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US 6,440,995 B1Granted
Quinolin-4-yl derivatives
AssigneeHoffman-La Roche Inc.
InventorsAlexander Alanine, Serge Burner, Bernd Buettelmann, Marie-Paule Heitz Neidhart, Georg Jaeschke, Emmanuel Pinard, René Wyler
Life of this patent
Estimating the term…
Abstract
Phenyl substituted quinolin 4-yl derivatives and pharmaceutical compositions with activity as NMDA-receptor subtype selective blockers. The compounds of the invention modulate neuronal activity and plasticity.
Claims35
A compound of formula I:
- wherein
- is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, nitro, cyano, lower alkyl-amino, di-lower alkyl-amino or halogen;
- R2 is 2,3-dihydro-benzofuran-5-yl, chroman-6-yl, naphthalen-2-yl, indan-5-yl, lower alkenyl-phenyl, 5,6,7,8-tetrahydro-naphthalenyl, 2,3-dihydro-isoindol-2-yl, 1,2,3,4-tetrahydro-naphthalenyl, benzofuran-2-yl, benzo[b]thiophen-2-yl, lower alkyl-phenyl, 3,4-dihydro-1H-isoquinolin-2-yl or thiophen-3-yl, or is unsubstituted phenyl, or phenyl substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl, amino, lower alkyl-amino or di-lower alkyl-amino;
- R3 and R4 are independently from each other hydrogen or lower alkyl;
- R5 is hydrogen, lower alkyl, —CH2OH or —CH2NR6R7;
- R6 and R7 are independently from each other hydrogen, lower alkyl, —(CH2)n-phenyl, cycloalkyl, —(CH2)m-morpholinyl or form together with the N-atom a saturated ring with 4-6 C-atoms;
- n is 0-3;
- m is 2 or 3;
- X is —NR8— or —O—;
- or
- X and R5 are together >N(CH2)2—;
- or
- X and R3 are together >N(CH2)3—;
- and
- R8 is hydrogen or lower alkyl;
- or a pharmaceutically acceptable acid addition salt thereof, with the exception of the following compounds
- (6-chloro-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol,
- (6-methyl-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol,
- (6-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol and
- (8-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol.
17 more elements
Dependencies are inferred from the claim text.