IP Library Granted Patent US 7,960,365
Granted Patent B2
US 7,960,365 · App. 11/641,524 · Granted Jun 14, 2011

Compounds with medicinal effects due to interaction with the glucocorticoid receptor

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Quick Facts
Patent No.
US 7,960,365
App. No.
11/641,524
Granted
Jun 14, 2011
Kind
B2
Abstract

The invention provides for compounds having the structure according to the formula I wherein: X is a carbon or nitrogen atom; Ar is phenyl or heteroaromatic ring; R 1 is hydrogen, halogen, CN or (1C-4C)alkyl; R 2 is hydrogen, halogen or optionally fluorinated (1C-3C)alkoxy; R 3 and R 5 are independently hydrogen, optionally halogenated (1C-4C)alkyl, optionally halogenated (1C-4C)alkoxy, optionally halogenated aryl(1C-4C)alkoxy, optionally halogenated (1C-4C)alkenyl or hydroxylmethyl; R 4 is hydrogen, halogen, optionally halogenated (1C-4C)alkoxy or optionally halogenated aryl(1C-4C)alkoxy; R 6 is hydrogen, benzyl, optionally substituted with one or more halogens or (1C-4C)alkyl, or R 6 is optionally halogenated (1C-4C)alkyl; each R 7 independently is hydrogen, halogen, optionally halogenated (1C-4C)alkyl or optionally halogenated (1C-4C)alkoxy and pharmaceutically suitable acid addition salts thereof for use as glucocorticoid receptor modulators, in particular for treatment of central nervous system disorders.

Claims (27)

1. A compound having the structure according to the formula I

wherein:

X is a nitrogen atom;

Ar is 1H-pyrazole;

R 1 is hydrogen, halogen, CN or (1C-4C)alkyl;

R 2 is hydrogen, halogen or optionally fluorinated (1C-3C)alkoxy;

R 3 and R 5 are independently hydrogen, optionally halogenated (1C-4C)alkyl, optionally halogenated (1C-4C)alkoxy, optionally halogenated aryl(1C-4C)alkoxy, optionally halogenated (1C-4C)alkenyl or hydroxylmethyl;

R 4 is hydrogen, halogen, optionally halogenated (1C-4C)alkoxy or optionally halogenated aryl(1C-4C)alkoxy;

R 6 is optionally halogenated (1C-4C)alkyl; and

each R 7 independently is hydrogen, halogen, optionally halogenated (1C-4C)alkyl or optionally halogenated (1C-4C)alkoxy;

or a pharmaceutically suitable acid addition salt thereof.

2. The compound according to claim 1 , whereby:

R 2 is halogen or optionally fluorinated (1C-3C)alkoxy;

at least one of R 3 , R 4 or R 5 is hydrogen;

R 6 is methyl;

or a pharmaceutically suitable addition salt thereof.

3. The compound according to claim 1 , whereby

R 1 is hydrogen, halogen, CN or methyl;

R 2 is hydrogen, halogen or optionally fluorinated (1C-2C)alkoxy;

R 3 and R 5 are independently hydrogen, (1C-3C)alkyl, benzyloxy, (2C-3C)alkenyl, hydroxylmethyl or optionally fluorinated methoxy;

R 4 is hydrogen, F, Cl or methoxy and at least one of R 3 , R 4 and R 5 is hydrogen;

R 6 is methyl;

each R 7 independently is hydrogen, optionally fluorinated methyl, optionally fluorinated methoxy, F, Cl or Br;

or a pharmaceutically suitable addition salt thereof.

4. The compound according to claim 1 , wherein the compound is N-[(1R)-1-(5-chloro-2-methoxy-3-pyridinyl)phenyl]ethyl-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-sulfonamide or a pharmaceutically suitable addition salt thereof.

5. A pharmaceutical composition comprising the compound according to claim 1 or a pharmaceutically suitable addition salt thereof and a pharmaceutically acceptable excipient.

6. A pharmaceutical composition comprising the compound according to claim 4 or a pharmaceutically suitable addition salt thereof and a pharmaceutically acceptable excipient.

Assignments (5)
MERGER Recorded Mar 8, 2013
From: ORGANON BIOSCIENCES NEDERLAND B.V.
To: MERCK SHARP & DOHME B.V.
Reel/Frame 029940/0296 →
MERGER Recorded Mar 7, 2013
From: MSD OSS B.V.
To: ORGANON BIOSCIENCES NEDERLAND B.V.
Reel/Frame 029939/0001 →
MERGER Recorded Dec 1, 2011
From: N.V. ORGANON
To: MSD OSS B.V.
Reel/Frame 027307/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2007
From: KINGSBURY, CELIA; OHLMEYER, MICHAEL; HO, KOC-KAN; KULTGEN, STEVEN G.
To: PHARMACOPEIA DRUG DISCOVERY, INC.
Reel/Frame 018927/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2007
From: HAMILTON, NIALL MORTON; BROWN, ANGUS RICHARD; GROVE, SIMON JAMES ANTHONY; KICZUN, MICHAEL JOHN; MORPHY, JOHN RICHARD; SHERBORNE, BRAD; LITTLEWOOD, PETER THOMAS ALBERT
To: N.V. ORGANON
Reel/Frame 018902/0425 →