Patents Assigned to Centre International de Recherches Dermatologiques
  • Patent number: 5587367
    Abstract: A pharmaceutical or cosmetic composition is disclosed comprising in combination a retinoid and a sterol capable of inhibiting the biosynthesis of cholesterol resulting in a synergistic effect in the treatment of disorders of epidermic keratinization, proliferation and/or sebaceous function.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: December 24, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Uwe Reichert, Rainer Schmidt, Braham Shroot
  • Patent number: 5574036
    Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted polycyclic acetylene compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(f): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: November 12, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Bruno Charpenter
  • Patent number: 5567721
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: October 22, 1996
    Assignee: Centre International de Recherches Dermatologiques
    Inventors: Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5556844
    Abstract: A pharmaceutical or cosmetic composition comprising in combination, a retinoid and a sterol inhibits the biosynthesis of cholesterol, is disclosed wherein a synergistic effect, principally in the treatment of disorders of epidermic keratinization, disorders of epidermic or epithelial proliferation and/or disorders of sebaceous function, is exhibited.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: September 17, 1996
    Assignee: Centre International De Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Uwe Reichert, Rainer Schmidt, Braham Shroot
  • Patent number: 5547983
    Abstract: Aromatic bicyclic compounds of formula (I) ##STR1## where R.sub.1 is specifically --H, CH.sub.3, --CH.sub.2 OH, --OH, --CHO, --CONH.sub.2, --COOH, --COOalkyl, --SH, S-alkyl, etc. . . . ; R.sub.2 is H; R.sub.3 is H, aryl, aralkyl or lower alkyl optionally substituted by a hydroxyl, a lower alkoxy or a --CO--R.sub.12, R.sub.12 being specifically H, lower alkyl, hydroxyl, lower alkoxy, or R.sub.2 and R.sub.3 together form a naphthalene ring with the benzene ring; R.sub.4 is a linear branched or unbranched alkyl having 1 to 15 carbon atoms or a cycloaliphatic radical; R.sub.5 represents specifically --(CH.sub.2).sub.n --R.sub.13, --CH.dbd.CH--(CH.sub.2).sub.n --R.sub.13, n being 0 or 1 to 6, R.sub.13 representing --COR.sub.15, monohydroxyalkyl, polyhydroxyalkyl, epoxy lower alkyl or --O--CO--R.sub.16, R.sub.15 representing specifically --OH, --Oalkyl, --Oaryl, R.sub.16 being specifically H, lower alkyl, aryl, or aralkyl; R.sub.6 and R.sub.7 are H, a halogen, lower alkyl or --OR.sub.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: August 20, 1996
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventor: Bruno Charpentier
  • Patent number: 5541073
    Abstract: The subject invention relates to a method of diagnosing epidermis differentiation disorders in a patient by obtaining an epidermis sample from the patient, adding to the sample, antibodies that specifically bind to an antigen of the stratum corneum, the said antigen being specifically recognized by BC 21 monoclonal antibody and detecting the presence or absence of the antibodies that are specifically bound to the epidermis sample.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: July 30, 1996
    Assignee: Centre International De Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Serge Michel, Jacques Bailly, Gaelle Saintigny, Uwe Reichert
  • Patent number: 5476860
    Abstract: Diaromatic compounds, characterized in that they correspond to the following general formula: ##STR1## in which: R.sub.1 is --CH.sub.3, --CH.sub.2 OH, --COR.sub.8 or --CH.sub.2 OCOR.sub.9, R.sub.8 is H, OH, --OR.sub.10, --N(rr') or alkyl, R.sub.10 is alkyl, alkenyl, aryl or aralkyl, r and r' being H, alkyl, aryl, aralkyl, etc., r and r' together form a heterocycle, R.sub.9 is alkyl, alkenyl or a sugar residue, R.sub.2 and R.sub.3 are --OR.sub.11 or --OCOR.sub.11, R.sub.11 is H, alkyl, fluoroalkyl, aryl or aralkyl, R.sub.3 in addition being H, R.sub.4 is H, OH, alkyl, alkoxy, F, Cl or --CF.sub.3, R.sub.5 and R.sub.7 are H, OH, alkoxy, .alpha.-substituted alkyl or .alpha.,.alpha.'-disubstituted alkyl, etc., R.sub.6 is H, OH, alkyl, alkoxy, cycloalkyl, etc., R.sub.5 and R.sub.7 cannot simultaneously be OH or alkoxy and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 cannot simultaneously be H, R.sub.5 and R.sub.6 or R.sub.6 and R.sub.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: December 19, 1995
    Assignee: Centre International de Recherches Dermatologiques (CIRD Galderma)
    Inventor: Jean-Michel Bernardon
  • Patent number: 5468897
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r" represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r" taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha., .alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: November 21, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5446059
    Abstract: Benzimidazole derivatives having general formula (I), wherein R.sub.1 and R.sub.2 are a hydrogen atom, a lower alkyl radical, an OR.sub.4 radical, a lower fluoroalkyl radical or a halogen atom; R.sub.3 is a hydrogen atom, a lower alkyl radical, a halogen, a hydroxyl or a lower alkoxy radical having 1-6 carbon atoms; R.sub.4 is a hydrogen atom, a lower alkyl radical, a benzyl radical or a (II) radical, PO.sub.3 H, SO.sub.3 H or an aminoacid residue; R.sub.7 is a lower alkyl radical, a lower alkoxy radical having 1-6 carbon atoms, a --(CH.sub.2).sub.n --COOH radical where n=1-6, or the radical (III), where r' and r" are a hydrogen atom or a lower alkyl radical, or form, together with the nitrogen atom, a 5 or 6-membered heterocyclic ring optionally interrupted by a heteroatom; R.sub.5 and R.sub.6 are different and represent the OR.sub.8 radical or a mono or polycyclic cycloalkyl radical having 5-12 carbon atoms bound to the phenyl core by a tertiary carbon; R.sub.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: August 29, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Jean-Philippe Rocher, Daniel Cavey
  • Patent number: 5439925
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use is in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: August 8, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, Willliam R. Pilgrim
  • Patent number: 5434180
    Abstract: The present invention relates to new polycyclic aromatic derivatives, to processes for their preparation and to their use in therapeutic and cosmetic formulations.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: July 18, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5387594
    Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: February 7, 1995
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5332856
    Abstract: Bi-aromatic esters have the formula ##STR1## wherein R.sub.1 represents H, OH, --CH.sub.3, --CH.sub.2 OH, --CH(OH)CH.sub.3, --COOR.sub.9, ##STR2## or SO.sub.2 R.sub.10 ; R.sub.9 represents H, C.sub.1 -C.sub.6 alkyl or mono or polyhydroxyalkyl; R.sub.10 represents OH, C.sub.1 -C.sub.6 alkyl or ##STR3## r' and r'' represent H, C.sub.1 -C.sub.6 alkyl, aryl, aralkyl, mono or polyhydroxyalkyl, or r' and r'' taken together form a heterocycle; R.sub.2 represents H, C.sub.1 -C.sub.6 alkyl, OR.sub.9, F or --CF.sub.3 ; R.sub.3, R.sub.4 and R.sub.5 represent H, F, OH, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --COOH or --CH.sub.2 OH; R.sub.6 and R.sub.8 represent H, .alpha.-substituted C.sub.3 -C.sub.15 alkyl, .alpha.,.alpha.'-disubstituted C.sub.4 -C.sub.12 alkyl, C.sub.3 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 mono or polycyclic cycloalkyl whose linking carbon is trisubstituted, --SR.sub.11, --SO.sub.2 R.sub.11 or --SOR.sub.11 ; R.sub.11 represents C.sub.1 -C.sub.6 alkyl or cycloalkyl; R.sub.6 and R.sub.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: July 26, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Braham Shroot, Jean-Michel Bernardon, William R. Pilgrim
  • Patent number: 5312751
    Abstract: The subject invention relates to monoclonal antibodies which react with antigenic determinants which are present of the stratus corneum of human epidermis. Furthermore, the invention also relates to methods of using such monoclonal antibodies in immunoassays. One monoclonal antibody of the present invention which is particularly useful is BC 21.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: May 17, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Serge Michel, Jacques Bailly, Gaelle Saintigny, Uwe Reichert
  • Patent number: 5310959
    Abstract: Processes for preparing 5,8,11-eicosatriynoic acid as well as esters and amides thereof involves initially preparing the acid by reacting 1-decyne with 1,4-dihalo-2-butyne in the presence of a strong base to form 1-halo-2,5-tetradecadiyne which is then reacted with 5-hexynoic acid so as to form 5,8,11-eicosatriynoic acid. This acid can then be converted to the acid chloride form and reacted with an alcohol to form an ester or converted to a potassium salt and reacted with a halide also to form an ester, or after conversion to an acid chloride reacted with an amine in the presence of a tertiary amine to form an amide, or the acid can be reacted with carbonyldiimidazole in the presence of a solvent and excess amine to form an amide.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: May 10, 1994
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
  • Patent number: 5288744
    Abstract: Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r" represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein Z is O or S, ##STR5## wherein R.sub.5 is lower alkyl or ##STR6## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: February 22, 1994
    Assignee: Centre International De Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5268494
    Abstract: Compounds corresponding to the formula: ##STR1## wherein A represents --CH.sub.2).sub.2 or --C.tbd.C--;n is equal to 0, 1 or 2;R represents hydroxyl, alkoxy having the formula --OR.sub.1, or amino having the formula ##STR2## R.sub.1 represents alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl;R.sub.2 and R.sub.3 represent hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl;R.sub.2 and R.sub.3 form, with the nitrogen atom, a heterocyclic ring.Application of these compounds in pharmacy and cosmetics.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: December 7, 1993
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Michel Colin
  • Patent number: 5260295
    Abstract: Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r" represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.6 is alkyl having 1-4 carbon atoms and R.sub.7 is branched alkyl having 4-12 atoms.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: November 9, 1993
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: RE34440
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radial; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: November 9, 1993
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: RE34805
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: December 6, 1994
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon