CN104447929A - 一种合成3-羰基-4-雄烯-17β羧酸的方法 - Google Patents
一种合成3-羰基-4-雄烯-17β羧酸的方法 Download PDFInfo
- Publication number
- CN104447929A CN104447929A CN201410592089.5A CN201410592089A CN104447929A CN 104447929 A CN104447929 A CN 104447929A CN 201410592089 A CN201410592089 A CN 201410592089A CN 104447929 A CN104447929 A CN 104447929A
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- Prior art keywords
- androstene
- carboxylic acid
- reaction
- carbonyl
- hydroxyl
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- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- YQACAXHKQZCEOI-UDCWSGSHSA-N 4-Androstene-3-oxo-17beta-carboxylic acid Natural products O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(O)=O)[C@@H]4[C@@H]3CCC2=C1 YQACAXHKQZCEOI-UDCWSGSHSA-N 0.000 title claims abstract description 32
- FOEOTLKUMCKCQW-YFWFAHHUSA-N C(=O)=C1C=C2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)C(=O)O Chemical compound C(=O)=C1C=C2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)C(=O)O FOEOTLKUMCKCQW-YFWFAHHUSA-N 0.000 title claims abstract description 32
- 230000002194 synthesizing effect Effects 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 230000001590 oxidative effect Effects 0.000 claims abstract description 11
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000007844 bleaching agent Substances 0.000 claims description 7
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000630 rising effect Effects 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 230000005945 translocation Effects 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 23
- 239000012065 filter cake Substances 0.000 abstract description 6
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 230000007935 neutral effect Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000017105 transposition Effects 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- MGMOLZNAUACBCR-CWQDBKDDSA-N (8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound OC1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(CC1)C)C(=O)O MGMOLZNAUACBCR-CWQDBKDDSA-N 0.000 abstract 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000009987 spinning Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000010189 synthetic method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 230000007613 environmental effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004080 punching Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- -1 carboxylate methyl ester Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229960004199 dutasteride Drugs 0.000 description 1
- JWJOTENAMICLJG-QWBYCMEYSA-N dutasteride Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)N[C@@H]4CC3)C)CC[C@@]21C)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F JWJOTENAMICLJG-QWBYCMEYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410592089.5A CN104447929B (zh) | 2014-10-28 | 2014-10-28 | 一种合成3-羰基-4-雄烯-17β羧酸的方法 |
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CN201410592089.5A CN104447929B (zh) | 2014-10-28 | 2014-10-28 | 一种合成3-羰基-4-雄烯-17β羧酸的方法 |
Publications (2)
Publication Number | Publication Date |
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CN104447929A true CN104447929A (zh) | 2015-03-25 |
CN104447929B CN104447929B (zh) | 2016-06-29 |
Family
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CN201410592089.5A Active CN104447929B (zh) | 2014-10-28 | 2014-10-28 | 一种合成3-羰基-4-雄烯-17β羧酸的方法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113429449A (zh) * | 2020-03-06 | 2021-09-24 | F.I.S.-菲博利佳意大利合成面料股份公司 | 纯化本胆烯酸的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101948495A (zh) * | 2010-10-19 | 2011-01-19 | 浙江仙琚制药股份有限公司 | 化合物19-去甲基-4-雄甾烯-3,17-二酮的制备方法 |
WO2011075701A2 (en) * | 2009-12-18 | 2011-06-23 | Kythera Biopharmaceuticals, Inc. | Methods for the purification of deoxycholic acid |
CN104098639A (zh) * | 2014-08-06 | 2014-10-15 | 赵云现 | 17β-羧基-4-雄烯-3-酮的制备方法 |
-
2014
- 2014-10-28 CN CN201410592089.5A patent/CN104447929B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011075701A2 (en) * | 2009-12-18 | 2011-06-23 | Kythera Biopharmaceuticals, Inc. | Methods for the purification of deoxycholic acid |
CN101948495A (zh) * | 2010-10-19 | 2011-01-19 | 浙江仙琚制药股份有限公司 | 化合物19-去甲基-4-雄甾烯-3,17-二酮的制备方法 |
CN104098639A (zh) * | 2014-08-06 | 2014-10-15 | 赵云现 | 17β-羧基-4-雄烯-3-酮的制备方法 |
Non-Patent Citations (3)
Title |
---|
吴玉萍等: "3- 酮基-4- 雄甾烯-17β- 羧酸甲酯的合成改进", 《中国医药工业杂志》 * |
罗金峰等: "3-羰基-雄甾-4-烯-17β-酸的合成", 《化学工业与工程》 * |
郑锦鸿等: "良性前列腺增生治疗新药非那甾胺的合成", 《中国药物化学杂志》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113429449A (zh) * | 2020-03-06 | 2021-09-24 | F.I.S.-菲博利佳意大利合成面料股份公司 | 纯化本胆烯酸的方法 |
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Publication number | Publication date |
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CN104447929B (zh) | 2016-06-29 |
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CB02 | Change of applicant information |
Address after: 422900 Xinshao Economic Development Zone, Shaoyang Province, Xing Road, economic development zone, Hunan Applicant after: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Address before: 422900 Xinshao Economic Development Zone, Shaoyang Province, Xing Road, economic development zone, Hunan Applicant before: HUNAN KEREY BIOTECHNOLOGY Co.,Ltd. |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A method for synthesis of 3-carbonyl-4-androstene-17 b - carboxylic acid Effective date of registration: 20200928 Granted publication date: 20160629 Pledgee: China Co. truction Bank Corp Xinshao branch Pledgor: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Registration number: Y2020980006554 |
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Date of cancellation: 20230131 Granted publication date: 20160629 Pledgee: China Co. truction Bank Corp Xinshao branch Pledgor: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Registration number: Y2020980006554 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A synthesis of 3-carbonyl-4-androsten-17 b Carboxylic acid method Granted publication date: 20160629 Pledgee: Industrial and Commercial Bank of China Limited Shaoyang Beita Branch Pledgor: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Registration number: Y2024980006163 |