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US 7,442,710 B2Granted
Substituted phenyl methanones
AssigneeHoffman-La Roche Inc.
InventorsSynese Jolidon, Robert Narquizian, Roger David Norcross, Emmanuel Pinard
Life of this patent
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Abstract
The present invention relates to compounds of general formula IA or IB wherein X1 and X2 are each independently N or C—R″ and R1, R2,R3, R4, R5, and R6 are as defined in the specification and to pharmaceutically acceptable acid addition salts thereof. The compounds can be used for the treatment of diseases related to the glycine transporter inhibitor, such as schizophrenia and Alzheimer's disease.
Claims19
A compound of formula IA-4
- wherein
- R1 is aryl, a cyclic amine selected from the group consisting of pyrrol-1-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxo-thiomorpholin-4-yl and 1, 1-dioxo-thiomorpholin-4-yl, OR11, SR11, or N(R12)2;
- R11 is lower alkyl, lower alkyl substituted by halogen, or —(CH2)n-cycloalkyl;
- each R12 is independently hydrogen or lower alkyl;
- R2 is NO2, CN or S(O)2-lower alkyl;
- R3 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, or lower alkoxy;
- R4 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, non cyclic amine, lower alkoxy, or benzyloxy optionally substituted by halogen;
- R5 and R6 are each independently hydrogen, halogen, lower alkyl, lower alkoxy, aryl or form together the keto group ═O;
- R′ is hydrogen, halogen, lower alkyl, lower alkoxy, or benzyloxy optionally substituted by halogen;
- R″ is hydrogen;
- alkyl substituted by halogen;
- halogen;
- nitro;
- lower alkoxy;
- cyano;
- COO-lower alkyl;
- benzyloxy optionally substituted by halogen;
- or S(O)2-cyclic amine, wherein the cyclic amine is selected from the group consisting of pyrrol-1-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxo-thiomorpholin-4-yl and 1,1-dioxo-thiomorpholin-4-yl;
- or
- R3 and R″ or R4 and R′ or R″ and R4 are together with the carbon atom to which they are attached —O—(CH2)n—O— or —O—(CH2)m— or —(CH2)m—O—, or
- n is 1 or 2;
- and
- m is 2 or 3;
- or a pharmaceutically acceptable acid addition salt thereof.
21 more elements
A pharmaceutical composition comprising a compound of formula IA-4
- wherein
- R1 is aryl, a cyclic amine selected from the group consisting of pyrrol-1-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxo-thiomorpholin-4-yl and 1,1-dioxo-thiomorpholin-4-yl, OR11, SR11 or N(R12)2;
- R11 is lower alkyl, lower alkyl substituted by halogen, or —(CH2)n-cycloalkyl;
- each R12 is independently hydrogen or lower alkyl;
- R2 is NO2, CN or S(O)2-lower alkyl;
- R3 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, or lower alkoxy;
- R4 is hydrogen, halogen, lower alkyl, lower alkyl substituted by halogen, non cyclic amine, lower alkoxy, or benzyloxy optionally substituted by halogen;
- R5 and R6 are each independently hydrogen, halogen, lower alkyl, lower alkoxy, aryl or form together the keto group ═O;
- R′ is hydrogen, halogen, lower alkyl, lower alkoxy, or benzyloxy optionally substituted by halogen;
- R″ is hydrogen, alkyl substituted by halogen, halogen, nitro, lower alkoxy, cyano, COO-lower alkyl, benzyloxy optionally substituted by halogen, or S(O)2-cyclic amine;
- wherein the cyclic amine is selected from the group consisting of pyrrol-1-yl, piperidin-1-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, 1-oxo-thiomorpholin-4-yl and 1,1-dioxo-thiomorpholin-4-yl;
- or
- R3 and R″ or R4 and R′ or R″ and R4 are together with the carbon atom to which they are attached —O—(CH2)n—O— or —O—(CH2)m— or —(CH2)m—O—, or
- n is 1 or 2;
- and
- m is 2 or 3;
- or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutically acceptable carrier.
14 more elements
Dependencies are inferred from the claim text.