17 Beta-amino and hydroxylamino-11 beta-arylsteroids and their derivatives having agonist or antagonist hormonal properties

A hormonal or antihormonal steroid compound of structure I,

• 13
• wherein
• R1 is (R2R3N(O)r)—, where r is 0 or 1 and R2 and R3 are each independently H, C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl or C2-6 alkynyl, any of which may be optionally substituted;
• or
• 14
• where q is 0 or 1, Y is —(CH2)m— where m is an integer of 0 to 5, or Y is —(CH2)n—Z—(CH2)p— where n is an integer of 0 to 2, p is an integer of 0 to 2, and Z is a heteroatom (optionally substituted) and where the CH2 groups may be optionally substituted;
• or
• R1 is N-imidazolyl,—N-pyrrolyl-, H, halo-, HO—, CF3SO2O—, C1-6 alkyl-O—, C6alkyl-S—, C1-6 alkyl-S(O)—, C1-6 alkyl-S(O2)—, C1-6 alkyl-CO—, C1-6 alkyl-CH(OH)—, NC—, HCC—, C6H5CC—, 2′-furyl, 3′-furyl, 2′-thiophenyl, 3′-thiophenyl, 2′-pyridyl, 3′-pyridyl, 4′-pyridyl, 2′-thiazolyl, 2′-N-methylimidazolyl, 5′-pyrimidinyl, C6H5—, H2C═CH—, C1-6 alkyl, or MeC(═CH2)—;
• R12 is H or halo;
• or
• R1 and R12 combine to form a ring
• 15
• where W is CH2, CH, NH, N, O, or S, and R4 is H or C1-6 alkyl;
• X is O or NOR5, where R5 is H or C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-12 aryl, or heteroaryl, any of which may be optionally substituted;
• or
• X is (H, H), (H, OH), (H, OSi(C1-6 alkyl)3), or (H, OCOR5), where R5 is C1-6 alkyl, C3-8 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, C6-12 aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroaralkyl, heteroaralkenyl or heteroaralkynyl, any of which may be optionally substituted;
• or
• 16
• where Y is —(CH2)m— where m is an integer of 0 to 3, or Y is —(CH2)n—Z—(CH2)p— where n is an integer of 0 to 2, p is an integer of 0 to 2 and Z is a heteroatom (optionally substituted) or Z is a carbon atom substituted with one or two C1-6 alkyl groups;
• R6 is H, C1-6 alkyl or halogen;
• R7 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-12 aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroaralkyl, heteroaralkenyl or heteroaralkynyl, any of which may be optionally substituted, CN, COOR10 or CONHR10, where R10 is H, C1-18 alkyl, C2-18 alkenyl, C2-18 alkynyl, C3-8 cycloalkyl, C6-12 aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroaralkyl, heteroaralkenyl or heteroaralkynyl, any of which may be optionally substituted;
• s is 0 or 1;
• R8 and R9 are each independently H, C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl, R10CO, OR11, any of which may be optionally substituted,
• where R10 is H, C1-18 alkyl, C2-18 alkenyl, C2-18 alkynyl, C3-8 cycloalkyl, C6-12 aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroaralkyl, heteroaralkenyl or heteroaralkynyl any of which may be optionally substituted, and
• where R11 is H, C1-6 alkyl, Si(C1-6 alkyl)3, 2′-tetrahydropyranyl or R10CO where R10 is as defined above;
• and
• wherein when s is 0, R8 may also be O and R9 is ═CH2 or ═C(H, C1-6), ═C(H, aryl) or ═C(C1-6)2 and the nitrogen attached to the 17-position is positively charged;
• and pharmaceutically acceptable salts thereof.