FI57113B - Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan - Google Patents
Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan Download PDFInfo
- Publication number
- FI57113B FI57113B FI771865A FI771865A FI57113B FI 57113 B FI57113 B FI 57113B FI 771865 A FI771865 A FI 771865A FI 771865 A FI771865 A FI 771865A FI 57113 B FI57113 B FI 57113B
- Authority
- FI
- Finland
- Prior art keywords
- gona
- water
- diene
- hydroxy
- methoxy
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Claims (2)
1 J_1 (IV) i vilken formel R och X betecknar detsamma som ovan, och behandlar den si erhillna föreningen med ett halogeneringsmedel, företrädesvis brom eller perbromid sisom pyridinperbromid, i ett inert lösningsmedel sisom metanol eller pyridin, lämpligen mellan -5 °C och + 5 °C, och sedan av-spjälker halogenväte medelst en tertiär organisk bas, sisom pyridin, vid rumstemperatur eller lätt förhöjd temperatur till 17g-hydroxi-17a-CH2X-13g-R-gona-H,9(10)-dien-3-on med den allmänna formeln (I).
1. Förfarande för framställning av en gona-4,9(1 O)-dien med progestagen verkanoch med den allmänna formeln (I) OH R L CH2X ; ,α$Ρ i vilken formel R betecknar en CHg- eller C2Hg-grupp och X betecknar en Cl-, Br-, Ng- eller CN-grupp, kännetecknat därav, att man spjälker oxiranringen ur 3-metoxi-133-R-gona-2,5(10)-dien-17β-spiro-1',2'-oxiranen med den allmänna formeln (II) 01,1 V.-CXJ i vilken formel R betecknar detsamma som ovan, med HC1, HBr, alkaliazid eller alkalicyanid i ett organiskt lösningsmedel, säsom etanol, etylen-glykol eller dimetylformamid under neutrala, basiska eller svagt sura förhällanden, vid rumstemperatur eller förhöjd temperatur tili mot-svarande 3-metoxi-17a-CH2X-133-R-gona-2,5(1 0)-dien-1 7β-ο1 med den allmänna formeln (III) 1S 5711 3 OH CH2X f _] (in) H3co i vilken formel R och X betecknar detsamma som ovan, hydrolyserar den erhillna föreningen med en sur katalysator sisom oxalsyra, i ett med vatten blandbart vattenhaltigt organiskt lösningsmedel, sisom metanol eller i en blandning av vatten, ett med vatten blandbart och ett med vatten inte blandbart lösningsmedel, sisom i en blandning av vatten, metanol och bensen eller en blandning av vatten och metylen-klorid, till 17g-hydroxi-17a-CH2X-13g-R-gona-5(10)-en-3-on med den allmänna formeln (IV) OH ^^xW--ch2x
2. Förfarande enligt patentkravet 1,kännetecknat därav, att man vid reaktionen mellan 3-metoxi-1 3|3-R-gona-2,5(1 0)-dien-1 7$-spiro-11,2'-oxiran (II) och HC1, HBr, alkaliazid eller alkalicyanid i svagt surt medium framställer 17g-hydroxi-17a-CH2X-13g-R-gona-5(10)-en-3-on (IV) utan mellanisolering av 3-metoxi-17x-CH2X-13B-R-gona-2,5(10)-dien-17g-ol (III) i en enda reaktionsfas.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD7600193348A DD132497A1 (de) | 1976-06-14 | 1976-06-14 | Verfahren zur herstellung von neuen gona-4,9(10)-dienen |
| DD19334876 | 1976-06-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771865A7 FI771865A7 (sv) | 1977-12-15 |
| FI57113B true FI57113B (fi) | 1980-02-29 |
| FI57113C FI57113C (fi) | 1980-06-10 |
Family
ID=5504816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771865A FI57113C (fi) | 1976-06-14 | 1977-06-14 | Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4248790A (sv) |
| JP (1) | JPS5312849A (sv) |
| BE (1) | BE855617A (sv) |
| BR (1) | BR7703832A (sv) |
| CH (1) | CH635594A5 (sv) |
| DE (1) | DE2718872A1 (sv) |
| DK (1) | DK259477A (sv) |
| ES (1) | ES461987A3 (sv) |
| FI (1) | FI57113C (sv) |
| FR (1) | FR2393008A1 (sv) |
| GB (1) | GB1524917A (sv) |
| HU (1) | HU177333B (sv) |
| IT (1) | IT1116654B (sv) |
| MX (1) | MX4685E (sv) |
| NL (1) | NL187167C (sv) |
| NO (2) | NO145244C (sv) |
| SE (1) | SE426833B (sv) |
| YU (1) | YU39804B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU201091B (en) | 1985-12-26 | 1990-09-28 | Mitsubishi Chem Ind | Process for producing gonatriene derivatives and pharmaceutical compositions comprising same |
| JPS6322598A (ja) * | 1986-07-14 | 1988-01-30 | Mitsubishi Chem Ind Ltd | ゴナトリエン誘導体およびその製造法 |
| JPS6372627A (ja) * | 1986-09-17 | 1988-04-02 | Mitsubishi Kasei Corp | 子宮内膜症治療薬 |
| JPH0780335B2 (ja) * | 1989-11-20 | 1995-08-30 | 富士通株式会社 | リボンカセット |
| PT654267E (pt) * | 1993-11-19 | 2002-09-30 | Jenapharm Gmbh | Carcinoestaticos para terapia hormonal contendo dienogest como componente eficaz |
| DK0780397T3 (da) * | 1995-12-22 | 1999-03-29 | Jenapharm Gmbh | 17alfa-cyanomethylestra-4,9-dien-derivater, fremgangsmåde til deres fremstilling og farmaceutiske præparater indeholdende d |
| US6451778B1 (en) | 1996-07-26 | 2002-09-17 | Wyeth | Oral contraceptive |
| US5858405A (en) * | 1996-07-26 | 1999-01-12 | American Home Products Corporation | Oral contraceptive |
| US5888543A (en) * | 1996-07-26 | 1999-03-30 | American Home Products Corporation | Oral contraceptives |
| US6479475B1 (en) | 1996-07-26 | 2002-11-12 | Wyeth | Oral contraceptive |
| HUP0501132A2 (en) * | 2005-12-05 | 2007-06-28 | Richter Gedeon Nyrt | 17-alpha-cyanomethyl-17betha-hydroxyestra-4,9-diene-3-one of high purity and process for its production |
| US8617597B2 (en) | 2006-07-06 | 2013-12-31 | Bayer Intellectual Property Gmbh | Pharmaceutical composition containing a tetrahydrofolic acid |
| ATE536362T1 (de) * | 2009-05-22 | 2011-12-15 | Heyl Chem Pharm | Verfahren zur synthese von dienogest aus estron-3-methylether |
| WO2011132045A2 (en) | 2010-04-20 | 2011-10-27 | Lupin Limited | Process for the preparation of dienogest substantially free of impurities |
| CN112724191B (zh) * | 2020-12-30 | 2022-11-15 | 上海汇伦医药股份有限公司 | 一种地诺孕素的精制方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502699A (en) * | 1962-05-15 | 1970-03-24 | Herchel Smith | Novel delta4,9-3-ketosteroids and method for preparing same |
| DE1214223B (de) * | 1962-11-22 | 1966-04-14 | Roussel Uclaf | Verfahren zur Herstellung von Hydroxy-hydroxymethyl-steroiden |
| US3624110A (en) * | 1964-08-03 | 1971-11-30 | Herchel Smith | 13-ethylgona-4,9-dienes |
| GB1130881A (en) * | 1964-08-06 | 1968-10-16 | Merck & Co Inc | Steroidal-í¸-dien-3-ones and derivatives thereof |
| FR2031807A5 (en) * | 1969-02-07 | 1970-11-20 | Jenapharm Veb | 17a-subst estratrienes |
| US3931154A (en) * | 1973-07-07 | 1976-01-06 | Schering Aktiengesellschaft | Process for the preparation of steroid oxiranes |
| US4029648A (en) * | 1976-01-15 | 1977-06-14 | Veb Jenapharm | Process of making gona-1,3,5(10),9(11)-tetraenes |
-
1977
- 1977-04-28 DE DE19772718872 patent/DE2718872A1/de active Granted
- 1977-06-01 IT IT49669/77A patent/IT1116654B/it active
- 1977-06-09 GB GB24086/77A patent/GB1524917A/en not_active Expired
- 1977-06-13 SE SE7706835A patent/SE426833B/sv unknown
- 1977-06-13 BE BE178379A patent/BE855617A/xx not_active IP Right Cessation
- 1977-06-13 YU YU1465/77A patent/YU39804B/xx unknown
- 1977-06-13 NL NLAANVRAGE7706465,A patent/NL187167C/xx not_active IP Right Cessation
- 1977-06-13 BR BR7703832A patent/BR7703832A/pt unknown
- 1977-06-13 NO NO772054A patent/NO145244C/no unknown
- 1977-06-13 FR FR7718009A patent/FR2393008A1/fr active Granted
- 1977-06-13 DK DK259477A patent/DK259477A/da not_active Application Discontinuation
- 1977-06-13 CH CH724177A patent/CH635594A5/de not_active IP Right Cessation
- 1977-06-14 HU HU77JE800A patent/HU177333B/hu unknown
- 1977-06-14 FI FI771865A patent/FI57113C/fi not_active IP Right Cessation
- 1977-06-14 MX MX775803U patent/MX4685E/es unknown
- 1977-06-14 JP JP7039777A patent/JPS5312849A/ja active Granted
- 1977-08-31 ES ES461987A patent/ES461987A3/es not_active Expired
-
1979
- 1979-02-13 US US06/011,951 patent/US4248790A/en not_active Expired - Lifetime
-
1981
- 1981-05-25 NO NO811764A patent/NO146574C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU39804B (en) | 1985-04-30 |
| FR2393008B1 (sv) | 1982-05-07 |
| BE855617A (fr) | 1977-12-13 |
| DK259477A (da) | 1977-12-15 |
| GB1524917A (en) | 1978-09-13 |
| IT1116654B (it) | 1986-02-10 |
| NL7706465A (nl) | 1977-12-16 |
| US4248790A (en) | 1981-02-03 |
| JPS5312849A (en) | 1978-02-04 |
| NO772054L (no) | 1977-12-15 |
| ES461987A3 (es) | 1978-06-01 |
| NL187167B (nl) | 1991-01-16 |
| FI57113C (fi) | 1980-06-10 |
| BR7703832A (pt) | 1978-04-25 |
| SE426833B (sv) | 1983-02-14 |
| DE2718872C2 (sv) | 1987-12-10 |
| NO145244C (no) | 1982-02-10 |
| NO146574B (no) | 1982-07-19 |
| DE2718872A1 (de) | 1977-12-22 |
| NL187167C (nl) | 1991-06-17 |
| SE7706835L (sv) | 1978-01-15 |
| FR2393008A1 (fr) | 1978-12-29 |
| FI771865A7 (sv) | 1977-12-15 |
| MX4685E (es) | 1982-07-30 |
| JPS616838B2 (sv) | 1986-03-01 |
| CH635594A5 (de) | 1983-04-15 |
| NO145244B (no) | 1981-11-02 |
| YU146577A (en) | 1982-06-30 |
| NO811764L (no) | 1977-12-15 |
| HU177333B (en) | 1981-09-28 |
| NO146574C (no) | 1982-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: VEB JENAPHARM |