Patents Assigned to Centre International De Recherches Dermatologiques (C.I.R.D.)
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Patent number: 5288744Abstract: 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: GrantFiled: June 18, 1992Date of Patent: February 22, 1994Assignee: Centre International De Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5268494Abstract: 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: GrantFiled: June 4, 1992Date of Patent: December 7, 1993Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Michel Colin
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Patent number: 5260295Abstract: 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: GrantFiled: May 7, 1991Date of Patent: November 9, 1993Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5173289Abstract: 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: GrantFiled: February 16, 1990Date of Patent: December 22, 1992Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5098895Abstract: 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: GrantFiled: March 30, 1990Date of Patent: March 24, 1992Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5059621Abstract: 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: GrantFiled: November 2, 1989Date of Patent: October 22, 1991Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5041639Abstract: 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: GrantFiled: September 15, 1989Date of Patent: August 20, 1991Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4927928Abstract: 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: GrantFiled: January 21, 1987Date of Patent: May 22, 1990Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 4920140Abstract: 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: GrantFiled: March 24, 1988Date of Patent: April 24, 1990Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 4892864Abstract: Pharmaceutical and cosmetic compositions contain as the active component 10-acetyl-1,8,9-triacetoxy anthracene.Type: GrantFiled: February 8, 1988Date of Patent: January 9, 1990Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Gerard Lang, Jean Maignan
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Patent number: 4889865Abstract: 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: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4886907Abstract: 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: GrantFiled: April 17, 1987Date of Patent: December 12, 1989Assignee: Centre International De Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Martine Bouclier
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Patent number: 4851541Abstract: 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: GrantFiled: June 5, 1986Date of Patent: July 25, 1989Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Jean Maignan, Serge Restle, Michel Colin
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Patent number: 4843097Abstract: 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: GrantFiled: April 4, 1988Date of Patent: June 27, 1989Assignee: 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
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Patent number: 4826969Abstract: 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: GrantFiled: October 14, 1986Date of Patent: May 2, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
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Patent number: 4810694Abstract: 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: GrantFiled: January 10, 1986Date of Patent: March 7, 1989Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Jean R. Maignan, Braham Shroot, Serge A. Restle
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Patent number: 4755530Abstract: 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: GrantFiled: April 16, 1986Date of Patent: July 5, 1988Assignee: Centre International de Recherches Dermatologiques (C.I.R.D)Inventors: Braham Shroot, Gerard Lang, Jean Maignan
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Patent number: 4740519Abstract: 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: GrantFiled: March 13, 1986Date of Patent: April 26, 1988Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 4717720Abstract: 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: GrantFiled: April 10, 1986Date of Patent: January 5, 1988Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: RE34440Abstract: 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: GrantFiled: July 16, 1992Date of Patent: November 9, 1993Assignee: Centre International de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon