Patents Assigned to Centre International de Recherches Dermatologiques
  • Patent number: 5212303
    Abstract: A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents (i) ##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 --0--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 conjuctive tissues.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: May 18, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5196577
    Abstract: 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzoic acid marked with tritium is used as a radioactive marker in the titration of nuclear receptors and CRABP, in the measurement of the affinity of retinoids for nuclear receptors and CRABP, in the titration of known retinoids, the characterization of antibodies directed against 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthracenyl) benzoic acid, and in the study of the distribution and metabolism of said benzoic acid derivative.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: March 23, 1993
    Assignee: Centre International de Recherches Dermatologiques
    Inventors: Braham Shroot, Yves M. Darmon, Philippe Nedoncelle, Claude Martin
  • Patent number: 5183889
    Abstract: A benzonphthalene 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 conjuctive tissues.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: February 2, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5173289
    Abstract: Aromatic esters and thioesters of the formula ##STR1## are useful in human and veterinary medicine and in cosmetic formulations. In the formula, X represents oxygen or sulfur, r' and 4" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle, R.sub.2 represents .alpha., .alpha.'- dissubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted and R.sub.3 and R.sub.4 represent hydrogen or lower alkyl.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: December 22, 1992
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5151534
    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: May 10, 1989
    Date of Patent: September 29, 1992
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Michel Colin
  • Patent number: 5149631
    Abstract: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid marked with tritium; its preparation; and its use as a radioactive marker, in the titration of nuclear receptors of retinoids in the presence of contaminating CRABP, or in the measurement of the affinity of retinoids for these nuclear receptors.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: September 22, 1992
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma)
    Inventors: Braham Shroot, Michel Darmon
  • Patent number: 5124473
    Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.In the formula, X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: June 23, 1992
    Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)
    Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5098895
    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: March 30, 1990
    Date of Patent: March 24, 1992
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5073361
    Abstract: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid marked with tritium; its preparation; and its use as a radioactive marker, in the titration of nuclear receptors of retinoids in the presence of contaminating CRABP, or in the measurement of the affinity of retinoids for these nuclear receptors.
    Type: Grant
    Filed: July 19, 1990
    Date of Patent: December 17, 1991
    Assignee: Centre International de Recherches Dermatologiques Galderma (CIRD Galderma
    Inventors: Braham Shroot, Michel Darmon
  • Patent number: 5066427
    Abstract: Compound, corresponding to the formulaC.sub.8 H.sub.17 (C.tbd.C--CH.sub.2).sub.3 CH.sub.2 CH.sub.2 COR (I)in which R is a C.sub.1 -C.sub.8 lower alkoxy or C.sub.4 -C.sub.6 cycloaly group, substituted with one or more hydroxyl groups and/or interrupted by one or more hetero atoms chosen from oxygen and sulphur, an amino group of structure ##STR1## in which R.sub.1 or R.sub.2, which may be identical or different, denote a hydrogen atom or a linear or branched C.sub.1 -C.sub.8 lower alkyl radical, optionally interrupted by one or more hetero atoms chosen from oxygen, sulphur and nitrogen, this alkyl radical being able to be substituted with one or more hydroxyl groups, R.sub.1 and R.sub.2 not being able to denote hydrogen simultaneously, or alternatively R.sub.1 and R.sub.2 form, together with the nitrogen atom, a heterocyclic system optionally containing oxygen, sulphur or nitrogen as an additional hetero atom, one of the radicals R.sub.1 and R.sub.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: November 19, 1991
    Assignee: Centre International de Recherches Dermatologiques dite CIRD
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
  • Patent number: 5059621
    Abstract: An aromatic heterocyclic compound has 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, mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r'and r" represent hydrogen or lower alkyl, 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 and X represents oxygen or sulfur, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C wherein R.sub.5 is CH.sub.3 and (ii) when Y is CH and X represents sulfur Ar is other than A.The compound is useful in the treatment of dermatologic ailments linked to a keratinization disorder.
    Type: Grant
    Filed: November 2, 1989
    Date of Patent: October 22, 1991
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5041639
    Abstract: New polysubstituted derivatives of naphthalene. These derivatives correspond to the following formula: ##STR1## in which: R.sub.1 to R.sub.4 is H or CH.sub.3R.sub.5 is ##STR2## or (iv) the radical: 2-oxazolinyl m is 0 or 1R.sub.8.sbsb.r is H, alkyl, OR.sub.11, R.sub.11 being H, alkyl or ##STR3## R.sub.13 being alkyl or aryl or R.sub.8 is ##STR4## when m=1, r' and r" representing H, alkyl mono or polyhydroxyalkyl, aryl or a heterocycle when they are taken together, R.sub.9 is H or alkyl, R.sub.10 is H, alkyl and the acetals of the said compounds ##STR5## --OR.sub.14, R.sub.14 being H, alkyl, mono or polyhydroxyalkyl, aryl or aralkyl a rest of a sugar or represents ##STR6## being 0, 1, 2 or 3 R.sub.6 represents a hydrogen atom or a lower alkyl radical,R.sub.7 represents H, alkyl, halogen, hydroxyl, sulfydryl, alkoxy, alkylthio, acyloxy, acylthio, acylamino or primary, secondari or tertiary amino and the salts of the said compounds.These compounds find an application in the cosmetic and pharmaceutical fields.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: August 20, 1991
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
  • Patent number: 5039793
    Abstract: A protein characterized by the fact that it is a nonkeratinic protein present in the cytoplasm of suprabasal epidermal cells, in particular in man, and absent in basocellular carcinoma, melanoma and naevus cells; antibodies directed against said protein, their preparation and their application as reagents; cellular stocks secreting such antibodies, and their preparation.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 13, 1991
    Assignee: Centre International de Recherches Dermatologiques
    Inventors: Bruno Bernard, Yves M. Darmon
  • Patent number: 5015758
    Abstract: A process for the preparation of 1-adamantane derivatives characterized by the fact that a 1-acyloxyadamantane, in which the acyl group contains 1 to 4 carbon atoms, is reacted with a receptor compound in a linear aliphatic or cycloaliphatic type solvent in the presence of concentrated sulfuric acid and at ambient temperature.
    Type: Grant
    Filed: September 6, 1989
    Date of Patent: May 14, 1991
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: William R. Pilgrim, Joel Lagiere
  • Patent number: 4983625
    Abstract: A bath composition for the treatment of psoriasis or other cutaneous disorders contains from 10-79.9 weight percent of a hydrophilic phase, from 20-89.9 weight percent of a fatty or lipophilic phase and from 0.1-2 weight percent of an active component belonging to the class of psoralenes.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: January 8, 1991
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Josiane Allec
  • Patent number: 4927928
    Abstract: An aromatic benzamido compound having the formula ##STR1## wherein R.sub.1 represents --CH.sub.2 OH, --CHOHCH.sub.3 or --COR.sub.5,R.sub.5 represents hydrogen, lower alkyl, or --OR.sub.6 or ##STR2## R.sub.6 represents hydrogen, lower alkyl or mono- or polyhydroxyalkyl, r' and r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar or taken together form a heterocycle,R.sub.2 represents an .alpha.,.alpha.'-disubstituted alkyl having 4-12 carbon atoms or mono or polycyclic cycloalkyl having 5-12 carbon atoms, the linking carbon of which is quaternary,R.sub.3 represents hydrogen or alkyl having 1-10 carbon atoms, andR.sub.4 represents a hydrogen, lower alkyl or hydroxy, andthe salts of this aromatic benzamido compound when R.sub.6 represents hydrogen.
    Type: Grant
    Filed: January 21, 1987
    Date of Patent: May 22, 1990
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4925658
    Abstract: Aromatic esters and thioesters have the formula ##STR1## wherein X represents oxygen or sulfur,R.sub.1 represents --CH.sub.2 OH, --CH(OH)--CH.sub.3, --COOR.sub.5 or ##STR2## R.sub.5 represents hydrogen, lower alkyl, lower alkenyl, monohydroxyalkyl or polyhydroxyalkyl,r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle,R.sub.2 represents .alpha.,.alpha.'-disubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted,R.sub.3 represents hydrogen, lower alkyl, or --Si(CH.sub.3).sub.2 R'.sub.3 wherein R'.sub.3 represents lower alkyl, andR.sub.4 represents hydrogen or lower alkyl, andthe salts of these aromatic esters and thioesters of formula (I) when R.sub.5 represents hydrogen.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: May 15, 1990
    Assignee: Centre International De Recherches dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4920140
    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: March 24, 1988
    Date of Patent: April 24, 1990
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4892864
    Abstract: Pharmaceutical and cosmetic compositions contain as the active component 10-acetyl-1,8,9-triacetoxy anthracene.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: January 9, 1990
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan
  • Patent number: RE33533
    Abstract: A polycyclic heterocyclic compound has the formula ##STR1## wherein n is 1 or 2, R.sub.1 represents (i) lower alkyl, (ii)--CH.sub.2 OH or (iii) ##STR2## R.sub.2 represents (a) hydrogen, (b) ##STR3## or (c)--OR.sub.3, R.sub.3 represents hydrogen, C.sub.1 -C.sub.20 alkyl mono or polyhydroxyalkyl, aryl or aralkyl optionally substituted, the residue of a sugar or wherein p is 1, 2, or 3, and r' and r" represent hydrogen, lower alkyl, mono or polyhydroxalkyl, aryl optionally substituted, amino acid residue, aminated sugar residue, or together form a heterocycle, X represents oxygen, sulfur, SO, SO.sub.2 or --NR.sub.4, Y represents CR.sub.4 or a nitrogen atom and R.sub.4 represents hydrogen or lower alkyl. This polycyclic heterocyclic compound can be used in human and veterinary medicine and especially in the topical or systemic treatment of determatologic diseases.
    Type: Grant
    Filed: April 24, 1990
    Date of Patent: February 5, 1991
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon, Philippe Nedoncelle