BE1002236A4 - NOVEL BENZYLIDENE-CYCLANONES DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTI-OXIDIZING AGENTS AND AS SOLAR FILTERS, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. - Google Patents

NOVEL BENZYLIDENE-CYCLANONES DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTI-OXIDIZING AGENTS AND AS SOLAR FILTERS, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. Download PDF

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Publication number
BE1002236A4
BE1002236A4 BE8900998A BE8900998A BE1002236A4 BE 1002236 A4 BE1002236 A4 BE 1002236A4 BE 8900998 A BE8900998 A BE 8900998A BE 8900998 A BE8900998 A BE 8900998A BE 1002236 A4 BE1002236 A4 BE 1002236A4
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BE
Belgium
Prior art keywords
preparation
derivatives
cyclanones
cosmetic
alkyl
Prior art date
Application number
BE8900998A
Other languages
French (fr)
Inventor
Alain Lagrange
Serge Forestier
Gerard Lang
Bernadette Luppi
Original Assignee
Oreal
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Publication date
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Publication of BE1002236A4 publication Critical patent/BE1002236A4/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne les dérivés de benzylidène cyclanone de formule : où R et R1 sont de l'hydrogène, OH, un reste alkyle linéaire ou ramifié en C1-C6 ou un reste alcoxy linéaire ou ramifié en C1-C8, l'un des radicaux R1 et R étant différent d'hydrogène ou hydroxyle, l'un au moins des deux étant hydroxyle, R4, R5, R6 et R7 représentent un reste alkyle en C1-C18, aralkyle ou aryle, R4 et R5 et/ou R6 et R7 pouvant foréer un cycle saturé en C5-C12 éventuellement substitué, X représente (CH2)n avec n = 1 ou 2 ou N-R8 avec R8 = H, alkyle en C1-C8, aralkyle, OH, ou -O-R9, R9 étant alkyle en C1-C8, ou bien X représente O ou S. Procédé de préparation de ces composés et leurs utilisations en tant qu'anti-oxydants, filtres solaires à large bande et médicaments pour le traitement des inflammations et allergies cutanées ainsi que pour la prévention de certains cancers.The invention relates to the benzylidene cyclanone derivatives of formula: where R and R1 are hydrogen, OH, a linear or branched C1-C6 alkyl residue or a linear or branched C1-C8 alkoxy residue, one of the radicals R1 and R being other than hydrogen or hydroxyl, at least one of the two being hydroxyl, R4, R5, R6 and R7 represent a C1-C18 alkyl, aralkyl or aryl residue, R4 and R5 and / or R6 and R7 being able to drill an optionally substituted C5-C12 saturated cycle, X represents (CH2) n with n = 1 or 2 or N-R8 with R8 = H, C1-C8 alkyl, aralkyl, OH, or -O-R9, R9 being C1-C8 alkyl, or X represents O or S. Process for the preparation of these compounds and their uses as antioxidants, broadband sunscreens and drugs for the treatment of skin inflammations and allergies as well as for the prevention of certain cancers.

BE8900998A 1988-09-20 1989-09-19 NOVEL BENZYLIDENE-CYCLANONES DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTI-OXIDIZING AGENTS AND AS SOLAR FILTERS, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. BE1002236A4 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU87339A LU87339A1 (en) 1988-09-20 1988-09-20 NOVEL BENZYLIDENE-CYCLANONES DERIVATIVES, THEIR PREPARATION PROCESS, THEIR USE AS ANTI-OXIDIZING AGENTS AND AS SOLAR FILTERS, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Publications (1)

Publication Number Publication Date
BE1002236A4 true BE1002236A4 (en) 1990-10-30

Family

ID=19731091

Family Applications (1)

Application Number Title Priority Date Filing Date
BE8900998A BE1002236A4 (en) 1988-09-20 1989-09-19 NOVEL BENZYLIDENE-CYCLANONES DERIVATIVES, PROCESS FOR THEIR PREPARATION, THEIR USE AS ANTI-OXIDIZING AGENTS AND AS SOLAR FILTERS, COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.

Country Status (10)

Country Link
JP (1) JPH02160741A (en)
AU (1) AU630371B2 (en)
BE (1) BE1002236A4 (en)
CH (1) CH679668A5 (en)
DE (1) DE3931269A1 (en)
FR (1) FR2636531B1 (en)
GB (1) GB2222829B (en)
IT (1) IT1233198B (en)
LU (1) LU87339A1 (en)
NL (1) NL8902326A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2638354B1 (en) * 1988-10-28 1993-10-15 Oreal FILTERING COSMETIC COMPOSITIONS, THEIR USE FOR PROTECTING THE SKIN AND HAIR AGAINST ULTRAVIOLET RADIATION, NOVEL 5-BENZYLIDENE 3-OXA CYCLOPENTANONE DERIVATIVES USED IN SUCH COMPOSITIONS AND THEIR PREPARATION PROCESS
DE4204922A1 (en) * 1992-02-19 1993-08-26 Merck Patent Gmbh KETOTRICYCLO (5.2.1.0) DECANE DERIVATIVES
US5840282A (en) * 1995-06-21 1998-11-24 Givaudan-Roure (International) Sa Light screening compositions
ID17907A (en) * 1997-02-20 1998-02-05 Fakultas Farmasi Uni Gajah Mad BENZILIDIN CYCYLOHEXANON BENZILIDINE CYCOPOPANANONE BINZYLIDINE ACETONE AND ITS PRODUCTION
DE19739447A1 (en) * 1997-09-02 1999-03-04 Coty Bv Emulsifier-free, clear sunscreen gel
DE19857252A1 (en) * 1998-12-11 2000-06-15 Haarmann & Reimer Gmbh Benzylidene-gamma-butyrolactones, process for their preparation and their use as UV absorbers
FR2840531B1 (en) * 2002-06-11 2004-10-29 Oreal COSMETIC COMPOSITION COMPRISING A MIMETIC AGENT FOR THE ACTIVITY OF DOPACHROME TAUTOMERASE (TRP-2) FOR COMBATING CANITIS
AU2003255653A1 (en) 2002-06-11 2003-12-22 L'oreal Use of an agent mimicking dopachrome tautomerase (trp-2) activity as protective agent for hair follicle melanocytes and uses thereof
FR2939438B1 (en) * 2008-12-09 2010-12-17 Oreal N- (1-OXO-1,3-DIHYDRO-2-BENZOFURAN-5-YL) ALKYLAMIDE DERIVATIVES; COSMETIC COMPOSITIONS; USES FOR ENHANCING AND / OR PRESERVING THE NATURAL ANTIOXIDANT PROTECTION OF THE SKIN

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2395023A1 (en) * 1977-06-23 1979-01-19 Henkel Kgaa COSMETIC PRODUCTS PROTECTING AGAINST LIGHT, MORE SPECIFICALLY AGAINST THE A REGION OF THE ULTRAVIOLET SPECTRUM
GB2025957A (en) * 1978-07-11 1980-01-30 Oreal Oxybenzylidenebornanones their preparation and their use in cosmetics
EP0044970A2 (en) * 1980-07-26 1982-02-03 BASF Aktiengesellschaft Use of etherified 2-(4-hydroxybenzylidene)-gamma-butyrolactones as light protectants
EP0057882A1 (en) * 1981-02-05 1982-08-18 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha 3,5-Di-tert-butylstyrene derivatives, processes for their preparations, and pharmaceutical compositions containing them

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU87008A1 (en) * 1987-10-05 1989-05-08 Oreal NOVEL TERTIOBUTYL DERIVATIVES OF BENZYLIDENE CAMPHOR, PREPARATION METHOD THEREOF, USE THEREOF AS ANTIOXIDANT AGENTS AND COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2645150B1 (en) * 1989-03-31 1994-07-22 Oreal NOVEL BENZYL-CYCLANONES DERIVATIVES, PROCESS FOR THEIR PREPARATION AND COSMETIC AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
ZA9010041B (en) * 1989-12-21 1992-08-26 Lilly Co Eli Compounds for treating inflammatory bowel disease

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2395023A1 (en) * 1977-06-23 1979-01-19 Henkel Kgaa COSMETIC PRODUCTS PROTECTING AGAINST LIGHT, MORE SPECIFICALLY AGAINST THE A REGION OF THE ULTRAVIOLET SPECTRUM
GB2025957A (en) * 1978-07-11 1980-01-30 Oreal Oxybenzylidenebornanones their preparation and their use in cosmetics
EP0044970A2 (en) * 1980-07-26 1982-02-03 BASF Aktiengesellschaft Use of etherified 2-(4-hydroxybenzylidene)-gamma-butyrolactones as light protectants
EP0057882A1 (en) * 1981-02-05 1982-08-18 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha 3,5-Di-tert-butylstyrene derivatives, processes for their preparations, and pharmaceutical compositions containing them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 89, no. 7, 14 août 1978, page 570, résumé no. 59846w, Columbus, Ohio, US; Y. SATO et al.: "Synthetic studies on cardiovascular agents. IV. Synthesis of fused dihydropyridine derivatives", & YAKUGAKU ZASSHI 1978, 98(4), 448-65 *

Also Published As

Publication number Publication date
JPH02160741A (en) 1990-06-20
AU630371B2 (en) 1992-10-29
FR2636531A1 (en) 1990-03-23
GB8921224D0 (en) 1989-11-08
IT1233198B (en) 1992-03-16
GB2222829B (en) 1992-04-15
GB2222829A (en) 1990-03-21
DE3931269A1 (en) 1990-03-22
FR2636531B1 (en) 1994-05-20
AU4146389A (en) 1990-03-29
LU87339A1 (en) 1990-04-06
CH679668A5 (en) 1992-03-31
NL8902326A (en) 1990-04-17
IT8967776A0 (en) 1989-09-19

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RE Patent lapsed

Owner name: L OREAL

Effective date: 19930930