CA2406212C - Substituted styryl benzylsulfones for treating proliferative disorders - Google Patents

Substituted styryl benzylsulfones for treating proliferative disorders Download PDF

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Publication number
CA2406212C
CA2406212C CA2406212A CA2406212A CA2406212C CA 2406212 C CA2406212 C CA 2406212C CA 2406212 A CA2406212 A CA 2406212A CA 2406212 A CA2406212 A CA 2406212A CA 2406212 C CA2406212 C CA 2406212C
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CA
Canada
Prior art keywords
alkoxy
compound according
halogen
hydrogen
group
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
CA2406212A
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English (en)
French (fr)
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CA2406212A1 (en
Inventor
E. Premkumar Reddy
M. V. Ramana Reddy
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Temple Univ School of Medicine
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Temple Univ School of Medicine
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Publication of CA2406212A1 publication Critical patent/CA2406212A1/en
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Publication of CA2406212C publication Critical patent/CA2406212C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Reproductive Health (AREA)
  • Molecular Biology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Biomedical Technology (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2406212A 2000-04-14 2001-04-13 Substituted styryl benzylsulfones for treating proliferative disorders Expired - Lifetime CA2406212C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US19784900P 2000-04-14 2000-04-14
US60/197,849 2000-04-14
US23470700P 2000-09-22 2000-09-22
US60/234,707 2000-09-22
US27164001P 2001-02-27 2001-02-27
US60/271,640 2001-02-27
PCT/US2001/012134 WO2001078712A1 (en) 2000-04-14 2001-04-13 Substituted styryl benzylsulfones for treating proliferative disorders

Publications (2)

Publication Number Publication Date
CA2406212A1 CA2406212A1 (en) 2001-10-25
CA2406212C true CA2406212C (en) 2011-02-01

Family

ID=27393791

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2406212A Expired - Lifetime CA2406212C (en) 2000-04-14 2001-04-13 Substituted styryl benzylsulfones for treating proliferative disorders

Country Status (13)

Country Link
US (2) US6486210B2 (enExample)
EP (2) EP1305015B1 (enExample)
JP (1) JP4677162B2 (enExample)
KR (1) KR100768415B1 (enExample)
AU (2) AU2001251615C1 (enExample)
CA (1) CA2406212C (enExample)
DK (1) DK1305015T3 (enExample)
ES (1) ES2427088T3 (enExample)
IL (2) IL152190A0 (enExample)
NZ (1) NZ522551A (enExample)
PT (1) PT1305015E (enExample)
SI (1) SI1305015T1 (enExample)
WO (1) WO2001078712A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6762207B1 (en) * 1999-04-02 2004-07-13 Temple University - Of The Commonwealth System Of Higher Education (E)-styryl sulfone anticancer agents
CA2424884C (en) 2000-10-05 2009-12-15 E. Premkumar Reddy Substituted (e)-styryl benzylsulfones for treating proliferative disorders
US6833480B2 (en) * 2001-02-27 2004-12-21 Temple University - Of The Commonwealth System Of Higher Education (Z)-styrylbenzylsulfones and pharmaceutical uses thereof
ATE406881T1 (de) 2001-02-28 2008-09-15 Univ Temple Verwendung von alpha, beta ungesättigten arylsulfonen zum schutz von zellen und geweben vor toxizität ionischer strahlung
MXPA04008356A (es) * 2002-02-28 2005-09-12 Univ Temple (e)-2,6-dialcoxiestiril bencilsulfonas sustituidas con un grupo amino y en la posicion 4 para tratar trastornos poliferativos.
ATE517626T1 (de) * 2002-02-28 2011-08-15 Univ Temple Aminosubstituierte sulphonanilide und ihre derivate zur behandlung von proliferativen erkrankungen
JP4182844B2 (ja) * 2003-09-03 2008-11-19 株式会社島津製作所 質量分析装置
HUE032523T2 (en) * 2003-11-14 2017-09-28 Temple Univ - Of The Commonwealth System Of Higher Education Alpha, beta-unsaturated sulfoxides for the treatment of proliferative disorders
ES2609084T3 (es) * 2004-03-16 2017-04-18 Temple University - Of The Commonwealth System Of Higher Education Derivados de fenoxi y feniltio sustituidos para tratar trastornos proliferativos
CA2577309C (en) 2004-06-24 2013-10-22 Temple University - Of The Commonwealth System Of Higher Education Alpha, beta-unsaturated sulfones, sulfoxides, sulfonimides, sulfinimides, acylsulfonamides and acylsulfinamides and therapeutic uses thereof
AU2006204103B2 (en) * 2005-01-05 2011-11-24 Temple University Of The Commonwealth System Of Higher Education Treatment of drug-resistant proliferative disorders
PT1896401E (pt) * 2005-02-25 2013-07-17 Univ Temple Síntese de sulfuretos, sulfonas, sulfóxidos e sulfonamidas não saturados
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
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
US8273787B2 (en) * 2006-09-15 2012-09-25 Onconova Therapeutics, Inc Activated cytotoxic compounds for attachment to targeting molecules for the treatment of mammalian disease conditions
US8735620B2 (en) * 2008-12-17 2014-05-27 Epr Pharmaceuticals Pvt. Ltd Processes for preparing (E)-styrylbenzylsulfone compounds and uses thereof for treating proliferative disorders
US10207989B2 (en) 2012-09-20 2019-02-19 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
WO2024186641A1 (en) * 2023-03-03 2024-09-12 Onconova Therapeutics, Inc. Methods and compositions for treating cancer

Family Cites Families (19)

* 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
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
YU213587A (en) * 1986-11-28 1989-06-30 Orion Yhtymae Oy Process for obtaining new pharmacologic active cateholic derivatives
FR2621038B1 (fr) * 1987-09-28 1989-12-29 Rhone Poulenc Sante Derives d'alcadienes, leurs preparations, les medicaments les contenant et produits intermediaires
GB8902409D0 (en) * 1989-02-03 1989-03-22 Ici Plc Aliphatic compounds
US5659087A (en) 1995-06-07 1997-08-19 Eli Lilly And Company Diarylvinyl sulfoxides
JP3660395B2 (ja) * 1995-06-22 2005-06-15 大鵬薬品工業株式会社 フェニルスルホン誘導体及びその製造方法
CZ290756B6 (cs) * 1995-10-19 2002-10-16 Ciba Specialty Chemicals Holding Inc. Substituované fenoly působící jako antioxidanty, kompozice, které je obsahují, a jejich pouľití
ATE284386T1 (de) 1997-10-03 2004-12-15 Univ Temple Styrolsulfone als antikrebsmittel
US6201154B1 (en) * 1999-03-31 2001-03-13 Temple University-Of The Commonwealth Of Higher Education Z-styryl sulfone anticancer agents
JP2002541101A (ja) * 1999-04-02 2002-12-03 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 スチリルスルホン抗癌剤
CA2366750C (en) * 1999-04-02 2010-06-01 Temple University - Of The Commonwealth System Of Higher Education (e)-styryl sulfone anticancer agents
AU780844B2 (en) * 1999-10-12 2005-04-21 Temple University-Of The Commonwealth System Of Higher Education Method for protecting normal cells from cytotoxicity of chemotherapeutic agents

Also Published As

Publication number Publication date
DK1305015T3 (da) 2013-08-26
IL152190A0 (en) 2003-05-29
US20030036536A1 (en) 2003-02-20
AU2001251615C1 (en) 2006-12-07
KR20030029044A (ko) 2003-04-11
AU2001251615B2 (en) 2005-08-11
WO2001078712A1 (en) 2001-10-25
US6642410B2 (en) 2003-11-04
EP2359819A1 (en) 2011-08-24
CA2406212A1 (en) 2001-10-25
EP1305015A1 (en) 2003-05-02
SI1305015T1 (sl) 2013-08-30
IL152190A (en) 2010-11-30
AU5161501A (en) 2001-10-30
EP1305015A4 (en) 2003-05-21
PT1305015E (pt) 2013-09-06
EP1305015B1 (en) 2013-06-12
JP2003530433A (ja) 2003-10-14
US6486210B2 (en) 2002-11-26
JP4677162B2 (ja) 2011-04-27
ES2427088T3 (es) 2013-10-28
KR100768415B1 (ko) 2007-10-18
NZ522551A (en) 2004-03-26
US20020115643A1 (en) 2002-08-22

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AU2001251615A1 (en) Substituted styryl benzylsulfones for treating proliferative disorders
CA2368653C (en) Z-styryl sulfone anticancer agents
US6787667B2 (en) (E)-styryl sulfone anticancer agents
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CA2424884C (en) Substituted (e)-styryl benzylsulfones for treating proliferative disorders
WO2002067913A8 (en) (z)-styrylbenzylsulfones and pharmaceutical uses thereof

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