CN105461776A - 一种黄体酮的合成方法 - Google Patents
一种黄体酮的合成方法 Download PDFInfo
- Publication number
- CN105461776A CN105461776A CN201510715996.9A CN201510715996A CN105461776A CN 105461776 A CN105461776 A CN 105461776A CN 201510715996 A CN201510715996 A CN 201510715996A CN 105461776 A CN105461776 A CN 105461776A
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- CN
- China
- Prior art keywords
- ether
- reaction
- synthetic method
- solvent
- epoxy
- 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.)
- Granted
Links
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 title claims abstract description 47
- 229960003387 progesterone Drugs 0.000 title claims abstract description 23
- 239000000186 progesterone Substances 0.000 title claims abstract description 23
- 238000010189 synthetic method Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract description 3
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- VKSJVMZEQNIBNA-UHFFFAOYSA-N 2-chloroethyl propanoate Chemical compound CCC(=O)OCCCl VKSJVMZEQNIBNA-UHFFFAOYSA-N 0.000 abstract 1
- 238000007259 addition reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- 150000007949 saponins Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960005471 androstenedione Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 244000008991 Curcuma longa Species 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 208000008899 Habitual abortion Diseases 0.000 description 1
- 208000019255 Menstrual disease Diseases 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 208000030270 breast disease Diseases 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000003373 curcuma longa Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 208000007106 menorrhagia Diseases 0.000 description 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510715996.9A CN105461776B (zh) | 2015-10-28 | 2015-10-28 | 一种黄体酮的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN201510715996.9A CN105461776B (zh) | 2015-10-28 | 2015-10-28 | 一种黄体酮的合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN105461776A true CN105461776A (zh) | 2016-04-06 |
CN105461776B CN105461776B (zh) | 2017-04-12 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CN201510715996.9A Active CN105461776B (zh) | 2015-10-28 | 2015-10-28 | 一种黄体酮的合成方法 |
Country Status (1)
Country | Link |
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CN (1) | CN105461776B (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3475464A (en) * | 1966-11-07 | 1969-10-28 | Syntex Corp | Process for the preparation of steroids and novel intermediates thereof |
CN103848879A (zh) * | 2013-11-28 | 2014-06-11 | 湖南科源生物制品有限公司 | 一种以1,4-雄烯二酮为原料制备黄体酮的方法 |
CN104098640A (zh) * | 2014-08-06 | 2014-10-15 | 赵云现 | 黄体酮的制备方法 |
CN104262442A (zh) * | 2014-10-10 | 2015-01-07 | 湖南科瑞生物科技有限公司 | 黄体酮的制备方法 |
-
2015
- 2015-10-28 CN CN201510715996.9A patent/CN105461776B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3475464A (en) * | 1966-11-07 | 1969-10-28 | Syntex Corp | Process for the preparation of steroids and novel intermediates thereof |
CN103848879A (zh) * | 2013-11-28 | 2014-06-11 | 湖南科源生物制品有限公司 | 一种以1,4-雄烯二酮为原料制备黄体酮的方法 |
CN104098640A (zh) * | 2014-08-06 | 2014-10-15 | 赵云现 | 黄体酮的制备方法 |
CN104262442A (zh) * | 2014-10-10 | 2015-01-07 | 湖南科瑞生物科技有限公司 | 黄体酮的制备方法 |
Also Published As
Publication number | Publication date |
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CN105461776B (zh) | 2017-04-12 |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
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 synthetic method of progesterone Effective date of registration: 20200928 Granted publication date: 20170412 Pledgee: China Co. truction Bank Corp Xinshao branch Pledgor: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Registration number: Y2020980006554 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230131 Granted publication date: 20170412 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 method of progesterone Granted publication date: 20170412 Pledgee: Industrial and Commercial Bank of China Limited Shaoyang Beita Branch Pledgor: HUNAN KEREY PHARMACEUTICAL Co.,Ltd. Registration number: Y2024980006163 |