Patents Assigned to Adir Et Cie
  • Patent number: 5047400
    Abstract: The invention relates to the compounds of general formula: ##STR1## in which: X denotes either an oxygen atom, or two hydrogen atoms;Y denotes either a hydrogen atom, or a hydroxyl group;or Y denotes an amino group on condition that X denotes two hydrogen atoms;R denotes a hydrogen atom, or a straight- or branched-chain alkyl group having 1 to 6 carbon atoms, optionally substituted with one or more hydroxy, amino, mercapto, methylthio or carboxy groups, or aryl groups such as phenyl, pyridyl or thienyl; ##STR2## denotes a polycyclic nitrogenous structure; their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: September 10, 1991
    Assignee: Adir et Cie
    Inventors: Michel Vincent, Georges Remond, Bernard Portevin, Claude Cudennec
  • Patent number: 5032581
    Abstract: Compounds of general formula: ##STR1## where A, B, G, R.sub.2, R.sub.3, R.sub.4 and are defined in the description.Medicinal products comprising a compound of the invention and useful in the treatment of bacterial infections are also disclosed.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: July 16, 1991
    Assignee: Adir Et Cie
    Inventors: Gabor Lukacs, Catherine Ruggeri-Duchatelle, Aimee Dessinges, Alain Olesker, Maria Laborde, Li Ming
  • Patent number: 4975455
    Abstract: Compounds of general formula (I): ##STR1## in which: R denotes a hydrogen atom, a halogen atom or a hydroxy, lower alkyl, lower alkyloxy, carboxyl, (lower alkyloxy)carbonyl, (lower arylalkyloxy)carbonyl, aminocarbonyl, (lower mono- or dialkyl)aminocarbonyl or (lower arylalkyl)aminocarbonyl group, an aminocarbonyl group N-substituted with a heterocyclic radical, or a thio, (lower alkyl)thio, sulfonyl or (lower alkyl)sulfonyl group,R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote a hydrogen atom, a halogen atom or a lower alkyl, lower alkenyl, lower alkyloxy or lower alkenyloxy group, optionally substituted with one or more halogen atoms,their isomers, enantiomers, diastereoisomers and also, when R denotes a carboxyl, their addition salts with a pharmaceutically acceptable base and, when R contains a basic group, their addition salts with a pharmaceutically acceptable acid.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: December 4, 1990
    Assignee: Adir et Cie
    Inventors: Jean-Daniel Brion, Guillaume Le Baut, Patrick Ducrey, Sylvie Piessard-Robert, Claude Cudennec, Genevieve Seurre
  • Patent number: 4970301
    Abstract: Compound of general formula I: ##STR1## in which: A is a single or double bond,R.sub.1 and R.sub.3, which may be identical or different, are each a hydrogen atom, an alkoxycarbonylmethylene radical of formula --CH.sub.2 CO.sub.2 R.sub.4 (in which R.sub.4 denotes an alkyl radical having 1 to 5 carbon atoms) or a radical of formula W: ##STR2## (in which n is equal to 0 or 1 and R.sub.5, R.sub.6 and R.sub.7, which may be identical or different, are each a hydrogen or halogen atom, a hydroxyl radical, a trifluoromethyl radical, a lower alkyl radical containing 1 to 5 carbon atoms or an alkoxy radical containing 1 to 5 carbon atoms),R.sub.2 is a hydrogen atom, an alkoxycarbonylmethylene radical of formula --CH.sub.2 CO.sub.2 R.sub.4, a radical of formula W, or a .beta.-glucose or rutinose molecule linked to the oxygen to which it is attached with a glycoside bond,on condition, however, that at least either R.sub.1 or R.sub.2 or R.sub.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: November 13, 1990
    Assignee: Adir et Cie
    Inventors: Yves Rolland, Jacques DuHault
  • Patent number: 4968705
    Abstract: New benzopyrrolidinone compounds, which can be used as medicaments and correspond to the formula ##STR1## in which: either: R.sub.1 and R.sub.2 together represent, with the bond of the etherocycle to which they are attached, an optionally substituted benzene nucleus and, simultaneously, R.sub.3 and R.sub.4 are hydrogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.5 -C.sub.6)cycloalkyl;or:R.sub.1 is hydrogen, R.sub.4 is a single bond and R.sub.2 and R.sub.3 together represent, with the bond of the heterocycle to which they are bonded, an optionally substituted benzene nucleus; andA is a straight or branched hydrocarbon chain having from 2 to 6 carbon atoms that is optionally substituted by hydroxy;X is a single bond, oxygen or sulphur; andY is hydrogen, halogen or (C.sub.1 -C.sub.5)alkyl or alkoxy.These new compounds and the physiologically tolerable salts thereof can be used therapeutically, especially in the treatment of bronchospastic disorders and inflammations in the ENT area.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: November 6, 1990
    Assignee: Adir et Cie
    Inventors: Gilbert Regnier, Alain Dhainaut, Jacques Duhault, Michel Lonchampt
  • Patent number: 4965250
    Abstract: Tetrapeptide compounds of general formula: ##STR1## in which R denotes:a hydrogen atom,a straight- or branched-chain alkyl radical containing from 1 to 4 carbon atoms,an aryl radical such as phenyl or a heterocyclic aromatic radical such as thienyl, optionally substituted with a hydroxy, amino, mercapto, methylthio or lower alkyl group,a lower aralkyl radical such as benzyl,R' denotes a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms,X denotes an oxygen atom or an NH group,Y denotes an oxygen or sulfur atom when X denotes an NH group, or Y denotes an NH group when X denotes an oxygen atom,t denotes 0 or 1, ##STR2## denotes a nitrogen-containing polycyclic structure, their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base.Medicinal products.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: October 23, 1990
    Assignee: Adir ET CIE
    Inventors: Michel Vincent, Georges Remond, Claude Cudennec
  • Patent number: 4960778
    Abstract: Compounds of the general formula (I): ##STR1## in which: X denotes a hydrogen atom,Y denotes a hydrogen atom or a hydroxyl group or alternatively X and Y together denote an oxygen atom,T denotes a hydrogen atom or a lower alkyl group,Z denotes a hydrogen atom or alternatively Z forms a .pi. bond with Y, in which case X denotes a hydrogen atom,R denotes a hydrogen atom or a lower alkyl group,Ar denotes an aryl or heteroaryl or (lower alkyl)aryl group, such as pyrimidinyl, optionally substituted with a halogen atom, or a lower alkyloxy or alkyl group, themselves optionally substituted with one or more halogen atoms,their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid.
    Type: Grant
    Filed: October 3, 1989
    Date of Patent: October 2, 1990
    Assignee: ADIR Et Cie
    Inventors: Daniel Lesieur, Nourddine Abdellatifi, Hocine Aichaoui, Jacqueline Bonnet
  • Patent number: 4954640
    Abstract: Process for the industrial synthesis of (2S,3 7aS)-2-carboxyperhydroindole by reduction of 2-carboxindole or of one of its esters to (R,S)-2-carboxyindo or of one of its esters which, after saponification, converted into the acid, the S isomer cf (R,S)-2-carboxyindoline being obtained by precipitation from the mixture of the two (R) and (S) isomers, in the presence of (+) methylbenzylamine, (S)-2-carboxyindoline being in its turn subjected to catalytic hydrogenation to give (2S, 3aS,7aS)-2-carboxyperhydroindole, after separation of (2S,3aR,7aR) isomer by crystallization.Application to the synthesis of carboxyalkyl d peptides capable of being employed in therapeutics.
    Type: Grant
    Filed: January 10, 1990
    Date of Patent: September 4, 1990
    Assignee: ADIR et Cie
    Inventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
  • Patent number: 4946833
    Abstract: The invention relates to N-(23-vinblastinoyl)compounds of 1-aminomethylphosphonic acid of general formula I ##STR1## in which: R.sub.1 denotes a hydrogen atom, a linear or branched alkyl radical containing from 1 to 6 carbon atoms, a linear or branched alkylene radical containing from 1 to 6 carbon atoms, an arylalkyl radical having 7 to 10 carbon atoms and capable of bearing a halogen atom as a substituent on the aromatic ring, a hydroxyl radical or an alkyl or alkoxy radical each containing from 1 to 5 carbon atoms, a 2-indolylmethyl radical, a 4-imidzolylmethyl radical or an alkoxycarbonylmethyl radical containing from 3 to 11 carbon atoms,R.sub.2 and R.sub.3, which may be identical or different, each denote a linear or branched alkyl radical containing from 1 to 4 carbon atoms,in the form of a mixture of diastereoisomers or of pure isomers, their N.sup.b' -oxides and their addition salts with a pharmaceutically acceptable inoranic or organic acid.These compounds are antitumor agents.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: August 7, 1990
    Assignee: Adir et Cie
    Inventors: Gilbert Lavielle, Patrick Hautefaye, Claude Cudennec
  • Patent number: 4943577
    Abstract: The invention relates to compounds of formula I ##STR1## in which R.sub.1 and R.sub.2 form together and with the piperazine-2,6-dione radical to which they are attached a hexahydropyrazino-.beta.-cabbolinedione radical,R.sub.3 denotes a pyrimidinyl radical or a phenyl radical optionally substituted by an alkyl radical of 1 to 4 carbon atoms or a trifluoromethyl radical,n is an integer of 2 to 4, inclusive.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: July 24, 1990
    Assignee: Adir Et Cie
    Inventors: Gilbert Lavielle, Jean C. Poignant
  • Patent number: 4935525
    Abstract: Process for the industrial synthesis of (2S, 3 7aS)-2-carboxyperhydroindole by reduction of 2-carbox indole or of one of its esters to (R,S)-2-carboxyindo or of one of its esters which, after saponification, converted into the acid, the S isomer cf (R,S)-2-carboxyindoline being obtained by precipitation from the mixture of the two (R) and (S) isomers, in the presence of (+) methylbenzylamine, (S)-2-carboxyindoline being in its turn subjected to catalytic hydrogenation to give (2S, 3aS,7aS)-2-carboxyperhydroindole, after separation of (2S,3aR,7aR) isomer by crystallization.Application to the synthesis of carboxyalkyl d peptides capable of being employed in therapeutics.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: June 19, 1990
    Assignee: Adir et Cie
    Inventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
  • Patent number: 4918058
    Abstract: Compounds of general formula: ##STR1## in which: A denotes either an oxygen atom, or a group of the formula N O-Y-R.sub.5,, B, X, Y, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.8, R.sub.9and R.sub.10 being defined in the description.Medicinal products containing the same, and their use in broad-spectrum antibiotic therapy for the treatment of infections.
    Type: Grant
    Filed: May 6, 1988
    Date of Patent: April 17, 1990
    Assignee: Adir Et Cie
    Inventors: Gabor Lukacs, Catherine Duchatelle-Ruggeri
  • Patent number: 4914214
    Abstract: Process for the industrial synthesis of perindopril, in which (2S,3aS,7aS)-2-carboxyperhydroindole is condensed with N-[(S)-1-carbethoxybutyl]-(S)-alanine after protection of the carboxyl group, the product resulting from the condensation being then subjected to deprotection of the carboxyl carried by the heterocyclic ring.The (2S,3aS,7aS)-2-carboxyperhydroindole and N-[(S)-1-carbethoxybutyl]-(S)-alanine are themselves obtained in excellent conditions from 2-carboxyindole and from L-alanine respectively, both available on an industrial scale.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: April 3, 1990
    Assignee: Adir Et Cie
    Inventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
  • Patent number: 4902817
    Abstract: Stereoselective process for the industrial synthesis of compounds of formula (I): ##STR1## where R.sub.1 is linear or branched lower alkyl with 1 to 6 carbon atoms,R.sub.2 is a linear or branched lower alkyl with 1 to 4 carbon atoms,employing inexpensive starting materials and obtaining optimum yields.Application to the synthesis of carboxyalkyl dipeptides.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: February 20, 1990
    Assignee: ADIR Et Cie
    Inventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
  • Patent number: 4886799
    Abstract: The invention relates to new acetamides derived from 2,3-dihydro-3-phenyl-2-benzofuranone, of general formula I ##STR1## in which: R.sub.1 denotes a hydrogen or halogen atom,R.sub.2 and R.sub.3, which may be identical or different, each denote a hydrogen atom or a linear or branched alkyl radical containing 1 to 4 carbon atoms, a benzyl radical optionally substituted with a halogen atom, with an alkoxy radical containing 1 to 4 carbon atoms or with an alkyl radical having 1 to 4 carbon atoms, or a 3,4-methylene-dioxybenzyl radical, or form, together with the nitrogen to which they are attached, a 4-morpholinyl radical or a 1-piperazinyl radical.
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: December 12, 1989
    Assignee: Adir Et Cie
    Inventors: Gilbert Lavielle, Jean Lepagnol
  • Patent number: 4885299
    Abstract: The invention relates to new 2-(2,3-dihydro-2-oxo-3-benzofuranyl)acetic acid compounds of general formula I: ##STR1## in which: R.sub.1 denotes a hydrogen atom, a linear or branched alkyl radical having 1 to 4 carbon atoms or a phenyl radical optionally substituted with a halogen atom or with an alkoxy radical containing 1 to 4 carbon atoms or an alkyl radical having 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen or halogen atom, a hydroxyl radical, an alkyl radical having 1 to 4 carbon atoms or an alkoxy radical containing 1 to 4 carbon atoms,R denotes a hydroxyl radical, a linear or branched alkoxy radical having 1 to 4 carbon atoms, a benzyloxy radical or a radical of general formula A: ##STR2## in which: X and Y, which may be identical or different, each denote a linear or branched alkyl radical containing 1 to 5 carbon atoms, a radical of general formula A.sub.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: December 5, 1989
    Assignee: ADIR Et Cie
    Inventors: Gilbert Lavielle, Jean Lepagnol
  • Patent number: 4885373
    Abstract: Compounds of general formula I, ##STR1## in which: R.sub.1 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 7-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.2 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 6-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms,R.sub.3 and R.sub.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: December 5, 1989
    Assignee: ADIR Et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4877788
    Abstract: The invention relates to the compounds selected from those of formula I ##STR1## in which, R.sub.1 and R.sub.2 form together and with the piperazine-2,6-dione radical to which they are attached a hexahydropyrazinoisoquinolinedione radical, a primidinyl radical or a phenyl radical optionally substituted by an alkyl radical of 1 to 4 carbon atoms or a trifluoromethyl radical,n is an integer from 2 to 4.
    Type: Grant
    Filed: June 14, 1988
    Date of Patent: October 31, 1989
    Assignee: Adir Et Cie
    Inventors: Gilbert Lavielle, Jean Claude Poignant
  • Patent number: 4874878
    Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 and R.sub.2, which may be identical or different, each denote a hydrogen atom, a benzyl radical, a cyclohexylmethyl radical or a linear or branched alkyl radical containing from 1 to 10 carbon atoms, optionally substituted with a hydroxy radical, with a carboxy radical or with an alkoxy radical having 1 to 5 carbon atoms, with an alkoxycarbonyl radical having 2 to 6 carbon atoms, with an alkylphenyl radical having 7 to 16 carbon atoms or with a 2-alkylthienyl radical having 5 to 14 carbon atoms,R.sub.3 denotes a hydrogen atom or a linear or branched alkyl radical containing from 1 to 4 carbon atoms,A denotes a single bond or a methylene radical, or a radical of formula ##STR2## in which R.sub.4 is a linear or branched alkyl radical containing from 1 to 4 carbon atoms.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: October 17, 1989
    Assignee: Adir Et Cie
    Inventors: Jean L. Peglion, Jean C. Poignant, Joel Vian
  • Patent number: 4870091
    Abstract: Compounds of general formula I: ##STR1## in which: Ar represents a phenyl radical optionally containing one to five identical or different substituents, representing a halogen atom, an alkoxy radical containing 1 to 4 carbon atoms, an alkylthio radical containing 1 to 4 carbon atoms, a trihalomethyl radical or a methylenedioxy radical,Y, Z, Y.sub.1, Z.sub.1, W, V, U, m, n, R.sub.1, R.sub.2 are as defined in the specification. The compounds are used as calcium modulators.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: September 26, 1989
    Assignee: ADIR Et Cie
    Inventors: Jean-Louis Peglion, Yves-Michel Gargouil, Jean-Paul Vilaine