JPS59501314A - 新規なビタミンｄ類似体 - Google Patents

新規なビタミンｄ類似体

Info

Publication number: JPS59501314A
Authority: JP; Japan
Prior art keywords: vitamin; fluoro; compounds; analogs; dihydroxyvitamin
Prior art date: 1982-07-26
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.): Pending

Application number

JP83502455A

Other languages

English (en)

Japanese (ja)

Inventor

デル−カ・ヘクタ−・エフ

シユノ−ズ・ハインリツヒ・ケ−

洋子田中

Original Assignee

ウイスコンシン　アラムナイ　リサ−チ　フオンデ−シヨン

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.)

1982-07-26

Filing date

1983-06-22

Publication date

1984-07-26

1983-06-22 Application filed by ウイスコンシン　アラムナイ　リサ−チ　フオンデ−シヨン filed Critical ウイスコンシン　アラムナイ　リサ−チ　フオンデ−シヨン

1984-07-26 Publication of JPS59501314A publication Critical patent/JPS59501314A/ja

Status Pending legal-status Critical Current

Links

QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 title claims description 9
229930003316 Vitamin D Natural products 0.000 title description 3
239000011710 vitamin D Substances 0.000 title description 3
235000019166 vitamin D Nutrition 0.000 title description 3
150000003710 vitamin D derivatives Chemical class 0.000 title description 3
229940046008 vitamin d Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 7
239000011647 vitamin D3 Substances 0.000 claims description 6
235000005282 vitamin D3 Nutrition 0.000 claims description 6
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims description 6
229940021056 vitamin d3 Drugs 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000005805 hydroxylation reaction Methods 0.000 description 8
229940088594 vitamin Drugs 0.000 description 7
229930003231 vitamin Natural products 0.000 description 7
239000011782 vitamin Substances 0.000 description 7
235000013343 vitamin Nutrition 0.000 description 7
150000003722 vitamin derivatives Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
-1 acyl anhydride Chemical class 0.000 description 4
239000011612 calcitriol Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000004060 metabolic process Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000287828 Gallus gallus Species 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
235000013330 chicken meat Nutrition 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
230000033444 hydroxylation Effects 0.000 description 3
239000002207 metabolite Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001263 acyl chlorides Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
229960005084 calcitriol Drugs 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
239000011654 magnesium acetate Substances 0.000 description 2
229940069446 magnesium acetate Drugs 0.000 description 2
235000011285 magnesium acetate Nutrition 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000005084 renal tissue Anatomy 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 2
GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 description 1
JWUBBDSIWDLEOM-DCHLRESJSA-N 25-Hydroxyvitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C/C=C1\C[C@@H](O)CCC1=C JWUBBDSIWDLEOM-DCHLRESJSA-N 0.000 description 1
JWUBBDSIWDLEOM-NQZHSCJISA-N 25-hydroxy-3 epi cholecalciferol Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@H](O)CCC1=C JWUBBDSIWDLEOM-NQZHSCJISA-N 0.000 description 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000020084 Bone disease Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
206010047626 Vitamin D Deficiency Diseases 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
208000022458 calcium metabolism disease Diseases 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000001721 carboxyacetyl group Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000007429 general method Methods 0.000 description 1
230000013632 homeostatic process Effects 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000003643 water by type Substances 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
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP83502455A 1982-07-26 1983-06-22 新規なビタミンｄ類似体 Pending JPS59501314A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US40199782A	1982-07-26	1982-07-26
US401997NLSE		1982-07-26
PCT/US1983/000965 WO1984000550A1 (en)	1982-07-26	1983-06-22	Novel vitamin d analogs

Publications (1)

Publication Number	Publication Date
JPS59501314A true JPS59501314A (ja)	1984-07-26

Family

ID=23590116

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP83502455A Pending JPS59501314A (ja)	1982-07-26	1983-06-22	新規なビタミンｄ類似体

Country Status (8)

Country	Link
JP (1)	JPS59501314A (da)
AU (1)	AU1821383A (da)
CH (1)	CH661047A5 (da)
DE (1)	DE3390125T1 (da)
DK (1)	DK161484D0 (da)
IL (1)	IL69061A0 (da)
NL (1)	NL8320218A (da)
WO (1)	WO1984000550A1 (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1985003299A1 (en) *	1984-01-30	1985-08-01	Wisconsin Alumni Research Foundation	Side-chain unsaturated 1-hydroxyvitamin d compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3847955A (en) *	1973-07-16	1974-11-12	Wisconsin Alumni Res Found	1,24,25-trihydroxycholecalciferol
US4229357A (en) *	1978-07-26	1980-10-21	Wisconsin Alumni Research Foundation	Fluorovitamin D compounds and processes for their preparation
US4305880A (en) *	1980-09-22	1981-12-15	Wisconsin Alumni Research Foundation	Process for preparing 24-fluoro-25-hydroxycholecalciferol

1983
- 1983-06-22 CH CH1547/84A patent/CH661047A5/de not_active IP Right Cessation
- 1983-06-22 DE DE19833390125 patent/DE3390125T1/de not_active Withdrawn
- 1983-06-22 AU AU18213/83A patent/AU1821383A/en not_active Abandoned
- 1983-06-22 NL NL8320218A patent/NL8320218A/nl unknown
- 1983-06-22 WO PCT/US1983/000965 patent/WO1984000550A1/en not_active Ceased
- 1983-06-22 JP JP83502455A patent/JPS59501314A/ja active Pending
- 1983-06-23 IL IL69061A patent/IL69061A0/xx unknown
1984
- 1984-03-21 DK DK1614/84A patent/DK161484D0/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK161484A (da)	1984-03-21
WO1984000550A1 (en)	1984-02-16
DE3390125T1 (de)	1984-09-20
DK161484D0 (da)	1984-03-21
NL8320218A (nl)	1984-06-01
AU1821383A (en)	1984-02-23
IL69061A0 (en)	1983-10-31
CH661047A5 (de)	1987-06-30

Publication	Publication Date	Title
US3598858A (en)	1971-08-10	Pge2 and pge3
DE2012167C2 (de)	1982-09-23	25-Hydroxycholecalciferol-hydrat und Verfahren sowie Zwischenprodukte zu seiner Herstellung
US4188345A (en)	1980-02-12	Fluorovitamin D compounds and processes for their preparation
US4022891A (en)	1977-05-10	Novel 1α,24-dihydroxycholecalciferol compositions, novel precursors thereof, and processes for preparing them
US4661294A (en)	1987-04-28	Biologically active 1-thio derivatives of vitamin D
WO1983000335A1 (en)	1983-02-03	26,26,26,27,27,27-HEXAFLUORO-1'alpha',25-DIHYDROXYCHOLECALCIFEROL AND PROCESS FOR PREPARING SAME
US5952317A (en)	1999-09-14	Calcitriol derivatives and their uses
US4248791A (en)	1981-02-03	25-Hydroxy-26,26,26,27,27,27-hexafluorocholecalciferol
US4226788A (en)	1980-10-07	24,24-Difluoro-1α,25-dihydroxycholecalciferol
US4201881A (en)	1980-05-06	24,24-Difluoro-1α,25-dihydroxycholecalciferol
US4307025A (en)	1981-12-22	1α, 25-dihydroxy-2β-fluorovitamin D3
FR2639045A2 (fr)	1990-05-18	Nouveaux produits derives de la structure 3-ceto-delta-4,9-19-nor steroides et leur application comme medicaments
US4495181A (en)	1985-01-22	1,25-Dihydroxy-24-oxo-vitamin D3 and 1,23,25-trihydroxy-24-oxo-vitamin D3
NL8420327A (nl)	1985-12-02	Isomeren van hydroxyvitamine d2.
DE69318142T2 (de)	1998-09-17	1 alpha-HYDROXY-24-(EPI)-VITAMIN D4
JPS59501314A (ja)	1984-07-26	新規なビタミンｄ類似体
GB2126234A (en)	1984-03-21	Novel vitamin D analogs
DE3590021C2 (de)	1992-09-10	1alpha-Hydroxyvitamin D-Derivat und dieses enthaltendes Arzneimittel
US4263214A (en)	1981-04-21	Fluorovitamin D compounds and processes for their preparation
IIDA et al.	1986	Potential bile acid metabolites. X.: Syntheses of stereoisomeric 3, 7-dihydroxy-5α-cholanic acids
US4229358A (en)	1980-10-21	Fluorovitamin D compounds and processes for their preparation
US4226787A (en)	1980-10-07	Fluorovitamin D compounds and processes for their preparation
US4229357A (en)	1980-10-21	Fluorovitamin D compounds and processes for their preparation
JPS58116459A (ja)	1983-07-11	トリヒドロキシビタミンｄ↓３化合物
CH387022A (fr)	1965-01-31	Procédé de préparation de 6-désoxy-tétracyclines