NL8320218A - Nieuwe vitamine d analogen. - Google Patents

Nieuwe vitamine d analogen. Download PDF

Info

Publication number: NL8320218A
Authority: NL; Netherlands
Prior art keywords: vitamin; fluoro; dihydroxyvitamin; compounds; analogs
Prior art date: 1982-07-26

Application number

NL8320218A

Other languages

English (en)

Dutch (nl)

Original Assignee

Wisconsin Alumni Res Found

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

1984-06-01

1983-06-22 Application filed by Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found

1984-06-01 Publication of NL8320218A publication Critical patent/NL8320218A/nl

Links

229930003231 vitamin Natural products 0.000 title description 9
239000011782 vitamin Substances 0.000 title description 9
229940088594 vitamin Drugs 0.000 title description 9
235000013343 vitamin Nutrition 0.000 title description 9
150000003722 vitamin derivatives Chemical class 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000005805 hydroxylation reaction Methods 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
-1 hydroxyl compound Chemical class 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
229930003316 Vitamin D Natural products 0.000 description 4
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 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
230000033444 hydroxylation Effects 0.000 description 4
230000004060 metabolic process Effects 0.000 description 4
239000002207 metabolite Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000019166 vitamin D Nutrition 0.000 description 4
239000011710 vitamin D Substances 0.000 description 4
150000003710 vitamin D derivatives Chemical class 0.000 description 4
229940046008 vitamin d Drugs 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
125000003118 aryl group Chemical group 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000002950 deficient Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 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
238000000034 method Methods 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
210000005084 renal tissue Anatomy 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 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
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000020084 Bone disease Diseases 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-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
AAXIIVBDXUWCCR-UHFFFAOYSA-N acetic acid;ethylaminomethanetriol Chemical compound CC(O)=O.CCNC(O)(O)O AAXIIVBDXUWCCR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 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
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
230000015556 catabolic process Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 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
238000006731 degradation reaction Methods 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000006331 halo benzoyl group Chemical group 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000011534 incubation Methods 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
238000006317 isomerization reaction Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
FYYHWMGAXLPEAU-OUBTZVSYSA-N magnesium-25 atom Chemical compound [25Mg] FYYHWMGAXLPEAU-OUBTZVSYSA-N 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 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 compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000000926 separation method Methods 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
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940124597 therapeutic agent Drugs 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)

NL8320218A 1982-07-26 1983-06-22 Nieuwe vitamine d analogen. NL8320218A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US40199782A	1982-07-26	1982-07-26
US40199782		1982-07-26
PCT/US1983/000965 WO1984000550A1 (en)	1982-07-26	1983-06-22	Novel vitamin d analogs
US8300965		1983-06-22

Publications (1)

Publication Number	Publication Date
NL8320218A true NL8320218A (nl)	1984-06-01

Family

ID=23590116

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8320218A NL8320218A (nl)	1982-07-26	1983-06-22	Nieuwe vitamine d analogen.

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
AU1821383A (en)	1984-02-23
IL69061A0 (en)	1983-10-31
CH661047A5 (de)	1987-06-30
JPS59501314A (ja)	1984-07-26

Publication	Publication Date	Title
KR950013636B1 (ko)	1995-11-13	I9-노르-비타민 d 화합물
US4661294A (en)	1987-04-28	Biologically active 1-thio derivatives of vitamin D
US4188345A (en)	1980-02-12	Fluorovitamin D compounds and processes for their preparation
EP0386793B1 (en)	1993-06-09	Novel 1 alpha-hydroxyvitamin d2 epimer and derivatives
US5952317A (en)	1999-09-14	Calcitriol derivatives and their uses
CA2229316C (en)	2005-04-12	Calcitriol derivatives and their uses
NL193245C (nl)	1999-04-02	Aan 1Ó,25-dihydroxyvitamine D2 verwante verbinding en farmaceutisch preparaat met een het calciummetabolisme regulerende werking dat een dergelijke verbinding bevat.
US4226788A (en)	1980-10-07	24,24-Difluoro-1α,25-dihydroxycholecalciferol
US4201881A (en)	1980-05-06	24,24-Difluoro-1α,25-dihydroxycholecalciferol
NL8420327A (nl)	1985-12-02	Isomeren van hydroxyvitamine d2.
WO1982002893A1 (en)	1982-09-02	1 alpha,25-dihydroxy-2 beta-fluorovitamin d3
NL8320218A (nl)	1984-06-01	Nieuwe vitamine d analogen.
AU4320999A (en)	1999-12-13	Method for making hydroxy-25-ene-vitamin d compounds
IE67953B1 (en)	1996-05-15	Side Chain Unsaturated 1alpha-Hydroxyvitamin D Homologs
JPH0449543B2 (da)	1992-08-11
US5354744A (en)	1994-10-11	Side chain unsaturated 1 alpha-hydroxyvitamin D analogs
GB2126234A (en)	1984-03-21	Novel vitamin D analogs
US5036061A (en)	1991-07-30	Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds
JPH0364498B2 (da)	1991-10-07
US4263214A (en)	1981-04-21	Fluorovitamin D compounds and processes for their preparation
US4229358A (en)	1980-10-21	Fluorovitamin D compounds and processes for their preparation
US4360472A (en)	1982-11-23	Trihydroxyvitamin D3 compounds
US4224230A (en)	1980-09-23	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