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US4358454A Expired / Lapsed US ⏱️ 0.0 years remaining

1,3,4-Triazolo[1,5-a]pyridines

Assignee: Merck Sharp & Dohme LLC
•
Filing: 1982-01-08
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Granted: 1982-11-09
•
Expires: 2002-01-08
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Abstract

Abstract There are disclosed herein certain 1,3,4-triazolo[1,5-a]pyridine compounds which are useful in the treatment of peptic ulcer diseases.

Inventors

  • 👤 James A. Bristol
  • 👤 Raymond G. Lovey

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 10:51
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 192 words
A compound represented by the formula: ##STR13## and the pharmaceutically acceptable salts thereof, wherein R represents hydrogen, lower alkyl of 1-3 carbons, arylalkyl, --CH 2 OH, --CH 2 CN, ##STR14## --NO 2 , --NO, --CH 2 --O--CO--R 1 , (wherein R 1 is lower alkyl or dimethylaminomethyl), --N(R 3 ) 2 (wherein each R 3 independently is hydrogen, lower alkyl of 1-3 carbon atoms or arylalkyl), --S(O) n --CH 3 or --CH 2 --S(O) n --CH 3 wherein n is zero, one or two; X represents hydrogen, lower alkyl, halogen, hydroxy, lower alkoxy, or trifluoromethyl; and Y represents --R 2 , --OR 2 , --NHR 2 , or --S(O) n R 2 wherein n is zero, one or two and R 2 is -lower alkylene-vinyl, -lower alkylene-Ar, -lower alkene-Ar, -lower alkene-lower alkylene-Ar, or -lower alkylene-O-Ar, wherein Ar is substituted-phenyl, phenyl, thienyl, or pyridyl wherein there are one or more substituents on the substituted-phenyl independently selected from --H, --Cl, --F, --CH 3 , -t-butyl, --CF 3 , --OCH 3 and --OH; provided that when --R 2 is lower alkylene-O--Ar, Y is not --OR 2 , --NHR 2 or --S(O) n R 2 .
Claim 2
Dependent Claim 192 words
A compound represented by the formula: ##STR13## and the pharmaceutically acceptable salts thereof, wherein R represents hydrogen, lower alkyl of 1-3 carbons, arylalkyl, --CH 2 OH, --CH 2 CN, ##STR14## --NO 2 , --NO, --CH 2 --O--CO--R 1 , (wherein R 1 is lower alkyl or dimethylaminomethyl), --N(R 3 ) 2 (wherein each R 3 independently is hydrogen, lower alkyl of 1-3 carbon atoms or arylalkyl), --S(O) n --CH 3 or --CH 2 --S(O) n --CH 3 wherein n is zero, one or two; X represents hydrogen, lower alkyl, halogen, hydroxy, lower alkoxy, or trifluoromethyl; and Y represents --R 2 , --OR 2 , --NHR 2 , or --S(O) n R 2 wherein n is zero, one or two and R 2 is -lower alkylene-vinyl, -lower alkylene-Ar, -lower alkene-Ar, -lower alkene-lower alkylene-Ar, or -lower alkylene-O-Ar, wherein Ar is substituted-phenyl, phenyl, thienyl, or pyridyl wherein there are one or more substituents on the substituted-phenyl independently selected from --H, --Cl, --F, --CH 3 , -t-butyl, --CF 3 , --OCH 3 and --OH; provided that when --R 2 is lower alkylene-O--Ar, Y is not --OR 2 , --NHR 2 or --S(O) n R 2 .
Claim 3
Dependent Claim 106 words
A compound of claim 1 wherein R represents --H, --CH 3 , --CH 2 OH, --CH 2 CN, --CH 2 OCOCH 3 , ##STR15## --NH 2 or --NO; X represents hydrogen; and Y is in the 8-position and represents --OR 2 , --NHR 2 or --R 2 wherein R 2 is --CH 2 --Ar, --CH 2 --CH 2 --Ar, ##STR16## --CH 2 --CH 2 --CH 2 --Ar, --CH═CH--Ar, --CH═CH--CH 2 --Ar or --CH 2 --O--Ar, wherein Ar is phenyl, o- or p-fluorophenyl, p-chlorophenyl, 2,4,6 trimethylphenyl, 2-thienyl or 3-thienyl, provided that when R 2 is --CH 2 --O--Ar, Y is not --OR 2 or --NHR 2 .
Claim 4
Dependent Claim 19 words
A compound of claim 1 wherein Y is phenylmethoxy, phenylmethanamino, thienylmethanamino, phenylethyl, phenylpropyl, thienylethyl, thienylpropyl, 2-phenylethenyl, 3-phenyl-1-propenyl or phenoxymethyl.
Claim 5
Dependent Claim 35 words
A compound of claim 1 represented by the formula: ##STR17## and pharmaceutically acceptable salts thereof, wherein R' represents hydrogen, methyl, amino or cyanomethyl; X' represents hydrogen; and Y' represents phenylmethoxy, phenylmethanamino, phenylethyl, 3-phenyl-1-propenyl or 2-phenylethenyl.
Claim 6
Dependent Claim 15 words
The compound of claim 4 wherein R' is methyl and Y' is phenylmethanamino, i.e. 2-methyl-8-phenylmethanamino-1,3,4-triazolo[1,5-a]pyridine.
Claim 7
Dependent Claim 15 words
The compound of claim 4 wherein R' is cyanomethyl, and Y' is phenylmethanamino, i.e. 8-phenylmethanamino-1,3,4-triazolo[1,5-a]pyridine-2-acetonitrile.
Claim 8
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 amount of a compound of claim 1.
Claim 9
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 amount of a compound of claim 1.
Claim 10
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 amount of a compound of claim 1.
Claim 11
Dependent Claim 59 words
A method for inhibiting the formation of gastrointestinal irritation and damage and ulcers due to administration of drugs which induce such effects which comprises administering to a patient in need of such treatment a therapeutically effective amount of a compound of claim 1 during the term said gastrointestinal irritating and damaging drug is being administered for its therapeutic effect.
Claim 12
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 amount of a compound of claim 1.
Claim 13
Dependent Claim 25 words
A method of claim 7 which comprises administering to a mammal having peptic ulcer disease, a therapeutically effective amount of a compound of claim 5.
Claim 14
Dependent Claim 25 words
A method of claim 7 which comprises administering to a mammal having peptic ulcer disease, a therapeutically effective amount of a compound of claim 6.
Claim 15
Dependent Claim 37 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 pharmaceutically acceptable carrier.
Claim 16
Dependent Claim 24 words
A pharmaceutical formulation of claim 14 which comprises a therapeutically effective amount of a compound of claim 5 together with a pharmaceutically acceptable carrier.
Claim 17
Dependent Claim 24 words
A pharmaceutical formulation of claim 14 which comprises a therapeutically effective amount of a compound of claim 6 together with a pharmaceutically acceptable carrier.
Claim 18
Dependent Claim 12 words
A composition of claim 14, 15 or 16 suitable for oral administration.

References Cited (Backward Citations)

US4209626A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-11-08 1986-05-10 1986-11-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-11-08 1990-05-10 1990-11-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-11-08 1994-05-10 1994-11-09 $7700.00 Window Closed / Lapsed

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