CA2546495C - Alpha, beta-unsaturated sulfoxides for treating proliferative disorders - Google Patents

Alpha, beta-unsaturated sulfoxides for treating proliferative disorders Download PDF

Info

Publication number
CA2546495C
CA2546495C CA2546495A CA2546495A CA2546495C CA 2546495 C CA2546495 C CA 2546495C CA 2546495 A CA2546495 A CA 2546495A CA 2546495 A CA2546495 A CA 2546495A CA 2546495 C CA2546495 C CA 2546495C
Authority
CA
Canada
Prior art keywords
methyl
sulfinyl
ethene
methoxyphenyl
fluorophenyl
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 - Lifetime
Application number
CA2546495A
Other languages
English (en)
French (fr)
Other versions
CA2546495A1 (en
Inventor
Premkumar E. Reddy
Ramana M. V. Reddy
Stanley C. Bell
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 University
Traws Pharma Inc
Original Assignee
Onconova Therapeutics Inc
Temple University
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 Onconova Therapeutics Inc, Temple University filed Critical Onconova Therapeutics Inc
Publication of CA2546495A1 publication Critical patent/CA2546495A1/en
Application granted granted Critical
Publication of CA2546495C publication Critical patent/CA2546495C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10—Sulfides; Sulfoxides; Sulfones
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/06—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/02—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms
    • C07C317/10—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; 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
    • 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
    • C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • 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
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C07D213/34—Sulfur atoms to which a second hetero atom is attached
    • 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
    • C07D277/26—Radicals substituted by 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
    • C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Vascular Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Steroid Compounds (AREA)
CA2546495A 2003-11-14 2004-11-08 Alpha, beta-unsaturated sulfoxides for treating proliferative disorders Expired - Lifetime CA2546495C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US52052303P 2003-11-14 2003-11-14
US60/520,523 2003-11-14
PCT/US2004/037293 WO2005046599A2 (en) 2003-11-14 2004-11-08 Alpha, beta-unsaturated sulfoxides for treating proliferative disorders

Publications (2)

Publication Number Publication Date
CA2546495A1 CA2546495A1 (en) 2005-05-26
CA2546495C true CA2546495C (en) 2012-10-09

Family

ID=34590471

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2546495A Expired - Lifetime CA2546495C (en) 2003-11-14 2004-11-08 Alpha, beta-unsaturated sulfoxides for treating proliferative disorders

Country Status (12)

Country Link
US (1) US7744889B2 (enExample)
EP (1) EP1689706B1 (enExample)
JP (1) JP5196787B2 (enExample)
KR (1) KR20060109871A (enExample)
AU (1) AU2004289281C1 (enExample)
CA (1) CA2546495C (enExample)
DK (1) DK1689706T3 (enExample)
ES (1) ES2621802T3 (enExample)
HU (1) HUE032523T2 (enExample)
IL (1) IL174426A (enExample)
NZ (1) NZ545995A (enExample)
WO (1) WO2005046599A2 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005222947B2 (en) * 2004-03-16 2010-12-23 Onconova Therapeutics Inc. Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders
US20090306207A1 (en) * 2005-01-05 2009-12-10 Reddy M V Ramana Treatment of Drug-Resistant Proliferative Disorders
WO2006104668A2 (en) * 2005-03-11 2006-10-05 Temple University - Of The Commonwealth System Of Higher Education Composition and methods for the treatment of proliferative diseases
WO2007005670A2 (en) * 2005-06-30 2007-01-11 The Research Foundation Of The State University Of New York Natural and synthetic sulfoxide, selenone and selenoxide analogs and polymer conjugated forms thereof for the modulation of angiogenesis
JP5734869B2 (ja) * 2008-12-16 2015-06-17 オンコノバ・セラピューティックス・インコーポレーテッド ヒトにおける細胞毒性物質の有害作用に対する治療レジメンの有効性を決定する方法
GB201010359D0 (en) 2010-06-21 2010-08-04 Univ Nottingham Compounds for treating proliferative disorders
EP2486923B1 (en) * 2011-02-11 2015-09-09 Dr. Felix Jäger und Dr. Stefan Drinkuth Laborgemeinschaft OHG Histone deacetylase (HDAC) inhibiting compounds and method of making same
CA2885217C (en) 2012-09-20 2019-10-08 Temple University - Of The Commonwealth System Of Higher Education Substituted alkyl diaryl derivatives, methods of preparation and uses
SG11201509194SA (en) * 2013-05-07 2015-12-30 Univ California Radiomitigating pharmaceutical formulations
CN104892471B (zh) * 2015-05-15 2020-03-27 中国人民解放军军事医学科学院放射与辐射医学研究所 具有蛋白酪氨酸激酶抑制活性的物质、其制备方法及用途
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
CN106432011B (zh) * 2016-09-18 2018-11-02 中国医学科学院放射医学研究所 一类具有辐射防护作用的新化合物、其制备方法及其药物应用

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3865867A (en) * 1967-06-19 1975-02-11 Monsanto Co Meta-bifunctional benzenes
US3975435A (en) * 1974-03-06 1976-08-17 Givaudan Corporation Substituted cinnamanilides
DK586175A (da) * 1974-12-28 1976-06-29 Asahi Chemical Ind Cephalosporin-forbindelser
JPH05262733A (ja) * 1992-03-23 1993-10-12 Sapporo Breweries Ltd 含硫黄化合物，その製造法及びそれを有効成分とする抗潰瘍剤
US5523302A (en) * 1993-11-24 1996-06-04 The Du Pont Merck Pharmaceutical Company Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists
EA200800375A1 (ru) * 1997-05-14 2008-06-30 Атеродженикс, Инк. Соединения и способы ингибирования экспрессии vcam-1
ATE284386T1 (de) * 1997-10-03 2004-12-15 Univ Temple Styrolsulfone als antikrebsmittel
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
WO2000059495A1 (en) * 1999-04-02 2000-10-12 Temple University - Of The Commonwealth System Of Higher Education (e)-styryl sulfone anticancer agents
WO2000059494A1 (en) * 1999-04-02 2000-10-12 Temple University- Of The Commonwealth System Of Higher Education 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
US6117364A (en) * 1999-05-27 2000-09-12 Nalco/Exxon Energy Chemicals, L.P. Acid corrosion inhibitor
CA2375511A1 (en) * 1999-06-16 2000-12-21 Temple University - Of The Commonwealth System Of Higher Education (z)-styryl acetoxyphenyl sulfides as cyclooxygenase inhibitors
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
IL149064A0 (en) * 1999-10-12 2002-11-10 Univ Temple Method for protecting normal cells from cytotoxicity of chemotherapeutic agents
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
US6486210B2 (en) * 2000-04-14 2002-11-26 Temple University—Of the Commonwealth System of Higher Education Substituted styryl benzylsulfones for treating proliferative disorders
CA2424884C (en) * 2000-10-05 2009-12-15 E. Premkumar Reddy Substituted (e)-styryl benzylsulfones for treating proliferative disorders
CN1401055A (zh) * 2000-10-12 2003-03-05 雅马哈发动机株式会社 气体燃料混合器
WO2002067913A1 (en) * 2001-02-27 2002-09-06 Temple University-Of The Commonwealth System Of Higher Education (z)-styrylbenzylsulfones and pharmaceutical uses thereof
US6667346B2 (en) * 2001-02-28 2003-12-23 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
DK1379508T3 (da) * 2001-02-28 2011-01-03 Univ Temple N-(aryl)-2arylethensulfonamider og terapeutiske anvendelser deraf
NZ535232A (en) * 2002-02-28 2007-05-31 Univ Temple Amino-substituted (E)-2,6-dialkoxystyryl 4-substituted benzylsulfones for treating proliferative disorders
AU2005222947B2 (en) * 2004-03-16 2010-12-23 Onconova Therapeutics Inc. Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders
WO2006104668A2 (en) * 2005-03-11 2006-10-05 Temple University - Of The Commonwealth System Of Higher Education Composition and methods for the treatment of proliferative diseases

Also Published As

Publication number Publication date
IL174426A0 (en) 2006-08-01
DK1689706T3 (da) 2017-04-03
JP2007513877A (ja) 2007-05-31
US20060280746A1 (en) 2006-12-14
ES2621802T3 (es) 2017-07-05
EP1689706A2 (en) 2006-08-16
AU2004289281C1 (en) 2011-12-08
IL174426A (en) 2012-01-31
HUE032523T2 (en) 2017-09-28
CA2546495A1 (en) 2005-05-26
AU2004289281A1 (en) 2005-05-26
EP1689706B1 (en) 2017-01-11
WO2005046599A3 (en) 2005-10-06
KR20060109871A (ko) 2006-10-23
EP1689706A4 (en) 2007-11-14
US7744889B2 (en) 2010-06-29
NZ545995A (en) 2009-04-30
JP5196787B2 (ja) 2013-05-15
AU2004289281B2 (en) 2011-05-26
WO2005046599A2 (en) 2005-05-26

Similar Documents

Publication Publication Date Title
AU2011201245B2 (en) Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders
KR101063462B1 (ko) 아릴 및 헤테로아릴 프로펜 아미드, 이들의 유도체 및 이의치료학적 용도
WO2008076270A2 (en) Sulfide, sulfoxide and sulfone chalcone analogues, derivatives thereof and therapeutic uses thereof
AU2004289281C1 (en) Alpha, beta-Unsaturated sulfoxides for treating proliferative disorders
US20020165412A1 (en) N-(aryl)-2-arylethenesulfonamides and therapeutic uses thereof
RS37603A (sr) Orto, meta-supstituisana bis-aril jedinjenja, postupak za njihovu proizvodnju, njihova primena u svojstvu leka i farmaceutski preparati koji sadrže ta jedinjenja
US8735620B2 (en) Processes for preparing (E)-styrylbenzylsulfone compounds and uses thereof for treating proliferative disorders
CA2646874C (en) Processes for preparing (e)-styrylbenzylsulfone compounds and uses thereof for treating proliferative disorders
NZ583093A (en) Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders
MXPA06010624A (en) Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders

Legal Events

Date Code Title Description
EEER Examination request