Abstract: Derivatives having the formula: ##STR1## in which R.sub.1 =C.sub.1 -C.sub.4 alkyl and Ar is an aryl or heteroaryl group chosen from among the following: ##STR2## where R.sub.2 represents a hydrogen atom one or two halogen atoms, a CN, NO.sub.2 or CF.sub.3 group, one, two or three C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups or an amino group substituted by two C.sub.1 -C.sub.4 alkyl groups, in which case the --W--V-- chain represents --N.dbd.N-- or ##STR3## and n=2-6; (ii) pyridyl, in which case the --W--V-- chain represents --N.dbd.N-- and n= 1-6, and acid addition salts of those derivatives (I) which are salt-forming.These derivatives are of use in therapy as agents for inhibiting type B monoamine oxydase.
Type:
Grant
Filed:
September 10, 1993
Date of Patent:
December 27, 1994
Assignee:
Delalande S.A.
Inventors:
Jean-Jacques Koenig, Luc L. Lebreton, Maryse F. Masson
Abstract: Derivatives having the formula: ##STR1## where R.sub.1 denotes C.sub.1 -C.sub.4 alkyl; X denotes oxygen or methylene; R.sub.2 denotes C.sub.1 -C.sub.4 alkyl or CF.sub.3 ; R.sub.3 denotes a CH.sub.2 R.sub.4 group in which R.sub.4 is (i) a pentagonal or hexagonal aromatic heterocyclic group comprising one or two nitrogen atoms and optionally fused with a benzene ring or (ii) a group having the formula ##STR2## where n=0 or 1, and R.sub.5 and R.sub.6 independently denote C.sub.1 -C.sub.4 alkyl or benzyl, and R.sub.5 and R.sub.6 also, together with the nitrogen atom to which they are bonded, form a piperidino or pyrrolidino or morpholino or N-methyl piperazino radical, and their N-oxide forms and acid addition salts of these derivatives and their N-oxide forms, the derivatives being in various stereoisomeric forms or in the form of a mixture of these forms, including the racemic form.
Abstract: Derivatives having the formula: ##STR1## in which R.sub.1 =C.sub.1 -C.sub.4 alkyl and Ar is an aryl or heteroaryl group chosen from among the following:(i) ##STR2## where R.sub.2 represents a hydrogen atom one or two halogen atoms, a CN, NO.sub.2 or CF.sub.3 group, one, two or three C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups or an amino group substituted by two C.sub.1 -C.sub.4 alkyl groups, in which case the --W--V-- chain represent ##STR3## and n=2-6; (ii) pyridyl, in which case the --W--V-- chain represents --N.dbd.N--and n=1-6, and acid addition salts of those derivatives (I) which are salt-forming.These derivatives are of use in therapy as agents for inhibiting type B monoamine oxydase.
Type:
Grant
Filed:
May 5, 1992
Date of Patent:
November 16, 1993
Assignee:
Delalande S.A.
Inventors:
Jean-Jacques Koenig, Luc L. Lebreton, Maryse F. Masson
Abstract: Compounds for therapeutic use of formula: ##STR1## where the chain--W--V--N--represents--N.dbd.N--N--, --N--N.dbd.N--,--O--CO--N--,--O--CS--N--, --S--CO--N--or--S--CS--N--; Ar is an aryl group; and A is a vinyl group or an alkylene chain terminated by CN, methoxy, ethoxy, OH, halogen or NH.sub.2 which may possibly be substituted.
Type:
Grant
Filed:
January 3, 1992
Date of Patent:
October 5, 1993
Assignee:
Delalande S.A.
Inventors:
Rene L. Milcent, Luc Lebreton, Fathi Mazouz, Claude Burstein, Salah Gueddari
Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and is 0 or 1 when X is a --CH.dbd.CH-- group;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl, benzyl, CHF.sub.2, CF.sub.3 or CF.sub.3 CF.sub.2 group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl group;R'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain; andeach of R.sub.4 and R'.sub.4 independently is a C.sub.1 -C.sub.4 alkyl group or R.sub.4 and R'.sub.4 form together either a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain, a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain substituted by one or two C.sub.1 -C.sub.4 alkyl groups, or a --(CH.sub.2).sub.2 -- chain substituted by one or two --CH.sub.2 --NH.sub.
Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group; each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CF.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 --or --(CH.sub.2).sub.5 --chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs, prepared by cyclizing N ethoxy carbonyl anilines with substituted 1, 3 dioxolane-2-ones.
Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.
Abstract: The present invention relates to compounds of formula: ##STR1## in which: R.sub.3 is hydrogen, 2-tetrahydropyranyl or benzyl;R.sub.1 and R.sub.2 are such that:either R.sub.1 represents a methoxy group in which case R.sub.2 is a group chosen from the following: hydroxyl; C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.5 -C.sub.7 cycloalkloxy; benzyloxy;or R.sub.2 represents a methoxy group in which case R.sub.1 is a group chosen from the following: hydroxyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.2 -C.sub.8 alkyloxy substituted by a methoxy group; C.sub.1 -C.sub.4 trifluoroalkyloxy; C.sub.3 -C.sub.4 alkenyloxy; C.sub.5 -C.sub.7 cycloalkyloxy; benzyloxy; C.sub.1 -C.sub.4 alkylthio;n=2 or 3; andp=4, 5 or 6,as well as their addition salts with mineral or organic acids, said compounds and salts being useful as drugs.
Type:
Grant
Filed:
January 3, 1991
Date of Patent:
September 1, 1992
Assignee:
Delalande S.A.
Inventors:
Mona Ward, Pierre-Andre Ph. Settembre, Alain Renaud, Michel Langlois
Abstract: The invention provides a method of synthesizing a copolymer of two .alpha.-amino acids which comprises the preparation of an N-carboxyanhydride of a first .alpha.-amino acid and the N-carboxyanhydride of a second .alpha.-amino acid, followed by the copolymerization of this mixture. The mixture is obtained by the reaction of phosgene with a mixture of a first and the second .alpha.-amino acids, the amino acids having similar reaction rates with phosgene. It also relates to the copolymer obtained by implementation of this method and an agent for covering skin wounds comprising this copolymer.
Abstract: Method of treatment of affections related to a disturbance of the intra and extra cellular movements of calcium at the cerebral level, which comprises administering an aromatic aminoalkoxy derivative of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which A represents a chain having any of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; `m takes the value 3.
Type:
Grant
Filed:
April 27, 1990
Date of Patent:
July 21, 1992
Assignee:
Delalande S.A.
Inventors:
Bernard M. Pourrias, Raphael Santamaria, Mona M. Ward
Abstract: Compounds for therapeutic use of formula: ##STR1## where the chain--W--V--N--represents--N.dbd.N--N--, --N--N.dbd.N--, --O--CO--N--, --O--CS--N--, --S--CO--N-- or --S--CS--N--; Ar is an aryl group; and A is a vinyl group or an alkylene chain terminated by CN, methoxy, ethoxy, OH, halogen or NH.sub.2 which may possibly be substituted.
Type:
Grant
Filed:
May 25, 1989
Date of Patent:
March 31, 1992
Assignee:
Delalande S.A.
Inventors:
Rene L. Milcent, Luc Lebreton, Fathi Mazouz, Claude Burstein, Salah Gueddari
Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and is 0 or 1 when X is a --CH.dbd.CH-- group;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl, benzyl, CHF.sub.2, CF.sub.3 or CF.sub.3 CF.sub.2 group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl group;R'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain; andeach of R.sub.4 and R'.sub.4 independently is a C.sub.1 -C.sub.4 alkyl group or R.sub.4 and R'.sub.4 form together either a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain, a --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 -- chain substituted by one or two C.sub.1 -C.sub.4 alkyl groups, or a --(CH.sub.2).sub.2 -- chain substituted by one or two --CH.sub.2 --NH.sub.
Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CH.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs.
Abstract: Method of preparing 4-disubstituted phenyl-1-tetralones of formula ##STR1## in which X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and Y, situated in position 2' or 3', represents halogen or C.sub.1 -C.sub.4 alkyl, this method being characterized in that it comprises the reaction, in the presence of an acid agent, of .alpha.-naphthol of formula (II) with a phenyl compound of formula (III): ##STR2## where X represents halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, and Y is situated in the ortho or meta position with respect to X and represents halogen or C.sub.1 -C.sub.4 alkyl.
Abstract: The present invention relates to compounds of formula: ##STR1## in which: R.sub.1 and R.sub.2 are such that:either R.sub.1 represents a methoxy group in which case R.sub.2 is a group chosen from the following: hydroxyl; C.sub.1 -C.sub.4 alkyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.5 -C.sub.7 cycloalkyloxy; benzyloxy;or R.sub.2 represents a methoxy group in which case R.sub.1 is a group chosen from the following: hydroxyl; C.sub.2 -C.sub.8 alkyloxy; C.sub.2 -C.sub.8 alkyloxy substituted by a methoxy group; C.sub.1 -C.sub.4 trifluoroalkyloxy; C.sub.3 -C.sub.4 alkenyloxy; C.sub.5 -C.sub.7 cycloalkyloxy; benzyloxy; C.sub.1 -C.sub.4 alkyhlthio;n=2 or 3; andp=4, 5 or 6,as well as their addition salts with mineral or organic acids, said compounds and salts being useful as drugs.
Type:
Grant
Filed:
April 18, 1989
Date of Patent:
May 21, 1991
Assignee:
Delalande S.A.
Inventors:
Mona Ward, Pierre-Andre Ph.Settembre, Alain Renaud, Michel Langlois
Abstract: The present invention relates to tricyclic carbamates coplying with the formula ##STR1## in which n=0, 1 or 2,p=0 or 1,R.sub.1 represents a hydrogen atom; a group which is alkyl in C.sub.1 -C.sub.4 ; a phenyl group; a group which is alkenyl in C.sub.2 -C.sub.3 ; or a methyl group substituted by a hydroxy group, a group which is alkoxy in C.sub.1 -C.sub.4, an amino group or an N-alkylamino or N,N-dialkylamino group where the alkyl radical is in C.sub.1 -C.sub.4, andR.sub.2 represents a hydrogen atom; a halogen atom; a group which is alkyl in C.sub.1 -C.sub.4, or a group which is alkoxy in C.sub.1 -C.sub.4, and their salts of addition of acid.These compounds are therapeutically useful, notably as antidepressant agents.
Type:
Grant
Filed:
December 13, 1988
Date of Patent:
March 19, 1991
Assignee:
Delalande S.A.
Inventors:
Alain J. L. Renaud, Alain R. Schoofs, Jean-Marc M. Guiraudie, Denis M. Brochet
Abstract: A mixture of the 4 stereoisomers of formula (I) below, each of the pairs of corresponding racemic diastereoisomers and each of the enantiomers corresponding to each pair, that is to say each of said stereoisomers: ##STR1## in which R.sub.1 represents: a hydrogen atom,an alkoxy group comprising from 1 to 4 carbon atoms,a trifluoromethyl group, orone or two halogen atoms;and the pair (R.sub.2, R.sub.3) has one of the following meanings: (H, H), (H, C.sub.1 -C.sub.4 alkyl), (C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl), as well as their organic and inorganic acid addition salts.The compounds of formula (I) are therapeutically useful.
Type:
Grant
Filed:
September 2, 1987
Date of Patent:
January 30, 1990
Assignee:
Delalande S.A.
Inventors:
Michel Langlois, Alain-Rene Schoofs, Jean-Francois Rumigny, Philippe Dostert, Margherita Strolin-Benedetti, Patrice Renaut
Abstract: Compounds of formula: ##STR1## wherein: Ar is an aromatic group; R and R.sub.1 are H or CH.sub.3 ; A represents a nitrogenized heterocyclic radical; B is OH or forms with the adjacent CO group, either an amido group, or a carbonyloxy group; R.sub.2 and R.sub.3 are H or alkyl; m=0 or 1; and n=0, 1, 2 or 3.These compounds are useful as drugs having stimulating, protecting and/or correcting activities of the cerebral functions.
Type:
Grant
Filed:
March 19, 1987
Date of Patent:
February 28, 1989
Assignee:
Delalande S.A.
Inventors:
Alain Y. Platel, Guy R. Bourgery, Patrick G. Guerret
Abstract: The present invention provides a process for preparing 6-(lower)alkoxy-1-naphthoic acids, the corresponding esters and 5-halo substituted derivatives thereof. The process comprises reacting furoic acid with an alkoxyphenyl compound, followed by acid hydrolysis to form a mixture of alkoxy and hydroxy substituted naphthoic acids, subjecting said mixture to the action of an alkylating agent, and optionally further treating the alkylated product to another hydrolysis step or a halogenation step.
Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
Type:
Grant
Filed:
June 26, 1985
Date of Patent:
March 22, 1988
Assignee:
Delalande S.A.
Inventors:
Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria