HUP0301332A2 - New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them - Google Patents
New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing themInfo
- Publication number
- HUP0301332A2 HUP0301332A2 HU0301332A HUP0301332A HUP0301332A2 HU P0301332 A2 HUP0301332 A2 HU P0301332A2 HU 0301332 A HU0301332 A HU 0301332A HU P0301332 A HUP0301332 A HU P0301332A HU P0301332 A2 HUP0301332 A2 HU P0301332A2
- Authority
- HU
- Hungary
- Prior art keywords
- general formula
- bismethylene
- mono
- group
- steroid derivatives
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000004480 active ingredient Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 239000003433 contraceptive agent Substances 0.000 abstract 1
- 230000002254 contraceptive effect Effects 0.000 abstract 1
- 229940011871 estrogen Drugs 0.000 abstract 1
- 239000000262 estrogen Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000000757 progestagenic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
A találmány tárgyát az (I) általános képletű új, mono- és biszmetilén-szteroidszármazékok - ahol Z két hidrogénatomot vagy egy oxocsoportot,X és Y egymástól függetlenül vagy két hidrogénatomot vagy egy CH2=csoportot jelent azzal a megszorítással, hogy közülük legalább azegyik CH2= csoport és Z oxo-csoport jelentése esetén Y kéthidrogénatomot jelent, R egy 1-4 szénatomos alkilcsoportot képvisel -,valamint a hatóanyagként ezeket tartalmazó gyógyászati készítmények,továbbá a hatóanyagok és a gyógyászati készítmények előállításáraszolgáló eljárások képezik. Az (I) általános képletű vegyületek közétartozó mono- és biszmetilén-származékok, progesztogén hatásúvegyületek, melyek önmagukban vagy valamely ösztrogénnel kombinálvafogamzásgátló készítmények hatóanyagaként kerülhetnek alkalmazásra.Továbbá felhasználásra kerülhetnek még az endometriózis gyógyításában,valamint az ösztrogénpótló terápiában az ösztrogén komponens gesztagénkísérőjeként. A találmány szerinti az (I) általános képletű mono- ésbiszmetilén-szteroidszármazékokat úgy állítják elő, hogy valamely (II)általános képletű vegyületet - ahol Z, X és Y jelentése az (I)általános képletnél megadott - erős sav jelenlétében egy (RCO)2Oáltalános képletű savanhidriddel vagy egy R-CO-CI általános képletűsavkloriddal - ahol R egy 1-4 szénatomos alkilcsoportot jelent -reagáltatják. ÓThe subject of the invention is the new, mono- and bismethylene steroid derivatives of the general formula (I) - where Z represents two hydrogen atoms or an oxo group, X and Y independently of each other or two hydrogen atoms or a CH2= group with the restriction that at least one of them is CH2= group and Z means an oxo group, Y means two hydrogen atoms, R represents an alkyl group with 1-4 carbon atoms - as well as the pharmaceutical preparations containing these as active ingredients, and also the processes for the production of the active ingredients and medicinal preparations. The compounds of general formula (I) include mono- and bismethylene derivatives, compounds with progestogenic effects, which can be used alone or in combination with an estrogen as the active ingredient of contraceptive preparations. According to the invention, the mono- and bismethylene steroid derivatives of the general formula (I) are prepared by reacting a compound of the general formula (II) - where Z, X and Y are as given in the general formula (I) - in the presence of a strong acid with a general formula (RCO)2O with an acid anhydride of the formula or an acid chloride of the general formula R-CO-CI - where R represents an alkyl group with 1-4 carbon atoms - are reacted. HE
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0301332A HUP0301332A3 (en) | 2003-05-14 | 2003-05-14 | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
| PCT/HU2004/000027 WO2004101594A1 (en) | 2003-05-14 | 2004-03-25 | New mono-and bismethylene-steroid derivatives and process for their synthesis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0301332A HUP0301332A3 (en) | 2003-05-14 | 2003-05-14 | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU0301332D0 HU0301332D0 (en) | 2003-07-28 |
| HUP0301332A2 true HUP0301332A2 (en) | 2004-12-28 |
| HUP0301332A3 HUP0301332A3 (en) | 2006-04-28 |
Family
ID=89981359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0301332A HUP0301332A3 (en) | 2003-05-14 | 2003-05-14 | New mono-and bismethylene steroid derivatives and process for their synthesis and pharmaceutical compositions containing them |
Country Status (2)
| Country | Link |
|---|---|
| HU (1) | HUP0301332A3 (en) |
| WO (1) | WO2004101594A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU227112B1 (en) * | 2006-06-14 | 2010-07-28 | Richter Gedeon Nyrt | Industrial process for the synthesis of 17alpha-acetoxy-11betha-[4-(n,n-dimethyl-amino)-phenyl]-19-norpregna-4,9-diene-3,20-dione and the new intermediates of the process |
| CN105237606B (en) * | 2014-07-11 | 2018-08-24 | 上海创诺制药有限公司 | It is a kind of to be used to synthesize intermediate of Desogestrel and its preparation method and application |
| CN106986911B (en) * | 2017-03-23 | 2019-05-10 | 湖南玉新药业有限公司 | The preparation method of dexamethasone key intermediate connection alkene sulfoxide object |
| CN106986908B (en) * | 2017-03-23 | 2019-05-10 | 湖南玉新药业有限公司 | The preparation method of betamethasone |
| CN112010919A (en) * | 2020-09-28 | 2020-12-01 | 湖南新合新生物医药有限公司 | Preparation method of levonorgestrel pharmacopoeia impurity S |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH581150A5 (en) * | 1967-05-05 | 1976-10-29 | Schering Ag | |
| US3927046A (en) * | 1972-12-09 | 1975-12-16 | Akzona Inc | Novel 11,11-alkylidene steroids |
| DE3042529A1 (en) * | 1980-11-07 | 1982-06-24 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 11-METHYLENE (DELTA) (UP ARROW) 1 (UP ARROW) (UP ARROW) 5 (UP ARROW) STEROIDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM |
| HU216828B (en) * | 1995-12-22 | 1999-09-28 | Richter Gedeon Vegyészeti Gyár Rt. | Steroids, process for producing them, pharmaceutical compositions containing them and their intermediates |
-
2003
- 2003-05-14 HU HU0301332A patent/HUP0301332A3/en unknown
-
2004
- 2004-03-25 WO PCT/HU2004/000027 patent/WO2004101594A1/en active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| HU0301332D0 (en) | 2003-07-28 |
| HUP0301332A3 (en) | 2006-04-28 |
| WO2004101594A1 (en) | 2004-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |