Androgenic steroid compounds and a method of making and using the same

An androgenic steroid compound of the formula (I):

• 5
• wherein:
• R1 is H or lower alkyl;
• Y—Z is CH═C or CH2—CH, wherein H is α to the rings;
• or Y—CH, wherein H is α to the rings and Y is S, O, or NR10, wherein R10 is H or lower alkyl;
• R2 is an α-substituent which is unsubstituted lower alkyl or fluoro-substituted lower alkyl;
• R3 is C1-C8 alkyl, or C2-C8 alkenyl or alkynyl which are optionally substituted;
• or R3 is C4-C8 cycloalkyl which is unsubstituted or substituted;
• or R3 is C6-C18 aryl which is unsubstituted or substituted;
• or R3 is a 5- to 15-membered heterocycle which is unsubstituted or substituted, and further wherein any of the above may be further substituted with 1 to 3 heteroatoms or 1 to 5 halogen atoms or both;
• or
• R3 is H or acyl group (CO)—R4, wherein R4 is C1-C18, alkyl, or C2-C18 alkenyl or C2-C18 alkynyl which are optionally substituted;
• or R4 is C4-C18 cycloalkyl or substituted cycloalkyl;
• or R4 is C6-C18 aryl or substituted aryl;
• or R4 is a 5- to 15-membered heterocycle or substituted heterocycle, and wherein R4 may be optionally substituted with 1 to 3 heteroatoms or 1 to 5 halogen atoms or both;
• R5 is α-H, and R6 is β-lower alkyl, alkenyl or alkynyl which are optionally substituted, or R5R6 is═CH2;
• and
• X is O, H2, (H, OH) or (H, OCOR4), wherein R4 is as defined above;
• or X is (H, OR3), wherein R3 is as defined above;
• or X is NOR7, wherein R7 is H or C1-C8 alkyl, or C2-C8 alkenyl or alkynyl which are optionally substituted;
• or R7 is C4-C8 cycloalkyl which is unsubstituted or substituted;
• or R7 is C6-C18 aryl or substituted aryl;
• or R7 is a 5- to 15-membered heterocycle which is unsubstituted or substituted, and R7 may be optionally substituted with 1 to 3 heteroatoms or 1 to 5 halogen atoms or both;
• or X is (OR8, OR9), where R8 and R9 are lower alkyl, or (OR8, OR9) is a cyclic structure containing 2 to 3 carbon atoms, optionally substituted with lower alkyl, or 1 or 2 heteroatoms or halogens.