# US 9,434,688 B2 · Indole derivatives as selective androgen receptor modulators (SARMS)

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- Number: US 9,434,688 B2
- Document ID: US9434688B2
- Status: Granted
- Kind: B2
- Application number: 14/277,429
- Filed: 2014-05-14
- Published: 2014-09-04
- Granted: 2016-09-06
- Earliest claimed: 2004-05-03
- Assignees: Janssen Pharmaceutica NV
- Applicants: Janssen Pharmaceutica, NV
- Inventors: James C Lanter; Zhihua Sui; James J Fiordeliso; Weiqin Jiang; Xuqing Zhang
- Web page: https://patentgrep.com/patent/US9434688B2

## CPC

- C07D 209/12: Radicals substituted by oxygen atoms
- A61K 31/407: condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
- A61K 31/4985: Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
- A61K 31/5025: ortho- or peri-condensed with heterocyclic ring systems
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 13/08: of the prostate
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/16: Masculine contraceptives
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/14: for baldness or alopecia
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C07D 209/30: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

## Claims

### Claim 1

A method of inhibiting an androgen receptor, in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of formula (III)
wherein
is a six membered heteroaryl ring structure containing one to two nitrogen atoms;
Y is NR1;
R1 is selected from the group consisting of hydrogen, lower alkyl, fluorinated lower alkyl, —SO2-(lower alkyl), —SO2-phenyl, —SO2-tolyl, —(CH2)-(fluorinated lower alkyl), -(lower alkyl)-CN, -(lower alkyl)-C(O)—O-(lower alkyl), -(lower alkyl)-O-(lower alkyl) and -(lower alkyl)—S(O)0-2-(lower alkyl);
R4 is selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl and cyano; wherein the lower alkyl, lower alkenyl or lower alkynyl is optionally substituted on the terminal carbon atom with —Si(lower alkyl)3;
a is an integer from 0 to 4;
R5 is selected from the group consisting halogen, hydroxy, carboxy, lower alkyl, halogen substituted lower alkyl, lower alkoxy, halogen substituted lower alkoxy, cyano, nitro, amino, lower alkylamino, di(lower alkyl)amino, —C(O)-(lower alkyl), —C(O)-(lower alkoxy), —C(O)—N(RA)2, —S(O)0-2-(lower alkyl), —SO2—N(RA)2, —N(RA)—C(O)-(lower alkyl), —N(RA)—C(O)-(halogen substituted lower alkyl) and aryl;
wherein each RA is independently selected from hydrogen or lower alkyl;
wherein the aryl is optionally substituted with one or more substituents independently selected from halogen, hydroxy, carboxy, lower alkyl, halogen substituted lower alkyl, lower alkoxy, halogen substituted lower alkoxy, cyano, nitro, amino, lower alkylamino or di(lower alkyl)amino;
b is an integer from 0 to 1;
c is an integer from 0 to 1;
R7 is selected from the group consisting of hydrogen, lower alkyl and —Si(lower alkyl)3;
R2 is selected from the group consisting of hydrogen, lower alkyl, halogen substituted lower alkyl and —(CH2)1-4—Z—R6;
R3 is selected from the group consisting of lower alkyl, halogen substituted lower alkyl and —(CH2)1-4—Z—R6;
wherein each Z is independently selected from the group consisting of —S(O)0-2—, —O—, —O—C(O)—, —NH— and —N(lower alkyl)-;
wherein each R6 is independently selected from the group consisting of lower alkyl, halogen substituted lower alkyl lower alkenyl, aryl, aralkyl, biphenyl, cycloalkyl, cycloalkyl-(lower alkyl), heteroaryl and heteroaryl-(lower alkyl);
wherein the cycloalkyl, aryl or heteroaryl group, whether alone or part of a substituent group is optionally substituted with one or more substituents independently selected from halogen, hydroxy, carboxy, lower alkyl, halogen substituted lower alkyl, lower alkoxy, cyano, nitro, amino, lower alkylamino, di(lower alkyl)amino, —S(O)0-2-(lower alkyl) and —SO2—N(RA)2;
provided that when Z is O, NH or N(lower alkyl) then Z is other than lower alkenyl;
or a pharmaceutically acceptable salt thereof.