JP2015528435A5 - - Google Patents
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- JP2015528435A5 JP2015528435A5 JP2015525727A JP2015525727A JP2015528435A5 JP 2015528435 A5 JP2015528435 A5 JP 2015528435A5 JP 2015525727 A JP2015525727 A JP 2015525727A JP 2015525727 A JP2015525727 A JP 2015525727A JP 2015528435 A5 JP2015528435 A5 JP 2015528435A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- carboxamide
- indazole
- tetrahydro
- dimethyl
- 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.)
- Pending
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- 125000000623 heterocyclic group Chemical group 0.000 claims 55
- 229910052736 halogen Inorganic materials 0.000 claims 40
- 150000002367 halogens Chemical class 0.000 claims 40
- -1 —OR 7 Chemical group 0.000 claims 38
- 125000004429 atom Chemical group 0.000 claims 33
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000002947 alkylene group Chemical group 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 11
- DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 8
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 7
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 125000004419 alkynylene group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- RINJMBVFDPSVNF-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(4-phenyloxolan-3-yl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C1COCC1C1=CC=CC=C1 RINJMBVFDPSVNF-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 1
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 claims 1
- KUWLIGSDXVIVJU-UHFFFAOYSA-N 5,5-dimethyl-n-[1-(2-methylsulfonyl-1-pyridin-3-ylethyl)pyrazol-4-yl]-4,6-dihydro-1h-cyclopenta[c]pyrazole-3-carboxamide Chemical compound C1=2CC(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1C(CS(C)(=O)=O)C1=CC=CN=C1 KUWLIGSDXVIVJU-UHFFFAOYSA-N 0.000 claims 1
- UNOQZKVEUMPMMM-UHFFFAOYSA-N 5a-methyl-n-[1-(2-methylsulfonyl-1-pyridin-3-ylethyl)pyrazol-4-yl]-4,4a,5,6-tetrahydro-1h-cyclopropa[f]indazole-3-carboxamide Chemical compound C1C2(C)CC2CC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CS(C)(=O)=O)C1=CC=CN=C1 UNOQZKVEUMPMMM-UHFFFAOYSA-N 0.000 claims 1
- QMTHDXTYDHZHFK-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(1-pyridin-3-ylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=CC=CN=C1 QMTHDXTYDHZHFK-UHFFFAOYSA-N 0.000 claims 1
- JUHYXBLLVCTKJA-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(1-pyridin-3-ylpropyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CC)C1=CC=CN=C1 JUHYXBLLVCTKJA-UHFFFAOYSA-N 0.000 claims 1
- BKAGOPPSLSHPMG-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(1-pyridin-4-ylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=CC=NC=C1 BKAGOPPSLSHPMG-UHFFFAOYSA-N 0.000 claims 1
- SFNLOYSFTSUDRG-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(2-methylsulfonyl-1-phenylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CS(C)(=O)=O)C1=CC=CC=C1 SFNLOYSFTSUDRG-UHFFFAOYSA-N 0.000 claims 1
- VRORKYZHKNPCSI-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(2-methylsulfonyl-1-pyridin-3-ylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CS(C)(=O)=O)C1=CC=CN=C1 VRORKYZHKNPCSI-UHFFFAOYSA-N 0.000 claims 1
- SNGCYBIKJUGIAR-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(2-morpholin-4-yl-1-phenylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)CN1CCOCC1 SNGCYBIKJUGIAR-UHFFFAOYSA-N 0.000 claims 1
- GLURFGLYQHSJCV-UHFFFAOYSA-N 6,6-dimethyl-n-[1-(3-methylsulfonyl-1-phenylpropyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CCS(C)(=O)=O)C1=CC=CC=C1 GLURFGLYQHSJCV-UHFFFAOYSA-N 0.000 claims 1
- JILRQTKSYVLOOY-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[(1-methylazetidin-3-yl)-phenylmethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1N(C)CC1C(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 JILRQTKSYVLOOY-UHFFFAOYSA-N 0.000 claims 1
- KBNVXLZPZMVNEN-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[(1-methylpiperidin-4-yl)-phenylmethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1CN(C)CCC1C(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 KBNVXLZPZMVNEN-UHFFFAOYSA-N 0.000 claims 1
- GDBJHEZNIGXEDJ-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[(1-methylsulfonylazetidin-3-yl)-phenylmethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CN(S(C)(=O)=O)C1 GDBJHEZNIGXEDJ-UHFFFAOYSA-N 0.000 claims 1
- WVLWPKJPQYEMSQ-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[(1-methylsulfonylpiperidin-4-yl)-phenylmethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CCN(S(C)(=O)=O)CC1 WVLWPKJPQYEMSQ-UHFFFAOYSA-N 0.000 claims 1
- LXKDSMIFVYYJAC-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[(3-methylsulfonylphenyl)-(oxolan-3-yl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=C(C=CC=1)S(C)(=O)=O)C1CCOC1 LXKDSMIFVYYJAC-UHFFFAOYSA-N 0.000 claims 1
- UJVOCVZJHMGNDD-IAXKEJLGSA-N 6,6-dimethyl-n-[1-[(s)-morpholin-2-yl(phenyl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1([C@@H](N2N=CC(=C2)NC(=O)C2=NNC3=C2CCC(C3)(C)C)C=2C=CC=CC=2)CNCCO1 UJVOCVZJHMGNDD-IAXKEJLGSA-N 0.000 claims 1
- NIYYTKSGRWRMSH-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(1,3-oxazol-2-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=NC=CO1 NIYYTKSGRWRMSH-UHFFFAOYSA-N 0.000 claims 1
- BIGQWWGFEYTQAB-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(1,3-thiazol-2-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=NC=CS1 BIGQWWGFEYTQAB-UHFFFAOYSA-N 0.000 claims 1
- CONJCHSVJHYERA-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(1,3-thiazol-4-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=CSC=N1 CONJCHSVJHYERA-UHFFFAOYSA-N 0.000 claims 1
- QCIKCBFQHBVZQW-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(1,3-thiazol-5-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=CN=CS1 QCIKCBFQHBVZQW-UHFFFAOYSA-N 0.000 claims 1
- NOEYOCSKBQIDIJ-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(1-methylpyrazol-4-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C=1C=NN(C)C=1 NOEYOCSKBQIDIJ-UHFFFAOYSA-N 0.000 claims 1
- QLTYLQZACKAOSX-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=NN=C(C)O1 QLTYLQZACKAOSX-UHFFFAOYSA-N 0.000 claims 1
- BFIGVZHTDCRWCX-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[1-(oxan-4-yl)ethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1CCOCC1 BFIGVZHTDCRWCX-UHFFFAOYSA-N 0.000 claims 1
- XUYMHBBOHOOBDR-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[2-(2-oxopyrrolidin-1-yl)-1-phenylethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)CN1CCCC1=O XUYMHBBOHOOBDR-UHFFFAOYSA-N 0.000 claims 1
- VYKWMYWGYDDQQL-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[2-(3-methyl-2-oxoimidazolidin-1-yl)-1-phenylethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound O=C1N(C)CCN1CC(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 VYKWMYWGYDDQQL-UHFFFAOYSA-N 0.000 claims 1
- VCGQMNXNXZUWMA-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[2-(3-oxomorpholin-4-yl)-1-phenylethyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)CN1CCOCC1=O VCGQMNXNXZUWMA-UHFFFAOYSA-N 0.000 claims 1
- GACUGHKGCWOZPW-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[3-(methylamino)-1-phenylpropyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CCNC)C1=CC=CC=C1 GACUGHKGCWOZPW-UHFFFAOYSA-N 0.000 claims 1
- STQQBHWTNZRIHV-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[3-[methyl(methylsulfonyl)amino]-1-phenylpropyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CCN(C)S(C)(=O)=O)C1=CC=CC=C1 STQQBHWTNZRIHV-UHFFFAOYSA-N 0.000 claims 1
- WWRFAPXORRNAFB-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[3-[methyl(oxetan-3-yl)amino]-1-phenylpropyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1OCC1N(C)CCC(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 WWRFAPXORRNAFB-UHFFFAOYSA-N 0.000 claims 1
- ZEAHUQGYVDWIML-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[oxan-4-yl(phenyl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CCOCC1 ZEAHUQGYVDWIML-UHFFFAOYSA-N 0.000 claims 1
- POQAFNUVBKCDJM-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[oxan-4-yl(pyridin-3-yl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=NC=CC=1)C1CCOCC1 POQAFNUVBKCDJM-UHFFFAOYSA-N 0.000 claims 1
- ILYQIAVPXLQYSF-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[phenyl(piperidin-4-yl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CCNCC1 ILYQIAVPXLQYSF-UHFFFAOYSA-N 0.000 claims 1
- AGUQEFAZNRJPNE-UHFFFAOYSA-N 6,6-dimethyl-n-[1-[thian-4-yl(1,3-thiazol-2-yl)methyl]pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1SC=CN=1)C1CCSCC1 AGUQEFAZNRJPNE-UHFFFAOYSA-N 0.000 claims 1
- CCIBZQOLDGJDQH-UHFFFAOYSA-N 6-cyano-6-methyl-N-[1-(1-pyridin-2-ylethyl)pyrazol-4-yl]-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C(#N)C1(CCC=2C(=NNC2C1)C(=O)NC=1C=NN(C1)C(C)C1=NC=CC=C1)C CCIBZQOLDGJDQH-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- PJEFXCIGUQFRIW-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-3,4,5,5a,6,6a-hexahydrocyclopropa[e]indazole-1-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2CCC3C(C12)C3 PJEFXCIGUQFRIW-UHFFFAOYSA-N 0.000 claims 1
- XJEZEQWBGAOABI-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-3,4-diazatricyclo[6.1.1.02,6]deca-2(6),4-diene-5-carboxamide Chemical compound N=1NC=2C(C3)CC3CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 XJEZEQWBGAOABI-UHFFFAOYSA-N 0.000 claims 1
- OKCPUKQECFOTAA-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-4,5-diazatricyclo[6.1.1.02,6]deca-2(6),3-diene-3-carboxamide Chemical compound N=1NC=2CC(C3)CC3C=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 OKCPUKQECFOTAA-UHFFFAOYSA-N 0.000 claims 1
- BMYKWBMPULIEKQ-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-4-methyl-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene-9-carboxamide Chemical compound C1C2(C)CC2C2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 BMYKWBMPULIEKQ-UHFFFAOYSA-N 0.000 claims 1
- BFRVPTUEMKMZQW-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-4-methyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxamide Chemical compound C1=2CC3(C)CC3C=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 BFRVPTUEMKMZQW-UHFFFAOYSA-N 0.000 claims 1
- PTAUUOJKBSTOTI-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-5a-methyl-4,5,6,6a-tetrahydro-1H-cyclopropa[g]indazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2C3C(CCC12)(C3)C PTAUUOJKBSTOTI-UHFFFAOYSA-N 0.000 claims 1
- ACTLMVHTAQBXLY-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-6-ethynyl-6-methyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2CC(CCC12)(C)C#C ACTLMVHTAQBXLY-UHFFFAOYSA-N 0.000 claims 1
- SJDFKEVJVPDPFT-UHFFFAOYSA-N N-(1-benzylpyrazol-4-yl)-6-methyl-6-morpholin-4-yl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2CC(CCC12)(N1CCOCC1)C SJDFKEVJVPDPFT-UHFFFAOYSA-N 0.000 claims 1
- HAUBNQSFKVXHKI-PVARCSIZSA-N N-[1-[(1S)-1-phenylpropyl]pyrazol-4-yl]-3,4,5,5a,6,6a-hexahydrocyclopropa[e]indazole-1-carboxamide Chemical compound C1(=CC=CC=C1)[C@H](CC)N1N=CC(=C1)NC(=O)C1=NNC=2CCC3C(C12)C3 HAUBNQSFKVXHKI-PVARCSIZSA-N 0.000 claims 1
- LGKBVWNCUCGFKN-UHFFFAOYSA-N N-[1-[(2-aminopyridin-4-yl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound NC1=NC=CC(=C1)CN1N=CC(=C1)NC(=O)C1=NNC=2CC(CCC12)(C)C LGKBVWNCUCGFKN-UHFFFAOYSA-N 0.000 claims 1
- GFUMZYSCYIBLKC-UHFFFAOYSA-N N-[1-[(3-fluoroazetidin-3-yl)-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound FC1(CNC1)C(N1N=CC(=C1)NC(=O)C1=NNC=2CC(CCC12)(C)C)C1=CC=CC=C1 GFUMZYSCYIBLKC-UHFFFAOYSA-N 0.000 claims 1
- ZUWLAULNDGZZCX-UHFFFAOYSA-N N-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indazole-3-carboxamide Chemical compound CN(CCC(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2CC3C(CC12)C3)C ZUWLAULNDGZZCX-UHFFFAOYSA-N 0.000 claims 1
- CZMAUPUNWICEAO-UHFFFAOYSA-N N-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]spiro[1,4,5,7-tetrahydroindazole-6,1'-cyclopropane]-3-carboxamide Chemical compound CN(CCC(C1=CC=CC=C1)N1N=CC(=C1)NC(=O)C1=NNC=2CC3(CC3)CCC12)C CZMAUPUNWICEAO-UHFFFAOYSA-N 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- OHGAJAWPYZELNO-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-1'-methyl-2'-oxospiro[1,4,5,7-tetrahydroindazole-6,3'-pyrrolidine]-3-carboxamide Chemical compound O=C1N(C)CCC11CC(NN=C2C(=O)NC3=CN(CC=4C=CC=CC=4)N=C3)=C2CC1 OHGAJAWPYZELNO-UHFFFAOYSA-N 0.000 claims 1
- SPABBLGEKOWLOG-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indazole-3-carboxamide Chemical compound N=1NC=2CC3CC3CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 SPABBLGEKOWLOG-UHFFFAOYSA-N 0.000 claims 1
- LDFWHPBGRCOZAQ-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide Chemical compound N=1NC=2CCCCCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 LDFWHPBGRCOZAQ-UHFFFAOYSA-N 0.000 claims 1
- SFQNMXFQDFOTAW-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-2'-oxospiro[1,4,5,7-tetrahydroindazole-6,1'-cyclopentane]-3-carboxamide Chemical compound N=1NC=2CC3(C(CCC3)=O)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 SFQNMXFQDFOTAW-UHFFFAOYSA-N 0.000 claims 1
- PCLGKHHZEIIYMO-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5'-oxospiro[1,4,5,7-tetrahydroindazole-6,2'-pyrrolidine]-3-carboxamide Chemical compound N=1NC=2CC3(NC(=O)CC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 PCLGKHHZEIIYMO-UHFFFAOYSA-N 0.000 claims 1
- LNVLOPALYJDPOM-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5,5-difluoro-1,4,6,7-tetrahydroindazole-3-carboxamide Chemical compound C1=2CC(F)(F)CCC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 LNVLOPALYJDPOM-UHFFFAOYSA-N 0.000 claims 1
- KWTDVQYZRZTJDG-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5,5-difluoro-5a-methyl-1,4,4a,6-tetrahydrocyclopropa[f]indazole-3-carboxamide Chemical compound C1=2CC(C3(F)F)C3(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 KWTDVQYZRZTJDG-UHFFFAOYSA-N 0.000 claims 1
- HRFBSHHNIMWMNO-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5,5-dimethyl-1,4,6,7-tetrahydroindazole-3-carboxamide Chemical compound C1=2CC(C)(C)CCC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 HRFBSHHNIMWMNO-UHFFFAOYSA-N 0.000 claims 1
- XEYYHIIUOPQQSR-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5,5-dimethyl-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound C1COC(C)(C)CC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 XEYYHIIUOPQQSR-UHFFFAOYSA-N 0.000 claims 1
- CRRPNPGNUNDKSO-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5,5-dimethyl-4,6-dihydro-1h-cyclopenta[c]pyrazole-3-carboxamide Chemical compound C1=2CC(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 CRRPNPGNUNDKSO-UHFFFAOYSA-N 0.000 claims 1
- HFDJVEOABAKWIF-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5-(hydroxymethyl)-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=2CC(CO)C(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 HFDJVEOABAKWIF-UHFFFAOYSA-N 0.000 claims 1
- LKIPENSELPRYRW-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5-cyano-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=2CC(C#N)C(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 LKIPENSELPRYRW-UHFFFAOYSA-N 0.000 claims 1
- FWXOSJGQGVYEPV-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5-hydroxy-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=2CC(O)C(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 FWXOSJGQGVYEPV-UHFFFAOYSA-N 0.000 claims 1
- PLSHXXFZMYTZHD-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5-methyl-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound C1=2CC(C)CCC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 PLSHXXFZMYTZHD-UHFFFAOYSA-N 0.000 claims 1
- CZAHTSYZRWGJOH-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-5a-methyl-4,4a,5,6-tetrahydro-1h-cyclopropa[f]indazole-3-carboxamide Chemical compound C1C2(C)CC2CC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 CZAHTSYZRWGJOH-UHFFFAOYSA-N 0.000 claims 1
- MEKYNOFETGQGRE-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6,6-difluoro-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(F)(F)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 MEKYNOFETGQGRE-UHFFFAOYSA-N 0.000 claims 1
- CMSVKLVKNBMOSI-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 CMSVKLVKNBMOSI-UHFFFAOYSA-N 0.000 claims 1
- QRRUPAAEUGALGR-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6-(hydroxymethyl)-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound C1C(CO)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 QRRUPAAEUGALGR-UHFFFAOYSA-N 0.000 claims 1
- SXIQTGHCRRJBCG-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6-(hydroxymethyl)-6-methyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(CO)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 SXIQTGHCRRJBCG-UHFFFAOYSA-N 0.000 claims 1
- MZQIGTONCACZFP-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6-cyano-6-methyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C#N)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 MZQIGTONCACZFP-UHFFFAOYSA-N 0.000 claims 1
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- QTGPFHRVNUSSMG-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6-methoxy-6-methyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(OC)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 QTGPFHRVNUSSMG-UHFFFAOYSA-N 0.000 claims 1
- DTMLASFEUYRUGI-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-6-methyl-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound C1C(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 DTMLASFEUYRUGI-UHFFFAOYSA-N 0.000 claims 1
- VFFKDTIEEFHDFN-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)-7,7-dimethyl-1,4,5,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound C1=2CCOC(C)(C)CC=2NN=C1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 VFFKDTIEEFHDFN-UHFFFAOYSA-N 0.000 claims 1
- STCNDRXGYAQSKS-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,5,7-tetrahydroindazole-6,1'-cyclopropane]-3-carboxamide Chemical compound N=1NC=2CC3(CC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 STCNDRXGYAQSKS-UHFFFAOYSA-N 0.000 claims 1
- ZUOPQTMTAPNAIK-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,5,7-tetrahydroindazole-6,2'-oxolane]-3-carboxamide Chemical compound N=1NC=2CC3(OCCC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 ZUOPQTMTAPNAIK-UHFFFAOYSA-N 0.000 claims 1
- RTZIZMCIJALUIE-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,5,7-tetrahydroindazole-6,3'-oxetane]-3-carboxamide Chemical compound N=1NC=2CC3(COC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 RTZIZMCIJALUIE-UHFFFAOYSA-N 0.000 claims 1
- DGTFAVKOOZFPJL-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,5,7-tetrahydroindazole-6,3'-oxolane]-3-carboxamide Chemical compound N=1NC=2CC3(COCC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 DGTFAVKOOZFPJL-UHFFFAOYSA-N 0.000 claims 1
- GTHSFCXOYQRRNR-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,5,7-tetrahydroindazole-6,3'-thietane]-3-carboxamide Chemical compound N=1NC=2CC3(CSC3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 GTHSFCXOYQRRNR-UHFFFAOYSA-N 0.000 claims 1
- PWHSNFDDYKFIGT-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[1,4,6,7-tetrahydroindazole-5,3'-oxetane]-3-carboxamide Chemical compound N=1NC=2CCC3(COC3)CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 PWHSNFDDYKFIGT-UHFFFAOYSA-N 0.000 claims 1
- XWGWITQJVBLBMW-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[4,6-dihydro-1h-cyclopenta[c]pyrazole-5,3'-oxetane]-3-carboxamide Chemical compound N=1NC=2CC3(COC3)CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 XWGWITQJVBLBMW-UHFFFAOYSA-N 0.000 claims 1
- STEOMDROILESOZ-UHFFFAOYSA-N n-(1-benzylpyrazol-4-yl)spiro[4,6-dihydro-1h-cyclopenta[c]pyrazole-5,3'-oxolane]-3-carboxamide Chemical compound N=1NC=2CC3(COCC3)CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC=C1 STEOMDROILESOZ-UHFFFAOYSA-N 0.000 claims 1
- NSYGGJLVOKBHDY-UHFFFAOYSA-N n-[1-(2-hydroxy-1-phenylethyl)pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CO)C1=CC=CC=C1 NSYGGJLVOKBHDY-UHFFFAOYSA-N 0.000 claims 1
- ZKMPHAWMBHQDBR-UHFFFAOYSA-N n-[1-(2-hydroxy-1-pyridin-3-ylethyl)pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CO)C1=CC=CN=C1 ZKMPHAWMBHQDBR-UHFFFAOYSA-N 0.000 claims 1
- QHKULHJHRSIBPG-UHFFFAOYSA-N n-[1-(2-hydroxy-2-methyl-1-phenylpropyl)pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C(C)(O)C)C1=CC=CC=C1 QHKULHJHRSIBPG-UHFFFAOYSA-N 0.000 claims 1
- UIFVFMQPPDLBFU-UHFFFAOYSA-N n-[1-(3-amino-1-phenylpropyl)pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CCN)C1=CC=CC=C1 UIFVFMQPPDLBFU-UHFFFAOYSA-N 0.000 claims 1
- LSVHNOXPQYWHQO-UHFFFAOYSA-N n-[1-(3-cyano-1-pyridin-3-ylpropyl)pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(CCC#N)C1=CC=CN=C1 LSVHNOXPQYWHQO-UHFFFAOYSA-N 0.000 claims 1
- XOQPGORGBSYSQC-UHFFFAOYSA-N n-[1-[(1,3-dimethyl-2-oxo-1,3-diazinan-5-yl)-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1N(C)C(=O)N(C)CC1C(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 XOQPGORGBSYSQC-UHFFFAOYSA-N 0.000 claims 1
- JEUBUUQJGLJDKQ-UHFFFAOYSA-N n-[1-[(1-acetylazetidin-3-yl)-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1N(C(=O)C)CC1C(N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1)C1=CC=CC=C1 JEUBUUQJGLJDKQ-UHFFFAOYSA-N 0.000 claims 1
- JHJRXGPGDSEWNC-UHFFFAOYSA-N n-[1-[(1-methylpyrazol-4-yl)-phenylmethyl]pyrazol-4-yl]-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indazole-3-carboxamide Chemical compound C1=NN(C)C=C1C(N1N=CC(NC(=O)C=2C=3CC4CC4CC=3NN=2)=C1)C1=CC=CC=C1 JHJRXGPGDSEWNC-UHFFFAOYSA-N 0.000 claims 1
- ROSFKGHTACMLTG-UHFFFAOYSA-N n-[1-[(1-methylpyrazol-4-yl)-phenylmethyl]pyrazol-4-yl]-3,4,5,5a,6,6a-hexahydrocyclopropa[e]indazole-1-carboxamide Chemical compound C1=NN(C)C=C1C(N1N=CC(NC(=O)C=2C=3C4CC4CCC=3NN=2)=C1)C1=CC=CC=C1 ROSFKGHTACMLTG-UHFFFAOYSA-N 0.000 claims 1
- MATYFMDTCOVGHR-ZOJXTTQQSA-N n-[1-[(1s)-1-phenylpropyl]pyrazol-4-yl]-1,4,4a,5,5a,6-hexahydrocyclopropa[f]indazole-3-carboxamide Chemical compound C1([C@H](CC)N2N=CC(NC(=O)C=3C=4CC5CC5CC=4NN=3)=C2)=CC=CC=C1 MATYFMDTCOVGHR-ZOJXTTQQSA-N 0.000 claims 1
- ULZGWUNLDDFEJJ-UHFFFAOYSA-N n-[1-[(2-aminopyridin-3-yl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CN=C1N ULZGWUNLDDFEJJ-UHFFFAOYSA-N 0.000 claims 1
- JBXDLDMVKCUMNW-UHFFFAOYSA-N n-[1-[(2-aminopyridin-4-yl)-(oxan-4-yl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=C(N)N=CC=1)C1CCOCC1 JBXDLDMVKCUMNW-UHFFFAOYSA-N 0.000 claims 1
- ZLCXWKGPVFCMNF-UHFFFAOYSA-N n-[1-[(3-chlorophenyl)-(oxan-4-yl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=C(Cl)C=CC=1)C1CCOCC1 ZLCXWKGPVFCMNF-UHFFFAOYSA-N 0.000 claims 1
- XJNPOZBJAFKRMY-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxamide Chemical compound N=1NC=2CCCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 XJNPOZBJAFKRMY-UHFFFAOYSA-N 0.000 claims 1
- VXUZVATZVGRSHS-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound N=1NC=2CCCCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 VXUZVATZVGRSHS-UHFFFAOYSA-N 0.000 claims 1
- NRJLSFKZAQFLCT-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-5-(1h-pyrazol-4-yl)-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound N=1NC=2CCC(C3=CNN=C3)CC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 NRJLSFKZAQFLCT-UHFFFAOYSA-N 0.000 claims 1
- GPDQRGLXYDGJIF-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-6-(1h-pyrazol-4-yl)-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound N=1NC=2CC(C3=CNN=C3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 GPDQRGLXYDGJIF-UHFFFAOYSA-N 0.000 claims 1
- YFXKQXQRMHZCJG-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-6-hydroxy-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound C1C(O)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 YFXKQXQRMHZCJG-UHFFFAOYSA-N 0.000 claims 1
- PMDWJWHRSTYSCR-UHFFFAOYSA-N n-[1-[(3-cyanophenyl)methyl]pyrazol-4-yl]-6-pyrimidin-5-yl-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound N=1NC=2CC(C=3C=NC=NC=3)CCC=2C=1C(=O)NC(=C1)C=NN1CC1=CC=CC(C#N)=C1 PMDWJWHRSTYSCR-UHFFFAOYSA-N 0.000 claims 1
- GVKVMWNOUNMKEX-UHFFFAOYSA-N n-[1-[(4-fluoropiperidin-4-yl)-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C1(F)CCNCC1)C1=CC=CC=C1 GVKVMWNOUNMKEX-UHFFFAOYSA-N 0.000 claims 1
- TVZMTJMOHLFIQK-UHFFFAOYSA-N n-[1-[1-(1-ethylpyrazol-4-yl)ethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=NN(CC)C=C1C(C)N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1 TVZMTJMOHLFIQK-UHFFFAOYSA-N 0.000 claims 1
- FJJGGWOSIIYTEA-UHFFFAOYSA-N n-[1-[1-(1-ethylpyrazol-4-yl)propyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CC)C=1C=NN(CC)C=1 FJJGGWOSIIYTEA-UHFFFAOYSA-N 0.000 claims 1
- STAIDRZITDIYCV-UHFFFAOYSA-N n-[1-[1-(5-fluoropyridin-3-yl)ethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(C)C1=CN=CC(F)=C1 STAIDRZITDIYCV-UHFFFAOYSA-N 0.000 claims 1
- DGAUNAIKKKXLFY-UHFFFAOYSA-N n-[1-[1-(6-methoxypyridin-3-yl)ethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(C)N1N=CC(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)=C1 DGAUNAIKKKXLFY-UHFFFAOYSA-N 0.000 claims 1
- GQXYNDIEHVQPDF-UHFFFAOYSA-N n-[1-[2-(azetidin-1-yl)-1-phenylethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)CN1CCC1 GQXYNDIEHVQPDF-UHFFFAOYSA-N 0.000 claims 1
- CKEGCZYMKAQMGU-UHFFFAOYSA-N n-[1-[2-(dimethylamino)-1-phenylethyl]pyrazol-4-yl]-5,5-dimethyl-4,6-dihydro-1h-cyclopenta[c]pyrazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CC(C)(C)CC=3NN=2)C=NN1C(CN(C)C)C1=CC=CC=C1 CKEGCZYMKAQMGU-UHFFFAOYSA-N 0.000 claims 1
- COBZZNVRTKQJFM-UHFFFAOYSA-N n-[1-[2-(dimethylamino)-1-phenylethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CN(C)C)C1=CC=CC=C1 COBZZNVRTKQJFM-UHFFFAOYSA-N 0.000 claims 1
- FHZRNUWRVITWDX-UHFFFAOYSA-N n-[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=NN(CCN(C)C)C=C1NC(=O)C1=NNC2=C1CCC(C)(C)C2 FHZRNUWRVITWDX-UHFFFAOYSA-N 0.000 claims 1
- GRBBUAPOZVJFMU-UHFFFAOYSA-N n-[1-[3-(3,3-difluoroazetidin-1-yl)-1-phenylpropyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)CCN1CC(F)(F)C1 GRBBUAPOZVJFMU-UHFFFAOYSA-N 0.000 claims 1
- IXJCBGOCROYMTK-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-(3-methylphenyl)propyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC(C)=C1 IXJCBGOCROYMTK-UHFFFAOYSA-N 0.000 claims 1
- JDYYDIODSDBUOO-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]propyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC(C(F)(F)F)=C1 JDYYDIODSDBUOO-UHFFFAOYSA-N 0.000 claims 1
- VUXWPPSAMPSGCH-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]-3,4,5,5a,6,6a-hexahydrocyclopropa[e]indazole-1-carboxamide Chemical compound C1=C(NC(=O)C=2C=3C4CC4CCC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC=C1 VUXWPPSAMPSGCH-UHFFFAOYSA-N 0.000 claims 1
- XFYUTGIEFKGWND-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC(C)(C)CC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC=C1 XFYUTGIEFKGWND-UHFFFAOYSA-N 0.000 claims 1
- JKFXNYLMKPQAFE-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]spiro[1,4,5,7-tetrahydroindazole-6,2'-oxolane]-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC4(OCCC4)CC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC=C1 JKFXNYLMKPQAFE-UHFFFAOYSA-N 0.000 claims 1
- LLDRMROKRCHQLF-UHFFFAOYSA-N n-[1-[3-(dimethylamino)-1-phenylpropyl]pyrazol-4-yl]spiro[1,4,5,7-tetrahydroindazole-6,3'-oxetane]-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=3CCC4(COC4)CC=3NN=2)C=NN1C(CCN(C)C)C1=CC=CC=C1 LLDRMROKRCHQLF-UHFFFAOYSA-N 0.000 claims 1
- SDIIYFQWCHUACH-UHFFFAOYSA-N n-[1-[[1-(2-fluoroethyl)azetidin-3-yl]-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CN(CCF)C1 SDIIYFQWCHUACH-UHFFFAOYSA-N 0.000 claims 1
- LSCNJMXUVMRNQD-UHFFFAOYSA-N n-[1-[[1-(2-fluoroethyl)piperidin-4-yl]-phenylmethyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CCN(CCF)CC1 LSCNJMXUVMRNQD-UHFFFAOYSA-N 0.000 claims 1
- AMTOVEXVNJFBNC-UHFFFAOYSA-N n-[1-[azetidin-3-yl(phenyl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=CC=CC=1)C1CNC1 AMTOVEXVNJFBNC-UHFFFAOYSA-N 0.000 claims 1
- YMIDLTLPGNYKHR-UHFFFAOYSA-N n-[1-[azetidin-3-yl-(3-methylphenyl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound CC1=CC=CC(C(C2CNC2)N2N=CC(NC(=O)C=3C=4CCC(C)(C)CC=4NN=3)=C2)=C1 YMIDLTLPGNYKHR-UHFFFAOYSA-N 0.000 claims 1
- YETMXNSCOAHUNE-UHFFFAOYSA-N n-[1-[cyclopropyl-(3-methylsulfonylphenyl)methyl]pyrazol-4-yl]-6,6-dimethyl-1,4,5,7-tetrahydroindazole-3-carboxamide Chemical compound C1C(C)(C)CCC2=C1NN=C2C(=O)NC(=C1)C=NN1C(C=1C=C(C=CC=1)S(C)(=O)=O)C1CC1 YETMXNSCOAHUNE-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 CC(C(*)c1c(C2*=C)[n]nc1C1OC1Nc1c[n](**)nc1)C2C=C Chemical compound CC(C(*)c1c(C2*=C)[n]nc1C1OC1Nc1c[n](**)nc1)C2C=C 0.000 description 1
Applications Claiming Priority (7)
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| US201261682063P | 2012-08-10 | 2012-08-10 | |
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| US61/764,434 | 2013-02-13 | ||
| US201361764930P | 2013-02-14 | 2013-02-14 | |
| US61/764,930 | 2013-02-14 | ||
| PCT/CN2013/081136 WO2014023258A1 (en) | 2012-08-10 | 2013-08-09 | Pyrazole carboxamide compounds, compositions and methods of use |
Publications (2)
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| JP2015528435A JP2015528435A (ja) | 2015-09-28 |
| JP2015528435A5 true JP2015528435A5 (https=) | 2016-06-30 |
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| US (2) | US20150158851A1 (https=) |
| EP (1) | EP2882718A4 (https=) |
| JP (1) | JP2015528435A (https=) |
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| CN (1) | CN104781238A (https=) |
| AR (1) | AR092088A1 (https=) |
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| RU (1) | RU2015106013A (https=) |
| TW (1) | TW201410654A (https=) |
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| GB201706102D0 (en) * | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| WO2019195810A2 (en) * | 2018-04-06 | 2019-10-10 | Praxis Biotech LLC | Atf6 inhibitors and uses thereof |
| MX2022007518A (es) | 2019-12-20 | 2022-09-19 | Pfizer | Derivados bencimidazol. |
| US20250002489A1 (en) * | 2021-10-19 | 2025-01-02 | Nurix Therapeutics, Inc. | Bifunctional compounds for degrading itk via ubiquitin proteosome pathway |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| BR0113697A (pt) * | 2000-09-06 | 2003-07-22 | Neurogen Corp | Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, uso de um composto ou sal, embalagem e métodos para, para alterar a atividade transdutora de sinal dos receptores de gabaa, para tratar ansiedade, depressão, um distúrbio do sono, ou demência de alzheimer, para demonstrar a presença dos receptores de gabaa em células ou amostras de tecido e para preparar um composto |
| WO2003037900A2 (en) * | 2001-11-01 | 2003-05-08 | Icagen, Inc. | Pyrazolopyrimidines |
| BR0307504A (pt) * | 2002-02-07 | 2004-12-07 | Neurogen Corp | Composto ou sal farmaceuticamente aceitável, composição farmacêutica, métodos tratar doenças, para potencializar um efeito terapêutico de um agente para o snc, para melhorar a memória de curto prazo em um paciente, para determinar a presença ou ausência de receptores gabaa em uma amostra, e para alterar a atividade transdutora de sinal do receptor gabaa, embalagem, e, uso de um composto ou sal |
| FR2845382A1 (fr) * | 2002-10-02 | 2004-04-09 | Sanofi Synthelabo | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| EP1960382A1 (en) * | 2005-11-03 | 2008-08-27 | ChemBridge Research Laboratories, Inc. | Heterocyclic compounds as tyrosine kinase modulators |
| UA110324C2 (en) * | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| US9073926B2 (en) * | 2009-12-07 | 2015-07-07 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds containing a pyrrolopyridine or benzimidazole core |
| AU2011329233A1 (en) * | 2010-11-15 | 2013-05-23 | Abbvie Deutschland Gmbh & Co Kg | NAMPT and ROCK inhibitors |
| CN103889976A (zh) * | 2011-08-12 | 2014-06-25 | 弗·哈夫曼-拉罗切有限公司 | 吲唑化合物、组合物及使用方法 |
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2013
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- 2013-08-09 TW TW102128696A patent/TW201410654A/zh unknown
- 2013-08-09 BR BR112015002938A patent/BR112015002938A2/pt not_active Application Discontinuation
- 2013-08-09 JP JP2015525727A patent/JP2015528435A/ja active Pending
- 2013-08-09 EP EP13827574.8A patent/EP2882718A4/en not_active Withdrawn
- 2013-08-09 CA CA2880232A patent/CA2880232A1/en not_active Abandoned
- 2013-08-09 WO PCT/CN2013/081136 patent/WO2014023258A1/en not_active Ceased
- 2013-08-09 MX MX2015001864A patent/MX2015001864A/es unknown
- 2013-08-09 CN CN201380049541.7A patent/CN104781238A/zh active Pending
- 2013-08-09 HK HK16100276.7A patent/HK1212344A1/xx unknown
- 2013-08-09 KR KR1020157006025A patent/KR20150041651A/ko not_active Abandoned
- 2013-08-09 AR ARP130102838A patent/AR092088A1/es unknown
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2015
- 2015-02-10 US US14/618,827 patent/US20150158851A1/en not_active Abandoned
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2016
- 2016-05-11 US US15/152,212 patent/US20160326142A1/en not_active Abandoned
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