EP0000742A1 - 17-Alcoylcarbonates de corticoides, leur procédé de préparation et compositions les contenant - Google Patents

17-Alcoylcarbonates de corticoides, leur procédé de préparation et compositions les contenant Download PDF

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Publication number
EP0000742A1
EP0000742A1 EP7878100524A EP78100524A EP0000742A1 EP 0000742 A1 EP0000742 A1 EP 0000742A1 EP 7878100524 A EP7878100524 A EP 7878100524A EP 78100524 A EP78100524 A EP 78100524A EP 0000742 A1 EP0000742 A1 EP 0000742A1
Authority
EP
European Patent Office
Prior art keywords
carbonate
acid chloride
methyl
chloroformate
prednisolone
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.)
Granted
Application number
EP7878100524A
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German (de)
English (en)
Other versions
EP0000742B1 (fr
Inventor
Ulrich Dr. Stache
Werner Dr. Fritsch
Hans Georg Dr. Alpermann
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Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Publication of EP0000742A1 publication Critical patent/EP0000742A1/fr
Application granted granted Critical
Publication of EP0000742B1 publication Critical patent/EP0000742B1/fr
Expired legal-status Critical Current

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Classifications

    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0061—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 substituted in position 17 alfa substituted in position 16
    • C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
    • 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

  • a carboxylic acid such as, for example, ants, vinegars, propions, butter is preferably , Valerian, oxalic, maleic, fumaric, succinic or adipic acid, or an organic sulfonic acid, such as, for example, p-toluene, benzene, p- or o- or m-chloro- or bromobenzenesulfonic acid or one inorganic acid, such as hydrochloric, sulfuric, carbonic, nitric acid used.
  • a carboxylic acid such as, for example, ants, vinegars, propions, butter is preferably , Valerian, oxalic, maleic, fumaric, succinic or adipic acid, or an organic sulfonic acid, such as, for example, p-toluene, benzene, p- or o- or m-chloro- or bromobenzenesulfonic acid or one inorganic
  • water or / and inert organic solvents such as alcohols, linear or cyclic ethers, esters, dialkylformamides, dialkylsulfoxides or hexamethylphosphoric acid triamide, for dilution, often in addition to the dilution effect a catalytic or regioselective effect in the direction of the desired course of the reaction is brought about.
  • the course of the reaction in the desired direction is expediently followed by thin-layer chromatography. It is advantageous to terminate the reaction by neutralizing, for example, with dilute ammonia or adjusting the pH to above 7 if the thin-layer diagram, after optimal formation of the desired steroid-17-monoalkylcarbonate-21-hydroxy compounds, isometrized to their undesired steroid -17-Hydroxy-21- monoalkyl carbonate compounds.
  • the corticoid-17,21-orthoalkylcarbonate is preferably dissolved in a carboxylic acid, such as, for example, in acetic acid or propionic acid, preferably about 0.1 to 1% water is added and the mixture is left at a temperature of 0 for up to about 8 hours ° react to the boiling point of the acid or solvent used.
  • a carboxylic acid such as, for example, in acetic acid or propionic acid
  • the reaction mixture is stirred into water or saline, neutralized, for example, with aqueous ammonia or another weak base, either the precipitate is suctioned off or extracted in the usual way with organic solvents, evaporates, recrystallizes the products obtained and chromatographs them, if starting material or 21-alkyl carbonate is still detectable in the TLC diagram, if necessary on silica gel or aluminum oxide.
  • the steroid component is dissolved in an inert solvent, such as, for example, in an ether, such as dioxane, tetrahydrofuran, diglyme, or optionally halogenated hydrocarbon, such as benzene, toluene, cyclohexane, methylene chloride, chloroform or in a mixture of these solvents.
  • an ether such as dioxane, tetrahydrofuran, diglyme
  • optionally halogenated hydrocarbon such as benzene, toluene, cyclohexane, methylene chloride, chloroform or in a mixture of these solvents.
  • a tertiary base such as pyridine, quinoline, triethylamine or dimethylaniline are added. You can also use an organic base such as sodium bicarbonate or calcium carbonate to remove the acid.
  • 1 to 200 molar equivalents, preferably 1 to 3 molar equivalents, of one of the above-mentioned acylating agents, optionally dissolved in one of the above-mentioned solvents, are added dropwise at a temperature between -40 ° C. and the boiling point of the solvent used, preferably between 0 ° C. and 25 0 C, too.
  • the reaction mixture is then left to stand for from one to 120 hours at a temperature between -40 ° C. and the boiling point of the solvent, preferably between 0 ° C. and 25 ° C.
  • reaction mixture For working up, the reaction mixture is poured into water, to which sodium bicarbonate has optionally been added, the reaction products generally precipitating out in crystalline form, often only after prolonged standing.
  • reaction products that remain oily are enriched by shaking with a suitable extractant and evaporation. , 'If necessary, be separated by recrystallization or by chromatography or purified the reaction products can. Intensive digestion is often sufficient, in one that dissolves the reaction product as little or as little as possible organic solvents, such as diethyl ether or cyclohexane or a mixture of these components, for further purification of the reaction products.
  • a hydroxy group in the 11-position can optionally be oxidized to the keto group by customary methods. This oxidation is preferably carried out with chromium trioxide in an acidic medium and in an inert organic solvent.
  • the process products have valuable pharmacological properties. They have a particularly strong local and topical anti-inflammatory activity and in some cases show an advantageous ratio of local to systemic anti-inflammatory activity, as can be derived from standard pharmacological tests.
  • the process products can be used in veterinary and human therapy for the treatment of inflammatory intestinal disorders of various origins in the form of suspensions, ointments, creams, sprays, etc. When applied topically, they can be in the form of crystal suspensions - e.g. with intra-articular injection. It should be emphasized as particularly advantageous for the local and topical form of therapy that, due to their favorable ratio of local to systemic antiphlogistic effect, the process products can cause practically only minor systemic side effects even with high-dose and long-lasting therapy. In addition, the process products used have a significantly better acid stability than the cyclic cortocoid-17,21-orthocarbonates on which they are based. This fact is of crucial importance for the safe and therapy-rich application of the products according to the invention.
  • ointments, creams, suspensions, etc. with a concentration of 0.01 to 2 (wt.) %, used in topical administrations in the form of local (non-systemic) injections doses from 0.1 mg to 100 mg.
  • the IR spectra (in KBr) are recorded with the Perkin-Elmer 521 grating spectrophotometer. Only the characteristic bands are listed.
  • the UV spectra (in methanol) were recorded using the Beckman DK 1 A spectrophotometer.
  • the mass spectrometric investigations (MS) are carried out using the MS 9 device (AEI).
  • the above substance is dissolved in 60 ml of absolute pyridine and, after cooling to 0 °, 2.3 ml of propionic acid chloride 10 are added. After 1 hour at 0 ° and a further hour at 20 °, the reaction mixture is stirred into 500 ml of semi-saturated aqueous sodium chloride solution. The mixture is then extracted with 15 methylene chloride, the organic phase washed neutral with water, dilute hydrochloric acid and water, dried and evaporated to dryness in vacuo. The 4.95 g of crude 6 ⁇ -fluoro-prednisolone-17 ⁇ -ethylcar-20bonate-21-propionate obtained can be purified as follows.
  • the 6 ⁇ -methyl-prednisolone-17 ⁇ , 21-diethyl carbonate used as starting material is obtained analogously according to DBP 16 68 079 as follows.
  • a solution of 17 g of Urbason in 600 ml of anhydrous dioxane is stirred for 5 hours at room temperature after the addition of 47.0 ml of tetraethyl orthocarbonate and 1.05 g of p-toluenesulfonic acid. Then the reaction mixture is poured into a solution of 6.0 g of sodium hydrogen carbonate in 4.0 l of water. The mixture is then worked up as described in Example 7. 21.1 g of 6 ⁇ -methyl-prednisolone-17 ⁇ 21-bis- (ethyl carbonate) of mp 109-112 ° are obtained.
  • bimedrazole-17-n-propyl carbonate (representation: bimedrazole + tetra-n-propyl-orthocarbonate instead of tetraethyl orthocarbonate initially gives the amorphous bimedrazole-17,21-di-n-propylorthocarbonate, the then selectively solvolysed analogously in glacial acetic acid / water), the corresponding -21-carboxylic acid esters, -21-carbonates and -21-sulfonic acid esters are shown.
  • the homologous corticoid-17-n-propyl-ocarbonates are used in the reaction, the corresponding corticoid-17-nipropyl carbonate-21-chloroacetates are obtained after the reaction has been carried out analogously and worked up .
  • reaction mixture is poured into water which contains a quantity of pyridine or alkali metal carbonate required for neutralization, extracted several times with methylene chloride, washed with water, dried and concentrated in Vacuum on.
  • the foam obtained is recrystallized from acetone / diisopropyl ether and gives 2.1 g of 11-dehydro-dexamethasone 17,21-bis- [ethylearbonate], mp. 212 ° C.
  • the corticoid 17-alkylearbonates shown in the previous examples which in 11-position have a hydroxyl and in the 21-position either an alkyl carbonate or alkyl carboxylic acid ester or alkyl or arylsulfonic acid ester group, used in the oxidation reaction just described, the corresponding 11-dehydrocorticoid-17 is obtained after an analogous reaction procedure and working up -alkyl carbonate -21-alkyl carbonates, or -21-alkyl carboxylic acid esters, or -21-alkyl sulfonic acid esters, or -21-aryl sulfonic acid esters.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
EP78100524A 1977-08-04 1978-07-27 17-Alcoylcarbonates de corticoides, leur procédé de préparation et compositions les contenant Expired EP0000742B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735110 DE2735110A1 (de) 1977-08-04 1977-08-04 Corticoid-17-alkylcarbonate und verfahren zu ihrer herstellung
DE2735110 1977-08-04

Publications (2)

Publication Number Publication Date
EP0000742A1 true EP0000742A1 (fr) 1979-02-21
EP0000742B1 EP0000742B1 (fr) 1982-05-12

Family

ID=6015590

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100524A Expired EP0000742B1 (fr) 1977-08-04 1978-07-27 17-Alcoylcarbonates de corticoides, leur procédé de préparation et compositions les contenant

Country Status (13)

Country Link
US (1) US4242334A (fr)
EP (1) EP0000742B1 (fr)
JP (1) JPS5436248A (fr)
AT (1) AT372093B (fr)
AU (1) AU522854B2 (fr)
CA (1) CA1118411A (fr)
DE (2) DE2735110A1 (fr)
DK (1) DK154145C (fr)
EG (1) EG13560A (fr)
ES (1) ES472147A1 (fr)
HU (1) HU182732B (fr)
IT (1) IT1097652B (fr)
ZA (1) ZA784417B (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004975A3 (en) * 1978-04-25 1979-11-14 Hoechst Aktiengesellschaft 17-alkylcarbonates of corticoids, process for their preparation and their use as medicines against dermatoses
FR2486529A1 (fr) * 1980-07-10 1982-01-15 Otsuka Pharma Co Ltd Steroides doux anti-inflammatoires et medicament contenant ces substances
EP0104746A1 (fr) * 1982-08-30 1984-04-04 The Upjohn Company Esters de 21-hydroxy-corticostéroides et compositions les contenant
EP0136586A3 (en) * 1983-09-07 1986-01-29 Mitsubishi Chemical Industries Limited Novel corticoid derivatives and process for production thereof
EP0266719A1 (fr) * 1986-11-06 1988-05-11 Hoechst Aktiengesellschaft Procédé de préparation du 17-éthylcarbonate de prédnisolone par transposition du 21 éthylcarbonate de prédnisolone
EP0470617A3 (en) * 1990-08-10 1992-04-01 Hoechst Aktiengesellschaft 17-substituted corticoid-17-alkylcarbonates, a process for their preparation and pharmaceutical compositions containing them
EP0646593A1 (fr) * 1993-10-05 1995-04-05 Hoechst Aktiengesellschaft Ester d'acide corticoide-17,21-dicarboxylique et ester d'acide corticostéroide-17-carboxylique-21-carbonique, procédé pour leur préparation et médicaments les contenant
EP0640616A3 (fr) * 1993-08-27 1995-06-28 Hoechst Ag Dérivés 17-alkylecarbonate, 21-0-esters des corticostéroides, un procédé de leur préparation et les compositions pharmaceutiques les contenant.
RU2171810C2 (ru) * 1999-07-21 2001-08-10 Научно-исследовательский институт наркологии 17α-АЦЕТАТ-21-ПИВАЛОАТ 17α, 21-ДИГИДРОКСИПРЕГН-4-ЕН-3,20-ДИОН, ОБЛАДАЮЩИЙ АНТИАЛКОГОЛЬНОЙ И АНКСИОЛИТИЧЕСКОЙ АКТИВНОСТЬЮ

Families Citing this family (28)

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US4996335A (en) * 1980-07-10 1991-02-26 Nicholas S. Bodor Soft steroids having anti-inflammatory activity
US4456602A (en) * 1982-08-23 1984-06-26 The Upjohn Company Amine containing ester prodrugs of corticosteroids
JPS6056997A (ja) * 1983-09-07 1985-04-02 Mitsubishi Chem Ind Ltd 新規な６−酸素化コルチコイド／７α−カ−ボネ−ト誘導体およびその製法
AU572589B2 (en) 1983-12-14 1988-05-12 Upjohn Company, The 11(alpha)-difluoromethyl and (e)-and (z)-11-fluoromethylene steroids
PT78973A (en) * 1984-07-25 1984-08-01 Joao Emerico Villax New preparation process of the 9alpha-fluoro 17,21-acylates or hidroxilades in 17 and 21 chloro-corticosteroid
US20060229258A1 (en) * 2003-07-30 2006-10-12 Daniela Serikaku Steroidal compositions containing hydroxycarboxylic acids and methods of using the same
AR045536A1 (es) * 2003-08-29 2005-11-02 Ranbaxy Lab Ltd Inhibidores de la fosfodiesterasa tipo -iv
US20070259874A1 (en) * 2003-11-26 2007-11-08 Palle Venkata P Phosphodiesterase Inhibitors
US7915286B2 (en) 2005-09-16 2011-03-29 Ranbaxy Laboratories Limited Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors
EP1948167A1 (fr) * 2005-10-19 2008-07-30 Ranbaxy Laboratories, Ltd. Compositions d'inhibiteurs de la phosphodiesterase de type iv
RU2008119323A (ru) 2005-10-19 2009-11-27 Рэнбакси Лабораториз Лимитед (In) Фармацевтические композиции мускаринового рецептора
JP2010504323A (ja) * 2006-09-22 2010-02-12 ランバクシー ラボラトリーズ リミテッド Ｉｖ型ホスホジエステラーゼの阻害物質
EP2066661A2 (fr) * 2006-09-22 2009-06-10 Ranbaxy Laboratories Limited Inhibiteurs de phosphodiesterase
CN101200484B (zh) * 2006-12-13 2010-12-08 天津天药药业股份有限公司 一种甾体开环物的生产工艺方法
US20080207659A1 (en) 2007-02-15 2008-08-28 Asit Kumar Chakraborti Inhibitors of phosphodiesterase type 4
SI2124944T1 (sl) * 2007-03-14 2012-05-31 Ranbaxy Lab Ltd Derivati pirazolo b piridina kot inhibitorji fosfodiesteraze
US20110130403A1 (en) * 2007-03-14 2011-06-02 Ranbaxy Laboratories Limited Pyrazolo [3, 4-b] pyridine derivatives as phosphodiesterase inhibitors
AU2008306593C1 (en) * 2007-10-04 2012-10-04 Astrazeneca Ab Steroidal [3, 2-C] pyrazole compounds, with glucocorticoid activity
CA2707618A1 (fr) * 2007-12-20 2009-07-02 Astrazeneca Ab Derives de steroides agissant comme des agonistes des recepteurs de glucocorticosteroides
EP2111861A1 (fr) 2008-04-21 2009-10-28 Ranbaxy Laboratories Limited Compositions d'inhibiteurs de type IV de la phosphodiestérase
UY32520A (es) * 2009-04-03 2010-10-29 Astrazeneca Ab Compuestos que tienen actividad agonista del receptor de glucocorticoesteroides
UY32523A (es) * 2009-04-03 2010-10-29 Astrazeneca Ab Compuestos que tienen actividad agonista del receptor de glucocorticosteroides
UY32521A (es) * 2009-04-03 2010-10-29 Astrazeneca Ab Combinación para emplear en el tratamiento de enfermedades respiratorias
UY32525A (es) * 2009-04-03 2010-10-29 Astrazeneca Ab Compuestos que tienen actividad agonista del receptor de glucocorticosteroides
UA116622C2 (uk) * 2011-11-11 2018-04-25 Аллерган, Інк. Похідні 4-прегенен-11ss-17-21-тріол-3,20-діону для лікування хвороб очей
CN102964414A (zh) * 2012-12-14 2013-03-13 中国科学院上海有机化学研究所 17位甾体羧酸酯的合成方法
CN110684068A (zh) * 2018-07-04 2020-01-14 成都文帆生物医药研发有限公司 一种制备泼尼卡松中间体的方法
CN116023425B (zh) * 2023-03-28 2023-06-20 南京师范大学 曲安西龙衍生物及其医药用途

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US3558675A (en) * 1969-06-30 1971-01-26 Merck & Co Inc Steroid carbonates and process
LU68212A1 (fr) * 1972-08-11 1973-10-16

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DE1195748B (de) * 1961-06-24 1965-07-01 Vismara Francesco Spa Verfahren zur Herstellung von 1'-substituierten 17alpha, 21-(1'-Alkoxy)-methylendioxysterioden
US3422193A (en) * 1966-08-11 1969-01-14 Schering Corp 17-mono esters of corticoids
DE1668079B2 (de) * 1968-01-18 1976-09-16 Hoechst Ag, 6000 Frankfurt Dialkylorthocarbonate von 17alpha, 21-dihydroxysteroiden und verfahren zu ihrer herstellung

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3558675A (en) * 1969-06-30 1971-01-26 Merck & Co Inc Steroid carbonates and process
LU68212A1 (fr) * 1972-08-11 1973-10-16

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0004975A3 (en) * 1978-04-25 1979-11-14 Hoechst Aktiengesellschaft 17-alkylcarbonates of corticoids, process for their preparation and their use as medicines against dermatoses
US4377575A (en) * 1978-04-25 1983-03-22 Hoechst Aktiengesellschaft Corticoid-17-(alkyl carbonates) and process for their manufacture
FR2486529A1 (fr) * 1980-07-10 1982-01-15 Otsuka Pharma Co Ltd Steroides doux anti-inflammatoires et medicament contenant ces substances
EP0104746A1 (fr) * 1982-08-30 1984-04-04 The Upjohn Company Esters de 21-hydroxy-corticostéroides et compositions les contenant
EP0136586A3 (en) * 1983-09-07 1986-01-29 Mitsubishi Chemical Industries Limited Novel corticoid derivatives and process for production thereof
EP0266719A1 (fr) * 1986-11-06 1988-05-11 Hoechst Aktiengesellschaft Procédé de préparation du 17-éthylcarbonate de prédnisolone par transposition du 21 éthylcarbonate de prédnisolone
EP0470617A3 (en) * 1990-08-10 1992-04-01 Hoechst Aktiengesellschaft 17-substituted corticoid-17-alkylcarbonates, a process for their preparation and pharmaceutical compositions containing them
AU646066B2 (en) * 1990-08-10 1994-02-03 Hoechst Aktiengesellschaft Corticoid-17-alkylcarbonates substituted in the 17-position process for their preparation and pharmaceuticals containing them
EP0640616A3 (fr) * 1993-08-27 1995-06-28 Hoechst Ag Dérivés 17-alkylecarbonate, 21-0-esters des corticostéroides, un procédé de leur préparation et les compositions pharmaceutiques les contenant.
EP0646593A1 (fr) * 1993-10-05 1995-04-05 Hoechst Aktiengesellschaft Ester d'acide corticoide-17,21-dicarboxylique et ester d'acide corticostéroide-17-carboxylique-21-carbonique, procédé pour leur préparation et médicaments les contenant
RU2171810C2 (ru) * 1999-07-21 2001-08-10 Научно-исследовательский институт наркологии 17α-АЦЕТАТ-21-ПИВАЛОАТ 17α, 21-ДИГИДРОКСИПРЕГН-4-ЕН-3,20-ДИОН, ОБЛАДАЮЩИЙ АНТИАЛКОГОЛЬНОЙ И АНКСИОЛИТИЧЕСКОЙ АКТИВНОСТЬЮ

Also Published As

Publication number Publication date
ES472147A1 (es) 1979-03-16
JPS5436248A (en) 1979-03-16
DK154145B (da) 1988-10-17
IT7826424A0 (it) 1978-08-02
DE2735110A1 (de) 1979-02-15
HU182732B (en) 1984-03-28
DK154145C (da) 1989-02-27
ATA564578A (de) 1983-01-15
CA1118411A (fr) 1982-02-16
IT1097652B (it) 1985-08-31
AT372093B (de) 1983-08-25
EG13560A (en) 1981-12-31
JPH0112758B2 (fr) 1989-03-02
US4242334A (en) 1980-12-30
DK344978A (da) 1979-02-05
ZA784417B (en) 1979-08-29
AU3861178A (en) 1980-02-07
DE2861809D1 (en) 1982-07-01
AU522854B2 (en) 1982-07-01
EP0000742B1 (fr) 1982-05-12

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