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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Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6112486B2 (ja) | 2010-04-27 | 2017-04-12 | カルシメディカ，インク． | 細胞内カルシウムを調節する化合物 |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2609095A4 (en) | 2010-08-27 | 2014-06-18 | Calcimedica Inc | COMPOUNDS MODULATING INTRACELLULAR CALCIUM |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| BR112014012815A8 (pt) * | 2011-11-28 | 2017-06-20 | Novartis Ag | derivados de trifluormetil-oxadiazol e uso dos mesmos no tratamento de doença |
| WO2013164773A1 (en) * | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyrazole compounds as crac modulators |
| AU2013296619B2 (en) * | 2012-07-30 | 2016-07-28 | The Ohio State University | Antibacterial protein kinase inhibitors |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| KR20150103752A (ko) * | 2013-01-10 | 2015-09-11 | 그뤼넨탈 게엠베하 | Crac 채널 억제제로서의 피라졸릴계 카복스아미드 ⅱ |
| AR094412A1 (es) | 2013-01-10 | 2015-07-29 | Gruenenthal Gmbh | Carboxamidas basadas en pirazolilo i |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| GB201309333D0 (en) | 2013-05-23 | 2013-07-10 | Agency Science Tech & Res | Purine diones as WNT pathway modulators |
| EP2848615A1 (en) * | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| EP2865758A1 (en) * | 2013-10-22 | 2015-04-29 | Sylentis, S.A.U. | siRNA and their use in methods and compositions for inhibiting the expression of the ORAI1 gene |
| WO2015143653A1 (en) | 2014-03-26 | 2015-10-01 | Merck Sharp & Dohme Corp. | TrkA KINASE INHIBITORS,COMPOSITIONS AND METHODS THEREOF |
| EP3144297A4 (en) * | 2014-05-14 | 2017-11-29 | Asahi Glass Company, Limited | Ethereal oxygen atom-containing perfluoroalkyl group-substituted pyrimidine ring compound, and method for producing same |
| KR101685993B1 (ko) | 2014-05-15 | 2016-12-13 | 한국과학기술연구원 | 전압개폐 칼슘이온채널 억제 활성화능을 갖는 ｎ-(피라졸릴메틸)아릴설폰아마이드 화합물 및 이를 포함하는 약학적 조성물 |
| CN106414429B (zh) * | 2014-06-03 | 2020-01-03 | 爱杜西亚药品有限公司 | 吡唑化合物及其作为t型钙通道阻断剂的用途 |
| WO2015187827A1 (en) * | 2014-06-03 | 2015-12-10 | The Trustees Of The University Of Pennsylvania | Novel effective antiviral compounds and methods using same |
| WO2015197187A1 (en) * | 2014-06-24 | 2015-12-30 | Grünenthal GmbH | Pyrazolyl-based carboxamides v |
| CN107207431B (zh) * | 2015-01-13 | 2021-02-09 | 维夫雷昂生物科学有限责任公司 | Ca2+释放激活的Ca2+(CRAC)通道的调节剂及其药物用途 |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| US20180161388A1 (en) | 2015-05-18 | 2018-06-14 | Beth Israel Deaconess Medical Center, Inc. | Substance p, mast cell degranulation inhibitors, and peripheral neuropathy |
| KR102229608B1 (ko) | 2015-08-03 | 2021-03-19 | 아이크노스 사이언스 에스. 아. | Ror 감마 조절제로서의 신규한 화합물 |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| WO2017109793A1 (en) * | 2015-12-21 | 2017-06-29 | Council Of Scientific & Industrial Research | Novel 1,2,3 triazole-thiazole compounds, process for preparation and use thereof |
| KR102398439B1 (ko) * | 2016-03-07 | 2022-05-16 | 이난타 파마슈티칼스, 인코포레이티드 | B형 간염 항바이러스제 |
| ITUA20164199A1 (it) * | 2016-06-08 | 2017-12-08 | Univ Degli Studi Del Piemonte Orientale Amedeo Avogadro | Modulatori di soce compisizioni e relativi usi |
| AU2017327539B2 (en) | 2016-09-15 | 2020-12-24 | Boehringer Ingelheim International Gmbh | Heteroaryl carboxamide compounds as inhibitors of RIPK2 |
| SG11202001685TA (en) | 2017-08-28 | 2020-03-30 | Enanta Pharm Inc | Hepatitis b antiviral agents |
| JP2021501160A (ja) * | 2017-10-30 | 2021-01-14 | ルヒゼン ファーマスティカルズ エスエー | 血液がんおよび固形がんの処置のためのカルシウム放出活性化カルシウムチャネルモジュレーター |
| US11724997B2 (en) | 2018-03-01 | 2023-08-15 | Annapurna Bio, Inc. | Compounds and compositions for treating conditions associated with APJ receptor activity |
| WO2020053834A1 (en) | 2018-09-14 | 2020-03-19 | Rhizen Pharmaceuticals Sa | Compositions comprising a crac inhibitor and a corticosteroid and methods of use thereof |
| CA3115230A1 (en) * | 2018-10-04 | 2020-04-09 | The Trustees Of Indiana University | Methods to treat renal disorders using calcium channel inhibitors |
| IL283190B2 (en) | 2018-11-21 | 2025-08-01 | Enanta Pharm Inc | Functionalized heterocycles as antiviral agents |
| JP7364783B2 (ja) * | 2019-08-15 | 2023-10-18 | エフ． ホフマン－ラ ロシュ アーゲー | アリールスルホンアミド誘導体 |
| CN115210229A (zh) | 2020-01-03 | 2022-10-18 | 博格有限责任公司 | 多环酰胺作为治疗癌症的ube2k调节剂 |
| WO2021188414A1 (en) | 2020-03-16 | 2021-09-23 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
| JP2023528537A (ja) | 2020-03-20 | 2023-07-04 | カルシメディカ，インク． | 急性肺傷害及び急性呼吸窮迫症候群を処置するための方法及び組成物 |
| CN111269097B (zh) * | 2020-04-02 | 2023-02-17 | 苏州爱玛特生物科技有限公司 | 一种多元环双取代的1,3-丙二酮类化合物的合成方法 |
| CA3198798A1 (en) | 2020-11-13 | 2022-05-19 | Kenneth Stauderman | Improved synthesis of crac channel inhibitors |
| CN115925649A (zh) * | 2022-10-09 | 2023-04-07 | 深圳市茵诺圣生物科技有限公司 | 一种连续流制备4-甲基噻唑-5-甲醛的方法 |
| WO2024118667A1 (en) * | 2022-11-29 | 2024-06-06 | The United States Government As Represented By The Department Of Veterans Affairs | Eif4a1 inhibitors with antitumor activity |
| JP2026504858A (ja) * | 2023-01-19 | 2026-02-10 | ルミスター バイオテクノロジー，インク． | カルシウム放出活性化カルシウムチャネルもしくはジスコイジンドメイン受容体２関連障害または状態の治療または予防に使用するための医薬組成物 |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4385414B2 (ja) * | 1997-10-13 | 2009-12-16 | アステラス製薬株式会社 | アミド若しくはアミン誘導体 |
| AU751139B2 (en) * | 1997-10-13 | 2002-08-08 | Astellas Pharma Inc. | Amide derivative |
| WO1999062885A1 (en) | 1998-06-05 | 1999-12-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
| JP2000256358A (ja) * | 1999-03-10 | 2000-09-19 | Yamanouchi Pharmaceut Co Ltd | ピラゾール誘導体 |
| US20010044445A1 (en) * | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| EP1143013A1 (en) * | 2000-04-03 | 2001-10-10 | Warner-Lambert Company | Methods and compositions for screening Icrac modulators |
| WO2002089793A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| AU2002333524A1 (en) | 2001-09-11 | 2003-03-24 | Glaxosmithkline K.K. | Furo-and thienopyrimidine derivatives as angiogenesis inhibitors |
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| US7452675B2 (en) * | 2002-01-25 | 2008-11-18 | The Queen's Medical Center | Methods of screening for TRPM4b modulators |
| US7645588B2 (en) * | 2003-03-04 | 2010-01-12 | Calcimedica, Inc. | Composition comprising a cell comprising a STIM1 protein and an agent that modulates intracellular calcium and methods of use |
| TWI376370B (en) | 2003-07-23 | 2012-11-11 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
| AU2005245389A1 (en) | 2004-05-12 | 2005-12-01 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| KR20070057965A (ko) | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| EP1805218A2 (en) | 2004-10-29 | 2007-07-11 | Chemicon International, Inc. | Compositions and methods for the assay of g-protein coupled receptors and their ligands |
| KR20140018997A (ko) * | 2005-01-07 | 2014-02-13 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| EP1846388A4 (en) | 2005-01-25 | 2011-12-07 | Synta Pharmaceuticals Corp | THIOPHEN COMPOUNDS FOR IGNITIONS AND THE IMMUNE SYSTEM APPLICATIONS |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| EP1875925A1 (en) | 2005-04-22 | 2008-01-09 | Astellas Pharma Inc. | Preventive or remedy for bowel disease |
| WO2007004038A1 (en) | 2005-07-05 | 2007-01-11 | Pfizer Products Inc. | Aminothiazole derivatives as agonists of the thrombopoietin receptor |
| US8455658B2 (en) | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| WO2007087429A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| TW200806290A (en) | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted biaryl compounds for inflammation and immune-related uses |
| TW200806641A (en) | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted aromatic compounds for inflammation and immune-related uses |
| US7816535B2 (en) * | 2006-01-25 | 2010-10-19 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| US20070254926A1 (en) | 2006-01-31 | 2007-11-01 | Jun Jiang | Pyridylphenyl compounds for inflammation and immune-related uses |
| AU2007227210A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceuticals Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| AU2007230911A1 (en) | 2006-03-23 | 2007-10-04 | Synta Pharmaceuticals Corp. | Benzimidazolyl-pyridine compounds for inflammation and immune-related uses |
| AU2007238225A1 (en) | 2006-04-10 | 2007-10-25 | Beth Israel Deaconess Medical Center | CRAC modulators and use of same for drug discovery |
| US20080039392A1 (en) | 2006-05-26 | 2008-02-14 | The Regents Of The University Of California | CRAC channel and modulator screening methods |
| WO2008016643A2 (en) | 2006-08-01 | 2008-02-07 | Cytokinetics, Incorporated | Certain chemical entities, compositions, and methods |
| US8779154B2 (en) | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| US20080207641A1 (en) | 2006-11-13 | 2008-08-28 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl compounds for inflammation and immune-related uses |
| JP2010519206A (ja) | 2007-02-16 | 2010-06-03 | シンタ ファーマシューティカルズ コーポレーション | 炎症及び免疫関連使用のための置換縮合環化合物 |
| NZ580195A (en) | 2007-03-05 | 2012-03-30 | Univ Queensland | Targeting crac for breast cancer therapy and/or diagnosis |
| KR101217754B1 (ko) * | 2007-03-23 | 2013-01-02 | 더 퀸스 메디컬 센터 | Ｓｔｉｍ2 활성을 측정하기 위한 분석 및 방법 |
| CA2688417C (en) | 2007-05-24 | 2017-04-25 | Calcimedica, Inc. | Calcium channel proteins and uses thereof |
| CA2695148A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Pyridine compounds for inflammation and immune-related uses |
| WO2009017831A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Vinyl-aryl derivatives for inflammation and immune-related uses |
| CA2695143A1 (en) | 2007-08-01 | 2009-02-05 | Synta Pharmaceuticals Corp. | Heterocycle-aryl compounds for inflammation and immune-related uses |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8324219B2 (en) | 2007-09-20 | 2012-12-04 | Synta Pharmaceuticals Corp. | Substituted benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US20110052643A1 (en) | 2008-01-07 | 2011-03-03 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| TWI392673B (zh) | 2008-08-27 | 2013-04-11 | Calcimedica Inc | 調控細胞內鈣離子濃度之化合物 |
| US20110269743A1 (en) | 2008-09-22 | 2011-11-03 | CalciMedica, Inc | Phenylthiophenyldihydrobenzothiazepine inhibitors of store operated calcium release |
| US8524763B2 (en) * | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US20110257177A1 (en) | 2008-09-22 | 2011-10-20 | Calcimedica, Inc. | Benzylthiotetrazole inhibitors of store operated calcium release |
| AU2009300317A1 (en) | 2008-10-01 | 2010-04-08 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| AU2009300316A1 (en) | 2008-10-01 | 2010-04-08 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| AU2009300318A1 (en) | 2008-10-01 | 2010-04-08 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US8143269B2 (en) * | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| WO2010048559A2 (en) | 2008-10-24 | 2010-04-29 | Calcimedica Inc. | Phenylpyrazole inhibitors of store operated calcium release |
| US8993612B2 (en) * | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
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