NO300209B1 - Analogifremgangsmåte for fremstilling av sidekjede-homologe vitamin-D-derivater - Google Patents
Analogifremgangsmåte for fremstilling av sidekjede-homologe vitamin-D-derivater Download PDFInfo
- Publication number
- NO300209B1 NO300209B1 NO913913A NO913913A NO300209B1 NO 300209 B1 NO300209 B1 NO 300209B1 NO 913913 A NO913913 A NO 913913A NO 913913 A NO913913 A NO 913913A NO 300209 B1 NO300209 B1 NO 300209B1
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- Norway
- Prior art keywords
- denotes
- hydroxy
- compound
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- bond
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- 150000003710 vitamin D derivatives Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 230000009467 reduction Effects 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
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- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
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- 125000004429 atom Chemical group 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
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- 235000005282 vitamin D3 Nutrition 0.000 description 2
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- 239000003872 25-hydroxy-cholecalciferol Substances 0.000 description 1
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- 229930182555 Penicillin Natural products 0.000 description 1
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
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- 101710183568 Serine/threonine-protein kinase PknK Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
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- 230000002159 abnormal effect Effects 0.000 description 1
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- JWUBBDSIWDLEOM-DTOXIADCSA-N calcidiol 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)CCC1=C JWUBBDSIWDLEOM-DTOXIADCSA-N 0.000 description 1
- 150000001668 calcitriol derivatives Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000004663 cell proliferation 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 group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 108010007093 dispase Proteins 0.000 description 1
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- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XCSNRICUVQIXEM-UHFFFAOYSA-N ethyl 2-(2-diethoxyphosphorylethoxy)acetate Chemical compound CCOC(=O)COCCP(=O)(OCC)OCC XCSNRICUVQIXEM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 210000004765 promyelocyte Anatomy 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
- 229960000342 retinol acetate Drugs 0.000 description 1
- 235000019173 retinyl acetate Nutrition 0.000 description 1
- 239000011770 retinyl acetate Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010626 work up procedure 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
- A61P35/00—Antineoplastic agents
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)
- 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)
- Lubricants (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4003854A DE4003854A1 (de) | 1990-02-06 | 1990-02-06 | Seitenketten-homologe vitamin d-derivate, verfahren zu ihrer herstellung, diese derivate enthaltende pharmazeutische praeparate sowie deren verwendung als arzneimittel |
| DE19904034730 DE4034730A1 (de) | 1990-10-30 | 1990-10-30 | Seitenketten-homologe vitamin-d-derivate, verfahren zu ihrer herstellung, diese derivate enthaltende pharmazeutische praeparate sowie deren verwendung als arzneimittel |
| PCT/DE1991/000104 WO1991012238A1 (fr) | 1990-02-06 | 1991-02-06 | Derives de vitamine d homologues en chaines laterales, leur procede de production, des compositions pharmaceutiques contenant ces derives et leur utilisation comme medicaments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO913913D0 NO913913D0 (no) | 1991-10-04 |
| NO913913L NO913913L (no) | 1991-12-05 |
| NO300209B1 true NO300209B1 (no) | 1997-04-28 |
Family
ID=25889898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO913913A NO300209B1 (no) | 1990-02-06 | 1991-10-04 | Analogifremgangsmåte for fremstilling av sidekjede-homologe vitamin-D-derivater |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0441467B1 (fr) |
| JP (1) | JPH05501718A (fr) |
| CN (1) | CN1029400C (fr) |
| AT (1) | ATE106391T1 (fr) |
| AU (1) | AU652739B2 (fr) |
| CA (1) | CA2058637A1 (fr) |
| CZ (1) | CZ280203B6 (fr) |
| DE (1) | DE59101738D1 (fr) |
| DK (1) | DK0441467T3 (fr) |
| ES (1) | ES2055521T3 (fr) |
| FI (1) | FI100598B (fr) |
| HU (1) | HUT59665A (fr) |
| IE (1) | IE70239B1 (fr) |
| IL (1) | IL97158A (fr) |
| NO (1) | NO300209B1 (fr) |
| PT (1) | PT96679B (fr) |
| WO (1) | WO1991012238A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5532228A (en) * | 1990-02-06 | 1996-07-02 | Schering Aktiengesellschaft | Side-chain homologous vitamin D derivatives, process for their production, pharmaceutical preparations containing these derivatives and their use as pharmaceutical agents |
| DE4221961A1 (de) * | 1992-06-30 | 1994-01-05 | Schering Ag | 22-En-25-oxa-Derivate in der Vitamin D-Reihe, Verfahren zu ihrer Herstellung, diese Derivate enthaltenen pharmazeutische Präparate sowie deren Verwendung als Arzneimittel |
| GB9223061D0 (en) * | 1992-11-04 | 1992-12-16 | Leo Pharm Prod Ltd | Chemical compounds |
| TW267161B (fr) * | 1992-11-20 | 1996-01-01 | Hoffmann La Roche | |
| DE4343694C2 (de) * | 1993-12-16 | 1997-02-13 | Schering Ag | Verfahren zur Homologisierung von geschützten C-22-Vitamin D-Aldehyden und Zwischenprodukte des Verfahrens |
| GB9524812D0 (en) * | 1995-12-05 | 1996-02-07 | Leo Pharm Prod Ltd | Chemical compounds |
| JP2001510183A (ja) * | 1997-07-17 | 2001-07-31 | エフ．ホフマン−ラ ロシュ アーゲー | 側鎖に２つの不飽和結合を有するジホモ−セコ−コレスタン |
| DE19935771A1 (de) | 1999-07-23 | 2001-02-01 | Schering Ag | Neue Vitamin D-Derivate mit cyclischen Substrukturen in den Seitenketten, Verfahren und Zwischenprodukte zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| JP2005257271A (ja) * | 2002-02-25 | 2005-09-22 | Chugai Pharmaceut Co Ltd | ビタミンｄ３誘導体とビタミンｄ３受容体の結合の検出方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| US4588528A (en) * | 1984-05-31 | 1986-05-13 | Wisconsin Alumni Research Foundation | 1,24-dihydroxy-Δ22 -vitamin D3 and process for preparing same |
| WO1987000834A1 (fr) * | 1985-08-02 | 1987-02-12 | Leo Pharmaceutical Products Ltd. A/S | Nouveaux analogues de la vitamine d |
-
1991
- 1991-02-06 ES ES91250032T patent/ES2055521T3/es not_active Expired - Lifetime
- 1991-02-06 AU AU72161/91A patent/AU652739B2/en not_active Ceased
- 1991-02-06 EP EP91250032A patent/EP0441467B1/fr not_active Expired - Lifetime
- 1991-02-06 IE IE38991A patent/IE70239B1/en not_active IP Right Cessation
- 1991-02-06 AT AT91250032T patent/ATE106391T1/de active
- 1991-02-06 IL IL9715891A patent/IL97158A/en not_active IP Right Cessation
- 1991-02-06 DK DK91250032.9T patent/DK0441467T3/da active
- 1991-02-06 CZ CS91281A patent/CZ280203B6/cs not_active IP Right Cessation
- 1991-02-06 CA CA002058637A patent/CA2058637A1/fr not_active Abandoned
- 1991-02-06 JP JP3503657A patent/JPH05501718A/ja active Pending
- 1991-02-06 PT PT96679A patent/PT96679B/pt not_active IP Right Cessation
- 1991-02-06 DE DE59101738T patent/DE59101738D1/de not_active Expired - Lifetime
- 1991-02-06 CN CN91101506A patent/CN1029400C/zh not_active Expired - Fee Related
- 1991-02-06 WO PCT/DE1991/000104 patent/WO1991012238A1/fr active IP Right Grant
- 1991-10-04 NO NO913913A patent/NO300209B1/no unknown
- 1991-10-04 FI FI914677A patent/FI100598B/fi active
- 1991-11-05 HU HU913475A patent/HUT59665A/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05501718A (ja) | 1993-04-02 |
| FI100598B (fi) | 1998-01-15 |
| IL97158A (en) | 1994-12-29 |
| IE70239B1 (en) | 1996-11-13 |
| DK0441467T3 (da) | 1994-10-03 |
| HU913475D0 (en) | 1992-05-28 |
| PT96679B (pt) | 1998-07-31 |
| NO913913L (no) | 1991-12-05 |
| WO1991012238A1 (fr) | 1991-08-22 |
| CS28191A3 (en) | 1992-04-15 |
| AU652739B2 (en) | 1994-09-08 |
| CN1054588A (zh) | 1991-09-18 |
| IE910389A1 (en) | 1991-08-14 |
| ATE106391T1 (de) | 1994-06-15 |
| PT96679A (pt) | 1991-10-31 |
| EP0441467A1 (fr) | 1991-08-14 |
| HUT59665A (en) | 1992-06-29 |
| FI914677A0 (fi) | 1991-10-04 |
| IL97158A0 (en) | 1992-05-25 |
| EP0441467B1 (fr) | 1994-06-01 |
| ES2055521T3 (es) | 1994-08-16 |
| CZ280203B6 (cs) | 1995-11-15 |
| NO913913D0 (no) | 1991-10-04 |
| CN1029400C (zh) | 1995-08-02 |
| AU7216191A (en) | 1991-09-03 |
| DE59101738D1 (de) | 1994-07-07 |
| CA2058637A1 (fr) | 1991-08-07 |
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