CA2535185C - 2-methylene-19-nor-vitamin d2 compounds - Google Patents

2-methylene-19-nor-vitamin d2 compounds Download PDF

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Publication number
CA2535185C
CA2535185C CA2535185A CA2535185A CA2535185C CA 2535185 C CA2535185 C CA 2535185C CA 2535185 A CA2535185 A CA 2535185A CA 2535185 A CA2535185 A CA 2535185A CA 2535185 C CA2535185 C CA 2535185C
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CA
Canada
Prior art keywords
compound
formula
pharmaceutically acceptable
mixture
acceptable salt
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
CA2535185A
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English (en)
French (fr)
Other versions
CA2535185A1 (en
Inventor
Hector F. Deluca
Rafal R. Sicinski
Sumithra Gowlugari
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.)
Wisconsin Alumni Research Foundation
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Wisconsin Alumni Research Foundation
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Publication date
Application filed by Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation
Publication of CA2535185A1 publication Critical patent/CA2535185A1/en
Application granted granted Critical
Publication of CA2535185C publication Critical patent/CA2535185C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • 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
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Emergency Medicine (AREA)
  • Rheumatology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2535185A 2003-08-20 2004-08-18 2-methylene-19-nor-vitamin d2 compounds Expired - Fee Related CA2535185C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US49641503P 2003-08-20 2003-08-20
US60/496,415 2003-08-20
PCT/US2004/026925 WO2005018658A1 (en) 2003-08-20 2004-08-18 2-methylene-19-nor-vitamin d2 compounds

Publications (2)

Publication Number Publication Date
CA2535185A1 CA2535185A1 (en) 2005-03-03
CA2535185C true CA2535185C (en) 2013-04-23

Family

ID=34215997

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2535185A Expired - Fee Related CA2535185C (en) 2003-08-20 2004-08-18 2-methylene-19-nor-vitamin d2 compounds

Country Status (8)

Country Link
US (1) US7232810B2 (enExample)
EP (1) EP1656157B1 (enExample)
JP (1) JP5009617B2 (enExample)
AT (1) ATE537834T1 (enExample)
AU (1) AU2004266706B2 (enExample)
CA (1) CA2535185C (enExample)
NZ (1) NZ545862A (enExample)
WO (1) WO2005018658A1 (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2544502A1 (en) * 2003-11-25 2005-06-09 Wisconsin Alumni Research Foundation Vitamin d analogs for obesity prevention and treatment
US8404667B2 (en) 2006-12-29 2013-03-26 Wisconsin Alumni Research Foundation Compounds, compositions, kits and methods of use to orally and topically treat acne and other skin conditions by 19-Nor vitamin D analog
WO2005079464A2 (en) * 2004-02-17 2005-09-01 Wisconsin Alumni Research Foundation Vitamin d receptor antagonists and their use in treating asthma
US7713951B2 (en) * 2004-04-09 2010-05-11 Wisconsin Alumni Research Foundation 2-alkylidene-18,19-dinor-vitamin D compounds
ATE499942T1 (de) * 2004-11-22 2011-03-15 Wisconsin Alumni Res Found 2-methylen-19,21-dinor-1alpha-hydroxy- bishomopregnacalciferol
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,25-dihydroxyvitamin-d2
EP1848442B1 (en) * 2005-02-11 2012-04-25 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24epi)-1alpha,25-dihydroxyvitamine-d2
US8193170B2 (en) * 2008-07-10 2012-06-05 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20R,22E,25R)-vitamin D analogs
US7888339B2 (en) 2008-07-10 2011-02-15 Wisconsin Alumni Research Foundation 2-methylene-20(21)-dehydro-19-nor-vitamin D analogs
US8399439B2 (en) * 2008-07-10 2013-03-19 Wisconsin Alumni Research Foundation 2-methylene-19,26-dinor-(20S,22E,25R)-vitamin D analogs
US8222236B2 (en) * 2008-07-10 2012-07-17 Wisconsin Alumni Research Foundation 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs
PL216135B1 (pl) * 2009-08-07 2014-03-31 Inst Farmaceutyczny Nowe syntony i ich zastosowanie do otrzymywania pochodnych 19-nor witamin D
MX2012003883A (es) * 2009-10-02 2012-06-27 Wisconsin Alumni Res Found Analogos de (20s,22e)-2-metileno-19-nor-22-ene-1a,25-dihidroxovita mina d3.
JP5931845B2 (ja) * 2010-03-23 2016-06-08 ウイスコンシン アラムニ リサーチ ファンデーション 2−メチレン−19−ノル−22−メチル−1α,25−ジヒドロキシビタミンD3のジアステレオマー
US8664206B2 (en) 2010-03-23 2014-03-04 Wisconsin Alumni Research Foundation Diastereomers of 2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D3
WO2011119610A2 (en) * 2010-03-23 2011-09-29 Wisconsin Alumni Research Foundation (20S)-2-METHYLENE-19-NOR-22-DIMETHYL-1α,25- DIHYDROXYVITAMIN D3 AND (20R)-2-METHYLENE-19-NOR-22- DIMETHYL-1α,25-HYDROXYVITAMIN D3
WO2012166938A2 (en) 2011-06-03 2012-12-06 Wisconsin Alumni Research Foundation (22e)-2-methylene-26,27-cyclo-22-dehydro-1alpha-hydroxy-19-norvitamin d3 derivatives
US8993547B2 (en) * 2011-06-14 2015-03-31 Wisconsin Alumni Research Foundation 3-desoxy-2-methylene-19-nor-vitamin D analogs and their uses
US9416102B2 (en) * 2013-01-23 2016-08-16 Wisconsin Alumni Research Foundation (22E)-2-methylene-22-dehydro-1α,24,25-trihydroxy-19-nor-vitamin D3 analogs

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5036061A (en) * 1983-05-09 1991-07-30 Deluca Hector F Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds
US4769181A (en) * 1983-11-07 1988-09-06 Wisconsin Alumni Research Foundation 1,25-dihydroxyvitamin D2 compounds
US4588716A (en) * 1984-05-04 1986-05-13 Wisconsin Alumni Research Foundation Method for treating metabolic bone disease in mammals
US4666634A (en) * 1984-12-05 1987-05-19 Chugai Seiyaku Kabushiki Kaisha vitamin D3 derivatives having a substituent at 2-position
DE3639488A1 (de) * 1986-11-18 1988-05-19 Basf Lacke & Farben Kathodisch abscheidbare wasserverduennbare bindemittel, wasserverduennbare ueberzugszusammensetzungen und verfahren zur herstellung von kathodisch abscheidbaren wasserverduennbaren bindemitteln
US4973584A (en) * 1989-03-09 1990-11-27 Deluca Hector F Novel 1α-hydroxyvitamin D2 epimer and derivatives
JP2818493B2 (ja) * 1990-02-14 1998-10-30 ウイスコンシン アラムナイ リサーチ フオンデーシヨン 25−ヒドロキシビタミンD2 化合物および対応する1α−ヒドロキシル化誘導体の製造方法
US5086191A (en) 1991-05-28 1992-02-04 Wisconsin Alumni Research Foundation Intermediates for the synthesis of 19-nor vitamin D compounds
JP2898882B2 (ja) * 1993-04-05 1999-06-02 ウイスコンシン アラムナイ リサーチ フオンデーシヨン 2−位に置換基を有する19−ノル−ビタミンd3 化合物
US5843928A (en) * 1997-03-17 1998-12-01 Wisconsin Alumni Research Foundation 2-alkylidene-19-nor-vitamin D compounds
US6392071B1 (en) * 1997-03-17 2002-05-21 Wisconsin Alumni: Research Foundation 26,27-homologated-20-EPI-2-alkylidene-19-nor-vitamin D compounds
US5945410A (en) * 1997-03-17 1999-08-31 Wisconsin Alumni Research Foundation 2-alkyl-19-nor-vitamin D compounds
US6316642B1 (en) * 1997-03-17 2001-11-13 Wisconsin Alumni Research Foundation 26,27-Homologated-20-EPI-2alkyl-19-nor-vitamin D compounds
US6673782B2 (en) * 1999-04-29 2004-01-06 Wisconsin Alumni Research Foundation Treatment of systemic lupus erythematosis
US6479474B2 (en) * 1999-07-08 2002-11-12 Wisconsin Alumni Research Foundation Dietary calcium as a supplement to vitamin D compound treatment of multiple sclerosis
ES2309069T3 (es) * 2000-05-31 2008-12-16 Wisconsin Alumni Research Foundation Compuestos de 2-etil y 2-etiliden-19-nor-vitamina d.
BR0113703A (pt) * 2000-09-08 2003-07-22 Wisconsin Alumni Researcg Foun Compostos e métodos de tratamento de psorìase, leucemia, câncer do cólon, do seio ou da próstata, osteodistrofia renal, de doenças auto-imune, inflamatória e de condição de pele
US7259143B2 (en) * 2002-09-05 2007-08-21 Wisconsin Alumni Research Foundation Method of extending the dose range of vitamin D compounds
CA2544502A1 (en) * 2003-11-25 2005-06-09 Wisconsin Alumni Research Foundation Vitamin d analogs for obesity prevention and treatment
CA2597624C (en) * 2005-02-11 2012-08-14 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24s)-1.alpha.,25-dihydroxyvitamin-d2
EP1848442B1 (en) * 2005-02-11 2012-04-25 Wisconsin Alumni Research Foundation 2-methylene-19-nor-(20s-24epi)-1alpha,25-dihydroxyvitamine-d2

Also Published As

Publication number Publication date
JP2007502832A (ja) 2007-02-15
EP1656157B1 (en) 2011-12-21
NZ545862A (en) 2010-01-29
ATE537834T1 (de) 2012-01-15
JP5009617B2 (ja) 2012-08-22
AU2004266706B2 (en) 2009-07-30
CA2535185A1 (en) 2005-03-03
WO2005018658A1 (en) 2005-03-03
US20050070511A1 (en) 2005-03-31
AU2004266706A1 (en) 2005-03-03
EP1656157A1 (en) 2006-05-17
EP1656157A4 (en) 2008-11-05
US7232810B2 (en) 2007-06-19

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