NO20060455L - Fremgangsmate for syntesen av hoyrent D-(17alfa)-13-etyl-17-hydroksy-18,19-dinor-pregn-4-en-20-yn-3-on-oksim. - Google Patents
Fremgangsmate for syntesen av hoyrent D-(17alfa)-13-etyl-17-hydroksy-18,19-dinor-pregn-4-en-20-yn-3-on-oksim.Info
- Publication number
- NO20060455L NO20060455L NO20060455A NO20060455A NO20060455L NO 20060455 L NO20060455 L NO 20060455L NO 20060455 A NO20060455 A NO 20060455A NO 20060455 A NO20060455 A NO 20060455A NO 20060455 L NO20060455 L NO 20060455L
- Authority
- NO
- Norway
- Prior art keywords
- water
- ethyl
- oxime
- dinorphregn
- acetoxy
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 239000000243 solution 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
- 150000002923 oximes Chemical class 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 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
- 239000008395 clarifying agent Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- -1 enol acetate Chemical class 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
- 230000003301 hydrolyzing effect Effects 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
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 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
- 239000000725 suspension 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Oppfinnelsen angår en fremgangsmåte for syntesen av høyrent d-(17a)-13etyl-17-hydroksy-18,19-dinorpregn-4-en-20-yn-3-on-oksim (heretter norelgestromin) via acetylering av d-norgestrel ved posisjon 17, oksimasjon av oksogruppen ved posisjon 3 i det oppnådde 17-acetoksyderivatet, og til slutt hydrolysering av acetoksygruppen ved posisjon 17 i det oppnådde 3-oksimderivatet. Fremgangsmåten ifølge vår oppfinnelse er som følger: utgangsmaterialet d-(17a)-17-hydroksy-13-etyl-18,19-dinorpregn-4-en-20-yn-3-on (d-norgestrel) - renhet 93-94% - acetyleres med eddiksyreanhydrid i eddiksyre, under nærvær av sinkklorid og hydrogenklorid, eller 70% perklorsyre i en inert gassatmosfære, og etter at reaksjonen er ferdig blir overskudd av eddiksyreanhydrid og "enolacetat"-biproduktet dekomponert med vannløsning av saltsyre, deretter blir det dannede d-(17a)-17-acetoksy-13etyl-18,19-dinorpregn-4-en-20-yn3-on isolert fra reaksjonsblandingen ved tilsetting av isvann, det utfelte produktet filtreres fra, vaskes med vann, tørkes, oppløses diklormetan eller aceton og klares med silikagel eller aluminiumoksid og aktivt kull, etter frafiltrering av klaringsmiddelet blir den resulterende løsningen konsentrert og residuet omkrystallisert, det oppnådde d-(17a)-17-acetoksy-13-etyl-18,19-dinorpregn-4-en-20-yn-3-on omsettes enten med hydroksylammoniumacetat eller med hydroksylammoniumklorid under nærvær av natriumacetat, i eddiksyre under nitrogenatmosfære ved kraftig omrøring i omtrent 1 time, etter at reaksjonen er ferdig tilsettes vann, det utfelte produktet filtreres fra, vaskes med vann, tørkes og omkrystalliseres, det oppnådde d-(17a)-17-acetoksy-13-etyl-18,19-dinorpregn-4-en-20-yn-3-on-oksim hydrolyseres med en ekvivalent mengde av et alkalimetallhydroksid i en C1-C4 alkanolløsning, under nitrogenatmosfære ved en temperatur på mellom 5-38 grader C , under kraftig omrøring, etter at reaksjonen er ferdig blir blandingen fortynnet med vann og den resulterende suspensjonens pH justeres til 7,5 - 9 med eddiksyre, det utfelte produktet filtreres fra, vaskes med vann, tørkes, det urene produktet oppløses i etanol, klares med aktivt kull, og etter frafiltrering av klaringsmiddelet tilsettes vann til den oppnådde løsningen, det utfelte høyrene d(17a)-17-acetoksy-13-etyl-18,19-dinorpregn-4-en-20-yn-3-on-oksim filtreres fra, vaskes med vann og i gitte tilfeller omkrystalliseres fra etanol.
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 |
|---|---|
| NO20060455L true NO20060455L (no) | 2006-03-29 |
Family
ID=90001694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20060455A NO20060455L (no) | 2003-06-30 | 2006-01-27 | Fremgangsmate for syntesen av hoyrent D-(17alfa)-13-etyl-17-hydroksy-18,19-dinor-pregn-4-en-20-yn-3-on-oksim. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1638988B1 (no) |
| JP (1) | JP2007516946A (no) |
| CN (1) | CN100355771C (no) |
| AT (1) | ATE462712T1 (no) |
| AU (1) | AU2004251118A1 (no) |
| BR (1) | BRPI0412186A (no) |
| CA (1) | CA2528952A1 (no) |
| DE (1) | DE602004026306D1 (no) |
| EA (1) | EA008411B1 (no) |
| HR (1) | HRP20060038A2 (no) |
| HU (1) | HUP0301982A2 (no) |
| MX (1) | MXPA05013948A (no) |
| NO (1) | NO20060455L (no) |
| NZ (1) | NZ544378A (no) |
| RS (1) | RS20050897A (no) |
| UA (1) | UA80059C2 (no) |
| WO (1) | WO2005000868A1 (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576226B2 (en) | 2003-06-30 | 2009-08-18 | Richter Gedeon Vegyeszeti Gyar Rt. | Process of making isomers of norelgestromin and methods using the same |
| 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 (no) * | 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 |
| CN1188189C (zh) * | 1995-06-07 | 2005-02-09 | 奥瑟－麦内尔制药公司 | 基质层含有17－脱乙酰基诺孕酯的经皮贴片及基质的用途 |
-
2003
- 2003-06-30 HU HU0301982A patent/HUP0301982A2/hu unknown
-
2004
- 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
- 2004-04-29 AT AT04730316T patent/ATE462712T1/de not_active IP Right Cessation
- 2004-04-29 JP JP2006518378A patent/JP2007516946A/ja active Pending
- 2004-04-29 CA CA002528952A patent/CA2528952A1/en not_active Abandoned
- 2004-04-29 BR BRPI0412186-4A patent/BRPI0412186A/pt not_active IP Right Cessation
- 2004-04-29 HR HR20060038A patent/HRP20060038A2/xx not_active Application Discontinuation
- 2004-04-29 EA EA200600119A patent/EA008411B1/ru not_active IP Right Cessation
- 2004-04-29 AU AU2004251118A patent/AU2004251118A1/en not_active Abandoned
- 2004-04-29 WO PCT/HU2004/000031 patent/WO2005000868A1/en not_active Ceased
- 2004-04-29 NZ NZ544378A patent/NZ544378A/en unknown
- 2004-04-29 MX MXPA05013948A patent/MXPA05013948A/es active IP Right Grant
- 2004-04-29 RS YUP-2005/0897A patent/RS20050897A/sr unknown
- 2004-04-29 DE DE602004026306T patent/DE602004026306D1/de not_active Expired - Fee Related
- 2004-04-29 UA UAA200600812A patent/UA80059C2/uk unknown
-
2006
- 2006-01-27 NO NO20060455A patent/NO20060455L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004026306D1 (de) | 2010-05-12 |
| UA80059C2 (en) | 2007-08-10 |
| CN100355771C (zh) | 2007-12-19 |
| NZ544378A (en) | 2008-02-29 |
| HUP0301982A2 (hu) | 2005-04-28 |
| CA2528952A1 (en) | 2005-01-06 |
| AU2004251118A1 (en) | 2005-01-06 |
| BRPI0412186A (pt) | 2006-08-22 |
| EA008411B1 (ru) | 2007-04-27 |
| ATE462712T1 (de) | 2010-04-15 |
| MXPA05013948A (es) | 2006-03-09 |
| WO2005000868A1 (en) | 2005-01-06 |
| HRP20060038A2 (en) | 2006-11-30 |
| EP1638988B1 (en) | 2010-03-31 |
| JP2007516946A (ja) | 2007-06-28 |
| EA200600119A1 (ru) | 2006-06-30 |
| EP1638988A1 (en) | 2006-03-29 |
| CN1805970A (zh) | 2006-07-19 |
| RS20050897A (sr) | 2007-08-03 |
| HUP0301982D0 (en) | 2003-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU191960B (en) | Process for preparing substituted 2-mercapto-imidazoles | |
| CN115884978A (zh) | 制备胆酸衍生物的方法及其原料 | |
| NO20060455L (no) | Fremgangsmate for syntesen av hoyrent D-(17alfa)-13-etyl-17-hydroksy-18,19-dinor-pregn-4-en-20-yn-3-on-oksim. | |
| JPH07285922A (ja) | グルタミン誘導体の製造法 | |
| KR100327621B1 (ko) | 7-카르복시메틸옥시-3',4',5-트리메톡시플라본의 제조방법 | |
| SATO et al. | The Chemistry of the Spiroaminoketal Side Chain of Solasodine and Tomatidine. I. 1 Improved Preparation of 3β-Acetoxy-5, 16-pregnadien-20-one and 3β-Acetoxy-5α-pregn-16-en-20-one from Solasodine and Tomatidine. | |
| CN109134576B (zh) | 一种以猪去氧胆酸为原料合成石胆酸的方法 | |
| US5977380A (en) | Process for preparing N-[1- (S)-ethoxycarbonyl-3- phenylpropyl]-L-alanine derivatives | |
| JP2007516946A5 (no) | ||
| JPH0316333B2 (no) | ||
| KR870001903B1 (ko) | 16α-하이드록시-17α-아미노프레그난 유도체의 제조방법 | |
| RU2337918C9 (ru) | СПОСОБ ПОЛУЧЕНИЯ 6α-МЕТИЛГИДРОКОРТИЗОНА ИЛИ ЕГО 11β-АЛКАНОИЛОКСИПРОИЗВОДНЫХ (ВАРИАНТЫ), СПОСОБ ПОЛУЧЕНИЯ 6α-МЕТИЛПРЕДНИЗОЛОНА ИЛИ ЕГО 11β-АЛКАНОИЛОКСИПРОИЗВОДНЫХ С ИСПОЛЬЗОВАНИЕМ ПОЛУЧЕННОГО 6α-МЕТИЛГИДРОКОРТИЗОНА ИЛИ ЕГО 11β-АЛКАНОИЛОКСИПРОИЗВОДНЫХ | |
| NZ243564A (en) | 17-beta-substituted-4-aza-5-alpha-androstan-3-one derivatives preparation by oxidation and amination of the corresponding and rostane derivative; product thereof | |
| NO154276B (no) | Innretning for ¨ skumme av stoffer som flyter p¨ vann. | |
| SU1711675A3 (ru) | Способ получени 22 /R, S/-11 @ , 21 - дигидрокси-16 @ , 17-бутилиденбисоксипрегна - 1,4-диен-3,20-диона | |
| KR100433566B1 (ko) | (11β,16β)-21-(3-카르복시-3-옥소프로폭시)-11-히드록시-2'-메틸-5'H-프레그나-1,4-디에노[17,16d]옥사졸-3,20-디온의제조방법 | |
| JPWO2003080561A1 (ja) | ボグリボースの製造法 | |
| US3013026A (en) | Process for the preparation of 3-keto-deta-20-alkylamino steroids | |
| JP2002332274A (ja) | スクアラミンの製造方法 | |
| RU2129125C1 (ru) | СПОСОБ ПОЛУЧЕНИЯ 13α--1,3,510-ТРИЕН-19-НОРАНДРОСТАН-3-ОЛ-17-ОНА И ЕГО МЕТИЛОВОГО ЭФИРА | |
| JPH04290894A (ja) | Ｃｍｐ−シアル酸アナログ体 | |
| JPS63303978A (ja) | 新規ブラシノステロイド誘導体及びその製法 | |
| JPH0156072B2 (no) | ||
| JPH05178888A (ja) | ４−アミノ−不飽和−アンドロスタンジオン誘導体の製造方法 | |
| JPH05345783A (ja) | アデニン誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC2A | Withdrawal, rejection or dismissal of laid open patent application |