JP2013507350A5 - - Google Patents
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- Publication number
- JP2013507350A5 JP2013507350A5 JP2012532675A JP2012532675A JP2013507350A5 JP 2013507350 A5 JP2013507350 A5 JP 2013507350A5 JP 2012532675 A JP2012532675 A JP 2012532675A JP 2012532675 A JP2012532675 A JP 2012532675A JP 2013507350 A5 JP2013507350 A5 JP 2013507350A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- trifluoromethyl
- cyclopropyl
- phenyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 108091006146 Channels Proteins 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 102000020167 Calcium release-activated calcium channel Human genes 0.000 claims description 5
- 108091022898 Calcium release-activated calcium channel Proteins 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 3
- -1 nitro, hydroxy Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 3
- QLEZWYHCXVFRKO-RFZPGFLSSA-N (2r,4r)-4-methoxypyrrolidine-1,2-dicarboxylic acid Chemical compound CO[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 QLEZWYHCXVFRKO-RFZPGFLSSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- GWFGTSREWAXBIS-UHFFFAOYSA-N 1-[3-chloro-5-[[4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]carbamoyl]pyridin-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C1=NC=C(C(=O)NC=2SC=C(N=2)C=2C(=C(C=CC=2)C(F)(F)F)F)C=C1Cl GWFGTSREWAXBIS-UHFFFAOYSA-N 0.000 claims 1
- GLFVXQLTWWLREF-UHFFFAOYSA-N 1-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-3-(4-methylpyrimidin-5-yl)urea Chemical compound CC1=NC=NC=C1NC(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 GLFVXQLTWWLREF-UHFFFAOYSA-N 0.000 claims 1
- ZYNMTGYQHCTIBE-UHFFFAOYSA-N 1-[6-[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]-3-(4-methyl-1,3-thiazol-5-yl)urea Chemical compound N1=CSC(NC(=O)NC=2C=NC(=CC=2)N2C(=CC(=N2)C2CC2)C(F)(F)F)=C1C ZYNMTGYQHCTIBE-UHFFFAOYSA-N 0.000 claims 1
- UBFCARIDRZXMJS-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]cyclopropane-1-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C1C(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)C1 UBFCARIDRZXMJS-UHFFFAOYSA-N 0.000 claims 1
- ICAJDZQXGRNALW-UHFFFAOYSA-N 2-chloro-n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-5-methylsulfanylbenzamide Chemical compound CSC1=CC=C(Cl)C(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1 ICAJDZQXGRNALW-UHFFFAOYSA-N 0.000 claims 1
- NMWFBGRXPMCMBD-UHFFFAOYSA-N 2-chloro-n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-5-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1 NMWFBGRXPMCMBD-UHFFFAOYSA-N 0.000 claims 1
- LRCVLUZEPLXIPR-UHFFFAOYSA-N 3,5-dichloro-n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]pyridine-4-carboxamide Chemical compound ClC1=CN=CC(Cl)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 LRCVLUZEPLXIPR-UHFFFAOYSA-N 0.000 claims 1
- IMRIYHZNPLWXAW-UHFFFAOYSA-N 3,5-dicyclopropyl-1h-pyrazole Chemical compound C1CC1C1=NNC(C2CC2)=C1 IMRIYHZNPLWXAW-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KWRNPTYEYIKSAW-UHFFFAOYSA-N 4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-n-(2,3-difluorophenyl)-3-fluorobenzamide Chemical compound FC1=CC=CC(NC(=O)C=2C=C(F)C(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1F KWRNPTYEYIKSAW-UHFFFAOYSA-N 0.000 claims 1
- BEBHBILBEVKHHU-UHFFFAOYSA-N 4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-n-(2,6-difluorophenyl)-3-fluorobenzamide Chemical compound FC1=CC=CC(F)=C1NC(=O)C1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 BEBHBILBEVKHHU-UHFFFAOYSA-N 0.000 claims 1
- MYWRMJZQVRBGIM-UHFFFAOYSA-N 4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-n-[(4-methyl-1,3-thiazol-5-yl)methyl]aniline Chemical compound N1=CSC(CNC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C MYWRMJZQVRBGIM-UHFFFAOYSA-N 0.000 claims 1
- KDBOALQBLLXYLI-UHFFFAOYSA-N 6-(3,5-dicyclopropylpyrazol-1-yl)-n-(2-methylphenyl)pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 KDBOALQBLLXYLI-UHFFFAOYSA-N 0.000 claims 1
- DXDCXYQMUUKCMI-UHFFFAOYSA-N 6-(3-cyano-1-methylpyrazol-4-yl)-2-[2-(3-fluorophenyl)ethylamino]-n-(pyridin-3-ylmethyl)pyridine-3-carboxamide Chemical compound N#CC1=NN(C)C=C1C(N=C1NCCC=2C=C(F)C=CC=2)=CC=C1C(=O)NCC1=CC=CN=C1 DXDCXYQMUUKCMI-UHFFFAOYSA-N 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- RYZBMEMJAVMCHK-UHFFFAOYSA-N C(C)(C)(C)OCC1=CC(=NN1C1=CC=C(C=C1)NC(C1=CC=C(C=C1)Cl)=O)C(F)(F)F Chemical compound C(C)(C)(C)OCC1=CC(=NN1C1=CC=C(C=C1)NC(C1=CC=C(C=C1)Cl)=O)C(F)(F)F RYZBMEMJAVMCHK-UHFFFAOYSA-N 0.000 claims 1
- JKTSXNHJZJOLIK-UHFFFAOYSA-N C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=CS1)C.C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C Chemical compound C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=CS1)C.C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C JKTSXNHJZJOLIK-UHFFFAOYSA-N 0.000 claims 1
- NMWSYCBPBUWKEZ-UHFFFAOYSA-N C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C=1C=NOC1C.C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=C(S1)C)C Chemical compound C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C=1C=NOC1C.C1(CC1)C1=NN(C(=C1)C1CC1)C1=CC=C(C=C1)NC(=O)C1=C(N=C(S1)C)C NMWSYCBPBUWKEZ-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 241000239366 Euphausiacea Species 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- MXLRZHXEBHQPKM-UHFFFAOYSA-N N-[4-[3-(methoxymethyl)-5-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-3-carboxamide Chemical compound COCC1=NN(C(=C1)C(F)(F)F)C1=CC=C(C=C1)NC(C1=CN=CC=C1)=O MXLRZHXEBHQPKM-UHFFFAOYSA-N 0.000 claims 1
- KOOLSTGISCCXKF-UHFFFAOYSA-N N-[4-[3-cyclopentyl-5-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-3-carboxamide Chemical compound C1(CCCC1)C1=NN(C(=C1)C(F)(F)F)C1=CC=C(C=C1)NC(C1=CN=CC=C1)=O KOOLSTGISCCXKF-UHFFFAOYSA-N 0.000 claims 1
- VKBIFBIGPUFKJD-UHFFFAOYSA-N N-[4-[5-(methoxymethyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-3-carboxamide Chemical compound COCC1=CC(=NN1C1=CC=C(C=C1)NC(C1=CN=CC=C1)=O)C(F)(F)F VKBIFBIGPUFKJD-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010009887 colitis Diseases 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- VXTTXPZCOFNKFY-UHFFFAOYSA-N ethyl 1-[4-[(4-chlorobenzoyl)amino]phenyl]-5-methylpyrazole-3-carboxylate Chemical compound ClC1=CC=C(C(=O)NC2=CC=C(C=C2)N2N=C(C=C2C)C(=O)OCC)C=C1 VXTTXPZCOFNKFY-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- FEIPNLUVWDTZAA-UHFFFAOYSA-N n-(2-chloro-6-fluorophenyl)-4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorobenzamide Chemical compound FC1=CC=CC(Cl)=C1NC(=O)C1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 FEIPNLUVWDTZAA-UHFFFAOYSA-N 0.000 claims 1
- OLBVHWVLKVATBM-UHFFFAOYSA-N n-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyrimidin-5-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CN=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)N=C1 OLBVHWVLKVATBM-UHFFFAOYSA-N 0.000 claims 1
- ZERPDVBVUIWHHT-UHFFFAOYSA-N n-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyrimidin-5-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=NC(=NC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C ZERPDVBVUIWHHT-UHFFFAOYSA-N 0.000 claims 1
- UQKBZWKRMAQMOD-UHFFFAOYSA-N n-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyrimidin-5-yl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CN=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)N=C1 UQKBZWKRMAQMOD-UHFFFAOYSA-N 0.000 claims 1
- DAJBKTAYRHGBNZ-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1F DAJBKTAYRHGBNZ-UHFFFAOYSA-N 0.000 claims 1
- FQBXOFLHBKDTPO-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=C1 FQBXOFLHBKDTPO-UHFFFAOYSA-N 0.000 claims 1
- HYVBUGBOCHROJO-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=C1 HYVBUGBOCHROJO-UHFFFAOYSA-N 0.000 claims 1
- RJBZJVCDPSSPHC-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=C1 RJBZJVCDPSSPHC-UHFFFAOYSA-N 0.000 claims 1
- XEFMLAQCTGIRHW-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1C XEFMLAQCTGIRHW-UHFFFAOYSA-N 0.000 claims 1
- MOXHODGYJMWHOR-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=C1 MOXHODGYJMWHOR-UHFFFAOYSA-N 0.000 claims 1
- UOXHLYMLCPPNGX-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1C UOXHLYMLCPPNGX-UHFFFAOYSA-N 0.000 claims 1
- NFZPYAVQNLTBTL-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]pyridine-3-carboxamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=CC=1NC(=O)C1=CC=CN=C1 NFZPYAVQNLTBTL-UHFFFAOYSA-N 0.000 claims 1
- CJSSCSFJKBMVPA-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]pyridine-4-carboxamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C(F)=CC=1NC(=O)C1=CC=NC=C1 CJSSCSFJKBMVPA-UHFFFAOYSA-N 0.000 claims 1
- RMKGWPJBXBQFQU-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1F RMKGWPJBXBQFQU-UHFFFAOYSA-N 0.000 claims 1
- CLCUBAQCPQZECR-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C=CC=1NC(=O)CN1CCOCC1 CLCUBAQCPQZECR-UHFFFAOYSA-N 0.000 claims 1
- OUJQSLUNDPQAFU-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]-2-phenylacetamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C=CC=1NC(=O)CC1=CC=CC=C1 OUJQSLUNDPQAFU-UHFFFAOYSA-N 0.000 claims 1
- AXHWFMNIDPYRFF-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]-2-pyridin-2-ylacetamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C=CC=1NC(=O)CC1=CC=CC=N1 AXHWFMNIDPYRFF-UHFFFAOYSA-N 0.000 claims 1
- IJQWLQPCTCKEPQ-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]-2-pyridin-3-ylacetamide Chemical compound C=1C=C(N2C(=CC(=N2)C2CC2)C2CC2)C=CC=1NC(=O)CC1=CC=CN=C1 IJQWLQPCTCKEPQ-UHFFFAOYSA-N 0.000 claims 1
- ADZPZBMIBOCSKO-UHFFFAOYSA-N n-[4-(3,5-dicyclopropylpyrazol-1-yl)phenyl]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CN=CC=1C(=O)NC(C=C1)=CC=C1N1N=C(C2CC2)C=C1C1CC1 ADZPZBMIBOCSKO-UHFFFAOYSA-N 0.000 claims 1
- RFTNCPFRYIPUHX-UHFFFAOYSA-N n-[4-(4-chloro-3,5-dicyclopropylpyrazol-1-yl)-3-fluorophenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=C(Cl)C(C3CC3)=N2)C2CC2)=C1C RFTNCPFRYIPUHX-UHFFFAOYSA-N 0.000 claims 1
- RSXBBIIEXWJJRE-UHFFFAOYSA-N n-[4-[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]phenyl]-5-methyl-1h-imidazole-4-carboxamide Chemical compound N1=CNC(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C2CC2)C(F)(F)F)=C1C RSXBBIIEXWJJRE-UHFFFAOYSA-N 0.000 claims 1
- KUXWRUPUAQQFBG-UHFFFAOYSA-N n-[4-[3-cyclopropyl-5-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC(C2CC2)=NN1C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 KUXWRUPUAQQFBG-UHFFFAOYSA-N 0.000 claims 1
- XNCWFJBFNVQYKC-UHFFFAOYSA-N n-[4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-2-pyridin-2-ylacetamide Chemical compound C=1C=C(N2C(=C(Cl)C(=N2)C(F)(F)F)C2CC2)C(F)=CC=1NC(=O)CC1=CC=CC=N1 XNCWFJBFNVQYKC-UHFFFAOYSA-N 0.000 claims 1
- KNDCIKVQPXZSNK-UHFFFAOYSA-N n-[4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CC=C(N2C(=C(Cl)C(=N2)C(F)(F)F)C2CC2)C(F)=C1 KNDCIKVQPXZSNK-UHFFFAOYSA-N 0.000 claims 1
- JQIHPFFLXQIRDI-UHFFFAOYSA-N n-[4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=C(Cl)C(=N2)C(F)(F)F)C2CC2)=C1C JQIHPFFLXQIRDI-UHFFFAOYSA-N 0.000 claims 1
- KOAUWBDKSVKMMA-UHFFFAOYSA-N n-[4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=CC(=CC=2)N2C(=C(Cl)C(=N2)C(F)(F)F)C2CC2)=C1C KOAUWBDKSVKMMA-UHFFFAOYSA-N 0.000 claims 1
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- MEACLAWLBLLLNT-UHFFFAOYSA-N n-[4-[5-cyano-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C#N)C=C1 MEACLAWLBLLLNT-UHFFFAOYSA-N 0.000 claims 1
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- XINKLXCYTHBPOA-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3,5-difluorophenyl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CC(F)=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 XINKLXCYTHBPOA-UHFFFAOYSA-N 0.000 claims 1
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- WCYNYRDMISKKIK-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 WCYNYRDMISKKIK-UHFFFAOYSA-N 0.000 claims 1
- ZZXATCCXNXZJSE-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 ZZXATCCXNXZJSE-UHFFFAOYSA-N 0.000 claims 1
- WZOCFUMVIUFWRF-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-4-methyl-1,3-oxazole-5-carboxamide Chemical compound N1=COC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C WZOCFUMVIUFWRF-UHFFFAOYSA-N 0.000 claims 1
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- LXBHQPCJVRNUPD-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=C1 LXBHQPCJVRNUPD-UHFFFAOYSA-N 0.000 claims 1
- GHVJBFUZYPACNM-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C GHVJBFUZYPACNM-UHFFFAOYSA-N 0.000 claims 1
- VEEFSWBIYMHIDZ-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(F)C(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C VEEFSWBIYMHIDZ-UHFFFAOYSA-N 0.000 claims 1
- JBEBFBSHFQIHMB-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]-n,4-dimethylpyrimidine-5-carboxamide Chemical compound C=1C=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=CC=1N(C)C(=O)C1=CN=CN=C1C JBEBFBSHFQIHMB-UHFFFAOYSA-N 0.000 claims 1
- OYSZVMLSJODPRA-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]pyridine-3-carboxamide Chemical compound C=1C=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=CC=1NC(=O)C1=CC=CN=C1 OYSZVMLSJODPRA-UHFFFAOYSA-N 0.000 claims 1
- AVNNWXCNOLKWDE-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]-3-fluorophenyl]pyridine-4-carboxamide Chemical compound C=1C=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C(F)=CC=1NC(=O)C1=CC=NC=C1 AVNNWXCNOLKWDE-UHFFFAOYSA-N 0.000 claims 1
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- IZKQBCKEKYHTTF-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-2-pyridin-2-ylacetamide Chemical compound C=1C=C(NC(=O)CC=2N=CC=CC=2)C=CC=1N1N=C(C(F)(F)F)C=C1C1CC1 IZKQBCKEKYHTTF-UHFFFAOYSA-N 0.000 claims 1
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- MPBVNNVYYBZUBT-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)C=C1 MPBVNNVYYBZUBT-UHFFFAOYSA-N 0.000 claims 1
- NYDXXCFKGFJZIR-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C NYDXXCFKGFJZIR-UHFFFAOYSA-N 0.000 claims 1
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- AFWWKCQISQJWEL-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C AFWWKCQISQJWEL-UHFFFAOYSA-N 0.000 claims 1
- JLGFZBLOESSPHG-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1C JLGFZBLOESSPHG-UHFFFAOYSA-N 0.000 claims 1
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- CMCMZPWFEIWORO-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C=NC=CC=2)C=CC=1N1N=C(C(F)(F)F)C=C1C1CC1 CMCMZPWFEIWORO-UHFFFAOYSA-N 0.000 claims 1
- GYSSXGLPYVGVEV-UHFFFAOYSA-N n-[4-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]phenyl]pyridine-4-carboxamide;hydrochloride Chemical compound Cl.C=1C=C(NC(=O)C=2C=CN=CC=2)C=CC=1N1N=C(C(F)(F)F)C=C1C1CC1 GYSSXGLPYVGVEV-UHFFFAOYSA-N 0.000 claims 1
- AKWFWOOHKZBSDK-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=NC(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1F AKWFWOOHKZBSDK-UHFFFAOYSA-N 0.000 claims 1
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- WRASVZRNENOMDQ-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 WRASVZRNENOMDQ-UHFFFAOYSA-N 0.000 claims 1
- BXVYKMSUNOTJRQ-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 BXVYKMSUNOTJRQ-UHFFFAOYSA-N 0.000 claims 1
- QPIHQEIAVDSDJD-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-3-fluoropyridine-4-carboxamide Chemical compound FC1=CN=CC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 QPIHQEIAVDSDJD-UHFFFAOYSA-N 0.000 claims 1
- GKFRLLUOEZYDNB-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=NC(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1C GKFRLLUOEZYDNB-UHFFFAOYSA-N 0.000 claims 1
- VDYGCNFZZUCSDS-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-4-methylpyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C2CC2)C2CC2)N=C1 VDYGCNFZZUCSDS-UHFFFAOYSA-N 0.000 claims 1
- SURSAZLFUNKFLA-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]-4-methylthiadiazole-5-carboxamide Chemical compound N1=NSC(C(=O)NC=2C=NC(=CC=2)N2C(=CC(=N2)C2CC2)C2CC2)=C1C SURSAZLFUNKFLA-UHFFFAOYSA-N 0.000 claims 1
- IWIGLAOOHISPFC-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]pyridine-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CN=CC=1C(=O)NC(C=N1)=CC=C1N1N=C(C2CC2)C=C1C1CC1 IWIGLAOOHISPFC-UHFFFAOYSA-N 0.000 claims 1
- MZPYIJFFZPQWJP-UHFFFAOYSA-N n-[6-(3,5-dicyclopropylpyrazol-1-yl)pyridin-3-yl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(C=N1)=CC=C1N1N=C(C2CC2)C=C1C1CC1 MZPYIJFFZPQWJP-UHFFFAOYSA-N 0.000 claims 1
- JLTCFSSBFYODOL-UHFFFAOYSA-N n-[6-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound N1=CSC(C(=O)NC=2C=NC(=CC=2)N2C(=C(Cl)C(=N2)C(F)(F)F)C2CC2)=C1C JLTCFSSBFYODOL-UHFFFAOYSA-N 0.000 claims 1
- WVXWEWXVLIUSCI-UHFFFAOYSA-N n-[6-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]-2,3-difluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=NC(=CC=2)N2C(=CC(=N2)C(F)(F)F)C2CC2)=C1F WVXWEWXVLIUSCI-UHFFFAOYSA-N 0.000 claims 1
- LUIVHTZNEFYWML-UHFFFAOYSA-N n-[6-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC1=CC=C(N2C(=CC(=N2)C(F)(F)F)C2CC2)N=C1 LUIVHTZNEFYWML-UHFFFAOYSA-N 0.000 claims 1
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