JPH0244312B2 - - Google Patents
Info
- Publication number
- JPH0244312B2 JPH0244312B2 JP57053686A JP5368682A JPH0244312B2 JP H0244312 B2 JPH0244312 B2 JP H0244312B2 JP 57053686 A JP57053686 A JP 57053686A JP 5368682 A JP5368682 A JP 5368682A JP H0244312 B2 JPH0244312 B2 JP H0244312B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- vitamin
- sulfur dioxide
- aromatic
- formula
- 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 - Lifetime
Links
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 14
- 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 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UPODXJOTVHSJMI-UHFFFAOYSA-M O=[S+]=O.CC([O-])=O Chemical compound O=[S+]=O.CC([O-])=O UPODXJOTVHSJMI-UHFFFAOYSA-M 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FCKJYANJHNLEEP-XRWYNYHCSA-N (24R)-24,25-dihydroxycalciol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CC[C@@H](O)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C FCKJYANJHNLEEP-XRWYNYHCSA-N 0.000 description 1
- GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- 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 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 235000020964 calcitriol Nutrition 0.000 description 1
- 239000011612 calcitriol Substances 0.000 description 1
- 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 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5368682A JPS58172388A (ja) | 1982-04-02 | 1982-04-02 | 新規なビタミンｄ↓３誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5368682A JPS58172388A (ja) | 1982-04-02 | 1982-04-02 | 新規なビタミンｄ↓３誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58172388A JPS58172388A (ja) | 1983-10-11 |
| JPH0244312B2 true JPH0244312B2 (enrdf_load_stackoverflow) | 1990-10-03 |
Family
ID=12949695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5368682A Granted JPS58172388A (ja) | 1982-04-02 | 1982-04-02 | 新規なビタミンｄ↓３誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58172388A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107325173A (zh) * | 2016-04-28 | 2017-11-07 | 上海惠斯生物科技有限公司 | 一种25羟基维生素d3人工抗原、制备方法及应用 |
-
1982
- 1982-04-02 JP JP5368682A patent/JPS58172388A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEMISTRY LETTERS=1979 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58172388A (ja) | 1983-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5892068A (en) | Preparation of sterol and stanol-esters | |
| HU199497B (en) | Process for producing acid addition salts, alcohol solvates and hydrates of 7-halogen-7-deoxylincomycin | |
| EP0168119A1 (en) | Chemiluminescent substituted epidoxy-polycycloalkyl polycycloalkanes and process for preparing these compounds | |
| GB1564808A (en) | 23,24-epoxy-25-hydroxycholestane derivatives | |
| JPH0244312B2 (enrdf_load_stackoverflow) | ||
| US4189596A (en) | Preparing 2-arylalkanoic acid derivatives | |
| JPH0420431B2 (enrdf_load_stackoverflow) | ||
| EP0243646B1 (en) | A process for the preparation of forskolin from 9-deoxy-forskolin and intermediates used therein | |
| Smith et al. | 11, 12-Secoprostaglandins. 3. 8-Alkylthio (sulfinyl and sulfonyl)-12-hydroxyalkanoic acids and related compounds | |
| US4008270A (en) | Process for preparing 2-(substituted phenyl)propionic acids | |
| JPS6228149B2 (enrdf_load_stackoverflow) | ||
| JPH08239340A (ja) | ベンゾキノン系誘導体の製造法 | |
| SU450405A3 (ru) | Способ получени 17 -этинилэстриолов | |
| JPH07206789A (ja) | コンブレタスタチン類縁化合物 | |
| SU715580A1 (ru) | Способ получени кремнийацетиленовых карбонильных соединений | |
| JP3256259B2 (ja) | スルホン誘導体の製造方法 | |
| EP0170506B1 (en) | Method for inversion of optically active 4-hydroxy-2-cyclopentenones | |
| US3308139A (en) | Cyclopropa-androstanone compounds | |
| JPS6241510B2 (enrdf_load_stackoverflow) | ||
| JPS6126553B2 (enrdf_load_stackoverflow) | ||
| US4208526A (en) | Process for the preparation of thiazolidin-4-one-acetic acid derivatives | |
| KR950001277B1 (ko) | 옥시벤젠 유도체의 제조방법 | |
| KR20010102330A (ko) | 3-메틸 비타민 ｄ 유도체 | |
| SU374296A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ 3-АЦЕТАТА 20-ЭТИЛКАРБОНАТА 16а-МЕТИЛПРЕГНАДИЕН-5,17 | |
| KR820001213B1 (ko) | 반합성 4"-옥소올레안도 마이신 중간물질의 제조방법 |