CH621131A5 - - Google Patents
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- Publication number
- CH621131A5 CH621131A5 CH113176A CH113176A CH621131A5 CH 621131 A5 CH621131 A5 CH 621131A5 CH 113176 A CH113176 A CH 113176A CH 113176 A CH113176 A CH 113176A CH 621131 A5 CH621131 A5 CH 621131A5
- Authority
- CH
- Switzerland
- Prior art keywords
- diol
- cholesta
- dien
- irradiated
- diene
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 14
- 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 claims description 7
- 239000003872 25-hydroxy-cholecalciferol Substances 0.000 claims description 7
- 235000021318 Calcifediol Nutrition 0.000 claims description 7
- 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 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- JJFYNCJHSCTBPW-TVQCKQBJSA-N cholesta-5,7-dien-3beta,25-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H](CCCC(C)(C)O)C)CC[C@H]33)C)C3=CC=C21 JJFYNCJHSCTBPW-TVQCKQBJSA-N 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical class 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 1
- 230000005855 radiation Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- UVVWRMXOHIVZBN-RPAZCORHSA-N 25-Hydroxytachysterol 3 Chemical compound C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2C(\C=C\C3=C(C)CC[C@H](O)C3)=CCC[C@]12C UVVWRMXOHIVZBN-RPAZCORHSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J15/00—Stereochemically pure steroids containing carbon, hydrogen, halogen or oxygen having a partially or totally inverted skeleton, e.g. retrosteroids, L-isomers
- C07J15/005—Retrosteroids (9 beta 10 alfa)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/551,698 US4001096A (en) | 1975-02-21 | 1975-02-21 | Process for preparing 25-hydroxycholecalciferol intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621131A5 true CH621131A5 (xx) | 1981-01-15 |
Family
ID=24202313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH113176A CH621131A5 (xx) | 1975-02-21 | 1976-01-29 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4001096A (xx) |
| JP (1) | JPS51110555A (xx) |
| CH (1) | CH621131A5 (xx) |
| DE (1) | DE2604310A1 (xx) |
| FR (1) | FR2301538A1 (xx) |
| GB (1) | GB1499262A (xx) |
| NL (1) | NL7601434A (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490226A (en) * | 1982-08-30 | 1984-12-25 | The Regents Of The University Of California | Efficient photochemical formation of 1-α-hydroxyprevitamin D3 |
| EP0536311A4 (en) * | 1990-06-21 | 1993-05-19 | Trustees Of Boston University | Compositions comprising vitamin d precursors, analogs thereof and their use |
| US5167953A (en) * | 1990-06-21 | 1992-12-01 | Trustees Of Boston University | Compositions comprising tachysteral and the use thereof to provide vitamin D |
| US5395829A (en) * | 1990-10-04 | 1995-03-07 | Trustees Of Boston University | Compositions comprising vitamin D lumisterol analog precursors |
| US7264713B2 (en) * | 2003-09-03 | 2007-09-04 | Thomas Kryzak | Apparatus, system and method for remediation of contamination |
| WO2017093192A1 (en) * | 2015-11-30 | 2017-06-08 | Dsm Ip Assets B.V. | Crystallization of 25-hydroxy-7-dehydrocholsterol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL112521C (xx) * | 1960-05-30 | |||
| US3198792A (en) * | 1962-06-12 | 1965-08-03 | Philips Corp | 10alpha methyl, 9beta hormonal steroids |
| US3833622A (en) * | 1969-03-17 | 1974-09-03 | Upjohn Co | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
| JPS5030068B1 (xx) * | 1969-12-16 | 1975-09-29 |
-
1975
- 1975-02-21 US US05/551,698 patent/US4001096A/en not_active Expired - Lifetime
-
1976
- 1976-01-29 CH CH113176A patent/CH621131A5/de not_active IP Right Cessation
- 1976-02-05 DE DE19762604310 patent/DE2604310A1/de not_active Withdrawn
- 1976-02-11 GB GB5269/76A patent/GB1499262A/en not_active Expired
- 1976-02-12 NL NL7601434A patent/NL7601434A/xx not_active Application Discontinuation
- 1976-02-20 FR FR7604850A patent/FR2301538A1/fr active Granted
- 1976-02-20 JP JP51017852A patent/JPS51110555A/ja active Pending
- 1976-08-26 US US05/717,876 patent/US4094890A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2301538A1 (fr) | 1976-09-17 |
| DE2604310A1 (de) | 1976-09-02 |
| NL7601434A (nl) | 1976-08-24 |
| US4094890A (en) | 1978-06-13 |
| GB1499262A (en) | 1978-01-25 |
| FR2301538B1 (xx) | 1979-08-31 |
| US4001096A (en) | 1977-01-04 |
| JPS51110555A (xx) | 1976-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |