US 2007/0185107 A1 · Chroman compounds

Abstract

Compounds according to Formula (I): wherein R1, R2, R3, and R4 are as defined in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.

Claims39

Dependent claims

A compound according to Formula I:

wherein:
R1 is F or OCH3;
R4is H, CH3, C2-4alkyl, CH2CH2OCH3, or CH2CF3;
and
R3is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3;
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine, and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —SO2CH3, —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

5 more elements

A compound selected from:

6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+) 6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
and
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
or a pharmaceutically-acceptable salt thereof.

68 more elements

A compound selected from:

(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide
(+)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(+)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+) 6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
and
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
or a pharmaceutically-acceptable salt thereof.

19 more elements

A method of treating anxiety disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is F or OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

A method of treating mood disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is F or OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

A method of treating cognitive disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is For OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

Dependencies are inferred from the claim text.

Facts

Application

11/592,686Filed 3 Nov 2006

Priority

4 Nov 2005

Published

9 Aug 2007

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07D 311/66
Other than with oxygen or sulphur atoms in position 2 or 4: with carbon atoms having three bonds to hetero atoms with at the most one bond to…
A61P 1/14
Drugs for disorders of the alimentary tract or the digestive system: prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics,…
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
A61P 25/20
Drugs for disorders of the nervous system: hypnotics; Sedatives

Abstract

Claims39

Dependent claims

A compound according to Formula I:

wherein:
R1 is F or OCH3;
R4is H, CH3, C2-4alkyl, CH2CH2OCH3, or CH2CF3;
and
R3is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3;
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine, and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —SO2CH3, —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

5 more elements

A compound selected from:

6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-acetylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-(2-methoxyethyl)piperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(−)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
(−)-6-methoxy-N-(4-morpholinophenyl)-8-(piperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(−)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+) 6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(−)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
and
(−)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
or a pharmaceutically-acceptable salt thereof.

68 more elements

A compound selected from:

(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-6-fluoro-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-N-(4-(4-(ethylsulfonyl)piperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide
(+)-8-(4-butylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-N-(4-morpholinophenyl)-8-(4-propylpiperazin-1-yl)chroman-2-carboxamide;
(+)-8-(4-isopropylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-8-(4-ethylpiperazin-1-yl)-6-methoxy-N-(4-morpholinophenyl)chroman-2-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-4-(4-(6-fluoro-8-(4-methylpiperazin-1-yl)chroman-2-carboxamido)phenyl)-N,N-dimethylpiperazine-1-carboxamide;
(+)-6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)chroman-2-carboxamide;
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
(+) 6-methoxy-8-(4-methylpiperazin-1-yl)-N-(4-(4-propanoylpiperazin-1-yl)phenyl)chroman-2-carboxamide;
and
(+)-N-(4-(4-ethanoylpiperazin-1-yl)phenyl)-6-methoxy-8-(4-methylpiperazin-1-yl)chroman-2-carboxamide;
or a pharmaceutically-acceptable salt thereof.

19 more elements

A method of treating anxiety disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is F or OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

A method of treating mood disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is F or OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4 is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

A method of treating cognitive disorders in a mammal comprising administering to such mammal an effective amount of a compound of formula I

wherein:
R1 is For OCH3;
R4 is CH3, or C2-4alkyl;
and
R3 is selected from morpholine or piperazine attached by nitrogen and optionally substituted on the other nitrogen (for piperazine) with —C(═O)CH3, —CH3, —C(═O)CH2CH3, —C(═O)N(CH3)2, —SO2CH2CH3, or —SO2CH3,
with the proviso that when R1 is F and R4 is methyl then R3 cannot be morpholine;
and
with the proviso that when R1 is F and R4is methyl then R3 cannot be piperazine substituted with —CH2OH, —CH2CH2OH, —SO2CH3, or —SO2CH2CH3;
or a pharmaceutically-acceptable salt thereof.

6 more elements

Dependencies are inferred from the claim text.

Chroman compounds

Life of this patent

Abstract

Claims39

Chroman compounds

Life of this patent

Abstract

Claims39