JP2017512794A5 - - Google Patents
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- Publication number
- JP2017512794A5 JP2017512794A5 JP2016559249A JP2016559249A JP2017512794A5 JP 2017512794 A5 JP2017512794 A5 JP 2017512794A5 JP 2016559249 A JP2016559249 A JP 2016559249A JP 2016559249 A JP2016559249 A JP 2016559249A JP 2017512794 A5 JP2017512794 A5 JP 2017512794A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- trifluoromethyl
- benzamide
- pyrazole
- fluoro
- 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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- -1 tetrahydronaphthyridinyl Chemical group 0.000 claims 346
- 125000000623 heterocyclic group Chemical group 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 102000015336 Nerve Growth Factor Human genes 0.000 claims 4
- 108010025020 Nerve Growth Factor Proteins 0.000 claims 4
- 229940053128 nerve growth factor Drugs 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000016192 Demyelinating disease Diseases 0.000 claims 2
- 206010012305 Demyelination Diseases 0.000 claims 2
- 206010067601 Dysmyelination Diseases 0.000 claims 2
- IOORZMBILFXYQY-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)CC(=O)O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)CC(=O)O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C IOORZMBILFXYQY-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 101150111783 NTRK1 gene Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NDGNKOKRFUFATL-UHFFFAOYSA-N 6-[5-[[2-fluoro-5-(1H-pyrazol-5-yl)-4-(trifluoromethyl)benzoyl]amino]-6-phenylpyridin-3-yl]-N-methylpyridine-3-carboxamide Chemical compound FC1=C(C(=O)NC=2C=C(C=NC2C2=CC=CC=C2)C2=NC=C(C=C2)C(=O)NC)C=C(C(=C1)C(F)(F)F)C1=NNC=C1 NDGNKOKRFUFATL-UHFFFAOYSA-N 0.000 claims 1
- GNBROKXSIMUYMP-UHFFFAOYSA-N C(C)(=O)N1CC=2C=C(C(=NC2CC1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NC=CC=N1)C(F)(F)F)F)=O Chemical compound C(C)(=O)N1CC=2C=C(C(=NC2CC1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NC=CC=N1)C(F)(F)F)F)=O GNBROKXSIMUYMP-UHFFFAOYSA-N 0.000 claims 1
- AEAGEILBJIDBFR-UHFFFAOYSA-N C(C)(=O)NCC1=NC=C(C(=N1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NNC=C1)C(F)(F)F)F)=O Chemical compound C(C)(=O)NCC1=NC=C(C(=N1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NNC=C1)C(F)(F)F)F)=O AEAGEILBJIDBFR-UHFFFAOYSA-N 0.000 claims 1
- FVJAUCAVHYAINU-UHFFFAOYSA-N C(C)(=O)NCC=1C=NC(=NC=1)C=1C=C(C(=NC=1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NC=CC=N1)C(F)(F)F)F)=O Chemical compound C(C)(=O)NCC=1C=NC(=NC=1)C=1C=C(C(=NC=1)C1=CC=CC=C1)NC(C1=C(C=C(C(=C1)C1=NC=CC=N1)C(F)(F)F)F)=O FVJAUCAVHYAINU-UHFFFAOYSA-N 0.000 claims 1
- JHJRTSFXFZTQBX-UHFFFAOYSA-N CC(=O)N1CCC2=NC(=C(NC(=O)C3=CC(C4=NC=CC=N4)=C(C=C3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 Chemical compound CC(=O)N1CCC2=NC(=C(NC(=O)C3=CC(C4=NC=CC=N4)=C(C=C3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 JHJRTSFXFZTQBX-UHFFFAOYSA-N 0.000 claims 1
- PSZAYWQTGPVGTP-UHFFFAOYSA-N CN1C=CC(=N1)C1=C(C=CC(=C1)C(=O)NC1=C(N=C2CCN(CC(O)=O)CC2=C1)C1=CC=CC=C1)C(F)(F)F Chemical compound CN1C=CC(=N1)C1=C(C=CC(=C1)C(=O)NC1=C(N=C2CCN(CC(O)=O)CC2=C1)C1=CC=CC=C1)C(F)(F)F PSZAYWQTGPVGTP-UHFFFAOYSA-N 0.000 claims 1
- XXAZNUDCXFTURA-UHFFFAOYSA-N CN1C=CC(=N1)C1=CC(C(=O)NC2=C(N=C3CCN(CC3=C2)C(N)=O)C2=CC=CC=C2)=C(F)C=C1C(F)(F)F Chemical compound CN1C=CC(=N1)C1=CC(C(=O)NC2=C(N=C3CCN(CC3=C2)C(N)=O)C2=CC=CC=C2)=C(F)C=C1C(F)(F)F XXAZNUDCXFTURA-UHFFFAOYSA-N 0.000 claims 1
- ATLNHWLHOWOCPK-UHFFFAOYSA-N CN1N=C(C=C1)C=1C=C(C=CC1C(F)(F)F)C(=O)NC=1C=C(C=NC1C1=CC=CC=C1)C(=O)N Chemical compound CN1N=C(C=C1)C=1C=C(C=CC1C(F)(F)F)C(=O)NC=1C=C(C=NC1C1=CC=CC=C1)C(=O)N ATLNHWLHOWOCPK-UHFFFAOYSA-N 0.000 claims 1
- YRZMKDCYKMJIOW-UHFFFAOYSA-N CNC(=O)N1CCC2=NC(=C(NC(=O)C3=C(F)C=C(C(=C3)C3=NC=CC=N3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 Chemical compound CNC(=O)N1CCC2=NC(=C(NC(=O)C3=C(F)C=C(C(=C3)C3=NC=CC=N3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 YRZMKDCYKMJIOW-UHFFFAOYSA-N 0.000 claims 1
- ARQMJVYNILTACL-UHFFFAOYSA-N CS(=O)(=O)N1CCC2=NC(=C(NC(=O)C3=C(F)C=C(C(=C3)C3=NC=CC=N3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 Chemical compound CS(=O)(=O)N1CCC2=NC(=C(NC(=O)C3=C(F)C=C(C(=C3)C3=NC=CC=N3)C(F)(F)F)C=C2C1)C1=CC=CC=C1 ARQMJVYNILTACL-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RJWTUKDPJFFNLD-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)C(C(=O)O)(C)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)C(C(=O)O)(C)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C RJWTUKDPJFFNLD-UHFFFAOYSA-N 0.000 claims 1
- NDKZGTKXNHDWAO-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NC=CC=N1 Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NC=CC=N1 NDKZGTKXNHDWAO-UHFFFAOYSA-N 0.000 claims 1
- ZANJVJFOGFOABD-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1OC(CC1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1OC(CC1)C ZANJVJFOGFOABD-UHFFFAOYSA-N 0.000 claims 1
- LBNDRHGWPOXBLZ-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=CC(=C1F)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)C)C2=CC=CC=C2)C=CC(=C1F)C LBNDRHGWPOXBLZ-UHFFFAOYSA-N 0.000 claims 1
- WSEWGTPRJVCSCN-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)CN2C(CCCC2)=O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)CN2C(CCCC2)=O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C WSEWGTPRJVCSCN-UHFFFAOYSA-N 0.000 claims 1
- KAHBJSTXGJGOJC-UHFFFAOYSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)CN2C(NCC2)=O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)CN2C(NCC2)=O)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C KAHBJSTXGJGOJC-UHFFFAOYSA-N 0.000 claims 1
- NQENVZQSBBRBTK-QHCPKHFHSA-N FC1=C(C(=O)NC=2C(=NC(=NC2)CNC(=O)[C@H]2NCCOC2)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C Chemical compound FC1=C(C(=O)NC=2C(=NC(=NC2)CNC(=O)[C@H]2NCCOC2)C2=CC=CC=C2)C=C(C(=C1)C(F)(F)F)C1=NN(C=C1)C NQENVZQSBBRBTK-QHCPKHFHSA-N 0.000 claims 1
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| CN108794414B (zh) * | 2018-06-22 | 2021-01-01 | 浙江大学 | 芳酰胺基取代的均三嗪类化合物及制备和应用 |
| CN108997224B (zh) * | 2018-08-28 | 2023-04-28 | 韶远科技（上海)有限公司 | 一种2-氯-5-氰基含氮六元杂环化合物的制备方法 |
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- 2015-03-23 BR BR112016022069A patent/BR112016022069A2/pt not_active Application Discontinuation
- 2015-03-23 JP JP2016559249A patent/JP2017512794A/ja active Pending
- 2015-03-23 KR KR1020167029501A patent/KR20160128420A/ko not_active Withdrawn
- 2015-03-23 CA CA2943858A patent/CA2943858A1/en not_active Abandoned
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