Patents Assigned to Metabio
  • Patent number: 4252804
    Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: February 24, 1981
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
  • Patent number: 4223039
    Abstract: There are provided compounds of the general formula ##STR1## in which Ar represents a phenyl group which is unsubstituted or substituted by a halogen atom or a lower alkyl group, or represents a thienyl group, R.sub.1 represents a hydrogen or halogen atom or, when the Ar--CO-- grouping is in the meta-position with respect to the nitrogen atom, a lower alkyl group, R.sub.2 represents a hydrogen atom, or a lower alkyl or an acyl group, and R.sub.3 represents a hydrogen atom, a lower alkyl or a phenyl group and a physiologically acceptable salt thereof.The compounds of the general formula I and their salts have therapeutic utility, especially as analgesics.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: September 16, 1980
    Assignee: Metabio Joullie
    Inventors: Francis E. E. Rose, Christian J. M. Warolin, Pierre Muller, Paul M. P. Fabiani, Bernard Gaudilliere
  • Patent number: 4203986
    Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 represents a hydrogen or fluorine atom, and R.sub.2 represents an alkyl group containing 2 to 6 carbon atoms, or a cycloalkyl or cycloalkyl-alkyl group containing 5 to 8 carbon atoms, each of these groups being substituted by one or two hydroxy groups or an oxo group and, if desired, also by a 4-(m-trifluoromethylphenyl)-piperazino or 4-(3-trifluoromethyl-4-fluoro-phenyl)-piperazino group with the proviso that, when R.sub.1 represents a hydrogen atom, R.sub.2 does not represent a monohydroxyalkyl group, and their pharmaceutically acceptable acid addition salts are novel and have therapeutic use, notably in the region of the central nervous system and in the cardiovascular region.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: May 20, 1980
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin, Yves R. A. Pascal
  • Patent number: 4172118
    Abstract: The invention concerns the use of diphenylamine as a detoxicant for halogen-containing drugs administered to animals, such as carbon tetrachloride, hexachlorophene, bithionol sulfoxide, etc. The diphenylamine may be administered separately to the animal or simultaneously with the halogen-containing drug in the form of a therapeutic composition.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: October 23, 1979
    Assignee: METABIO
    Inventor: Jacques L. E. Baetz
  • Patent number: 4110460
    Abstract: This invention relates to 2,3-dihydro-imidazo[2,1-b]-thiazole derivatives of the formula: ##STR1## in which R represents a phenyl or substituted phenyl group,R.sub.1 represents a hydrogen atom or a phenyl substituted with a halogen atom or a C.sub.1-4 alkoxy group,R.sub.2, r.sub.3, r.sub.4 and R.sub.5, which may be the same or different, represent each a hydrogen atom, a C.sub.1-4 alkyl group or a phenyl radical,R.sub.1, r.sub.2, r.sub.3, r.sub.4 and R.sub.5 not being simultaneously hydrogen when R represents a phenyl group or a phenyl group substituted with a halogen atom or a nitro group, and their pharmaceutically acceptable acid addition salts.Said compounds have an anti-inflammatory and analgesic activity.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: August 29, 1978
    Assignee: Metabio
    Inventor: Jacques Louis Edouard Baetz