RU2638537C2 - Ингибирование ферментов - Google Patents

Info

Publication number

RU2638537C2

RU2638537C2 RU2015104644A RU2015104644A RU2638537C2 RU 2638537 C2 RU2638537 C2 RU 2638537C2 RU 2015104644 A RU2015104644 A RU 2015104644A RU 2015104644 A RU2015104644 A RU 2015104644A RU 2638537 C2 RU2638537 C2 RU 2638537C2

Authority

RU

Russia

Prior art keywords

methyl

trifluoromethylphenyl

triazolo

pyrazol

pyridin

Prior art date

2012-07-12

Links

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• 102000004190 Enzymes Human genes 0.000 title description 4
• 108090000790 Enzymes Proteins 0.000 title description 4
• 230000005764 inhibitory process Effects 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 370
• 238000000034 method Methods 0.000 claims abstract description 201
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 123
• 239000001257 hydrogen Substances 0.000 claims abstract description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 50
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 claims abstract description 26
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 25
• 102000052502 human ELANE Human genes 0.000 claims abstract description 24
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 22
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 125000006413 ring segment Chemical group 0.000 claims abstract description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract 3
• -1 4-methanesulfonylphenylamino Chemical group 0.000 claims description 209
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 105
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 104
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 59
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 48
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 42
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
• HDHYOIKLJGKTIB-UHFFFAOYSA-N 4-[5-[2-amino-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(N)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 HDHYOIKLJGKTIB-UHFFFAOYSA-N 0.000 claims description 21
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• DACWQSNZECJJGG-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CN=C21 DACWQSNZECJJGG-UHFFFAOYSA-N 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 14
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 206010014561 Emphysema Diseases 0.000 claims description 12
• VHVYIAMNGDUUOQ-UHFFFAOYSA-N 4-[5-[7-methyl-3-oxo-8-[3-(trifluoromethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN(C(NN=2)=O)C=2C=1C1=CC=CC(C(F)(F)F)=C1 VHVYIAMNGDUUOQ-UHFFFAOYSA-N 0.000 claims description 11
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 11
• HSBSYNFWDGVDBH-UHFFFAOYSA-N 1-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-piperidin-4-ylurea Chemical compound N1=C2C(C=3C=C(C=CC=3)C(F)(F)F)=C(C)C(C=3N(N=CC=3)C=3C=CC(=CC=3)C#N)=CN2N=C1NC(=O)NC1CCNCC1 HSBSYNFWDGVDBH-UHFFFAOYSA-N 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• RRWZVEZXQDDCOH-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-methylsulfonylpropanamide Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(NC(=O)CCS(C)(=O)=O)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 RRWZVEZXQDDCOH-UHFFFAOYSA-N 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• IUXIOFICFSXEDD-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]acetamide Chemical compound C=1N2N=C(NC(=O)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 IUXIOFICFSXEDD-UHFFFAOYSA-N 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 8
• RPVWYEGQTXQGMH-UHFFFAOYSA-O 3-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]carbamoylamino]propyl-trimethylazanium Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(NC(=O)NCCC[N+](C)(C)C)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 RPVWYEGQTXQGMH-UHFFFAOYSA-O 0.000 claims description 7
• LJVZXKFEAWRSJD-UHFFFAOYSA-N 4-[5-[2,7-dimethyl-8-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC1=C(C=2C=C(C=CC=2)C(F)(F)F)C2=NC(C)=CN2C=C1C1=CC=NN1C1=CC=C(C#N)C=C1 LJVZXKFEAWRSJD-UHFFFAOYSA-N 0.000 claims description 7
• DLBPIPKSUXWRGD-UHFFFAOYSA-N 4-[5-[2-amino-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]pyrazol-1-yl]-3-methylsulfonylbenzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C(=CC(=CC=2)C#N)S(C)(=O)=O)=CN2N=C(N)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 DLBPIPKSUXWRGD-UHFFFAOYSA-N 0.000 claims description 7
• XXDXYCAVBPBMSE-UHFFFAOYSA-N 4-[5-[7-methyl-2-[(4-methylsulfonylphenyl)methyl]-3-oxo-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1=C(C)C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN(C2=O)C1=NN2CC1=CC=C(S(C)(=O)=O)C=C1 XXDXYCAVBPBMSE-UHFFFAOYSA-N 0.000 claims description 7
• NKIGFRNRWNBYOE-UHFFFAOYSA-N 4-[5-[7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=CN=C2C=1C1=CC=CC(C(F)(F)F)=C1 NKIGFRNRWNBYOE-UHFFFAOYSA-N 0.000 claims description 7
• CPGWEUYHMMXUIA-UHFFFAOYSA-N 4-[5-[7-methyl-8-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2C=CN=C2C=1C1=CC=CC(C(F)(F)F)=C1 CPGWEUYHMMXUIA-UHFFFAOYSA-N 0.000 claims description 7
• WCKQOFHFSNTTJK-UHFFFAOYSA-N 4-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-methylbutanamide Chemical compound C=1N2N=C(NCCCC(=O)NC)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 WCKQOFHFSNTTJK-UHFFFAOYSA-N 0.000 claims description 7
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 7
• AJGFASRKZWBWML-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)-1,2,4-triazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]acetamide Chemical compound C=1N2N=C(NC(=O)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=NC=NN1C1=CC=C(C#N)C=C1 AJGFASRKZWBWML-UHFFFAOYSA-N 0.000 claims description 7
• TYMYBXLYJIOHCW-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)-4-methylpyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]acetamide Chemical compound C=1N2N=C(NC(=O)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=C(C)C=NN1C1=CC=C(C#N)C=C1 TYMYBXLYJIOHCW-UHFFFAOYSA-N 0.000 claims description 7
• HTFLSSZGKNGUTI-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(methylamino)butanamide Chemical compound C=1N2N=C(NC(=O)CCCNC)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 HTFLSSZGKNGUTI-UHFFFAOYSA-N 0.000 claims description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• PGOZRUHIGFOGLW-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-morpholin-4-ylacetamide Chemical compound N1=C2C(C=3C=C(C=CC=3)C(F)(F)F)=C(C)C(C=3N(N=CC=3)C=3C=CC(=CC=3)C#N)=CN2N=C1NC(=O)CN1CCOCC1 PGOZRUHIGFOGLW-UHFFFAOYSA-N 0.000 claims description 6
• KOKATMWKTLHLEW-UHFFFAOYSA-N 4-[5-[2,7-dimethyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound C=1N2N=C(C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 KOKATMWKTLHLEW-UHFFFAOYSA-N 0.000 claims description 5
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 5
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
• 206010035664 Pneumonia Diseases 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 206010006451 bronchitis Diseases 0.000 claims description 5
• 208000007451 chronic bronchitis Diseases 0.000 claims description 5
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
• YWKCOWXYFKWGSW-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)phenyl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]acetamide Chemical compound CC=1C(C=2C(=CC=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(NC(=O)C)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 YWKCOWXYFKWGSW-UHFFFAOYSA-N 0.000 claims description 5
• KRAHROKJLPCJEB-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-(dimethylamino)acetamide Chemical compound C=1N2N=C(NC(=O)CN(C)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 KRAHROKJLPCJEB-UHFFFAOYSA-N 0.000 claims description 5
• RHJDDPCYJBOYBU-UHFFFAOYSA-N n-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(dimethylamino)butanamide Chemical compound C=1N2N=C(NC(=O)CCCN(C)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 RHJDDPCYJBOYBU-UHFFFAOYSA-N 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 229940080818 propionamide Drugs 0.000 claims description 5
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
• XWSVUETZOWEPHI-UHFFFAOYSA-N 1-(1-acetylpiperidin-4-yl)-3-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]urea Chemical compound C1CN(C(=O)C)CCC1NC(=O)NC1=NN2C=C(C=3N(N=CC=3)C=3C=CC(=CC=3)C#N)C(C)=C(C=3C=C(C=CC=3)C(F)(F)F)C2=N1 XWSVUETZOWEPHI-UHFFFAOYSA-N 0.000 claims description 4
• GGXOSOIDWVMOHE-UHFFFAOYSA-N 1-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-1-(1-methylpiperidin-4-yl)urea Chemical compound C1CN(C)CCC1N(C(N)=O)C1=NN2C=C(C=3N(N=CC=3)C=3C=CC(=CC=3)C#N)C(C)=C(C=3C=C(C=CC=3)C(F)(F)F)C2=N1 GGXOSOIDWVMOHE-UHFFFAOYSA-N 0.000 claims description 4
• KUOGKOIBQSPHIG-UHFFFAOYSA-N 1-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-(1-methylsulfonylpiperidin-4-yl)urea Chemical compound N1=C2C(C=3C=C(C=CC=3)C(F)(F)F)=C(C)C(C=3N(N=CC=3)C=3C=CC(=CC=3)C#N)=CN2N=C1NC(=O)NC1CCN(S(C)(=O)=O)CC1 KUOGKOIBQSPHIG-UHFFFAOYSA-N 0.000 claims description 4
• FLHLKZDQMFRSPF-UHFFFAOYSA-N 1-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-ethylurea Chemical compound C=1N2N=C(NC(=O)NCC)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 FLHLKZDQMFRSPF-UHFFFAOYSA-N 0.000 claims description 4
• XKGIKFJIRSXCHI-UHFFFAOYSA-N 2-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-3-oxo-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]-n,n-dimethylacetamide Chemical compound C=1N2C(=O)N(CC(=O)N(C)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 XKGIKFJIRSXCHI-UHFFFAOYSA-N 0.000 claims description 4
• GRYQPVQRKIVFNJ-UHFFFAOYSA-N 2-[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-3-oxo-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]-n-methylacetamide Chemical compound C=1N2C(=O)N(CC(=O)NC)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 GRYQPVQRKIVFNJ-UHFFFAOYSA-N 0.000 claims description 4
• PRSOXHJHWRIYCJ-UHFFFAOYSA-N 2-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n,n-dimethylacetamide Chemical compound C=1N2N=C(NCC(=O)N(C)C)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 PRSOXHJHWRIYCJ-UHFFFAOYSA-N 0.000 claims description 4
• HCCUBQOMLGTCDU-UHFFFAOYSA-O 3-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]carbamoyloxy]propyl-trimethylazanium Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(NC(=O)OCCC[N+](C)(C)C)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 HCCUBQOMLGTCDU-UHFFFAOYSA-O 0.000 claims description 4
• XVDWNCVRECCTIA-UHFFFAOYSA-N 4-[5-[2-methoxy-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound C=1N2N=C(OC)N=C2C(C=2C=C(C=CC=2)C(F)(F)F)=C(C)C=1C1=CC=NN1C1=CC=C(C#N)C=C1 XVDWNCVRECCTIA-UHFFFAOYSA-N 0.000 claims description 4
• RRRCMXMSNOHOOI-UHFFFAOYSA-N 4-[5-[7-methyl-2-(3-methylsulfonylpropyl)-3-oxo-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyrazol-1-yl]benzonitrile Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN(C(N(CCCS(C)(=O)=O)N=2)=O)C=2C=1C1=CC=CC(C(F)(F)F)=C1 RRRCMXMSNOHOOI-UHFFFAOYSA-N 0.000 claims description 4
• AYSPRDHJYWDHLH-UHFFFAOYSA-N 4-[[6-[2-(4-cyanophenyl)pyrazol-3-yl]-7-methyl-8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]butyl-trimethylazanium Chemical compound CC=1C(C=2N(N=CC=2)C=2C=CC(=CC=2)C#N)=CN2N=C(NCCCC[N+](C)(C)C)N=C2C=1C1=CC=CC(C(F)(F)F)=C1 AYSPRDHJYWDHLH-UHFFFAOYSA-N 0.000 claims description 4
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 4
• 229940077388 benzenesulfonate Drugs 0.000 claims description 4
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