CN1324041C - 替勃龙晶型i的制备方法 - Google Patents
替勃龙晶型i的制备方法 Download PDFInfo
- Publication number
- CN1324041C CN1324041C CNB031161030A CN03116103A CN1324041C CN 1324041 C CN1324041 C CN 1324041C CN B031161030 A CNB031161030 A CN B031161030A CN 03116103 A CN03116103 A CN 03116103A CN 1324041 C CN1324041 C CN 1324041C
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- CN
- China
- Prior art keywords
- tibolone
- preparation
- crystal formation
- organic solvent
- water
- 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 - Fee Related
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- 239000013078 crystal Substances 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims description 21
- WZDGZWOAQTVYBX-XOINTXKNSA-N tibolone Chemical compound C([C@@H]12)C[C@]3(C)[C@@](C#C)(O)CC[C@H]3[C@@H]1[C@H](C)CC1=C2CCC(=O)C1 WZDGZWOAQTVYBX-XOINTXKNSA-N 0.000 claims abstract description 45
- 229960001023 tibolone Drugs 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002425 crystallisation Methods 0.000 claims abstract description 16
- 230000008025 crystallization Effects 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 2
- 150000003053 piperidines Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 14
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000757 progestagenic effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB031161030A CN1324041C (zh) | 2003-04-01 | 2003-04-01 | 替勃龙晶型i的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB031161030A CN1324041C (zh) | 2003-04-01 | 2003-04-01 | 替勃龙晶型i的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1534041A CN1534041A (zh) | 2004-10-06 |
CN1324041C true CN1324041C (zh) | 2007-07-04 |
Family
ID=34284588
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB031161030A Expired - Fee Related CN1324041C (zh) | 2003-04-01 | 2003-04-01 | 替勃龙晶型i的制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN1324041C (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103772462B (zh) * | 2012-10-19 | 2015-12-02 | 华润紫竹药业有限公司 | 替勃龙晶型ⅰ的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4701450A (en) * | 1984-03-21 | 1987-10-20 | Akzo N.V. | Steroids for use as immunomodulators |
US5037817A (en) * | 1989-03-18 | 1991-08-06 | Akzo N.V. | Pharmaceutical composition which contains a pharmaceutically suitable carrier and the compound having the structure (7α,17α)-17-hydroxy-7-methyl-19-nor-17-pregn-5(10)-en-20-yn-3-one |
CN1253503A (zh) * | 1997-04-22 | 2000-05-17 | 阿克佐诺贝尔公司 | 稳定的替勃龙组合物 |
-
2003
- 2003-04-01 CN CNB031161030A patent/CN1324041C/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4701450A (en) * | 1984-03-21 | 1987-10-20 | Akzo N.V. | Steroids for use as immunomodulators |
US5037817A (en) * | 1989-03-18 | 1991-08-06 | Akzo N.V. | Pharmaceutical composition which contains a pharmaceutically suitable carrier and the compound having the structure (7α,17α)-17-hydroxy-7-methyl-19-nor-17-pregn-5(10)-en-20-yn-3-one |
CN1253503A (zh) * | 1997-04-22 | 2000-05-17 | 阿克佐诺贝尔公司 | 稳定的替勃龙组合物 |
Non-Patent Citations (3)
Title |
---|
in situ observation of epitaxial polymorphic nucleation of themodel steroid methyl analogue 17 northindrone S. X.M. BOERRIGTER ET.AL,J.phys.Chem. B,Vol.106 2002 * |
Synthesisof(3a,7b,17a)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol,a metabolite of ORG OD14, and its7-epimer RALF PLATE,ET. AL,STEROIDS,Vol.65 2000 * |
Synthesisof(3a,7b,17a)-7-methyl-19-norpregn-5(10)-en-20-yne-3,7,17-triol,a metabolite of ORG OD14, and its7-epimer RALF PLATE,ET. AL,STEROIDS,Vol.65 2000;in situ observation of epitaxial polymorphic nucleation of themodel steroid methyl analogue 17 northindrone S. X.M. BOERRIGTER ET.AL,J.phys.Chem. B,Vol.106 2002 * |
Also Published As
Publication number | Publication date |
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CN1534041A (zh) | 2004-10-06 |
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Free format text: FORMER OWNER: SHANGHAI DISAINUO CHEMICAL INDUSTRY CO., LTD. Owner name: JIANGSU XIDI PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: SHANGHAI DISAINUO MEDICINE SCIENCE AND TECHNOLOGY DEVELOPMENT CO., LTD. Effective date: 20101227 |
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Free format text: CORRECT: ADDRESS; FROM: 201908 NO.6950 (NO.104, ZONE N), HUTAI ROAD, BAOSHAN DISTRICT, SHANGHAI TO: 226200 NO.3, JIANGFENG ROAD, BINJIANG FINE CHEMICAL INDUSTRY PARK, ECONOMIC DEVELOPMENT ZONE, QIDONG CITY, JIANGSU PROVINCE |
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Effective date of registration: 20101227 Address after: 226200 Jiangsu city in Qidong Province Economic Development Zone Binjiang fine chemical industry park Jiangfeng Road No. 3 Patentee after: Jiangsu Xidi Pharmaceutical Co., Ltd. Address before: 201908, No. 6950 Hu Tai Road, Shanghai, Baoshan District (No. 104, N District) Co-patentee before: Shanghai Disainuo Chemical Industry Co., Ltd. Patentee before: Shanghai Desano Pharmaceutical Technology Development Co., Ltd. |
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CP01 | Change in the name or title of a patent holder |
Address after: 226200 No. 3 Jiang Feng Road, Binjiang Fine Chemical Industrial Park, Qidong Economic Development Zone, Jiangsu Patentee after: Jiangsu creation Pharmaceutical Co., Ltd. Address before: 226200 No. 3 Jiang Feng Road, Binjiang Fine Chemical Industrial Park, Qidong Economic Development Zone, Jiangsu Patentee before: Jiangsu Xidi Pharmaceutical Co., Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070704 Termination date: 20200401 |
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