Synthelabo

Jean-Pierre Kaplan

Don Pierre Giudicelli

Bernard M Raizon

Maurice Jalfre

Pascal George

Philippe Michel Manoury

Henry Najer

Daniel C Obitz

Naurice Jalfre

Jean-Michel Bernardon

Benzylidene derivatives of the formula: ##STR1## wherein n is 3, R represents an amino or hydroxy radical, or a group --OM in which M is an alkali metal, X.sub.1 and X.sub.2 are both Cl, and X.sub.3 is hydrogen are new compounds possessing useful pharmacological properties; they are, more particularly, useful in the treatment of various diseases of the central nervous system.

Therapeutically useful benzylidene derivatives

Diphenylazomethines of the formula ##STR1## in which X.sub.1, X.sub.2, X.sub.3 and X.sub.4, which may be the same or different, each represent a hydrogen or halogen atom or a nitro, cyano, hydroxy, methoxy, C.sub.1 -C.sub.3 -alkyl, allyl or phenyl group, and either R represents a 2-(1H-imidazolyl) radical and n is 1 or R represents a 4- (1H-imidazolyl) radical and n is 1 or 2 have antidepressant, analgesic and antiulcerative properties.

Diphenylazomethines bearing an imidazolyl group and pharmaceutical

Benzylidene derivatives of the formula: ##STR1## wherein n represents an integer from 1 through 4, R represents an amino radical, a monoalkylamino group containing 1 through 4 carbon atoms in the alkyl radical, a dialkylamino group containing 1 through 4 carbon atoms in each alkyl radical, or when n represents 2, 3 or 4 a group ##STR2## in which m represents 4 or 5, or a group --OM in which M represents an alkali metal or alkaline earth metal, and X.sub.1 X.sub.2, X.sub.3 and X.sub.4 each represent a hydrogen atom, a halogen atom, or an alkyl radical containing 1 through 6 carbon atoms, are new therapeutically useful compounds. They possess antidepressant, anticonvulsant, anxiolytic, analgesic, anti-inflammatory, ulcer-inhibiting, gastric antisecretory and antihypertensive properties.

Therapeutically useful sulphur-containing benzylidene derivatives

Imidazo[1,2-a]pyridine derivatives of the general formula: ##STR1## wherein n represents 2, 3 or 4, Y represents a hydrogen or halogen atom or a C.sub.1-4 alkyl radical, Z represents a naphthyl radical; a phenyl radical ##STR2## in which X.sub.1 and X.sub.2 independently of one another each represent a hydrogen or halogen atom, a C.sub.1-4 alkoxy radical, a C.sub.1-6 alkyl radical or the group --CF.sub.3, CH.sub.3 S--, CH.sub.3 SO.sub.2 -- or --NO.sub.2 ; or a thien-2-yl, furan-2-yl or pyridine-2-yl radical optionally carrying a halogen atom or the methyl or ethyl radical in the 5-position, and R represents the hydroxy radical, or a group --NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 independently of one another each represent a hydrogen atom; a straight- or branched-chain C.sub.1-5 alkyl radical optionally carrying one or more halogen atoms, a hydroxy radical, a group --N(C.sub.1-4 alkyl).sub.2, a carbamoyl radical or a C.sub.1-4 alkoxy radical; the allyl radical; the propargyl radical; a C.sub.3-6 cycloalkyl radical; the benzyl radical; or the phenyl radical; or alternatively --NR.sub.1 R.sub.2 together represent a heterocyclic ring containing from 3 to 6 carbon atoms, or a heterocyclic ring of the formula ##STR3## in which X is O, S, CHOR' or NR', R' being a hydrogen atom or the benzyl radical and R' being a hydrogen atom, a C.sub.1-4 alkyl radical or the phenyl radical optionally carrying a methoxy radical or a halogen atom, are new compounds. They are therapeutically useful as they possess anxiolytic, antianoxic, sleep-inducing, hypnotic and anticonvulsant properties.

Anxiolytic imidazo[1,2-a]pyridine derivatives

An imidazo[1,2-a]pyridine derivative of the formula: ##STR1## wherein Y represents a hydrogen or halogen atom or a C.sub.1-4 alkyl radical, Z represents a furan-2-yl, thien-2-yl or pyridin-2-yl radical optionally carrying a halogen atom or a methyl or ethyl radical in the 5-position, and R represents the hydroxy radical, a C.sub.1-4 alkoxy radical or a group --NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 independently of one another each represent a hydrogen atom; a straight- or branched-chain C.sub.1-5 alkyl radical optionally carrying one or more halogen atoms or a hydroxy radical, a group --N(C.sub.1-4 alkyl).sub.2, a carbamoyl radical or a C.sub.1-4 alkoxy radical; the allyl radical; the propargyl radical; a C.sub.3-6 cycloalkyl radical; the benzyl radical; or the phenyl radical, or alternatively --NR.sub.1 R.sub.2 together represent a heterocyclic ring containing from 3 to 6 carbon atoms, or a heterocyclic ring of the formula ##STR2## in which X is O, S, CHOR' or N-R', R' being a hydrogen atom or the benzyl radical and R' being a hydrogen atom, a C.sub.1-4 alkyl radical or the phenyl radical optionally carrying a methoxy radical or a halogen atom, are new compounds. They are therapeutically useful as they possess anxiolytic, antianoxic, sleep-inducing, hypnotic and anticonvulsant properties.

Therapeutically useful imidazo[1,2-a]pyridine derivatives

Benzylidene derivatives of the formula: ##STR1## in which each of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 independently of one another represents hydrogen, halogen, a linear or branched alkyl radical of 1 to 4 carbon atoms, CF.sub.3, NO.sub.2, phenyl, methoxy, or amino, at least two of the substituents X.sub.1, X.sub.2, X.sub.3 and X.sub.4 being different from hydrogen, and R represents a linear or branched alkyl radical of 1 to 16 carbon atoms or an alkenyl radical of 2 to 8 carbon atoms, which may be produced by reaction of the corresponding ketones with an amine, are active on the central nervous system, especially as anti-convulsants.

Benzylidene derivatives and compositions containing them

6-Methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylaceta mide is provided, preferably in the form of a pharmaceutically acceptable salt, for example, 6-methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylacet amide methylsulfate. Also provided is a method of providing a patient with a hypnotic effect which comprises administering to said patient a hynotically effective amount of the compound 6-methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylacet amide or a pharmaceutically acceptable salt thereof.

6-Methyl-2-(4-methylthiophenyl)-i

Compounds of the formula: ##STR1## in which X.sub.1, X.sub.2 and X.sub.3, which are identical or different, each represent hydrogen, halogen, methyl, or methoxy, n represents an integer from 1 to 10, and R represents hydroxyl, OM, NH.sub.2, NH(CH.sub.2).sub.3 --COOH, --NH(CH.sub.2).sub.3 --COOM, (where M represents an alkali metal atom), NH(CH.sub.2).sub.3 --COOC.sub.2 H.sub.5, NH-cycloalkyl, NH-phenyl, NH-benzyl (where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl), NH-alkyl, N(alkyl).sub.2 and N-(alkyl)-(benzyl), the aforesaid alkyls being straight or branched and having from 1 to 4 carbon atoms and the aforesaid cycloalkyls having from 3 to 6 carbon atoms, except that when X.sub.1 and X.sub.3 are both hydrogen, n is 1 and R is OH, X.sub.2 is not chlorine in the 5-position are useful in the treatment of epilepsy by oral or parenteral administration.

Benzylidene derivatives

Imidazo[1,2-a] pyridines of the formula: ##STR1## and their acid addition salts in which Y represents a hydrogen or halogen atom or a C.sub.1-4 alkyl radical, Z represents a naphthyl radical or a radical ##STR2## in which each of X.sub.1 and X.sub.2 independently of one another is a hydrogen or halogen atom, a C.sub.1-4 alkoxy radical, a C.sub.1-6 alkyl radical or CF.sub.3, CH.sub.3 S--, CH.sub.3 SO.sub.2 --, --NO.sub.2, --NH.sub.2 or --NHCOCH.sub.3, and each of R.sub.1 and R.sub.2 independently of one another represents a hydrogen atom, a straight or branched C.sub.1-5 alkyl radical which is unsubstituted or substituted by one or more halogen atoms or hydroxyl, --N(C.sub.1-4 alkyl).sub.2, carbamoyl or C.sub.1-4 alkoxy radicals, allyl, propargyl, a C.sub.3-6 cycloalkyl radical, benzyl, or phenyl, not both R.sub.1 and R.sub.2 being hydrogen, or --NR.sub.1 R.sub.2 represents a heterocyclic ring containing from 3 to 6 carbon atoms, or a heterocyclic ring of the formula ##STR3## in which X is O, S, CHOR' or &gt;N--R, R' being hydrogen or benzyl and R being hydrogen, a C.sub.1-4 alkyl radical, or phenyl which is unsubstituted or substituted by methoxy or a halogen atom, which may be made from the corresponding acids, have valuable pharmacological properties, especially anxiolytic, anti-anoxic, sleep-inducing, hypnotic and anticonvulsant properties.

Imidazo[1,2-a] pyridine derivatives and their application as

The invention provides novel 2-methoxy-benzamide derivatives of the formula: ##STR1## in which n is 1 or 2; R.sub.1 represents a cycloalkyl-alkyl radical of formula: ##STR2## a phenylalkyl radical of formula ##STR3## (in which m is an integer from 2 to 5, A is a linear or branched alkylene chain of 1 to 4 carbon atoms, and R.sub.4 is hydrogen, halogen, especially fluorine or chlorine, trifluoromethyl, or alkyl or alkoxy of 1 to 3 carbon atoms), CNCH.sub.2 --CH.sub.2 --, CH.tbd.C--CH.sub.2 --, ##STR4## R.sub.2 is either chlorine, SO.sub.2 R.sub.5 (in which R.sub.5 is alkyl of 1 to 4 carbon atoms), or SO.sub.2 NR.sub.6 R.sub.7 (in which, R.sub.6 and R.sub.7, which are identical or different, represent, independently of one another, hydrogen or alkyl of 1 to 4 carbon atoms); and R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms; in the form of racemates or optical isomers, and their pharmaceutically acceptable acid addition salts, which are useful in the treatment of psychosomatic and pyschotic disturbances.

2-Methoxy-benzamide derivatives

The invention provides novel 2-methoxy-benzamide derivatives of the formula: ##STR1## WHEREIN,

The invention provides novel 2-methoxy-benzamide derivatives of the formula: ##STR1## in which n is 1 or 2; R.sub.1 represents a cycloalkyl-alkyl radical of formula: ##STR2## a phenylalkyl radical of formula ##STR3## (in which m is an integer from 2 to 5, A is a linear or branched alkylene chain of 1 to 4 carbon atoms, and R.sub.4 is hydrogen, halogen, especially fluorine or chlorine, trifluoromethyl, or alkyl or alkoxy of 1 to 3 carbon atoms), CNCH.sub.2 --CH.sub.2 --, CH.tbd.C--CH.sub.2 --, ##STR4## R.sub.2 is either chlorine, SO.sub.2 R.sub.5 (in which R.sub.5 is alkyl of 1 to 4 carbon atoms), or SO.sub.2 NR.sub.6 R.sub.7 (in which, R.sub.6 and R.sub.7, which are identical or different, represent, independently of one another, hydrogen or alkyl of 1 to 4 carbon atoms); and R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms; in the form of racemates or optical isomers, and their pharmaceutically acceptable acid addition salts, which are useful in the treatment of psychosomatic and psychotic disturbances.

Compounds of the formula: ##STR1## in which X.sub.1, X.sub.2 and X.sub.3, which are identical or different each represent hydrogen, halogen, methyl, or methoxy, n represents an integer from 1 to 10, and R represents hydroxyl, OM, NH.sub.2, NH(CH.sub.2).sub.3 --COH, --NH(CH.sub.2).sub.3 --COOM, (where M represents an alkali metal atom), NH(CH.sub.2).sub.3 --COOC.sub.2 H.sub.5, NH-cycloalkyl, NH-phenyl, NH-benzyl (where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl), NH-alkyl, N(alkyl).sub.2 and N-(alkyl)-(benzyl), the aforesaid alkyls being straight or branched and having from 1 to 4 carbon atoms and the aforesaid cycloalkyls having from 3 to 6 carbon atoms, except that when X.sub.1 and X.sub.3 are both hydrogen, n is 1 and R is OH, X.sub.2 is not chlorine in the 5-position are useful in the treatment of epilepsy by oral or parenteral administration.

The invention provides novel 2-methoxy-benzamide derivatives of the formula: ##STR1## in which n is 1 or 2; R.sub.1 represents a cycloalkyl-alkyl radical of formula: (CH.sub.2).sub.m -CH-A- , a phenylalkyl radical of formula ##STR2## (in which m is an integer from 2 to 5, A is a linear or branched alkylene chain of 1 to 4 carbon atoms, and R.sub.4 is hydrogen, halogen, especially fluorine or chlorine, trifluoromethyl, or alkyl or alkoxy of 1 to 3 carbon atoms), CNCH.sub.2 -CH.sub.2 -, CH.tbd.C-CH.sub.2 -, ##STR3## R.sub.2 is either chlorine, SO.sub.2 R.sub.5 (in which R.sub.5 is alkyl of 1 to 4 carbon atoms), or SO.sub.2 NR.sub.6 R.sub.7 (in which, R.sub.6 and R.sub.7, which are identical or different, represent, independently of one another, hydrogen or alkyl of 1 to 4 carbon atoms); and R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms; in the form of racemates or optical isomers, and their pharmaceutically acceptable acid addition salts, which are useful in the treatment of psychosomatic and psychotic disturbances.

Growing community of inventors

Bourg la Reine, France

Jean-Pierre Kaplan