EP0000471A1 - Nouveaux corticoides, procédé pour leur préparation et compositions pharmaceutiques les contenant - Google Patents
Nouveaux corticoides, procédé pour leur préparation et compositions pharmaceutiques les contenant Download PDFInfo
- Publication number
- EP0000471A1 EP0000471A1 EP78100135A EP78100135A EP0000471A1 EP 0000471 A1 EP0000471 A1 EP 0000471A1 EP 78100135 A EP78100135 A EP 78100135A EP 78100135 A EP78100135 A EP 78100135A EP 0000471 A1 EP0000471 A1 EP 0000471A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- corticoids
- general formula
- dihydroxy
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0047—Nitrogen only at position 2(3)
Definitions
- the invention relates to new corticoids, a process for their preparation and pharmaceutical preparations which contain these corticoids as an active ingredient.
- New corticoids processes for their preparation and pharmaceutical preparations containing them.
- alkanoyloxy group Y should preferably be understood to mean a group which is derived from a saturated aliphatic monocarboxylic acid containing 1 to 8 carbon atoms.
- alkanoyloxy groups include:
- the acetoxy group, the propionyloxy group, the butyryloxy group, the pentanoyloxy group and the hexanoyioxy group are acetoxy groups, the propionyloxy group, the butyryloxy group, the pentanoyloxy group and the hexanoyioxy group.
- An alkoxy group Y is preferably understood to mean an alkoxy group containing 1 to 6 carbon atoms, such as, for example, the methoxy group, ethoxy group, propyloxy group or butyloxy group.
- the process according to the invention for the preparation of the new corticosteroid is characterized in that the methylenedioxy groups of a compound of the general formula II hydrolytically cleaves,
- the 21-hydroxy group esterified or to the aldehyde group is oxidized and the aldehyde obtained is oxidized in the presence of an alcohol with atmospheric oxygen or manganese (IV) oxide.
- the cleavage of the methylenedioxy groups and the acylation of the 21-hydroxysteroid formed can be carried out, for example, under the conditions described in German Patent 1,072,622.
- the reaction conditions are suitable, as described in German Offenlegungsschrift 24 41-284.
- the new corticoids of the general formula I are pharmacologically active substances which are distinguished in particular by the fact that, when applied topically, they have a pronounced anti-inflammatory activity, while they are systemically poorly effective or ineffective.
- these compounds are often distinguished by a rapid onset of action, a high intensity and a long duration of action, they are inexpensive to absorb and, in galenical formulations, have relatively good stability.
- the new compounds are suitable in combination with the excipients common in Galician pharmacy for the local treatment of contact dermatitis, various types of eczema, neurodermatoses, erythroderma, burns, pruritis vulvae et ani, rosacea erythematosus cutaneus, psoriasis, lichen planus et verrucosus and the like Skin diseases
- the pharmaceutical specialties are produced in the usual way. Way, by converting the active ingredients with suitable additives in the desired application form, such as: solutions, lotions, ointments, creams or plasters.
- suitable additives such as: solutions, lotions, ointments, creams or plasters.
- the active substance concentration depends on the form of administration.
- an active ingredient concentration of 0.01% to 1% is preferably avoided.
- the new compounds if appropriate in combination with the customary carriers and auxiliaries, are also well suited for the production of inhalants.
- the residue consists of 1.8 g of 2 '- (4-fluoro-phenyl) -11ß, 17 ⁇ -dihydroxy-20-oxo-2H'-2,4-pregnadieno [3,2-c] pyrazol-21-al.
- Ma receives 251 mg of 2 '- (4-fluoro-phenyl) -11ß, 17 ⁇ -dihydroxy-20-oxo-2H'-2,4-pregnadieno [3,2-c] pyrazole-21-acidic acid methyl ester. Melting point 192 ° C (recrystallized from acetone-hexane).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19772727367 DE2727367A1 (de) | 1977-06-14 | 1977-06-14 | Neue kortikoide |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0000471A1 true EP0000471A1 (fr) | 1979-02-07 |
Family
ID=6011715
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100135A Withdrawn EP0000471A1 (fr) | 1977-06-14 | 1978-06-12 | Nouveaux corticoides, procédé pour leur préparation et compositions pharmaceutiques les contenant |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0000471A1 (fr) |
DE (1) | DE2727367A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1496892A2 (fr) * | 2002-04-11 | 2005-01-19 | Merck & Co., Inc. | Derives de 1h-benzo(f)indazol-5-yl utilises en tant que modulateurs selectifs du recepteur glucocorticoide |
WO2009044200A1 (fr) * | 2007-10-04 | 2009-04-09 | Astrazeneca Ab | Composés [3, 2-c] pyrazole stéroïdes à activité glucocorticoïde |
US7625920B2 (en) | 2003-03-07 | 2009-12-01 | Merck & Co., Inc. | Fluorinated 4-azasteroid derivatives as androgen receptor modulators |
WO2010147947A3 (fr) * | 2009-06-16 | 2011-03-03 | Schering Corporation | Nouveaux [3,2-c] hétéroaryl stéroïdes en tant qu'agonistes des récepteurs glucocorticoïdes, compositions et utilisations de ceux-ci |
CN102459306A (zh) * | 2009-04-03 | 2012-05-16 | 阿斯利康(瑞典)有限公司 | 具有糖皮质激素活性的甾族[3,2-c]吡唑化合物的新酰胺衍生物 |
US8338587B2 (en) | 2009-04-03 | 2012-12-25 | Astrazeneca Ab | Compounds |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1418994A1 (de) * | 1960-11-23 | 1969-04-24 | Merck & Co Inc | 17 alpha,21-Dihydroxy-20-oxo-4-pregnen[3,2-c]pyrazol-Verbindungen und ihre 21-Ester und ein Verfahren zu ihrer Herstellung |
US3704295A (en) * | 1959-02-16 | 1972-11-28 | Sterling Drug Inc | Steroido(3,2-c)pyrazoles and preparation thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3299054A (en) * | 1961-12-01 | 1967-01-17 | Merck & Co Inc | 4-pregneno-[3, 2-c] pyrazoles and processes of preparing them |
-
1977
- 1977-06-14 DE DE19772727367 patent/DE2727367A1/de active Granted
-
1978
- 1978-06-12 EP EP78100135A patent/EP0000471A1/fr not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3704295A (en) * | 1959-02-16 | 1972-11-28 | Sterling Drug Inc | Steroido(3,2-c)pyrazoles and preparation thereof |
DE1418994A1 (de) * | 1960-11-23 | 1969-04-24 | Merck & Co Inc | 17 alpha,21-Dihydroxy-20-oxo-4-pregnen[3,2-c]pyrazol-Verbindungen und ihre 21-Ester und ein Verfahren zu ihrer Herstellung |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 67 (1967) 107174v & J. Pharm. Pharmacol 19(9) 590-5, (1967) & CHEMICAL ABSTRACTS, 8th Collective Index Formulas S10035 f. * |
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Band 86 (1964) Seite 1520 bis 1527. * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7625937B2 (en) | 2002-04-11 | 2009-12-01 | Merck & Co., Inc. | 1H-benzo[F]indazol-5-YL derivatives as selective glucocorticoid receptor modulators |
JP2005528385A (ja) * | 2002-04-11 | 2005-09-22 | メルク エンド カムパニー インコーポレーテッド | 選択的糖質コルチコイド受容体モジュレーターとしての1H−ベンゾ[f]インダゾール−5−イル誘導体 |
EP1496892A4 (fr) * | 2002-04-11 | 2006-01-25 | Merck & Co Inc | Derives de 1h-benzo(f)indazol-5-yl utilises en tant que modulateurs selectifs du recepteur glucocorticoide |
US7282591B2 (en) | 2002-04-11 | 2007-10-16 | Merck & Co., Inc. | 1h-benzo{f}indazol-5-yl derivatives as selective glucocorticoid receptor modulators |
EP1496892A2 (fr) * | 2002-04-11 | 2005-01-19 | Merck & Co., Inc. | Derives de 1h-benzo(f)indazol-5-yl utilises en tant que modulateurs selectifs du recepteur glucocorticoide |
US7625920B2 (en) | 2003-03-07 | 2009-12-01 | Merck & Co., Inc. | Fluorinated 4-azasteroid derivatives as androgen receptor modulators |
US8163724B2 (en) | 2007-10-04 | 2012-04-24 | Astrazeneca Ab | Glucocorticosteroids, processes for their preparation, pharmaceutical compositions containing them and their use in therapy |
WO2009044200A1 (fr) * | 2007-10-04 | 2009-04-09 | Astrazeneca Ab | Composés [3, 2-c] pyrazole stéroïdes à activité glucocorticoïde |
AU2008306593B2 (en) * | 2007-10-04 | 2012-04-12 | Astrazeneca Ab | Steroidal [3, 2-C] pyrazole compounds, with glucocorticoid activity |
JP2010540612A (ja) * | 2007-10-04 | 2010-12-24 | アストラゼネカ・アクチエボラーグ | グルココルチコイド活性を有するステロイド[3,2−c]ピラゾール化合物 |
AU2008306593C1 (en) * | 2007-10-04 | 2012-10-04 | Astrazeneca Ab | Steroidal [3, 2-C] pyrazole compounds, with glucocorticoid activity |
CN102459306A (zh) * | 2009-04-03 | 2012-05-16 | 阿斯利康(瑞典)有限公司 | 具有糖皮质激素活性的甾族[3,2-c]吡唑化合物的新酰胺衍生物 |
US8338587B2 (en) | 2009-04-03 | 2012-12-25 | Astrazeneca Ab | Compounds |
WO2010147947A3 (fr) * | 2009-06-16 | 2011-03-03 | Schering Corporation | Nouveaux [3,2-c] hétéroaryl stéroïdes en tant qu'agonistes des récepteurs glucocorticoïdes, compositions et utilisations de ceux-ci |
CN102834406A (zh) * | 2009-06-16 | 2012-12-19 | 默沙东公司 | 作为糖皮质激素受体激动剂的新的[3.2-c]杂芳基甾体、其组合物和用途 |
Also Published As
Publication number | Publication date |
---|---|
DE2727367A1 (de) | 1979-01-04 |
DE2727367C2 (fr) | 1988-12-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): BE CH DE FR GB LU NL |
|
17P | Request for examination filed | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Withdrawal date: 19821028 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: WENDT, HANS, DR Inventor name: LAURENT, HENRY, DR. Inventor name: WIECHERT, RUDOLF, PROF. |