US4450164A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Imidazo[1,2-A]pyridines and use
Assignee: Merck Sharp & Dohme LLC
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Filing: 1982-12-20
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Granted: 1984-05-22
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Expires: 2002-12-20
Abstract
Abstract This invention relates to imidazo[1,2-a]pyridine derivatives which are useful in the treatment of peptic ulcer diseases.
Inventors
- 👤 James A. Bristol
- 👤 Chester Puchalski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 00:54
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/73; C07D471/00; C07D471/02; C07D471/04; C07D487/00; C07D487/02; C07D487/04; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
187 words
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 2 is hydrogen, lower alkyl or hydroxyloweralkyl; R 3 is lower alkyl, --CH 2 CN, hydroxyloweralkyl, --NO, --CH 2 N═C or ##STR9## (wherein R 6 and R 7 are independently selected from the group consisting of hydrogen and lower alkyl) or hydrogen, provided R 2 is not hydrogen; R 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 5 is hydrogen, halogen or lower alkyl.
Claim 2
Dependent Claim
187 words
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 2 is hydrogen, lower alkyl or hydroxyloweralkyl; R 3 is lower alkyl, --CH 2 CN, hydroxyloweralkyl, --NO, --CH 2 N═C or ##STR9## (wherein R 6 and R 7 are independently selected from the group consisting of hydrogen and lower alkyl) or hydrogen, provided R 2 is not hydrogen; R 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 5 is hydrogen, halogen or lower alkyl.
Claim 3
Dependent Claim
80 words
A compound of claim 1 wherein R 2 is methyl or ethyl; R 3 is --NH 2 , --NHC 2 H 5 , --CH 2 CN, --CH 3 , --CH 2 OH or --CH 2 NC; R 4 is --OCH 2 Ar, --CH═CH--(CH 2 ) n Ar or --CH 2 CH 2 (CH 2 ) n Ar wherein n is zero or one and Ar is as defined in claim 1; and R 5 is hydrogen, fluoro, chloro or methyl.
Claim 4
Dependent Claim
12 words
A compound of claim 1 wherein R 4 is at the 8-position.
Claim 5
Dependent Claim
17 words
A compound of claim 3 wherein R 4 is phenylmethoxy, phenylethyl, 3-phenyl-1-propenyl, phenylethenyl, benzylamino, 3-thienylmethoxy or 3-thienylmethanamino.
Claim 6
Dependent Claim
23 words
A compound of claim 4 wherein: R 2 is methyl; R 3 is amino, cyanomethyl or methyl; R 5 is hydrogen or methyl.
Claim 7
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-6-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 8
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-6-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 9
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-5-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 10
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-5-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 11
Dependent Claim
8 words
A compound of claim 1 which is 2,3-dimethyl-5-benzyloxyimidazo[1,2-a]pyridine.
Claim 12
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-7-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 13
Dependent Claim
8 words
A compound of claim 1 which is 2-methyl-7-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 14
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 15
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-phenylethoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 16
Dependent Claim
8 words
A compound of claim 3 which is 8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 17
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-(4-chlorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 18
Dependent Claim
8 words
A compound of claim 3 which is 2-hydroxymethyl-8-benzyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 19
Dependent Claim
9 words
A compound of claim 3, said compound being 2-methyl-8-(2-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 20
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-(4-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 21
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-(2-fluorophenyl)methoxyimidazo[1,2-a]pyridine-3-methanol.
Claim 22
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-(3-thienyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 23
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-(2-thienyl)methoxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 24
Dependent Claim
8 words
A compound of claim 3 which is 8-benzyloxy-2,7-dimethylimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 25
Dependent Claim
8 words
A compound of claim 3 which is 2-methyl-8-benzylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 26
Dependent Claim
9 words
A compound according to claim 3 which is 2-methyl-8-(3-thienyl)methylaminoimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 27
Dependent Claim
10 words
A compound of claim 1 wherein R 4 is allyloxy.
Claim 28
Dependent Claim
8 words
A compound of claim 26 which is 2-methyl-8-allyloxyimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 29
Dependent Claim
8 words
A compound of claim 3 which is 8-benzyloxy-2-ethylimidazo[1,2-a]pyridine-3-acetonitrile.
Claim 30
Dependent Claim
8 words
A compound of claim 3 which is 3-amino-2-methyl-8-benzyloxyimidazo[1,2-a]pyridine.
Claim 31
Dependent Claim
8 words
A compound of claim 3 which is 3-amino-2-methyl-8-phenylethylimidazo[1,2-a]pyridine.
Claim 32
Dependent Claim
8 words
A compound of claim 3 which is 3-nitroso-2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridine.
Claim 33
Dependent Claim
8 words
A compound of claim 4 which is 2,3-dimethyltrans(8-phenylethenyl)imidazo[1,2-a]pyridine.
Claim 34
Dependent Claim
9 words
A compound of claim 3 which is 2-methyl-8-(trans 3-phenyl-1-propenyl)-imidazo[1,2-a]pyridine-a-acetinitrile.
Claim 35
Dependent Claim
8 words
A compound of claim 3 which is 3-nitroso-2-methyl-8-phenylethylimidazo[1,2-a]pyridine.
Claim 36
Dependent Claim
34 words
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.
Claim 37
Dependent Claim
29 words
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.
Claim 38
Dependent Claim
29 words
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.
Claim 39
Dependent Claim
48 words
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.
Claim 40
Dependent Claim
31 words
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.
Claim 41
Dependent Claim
38 words
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.
Claim 42
Dependent Claim
20 words
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.
Claim 43
Dependent Claim
13 words
A pharmaceutical formulation of claim 40 comprising a therapeutically effect amount of 8-benzyloxy-2,7-dimethylimidazo[1,2-a]pyridine-3-acetonitrile.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-22 | 1987-11-21 | 1988-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-22 | 1991-11-21 | 1992-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-22 | 1995-11-21 | 1996-05-22 | $7700.00 | Window Closed / Lapsed |