# US 7,608,712 B2 · Pyridine imidazoles and aza-indoles as progesterone receptor modulators

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- Number: US 7,608,712 B2
- Document ID: US7608712B2
- Status: Granted
- Kind: B2
- Application number: 12/024,189
- Filed: 2008-02-01
- Published: 2008-05-22
- Granted: 2009-10-27
- Earliest claimed: 2004-10-27
- Assignees: Janssen Pharmaceutica NV
- Inventors: Weiqin Jiang; James J. Fiordeliso; Zhihua Sui
- Web page: https://patentgrep.com/patent/US7608712B2

## CPC

- C07D 471/10: Spiro-condensed systems
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/18: Feminine contraceptives
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is directed to novel heteroatom containing tetracyclic derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders mediated by one or more estrogen receptors. The compounds of the invention are useful in the treatment of disorders associated with the depletion of estrogen such as hot flashes, vaginal dryness, osteopenia and osteoporosis; hormone sensitive cancers and hyperplasia of the breast, endometrium, cervix and prostate; endometriosis, uterine fibroids, osteoarthritis and as contraceptive agents, alone or in combination with a progestogen or progestogen antagonist.

## Claims

### Claim 1

A compound of formula (II):
wherein
R1 and R2 are the same and are unsubstituted alkyl groups or R1 and R2-are connected by —(CH2)n— to form a 5 or 6 membered ring;
wherein n is 4 or 5;
R3 is halogen or phenyl substituted with one or more substituents independently selected from halogenated alkyl, alkoxy, halogen, nitro and cyano;
R4 is hydrogen;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R1 and R2 are methyl.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R1 and R2 are connected by —(CH2)4— to form a 5-membered spiro ring.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R1 and R2 are connected by —(CH2)5— to form a 6-membered spiro ring.

### Claim 5 (depends on 1)

The compound of claim 1 wherein said phenyl of R3 is mono-, di-, or tri-substituted by halogen, NO2, CF3 or CN.

### Claim 6 (depends on 1)

The compound of claim 1 selected from the group consisting of:
5-(3-Fluoro-phenyl)-3,3-dimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one; and
5-(3-Fluoro-phenyl)-3,3-spiro[cyclohexane]-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one.