US4831041A
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US
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Imidazopyridine compounds and processes for preparation thereof
Assignee: Astellas Pharma Inc
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Filing: 1987-11-12
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Granted: 1989-05-16
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Expires: 2007-11-12
Abstract
Abstract The invention relates to an imidazopyridine compound of the formula: ##STR1## wherein R 1 is lower alkynyl, lower alkynyloxy(lower)alkyl or N,N-di(lower)alkylamino(lower)alkynyl, R 2 is lower alkyl, R 3 is mono (or di or tri)-phenyl(lower)alkyl substituted by one or more substituent(s) selected from cyano, carbamoyl, mono (or di or tri(phenyl(lower)alkylamino, acylamino, carboxy, esterified carboxy, hydroxy, hydroxy(lower)alkyl, acyloxy(lower)alkyl, acyloxy, mono (or di or tri)phenyl(lower)alkoxy, lower alkoxy(lower)alkoxy, tetrahydropyranyloxy, and acylamino(lower)alkyl or mono (or di or tri) phenyl(lower)alkyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, N-lower alkyl-N-acylamino, mono (or di or tri)phenyl(lower)alkylamino, acylamino and lower alkylamino, and R 4 is hydrogen or lower alkyl, and a pharmaceutically acceptable salt thereof, useful in the treatment of ulcers.
Inventors
- 👤 Youichi Shiokawa
- 👤 Masanobu Nagano
- 👤 Hiromichi Itani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 00:41
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/73; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
109 words
An imidazopyridine compound of the formula: ##STR5## wherein R 1 is lower alkynyl, lower alkynyloxy(lower)alkyl or N,N-di(lower)alkylamino(lower)alkynyl, R 2 is lower alkyl, R 3 is mono (or di or tri)phenyl(lower)alkyl substituted by one or more substituent(s) selected from cyano, carbamoyl, mono (or di or tri)phenyl(lower)alkylamino, acylamino, carboxy, esterified carboxy, hydroxy, hydroxy(lower)alkyl, acyloxy(lower)alkyl, acyloxy, mono (or di or tri)-phenyl(lower)alkoxy, lower alkoxy(lower)alkoxy, tetrahydropyranyloxy, and acylamino(lower)alkyl or mono (or di or tri) phenyl (lower) alkyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, N-lower alkyl-N-acylamino, mono (or di or tri)phenyl(lower)alkylamino, acylamino and lower alkylamino, and R 4 is hydrogen or lower alkyl, and a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
109 words
An imidazopyridine compound of the formula: ##STR5## wherein R 1 is lower alkynyl, lower alkynyloxy(lower)alkyl or N,N-di(lower)alkylamino(lower)alkynyl, R 2 is lower alkyl, R 3 is mono (or di or tri)phenyl(lower)alkyl substituted by one or more substituent(s) selected from cyano, carbamoyl, mono (or di or tri)phenyl(lower)alkylamino, acylamino, carboxy, esterified carboxy, hydroxy, hydroxy(lower)alkyl, acyloxy(lower)alkyl, acyloxy, mono (or di or tri)-phenyl(lower)alkoxy, lower alkoxy(lower)alkoxy, tetrahydropyranyloxy, and acylamino(lower)alkyl or mono (or di or tri) phenyl (lower) alkyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, N-lower alkyl-N-acylamino, mono (or di or tri)phenyl(lower)alkylamino, acylamino and lower alkylamino, and R 4 is hydrogen or lower alkyl, and a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
59 words
A compound of claim 1, wherein R 3 is mono (or di or tri)phenyl(lower)alkyl substituted by one or more substituent(s) selected from cyano, carbamoyl, acylamino, carboxy, esterified carboxy, hydroxy, hydroxy(lower)alkyl, acyloxy(lower)alkyl, lower alkoxy(lower)alkoxy and acylamino(lower)alkyl or mono (or di or tri)phenyl(lower)alkyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, N-lower alkyl-N-acylamino, acylamino and lower alkylamino.
Claim 4
Dependent Claim
105 words
A compound of claim 2, wherein R 3 is mono (or di or tri)phenyl(lower)alkyl substituted by one or more substituent(s) selected from cyano, carbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, ureido, carboxy, lower alkoxycarbonyl, hydroxy, hydroxy(lower)alkyl, lower alkanoyloxy(lower)alkyl, lower alkoxy(lower)alkoxy and lower alkoxycarbonylamino(lower)alkyl; or mono (or di or tri)phenyl(lower)alkyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, lower alkanoylamino, lower alkanesulfonylamino, lower alkoxycarbonylamino, isonicotinamido, ureido, ureido having lower alkyl, lower alkoxycarbonylamino(lower)alkanoylamino, phenyl(lower)alkoxycarbonylamino, N-lower alkoxycarbonyl-N-lower alkylamino, N-lower alkanoyl-N-lower alkylamino, N-carbamoyl-N-lower alkylamino, 1,3-di(lower)alkylureido, N-lower alkanesulfonyl-N-lower alkylamino, lower alkylamino, 3-aroylthioureido, thioureido, hydroxy(lower)alkanoylamino, lower alkanoyloxy(lower)alkanoylamino, lower alkanoylcarbonylamino, lower alkoxycarbonylcarbonylamino, sulfamido, lower alkanoylamino substituted by hydroxy and amino(lower)alkanoylamino.
Claim 5
Dependent Claim
37 words
A compound of claim 3, wherein R 3 is benzyl substituted by one or more substituent(s) selected from cyano, carbamoyl, lower alkanoylamino, lower alkoxycarbonylamino, ureido, carboxy, lower alkoxycarbonyl, hydroxy, hydroxy(lower)alkyl, lower alkanoyloxy(lower)alkyl, lower alkoxy(lower)alkoxy and lower alkoxycarbonylamino(lower)alkyl.
Claim 6
Dependent Claim
47 words
A compound of claim 4, wherein R 1 is propynyl or propynyloxymethyl, R 2 is methyl, R 3 is benzyl substituted by one or more substituent(s) selected from cyano, carbamoyl, formamido, acetamido, methoxycarbonylamino, ureido, carboxy, ethoxycarbonyl, hydroxy, hydroxymethyl, acetoxymethyl, methoxymethoxy and methoxycarbonylaminomethyl, and R 4 is hydrogen.
Claim 7
Dependent Claim
33 words
A compound of claim 5, wherein R 1 is 2-propynyl or 2-propynyloxymethyl, R 3 is 2-cyanobenzyl, 2-carbamoylbenzyl, 4-carbamoylbenzyl, 2-formamidobenzyl, 2-acetamidobenzyl, 2,6-bis(acetamido)benzyl, 2-methoxycarbonylaminobenzyl, 2-ureidobenzyl, 4-carboxybenzyl, 4-ethoxycarbonylbenzyl, 3-hydroxybenzyl, 2-hydroxymethylbenzyl, 4-hydroxymethylbenzyl, 2,6-bis(hydroxymethyl)benzyl, 2-acetoxymethylbenzyl, 2-methoxymethoxybenzyl and 2-methoxycarbonylaminomethylbenzyl.
Claim 8
Dependent Claim
70 words
A compound of claim 3, wherein R 3 is benzyl substituted by lower alkyl and one additional substituent selected from hydroxy(lower)alkyl, amino, lower alkanoylamino, lower alkanesulfonylamino, lower alkoxycarbonylamino, isonicotinamido, ureido, ureido having lower alkyl, lower alkoxycarbonylamino(lower)alkanoylamino, phenyl(lower)alkoxycarbonylamino, N-lower alkoxycarbonyl-N-lower alkylamino, N-lower alkanoyl-N-lower alkylamino, N-carbamoyl-N-lower alkylamino, 1,3-di(lower)alkylureido, N-lower alkanesulfonyl-N-lower alkylamino, lower alkylamino, 3-aroylthioureido, thioureido, hydroxy(lower)alkanoylamino, lower alkanoyloxy (lower) alkanoylamino, lower alkanoylcarbonylamino, lower alkoxycarbonylcarbonylamino, sulfamido, lower alkanoylamino substituted by hydroxy and amino(lower)alkanoylamino.
Claim 9
Dependent Claim
68 words
A compound of claim 7, wherein R 1 is propynyl or N,N-dimethylaminobutynyl, R 2 is methyl, R 3 is benzyl substituted by methyl and one additional substituent selected from hydroxymethyl, amino, formamido, acetamido, propionamido, n-butyramido, methanesulfonylamino, methoxycarbonylamino, ethoxycarbonylamino, iso-propoxycarbonylamino, tert-butoxyarbonylamino, isonicotinamido, ureido, methylureido, tert-butoxycarbonylaminoacetamido, benzyloxycarbonylamino, N-methoxycarbonyl-N-methylamino, N-tert-butoxycarbonyl-N-methylamino, N-acetyl-N-methylamino, N-carbamoyl-N-methylamino, 1,3-dimethylureido, N-mesyl-N-methylamino, methylamino,3-benzoylthioureido, thioureido, hydroxyacetamido, acetoxyacetamido, pyruvamido, methoxalylamino, sulfamido, lactamido and aminoacetamido, and R 4 is hydrogen or methyl.
Claim 10
Dependent Claim
50 words
A compound of claim 8, wherein R 1 is 2-propynyl or N,N-dimethylamino-2-butynyl, R 3 is 2-hydroxymethyl-6-methylbenzyl, 2-amino-6-methylbenzyl, 2-formamido-6-methylbenzyl, 2-acetamido-6-methylbenzyl, 3-acetamido-2-methylbenzyl, 4-acetamido-2-methylbenzyl, 5-acetamido-2-methylbenzyl, 2-methyl-6-propionamidobenzyl, 2-n-butyramido-6-methylbenzyl, 2-methanesulfonylamino-6-methylbenzyl, 2-methoxycarbonylamino-6-methylbenzyl, 2-ethoxycarbonylamino-6-methylbenzyl, 2-iso-propoxycarbonylamino-6-methylbenzyl, 2-methyl-6-tert-butoxycarbonylaminobenzyl, 2-isonicotinamido-6-methylbenzyl, 2-methyl-6-ureidobenzyl, 2-methyl-6-(3-methylureido)benzyl, 2-methyl-6-tert-butoxycarbonylaminoacetamidobenzyl, 2-benzyloxycarbonylamino-6-methylbenzyl, 2-(N-methoxycarbonyl-N-methylamino)-6-methylbenzyl, 2-methyl-6-(N-tert-butoxycarbonyl-N-methylamino)benzyl, 2-(N-acetyl-N-methylamino)-6-methylbenzyl, 2-(N-carbamoyl-N-methylamino)-6-methylbenzyl, 2-(1,3-dimethylureido)-6-methylbenzyl, 2-(N-mesyl-N-methylamino)-6-methylbenzyl, 2-methyl-6-methylaminobenzyl, 2-(3-benzoylthioureido)-6-methylbenzyl, 2-methyl-6-thioureidobenzyl, 2-hydroxyacetamido-6-methylbenzyl, 2-acetoxyacetamido-6-methylbenzyl, 2-methyl-6-pyruvamidobenzyl, 2-methoxalylamino-6-methylbenzyl, 2-methyl-6-sulfamidobenzyl, 2-lactamido-6-methylbenzyl, 2-aminoacetamido-6-methylbenzyl.
Claim 11
Dependent Claim
13 words
A compound of claim 9, which is 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine, its hydrochloride or its sulfate.
Claim 12
Dependent Claim
8 words
A compound of claim 9, which is 2-methyl-8-(2-methyl-6-thioureidobenzyloxy)-3-(2-propynyl)imidazo[1,2-a]pyrridine.
Claim 13
Dependent Claim
31 words
A pharmaceutical composition which comprises, as an active ingredient, an antiulcerative effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof in admixture with pharmaceutically acceptable carriers.
Claim 14
Dependent Claim
30 words
A method for the treatment of ulcer which comprises administering an antiulcerative effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof to human or animal.
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) | 1992-05-15 | 1992-11-14 | 1993-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-15 | 1996-11-14 | 1997-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-15 | 2000-11-14 | 2001-05-16 | $7700.00 | Window Closed / Lapsed |