jun 1981 |
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Parent |
114473 |
Jan 1980 |
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