Patent EP0112191B1 successfully refreshed from Google Patents.
EP0112191B1
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4-(1h-indolyl-3-)-alpha-methyl piperidine-1-ethanol derivatives, their salts, process for their preparation, compositions containing them and their use as medicines
Assignee: Sanofi Aventis France
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Filing: 1983-09-29
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Granted: 1987-02-04
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Expires: 2003-09-29
Abstract
Abstract Novel 4-(1H-indol-3-yl)- alpha -methyl-piperidine-1-ethanol derivatives of the formula <IMAGE> I wherein R is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, -NO2, -NH2, CF3- and CH3S-, R1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and -OH, Ar is selected from the group consisting of optionally substituted aryl and heteroaryl, the dotted line indicates the optional presence of a double bond and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable antagonistic properties toward calcium ion and antihypertensive activity and certain compounds possess alpha and/or beta -blocking properties.
Inventors
- 👤 François Clemence
- 👤 Neil Leslie Brown
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 05:58
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; A; A61; A61P; A61P25/00; A61P25/02; A61P3/00; A61P43/00; A61P9/00; A61P9/06; A61P9/12
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
157 words
1) The derivatives of 4-(1H-indol-3-yl)α-methyl piperidine-1-ethanol, as well as their salts of addition with mineral or organic acids, characterised in that they answer to the general formula (I): in which R represents a hydrogen or halogen atom, or an alkyl or alkoxy radical containing from 1 to 5 carbon, nitro, amino, trifluoromethyl or methylthio atoms, R, represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms, R 2 represents a hydrogen atom, an alkyl radical containing from 1 to 5 carbon atoms or a hydroxy radical, Ar represents an aryl or hetero-aryl radical containing from 4 to 14 carbon atoms possibly substituted by one or more chlorine, bromine or fluorine atoms, or hydroxy, hydroxymethyl, hydroxybutyl, methoxy, ethoxy, propoxy, methoxy-ethyl, carbamoyl, propenyl, propenyloxy, acetamido, butyrylamino, acetyl, nitro, amino, methyl, ethyl, propyl, methylsulphonamido, cyano, methoxy-carbonyl, cyclohexyl, propynyl, ethynyl, propynyloxy or trifluoromethyl radicals, and the dotted line represents the possible presence of a carbon-carbon bond.
Claim 2
Dependent Claim
157 words
1) The derivatives of 4-(1H-indol-3-yl)α-methyl piperidine-1-ethanol, as well as their salts of addition with mineral or organic acids, characterised in that they answer to the general formula (I): in which R represents a hydrogen or halogen atom, or an alkyl or alkoxy radical containing from 1 to 5 carbon, nitro, amino, trifluoromethyl or methylthio atoms, R, represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms, R 2 represents a hydrogen atom, an alkyl radical containing from 1 to 5 carbon atoms or a hydroxy radical, Ar represents an aryl or hetero-aryl radical containing from 4 to 14 carbon atoms possibly substituted by one or more chlorine, bromine or fluorine atoms, or hydroxy, hydroxymethyl, hydroxybutyl, methoxy, ethoxy, propoxy, methoxy-ethyl, carbamoyl, propenyl, propenyloxy, acetamido, butyrylamino, acetyl, nitro, amino, methyl, ethyl, propyl, methylsulphonamido, cyano, methoxy-carbonyl, cyclohexyl, propynyl, ethynyl, propynyloxy or trifluoromethyl radicals, and the dotted line represents the possible presence of a carbon-carbon bond.
Claim 3
Dependent Claim
47 words
2) The derivatives of 4-(1 H-indol-3-yl)α-methyl piperidine-1-ethanol, as defined by formula (I) of claim 1, as well as their salts of addition with mineral or organic acids, characterised in that R 2 represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms.
Claim 4
Dependent Claim
31 words
3) The derivatives according to claim 1 or 2, as well as their salts of addition with mineral or organic acids, characterized in that the dotted line represents a carbon-carbon bond.
Claim 5
Dependent Claim
31 words
4) The derivatives according to claim 1,2 or 3 as well as their salts of addition with mineral or organic acids, characterized in that Ar represents a possibly substituted phenyl radical.
Claim 6
Dependent Claim
35 words
5) The derivatives according to claim 1, 2, 3 or 4, as well as their salts of addition with mineral or organic acids, characterized in that R 1 and R 2 represent a hydrogen atom.
Claim 7
Dependent Claim
16 words
6) 4-(6-methoxy 1 H-indol-3-yl)α-([2-(prop-2-enyloxy)phenoxy]-methyl]piperidine-1-ethanol, as well as its salts of addition with mineral or organic acids.
Claim 8
Dependent Claim
16 words
6) 4-(6-methoxy 1 H-indol-3-yl)α-([2-(prop-2-enyloxy)phenoxy]-methyl]piperidine-1-ethanol, as well as its salts of addition with mineral or organic acids.
Claim 9
Dependent Claim
16 words
7) 4-(1 H-indol-3-yl)α-([2-(prop-2-enyloxy)phenyloxy]methyl]-1,2,3,6-tetrahydro pyridine-1-ethanoi as well as its salts of addition with mineral or organic acids.
Claim 10
Dependent Claim
16 words
7) 4-(1 H-indol-3-yl)α-([2-(prop-2-enyloxy)phenyloxy]methyl]-1,2,3,6-tetrahydro pyridine-1-ethanoi as well as its salts of addition with mineral or organic acids.
Claim 11
Dependent Claim
146 words
8) Preparation process for the new derivatives of 4-(1 H-indol-3-yl)α-methyl piperidine-1-ethanol, as defined by formula (I) of claim 1, as well as their salts of addition with mineral or organic acids characterized in that a derivative of indole with the formula (II): in which R, R 1 and R 2 have the significance already indicated, is made to react with an epoxide with the formula (III): in which Ar has the significance already indicated, so as to obtain a product with the formula (I) which is isolated and, if desired, salified or is submitted, if necessary or desired, to one or more of the following reactions in an appropriate order: - deprotection of the protected hydroxy group or groups; - reduction of the nitro group or groups into amino groups; - acylation of the amino group or groups; - salification by a mineral or organic acid.
Claim 12
Dependent Claim
133 words
9) Process according to claim 8, characterized in that: - the reaction of the indole with the formula (II) with the epoxide with the formula (III) is carried out in a benzenemethanol solvent mixture at reflux; - when the Ar group is substituted by one or more hydroxy groups, the latter are protected in the form of benzyl derivatives; - the deprotection of the hydroxy group or groups is carried out by reduction with hydrogen in the presence of a catalyst such as palladium; - the reduction of the nitro group or groups is carried out by hydrogen in the presence of a catalyst such as palladium; - the acylation of the amino group or groups is carried out by a functional derivative of an acyl such as a chloride or an anhydride.
Claim 13
Dependent Claim
36 words
10) Medicaments, characterized in that they are constituted by the new derivatives of 4-(1 H-indol-3-yl)α-methyl piperidine-1-ethanol, as defined by formula (I) of claim 1, as well as by their salts of addition with pharmaceutically acceptable acids.
Claim 14
Dependent Claim
32 words
11) Medicaments, characterized in that they are constituted by the new derivatives of 4-(lH-indol-3-yl)a-methyl piperidine-1-ethanol as defined in claim 2, as well as by their salts of addition with pharmaceutically acceptable acids.
Claim 15
Dependent Claim
39 words
12) Medicaments, characterized in that they are constituted by the derivatives of 4-(1 H-indol-3-yl)a-methyl piperidine-1-ethanol, as defined in any one of the claims 3, 4 or 5, as well as by their salts of addition with pharmaceutically acceptable acids.
Claim 16
Dependent Claim
36 words
13) Medicaments, characterized in that they are constituted by the derivatives of 4-(1H-indol-3-yl)a-methyl piperidine-1-ethanol as defined in either one of the claims 6 or 7, as well as their salts of addition with pharmaceutically acceptable acids.
Claim 17
Dependent Claim
28 words
14) Pharmaceutical compositions, characterized in that they contain, as active principle, one at least of the medicaments, as defined in any one of the claims 10,11,12 or 13.
References Cited (Backward Citations)
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