JP2017508763A5

JP2017508763A5 -

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Publication number: JP2017508763A5
Authority: JP; Japan
Prior art keywords: pyridin; carboxamide; indazole; ylmethyl; piperidin
Prior art date: 2015-03-20
Legal status : Granted

Application number

JP2016558073A

Other languages

English (en)

Japanese (ja)

Other versions

JP2017508763A (ja

JP6586104B2 (ja

Filing date

2015-03-20

Publication date

2018-05-10

2015-03-20 Application filed filed Critical

2015-03-20 Priority claimed from PCT/US2015/021847 external-priority patent/WO2015143380A1/en

2017-03-30 Publication of JP2017508763A publication Critical patent/JP2017508763A/ja

2018-05-10 Publication of JP2017508763A5 publication Critical patent/JP2017508763A5/ja

2019-10-02 Application granted granted Critical

2019-10-02 Publication of JP6586104B2 publication Critical patent/JP6586104B2/ja

Status Active legal-status Critical Current

2035-03-20 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims description 367
-1 40 Chemical compound 0.000 claims description 166
125000001424 substituent group Chemical group 0.000 claims description 158
150000004820 halides Chemical class 0.000 claims description 146
125000000623 heterocyclic group Chemical group 0.000 claims description 142
125000003118 aryl group Chemical group 0.000 claims description 94
150000001875 compounds Chemical class 0.000 claims description 67
MUJCJYXCJZCTGK-YLJYHZDGSA-N O=C(N[C@@H]1C[C@@H]1C1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound O=C(N[C@@H]1C[C@@H]1C1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 MUJCJYXCJZCTGK-YLJYHZDGSA-N 0.000 claims description 53
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
229910052757 nitrogen Inorganic materials 0.000 claims description 42
BZOFNZCOJLNGRM-UHFFFAOYSA-N CN(C)CC1=CN=CC(=C1)C1=CC2=C(NN=C2C(=O)NC2(CC2)C2=CC=CC=C2)C=C1 Chemical compound CN(C)CC1=CN=CC(=C1)C1=CC2=C(NN=C2C(=O)NC2(CC2)C2=CC=CC=C2)C=C1 BZOFNZCOJLNGRM-UHFFFAOYSA-N 0.000 claims description 40
URLNZXIOSFZUTM-UHFFFAOYSA-N FC(F)(F)C1=CC(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC=CN=C2)=NC=C1 Chemical compound FC(F)(F)C1=CC(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC=CN=C2)=NC=C1 URLNZXIOSFZUTM-UHFFFAOYSA-N 0.000 claims description 40
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
125000004452 carbocyclyl group Chemical group 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 29
KDILLWUWCNHGSF-UHFFFAOYSA-N FC1=CC(CNC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(F)=CC(CN3CCCCC3)=C2)=CC(F)=C1 Chemical compound FC1=CC(CNC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(F)=CC(CN3CCCCC3)=C2)=CC(F)=C1 KDILLWUWCNHGSF-UHFFFAOYSA-N 0.000 claims description 28
ZGKMMVQSJWEOIZ-UHFFFAOYSA-N FC1(F)CCN(CC2=CN=CC(=C2)C2=CC3=C(NN=C3C(=O)NC3(CC3)C3=CC=CC=C3)C=C2)C1 Chemical compound FC1(F)CCN(CC2=CN=CC(=C2)C2=CC3=C(NN=C3C(=O)NC3(CC3)C3=CC=CC=C3)C=C2)C1 ZGKMMVQSJWEOIZ-UHFFFAOYSA-N 0.000 claims description 26
125000001072 heteroaryl group Chemical group 0.000 claims description 26
125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
GUZUCDBAKLABBD-UHFFFAOYSA-N CC(C)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound CC(C)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 GUZUCDBAKLABBD-UHFFFAOYSA-N 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 23
201000010099 disease Diseases 0.000 claims description 22
208000035475 disorder Diseases 0.000 claims description 21
JPDZJTQRSPOKQM-UHFFFAOYSA-N FC(F)(F)C1=CN=C(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCC3)=CN=C2)C=C1 Chemical compound FC(F)(F)C1=CN=C(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCC3)=CN=C2)C=C1 JPDZJTQRSPOKQM-UHFFFAOYSA-N 0.000 claims description 20
NCWBNLBKELXOEL-UHFFFAOYSA-N CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCC2)=CN=C1 Chemical compound CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCC2)=CN=C1 NCWBNLBKELXOEL-UHFFFAOYSA-N 0.000 claims description 18
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QBICVULYPZHONS-UHFFFAOYSA-N FC1=CC(CN2CCCCC2)=CC(=C1)C1=CC2=C(NN=C2C(=O)NC2CC2)C=C1 Chemical compound FC1=CC(CN2CCCCC2)=CC(=C1)C1=CC2=C(NN=C2C(=O)NC2CC2)C=C1 QBICVULYPZHONS-UHFFFAOYSA-N 0.000 claims description 16
NCGCGIIOFAPBDI-UHFFFAOYSA-N O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 NCGCGIIOFAPBDI-UHFFFAOYSA-N 0.000 claims description 16
OUIZONDSSAUAJU-UHFFFAOYSA-N O=C(NC1CC2=CC=CC=C2C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCC2)=CN=C1 Chemical compound O=C(NC1CC2=CC=CC=C2C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCC2)=CN=C1 OUIZONDSSAUAJU-UHFFFAOYSA-N 0.000 claims description 15
VKCGOSIANKZDIT-UHFFFAOYSA-N O=C(NC1CCOCC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound O=C(NC1CCOCC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 VKCGOSIANKZDIT-UHFFFAOYSA-N 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
LIXXQBRPVXEVJX-UHFFFAOYSA-N CC1=CN=CC(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCC3)=CN=C2)=C1 Chemical compound CC1=CN=CC(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCC3)=CN=C2)=C1 LIXXQBRPVXEVJX-UHFFFAOYSA-N 0.000 claims description 12
SRHQFOACTVSFJA-UHFFFAOYSA-N CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 SRHQFOACTVSFJA-UHFFFAOYSA-N 0.000 claims description 12
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
USOXYAQJCZZVAQ-UHFFFAOYSA-N O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 Chemical compound O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 USOXYAQJCZZVAQ-UHFFFAOYSA-N 0.000 claims description 11
RLDCHLUXJJZGRL-UHFFFAOYSA-N O=C(NCC1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 Chemical compound O=C(NCC1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 RLDCHLUXJJZGRL-UHFFFAOYSA-N 0.000 claims description 11
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
BLBHPRNNBWUXDY-UHFFFAOYSA-N CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=C(F)C(F)=CC=C1 Chemical compound CN1CCC(CC1)NC(=O)C1=NNC2=C1C=C(C=C2)C1=C(F)C(F)=CC=C1 BLBHPRNNBWUXDY-UHFFFAOYSA-N 0.000 claims description 10
KNUGXANPSAQNIA-UHFFFAOYSA-N FC1=CC(CN2CCCCC2)=CC(=C1)C1=CC2=C(NN=C2C(=O)NCC2=CC=CC=C2)C=C1 Chemical compound FC1=CC(CN2CCCCC2)=CC(=C1)C1=CC2=C(NN=C2C(=O)NCC2=CC=CC=C2)C=C1 KNUGXANPSAQNIA-UHFFFAOYSA-N 0.000 claims description 10
150000003857 carboxamides Chemical class 0.000 claims description 10
HVEOEVJLUUUHNZ-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-5-[5-(piperidin-1-ylmethyl)pyridin-3-yl]-1h-indazole-3-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=NNC2=CC=C(C=3C=C(CN4CCCCC4)C=NC=3)C=C12 HVEOEVJLUUUHNZ-UHFFFAOYSA-N 0.000 claims description 10
208000011580 syndromic disease Diseases 0.000 claims description 10
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KAVIAEXRPPAATG-UHFFFAOYSA-N CC1CCN(CC2=CN=CC(=C2)C2=CC3=C(NN=C3C(=O)NC3=CC=C(N=C3)N3CC(F)(F)C3)C=C2)CC1 Chemical compound CC1CCN(CC2=CN=CC(=C2)C2=CC3=C(NN=C3C(=O)NC3=CC=C(N=C3)N3CC(F)(F)C3)C=C2)CC1 KAVIAEXRPPAATG-UHFFFAOYSA-N 0.000 claims description 8
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WIMYCASGDIOWFC-UHFFFAOYSA-N FC1(F)CN(C1)C1=CC=C(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCCC3)=CN=C2)C=N1 Chemical compound FC1(F)CN(C1)C1=CC=C(NC(=O)C2=NNC3=C2C=C(C=C3)C2=CC(CN3CCCCCC3)=CN=C2)C=N1 WIMYCASGDIOWFC-UHFFFAOYSA-N 0.000 claims description 8
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ARFXMLYKZKPYTI-UHFFFAOYSA-N O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCC2)=CN=C1 Chemical compound O=C(NC1CC1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCC2)=CN=C1 ARFXMLYKZKPYTI-UHFFFAOYSA-N 0.000 claims description 8
OKUXQHPECQJHNG-UHFFFAOYSA-N O=C(NC1CCCCC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 Chemical compound O=C(NC1CCCCC1)C1=NNC2=C1C=C(C=C2)C1=CC=CN=C1 OKUXQHPECQJHNG-UHFFFAOYSA-N 0.000 claims description 8
IRPXEKYAMSRCMG-ZEQKJWHPSA-N O=C(N[C@@H]1C[C@@H]1C1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 Chemical compound O=C(N[C@@H]1C[C@@H]1C1=CC=CC=C1)C1=NNC2=C1C=C(C=C2)C1=CC(CN2CCCCC2)=CN=C1 IRPXEKYAMSRCMG-ZEQKJWHPSA-N 0.000 claims description 8
RPSADMWPPVLGTD-UHFFFAOYSA-N 5-[5-(piperidin-1-ylmethyl)pyridin-3-yl]-n-pyridin-2-yl-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C=3C=C(CN4CCCCC4)C=NC=3)C=C2C=1C(=O)NC1=CC=CC=N1 RPSADMWPPVLGTD-UHFFFAOYSA-N 0.000 claims description 7
NEERNGSOLFEXCN-UHFFFAOYSA-N 5-[5-(pyrrolidin-1-ylmethyl)pyridin-3-yl]-n-(6-pyrrolidin-1-ylpyridin-3-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C=3C=C(CN4CCCC4)C=NC=3)C=C2C=1C(=O)NC(C=N1)=CC=C1N1CCCC1 NEERNGSOLFEXCN-UHFFFAOYSA-N 0.000 claims description 7
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JP2016558073A 2014-03-20 2015-03-20 ５−置換インダゾール−３−カルボキサミドならびにその調製および使用の方法 Active JP6586104B2 (ja)