CA2097997C - Composes de vitamine d et methode de preparation de ces composes - Google Patents

Composes de vitamine d et methode de preparation de ces composes Download PDF

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Publication number: CA2097997C
Authority: CA; Canada
Prior art keywords: compound; general formula; group; vitamin; compounds
Prior art date: 1993-06-08
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

CA002097997A

Other languages

English (en)

Other versions

CA2097997A1 (fr

Inventor

Jose P. Sestelo

Antonio Mourino

Jose Mascarenas

Sebastianus J. Halkes

Jan Zorgdrager

Gerhardus D.H. Dijkstra

Jan-Paul Van De Velde

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

Duphar International Research BV

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.)

1993-06-08

Filing date

1993-06-08

Publication date

2006-01-10

1993-06-08 Application filed by Duphar International Research BV filed Critical Duphar International Research BV

1993-06-08 Priority to CA002097997A priority Critical patent/CA2097997C/fr

1993-06-29 Priority to JP18547893A priority patent/JP3633639B2/ja

1994-12-09 Publication of CA2097997A1 publication Critical patent/CA2097997A1/fr

2006-01-10 Application granted granted Critical

2006-01-10 Publication of CA2097997C publication Critical patent/CA2097997C/fr

2013-06-08 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

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238000000034 method Methods 0.000 title claims abstract description 18
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235000019166 vitamin D Nutrition 0.000 claims abstract description 63
239000011710 vitamin D Substances 0.000 claims abstract description 63
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SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
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235000010216 calcium carbonate Nutrition 0.000 description 1
244000309466 calf Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
RVIQSSNDHKQZHH-UHFFFAOYSA-N carbonyl diiodide Chemical compound IC(I)=O RVIQSSNDHKQZHH-UHFFFAOYSA-N 0.000 description 1
KIGALSBMRYYLFJ-UHFFFAOYSA-N chloro-(2,3-dimethylbutan-2-yl)-dimethylsilane Chemical compound CC(C)C(C)(C)[Si](C)(C)Cl KIGALSBMRYYLFJ-UHFFFAOYSA-N 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
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239000012141 concentrate Substances 0.000 description 1
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230000008878 coupling Effects 0.000 description 1
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239000012043 crude product Substances 0.000 description 1
238000012258 culturing Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000002380 cytological effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
230000037336 dry skin Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
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RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
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150000002500 ions Chemical class 0.000 description 1
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DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
AAWGSOZCJNFZAG-UHFFFAOYSA-M magnesium;cyclopropane;chloride Chemical compound [Mg+2].[Cl-].C1C[CH-]1 AAWGSOZCJNFZAG-UHFFFAOYSA-M 0.000 description 1
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VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
208000005368 osteomalacia Diseases 0.000 description 1
201000008968 osteosarcoma Diseases 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
230000008845 photoaging Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
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239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
201000006409 renal osteodystrophy Diseases 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
208000008281 urolithiasis Diseases 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dermatology (AREA)
Birds (AREA)
Epidemiology (AREA)
Hematology (AREA)
Obesity (AREA)
Nutrition Science (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Emergency Medicine (AREA)
Gerontology & Geriatric Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)

CA002097997A 1993-06-08 1993-06-08 Composes de vitamine d et methode de preparation de ces composes Expired - Fee Related CA2097997C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA002097997A CA2097997C (fr)	1993-06-08	1993-06-08	Composes de vitamine d et methode de preparation de ces composes
JP18547893A JP3633639B2 (ja)	1993-06-08	1993-06-29	ビタミンｄ化合物およびそれらの製造方法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA002097997A CA2097997C (fr)	1993-06-08	1993-06-08	Composes de vitamine d et methode de preparation de ces composes
JP18547893A JP3633639B2 (ja)	1993-06-08	1993-06-29	ビタミンｄ化合物およびそれらの製造方法

Publications (2)

Publication Number	Publication Date
CA2097997A1 CA2097997A1 (fr)	1994-12-09
CA2097997C true CA2097997C (fr)	2006-01-10

Family

ID=25676261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002097997A Expired - Fee Related CA2097997C (fr)	1993-06-08	1993-06-08	Composes de vitamine d et methode de preparation de ces composes

Country Status (2)

Country	Link
JP (1)	JP3633639B2 (fr)
CA (1)	CA2097997C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1272154T3 (da)	2000-04-04	2005-01-31	Color Access Inc	Præparat til forbedring af hudlipidbarrierefunktionen

1993
- 1993-06-08 CA CA002097997A patent/CA2097997C/fr not_active Expired - Fee Related
- 1993-06-29 JP JP18547893A patent/JP3633639B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH0717947A (ja)	1995-01-20
JP3633639B2 (ja)	2005-03-30
CA2097997A1 (fr)	1994-12-09

Legal Events

Date	Code	Title	Description
2000-05-31	EEER	Examination request
2009-06-08	MKLA	Lapsed
2022-09-10	MKLA	Lapsed	Effective date: 20090608

Publication	Publication Date	Title
US5449668A (en)	1995-09-12	Vitamin D compounds and method of preparing these compounds
US5929056A (en)	1999-07-27	Vitamin D compounds and method of preparing these compounds
US5545633A (en)	1996-08-13	17-ene vitamine D analogues
FI92929B (fi)	1994-10-14	Menetelmä uusien farmaseuttisesti vaikuttavien vitamiini D analogien valmistamiseksi
FI112361B (fi)	2003-11-28	Menetelmä terapeuttisesti käyttökelpoisten D-vitamiinin johdannaisten valmistamiseksi
JP2007326871A (ja)	2007-12-20	ビタミンｄ化合物類
AU707942B2 (en)	1999-07-22	New vitamin D derivatives with substituents at C-25, process for their production, intermediate products and use for the production of pharmaceutical agents
DE69806035T2 (de)	2003-01-30	Neue vitamin d-analoga
JPH06500089A (ja)	1994-01-06	新規ビタミンｄ類似体
AU2007212185A1 (en)	2007-08-16	Vitamin D analog - RAK, methods and uses thereof
RU2235721C2 (ru)	2004-09-10	Аналоги витамина d3
RU2165923C2 (ru)	2001-04-27	Аналоги витамина d, способ их получения, фармацевтическая композиция
JPH09511224A (ja)	1997-11-11	ビタミンｄアミンおよびアミド誘導体
RO120133B1 (ro)	2005-09-30	Derivaţi analogi ai vitaminei d
CA2097997C (fr)	2006-01-10	Composes de vitamine d et methode de preparation de ces composes
IL97158A (en)	1994-12-29	Homologous histories of vitamin D in the side chain, processes for their preparation and pharmaceutical preparations containing them
US5378695A (en)	1995-01-03	Vitamin D analogues
EP0944592B1 (fr)	2005-01-26	Derives de vitamine d3
WO1995019963A1 (fr)	1995-07-27	Nouveaux composes a activite pharmacotherapeutique
JP2004277433A (ja)	2004-10-07	ビタミンｄ化合物およびそれらの製造方法
PL177676B1 (pl)	1999-12-31	Nowe analogi witamin D, sposób ich wytwarzania igawierająneje środkitarmaneutycone i Oosmetycone