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Alkyl- or aryl-aminoalkoxy-benzene-sulfonyl indoles

Assignee: Elf Sanofi SA
•
Filing: 1989-02-06
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Granted: 1991-02-19
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Expires: 2009-02-06
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Abstract

Abstract The present invention relates to aminoalkoxyphenyl derivatives of formula: ##STR1## and its N-oxide and pharmaceutically acceptable salts, 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 radial or a halogen atom, A denotes a straight-or branched-alkylene radical having from 2 to 5 carbon atoms or a 2-hydroxypropylene radial in which the hydroxy is optionally substituted by a lower alkyl radical, R 3 denotes an alkkyl radical or a radical of formula: --Alk--Ar in which Alk denotes a single bond or a linear- or branched-alkylene radical having from 1 to 5 carbon atoms and Ar 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 group or lower alkoxy groups, R 11 denotes hydrogen or a lower alkyl, phenyl, diphenylmethyl, benzyl or halogenobenzyl radical, 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 ##STR2## R represent hydrogen, an alkyl radical, a cycloalkyl radical, a benzyl radical or a phenyl radical optionally substituted with one or more substituents, which may be identical or different, selected from halogen atoms and from lower alkyl, lower alkoxy or nitro groups, are described. The compounds of the invention possess exceptional pharmacological properties, especially calcium transport inhibitory properties, as well as bradycardic, hypotensive and antiadrenergic properties.

Inventors

  • 👤 Jean Gubin
  • 👤 Pierre Chatelain
  • 👤 Henri Inion

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 17:41
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P25/00; A61P25/02; A61P3/00; A61P35/00; A61P9/00; A61P9/06; A61P9/08; A61P9/10; A61P9/12

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 206 words
An aminoalkoxyphenyl compound of formula: ##STR168## and pharmaceutically acceptable salts, 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 atom, 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--Ar in which Alk denotes a single bond or a linear-or branched-alkylene radical having from 1 to 5 carbon atoms and Ar 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 group or lower alkoxy groups, R 11 denotes hydrogen or a lower alkyl, phenyl, diphenylmethyl, benzyl or halogenobenzyl radical, R 4 denotes hydrogen or a C 1-8 alkyl radical, R represents hydrogen, an alkyl radical, a cycloalkyl radical, a benzyl radical or a phenyl radical optionally substituted with one or more substituents, which may be identical or different, selected from halogen atoms and from lower alkyl, lower alkoxy or nitro groups.
Claim 2
Dependent Claim 206 words
An aminoalkoxyphenyl compound of formula: ##STR168## and pharmaceutically acceptable salts, 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 atom, 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--Ar in which Alk denotes a single bond or a linear-or branched-alkylene radical having from 1 to 5 carbon atoms and Ar 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 group or lower alkoxy groups, R 11 denotes hydrogen or a lower alkyl, phenyl, diphenylmethyl, benzyl or halogenobenzyl radical, R 4 denotes hydrogen or a C 1-8 alkyl radical, R represents hydrogen, an alkyl radical, a cycloalkyl radical, a benzyl radical or a phenyl radical optionally substituted with one or more substituents, which may be identical or different, selected from halogen atoms and from lower alkyl, lower alkoxy or nitro groups.
Claim 3
Dependent Claim 16 words
An aminoalkoxyphenyl compound according to claim 1 in which B represents a --SO 2 -- group.
Claim 4
Dependent Claim 29 words
An aminoalkoxyphenyl compound according to claim 1 in which R 3 represents hydrogen and R 4 represents tert-butyl or R 3 and R 4 each represent n-propyl or n-butyl.
Claim 5
Dependent Claim 16 words
An aminoalkoxyphenyl compound according to claim 1 in which-O-A-NR 3 R 4 represents a N-methyl-N-[(3,4-dimethoxy-β-phenethyl)amino]propyloxy group.
Claim 6
Dependent Claim 17 words
An aminoalkoxyphenyl compound according to claim 1 in which R 1 and R 2 each represent hydrogen.
Claim 7
Dependent Claim 16 words
An aminoalkoxyphenyl compound according to claim 1 in which R represents an isopropyl or cyclopropyl group.
Claim 8
Dependent Claim 17 words
An aminoalkoxyphenyl compound according to claim 1 wherein the pharmaceutically acceptable salt is the oxalate or hydrochloride.
Claim 9
Dependent Claim 15 words
An aminoalkoxyphenyl compound according to claim 1 which is 2-isopropyl-3-[4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulfonyl]indole and its pharmaceutically acceptable salts.
Claim 10
Dependent Claim 15 words
An aminoalkoxyphenyl compound according to claim 1 which is 2-isopropyl-3-[4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulfonyl]-1-methyl-indole and its pharmaceutically acceptable salts.
Claim 11
Dependent Claim 15 words
An aminoalkoxyphenyl compound according to claim 1 which is 3-isopropyl-2-[4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulfonyl]indole and its pharmaceutically acceptable salts.
Claim 12
Dependent Claim 15 words
An aminoalkoxyphenyl compound according to claim 1 which is 1-methyl-2-isopropyl-3-[4-{3-[N-methyl-N-(3,4-dimethoxy-benzyl)amino]propyloxy}benzenesulfonyl]indole and its pharmaceutically acceptable salts.
Claim 13
Dependent Claim 15 words
An aminoalkoxyphenyl compound according to claim 1 which is 1-methyl-3-isopropyl-2-[4-{3-[N-methyl-N-(3,4-dimethoxy-β-phenethyl)amino]propyloxy}benzenesulfonyl]indole and its pharmaceutically acceptable salts.
Claim 14
Dependent Claim 41 words
A pharmaceutical or veterinary composition for the treatment of angina pectoris, hypertension and arrhythmia containing, as active principle, an effective amount of at least one aminoalkoxyphenyl compound according to claim 1 in combination with a pharmaceutical vehicle or a suitable excipient.
Claim 15
Dependent Claim 35 words
A method of treating angina pectoris, hypertension and arrhythmia in a host in need of such treatment comprising the administration of the host of an effective amount of an aminoalkoxyphenyl compound according to claim 1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-02-18 1994-08-20 1995-02-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-02-18 1998-08-20 1999-02-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-02-18 2002-08-20 2003-02-19 $7700.00 Window Closed / Lapsed

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