RU2004125580A - Способ получения 7альфа-метилстероидов - Google Patents
Способ получения 7альфа-метилстероидов Download PDFInfo
- Publication number
- RU2004125580A RU2004125580A RU2004125580/04A RU2004125580A RU2004125580A RU 2004125580 A RU2004125580 A RU 2004125580A RU 2004125580/04 A RU2004125580/04 A RU 2004125580/04A RU 2004125580 A RU2004125580 A RU 2004125580A RU 2004125580 A RU2004125580 A RU 2004125580A
- Authority
- RU
- Russia
- Prior art keywords
- steroid
- copper
- grignard reagent
- formula
- hydroxy
- Prior art date
Links
Classifications
-
- 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
- C07J1/0085—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
-
- 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
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0007—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
- C07J5/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Claims (10)
1. Способ получения 7α-метилстероидов формулы I
где R1 представляет собой водород, метил или С≡СН;
R2 представляет собой (СН2)nOH, где n равно 0, 1 или 2,
опосредованным медью 1,6-сопряженным присоединением реактива Гриньяра СН3MgX, причем Х является галогеном, к 4,6-ненасыщенному 3-кетостероиду формулы II
где R1 и R2 имеют значения, указанные ранее,
включающий защиту гидроксигруппы стероида формулы II триалкилсилильной группой с последующей обработкой гидроксизащищенного стероида реактивом Гриньяра.
2. Способ по п. 1, где R1 представляет собой водород, метил или С≡СН и R2 представляет собой ОН или R1 представляет собой водород и R2 представляет собой (СН2)2ОН.
3. Способ по п. 1 или 2, где реактив Гриньяра представляет собой СН3MgCl.
4. Способ по п. 1 или 2, где триалкилсилильной группой является триметилсилильная группа.
5. Способ по п. 1 или 2, где растворителем реакции Гриньяра является тетрагидрофуран, диэтиловый эфир или их смесь.
6. Способ по п. 1 или 2, где концентрация стероида является 0,1-0,3 молярной.
7. Способ по п. 1 или 2, где молярное отношение стероида к реактиву Гриньяра составляет 1:1 - 1:7.
8. Способ по п. 1 или 2, где в качестве медного катализатора используют ацетат меди(II) или хлорид меди(II).
9. Способ по п. 1 или 2, где температура реакции Гриньяра составляет от -78 до 0°С.
10. Соединение 21-гидрокси-19-норпрегн-4,6-диен-3-он.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02075230 | 2002-01-21 | ||
| EP02075230.9 | 2002-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004125580A true RU2004125580A (ru) | 2006-01-27 |
| RU2305105C2 RU2305105C2 (ru) | 2007-08-27 |
Family
ID=8185555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004125580/04A RU2305105C2 (ru) | 2002-01-21 | 2003-01-14 | СПОСОБ ПОЛУЧЕНИЯ 7α-МЕТИЛСТЕРОИДОВ, СОЕДИНЕНИЕ |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US20050090476A1 (ru) |
| EP (1) | EP1470151B1 (ru) |
| JP (1) | JP5250174B2 (ru) |
| KR (1) | KR100937179B1 (ru) |
| CN (1) | CN100372864C (ru) |
| AR (1) | AR038165A1 (ru) |
| AT (1) | ATE453659T1 (ru) |
| AU (1) | AU2003205604B8 (ru) |
| BR (1) | BRPI0306736B8 (ru) |
| CA (1) | CA2472379C (ru) |
| DE (1) | DE60330749D1 (ru) |
| EC (1) | ECSP045180A (ru) |
| EG (1) | EG23417A (ru) |
| ES (1) | ES2336439T3 (ru) |
| HR (1) | HRP20040634B1 (ru) |
| IL (2) | IL162770A0 (ru) |
| IS (1) | IS2740B (ru) |
| MX (1) | MXPA04007049A (ru) |
| NO (1) | NO327095B1 (ru) |
| NZ (1) | NZ533970A (ru) |
| PE (1) | PE20030926A1 (ru) |
| PL (1) | PL208163B1 (ru) |
| RO (1) | RO122913B1 (ru) |
| RS (1) | RS51490B (ru) |
| RU (1) | RU2305105C2 (ru) |
| TW (1) | TWI322813B (ru) |
| WO (1) | WO2003059931A1 (ru) |
| ZA (1) | ZA200405257B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10213371C1 (de) * | 2002-03-21 | 2003-12-24 | Schering Ag | Verfahren zur Herstellung von 7alpha-Methylsteroiden |
| GB0304927D0 (en) * | 2003-03-04 | 2003-04-09 | Resolution Chemicals Ltd | Process for the production of tibolone |
| KR100716981B1 (ko) * | 2004-09-30 | 2007-05-10 | 삼성전자주식회사 | 대중교통의 최적경로 검색방법 및 이를 이용한 휴대용 기기 |
| JP5749261B2 (ja) * | 2009-06-29 | 2015-07-15 | メルツ・ファルマ・ゲーエムベーハー・ウント・コ・カーゲーアーアー | ３，３，５，５−テトラメチルシクロヘキサノンを調製する方法 |
| CN111944001A (zh) * | 2020-07-09 | 2020-11-17 | 浙江神洲药业有限公司 | 一种替勃龙的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3341557A (en) * | 1961-06-05 | 1967-09-12 | Upjohn Co | 7-methyltestosterones |
| US3470216A (en) * | 1966-11-29 | 1969-09-30 | Du Pont | Selected 17,17-difluoro unsaturated androstanes |
| FR2054527B1 (ru) * | 1969-07-28 | 1973-06-08 | Roussel Uclaf | |
| US3798213A (en) * | 1971-01-25 | 1974-03-19 | Merck & Co Inc | 7 alpha-methyl-20-spiroxane-3-ones and process |
| DE2558088C2 (de) * | 1975-12-19 | 1985-05-30 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 4-Androsten-3,17-dion-Derivaten |
| JPS56145239A (en) * | 1980-04-11 | 1981-11-11 | Sumitomo Chem Co Ltd | Novel bicyclooctane derivative and its preparation |
| US4298559A (en) * | 1980-07-23 | 1981-11-03 | Dow Corning Corporation | High yield silicon carbide from alkylated or arylated pre-ceramic polymers |
| US6054446A (en) * | 1997-12-24 | 2000-04-25 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| US6548491B2 (en) * | 1997-12-24 | 2003-04-15 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| ES2204613T3 (es) * | 1999-04-06 | 2004-05-01 | Akzo Nobel N.V. | Androgenos 7-alfa alquilo oralmente activos. |
| TW548277B (en) * | 1999-07-16 | 2003-08-21 | Akzo Nobel Nv | Orally active androgens |
| IL149424A (en) * | 1999-12-02 | 2007-05-15 | Organon Nv | Androgens are converted to methylene at positions 15,14 |
| WO2001058919A2 (en) * | 2000-02-11 | 2001-08-16 | Sri International | Synthesis of anti-estrogenic and other therapeutic steroids from 21-hydroxy-19-norpregna-4-en-3-one |
| AU8201601A (en) * | 2000-07-28 | 2002-02-13 | Akzo Nobel Nv | 16alpha-methyl or ethyl substituted estrogens |
| US20040010138A1 (en) * | 2002-03-21 | 2004-01-15 | Schering Ag | Process for the production of 7alpha-methyl steroids |
| US7304157B2 (en) * | 2004-09-28 | 2007-12-04 | Bristol-Myers Squibb Company | Efficient synthesis of 4,5-dihydro-pyrazolo[3,4-c]pyrid-2-ones |
-
2003
- 2003-01-14 TW TW092100693A patent/TWI322813B/zh not_active IP Right Cessation
- 2003-01-14 PL PL371583A patent/PL208163B1/pl unknown
- 2003-01-14 AT AT03702441T patent/ATE453659T1/de not_active IP Right Cessation
- 2003-01-14 CA CA2472379A patent/CA2472379C/en not_active Expired - Lifetime
- 2003-01-14 CN CNB038024918A patent/CN100372864C/zh not_active Expired - Lifetime
- 2003-01-14 EP EP03702441A patent/EP1470151B1/en not_active Expired - Lifetime
- 2003-01-14 IL IL16277003A patent/IL162770A0/xx unknown
- 2003-01-14 NZ NZ533970A patent/NZ533970A/en not_active IP Right Cessation
- 2003-01-14 RU RU2004125580/04A patent/RU2305105C2/ru active
- 2003-01-14 JP JP2003560033A patent/JP5250174B2/ja not_active Expired - Lifetime
- 2003-01-14 RS YUP-630/04A patent/RS51490B/sr unknown
- 2003-01-14 AU AU2003205604A patent/AU2003205604B8/en not_active Expired
- 2003-01-14 RO ROA200400656A patent/RO122913B1/ro unknown
- 2003-01-14 DE DE60330749T patent/DE60330749D1/de not_active Expired - Lifetime
- 2003-01-14 MX MXPA04007049A patent/MXPA04007049A/es active IP Right Grant
- 2003-01-14 ES ES03702441T patent/ES2336439T3/es not_active Expired - Lifetime
- 2003-01-14 KR KR1020047010985A patent/KR100937179B1/ko active IP Right Grant
- 2003-01-14 BR BRPI0306736A patent/BRPI0306736B8/pt not_active IP Right Cessation
- 2003-01-14 US US10/502,259 patent/US20050090476A1/en not_active Abandoned
- 2003-01-14 WO PCT/EP2003/000339 patent/WO2003059931A1/en active IP Right Grant
- 2003-01-19 EG EG2003010051A patent/EG23417A/xx active
- 2003-01-20 AR ARP030100149A patent/AR038165A1/es unknown
- 2003-01-20 PE PE2003000062A patent/PE20030926A1/es active IP Right Grant
-
2004
- 2004-06-28 IS IS7339A patent/IS2740B/is unknown
- 2004-06-29 IL IL162770A patent/IL162770A/en active IP Right Grant
- 2004-07-01 ZA ZA2004/05257A patent/ZA200405257B/en unknown
- 2004-07-06 EC EC2004005180A patent/ECSP045180A/es unknown
- 2004-07-12 HR HRP20040634AA patent/HRP20040634B1/hr not_active IP Right Cessation
- 2004-08-19 NO NO20043455A patent/NO327095B1/no not_active IP Right Cessation
-
2010
- 2010-04-22 US US12/765,629 patent/US20100204497A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20120326 |
|
| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20130917 |
|
| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20140402 |