JP2014532626A5 - - Google Patents
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- JP2014532626A5 JP2014532626A5 JP2014537274A JP2014537274A JP2014532626A5 JP 2014532626 A5 JP2014532626 A5 JP 2014532626A5 JP 2014537274 A JP2014537274 A JP 2014537274A JP 2014537274 A JP2014537274 A JP 2014537274A JP 2014532626 A5 JP2014532626 A5 JP 2014532626A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- trifluoromethyl
- imidazo
- hydrogen
- methyl
- 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.)
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 236
- 239000001257 hydrogen Substances 0.000 claims description 236
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 142
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 140
- -1 difluoromethoxy, trifluoromethoxy, oxazolyl Chemical group 0.000 claims description 139
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 110
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 104
- 150000002431 hydrogen Chemical class 0.000 claims description 96
- 150000002825 nitriles Chemical class 0.000 claims description 96
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 94
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 82
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 80
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 72
- 125000001246 bromo group Chemical group Br* 0.000 claims description 68
- 125000001153 fluoro group Chemical group F* 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 57
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 52
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 52
- 125000005475 oxolanyl group Chemical group 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000002757 morpholinyl group Chemical group 0.000 claims description 45
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 44
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 44
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 36
- 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 description 36
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 125000003386 piperidinyl group Chemical group 0.000 claims description 34
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 34
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
- 125000002541 furyl group Chemical group 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 28
- 125000002883 imidazolyl group Chemical group 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 28
- 230000009385 viral infection Effects 0.000 claims description 28
- 208000036142 Viral infection Diseases 0.000 claims description 27
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 27
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 27
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 26
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000001544 thienyl group Chemical group 0.000 claims description 24
- 201000010153 skin papilloma Diseases 0.000 claims description 21
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229940124530 sulfonamide Drugs 0.000 claims description 16
- 150000003456 sulfonamides Chemical class 0.000 claims description 16
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 16
- 208000000260 Warts Diseases 0.000 claims description 15
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 14
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 14
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 13
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 150000003457 sulfones Chemical class 0.000 claims description 12
- 150000003462 sulfoxides Chemical class 0.000 claims description 12
- 241000701806 Human papillomavirus Species 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000012190 activator Substances 0.000 claims description 9
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 8
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims description 8
- 210000004400 mucous membrane Anatomy 0.000 claims description 8
- RXFCBIOFXJLRDT-UHFFFAOYSA-N 2-[2-cyclopentyl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2CCCC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 RXFCBIOFXJLRDT-UHFFFAOYSA-N 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
- NXWFZLSDGBWCMN-UHFFFAOYSA-N 1,3-oxazol-4-amine Chemical compound NC1=COC=N1 NXWFZLSDGBWCMN-UHFFFAOYSA-N 0.000 claims description 4
- UEEBKQWDBWDPKD-UHFFFAOYSA-N 1,3-oxazole-4-carbonitrile Chemical compound N#CC1=COC=N1 UEEBKQWDBWDPKD-UHFFFAOYSA-N 0.000 claims description 4
- NVZFORKBKKRTPC-UHFFFAOYSA-N 1-[2-(1,3,4-oxadiazol-2-yl)-6,8-bis(trifluoromethyl)pyrrolo[3,2-h]quinolin-1-yl]ethanone Chemical compound C=1C2=CC=C3C(C(F)(F)F)=CC(C(F)(F)F)=NC3=C2N(C(=O)C)C=1C1=NN=CO1 NVZFORKBKKRTPC-UHFFFAOYSA-N 0.000 claims description 4
- AARLOGDETIISCE-UHFFFAOYSA-N 1-cyano-N-ethoxy-N-propan-2-yloxyformamide Chemical compound CCON(OC(C)C)C(=O)C#N AARLOGDETIISCE-UHFFFAOYSA-N 0.000 claims description 4
- FLVFPAIGVBQGET-UHFFFAOYSA-N 1-methylpyrrolidin-3-ol Chemical compound CN1CCC(O)C1 FLVFPAIGVBQGET-UHFFFAOYSA-N 0.000 claims description 4
- PWIDBQONFRLSHB-UHFFFAOYSA-N 2-(2,4-dimethylimidazo[1,2-a][1,8]naphthyridin-8-yl)-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C)=CC(C)=C3C=CC2=NC=1C1=NN=CO1 PWIDBQONFRLSHB-UHFFFAOYSA-N 0.000 claims description 4
- OVDQMFOFJGKNQJ-UHFFFAOYSA-N 2-(4-chloro-2-propan-2-ylimidazo[1,2-a][1,8]naphthyridin-8-yl)-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C(C)C)=CC(Cl)=C3C=CC2=NC=1C1=NN=CO1 OVDQMFOFJGKNQJ-UHFFFAOYSA-N 0.000 claims description 4
- SXJCXTRJWBFKTG-UHFFFAOYSA-N 2-(4-phenyl-2-propan-2-ylimidazo[1,2-a][1,8]naphthyridin-8-yl)-1,3,4-oxadiazole Chemical compound C=12C=CC3=NC(C=4OC=NN=4)=CN3C2=NC(C(C)C)=CC=1C1=CC=CC=C1 SXJCXTRJWBFKTG-UHFFFAOYSA-N 0.000 claims description 4
- GKAUJNGBWGBWPN-UHFFFAOYSA-N 2-[1-benzyl-6,8-bis(trifluoromethyl)pyrrolo[3,2-h]quinolin-2-yl]-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1CN1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=NN=CO1 GKAUJNGBWGBWPN-UHFFFAOYSA-N 0.000 claims description 4
- FYDPIVQTBUDNFZ-UHFFFAOYSA-N 2-[1-methyl-6,8-bis(trifluoromethyl)pyrrolo[3,2-h]quinolin-2-yl]-1,3,4-oxadiazole Chemical compound C=1C2=CC=C3C(C(F)(F)F)=CC(C(F)(F)F)=NC3=C2N(C)C=1C1=NN=CO1 FYDPIVQTBUDNFZ-UHFFFAOYSA-N 0.000 claims description 4
- GRHYZVJEXKTJOS-UHFFFAOYSA-N 2-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 GRHYZVJEXKTJOS-UHFFFAOYSA-N 0.000 claims description 4
- QWVRUQREZXNEJA-UHFFFAOYSA-N 2-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3-oxazole Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NC=CO1 QWVRUQREZXNEJA-UHFFFAOYSA-N 0.000 claims description 4
- FMTRHOIWPWHRKP-UHFFFAOYSA-N 2-[2,4-di(propan-2-yl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C(C)C)=CC(C(C)C)=C3C=CC2=NC=1C1=NN=CO1 FMTRHOIWPWHRKP-UHFFFAOYSA-N 0.000 claims description 4
- OZSBUQCOVZFGGH-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(OC(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 OZSBUQCOVZFGGH-UHFFFAOYSA-N 0.000 claims description 4
- QBUBXOFXOWEBHR-UHFFFAOYSA-N 2-[2-(furan-3-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2=COC=C2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 QBUBXOFXOWEBHR-UHFFFAOYSA-N 0.000 claims description 4
- XSRCLMHZKWWMMN-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(Cl)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 XSRCLMHZKWWMMN-UHFFFAOYSA-N 0.000 claims description 4
- FAYSDPVMSHSKCO-UHFFFAOYSA-N 2-[2-cyclopropyl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2CC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 FAYSDPVMSHSKCO-UHFFFAOYSA-N 0.000 claims description 4
- YVDRGFKZVNBSHE-UHFFFAOYSA-N 2-[2-ethoxy-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(OCC)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 YVDRGFKZVNBSHE-UHFFFAOYSA-N 0.000 claims description 4
- KNEJRARJYGTLGH-UHFFFAOYSA-N 2-[2-ethyl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(CC)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 KNEJRARJYGTLGH-UHFFFAOYSA-N 0.000 claims description 4
- MLTVDJZRACHHIX-UHFFFAOYSA-N 2-[2-methyl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 MLTVDJZRACHHIX-UHFFFAOYSA-N 0.000 claims description 4
- BNWCHNKOUUUCMU-UHFFFAOYSA-N 2-[2-phenyl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C=2C=CC=CC=2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 BNWCHNKOUUUCMU-UHFFFAOYSA-N 0.000 claims description 4
- PKUZIWSJMAJAFL-UHFFFAOYSA-N 2-[2-propan-2-yl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C(C)C)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 PKUZIWSJMAJAFL-UHFFFAOYSA-N 0.000 claims description 4
- PZOGDYJGGWPWII-UHFFFAOYSA-N 2-[2-pyridin-3-yl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C=2C=NC=CC=2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 PZOGDYJGGWPWII-UHFFFAOYSA-N 0.000 claims description 4
- RXORGTVUKXHNKO-UHFFFAOYSA-N 2-[2-thiophen-3-yl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2=CSC=C2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 RXORGTVUKXHNKO-UHFFFAOYSA-N 0.000 claims description 4
- LKUWFBQVSIRPML-UHFFFAOYSA-N 2-[6,8-bis(trifluoromethyl)imidazo[1,2-a]quinolin-2-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 LKUWFBQVSIRPML-UHFFFAOYSA-N 0.000 claims description 4
- ODUJRHUJULQYER-UHFFFAOYSA-N 2-[9-chloro-2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound ClC=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 ODUJRHUJULQYER-UHFFFAOYSA-N 0.000 claims description 4
- DJEMXTIXIBTHNG-UHFFFAOYSA-N 2-[9-methyl-2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound N1=C2C=CC3=C(C(F)(F)F)C=C(C(F)(F)F)N=C3N2C(C)=C1C1=NN=CO1 DJEMXTIXIBTHNG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- CQRMHSRHWONGKT-UHFFFAOYSA-N 5-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3-oxazole Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=CN=CO1 CQRMHSRHWONGKT-UHFFFAOYSA-N 0.000 claims description 4
- MYAVWTCDDATPRC-UHFFFAOYSA-N 5-[6,8-bis(trifluoromethyl)-3h-imidazo[4,5-h]quinolin-2-yl]-1,3-oxazole Chemical compound N=1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2NC=1C1=CN=CO1 MYAVWTCDDATPRC-UHFFFAOYSA-N 0.000 claims description 4
- MPTASBRELSDHLR-UHFFFAOYSA-N 8-(furan-2-yl)-2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridine Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=CC=CO1 MPTASBRELSDHLR-UHFFFAOYSA-N 0.000 claims description 4
- XLHJXZQVTKBZGE-UHFFFAOYSA-N C=1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2NC=1C1=NN=CO1 Chemical compound C=1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2NC=1C1=NN=CO1 XLHJXZQVTKBZGE-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 206010061598 Immunodeficiency Diseases 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- IYKWLKMNKIDWIV-UHFFFAOYSA-N N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=NN=CO1 Chemical compound N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=NN=CO1 IYKWLKMNKIDWIV-UHFFFAOYSA-N 0.000 claims description 4
- 208000009608 Papillomavirus Infections Diseases 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- OIKZFUOILGIONH-UHFFFAOYSA-N cyclobutyl-[2-(1,3,4-oxadiazol-2-yl)-6,8-bis(trifluoromethyl)pyrrolo[3,2-h]quinolin-1-yl]methanone Chemical compound C1CCC1C(=O)N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=NN=CO1 OIKZFUOILGIONH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- SKQVDXYIOKNAMW-UHFFFAOYSA-N difluoromethyl hypochlorite Chemical compound FC(F)OCl SKQVDXYIOKNAMW-UHFFFAOYSA-N 0.000 claims description 4
- 208000021145 human papilloma virus infection Diseases 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 206010040882 skin lesion Diseases 0.000 claims description 4
- 231100000444 skin lesion Toxicity 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000012049 topical pharmaceutical composition Substances 0.000 claims description 4
- 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 claims description 3
- 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 claims description 3
- 230000028993 immune response Effects 0.000 claims description 3
- WELMECWTULNKJJ-ZDUSSCGKSA-N (5r)-5-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)N=CO[C@H]1C1=CN2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=N1 WELMECWTULNKJJ-ZDUSSCGKSA-N 0.000 claims description 2
- VVDNEMLZPLYFGY-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-n,n-dimethylmethanamine Chemical compound C1=C(C(F)(F)F)N=C2N3C=C(CN(C)C)N=C3C=CC2=C1C(F)(F)F VVDNEMLZPLYFGY-UHFFFAOYSA-N 0.000 claims description 2
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| US9758518B2 (en) | 2015-03-04 | 2017-09-12 | Pimera, Inc. | Compositions, uses and methods for making them |
| CA2963090A1 (en) | 2014-09-29 | 2016-04-07 | The Trustees Of The University Of Pennsylvania | Antivirals against molluscum contagiosum virus |
| CN104529893B (zh) * | 2014-12-30 | 2016-08-24 | 中国科学技术大学 | 一类可以作为高尔基体细胞器探针的喹啉染料 |
| CN105175277B (zh) * | 2015-05-18 | 2018-04-03 | 中山大学肿瘤防治中心 | 一种3‑磷酸甘油醛脱氢酶的抑制剂及其制备方法和应用 |
| WO2018043747A1 (ja) * | 2016-09-05 | 2018-03-08 | 国立大学法人京都大学 | 抗ｂ型肝炎ウイルス剤 |
| JP2020512975A (ja) | 2017-03-28 | 2020-04-30 | ピメラ，インク． | Ｐｏｌ１阻害剤の新規な結晶形態 |
| US12134616B2 (en) | 2018-10-23 | 2024-11-05 | Basf Se | Tricyclic pesticidal compounds |
| CN114681472B (zh) * | 2019-03-13 | 2023-06-30 | 中国人民解放军军事科学院军事医学研究院 | 氨基葡萄糖及其衍生物作为抗病毒药物的应用 |
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| JP2023539896A (ja) * | 2020-09-03 | 2023-09-20 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッド | Ｓａｒｓ－ｃｏｖ－２感染を治療するためのｉｆｎａｒ２アゴニストとしてのイミダゾナフチリジンおよびイミダゾピリドピリミジン |
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| US12030883B2 (en) | 2021-09-21 | 2024-07-09 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of KRAS |
| US12030884B2 (en) | 2021-10-01 | 2024-07-09 | Incyte Corporation | Pyrazoloquinoline KRAS inhibitors |
| KR20240101561A (ko) | 2021-10-14 | 2024-07-02 | 인사이트 코포레이션 | Kras의 저해제로서의 퀴놀린 화합물 |
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| SE441449B (sv) * | 1979-02-09 | 1985-10-07 | Roussel Uclaf | Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat |
| US4492697A (en) * | 1983-08-16 | 1985-01-08 | Ayerst, Mckenna & Harrison, Inc. | 4H-Imidazo[2,3-c]pyrido[2,3-e][1,4]oxazine derivatives |
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| RU2310657C2 (ru) * | 2002-04-03 | 2007-11-20 | Ф.Хоффманн-Ля Рош Аг | Имидазоконденсированные соединения и фармацевтическая композиция, содержащая их |
| US8592368B2 (en) * | 2003-12-19 | 2013-11-26 | University Of South Florida | JAK/STAT inhibitors and MAPK/ERK inhibitors for RSV infection |
| DE102005019181A1 (de) * | 2005-04-25 | 2006-10-26 | Novartis Ag | Peptid-Deformylase (PDF) Inhibitoren 1 |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| JP5481671B2 (ja) * | 2009-03-31 | 2014-04-23 | ダイキン工業株式会社 | 高分子アクチュエータ素子用電極膜及びそれを有する高分子アクチュエータ素子 |
| GB0919432D0 (en) * | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Use |
| GB201002409D0 (en) * | 2010-02-12 | 2010-03-31 | Univ Nottingham | Methods |
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