JP2018521119A5 - - Google Patents
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- Publication number
- JP2018521119A5 JP2018521119A5 JP2018515175A JP2018515175A JP2018521119A5 JP 2018521119 A5 JP2018521119 A5 JP 2018521119A5 JP 2018515175 A JP2018515175 A JP 2018515175A JP 2018515175 A JP2018515175 A JP 2018515175A JP 2018521119 A5 JP2018521119 A5 JP 2018521119A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- isopropylthio
- pyrazole
- thiazol
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 amino, thio Chemical group 0.000 claims 92
- 239000002253 acid Substances 0.000 claims 34
- 239000005973 Carvone Substances 0.000 claims 26
- 229910052799 carbon Inorganic materials 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 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 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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
- QQRGKMYCQHDEGV-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound N1=C(C)C=C(C(O)=O)N1C1=CC=CC(F)=C1 QQRGKMYCQHDEGV-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
- 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
- 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 1
- 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 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
- 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 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
- 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 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
- 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 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
- 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
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
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- 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 1
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- 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 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
- 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 1
- 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 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
- 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 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
- 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 1
- 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 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
- 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 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
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 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
- IWEPNNGJGKPAEA-UHFFFAOYSA-N C1=C(C(C)=NN1C1=NC(=C(SC(C)C)S1)C1=CC=C(Cl)C(Cl)=C1)C1=CN(CC(C)C)N=C1 Chemical compound C1=C(C(C)=NN1C1=NC(=C(SC(C)C)S1)C1=CC=C(Cl)C(Cl)=C1)C1=CN(CC(C)C)N=C1 IWEPNNGJGKPAEA-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- HSGPTUYUMZQNJZ-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)C=1N=C(SC1SC(C)C)N1N=C(C(=C1)C1=CN(N=C1)CC)C Chemical compound ClC=1C=C(C=CC1Cl)C=1N=C(SC1SC(C)C)N1N=C(C(=C1)C1=CN(N=C1)CC)C HSGPTUYUMZQNJZ-UHFFFAOYSA-N 0.000 claims 1
- MIRKROSKUBLGGU-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1)C=1N(N=C(C=1)C)C)C Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1)C=1N(N=C(C=1)C)C)C MIRKROSKUBLGGU-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 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 1
- 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 1
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
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| PCT/US2016/035288 WO2016196644A1 (en) | 2015-06-01 | 2016-06-01 | Substituted pyrazole and pyrrole compounds and methods for using them for inhibition of initiation of translation and treatment of diseases and disorders relating thereto |
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| JP2018521119A JP2018521119A (ja) | 2018-08-02 |
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| JP (1) | JP6707630B2 (https=) |
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| IL (1) | IL255898A (https=) |
| MX (1) | MX2017015456A (https=) |
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| EP3303332A1 (en) | 2015-06-01 | 2018-04-11 | Bantam Pharmaceutical, LLC | Substituted pyrazole and pyrrole compounds and methods for using them for inhibition of initiation of translation and treatment of diseases and disorders relating thereto |
| MX2019006296A (es) * | 2016-11-30 | 2019-11-12 | Bantam Pharmaceutical Llc | Métodos de uso de compuestos de pirazol y pirazol sustituido y para el tratamiento de enfermedades hiperproliferativas. |
| AU2017366901B2 (en) * | 2016-11-30 | 2022-09-29 | Bantam Pharmaceutical, Llc | Substituted pyrazole compounds and methods of using them for treatment of hyperproliferative diseases |
| EP3778583B1 (en) | 2018-03-30 | 2025-06-18 | Sumitomo Chemical Company, Limited | Heterocyclic compound and arthropod pest control composition containing same |
| WO2019236966A2 (en) | 2018-06-07 | 2019-12-12 | Bantam Pharmaceutical, Llc | Methods of treatment of cancer with substituted pyrrole and pyrazole compounds and diagnosis of cancers susceptible to treatment with substituted pyrrole and pyrazole compounds |
| US12030875B2 (en) | 2018-09-07 | 2024-07-09 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
| CN110950848B (zh) * | 2018-09-27 | 2024-03-26 | 徐诺药业 | 新型氨基吡唑类衍生物的合成与应用 |
| WO2020243582A1 (en) * | 2019-05-31 | 2020-12-03 | Bantam Pharmaceutical, Llc | Methods for making thiszolylpyrazole carboxylic acids and intermediates therefor |
| JP7085697B2 (ja) | 2019-11-01 | 2022-06-16 | ユニマテック株式会社 | 含フッ素ピリミジン化合物およびその製造方法 |
| AU2021230289A1 (en) * | 2020-03-03 | 2022-09-29 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| US12157732B2 (en) | 2021-08-25 | 2024-12-03 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| JP2024534127A (ja) | 2021-08-25 | 2024-09-18 | ピク セラピューティクス， インコーポレイテッド | ｅＩＦ４Ｅ阻害剤及びその使用 |
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| US5342851A (en) * | 1992-10-07 | 1994-08-30 | Mcneil-Ppc, Inc. | Substituted thiazole derivatives useful as platelet aggregation inhibitors |
| IT1301968B1 (it) * | 1998-07-30 | 2000-07-20 | Zambon Spa | Derivati di eritromicina ad attivita' antibiotica |
| DE60006057T2 (de) * | 1999-12-03 | 2004-05-27 | Pfizer Products Inc., Groton | Heteroarylphenylpyrazolverbindungen zur Verwendung als analgetisches/entzündungshemmendes Mittel |
| US6900219B2 (en) | 2002-04-04 | 2005-05-31 | Cv Therapeutics, Inc. | ABCA-1 elevating compounds |
| AU2004228057A1 (en) | 2003-04-03 | 2004-10-21 | Merck & Co., Inc. | Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| EP1618099A4 (en) | 2003-04-18 | 2008-07-16 | Merck & Co Inc | BIARYLSUBSTITUTED DIAZOLE, OXAZOLE AND IMIDAZOLE AS SODIUM CHANNEL BLOCKERS |
| WO2007138110A2 (en) * | 2006-06-01 | 2007-12-06 | Devgen N.V. | Compounds that interact with ion channels, in particular with ion channels from the kv family |
| WO2008121861A2 (en) | 2007-03-28 | 2008-10-09 | Xenon Pharmaceuticals Inc. | Pyrazole and pyrrole compounds useful in treating iron disorders |
| US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| CN102056907B (zh) | 2008-04-04 | 2014-12-31 | 武田药品工业株式会社 | 杂环衍生物及其用途 |
| SI2275414T1 (sl) | 2008-04-28 | 2015-10-30 | Kyorin Pharmaceutical Co., Ltd., | Ciklopentilakrilamidni derivat |
| EP2651405A2 (en) * | 2010-12-14 | 2013-10-23 | Electrophoretics Limited | Casein kinase 1 (ck1 ) inhibitors |
| US9409901B2 (en) | 2012-10-22 | 2016-08-09 | Bantam Pharmaceutical, Llc | Compositions and methods for treating or preventing diseases or disorders associated with misregulated EIF4E |
| JP6434989B2 (ja) | 2014-03-27 | 2018-12-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ピリジルピペリジン |
| US10125139B2 (en) | 2015-04-24 | 2018-11-13 | Syngenta Crop Protection Ag | Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocycles |
| EP3303332A1 (en) | 2015-06-01 | 2018-04-11 | Bantam Pharmaceutical, LLC | Substituted pyrazole and pyrrole compounds and methods for using them for inhibition of initiation of translation and treatment of diseases and disorders relating thereto |
-
2016
- 2016-06-01 EP EP16728546.9A patent/EP3303332A1/en not_active Withdrawn
- 2016-06-01 CN CN201680045318.9A patent/CN108349962A/zh active Pending
- 2016-06-01 WO PCT/US2016/035288 patent/WO2016196644A1/en not_active Ceased
- 2016-06-01 MX MX2017015456A patent/MX2017015456A/es unknown
- 2016-06-01 US US15/578,585 patent/US10537558B2/en active Active
- 2016-06-01 CA CA3025492A patent/CA3025492A1/en not_active Abandoned
- 2016-06-01 BR BR112017025851-0A patent/BR112017025851A2/pt not_active Application Discontinuation
- 2016-06-01 JP JP2018515175A patent/JP6707630B2/ja not_active Expired - Fee Related
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2017
- 2017-11-26 IL IL255898A patent/IL255898A/en unknown
-
2020
- 2020-01-21 US US16/748,429 patent/US11602526B2/en active Active
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