CN100436474C - 胆甾-3β,5α,6β,19-四羟基-24-酮及其衍生物的合成方法 - Google Patents
胆甾-3β,5α,6β,19-四羟基-24-酮及其衍生物的合成方法 Download PDFInfo
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- CN100436474C CN100436474C CNB200510121374XA CN200510121374A CN100436474C CN 100436474 C CN100436474 C CN 100436474C CN B200510121374X A CNB200510121374X A CN B200510121374XA CN 200510121374 A CN200510121374 A CN 200510121374A CN 100436474 C CN100436474 C CN 100436474C
- Authority
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- Prior art keywords
- beta
- ketone
- courage steroid
- cholest
- solution
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- 241001175904 Labeo bata Species 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010189 synthetic method Methods 0.000 claims abstract description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000005855 radiation Effects 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 9
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960000583 acetic acid Drugs 0.000 claims abstract description 6
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 claims abstract description 3
- -1 isopropyl cadion Chemical compound 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- 239000007787 solid Substances 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
- 238000001035 drying Methods 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 20
- 238000010898 silica gel chromatography Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 15
- 238000010025 steaming Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 14
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 14
- 239000012153 distilled water Substances 0.000 claims description 12
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 150000007857 hydrazones Chemical class 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- 235000010265 sodium sulphite Nutrition 0.000 claims description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- 239000010410 layer Substances 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001263 acyl chlorides Chemical class 0.000 abstract description 3
- UFDULEKOJAEIRI-UHFFFAOYSA-N (2-acetyloxy-3-iodophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(I)=C1OC(C)=O UFDULEKOJAEIRI-UHFFFAOYSA-N 0.000 abstract 1
- 230000006907 apoptotic process Effects 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000019581 neuron apoptotic process Effects 0.000 description 2
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241001400381 Nephthea Species 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229940115088 sea soft Drugs 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510121374XA CN100436474C (zh) | 2005-12-31 | 2005-12-31 | 胆甾-3β,5α,6β,19-四羟基-24-酮及其衍生物的合成方法 |
AU2006332419A AU2006332419A1 (en) | 2005-12-31 | 2006-07-10 | The use of phthalide derivatives |
PCT/CN2006/001627 WO2007076655A1 (en) | 2005-12-31 | 2006-07-10 | METHOD FOR SYNTHESIS OF CHOLEST-3β,5α,6β,19-TETRAHYDROXY-24-ONE AND ITS DERIVATIVES |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB200510121374XA CN100436474C (zh) | 2005-12-31 | 2005-12-31 | 胆甾-3β,5α,6β,19-四羟基-24-酮及其衍生物的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1793159A CN1793159A (zh) | 2006-06-28 |
CN100436474C true CN100436474C (zh) | 2008-11-26 |
Family
ID=36804818
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB200510121374XA Active CN100436474C (zh) | 2005-12-31 | 2005-12-31 | 胆甾-3β,5α,6β,19-四羟基-24-酮及其衍生物的合成方法 |
Country Status (2)
Country | Link |
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CN (1) | CN100436474C (zh) |
WO (1) | WO2007076655A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104497086B (zh) * | 2014-12-12 | 2016-08-17 | 中山大学 | 雄甾-3β,5α,6β,19-四醇及其制备方法与应用 |
CN106146593B (zh) * | 2015-04-14 | 2021-06-01 | 南京迈诺威医药科技有限公司 | 一种制备去氧胆酸的方法 |
CN114671796B (zh) * | 2022-04-22 | 2024-06-11 | 宁波工程学院 | 一种光催化合成n-烷基邻苯二甲酰亚胺的方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4298537A (en) * | 1978-11-30 | 1981-11-03 | Teijin Limited | Process for producing steroid compounds having an oxo group in the side chain |
CN1448399A (zh) * | 2003-04-24 | 2003-10-15 | 中山大学 | 24-亚甲基-胆甾-5-烯-3β,19-二醇的合成方法 |
CN1448400A (zh) * | 2003-05-06 | 2003-10-15 | 中山大学 | 24-亚甲基-胆甾-3β,5α,6β,19-四醇的合成方法 |
CN1583782A (zh) * | 2004-05-28 | 2005-02-23 | 中山大学 | 24-亚甲基-胆甾-5 -烯-3β,7β,19-三醇的合成方法 |
CN1583781A (zh) * | 2004-05-28 | 2005-02-23 | 中山大学 | 3β,7β,19-三羟基-5-烯-胆甾烷的合成方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK0688333T3 (da) * | 1993-03-10 | 1999-02-08 | Magainin Pharma | Steroidderivater, farmaceutiske præparater indeholdende disse og deres anvendelse som antibiotika eller desinfektionsmidler |
-
2005
- 2005-12-31 CN CNB200510121374XA patent/CN100436474C/zh active Active
-
2006
- 2006-07-10 WO PCT/CN2006/001627 patent/WO2007076655A1/zh active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4298537A (en) * | 1978-11-30 | 1981-11-03 | Teijin Limited | Process for producing steroid compounds having an oxo group in the side chain |
CN1448399A (zh) * | 2003-04-24 | 2003-10-15 | 中山大学 | 24-亚甲基-胆甾-5-烯-3β,19-二醇的合成方法 |
CN1448400A (zh) * | 2003-05-06 | 2003-10-15 | 中山大学 | 24-亚甲基-胆甾-3β,5α,6β,19-四醇的合成方法 |
CN1583782A (zh) * | 2004-05-28 | 2005-02-23 | 中山大学 | 24-亚甲基-胆甾-5 -烯-3β,7β,19-三醇的合成方法 |
CN1583781A (zh) * | 2004-05-28 | 2005-02-23 | 中山大学 | 3β,7β,19-三羟基-5-烯-胆甾烷的合成方法 |
Non-Patent Citations (9)
Title |
---|
24-亚甲基胆甾-4-烯-3β ,6β-二醇的合成. 陆伟刚,何延红,苏镜娱,曾陇梅.中山大学学报(自然科学版),第43卷第4期. 2004 |
24-亚甲基胆甾-4-烯-3β,6β-二醇的合成. 陆伟刚,何延红,苏镜娱,曾陇梅.中山大学学报(自然科学版),第43卷第4期. 2004 * |
24-亚甲基胆甾-5-烯-3β,19-二醇的合成. 陆伟刚等.高等学校化学学报,第25卷第9期. 2004 |
24-亚甲基胆甾-5-烯-3β,19-二醇的合成. 陆伟刚等.高等学校化学学报,第25卷第9期. 2004 * |
3-乙酰氧基胆甾-5-烯-19-羟基-24-酮的制备与表征. 崔建国等.广西科学,第10卷第1期. 2003 |
3-乙酰氧基胆甾-5-烯-19-羟基-24-酮的制备与表征. 崔建国等.广西科学,第10卷第1期. 2003 * |
Reduction of 3b-chloro-6-nitrocholest-5-ene withRaneynickel-hydrazine hydrate: a synthesis of dimers.. Shafiullah,Husain Shakir,Basha D. M., Ansari M. R.Indian J. Chem., Sect. B,Vol.28B No.8. 1989 |
Synthesis of polyhydroxysterols (IV): synthesis of24-methylene-cholesta-3b,5a,6b,19-tetrol,a cytotoxic naturalhydroxylated sterol. Weigang Lu, Longmei Zeng, Jingyu Su.Steroids,Vol.69 . 2004 |
Δ5 23β,7β2二羟基甾醇和Δ5 23β,7α2二羟基甾醇的立体选择合成及其对胆碱酯酶的抑制活性. 陆伟刚,张军,苏镜娱,曾陇梅.中国药物化学杂志,第15卷第4期. 2005 |
Also Published As
Publication number | Publication date |
---|---|
WO2007076655A1 (en) | 2007-07-12 |
CN1793159A (zh) | 2006-06-28 |
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