JP2019536785A5 - - Google Patents
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- JP2019536785A5 JP2019536785A5 JP2019528861A JP2019528861A JP2019536785A5 JP 2019536785 A5 JP2019536785 A5 JP 2019536785A5 JP 2019528861 A JP2019528861 A JP 2019528861A JP 2019528861 A JP2019528861 A JP 2019528861A JP 2019536785 A5 JP2019536785 A5 JP 2019536785A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazole
- fluorophenyl
- alkyl
- thiazole
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 29
- 229910052799 carbon Inorganic materials 0.000 claims 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Chemical group 0.000 claims 11
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 239000001301 oxygen Chemical group 0.000 claims 9
- 239000011593 sulfur Chemical group 0.000 claims 9
- -1 4- (4-Ethylpiperazin-1-yl) -5- (isopropylthio) thiazole-2-yl Chemical group 0.000 claims 6
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 4
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 4
- 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
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- SFTZRUZMNGBFFL-UHFFFAOYSA-N methyl 4-(3-fluorophenyl)-5-methyl-2-[5-propan-2-ylsulfanyl-4-[4-(trifluoromethyl)cyclohexen-1-yl]-1,3-thiazol-2-yl]pyrazole-3-carboxylate Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1C(=O)OC)C=1SC(=C(N=1)C1=CCC(CC1)C(F)(F)F)SC(C)C)C SFTZRUZMNGBFFL-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims 1
- WUNOVGVMJGWMIW-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n-methylacetamide Chemical compound CNC(=O)COCCOC WUNOVGVMJGWMIW-UHFFFAOYSA-N 0.000 claims 1
- IGMNPRJAMCOILX-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetamide Chemical compound COCCOCC(N)=O IGMNPRJAMCOILX-UHFFFAOYSA-N 0.000 claims 1
- HEMIXKBRKYHBND-UHFFFAOYSA-N 2-[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound COC1=CC=C(C=C1)C=1N=C(SC=1C1=CC=C(C=C1)OC)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C HEMIXKBRKYHBND-UHFFFAOYSA-N 0.000 claims 1
- KLXJYYCBHROYPO-UHFFFAOYSA-N 2-[4,5-bis[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound FC(C1=CC=C(C=C1)C=1N=C(SC=1C1=CC=C(C=C1)C(F)(F)F)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)(F)F KLXJYYCBHROYPO-UHFFFAOYSA-N 0.000 claims 1
- MXACZLIQEYYSHM-UHFFFAOYSA-N 2-[4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-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=CCC2(OCCO2)CC1)SC(C)C)C MXACZLIQEYYSHM-UHFFFAOYSA-N 0.000 claims 1
- WWQFHKYCDFDXOY-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)-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)-c1cccc(F)c1 WWQFHKYCDFDXOY-UHFFFAOYSA-N 0.000 claims 1
- ARJRMFMVIMXNAJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)-3-methylpyrazol-1-yl]-4,5-bis[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound FC=1C=C(C=CC=1)C=1C(=NN(C=1)C=1SC(=C(N=1)C1=CC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F)C ARJRMFMVIMXNAJ-UHFFFAOYSA-N 0.000 claims 1
- QODPSINGCLBNLF-UHFFFAOYSA-N 2-[4-(4,4-difluoropiperidin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound FC1(CCN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)F QODPSINGCLBNLF-UHFFFAOYSA-N 0.000 claims 1
- AFTBBPCVOXLMJW-UHFFFAOYSA-N 2-[4-(4,4-dimethylcyclohexen-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC1(CC=C(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C AFTBBPCVOXLMJW-UHFFFAOYSA-N 0.000 claims 1
- OSMVVLIXEOTTAI-UHFFFAOYSA-N 2-[4-(4,4-dimethylpiperidin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound CC1(CCN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C OSMVVLIXEOTTAI-UHFFFAOYSA-N 0.000 claims 1
- VBNPMHGEOJTKAD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)(=O)N1CCN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C VBNPMHGEOJTKAD-UHFFFAOYSA-N 0.000 claims 1
- CCNGVHKBAFQHLJ-UHFFFAOYSA-N 2-[4-(4-cyanopiperidin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(#N)C1CCN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C CCNGVHKBAFQHLJ-UHFFFAOYSA-N 0.000 claims 1
- LULUEXOUOGDMHT-UHFFFAOYSA-N 2-[4-(4-cyclopropylpiperazin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C1(CC1)N1CCN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C LULUEXOUOGDMHT-UHFFFAOYSA-N 0.000 claims 1
- MBIXOWVGXJGNGS-UHFFFAOYSA-N 2-[4-(4-tert-butyl-3-oxopiperazin-1-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)(C)(C)N1C(CN(CC1)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)=O MBIXOWVGXJGNGS-UHFFFAOYSA-N 0.000 claims 1
- WIKUALXMWADVNC-UHFFFAOYSA-N 2-[4-(6-azaspiro[2.5]octan-6-yl)-5-propan-2-ylsulfanyl-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-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)N1CCC2(CC2)CC1)SC(C)C)C WIKUALXMWADVNC-UHFFFAOYSA-N 0.000 claims 1
- KYQAWTUXPJTFKH-UHFFFAOYSA-N 2-[4-[4-chloro-2-(oxetan-3-yloxy)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-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)C)OC1COC1 KYQAWTUXPJTFKH-UHFFFAOYSA-N 0.000 claims 1
- CGGOKPPVHPSIDS-UHFFFAOYSA-N 2-[4-[4-chloro-3-(morpholine-4-carbonyl)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(=O)N1CCOCC1 CGGOKPPVHPSIDS-UHFFFAOYSA-N 0.000 claims 1
- RASYQZCHAFQHCZ-UHFFFAOYSA-N 2-[4-[4-chloro-3-(oxetan-3-yloxy)phenyl]-5-propan-2-ylsulfanyl-1,3-thiazol-2-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)C)OC1COC1 RASYQZCHAFQHCZ-UHFFFAOYSA-N 0.000 claims 1
- YTSYITZBAHXPFA-UHFFFAOYSA-N 2-[5-(3,4-dichlorophenyl)-1-(2-methylpropyl)-1,2,4-triazol-3-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C1=NC(=NN1CC(C)C)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C YTSYITZBAHXPFA-UHFFFAOYSA-N 0.000 claims 1
- PZERARTUCDKDRE-UHFFFAOYSA-N 2-[5-(3,4-dichlorophenyl)-2-(2-methylpropyl)-1,2,4-triazol-3-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound ClC=1C=C(C=CC=1Cl)C1=NN(C(=N1)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)CC(C)C PZERARTUCDKDRE-UHFFFAOYSA-N 0.000 claims 1
- ILOOJEWVWVLTQT-UHFFFAOYSA-N 2-[5-[4-[2-(2-ethoxyethoxy)ethoxy]phenyl]-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-4-(3-fluorophenyl)-5-methylpyrazole-3-carboxylic acid Chemical compound C(C)OCCOCCOC1=CC=C(C=C1)C1=C(N=C(S1)N1N=C(C(=C1C(=O)O)C1=CC(=CC=C1)F)C)C1=CC=C(C=C1)C(F)(F)F ILOOJEWVWVLTQT-UHFFFAOYSA-N 0.000 claims 1
- DYJPVSYLWLJPEE-UHFFFAOYSA-N 2-methoxy-n-methylacetamide Chemical compound CNC(=O)COC DYJPVSYLWLJPEE-UHFFFAOYSA-N 0.000 claims 1
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 claims 1
- VBGNUHKNSSJROF-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[4-(2,6-dimethylpyridin-4-yl)-3-methylpyrazol-1-yl]-5-propan-2-ylsulfanyl-1,3-thiazole Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(SC=1SC(C)C)N1N=C(C(=C1)C1=CC(=NC(=C1)C)C)C VBGNUHKNSSJROF-UHFFFAOYSA-N 0.000 claims 1
- FGVVCPHMRVSKQO-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(3-fluorophenyl)-5-[4-(trifluoromethyl)phenyl]-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)C1=CC=C(C=C1)C(F)(F)F)C FGVVCPHMRVSKQO-UHFFFAOYSA-N 0.000 claims 1
- ZBVZNYYQZRSPRM-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-(4-methoxyphenyl)-5-[4-(trifluoromethyl)phenyl]-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)C1=CC=C(C=C1)C(F)(F)F)C ZBVZNYYQZRSPRM-UHFFFAOYSA-N 0.000 claims 1
- FAVQFPULQZOYNO-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-[4-(2-methoxyethoxy)-4-(trifluoromethyl)piperidin-1-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)N1CCC(CC1)(C(F)(F)F)OCCOC)SC(C)C)C FAVQFPULQZOYNO-UHFFFAOYSA-N 0.000 claims 1
- AWPZZTBRRNIBJH-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[4-[4-methoxy-4-(trifluoromethyl)piperidin-1-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)N1CCC(CC1)(C(F)(F)F)OC)SC(C)C)C AWPZZTBRRNIBJH-UHFFFAOYSA-N 0.000 claims 1
- MOJWDINGMVNHPX-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(1-hydroxyethyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C(C)O)C MOJWDINGMVNHPX-UHFFFAOYSA-N 0.000 claims 1
- IRFGSCOKPCDOAM-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(1-methoxyethyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C(C)OC)C IRFGSCOKPCDOAM-UHFFFAOYSA-N 0.000 claims 1
- OTVZZJAIAXAJJW-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(2-hydroxyethyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)CCO)C OTVZZJAIAXAJJW-UHFFFAOYSA-N 0.000 claims 1
- YDRDXVSBBVJBHG-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(3-fluorophenyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C1=CC(=CC=C1)F)C YDRDXVSBBVJBHG-UHFFFAOYSA-N 0.000 claims 1
- CYRQULRVUOCILV-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(4-methoxyphenyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C1=CC=C(C=C1)OC)C CYRQULRVUOCILV-UHFFFAOYSA-N 0.000 claims 1
- YPLCMRXNEOKHGI-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(hydroxymethyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)CO)C YPLCMRXNEOKHGI-UHFFFAOYSA-N 0.000 claims 1
- PYXQFFSDMQRZKG-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-(methoxymethyl)-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)COC)C PYXQFFSDMQRZKG-UHFFFAOYSA-N 0.000 claims 1
- ANQVCHHDHFBBAZ-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-[2-methoxyethyl(methyl)amino]-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)N(C)CCOC)C ANQVCHHDHFBBAZ-UHFFFAOYSA-N 0.000 claims 1
- GBARCWRQYBYIQH-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-[3-(2-methoxyethylamino)-3-oxopropyl]-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)CCC(=O)NCCOC)C GBARCWRQYBYIQH-UHFFFAOYSA-N 0.000 claims 1
- ZKDVPTRNSAKTNV-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[5-[4-(2-methoxyethoxy)phenyl]-4-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C1=CC=C(C=C1)OCCOC)C ZKDVPTRNSAKTNV-UHFFFAOYSA-N 0.000 claims 1
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| SI2275414T1 (sl) | 2008-04-28 | 2015-10-30 | Kyorin Pharmaceutical Co., Ltd., | Ciklopentilakrilamidni derivat |
| 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 |
| AU2017366901B2 (en) * | 2016-11-30 | 2022-09-29 | Bantam Pharmaceutical, Llc | Substituted pyrazole compounds and methods of using them for treatment of hyperproliferative diseases |
| 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. |
| EP3976606A1 (en) * | 2019-05-31 | 2022-04-06 | Bantam Pharmaceutical, LLC | Crystalline polymorphs of a 1-thiazol-2-yl-pyrazole-5-carboxylic acid derivative |
-
2017
- 2017-11-29 AU AU2017366901A patent/AU2017366901B2/en active Active
- 2017-11-29 CA CA3081983A patent/CA3081983A1/en active Pending
- 2017-11-29 US US16/465,136 patent/US11325903B2/en active Active
- 2017-11-29 JP JP2019528861A patent/JP7373992B2/ja active Active
- 2017-11-29 EP EP17876486.6A patent/EP3548482A4/en active Pending
- 2017-11-29 WO PCT/US2017/063774 patent/WO2018102453A1/en not_active Ceased
- 2017-11-29 CN CN202410345199.5A patent/CN118930533A/zh active Pending
- 2017-11-29 BR BR112019011044-5A patent/BR112019011044A2/pt active IP Right Grant
- 2017-11-29 MX MX2019006299A patent/MX2019006299A/es unknown
- 2017-11-29 IL IL266930A patent/IL266930B2/en unknown
- 2017-11-29 CN CN201780084999.4A patent/CN110603254B/zh active Active
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2022
- 2022-05-10 US US17/741,153 patent/US20230076820A1/en active Pending
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