JPH0318626B2 - - Google Patents
Info
- Publication number
- JPH0318626B2 JPH0318626B2 JP9937682A JP9937682A JPH0318626B2 JP H0318626 B2 JPH0318626 B2 JP H0318626B2 JP 9937682 A JP9937682 A JP 9937682A JP 9937682 A JP9937682 A JP 9937682A JP H0318626 B2 JPH0318626 B2 JP H0318626B2
- Authority
- JP
- Japan
- Prior art keywords
- methylene chloride
- solvent
- water
- epoxide
- dihydroxyvitamin
- Prior art date
- 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.)
- Expired
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000003704 vitamin D3 derivatives Chemical class 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 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 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 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 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000011612 calcitriol Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BJYLYJCXYAMOFT-RRXOBRNQSA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCC(O)C(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C BJYLYJCXYAMOFT-RRXOBRNQSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol 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)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9937682A JPS58216179A (ja) | 1982-06-11 | 1982-06-11 | 7,8−エポキシ化ビタミンd↓3誘導体 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9937682A JPS58216179A (ja) | 1982-06-11 | 1982-06-11 | 7,8−エポキシ化ビタミンd↓3誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58216179A JPS58216179A (ja) | 1983-12-15 |
JPH0318626B2 true JPH0318626B2 (de) | 1991-03-13 |
Family
ID=14245804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9937682A Granted JPS58216179A (ja) | 1982-06-11 | 1982-06-11 | 7,8−エポキシ化ビタミンd↓3誘導体 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58216179A (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2011781B1 (de) * | 2006-03-15 | 2014-03-05 | MicroBiopharm Japan Co., Ltd. | Verfahren zur herstellung eines indenderivats, und zwischenprodukt für die herstellung des derivats |
WO2020004541A1 (ja) | 2018-06-27 | 2020-01-02 | 中外製薬株式会社 | 油脂中にed-71およびそのエポキシ体を含む油分分散体を含む医薬組成物 |
-
1982
- 1982-06-11 JP JP9937682A patent/JPS58216179A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58216179A (ja) | 1983-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR940010767B1 (ko) | 신규 비타민 d 동족체 | |
CA2125476C (en) | 20-methyl-substituted vitamin d derivatives | |
US5545633A (en) | 17-ene vitamine D analogues | |
KR100294600B1 (ko) | 비타민d계열의25-카르복실산유도체,그의제조방법,그제조방법의중간생성물,그들유도체를함유하는제약조성물및약제의제조를위한그들의용도 | |
DE69307929T2 (de) | Neuen vitamin d derivate | |
FR2634200A1 (fr) | Nouveaux composes derives de la vitamine d, leur procede de preparation et compositions pharmaceutiques contenant ces composes | |
FR2554444A1 (fr) | 1,25-dihydroxyvitamines d2 et procedes pour les preparer | |
GB2142922A (en) | Steroid intermediates in the synthesis of-hydroxyvitamin d2 | |
FR2630740A1 (fr) | Composes derives de vitamine d3, procede pour les preparer et leur utilisation | |
JP2731839B2 (ja) | 同族化されたビタミンD▲下2▼化合物および対応する1α―ヒドロキシル化誘導体 | |
JPH10509715A (ja) | 18,19−ジノル−ビタミンd 化合物 | |
US4505906A (en) | Hydroxyvitamin D2 isomers | |
FR2573760A1 (fr) | Composes derives du cholecalciferol, composition pharmaceutique antitumorale et utilisation desdits composes dans la preparation de cette composition pharmaceutique | |
US5250523A (en) | Side chain unsaturated 1α-hydroxyvitanim D homologs | |
RU2163234C2 (ru) | Аналоги витамина d, способ их получения, диастереоизомер, фармацевтическая композиция | |
EP0562497A1 (de) | 1-Alpha-Hydroxy-Vitamine D7 und D4', Verfahren zur ihren Herstellung und pharmazeutische Präparate davon | |
JPH08501572A (ja) | 新規ビタミンd類似体 | |
US5380720A (en) | Iodo vitamin D3 compounds and method for preparing same | |
JP2003176250A (ja) | (D)−グルコースからの19−ノル−1α,25−ジヒドロキシビタミンD3のA−環合成単位(synthon)の合成 | |
EP1047671B1 (de) | Verfahren zur herstellung von cholecalciferol-derivaten und zwischenverbindungen | |
IE67953B1 (en) | Side Chain Unsaturated 1alpha-Hydroxyvitamin D Homologs | |
JPH0318626B2 (de) | ||
EP0084199B1 (de) | Verfahren zur Herstellung von delta 5,7 Steroiden | |
PT96679B (pt) | Processo para a preparacao de derivados de vitamina d homologos de cadeias laterais e de composicoes farmaceuticas que os contem | |
US5354744A (en) | Side chain unsaturated 1 alpha-hydroxyvitamin D analogs |