CA2424884C - Substituted (e)-styryl benzylsulfones for treating proliferative disorders - Google Patents

Substituted (e)-styryl benzylsulfones for treating proliferative disorders Download PDF

Info

Publication number
CA2424884C
CA2424884C CA002424884A CA2424884A CA2424884C CA 2424884 C CA2424884 C CA 2424884C CA 002424884 A CA002424884 A CA 002424884A CA 2424884 A CA2424884 A CA 2424884A CA 2424884 C CA2424884 C CA 2424884C
Authority
CA
Canada
Prior art keywords
alkoxy
group
amino
halogen
pharmaceutically acceptable
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.)
Expired - Fee Related
Application number
CA002424884A
Other languages
English (en)
French (fr)
Other versions
CA2424884A1 (en
Inventor
E. Premkumar Reddy
M. V. Ramana Reddy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Temple Univ School of Medicine
Original Assignee
Temple Univ School of Medicine
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 Temple Univ School of Medicine filed Critical Temple Univ School of Medicine
Publication of CA2424884A1 publication Critical patent/CA2424884A1/en
Application granted granted Critical
Publication of CA2424884C publication Critical patent/CA2424884C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/095Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10Sulfides; Sulfoxides; Sulfones
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/02Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/10Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/26Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Transplantation (AREA)
  • Urology & Nephrology (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)
CA002424884A 2000-10-05 2001-10-05 Substituted (e)-styryl benzylsulfones for treating proliferative disorders Expired - Fee Related CA2424884C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US23822200P 2000-10-05 2000-10-05
US60/238,222 2000-10-05
PCT/US2001/031337 WO2002028828A1 (en) 2000-10-05 2001-10-05 Substituted (e)-styryl benzylsulfones for treating proliferative disorders

Publications (2)

Publication Number Publication Date
CA2424884A1 CA2424884A1 (en) 2002-04-11
CA2424884C true CA2424884C (en) 2009-12-15

Family

ID=22896982

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002424884A Expired - Fee Related CA2424884C (en) 2000-10-05 2001-10-05 Substituted (e)-styryl benzylsulfones for treating proliferative disorders

Country Status (8)

Country Link
US (1) US7053123B2 (https=)
EP (1) EP1328511B1 (https=)
JP (1) JP2004510761A (https=)
AT (1) ATE461915T1 (https=)
AU (1) AU2001296677A1 (https=)
CA (1) CA2424884C (https=)
DE (1) DE60141641D1 (https=)
WO (1) WO2002028828A1 (https=)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548553B2 (en) * 1997-10-03 2003-04-15 Temple University-Of The Commonwealth System Of Higher Education Styryl sulfone anticancer agents
US6767926B1 (en) * 1999-10-12 2004-07-27 Temple University - Of The Commonwealth System Of Higher Education Method for protecting normal cells from cytotoxicity of chemotherapeutic agents
EP1534284B1 (en) * 2002-02-28 2011-07-27 Temple University - Of The Commonwealth System of Higher Education Amino-substituted sulfonanilides and derivatives thereof for treating proliferative disorders
NZ535232A (en) * 2002-02-28 2007-05-31 Univ Temple Amino-substituted (E)-2,6-dialkoxystyryl 4-substituted benzylsulfones for treating proliferative disorders
WO2005046599A2 (en) * 2003-11-14 2005-05-26 Temple University - Of The Commonwealth System Of Higher Education Alpha, beta-unsaturated sulfoxides for treating proliferative disorders
NZ549962A (en) 2004-03-16 2010-04-30 Univ Temple Substituted phenoxy-and phenylthio-derivatives for treating proliferative disorders
US8058313B2 (en) 2004-06-24 2011-11-15 Temple University—Of the Commonwealth System of Higher Education Alpha, beta-unsaturated sulfones, sulfoxides, sulfonimides, sulfinimides, acylsulfonamides and acylsulfinamides and therapeutic uses thereof
JP5278968B2 (ja) 2006-08-30 2013-09-04 テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション 骨髄異形性症候群及び急性骨髄性白血病の治療のための組成物及び方法
AU2013318206B2 (en) 2012-09-20 2018-07-26 Temple University - Of The Commonwealth System Of Higher Education Substituted alkyl diaryl derivatives, methods of preparation and uses
WO2014089483A1 (en) 2012-12-07 2014-06-12 Onconova Therapeutics, Inc. Methods and compositions for treatment of cancer
US10383831B2 (en) 2015-08-03 2019-08-20 Temple University—Of the Commonwealth System of Higher Education 2,4,6-trialkoxystryl aryl sulfones, sulfonamides and carboxamides, and methods of preparation and use

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2532612A (en) 1945-08-29 1950-12-05 Union Oil Co Preparation of unsaturated thio-ethers
US3185743A (en) 1960-08-24 1965-05-25 Union Carbide Corp Production of olefinic compounds from allyl sulfones
US3463774A (en) 1963-03-18 1969-08-26 Hoffmann La Roche Novel 4,1-benzothiazepin-2-(1h)-ones and 4,1-benzothiazepines
US3418101A (en) 1965-12-15 1968-12-24 Pennsalt Chemicals Corp Process for plant desiccation
US3514386A (en) 1967-12-11 1970-05-26 Exxon Research Engineering Co Stereoselective addition of thiols to acetylenic compounds
US3917714A (en) 1972-09-06 1975-11-04 American Cyanamid Co Bis(alkylsulfonyl)vinylbenzenes
US4161407A (en) 1977-10-06 1979-07-17 Eastman Kodak Company Crosslinkable polymers having vinylsulfonyl groups or styrylsulfonyl groups and their use as hardeners for gelatin
US4386221A (en) 1981-10-28 1983-05-31 Eastman Kodak Company Process for the preparation of aryl alkyl sulfones and aryl vinyl sulfones
US4937388A (en) 1985-08-09 1990-06-26 Imperial Chemical Industries Plc Insecticidal ethers
US5659087A (en) 1995-06-07 1997-08-19 Eli Lilly And Company Diarylvinyl sulfoxides
US5733909A (en) 1996-02-01 1998-03-31 Merck Frosst Canada, Inc. Diphenyl stilbenes as prodrugs to COX-2 inhibitors
US6030961A (en) * 1997-03-11 2000-02-29 Bar-Ilan Research & Development Co., Ltd. Oxyalkylene phosphate compounds and uses thereof
CN1163480C (zh) 1997-10-03 2004-08-25 坦普尔大学 苯乙烯砜抗癌剂
US6548553B2 (en) 1997-10-03 2003-04-15 Temple University-Of The Commonwealth System Of Higher Education Styryl sulfone anticancer agents
US6201154B1 (en) 1999-03-31 2001-03-13 Temple University-Of The Commonwealth Of Higher Education Z-styryl sulfone anticancer agents
US6762207B1 (en) * 1999-04-02 2004-07-13 Temple University - Of The Commonwealth System Of Higher Education (E)-styryl sulfone anticancer agents
US6418101B1 (en) * 1999-09-03 2002-07-09 Zen Research (Ireland), Ltd. Digital read channel for optical disk reader
US6767926B1 (en) * 1999-10-12 2004-07-27 Temple University - Of The Commonwealth System Of Higher Education Method for protecting normal cells from cytotoxicity of chemotherapeutic agents
WO2001026645A1 (en) 1999-10-12 2001-04-19 Temple University-Of The Commonwealth System Of Higher Education Method for protecting normal cells from cytotoxicity of chemotherapeutic agents
US6486210B2 (en) 2000-04-14 2002-11-26 Temple University—Of the Commonwealth System of Higher Education Substituted styryl benzylsulfones for treating proliferative disorders
US6541475B2 (en) * 2000-04-14 2003-04-01 Temple University - Of The Commonwealth System Of Higher Education α, β-unsaturated sulfones for treating proliferative disorders
WO2002069892A2 (en) 2001-02-28 2002-09-12 Temple University Of The Commonwealth System Of Higher Education METHOD FOR PROTECTING CELLS AND TISSUES FROM IONIZING RADIATION TOXICITY WITH α, β UNSATURATED ARYL SULFONES

Also Published As

Publication number Publication date
WO2002028828A1 (en) 2002-04-11
EP1328511A1 (en) 2003-07-23
DE60141641D1 (de) 2010-05-06
US7053123B2 (en) 2006-05-30
EP1328511A4 (en) 2005-11-30
US20050101528A1 (en) 2005-05-12
JP2004510761A (ja) 2004-04-08
AU2001296677A1 (en) 2002-04-15
EP1328511B1 (en) 2010-03-24
ATE461915T1 (de) 2010-04-15
CA2424884A1 (en) 2002-04-11

Similar Documents

Publication Publication Date Title
US6486210B2 (en) Substituted styryl benzylsulfones for treating proliferative disorders
AU2001251615A1 (en) Substituted styryl benzylsulfones for treating proliferative disorders
US6762207B1 (en) (E)-styryl sulfone anticancer agents
CA2424884C (en) Substituted (e)-styryl benzylsulfones for treating proliferative disorders
JP4468593B2 (ja) Z−スチリルスルホン抗癌剤
EP1173160B1 (en) (e)-styryl sulfone anticancer agents
US6833480B2 (en) (Z)-styrylbenzylsulfones and pharmaceutical uses thereof

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20181005