CA2611712C - Combretastatin analogs with tubulin binding activity - Google Patents

Combretastatin analogs with tubulin binding activity Download PDF

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Publication number
CA2611712C
CA2611712C CA2611712A CA2611712A CA2611712C CA 2611712 C CA2611712 C CA 2611712C CA 2611712 A CA2611712 A CA 2611712A CA 2611712 A CA2611712 A CA 2611712A CA 2611712 C CA2611712 C CA 2611712C
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CA
Canada
Prior art keywords
methoxy
trimethoxy
dihydro
group
benzocyclohepten
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2611712A
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English (en)
French (fr)
Other versions
CA2611712A1 (en
Inventor
Kevin G. Pinney
Madhavi Sriram
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Baylor University
Original Assignee
Baylor University
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Filing date
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Publication of CA2611712A1 publication Critical patent/CA2611712A1/en
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Publication of CA2611712C publication Critical patent/CA2611712C/en
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • 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
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • 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
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • 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
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Oncology (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2611712A 2005-06-14 2006-06-14 Combretastatin analogs with tubulin binding activity Active CA2611712C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US69068905P 2005-06-14 2005-06-14
US60/690,689 2005-06-14
PCT/US2006/023251 WO2006138427A2 (en) 2005-06-14 2006-06-14 Combretastatin analogs with tubulin binding activity

Publications (2)

Publication Number Publication Date
CA2611712A1 CA2611712A1 (en) 2006-12-28
CA2611712C true CA2611712C (en) 2014-05-13

Family

ID=37076178

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2611712A Active CA2611712C (en) 2005-06-14 2006-06-14 Combretastatin analogs with tubulin binding activity

Country Status (6)

Country Link
US (2) US7429681B2 (https=)
EP (1) EP1896391B1 (https=)
JP (1) JP5354775B2 (https=)
CA (1) CA2611712C (https=)
ES (1) ES2551086T3 (https=)
WO (1) WO2006138427A2 (https=)

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EP2048126A1 (de) * 2007-10-11 2009-04-15 Bayer Schering Pharma AG Benzocycloheptanderivate als selektiv wirksame Estrogene
WO2009067706A1 (en) 2007-11-21 2009-05-28 Oxigene, Inc. Method for treating hematopoietic neoplasms
WO2010132498A1 (en) * 2009-05-11 2010-11-18 Oxigene, Inc. Vascular disrupting agents for treatment of polypoidal choroidal vasculopathy
WO2011022772A1 (en) 2009-08-27 2011-03-03 Bionomics Limited Combination therapy for treating proliferative diseases
US20150018566A1 (en) 2011-08-25 2015-01-15 The Provost, Fellows, Foundation Scholars, & the Other Members of Board, of The College of the Holy Tubulin binding agents
AU2013204313C1 (en) 2012-06-01 2016-04-07 Bionomics Limited Combination Therapy
CN104817519B (zh) * 2015-05-11 2016-11-16 中国药科大学 一类ca-4的衍生物、其制法及其医药用途
US11419934B2 (en) 2015-08-18 2022-08-23 Oncotelic Therapeutics, Inc. Use of VDAS to enhance immunomodulating therapies against tumors
WO2017066668A1 (en) * 2015-10-15 2017-04-20 Baylor University Drug-linker conjugate pharmaceutical compositions
EA034994B1 (ru) * 2016-02-15 2020-04-15 Санофи 6,7-дигидро-5h-бензо[7]аннуленовые производные в качестве модуляторов эстрогеновых рецепторов
US20180002355A1 (en) * 2016-07-01 2018-01-04 Baylor University Benzocyclooctene-based and indene-based anticancer agents
ES3039455T3 (en) 2016-11-17 2025-10-21 Sanofi Sa Novel substituted n-(3-fluoropropyl)-pyrrolidine compounds, processes for their preparation and therapeutic uses thereof
EP3434272A1 (en) 2017-07-25 2019-01-30 Sanofi Combination comprising palbociclib and 6-(2,4-dichlorophenyl)-5-[4-[(3s)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7h-benzo[7]annulene-2-carboxylic acid
US10807932B2 (en) * 2018-08-17 2020-10-20 Baylor University Benzosuberene analogues and related compounds with activity as anticancer agents
BR112021003440A2 (pt) 2018-09-07 2021-05-18 Sanofi sais de 6-(2,4-diclorofenil)-5-[4-[(3s)-1-(3-fluoropropil) pirrolidin-3-il]oxifenil]-8,9-di-hidro-7h-benzo[7]anuleno-2-carboxilato de metila e seu processo de preparação
EP4037768B1 (en) 2019-10-01 2023-10-11 Sanofi Novel substituted 6,7-dihydro-5h-benzo[7]annulene compounds, processes for their preparation and therapeutic uses thereof
AU2020399168A1 (en) 2019-12-09 2022-07-28 Sanofi Crystalline form of a 7H-benzo[7]annulene-2-carboxylic acid derivative
TW202146007A (zh) 2020-02-27 2021-12-16 法商賽諾菲公司 包含阿培利司（ａｌｐｅｌｉｓｉｂ）與６－（２，４－二氯苯基）－５－［４－［（３ｓ）－１－（３－氟丙基）吡咯啶－３－基］氧苯基］－８，９－二氫－７ｈ－苯并［７］輪烯－２－羧酸之組合
TW202233572A (zh) 2020-10-19 2022-09-01 法商賽諾菲公司 新穎之經取代的6,7-二氫-5h-苯並[7]輪烯衍生物，其製備方法及其治療用途
WO2022084280A1 (en) 2020-10-19 2022-04-28 Sanofi Substituted 6,7-dihydro-5h-benzo[7]annulene compounds and their derivatives, processes for their preparation and therapeutic uses thereof

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US2493730A (en) * 1946-10-23 1950-01-03 Hoffmann La Roche 2-(p-oxyphenyl)-3-isopropyl-6-oxyindanes
US3859358A (en) * 1967-12-20 1975-01-07 Standard Oil Co Ohio Process for the oxidation of olefins to unsaturated aldehydes
US3813430A (en) * 1970-10-26 1974-05-28 Sterling Drug Inc 1-aryl-2-alkyl or-alkenyl-3,4-dihydronaphthalenes
US3859356A (en) 1972-07-24 1975-01-07 Sandoz Ag Benzylidene substituted bicyclic and tricyclic compounds
FR2320734A1 (fr) 1975-08-14 1977-03-11 Roussel Uclaf Nouveaux derives de l'aminomethyl benzocycloheptene et leurs sels, procede de preparation et application a titre de medicaments de ces produits
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Also Published As

Publication number Publication date
ES2551086T3 (es) 2015-11-16
US20060293394A1 (en) 2006-12-28
WO2006138427A2 (en) 2006-12-28
JP2008546706A (ja) 2008-12-25
WO2006138427A3 (en) 2007-06-28
EP1896391B1 (en) 2015-08-12
CA2611712A1 (en) 2006-12-28
US20090075943A1 (en) 2009-03-19
EP1896391A2 (en) 2008-03-12
JP5354775B2 (ja) 2013-11-27
US7429681B2 (en) 2008-09-30
US8394859B2 (en) 2013-03-12

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EEER Examination request
H11 Ip right ceased following rejected request for revival

Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED

Effective date: 20241216