CA2657670C - Triazolyl pyridyl benzenesulfonamides as ccr2 or ccr9 modulators for the treatment of inflammation - Google Patents

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Publication number

CA2657670C

CA2657670C CA2657670A CA2657670A CA2657670C CA 2657670 C CA2657670 C CA 2657670C CA 2657670 A CA2657670 A CA 2657670A CA 2657670 A CA2657670 A CA 2657670A CA 2657670 C CA2657670 C CA 2657670C

Authority

CA

Canada

Prior art keywords

substituted

unsubstituted

chloro

pyridin

triazol

Prior art date

2006-07-14

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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• 238000011282 treatment Methods 0.000 title claims description 32
• -1 Triazolyl pyridyl benzenesulfonamides Chemical class 0.000 title description 41
• 206010061218 Inflammation Diseases 0.000 title description 19
• 230000004054 inflammatory process Effects 0.000 title description 19
• 150000001875 compounds Chemical class 0.000 claims abstract description 287
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 103
• 101710149815 C-C chemokine receptor type 2 Proteins 0.000 claims abstract description 99
• 102100031151 C-C chemokine receptor type 2 Human genes 0.000 claims abstract description 99
• 201000010099 disease Diseases 0.000 claims abstract description 95
• 230000001404 mediated effect Effects 0.000 claims abstract description 58
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 30
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 23
• 208000008589 Obesity Diseases 0.000 claims abstract description 15
• 235000020824 obesity Nutrition 0.000 claims abstract description 15
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
• 102100022718 Atypical chemokine receptor 2 Human genes 0.000 claims abstract description 8
• 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 claims abstract description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
• 201000002793 renal fibrosis Diseases 0.000 claims abstract description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
• 208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 4
• 208000009329 Graft vs Host Disease Diseases 0.000 claims abstract description 4
• 208000024908 graft versus host disease Diseases 0.000 claims abstract description 4
• 208000037803 restenosis Diseases 0.000 claims abstract description 4
• 238000002054 transplantation Methods 0.000 claims abstract description 4
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 3
• 206010063725 Idiopathic pneumonia syndrome Diseases 0.000 claims abstract description 3
• 208000007915 ichthyosis prematurity syndrome Diseases 0.000 claims abstract description 3
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 3
• 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 claims abstract 7
• 206010058019 Cancer Pain Diseases 0.000 claims abstract 2
• 208000004296 neuralgia Diseases 0.000 claims abstract 2
• 208000021722 neuropathic pain Diseases 0.000 claims abstract 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 60
• 239000001257 hydrogen Substances 0.000 claims description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000003342 alkenyl group Chemical group 0.000 claims description 28
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 26
• 125000004429 atom Chemical group 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 18
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
• 239000000730 antalgic agent Substances 0.000 claims description 5
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
• 230000000699 topical effect Effects 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• IGLLECSQBYFOED-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-[5-(2-hydroxypropan-2-yl)-4-propan-2-yl-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound N1=C(C(C)(C)O)N(C(C)C)C(C=2C(=CC(Cl)=CN=2)NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)=N1 IGLLECSQBYFOED-UHFFFAOYSA-N 0.000 claims description 3
• KPBBXPDMTLDHTE-UHFFFAOYSA-N 5-[3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-5-methylpyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C=1C=C(Cl)C(C(F)(F)F)=CC=1S(=O)(=O)NC1=CC(C)=CN=C1C1=NN=C(C(N)=O)N1C=1C=CON=1 KPBBXPDMTLDHTE-UHFFFAOYSA-N 0.000 claims description 3
• CWEXICJJEOCLLQ-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 CWEXICJJEOCLLQ-UHFFFAOYSA-N 0.000 claims description 3
• QDTKHLLJQIJDAD-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(N)=O)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 QDTKHLLJQIJDAD-UHFFFAOYSA-N 0.000 claims description 3
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• VXHXALJHPTYTDH-UHFFFAOYSA-N ethyl 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-4-propan-2-yl-1,2,4-triazole-3-carboxylate Chemical compound CC(C)N1C(C(=O)OCC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 VXHXALJHPTYTDH-UHFFFAOYSA-N 0.000 claims description 3
• IVWRGIVDRLRAAX-UHFFFAOYSA-N 3,4-dichloro-n-[5-chloro-2-[4-(1,2-oxazol-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C=1C=CON=1 IVWRGIVDRLRAAX-UHFFFAOYSA-N 0.000 claims description 2
• RHJNSFYZLNEUAN-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-(4-propyl-1,2,4-triazol-3-yl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound CCCN1C=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 RHJNSFYZLNEUAN-UHFFFAOYSA-N 0.000 claims description 2
• CHLQUWDUVGXBII-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[4-(5-fluoro-2-methoxyphenyl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound COC1=CC=C(F)C=C1N1C(C=2C(=CC(Cl)=CN=2)NS(=O)(=O)C=2C=C(C(Cl)=CC=2)C(F)(F)F)=NN=C1 CHLQUWDUVGXBII-UHFFFAOYSA-N 0.000 claims description 2
• FSVGXDUCCAPWHU-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[4-(5-methyl-1h-pyrazol-4-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=NNC=C1N1C(C=2C(=CC(Cl)=CN=2)NS(=O)(=O)C=2C=C(C(Cl)=CC=2)C(F)(F)F)=NN=C1 FSVGXDUCCAPWHU-UHFFFAOYSA-N 0.000 claims description 2
• DETFXINXMZRPDU-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[5-(methoxymethyl)-4-(1,2-oxazol-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CON=C1N1C(COC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 DETFXINXMZRPDU-UHFFFAOYSA-N 0.000 claims description 2
• ZBKAQIOYWNGCKO-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[5-(morpholine-4-carbonyl)-4-(1,2-oxazol-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=C(Cl)C=2)C=2N(C(C(=O)N3CCOCC3)=NN=2)C2=NOC=C2)=C1 ZBKAQIOYWNGCKO-UHFFFAOYSA-N 0.000 claims description 2
• MRPYYDJYKUEABC-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[5-propan-2-yl-4-(1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CNN=C1N1C(C(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 MRPYYDJYKUEABC-UHFFFAOYSA-N 0.000 claims description 2
• SMVWBIYENSWUNX-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4,5-dimethyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CN1C(C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SMVWBIYENSWUNX-UHFFFAOYSA-N 0.000 claims description 2
• SHHWPVJOEJFQCM-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-cyclopropyl-5-methyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound C1CC1N1C(C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SHHWPVJOEJFQCM-UHFFFAOYSA-N 0.000 claims description 2
• BXSXXHMUFKTGHH-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-ethyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CCN1C=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 BXSXXHMUFKTGHH-UHFFFAOYSA-N 0.000 claims description 2
• HLXWKMFIGKMJDD-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-ethyl-5-methyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CCN1C(C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HLXWKMFIGKMJDD-UHFFFAOYSA-N 0.000 claims description 2
• KRSLPIOTISQBDG-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-methyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CN1C=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 KRSLPIOTISQBDG-UHFFFAOYSA-N 0.000 claims description 2
• KSKXPBYWJVPXQK-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-methyl-5-propan-2-yl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CN1C(C(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 KSKXPBYWJVPXQK-UHFFFAOYSA-N 0.000 claims description 2
• MRDSSVOCUFDQHI-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-phenyl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C1=CC=CC=C1 MRDSSVOCUFDQHI-UHFFFAOYSA-N 0.000 claims description 2
• FRNSKNFPAPCIPK-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(4-propan-2-yl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CC(C)N1C=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 FRNSKNFPAPCIPK-UHFFFAOYSA-N 0.000 claims description 2
• FMBHTODGYGFVLH-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=C2N1CCNC2 FMBHTODGYGFVLH-UHFFFAOYSA-N 0.000 claims description 2
• REWZJVONYAGOJV-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(5-methyl-4-propan-2-yl-1,2,4-triazol-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound CC(C)N1C(C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 REWZJVONYAGOJV-UHFFFAOYSA-N 0.000 claims description 2
• ZSBVYYGCIUDHDG-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-(6,8-dihydro-5h-[1,2,4]triazolo[3,4-c][1,4]oxazin-3-yl)pyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=C2N1CCOC2 ZSBVYYGCIUDHDG-UHFFFAOYSA-N 0.000 claims description 2
• NIHIQEBRJMOZPB-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-[4-(2-fluorophenyl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C1=CC=CC=C1F NIHIQEBRJMOZPB-UHFFFAOYSA-N 0.000 claims description 2
• LYPVETOSZCZAGI-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-[4-methyl-5-(1,2-oxazol-5-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound CN1C(C=2ON=CC=2)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 LYPVETOSZCZAGI-UHFFFAOYSA-N 0.000 claims description 2
• ZGCDEFWQIAZREQ-KRWDZBQOSA-N 4-tert-butyl-n-[5-chloro-2-[4-methyl-5-[(2s)-pyrrolidin-2-yl]-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound CN1C([C@H]2NCCC2)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ZGCDEFWQIAZREQ-KRWDZBQOSA-N 0.000 claims description 2
• VBMBAZMIWCNCTP-UHFFFAOYSA-N 4-tert-butyl-n-[5-chloro-2-[5-(methoxymethyl)-4-propan-2-yl-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound CC(C)N1C(COC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 VBMBAZMIWCNCTP-UHFFFAOYSA-N 0.000 claims description 2
• UCTRWFZNSGGYBI-UHFFFAOYSA-N 4-tert-butyl-n-[5-methyl-2-[4-(1-methylpyrrolidin-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C1N(C)CCC1N1C(C=2C(=CC(C)=CN=2)NS(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)=NN=C1 UCTRWFZNSGGYBI-UHFFFAOYSA-N 0.000 claims description 2
• JELORYBSSKXTKS-UHFFFAOYSA-N 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-n,n-dimethyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 JELORYBSSKXTKS-UHFFFAOYSA-N 0.000 claims description 2
• HMCRGZKZGJIKHJ-UHFFFAOYSA-N 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-n-methyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HMCRGZKZGJIKHJ-UHFFFAOYSA-N 0.000 claims description 2
• QHAFGHWVHRRHSV-UHFFFAOYSA-N 5-[3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-5-methylpyridin-2-yl]-4-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C=1C=C(Cl)C(C(F)(F)F)=CC=1S(=O)(=O)NC1=CC(C)=CN=C1C1=NN=C(C(N)=O)N1C1=CC=CC=C1 QHAFGHWVHRRHSV-UHFFFAOYSA-N 0.000 claims description 2
• NUOLRQJDNCPPQU-UHFFFAOYSA-N 5-[5-chloro-3-[(3,4-dichlorophenyl)sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 NUOLRQJDNCPPQU-UHFFFAOYSA-N 0.000 claims description 2
• MYDSZQFQVRXQPG-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n,n-dimethyl-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 MYDSZQFQVRXQPG-UHFFFAOYSA-N 0.000 claims description 2
• BTFFJIJPEWHEEM-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n,n-dimethyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 BTFFJIJPEWHEEM-UHFFFAOYSA-N 0.000 claims description 2
• ZOPRRQNFZVBNDG-UHFFFAOYSA-N 5-[5-chloro-3-[[4-methyl-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=C(C(N)=O)N1C1=NOC=C1 ZOPRRQNFZVBNDG-UHFFFAOYSA-N 0.000 claims description 2
• MCUNGNKSMZSFRI-UHFFFAOYSA-N n-[5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-4-propan-2-yl-1,2,4-triazol-3-yl]acetamide Chemical compound CC(C)N1C(NC(C)=O)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 MCUNGNKSMZSFRI-UHFFFAOYSA-N 0.000 claims description 2
• WPOHKZVWAATZAM-UHFFFAOYSA-N n-[5-bromo-2-[4-(1,2-oxazol-3-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-4-chloro-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=C(Br)C=2)C=2N(C=NN=2)C2=NOC=C2)=C1 WPOHKZVWAATZAM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 23
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 18
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 16
• XQQNPZZMXRJVDN-UHFFFAOYSA-N 3,4-dichloro-n-[5-chloro-2-[4-(1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C=1C=CNN=1 XQQNPZZMXRJVDN-UHFFFAOYSA-N 0.000 claims 1
• IPOYDFZVKIIIMX-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-(4-piperidin-4-yl-1,2,4-triazol-3-yl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=C(Cl)C=2)C=2N(C=NN=2)C2CCNCC2)=C1 IPOYDFZVKIIIMX-UHFFFAOYSA-N 0.000 claims 1
• YURPEELVLKBRLQ-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-(4-pyrrolidin-3-yl-1,2,4-triazol-3-yl)pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=C(Cl)C=2)C=2N(C=NN=2)C2CNCC2)=C1 YURPEELVLKBRLQ-UHFFFAOYSA-N 0.000 claims 1
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