PROCESS FOR THE PREPARATION OF 4-AZASTEROIDS

The invention relates to a process for the preparation of 4-steroids of the formula R 1 and R 2 are independently selected from the group consisting of hydrogen, F, Cl, Br, I, C 1-6 -alkyl and C 1-6 -alkoxy, and R 4 is selected from the group consisting of hydrogen, ( N , N -di-C 1-6 -alkylamino)methyl, 2-( N , N -di-C 1-6 -alkylamino)ethyl, C 1-6 -alkyl, C 1-6 -alkoxy, phenyl and benzyl, and Q 7 represents a carbonyl oxygen atom or is R 7-1 and R 7-2 , wherein one of R 7-1 and R 7-2 is hydrogen and the other is selected from the group consisting of hydrogen, F, Cl, Br, I, C 1-6 -alkyl and C 1-6 -alkoxy, and R 9 represents hydrogen or F, and Q 11 represents a carbonyl oxygen atom or is R 11-1 and R 11-2 , wherein one of R 11-1 and R 11-2 is hydrogen and the other is selected from the group consisting of hydrogen, cyano, cyano-C 1-3 -alkyl, acetoxy, COOH and COO - M + , wherein M + is Na + , K + or NH + 4 , and R 16 is selected from the group consisting of hydrogen, cyano, C 1-3 -alkyl, cyano-C 1-3 -alkyl, acetoxy, COOH and COO - M + , wherein M + is Na + , K + or NH + 4 , and COOR represents COOH or COO - M + , wherein M + is Na + , K + or NH + 4 . The three step process comprises (i) a haloform reaction of a 17-acetyl steroid converting the acetyl group into a -COOR group, (ii) subsequent ozonolysis of the A-ring and (iii) re-closure of the A-ring by reaction with an appropriate nitrogen compound of formula H 2 NR 4 to afford a compound of formula I above.