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US 6,548,498 B1Granted
Substituted indan derivatives
AssigneeAstraZeneca AB
InventorsStefan Berg, Lennart Florvall, Svante Ross, Seth-Olov Thorberg
Life of this patent
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Abstract
The present invention relates to new piperidyl- or piperazinyl-substituted indan derivatives of the formula I as (R)-enantiomers, (S)-enantiomers, or racemates in the form of a free base or pharmaceutically acceptable salts or solvates thereof. The present invention further relates to a process for the preparation of the compounds, to pharmaceutical compositions containing the compounds and to methods of treatment of 5-hydroxytryptamine-mediated disorders comprising administering the compounds.
Claims23
A compound of the formula I
- wherein
- X is N;
- Y is NR2CH2, CH2NR2, NR2CO, CONR2 or NR2SO2 wherein R2 is H or C1-C6 alkyl;
- R1 is H, C1-C6 alkyl or C3-C6 cycloalkyl;
- R3 is C1-C6 alkyl, C3-C6 cycloalkyl or (CH2)n-aromatic ring, wherein the aromatic ring is phenyl or a heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S and wherein the aromatic ring may be mono- or di-substituted with R4 and/or R5;
- wherein R4 is H, C1-C6 alkyl, C3-C6 cycloalkyl, halogen, CN, CF3, OH, C3-C6 alkoxy, NR6R7, OCF3, SO3CH3, SO3CF3, SO2NR6R7, phenyl, phenyl-C1-C6 alkyl, phenoxy, C1-C6 alkylphenyl, an optionally substituted heterocyclic ring containing one or two heteroatoms selected from the group consisting of N, O, S, SO and SO2 wherein the substituent(s) is(are) selected from the group consisting of C1-C6 alkyl C3-C6 cycloalkyl and phenyl-C1-C6 alkyl, an optionally substituted heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S, wherein the substituent(s) is (are) selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl and phenyl-C1-C6 alkyl, or COR8;
- wherein R6 is H, C1-C6 alkyl or C3-C6 cycloalkyl;
- R7 is H, C1-C6 alkyl or C3-C6 cycloalkyl;
- and
- R8 is C1-C6 alkyl, C3-C6 cycloalkyl, CF3 NR6R7, phenyl, a heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S, or a heterocyclic ring containing one or two heteroatoms selected from the group consisting of N, O, S, SO and SO2;
- wherein R5 is H, OH, CF3, OCF3, halogen, C1-C6 alkyl or C1-C6 alkoxy;
- n is 0-4;
- R9 is H, C1-C6 alkyl, C3-C6 cycloalkyl, OCF3, OCHF2, OCH2F, halogen, CN, CF3, OH, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, NR6R7, SO3CH3, SO3CF3, SO2NR6R7, an unsubstituted or substituted heterocyclic or heteroaromatic ring containing one or two heteroatoms selected from the group consisting of N, O and S, wherein the substituent(s) is(are) C1-C6 alkyl;
- or COR8;
- wherein R6, R7 and R8 are as defined above,
- wherein the compound is an (R)-enantiomer, an (S)-enantiomer, or a racemate in the form of a free base or a pharmaceutically acceptable salt or solvate thereof.
13 more elements
Dependencies are inferred from the claim text.