JP2016535097A5 - - Google Patents
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- JP2016535097A5 JP2016535097A5 JP2016551052A JP2016551052A JP2016535097A5 JP 2016535097 A5 JP2016535097 A5 JP 2016535097A5 JP 2016551052 A JP2016551052 A JP 2016551052A JP 2016551052 A JP2016551052 A JP 2016551052A JP 2016535097 A5 JP2016535097 A5 JP 2016535097A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- fluoro
- indol
- indole
- alkyl
- 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.)
- Pending
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- 229910052736 halogen Inorganic materials 0.000 claims 50
- 150000002367 halogens Chemical class 0.000 claims 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 43
- -1 carboxy, amino Chemical group 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 150000001336 alkenes Chemical class 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical group [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 2
- LAESKFXZAPUKGC-FQEVSTJZSA-N (2S)-2-amino-1-[4-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]piperidin-1-yl]-3-methylbutan-1-one Chemical compound N[C@H](C(=O)N1CCC(CC1)N1N=CC(=C1)C1=CNC2=CC(=CC=C12)F)C(C)C LAESKFXZAPUKGC-FQEVSTJZSA-N 0.000 claims 1
- IIMSGVQGXKBDPG-UHFFFAOYSA-N 1-[3-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]azetidin-1-yl]ethanone Chemical compound CC(=O)N1CC(C1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 IIMSGVQGXKBDPG-UHFFFAOYSA-N 0.000 claims 1
- NUDIHFHPQOUZNB-UHFFFAOYSA-N 1-[4-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NUDIHFHPQOUZNB-UHFFFAOYSA-N 0.000 claims 1
- RURXZTRISPSIKX-UHFFFAOYSA-N 1-[4-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCN(CC1)C(=O)C=C RURXZTRISPSIKX-UHFFFAOYSA-N 0.000 claims 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
- GRXOMNRODRJLBJ-UHFFFAOYSA-N 2-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]-N,N-dimethylacetamide Chemical compound CN(C)C(=O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 GRXOMNRODRJLBJ-UHFFFAOYSA-N 0.000 claims 1
- POCBEPZEWFSEBF-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)pyrazol-4-yl]-1H-indole Chemical compound FC1=CC=C(C=C1)N1N=CC(=C1)C1=CNC2=CC=CC=C12 POCBEPZEWFSEBF-UHFFFAOYSA-N 0.000 claims 1
- AEVFEIKEJIOXPZ-UHFFFAOYSA-N 3-[1-(azetidin-3-ylmethyl)pyrazol-4-yl]-6-fluoro-1H-indole Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(CC2CNC2)c1 AEVFEIKEJIOXPZ-UHFFFAOYSA-N 0.000 claims 1
- XTCIAFUWYIAFBA-UHFFFAOYSA-N 3-[3,5-dimethyl-1-(piperidin-4-ylmethyl)pyrazol-4-yl]-6-fluoro-1H-indole 6-fluoro-3-[3-methyl-1-(piperidin-4-ylmethyl)pyrazol-4-yl]-1H-indole Chemical compound Cc1nn(CC2CCNCC2)cc1-c1c[nH]c2cc(F)ccc12.Cc1nn(CC2CCNCC2)c(C)c1-c1c[nH]c2cc(F)ccc12 XTCIAFUWYIAFBA-UHFFFAOYSA-N 0.000 claims 1
- GPBZDMPJRCOOOV-UHFFFAOYSA-N 3-[4-(6-fluoro-1H-indol-3-yl)-3,5-dimethylpyrazol-1-yl]propanamide Chemical compound Cc1nn(CCC(N)=O)c(C)c1-c1c[nH]c2cc(F)ccc12 GPBZDMPJRCOOOV-UHFFFAOYSA-N 0.000 claims 1
- XMXGWSFXXJAABK-UHFFFAOYSA-N 3-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]-2-hydroxypropanamide Chemical compound NC(=O)C(O)Cn1cc(cn1)-c1c[nH]c2cc(F)ccc12 XMXGWSFXXJAABK-UHFFFAOYSA-N 0.000 claims 1
- NAOSAFXZAVILCY-UHFFFAOYSA-N 4-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]-N-methylpiperidine-1-carboxamide Chemical compound CNC(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NAOSAFXZAVILCY-UHFFFAOYSA-N 0.000 claims 1
- LQVVMGPFGOHGNL-UHFFFAOYSA-N 5,6-difluoro-3-(1H-pyrazol-4-yl)-1H-indole Chemical compound Fc1cc2[nH]cc(-c3cn[nH]c3)c2cc1F LQVVMGPFGOHGNL-UHFFFAOYSA-N 0.000 claims 1
- YYFFEPUCAKVRJX-UHFFFAOYSA-N 6-fluoro-1h-indole Chemical compound FC1=CC=C2C=CNC2=C1 YYFFEPUCAKVRJX-UHFFFAOYSA-N 0.000 claims 1
- STCVAWGKRPLXNH-UHFFFAOYSA-N 6-fluoro-3-(1-piperidin-4-ylpyrazol-4-yl)-1H-indole Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)C1CCNCC1 STCVAWGKRPLXNH-UHFFFAOYSA-N 0.000 claims 1
- QYGLYXKNZBRWME-UHFFFAOYSA-N 6-fluoro-3-(1-pyridazin-3-ylpyrazol-4-yl)-1H-indole Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnn1 QYGLYXKNZBRWME-UHFFFAOYSA-N 0.000 claims 1
- MAGPDBMSRVAGBS-UHFFFAOYSA-N 6-fluoro-3-(1-pyridin-3-ylpyrazol-4-yl)-1H-indole Chemical compound Fc1ccc2c(c[nH]c2c1)-c1cnn(c1)-c1cccnc1 MAGPDBMSRVAGBS-UHFFFAOYSA-N 0.000 claims 1
- NBPWFYAZPCFOSD-UHFFFAOYSA-N 6-fluoro-3-[1-[1-(2-methoxyethylsulfonyl)piperidin-4-yl]pyrazol-4-yl]-1H-indole Chemical compound COCCS(=O)(=O)N1CCC(CC1)n1cc(cn1)-c1c[nH]c2cc(F)ccc12 NBPWFYAZPCFOSD-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZXNMJOMKLVKNFN-UHFFFAOYSA-N C1(CC1)N1CCC(CC1)CN1N=CC(=C1)C1=CNC2=CC(=CC=C12)F.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)C(C)=O Chemical compound C1(CC1)N1CCC(CC1)CN1N=CC(=C1)C1=CNC2=CC(=CC=C12)F.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)C(C)=O ZXNMJOMKLVKNFN-UHFFFAOYSA-N 0.000 claims 1
- HNRJLZGYVIMSNS-UHFFFAOYSA-N CN1N=CC(=C1)C1=CNC2=CC=CC=C12.C(C)N1N=CC(=C1)C1=CNC2=CC=CC=C12.C(C)(C)(C)N1N=CC(=C1)C1=CNC2=CC=CC=C12.N1C=C(C2=CC=CC=C12)C=1C(=NN(C1C)CCN)C Chemical compound CN1N=CC(=C1)C1=CNC2=CC=CC=C12.C(C)N1N=CC(=C1)C1=CNC2=CC=CC=C12.C(C)(C)(C)N1N=CC(=C1)C1=CNC2=CC=CC=C12.N1C=C(C2=CC=CC=C12)C=1C(=NN(C1C)CCN)C HNRJLZGYVIMSNS-UHFFFAOYSA-N 0.000 claims 1
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- OJKIRJBWOUHGGN-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CC(N(CC1)C)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CC(NCC1)=O Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CC(N(CC1)C)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CC(NCC1)=O OJKIRJBWOUHGGN-UHFFFAOYSA-N 0.000 claims 1
- WPBHZXWBNMAWPE-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)C(CCOC)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)C(CCC(=O)O)=O Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)C(CCOC)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)C(CCC(=O)O)=O WPBHZXWBNMAWPE-UHFFFAOYSA-N 0.000 claims 1
- SFDDZCAZQYBAJP-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)CCO.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCNCC1 Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)CCO.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCNCC1 SFDDZCAZQYBAJP-UHFFFAOYSA-N 0.000 claims 1
- SAJVHVOHWRXLMG-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)S(=O)(=O)C(C)C.C(C)S(=O)(=O)N1CCC(CC1)N1N=CC(=C1)C1=CNC2=CC(=CC=C12)F Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)C1CCN(CC1)S(=O)(=O)C(C)C.C(C)S(=O)(=O)N1CCC(CC1)N1N=CC(=C1)C1=CNC2=CC(=CC=C12)F SAJVHVOHWRXLMG-UHFFFAOYSA-N 0.000 claims 1
- BHPFJCGZNYVLEJ-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)CCF.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)CC(F)(F)F Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)CCF.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)CC(F)(F)F BHPFJCGZNYVLEJ-UHFFFAOYSA-N 0.000 claims 1
- YWKVFPTVKJXRTL-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)S(=O)(=O)C.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)C Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)S(=O)(=O)C.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCN(CC1)C YWKVFPTVKJXRTL-UHFFFAOYSA-N 0.000 claims 1
- ZNAWHPZKIMSPGY-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCOCC1.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1C)CC1CCNCC1 Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCOCC1.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1C)CC1CCNCC1 ZNAWHPZKIMSPGY-UHFFFAOYSA-N 0.000 claims 1
- ZYGSQTIKXPZTGT-UHFFFAOYSA-N FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCS(CC1)(=O)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1(CCOCC1)O Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1CCS(CC1)(=O)=O.FC1=CC=C2C(=CNC2=C1)C=1C=NN(C1)CC1(CCOCC1)O ZYGSQTIKXPZTGT-UHFFFAOYSA-N 0.000 claims 1
- 101000892398 Homo sapiens Tryptophan 2,3-dioxygenase Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- JPLVIUXYLOEZLN-UHFFFAOYSA-N N-[2-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]ethyl]methanesulfonamide 2-[4-(6-fluoro-1H-indol-3-yl)pyrazol-1-yl]-N-methylethanamine Chemical compound CNCCn1cc(cn1)-c1c[nH]c2cc(F)ccc12.CS(=O)(=O)NCCn1cc(cn1)-c1c[nH]c2cc(F)ccc12 JPLVIUXYLOEZLN-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 102100040653 Tryptophan 2,3-dioxygenase Human genes 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 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 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 0 **(C=C1)=*=C1[n](c(N)c1-c2c[n]c3c2cc(*)c(I)c3)nc1N Chemical compound **(C=C1)=*=C1[n](c(N)c1-c2c[n]c3c2cc(*)c(I)c3)nc1N 0.000 description 1
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| US14/076,016 | 2013-11-08 | ||
| US14/076,016 US9126984B2 (en) | 2013-11-08 | 2013-11-08 | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| BE201400845 | 2014-11-03 | ||
| BE2014/0845 | 2014-11-03 | ||
| PCT/EP2014/074099 WO2015067782A1 (en) | 2013-11-08 | 2014-11-07 | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
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| JP2016535097A JP2016535097A (ja) | 2016-11-10 |
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| TWI695831B (zh) | 2014-09-13 | 2020-06-11 | 香港商南北兄弟藥業投資有限公司 | Ｃｒｔｈ２拮抗劑化合物及其用途 |
| SG11201808108XA (en) * | 2016-04-29 | 2018-10-30 | Bayer Pharma AG | Synthesis of indazoles |
| EP3269714A1 (en) | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
| WO2018054365A1 (en) | 2016-09-24 | 2018-03-29 | Beigene, Ltd. | NOVEL 5 or 8-SUBSTITUTED IMIDAZO [1, 5-a] PYRIDINES AS SELECTIVE INHIBITORS OF INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES |
| US20230278983A1 (en) * | 2020-07-06 | 2023-09-07 | Universite Claude Bernard Lyon 1 | Indole derivatives and uses thereof for treating a cancer |
| US20230391786A1 (en) * | 2022-06-02 | 2023-12-07 | Eli Lilly And Company | cGAS INHIBITORS |
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| FR2862647B1 (fr) * | 2003-11-25 | 2008-07-04 | Aventis Pharma Sa | Derives de pyrazolyle, procede de preparation et intermediaires de ce procede a titre de medicaments et de compositions pharmaceutiques les renfermant |
| GB0516156D0 (en) * | 2005-08-05 | 2005-09-14 | Eisai London Res Lab Ltd | JNK inhibitors |
| US20110159017A1 (en) * | 2008-04-11 | 2011-06-30 | Ludwig Institute For Cancer Research Ltd. | Trytophan catabolism in cancer treatment and diagnosis |
| WO2010136491A1 (en) | 2009-05-27 | 2010-12-02 | F. Hoffmann-La Roche Ag | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| ES2533798T3 (es) | 2009-10-12 | 2015-04-14 | Bayer Cropscience Ag | 1-(pirid-3-il)-pirazol y 1-(pirimid-5-il)- pirazol como agentes para combatir parásitos |
| MX2013000103A (es) * | 2010-06-23 | 2013-06-13 | Vertex Pharma | Derivados de pirrolo-pirazina utiles como inhibidores de cinasa art. |
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- 2014-11-07 EP EP14796082.7A patent/EP3066090A1/en not_active Withdrawn
- 2014-11-07 JP JP2016551052A patent/JP2016535097A/ja active Pending
- 2014-11-07 WO PCT/EP2014/074099 patent/WO2015067782A1/en not_active Ceased
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