Patents Assigned to Centre International de Recherches Dermatologiques
  • Patent number: 4889865
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4886907
    Abstract: New polysubstituted derivatives of naphtalene.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(i) ##STR2## (ii) --C.tbd.N (iii) ##STR3## or (iv) the radical: 2-oxazolinylm is 0 or 1R.sub.8 is H, alkyl, OR.sub.11, R.sub.11 being H, alkyl or ##STR4## R.sub.13 being alkyl or aryl or R.sub.8 is ##STR5## 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, ##STR6## --OR.sub.14, R.sub.14 being H, alkyl, mono or polyhydroxyalkyl, aryl or aralkyl a rest of a sugar or represents ##STR7## 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, secondary or tertiary amino and the salts of the said compounds.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: December 12, 1989
    Assignee: Centre International De Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
  • Patent number: 4880941
    Abstract: 2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-6-benzo [b] thiophene carboxylic acid labelled with tritium, its preparation and its use as a radioactive marker in the determination of the affinity of, the presence of, or the amount of, retinoids having a carboxylic group and/or in the characterization of antibodies directed against this acid and/or in the quantification of the cRABP receptor of said retinoids.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: November 14, 1989
    Assignee: Centre International de Recherches Dermatologique (CIRD)
    Inventors: Braham Shroot, Oliver Watts, Joseph Gazith, Marie-Therese Cavey
  • Patent number: 4877789
    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 CH.sub.2 R O (I)in which R is a C.sub.1 -C.sub.8 lower alkoxy or C.sub.4 -C.sub.6 cycloalkoxy 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: July 3, 1986
    Date of Patent: October 31, 1989
    Assignee: Centre International de Recherches Dermatologiques dite C.I.R.D.
    Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
  • Patent number: 4874747
    Abstract: A polycyclic heterocyclic compound has the formula ##STR1## wherein n is 1 or 2,R.sub.1 l 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 ##STR4## wherein p is 1, 2, or 3, and r' and r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, 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 andR.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 29, 1988
    Date of Patent: October 17, 1989
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 4851541
    Abstract: A process for preparing a 4,5-tri or tetramethylene-4-isothiazoline-3-one comprises cyclizing a 2-alkyl or aralkyl thio-1-cycloalkene-1-carboxamide in the form of its sulfoxide in an organic solvent in the presence of a acid chloride and adding to the resulting 4,5-tri or tetramethylene-4-isothiazoline-3-one hydrochloride a mineral or organic base or water so as to free the 4,5-tri or tetramethylene-4-isothiazoline-3-one in the form of a free base.
    Type: Grant
    Filed: June 5, 1986
    Date of Patent: July 25, 1989
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Jean Maignan, Serge Restle, Michel Colin
  • Patent number: 4843097
    Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: June 27, 1989
    Assignee: Groupement d'Interet Economique dit: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4833240
    Abstract: Bicyclic aromatic compounds, having the following formula: ##STR1## in which: n=0 or 1;R' represents H, OH, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 acyloxy;R" represents H or C.sub.1 -C.sub.4 alkoxy;or R' and R" taken together form an oxo (.dbd.O), methano (.dbd.CH.sub.2) or hydroximino (.dbd.N--OH) radical;R represents --CH.sub.2 OH or --COR.sub.7 ;R.sub.7 represents H, OR.sub.8, or ##STR2## R.sub.8 represents H, C.sub.1 -C.sub.4 alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or aralkyl, optionally substituted, a sugar residue or ##STR3## where p is 1, 2 or 3 and r' and r" represent H, lower alkyl, monohydroxyalkyl, optionally interrupted by a heteroatom, polyhydroxyalkyl, optionally substituted aryl or benzyl, an amino acid residue or an aminated sugar residue or taken together with the nitrogen atom to which they are attached form a heterocycle;A represents methylene or dimethylene, substituted or not with lower alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent H or lower alkyl,R.sub.1 and R.sub.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: May 23, 1989
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
  • Patent number: 4826969
    Abstract: A bicyclic naphthalenic compound has the formula ##STR1## wherein A represents methylene or dimethylene, substituted or not by lower alkyl,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen or lower alkyl, orR.sub.1 and R.sub.3 taken together form a methylene or dimethylene bridge when A represents dimethylene,R' represents hydrogen, OH, alkoxy having 1-4 carbon atoms, acyloxy having 1-4 carbon atoms or amino,R" represents hydrogen or alkoxy having 1-4 carbon atoms, orr' and R" taken together form an oxo, methano or hydroxyimino group,R represents --CH.sub.2 OH or --COR.sub.5,R.sub.5 represents hydrogen, --OR.sub.6 or ##STR2## R.sub.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: May 2, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
  • Patent number: 4810694
    Abstract: The invention relates to a compound of formula (I) ##STR1## in which formula: R.sub.1, R.sub.3 and R.sub.4 denote, independently of each other a hydrogen atom, a C.sub.1 -C.sub.8 alkyl radical, a C.sub.1 -C.sub.8 alkoxy radical, a C.sub.1 -C.sub.8 acryloxy radical or a hydroxy ra dical;R, R' and R" denote, independently of each other, either one of the meanings given above for R.sub.1, R.sub.3 and R.sub.4, or a halogen atom, or a primary, secondary or tertiary amino radical,A having various meanings.The invention also relates to a process for the preparation of compounds of formula (I) and to medicinal and cosmetic compositions in which they are present.
    Type: Grant
    Filed: January 10, 1986
    Date of Patent: March 7, 1989
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Jean R. Maignan, Braham Shroot, Serge A. Restle
  • Patent number: 4755530
    Abstract: 1-hydroxy-8-axyloxy-10-acyl anthrones have the formula ##STR1## wherein R.sub.1 represents hydrogen or linear lower alkyl,R.sub.2 represents hydrogen, linear or branched alkyl having 1-6 carbon atoms, or linear or branched alkenyl having 2-6 carbon atoms, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached form a cycloalkyl radical having 3-6 carbon atoms,R.sub.3 represents linear or branched alkyl having 1-6 carbon atoms, linear or branched alkenyl having 2-6 carbon atoms, cycloalkyl having 3-6 carbon atoms, 2- or 3-furyl, 3- or 4-pyridyl or 2-thienyl.
    Type: Grant
    Filed: April 16, 1986
    Date of Patent: July 5, 1988
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D)
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan
  • Patent number: 4740519
    Abstract: Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents ##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.6 is alkyl having 1-4 carbon atoms and R.sub.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: April 26, 1988
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4717720
    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 --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: April 10, 1986
    Date of Patent: January 5, 1988
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 4708959
    Abstract: A 4,5-trimethylene-4-isothiazoline-3-one of the formula ##STR1## wherein R.sub.1 represents (i) hydrogen, (ii) alkyl having 1-12 carbon atoms, (iii) alkyl having 2 or 3 carbon atoms and substituted by one or two hydroxy groups, (iv) alkenyl having 3 to 6 carbon atoms, (v) ##STR2## wherein n is 0 or 1, m is 1 or 2, R.sup.1 is hydrogen or lower alkyl having from 1 to 5 carbon atoms and R.sub.2 is hydrogen, lower alkyl, nitro, trifluoromethyl or halogen, (vi) cycloalkyl having 3 to 6 carbon atoms and (vii) ##STR3## wherein R.sub.3 is hydrogen, alkyl having 1-12 carbon atoms or ##STR4## defined above, or the salt thereof with a mineral or organic acid. These compounds are useful as bactericides or fungicides.
    Type: Grant
    Filed: July 27, 1983
    Date of Patent: November 24, 1987
    Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jean Maignan
  • Patent number: 4696941
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent a straight-chain or branched alkyl group of 1 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a 2-furyl, 3-furyl, 3-pyridyl, 4-pyridyl or 2-thienyl group or an aromatic group of the formula ##STR2## wherein X, Y and Z are the same or different and represent hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, alkoxy with 1 to 4 carbon atoms, halogen, nitro or hydroxy groups are useful as pharmaceutical, veterinary and cosmetic agents.
    Type: Grant
    Filed: June 28, 1985
    Date of Patent: September 29, 1987
    Assignee: Groupement d'Interet Economique dit: Centre International 'de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan
  • Patent number: 4677123
    Abstract: Pharmaceutical or cosmetic composition containing as the active component 1,8-dihydroxy-10-phenyl-9-anthrone, and a process for preparing said active component.
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: June 30, 1987
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan
  • Patent number: 4654354
    Abstract: The invention provides compounds of formula ##STR1## in which formula R.sub.1 and R.sub.2 are identical or different and denote:(1) taken separately: a hydrogen atom, a linear or branched C.sub.1 -C.sub.4 alkyl radical, an unsubstituted phenyl radical or a phenyl radical substituted with a halogen atom, with a C.sub.1 -C.sub.4 alkoxy radical or with a C.sub.1 -C.sub.4 alkoxy radical;(2) taken together either(a) a polymethylene linkage; or(b) a benzene ring; or(c) a cyclic linkage containing a nitrogen atom to constitute an isothiazolopyridinone derivative; m being able to have the values 0 or 1;the group A in the formula (IV) denoting the group ##STR2## where R.sub.8 corresponds to a hydrogen atom, a methyl radical, a hydroxymethyl radical or a --CH.sub.2 O--CO--Ret group. The invention also provides a process for preparing the abovementioned compounds and also drug compositions and cosmetic compositions containing them.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: March 31, 1987
    Assignee: Centre International De Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Michel Colin
  • Patent number: 4558069
    Abstract: 1,8-dihydroxy-9-anthrone derivatives, substituted in the 10-position by an unsaturated radical, are described which have utility as ingredients in human and veterinary pharmaceutical and cosmetic preparations and which are compounds of the structural formula ##STR1## wherein R.sub.1 represents a hydrogen atom or a --CO.sub.2 R'.sub.2 radical,R.sub.2 and R'.sub.2 identical or different, represent a hydrogen atom, a linear or branched chain alkyl radical having 1 to 6 carbon atoms, a cycloalkyl radical having 4 to 6 carbon atoms or a benzyl radical,or R.sub.1 and R.sub.2 taken together form a radical --CO--, andn is 0 or 1,with the proviso that when n is 0 and R.sub.1 is --CO.sub.2 R'.sub.2, R.sub.2 and R'.sub.2 do not simultaneously represent the radical CH.sub.3,and the isomers of the compounds of formula (I) and mixtures thereof.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: December 10, 1985
    Assignee: Groupement d'Interet Economique dit: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jean Maignan, Gerard Lang
  • Patent number: 4548942
    Abstract: An anti-acne composition comprises in a carrier suitable for topical application to the skin an active compound having the formula ##STR1## wherein R.sub.1 is linear or branched alkyl having 1-12 carbon atoms, mono- or polyhydroxyalkyl having 2-5 carbon atoms, alkenyl having 3-6 carbon atoms, cycloalkyl having 3-6 carbon atoms, or a radical of the formula ##STR2## wherein n is 0 or 1, m is 1, 2 or 3, R.sub.2 is hydrogen or lower alkyl having 1-3 carbon atoms and R.sub.3 represents hydrogen, alkyl having 1-4 carbon atoms, nitro, --CF.sub.3 or halogen. The acid salts of these active compounds can also be used.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: October 22, 1985
    Assignees: Societe Anonyme dite: L'Oreal, Groupement d'Interet Economique dit: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jean Maignan
  • Patent number: 4465688
    Abstract: The invention concerns adducts of 1,8-dihydroxy-9-anthrone, of formula: ##STR1## in which: R.sub.1 and R.sub.2, taken together, form one of the following divalent residues: ##STR2## R.sub.3, R.sub.4, R'.sub.4, R.sub.5 and R'.sub.5 representing H, an alkyl group having 1-8 C with the exception of R.sub.5 =R'.sub.5 =CH.sub.3, a monohydroxyalkyl group with 2-8 C, possibly interrupted by one or more oxygens, a cycloalkyl group having 4-6 C, a phenyl group, or a benzyl group.Utilization of the compounds (I) in human or veterinary medicine, in particular in the treatment of psoriasis and or warts, and in cosmetics.
    Type: Grant
    Filed: June 29, 1982
    Date of Patent: August 14, 1984
    Assignee: Groupement d'Interet Economique Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Jean Maignan, Gerard Lang