LT3666B - Novel vitamin d analogues - Google Patents

Novel vitamin d analogues Download PDF

Info

Publication number: LT3666B
Authority: LT; Lithuania
Prior art keywords: compound; formula; treatment; compounds; diseases
Prior art date: 1990-08-15

Application number

LTIP965A

Other languages

English (en)

Lithuanian (lt)

Inventor

Claus Aage Svensgaard Bretting

Original Assignee

Leo Pharm Prod Ltd

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.)

1990-08-15

Filing date

1993-09-10

Publication date

1996-01-25

1993-09-10 Application filed by Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd

1995-03-27 Publication of LTIP965A publication Critical patent/LTIP965A/xx

1996-01-25 Publication of LT3666B publication Critical patent/LT3666B/lt

Links

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229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
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230000007812 deficiency Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
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239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
208000024908 graft versus host disease Diseases 0.000 description 1
230000003779 hair growth Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
230000000148 hypercalcaemia Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000000411 inducer Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
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125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
150000002921 oxetanes Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
229940069338 potassium sorbate Drugs 0.000 description 1
235000010241 potassium sorbate Nutrition 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
210000001732 sebaceous gland Anatomy 0.000 description 1
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210000003491 skin Anatomy 0.000 description 1
210000004927 skin cell Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- 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
- 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
- A61P37/04—Immunostimulants
- 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
- 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
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Rheumatology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Nutrition Science (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

LTIP965A 1990-08-15 1993-09-10 Novel vitamin d analogues LT3666B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB909017890A GB9017890D0 (en)	1990-08-15	1990-08-15	Chemical compounds i

Publications (2)

Publication Number	Publication Date
LTIP965A LTIP965A (en)	1995-03-27
LT3666B true LT3666B (en)	1996-01-25

Family

ID=10680686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP965A LT3666B (en)	1990-08-15	1993-09-10	Novel vitamin d analogues

Country Status (20)

Country	Link
US (1)	US5447924A (fr)
EP (1)	EP0543864B1 (fr)
JP (1)	JP3246914B2 (fr)
KR (1)	KR100203227B1 (fr)
AT (1)	ATE115562T1 (fr)
AU (1)	AU636510B2 (fr)
CA (1)	CA2078555C (fr)
CZ (1)	CZ286485B6 (fr)
DE (1)	DE69105981T2 (fr)
DK (1)	DK0543864T3 (fr)
ES (1)	ES2068601T3 (fr)
FI (1)	FI103791B (fr)
GB (1)	GB9017890D0 (fr)
GR (1)	GR3014922T3 (fr)
IE (1)	IE66241B1 (fr)
LT (1)	LT3666B (fr)
LV (1)	LV10089B (fr)
RU (1)	RU2126384C1 (fr)
SK (1)	SK281443B6 (fr)
WO (1)	WO1992003414A1 (fr)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2062520C (fr) *	1991-03-11	1998-08-11	Hector F. Deluca	Synthese de composes de type 1-alpha-hydroxy-secosterol
US5486509A (en) *	1991-06-28	1996-01-23	University Of Miami	Method of preventing and treating chemotherapy-induced alopecia
GB9206648D0 (en) *	1992-03-26	1992-05-06	Leo Pharm Prod Ltd	Chemical compounds
GB9214202D0 (en) *	1992-07-03	1992-08-12	Leo Pharm Prod Ltd	Chemical compounds
GB9226860D0 (en) *	1992-12-23	1993-02-17	Leo Pharm Prod Ltd	Novel treatment
US5449668A (en) *	1993-06-04	1995-09-12	Duphar International Research B.V.	Vitamin D compounds and method of preparing these compounds
US6291444B1 (en)	1993-06-16	2001-09-18	Wisconsin Alumni Research Foundation	Treatment of t-cell immunodeficiencies with vitamin D compounds
US5880114A (en) *	1993-06-16	1999-03-09	Wisconsin Alumni Research Foundation	Treatment of immune deficiency with vitamin D compounds
US5552392A (en) *	1993-11-03	1996-09-03	Wisconsin Alumni Research Foundation	Method of treating hypoparathyroidism with (20S) vitamin D compounds
US5384314B1 (en) *	1994-03-11	1997-08-05	Hoffmann La Roche	1alpha-fluoro-25-hydroxy-16-ene-23-yne-cholecalciferol
US5661140A (en) *	1994-11-21	1997-08-26	Wisconsin Alumni Research Foundation	18-nor-vitamin D compounds
DE19519273A1 (de) *	1995-05-22	1996-11-28	Schering Ag	Topisch applizierbare Mittel zur Behandlung und Prophylaxe der Alopezie
SG70009A1 (en) *	1996-05-23	2000-01-25	Hoffmann La Roche	Vitamin d3 analogs
NO971934L (no) *	1996-05-23	1997-11-24	Hoffmann La Roche	Flourinerte vitamin D3 -analoger
US5939408A (en)	1996-05-23	1999-08-17	Hoffman-La Roche Inc.	Vitamin D3 analogs
GB9622590D0 (en) *	1996-10-30	1997-01-08	Leo Pharm Prod Ltd	Chemical compounds
MA26481A1 (fr) *	1997-04-21	2004-12-20	Hoffmann La Roche	Derives d'arylsecocholadiene
ES2206981T3 (es) *	1997-07-17	2004-05-16	F.Hoffmann-La Roche Ag	Dihomo-seco-colestanos con dos enlaces insaturados en la cadena lateral.
CA2303248A1 (fr) *	1997-09-08	1999-03-18	F. Hoffmann-La Roche Ag	Analogues de vitamine d3 de 1,3-dihydroxy-20,20-dialkyle
US20030220234A1 (en) *	1998-11-02	2003-11-27	Selvaraj Naicker	Deuterated cyclosporine analogs and their use as immunodulating agents
EP1064000B1 (fr)	1998-03-27	2011-07-06	Oregon Health & Science University	Vitamine d et ses analogues pour le traitement de tumeurs et d'autres troubles d'hyperproliferation
DE60231570D1 (de)	2001-10-19	2009-04-23	Isotechnika Inc	Synthese von Cyclosporinanalogen
AR041696A1 (es)	2002-10-23	2005-05-26	Leo Pharm Prod Ltd	Compuestos analogos de vitamina d, composiciones que comprenden dichos compuestos analogos y su uso
CA2500640A1 (fr) *	2002-10-23	2004-05-06	Leo Pharma A/S	Analogues de la vitamine d, compositions comprenant lesdits analogues et leur utilisation
US7351869B2 (en) *	2002-11-18	2008-04-01	Teva Pharmaceutical Industries Ltd	Crystallization method for purification of calcipotriene
ES2233209B1 (es) *	2003-11-28	2006-04-01	Laboratorios Viñas S.A.	Compuestos monohalogenovinilderivados de vitamina d.
ES2234423B1 (es) *	2003-12-05	2006-03-01	Laboratorios Viñas, S.A.	Procedimiento para la obtencion de derivados de vitamina d a partir de compuestos monohalogenovinilicos.
CA2608021A1 (fr) *	2005-05-10	2006-11-16	Dermipsor Ltd.	Compositions et procedes de soin de la peau
CA2608023C (fr)	2005-05-10	2015-08-18	Dermipsor Ltd.	Compositions comprenant du calcipotriol et de la nicotinamide pour traiter des maladies epidermiques hyperproliferatives
KR20090039833A (ko) *	2006-08-29	2009-04-22	테바 파마슈티컬 인더스트리즈 리미티드	비타민 ｄ 및 코르티코스테로이드를 포함하는 약학 조성물
SG2014006324A (en)	2009-01-27	2014-03-28	Berg Llc	Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy
CN102655869B (zh)	2009-08-14	2016-08-10	博格有限责任公司	用于治疗脱发的维生素d3及其类似物
US9006220B2 (en)	2010-10-25	2015-04-14	Teijin Pharma Limited	23-yne-vitamin D3 derivative
HK1222819A1 (zh)	2013-05-29	2017-07-14	博格有限责任公司	使用维生素d预防或减轻化疗诱发的脱发
WO2017209934A1 (fr)	2016-05-13	2017-12-07	Case Western Reserve University	Activateurs de l'autophagie pour le traitement ou la prévention de lésions cutanées

Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0227826A1 (fr)	1985-08-02	1987-07-08	Leo Pharm Prod Ltd	Nouveaux analogues de la vitamine d.
US4804502A (en)	1988-01-20	1989-02-14	Hoffmann-La Roche Inc.	Vitamin D compounds
WO1989010351A1 (fr)	1988-04-21	1989-11-02	Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis	Nouveaux analogues de vitamine d
US4948789A (en)	1989-03-28	1990-08-14	Chugai Seiyaku Kabushiki Kaisha	Suppression of parathyroid hormone synthesis and secretion
EP0385446A2 (fr)	1989-02-28	1990-09-05	Chugai Seiyaku Kabushiki Kaisha	Ostéogénèse avec des dérivés de vitamine D
WO1991000271A1 (fr)	1989-06-29	1991-01-10	Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab)	Nouveaux analogues de vitamine d

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4594432A (en) *	1983-01-28	1986-06-10	Hoffman-La Roche Inc.	Process for the synthesis of 1α,23(S),25-trihydroxycholecalciferol and 1α,23(R),25-trihydroxycholecalciferol
US4719205A (en) *	1984-01-30	1988-01-12	Wisconsin Alumini Research Foundation	Side-chain unsaturated 1-hydroxyvitamin D compounds
JPS6144860A (ja) *	1984-08-10	1986-03-04	Taisho Pharmaceut Co Ltd	１α．２５−ジヒドロキシ−２６．２７−ジメチルビタミンＤ↓３
JPS6172652A (ja) *	1984-09-14	1986-04-14	Asahi Glass Co Ltd	歯科材料用リン酸カルシウム系結晶性ガラス
DE3577552D1 (de) *	1984-11-27	1990-06-13	Chugai Pharmaceutical Co Ltd	Vitamin d-derivate und verfahren zu deren herstellung.
US4612308A (en) *	1984-11-29	1986-09-16	Hoffmann-La Roche Inc.	25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers
ATE45347T1 (de) *	1985-05-30	1989-08-15	Taisho Pharmaceutical Co Ltd	Vitamin d3-derivate.
WO1987003282A1 (fr) *	1985-11-21	1987-06-04	Taisho Pharmaceutical Co., Ltd.	Derive de la vitamine d3
DE3865544D1 (de) *	1987-06-23	1991-11-21	Yamanouchi Pharma Co Ltd	Vitamin d3-derivate.
US4851401A (en) *	1988-07-14	1989-07-25	Wisconsin Alumni Research Foundation	Novel cyclopentano-vitamin D analogs
DK0398217T3 (da) *	1989-05-18	1994-02-14	Hoffmann La Roche	Dehydrocholecalciferolderivater
GB8915770D0 (en) *	1989-07-10	1989-08-31	Leo Pharm Prod Ltd	Chemical compounds
US5260290A (en) *	1990-02-14	1993-11-09	Wisconsin Alumni Research Foundation	Homologated vitamin D2 compounds and the corresponding 1α-hydroxylated derivatives
DE4011682A1 (de) *	1990-04-06	1991-10-10	Schering Ag	24-oxa-derivate in der vitamin d-reihe
US5200536A (en) *	1992-02-10	1993-04-06	Daikin Industries Ltd.	Fluorine-containing vitamin D3 analogues
US5194431A (en) *	1992-07-08	1993-03-16	Wisconsin Alumni Research Foundation	24-cyclopropane vitamin D derivatives

1990
- 1990-08-15 GB GB909017890A patent/GB9017890D0/en active Pending
1991
- 1991-07-11 WO PCT/DK1991/000200 patent/WO1992003414A1/fr not_active Ceased
- 1991-07-11 AT AT91914384T patent/ATE115562T1/de not_active IP Right Cessation
- 1991-07-11 RU RU92016313A patent/RU2126384C1/ru not_active IP Right Cessation
- 1991-07-11 CA CA002078555A patent/CA2078555C/fr not_active Expired - Fee Related
- 1991-07-11 AU AU84223/91A patent/AU636510B2/en not_active Ceased
- 1991-07-11 EP EP91914384A patent/EP0543864B1/fr not_active Expired - Lifetime
- 1991-07-11 ES ES91914384T patent/ES2068601T3/es not_active Expired - Lifetime
- 1991-07-11 JP JP51385491A patent/JP3246914B2/ja not_active Expired - Fee Related
- 1991-07-11 DE DE69105981T patent/DE69105981T2/de not_active Expired - Fee Related
- 1991-07-11 DK DK91914384.2T patent/DK0543864T3/da active
- 1991-07-15 IE IE246291A patent/IE66241B1/en not_active IP Right Cessation
1992
- 1992-09-22 US US07/927,420 patent/US5447924A/en not_active Expired - Fee Related
- 1992-09-30 KR KR1019920702385A patent/KR100203227B1/ko not_active Expired - Fee Related
- 1992-12-07 FI FI925547A patent/FI103791B/fi active
- 1992-12-17 CZ CZ19923726A patent/CZ286485B6/cs not_active IP Right Cessation
- 1992-12-17 SK SK3726-92A patent/SK281443B6/sk unknown
1993
- 1993-02-15 LV LVP-93-243A patent/LV10089B/en unknown
- 1993-09-10 LT LTIP965A patent/LT3666B/lt not_active IP Right Cessation
1995
- 1995-02-01 GR GR950400186T patent/GR3014922T3/el unknown

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0227826A1 (fr)	1985-08-02	1987-07-08	Leo Pharm Prod Ltd	Nouveaux analogues de la vitamine d.
US4804502A (en)	1988-01-20	1989-02-14	Hoffmann-La Roche Inc.	Vitamin D compounds
WO1989010351A1 (fr)	1988-04-21	1989-11-02	Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis	Nouveaux analogues de vitamine d
EP0385446A2 (fr)	1989-02-28	1990-09-05	Chugai Seiyaku Kabushiki Kaisha	Ostéogénèse avec des dérivés de vitamine D
US4948789A (en)	1989-03-28	1990-08-14	Chugai Seiyaku Kabushiki Kaisha	Suppression of parathyroid hormone synthesis and secretion
WO1991000271A1 (fr)	1989-06-29	1991-01-10	Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab)	Nouveaux analogues de vitamine d

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
A. BURGER ET AL.: "Acetylenic cholesteryl derivatives as irreversible inhibitors of ecdysone biosynthesis", TETRAHEDRON, 1988, pages 1141
ABE E ET AL.: "Differentiation of mouse myeloid leukemia cells induced by 1 alpha,25-dihydroxyvitamin D3", PROC NATL ACAD SCI USA., 1981, pages 4990 - 4994
DONALD S. MATTESON, ROBERT J. MOODY: "Homologation of carbonyl compounds to aldehydes with lithium bis(ethylenedioxyboryl)methide", J. ORG. CHEM., 1980, pages 1091
IKEKAWA, N. ET AL.: "26,27-Diethyl-1 alpha,25-dihydroxyvitamin D3 and 24,24-difluoro-24-homo-1 alpha,25-dihydroxyvitamin D3: highly potent inducer for differentiation of human leukemia cells HL-60", CHEM PHARM BULL, 1987, pages 4362 - 4365
INOMATA S ET AL.: "Effect of 1 alpha (OH)-vitamin D3 on insulin secretion in diabetes mellitus", BONE MINER., 1986, pages 187 - 192
L. LIND ET AL.: "Blood pressure is lowered by vitamin D (alphacalcidol) during long-term treatment of patients with intermittent hypercalcaemia", ACTA MED. SCAND., 1987, pages 423 - 427
LISE BINDERUP ET AL.: "Effects of a novel vitamin D analogue MC 903 on cell proliferation and differentiation in vitro and on calcium metabolism in vivo", BIOCHEMICAL PHARMACOLOGY, 1988, pages 889 - 895
MARTIN J. CALVERLEY: "Synthesis of mc 903, a biologically active vitamin D metabolite analogue", TETRAHEDRON, 1987, pages 4609, XP002336467, DOI: doi:10.1016/S0040-4020(01)86903-9
MULLER, K, SVENSON, M, BENDTZEN, K.: "1-alpha, 25-dihydroxyvitamin D3 and a novel vitamin D analogue MC903 are potent inhibitors of human interleukin 1 in vitro", IMMUNOL LETT., 1988, pages 361 - 366
OSTREM VK, TANAKA Y ET AL.: "N. 24- and 26-homo-1,25-dihydroxyvitamin D3: preferential activity in inducing differentiation of human leukemia cells HL-60 in vitro", PROC NATL ACAD SCI USA., 1987, pages 2610 - 2614, XP002009787, DOI: doi:10.1073/pnas.84.9.2610
R. C. LAROCK: "Comprehensive Organic Transformations", pages: 733
SAI, H., TAKATSUTO, S., HARA, N., AND IKEKAWA: "Synthesis of 1 alpha,25-dihydroxy-26,27-dimethylvitamin D3, a highly active analogue of 1 alpha,25-dihydroxyvitamin D3", CHEM PHARM BULL, 1985, pages 878 - 881
V. L. MALLOY: "The Tricontinental Meeting for Investigative Dermatology"

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FI103791B1 (fi)	1999-09-30
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CA2078555A1 (fr)	1992-02-16
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CA2078555C (fr)	2002-11-26
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AU636510B2 (en)	1993-04-29
KR100203227B1 (ko)	1999-06-15
WO1992003414A1 (fr)	1992-03-05
US5447924A (en)	1995-09-05
DE69105981T2 (de)	1995-04-20
SK372692A3 (en)	1995-04-12
IE66241B1 (en)	1995-12-13
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AU8422391A (en)	1992-03-17
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LT3666B (en)	1996-01-25	Novel vitamin d analogues
EP0648207B1 (fr)	1997-03-12	Analogues de la vitamine d
RU2136660C1 (ru)	1999-09-10	Аналоги витамина d, способы их получения и фармацевтическая композиция
JP3553591B2 (ja)	2004-08-11	新規ビタミンｄ類似体
EP0667856A1 (fr)	1995-08-23	Nouveaux analogues de la vitamine d
EP0662954B1 (fr)	1997-08-20	Nouveaux analogues de vitamine d
NZ256386A (en)	1997-07-27	20-(substituted alkoxy)-9,10-seco-pregnatriene derivatives and medicaments
JP4988551B2 (ja)	2012-08-01	２−アルキリデン１８，１９−ジノル−ビタミンｄ化合物
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