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AR037341A1 - COMPOUNDS DERIVED FROM 1-OXA-ESPIRO [2,5] OCTAN-6-OL, METHOD OF SYNTHESIS OF COMPOUNDS DERIVED FROM FUMAGILINE, PHARMACEUTICAL AND COSMETIC COMPOSITIONS THAT INCLUDE THEM, USE OF PHARMACEUTICAL COMPOSITIONS AND USE OF COSMETIC COMPOSITION COSMETICS COMPOSITIONS - Google Patents

COMPOUNDS DERIVED FROM 1-OXA-ESPIRO [2,5] OCTAN-6-OL, METHOD OF SYNTHESIS OF COMPOUNDS DERIVED FROM FUMAGILINE, PHARMACEUTICAL AND COSMETIC COMPOSITIONS THAT INCLUDE THEM, USE OF PHARMACEUTICAL COMPOSITIONS AND USE OF COSMETIC COMPOSITION COSMETICS COMPOSITIONS

Info

Publication number
AR037341A1
AR037341A1 ARP020104286A ARP020104286A AR037341A1 AR 037341 A1 AR037341 A1 AR 037341A1 AR P020104286 A ARP020104286 A AR P020104286A AR P020104286 A ARP020104286 A AR P020104286A AR 037341 A1 AR037341 A1 AR 037341A1
Authority
AR
Argentina
Prior art keywords
carbon atoms
radical
compositions
linear
formula
Prior art date
Application number
ARP020104286A
Other languages
Spanish (es)
Inventor
Jacques Eustache
Jean-Guy Boiteau
Celine Tarnus
Vincent Rodeschini
De Weghe Pierre Van
Original Assignee
Galderma Res & Dev
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Galderma Res & Dev filed Critical Galderma Res & Dev
Publication of AR037341A1 publication Critical patent/AR037341A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/10Anti-acne agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • A61P27/06Antiglaucoma agents or miotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Transplantation (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Compuestos derivados de 1-oxa-espiro [2,5] octan-6-ol, que responden a la formula general (1), en la cual: Rx representa H, un radical alquilo lineal o ramificado de 1 a 5 átomos de carbono o un radical 1-hidroxialquilo lineal o ramificado de 1 a 5 átomos de carbono; R1 representa un radical alquilo lineal o ramificado de 1 a 5 átomos de carbono, o un radical alquenilo que tiene la estructura de fórmula (2) o el epóxido correspondiente representado por la estructura de la formula (3); R5 y R6 tienen las significaciones dadas anteriormente, R2 es H o un radical alquilo lineal de 1 a 5 átomos de carbono, R3 es H o un radical representado por las fórmulas (4) ó (5); R7 e Y tienen las significaciones dadas anteriormente; R4 es H, un radical alquilo lineal o ramificado de 1 a 5 átomos de carbono, o un radical XR11, R4 es preferentemente un radical metilo o etilo; X y R11 tienen las significaciones dadas anteriormente; R5 es H o un radical metilo; R6 es H o un radical alquilo lineal o ramificado de 1 a 5 átomos de carbono, los radicales R5 y R6 tomados en forma conjunta, pueden tomar un carbociclo de 3 a 10 átomos de carbono insaturado o no, como, por ejemplo, un ciclohexeno; R7 es una cadena poliinsaturada que presenta de 5 a 7 átomos de carbono y una función carboxilo terminal o un núcleo aromático correspondiente a la fórmula general (6); R8, R9, R10, valen independientemente H o OCH3, R11 es H, un radical alquilo de 1 a 5 átomos de carbono o un núcleo aromático; X representa O ó S; Y representa un átomo de halógeno elegido entre el cloro, el bromo, el yodo y el flúor, y se entiende que, cuando R2 representa un alquilo de 1 a 5 átomos de carbono y R4 representa H, entonces R1 representa un alquilo de 1 a 5 átomos de carbono o un alquenilo que tiene la estructura (a) y cuando R1 representa el radical (b) entonces Rx y R4 no pueden simultáneamente representar H, y los isómeros ópticos y geométricos, las sales así como las mezclas de dichos compuestos de fórmula (1). Método para la síntesis de compuestos derivados de fumagilina, composiciones farmacéuticas y cosméticas, utilización de las composiciones farmacéuticas y utilización cosmética de las composiciones cosméticas. Los compuestos de formula (1) son útiles por ejemplo para el tratamiento de las afecciones relacionadas con un desorden de la angiogénesis, con la proliferación celular, de carácter inflamatorio o no, tales como los hemangiomas, los tumores malignos o benignos, los cánceres, los melanomas, los carcinomas de las células basales, el granuloma piogénico, los angiofibromas, la esclerodermia, los tumores oculares, la isquemia coriorretiniana, los neovasos retinianos, el glaucoma neovascular, las cicatrices tracomatosas, las enfermedades reumatoides , la artritis reumática, la psoriasis, el sarcoma de Kaposi, el angiosarcoma, el lupus, la rosácea, la retinopatía proliferativa de origen diabético, el rechazo de injerto, los trastornos de la cicatrización tales como las queloides y las cicatrices hipertróficas. Los compuestos de fórmula (1) son también útiles en el campo cosmético, por ejemplo para la higiene corporal o capilar; para el tratamiento de las pieles con tendencia acneica, para la recuperación del cabello, contra la caída del cabello, para luchar contra el aspecto graso de la piel o del cabello, para la protección contra los efectos nefastos del sol o para el tratamiento de las pieles fisiológicamente secas, y para prevenir y/o luchar contra el envejecimiento fotoinducido o cronológico.Compounds derived from 1-oxa-spiro [2,5] octan-6-ol, which respond to the general formula (1), in which: Rx represents H, a linear or branched alkyl radical of 1 to 5 carbon atoms or a linear or branched 1-hydroxyalkyl radical of 1 to 5 carbon atoms; R1 represents a linear or branched alkyl radical of 1 to 5 carbon atoms, or an alkenyl radical having the structure of formula (2) or the corresponding epoxide represented by the structure of formula (3); R5 and R6 have the meanings given above, R2 is H or a linear alkyl radical of 1 to 5 carbon atoms, R3 is H or a radical represented by formulas (4) or (5); R7 and Y have the meanings given above; R4 is H, a linear or branched alkyl radical of 1 to 5 carbon atoms, or an XR11 radical, R4 is preferably a methyl or ethyl radical; X and R11 have the meanings given above; R5 is H or a methyl radical; R6 is H or a linear or branched alkyl radical of 1 to 5 carbon atoms, the radicals R5 and R6 taken together can take a carbocycle of 3 to 10 carbon atoms unsaturated or not, such as a cyclohexene ; R7 is a polyunsaturated chain having 5 to 7 carbon atoms and a carboxyl terminal function or an aromatic nucleus corresponding to the general formula (6); R8, R9, R10, independently worth H or OCH3, R11 is H, an alkyl radical of 1 to 5 carbon atoms or an aromatic nucleus; X represents O or S; Y represents a halogen atom chosen from chlorine, bromine, iodine and fluorine, and it is understood that when R2 represents an alkyl of 1 to 5 carbon atoms and R4 represents H, then R1 represents an alkyl of 1 to 5 carbon atoms or an alkenyl having the structure (a) and when R1 represents the radical (b) then Rx and R4 cannot simultaneously represent H, and the optical and geometric isomers, salts as well as mixtures of said compounds of Formula 1). Method for the synthesis of compounds derived from fumagiline, pharmaceutical and cosmetic compositions, use of pharmaceutical compositions and cosmetic use of cosmetic compositions. The compounds of formula (1) are useful, for example, for the treatment of conditions related to an angiogenesis disorder, with cellular proliferation, inflammatory or not, such as hemangiomas, malignant or benign tumors, cancers, melanomas, basal cell carcinomas, pyogenic granuloma, angiofibromas, scleroderma, ocular tumors, chorioretinal ischemia, retinal neovases, neovascular glaucoma, tracomatous scars, rheumatoid diseases, rheumatic arthritis, psoriasis , Kaposi's sarcoma, angiosarcoma, lupus, rosacea, proliferative retinopathy of diabetic origin, graft rejection, scarring disorders such as keloids and hypertrophic scars. The compounds of formula (1) are also useful in the cosmetic field, for example for body or hair hygiene; for the treatment of skins with acneic tendency, for the recovery of hair, against hair loss, to fight against the oily appearance of the skin or hair, for protection against the harmful effects of the sun or for the treatment of physiologically dry skin, and to prevent and / or fight against photoinduced or chronological aging.

ARP020104286A 2001-11-09 2002-11-08 COMPOUNDS DERIVED FROM 1-OXA-ESPIRO [2,5] OCTAN-6-OL, METHOD OF SYNTHESIS OF COMPOUNDS DERIVED FROM FUMAGILINE, PHARMACEUTICAL AND COSMETIC COMPOSITIONS THAT INCLUDE THEM, USE OF PHARMACEUTICAL COMPOSITIONS AND USE OF COSMETIC COMPOSITION COSMETICS COMPOSITIONS AR037341A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0114542A FR2832149B1 (en) 2001-11-09 2001-11-09 NOVEL INHIBITORS OF ANGIOGENESIS AND THEIR PHARMACEUTICAL AND COSMETIC USE

Publications (1)

Publication Number Publication Date
AR037341A1 true AR037341A1 (en) 2004-11-03

Family

ID=8869256

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP020104286A AR037341A1 (en) 2001-11-09 2002-11-08 COMPOUNDS DERIVED FROM 1-OXA-ESPIRO [2,5] OCTAN-6-OL, METHOD OF SYNTHESIS OF COMPOUNDS DERIVED FROM FUMAGILINE, PHARMACEUTICAL AND COSMETIC COMPOSITIONS THAT INCLUDE THEM, USE OF PHARMACEUTICAL COMPOSITIONS AND USE OF COSMETIC COMPOSITION COSMETICS COMPOSITIONS

Country Status (5)

Country Link
EP (1) EP1480964A1 (en)
JP (1) JP2005519026A (en)
AR (1) AR037341A1 (en)
FR (1) FR2832149B1 (en)
WO (1) WO2003040119A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2872511B1 (en) * 2004-06-30 2006-08-11 Galderma Res & Dev NOVEL INHIBITORS OF ANGIOGENESIS AND THEIR PHARMACEUTICAL AND COSMETIC USE
US8299067B2 (en) * 2008-03-27 2012-10-30 Versitech Limited 5-demethoxyfumagillol and derivatives thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68927904T2 (en) * 1988-09-01 1997-09-04 Takeda Chemical Industries Ltd Fumagillol derivatives
DE68915900T2 (en) * 1988-09-01 1994-11-24 Childrens Medical Center Angiogenesis inhibitor.
ATE87623T1 (en) * 1989-03-06 1993-04-15 Takeda Chemical Industries Ltd 6-EPIFUMAGILLOLS, THEIR PREPARATION AND USE.
US6017954A (en) * 1989-08-10 2000-01-25 Children's Medical Center Corp. Method of treating tumors using O-substituted fumagillol derivatives
AU719106B2 (en) * 1995-02-28 2000-05-04 Gillette Company, The Use of angiogenesis suppressors for inhibiting hair growth
WO1998056372A1 (en) * 1997-06-09 1998-12-17 Massachusetts Institute Of Technology TYPE 2 METHIONINE AMINOPEPTIDASE (MetAP2) INHIBITORS AND USES THEROF
WO1999061432A1 (en) * 1998-05-12 1999-12-02 Biochem Pharma Inc. Fumagillin analogs and their use as angiogenesis inhibitors

Also Published As

Publication number Publication date
JP2005519026A (en) 2005-06-30
FR2832149A1 (en) 2003-05-16
EP1480964A1 (en) 2004-12-01
WO2003040119A1 (en) 2003-05-15
WO2003040119A8 (en) 2003-11-27
FR2832149B1 (en) 2006-01-06

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