CA2471910A1 - Derives de benzocyclodecane a activite antitumorale - Google Patents

Derives de benzocyclodecane a activite antitumorale Download PDF

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Publication number
CA2471910A1
CA2471910A1 CA002471910A CA2471910A CA2471910A1 CA 2471910 A1 CA2471910 A1 CA 2471910A1 CA 002471910 A CA002471910 A CA 002471910A CA 2471910 A CA2471910 A CA 2471910A CA 2471910 A1 CA2471910 A1 CA 2471910A1
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Canada
Prior art keywords
formula
compound
methyl
group
represents hydrogen
Prior art date
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Abandoned
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CA002471910A
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English (en)
Inventor
Sylvie Ducki
Maria Menichincheri
Nicola Mongelli
Ermes Vanotti
Marina Ciomei
Mauro Angiolini
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Pfizer Italia SRL
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Individual
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Publication of CA2471910A1 publication Critical patent/CA2471910A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic 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
    • C07C45/673—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 change of size of the carbon skeleton
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Biotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un composé de benzocyclodécane de formule I, dans laquelle: ----- en positions 8-9 et 11-12 représentent indépendamment une liaison simple ou double, -R1 représente =O, ou -OR7, R7 représente H, C1-C7 alkanoyle, benzoyle, C1-C10 alkyle, C2-C10 alkényle ou COCH=CHR8, R8 représente aryle ou hétérocyclyle;-R2 et -R3 représentent H, =O ou -OR9, R9 représente H, C1-C7 alkanoyle ou benzoyle; lorsqu'en position 11-12 il y a une seule liaison, alors -R4 représente =O, =CH2, =CHCOOR10, R10 représente C1-C10 alkyle ou aryle; =CH(OCH3), -OR9; -CH2OR11, R11 représente H ou un résidu de sucre, -COR12, R12 représente H, -OH ou -OR10; ou lorsqu'ils sont en position 11-12 il y a une double liaison, alors -R4 représente -CH2OR11 ou -COR12; - R5 et -R6 représentent H ou, lorsqu'ils sont en position 8-9 il y a une liaison simple, ils forment ensemble un cycle de cyclopropane; R13 représente H ou 1-3 substituants sélectionnés parmi alkyle C1-C6, alkényle C2-C6, phényle, phényle C1-C6 alkyle, halogène, hydroxy, alkoxy C1-C6, aryloxy, cyano, nitro, amino, alkylamino C1-C10, arylamino, alkanoylamino C1-C7, aroylamino, hydroxycarbonyle, aminocarbonyle, alkylcarbonyle C1-C6, alkylaminosulfonyle C1-C6 et un groupe arylaminosulfonyle; à la condition que si R1 et R4 =O, alors un des R2, R3, R5, R6 et R13 ne représente pas un atome H; ou un sel pharmaceutiquement acceptable de celui-ci. Ces dérivés de benzocyclodécane sont dotés d'une activité antitumorale. Un procédé et de nouveaux intermédiaires pour la préparation des dérivés de benzocyclodécane, les compositions pharmaceutiques contenant lesdits dérivés, et leur utilisation dans la prévention, le contrôle et le traitement du cancer sont également décrits.
CA002471910A 2001-12-28 2002-12-18 Derives de benzocyclodecane a activite antitumorale Abandoned CA2471910A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0131034.1 2001-12-28
GBGB0131034.1A GB0131034D0 (en) 2001-12-28 2001-12-28 Benzocyclodecane derivatives with antitumor activity
PCT/EP2002/014514 WO2003055861A1 (fr) 2001-12-28 2002-12-18 Derives de benzocyclodecane a activite antitumorale

Publications (1)

Publication Number Publication Date
CA2471910A1 true CA2471910A1 (fr) 2003-07-10

Family

ID=9928451

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002471910A Abandoned CA2471910A1 (fr) 2001-12-28 2002-12-18 Derives de benzocyclodecane a activite antitumorale

Country Status (8)

Country Link
EP (1) EP1458686A1 (fr)
JP (1) JP2005520800A (fr)
AU (1) AU2002358160A1 (fr)
BR (1) BR0215463A (fr)
CA (1) CA2471910A1 (fr)
GB (1) GB0131034D0 (fr)
MX (1) MXPA04006421A (fr)
WO (1) WO2003055861A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9034861B2 (en) * 2009-10-13 2015-05-19 Allomek Therapeutics Llc MEK inhibitors useful in the treatment of diseases
CN105152895A (zh) * 2015-10-09 2015-12-16 富阳鸿祥技术服务有限公司 一种新的杂萜化合物及其制备方法和医药用途
CN105237382A (zh) * 2015-10-29 2016-01-13 淄博夸克医药技术有限公司 一种新的杂萜化合物及其制备方法和医药用途
CN105254482A (zh) * 2015-11-12 2016-01-20 庄立 一种新的杂帖类化合物及其制备方法和医药用途

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9509888D0 (en) * 1995-05-16 1995-07-12 Pharmacia Spa Terpenoidic derivatives useful as antitumour agents

Also Published As

Publication number Publication date
AU2002358160A1 (en) 2003-07-15
BR0215463A (pt) 2005-04-05
GB0131034D0 (en) 2002-02-13
WO2003055861A1 (fr) 2003-07-10
EP1458686A1 (fr) 2004-09-22
JP2005520800A (ja) 2005-07-14
MXPA04006421A (es) 2005-07-13

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