Novel pregnanoic acid derivatives
AssigneeSchering Corporation
InventorsHenry Laurent, Klaus Annen, Rudolf Wiechert, Helmut Hofmeister
Life of this patent
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Abstract
Pregnanoic acid derivatives of general formula ##STR1## wherein is a single bond or a double bond; X is hydrogen, fluorine or methyl; Y is hydrogen, fluorine or chlorine; Z is .beta.-hydroxymethylene, .beta.-acyloxymethylene, .beta.-fluoromethylene, .beta.-chloromethylene, carbonyl or methylene; R.sub.1 is hydrogen, methyl in the .alpha.- or .beta.-position or methylene and R.sub.2 is hydrogen, hydroxy or acyloxy, or R.sub.1 and R.sub.2 collectively are alkylidendioxy and U.sub.1 is halogen, halogenated alkyl of 1-5 carbon atoms or halogenated phenyl, are topically effective anti-inflammatory agents.
Claims81
A pregnanoic acid compound of the formula ##STR9## wherein is a single bond or a double bond;
- X is hydrogen, fluorine or methyl;
- Y is hydrogen, fluorine or chlorine;
- Z is .beta.-hydroxymethylene, .beta.-alkanoyloxymethylene of 1-8 carbon atoms in the alkanoyl, .beta.-fluoromethylene, .beta.-chloromethylene, carbonyl or methylene;
- R.sub.1 is hydrogen, methyl in the .alpha.- or .beta.-position or methylene and R.sub.2 is hydrogen, hydroxy, alkanoyloxy of 1-8 carbon atoms or benzoyloxy or R.sub.1 and R.sub.2 collectively are alkylidenedioxy of up to 6 carbon atoms;
- and U.sub.1 is halogen, halogenated alkyl of 1-5 carbon atoms or halogenated phenyl with the provision that when R.sub.2 is hydrogen, U.sub.1 is halogenated phenyl.
A pregnanoic acid compound of the formula ##STR10## wherein is a single bond or a double bond;
- X is hydrogen, fluorine or methyl;
- Y is hydrogen, fluorine or chlorine;
- Z is .beta.-hydroxymethylene;
- R.sub.1 is hydrogen, methyl in the .alpha.- or .beta.-position or methylene and R.sub.2 is hydrogen;
- and U.sub.1 is chloromethyl, fluoromethyl, 2-chloroethyl, 2-fluoroethyl, 2-bromoethyl, 2-iodoethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, or halogenated phenyl.
A method for preparing a pregnanoic acid compound of the formula ##STR11## wherein is a single bond or a double bond;
- X is hydrogen, fluorine or methyl;
- Y is hydrogen, fluorine or chlorine;
- Z is .beta.-hydroxymethylene, .beta.-alkanoyloxymethylene of 1-8 carbon atoms in the alkanoyl, .beta.-fluoromethylene, .beta.-chloromethylene, carbonyl or methylene;
- R.sub.1 is hydrogen, methyl in the .alpha.- or .beta.-position or methylene and R.sub.2 is hydrogen, hydroxy, alkanoyloxy of 1-8 carbon atoms or benzoyloxy or R.sub.1 and R.sub.2 collectively are alkylidenedioxy of up to 6 atoms;
- and wherein U.sub.1 is halogenated alkyl of 1-5 carbon atoms or halogenated phenyl, comprising treating a compound of the formula ##STR12## wherein Q is formyl, including hydrates and hemiacetals thereof, with an aliphatic alcohol of the formula
- HO--CH.sub.2 U.sub.2
- wherein U.sub.2 is halogenated alkyl of 1-5 carbon atoms or halogenated phenyl, in a mixture of lower aliphatic alcohol and a dipolar aprotic solvent, buffered to pH 4-7 and containing cyanide ions, in the presence of atmospheric oxygen or manganese (IV) oxide.
Dependencies are inferred from the claim text.