CA2072915A1 - Vitamin d compound, method of preparing this compound and intermediate therefor - Google Patents

Vitamin d compound, method of preparing this compound and intermediate therefor

Info

Publication number
CA2072915A1
CA2072915A1 CA002072915A CA2072915A CA2072915A1 CA 2072915 A1 CA2072915 A1 CA 2072915A1 CA 002072915 A CA002072915 A CA 002072915A CA 2072915 A CA2072915 A CA 2072915A CA 2072915 A1 CA2072915 A1 CA 2072915A1
Authority
CA
Canada
Prior art keywords
compound
vitamin
group
preparing
intermediate therefor
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.)
Granted
Application number
CA002072915A
Other languages
French (fr)
Other versions
CA2072915C (en
Inventor
Maria Jose Valles
Jose Luis Mascarenas
Antonio Mourino
Sebastianus J. Halkes
Jan Zorgdrager
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.)
Duphar International Research BV
Original Assignee
Maria Jose Valles
Jose Luis Mascarenas
Antonio Mourino
Sebastianus J. Halkes
Jan Zorgdrager
Duphar International Research B.V.
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 Maria Jose Valles, Jose Luis Mascarenas, Antonio Mourino, Sebastianus J. Halkes, Jan Zorgdrager, Duphar International Research B.V. filed Critical Maria Jose Valles
Publication of CA2072915A1 publication Critical patent/CA2072915A1/en
Application granted granted Critical
Publication of CA2072915C publication Critical patent/CA2072915C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • 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
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/532—Cycloaliphatic phosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • 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
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

Abstract

The invention relates to a new vitamin D compound, substituted in the 18-position with an alkyl group, a hydroxy group, an alkoxy group, an alkenyl group, an alkynyl group, a fluorinated alkyl group or a fluorinated alkenyl group.
The invention also relates to a method of preparing said vitamin D
compound and to a lactone and a hydrindane intermediate.
The vitamin D compound is of the general formula <see formula I>
CA002072915A 1991-07-05 1992-07-02 Vitamin d compound, method of preparing this compound and intermediate therefor Expired - Fee Related CA2072915C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP91201746.4 1991-07-05
EP91201746 1991-07-05
EP92200154 1992-01-20
EP92200154.0 1992-01-20

Publications (2)

Publication Number Publication Date
CA2072915A1 true CA2072915A1 (en) 1993-01-06
CA2072915C CA2072915C (en) 2005-11-01

Family

ID=26129316

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002072915A Expired - Fee Related CA2072915C (en) 1991-07-05 1992-07-02 Vitamin d compound, method of preparing this compound and intermediate therefor

Country Status (12)

Country Link
US (3) US5403940A (en)
EP (1) EP0521550B1 (en)
JP (1) JP3342047B2 (en)
AT (1) ATE143007T1 (en)
AU (1) AU650148B2 (en)
CA (1) CA2072915C (en)
DE (1) DE69213844T2 (en)
DK (1) DK0521550T3 (en)
ES (1) ES2093180T3 (en)
GR (1) GR3022053T3 (en)
IL (1) IL102385A (en)
NZ (1) NZ243409A (en)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1333616C (en) * 1989-03-09 1994-12-20 Hector F. Deluca 19-nor-vitamin d compounds
US20040009958A1 (en) * 1991-01-08 2004-01-15 Bone Care International, Inc. Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2
US5830885A (en) * 1992-03-12 1998-11-03 The Johns Hopkins University Antiproliferative vitamin D3 hybrids
DE4220757A1 (en) * 1992-06-24 1994-01-05 Schering Ag Derivatives in the vitamin D series with modifications in the 20-position, process for their preparation, intermediates for this process, pharmaceutical preparations containing these derivatives and their use in the manufacture of medicaments
GB9220272D0 (en) * 1992-09-25 1992-11-11 Leo Pharm Prod Ltd Chemical compounds
GB9220439D0 (en) * 1992-09-28 1992-11-11 Leo Pharm Prod Ltd Chemical compounds
TW267161B (en) * 1992-11-20 1996-01-01 Hoffmann La Roche
US5449668A (en) * 1993-06-04 1995-09-12 Duphar International Research B.V. Vitamin D compounds and method of preparing these compounds
US5763429A (en) * 1993-09-10 1998-06-09 Bone Care International, Inc. Method of treating prostatic diseases using active vitamin D analogues
US5565589A (en) * 1993-11-03 1996-10-15 Wisconsin Alumni Research Foundation 17-formyl-5,6-trans-vitamin D compounds
US6121469A (en) 1993-12-23 2000-09-19 The Regents Of The University Of California Therapeutically effective 1α,25-dihydroxyvitamin D3 analogs
DK0717034T3 (en) * 1994-12-14 1999-10-18 Duphar Int Res Vitamin D compounds and methods for preparing these compounds
US20020183288A1 (en) * 1995-04-03 2002-12-05 Bone Care International, Inc. Method for treating and preventing hyperparathyroidism
US6242434B1 (en) * 1997-08-08 2001-06-05 Bone Care International, Inc. 24-hydroxyvitamin D, analogs and uses thereof
US20040043971A1 (en) * 1995-04-03 2004-03-04 Bone Care International, Inc. Method of treating and preventing hyperparathyroidism with active vitamin D analogs
CA2175881A1 (en) * 1995-05-09 1996-11-10 Andrzej Kutner Vitamin d compounds and methods of preparing these compounds
GB9607034D0 (en) * 1996-04-03 1996-06-05 Leo Pharm Prod Ltd Chemical compounds
US6566353B2 (en) * 1996-12-30 2003-05-20 Bone Care International, Inc. Method of treating malignancy associated hypercalcemia using active vitamin D analogues
US20020128240A1 (en) * 1996-12-30 2002-09-12 Bone Care International, Inc. Treatment of hyperproliferative diseases using active vitamin D analogues
US20030129194A1 (en) * 1997-02-13 2003-07-10 Bone Care International, Inc. Targeted therapeutic delivery of vitamin D compounds
CA2279590A1 (en) * 1997-02-13 1998-08-20 Bone Care International, Inc. Targeted therapeutic delivery of vitamin d compounds
US6359152B2 (en) 1997-07-21 2002-03-19 Wisconsin Alumni Research Foundation 18-substituted-19-nor-vitamin D compounds
US5939406A (en) 1997-07-21 1999-08-17 Wisconsin Alumni Research Foundation 18-substituted-19-nor-vitamin D compounds
US6087350A (en) * 1997-08-29 2000-07-11 University Of Pittsburgh Of The Commonwealth System Of Higher Education Use of pretreatment chemicals to enhance efficacy of cytotoxic agents
CA2303248A1 (en) 1997-09-08 1999-03-18 F. Hoffmann-La Roche Ag 1,3-dihydroxy-20,20-dialkyl-vitamin d3 analogs
AU762481C (en) 1998-03-27 2004-08-19 Oregon Health Sciences University Vitamin D and its analogs in the treatment of tumors and other hyperproliferative disorders
CA2414407A1 (en) * 2000-07-18 2002-01-24 Bone Care International, Inc. Stabilized 1.alpha.-hydroxy vitamin d
DE10129108A1 (en) * 2001-06-16 2003-01-02 Harman Becker Automotive Sys Method and circuit arrangement for data transmission
CA2461295A1 (en) * 2001-09-27 2003-04-03 The Coca-Cola Company Vitamin fortification of foodstuffs
US20040053895A1 (en) * 2002-09-18 2004-03-18 Bone Care International, Inc. Multi-use vessels for vitamin D formulations
US7148211B2 (en) * 2002-09-18 2006-12-12 Genzyme Corporation Formulation for lipophilic agents
US7094775B2 (en) * 2004-06-30 2006-08-22 Bone Care International, Llc Method of treating breast cancer using a combination of vitamin D analogues and other agents
US20060003950A1 (en) * 2004-06-30 2006-01-05 Bone Care International, Inc. Method of treating prostatic diseases using a combination of vitamin D analogues and other agents
CA2608021A1 (en) * 2005-05-10 2006-11-16 Dermipsor Ltd. Compositions and methods for skin care
AU2006245283B2 (en) * 2005-05-10 2012-11-01 Dermipsor Ltd. Compositions and methods for treating hyperproliferative epidermal diseases
WO2007070853A2 (en) * 2005-12-14 2007-06-21 Digital Signal Corporation System and method for tracking eyeball motion
EA201691980A1 (en) 2009-01-27 2017-07-31 БЕРГ ЭлЭлСи WAYS TO REDUCE SIDE EFFECTS ASSOCIATED WITH CHEMOTHERAPY
SG10201404883YA (en) 2009-08-14 2014-10-30 Berg Llc Vitamin d3 and analogs thereof for treating alopecia
AU2014274099A1 (en) 2013-05-29 2015-12-24 Berg Llc Preventing or mitigating chemotherapy induced alopecia using vitamin D
US20190183908A1 (en) 2016-05-13 2019-06-20 Case Western Reserve University Autophagy activators for treating or preventing skin injury
US9989699B2 (en) 2016-10-27 2018-06-05 Corning Incorporated Low bend loss single mode optical fiber
US11512107B2 (en) 2018-09-07 2022-11-29 Trustees Of Dartmouth College Methods for assembly of tetracyclic compounds by stereoselective C9-C10 bond formation
AU2019335005A1 (en) * 2018-09-07 2021-03-18 Trustees Of Dartmouth College C19 scaffolds and steroids and methods of use and manufacture thereof

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617297A (en) * 1982-02-12 1986-10-14 Hoffmann-La Roche Inc. Method of treating disease states by the administration of 1α,25,26-trihydroxycholecalciferol
US4508651A (en) * 1983-03-21 1985-04-02 Hoffmann-La Roche Inc. Synthesis of 1α,25-dihydroxyergocalciferol
US4613594A (en) * 1984-11-16 1986-09-23 Hoffmann-La Roche Inc. Fluorinated vitamin D3 compounds
US4612308A (en) * 1984-11-29 1986-09-16 Hoffmann-La Roche Inc. 25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers
EP0205025A1 (en) * 1985-05-27 1986-12-17 Sumitomo Pharmaceuticals Company, Limited Fluorine derivatives of vitamin D3 and cell differentiation-inducing agents containing the same as an active ingredient
US4755329A (en) * 1985-06-10 1988-07-05 Wisconsin Alumni Research Foundation Process and intermediates for preparing 1α-hydroxyvitamin D compounds
AU603340B2 (en) * 1985-08-02 1990-11-15 Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) Novel vitamin d analogues
IL77668A (en) * 1986-01-21 1989-03-31 Teva Pharma Production of cholecalciferol derivatives and novel intermediates used therefor
US4804502A (en) * 1988-01-20 1989-02-14 Hoffmann-La Roche Inc. Vitamin D compounds
NZ232734A (en) * 1989-03-09 1991-11-26 Wisconsin Alumni Res Found 19-nor vitamin d derivatives and pharmaceutical compositions
CA1333616C (en) * 1989-03-09 1994-12-20 Hector F. Deluca 19-nor-vitamin d compounds
US5246925A (en) * 1989-03-09 1993-09-21 Wisconsin Alumni Research Foundation 19-nor-vitamin D compounds for use in treating hyperparathyroidism
US5449668A (en) * 1993-06-04 1995-09-12 Duphar International Research B.V. Vitamin D compounds and method of preparing these compounds
US5617297A (en) * 1995-09-25 1997-04-01 National Semiconductor Corporation Encapsulation filler technology for molding active electronics components such as IC cards or PCMCIA cards

Also Published As

Publication number Publication date
EP0521550B1 (en) 1996-09-18
JPH05221961A (en) 1993-08-31
EP0521550A3 (en) 1993-06-16
US5403940A (en) 1995-04-04
US6072062A (en) 2000-06-06
AU650148B2 (en) 1994-06-09
US5637742A (en) 1997-06-10
NZ243409A (en) 1995-02-24
AU1864992A (en) 1993-01-07
DK0521550T3 (en) 1996-11-04
EP0521550A2 (en) 1993-01-07
ES2093180T3 (en) 1996-12-16
IL102385A0 (en) 1993-01-14
DE69213844D1 (en) 1996-10-24
ATE143007T1 (en) 1996-10-15
DE69213844T2 (en) 1997-04-10
GR3022053T3 (en) 1997-03-31
CA2072915C (en) 2005-11-01
JP3342047B2 (en) 2002-11-05
IL102385A (en) 1996-09-12

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Legal Events

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