FI90764B - Förfarande för framställning av terapeutiskt användbara 25-hydroxi-vitamin D-derivat - Google Patents
Förfarande för framställning av terapeutiskt användbara 25-hydroxi-vitamin D-derivat Download PDFInfo
- Publication number
- FI90764B FI90764B FI890283A FI890283A FI90764B FI 90764 B FI90764 B FI 90764B FI 890283 A FI890283 A FI 890283A FI 890283 A FI890283 A FI 890283A FI 90764 B FI90764 B FI 90764B
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- Finland
- Prior art keywords
- compound
- formula
- mixture
- solution
- hydroxy
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- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- JWUBBDSIWDLEOM-XHQRYOPUSA-N (3e)-3-[(2e)-2-[1-(6-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol Chemical class C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2\C1=C\C=C1/CC(O)CCC1=C JWUBBDSIWDLEOM-XHQRYOPUSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
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- 239000000047 product Substances 0.000 description 28
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- CMVIVIVCPJNCMF-UHFFFAOYSA-N (4-bromo-2-methylbutan-2-yl)oxy-triethylsilane Chemical compound CC[Si](CC)(CC)OC(C)(C)CCBr CMVIVIVCPJNCMF-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- RBFVGQWGOARJRU-UHFFFAOYSA-N 4-bromo-2-methylbutan-2-ol Chemical compound CC(C)(O)CCBr RBFVGQWGOARJRU-UHFFFAOYSA-N 0.000 description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
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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
- 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
- A61P35/00—Antineoplastic agents
-
- 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 Table
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nutrition Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (5)
1. Förfarande för framställning av terapeutiskt användbara 25-hydroxi-vitamin D-derivat med formeln 5 f^OH l 1 . 15 väri R är väte eller hydroxi och A är -ChC-, -CH=CH-, som har E-konfiguration, eller -CH2-CH2-, känneteck-n a t därav, att motsvarande förening med formel I, som i stäilet för tvä eller tre hydroxigrupper innehäller tvä eller tre skyddade hydroxigrupper, med formeln
20 -OSi(R1,R2,R3), väri Rx och R3 betecknar C1.4-alkyl och R2 är C1.4-alkyl, aryl eller aryl-C1.4-alkyl, bringas att reagera med ett ämne som förmär avlägsna-skyddsgrupperna. 25 2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer en förening enligt patentkrav 1, ur en grupp bestäende av: 1.25- dihydroxi-16-dehydro-23-didehydrokolekalcife- rol, 30 1,25-dihydroxi-16,23E-bisdehydrokolekalciferol, och 1.25- dihydroxi-16-dehydrokolekalciferol. Il 90764 35
3. En förening med formeln 5 Γ ^—\ I os;—r, 5. y i R3 T H o kännetecknad därav, att A är -CH=CH-, som har 10 E-konfiguration, -CH2-CH2- eller speciellt -CsC-, och R2 och R3 betecknar oberoende av varandra lägre alkyl, speciellt metyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14593288A | 1988-01-20 | 1988-01-20 | |
| US14593288 | 1988-01-20 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI890283A0 FI890283A0 (sv) | 1989-01-19 |
| FI890283A FI890283A (sv) | 1989-07-21 |
| FI90764B true FI90764B (sv) | 1993-12-15 |
| FI90764C FI90764C (sv) | 1994-03-25 |
Family
ID=22515181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI890283A FI90764C (sv) | 1988-01-20 | 1989-01-19 | Förfarande för framställning av terapeutiskt användbara 25-hydroxi-vitamin D-derivat |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0325279B1 (sv) |
| JP (1) | JPH0764806B2 (sv) |
| KR (1) | KR960009119B1 (sv) |
| AR (1) | AR247551A1 (sv) |
| AT (1) | ATE74350T1 (sv) |
| AU (1) | AU622139B2 (sv) |
| BG (1) | BG60530B2 (sv) |
| CA (1) | CA1337529C (sv) |
| DE (1) | DE58901056D1 (sv) |
| DK (1) | DK169945B1 (sv) |
| ES (1) | ES2033467T3 (sv) |
| FI (1) | FI90764C (sv) |
| GR (1) | GR3004786T3 (sv) |
| HU (1) | HU201007B (sv) |
| IE (1) | IE60921B1 (sv) |
| IL (1) | IL88989A (sv) |
| MC (1) | MC1998A1 (sv) |
| NO (1) | NO175429C (sv) |
| NZ (1) | NZ227641A (sv) |
| PH (1) | PH25605A (sv) |
| PT (1) | PT89486B (sv) |
| YU (1) | YU47298B (sv) |
| ZA (1) | ZA8923B (sv) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804502A (en) * | 1988-01-20 | 1989-02-14 | Hoffmann-La Roche Inc. | Vitamin D compounds |
| ATE99942T1 (de) * | 1989-05-18 | 1994-01-15 | Hoffmann La Roche | Dehydrocholecalciferolderivate. |
| AU650751B2 (en) * | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
| EP0580968B1 (en) * | 1992-05-20 | 1996-08-28 | F. Hoffmann-La Roche Ag | Vitamin D3 fluorinated analogs |
| US5753638A (en) * | 1992-10-07 | 1998-05-19 | Hoffmann-La Roche Inc. | Method of treating hyperproliferative skin disease with Vitamin D3 fluorinated analogs |
| CA2096105A1 (en) * | 1992-10-07 | 1994-04-08 | Enrico Giuseppe Baggiolini (Deceased) | Vitamin d3 fluorinated analogs |
| TW267161B (sv) * | 1992-11-20 | 1996-01-01 | Hoffmann La Roche | |
| US5401733A (en) * | 1993-10-01 | 1995-03-28 | Hoffmann-La Roche Inc. | Stable and active metabolites of 1,25-dihydroxy-16-ene-cholecalciferol |
| US5428029A (en) * | 1993-11-24 | 1995-06-27 | Hoffmann-La Roche Inc. | Vitamin D3 fluorinated analogs |
| TW403735B (en) * | 1995-11-22 | 2000-09-01 | Hoffmann La Roche | 25-hydroxy-16-ene-26, 27-bishomo-cholecalciferol |
| AU708679B2 (en) * | 1996-03-21 | 1999-08-12 | F. Hoffmann-La Roche Ag | 1,25-dihydroxy-16,22,23-trisdehydro-cholecalciferol derivatives |
| US5939408A (en) * | 1996-05-23 | 1999-08-17 | Hoffman-La Roche Inc. | Vitamin D3 analogs |
| SG70009A1 (en) * | 1996-05-23 | 2000-01-25 | Hoffmann La Roche | Vitamin d3 analogs |
| DK0884308T3 (da) * | 1997-05-02 | 2003-07-21 | Duphar Int Res | Fremgangsmåde til at fremstille 16-dehydro vitamin D forbindelser |
| US6331642B1 (en) * | 1999-07-12 | 2001-12-18 | Hoffmann-La Roche Inc. | Vitamin D3 analogs |
| JP4795023B2 (ja) * | 2004-02-03 | 2011-10-19 | 中外製薬株式会社 | ビタミンｄ化合物及びそれらの合成中間体の合成方法 |
| EP1883626B1 (en) * | 2005-04-25 | 2017-10-11 | OPKO Ireland Global Holdings, Ltd. | Low-calcemic 16,23-diene 25-oxime analogs of 1alpha,25-dihydroxy vitamin d3 |
| AU2006279331A1 (en) * | 2005-08-18 | 2007-02-22 | Bioxell S.P.A. | Synthesis of 1alpha-fluoro-25-hydroxy-16-23e-diene-26,27-bishomo-20-epi-cholecalciferol |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2812741A1 (de) * | 1977-03-24 | 1978-10-05 | Wisconsin Alumni Res Found | Vitamin d tief 3 -derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| FR2426044A2 (fr) * | 1978-05-19 | 1979-12-14 | Wisconsin Research Foundation | Derives de la vitamine d3 ayant une activite anti-vitamine d |
| US4360471A (en) * | 1981-12-11 | 1982-11-23 | Wisconsin Alumni Research Foundation | 23-Dehydro-25-hydroxyvitamin D3 |
| US4508651A (en) * | 1983-03-21 | 1985-04-02 | Hoffmann-La Roche Inc. | Synthesis of 1α,25-dihydroxyergocalciferol |
| US4505906A (en) * | 1984-01-30 | 1985-03-19 | Wisconsin Alumni Research Foundation | Hydroxyvitamin D2 isomers |
| US4612308A (en) * | 1984-11-29 | 1986-09-16 | Hoffmann-La Roche Inc. | 25,26-Dehydro-1α,23(S,R)-dihydroxycholecalciferol and its epimers |
| US4898855A (en) * | 1987-09-14 | 1990-02-06 | Hoffman-La Roche Inc. | Deuterated analogs of 1,25-dihydroxycholecalciferol |
| US4804502A (en) * | 1988-01-20 | 1989-02-14 | Hoffmann-La Roche Inc. | Vitamin D compounds |
| ATE99942T1 (de) * | 1989-05-18 | 1994-01-15 | Hoffmann La Roche | Dehydrocholecalciferolderivate. |
-
1989
- 1989-01-03 ZA ZA8923A patent/ZA8923B/xx unknown
- 1989-01-17 NZ NZ227641A patent/NZ227641A/en unknown
- 1989-01-17 CA CA000588384A patent/CA1337529C/en not_active Expired - Fee Related
- 1989-01-17 DK DK019789A patent/DK169945B1/da not_active IP Right Cessation
- 1989-01-17 PH PH38057A patent/PH25605A/en unknown
- 1989-01-18 HU HU89175A patent/HU201007B/hu not_active IP Right Cessation
- 1989-01-18 AR AR89313011A patent/AR247551A1/es active
- 1989-01-18 IL IL88989A patent/IL88989A/xx not_active IP Right Cessation
- 1989-01-19 JP JP1008782A patent/JPH0764806B2/ja not_active Expired - Fee Related
- 1989-01-19 NO NO890239A patent/NO175429C/no unknown
- 1989-01-19 YU YU11789A patent/YU47298B/sh unknown
- 1989-01-19 AU AU28644/89A patent/AU622139B2/en not_active Ceased
- 1989-01-19 FI FI890283A patent/FI90764C/sv not_active IP Right Cessation
- 1989-01-19 MC MC902029A patent/MC1998A1/xx unknown
- 1989-01-19 KR KR89000514A patent/KR960009119B1/ko not_active IP Right Cessation
- 1989-01-19 PT PT89486A patent/PT89486B/pt not_active IP Right Cessation
- 1989-01-19 IE IE15789A patent/IE60921B1/en not_active IP Right Cessation
- 1989-01-20 AT AT89100974T patent/ATE74350T1/de not_active IP Right Cessation
- 1989-01-20 DE DE8989100974T patent/DE58901056D1/de not_active Expired - Fee Related
- 1989-01-20 ES ES198989100974T patent/ES2033467T3/es not_active Expired - Lifetime
- 1989-01-20 EP EP89100974A patent/EP0325279B1/de not_active Expired - Lifetime
-
1992
- 1992-06-03 GR GR920401138T patent/GR3004786T3/el unknown
-
1994
- 1994-02-24 BG BG98544A patent/BG60530B2/bg unknown
Also Published As
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