Patent US4103012A successfully refreshed from Google Patents.
US4103012A
Expired / Lapsed
US
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Indolizine derivatives, pharmaceutical compositions and methods containing same
Assignee: Sanofi SA
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Filing: 1977-02-16
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Granted: 1978-07-25
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Expires: 1997-02-16
Abstract
Abstract Novel indolizine derivatives of the general formula: <IMAGE> and pharmaceutically acceptable acid addition salts thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, a phenyl radical, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R1 and R2, which are different, represent a hydrogen atom or a group of the formula: <IMAGE> wherein R3 and R4+L, which are identical, each represent a hydrogen atom or a methyl radical, Am represents a dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, morpholino, piperidino, pyrrolidino or 4-methyl-piperazino group and n is an integer in the range of from 2 to 6 inclusive.
Inventors
- 👤 Jean Gubin
- 👤 Gilbert Rosseels
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 07:12
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P9/00; A61P9/06; A61P9/08; A61P9/10; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
125 words
An indolizine derivative corresponding to the formula: ##STR14## or a pharmaceutically acceptable acid addition salt thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, phenyl, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R 1 and R 2 , which are different, represent a hydrogen atom or a group of the formula: ##STR15## wherein R 3 and R 4 , which are identical, each represent a hydrogen atom or a methyl radical, Am represents dimethylamino, diethylamino, di-n-propylamino di-n-butylamino, and n is an integer in the range of from 2 to 6 inclusive.
Claim 2
Dependent Claim
125 words
An indolizine derivative corresponding to the formula: ##STR14## or a pharmaceutically acceptable acid addition salt thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, phenyl, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R 1 and R 2 , which are different, represent a hydrogen atom or a group of the formula: ##STR15## wherein R 3 and R 4 , which are identical, each represent a hydrogen atom or a methyl radical, Am represents dimethylamino, diethylamino, di-n-propylamino di-n-butylamino, and n is an integer in the range of from 2 to 6 inclusive.
Claim 3
Dependent Claim
8 words
2-Ethyl-3-[4-(3-di-n-butylaminopropoxy]-benzoyl-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
8 words
2-Ethyl-3-[4-(3-di-n-butylaminopropoxy]-benzoyl-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
2 words
2-Ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine hydrochloride.
Claim 6
Dependent Claim
2 words
2-Ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine hydrochloride.
Claim 7
Dependent Claim
8 words
2-n-Pentyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
8 words
2-n-Pentyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
8 words
2-n-Butyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim
8 words
2-n-Butyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim
8 words
2-Ethyl-3-[4-(4-di-n-butylaminobutoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim
8 words
2-Ethyl-3-[4-(4-di-n-butylaminobutoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim
8 words
2-(2-Bromo-phenyl)-3-[4-(3-diethylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 14
Dependent Claim
8 words
2-(2-Bromo-phenyl)-3-[4-(3-diethylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 15
Dependent Claim
8 words
2-(3,4-Dichloro-phenyl)-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
8 words
2-(3,4-Dichloro-phenyl)-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine and pharmaceutically acceptable acid addition salts thereof.
Claim 17
Dependent Claim
147 words
A pharmaceutical composition containing as active ingredient an effective amount of an indolizine derivative of the formula: ##STR16## or a pharmaceutically acceptable acid addition salt thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, a phenyl radical, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R 1 and R 2 , which are different, represent a hydrogen atom or a group of the formula: ##STR17## wherein R 3 and R 4 , which are identical, each represent a hydrogen atom or a methyl radical, Am represents dimethylamino, diethylamino, di-n-propylamino or di-n-butylamino, and n is an integer in the range of from 2 to 6 inclusive, in association with a pharmaceutical carrier or excipient therefor.
Claim 18
Dependent Claim
147 words
A pharmaceutical composition containing as active ingredient an effective amount of an indolizine derivative of the formula: ##STR16## or a pharmaceutically acceptable acid addition salt thereof, wherein R represents a branched- or straight-chain alkyl radical having from 1 to 5 carbon atoms, a phenyl radical, a mono-fluoro-, mono-chloro- or mono-bromo-phenyl, a di-fluoro-, di-chloro- or di-bromo-phenyl radical, a methoxy-phenyl radical or a methyl-phenyl radical optionally substituted on the aromatic moiety by an atom of fluorine, chlorine or bromine and R 1 and R 2 , which are different, represent a hydrogen atom or a group of the formula: ##STR17## wherein R 3 and R 4 , which are identical, each represent a hydrogen atom or a methyl radical, Am represents dimethylamino, diethylamino, di-n-propylamino or di-n-butylamino, and n is an integer in the range of from 2 to 6 inclusive, in association with a pharmaceutical carrier or excipient therefor.
Claim 19
Dependent Claim
25 words
A pharmaceutical composition containing as active ingredient 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier or excipient therefor.
Claim 20
Dependent Claim
25 words
A pharmaceutical composition containing as active ingredient 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or a pharmaceutically acceptable acid addition salt thereof, in association with a pharmaceutical carrier or excipient therefor.
Claim 21
Dependent Claim
18 words
A pharmaceutical composition containing as active ingredient 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine hydrochloride, in association with a pharmaceutical carrier or excipient therefor.
Claim 22
Dependent Claim
18 words
A pharmaceutical composition containing as active ingredient 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine hydrochloride, in association with a pharmaceutical carrier or excipient therefor.
Claim 23
Dependent Claim
31 words
A method for treating tachycardia in a subject in need of such treatment which method comprises administering to said subject an effective dose of an indolizine derivative according to claim 1.
Claim 24
Independent Claim
48 words
A method of treating angina pectoris in a subject in need of such treatment which method comprises administering to said subject an effective dose of an indolizine derivative selected from the group consisting of: 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-n-pentyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-n-butyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-ethyl-3-[4-(4-di-n-butylaminobutoxy)-benzoyl]-indolizine, 2-(2-bromophenyl)-3-[4-(3-diethylaminopropoxy)-benzoyl]-indolizine, and 2-(3,4-dichlorophenyl)-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, and pharmaceutically acceptable acid addition salts thereof.
Claim 25
Independent Claim
48 words
A method of treating angina pectoris in a subject in need of such treatment which method comprises administering to said subject an effective dose of an indolizine derivative selected from the group consisting of: 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-n-pentyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-n-butyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, 2-ethyl-3-[4-(4-di-n-butylaminobutoxy)-benzoyl]-indolizine, 2-(2-bromophenyl)-3-[4-(3-diethylaminopropoxy)-benzoyl]-indolizine, and 2-(3,4-dichlorophenyl)-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine, and pharmaceutically acceptable acid addition salts thereof.
Claim 26
Independent Claim
35 words
A method of treating angina pectoris in a subject in need of such treatment which method comprises administering to said subject an effective dose of 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or of a pharmaceutically acceptable acid addition salt thereof.
Claim 27
Independent Claim
35 words
A method of treating angina pectoris in a subject in need of such treatment which method comprises administering to said subject an effective dose of 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or of a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim
35 words
A method according to claim 14 wherein the effective dose is 100 mg to 300 mg by oral route or 2 to 3 mg by parenteral route per day to a subject weighing 60 kgs.
Claim 29
Independent Claim
35 words
A method of treating cardiac arrhythmia in a subject in need of such treatment which method comprises administering to said subject an effective dose of 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or of a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Independent Claim
35 words
A method of treating cardiac arrhythmia in a subject in need of such treatment which method comprises administering to said subject an effective dose of 2-ethyl-3-[4-(3-di-n-butylaminopropoxy)-benzoyl]-indolizine or of a pharmaceutically acceptable acid addition salt thereof.
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) | 1981-07-24 | 1982-01-23 | 1982-07-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-24 | 1986-01-23 | 1986-07-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-24 | 1990-01-23 | 1990-07-25 | $7700.00 | Window Closed / Lapsed |