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US4468400A Expired / Lapsed US ⏱️ 0.0 years remaining

Antiulcer tricyclic imidazo [1,2-a]pyridines

Assignee: Merck Sharp & Dohme LLC
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Filing: 1982-12-20
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Granted: 1984-08-28
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Expires: 2002-12-20
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Abstract

Abstract There are disclosed certain substituted tricyclic imidazo[1,2-a]pyridines which are useful in the treatment of peptic ulcer diseases.

Inventors

  • 👤 Elijah H. Gold
  • 👤 James J. Kaminski
  • 👤 Chester Puchalski

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 13:12
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; C07D491/00; C07D491/12; C07D491/14

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 176 words
A compound represented by the formula ##STR11## or a pharmaceutically acceptable salt thereof; wherein R 2 represents hydroxy, lower alkyl or hydroxyloweralkyl; R 3 represents hydrogen, lower alkyl, --CH 2 CN, hydroxyloweralkyl, --NO, --CH 2 NC or ##STR12## wherein R 4 and R 5 are independently selected from the group consisting of hydrogen and lower alkyl; X represents hydrogen, lower alkyl, halogen, hydroxy, lower alkoxy or trifluoromethyl; A is a non-aromatic ring fused to the pyridine ring containing, with the carbon atoms of the pyridine ring to which it is attached, 5 or 6 ring atoms of which all are carbon or one is selected from nitrogen, sulfur or oxygen with the remaining atoms being carbon wherein the heteroatom of the 5-membered ring is at the 7 or 9 position and the heteroatom of the 6-membered ring is at the 10 position; Ar represents phenyl, pyridyl, thienyl, imidazolyl, furanyl or X'- Y'- and Z'- substituted- phenyl wherein each of X'-, Y'- and Z'- independently is as defined for X; and n is zero, one or two.
Claim 2
Dependent Claim 176 words
A compound represented by the formula ##STR11## or a pharmaceutically acceptable salt thereof; wherein R 2 represents hydroxy, lower alkyl or hydroxyloweralkyl; R 3 represents hydrogen, lower alkyl, --CH 2 CN, hydroxyloweralkyl, --NO, --CH 2 NC or ##STR12## wherein R 4 and R 5 are independently selected from the group consisting of hydrogen and lower alkyl; X represents hydrogen, lower alkyl, halogen, hydroxy, lower alkoxy or trifluoromethyl; A is a non-aromatic ring fused to the pyridine ring containing, with the carbon atoms of the pyridine ring to which it is attached, 5 or 6 ring atoms of which all are carbon or one is selected from nitrogen, sulfur or oxygen with the remaining atoms being carbon wherein the heteroatom of the 5-membered ring is at the 7 or 9 position and the heteroatom of the 6-membered ring is at the 10 position; Ar represents phenyl, pyridyl, thienyl, imidazolyl, furanyl or X'- Y'- and Z'- substituted- phenyl wherein each of X'-, Y'- and Z'- independently is as defined for X; and n is zero, one or two.
Claim 3
Dependent Claim 59 words
A compound of claim 1 wherein ring A is dihydropyrano, R 2 represents hydrogen, lower alkyl with 1 to 3 carbon atoms or --CH 2 OH; R 3 represents hydrogen, lower alkyl with 1 to 3 carbon atoms, --CH 2 OH, --CH 2 CN or --NH 2 ; X represents hydrogen or methyl; and n is zero or 1.
Claim 4
Dependent Claim 17 words
A compound of claim 2 wherein --(CH 2 )nAr is at the 9-position of the A ring.
Claim 5
Dependent Claim 13 words
A compound of claim 3 wherein n is zero and Ar is phenyl.
Claim 6
Dependent Claim 25 words
A compound of claim 4 wherein R 2 represents methyl; R 3 represents methyl, --CH 2 CN or NH 2 ; and X represents hydrogen.
Claim 7
Dependent Claim 28 words
The compound of claim 5 wherein R 2 is methyl and R 3 is acetonitrile, i.e. 2-methyl-9-phenyl-7H-8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridine-3-acetonitrile represented by the structure ##STR13## or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim 14 words
A compound of claim 6 wherein the pharmaceutically acceptable salt is the hydrochloride salt.
Claim 9
Dependent Claim 28 words
The compound of claim 5 wherein R 2 is methyl and R 3 is amino, i.e. 3-Amino-2-methyl-9-phenyl-7H-8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridine represented by the structure ##STR14## or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim 38 words
A compound of claim 1 where R 2 and R 3 are each methyl, the A ring is cyclohexeno and phenyl is at the 9-position, i.e. 2,3-Dimethyl-9-phenyl-7,8-dihydroimidazo-[2,1-a]isoquinoline represented by the structure ##STR15## or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim 38 words
A compound of claim 1 wherein R 2 is methyl, R 3 is amino, the A ring is cyclohexeno and phenyl is at the 9-position, i.e. 3-Amino-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[2,1-a]isoquinoline represented by the structure ##STR16## or a pharmaceutical acceptable salt thereof.
Claim 12
Dependent Claim 38 words
A compound of claim 1 wherein R 2 is methyl, R 3 is acetonitrile, the A ring is cyclohexeno and phenylmethyl is at the 9-position, i.e. 2-Methyl-9-phenylmethyl-7,8-dihydroimidazo[2,1-a]isoquinoline-3-acetonitrile represented by the structure ##STR17## or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim 39 words
A pharmaceutical formulation for use in the treatment of peptic ulcer disease 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 14
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 15
Dependent Claim 28 words
A method for the treatment of gastric ulcers in mammals which comprises administering to mammal having gastric ulcers, a therapeutically effective amount of a compound of claim 1.
Claim 16
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 17
Dependent Claim 49 words
A method for inhibiting gastrointestinal irritation and damage in mammals due to administration of drugs which induce gastrointestinal 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 18
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.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-08-28 1988-02-27 1988-08-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-08-28 1992-02-27 1992-08-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-08-28 1996-02-27 1996-08-28 $7700.00 Window Closed / Lapsed

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