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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| US10537558B2 (en) | 2015-06-01 | 2020-01-21 | 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 |
| US11779018B2 (en) | 2018-03-30 | 2023-10-10 | Sumitomo Chemical Company, Limited | Heterocyclic compound and arthropod pest control composition containing same |
| CN112770813A (zh) * | 2018-06-07 | 2021-05-07 | 班塔姆制药有限责任公司 | 用经取代的吡咯和吡唑化合物治疗癌症及诊断对用经取代的吡咯和吡唑化合物的治疗敏感的癌症的方法 |
| 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 |
| EP3976605B1 (en) * | 2019-05-31 | 2025-08-20 | Bantam Pharmaceutical, LLC | Methods for making thiazolylpyrazole carboxylic acids and intermediates therefor |
| EP4053123A4 (en) | 2019-11-01 | 2023-10-11 | Unimatec Co., Ltd. | FLUORINATED PYRIMIDINE COMPOUND AND METHOD FOR THE PRODUCTION THEREOF |
| CA3170411A1 (en) | 2020-03-03 | 2021-09-10 | Christopher L. Vandeusen | Eif4e inhibitors and uses thereof |
| CN118019739A (zh) | 2021-08-25 | 2024-05-10 | 皮克医疗公司 | Eif4e抑制剂及其用途 |
| US12234231B2 (en) | 2021-08-25 | 2025-02-25 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
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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 |
| DK1104759T3 (da) * | 1999-12-03 | 2004-01-26 | Pfizer Prod Inc | Heteroarylphenylpyrazolforbindelser som antiinflammatoriske/analgetiske midler |
| EP1513534A2 (en) * | 2002-04-04 | 2005-03-16 | Cv Therapeutics, Inc. | Compounds for increasing abca-1 expression useful for treating coronary artery disease and atherosclerosis |
| US20060194807A1 (en) | 2003-04-03 | 2006-08-31 | Cosford Nicholas D P | Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| WO2004094395A2 (en) | 2003-04-18 | 2004-11-04 | Merck & Co., Inc. | Biaryl substituted thiazoles, oxazoles and imidazoles 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 |
| KR20100065340A (ko) * | 2007-08-27 | 2010-06-16 | 바스프 에스이 | 무척추 해충을 방제하기 위한 피라졸 화합물 |
| US8461348B2 (en) | 2008-04-04 | 2013-06-11 | Takeda Pharmaceutical Company Limited | Heterocyclic derivative and use thereof |
| PT2275414E (pt) | 2008-04-28 | 2015-09-09 | Teijin Pharma Ltd | Derivado de amida do ácido ciclopentacrílico |
| AU2011343039B2 (en) * | 2010-12-14 | 2017-03-02 | Electrophoretics Limited | Casein kinase 1delta (CK1delta) inhibitors |
| JP2015534990A (ja) * | 2012-10-22 | 2015-12-07 | イージェニックス インコーポレイテッド | 誤制御されたｅＩＦ４Ｅに関連する疾患又は障害を治療又は予防するための組成物及び方法 |
| CA2943659C (en) | 2014-03-27 | 2023-04-25 | Merck Patent Gmbh | Pyridyl piperidines |
| US10125139B2 (en) | 2015-04-24 | 2018-11-13 | Syngenta Crop Protection Ag | Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocycles |
| US10537558B2 (en) | 2015-06-01 | 2020-01-21 | 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 |
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2016
- 2016-06-01 US US15/578,585 patent/US10537558B2/en active Active
- 2016-06-01 JP JP2018515175A patent/JP6707630B2/ja not_active Expired - Fee Related
- 2016-06-01 BR BR112017025851-0A patent/BR112017025851A2/pt not_active Application Discontinuation
- 2016-06-01 WO PCT/US2016/035288 patent/WO2016196644A1/en not_active Ceased
- 2016-06-01 CN CN201680045318.9A patent/CN108349962A/zh active Pending
- 2016-06-01 MX MX2017015456A patent/MX2017015456A/es unknown
- 2016-06-01 EP EP16728546.9A patent/EP3303332A1/en not_active Withdrawn
- 2016-06-01 CA CA3025492A patent/CA3025492A1/en not_active Abandoned
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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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