US 9,006,442 B2Granted

Cannabinoid receptor modulators

AssigneeLupin Limited

InventorsSanjeev Anant Kulkarni, Sachin Madan, Nirmal Kumar Jana, Prashant Vitthalrao Tale, Narasimha Murthy Cheemala, Sachin Jaysing Mahangare, Prashant Popatrao Vidhate, Chaitanya Prabhakar Kulkarni, Sapana Suresh Patel, Amolsing Dattu Patil, Seema Prabhakar Zade, Rohan Mahadev Shinde, Venkata P. Palle, Rajender Kumar Kamboj

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Abstract

Compounds of Formula (I) along with processes for their preparation that are useful for treating, managing and/or lessening the diseases, disorders, syndromes or conditions associated with the modulation of cannabinoid (CB) receptors. Methods of treating, managing and/or lessening the diseases, disorders, syndromes or conditions associated with the modulation of cannabinoid (CB) receptors of Formula (I).

Claims22

Dependent claims

A compound of Formula (I):

wherein,
W is —N— or —CH—;
when W is N, X is selected from NRa and O;
when W is —CH—, X is NRa;
Y is —C(O)—;
R1 is selected from hydrogen, alkyl, halogen, cycloalkyl, and haloalkyl;
with the proviso that when W is —N— then R1 is not hydrogen;
R2 is selected from hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
R3 is selected from alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, and heterocyclylalkyl;
or
R2 and R3, together with the nitrogen atom to which they are attached, may form a substituted or an unsubstituted 4 to 10 membered heterocyclic ring;
R4 is selected from aryl, cycloalkyl, heteroaryl and heterocyclyl;
Ra is selected from hydrogen, alkyl or cycloalkyl;
Rb is selected from hydrogen, alkyl or cycloalkyl;
and
wherein alkyl, cycloalkyl, aryl, heteroaryl, heterocyclyl, heterocyclic ring, cycloalkylalkyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, haloalkyl, wherever they occur may optionally be substituted with one or more, same or different substituents, and wherein the substitutents are independently selected from hydroxy, halo, cyano, nitro, oxo (═O), alkyl, haloalkyl, alkenyl, alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, heteroaryl, heterocyclic ring, heterocyclylalkyl, heteroarylalkyl, alkyl-C(O)ORx, —C(O)ORx, —C(O)Rx, —C(S)Rx, —C(O)NRaRb, —NRxC(O)NRaRb, —N(Rx)S(O)Ry, —N(Rx)S(O)2Ry, —NRaRb, —NRxC(O)Ry, —NRxC(S)Ry, —NRxC(S)NRaRb, —S(O)2NRaRb, —ORx, —OC(O)Rx, —OC(O)NRaRb, —RxC(O)ORy, —RxC(O)NRaRb, —RxC(O)Ry, —SRy, and —S(O)2Rx;
wherein at each occurrence, Rx, Ry and Rz are independently selected from hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, heterocyclylalkyl and heteroarylalkyl;
or its pharmaceutically acceptable salt thereof.

15 more elements

A compound which is selected from:

(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((3-Fluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((3,5-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(5-Methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(1-((4-Fluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((2,4-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((3,4-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((2,3-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chloro-2-fluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chloro-4-fluorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-(((3-Fluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-(((3-Difluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
1-((3-Chlorophenyl)amino)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)isoquinolin-4-carboxamide;
1-((3,5-Difluorophenyl)amino)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)isoquinolin-4-carboxamide;
1-((3-Fluorophenyl)amino)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)isoquinolin-4-carboxamide;
1-((4-Fluorophenyl)amino)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)isoquinolin-4-carboxamide;
N-(tert-Butyl)-1-((3-chlorophenyl)amino)-5-methylisoquinolin-4-carboxamide;
N-(tert-Butyl)-1-((3-fluorophenyl)amino)-5-methylisoquinolin-4-carboxamide;
N-(tert-Butyl)-1-((3,5-difluorophenyl)amino)-5-methylisoquinolin-4-carboxamide;
(1-((3-Fluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidino)methanone;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Methyl-1-(((3-trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3,5-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,4-Dichlorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((4-Fluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,4,5-Trifluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,4-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3,4-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Methyl-1-(((4-trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2-Chloro-4-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,3-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,5-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((4-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Chloro-4-fluorophenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-(Fluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-(Difluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-chlorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(5-methyl-1-((3-(trifluoromethyl)phenyl)amino) isoquinolin-4-yl)methanone;
(5-Methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((3-chlorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((2,4,5-trifluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(1-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((3-fluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((2,3-difluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((4-fluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((2,4-difluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(5-Methyl-1-((3,5-difluorophenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(2-oxa-6-azaspiro[3.5]nonan-6-yl)methanone;
(5-Methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(2-oxa-6-azaspiro[3.5]nonan-6-yl)methanone;
(3,5-Dimethylpiperazin-1-yl)(5-methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)methanone;
(3,5-Dimethylpiperazin-1-yl)(5-methyl-1-((3-chlorophenyl)amino)isoquinolin-4-yl)methanone;
(1-(4-Fluorophenoxy)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-(3,4-Difluorophenoxy)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-(2-Chloro-4-fluorophenoxy)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(1-(4-Fluorophenoxy)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-(3,4-Difluorophenoxy)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-(2-Chloro-4-fluorophenoxy)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-chloro-4-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-chloro-2-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-methylphenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-fluoro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3-chloro-2-methylphenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((5-chloro-2-methylphenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((2-fluoro-3-methylphenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((2,3-difluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((3,5-difluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(1-((3-chlorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(1-((3-(trifluoromethyl)phenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(1-((3-chloro-2-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(1-((3-chloro-4-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(1-((3-methylphenyl)amino)-5-methylisoquinolin-4-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(1-((3-chlorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(1-((3-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(1-((3-fluoro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)methanone;
3-Oxa-9-azabicyclo[3.3.1]nonan-9-yl(1-((3-chlorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
3-Oxa-9-azabicyclo[3.3.1]nonan-9-yl(1-((3-(trifluoromethyl)phenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
3-Oxa-9-azabicyclo[3.3.1]nonan-9-yl(1-((3-fluoro-2-methylphenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
(5-Methyl-1-(m-tolylamino)isoquinolin-4-yl)(morpholino)methanone;
(1-((3-Fluoro-4-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((3-Fluoro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((2-Fluoro-3-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((4-Fluoro-3-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((2-Chloro-5-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((3-Chloro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((5-Chloro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((3-Chloro-4-methylphenyl)amino)-5-methylisoquinolin-4-yl)(morpholino) methanone;
(1-((2,4-Dichlorophenyl)amino)-5-methylisoquinolin-4-yl)(morpholino)methanone;
(5-Methyl-1-(m-tolylamino)isoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Chloro-4-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2-Chloro-5-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((4-Fluoro-3-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Fluoro-4-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Fluoro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2-Fluoro-3-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(2-phenylmorpholino) methanone;
N-cyclohexyl-1-((3-fluorophenyl)amino)-5-methylisoquinolin-4-carboxamide;
N-cyclohexyl-1-((3,5-difluorophenyl)amino)-5-methylisoquinolin-4-carboxamide;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(pyrrolidin-1-yl)methanone;
(1-((3-Fluorophenyl)amino)-5-methylisoquinolin-4-yl)(pyrrolidin-1-yl)methanone;
(1-((3,5-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(pyrrolidin-1-yl)methanone;
(1-((2,4-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(pyrrolidin-1-yl)methanone;
Azetidin-1-yl(1-((3,5-difluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
Azetidin-1-yl(1-((4-fluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
(1-((3-Chloro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((5-Chloro-2-methylphenyl)amino)-5-methylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Methyl-1-((3-(trilluoromethyl)phenyl)amino)isoquinolin-4-yl) (2-oxa-7-azaspiro[3.5]nonan-7-yl)methanone;
(1-((3-Fluorophenyl)amino)-5-methylisoquinolin-4-yl) (2-oxa-7-azaspiro[3.5]nonan-7-yl)methanone;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(2-oxa-7-azaspiro[3.5]nonan-7-yl)methanone;
(5-Cyclopropyl-1-(m-tolylamino)isoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chlorophenyl)amino)-5-cyclopropylisoquinolin-4-yl)(morpholino)methanone;
(5-Cyclopropyl-1-(2-fluoro-3-methylphenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(5-Cyclopropyl-1-(2,3-difluorophenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(5-Cyclopropyl-1-(2,3,6-trifluorophenyl)amino)isoquinolin-4-yl)(morpholino) methanone;
(5-Cyclopropyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(morpholino)methanone
(5-Cyclopropyl-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chlorophenyl)amino)-5-cyclopropylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Chloro-2-fluorophenyl)amino)-5-cyclopropylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((2,3-Difluorophenyl)amino)-5-cyclopropylisoquinolin-4-yl)(piperidin-1-yl)methanone
(1-((2,3-Difluorophenyl)amino)-5-ethylisoquinolin-4-yl)(morpholino)methanone;
(1-((2,3-Difluorophenyl)amino)-5-ethylisoquinolin-4-yl) (piperidin-1-yl)methanone;
(1-((2,4-Difluorophenyl)amino)-5-ethylisoquinolin-4-yl) (piperidin-1-yl)methanone;
(1-((3,5-Difluorophenyl)amino)-5-ethylisoquinolin-4-yl) (piperidin-1-yl)methanone;
(1-((3-Chlorophenyl)amino)-5-ethylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Chloro-2-fluorophenyl)amino)-5-ethylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Ethyl-1-((2-Fluoro-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Fluoro-2-methylphenyl)amino)-5-ethylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(1-((3-Chloro-2-methylphenyl)amino)-5-ethylisoquinolin-4-yl)(piperidin-1-yl)methanone;
(4-((3-Chlorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3-Fluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(8-Methyl-4-((3-trifluoromethyl)phenyl)amino)naphthalen-1-yl)(morpholino) methanone;
(4-((2,3-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3,4-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((2,4-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3,5-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3-Chloro-4-fluorophenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl) (morpholino)methanone;
(4-((3-Chlorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-Fluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(8-Methyl-4-((3-trifluoromethyl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((2,3-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3,4-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((2,4-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3,5-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-Chloro-4-fluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(8-Methyl-4-(m-tolylamino)naphthalen-1-yl)(morpholino)methanone;
(4-((4-Fluoro-3-methylphenyl)amino)-8-methylnaphthalen-1-yl)(morpholino) methanone;
(4-((3-Fluoro-4-methylphenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3-Fluoro-2-methylphenyl)amino)-8-methylnaphthalen-1-yl)(morpholino) methanone;
(4-((3-Chloro-4-methylphenyl)amino)-8-methylnaphthalen-1-yl)(morpholino) methanone;
(4-((3-Chloro-2-methylphenyl)amino)-8-methylnaphthalen-1-yl)(morpholino) methanone;
(4-((3-(Fluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)(morpholino)methanone;
(4-((3-(Difluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)(morpholino) methanone;
(4-((4-Chlorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((4-Fluorophenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-(Difluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-Methoxyphenyl)amino)-8-methylnaphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-(Trifluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)(pyrrolidin-1-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(4-((2,3-difluorophenyl)amino)-8-methyl naphthalen-1-yl)methanone;
2-Oxa-5-azabicyclo[2.2.1]heptan-5-yl(4-((3-(difluoromethyl)phenyl)amino)-8-methyl naphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((3-fluorophenyl)amino)-8-methylnaphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((2,3-difluorophenyl)amino)-8-methylnaphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((3-(difluoromethyl)phenyl)amino)-8-methylnaphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(8-methyl-4-(m-tolylamino)naphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((3-chlorophenyl)amino)-8-methylnaphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((3-fluoro-2-methylphenyl)amino)-8-methylnaphthalen-1-yl)methanone;
3-Azabicyclo[3.1.0]hexan-3-yl(4-((3-fluoro-4-methylphenyl)amino)-8-methyl naphthalen-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((2,3-difluorophenyl)amino)-8-methyl naphthalen-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((3-fluoro-2-methylphenyl)amino)-8-methyl naphthalen-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((3-chlorophenyl)amino)-8-methyl naphthalene-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((3-(trifluoromethyl)phenyl)amino)-8-methyl naphthalene-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((3-chloro-2-fluorophenyl)amino)-8-methylnaphthalen-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(4-((3-chloro-4-fluorophenyl)amino)-8-methylnaphthalen-1-yl)methanone;
(4-((2,3-Difluorophenyl)amino)-8-methylnaphthalen-1-yl)(2-oxa-6-azaspiro[3.3]heptan-6-yl methanone;
(4-((3-Chlorophenyl)amino)naphthalen-1-yl)(morpholino)methanone;
4-((3-Chlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-1-naphthamide;
4-((3-Chlorophenyl)amino)-N-(pyridin-4-ylmethyl)-1-naphthamide;
N-Butyl-4-((3-chlorophenyl)amino)-1-naphthamide;
(4-((3-Fluorophenyl)amino)naphthalen-1-yl)(morpholino)methanone;
4-((3-Fluorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-1-naphthamide;
4-((3-Fluorophenyl)amino)-N-(pyridin-4-ylmethyl)-1-naphthamide;
N-Butyl-4-((3-fluorophenyl)amino)-1-naphthamide;
(4-((3,5-Difluorophenyl)amino)naphthalen-1-yl)(morpholino)methanone;
4-((3,5-Difluorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-1-naphthamide;
4-((3,5-Difluorophenyl)amino)-N-(pyridin-4-ylmethyl)-1-naphthamide;
(4-((3,5-Difluorophenyl)amino)naphthalen-1-yl)(3,5-dimethylmorpholino)methanone;
(4-((3,5-Difluorophenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((2,4-Difluorophenyl)amino)naphthalen-1-yl)(morpholino)methanone;
4-((2,4-Difluorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-1-naphthamide;
4-((2,4-Difluorophenyl)amino)-N-(pyridin-4-ylmethyl)-1-naphthamide;
N-Butyl-4-((2,4-difluorophenyl)amino)-1-naphthamide;
(4-((2,4-Difluorophenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((2,4-Dichlorophenyl)amino)naphthalen-1-yl)(morpholino)methanone;
4-((2,4-Dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-1-naphthamide;
4-((2,4-Dichlorophenyl)amino)-N-(pyridin-4-ylmethyl)-1-naphthamide;
N-Butyl-4-((2,4-dichlorophenyl)amino)-1-naphthamide;
Morpholino(4-((3-(trifluoromethyl)phenyl)amino)naphthalen-1-yl)methanone;
Piperidin-1-yl(4-((3-(trifluoromethyl)phenyl)amino)naphthalen-1-yl)methanone;
(4-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)naphthalen-1-yl)(morpholino) methanone;
(4-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
Morpholino(4-((3-(fluoromethyl)phenyl)amino)naphthalen-1-yl)methanone;
(4-((3-(Fluoromethyl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(4-((3-(Difluoromethyl)phenyl)amino)naphthalen-1-yl)(morpholino)methanone;
(4-((3-(Difluoromethyl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(5-Chloro-1-((3-chlorophenyl)amino)isoquinolin-4-yl)(piperidin-1-yl)methanon;
(5-Chloro-1-((3-fluoro-2-methylphenyl)amino)isoquinolin-4-yl)(piperidin-1-yl)methanone;
(5-Chloro-1-((2,3-difluorophenyl)amino)isoquinolin-4-yl) (piperidin-1-yl)methanone;
(5-Chloro-1-((3-chlorophenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(5-Chloro-1-((3-fluoro-2-methylphenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(5-Chloro-1-((2,3-difluorophenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(1-((3-Fluoro-2-methylphenyl)amino)-5-ethylisoquinolin-4-yl)(morpholino)methanone;
(5-Ethyl-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chloro-2-fluorophenyl)amino)-5-ethylisoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chloro-2-methylphenyl)amino)-5-ethylisoquinolin-4-yl)(morpholino)methanone;
(1-((3-Chloro-2-fluorophenyl)amino)-5-methylisoquinolin-4-yl)(1,1-dioxidothiomorpholino) methanone;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(1,1-dioxidothiomorpholino) methanone;
(1-((3,5-Difluorophenyl)amino)-5-methylisoquinolin-4-yl)(1,1-dioxidothiomorpholino) methanone;
(1-((3-Chlorophenyl)amino)-5-methylisoquinolin-4-yl)(4,4-difluoropiperidin-1-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((2,4-difluorophenyl)amino)-5-methylisoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((2-chloro-3-fluorophenyl)amino)-5-methyl isoquinolin-4-yl)methanone;
6-Oxa-3-azabicyclo[3.1.1]heptan-3-yl(1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-5-methylisoquinolin-4-yl)methanone;
1-((2,5-Bis(trifluoromethyl)phenyl)amino)-N,N,5-trimethyl isoquinolin-4-carboxamide;
Methyl 3-((5-chloro-4-(diethyl carbamoyl)isoquinolin-1-yl)amino)benzoate;
Methyl 3-((5-chloro-4-(diethyl carbamoyl)isoquinolin-1-yl)amino)-2-methylbenzoate;
Methyl 3-((5-chloro-4-(diethyl carbamoyl)isoquinolin-1-yl)amino)benzoate;
Methyl 2-methyl-3-((5-chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)benzoate;
Methyl 2-chloro-3-((5-methyl-4-(piperidin-1-carbonyl)isoquinolin-1-yl)amino)benzoate;
N-Ethyl-1-((4-fluoro-3-(trifluoro methyl)phenyl)amino)-N,5-dimethyl isoquinolin-4-carboxamide;
1-((2,3-Dimethylphenyl)amino)-N-ethyl-N,5-dimethylisoquinolin-4-carboxamide;
N-Ethyl-1-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-N,5-dimethyl isoquinolin-4-carboxamide;
1-((3-Fluoro-2-methylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((3-Chloro-2-methylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((5-Fluoro-2-methylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((2-Fluoro-3-(trifluoromethyl)phenyl)amino)-N,N,5-trimethyl isoquinolin-4-carboxamide;
1-((3-Fluoro-2-(trifluoromethyl)phenyl)amino)-N,N,5-trimethyl isoquinolin-4-carboxamide;
N,N,5-Trimethyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
1-((2-Chloro-3-fluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((3-Chloro-4-fluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((3-Chloro-2-fluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((2,3-Difluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((5-Chloro-2-fluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((2-Chloro-5-fluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((2,3-Dimethylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((3,5-Difluorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((3-Chlorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
N,N,5-Trimethyl-1-((3-(trifluoro methyl)phenyl)amino)isoquinolin-4-carboxamide;
1-((2,3-Dichlorophenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((5-Chloro-2-methylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((4-Chloro-3-methylphenyl)amino)-N,N,5-trimethylisoquinolin-4-carboxamide;
1-((2,5-Bis(trifluoromethyl)phenyl)amino)-N,N,5-trimethyl isoquinolin-4-carboxamide;
1-((2-Methoxy-5-(trifluoromethyl)phenyl)amino)-N,N,5-trimethyl isoquinolin-4-carboxamide;
N,N-Diethyl-1-((3-fluoro-2-methyl phenyl)amino)-5-methylisoquinolin-4-carboxamide;
1-((3-Chloro-2-methylphenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
N,N-Diethyl-1-((2-fluoro-3-(trifluoro methyl)phenyl)amino)-5-methyl isoquinolin-4-carboxamide;
N,N-Diethyl-1-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-5-methyl isoquinolin-4-carboxamide;
N,N-Diethyl-5-methyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino) isoquinolin-4-carboxamide;
1-((2-Chloro-3-fluorophenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
1-((3-Chloro-4-fluorophenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
1-((3-Chloro-2-fluorophenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
1-((2,3-Difluorophenyl)amino)-N,N-diethyl-5-methylisoquinolin-4-carboxamide;
1-((5-Chloro-2-fluorophenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
1-((2-Chloro-5-fluorophenyl)amino)-N,N-diethyl-5-methyl isoquinolin-4-carboxamide;
1-((2,3-Dimethylphenyl)amino)-N,N-diethyl-5-methylisoquinolin-4-carboxamide;
1-((3,5-Difluorophenyl)amino)-N,N-diethyl-5-methylisoquinolin-4-carboxamide;
1-((3-Chlorophenyl)amino)-N,N-diethyl-5-methylisoquinolin-4-carboxamide;
N,N-Diethyl-5-methyl-1-((3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
N-Ethyl-1-((3-fluoro-2-methyl phenyl)amino)-N,5-dimethyl isoquinolin-4-carboxamide;
1-((3-Chloro-2-methylphenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
N-Ethyl-1-((2-fluoro-3-(trifluoro methyl)phenyl)amino)-N,5-dimethyl isoquinolin-4-carboxamide;
N-Ethyl-N,5-dimethyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
1-((2-Chloro-3-fluorophenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
1-((3-Chloro-2-fluorophenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
1-((2,3-Difluorophenyl)amino)-N-ethyl-N,5-dimethylisoquinolin-4-carboxamide;
1-((3-Chloro-4-fluorophenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
1-((5-Chloro-2-fluorophenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
1-((2-Chloro-5-fluorophenyl)amino)-N-ethyl-N,5-dimethyl isoquinolin-4-carboxamide;
1-((3,5-Difluorophenyl)amino)-N-ethyl-N,5-dimethylisoquinolin-4-carboxamide;
1-((3-Chlorophenyl)amino)-N-ethyl-N,5-dimethylisoquinolin-4-carboxamide;
N-ethyl-N,5-dimethyl-1-((3-(trifluoromethyl)phenyl)amino) isoquinolin-4-carboxamide;
1-((3-Fluoro-2-methylphenyl)amino)-5-methyl-N,N-dipropyl isoquinolin-4-carboxamide;
1-((3-Chloro-2-methylphenyl)amino)-5-methyl-N,N-dipropyl isoquinolin-4-carboxamide;
1-((2-Fluoro-3-(trifluoromethyl)phenyl)amino)-5-methyl-N,N-dipropylisoquinolin-4-carboxamide;
1-((3-Fluoro-2-(trifluoromethyl)phenyl)amino)-5-methyl-N,N-dipropylisoquinolin-4-carboxamide;
5-Methyl-1-((2-methyl-3-(trifluoro methyl)phenyl)amino)-N,N-dipropylisoquinolin-4-carboxamide;
1-((2-Chloro-3-fluorophenyl)amino)-5-methyl-N,N-dipropyl isoquinolin-4-carboxamide;
N-Ethyl-1-((3-fluoro-2-methyl phenyl)amino)-5-methyl-N-propyl isoquinolin-4-carboxamide;
1-((3-Chloro-2-methylphenyl)amino)-N-ethyl-5-methyl-N-propyl isoquinolin-4-carboxamide;
N-Ethyl-1-((5-fluoro-2-methyl phenyl)amino)-5-methyl-N-propyl isoquinolin-4-carboxamide;
N-Ethyl-1-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-5-methyl-N-propylisoquinolin-4-carboxamide;
2-Methyl-3-((5-methyl-4-(piperidin-1-carbonyl)isoquinolin-1-yl)amino)benzoic acid;
2-Methyl-3-((5-methyl-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)benzoic acid;
3-((4-(Dimethylcarbamoyl)-5-methylisoquinolin-1-yl)amino)-2-methylbenzoic acid;
3-((4-(Diethylcarbamoyl)-5-methylisoquinolin-1-yl)amino)-2-methylbenzoic acid;
5-Chloro-1-((2-chloro-3-(trifluoro methyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((2-chloro-3-fluoro phenyl)amino)-N,N-dimethyl isoquinolin-4-carboxamide;
5-Chloro-1-((2,3-dimethylphenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((2,3-dimethylphenyl)amino)-N-ethyl-N-methyl isoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-2-fluoro phenyl)amino)-N,N-diethyl isoquinoline-4-carboxamide;
5-Chloro-1-((3-chloro-2-methyl phenyl)amino)-N,N-diethyl isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((3-fluoro-2-methylphenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((3-fluoro-2-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((2,3-dichlorophenyl)amino)-N,N-diethylisoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((2,3,6-trifluorophenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-dimethyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-N-ethyl-N-methyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-2-methylphenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((3-fluoro-2-(trifluoromethyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-N-ethyl-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-N-methylisoquinolin-4-carboxamide;
5-Chloro-N-ethyl-1-((3-fluoro-2-(trifluoromethyl)phenyl)amino)-N-methylisoquinolin-4-carboxamide;
5-Chloro-1-((2-chloro-3-fluoro phenyl)amino)-N-ethyl-N-methyl isoquinolin-4-carboxamide;
3-((5-Chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)-2-methyl benzoic acid;
3-((5-Chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)-2-methylbenzoic acid;
5-Chloro-1((2-methyl-3-(trifluoro methyl)phenyl)amino)-N,N-dipropylisoquinolin-4-carboxamide;
2-Chloro-4-((5-chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)benzoic acid;
3-((5-Chloro-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)-2-methylbenzoic acid;
5-Chloro-N,N-diethyl-1-((3-(trifluoromethyl)phenyl)amino) isoquinolin-4-carboxamide;
5-Chloro-1-((2,4-dichlorophenyl)amino)-N,N-diethylisoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((2,3,4-trifluorophenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((2,3,5-trifluorophenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((2,3-difluorophenyl)amino)-N,N-diethylisoquinolin-4-carboxamide;
5-Chloro-1-((2-chloro-3-fluoro phenyl)amino)-N,N-diethyl isoquinolin-4-carboxamide;
3-((5-Chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)benzoic acid;
5-Chloro-1-((3-fluoro-2-methyl phenyl)amino)-N,N-dimethyl isoquinolin-4-carboxamide;
5-Chloro-1-((2,3-difluorophenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
3-((5-Chloro-4-(dipropylcarbamoyl) isoquinolin-1-yl)amino)-2-methyl benzoic acid;
3-((5-Chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)-2-fluorobenzoic acid;
3-((5-Chloro-4-(dipropylcarbamoyl)isoquinolin-1-yl)amino)-4-methyl benzoic acid;
3-((5-Chloro-4-(ethyl(methyl)carbamoyl)isoquinolin-1-yl)amino)-2-methylbenzoic acid;
5-Chloro-N-ethyl-N-methyl-1-((2,3,6-trifluorophenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N-ethyl-1-((3-fluoro-2-methylphenyl)amino)-N-methylisoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-2-methylphenyl)amino)-N-ethyl-N-methylisoquinolin-4-carboxamide;
3-((5-Chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)-2-fluoro benzoic acid;
3-((5-Chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)-4-methylbenzoic acid;
5-Chloro-N,N-diethyl-1-((2-methyl-3-(methylcarbamoyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((2,3-dimethylphenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
3-((5-Chloro-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)-4-methylbenzoic acid;
5-Chloro-1-((2,3-dichlorophenyl)amino)-N-ethyl-N-methyl isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((3-(methyl carbamoyl)phenyl)amino)isoquinolin-4-carboxamide;
3-((5-Chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)-4-methyl benzoic acid;
3-((5-Chloro-4-(piperidine-1-carbonyl)isoquinolin-1-yl)amino)-4-methylbenzoic acid;
5-Chloro-1-((2-chloro-3-fluoro phenyl)amino)-N,N-dimethyl isoquinolin-4-carboxamide;
5-Chloro-1-((2-fluoro-3-(methyl carbamoyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
3-((5-Chloro-4-(piperidine-1-carbonyl)isoquinolin-1-yl)amino)-2-methylbenzoic acid;
4-((5-Chloro-4-(ethyl(methyl)carbamoyl)isoquinolin-1-yl)amino)-2-methylbenzoic acid;
2-Chloro-4-((5-chloro-4-(ethyl(methyl)carbamoyl)isoquinolin-1-yl)amino)benzoic acid;
1-((3,5-Bis(trifluoromethyl)phenyl)amino)-5-chloro-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((5-chloro-2-fluoro phenyl)amino)-N,N-dimethyl isoquinolin-4-carboxamide;
5-Chloro-1-((4-chloro-3-methyl phenyl)amino)-N,N-dimethyl isoquinolin-4-carboxamide;
4-((5-Chloro-4-(ethyl(methyl)carbamoyl)isoquinolin-1-yl)amino)-3-methylbenzoic acid;
5-Chloro-1-((2-chloro-3-(trifluoromethyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
4-((5-Chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)-3-methylbenzoic acid;
4-((5-chloro-4-(dimethylcarbamoyl)isoquinolin-1-yl)amino)-3-fluoro benzoic acid;
5-Chloro-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-N-isopropyl-N-methyl isoquinolin-4-carboxamide;
5-Chloro-1-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-N-isopropyl-N-methylisoquinolin-4-carboxamide;
5-Chloro-N-isopropyl-N-methyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((2-chloro-3-(trifluoromethyl)phenyl)amino)-N-isopropyl-N-methyl isoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-2-methylphenyl)amino)-N-isopropyl-N-methylisoquinolin-4-carboxamide;
5-Chloro-1-((3-fluoro-2-methylphenyl)amino)-N-isopropyl-N-methylisoquinolin-4-carboxamide;
2-(5-Chloro-1-((3-chloro-2-methylphenyl)amino)-N-methylisoquinolin-4-carboxamido) acetic acid;
2-(5-Chloro-1-((3-fluoro-2-methylphenyl)amino)-N-methylisoquinolin-4-carboxamido) acetic acid;
2-(5-Chloro-N-methyl-1-((2-methyl-3-(trifluoromethyl)phenyl)amino)isoquinolin-4-carboxamido)acetic acid;
2-(5-Chloro-1-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-N-methylisoquinolin-4-carboxamido)acetic acid
2-(5-Chloro-1-((3-fluoro-2-(trifluoromethyl)phenyl)amino)-N-methylisoquinolin-4-carboxamido)acetic acid;
5-Chloro-1-((3-(dimethylcarbamoyl)-2-methylphenyl)amino)-N,N-diethylisoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((3-(methyl carbamoyl)-2-methylphenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-diethyl-1-((3-(methylcarbamoyl)phenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-N,N-dimethyl-1-((3-(methylcarbamoyl)-2-fluorophenyl)amino)isoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-4-(methylcarbamoyl)phenyl)amino)-N,N-dimethylisoquinolin-4-carboxamide;
5-Chloro-1-((3-chloro-4-(methylcarbamoyl)phenyl)amino)-N-ethyl-N-methylisoquinolin-4-carboxamide;
3-((5-Chloro-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)-N-ethyl-2-methyl benzamide;
3-((5-Chloro-4-(piperidin-1-carbonyl)isoquinolin-1-yl)amino)-N-ethyl-2-methyl benzamide;
Methyl 3-((5-methyl-4-(piperidin-1-carbonyl)isoquinolin-1-yl)amino)benzoate;
3-((5-Methyl-4-(piperidine-1-carbonyl)isoquinolin-1-yl)amino)benzoic acid;
Methyl 3-((5-methyl-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)benzoate;
3((5-Methyl-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)benzoic acid;
4-((5-Chloro-4-(dimethyl carbamoyl)isoquinolin-1-yl)amino)-3-methylbenzoic acid;
3-((5-Chloro-4-(diethylcarbamoyl)isoquinolin-1-yl)amino)-2-fluoro benzoic acid;
N,N-Dimethyl-3-((5-methyl-4-(morpholin-4-carbonyl)isoquinolin-1-yl)amino)benzamide;
(5-Methyl-1-((3-(morpholin-4-carbonyl)phenyl)amino)isoquinolin-4-yl)(morpholino)methanone;
Methyl 3-((5-methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)benzoate;
Methyl 3-((5-methyl-4-(morpholin-4-carbonyl)naphthalen-1-yl)amino)benzoate;
Methyl 2-methyl-3-((5-methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)benzoate;
Methyl 2-methyl-3-((5-methyl-4-(morpholin-4-carbonyl)naphthalen-1-yl)amino)benzoate;
Methyl 2-methyl-3-((5-methyl-4-(diethylcarbamoyl)naphthalen-1-yl)amino)benzoate;
Methyl 3-(3-((5-methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)propanoate;
N-Ethyl-4-((2-fluoro-3-(trifluoro methyl)phenyl)amino)-N,8-dimethyl-1-naphthamide;
N-Ethyl-4-((5-fluoro-2-methyl phenyl)amino)-N,8-dimethyl-1-naphthamide;
N-Ethyl-4-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-N,8-dimethyl-1-naphthamide;
N,N-Diethyl-8-methyl-4-((2-methyl-3-(trifluoromethyl)phenyl)amino)-1-naphthamide;
N,N-Diethyl-4-((3-fluoro-2-methyl phenyl)amino)-8-methyl-1-naphthamide;
4-((3-Chloro-2-methylphenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
N,N-Diethyl-4-((2-fluoro-3-(trifluoro methyl)phenyl)amino)-8-methyl-1-naphthamide;
4-((2-Chloro-3-fluorophenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
4-((3-Chloro-2-fluorophenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
4-((2,3-Dimethylphenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
N,N-Diethyl-4-((3-fluoro-2-(trifluoro methyl)phenyl)amino)-8-methyl-1-naphthamide;
4-((2-Chloro-3-fluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((2-Fluoro-3-(trifluoromethyl)phenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((2,3-Dimethylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
N,N,8-Trimethyl-4-((2-methyl-3-(trifluoromethyl)phenyl)amino)-1-naphthamide;
4-((3-Fluoro-2-(trifluoromethyl)phenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((3-Fluoro-2-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((3-Chloro-2-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((3-Chloro-2-fluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
N,N-Diethyl-4-((5-fluoro-2-methyl phenyl)amino)-8-methyl-1-naphthamide;
3-((4-(Diethylcarbamoyl)-5-methyl naphthalen-1-yl)amino)-2-methyl benzoic acid;
4-((2,3-Difluorophenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
2-Chloro-3-((4-(diethylcarbamoyl)-5-methylnaphthalen-1-yl)amino)benzoic acid;
4-((2,5-Bis(trifluoromethyl)phenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
N,N-Diethyl-4-((2-methoxy-5-(trifluoromethyl)phenyl)amino)-8-methyl-1-naphthamide;
3-((4-(Dimethylcarbamoyl)-5-methylnaphthalen-1-yl)amino)-2-methylbenzoic acid;
3-((4-(Dimethylcarbamoyl)-5-methylnaphthalen-1-yl)amino)-2-fluorobenzoic acid;
4-((5-Chloro-2-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((5-Chloro-2-fluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((2-Chloro-5-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((4-Chloro-3-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((2,3-Difluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((5-Fluoro-2-methylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((4-Fluoro-3-(trifluoromethyl)phenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((2-Chloro-5-fluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((3-Chloro-4-fluorophenyl)amino)-N,N,8-trimethyl-1-naphthamide;
N-Ethyl-4-((2-fluoro-3-(trifluoro methyl)phenyl)amino)-N,8-dimethyl-1-naphthamide;
N-Ethyl-4-((3-fluoro-2-methyl phenyl)amino)-N,8-dimethyl-1-naphthamide;
4-((2-Chloro-3-fluorophenyl)amino)-N-ethyl-N,8-dimethyl-1-naphthamide;
N-Ethyl-N,8-dimethyl-4-((2-methyl-3-(trifluoromethyl)phenyl)amino)-1-naphthamide;
4-((2,3-Dimethylphenyl)amino)-N-ethyl-N,8-dimethyl-1-naphthamide;
N-Ethyl-4-((5-fluoro-2-methyl phenyl)amino)-N,8-dimethyl-1-naphthamide;
N-Ethyl-4-((4-fluoro-3-(trifluoro methyl)phenyl)amino)-N,8-dimethyl-1-naphthamide;
4-((3-Chloro-2-methylphenyl)amino)-N-ethyl-N,8-dimethyl-1-naphthamide;
4-((5-Chloro-2-methylphenyl)amino)-N-ethyl-N,8-dimethyl-1-naphthamide;
4-((2,3-Difluorophenyl)amino)-N-ethyl-N, 8-dimethyl-1-naphthamide;
4-((2-Chloro-5-fluorophenyl)amino)-N-ethyl-N,8-dimethyl-1-naphthamide;
3-((4-(Dipropylcarbamoyl)-5-methylnaphthalen-1-yl)amino)-2-methylbenzoic acid;
2-Methyl-3-((5-methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)benzoic acid;
2-Methyl-3-((5-methyl-4-(morpholin-4-carbonyl)naphthalen-1-yl)amino)benzoic acid;
4-Methyl-3-((5-methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)benzoic acid;
4-((5-Methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)-3-(trifluoromethyl)benzoic acid;
3-(3-((5-Methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino) propanoic acid;
3-((5-Methyl-4-(piperidin-1-carbonyl)naphthalen-1-yl)amino)benzoic acid;
3-((5-Methyl-4-(morpholin-4-carbonyl)naphthalen-1-yl)amino)benzoic acid;
8-Chloro-N,N-dimethyl-4-((2-methyl-3-(trifluoromethyl)phenyl)amino)-1-naphthamide;
8-Chloro-4-((3-fluoro-2-(trifluoromethyl)phenyl)amino)-N,N-dimethyl-1-naphthamide;
8-Chloro-4-((2-fluoro-3-(trifluoromethyl)phenyl)amino)-N,N-dimethyl-1-naphthamide;
2-Methyl-3-((5-methyl-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)benzonitrile;
(8-Methyl-4-((2-methyl-3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
N,N,8-Trimethyl-4-((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
N,N-diethyl-8-methyl-4-((2-methyl-3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
2-Methyl-3-((5-methyl-4-(morpholine-4-carbonyl)naphthalen-1-yl)amino)benzonitrile;
3-((5-Chloro-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)-2-methylbenzonitrile;
8-Chloro-N,N-dimethyl-4-((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
8-Chloro-N,N-diethyl-4-((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
(8-Chloro-4-((2-methyl-3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(8-Chloro-4-((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
3-((5-Fluoro-4-(morpholine-4-carbonyl)naphthalen-1-yl)amino)-2-methylbenzonitrile;
N,N-Diethyl-8-fluoro-4-((2-methyl-3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
8-fluoro-N,N-dimethyl-4((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)-1-naphthamide;
(8-Fluoro-4-((2-methyl-3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
(8-Fluoro-4-((3-(1-methyl-1H-tetrazol-5-yl)phenyl)amino)naphthalen-1-yl)(piperidin-1-yl)methanone;
3-((5-Fluoro-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)-2-methylbenzoic acid;
Methyl 3-((5-chloro-4-(diethylcarbamoyl)naphthalen-1-yl)amino)benzoate;
Methyl 3-((4-(dimethylcarbamoyl)-5-fluoronaphthalen-1-yl)amino)-2-methyl benzoate;
5-((5-Chloro-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)-2-methylbenzoic acid;
Methyl 3-((5-fluoro-4-(morpholine-4-carbonyl)naphthalen-1-yl)amino)-4-methyl benzoate;
2-Methyl-3-((5-methyl-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)benzamide;
N,N,2-Trimethyl-3-((5-methyl-4-(morpholine-4-carbonyl)naphthalen-1-yl)amino)benzamide;
4-((3-Carbamoylphenyl)amino)-N,N,8-trimethyl-1-naphthamide;
4-((3-Carbamoyl-2-methylphenyl)amino)-N,N-diethyl-8-methyl-1-naphthamide;
N,N,2-Trimethyl-5-((5-methyl-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)benzamide;
5-((5-Fluoro-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)-N,N,2-trimethylbenzamide;
3-((5-Tluoro-4-(morpholine-4-carbonyl)naphthalen-1-yl)amino)-N,N,2-trimethylbenzamide;
4-((3-Carbamoyl-2-methylphenyl)amino)-8-chloro-N,N-dimethyl-1-naphthamide;
8-Chloro-4-((3-(dimethylcarbamoyl)phenyl)amino)-N,N-diethyl-1-naphthamide;
and
3-((5-Fluoro-4-(piperidine-1-carbonyl)naphthalen-1-yl)amino)-2-methylbenzamide or pharmaceutically acceptable salt thereof.

478 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/542,234Filed 5 Jul 2012 · continuation in part
Priority: IN 905/KOL/20115 Jul 2011
Published: US 2013/0178457 A111 Jul 2013
Granted: 14 Apr 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification28 codes

C07D 217/26
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A61K 31/4725
Non-condensed isoquinolines, e.g. papaverine: containing further heterocyclic rings
A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol
A61K 31/541
Having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame: non-condensed thiazines containing…

Family

PCT/IB2011/056007Parent of this continuation-in-part · filed 29 Dec 2011
US 2013/0178457 A1Pre-grant publication · published 11 Jul 2013
US 9,006,442 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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