Roussel Uclaf

Robert Fournex

Lucien Nedelec

Francois Clemence

Yani Christidis

Vesperto Torelli

Colette Tournemine

Daniel Humbert

Italo Medici

Jacques Guillaume

Fernando Barzaghi

Claude Dumont

Andre Poittevin

Pierre Henri Derible

Andre Farcilli

Novel 20,21-dinoreburnamenines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and .dbd.CH.sub.2, the wavy line connecting to the E ring being a single bond when R is hydrogen or alkyl of 1 to 4 carbon atoms or a double bond when R is .dbd.CH.sub.2 and the dotted line being possibly an endo carbon-carbon bond when R is hydrogen or alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts in all their possible isomers forms, racemic mixtures and optical isomers having oxygenating and cerebral vasoregulating activity of great value and a novel process and intermediates for their preparation.

Blood oxygenating and cerebral vasoregulating 20,21-dinoreburnamenines

Diseases and ailments accompanied by gastric and gastroduodenal lesions treated by administering a compound of the formula (I) ##STR1## in which R represents hydrogen or alkyl containing 1 to 5 carbon atoms and R.sub.1 and R.sub.2, identical or different, both represent alkoxy containing 1 to 3 carbon atoms, or both represent halogen, or R.sub.1 represents hydrogen and R.sub.2 represents halogen, nitro or trifluoromethyl, or R.sub.1 and R.sub.2 form a methylenedioxy group at adjacent carbon atoms, as well as pharmaceutically acceptable salts thereof, particularly alkali metal, alkaline earth metal, or amine salts of said acid.

Gastro-protecting activity

A compound of the formula (I) ##STR1## in which the three methoxy radicals are in the 3,4,5, or 2,4,6 or 2,4,5 or 2,3,5 or 2,3,6 positions, in which either A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydroxy radical, and in which R represents a hydrogen atom or an alkyl containing 1 to 5 carbon atoms, in the various possible stereoisomeric forms, as well as the alkali metal, alkaline-earth metal, or amine salts thereof in which R represents a hydrogen atom, methods of producing the same, pharmaceutical compositions containing the same and treatment of various gastric ailments are disclosed.

Derivatives of phenyl aliphatic carboxylic acids, and use thereof in

Gastric and gastro-duodenal disorders are treated by administering a compound of formula (I) ##STR1## in which A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydroxy radical, and in which R represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms, in the various possible stereoisomeric forms, as well as the pharmaceutically acceptable alkali metal, alkaline earth metal or amine salts of the compound of formula (I) in which R represents a hydrogen atom.

Treatment of gastric and gastro-duodenal disorders with derivatives of

Diseases and ailments accompanied by gastric and gastroduodenal lesions treated by administering a compound of the formula (I) ##STR1## in which R represents hydrogen or alkyl containing 1 to 5 carbon atoms and R.sub.1 and R.sub.2, identical or different, both represent alkoxy containing 1 to 3 carbon atoms, or both represent halogen, or R.sub.1 represents hydrogen and R.sub.2 represents halogen, nitro or trifluoromethyl, or R.sub.1 and R.sub.2 form a methylenedioxy group at adjacent carbon atoms, in their racemic and optically active forms, as well as pharmaceutically acceptable salts thereof, particularly alkali metal, alkaline earth metal, or amine salts of said acid.

Gastro-protecting activity of substituted derivatives of

Novel indoles of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, X is selected from the group consisting of hydrogen and alkyl of 1 to 18 carbon atoms, Y is selected from the group consisting of hydrogen and halogen, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxy alkyl of 1 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms, arylalkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, --OH, --CF.sub.3, --OCF.sub.3, --NO.sub.2 and NH.sub.2, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl of 3 to 8 carbon atoms and alkynyl of 3 to 8 carbon atoms, and a and b may each be hydrogen or form a double bond or a is hydrogen and b is selected from the group consisting of --OH and alkoxy of 1 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having dopaminergic stimulating properties optionally accompanied with adrenergic and serotoninergic activity and their preparation and novel intermediates.

Dopaminergically stimulating 4-substituted indoles

New 20,21-dinoreburnamenine derivatives are disclosed which have the formula I ##STR1## wherein the hydroxyl in the 14-position of the molecule is in either of the two possible positions at the carbon atom in the 14-position to which the isomers A and B correspond and the hydrogens in the 3-position and the 16-position of the molecule are in cis- or in trans-position to each other, and their pharmaceutically acceptable acid addition salts, as well as pharmaceutical formulations thereof. The new compounds of formula I are prepared by reducing the corresponding 14-oxoderivatives. They are effective in favorably influencing the cerebral vascular circulation.

Cerebral vasodilating 20,21-dinoreburnamenine derivatives

Novel 19-nor-steroids of the formula ##STR1## wherein R.sub.1 and R.sub.2 taken together form a cycloalkyl of 3 to 8 carbon atoms or are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms with the proviso that both cannot be hydrogen, R.sub.3 is alkyl of 2 to 4 carbon atoms, R.sub.4 ' is selected from the group consisting of hydrogen, hydroxyl, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms and ##STR2## and M is selected from the group consisting of hydrogen and alkali metal, having antagonistic properties to aldosterone and increasing sodium-water diuresis with conservation of organic potassium and a novel process and novel intermediates for their preparation.

Novel 19-nor-steroids

Novel 7-alkyl-.DELTA..sup.4 -17.alpha.-pregnene-3-ones of the formula ##STR1## wherein R is selected from the group consisting of saturated and unsaturated alkyl of 2 to 8 carbon atoms, cycloalkyl alkyl of 4 to 8 carbon atoms and arylalkyl of 7 to 12 carbon atoms and X and Y form the group ##STR2## or X is OH and Y is ##STR3## and M is selected from the group consisting of hydrogen, alkali metal and NH.sub.4 and the wavy line indicates the .alpha.- or .beta.-position or mixtures thereof having aldosterone antagonistic activity and increased hydrosodium diuresis with organic potassium conservation while devoid of secondary hormonal effects and their preparation.

Novel 7-alkyl-steroids

Novel optically active isomers or racemates of 1,3-dihydro-3-{1-[2-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-hydroxyethyl]-pip eridin-4-yl}-2H-indol-2-ones of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, chlorine, bromine, fluorine and alkoxy of 1 to 5 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antihypertensive activity and a novel process and intermediates for their preparation.

Antihypertensive 2H-indol-2-ones

Novel 5-thiazole-alkylamines of the formula ##STR1## wherein R is alkyl of 1 to 6 carbon atoms and n is a whole number of 2 to 7 and their non-toxic, pharmaceutically acceptable acid addition salts having marked antilipolytic activity.

5-Thiazole-alkylamines used as antilipolytics

2,2-DIMETHYL-19-NOR-STEROIDS OF THE FORMULA ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, ##STR2## and R.sub.2 is selected from the group consisting of hydrogen and hydrocarbon of 1 to 17 carbon atoms and the dotted lines indicate the optional presence of a double bond in 9(10) and 11(12) positions having antialdosteronic activity and an increased sodium diuresis with conservation of organic potassium and their preparation and novel intermediates.

2,2-Dimethyl-19-nor-steroids

A 5-thiazole-methane-amine selected from the group consisting of (1) compounds having the formula ##STR1## wherein R.sub.1 represents an alkyl having from 1 to 6 carbon atoms and R.sub.2 and R.sub.3 represent members selected from the group consisting of hydrogen, alkyl having from 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, and, taken together, alkylene having up to 5 carbon atoms, azaalkylene having up to 4 carbon atoms, alkylalkylene having up to 5 carbon atoms in the alkylene and 1 to 4 carbon atoms in the alkyl, and alkylazaalkylene having up to 4 carbon atoms in the azaalkylene and 1 to 4 carbon atoms in the alkyl which may be in any position, and (2) its acid addition salts with non-toxic, pharmaceutically-acceptible acids; as well as processes for the preparation of the compounds and a process for use of the compounds as an antilipolytic agent.

5-Thiazole-methane-amines, and their use as antilipolytics

Novel 2,2-dimethyl steroids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, --OH and ##STR2## R.sub.1 is selected from the group consisting of hydrogen and hydrocarbon of 1 to 17 carbon atoms Z is selected from the group consisting of hydrogen and ##STR3## in the .alpha.-position, R.sub.2 is alkyl of 1 to 4 carbon atoms and the dotted line in the B ring indicates the optional presence of a double bond in the 6(7) position having antialdosterone activity and increasing sodium diuresis while conserving organic potassium.

Novel 2,2-dimethyl steroids

Novel pyranic derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and cations of alkali metals, alkaline earth metals, aluminum, amines and ammonium R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and X is selected from the group consisting of hydrogen, chlorine and bromine having hypolipemic activity and reducing the level of total lipids in plasma.

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Paris, France

Robert Fournex