HRP20060038A2 - PROCESS FOR THE SYNTHESIS OF HIGH PURITY D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINOPREGN-4-ENE-20-YNE-3-OXIME - Google Patents
PROCESS FOR THE SYNTHESIS OF HIGH PURITY D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINOPREGN-4-ENE-20-YNE-3-OXIMEInfo
- Publication number
- HRP20060038A2 HRP20060038A2 HR20060038A HRP20060038A HRP20060038A2 HR P20060038 A2 HRP20060038 A2 HR P20060038A2 HR 20060038 A HR20060038 A HR 20060038A HR P20060038 A HRP20060038 A HR P20060038A HR P20060038 A2 HRP20060038 A2 HR P20060038A2
- Authority
- HR
- Croatia
- Prior art keywords
- water
- ethyl
- acetoxy
- oxime
- dinorpregn
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000000243 solution Substances 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 229960004400 levonorgestrel Drugs 0.000 abstract 2
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- ISHXLNHNDMZNMC-VTKCIJPMSA-N (3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol Chemical compound O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C\1 ISHXLNHNDMZNMC-VTKCIJPMSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- HMNQNULAYXDEEQ-UHFFFAOYSA-N acetic acid;hydroxylamine Chemical compound ON.CC(O)=O HMNQNULAYXDEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000012298 atmosphere Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 1
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 abstract 1
- 239000005457 ice water Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960002667 norelgestromin Drugs 0.000 abstract 1
- 238000006146 oximation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0301982A HUP0301982A2 (hu) | 2003-06-30 | 2003-06-30 | Eljárás nagy tisztaságú d-(17alfa)-13-etil-17-hidroxi-18,19-dinor-pregn-4-én-20-in-3-on-oxim előállítására |
| PCT/HU2004/000031 WO2005000868A1 (en) | 2003-06-30 | 2004-04-29 | Process for the synthesis of high purity d-(17alpha)-13-ethyl-17hydroxy-18,19-dinorpre:gn-4-ene-20-yne-3-one-oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20060038A2 true HRP20060038A2 (en) | 2006-11-30 |
Family
ID=90001694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20060038A HRP20060038A2 (en) | 2003-06-30 | 2006-01-27 | PROCESS FOR THE SYNTHESIS OF HIGH PURITY D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINOPREGN-4-ENE-20-YNE-3-OXIME |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1638988B1 (ru) |
| JP (1) | JP2007516946A (ru) |
| CN (1) | CN100355771C (ru) |
| AT (1) | ATE462712T1 (ru) |
| AU (1) | AU2004251118A1 (ru) |
| BR (1) | BRPI0412186A (ru) |
| CA (1) | CA2528952A1 (ru) |
| DE (1) | DE602004026306D1 (ru) |
| EA (1) | EA008411B1 (ru) |
| HR (1) | HRP20060038A2 (ru) |
| HU (1) | HUP0301982A2 (ru) |
| MX (1) | MXPA05013948A (ru) |
| NO (1) | NO20060455L (ru) |
| NZ (1) | NZ544378A (ru) |
| RS (1) | RS20050897A (ru) |
| UA (1) | UA80059C2 (ru) |
| WO (1) | WO2005000868A1 (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7816546B2 (en) | 2003-06-30 | 2010-10-19 | Richter Gedeon Vegyeszeti Gyar Rt. | Process for the synthesis of high purity d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime |
| ITMI20052464A1 (it) * | 2005-12-22 | 2007-06-23 | S N I F F Italia S P A | Procedimento per la preparazi9one di norelgestromin norelgestromina |
| CN108827950B (zh) * | 2018-05-31 | 2020-08-21 | 成都市科隆化学品有限公司 | 乙酸中微量乙酸酐的检测方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7306609A (ru) * | 1972-05-26 | 1973-11-28 | ||
| US4027019A (en) * | 1975-07-24 | 1977-05-31 | Ortho Pharmaceutical Corporation | 3-Oximes of D-17α-ethynyl-19-nortestosterone esters and method |
| PL181582B1 (pl) * | 1995-06-07 | 2001-08-31 | Ortho Mcneil Pharm Inc | Plaster na skóre do zapobiegania owulacji u kobiety oraz plaster na skóre do przeprowadzania hormonalnej terapii substytucyjnej PL PL PL PL PL PL PL PL |
-
2003
- 2003-06-30 HU HU0301982A patent/HUP0301982A2/hu unknown
-
2004
- 2004-04-29 CA CA002528952A patent/CA2528952A1/en not_active Abandoned
- 2004-04-29 JP JP2006518378A patent/JP2007516946A/ja active Pending
- 2004-04-29 RS YUP-2005/0897A patent/RS20050897A/sr unknown
- 2004-04-29 MX MXPA05013948A patent/MXPA05013948A/es active IP Right Grant
- 2004-04-29 AU AU2004251118A patent/AU2004251118A1/en not_active Abandoned
- 2004-04-29 EA EA200600119A patent/EA008411B1/ru not_active IP Right Cessation
- 2004-04-29 BR BRPI0412186-4A patent/BRPI0412186A/pt not_active IP Right Cessation
- 2004-04-29 WO PCT/HU2004/000031 patent/WO2005000868A1/en active Application Filing
- 2004-04-29 UA UAA200600812A patent/UA80059C2/uk unknown
- 2004-04-29 DE DE602004026306T patent/DE602004026306D1/de not_active Expired - Fee Related
- 2004-04-29 NZ NZ544378A patent/NZ544378A/en unknown
- 2004-04-29 AT AT04730316T patent/ATE462712T1/de not_active IP Right Cessation
- 2004-04-29 CN CNB2004800165780A patent/CN100355771C/zh not_active Expired - Fee Related
- 2004-04-29 EP EP04730316A patent/EP1638988B1/en not_active Expired - Lifetime
-
2006
- 2006-01-27 NO NO20060455A patent/NO20060455L/no not_active Application Discontinuation
- 2006-01-27 HR HR20060038A patent/HRP20060038A2/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005000868A1 (en) | 2005-01-06 |
| CN100355771C (zh) | 2007-12-19 |
| CN1805970A (zh) | 2006-07-19 |
| AU2004251118A1 (en) | 2005-01-06 |
| JP2007516946A (ja) | 2007-06-28 |
| HUP0301982D0 (en) | 2003-09-29 |
| EP1638988B1 (en) | 2010-03-31 |
| NZ544378A (en) | 2008-02-29 |
| EA200600119A1 (ru) | 2006-06-30 |
| MXPA05013948A (es) | 2006-03-09 |
| EP1638988A1 (en) | 2006-03-29 |
| EA008411B1 (ru) | 2007-04-27 |
| RS20050897A (sr) | 2007-08-03 |
| NO20060455L (no) | 2006-03-29 |
| ATE462712T1 (de) | 2010-04-15 |
| DE602004026306D1 (de) | 2010-05-12 |
| UA80059C2 (en) | 2007-08-10 |
| CA2528952A1 (en) | 2005-01-06 |
| BRPI0412186A (pt) | 2006-08-22 |
| HUP0301982A2 (hu) | 2005-04-28 |
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| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20090414 Year of fee payment: 6 |
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| OBST | Application withdrawn |