US4716169A
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US
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Imidazo[1,2a]pyridines and their use as cardiotonic agents
Assignee: Boehringer Ingelheim Pharma GmbH and Co KG
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Filing: 1985-12-17
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Granted: 1987-12-29
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Expires: 2005-12-17
Abstract
Abstract The invention relates to new imidazo derivatives of the formula ##STR1## wherein "A-D and R 1 -R 3 are as defined in the specification". The new compounds have valuable pharmacological properties, particularly antithrombotic and cardiovascular properties such as a cardiotonic activity and/or an effect on blood pressure, and can be prepared using methods known per se.
Inventors
- 👤 Joachim Heider
- 👤 Norbert Hauel
- 👤 Volkhard Austel
- 👤 Klaus Noll
- 👤 Andreas Bomhard
- 👤 Jacques van Meel
- 👤 Willi Diederen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 01:11
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P7/00; A61P7/02; A61P9/00; A61P9/04; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
231 words
An imidazo[1,2-a]pyridine of the formula ##STR11## wherein one of the groups A, B, C or D is a --CH═ group optionally substituted by a halogen atom or by an alkylmercapto, alkylsulphonyloxy, amino, alkylamino, dialkylamino or acetamido group; another of the groups A, B, C or D is a --CH═ group optionally substituted by an alkylmercapto group; and, the other groups A, B, C or D are --CH═ groups; R 1 and R 2 together with two carbon atoms of the phenyl ring between them form a phenyl ring optionally substituted by an alkoxy group; and, when R 1 and R 2 do form such a phenyl ring, R 3 is a hydrogen atom, a hydroxy, alkoxy or alkylsulphonyloxy group; or, R 1 a phenylalkoxy, alkylsulphonyloxy, alkylsulphonamido, N-alkyl-alkylsulphonamido, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group or in the 4 position an acetamido, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, it being provided that if one or two of the groups A, B, C or D are one of the above-mentioned substituted --CH═ groups, then R 1 may also represent an amino, hydroxy, methoxy or cyano group in the 4 position; R 2 is a hydrogen atom, a hydroxy or alkoxy group; and, R 3 is a hydrogen atom or an alkoxy group; wherein in all the above-mentioned groups the alkyl part may contain one or two carbon atoms; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
231 words
An imidazo[1,2-a]pyridine of the formula ##STR11## wherein one of the groups A, B, C or D is a --CH═ group optionally substituted by a halogen atom or by an alkylmercapto, alkylsulphonyloxy, amino, alkylamino, dialkylamino or acetamido group; another of the groups A, B, C or D is a --CH═ group optionally substituted by an alkylmercapto group; and, the other groups A, B, C or D are --CH═ groups; R 1 and R 2 together with two carbon atoms of the phenyl ring between them form a phenyl ring optionally substituted by an alkoxy group; and, when R 1 and R 2 do form such a phenyl ring, R 3 is a hydrogen atom, a hydroxy, alkoxy or alkylsulphonyloxy group; or, R 1 a phenylalkoxy, alkylsulphonyloxy, alkylsulphonamido, N-alkyl-alkylsulphonamido, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group or in the 4 position an acetamido, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl group, it being provided that if one or two of the groups A, B, C or D are one of the above-mentioned substituted --CH═ groups, then R 1 may also represent an amino, hydroxy, methoxy or cyano group in the 4 position; R 2 is a hydrogen atom, a hydroxy or alkoxy group; and, R 3 is a hydrogen atom or an alkoxy group; wherein in all the above-mentioned groups the alkyl part may contain one or two carbon atoms; or, a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
169 words
An imidazo[1,2-a]pyridine of formula I, as claimed in claim 1, wherein one of the group A, B, C or D is a --CH═ group optionally substituted by a chlorine or bromine atom or by a methylmercapto, methylsulphonyloxy, amino, methylamino, dimethylamino or acetamido group; another of the groups A, B, C or D is a --CH═ group optionally substituted by a methylmercapto group; and, the other group, A, B, C or D are --CH═ groups; R 1 and R 2 together with two carbon atoms of the phenyl ring between them form a phenyl ring optionally substituted by a methoxy group and, when R 1 and R 2 form such a phenyl ring, R 3 represents a hydrogen atom, a hydroxy, methoxy or methanesulphonyloxy group; or, R 1 is a methylsulphonyloxy, methylsulphonamido, N-methyl-methylsulphonamido, aminosulphonyl, methylaminosulphonyl or dimethylaminosulphonyl or in the 4-position an acetamido, aminocarbonyl, methylaminocarbonyl or dimethylaminocarbonyl group; R 2 is a hydrogen atom or a hydroxy or methoxy group; and R 3 is a hydrogen or a methoxy group.
Claim 4
Dependent Claim
21 words
An imidazo[1,2-a]pyridine of formula I, as claimed in claim 1, wherein the groups A, B, C and D are --CH═ groups.
Claim 5
Dependent Claim
31 words
An imidazo[1,2-a]pyridine of formula I, as claimed in claim 3, wherein R 1 is in the 2 or 4 position and R 2 is in the remaining 2 or 4 position.
Claim 6
Dependent Claim
53 words
An imidazo[1,2-a]pyridine of formula I, as claimed in claim 3, wherein R 1 is in the 2 or 4 position and is a methylsulphonyloxy, methylsulphonamido, N-methyl-methylsulphonamido, aminosulphonyl, methylaminosulphonyl or dimethylaminosulphonyl group; R 2 is in the remaining 2 or 4 position and is a methoxy group; and, R 3 is a hydrogen atom.
Claim 7
Dependent Claim
9 words
2-(2-methoxy-4-methylsulphon-amidophenyl)-imidazo[1,2-a]pyridine or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
9 words
2-(2-methoxy-4-methylsulphon-amidophenyl)-imidazo[1,2-a]pyridine or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
30 words
A pharmaceutical composition for treating heart failure characterized by reduced cardiac output containing an effective positive inotropic amount of a compound of claim 1 together with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
37 words
A method of treating heart failure characterized by reduced cardiac output which comprises administering to a host suffering from same an effective positive inotropic amount of a compound of claim 1, 2, 3, 4, 5 or 6.
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) | 1990-12-28 | 1991-06-29 | 1991-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-28 | 1995-06-29 | 1995-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-28 | 1999-06-29 | 1999-12-29 | $7700.00 | Window Closed / Lapsed |