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 PDF

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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Withdrawn
Application number
EP78100135A
Other languages
German (de)
English (en)
Inventor
Henry Dr. Laurent
Rudolf Prof. Wiechert
Hans Dr Wendt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Publication of EP0000471A1 publication Critical patent/EP0000471A1/fr
Withdrawn legal-status Critical Current

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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)
EP78100135A 1977-06-14 1978-06-12 Nouveaux corticoides, procédé pour leur préparation et compositions pharmaceutiques les contenant Withdrawn EP0000471A1 (fr)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
DE2727367C2 (fr) 1988-12-29
DE2727367A1 (de) 1979-01-04

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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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.