US5182291A
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Pyrozala-pyridyl aminoabkoxyphenol compounds
Assignee: Elf Sanofi SA
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Filing: 1991-06-17
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Granted: 1993-01-26
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Expires: 2011-06-17
Abstract
Abstract Aminoalkoxyphenyl derivatives useful in the treatment of certain pathological syndromes of the cardiovascular system of formula: ##STR1## in which: B represents a --S--, --SO-- or --SO 2 -- group, R 1 and R 2 , which are identical or different, each denote hydrogen, a methyl or ethyl radical or a halogen, A denotes a straight- or branched-alkylene radical having from 2 to 5 carbon atoms or a 2-hydroxypropylene radical, in which the hydroxy is optionally substituted by a lower alkyl radical, R 3 denotes an alkyl radical or a radical of formula: --Alk--R.sub.5 in which Alk denotes a single bond or a linear- or branched-alkylene radical having from 1 to 5 carbon atoms and R 5 denotes a pyridyl, phenyl, 2,3-methylenedioxyphenyl or 3,4-methylenedioxyphenyl radical or a phenyl group substituted with one or more substituents, which may be identical or different, selected from halogen atoms, lower alkyl groups or lower alkoxy groups, R 4 denotes hydrogen or an alkyl radical or R 3 and R 4 when taken together, denote an alkylene or alkenylene radical having from 3 to 6 carbon atoms and optionally substituted with a phenyl radical or optionally interrupted by --O--, ##STR2## R 6 denoting hydrogen or a lower alkyl or pheny radical, Cy represents a cyclic group with the proviso that when Cy represents a benzo[b]furyl or benzo[b]thienyl group and B represents a --SO 2 -- group, R 3 represents a radical --Alk--R 5 , as well as the N-oxide derivative thereof and a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Jean Gubin
- 👤 Pierre Chatelain
- 👤 Marcel Descamps
- 👤 Dino Nisato
- 👤 Henri Inion
- 👤 Jean Lucchetti
- 👤 Jean-Marie Mahaux
- 👤 Jean-Noel Vallat
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 08:26
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; C07C; C07C309/00; C07C317/00; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D213/71; C07D215/00; C07D215/02; C07D215/16; C07D215/36; C07D235/00; C07D235/02; C07D235/04; C07D235/22; C07D261/00; C07D261/02; C07D261/06; C07D261/10; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/36; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/64; C07D471/00; C07D471/02; C07D471/04; C07D495/00; C07D495/02; C07D495/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
221 words
An aminoalkoxyphenyl compound of formula: ##STR173## in which: B is selected from --S--, --SO-- and --SO 2 --; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; R 3 is selected from alkyl having from 1 to 8 carbon atoms and a radical of formula Alk-R 5 , in which Alk is selected from a single bond and a linear- or branched-alkylene radical having from 1 to 5 carbon atoms, and R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents, which may be identical or different, selected from halogen atoms, lower alkyl groups having from 1 to 4 carbon atoms, and lower alkoxy groups having from 1 to 4 carbon atoms; R 4 is selected from hydrogen and alkyl having from 1 to 8 carbon atoms; R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; as well as the N-oxide derivative thereof and a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
221 words
An aminoalkoxyphenyl compound of formula: ##STR173## in which: B is selected from --S--, --SO-- and --SO 2 --; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; R 3 is selected from alkyl having from 1 to 8 carbon atoms and a radical of formula Alk-R 5 , in which Alk is selected from a single bond and a linear- or branched-alkylene radical having from 1 to 5 carbon atoms, and R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents, which may be identical or different, selected from halogen atoms, lower alkyl groups having from 1 to 4 carbon atoms, and lower alkoxy groups having from 1 to 4 carbon atoms; R 4 is selected from hydrogen and alkyl having from 1 to 8 carbon atoms; R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; as well as the N-oxide derivative thereof and a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
168 words
An aminoalkoxyphenyl compound of formula: ##STR174## in which: R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 -alkyl, lower C 1-4 alkoxy and nitro; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; Alk is selected from a single bond and a linear- or a branched-alkylene radical having from 1 to 5 carbon atoms; R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents which may be identical or different, selected from halogen, C 1-8 alkyl and C 1-8 alkoxy; R 4 is selected from hydrogen and C 1-8 alkyl, as well as the N-oxide derivative thereof and the pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
168 words
An aminoalkoxyphenyl compound of formula: ##STR174## in which: R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 -alkyl, lower C 1-4 alkoxy and nitro; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; Alk is selected from a single bond and a linear- or a branched-alkylene radical having from 1 to 5 carbon atoms; R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents which may be identical or different, selected from halogen, C 1-8 alkyl and C 1-8 alkoxy; R 4 is selected from hydrogen and C 1-8 alkyl, as well as the N-oxide derivative thereof and the pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
15 words
An aminoalkoxyphenyl compound according to claim 2 in which Alk-R 5 represents a [N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy group.
Claim 6
Dependent Claim
16 words
An aminoalkoxyphenyl compound according to claim 2 in which R represents an isopropyl or cyclopropyl group.
Claim 7
Dependent Claim
33 words
An aminoalkoxyphenyl compound according to claim 2 which is 2-isopropyl-3-[4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulphonyl]pyrazolo[1,5-a]pyridine and its N-oxide and pharmaceutically acceptable salts; 2-isopropyl-3-{4-[3-(di-n-butylamino)propyloxy]benzenesulphonyl}pyrazolo[1,5-a]pyridine and its N-oxide and pharmaceutically acceptable salts; 2-isopropyl-3-{4-[3-(tertiobutylamino)propyloxy]benzenesulphonyl}pyrazolo[1,5-a]pyridine and its N-oxide and pharmaceutically acceptable salts.
Claim 8
Dependent Claim
17 words
An aminoalkoxyphenyl compound according to claim 2 wherein the pharmaceutically acceptable salt is the oxalate or hydrochloride.
Claim 9
Dependent Claim
122 words
An aminoalkoxyphenyl compound of formula: ##STR175## in which: R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; R 3 represents a C 1-8 alkyl radical; R 4 is selected from hydrogen and C 1-8 alkyl; R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; as well as the N-oxide derivative thereof and a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
122 words
An aminoalkoxyphenyl compound of formula: ##STR175## in which: R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from a straight- or branched-alkylene radical having from 2 to 5 carbon atoms, a 2-hydroxypropylene radical, and a 2-(lower alkoxy)propylene radical; R 3 represents a C 1-8 alkyl radical; R 4 is selected from hydrogen and C 1-8 alkyl; R is selected from hydrogen, C 1-8 alkyl, C 3-6 cycloalkyl, benzyl and phenyl optionally substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; as well as the N-oxide derivative thereof and a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
16 words
An aminoalkoxyphenyl derivative according to claim 7 in which R represents an isopropyl or cyclopropyl group.
Claim 12
Dependent Claim
43 words
A pharmaceutical or veterinary composition for use in the treatment of angina pectoris, hypertension, arrhythmia, and cerebral vascular insufficiency, comprising an effective amount for treating angina pectoris, hypertension, arrhythmia or cerebral vascular insufficiency of at least one aminoalkoxyphenyl compound according to claim 1.
Claim 13
Dependent Claim
38 words
A method of treating angina pectoris, hypertension, arrhythmia and cerebral vascular insufficiency in a host in need of such treatment comprising the administration to the host of an effective dose of an aminoalkoxyphenyl compound according to claim 1.
Claim 14
Dependent Claim
191 words
An aminoalkoxyphenyl derivative of formula: ##STR176## in which: B is selected from --S--, --SO-- and --SO 1 --; R is selected from hydrogen, linear- or branched-alkyl, cycloalkyl containing at most 6 carbon atoms and phenyl which is unsubstituted or substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from linear- or branched-alkylene having from 2 to 5 carbon atoms and 2-hydroxypropylene; R 3 is selected from linear- or branched-C 1-8 alkyl and a radical of formula Alk-R 5 , in which Alk denotes a single bond or a linear- or branched-alkylene radical having from 1 to 5 carbon atoms, and R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents which may be identical or different, selected from halogen, lower C 1-4 -alkyl and lower C 1-4 alkoxy; R 4 is selected from hydrogen and alkyl; as well as a pharmaceutically acceptable salt of this derivative.
Claim 15
Dependent Claim
191 words
An aminoalkoxyphenyl derivative of formula: ##STR176## in which: B is selected from --S--, --SO-- and --SO 1 --; R is selected from hydrogen, linear- or branched-alkyl, cycloalkyl containing at most 6 carbon atoms and phenyl which is unsubstituted or substituted with one or more substituents, which may be identical or different, selected from halogen, lower C 1-4 alkyl, lower C 1-4 alkoxy and nitro; R 1 and R 2 , which are identical or different, are selected from hydrogen, methyl, ethyl and halogen; A is selected from linear- or branched-alkylene having from 2 to 5 carbon atoms and 2-hydroxypropylene; R 3 is selected from linear- or branched-C 1-8 alkyl and a radical of formula Alk-R 5 , in which Alk denotes a single bond or a linear- or branched-alkylene radical having from 1 to 5 carbon atoms, and R 5 is selected from pyridyl, phenyl, 2,3-methylenedioxyphenyl, 3,4-methylenedioxyphenyl and phenyl substituted with one or more substituents which may be identical or different, selected from halogen, lower C 1-4 -alkyl and lower C 1-4 alkoxy; R 4 is selected from hydrogen and alkyl; as well as a pharmaceutically acceptable salt of this derivative.
Claim 16
Dependent Claim
156 words
An aminoalkoxyphenyl compound of formula: ##STR177## in which: B is selected from --S--, --SO-- and --SO 1 --; R is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertbutyl, 1-methyl-propyl, n-pentyl, neopentyl, phenyl, monofluoro-, monochloro- or monobromophenyl, difluoro-, dichloro-, or dibromophenyl, monomethyl- or dimethylphenyl, monomethoxy or dimethoxyphenyl, nitrophenyl and methylphenyl substituted with a halogen atom; R 1 and R 2 , which are identical or different, are selected from hydrogen, chlorine, bromine, iodine and methyl; A is selected from 1,2-ethylene, 1,3-propylene, 2-methyl-1,3-propylene, 1,4-tetramethylene, 1,5-pentamethylene and 2-hydroxypropylene; R 3 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 1-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, phenyl, benzyl, phenethyl, methoxyphenethyl, dimethoxyphenethyl, dimethylphenethyl, dimethoxyphenyl, dimethoxybenzyl and pyridyl ethyl or phenethyl substituted in the aromatic portion with methyl and methoxy radicals; R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertbutyl, n-pentyl, neopentyl, n-hexyl, n-heptyl and n-octyl; as well as a pharmaceutically acceptable salt of this derivative.
Claim 17
Dependent Claim
156 words
An aminoalkoxyphenyl compound of formula: ##STR177## in which: B is selected from --S--, --SO-- and --SO 1 --; R is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertbutyl, 1-methyl-propyl, n-pentyl, neopentyl, phenyl, monofluoro-, monochloro- or monobromophenyl, difluoro-, dichloro-, or dibromophenyl, monomethyl- or dimethylphenyl, monomethoxy or dimethoxyphenyl, nitrophenyl and methylphenyl substituted with a halogen atom; R 1 and R 2 , which are identical or different, are selected from hydrogen, chlorine, bromine, iodine and methyl; A is selected from 1,2-ethylene, 1,3-propylene, 2-methyl-1,3-propylene, 1,4-tetramethylene, 1,5-pentamethylene and 2-hydroxypropylene; R 3 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 1-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, phenyl, benzyl, phenethyl, methoxyphenethyl, dimethoxyphenethyl, dimethylphenethyl, dimethoxyphenyl, dimethoxybenzyl and pyridyl ethyl or phenethyl substituted in the aromatic portion with methyl and methoxy radicals; R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertbutyl, n-pentyl, neopentyl, n-hexyl, n-heptyl and n-octyl; as well as a pharmaceutically acceptable salt of this derivative.
Claim 18
Dependent Claim
15 words
An aminoalkoxyphenyl compound according to claim 11 wherein B represents a --SO 2 -- group.
Claim 19
Dependent Claim
17 words
An aminoalkoxyphenyl compound according to claim 11 wherein R 3 represents a 3,4-dimethoxyphenyl, 3,4-dimethoxybenzyl or 3,4-dimethoxyphenethyl radical.
Claim 20
Dependent Claim
15 words
An aminoalkoxyphenyl compound according to claim 11 wherein the pharmaceutically acceptable salt is the hydrochloride.
Claim 21
Dependent Claim
53 words
A pharmaceutical or veterinary composition for use in the treatment of angina pectoris, hypertension, arrhythmia, and cerebral vascular insufficiency, comprising an effective amount for treating angina pectoris, hypertension, arrhythmia and cerebral vascular insufficiency of at least one aminoalkoxyphenyl compound according to claim 11 in combination with a pharmaceutical vehicle or a suitable excipient.
Claim 22
Dependent Claim
53 words
A pharmaceutical or veterinary composition for use in the treatment of angina pectoris, hypertension, arrhythmia, and cerebral vascular insufficiency, comprising an effective amount for treating angina pectoris, hypertension, arrhythmia and cerebral vascular insufficiency of at least one aminoalkoxyphenyl compound according to claim 13 in combination with a pharmaceutical vehicle or a suitable excipient.
Claim 23
Dependent Claim
31 words
A pharmaceutical or veterinary composition according to claim 17 for the treatment of pathological syndromes of the cardiovascular system, containing from 50 mg to 500 mg of the said aminoalkoxyphenyl compound.
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) | 1996-01-26 | 1996-07-27 | 1997-01-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-01-26 | 2000-07-27 | 2001-01-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-01-26 | 2004-07-27 | 2005-01-26 | $7700.00 | Window Closed / Lapsed |