CN1887897A - Chemical synthesis of free megestrol - Google Patents
Chemical synthesis of free megestrol Download PDFInfo
- Publication number
- CN1887897A CN1887897A CN 200610052632 CN200610052632A CN1887897A CN 1887897 A CN1887897 A CN 1887897A CN 200610052632 CN200610052632 CN 200610052632 CN 200610052632 A CN200610052632 A CN 200610052632A CN 1887897 A CN1887897 A CN 1887897A
- Authority
- CN
- China
- Prior art keywords
- methyne
- megestrol
- thing
- free
- palladium
- 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
- 229960001786 megestrol Drugs 0.000 title claims abstract description 24
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 title claims abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229950000801 hydroxyprogesterone caproate Drugs 0.000 claims abstract description 16
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000007069 methylation reaction Methods 0.000 claims abstract description 4
- DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-N 0.000 claims abstract 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 18
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 17
- 239000002994 raw material Substances 0.000 claims description 7
- 238000005303 weighing Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- JBVNBBXAMBZTMQ-CEGNMAFCSA-N megestrol Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JBVNBBXAMBZTMQ-CEGNMAFCSA-N 0.000 description 19
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 13
- 239000012141 concentrate Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000007670 refining Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000009413 insulation Methods 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product 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
- 230000000694 effects Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2006100526328A CN100398553C (en) | 2006-07-24 | 2006-07-24 | Chemical synthesis of free megestrol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2006100526328A CN100398553C (en) | 2006-07-24 | 2006-07-24 | Chemical synthesis of free megestrol |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1887897A true CN1887897A (en) | 2007-01-03 |
CN100398553C CN100398553C (en) | 2008-07-02 |
Family
ID=37577179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2006100526328A Expired - Fee Related CN100398553C (en) | 2006-07-24 | 2006-07-24 | Chemical synthesis of free megestrol |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100398553C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103087136A (en) * | 2012-11-06 | 2013-05-08 | 湖南科源生物制品有限公司 | Novel process for preparing progesterone |
CN113583074A (en) * | 2021-06-28 | 2021-11-02 | 佳尔科生物科技南通有限公司 | Novel preparation method of 6-methyl-17 alpha-hydroxyprogesterone and precursor thereof |
CN114057821A (en) * | 2021-11-30 | 2022-02-18 | 黑龙江中医药大学 | Preparation method of medroxyprogesterone acetate for perimenopausal syndrome |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3004508C2 (en) * | 1980-02-05 | 1981-12-10 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Process for the preparation of 6-methylene steroids |
US4346037A (en) * | 1981-07-10 | 1982-08-24 | The Upjohn Company | Base catalyzed acylation with enol esters |
FR2676740B1 (en) * | 1991-05-23 | 1993-11-05 | Roussel Uclaf | NOVEL STEROUID DERIVATIVES OF PREGNA-4,9 (11), 17 (20) -TRIE-3-ONE, THEIR PREPARATION, THEIR APPLICATION TO THE PREPARATION OF PREGNA-4,9 (11), 16-TRIENE- STEROUID COMPOUNDS 3.20-DIONE AND NEW INTERMEDIATES. |
US6828120B2 (en) * | 2001-06-18 | 2004-12-07 | Pharmacia And Upjohn Company | Process to prepare 11β, 17α,21-trihydroxy-6α-methylpregna-1,4-diene-3,20-dione 21-acetate |
-
2006
- 2006-07-24 CN CNB2006100526328A patent/CN100398553C/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103087136A (en) * | 2012-11-06 | 2013-05-08 | 湖南科源生物制品有限公司 | Novel process for preparing progesterone |
CN113583074A (en) * | 2021-06-28 | 2021-11-02 | 佳尔科生物科技南通有限公司 | Novel preparation method of 6-methyl-17 alpha-hydroxyprogesterone and precursor thereof |
CN114057821A (en) * | 2021-11-30 | 2022-02-18 | 黑龙江中医药大学 | Preparation method of medroxyprogesterone acetate for perimenopausal syndrome |
CN114057821B (en) * | 2021-11-30 | 2022-12-09 | 黑龙江中医药大学 | Preparation method of medroxyprogesterone acetate for perimenopausal syndrome |
Also Published As
Publication number | Publication date |
---|---|
CN100398553C (en) | 2008-07-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20070103 Assignee: Taizhou Taifa Pharmaceuticals Co., Ltd. Assignor: Wang Jiazhen Contract record no.: 2010330000450 Denomination of invention: Chemical synthesis of free megestrol Granted publication date: 20080702 License type: Exclusive License Record date: 20100409 |
|
ASS | Succession or assignment of patent right |
Owner name: TAIZHOU TAIFA PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: WANG JIAZHEN Effective date: 20130620 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20130620 Address after: 317300 No. 14 Industrial East Road, Xianju County, Zhejiang, Taizhou Patentee after: Taizhou Taifa Pharmaceuticals Co., Ltd. Address before: The 317300 industry in Zhejiang province Xianju County Road No. 14 Taizhou Baida Pharmaceutical Co Ltd Patentee before: Wang Jiazhen |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080702 Termination date: 20150724 |
|
EXPY | Termination of patent right or utility model |