Schering Aktiengesellschaft

Otto Engelfried

Ulrich Kerb

Rudolf Wiechert

Helmut Wachtel

Karl Petzoldt

Wolfgang Kehr

Reinhard Horowski

Klaus Kieslich

Dieter Palenschat

Gert Paschelke

Bob Nieuweboer

Klaus Lubke

3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-D-homo-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodo-benzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.

.DELTA..sup.9 (11) -5.alpha.-D-homo-20-keto steroids

3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodobenzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.

.DELTA..sup.9(11) -5.alpha.-20-KETO STEROIDS AND PROCESS FOR THEIR

D-homo-20-ketopregnanes of the formula ##STR1## wherein R.sub.1 is hydrogen, fluorine, chlorine, bromine, alkyl, alkoxy, or azido; R.sub.2 is oxygen, ##STR2## and R.sub.7 is hydrogen, lower alkyl, or acyl of up to 5 carbon atoms; R.sub.3 is hydrogen or methyl R.sub.4 is oxygen, two hydrogens, ##STR3## R.sub.5 is hydrogen, hydroxy, alkoxy, azido, mercapto, thiocyano, cyano, dialkylamino, morpholino, thiomorpholino, or piperazino; R.sub.6 is methyl or ethyl; The hydrogen atom in the 5-position is of the .alpha.- or .beta.-configuration; And acid addition salts thereof, possess narcotic-anesthetic activity.

D-homo-20-ketopregnanes and method for inducing anesthesia or narcosis

18-Methyl-19-nor-20-keto steroids of the formula ##STR1## wherein R.sub.1 and R.sub.2 collectively are an oxygen atom, or each is hydrogen, or one of R.sub.1 and R.sub.2 is hydrogen and the other is hydroxy, and R.sub.3 is a ketonic oxygen atom or two hydrogen atoms, possess CNS-depressant activity, especially anesthetic-narcotic activity.

18-Methyl-19-nor-20-ketopregnanes and process for the preparation thereof

Steroids bearing the substituent --X-NR.sub.1 R.sub.2 wherein --NR.sub.1 R.sub.2 is a tritium of carbon-14 labeled amino or amino-acid group and --X-- is --R.sub.3 --, --OCOR.sub.3 --, =N--O--R.sub.3 -- or --NHCOR.sub.3 -- wherein R.sub.3 is --(CH.sub.2).sub.n CO-- in which n is 0-4, are useful as diagnostic agents.

Growing community of inventors

Berlin, Germany

Otto Engelfried