JPS6129360B2 - - Google Patents
Info
- Publication number
- JPS6129360B2 JPS6129360B2 JP6892878A JP6892878A JPS6129360B2 JP S6129360 B2 JPS6129360 B2 JP S6129360B2 JP 6892878 A JP6892878 A JP 6892878A JP 6892878 A JP6892878 A JP 6892878A JP S6129360 B2 JPS6129360 B2 JP S6129360B2
- Authority
- JP
- Japan
- Prior art keywords
- ene
- group
- epoxy
- epoxycholest
- dibenzoyloxy
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- -1 t-butyldimethylsilyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QOWCBCXATJITSI-ZLNGONTQSA-N (6r)-6-[(1r,3as,4e,7ar)-4-[(2z)-2-[(5s)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-1-yl]-2-methylheptane-1,2-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(O)CO)C)=C\C=C1\C[C@@H](O)CCC1=C QOWCBCXATJITSI-ZLNGONTQSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- HIAJCGFYHIANNA-QIZZZRFXSA-N 3b-Hydroxy-5-cholenoic acid Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 HIAJCGFYHIANNA-QIZZZRFXSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- TWWQSIQFQAWJJU-GPPBBECHSA-N (6r)-6-[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-1-ol Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(CO)C)[C@@]1(C)CC2 TWWQSIQFQAWJJU-GPPBBECHSA-N 0.000 description 2
- YCUIAJHAAAVRIH-HGUAUECJSA-N (6r)-6-[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-1,1-diol Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C(O)O)[C@@]1(C)CC2 YCUIAJHAAAVRIH-HGUAUECJSA-N 0.000 description 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical group 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 2
- WYLBDLGJLBJKSV-GHMQSXNDSA-N (6r)-6-[(3s,8s,9s,10r,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-1,2-diol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(O)CO)C)[C@@]1(C)CC2 WYLBDLGJLBJKSV-GHMQSXNDSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6892878A JPS54163565A (en) | 1978-06-09 | 1978-06-09 | 24*255epoxyy3beta * 266 dihydroxyychlestoo55ene or protected derivative of hydroxyl group thereof and production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6892878A JPS54163565A (en) | 1978-06-09 | 1978-06-09 | 24*255epoxyy3beta * 266 dihydroxyychlestoo55ene or protected derivative of hydroxyl group thereof and production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54163565A JPS54163565A (en) | 1979-12-26 |
| JPS6129360B2 true JPS6129360B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-07-05 |
Family
ID=13387797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6892878A Granted JPS54163565A (en) | 1978-06-09 | 1978-06-09 | 24*255epoxyy3beta * 266 dihydroxyychlestoo55ene or protected derivative of hydroxyl group thereof and production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54163565A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI2753632T3 (fi) | 2011-09-08 | 2023-08-02 | Sage Therapeutics Inc | Neuroaktiivisia steroideja, koostumuksia ja niiden käyttöjä |
| US20160031930A1 (en) | 2013-03-13 | 2016-02-04 | Sage Therapeutics, Inc. | Neuroactive steroids and methods of use thereof |
| ES2970222T3 (es) | 2014-06-18 | 2024-05-27 | Sage Therapeutics Inc | Oxiesteroles y procedimientos de uso de los mismos |
| HRP20210526T8 (hr) | 2015-07-06 | 2021-08-20 | Sage Therapeutics, Inc. | Oksisteroli i postupci za njihovu uporabu |
| WO2017007832A1 (en) * | 2015-07-06 | 2017-01-12 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| SMT202500264T1 (it) | 2015-07-06 | 2025-09-12 | Sage Therapeutics Inc | Ossisteroli e metodi di uso degli stessi |
| JP7112331B2 (ja) | 2016-04-01 | 2022-08-03 | セージ セラピューティクス， インコーポレイテッド | オキシステロールおよびその使用方法 |
| US10752653B2 (en) | 2016-05-06 | 2020-08-25 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| WO2018009867A1 (en) | 2016-07-07 | 2018-01-11 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| MX392270B (es) | 2016-09-30 | 2025-03-24 | Sage Therapeutics Inc | Oxisteroles sustituidos en c7 y metodos de uso de los mismos. |
| KR20230051723A (ko) | 2016-10-18 | 2023-04-18 | 세이지 테라퓨틱스, 인크. | 옥시스테롤 및 그의 사용 방법 |
| TWI815800B (zh) | 2016-10-18 | 2023-09-21 | 美商賽吉醫療公司 | 氧固醇(oxysterol)及其使用方法 |
-
1978
- 1978-06-09 JP JP6892878A patent/JPS54163565A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54163565A (en) | 1979-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4772433A (en) | Vitamin D analogues | |
| US3822254A (en) | Synthesis of 25-hydroxycholesterol | |
| US4554105A (en) | Process for the preparation of 1-hydroxylated vitamin D compounds | |
| JPS6129360B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS5840960B2 (ja) | ヒドロキシコレステロ−ル立体異性体間の相互変換法 | |
| JP2741497B2 (ja) | １α−ヒドロキシビタミンＤ化合物の中間体 | |
| FR2569408A1 (fr) | Nouveaux steroides substitues en position 10 par un radical comportant une double ou triple liaison, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant | |
| JPS6246556B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0639468B2 (ja) | ヒドロキノン誘導体 | |
| EP0045524B1 (en) | 22-arylsulfonyl-24,25-dihydroxycholestanes and process for preparing the same | |
| JP2975705B2 (ja) | ステロイド誘導体 | |
| JP2517743B2 (ja) | 光学活性アルコ―ルの製造法 | |
| JP2984406B2 (ja) | ステロイド誘導体の製造法 | |
| US5283345A (en) | 1β,7,8-trihydroxy vitamin D2, 1∘,7,8-trihydroxy vitamin D3 and their derivatives and method of manufacturing these chemicals | |
| JPH05208995A (ja) | ビタミンｄ誘導体のための中間体および製造方法 | |
| CA1338832C (en) | 1.beta., 7, 8-trihydroxy vitamin d_ and 1.beta., 7, 8-trihydroxy vit amin d , or derivatives therefrom and method of preparing the same | |
| JP3483155B2 (ja) | １α，２５−ジヒドロキシビタミンＤ４およびＤ７の製造法 | |
| CA1053669A (en) | Intermediate cyclopentane derivatives | |
| JPH0825993B2 (ja) | ビタミンｄ２およびｄ３又は活性型ビタミンｄ２およびｄ３の製造方法，並びにその中間体 | |
| JP2683395B2 (ja) | ステロイド誘導体 | |
| JP2975704B2 (ja) | ステロイド誘導体 | |
| JPS6148499B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0912594A (ja) | ステロイド骨格を有する化合物類及びそれらによるゴキブリ拘束物質の製造方法ならびにステロイド骨格を有する新規化合物 | |
| JPH0672928A (ja) | ７−オクチン−１−エン誘導体およびその製造方法 | |
| JPS6352636B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |