IP Library Granted Patent US 10,093,652
Granted Patent B2
US 10,093,652 · App. 15/038,287 · Granted Oct 9, 2018

Tetrahydrobenzimidazole derivatives as modulators of TNF activity

Inventors: Jag Paul Heer (Brussels, BE); Victoria Elizabeth Jackson (Slough, GB); Boris Kroeplien (Slough, GB); Fabien Claude Lecomte (Slough, GB); John Robert Porter (Slough, GB)
Assignee: UCB BIOPHARMA SPRL
C07D401/10A61K31/4439C07D235/12
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Quick Facts
Patent No.
US 10,093,652
App. No.
15/038,287
Granted
Oct 9, 2018
Kind
B2
Abstract

A series of substituted 4,5,6,7-tetrahydrobenzimidazole derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

Claims (13)

1. A compound represented by formula (IIA) or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, or a glucuronide derivative thereof:

wherein

E represents —CH 2 —;

Q represents —CH 2 — or —CH(OH)—;

Z represents hydrogen, methyl, phenyl, methylsulfonylphenyl, pyridinyl, methyl sulfonylpyridinyl, oxopyrrolidinylphenyl, (hydroxy)(oxo)pyrrolidinylphenyl or (oxo)oxazolidinylphenyl;

R 11 represents hydrogen or halogen;

R 12 represents hydrogen, fluoro, chloro, trifluoro-methyl, methyl or ethoxycarbonylethyl;

R 15 represents hydrogen, halogen, C 1-6 alkyl, trifluoro-methyl, C 1-6 alkoxy, difluoromethoxy or trifluoromethoxy; and

R 16 represents hydrogen, halogen, cyano, C 1-6 alkyl, trifluoromethyl, difluoromethoxy or amino.

2. A compound that is {1-[(2,5-Dimethylphenyl)methyl]-4,5,6,7-tetrahydrobenzimidazol-2-yl}(pyridin-4-yl)methanol.

3. A pharmaceutical composition comprising a compound of formula (IIA) as defined in claim 1 or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, or a glucuronide derivative thereof, in association with a pharmaceutically acceptable carrier.

4. The pharmaceutical composition as claimed in claim 3 further comprising an additional pharmaceutically active ingredient.

5. A method for the treatment of Crohn's disease or rheumatoid arthritis, which method comprises administering to a patient in need of such treatment an effective amount of a compound of formula (IIA) as defined in claim 1 or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, or a glucuronide derivative thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2017
From: UCB PHARMA S.A.
To: UCB BIOPHARMA SPRL
Reel/Frame 042572/0783 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2017
From: HEER, JAG PAUL
To: UCB BIOPHARMA SPRL
Reel/Frame 042254/0151 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2017
From: JACKSON, VICTORIA ELIZABETH; KROEPLIEN, BORIS; LECOMTE, FABIEN CLAUDE; PORTER, JOHN ROBERT
To: CELLTECH R&D LIMITED
Reel/Frame 041947/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2017
From: CELLTECH R&D LIMITED
To: UCB S.A.
Reel/Frame 041947/0854 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2017
From: UCB S.A.
To: UCB PHARMA S.A.
Reel/Frame 041947/0906 →
Priority Claims (1)
GB 1321744.3 · Dec 9, 2013 · national
Continuity (1)
Related Publication 20160297795A1 · Oct 13, 2016
Cited By (1)
US 12,247,071