JP2014527511A - Trpm8拮抗剤及び治療におけるそれらの使用 - Google Patents
Trpm8拮抗剤及び治療におけるそれらの使用 Download PDFInfo
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- JP2014527511A JP2014527511A JP2014517168A JP2014517168A JP2014527511A JP 2014527511 A JP2014527511 A JP 2014527511A JP 2014517168 A JP2014517168 A JP 2014517168A JP 2014517168 A JP2014517168 A JP 2014517168A JP 2014527511 A JP2014527511 A JP 2014527511A
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- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- trifluoromethyl
- pyridin
- 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.)
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- 239000005557 antagonist Substances 0.000 title abstract description 5
- 102000003610 TRPM8 Human genes 0.000 title abstract 3
- 101150111302 Trpm8 gene Proteins 0.000 title abstract 3
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 336
- 208000004296 neuralgia Diseases 0.000 claims abstract description 52
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 32
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- 206010027599 migraine Diseases 0.000 claims abstract description 26
- 229940079593 drug Drugs 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 376
- 150000003839 salts Chemical class 0.000 claims description 367
- 239000000203 mixture Substances 0.000 claims description 333
- -1 oxadiazolonyl Chemical group 0.000 claims description 184
- 229920006395 saturated elastomer Polymers 0.000 claims description 110
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 125000005843 halogen group Chemical group 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 52
- 208000004454 Hyperalgesia Diseases 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 230000002757 inflammatory effect Effects 0.000 claims description 46
- 208000002193 Pain Diseases 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 35
- 125000004043 oxo group Chemical group O=* 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 230000002792 vascular Effects 0.000 claims description 27
- 206010053552 allodynia Diseases 0.000 claims description 24
- 206010065390 Inflammatory pain Diseases 0.000 claims description 23
- 208000035154 Hyperesthesia Diseases 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 208000011580 syndromic disease Diseases 0.000 claims description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
- 230000036407 pain Effects 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
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- 125000002619 bicyclic group Chemical group 0.000 claims description 13
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- 206010012735 Diarrhoea Diseases 0.000 claims description 10
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 10
- 230000002889 sympathetic effect Effects 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- 230000001771 impaired effect Effects 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 8
- VQOWLYUIIHGMNV-FQEVSTJZSA-N n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC=N2)C2=C1 VQOWLYUIIHGMNV-FQEVSTJZSA-N 0.000 claims description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- ODUSZXFCJHEXBU-SFHVURJKSA-N 2-oxo-n-[(s)-pyridin-2-yl-[4-(trifluoromethoxy)phenyl]methyl]-3h-1,3-benzoxazole-5-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1[C@@H](C=1N=CC=CC=1)NC(=O)C1=CC=C(OC(=O)N2)C2=C1 ODUSZXFCJHEXBU-SFHVURJKSA-N 0.000 claims description 6
- QEBYISWYMFIXOZ-INIZCTEOSA-N 6-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 QEBYISWYMFIXOZ-INIZCTEOSA-N 0.000 claims description 6
- FHDVDXXLSCUTNI-INIZCTEOSA-N 6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 FHDVDXXLSCUTNI-INIZCTEOSA-N 0.000 claims description 6
- XXJIZSMSQIOOJK-KRWDZBQOSA-N 6-oxo-n-[(s)-pyridin-2-yl-[4-(trifluoromethoxy)phenyl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1[C@@H](C=1N=CC=CC=1)NC(=O)C1=CNC(=O)C=C1 XXJIZSMSQIOOJK-KRWDZBQOSA-N 0.000 claims description 6
- 206010028851 Necrosis Diseases 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 210000004204 blood vessel Anatomy 0.000 claims description 6
- XKOBBYARBOFGES-SFHVURJKSA-N n-[(s)-(2-fluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 XKOBBYARBOFGES-SFHVURJKSA-N 0.000 claims description 6
- KZJHWEJVIDNHJM-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 KZJHWEJVIDNHJM-INIZCTEOSA-N 0.000 claims description 6
- UDOMJNZQWLGPMB-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 UDOMJNZQWLGPMB-INIZCTEOSA-N 0.000 claims description 6
- QAZDWNMMNRMJOG-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(NC(=O)C2)C2=C1 QAZDWNMMNRMJOG-IBGZPJMESA-N 0.000 claims description 6
- LUAULFMJAXGGPA-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 LUAULFMJAXGGPA-INIZCTEOSA-N 0.000 claims description 6
- OTXZQFZKKCWTGZ-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 OTXZQFZKKCWTGZ-KRWDZBQOSA-N 0.000 claims description 6
- IJTSMWHYNKDXNG-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 IJTSMWHYNKDXNG-INIZCTEOSA-N 0.000 claims description 6
- ZCQCYFZVMCAXRY-IBGZPJMESA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-pyridin-2-ylmethyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3N=CNC3=CC=2)C=2N=CC=CC=2)=C1 ZCQCYFZVMCAXRY-IBGZPJMESA-N 0.000 claims description 6
- GHJSBAUYVRHTKX-KRWDZBQOSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-pyridin-2-ylmethyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C2=CNC(=O)C=C2)C=2N=CC=CC=2)=C1 GHJSBAUYVRHTKX-KRWDZBQOSA-N 0.000 claims description 6
- 230000017074 necrotic cell death Effects 0.000 claims description 6
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000000552 rheumatic effect Effects 0.000 claims description 6
- HEZZUCRUSGBFJH-SFHVURJKSA-N 1-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-2,3-dihydroisoindole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C(=O)NC2)C2=C1 HEZZUCRUSGBFJH-SFHVURJKSA-N 0.000 claims description 5
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- WFBSFIDRLBBQMO-INIZCTEOSA-N 6-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 WFBSFIDRLBBQMO-INIZCTEOSA-N 0.000 claims description 5
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- RCIICRRQCUOTQX-SFHVURJKSA-N 2-methyl-1,3-dioxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]isoindole-5-carboxamide Chemical compound C1([C@H](NC(=O)C2=CC=C3C(=O)N(C(C3=C2)=O)C)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 RCIICRRQCUOTQX-SFHVURJKSA-N 0.000 claims description 4
- GFHPJASOKWOTSI-AWEZNQCLSA-N 2-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyrimidine-5-carboxamide Chemical compound C1=NC(O)=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 GFHPJASOKWOTSI-AWEZNQCLSA-N 0.000 claims description 4
- PREKQNRJOBFOPL-SFHVURJKSA-N 3-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,2-dihydroisoindole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(CNC2=O)C2=C1 PREKQNRJOBFOPL-SFHVURJKSA-N 0.000 claims description 4
- QMXZSQMCZBUEQM-HNNXBMFYSA-N 5-bromo-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C(Br)=C1 QMXZSQMCZBUEQM-HNNXBMFYSA-N 0.000 claims description 4
- NPQYDTVEJXZHIY-INIZCTEOSA-N 5-bromo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(Br)C=N1 NPQYDTVEJXZHIY-INIZCTEOSA-N 0.000 claims description 4
- RSARLQRUEFGCIV-INIZCTEOSA-N 5-cyano-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C(C#N)=C1 RSARLQRUEFGCIV-INIZCTEOSA-N 0.000 claims description 4
- HVPAWWKPTMDJEM-HNNXBMFYSA-N 5-fluoro-n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C(F)=C1 HVPAWWKPTMDJEM-HNNXBMFYSA-N 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- XSDZJNCGYWWAOV-IBGZPJMESA-N [2-amino-4-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl] acetate Chemical compound C1=C(N)C(OC(=O)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 XSDZJNCGYWWAOV-IBGZPJMESA-N 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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- KVEOTVDCHOSVKD-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-1h-[1,3]oxazolo[5,4-b]pyridine-5-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(NC(=O)O2)C2=N1 KVEOTVDCHOSVKD-HNNXBMFYSA-N 0.000 claims description 4
- UDOMESTYOFAYAU-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-3h-[1,3]oxazolo[4,5-b]pyridine-5-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(OC(=O)N2)C2=N1 UDOMESTYOFAYAU-HNNXBMFYSA-N 0.000 claims description 4
- LTGWPRHIHYEKSH-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-3h-[1,3]oxazolo[4,5-b]pyridine-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CN=C(NC(=O)O2)C2=C1 LTGWPRHIHYEKSH-HNNXBMFYSA-N 0.000 claims description 4
- HVMMEAKWXIYCSQ-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(OC(=O)N2)C2=C1 HVMMEAKWXIYCSQ-KRWDZBQOSA-N 0.000 claims description 4
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- YTRTYNWYHOJNPM-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-5-hydroxypyridine-2-carboxamide Chemical compound N1=CC(O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 YTRTYNWYHOJNPM-INIZCTEOSA-N 0.000 claims description 4
- CFQOPFUUIWPJGH-INIZCTEOSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C2=CNC(=O)C=C2)C=2C(=CC=CN=2)C(F)(F)F)=C1 CFQOPFUUIWPJGH-INIZCTEOSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- YMNAJWHTELQUJU-UHFFFAOYSA-N quinoline-6-carboxamide Chemical compound N1=CC=CC2=CC(C(=O)N)=CC=C21 YMNAJWHTELQUJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- KXZFNTIQRXCMQT-FQEVSTJZSA-N 1,3-dioxo-2-propyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]isoindole-5-carboxamide Chemical compound C1([C@H](NC(=O)C2=CC=C3C(=O)N(C(C3=C2)=O)CCC)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 KXZFNTIQRXCMQT-FQEVSTJZSA-N 0.000 claims description 3
- DGICAGJGZMEEHI-SFHVURJKSA-N 2-[6-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]carbamoyl]pyridin-3-yl]oxyacetic acid Chemical compound N1=CC(OCC(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 DGICAGJGZMEEHI-SFHVURJKSA-N 0.000 claims description 3
- OZOMHVGZHYTLQX-HNNXBMFYSA-N 2-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 OZOMHVGZHYTLQX-HNNXBMFYSA-N 0.000 claims description 3
- PMXDTJIHYSMSFG-IBGZPJMESA-N 3-pyridin-2-yl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CCC1=CC=CC=N1 PMXDTJIHYSMSFG-IBGZPJMESA-N 0.000 claims description 3
- FXZCBPORQDEBAL-KRWDZBQOSA-N 4-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 FXZCBPORQDEBAL-KRWDZBQOSA-N 0.000 claims description 3
- BZPJHUMUPYZDQX-KRWDZBQOSA-N 5-cyano-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C#N)C=N1 BZPJHUMUPYZDQX-KRWDZBQOSA-N 0.000 claims description 3
- DAALNGYIAVZYSD-SFHVURJKSA-N 6-(dimethylamino)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 DAALNGYIAVZYSD-SFHVURJKSA-N 0.000 claims description 3
- QEBYISWYMFIXOZ-MRXNPFEDSA-N 6-[[(r)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C(=O)N[C@@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 QEBYISWYMFIXOZ-MRXNPFEDSA-N 0.000 claims description 3
- BDPRYHIGFCOXIA-INIZCTEOSA-N 6-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C=C1 BDPRYHIGFCOXIA-INIZCTEOSA-N 0.000 claims description 3
- MNWACGOJPRBIHK-INIZCTEOSA-N 6-chloro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(Cl)N=C1 MNWACGOJPRBIHK-INIZCTEOSA-N 0.000 claims description 3
- AEVSUIGFTMEVLP-FQEVSTJZSA-N 6-oxo-n-[(s)-(3-propylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1h-pyridine-3-carboxamide Chemical compound CCCC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 AEVSUIGFTMEVLP-FQEVSTJZSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- XGVGZKKUNSGABP-KRWDZBQOSA-N methyl 6-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 XGVGZKKUNSGABP-KRWDZBQOSA-N 0.000 claims description 3
- UWFCEGYMDAHSLN-FQEVSTJZSA-N n-[(s)-(3-bromopyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]quinoline-7-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)Br)NC(=O)C1=CC=C(C=CC=N2)C2=C1 UWFCEGYMDAHSLN-FQEVSTJZSA-N 0.000 claims description 3
- POICLAZZODVADD-IBGZPJMESA-N n-[(s)-(3-ethenylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C=C)NC(=O)C1=CNC(=O)C=C1 POICLAZZODVADD-IBGZPJMESA-N 0.000 claims description 3
- KSMUVTWLHNWGEC-IBGZPJMESA-N n-[(s)-(3-ethylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CCC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 KSMUVTWLHNWGEC-IBGZPJMESA-N 0.000 claims description 3
- NHXXGLJGGBDKQC-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-hydroxy-4-methyl-2,3-dioxoquinoxaline-6-carboxamide Chemical compound C1([C@H](NC(=O)C=2C=C3N(C(C(=O)N(O)C3=CC=2)=O)C)C=2C(=CC=CN=2)F)=CC=C(OC(F)(F)F)C(F)=C1 NHXXGLJGGBDKQC-SFHVURJKSA-N 0.000 claims description 3
- UULYUZDWOPRLRG-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]imidazo[1,2-a]pyridine-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CN2C=CN=C2C=C1 UULYUZDWOPRLRG-SFHVURJKSA-N 0.000 claims description 3
- IFQNMPDIUQRLQY-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-methoxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 IFQNMPDIUQRLQY-HNNXBMFYSA-N 0.000 claims description 3
- DMABRZKWOQQPOT-FQEVSTJZSA-N n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,2,3,4-tetrahydroquinoline-7-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(CCCN2)C2=C1 DMABRZKWOQQPOT-FQEVSTJZSA-N 0.000 claims description 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- BZUMXQIRVWAAME-CABCVRRESA-N (2r)-n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]oxolane-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)[C@@H]2OCCC2)C=2C(=CC=CN=2)C(F)(F)F)=C1 BZUMXQIRVWAAME-CABCVRRESA-N 0.000 claims description 2
- BZUMXQIRVWAAME-GJZGRUSLSA-N (2s)-n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]oxolane-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)[C@H]2OCCC2)C=2C(=CC=CN=2)C(F)(F)F)=C1 BZUMXQIRVWAAME-GJZGRUSLSA-N 0.000 claims description 2
- WLSSMJSWJWRFLK-GJZGRUSLSA-N (2s)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]oxolane-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)[C@H]1OCCC1 WLSSMJSWJWRFLK-GJZGRUSLSA-N 0.000 claims description 2
- NJQRAAHKQQPUIT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CNC1 NJQRAAHKQQPUIT-UHFFFAOYSA-N 0.000 claims description 2
- GTWMFGTZKVNMMD-QFIPXVFZSA-N 1,3-dioxo-2-pyridin-2-yl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]isoindole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C(=O)N(C2=O)C=3N=CC=CC=3)C2=C1 GTWMFGTZKVNMMD-QFIPXVFZSA-N 0.000 claims description 2
- HWCSPJDWYHAYQP-KRWDZBQOSA-N 1,3-dioxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]isoindole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C(=O)NC2=O)C2=C1 HWCSPJDWYHAYQP-KRWDZBQOSA-N 0.000 claims description 2
- DITJMBBTMRSDOP-INIZCTEOSA-N 1-(difluoromethyl)-n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C(F)F)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 DITJMBBTMRSDOP-INIZCTEOSA-N 0.000 claims description 2
- MSCFTHLFIJPMLH-INIZCTEOSA-N 1-(difluoromethyl)-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C(F)F)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 MSCFTHLFIJPMLH-INIZCTEOSA-N 0.000 claims description 2
- NNYRGXUWCPLNNG-QHCPKHFHSA-N 1-benzyl-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CN(CC=2C=CC=CC=2)C(=O)C=C1 NNYRGXUWCPLNNG-QHCPKHFHSA-N 0.000 claims description 2
- HRYZPYQXQXXRFE-SFHVURJKSA-N 1-ethyl-n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 HRYZPYQXQXXRFE-SFHVURJKSA-N 0.000 claims description 2
- SXDHJUZNRLFNIJ-SFHVURJKSA-N 1-ethyl-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C=C1 SXDHJUZNRLFNIJ-SFHVURJKSA-N 0.000 claims description 2
- SKWGBPVQURSZAL-SFHVURJKSA-N 1-ethyl-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 SKWGBPVQURSZAL-SFHVURJKSA-N 0.000 claims description 2
- BZJXIMVTUPZQJD-KRWDZBQOSA-N 1-methyl-2-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-4-carboxamide Chemical compound O=C1N(C)C=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 BZJXIMVTUPZQJD-KRWDZBQOSA-N 0.000 claims description 2
- LLFPBXHJLZVJME-KRWDZBQOSA-N 1-methyl-6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 LLFPBXHJLZVJME-KRWDZBQOSA-N 0.000 claims description 2
- GUQYHFUJPXNOGL-SFHVURJKSA-N 1-methyl-6-oxo-n-[(s)-pyridin-2-yl-[4-(trifluoromethoxy)phenyl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C=C1C(=O)N[C@H](C=1N=CC=CC=1)C1=CC=C(OC(F)(F)F)C=C1 GUQYHFUJPXNOGL-SFHVURJKSA-N 0.000 claims description 2
- JADUTIBUHKHILF-IBGZPJMESA-N 1-methyl-n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CN(C)C(=O)C=C1 JADUTIBUHKHILF-IBGZPJMESA-N 0.000 claims description 2
- JUTYIQGGTKKZOQ-IBGZPJMESA-N 1-methyl-n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CN(C)C(=O)C=C1 JUTYIQGGTKKZOQ-IBGZPJMESA-N 0.000 claims description 2
- YIIJDKBHXAEZDY-AWEZNQCLSA-N 1-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]imidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 YIIJDKBHXAEZDY-AWEZNQCLSA-N 0.000 claims description 2
- OLCYOCCVXTYEIN-SFHVURJKSA-N 1-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]indazole-3-carboxamide Chemical compound C1([C@H](NC(=O)C2=NN(C3=CC=CC=C32)C)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 OLCYOCCVXTYEIN-SFHVURJKSA-N 0.000 claims description 2
- LJCCZDCZQWTFBK-HNNXBMFYSA-N 1-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=N1 LJCCZDCZQWTFBK-HNNXBMFYSA-N 0.000 claims description 2
- SATOBHVAZUERBJ-UHFFFAOYSA-N 2,3-dihydro-1h-indole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NCCC2=C1 SATOBHVAZUERBJ-UHFFFAOYSA-N 0.000 claims description 2
- MCZOAPSTTZIFQS-UHFFFAOYSA-N 2,3-dihydro-1h-indole-6-carboxamide Chemical compound NC(=O)C1=CC=C2CCNC2=C1 MCZOAPSTTZIFQS-UHFFFAOYSA-N 0.000 claims description 2
- ZKIGRDFMYJDXFE-INIZCTEOSA-N 2-(1h-imidazol-5-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CC1=CNC=N1 ZKIGRDFMYJDXFE-INIZCTEOSA-N 0.000 claims description 2
- DISXCSVSNYYVNN-KRWDZBQOSA-N 2-(2-methylimidazol-1-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound CC1=NC=CN1CC(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 DISXCSVSNYYVNN-KRWDZBQOSA-N 0.000 claims description 2
- QIWHUENADNQDHQ-HNNXBMFYSA-N 2-(2-oxo-1,3-oxazolidin-3-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CN1C(=O)OCC1 QIWHUENADNQDHQ-HNNXBMFYSA-N 0.000 claims description 2
- CHELIFKYUMYASP-KRWDZBQOSA-N 2-(5-methylpyrazol-1-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound CC1=CC=NN1CC(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 CHELIFKYUMYASP-KRWDZBQOSA-N 0.000 claims description 2
- SLAPTPLFRFOPGT-TYJDENFWSA-N 2-(oxolan-3-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CC1COCC1 SLAPTPLFRFOPGT-TYJDENFWSA-N 0.000 claims description 2
- CRPNRUTYMYVOFC-IBGZPJMESA-N 2-[2-(trifluoromethoxy)phenyl]-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound FC(F)(F)OC1=CC=CC=C1CC(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 CRPNRUTYMYVOFC-IBGZPJMESA-N 0.000 claims description 2
- BQGRATCBLFJVPM-SFHVURJKSA-N 2-[5-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]carbamoyl]-2-oxopyridin-1-yl]acetic acid Chemical compound C1=CC(=O)N(CC(=O)O)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 BQGRATCBLFJVPM-SFHVURJKSA-N 0.000 claims description 2
- AWNADXZCVQVUCJ-WRXSAAJRSA-N 2-acetamido-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound C1([C@H](NC(=O)C(NC(C)=O)C)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 AWNADXZCVQVUCJ-WRXSAAJRSA-N 0.000 claims description 2
- NOZMMOKTSFFPPV-ZDUSSCGKSA-N 2-amino-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,3-thiazole-4-carboxamide Chemical compound S1C(N)=NC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 NOZMMOKTSFFPPV-ZDUSSCGKSA-N 0.000 claims description 2
- UBFAYAHYVJSPFW-KRWDZBQOSA-N 2-bromo-4-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]benzoic acid Chemical compound C1=C(Br)C(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 UBFAYAHYVJSPFW-KRWDZBQOSA-N 0.000 claims description 2
- SFGIWQFQWGXULR-SFHVURJKSA-N 2-cyano-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC=C1C#N SFGIWQFQWGXULR-SFHVURJKSA-N 0.000 claims description 2
- QFZOHQWBKADJMP-INIZCTEOSA-N 2-imidazol-1-yl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CN1C=NC=C1 QFZOHQWBKADJMP-INIZCTEOSA-N 0.000 claims description 2
- QBLJHVJTOGZNES-KRWDZBQOSA-N 2-iodo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC=C1I QBLJHVJTOGZNES-KRWDZBQOSA-N 0.000 claims description 2
- POEMFCURBJBPTB-AWEZNQCLSA-N 2-methoxy-2-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound C1([C@H](NC(=O)C(C)(C)OC)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 POEMFCURBJBPTB-AWEZNQCLSA-N 0.000 claims description 2
- FEQKQUXSRDUAIQ-SFHVURJKSA-N 2-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 FEQKQUXSRDUAIQ-SFHVURJKSA-N 0.000 claims description 2
- NVLMOJHKXGWZNO-INIZCTEOSA-N 2-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 NVLMOJHKXGWZNO-INIZCTEOSA-N 0.000 claims description 2
- ZXJDGEVHTFHDPG-KRWDZBQOSA-N 2-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-4-carboxamide Chemical compound C1=NC(C)=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 ZXJDGEVHTFHDPG-KRWDZBQOSA-N 0.000 claims description 2
- AWYJXIKQDBAMJW-INIZCTEOSA-N 2-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrimidine-5-carboxamide Chemical compound C1=NC(C)=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 AWYJXIKQDBAMJW-INIZCTEOSA-N 0.000 claims description 2
- WHWGSEHDZDQIPJ-KRWDZBQOSA-N 2-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-5-n-methylpyridine-2,5-dicarboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 WHWGSEHDZDQIPJ-KRWDZBQOSA-N 0.000 claims description 2
- VBSDWUXCRNXSHL-INIZCTEOSA-N 2-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]pyridine-2,5-dicarboxamide Chemical compound N1=CC(C(=O)N)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 VBSDWUXCRNXSHL-INIZCTEOSA-N 0.000 claims description 2
- YXCNMJQLMQBTGB-HNNXBMFYSA-N 2-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CNC1=O YXCNMJQLMQBTGB-HNNXBMFYSA-N 0.000 claims description 2
- YRWUMEGIDWTGBS-INIZCTEOSA-N 2-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridine-4-carboxamide Chemical compound C1=NC(O)=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 YRWUMEGIDWTGBS-INIZCTEOSA-N 0.000 claims description 2
- TYZITLNTZTXYLV-SFHVURJKSA-N 2-oxo-n-[(s)-pyridin-2-yl-[4-(trifluoromethyl)phenyl]methyl]-3h-1,3-benzoxazole-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1N=CC=CC=1)NC(=O)C1=CC=C(OC(=O)N2)C2=C1 TYZITLNTZTXYLV-SFHVURJKSA-N 0.000 claims description 2
- QFJAJJQHWZMCTL-IBGZPJMESA-N 2-phenyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CC1=CC=CC=C1 QFJAJJQHWZMCTL-IBGZPJMESA-N 0.000 claims description 2
- HEKRWBHOEXBBON-SFHVURJKSA-N 2-pyridin-3-yl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)CC1=CC=CN=C1 HEKRWBHOEXBBON-SFHVURJKSA-N 0.000 claims description 2
- VSBGKKVABBAFNB-YMXDCFFPSA-N 3,3,3-trifluoro-2-methoxy-2-phenyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound C1([C@H](NC(=O)C(OC)(C=2C=CC=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 VSBGKKVABBAFNB-YMXDCFFPSA-N 0.000 claims description 2
- FHRJSKZHDYBNDU-SFHVURJKSA-N 3-(4-methyl-1,3-thiazol-5-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound N1=CSC(CCC(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1C FHRJSKZHDYBNDU-SFHVURJKSA-N 0.000 claims description 2
- OPNUZVJQAUWWKV-IBGZPJMESA-N 3-(dimethylamino)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound CN(C)C1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 OPNUZVJQAUWWKV-IBGZPJMESA-N 0.000 claims description 2
- UNSODDYOLNOQHS-KRWDZBQOSA-N 3-(trifluoromethoxy)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound FC(F)(F)OC1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 UNSODDYOLNOQHS-KRWDZBQOSA-N 0.000 claims description 2
- FLVOWMHIEASMDE-KRWDZBQOSA-N 3-(trifluoromethyl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC(C(F)(F)F)=C1 FLVOWMHIEASMDE-KRWDZBQOSA-N 0.000 claims description 2
- PKUAPGNIOAWLLS-KRWDZBQOSA-N 3-[[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)F)=C1 PKUAPGNIOAWLLS-KRWDZBQOSA-N 0.000 claims description 2
- FSDDDQBZQAALTI-NSHDSACASA-N 3-amino-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-1,2,4-triazole-5-carboxamide Chemical compound NC1=NNC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=N1 FSDDDQBZQAALTI-NSHDSACASA-N 0.000 claims description 2
- HLIZUCLDLCGQQK-HNNXBMFYSA-N 3-amino-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound NC1=CC=CN=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 HLIZUCLDLCGQQK-HNNXBMFYSA-N 0.000 claims description 2
- QFIRSOWQXYBJDR-INIZCTEOSA-N 3-amino-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-4-carboxamide Chemical compound NC1=CN=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 QFIRSOWQXYBJDR-INIZCTEOSA-N 0.000 claims description 2
- DJVCJHUNJBZWHL-QHCPKHFHSA-N 3-benzoyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DJVCJHUNJBZWHL-QHCPKHFHSA-N 0.000 claims description 2
- LZXCDEXJCMOQHI-KRWDZBQOSA-N 3-chloro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC(Cl)=C1 LZXCDEXJCMOQHI-KRWDZBQOSA-N 0.000 claims description 2
- OAPFTHJXXNOKLO-SFHVURJKSA-N 3-cyano-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=CC(C#N)=C1 OAPFTHJXXNOKLO-SFHVURJKSA-N 0.000 claims description 2
- HPFZQUGXNNQYDJ-UHFFFAOYSA-N 3-fluoro-n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC(C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)F)=C1 HPFZQUGXNNQYDJ-UHFFFAOYSA-N 0.000 claims description 2
- HPFZQUGXNNQYDJ-KRWDZBQOSA-N 3-fluoro-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)F)=C1 HPFZQUGXNNQYDJ-KRWDZBQOSA-N 0.000 claims description 2
- HXQDIWGWQQDSEF-KRWDZBQOSA-N 3-fluoro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound FC1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 HXQDIWGWQQDSEF-KRWDZBQOSA-N 0.000 claims description 2
- ZLCUPHHZKPKYBM-KRWDZBQOSA-N 3-iodo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC(I)=C1 ZLCUPHHZKPKYBM-KRWDZBQOSA-N 0.000 claims description 2
- TYXMKILHUSLSMH-SFHVURJKSA-N 3-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 TYXMKILHUSLSMH-SFHVURJKSA-N 0.000 claims description 2
- OMSCYKYOOQIIAP-HNNXBMFYSA-N 3-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]propanamide Chemical compound C1([C@H](NC(=O)CCOC)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 OMSCYKYOOQIIAP-HNNXBMFYSA-N 0.000 claims description 2
- XKIYTXYLTXNPOV-KRWDZBQOSA-N 3-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-4-carboxamide Chemical compound COC1=CN=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 XKIYTXYLTXNPOV-KRWDZBQOSA-N 0.000 claims description 2
- LZPIKKGAAWAGNH-FQEVSTJZSA-N 3-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,2-dihydroindene-5-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(CCC2=O)C2=C1 LZPIKKGAAWAGNH-FQEVSTJZSA-N 0.000 claims description 2
- UPOWIHDSVLTKRT-RUINGEJQSA-N 3-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]cyclohexane-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1CC(=O)CCC1 UPOWIHDSVLTKRT-RUINGEJQSA-N 0.000 claims description 2
- YCOBFDXHOZSBLN-IBGZPJMESA-N 4-(2-hydroxypropan-2-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 YCOBFDXHOZSBLN-IBGZPJMESA-N 0.000 claims description 2
- HFDONCKSCOGCIK-KRWDZBQOSA-N 4-(2h-tetrazol-5-yl)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C=2NN=NN=2)C=C1 HFDONCKSCOGCIK-KRWDZBQOSA-N 0.000 claims description 2
- KJKKUBKHZCDGLS-IBGZPJMESA-N 4-(dimethylamino)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 KJKKUBKHZCDGLS-IBGZPJMESA-N 0.000 claims description 2
- RCTDEUQWHDHPPS-KRWDZBQOSA-N 4-(trifluoromethoxy)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 RCTDEUQWHDHPPS-KRWDZBQOSA-N 0.000 claims description 2
- BNOWMCGRHMSAQE-KRWDZBQOSA-N 4-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 BNOWMCGRHMSAQE-KRWDZBQOSA-N 0.000 claims description 2
- SRYXTFOOKCVNML-KVULBXGLSA-N 4-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 SRYXTFOOKCVNML-KVULBXGLSA-N 0.000 claims description 2
- BLYBYCMUBNOAGB-IBGZPJMESA-N 4-acetamido-n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-3-hydroxybenzamide Chemical compound C1=C(O)C(NC(=O)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 BLYBYCMUBNOAGB-IBGZPJMESA-N 0.000 claims description 2
- XTDFEKNGLLLRJC-HNNXBMFYSA-N 4-amino-2-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrimidine-5-carboxamide Chemical compound NC1=NC(C)=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 XTDFEKNGLLLRJC-HNNXBMFYSA-N 0.000 claims description 2
- JJOXZTPSWQOQPI-KRWDZBQOSA-N 4-chloro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(Cl)C=C1 JJOXZTPSWQOQPI-KRWDZBQOSA-N 0.000 claims description 2
- IFWPHGPYFYLKKF-FQEVSTJZSA-N 4-chloro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-6-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(N=CC=C2Cl)C2=C1 IFWPHGPYFYLKKF-FQEVSTJZSA-N 0.000 claims description 2
- YIVCUUMZNIIQKB-FQEVSTJZSA-N 4-chloro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C(Cl)=CC=N2)C2=C1 YIVCUUMZNIIQKB-FQEVSTJZSA-N 0.000 claims description 2
- BDIOIDGNEIPNFL-UHFFFAOYSA-N 4-cyano-n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CN=C1C(C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C#N)C=C1 BDIOIDGNEIPNFL-UHFFFAOYSA-N 0.000 claims description 2
- BDIOIDGNEIPNFL-SFHVURJKSA-N 4-cyano-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C#N)C=C1 BDIOIDGNEIPNFL-SFHVURJKSA-N 0.000 claims description 2
- ZTQJAXODDVWNCC-SFHVURJKSA-N 4-cyano-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C#N)C=C1 ZTQJAXODDVWNCC-SFHVURJKSA-N 0.000 claims description 2
- OPLJTFDQWXGYNN-KRWDZBQOSA-N 4-fluoro-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 OPLJTFDQWXGYNN-KRWDZBQOSA-N 0.000 claims description 2
- QQCHVKTVDYSQPF-PGEKIEPBSA-N 4-hydroxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]cyclohexane-1-carboxamide Chemical compound C1CC(O)CCC1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 QQCHVKTVDYSQPF-PGEKIEPBSA-N 0.000 claims description 2
- LLWJXGXGWIKFNL-SFHVURJKSA-N 4-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 LLWJXGXGWIKFNL-SFHVURJKSA-N 0.000 claims description 2
- BVTBDKTVEWTWHA-KRWDZBQOSA-N 4-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound COC1=CC=NC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 BVTBDKTVEWTWHA-KRWDZBQOSA-N 0.000 claims description 2
- OKIFPOICHLAXOR-KRWDZBQOSA-N 4-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound COC1=CC=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 OKIFPOICHLAXOR-KRWDZBQOSA-N 0.000 claims description 2
- MOKVEFADUQNSGG-AWEZNQCLSA-N 4-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,3-oxazole-5-carboxamide Chemical compound N1=COC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1C MOKVEFADUQNSGG-AWEZNQCLSA-N 0.000 claims description 2
- OPTSEYPOBLHSAK-INIZCTEOSA-N 4-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrimidine-5-carboxamide Chemical compound CC1=NC=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 OPTSEYPOBLHSAK-INIZCTEOSA-N 0.000 claims description 2
- DKJLSOMIKDSXNQ-INIZCTEOSA-N 4-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridine-2-carboxamide Chemical compound OC1=CC=NC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 DKJLSOMIKDSXNQ-INIZCTEOSA-N 0.000 claims description 2
- ANFLAPICPKPMAP-FQEVSTJZSA-N 4-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-quinoline-6-carboxamide Chemical compound C1([C@H](NC(=O)C2=CC=C3N=CC=C(C3=C2)O)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 ANFLAPICPKPMAP-FQEVSTJZSA-N 0.000 claims description 2
- JJVFPOOMRIYWKC-FQEVSTJZSA-N 4-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-quinoline-7-carboxamide Chemical compound C1([C@H](NC(=O)C=2C=C3N=CC=C(C3=CC=2)O)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C(F)(F)F)C=C1 JJVFPOOMRIYWKC-FQEVSTJZSA-N 0.000 claims description 2
- AYXXABHYVVPPPA-FQEVSTJZSA-N 4-propan-2-yl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(C(C)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 AYXXABHYVVPPPA-FQEVSTJZSA-N 0.000 claims description 2
- HHHXTJLWQHICOT-INIZCTEOSA-N 5-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 HHHXTJLWQHICOT-INIZCTEOSA-N 0.000 claims description 2
- KBUYCLXMLOZIAA-HNNXBMFYSA-N 5-bromo-6-chloro-n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CN=C(Cl)C(Br)=C1 KBUYCLXMLOZIAA-HNNXBMFYSA-N 0.000 claims description 2
- DHSBHFRVQWEFJH-INIZCTEOSA-N 5-hydroxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound OC1=CN=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 DHSBHFRVQWEFJH-INIZCTEOSA-N 0.000 claims description 2
- LBMFXTXUXLSAHP-KRWDZBQOSA-N 5-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 LBMFXTXUXLSAHP-KRWDZBQOSA-N 0.000 claims description 2
- WPAJSVUFCVRTMI-KRWDZBQOSA-N 5-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound COC1=CN=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 WPAJSVUFCVRTMI-KRWDZBQOSA-N 0.000 claims description 2
- DQMPZRWRJNKSIY-KRWDZBQOSA-N 5-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound CC1=CN=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 DQMPZRWRJNKSIY-KRWDZBQOSA-N 0.000 claims description 2
- AYHCVNLMEHUSOM-MHTVFEQDSA-N 5-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrrolidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1CC(=O)NC1 AYHCVNLMEHUSOM-MHTVFEQDSA-N 0.000 claims description 2
- KMGYPOWQLCDZTG-SFHVURJKSA-N 6-(ethylamino)-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(NCC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 KMGYPOWQLCDZTG-SFHVURJKSA-N 0.000 claims description 2
- BIGVZFDXRGJOHN-NTISSMGPSA-N 6-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]pyridine-2-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C1=CC=CC(C(=O)N[C@@H](C=2C=C(F)C(OC(F)(F)F)=CC=2)C=2C(=CC=CN=2)F)=N1 BIGVZFDXRGJOHN-NTISSMGPSA-N 0.000 claims description 2
- IBKJTCAKTVORBE-INIZCTEOSA-N 6-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 IBKJTCAKTVORBE-INIZCTEOSA-N 0.000 claims description 2
- GTQATQHEDPCCOE-SFHVURJKSA-N 6-acetamido-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(NC(=O)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 GTQATQHEDPCCOE-SFHVURJKSA-N 0.000 claims description 2
- WBKPDKSJAONCAQ-INIZCTEOSA-N 6-amino-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(N)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 WBKPDKSJAONCAQ-INIZCTEOSA-N 0.000 claims description 2
- OSJCKOSIKSAPNJ-KRWDZBQOSA-N 6-cyano-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C#N)N=C1 OSJCKOSIKSAPNJ-KRWDZBQOSA-N 0.000 claims description 2
- IUIQPSISHPGMKO-INIZCTEOSA-N 6-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridazine-3-carboxamide Chemical compound N1=NC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 IUIQPSISHPGMKO-INIZCTEOSA-N 0.000 claims description 2
- UILGYADRGCMENZ-KRWDZBQOSA-N 6-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-2-carboxamide Chemical compound COC1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=N1 UILGYADRGCMENZ-KRWDZBQOSA-N 0.000 claims description 2
- OOCHUFGLVITKLT-KRWDZBQOSA-N 6-methoxy-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 OOCHUFGLVITKLT-KRWDZBQOSA-N 0.000 claims description 2
- WWVGGYAVSSJGER-KRWDZBQOSA-N 6-methyl-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]pyridine-3-carboxamide Chemical compound C1=NC(C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 WWVGGYAVSSJGER-KRWDZBQOSA-N 0.000 claims description 2
- SJNAAFJQHINDBO-HNNXBMFYSA-N 6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridazine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=NNC(=O)C=C1 SJNAAFJQHINDBO-HNNXBMFYSA-N 0.000 claims description 2
- SUZQOQMRFUNGMA-INIZCTEOSA-N 6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyridine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC(=O)N1 SUZQOQMRFUNGMA-INIZCTEOSA-N 0.000 claims description 2
- FUCMOMRLRFVRTF-AWEZNQCLSA-N 6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1h-pyrimidine-5-carboxamide Chemical compound OC1=NC=NC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 FUCMOMRLRFVRTF-AWEZNQCLSA-N 0.000 claims description 2
- NVNHSPGPBZPXKC-INSVYWFGSA-N 6-oxo-n-[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]piperidine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1CNC(=O)CC1 NVNHSPGPBZPXKC-INSVYWFGSA-N 0.000 claims description 2
- IFQPPSJDRNBIKT-KRWDZBQOSA-N 6-oxo-n-[(s)-pyridin-2-yl-[4-(trifluoromethyl)phenyl]methyl]-1h-pyridine-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1[C@@H](C=1N=CC=CC=1)NC(=O)C1=CNC(=O)C=C1 IFQPPSJDRNBIKT-KRWDZBQOSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- WGXIYUXPBMIEAZ-SFHVURJKSA-N methyl 3-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)C(F)(F)F)=C1 WGXIYUXPBMIEAZ-SFHVURJKSA-N 0.000 claims description 2
- XEBLMAHANNXTFZ-SFHVURJKSA-N methyl 4-[[(s)-[4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 XEBLMAHANNXTFZ-SFHVURJKSA-N 0.000 claims description 2
- LGOGBBCKELLDJU-UHFFFAOYSA-N n-[(2,3-difluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CC(C(NC(=O)C2=CNC(=O)C=C2)C=2C=C(F)C(OC(F)(F)F)=CC=2)=C1F LGOGBBCKELLDJU-UHFFFAOYSA-N 0.000 claims description 2
- UOQKLRABAUYYSH-UHFFFAOYSA-N n-[(2,4-difluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1C(C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 UOQKLRABAUYYSH-UHFFFAOYSA-N 0.000 claims description 2
- VJORDDIYNREJFE-UHFFFAOYSA-N n-[(2,5-difluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=C(F)C(C(NC(=O)C2=CNC(=O)C=C2)C=2C=C(F)C(OC(F)(F)F)=CC=2)=C1 VJORDDIYNREJFE-UHFFFAOYSA-N 0.000 claims description 2
- XIBLZEAPTRODHX-UHFFFAOYSA-N n-[(2,6-difluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CC(F)=C1C(C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 XIBLZEAPTRODHX-UHFFFAOYSA-N 0.000 claims description 2
- VAXUHYOVHRTBGT-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)-pyridin-2-ylmethyl]isoquinoline-6-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(C=1N=CC=CC=1)NC(=O)C1=CC=C(C=NC=C2)C2=C1 VAXUHYOVHRTBGT-UHFFFAOYSA-N 0.000 claims description 2
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- RXQHMHJSHHBPNC-UHFFFAOYSA-N n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-4-methyl-1,3-oxazole-5-carboxamide Chemical compound N1=COC(C(=O)NC(C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)F)=C1C RXQHMHJSHHBPNC-UHFFFAOYSA-N 0.000 claims description 2
- MWENAQBCCLYYIM-UHFFFAOYSA-N n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-methoxypyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)NC(C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 MWENAQBCCLYYIM-UHFFFAOYSA-N 0.000 claims description 2
- RZNQRJQJUGWGHP-UHFFFAOYSA-N n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound FC1=CC=CN=C1C(C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=CC=C1 RZNQRJQJUGWGHP-UHFFFAOYSA-N 0.000 claims description 2
- LFYDVBJARILFSP-UHFFFAOYSA-N n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]quinoline-7-carboxamide Chemical compound FC1=CC=CN=C1C(C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC=N2)C2=C1 LFYDVBJARILFSP-UHFFFAOYSA-N 0.000 claims description 2
- YRIQLRKMHPJJER-UHFFFAOYSA-N n-[(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]quinoxaline-6-carboxamide Chemical compound FC1=CC=CN=C1C(C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(N=CC=N2)C2=C1 YRIQLRKMHPJJER-UHFFFAOYSA-N 0.000 claims description 2
- GOIXSEPEABNAFO-UHFFFAOYSA-N n-[(4-fluorophenyl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1C(C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 GOIXSEPEABNAFO-UHFFFAOYSA-N 0.000 claims description 2
- WFXMRLADDAFMPO-UHFFFAOYSA-N n-[(4-iodophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1C(C=1C=CC(I)=CC=1)NC(=O)C1=CNC(=O)C=C1 WFXMRLADDAFMPO-UHFFFAOYSA-N 0.000 claims description 2
- KZJHWEJVIDNHJM-MRXNPFEDSA-N n-[(r)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 KZJHWEJVIDNHJM-MRXNPFEDSA-N 0.000 claims description 2
- IJTSMWHYNKDXNG-MRXNPFEDSA-N n-[(r)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 IJTSMWHYNKDXNG-MRXNPFEDSA-N 0.000 claims description 2
- XELMWLYVXJUVAL-SFHVURJKSA-N n-[(s)-(2,6-difluorophenyl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CC(F)=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 XELMWLYVXJUVAL-SFHVURJKSA-N 0.000 claims description 2
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- ITIVSAABNNUPIB-INIZCTEOSA-N n-[(s)-(3,4-dichlorophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=NC(O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(Cl)C(Cl)=C1 ITIVSAABNNUPIB-INIZCTEOSA-N 0.000 claims description 2
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- GAOUPSMKMKDJBD-SFHVURJKSA-N n-[(s)-(3-fluoro-4-methylphenyl)-(3-fluoropyridin-2-yl)methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC=C1[C@@H](C=1C(=CC=CN=1)F)NC(=O)C1=CN(C)C(=O)C=C1 GAOUPSMKMKDJBD-SFHVURJKSA-N 0.000 claims description 2
- BJCQSVQWOBZTEY-KRWDZBQOSA-N n-[(s)-(3-fluoro-4-methylphenyl)-(3-fluoropyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC=C1[C@@H](C=1C(=CC=CN=1)F)NC(=O)C1=CNC(=O)C=C1 BJCQSVQWOBZTEY-KRWDZBQOSA-N 0.000 claims description 2
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- ZSEQFYRDASNGHV-KRWDZBQOSA-N n-[(s)-(3-fluoro-5-methylphenyl)-(3-fluoropyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC(F)=CC([C@H](NC(=O)C2=CNC(=O)C=C2)C=2C(=CC=CN=2)F)=C1 ZSEQFYRDASNGHV-KRWDZBQOSA-N 0.000 claims description 2
- LNTWPYVQLNGODX-KRWDZBQOSA-N n-[(s)-(3-fluoro-6-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC=C(F)C([C@@H](NC(=O)C2=CNC(=O)C=C2)C=2C=CC(=CC=2)C(F)(F)F)=N1 LNTWPYVQLNGODX-KRWDZBQOSA-N 0.000 claims description 2
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- GXNIICNEQMCJBN-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-(4-methoxyphenyl)methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H](C=1C(=CC=CN=1)F)NC(=O)C1=CN(C)C(=O)C=C1 GXNIICNEQMCJBN-SFHVURJKSA-N 0.000 claims description 2
- WHLLNCSIKLJEFU-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-(4-methoxyphenyl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H](C=1C(=CC=CN=1)F)NC(=O)C1=CNC(=O)C=C1 WHLLNCSIKLJEFU-KRWDZBQOSA-N 0.000 claims description 2
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- OTUJJEBIUCTQJC-NTISSMGPSA-N n-[(s)-(3-fluoropyridin-2-yl)-[2-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=CN=C1[C@H](C=1C(=CC(OC(F)(F)F)=CC=1)F)NC(=O)C1=CNC(=O)C=C1 OTUJJEBIUCTQJC-NTISSMGPSA-N 0.000 claims description 2
- NVJFGAQLWVMBEU-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-(2-hydroxy-2-methylpropyl)-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC(C)(O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 NVJFGAQLWVMBEU-IBGZPJMESA-N 0.000 claims description 2
- OLBHLGSGNNZDLV-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-(2-hydroxyethyl)-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CCO)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 OLBHLGSGNNZDLV-SFHVURJKSA-N 0.000 claims description 2
- PZNYIXGUCVYCMX-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-(oxetan-3-yl)-6-oxopyridine-3-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C2=CN(C(=O)C=C2)C2COC2)C=2C(=CC=CN=2)F)=C1 PZNYIXGUCVYCMX-IBGZPJMESA-N 0.000 claims description 2
- CLLPOYRPRPPDTL-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-[(1-hydroxycyclopropyl)methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=C(C(=O)N[C@@H](C=2C=C(F)C(OC(F)(F)F)=CC=2)C=2C(=CC=CN=2)F)C=CC(=O)N1CC1(O)CC1 CLLPOYRPRPPDTL-IBGZPJMESA-N 0.000 claims description 2
- HPZUAJFPXWSKBH-BLVKFPJESA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-[(2r)-2-hydroxypropyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C[C@H](O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 HPZUAJFPXWSKBH-BLVKFPJESA-N 0.000 claims description 2
- HPZUAJFPXWSKBH-BUXKBTBVSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-[(2s)-2-hydroxypropyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C[C@@H](O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 HPZUAJFPXWSKBH-BUXKBTBVSA-N 0.000 claims description 2
- BTIXROKVVCGVGQ-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 BTIXROKVVCGVGQ-KRWDZBQOSA-N 0.000 claims description 2
- TZKVJUFUHCKKBV-UQKRIMTDSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-1-methylimidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN1C=CN=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 TZKVJUFUHCKKBV-UQKRIMTDSA-N 0.000 claims description 2
- RPACLJVMIZLRSB-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3CC(=O)NC3=CC=2)C=2C(=CC=CN=2)F)=C1 RPACLJVMIZLRSB-IBGZPJMESA-N 0.000 claims description 2
- HTDURSLFCORSAD-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-1h-[1,3]oxazolo[5,4-c]pyridine-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C(N=C1)=CC2=C1OC(=O)N2 HTDURSLFCORSAD-INIZCTEOSA-N 0.000 claims description 2
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- PYILUMMLVHGCQG-FQEVSTJZSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3CCC(=O)NC3=CC=2)C=2C(=CC=CN=2)F)=C1 PYILUMMLVHGCQG-FQEVSTJZSA-N 0.000 claims description 2
- MNCXKKLFGRLNDC-NTISSMGPSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-5-hydroxypyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CC(O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 MNCXKKLFGRLNDC-NTISSMGPSA-N 0.000 claims description 2
- KGPOFFAORVXVMB-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-5-methoxy-6-oxo-1h-pyridine-2-carboxamide Chemical compound N1C(=O)C(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 KGPOFFAORVXVMB-INIZCTEOSA-N 0.000 claims description 2
- PQPVGVRCJWSPBA-UQKRIMTDSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-5-methyl-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C(C)=CN=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 PQPVGVRCJWSPBA-UQKRIMTDSA-N 0.000 claims description 2
- YMUCGHBLIUKIHK-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-5-methyl-6-oxo-1h-pyridine-3-carboxamide Chemical compound N1C(=O)C(C)=CC(C(=O)N[C@@H](C=2C=C(F)C(OC(F)(F)F)=CC=2)C=2C(=CC=CN=2)F)=C1 YMUCGHBLIUKIHK-INIZCTEOSA-N 0.000 claims description 2
- RBZUGDMXCWJLCD-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6,7-dihydro-5h-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C2=NN3CCCOC3=C2)C=2C(=CC=CN=2)F)=C1 RBZUGDMXCWJLCD-KRWDZBQOSA-N 0.000 claims description 2
- OFOICMNFWXONMR-AEFFLSMTSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1-[(2r)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-3-carboxamide Chemical compound C1=CC(=O)N(C[C@@H](O)C(F)(F)F)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(OC(F)(F)F)C(F)=C1 OFOICMNFWXONMR-AEFFLSMTSA-N 0.000 claims description 2
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- WKEOHPDXDROTDF-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyrazine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=N1 WKEOHPDXDROTDF-HNNXBMFYSA-N 0.000 claims description 2
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- SMDDNYFJHJHSCD-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC([C@H](NC(=O)C2=CNC(=O)C=C2)C=2C(=CC=CN=2)F)=C1 SMDDNYFJHJHSCD-INIZCTEOSA-N 0.000 claims description 2
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- ZQEHBKWGFNADAB-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridazine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=NNC(=O)C=C1 ZQEHBKWGFNADAB-HNNXBMFYSA-N 0.000 claims description 2
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- STUYVTIMPIRQLK-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]imidazo[1,2-a]pyridine-7-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CC2=NC=CN2C=C1 STUYVTIMPIRQLK-SFHVURJKSA-N 0.000 claims description 2
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- HQRPNNDOZZWVKO-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethoxy)phenyl]methyl]tetrazolo[1,5-a]pyridine-7-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(OC(F)(F)F)=CC=1)NC(=O)C1=CC2=NN=NN2C=C1 HQRPNNDOZZWVKO-INIZCTEOSA-N 0.000 claims description 2
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- LPCKWNRHPGZHNN-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=NNC2=C1CCC2 LPCKWNRHPGZHNN-INIZCTEOSA-N 0.000 claims description 2
- FGMAFOSLNCITDL-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-(2-hydroxy-2-methylpropyl)-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CC(C)(O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 FGMAFOSLNCITDL-IBGZPJMESA-N 0.000 claims description 2
- LNVHVEYUEJFCEP-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-(2-hydroxyethyl)-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(CCO)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 LNVHVEYUEJFCEP-SFHVURJKSA-N 0.000 claims description 2
- GOIZSHGHLFXNIO-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-(oxetan-3-yl)-6-oxopyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CN(C2COC2)C(=O)C=C1 GOIZSHGHLFXNIO-IBGZPJMESA-N 0.000 claims description 2
- QWOYTSCKSBWHAI-YJYMSZOUSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-[(2r)-2-hydroxypropyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C[C@H](O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 QWOYTSCKSBWHAI-YJYMSZOUSA-N 0.000 claims description 2
- QWOYTSCKSBWHAI-DJJJIMSYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1-[(2s)-2-hydroxypropyl]-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C[C@@H](O)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 QWOYTSCKSBWHAI-DJJJIMSYSA-N 0.000 claims description 2
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- FYQTUYZNRPTNKC-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-1h-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC2=NC=CC=C12 FYQTUYZNRPTNKC-KRWDZBQOSA-N 0.000 claims description 2
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- UZVHBDHCQROTBJ-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-methyl-3h-benzimidazole-5-carboxamide Chemical compound C1([C@H](NC(=O)C=2C=C3N=C(NC3=CC=2)C)C=2C(=CC=CN=2)F)=CC=C(C(F)(F)F)C=C1 UZVHBDHCQROTBJ-IBGZPJMESA-N 0.000 claims description 2
- XIZCHJIHIDNJBY-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-methylpyridine-4-carboxamide Chemical compound C1=NC(C)=CC(C(=O)N[C@@H](C=2C=CC(=CC=2)C(F)(F)F)C=2C(=CC=CN=2)F)=C1 XIZCHJIHIDNJBY-KRWDZBQOSA-N 0.000 claims description 2
- WUNIVRIBKWWKNK-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-1,3-dihydrobenzimidazole-5-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)N2)C2=C1 WUNIVRIBKWWKNK-KRWDZBQOSA-N 0.000 claims description 2
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- SHMZHDGBNQMZBW-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-1,3-dihydroindole-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(CC(=O)N2)C2=C1 SHMZHDGBNQMZBW-IBGZPJMESA-N 0.000 claims description 2
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- WJEONQAOCDRZSX-FQEVSTJZSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-1h-quinoline-7-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC(=O)N2)C2=C1 WJEONQAOCDRZSX-FQEVSTJZSA-N 0.000 claims description 2
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- NCJUMDRNRKFLKP-FQEVSTJZSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)CC2)C2=C1 NCJUMDRNRKFLKP-FQEVSTJZSA-N 0.000 claims description 2
- HKKWDOGXHNTFNR-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)O2)C2=C1 HKKWDOGXHNTFNR-KRWDZBQOSA-N 0.000 claims description 2
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- CBLPCFZBENMXMW-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-3-oxo-4h-1,4-benzoxazine-7-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)CO2)C2=C1 CBLPCFZBENMXMW-IBGZPJMESA-N 0.000 claims description 2
- FNRYKIOMVCMNRY-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-3-oxo-4h-1,4-benzoxazine-8-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=CC2=C1OCC(=O)N2 FNRYKIOMVCMNRY-SFHVURJKSA-N 0.000 claims description 2
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- RNEMEYZMWYINOF-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-4,5,6,7-tetrahydro-1h-indazole-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=NNC2=C1CCCC2 RNEMEYZMWYINOF-KRWDZBQOSA-N 0.000 claims description 2
- QRITYGGYIDSATP-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 QRITYGGYIDSATP-SFHVURJKSA-N 0.000 claims description 2
- XXOZZJOOBDCOBA-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-4-methylsulfonylbenzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 XXOZZJOOBDCOBA-SFHVURJKSA-N 0.000 claims description 2
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- ACCUWDDEGMHYQT-KRWDZBQOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6,7-dihydro-5h-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=NN2CCCOC2=C1 ACCUWDDEGMHYQT-KRWDZBQOSA-N 0.000 claims description 2
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- HKVRGNXSZPYERK-IBGZPJMESA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1-propan-2-ylpyridine-3-carboxamide Chemical compound C1=CC(=O)N(C(C)C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(C(F)(F)F)C=C1 HKVRGNXSZPYERK-IBGZPJMESA-N 0.000 claims description 2
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- GLFJVPICGCBFDW-HNNXBMFYSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridazine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=NNC(=O)C=C1 GLFJVPICGCBFDW-HNNXBMFYSA-N 0.000 claims description 2
- GCAYTEBIQXONEI-SFHVURJKSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]imidazo[1,2-a]pyridine-6-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CN2C=CN=C2C=C1 GCAYTEBIQXONEI-SFHVURJKSA-N 0.000 claims description 2
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- DPNHRLVCCNOELT-INIZCTEOSA-N n-[(s)-(3-fluoropyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]tetrazolo[1,5-a]pyridine-7-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC2=NN=NN2C=C1 DPNHRLVCCNOELT-INIZCTEOSA-N 0.000 claims description 2
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- FGLSBKWCMCLPAN-NRFANRHFSA-N n-[(s)-(3-methoxyphenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound COC1=CC=CC([C@H](NC(=O)C=2C=C3N=CC=CC3=CC=2)C=2C(=CC=CN=2)C(F)(F)F)=C1 FGLSBKWCMCLPAN-NRFANRHFSA-N 0.000 claims description 2
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- NZFCKVJDQVLILS-IBGZPJMESA-N n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(OC(=O)N2)C2=C1 NZFCKVJDQVLILS-IBGZPJMESA-N 0.000 claims description 2
- NZRNEAJKOFWCNG-IBGZPJMESA-N n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)O2)C2=C1 NZRNEAJKOFWCNG-IBGZPJMESA-N 0.000 claims description 2
- WZAJTYGBCKTHOR-NRFANRHFSA-N n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-3-oxo-4h-1,4-benzoxazine-7-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(NC(=O)CO2)C2=C1 WZAJTYGBCKTHOR-NRFANRHFSA-N 0.000 claims description 2
- YVYOBRJPTHSKNI-SFHVURJKSA-N n-[(s)-(3-methylpyridin-2-yl)-[4-(trifluoromethyl)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CNC(=O)C=C1 YVYOBRJPTHSKNI-SFHVURJKSA-N 0.000 claims description 2
- UZFYWJVUDBMSDL-FQEVSTJZSA-N n-[(s)-(4-chlorophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1[C@H](C=1C=CC(Cl)=CC=1)NC(=O)C1=CC=C(C=CC=N2)C2=C1 UZFYWJVUDBMSDL-FQEVSTJZSA-N 0.000 claims description 2
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- WFRBDTMIJJXNLJ-KRWDZBQOSA-N n-[(s)-(4-fluoro-3-methylphenyl)-(3-fluoropyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC([C@H](NC(=O)C2=CNC(=O)C=C2)C=2C(=CC=CN=2)F)=C1 WFRBDTMIJJXNLJ-KRWDZBQOSA-N 0.000 claims description 2
- KOXMAFUAAYZOJS-KRWDZBQOSA-N n-[(s)-(4-fluorophenyl)-(3-fluoropyridin-2-yl)methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound C1=CC(=O)N(C)C=C1C(=O)N[C@H](C=1C(=CC=CN=1)F)C1=CC=C(F)C=C1 KOXMAFUAAYZOJS-KRWDZBQOSA-N 0.000 claims description 2
- LWSDEFDZXLHSAO-INIZCTEOSA-N n-[(s)-(4-fluorophenyl)-(3-fluoropyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1[C@@H](C=1C(=CC=CN=1)F)NC(=O)C1=CNC(=O)C=C1 LWSDEFDZXLHSAO-INIZCTEOSA-N 0.000 claims description 2
- CSWQGEPMNGFTJR-KRWDZBQOSA-N n-[(s)-(4-fluorophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-6-methoxypyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CC=C(F)C=C1 CSWQGEPMNGFTJR-KRWDZBQOSA-N 0.000 claims description 2
- KXOYDKDBJCQFMC-KRWDZBQOSA-N n-[(s)-(4-fluorophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]benzamide Chemical compound C1=CC(F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=CC=C1 KXOYDKDBJCQFMC-KRWDZBQOSA-N 0.000 claims description 2
- KHLQJMXGNUKLQZ-FQEVSTJZSA-N n-[(s)-(4-fluorophenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1=CC(F)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC=N2)C2=C1 KHLQJMXGNUKLQZ-FQEVSTJZSA-N 0.000 claims description 2
- SNGJRCXXXCPGOB-NRFANRHFSA-N n-[(s)-(4-methoxyphenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1=CC(OC)=CC=C1[C@@H](C=1C(=CC=CN=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC=N2)C2=C1 SNGJRCXXXCPGOB-NRFANRHFSA-N 0.000 claims description 2
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- HMGFTTHOFJEGFV-QHCPKHFHSA-N n-[(s)-(5-chloroquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1[C@H](C=1C=C2C(Cl)=CC=CC2=NC=1)NC(=O)C1=CC=C(C=CC=N2)C2=C1 HMGFTTHOFJEGFV-QHCPKHFHSA-N 0.000 claims description 2
- CWAVBFBSDWWKKH-KRWDZBQOSA-N n-[(s)-(5-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound N1=CC(F)=CC=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 CWAVBFBSDWWKKH-KRWDZBQOSA-N 0.000 claims description 2
- WPGAFVOIENGATI-IBGZPJMESA-N n-[(s)-(6-chloroquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=NC(O)=CC=C1C(=O)N[C@H](C=1C(=CC=CN=1)C(F)(F)F)C1=CN=C(C=CC(Cl)=C2)C2=C1 WPGAFVOIENGATI-IBGZPJMESA-N 0.000 claims description 2
- WDLSOHLKTQASSY-QHCPKHFHSA-N n-[(s)-(6-chloroquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]isoquinoline-6-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1[C@H](C=1C=C2C=C(Cl)C=CC2=NC=1)NC(=O)C1=CC=C(C=NC=C2)C2=C1 WDLSOHLKTQASSY-QHCPKHFHSA-N 0.000 claims description 2
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- CDKKXHHJVXOUKJ-DEOSSOPVSA-N n-[(s)-(7-methoxyquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1([C@@H](NC(=O)C=2C=C3N=CC=CC3=CC=2)C2=CC3=CC=C(C=C3N=C2)OC)=NC=CC=C1C(F)(F)F CDKKXHHJVXOUKJ-DEOSSOPVSA-N 0.000 claims description 2
- TYFXMXUWCRVMRS-QHCPKHFHSA-N n-[(s)-(8-chloroquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1[C@H](C=1C=C2C=CC=C(Cl)C2=NC=1)NC(=O)C1=CC=C(C=CC=N2)C2=C1 TYFXMXUWCRVMRS-QHCPKHFHSA-N 0.000 claims description 2
- VWDIIJQCQXDIEV-QHCPKHFHSA-N n-[(s)-(8-fluoroquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1([C@@H](NC(=O)C=2C=C3N=CC=CC3=CC=2)C=2C=C3C=CC=C(C3=NC=2)F)=NC=CC=C1C(F)(F)F VWDIIJQCQXDIEV-QHCPKHFHSA-N 0.000 claims description 2
- ZOPJVKGPINXZJI-DEOSSOPVSA-N n-[(s)-(8-methoxyquinolin-3-yl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound C1([C@@H](NC(=O)C=2C=C3N=CC=CC3=CC=2)C=2C=C3C=CC=C(C3=NC=2)OC)=NC=CC=C1C(F)(F)F ZOPJVKGPINXZJI-DEOSSOPVSA-N 0.000 claims description 2
- ZTFKQUILAZIJEA-VWLOTQADSA-N n-[(s)-[3-(2,2-dimethylpropyl)pyridin-2-yl]-[4-(trifluoromethyl)phenyl]methyl]quinoline-6-carboxamide Chemical compound CC(C)(C)CC1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(N=CC=C2)C2=C1 ZTFKQUILAZIJEA-VWLOTQADSA-N 0.000 claims description 2
- YNRFVYBOUKLFOD-FQEVSTJZSA-N n-[(s)-[3-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-7-carboxamide Chemical compound FC(F)(F)C1=CC=CC([C@H](NC(=O)C=2C=C3N=CC=CC3=CC=2)C=2C(=CC=CN=2)C(F)(F)F)=C1 YNRFVYBOUKLFOD-FQEVSTJZSA-N 0.000 claims description 2
- SYUGVDKKWWRART-UPVQGACJSA-N n-[(s)-[3-[(1r)-2,2-dimethylcyclopropyl]pyridin-2-yl]-[4-(trifluoromethyl)phenyl]methyl]quinoline-6-carboxamide Chemical compound CC1(C)C[C@H]1C1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(N=CC=C2)C2=C1 SYUGVDKKWWRART-UPVQGACJSA-N 0.000 claims description 2
- DYRFYPLVLCZUPR-UPVQGACJSA-N n-[(s)-[3-[(1r)-2,2-dimethylcyclopropyl]pyridin-2-yl]-[4-(trifluoromethyl)phenyl]methyl]quinoline-7-carboxamide Chemical compound CC1(C)C[C@H]1C1=CC=CN=C1[C@H](C=1C=CC(=CC=1)C(F)(F)F)NC(=O)C1=CC=C(C=CC=N2)C2=C1 DYRFYPLVLCZUPR-UPVQGACJSA-N 0.000 claims description 2
- JMDXDCXUPKHVCF-SANMLTNESA-N n-[(s)-[3-[2-(3-methyloxetan-3-yl)ethynyl]pyridin-2-yl]-[4-(trifluoromethyl)phenyl]methyl]quinoline-6-carboxamide Chemical compound C=1C=CN=C([C@@H](NC(=O)C=2C=C3C=CC=NC3=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C=1C#CC1(C)COC1 JMDXDCXUPKHVCF-SANMLTNESA-N 0.000 claims description 2
- NATNQWGKUUUZDL-IBGZPJMESA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-(3-methylpyridin-2-yl)methyl]-1-methyl-6-oxopyridine-3-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CN(C)C(=O)C=C1 NATNQWGKUUUZDL-IBGZPJMESA-N 0.000 claims description 2
- PQBLCHWQOYORNO-IBGZPJMESA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-(3-methylpyridin-2-yl)methyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(OC(=O)N2)C2=C1 PQBLCHWQOYORNO-IBGZPJMESA-N 0.000 claims description 2
- MYQUYWRMGIFMGK-NRFANRHFSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-(3-methylpyridin-2-yl)methyl]-3-oxo-4h-1,4-benzoxazine-7-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CC=C(NC(=O)CO2)C2=C1 MYQUYWRMGIFMGK-NRFANRHFSA-N 0.000 claims description 2
- QVKWMCBWBCDSKZ-SFHVURJKSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-(3-methylpyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC=CN=C1[C@H](C=1C=C(F)C(OC(F)(F)F)=CC=1)NC(=O)C1=CNC(=O)C=C1 QVKWMCBWBCDSKZ-SFHVURJKSA-N 0.000 claims description 2
- IUIVWCNPYGFDNI-KRWDZBQOSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-2-oxo-3h-1,3-benzoxazole-5-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3NC(=O)OC3=CC=2)C=2C(=CC=CN=2)C(F)(F)F)=C1 IUIVWCNPYGFDNI-KRWDZBQOSA-N 0.000 claims description 2
- NCEYOKAQKJSYLJ-SFHVURJKSA-N n-[(s)-[3-fluoro-4-(trifluoromethoxy)phenyl]-pyridin-2-ylmethyl]-2-oxo-3h-1,3-benzoxazole-6-carboxamide Chemical compound C1=C(OC(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3OC(=O)NC3=CC=2)C=2N=CC=CC=2)=C1 NCEYOKAQKJSYLJ-SFHVURJKSA-N 0.000 claims description 2
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- GNJGCLVNLMEHTE-SFHVURJKSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-1,8-naphthyridine-2-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)C=2N=C3N=CC=CC3=CC=2)C=2C(=CC=CN=2)C(F)(F)F)=C1 GNJGCLVNLMEHTE-SFHVURJKSA-N 0.000 claims description 2
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- OKNXXVIQMJKVCP-FQEVSTJZSA-N n-[(s)-[3-fluoro-4-(trifluoromethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]quinoline-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC([C@H](NC(=O)C=2C=C3C=CC=NC3=CC=2)C=2C(=CC=CN=2)C(F)(F)F)=C1 OKNXXVIQMJKVCP-FQEVSTJZSA-N 0.000 claims description 2
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- IKQUJPCLYPKUHP-INIZCTEOSA-N n-[(s)-(4-chloro-3-fluorophenyl)-(3-fluoropyridin-2-yl)methyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound FC1=CC=CN=C1[C@H](C=1C=C(F)C(Cl)=CC=1)NC(=O)C1=CNC(=O)C=C1 IKQUJPCLYPKUHP-INIZCTEOSA-N 0.000 description 1
- ALVOQMUNZLWHAR-HAWMADMCSA-N n-[(s)-(4-formylphenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-2-methylpropane-2-sulfinamide Chemical compound C1([C@H](N[S@@](=O)C(C)(C)C)C=2C(=CC=CN=2)C(F)(F)F)=CC=C(C=O)C=C1 ALVOQMUNZLWHAR-HAWMADMCSA-N 0.000 description 1
- UQAOPEBLJBFMHS-HAWMADMCSA-N n-[(s)-(4-methoxyphenyl)-[3-(trifluoromethyl)pyridin-2-yl]methyl]-2-methylpropane-2-sulfinamide Chemical compound C1=CC(OC)=CC=C1[C@H](N[S@@](=O)C(C)(C)C)C1=NC=CC=C1C(F)(F)F UQAOPEBLJBFMHS-HAWMADMCSA-N 0.000 description 1
- CWLJIUVHLJXEQB-YXMWSKHCSA-N n-[(s)-[4-(1-hydroxyethyl)phenyl]-[3-(trifluoromethyl)pyridin-2-yl]methyl]-2-methylpropane-2-sulfinamide Chemical compound C1=CC(C(O)C)=CC=C1[C@H](N[S@@](=O)C(C)(C)C)C1=NC=CC=C1C(F)(F)F CWLJIUVHLJXEQB-YXMWSKHCSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical compound C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OOUHCAOKCRDABZ-UHFFFAOYSA-N potassium oxido(oxo)silane Chemical compound [K+].[O-][SiH]=O OOUHCAOKCRDABZ-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- AVTYONGGKAJVTE-UHFFFAOYSA-L potassium tartrate Chemical compound [K+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O AVTYONGGKAJVTE-UHFFFAOYSA-L 0.000 description 1
- QGLVEAGMVUQOJP-UHFFFAOYSA-N prop-2-enylboronic acid Chemical compound OB(O)CC=C QGLVEAGMVUQOJP-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000012363 selectfluor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 210000001044 sensory neuron Anatomy 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003238 somatosensory effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- CESUXLKAADQNTB-UHFFFAOYSA-N tert-butanesulfinamide Chemical group CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OSWULUXZFOQIRU-UHFFFAOYSA-N tert-butyl 2-aminoacetate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CN OSWULUXZFOQIRU-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- ZULCNBGGVUMSCW-SFHVURJKSA-N tert-butyl n-[5-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]-2-oxo-1h-pyridin-3-yl]carbamate Chemical compound N1=C(O)C(NC(=O)OC(C)(C)C)=CC(C(=O)N[C@@H](C=2C=C(F)C(OC(F)(F)F)=CC=2)C=2C(=CC=CN=2)F)=C1 ZULCNBGGVUMSCW-SFHVURJKSA-N 0.000 description 1
- QICJOKYTDMOGMR-VWLOTQADSA-N tert-butyl n-[5-[[(s)-(3-fluoropyridin-2-yl)-[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]carbamoyl]-2-phenylmethoxypyridin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(=O)N[C@@H](C=2C=C(F)C(OC(F)(F)F)=CC=2)C=2C(=CC=CN=2)F)=CN=C1OCC1=CC=CC=C1 QICJOKYTDMOGMR-VWLOTQADSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/61—Halogen atoms or nitro radicals
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| JP2018528948A (ja) * | 2015-08-28 | 2018-10-04 | サイノファーム タイワン,リミティド | アプレミラストの新規形態及びその作成方法 |
| JP2023530320A (ja) * | 2020-06-17 | 2023-07-14 | メルク・シャープ・アンド・ドーム・エルエルシー | Nav1.8阻害剤としての5-オキソピロリジン-3-カルボキサミド |
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| CN107001806B (zh) * | 2014-09-29 | 2020-12-04 | 斯克利普斯研究院 | 用于治疗心肺疾病的鞘氨醇-1-磷酸盐受体调节剂 |
| CN113384577A (zh) * | 2016-06-13 | 2021-09-14 | 田边三菱制药株式会社 | 用于治疗或预防血管舒缩症状的组合物 |
| WO2018234808A1 (en) | 2017-06-22 | 2018-12-27 | Curadev Pharma Limited | Small molecule modulators of human sting |
| JP2020524717A (ja) * | 2017-06-22 | 2020-08-20 | キュラデブ・ファーマ・リミテッドCuradev Pharma Limited | ヒトstingの小分子調節因子 |
| TW201929855A (zh) | 2017-12-19 | 2019-08-01 | 日商田邊三菱製藥股份有限公司 | 用於治療或預防血管舒縮症狀的組成物及方法 |
| WO2019180627A1 (en) * | 2018-03-21 | 2019-09-26 | Piramal Enterprises Limited | AN IMPROVED ASYMMETRIC SYNTHESIS OF alpha-(DIARYLMETHYL) ALKYL AMINES |
| US11279672B2 (en) * | 2018-04-18 | 2022-03-22 | Piramal Pharma Limited | Asymmetric synthesis of alpha-branched chiral amines |
| CN110981795B (zh) * | 2019-12-18 | 2021-02-12 | 武汉世纪久海检测技术有限公司 | 一种利用2-氰基异烟酸甲酯制备2-氨酰基异烟酸的方法 |
| MX2022015581A (es) | 2020-06-17 | 2023-01-24 | Merck Sharp & Dohme Llc | 2-oxoimidazolidin-4-carboxamidas como inhibidores de nav1.8. |
| JP2023530319A (ja) * | 2020-06-17 | 2023-07-14 | メルク・シャープ・アンド・ドーム・エルエルシー | Nav1.8阻害剤としての2-オキソ-オキサゾリジン-5-カルボキサミド |
| CA3221549A1 (en) * | 2021-06-08 | 2022-12-15 | Liqiang Fu | Isoindolinone compounds, and uses thereof |
| CN115108980B (zh) * | 2022-06-22 | 2023-06-16 | 济南大学 | 一种2-甲基喹啉类化合物的4号位酰基化衍生物的制备方法 |
| WO2025113520A1 (zh) * | 2023-11-28 | 2025-06-05 | 成都地奥制药集团有限公司 | 酰胺类化合物及其用途 |
| CN119118901B (zh) * | 2024-09-09 | 2025-09-30 | 中国人民解放军北部战区总医院 | 一种氧吲哚类衍生物及其制备方法与在trpa1抑制剂方向的应用 |
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| BR112013033316A2 (pt) | 2017-01-31 |
| AU2012272895B2 (en) | 2015-01-22 |
| EA201490152A1 (ru) | 2014-05-30 |
| AP2013007331A0 (en) | 2013-12-31 |
| US20130157996A1 (en) | 2013-06-20 |
| PE20140868A1 (es) | 2014-07-18 |
| AR086750A1 (es) | 2014-01-22 |
| EP2723717A2 (en) | 2014-04-30 |
| TN2013000529A1 (en) | 2015-03-30 |
| AU2012272895A1 (en) | 2013-04-11 |
| MY157429A (en) | 2016-06-15 |
| TWI448454B (zh) | 2014-08-11 |
| MX2013015274A (es) | 2014-03-31 |
| CN103906733A (zh) | 2014-07-02 |
| TW201311643A (zh) | 2013-03-16 |
| US20140171406A1 (en) | 2014-06-19 |
| WO2012177893A2 (en) | 2012-12-27 |
| CL2013003715A1 (es) | 2014-06-27 |
| CA2839699A1 (en) | 2012-12-27 |
| WO2012177893A3 (en) | 2013-06-13 |
| US20140171639A1 (en) | 2014-06-19 |
| KR20140045507A (ko) | 2014-04-16 |
| US8710043B2 (en) | 2014-04-29 |
| MA35271B1 (fr) | 2014-07-03 |
| TW201429948A (zh) | 2014-08-01 |
| PH12013502611A1 (en) | 2014-04-28 |
| US9096527B2 (en) | 2015-08-04 |
| CR20140037A (es) | 2014-03-13 |
| UY34160A (es) | 2012-08-31 |
| CO6852073A2 (es) | 2014-01-30 |
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