Tetracyclic heteroatom containing derivatives useful as sex steroid hormone receptor modulators

1. A compound of formula (I)

wherein

X is —O—;

R 1 is selected from the group consisting of hydrogen, C 1-6 alkyl, -C 1-4 alkyl—NR C R D and -L 1 R 4 -(L 2 ) c -R 5 ;

is phenyl;

a is 1;

R 2 is selected from the group consisting of C 1-4 alkoxy, —O-aralkyl, —OC(O)—C 1-4 alkyl, —O—SO 2 —C 1-4 alkyl, —O—SO 2 -(halogenated C 1-4 alkyl) and —O—Si(CH 3 ) 2 (t-butyl);

b is 1;

R 3 is selected from the group consisting of halogen, hydroxy, carboxy, oxo, cyano, nitro, amino, C 1-4 alkylamino, di(C 1-4 alkyl)amino, C 1-4 alkyl, C 1-4 alkoxy, halogenated C 1-4 alkyl, —O-aralkyl, —C(O)—C 1-4 alkyl, —C(O)O—C 1-4 alkyl, —OC(O)—C 1-4 alkyl, —O—SO 2 —C 1-4 alkyl, —O—SO 2 -(halogenated C 1-4 alkyl) and —O—Si(CH 3 ) 2 (t-butyl);

L 1 is selected from the group consisting of —CH 2 — and —C(O)—;

R 4 is selected from the group consisting of a five to six membered aryl and a five to six membered heteroaryl;

c is an integer selected from 0 to 1;

L 2 is selected from the group consisting of —C 1-4 alkyl-, —C 2-4 alkenyl-, —O—C 1-3 alkyl-, —S—C 1-3 alkyl- and —NR B —C 1-3 alkyl-; wherein R B is selected from hydrogen or C 1-4 alkyl;

R 5 is selected from the group consisting of —NR C R D , —C(O)—C 1-4 alkyl, —CO 2 H, —C(O)O—C 1-4 alkyl and —OC(O)—C 1-4 alkyl;

wherein R C and R D are independently selected from hydrogen or C 1-4 alkyl; alternatively, R C and R D are taken together with the nitrogen atom to which they are bound to form a five to seven membered aromatic, partially aromatic or saturated ring structure; wherein the ring structure optionally contains one to two additional heteroatoms selected from O, N or S;

or a pharmaceutically acceptable salt thereof.

2. A compound as in claim 1 wherein

X is —O—;

R 1 is selected from the group consisting of hydrogen and 4-(di(C 1-4 alkyl)amino-C 1-4 alkoxy)-benzyl;

is phenyl;

a is 1;

R 2 is C 1-4 alkoxy;

b is 1;

R 3 is selected from the group consisting of hydroxy and —O-aralkyl;

or a pharmaceutically acceptable salt thereof.

3. A compound as in claim 2 wherein

X is —O—;

R 1 is selected from the group consisting of hydrogen and 4-(diethylamino-ethoxy)-benzyl;

is phenyl;

a is 1;

R 2 is methoxy;

b is 1;

R 3 is selected from the group consisting of hydroxy and benzyloxy;

or a pharmaceutically acceptable salt thereof.

4. A compound as in claim 1 selected from

7-benzyloxy-3-methoxy-10H-benzo[4,5]furo[3,2-b]indole;

{2-[4-(7-benzyloxy-3-methoxy-benzo[4,5]furo[3,2-b]indol-10-ylmethyl)-phenoxy]-ethyl}-diethyl-amine; and

10-[4-(2-biethylamino-ethoxy)-benzyl]-3-methoxy-10H-benzo[4,5]furo[3,2-b]indol-7-ol;

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 1 .

6. A process for making a pharmaceutical composition comprising mixing a compound of claim 1 and a pharmaceutically acceptable carrier.