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US 2013/0158042 A1Published application
Novel compounds
AssigneeBoehringer Ingelheim International GmbH
InventorsAnnekatrin HEIMANN, Georg DAHMANN, Marc GRUNDL, Stephan Georg MUELLER, Bernd WELLENZOHN
Life of this patent
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Abstract
This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. R1, R2, R3, R4, Q have meanings given in the description.
Claims14
A compound of formula I
- in which
- R1 represents phenyl or pyridyl which latter two groups are optionally substituted with one to three groups selected independently of one another from halogen, cyano, nitro, amino, C1-5alkyl, C3-6cycloalkyl, —O—C1-5alkyl, —N(R5)(R6) and —C(O)N(R5)(R6) which latter five groups are optionally substituted with one or more fluorine atoms;
- R2 represents a 5-14-membered aryl or 5-14-membered heteroaryl which latter two groups are optionally substituted with 1 to 4 groups selected from —OH, halogen, cyano, 4-9-membered heterocyclyl, C6-10 aryl, 5-9 membered heteroaryl, C1-5alkyl, —C1-5alkyl-OH, —O—C1-5-alkyl, —O—C1-5alkyl-O—C1-5-alkyl, —O—C3-5 alkynyl, —C1-5alkyl-O—C1-5-alkyl, C3-7cycloalkyl, —O—C3-7cycloalkyl, —O—CH2—C3-7cycloalkyl, C1-5alkyl-CO—, —C1-5alkyl-N(R5)(R6), —N(R5)(R6) and —S(O)2—C1-5alkyl which latter sixteen groups are optionally substituted with one or more fluorine atoms;
- R3 and R4 independently represent hydrogen, C1-3alkyl and —C1-3alkyl-O—C1-3alkyl which latter three groups are optionally substituted with one or more fluorine atoms, with the proviso that R3 and R4 both are not hydrogen;
- or
- R3 and R4 if both are attached to the same carbon atom, they may together with the carbon atom to which they are attached form a ring selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, piperidinyl, tetrahydrofuranyl and tetrahydropyranyl which latter seven groups are optionally substituted with one or more fluorine atoms;
- R5 and R6 independently represent hydrogen, C1-5alkyl, benzyl, —C(O)—C1-5alkyl, —C(S)—C1-5alkyl and —S(O)2—C1-5alkyl which latter five groups are optionally substituted with one or more fluorine atoms,
- or
- R5 and R6 together with the nitrogen atom to which they are attached form a 4-6-membered heterocyclyl, piperidinyl, tetrahydrofuranyl or tetrahydropyranyl ring which latter four groups are optionally substituted with one or more fluorine atoms;
- Q represents CH or N;
- or a physiologically acceptable salt thereof.
8 more elements
A compound of formula II
- in which
- R2 represents phenyl, naphthyl, 3-isochinolyl,
- R7 represents hydrogen, fluoro, bromo, chloro, cyano or methyl;
- R9 represents fluoro, chloro, bromo, cyano, C1-4-alkyl, C3-6-cycloalkyl, —O—C3-6cycloalkyl, —O—CH2—C3-6cycloalkyl, 4-6-membered heterocyclyl, —O—C1-4-alkyl, —O—CH2-ethynyl, —O—C1-2alkyl-OC1-2alkyl, CF3, —O—CF3, CF2H, —NMe2, phenyl,
- R10, R11 independently represents hydrogen, chloro, fluoro, methyl, ethyl, propyl, iso-propyl, CF3, —CF2H, —OCH3, —OCF3 or —NH—COCH3;
- or a physiologically acceptable salt thereof.
3 more elements
A compound according to formula III
- in which
- R2 represents phenyl, naphthyl, 3-isochinolyl,
- R7 represents hydrogen, fluoro, bromo, chloro, cyano or methyl;
- R9 represents fluoro, chloro, bromo, cyano, C1-4-alkyl, C3-6-cycloalkyl, —O—C3-6cycloalkyl, —O—CH2—C3-6cycloalkyl, 4-6-membered heterocyclyl, —O—C1-4-alkyl, —O—CH2-ethynyl, —O—C1-2alkyl-OC1-2alkyl, CF3, —O—CF3, CF2H, —NMe2, phenyl,
- R10, R11 independently represents hydrogen, chloro, fluoro, methyl, ethyl, propyl, iso-propyl, CF3, —CF2H, —OCH3, —OCF3 or —NH—COCH3;
- or a physiologically acceptable salt thereof.
3 more elements
A compound selected from the group consisting of
- or a physiologically acceptable salt thereof.
Dependencies are inferred from the claim text.