Societe De Conseils De Recherches Et D'applications Scientifiques

Societe D'etudes De Produits Chimiques

Societe De Conseils De Recherches Et D'applications Scientifiques (s.c.r.a.s.)

Andre Esanu

Pierre Braquet

Jean-Pierre Laurent

Jacques Pommier

Alain Rolland

Charles Eck

Christiane Martin

The invention relates to thieno-triazolo-diazepine derivatives of the formula: ##STR1## wherein Y stands for oxygen or sulphur and R stands for various substituents, to a preparation process of said compounds and to therapeutic compositions containing the same. The compounds are particularly interesting as anti-asthmatic, anti-allergic and gastro-intestinal protectors.

Derivatives of thieno-triazolo-diazepine and therapeutic compositions

The invention relates to pyrrolo-pyridine derivatives of the formula: ##STR1## wherein R represents a phenyl group, optionally substituted by one or more of various groups and therapeutically acceptable salts of these compounds, to a preparation process of the same comprising reacting, in an inert atmosphere and in a protic solvent, the 2-methyl 3-hydroxy 4,5-diboromomethyl pyridine, on a stoichiometric excess of the compound of the formula NH.sub.2 -R. The invention relates also to therapeutic compositions containing said derivatives as active ingredient. The compounds according to the invention have antiallergic activity.

Pyrrolo-pyridine derivatives and therapeutic compositions containing them

This invention relates to thieno-triazolo-diazepine derivatives of the formula ##STR1## wherein R represents various substituents, to a preparation process of these compounds consisting in reacting the thieno-triazolo-diazepine compound of the formula ##STR2## on RSO.sub.2 Cl and to therapeutic compositions containing the same. The compounds are particularly interesting as anti-PAF and anti-ischemic agents.

Sulfonyl derivatives of thieno-triazolo-diazepines useful as anti-PAF

The invention relates to thieno-triazolo-diazepine derivatives of the formula ##STR1## wherein Y stands for oxygen or sulphur and R stands for various substituents, to a preparation process of said compounds and to therapeutic compositions containing the same. The compounds are particularly interesting in the treatment of ischemia.

Thieno-triazolo-diazepine derivatives useful as anti-ischemic agents

Separation of isomers of furo (3,4-C) pyridine derivatives

The invention relates to new quinoline derivatives of the formula: ##STR1## wherein R stands for C.sub.2 H.sub.5, C.sub.2 H.sub.4 F, CH.sub.2 -O-CH.sub.2 -CH.sub.2 OH, ##STR2## to a process for their preparation comprising reacting, for 12-24 hours, at 70.degree.-95.degree. C., in dimethylformamide, the 1,4-dihydro- 3-ethoxycarbonyl- 6,8- difluoro-4-oxo-quinoline with an excess of RX (2-5 mol of RX for one mol of quinoline), in the presence of K.sub.2 CO.sub.3 and subsequently hydrolysing the obtained 3-ester by HCl under reflux conditions and to pharmaceutical compositions comprising at least one 1,4-dihydro- 3-carboxy- 6,8-difluoro- 1-R-4-oxo-quinoline derivative in admixture with a pharmaceutically acceptable diluent or carrier.

Quinoline derivatives, their preparation and therapeutic compositions

This invention relates to indenofuran derivatives of the formula: ##STR1## wherein R stands for H or for a ##STR2## group optionally substituted on the phenyl ring by Alk, OH or OAlk, Alk being a lower straight or branched alkyl group up to C.sub.5, to the preparation of these compounds and to therapeutic compositions containing the same in the field of anaphylaxis.

Octahydro indenofuran derivatives and their therapeutic compositions

The invention relates to new quinoline derivatives of the formula: ##STR1## wherein R stands for C.sub.2 H.sub.5, C.sub.2 H.sub.4 F, CH.sub.2 --O--CH.sub.2 --CH.sub.2 OH, ##STR2## to a process for their preparation comprising reacting, for 12-24 hours, at 70.degree.-95.degree. C., in dimethylformamide, the 1,4-dihydro- 3-ethoxycarbonyl- 6,8- difluoro-4-oxo-quinoline with an excess of RX (2-5 mol of RX for one mol of quinoline), in the presence of K.sub.2 CO.sub.3 and subsequently hydrolyzing the obtained 3-ester by HCl under reflux conditions and to pharmaceutical compositions comprising at least one 1,4-dihydro- 3-carboxy- 6,8-difluoro- 1-R-4-oxo-quinoline derivative in admixture with a pharmaceutically acceptable diluent or carrier.

New quinoline derivatives, their preparation and therapeutic

This invention relates to 1,3-dihydro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula I ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various hydrocarbon groups and therapeutically acceptable addition salts thereof; to a process for the preparation of the same comprising oxidizing the secondary alcohol .alpha..sup.4, 3-o-isopropylidene-1-methyl-5-(1-hydroxy-1-A.sub.1)-methyl pyridine by any usual technique, reacting the resultant ketone with a compound of the general formula XA.sub.2 wherein X stands for Br or I in the presence of magnesium in diethyl ether at the boil and treating the resultant tertiary alcohol with an acidic agent to provoke breaking of the isopropylidene ring and 3,4-cyclisation; and to pharmaceutical compositions containing these derivatives useful for example in diuresis.

Furo-(3,4-C)-pyridine derivatives and therapeutic composition containing

This invention relates to bornane derivatives of the formula: ##STR1## wherein Z stands for: ##STR2## and Y stands for an arabinose, xylose or ribose rest, the acetylated form of the same, with either a pyrane or furane configuration and bound to the R rest to lead either to the .alpha. or to the .beta. anomer, to a process for the preparation of these compounds and to therapeutic compositions comprising one of them as an essential ingredient.

Bornane derivatives, their preparation and therapeutic compositions

This invention relates to new pyranoderivatives of the formula: ##STR1## wherein X.sub.1 is H, Cl or Br and Z stands for: ##STR2## wherein X.sub.2 is H, Cl or Br, T is O or S and Y stands for an arabinose, xylose or ribose moiety, the acetylated form of the same, with either a pyranose or furanose configuration and bound to the R moiety of either the .alpha. or the .beta. anomer, to a preparation process of said compounds from stoichiometric proportions of the compound R--H and of the selected ose, and to therapeutic compositions, the active ingredient of which comprises at least one of these compounds associated with an appropriate diluent or carrier.

Pyranoderivatives, their preparation and therapeutic compositions

This invention relates to new derivatives of 5-(.omega.-phenethylamino-alkyl) -4,5,6,7-tetrahydro-thieno-(3,2-c)-pyridine of the formula ##STR1## wherein n is an integer of from 2 to 5, R.sub.1 represents a hydrogen atom or a 3,4-dimethoxyphenyl group, R.sub.2 represents a hydrogen atom, an alkyl group having up to 4 carbon atoms or a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group and R.sub.3 represents two or three methoxy groups, to therapeutically acceptable salts thereof, to a process for the preparation of these derivatives comprising condensing a 5-(.omega.-chloroalkyl)-4,5,6,7- tetrahydro- thieno- (3,2-c)-pyridine with the appropriate phenethyl derivative at from 90.degree. to 130.degree. C. under nitrogen circulation and to therapeutic compositions containing said compounds.

Thienopyridine derivatives and anti-thrombotic compositions containing

This invention relates to new 1,3-dihydro-6-[1-cyano-1-isopropyl-N-phenethyl-N-methyl-.omega.-aminoalkyl ]-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various substituents and to pharmaceutically acceptable salts of said derivatives, to a process for the preparation of the same, comprising reacting, in stoichiometric proportions, at 15.degree.-65.degree. C., in dimethylsulphoxide, a 6-(1-cyano-2-methyl-propyl)-7-hydroxy-furo-(3,4-c)-pyridine derivative with the appropriate N-methyl-N-phenethyl-.omega.-aminoalkyl choride and, finally, to a therapeutic composition of matter comprising as an essential ingredient therein any of said compounds in an amount effective to act as a calcium antagonist or a serotonin antagonist together with an appropriate diluent or carrier.

6-phenethylaminoalkyl-furo-(3,4-c)-pyridine derivatives and therapeutic

The invention relates to new 5-(1-cyano-1-alkyl-N-methyl-N-methoxy-phenethyl)-alkylamino-2,2,8-trimethy l-4H-dioxino-(4,5-c)-pyridine derivatives of the formula ##STR1## and therapeutically acceptable salts of these compounds, to a preparation process of the same comprising reacting, in stoichiometric proportions, the corresponding 5-(1-cyano-1-R.sub.1)-methyl-2,2,8-trimethyl-4H-dioxino-(4,5-c)-pyridine of the formula ##STR2## on the appropriate [N-methyl-N-(methoxy-phenethyl)]-.omega.-alkyl chloride of the formula ##STR3## The invention relates also to therapeutic compositions containing said derivatives as active ingredients.

5-(1-cyano-1-alkyl-N-methyl-N-methoxy-phenethyl)-alkylamino-2,2,8-trimeth

This invention relates to 1,3 - dihydro-6-aminomethyl-7-hydroxy-furo-(3,4-c)- pyridine derivatives of the general formula I ##STR1## wherein A.sub.1, A.sub.2, R.sub.1 and R.sub.2 represent various substituents, to pharmaceutically acceptable salts of such compounds, to a process for the preparation of compounds comprising reacting a 6-chloromethyl-7-benzoxy derivative of the general formula II ##STR2## with an excess of an amine derivative ##STR3## in a non-polar solvent, at a temperature not exceeding 20.degree. C., which leads to the desired substitution in position 6, followed by an acidic treatment to cleave the benzyl group and, finally to an anti-allergic composition of matter comprising, as an essential ingredient therein, an effective amount of one of these compounds together with an appropriate diluent or carrier.

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Paris, France

Andre Esanu