Patents Assigned to Rhone-Poulenc Sante
  • Patent number: 4529728
    Abstract: New compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 =H or alkyl and(a) R=CN or alkylcarbonyl, or(b) R=CON(R.sub.3)R.sub.4, in which R.sub.3 =H and R.sub.4 =NH.sub.2, alkylamino, dialkylamino, phenylamino or diphenylamino; or R.sub.3 and R.sub.4 =H, alkyl (1 to 5 C) or substituted phenyl; or R.sub.3 =H and R.sub.4 =pyridyl or alkyl (1 to 5 C) substituted by COOH, NH.sub.2, alkylamino, dialkylamino, morpholino, piperidino, pyrrolidin-1-yl, piperazin-1-yl (optionally substituted by alkyl, pyridyl or optionally substituted phenyl or benzyl), optionally substituted phenyl, pyridyl or imidazolyl; or R.sub.3 and R.sub.4 form an imidazolyl radical or a 5-membered or 6-membered heterocycle which can contain an oxygen, sulphur or nitrogen atom and which is optionally substituted by alkyl, alkoxycarbonyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, pyridyl, pyrimidinyl, pyrazinyl, optionally substituted phenyl or optionally substituted benzyl; or(c) R=--C(.dbd.NOH)NH.sub.2 or --C[.dbd.
    Type: Grant
    Filed: January 11, 1984
    Date of Patent: July 16, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Louis Fabre, Daniel Farge, Claude James, Daniel Lave
  • Patent number: 4526962
    Abstract: New cephalosporin derivatives of the formula: ##STR1## in which R' represents a protected carboxyl radical, Hal represents a halogen atom, X.sub.1 represents a sulphur or oxygen atom or a sulphinyl radical and R represents an acyl radical or an amine-protecting radical, are useful as intermediates for the preparation of cephalosporins having antibacterial activity.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: July 2, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Daniel Farge, Pierre Le Roy, Claude Moutonnier, Jean-Francois Peyronel, Bernard Plau
  • Patent number: 4510330
    Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula: ##STR1## by the oxy-Cope rearrangement of a diethylenic alcohol of the formula: ##STR2## in which the transformation is carried out in the presence of a catalytic amount of a divalent palladium compound.In the depicted formulae R.sub.1, R.sub.4 and R.sub.6 each represent a hydrogen atom or a hydrocarbon radical, R.sub.2 represents a hydrogen atom and R.sub.3 and R.sub.5 each represent a hydrocarbon radical, or R.sub.3 and R.sub.4 together represent an alkylene radical (--CH.sub.2 --).sub.n (wherein n is an integer from 3 to 20 inclusive) in which one or more carbon atoms can optionally carry as substituent(s) one or more alkyl radicals containing 1 to 4 carbon atoms.The carbonyl products are useful as starting materials for the preparation of compounds intended for use in pharmacy, in agriculture or perfumery.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: April 9, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Norbert Bluthe, Jacques Gore, Max Malacria
  • Patent number: 4508717
    Abstract: Cephalosporin derivatives of the formula: ##STR1## in which A is a single bond or a radical --CH.sub.2 --, --NH-- or --NHCO--, attached to the 3-position or 4-position of the pyridinio radical, R is a methyl, carboxymethyl, carbamoylmethyl, benzyl or allyl radical, R.sub.a, R.sub.b and R.sub.c are hydrogen atoms, or alternatively R.sub.a is carboxyl and R.sub.b and R.sub.c, which are identical or different, are hydrogen atoms or alkyl radicals, or together form an alkylene radical, and n equals 0 or 1, in their syn form, and also their addition salts with acids, metal salts and addition salts with nitrogen-containing bases are antibacterial agents having a broad spectrum of activity.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: April 2, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Christian Berger, Daniel Farge, Claude Moutonnier, Jean-Francois Peyronel, Bernard Plau
  • Patent number: 4508902
    Abstract: Process for the preparation of a 4-hydroxyquinoline of the formula: ##STR1## in which R represents a hydrogen atom or one, two or three substituents, which may be the same or different, selected from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms, and the trifluoromethyl radical, the substituent(s) being in the 2-, 3-, 5-, 6-, 7- or 8-position, which comprises oxidizing a 1,2,3,4-tetrahydroquinolin-4-one of the general formula: ##STR2## in which R is as hereinbefore defined, in a basic medium, under pressure, by means of excess oxygen or air at a temperature between 80.degree. and 150.degree. C.The 4-hydroxyquinoline products are useful for the preparation of therapeutically useful substances.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: April 2, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Dominique Petre, Daniel Michelet
  • Patent number: 4503239
    Abstract: Process for the preparation of halogenoacetals of the general formula: ##STR1## wherein X represents chlorine or bromine, the symbols R each represent a linear or branched alkyl radical (1 to 6 carbon atoms) or together form a linear or branched alkylene radical (2 to 6 carbon atoms), and the symbols R.sub.1 and R.sub.2, which are identical or different, represent a hydrogen atom or an alkyl radical (1 to 6 carbon atoms), by reaction of chlorine or bromine with a .beta.,.gamma.-ethylenic aldehyde, in the presence of a tertiary amide, followed by reaction with a primary or secondary aliphatic alcohol, a diol (preferably a glycol) or an alkyl orthoformate.
    Type: Grant
    Filed: December 16, 1982
    Date of Patent: March 5, 1985
    Assignee: Rhone-Poulenc Sante
    Inventor: Jean Desmurs
  • Patent number: 4503220
    Abstract: 3-Vinylcephalosporin derivatives of the formula: ##STR1## in which the symbols R.sub.1 are phenyl radicals or radicals --OZ.sub.1 (it being possible for Z.sub.1 to be alkyl, 2,2,2-trichloroethyl or optionally substituted phenyl or benzyl, or for the radicals Z.sub.1 to form an alkylene radical), R.sub.2 is a radical which can be removed by an enzymatic method, or a protecting radical, and R.sub.3 and R.sub.4 are optionally substituted alkyl, or phenyl, or together form a saturated 5-membered or 6-membered heterocyclic ring optionally containing another hetero-atom, are new, crystallizable intermediates useful for the preparation of anti-bacterial cephalosporins.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: March 5, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Daniel Farge, Pierre L. Roy, Claude Moutonnier, Jean-Francois Peyronel
  • Patent number: 4496560
    Abstract: New cephalosporin derivatives, of the formula: ##STR1## in which R.sub.1 is a heterocyclic, phenyl, p-hydroxyphenyl, phenoxy or dichlorophenylthio radical and R.sub.2 is a hydrogen atom, or R.sub.1 is phenyl or p-hydroxyphenyl and R.sub.2 is an amino radical, R.sub.3 is hydrogen, phenyl, substituted phenyl, alkylthio or substituted amino or a radical of the structure --A--R'.sub.3, which A is --CH.sub.2 --, --NH-- or --NHCO-- and R'.sub.3 is a substituted pyridinio radical, R is a carboxyl radical or a carboxylato radical if R.sub.3 is a --AR'.sub.3 radical and X is a sulphur or oxygen atom, the said alkyl moieties or radicals containing 1 to 4 carbon atoms each in their D, L and D,L forms, where these exist, and their salts are narrow-spectrum anti-bacterial agents which are active against gram-positive bacteria.
    Type: Grant
    Filed: August 16, 1982
    Date of Patent: January 29, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Daniel Farge, Pierre Le Roy, Claude Moutonnier, Jean-Francois Peyronel, Bernard Plau
  • Patent number: 4466866
    Abstract: Sulphoxides of thioformamide derivatives of the formula: ##STR1## wherein R represents hydrogen or a C.sub.1 -C.sub.4 alkyl radical, Het represents a heterocyclic radical selected from pyridin-3-yl (optionally substituted by a C.sub.1 -C.sub.4 alkyl radical or by a halogen atom), quinolin-3-yl, pyridazin-4-yl, pyrimidin-5-yl, thiazol-5-yl, thieno[2,3-b]pyridin-5-yl and thieno[3,2-b]pyridin-6-yl, and Y represents a valency bond or a methylene radical, are prepared by oxidizing the ring sulphur atom of a thioformamide derivative of the general formula: ##STR2## by an electrochemical method. The reaction is carried out in an electrolyte with a considerable water content, at a pH of between 7 and 7.5 and in the presence of a specific oxidizing agent X.sup.+ obtained in situ from a halide X.sup.- by an electrochemical method, and at an imposed electrode potential similar to the oxidation potential of X.sup.-.The sulphoxide products are useful as medicaments for treating hypertension.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: August 21, 1984
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean Bizot, Dominique Deprez
  • Patent number: 4456758
    Abstract: New heterocyclic nitriles of the formula: ##STR1## wherein (i) Het represents a heterocyclic radical of aromatic character containing one or two nitrogen atoms selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents an oxygen atom and Y represents a valency bond or a methylene radical, or altenatively X represents a sulphur atom and Y represents a sulphur atom, a valency bond or a methylene radical, or(ii) Het represents the pyrid-2-yl radical, X represents an oxygen atom and Y represents a valency bond or a methylene radical, or alternatively X represents a sulphur atom and Y represents a sulphur atom or a methylene radical, are useful, in particular, as intermediates for the preparation of therapeutically useful heterocyclic thioformamides by converting the depicted cyano radical into a grouping --CSNHR wherein R represents a hydrogen atom or an alkyl (C.sub.1-4) radical.
    Type: Grant
    Filed: August 10, 1982
    Date of Patent: June 26, 1984
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Aloup, Jean Bouchaudon, Daniel Farge, Claude James
  • Patent number: 4421920
    Abstract: 4-Amino-chloroquinolines of the formula: ##STR1## in which R.sub.1 represents a hydrogen atom or an alkyl radical (1 to 5 carbon atoms), and R.sub.2 represents an alkyl radical (1 to 5 carbon atoms) optionally substituted by a dialkylamino group, or a phenyl radical optionally substituted by one or more carboxy and hydroxy radicals and alkyl radicals (1 to 4 carbon atoms) optionally substituted by a dialkylamino group, are prepared by the condensation of an amine of the formula: ##STR2## with a chloro-1,2,3,4-tetrahydroquinolin-4-one of the formula: ##STR3## with aromatization of the tetrahydroquinoline, the reaction being carried out in the presence of a ruthenium based catalyst on a support.The 4-amino-chloroquinoline products are useful as pharmaceuticals.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: December 20, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Baudouin, Daniel Michelet
  • Patent number: 4421934
    Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula (I) by the oxy-Cope rearrangement of a diethylenic alcohol of the formula (II), in the presence of a mercuric salt: in formulae (I) and (II), R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6, which are identical or different, represent a hydrogen atom or an acyclic hydrocarbon radical and R.sub.3 represents an acyclic hydrocarbon radical, it being understood that R.sub.1 and R.sub.3 can together form a trimethylene radical, or alternatively that R.sub.3 and R.sub.4 can together form an alkylene radical containing 3 to 20 carbon atoms.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: December 20, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Norbert Bluthe, Jacques Gore, Max Malacria
  • Patent number: 4421918
    Abstract: Process for the preparation of 7-chloro-1,2,3,4-tetrahydroquinolin-4-one by cyclizing 3-m-chloroanilinopropionic acid by means of an oleum, and desulphonating the resulting aromatic sulphonic acids by means of dilute sulphuric acid. The quinolinone product is useful as a starting material for the preparation of pharmaceuticals.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: December 20, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Baudouin, Hubert Linares
  • Patent number: 4412075
    Abstract: 1,2,3,4-Tetrahydroquinolin-4-ones of the formula: ##STR1## wherein R represents a hydrogen or halogen atom, an alkyl radical (1 to 4 carbon atoms), an alkoxy radical (1 to 4 carbon atoms) or the trifluoromethyl radical, and R.sub.1 represents a hydrogen atom, an alkyl radical (1 to 4 carbon atoms) or the trifluoromethyl radical, are prepared by cyclizing a 3-anilinopropionic acid of the formula: ##STR2## (wherein R and R.sub.1 are as hereinbefore defined) in a mixture of hydrofluoric acid and boron trifluoride.The quinolinone products are useful intermediates in the synthesis of therapeutically active substances.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: October 25, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Baudouin, Michel Desbois
  • Patent number: 4412076
    Abstract: Process for the preparation of 4-hydroxyquinolines of the general formula: ##STR1## in which R represents a hydrogen atom, or one, two or three substituents, which may be the same or different, selected from halogen atoms, alkyl radicals containing 1 to 4 carbon atoms, alkoxy radicals containing 1 to 4 carbon atoms, and the trifluoromethyl radical, the substituent(s) being in the 2-, 3-, 5-, 6-, 7- or 8-position, by the oxidation, by means of oxygen or air, in the presence of a catalyst based on platinum or ruthenium, or alloys thereof, of a 1,2,3,4-tetrahydroquinolin-4-one of the general formula: ##STR2## in which R is as defined above.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: October 25, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Baudouin, Daniel Michelet
  • Patent number: 4407797
    Abstract: New compounds of the formula: ##STR1## wherein X.sup..crclbar. is an anion, R is (C.sub.1-7) alkyl [unsubstituted or substituted by hydroxy, carboxy, alkoxycarbonyl, cyano, dialkylamino, alkylcarbonyl, or benzoyl which is unsubstituted or substituted by one or more halogen atoms or radicals selected from alkyl (optionally substituted by one or more halogens), alkoxy, hydroxy, amino, alkylamino, dialkylamino, cyano and nitro, or by a thenoyl radical (which is unsubstituted or substituted by one or more halogens or radicals selected from alkyl, cyano and nitro), or a pyridinecarbonyl, carbamoyl or dialkylcarbamoyl radical (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring) or a pyridyl radical], dialkylcarbamoyl (the alkyl radicals of which can form a 5-membered or 6-membered heterocyclic ring), (C.sub.2-4) alkenyl, (C.sub.2-4) alkynyl, alkoxycarbonyl or a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydropyran-3-yl ring, and either R.sub.1 and R.sub.
    Type: Grant
    Filed: August 10, 1982
    Date of Patent: October 4, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Claude Cotrel, Daniel Farge, Gerard Taurand
  • Patent number: 4401658
    Abstract: The invention provides tri-, tetra- or penta-peptides of the general formula: ##STR1## in which RCO is a fatty acid residue, R.sub.1 is hydroxyl, amino, alkoxy or benzyloxy, R.sub.2 and R.sub.4 (identical or different) represent hydrogen, carboxyl, alkoxycarbonyl or benzyloxycarbonyl or an optionally esterified N-carbonylglycyl or N-carbonyl-D-alanyl radical, it being impossible for R.sub.2 and R.sub.4 simultaneously to represent hydrogen, R.sub.3 is hydrogen, or represents a glycyl or D-alanyl residue (in which case, only one of the radicals R.sub.2 and R.sub.4 can represent an N-carbonylglycyl or N-carbonyl-D-alanyl radical), X is a sulphur atom or methylene, and m and n=1 or 2, it being understood that if X is methylene, m and n are different from 1, their salts, their preparation and compositions containing them: the compounds are useful as vaccine adjuvants or as non-specific stimulants of anti-infectious or anti-tumoral activity.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: August 30, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean Bouchaudon, Gilles Dutruc-Rosset, Daniel Farge, Claude James
  • Patent number: 4379154
    Abstract: Thioformamide derivatives of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and (i) Het represents a heterocyclic radical selected from pyrid-3-yl, pyrid-4-yl, pyridazinyl, pyrazinyl, pyrimidinyl, quinolyl, imidazolyl, naphthyridinyl, quinoxalinyl and quinazolinyl, X represents sulphur or oxygen and Y represents sulphur or oxygen, a valency bond or methylene, or (ii) Het represents pyrid-2-yl, X represents sulphur or oxygen and Y represents sulphur or oxygen or methylene, or (iii) Het represents pyrid-2-yl, X represents oxygen and Y represents a valency bond, are new compounds possessing useful pharmacological properties. They are particularly useful in the treatment of gastrointestinal ulcers and in the treatment of hypertension, depending on the definition of the symbol Het.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: April 5, 1983
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Aloup, Jean Bouchaudon, Daniel Farge, Claude James