JP6707630B2 - 置換ピラゾールおよびピロール化合物、および翻訳開始の阻害およびこれらに関連する疾患および障害の治療のためにこれらを用いる方法 - Google Patents

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Publication number

JP6707630B2

JP6707630B2 JP2018515175A JP2018515175A JP6707630B2 JP 6707630 B2 JP6707630 B2 JP 6707630B2 JP 2018515175 A JP2018515175 A JP 2018515175A JP 2018515175 A JP2018515175 A JP 2018515175A JP 6707630 B2 JP6707630 B2 JP 6707630B2

Authority

JP

Japan

Prior art keywords

methyl

pyrazole

isopropylthio

thiazol

carboxylic acid

Prior art date

2015-06-01

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.)

Expired - Fee Related

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• 238000000034 method Methods 0.000 title description 17
• 230000014621 translational initiation Effects 0.000 title description 14
• 230000002401 inhibitory effect Effects 0.000 title description 8
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 title 1
• 208000037765 diseases and disorders Diseases 0.000 title 1
• 150000003233 pyrroles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 311
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 196
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 170
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 229910052739 hydrogen Inorganic materials 0.000 claims description 130
• -1 amino, thio Chemical group 0.000 claims description 120
• 229910052757 nitrogen Inorganic materials 0.000 claims description 113
• 125000003342 alkenyl group Chemical group 0.000 claims description 97
• 125000001072 heteroaryl group Chemical group 0.000 claims description 83
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 81
• 125000000304 alkynyl group Chemical group 0.000 claims description 80
• 229910052799 carbon Inorganic materials 0.000 claims description 78
• 239000001257 hydrogen Substances 0.000 claims description 68
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
• 125000002947 alkylene group Chemical group 0.000 claims description 63
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 239000002253 acid Substances 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 239000005973 Carvone Substances 0.000 claims description 48
• 125000004419 alkynylene group Chemical group 0.000 claims description 41
• 125000004450 alkenylene group Chemical group 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 39
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 36
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 34
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 33
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 150000001204 N-oxides Chemical class 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 20
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 19
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims description 17
• 239000001301 oxygen Chemical group 0.000 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
• 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims description 15
• 239000000460 chlorine Substances 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 10
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 10
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 10
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 10
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 10
• 229930192474 thiophene Natural products 0.000 claims description 10
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• SPXQGJRTQRWZCG-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F SPXQGJRTQRWZCG-UHFFFAOYSA-N 0.000 claims description 7
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 6
• ZYHABNFDFIHEFJ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-[3-methyl-5-(oxetan-3-yloxy)phenyl]pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)OC1COC1)C)C ZYHABNFDFIHEFJ-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• FTQXWYBRAYQEDN-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(1,3-dimethylpyrazol-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CN(N=C1C)C)C FTQXWYBRAYQEDN-UHFFFAOYSA-N 0.000 claims description 3
• WZSIZQBEXCGFBO-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,5-dimethylpyrazol-3-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1N(N=C(C=1)C)C)C WZSIZQBEXCGFBO-UHFFFAOYSA-N 0.000 claims description 3
• ZCVPQQUCFNXFNZ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C ZCVPQQUCFNXFNZ-UHFFFAOYSA-N 0.000 claims description 3
• SLXGLIYUQYJCNL-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-imidazol-1-yl-5-methylphenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound N1(C=NC=C1)C=1C=C(C=C(C=1)C)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C SLXGLIYUQYJCNL-UHFFFAOYSA-N 0.000 claims description 3
• HJDIKUMLROUTKZ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-methoxyphenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)OC)C HJDIKUMLROUTKZ-UHFFFAOYSA-N 0.000 claims description 3
• TXUUSLFWGCBLFM-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(2-methyl-6-morpholin-4-ylpyridin-4-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)N1CCOCC1)C)C TXUUSLFWGCBLFM-UHFFFAOYSA-N 0.000 claims description 3
• HXIAHOSYXKRDKO-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(3-methyl-5-propan-2-yloxyphenyl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)C)OC(C)C)C HXIAHOSYXKRDKO-UHFFFAOYSA-N 0.000 claims description 3
• NMGNNTDQDGNCMF-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(3-methylphenyl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1C=C(C=CC=1)C)C NMGNNTDQDGNCMF-UHFFFAOYSA-N 0.000 claims description 3
• YADNNXVQXLFPNK-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(3-nitrophenyl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)[N+](=O)[O-])C YADNNXVQXLFPNK-UHFFFAOYSA-N 0.000 claims description 3
• DKEAWIWYEVCZRI-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-phenylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC=CC=C1)C DKEAWIWYEVCZRI-UHFFFAOYSA-N 0.000 claims description 3
• ZFNWONWIYDABIQ-UHFFFAOYSA-N 2-[4-(5-chloro-2-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=CC(=C(C=1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)F ZFNWONWIYDABIQ-UHFFFAOYSA-N 0.000 claims description 3
• JQSPKELXHMTKCP-UHFFFAOYSA-N 2-[5-butan-2-ylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)(CC)SC1=C(N=C(S1)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)C1=CC(=C(C=C1)Cl)Cl JQSPKELXHMTKCP-UHFFFAOYSA-N 0.000 claims description 3
• VUCMGZNEECFOJJ-UHFFFAOYSA-N 2-[5-butan-2-ylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-(3,5-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)(CC)SC1=C(N=C(S1)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)Cl)Cl)C)C1=CC(=C(C=C1)Cl)Cl VUCMGZNEECFOJJ-UHFFFAOYSA-N 0.000 claims description 3
• GGQMECZUGFSNLO-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-2-[4-(3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=CC=C1)OC)SC(C)C)C)C GGQMECZUGFSNLO-UHFFFAOYSA-N 0.000 claims description 3
• JDHFXUABCVDJAQ-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-(4-phenyl-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=CC=C1)SC(C)C)C)C JDHFXUABCVDJAQ-UHFFFAOYSA-N 0.000 claims description 3
• GBUOPKAGDIQVTN-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[4-(2-phenylethynyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C#CC1=CC=CC=C1)SC(C)C)C)C GBUOPKAGDIQVTN-UHFFFAOYSA-N 0.000 claims description 3
• MOKJTKYOFMWHRV-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[4-(3-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=C(C=CC=1)C)SC(C)C)C)C MOKJTKYOFMWHRV-UHFFFAOYSA-N 0.000 claims description 3
• DIXZHIXNBFQRDR-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C(=NOC=1C)C)SC(C)C)C DIXZHIXNBFQRDR-UHFFFAOYSA-N 0.000 claims description 3
• CMESLHPIQDIEGL-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-5-methyl-2-[4-(1-methylpyrazol-4-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NN(C=1)C)SC(C)C)C CMESLHPIQDIEGL-UHFFFAOYSA-N 0.000 claims description 3
• CECDCHBVADXEHN-UHFFFAOYSA-N 4-(3-benzyl-5-methyl-1,2-oxazol-4-yl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)C1=NOC(=C1C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)C CECDCHBVADXEHN-UHFFFAOYSA-N 0.000 claims description 3
• VHQGALFAMVLQLA-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C VHQGALFAMVLQLA-UHFFFAOYSA-N 0.000 claims description 3
• QDERFYINTAKVBB-UHFFFAOYSA-N 4-[3-cyano-5-(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound C(#N)C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C QDERFYINTAKVBB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• FXJWKBXZBSCNKY-UHFFFAOYSA-N methyl 2-[5-butan-2-ylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylate Chemical compound C(C)(CC)SC1=C(N=C(S1)N1N=C(C(=C1C(=O)OC)C1=CC(=NC(=C1)C)C)C)C1=CC(=C(C=C1)Cl)Cl FXJWKBXZBSCNKY-UHFFFAOYSA-N 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• SMVNDYKPVGNTMG-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C SMVNDYKPVGNTMG-UHFFFAOYSA-N 0.000 claims description 2
• PBRDGBTWDZRCOW-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(1,5-dimethyl-6-oxopyridin-3-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CN(C(C(=C1)C)=O)C)C PBRDGBTWDZRCOW-UHFFFAOYSA-N 0.000 claims description 2
• QZFYRPYHSUVUET-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3,5-difluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)F)F)C QZFYRPYHSUVUET-UHFFFAOYSA-N 0.000 claims description 2
• FRQQCYFOYWIVFT-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3,5-dimethylphenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)C)C)C FRQQCYFOYWIVFT-UHFFFAOYSA-N 0.000 claims description 2
• GHVGRKSEXVZNGF-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C GHVGRKSEXVZNGF-UHFFFAOYSA-N 0.000 claims description 2
• UZNQVSSGSASJAF-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-methoxy-5-(trifluoromethyl)phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)C(F)(F)F)OC)C UZNQVSSGSASJAF-UHFFFAOYSA-N 0.000 claims description 2
• BWZUQNHFWBSMAB-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(1-methylindol-7-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1C=CC=C2C=CN(C=12)C)C BWZUQNHFWBSMAB-UHFFFAOYSA-N 0.000 claims description 2
• OOANXQQUPKQTTJ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(2-methylphenyl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=C(C=CC=C1)C)C OOANXQQUPKQTTJ-UHFFFAOYSA-N 0.000 claims description 2
• LYQKAZZHUBBREW-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(3-methyl-1,2-thiazol-5-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NS1)C)C LYQKAZZHUBBREW-UHFFFAOYSA-N 0.000 claims description 2
• DVYCFNZMSKHLDX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(3-propan-2-ylphenyl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)C(C)C)C DVYCFNZMSKHLDX-UHFFFAOYSA-N 0.000 claims description 2
• IRMDSVOXTWCHSR-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-pyrimidin-5-ylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1C=NC=NC=1)C IRMDSVOXTWCHSR-UHFFFAOYSA-N 0.000 claims description 2
• HMFLZQRJNRRHSW-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-N-methylsulfonylpyrazole-3-carboxamide Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)NS(=O)(=O)C)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F HMFLZQRJNRRHSW-UHFFFAOYSA-N 0.000 claims description 2
• YPOPOSCHIMBRSP-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxamide Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)N)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F YPOPOSCHIMBRSP-UHFFFAOYSA-N 0.000 claims description 2
• VYQHJFFXRUQLFN-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-N,N,5-trimethylpyrazole-3-carboxamide Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)N(C)C)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F VYQHJFFXRUQLFN-UHFFFAOYSA-N 0.000 claims description 2
• NWGAOOYLLAKCQP-UHFFFAOYSA-N 4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-N-(2-hydroxyethyl)-N,5-dimethylpyrazole-3-carboxamide Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)N(C)CCO)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F NWGAOOYLLAKCQP-UHFFFAOYSA-N 0.000 claims description 2
• QLDAMYPDANIFDH-UHFFFAOYSA-N N-(2-aminoethyl)-4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-N,5-dimethylpyrazole-3-carboxamide Chemical compound NCCN(C(=O)C1=C(C(=NN1C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C QLDAMYPDANIFDH-UHFFFAOYSA-N 0.000 claims description 2
• XUISQVPDUNMFRC-UHFFFAOYSA-N [4-(aminomethyl)piperidin-1-yl]-[4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazol-3-yl]methanone Chemical compound NCC1CCN(CC1)C(=O)C1=C(C(=NN1C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F XUISQVPDUNMFRC-UHFFFAOYSA-N 0.000 claims description 2
• TXEPASFKYCLCSI-UHFFFAOYSA-N [4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazol-3-yl]-[4-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)N1CCC(CC1)CO)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F TXEPASFKYCLCSI-UHFFFAOYSA-N 0.000 claims description 2
• YEQKNFWDLQVYLX-UHFFFAOYSA-N [4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazol-3-yl]-morpholin-4-ylmethanone Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)C=1C(=NN(C=1C(=O)N1CCOCC1)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C)(F)F YEQKNFWDLQVYLX-UHFFFAOYSA-N 0.000 claims description 2
• MAGIWMNZKZNOJX-UHFFFAOYSA-N methyl 2-[5-butan-2-ylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-(3,5-dichlorophenyl)-5-methylpyrazole-3-carboxylate Chemical compound C(C)(CC)SC1=C(N=C(S1)N1N=C(C(=C1C(=O)OC)C1=CC(=CC(=C1)Cl)Cl)C)C1=CC(=C(C=C1)Cl)Cl MAGIWMNZKZNOJX-UHFFFAOYSA-N 0.000 claims description 2
• KYCNFLXMOJWIKM-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[4-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazol-3-yl]methanone Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(=O)N1CC(N)C1)-c1cc(cc(c1)C(F)(F)F)C(F)(F)F KYCNFLXMOJWIKM-UHFFFAOYSA-N 0.000 claims 1
• NOAUQEDTMWBIPH-UHFFFAOYSA-N 2-[4-(1,5-dimethyl-6-oxopyridin-3-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CN1C=C(C=C(C1=O)C)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C NOAUQEDTMWBIPH-UHFFFAOYSA-N 0.000 claims 1
• ROWKJAIHSSRAAB-UHFFFAOYSA-N 2-[4-(1-benzofuran-2-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound O1C(=CC2=C1C=CC=C2)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C ROWKJAIHSSRAAB-UHFFFAOYSA-N 0.000 claims 1
• XIGCXLSBFVRWDE-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=CC(=C1)Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C XIGCXLSBFVRWDE-UHFFFAOYSA-N 0.000 claims 1
• UWWPBPYFPFUZNU-UHFFFAOYSA-N 2-[4-(2,5-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1cc(Cl)ccc1Cl)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 UWWPBPYFPFUZNU-UHFFFAOYSA-N 0.000 claims 1
• DAGKNEHTYSRRKR-UHFFFAOYSA-N 2-[4-(2,5-dimethylpyrazol-3-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1cc(C)nn1C)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 DAGKNEHTYSRRKR-UHFFFAOYSA-N 0.000 claims 1
• JBEKYUBGXZLICQ-UHFFFAOYSA-N 2-[4-(2,6-dimethylpyridin-4-yl)-3,5-dimethylpyrazol-1-yl]-5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(F)(F)F)-n1nc(C)c(c1C)-c1cc(C)nc(C)c1 JBEKYUBGXZLICQ-UHFFFAOYSA-N 0.000 claims 1
• YPLVPCMOJJJSTQ-UHFFFAOYSA-N 2-[4-(2-cyanophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(#N)C1=C(C=CC=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C YPLVPCMOJJJSTQ-UHFFFAOYSA-N 0.000 claims 1
• SMWZZSCNDZZXQM-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(1H-imidazol-2-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2ncc[nH]2)c1C(O)=O SMWZZSCNDZZXQM-UHFFFAOYSA-N 0.000 claims 1
• KUWLKOPHYVOZFA-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2-methoxy-6-methylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)OC)C KUWLKOPHYVOZFA-UHFFFAOYSA-N 0.000 claims 1
• RAUHSDFGZIRUAC-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2-methoxyphenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound COc1ccccc1-c1c(C)nn(-c2nc(c(SC(C)C)s2)-c2ccc(Cl)c(Cl)c2)c1C(O)=O RAUHSDFGZIRUAC-UHFFFAOYSA-N 0.000 claims 1
• BSEVELVVEZCQES-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3,5-dimethyl-1,2-oxazol-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2c(C)noc2C)c1C(O)=O BSEVELVVEZCQES-UHFFFAOYSA-N 0.000 claims 1
• UWTBIFKQUHBOEJ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-propan-2-ylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C(C)C UWTBIFKQUHBOEJ-UHFFFAOYSA-N 0.000 claims 1
• VCEIHLJHLFKSBZ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(4,6-dimethylpyrimidin-2-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=NC(=CC(=N1)C)C)C VCEIHLJHLFKSBZ-UHFFFAOYSA-N 0.000 claims 1
• UZRUYXNBGCPHKM-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(4-methoxyphenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound COc1ccc(cc1)-c1c(C)nn(-c2nc(c(SC(C)C)s2)-c2ccc(Cl)c(Cl)c2)c1C(O)=O UZRUYXNBGCPHKM-UHFFFAOYSA-N 0.000 claims 1
• WZLOODZZJVIIJE-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[1-(2-methoxyethyl)pyrazol-4-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CN(N=C1)CCOC)C WZLOODZZJVIIJE-UHFFFAOYSA-N 0.000 claims 1
• FUCFDUUESODUTF-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[1-(dimethylcarbamoyl)pyrazol-4-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2cnn(c2)C(=O)N(C)C)c1C(O)=O FUCFDUUESODUTF-UHFFFAOYSA-N 0.000 claims 1
• CRQNIAVUIHMPOW-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[2-(2-methoxyethoxy)-6-methylpyridin-4-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)OCCOC)C CRQNIAVUIHMPOW-UHFFFAOYSA-N 0.000 claims 1
• ZUXHJDXGIOUGGZ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-(dimethylamino)-5-methylphenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)C)N(C)C)C ZUXHJDXGIOUGGZ-UHFFFAOYSA-N 0.000 claims 1
• WZMRXKKRAKRMLX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-(hydroxymethyl)-5-methyl-1,2-oxazol-4-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2c(C)onc2CO)c1C(O)=O WZMRXKKRAKRMLX-UHFFFAOYSA-N 0.000 claims 1
• KQUGRTGWCAZPHE-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-(hydroxymethyl)phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1cccc(CO)c1 KQUGRTGWCAZPHE-UHFFFAOYSA-N 0.000 claims 1
• FXYLOVCJVYAFFU-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-(methoxymethyl)-5-methyl-1,2-oxazol-4-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound COCc1noc(C)c1-c1c(C)nn(-c2nc(c(SC(C)C)s2)-c2ccc(Cl)c(Cl)c2)c1C(O)=O FXYLOVCJVYAFFU-UHFFFAOYSA-N 0.000 claims 1
• WLWCAAXRVDQGJH-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-(methoxymethyl)phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)COC)C WLWCAAXRVDQGJH-UHFFFAOYSA-N 0.000 claims 1
• LPCCCTKLINIWAJ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-[(dimethylamino)methyl]phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1cccc(CN(C)C)c1 LPCCCTKLINIWAJ-UHFFFAOYSA-N 0.000 claims 1
• NKBKGZJISGHNPB-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[3-fluoro-5-(oxetan-3-yloxy)phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC(=C1)OC1COC1)F)C NKBKGZJISGHNPB-UHFFFAOYSA-N 0.000 claims 1
• CIFOXLJQSLUULJ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[4-(hydroxymethyl)phenyl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1ccc(CO)cc1 CIFOXLJQSLUULJ-UHFFFAOYSA-N 0.000 claims 1
• TXYJFSSQZMISLF-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-imidazo[1,2-a]pyridin-3-yl-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CN=C2N1C=CC=C2)C TXYJFSSQZMISLF-UHFFFAOYSA-N 0.000 claims 1
• XSQZPLDAGRTMDC-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(1,2-thiazol-4-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1C=NSC=1)C XSQZPLDAGRTMDC-UHFFFAOYSA-N 0.000 claims 1
• BCLIUOTVGBQKPC-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(1-methyl-2-oxopyridin-4-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(N(C=C1)C)=O)C BCLIUOTVGBQKPC-UHFFFAOYSA-N 0.000 claims 1
• DDRZSAYZFVOIHA-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(1-methylpyrazol-4-yl)pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2cnn(C)c2)c1C(O)=O DDRZSAYZFVOIHA-UHFFFAOYSA-N 0.000 claims 1
• XNWJIQSWKDXBFO-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(1H-pyrazol-4-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CNN=C1)C XNWJIQSWKDXBFO-UHFFFAOYSA-N 0.000 claims 1
• HUDGHKUNUOHSFB-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(4-methylphenyl)pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1ccc(C)cc1 HUDGHKUNUOHSFB-UHFFFAOYSA-N 0.000 claims 1
• XMDBLGXZZHYRKC-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C=1SC(=NN=1)C)C XMDBLGXZZHYRKC-UHFFFAOYSA-N 0.000 claims 1
• CMRNNUOMLDOYLV-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-[2-(methylamino)pyridin-4-yl]pyrazole-3-carboxylic acid Chemical compound CNc1cc(ccn1)-c1c(C)nn(-c2nc(c(SC(C)C)s2)-c2ccc(Cl)c(Cl)c2)c1C(O)=O CMRNNUOMLDOYLV-UHFFFAOYSA-N 0.000 claims 1
• GLHVEXREDGAVAX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-pyrazin-2-ylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=NC=CN=C1)C GLHVEXREDGAVAX-UHFFFAOYSA-N 0.000 claims 1
• IGBQLNJDAUKXHU-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-pyridin-3-ylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1cccnc1 IGBQLNJDAUKXHU-UHFFFAOYSA-N 0.000 claims 1
• YOTBRZLOECNIQH-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-pyridin-4-ylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC=NC=C1)C YOTBRZLOECNIQH-UHFFFAOYSA-N 0.000 claims 1
• DTODNZCFHDWJHA-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-N-(2-methoxyethyl)-5-methyl-4-(3-methylphenyl)pyrazole-3-carboxamide Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)NCCOC)C=1C=C(C=CC=1)C)C DTODNZCFHDWJHA-UHFFFAOYSA-N 0.000 claims 1
• NJBHUIGRERBCTQ-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfonyl-1,3-thiazol-2-yl]-5-methyl-4-(1-methylpyrazol-4-yl)pyrazole-3-carboxylic acid Chemical compound CC(C)S(=O)(=O)c1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(-c2cnn(C)c2)c1C(O)=O NJBHUIGRERBCTQ-UHFFFAOYSA-N 0.000 claims 1
• CJPBBCPHXNTNRY-UHFFFAOYSA-N 2-[4-(3-chloro-4-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1C)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C CJPBBCPHXNTNRY-UHFFFAOYSA-N 0.000 claims 1
• SMFOVGUUZLFUAR-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C SMFOVGUUZLFUAR-UHFFFAOYSA-N 0.000 claims 1
• UPTHXPRMQXSQOZ-UHFFFAOYSA-N 2-[4-(3-fluoro-4-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(C)c(F)c1)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 UPTHXPRMQXSQOZ-UHFFFAOYSA-N 0.000 claims 1
• LDLCABFBODCIAY-UHFFFAOYSA-N 2-[4-(4-chloro-2,6-dimethylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=CC(=C(C(=C1)C)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C LDLCABFBODCIAY-UHFFFAOYSA-N 0.000 claims 1
• UAIBGLFUKRZFOL-UHFFFAOYSA-N 2-[4-(4-chloro-2-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=CC(=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)OC UAIBGLFUKRZFOL-UHFFFAOYSA-N 0.000 claims 1
• APERRSOLTNTBAT-UHFFFAOYSA-N 2-[4-(4-chloro-2-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound COc1cc(Cl)ccc1-c1nc(sc1SC(C)C)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 APERRSOLTNTBAT-UHFFFAOYSA-N 0.000 claims 1
• ZZRFJOXPLSEOKX-UHFFFAOYSA-N 2-[4-(4-chloro-2-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)cc1C)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 ZZRFJOXPLSEOKX-UHFFFAOYSA-N 0.000 claims 1
• VVOBMFBSUFCBTG-UHFFFAOYSA-N 2-[4-(4-chloro-3,5-difluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1F)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)F VVOBMFBSUFCBTG-UHFFFAOYSA-N 0.000 claims 1
• ORSQSKGGBCEGMI-UHFFFAOYSA-N 2-[4-(4-chloro-3,5-difluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1F)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)F ORSQSKGGBCEGMI-UHFFFAOYSA-N 0.000 claims 1
• HFIQXKIONITWLB-UHFFFAOYSA-N 2-[4-(4-chloro-3-cyanophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C#N HFIQXKIONITWLB-UHFFFAOYSA-N 0.000 claims 1
• CPPCVBKYOCIASF-UHFFFAOYSA-N 2-[4-(4-chloro-3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)OC CPPCVBKYOCIASF-UHFFFAOYSA-N 0.000 claims 1
• VCRMCFNBVQTSME-UHFFFAOYSA-N 2-[4-(4-chloro-3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)OC VCRMCFNBVQTSME-UHFFFAOYSA-N 0.000 claims 1
• SDKJDOIQFOZQQE-UHFFFAOYSA-N 2-[4-(4-chloro-3-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=NC(=C1)C)C)C)C SDKJDOIQFOZQQE-UHFFFAOYSA-N 0.000 claims 1
• SRXLJVVLZGIGPV-UHFFFAOYSA-N 2-[4-(4-chloro-3-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C SRXLJVVLZGIGPV-UHFFFAOYSA-N 0.000 claims 1
• PTKVAGYCDFWYNI-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=CC=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C PTKVAGYCDFWYNI-UHFFFAOYSA-N 0.000 claims 1
• YSMZHPPXKHMYMV-UHFFFAOYSA-N 2-[4-(4-cyano-3-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(C#N)c(C)c1)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 YSMZHPPXKHMYMV-UHFFFAOYSA-N 0.000 claims 1
• KDSZWLSDLLFKBY-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(#N)C1=CC=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C KDSZWLSDLLFKBY-UHFFFAOYSA-N 0.000 claims 1
• GSIPKLJPLASQCB-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)C1=CC=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C GSIPKLJPLASQCB-UHFFFAOYSA-N 0.000 claims 1
• QKQVPPXAHQNESG-UHFFFAOYSA-N 2-[4-(4-fluoro-3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound FC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)OC QKQVPPXAHQNESG-UHFFFAOYSA-N 0.000 claims 1
• GJKXXTLZLMMUDN-UHFFFAOYSA-N 2-[4-(5-cyanopyridin-3-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1cncc(c1)C#N)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 GJKXXTLZLMMUDN-UHFFFAOYSA-N 0.000 claims 1
• PMYHLBILMVFUPH-UHFFFAOYSA-N 2-[4-[2-amino-4-(trifluoromethyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound NC1=C(C=CC(=C1)C(F)(F)F)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C PMYHLBILMVFUPH-UHFFFAOYSA-N 0.000 claims 1
• QLIJYPLNVMJMFJ-UHFFFAOYSA-N 2-[4-[2-chloro-5-(trifluoromethoxy)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1cc(OC(F)(F)F)ccc1Cl)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 QLIJYPLNVMJMFJ-UHFFFAOYSA-N 0.000 claims 1
• ZSZPDRBEGJCYEF-UHFFFAOYSA-N 2-[4-[4-(1,1-difluoroethyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(C)(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 ZSZPDRBEGJCYEF-UHFFFAOYSA-N 0.000 claims 1
• JOIKSTXYOXVAMT-UHFFFAOYSA-N 2-[4-[4-(difluoromethyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 JOIKSTXYOXVAMT-UHFFFAOYSA-N 0.000 claims 1
• WPDNASVPISYKQN-UHFFFAOYSA-N 2-[4-[4-(dimethylcarbamoyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CN(C(=O)C1=CC=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C WPDNASVPISYKQN-UHFFFAOYSA-N 0.000 claims 1
• ICVPLYYMPUXQQH-UHFFFAOYSA-N 2-[4-[4-chloro-3-(ethylcarbamoyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C(NCC)=O ICVPLYYMPUXQQH-UHFFFAOYSA-N 0.000 claims 1
• QLLYRQZOCSEFIF-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-2-[4-(2-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound COc1ccccc1-c1nc(sc1SC(C)C)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 QLLYRQZOCSEFIF-UHFFFAOYSA-N 0.000 claims 1
• UVMDQXFLRAXSHM-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-2-[4-(4-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(F)cc1)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 UVMDQXFLRAXSHM-UHFFFAOYSA-N 0.000 claims 1
• AFQXRNDMIMXCPC-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-2-[4-(4-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound COc1ccc(cc1)-c1nc(sc1SC(C)C)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 AFQXRNDMIMXCPC-UHFFFAOYSA-N 0.000 claims 1
• LQHPVOVCRXWRIZ-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[4-(2-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccccc1C)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 LQHPVOVCRXWRIZ-UHFFFAOYSA-N 0.000 claims 1
• KUNBHHGAFAIHBJ-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[4-(4-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(C)cc1)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(C)c1 KUNBHHGAFAIHBJ-UHFFFAOYSA-N 0.000 claims 1
• LJRJNGCNARWYBW-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)SC(C)C)C)C LJRJNGCNARWYBW-UHFFFAOYSA-N 0.000 claims 1
• AENDHTKVUZVCGR-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1ccccc1Cl AENDHTKVUZVCGR-UHFFFAOYSA-N 0.000 claims 1
• WCFJEFYTTOAEAO-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1ccc(F)c(F)c1 WCFJEFYTTOAEAO-UHFFFAOYSA-N 0.000 claims 1
• YHBFECVIZKHLOV-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C YHBFECVIZKHLOV-UHFFFAOYSA-N 0.000 claims 1
• AKRHBYATBBQGSH-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-[4-(3,5-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=CC(=C1)Cl)Cl)SC(C)C)C AKRHBYATBBQGSH-UHFFFAOYSA-N 0.000 claims 1
• RZMTURMKQKQTPV-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-5-methyl-2-(5-propan-2-ylsulfanyl-4-pyridin-3-yl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NC=CC=1)SC(C)C)C RZMTURMKQKQTPV-UHFFFAOYSA-N 0.000 claims 1
• IZCLSWLUQVPKDB-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-5-methyl-2-(5-propan-2-ylsulfanyl-4-pyridin-4-yl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=NC=C1)SC(C)C)C IZCLSWLUQVPKDB-UHFFFAOYSA-N 0.000 claims 1
• ZZHGJRLMSHTOID-UHFFFAOYSA-N 4-(3-chloro-5-methoxyphenyl)-5-methyl-2-(4-phenyl-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)OC)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=CC=C1)SC(C)C)C ZZHGJRLMSHTOID-UHFFFAOYSA-N 0.000 claims 1
• AGZCDYPFUZKGRO-UHFFFAOYSA-N 4-(3-chloro-5-methoxyphenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)OC)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)SC(C)C)C AGZCDYPFUZKGRO-UHFFFAOYSA-N 0.000 claims 1
• DDHXDZIUPLUIJN-UHFFFAOYSA-N 4-(3-chloro-5-propan-2-yloxyphenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)OC(C)C)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C DDHXDZIUPLUIJN-UHFFFAOYSA-N 0.000 claims 1
• PTQKNXFCSPKCSJ-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(3-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=CC=C1)F)SC(C)C)C PTQKNXFCSPKCSJ-UHFFFAOYSA-N 0.000 claims 1
• GEBIACHNTAMPIG-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(4-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)F)SC(C)C)C GEBIACHNTAMPIG-UHFFFAOYSA-N 0.000 claims 1
• LJDBULUBFCYDIC-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(4-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)OC)SC(C)C)C LJDBULUBFCYDIC-UHFFFAOYSA-N 0.000 claims 1
• WPGKCFWTBCKSBL-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(5-fluoropyridin-3-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NC=C(C=1)F)SC(C)C)C WPGKCFWTBCKSBL-UHFFFAOYSA-N 0.000 claims 1
• BKERHSQEIPQBPR-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-[4-(2-methoxyethylcarbamoyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)C(NCCOC)=O)SC(C)C)C BKERHSQEIPQBPR-UHFFFAOYSA-N 0.000 claims 1
• ZQPHEIORKWOJDL-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-(4-phenyl-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccccc1)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 ZQPHEIORKWOJDL-UHFFFAOYSA-N 0.000 claims 1
• JJWDZEXJXQTQMU-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-(5-propan-2-ylsulfanyl-4-pyrimidin-5-yl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NC=NC=1)SC(C)C)C JJWDZEXJXQTQMU-UHFFFAOYSA-N 0.000 claims 1
• OTDNZOBVLFHQIT-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[4-(4-methylsulfonylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)S(=O)(=O)C)SC(C)C)C OTDNZOBVLFHQIT-UHFFFAOYSA-N 0.000 claims 1
• BMXYRXJERBXSLF-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[4-[2-methyl-4-(trifluoromethoxy)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=C(C=C(C=C1)OC(F)(F)F)C)SC(C)C)C BMXYRXJERBXSLF-UHFFFAOYSA-N 0.000 claims 1
• MDMHLVQMOMDXDC-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[4-[2-methyl-4-(trifluoromethyl)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1C)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 MDMHLVQMOMDXDC-UHFFFAOYSA-N 0.000 claims 1
• FMHNBTKLMIOMFW-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NN(C=1)CC(F)(F)F)SC(C)C)C FMHNBTKLMIOMFW-UHFFFAOYSA-N 0.000 claims 1
• YVGHAXQJAUYQMP-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[2-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccccc1C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 YVGHAXQJAUYQMP-UHFFFAOYSA-N 0.000 claims 1
• CZDYAUBEINGBFB-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[2-(trifluoromethyl)pyrimidin-5-yl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NC(=NC=1)C(F)(F)F)SC(C)C)C CZDYAUBEINGBFB-UHFFFAOYSA-N 0.000 claims 1
• IQWLUTBGTQWWRQ-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[2-[4-(trifluoromethyl)phenyl]ethynyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1C#Cc1ccc(cc1)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 IQWLUTBGTQWWRQ-UHFFFAOYSA-N 0.000 claims 1
• QRYIRPDCNYIDNR-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1cccc(c1)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 QRYIRPDCNYIDNR-UHFFFAOYSA-N 0.000 claims 1
• MLOGPPXSMZEAKY-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(2,2,2-trifluoroethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(CC(F)(F)F)cc1)-n1nc(C)c(c1C(O)=O)-c1cccc(F)c1 MLOGPPXSMZEAKY-UHFFFAOYSA-N 0.000 claims 1
• GSNFPWJBJXXVOS-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)OC(F)(F)F)SC(C)C)C GSNFPWJBJXXVOS-UHFFFAOYSA-N 0.000 claims 1
• SUCBTCNLOGPBJT-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-N-propylsulfonylpyrazole-3-carboxamide Chemical compound CCCS(=O)(=O)NC(=O)c1c(c(C)nn1-c1nc(c(SC(C)C)s1)-c1ccc(cc1)C(F)(F)F)-c1cccc(F)c1 SUCBTCNLOGPBJT-UHFFFAOYSA-N 0.000 claims 1
• CSKLESTWCMVVHO-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)SC(C)C)C CSKLESTWCMVVHO-UHFFFAOYSA-N 0.000 claims 1
• UMHGEDUTBGXZAN-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[5-(trifluoromethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=NC=C(C=N1)C(F)(F)F)SC(C)C)C UMHGEDUTBGXZAN-UHFFFAOYSA-N 0.000 claims 1
• PDLSEKVRFZWELZ-UHFFFAOYSA-N 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[6-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C=1C=NC(=CC=1)C(F)(F)F)SC(C)C)C PDLSEKVRFZWELZ-UHFFFAOYSA-N 0.000 claims 1
• IYLDRJUEJLXASM-UHFFFAOYSA-N 4-(3-fluorophenyl)-N-(2-methoxyethyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxamide Chemical compound COCCNC(=O)c1c(c(C)nn1-c1nc(c(SC(C)C)s1)-c1ccc(cc1)C(F)(F)F)-c1cccc(F)c1 IYLDRJUEJLXASM-UHFFFAOYSA-N 0.000 claims 1
• IYNHFFAOCNUHNF-UHFFFAOYSA-N 4-(3-fluorophenyl)-N-(2-methoxyethyl)-N,5-dimethyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxamide Chemical compound COCCN(C)C(=O)c1c(c(C)nn1-c1nc(c(SC(C)C)s1)-c1ccc(cc1)C(F)(F)F)-c1cccc(F)c1 IYNHFFAOCNUHNF-UHFFFAOYSA-N 0.000 claims 1
• ARAPAQQMVXGSCE-UHFFFAOYSA-N 4-(3-fluorophenyl)-N-methoxy-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxamide Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)NOC)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)SC(C)C)C ARAPAQQMVXGSCE-UHFFFAOYSA-N 0.000 claims 1
• FWUDFVACFNSXDA-UHFFFAOYSA-N 4-(4-acetamidophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1ccc(NC(C)=O)cc1 FWUDFVACFNSXDA-UHFFFAOYSA-N 0.000 claims 1
• NPPJLFZNGOBJHY-UHFFFAOYSA-N 4-(4-aminophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound NC1=CC=C(C=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C NPPJLFZNGOBJHY-UHFFFAOYSA-N 0.000 claims 1
• LTQHZDWRLACDRH-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1ccc(Cl)cc1 LTQHZDWRLACDRH-UHFFFAOYSA-N 0.000 claims 1
• CQQNXQACOPFDDK-UHFFFAOYSA-N 4-(4-fluoro-3,5-dimethylphenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1cc(C)c(F)c(C)c1 CQQNXQACOPFDDK-UHFFFAOYSA-N 0.000 claims 1
• COHDOOWSZNXKMR-UHFFFAOYSA-N 4-(4-fluoro-3-methoxyphenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound COc1cc(ccc1F)-c1c(C)nn(-c2nc(c(SC(C)C)s2)-c2ccc(cc2)C(F)(F)F)c1C(O)=O COHDOOWSZNXKMR-UHFFFAOYSA-N 0.000 claims 1
• HQPGIDYZTWGHPO-UHFFFAOYSA-N 4-(4-fluoro-3-methylphenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound FC1=C(C=C(C=C1)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)SC(C)C)C)C HQPGIDYZTWGHPO-UHFFFAOYSA-N 0.000 claims 1
• PFUVUIKPNUDZPW-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(cc1)C(F)(F)F)-n1nc(C)c(c1C(O)=O)-c1ccc(F)cc1 PFUVUIKPNUDZPW-UHFFFAOYSA-N 0.000 claims 1
• WWNUVUUICLZWNY-UHFFFAOYSA-N 4-[2-(azetidin-1-yl)-6-methylpyridin-4-yl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1cc(C)nc(c1)N1CCC1 WWNUVUUICLZWNY-UHFFFAOYSA-N 0.000 claims 1
• CZNHTBFQFSUNLX-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccc(Cl)c(Cl)c1)-n1nc(C)c(c1C(O)=O)-c1cccc(CN)c1 CZNHTBFQFSUNLX-UHFFFAOYSA-N 0.000 claims 1
• KZSMQEYSHVBZKW-UHFFFAOYSA-N 4-[3-chloro-5-(2-methoxyethoxy)phenyl]-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=C(C=1)OCCOC)C=1C(=NN(C=1C(=O)O)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C KZSMQEYSHVBZKW-UHFFFAOYSA-N 0.000 claims 1
• ZTAMWGNUFWHFAG-UHFFFAOYSA-N 5-methyl-4-(1-methylpyrazol-4-yl)-2-(4-phenyl-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)pyrazole-3-carboxylic acid Chemical compound CC(C)Sc1sc(nc1-c1ccccc1)-n1nc(C)c(-c2cnn(C)c2)c1C(O)=O ZTAMWGNUFWHFAG-UHFFFAOYSA-N 0.000 claims 1
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• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
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• ZVZXNCOCDRJNRA-UHFFFAOYSA-N methyl 2-[5-cyclohexylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-5-methyl-4-[(2-nitrophenyl)methyl]pyrazole-3-carboxylate Chemical compound C1(CCCCC1)SC1=C(N=C(S1)N1N=C(C(=C1C(=O)OC)CC1=C(C=CC=C1)[N+](=O)[O-])C)C1=CC(=C(C=C1)Cl)Cl ZVZXNCOCDRJNRA-UHFFFAOYSA-N 0.000 description 2
• GSAWNWSBZIJKAS-UHFFFAOYSA-N methyl 4-(1H-benzimidazol-2-yl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound N1C(=NC2=C1C=CC=C2)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C GSAWNWSBZIJKAS-UHFFFAOYSA-N 0.000 description 2
• QFNVHOXQKVZENZ-UHFFFAOYSA-N methyl 4-(3-cyano-5-methylphenyl)-2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound C(#N)C=1C=C(C=C(C=1)C)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)SC(C)C)C QFNVHOXQKVZENZ-UHFFFAOYSA-N 0.000 description 2
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• PWBBDNGOMBNJJF-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-(2-methylpropyl)-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1CC(C)C)N1N=C(C=C1C(=O)OC)C PWBBDNGOMBNJJF-UHFFFAOYSA-N 0.000 description 1
• MKLSLSHAIWQYMW-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(1,3-dimethylpyrazol-4-yl)-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C1=CN(N=C1C)C)C MKLSLSHAIWQYMW-UHFFFAOYSA-N 0.000 description 1
• APIBYVHVMUCHCW-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,5-dimethylpyrazol-3-yl)-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C=1N(N=C(C=1)C)C)C APIBYVHVMUCHCW-UHFFFAOYSA-N 0.000 description 1
• XVVPSCYGNPJSHF-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3,5-dimethylphenyl)-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C1=CC(=CC(=C1)C)C)C XVVPSCYGNPJSHF-UHFFFAOYSA-N 0.000 description 1
• FCQUTKBLFXGPNN-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-[hydroxy(phenyl)methyl]-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C(C1=CC=CC=C1)O)C FCQUTKBLFXGPNN-UHFFFAOYSA-N 0.000 description 1
• XDYUGVNSSGALFR-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-[(2-nitrophenyl)methyl]pyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)CC1=C(C=CC=C1)[N+](=O)[O-])C XDYUGVNSSGALFR-UHFFFAOYSA-N 0.000 description 1
• NKVFWPWXSZPBPT-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-phenylpyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C1=CC=CC=C1)C NKVFWPWXSZPBPT-UHFFFAOYSA-N 0.000 description 1
• ZMUQIQNQGXPVCP-UHFFFAOYSA-N methyl 2-[4-(3,4-dichlorophenyl)-5-propylsulfanyl-1,3-thiazol-2-yl]-5-methyl-4-[(2-nitrophenyl)methyl]pyrazole-3-carboxylate Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SCCC)N1N=C(C(=C1C(=O)OC)CC1=C(C=CC=C1)[N+](=O)[O-])C ZMUQIQNQGXPVCP-UHFFFAOYSA-N 0.000 description 1
• DDLGZJSCMPMJOV-UHFFFAOYSA-N methyl 2-[4-(4-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(2,6-dimethylpyridin-4-yl)-5-methylpyrazole-3-carboxylate Chemical compound ClC1=CC=C(C=C1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)OC)C1=CC(=NC(=C1)C)C)C DDLGZJSCMPMJOV-UHFFFAOYSA-N 0.000 description 1
• OCMMILXLVYIKAV-UHFFFAOYSA-N methyl 2-[4-(5-chloro-2-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound ClC=1C=CC(=C(C=1)C=1N=C(SC=1SC(C)C)N1N=C(C=C1C(=O)OC)C)F OCMMILXLVYIKAV-UHFFFAOYSA-N 0.000 description 1
• FUVOOVXPGLIROC-UHFFFAOYSA-N methyl 2-[5-butan-2-ylsulfanyl-4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound C(C)(CC)SC1=C(N=C(S1)N1N=C(C=C1C(=O)OC)C)C1=CC(=C(C=C1)Cl)Cl FUVOOVXPGLIROC-UHFFFAOYSA-N 0.000 description 1
• MGIYCRUAYQQSNL-UHFFFAOYSA-N methyl 2-bromo-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1Br MGIYCRUAYQQSNL-UHFFFAOYSA-N 0.000 description 1
• ZJHHUMNZUAHZTL-UHFFFAOYSA-N methyl 4-(2,6-dimethylpyridin-4-yl)-2-[4-(3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=CC=C1)OC)SC(C)C)C)C ZJHHUMNZUAHZTL-UHFFFAOYSA-N 0.000 description 1
• BBVYAQVNSCZZNM-UHFFFAOYSA-N methyl 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-(4-phenyl-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)pyrazole-3-carboxylate Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC=CC=C1)SC(C)C)C)C BBVYAQVNSCZZNM-UHFFFAOYSA-N 0.000 description 1
• JYQKMSLLHRLWPJ-UHFFFAOYSA-N methyl 4-(2,6-dimethylpyridin-4-yl)-5-methyl-2-[4-(3-methylphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]pyrazole-3-carboxylate Chemical compound CC1=NC(=CC(=C1)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C=1C=C(C=CC=1)C)SC(C)C)C)C JYQKMSLLHRLWPJ-UHFFFAOYSA-N 0.000 description 1
• WGHNTAIAYWABNC-UHFFFAOYSA-N methyl 4-bromo-2-(4-bromo-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl)-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)Br)SC(C)C)C WGHNTAIAYWABNC-UHFFFAOYSA-N 0.000 description 1
• HNZMFVZPULTADD-UHFFFAOYSA-N methyl 4-bromo-2-[4-(2,4-dichlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=C(C=C(C=C1)Cl)Cl)SC(C)C)C HNZMFVZPULTADD-UHFFFAOYSA-N 0.000 description 1
• LAMIGYPXTOVASE-UHFFFAOYSA-N methyl 4-bromo-2-[4-(2-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=C(C=CC=C1)Cl)SC(C)C)C LAMIGYPXTOVASE-UHFFFAOYSA-N 0.000 description 1
• AKIPKPIILGRXOC-UHFFFAOYSA-N methyl 4-bromo-2-[4-(3,4-dichlorophenyl)-5-(2-methylpropyl)-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=C(C=C1)Cl)Cl)CC(C)C)C AKIPKPIILGRXOC-UHFFFAOYSA-N 0.000 description 1
• ZZFVLDNIFGXNHU-UHFFFAOYSA-N methyl 4-bromo-2-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C=1C(=NOC=1C)C)SC(C)C)C ZZFVLDNIFGXNHU-UHFFFAOYSA-N 0.000 description 1
• WIBZSDIJQZMGJH-UHFFFAOYSA-N methyl 4-bromo-2-[4-(3-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=CC=C1)Cl)SC(C)C)C WIBZSDIJQZMGJH-UHFFFAOYSA-N 0.000 description 1
• SLERBGLUNPGWQT-UHFFFAOYSA-N methyl 4-bromo-2-[4-(3-methoxyphenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC(=CC=C1)OC)SC(C)C)C SLERBGLUNPGWQT-UHFFFAOYSA-N 0.000 description 1
• YQLZJJBURLEQFE-UHFFFAOYSA-N methyl 4-bromo-2-[4-(4-chlorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CC=C(C=C1)Cl)SC(C)C)C YQLZJJBURLEQFE-UHFFFAOYSA-N 0.000 description 1
• SEJKMGXZLRJYKA-UHFFFAOYSA-N methyl 4-bromo-2-[4-(5-chloro-2-fluorophenyl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-5-methylpyrazole-3-carboxylate Chemical compound BrC=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=C(C=CC(=C1)Cl)F)SC(C)C)C SEJKMGXZLRJYKA-UHFFFAOYSA-N 0.000 description 1
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