Roussel Uclaf

Other

Jean-Claude Gasc

Daniel Humbert

Lucien Nedelec

Daniel Coussediere

Claude Rettien

Jean-Bernard Chazan

Peter F Hunt

Dinah W Nanopoulos

Francoise Delevallee

Patrick Fauveau

Andre Lutz

Jean-Paul Vevert

Solange Gouin d'Ambrieres

Francis Petit

Jacques Laurent

Serge Geoffre

Ana Maria Boaventura

Jean Bernard Chazan

Mario Vekens

Michel Hospital

All possible isomeric forms and mixtures thereof of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of indolyl, pyridyl, piperidinyl, quinolyl, thiazolyl and aryl of 6 to 14 carbon atoms and aralkyl of 7 to 18 carbon atoms with the latter two being unsubstituted or substituted with at least one member of the group consisting of halogen, alkyl and alkoxy of 1 to 8 carbon atoms, dialkylamino with alkyls of 1 to 8 carbon atoms, --CF.sub.3, --CN and --NO.sub.2, R.sub.2 is selected from the group consisting of ##STR2## Ar' are selected from the group consisting of pyridyl, indolyl, thiazolyl and aryl of 6 to 14 carbon atoms with the latter and the phenyl ring of b) being substituted or substrituted with at least one member of the group consisting of halogen, alkyl and alkoxy of 1 to 8 carbon atoms, dialkylamino with alkyls of 1 to 8 carbon atoms, --CF.sub.3, --CN and --NO.sub.2 and R.sub.3 is hydrogen or R.sub.2 and R.sub.3 together with the nitrogen to which they are attached form a 5 to 7 member hydrocarbyl ring optionally containing an oxygen or a second nitrogen unsubstituted or substituted with at least one member of the group consisting of alkyl of 1 to 8 carbon atoms, aryl of 6 to 14 carbon atoms and ##STR3## Ar and Ar' having the above definitions and R.sub.4 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, ##STR4## and aralkyl of 7 18 carbon atoms unsubstituted or substituted with at least one member of the group consisting of halogen, alkyl and alkoxy of 1 to 8 carbon atoms, dialkylamino with alkyls of 1 to 8 carbon atoms, --CF.sub.3, --CN and --NO.sub.2, Alk.sub.1 is an alkylene of 2 to 8 carbon atoms and alk.sub.2 and Alk.sub.3 are individually alkyl of 1 to 8 carbon atoms or cycloalkyl of 3 to 8 carbon atoms having cholecystokinin agonistic or antagonistic activity.

4(2-indolyl)2-amino-pentanedioic acids and cholecyostokinin use thereof

A compound in all possible isomeric forms and mixtures thereof of the formula ##STR1## wherein X and X' are individually selected from the group consisting of hydrogen, halogen, cyano, --NO.sub.2, --CF.sub.3 and alkyl and alkoxy of 1 to 8 carbon atoms, R is hydrogen or alkyl of 1 to 8 carbon atoms and Ar is selected from the group consisting of an unsubstituted or substituted aryl of 6 to 14 carbon atoms, an unsubstituted or substituted aromatic heterocyclic or a heterocyclic united with an unsubstituted or substituted aryl having cholecystokinine antagonistic activity.

2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepines

A compound selected from the group consisting of azaspirodecane derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkoxy of 1 to 3 carbon atoms, --NO.sub.2, --NH.sub.2 and CH.sub.3 S-- in the 4,5 or 6 position of the ring, R' is oxo or hydrogen or --OH or alkyl of 1 to 3 carbon atoms and the dotted line indicates a carbon-carbon bond in the 2,3-position, n is 2,3,4 or 5 and the dotted line in the piperidyl ring is an optional carbon-carbon bond and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anxiolytic activity.

Certain azaspirodecane compounds and a method of inducing an anxiolytic

Novel .alpha.-mercaptomethyl-benzene propanamides of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and ##STR2## R.sub.1 ' is selected from the group consisting of alkyl of 1 to 5 carbon atoms and aryl optionally substituted with at least one member of the group consisting of --OH, --NO.sub.2, halogen and alkyl and alkoxy of 1 to 5 carbon atoms, X and X' are individually selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 5 carbon atoms, --OH, halogen and --CF.sub.3, R.sub.2 is selected from the group consisting of pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, tetrahydrothiazinyl and hexahydroazepinyl, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, --OH, --NO.sub.2, --CF.sub.3, halogen and acyl of an organic carboxylic acid of 1 to 7 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic activity, antidepression and anxiolytic properties.

Alpha-mercaptomethyl-benzene propanamides, pharmaceutical compositions

Novel racemic mixtures and optical isomers of 4-morpholinyl-1H-indoles of the formula: ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of hydroxymethyl, alkylthiomethyl of 1 to 3 alkyl carbons, cyanomethyl and carboxy optionally esterified with an aliphatic alcohol of 1 to 5 carbon atoms or optionally amidified with an amine of the formula ##STR2## R.sub.3 is alkyl of 1 to 4 carbon atoms and R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having the ability to activate neurons and to protect the same against ischemic or anoxic aggressions.

2,3-dihydro indoles

4-morpholinyl-1H-indoles, pharmaceutical compositions and use

Novel pyrazolo[4,3-c]cinnolin-3-one derivatives of the formula ##STR1## wherein R may be in the 7- or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2 and --CF.sub.3 and R' is hydrogen or R and R' taken together form an alkylenedioxy of 1 to 4 carbon atoms at the 7- or 8-positions and R.sub.1 is selected from the group consisting of phenyl, pyridyl, thiazolyl, dihydrothiazolyl and thienyl, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, halogen, mono-, di- and tri- halomethyl and aralkoxy of 7 to 12 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anxiolytic properties and novel intermediates therefore.

2-aryl pyrazolo[4,3-c]cinnolin-3-ones

Novel isoxazoloquinolinones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2 and CF.sub.3 -- and R.sub.1 is phenyl optionally substituted by at least one member selected from the group consisting of halogen and alkyl and alkoxy of 1 to 5 carbon atoms having anxiolytic activity and their preparation and novel intermediates.

Derivatives of isoxazolo[4,5-c]quinoline(2H)-3-one and method of

Novel C-homo-9-oxa-ergolines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen, chlorine and bromine or taken with b forms .dbd.0, a and b form a carbon-carbon bond or a is hydrogen when R.sub.1 and b form .dbd.0, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, aralkyl of 7 to 12 carbon atoms and cycloalkylalkyl of 4 to 7 carbon atoms, R.sub.3 is selected from the group consisting of hydroxymethyl, alkylthiomethyl of 1 to 5 alkyl carbon atoms, cyanomethyl, carboxy optionally esterified with an aliphatic alcohol of 1 to 5 carbon atoms and ##STR2## R.sub.4 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.5 is alkyl of 1 to 4 carbon atoms or R.sub.4 and R.sub.5 taken with the nitrogen atom form a saturated heterocycle optionally containing a second heteroatom having dopaminergic agonist, serotoninergic and antihypertensive activity as well as prolactin secretion inhibition and antianoxic activities and their preparation and intermediates.

C-Homo-9-oxa-ergolines

Hexapeptides

Novel erythromycin derivatives in the syn form or anti form or mixtures of the syn and anti forms of the formula ##STR1## wherein A is a linear or branched alkylene of 1 to 6 carbon atoms, R is selected from the group consisting of optionally substituted alkoxy of 1 to 6 carbon atoms, optionally substituted alkenyloxy and alkynyloxy of 2 to 6 carbon atoms, optionally substituted alkylthio of 1 to 6 carbon atoms, optionally substituted alkenylthio and alkynylthio of 2 to 6 carbon atoms with the thio group optionally oxidized to the sulfoxide or sulfone form, optionally substituted aryloxy and arylthio, optionally substituted aralkyloxy and arylalkylthio, the thio derivatives optionally oxidized to sulfoxide or sulfone, ##STR2## optionally substituted quaternary ammonium group, halogen, optionally substituted 1,2-epoxyethyl and the group resulting from opening of the epoxy with a nucleophilic reactant, ##STR3## a free or protected formyl, --COOR', thiocyanate, --CN, acyl and carbamoyl, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, and optionally substituted alkyl of 1 to 6 carbon atoms or taken together with the nitrogen atom to which they are attached form an optionally substituted, optionally unsaturated heterocycle which can contain another heteroatom, B is selected from the group consisting of optionally substituted alkyl and alkoxy of 1 to 6 carbon atoms, optionally substituted aryl and aryloxy and optionally substituted aralkyl and aralkoxy of 1 to 6 alkyl carbon atoms, R' is selected from the group consisting of hydrogen, a cation and an ester group, R.sub.a is selected from the group consisting of hydrogen and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having very good antibiotic activity and their preparation.

Novel erythromycin a derivatives

Novel aminoglycoside derivatives of desoxystreptamines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and hydroxyl with at least one of them being hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and their preparation.

Aminoglycosides and method of use

The present invention has as its objects a new derivative of the aminoglycoside family, namely N.sub.1 [L-(-)2-hydroxy-4-amino butyroyl]4-0[2',6'-diamino 2',6'-didesoxya, D glucopyranosyl]6-0[3'-methylamino 3',4',6'-tridesoxy .alpha., D-xylohexopyranosyl]2-desoxy streptamine, as well as its mineral or organic acid addition salts, its process of preparation and methods of treatment using the same.

Desoxystreptamine derivatives, salts, pharmaceutical compositions and

There are disclosed pharmaceutically-active aminoglycosides comprising 4-O-(2',6'-diamino 2',6'-didesoxy .alpha.,D-glucopyrannosyl) 6-O-(3'-amino 3',4',6'-tridesoxy .alpha., D-xylohexopyrannosyl) 2-desoxy streptamine of the formula: ##STR1## and the addition salts thereof with mineral acids or organic acids. Also disclosed are methods for preparation of the novel products as well as certain novel intermediate products. There are also disclosed pharmaceutical compositions in which the novel products are the active agents as well as methods for use of compositions as antibiotic agents.

Antibiotic aminoglycosides, processes of preparation and pharmaceutical

There are disclosed pharmaceutically-active aminoglycosides comprising 4-O-[2',6'-diamino 2',3',6'-tridesoxy .alpha.,D-ribohexopyranosyl] 6-O-[3'-methylamino 3',4',6'-tridesoxy .alpha.,D-xylohexopyranosyl] 2-desoxystreptamine of the formula: ##STR1## and the addition salts thereof with mineral acids or organic acids. Also disclosed are methods for preparation of the novel products as well as certain novel intermediate products. There are also disclosed pharmaceutical compositions in which the novel products are the active agents and a method for the treatment of bacteria infections in humans and animals.

Growing community of inventors

Bondy, France

Jean-Claude Gasc