Corticoid 21-sulfopropionates and the salts thereof, a process for the production thereof and pharmaceutical preparations thereof
AssigneeSchering Corporation
InventorsHenry Laurent, Peter Esperling, Joachim-Friedrich Kapp, Rudolf Wiechert
Life of this patent
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Abstract
Corticoid 21-sulfopropionates of the formula ##STR1## wherein St is a steroid nucleus of a corticoid having anti-inflammatory activity, and the salts thereof with physiologically acceptable bases, simultaneously form stable, sterilizable and storable solutions and also are very rapidly cleaved after i.v. administration, yielding the free corticoids as the cleavage product.
Claims28
A corticoid 21-sulfopropionate of the formula ##STR11## wherein represents a single of double bond;
- X is hydrogen, chlorine, fluorine or methyl;
- Y is hydrogen, fluorine or chlorine;
- Z is oxo, or hydrogen in the .alpha.-position and hydroxy in the .beta.-position;
- --U--V represents --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or ##STR12## wherein R.sub.1 is hydrogen, hydroxy or acyloxy, wherein the acyl group is derived from a C.sub.1-8 hydrocarbon carboxylic acid;
- R.sub.2 is hydrogen or methyl;
- and R.sub.3 and R.sub.4 are independently each alkyl of 1-4 carbon atoms;
- and the salts thereof with physiologically acceptable bases.
6.alpha.-Fluoro-11.beta.-hyd roxy-16.alpha.-methyl-21-(3-sulfopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium, potassium, lithium or ammonium salts thereof.
6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methy l-21-(3-sulfopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium, potassium, lithium, calcium or ammonium salts thereof.
11.beta.,17.alpha.-Dihydroxy-21-(3-sulfopropionylox y)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
11.beta.,17.alpha.-Dihydroxy-6.alpha.-methyl-21-(3-sul fopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
9.alpha.-Fluoro-11.beta.-hydroxy-16.alpha.,17.alpha.-isopropylidene-dio xy-21-(3-sulfopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
9.alp ha.-Fluoro-11.beta.,17.alpha.-dihydroxy-16.alpha.-methyl-21-(3-sulfopropion yloxy)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
9.alpha.-Chloro-6.alpha.-fluoro-11.beta.-hydroxy-16.alpha. -methyl-21-(3-sulfopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
9.alpha.-F luoro-11.beta.-hydroxy-16.alpha.-methyl-21-(3-sulfopropionyloxy)-1,4-pregna diene-3,20-dione and the sodium salt thereof.
9.alpha.-Fluoro-11.beta.,17.alpha.-dihydr oxy-16.beta.-methyl-21-(3-sulfopropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
11.beta.,17.alpha.-Di hydroxy-21-(3-sulfopropionyloxy)-4-pregnene-3,20-dione and the sodium salt thereof.
9.alp ha.-Fluoro-11.beta.-hydroxy-16.beta.-methyl-17.alpha.-valeryloxy-21-(3-sulf opropionyloxy)-1,4-pregnadiene-3,20-dione and the sodium or potassium salts thereof.
9.alp ha.-Fluoro-11.beta.,17.alpha.-dihydroxy-21-(3-sulfopropionyloxy)-4-pregnene -3,20-dione and the sodium salt thereof.
17.alpha.-Butyryloxy-11.beta.-hydrox y-21-(3-sulfopropionyloxy)-4-pregnene-3,20-dione and the sodium salt thereof.
6.alp ha.-Fluoro-11.beta.,17.alpha.-dihydroxy-21-(3-sulfopropionyloxy)-1,4-pregna diene-3,20-dione and the sodium salt thereof.
11.beta.,17a.alpha.-Dihydroxy-21-(3-sulfo propionyloxy)-D-homo-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
9.alpha.-Fluoro-11.beta.,17a.alpha.-dihydroxy-21-(3-sulfopropionyloxy)- D-homo-1,4-pregnadiene-3,20-dione and the sodium salt thereof.
6-Chloro-11.beta.,17.alpha.-dihydroxy-21-(3-sulfopropionyl oxy)-1,4,6-pregnatriene-3,20-dione and the sodium salt thereof.
6-Chloro-11.beta.,17.alpha.-dihydroxy-1.alpha.,2.alpha.-met hylene-21-(3-sulfopropionyloxy)-4,6-pregnadiene-3,20-dione and the sodium salt thereof.
Dependencies are inferred from the claim text.