Steroid 5-alpha-reductase inhibitors

A compound represented by the formula:

• ##STR33## in which:
• the A ring has up to 2 double bonds;
• the B, C, and D rings have optimal double bonds where indicated by the broken lines, provided that the A, B, and C rings do not have adjacent double bonds and the D ring does not have a C.sub.16 -C.sub.17 double bond when R.sub.3 represents two substiuents or a divalent substituent;
• Z is (CH.sub.2).sub.n and n is 0 or 2, provided that Z is (CH).sub.n when adjacent to a double bond;
• X is H, Cl, F, Br, I, CF.sub.3, or C.sub.1-6 alkyl;
• Y is H, CF.sub.3, F, Cl, or CH.sub.3, provided that Y is H when there is no C.sub.5 -C.sub.6 double bond;
• R.sup.1 is H or C.sub.1-8 alkyl;
• R.sup.2 is absent or present as H or CH.sub.3, provided R.sup.2 is absent when the carbon to which it is attached is unsaturated;
• and
• R.sup.3 is
• (1) .alpha.-hydrogen, or .alpha.-hydroxyl, or .alpha.-acetoxy and/or
• (a) ##STR34## where W is a bond or C.sub.1-12 alkylidene, and R.sup.4 is (i) hydrogen,
• (ii) hydroxyl,
• (iii) C.sub.1-8 alkyl,
• (iv) hydroxylic.sub.1-8 alkyl,
• (v) C.sub.1-8 alkoxy,
• (vi) NR.sup.5 R.sup.6, where R.sup.5 and R.sup.6 are each independently selected from hydrogen, C.sub.1-8 alkyl, C.sub.3-6 cycloalkyl, phenyl;
• or R.sup.5 and R.sup.6 taken together with the nitrogen to which they are attached represent a 5-6 membered saturated ring
• (vii) OR.sup.7, where R.sup.7 is hydrogen, alkali metal C.sub.1-18 alkyl, benzyl, or
• (b) --Alk--OR.sup.8, where Alk is C.sub.1-12 alkylidene, and R.sup.8 is
• (i) phenyl C.sub.1-6 alklylcarbonyl,
• (ii) C.sub.5-10 cycloalkylcarbonyl,
• (iii) benzoyl,
• (iv) C.sub.1-8 alkoxycarbonyl,
• (v) aminocarbonyl, or C.sub.1-8 alkyl substituted aminocarbonyl,
• (vi) hydrogen, or
• (vii) C.sub.1-8 alkyl,
• (2) .dbd.CH--W--CO--R.sup.4 or .dbd.CH--W--OR.sup.8, where W is a bond or C.sub.1-12 alkylidene and R.sup.4 and R.sup.8 have the same meaning as above and R.sup.8 also is hydrogen or C.sub.1-20 alkylcarbonyl,
• (3) ##STR35## where the dashed bond replaces the 17-.alpha.-hydrogen, (4) .alpha.-hydrogen and NHCOR.sup.9 where R.sup.9 is C.sub.1-12 alkyl or NR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 have the same meaning as above,
• (5) .alpha.-hydrogen and cyano,
• (6) .alpha.-hydrogen and tetrazolyl, or
• (7) keto;
• or a pharmaceutically acceptable salt thereof;
• except compounds in which:
• (i) the B ring has a C.sub.5 -C.sub.6 double bond, R.sup.1 is CH.sub.3, and R.sup.3 is keto, methoxycarbonyl, or acetyl;
• or
• (ii) the A-nor ring has a C.sub.3 -C.sub.4 double bond and R.sup.3 is acetoxy or acetyl;
• (iii) R.sup.1 is CH.sub.3 and R.sup.3 is acetoxy or acetyl;
• or
• (iv) the A-nor ring has a C.sub.3 -C.sub.4 double bond and R.sup.1 is methyl;
• or
• (v) the B ring has a C.sub.3 -C.sub.4 double bond and R.sup.3 is .beta.-hydroxy.