CA2851801A1 - Compounds and methods for enhancing innate immune responses - Google Patents

Info

Publication number

CA2851801A1

CA2851801A1 CA2851801A CA2851801A CA2851801A1 CA 2851801 A1 CA2851801 A1 CA 2851801A1 CA 2851801 A CA2851801 A CA 2851801A CA 2851801 A CA2851801 A CA 2851801A CA 2851801 A1 CA2851801 A1 CA 2851801A1

Authority

CA

Canada

Prior art keywords

group

trifluoromethyl

hydrogen

imidazo

methyl

Prior art date

2011-10-21

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 254
• 238000000034 method Methods 0.000 title claims abstract description 95
• 230000002708 enhancing effect Effects 0.000 title claims description 13
• 230000015788 innate immune response Effects 0.000 title description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 96
• 208000036142 Viral infection Diseases 0.000 claims abstract description 92
• 230000009385 viral infection Effects 0.000 claims abstract description 92
• 238000011282 treatment Methods 0.000 claims abstract description 43
• 230000028993 immune response Effects 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 382
• 239000001257 hydrogen Substances 0.000 claims description 382
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 291
• -1 -R12 Chemical group 0.000 claims description 266
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 218
• 150000002825 nitriles Chemical class 0.000 claims description 202
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 194
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 186
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 185
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 183
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 164
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 149
• 125000001153 fluoro group Chemical group F* 0.000 claims description 147
• 125000001246 bromo group Chemical group Br* 0.000 claims description 146
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 124
• 229910052757 nitrogen Inorganic materials 0.000 claims description 119
• 125000001072 heteroaryl group Chemical group 0.000 claims description 111
• 125000000623 heterocyclic group Chemical group 0.000 claims description 111
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 105
• 125000005475 oxolanyl group Chemical group 0.000 claims description 105
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 104
• 125000002757 morpholinyl group Chemical group 0.000 claims description 99
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 93
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 87
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 85
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
• 125000005843 halogen group Chemical group 0.000 claims description 82
• 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 78
• 125000003386 piperidinyl group Chemical group 0.000 claims description 78
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 78
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 76
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 74
• 125000002541 furyl group Chemical group 0.000 claims description 71
• 125000002883 imidazolyl group Chemical group 0.000 claims description 68
• 125000004076 pyridyl group Chemical group 0.000 claims description 68
• 201000010153 skin papilloma Diseases 0.000 claims description 68
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 67
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 66
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 63
• 125000001544 thienyl group Chemical group 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 241000700605 Viruses Species 0.000 claims description 53
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 47
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 44
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 42
• 208000000260 Warts Diseases 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 40
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
• 229940124530 sulfonamide Drugs 0.000 claims description 36
• 150000003456 sulfonamides Chemical class 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 32
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 32
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 32
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 32
• 125000004043 oxo group Chemical group O=* 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
• 150000003457 sulfones Chemical class 0.000 claims description 27
• 150000003462 sulfoxides Chemical class 0.000 claims description 27
• 241000701806 Human papillomavirus Species 0.000 claims description 26
• 125000002971 oxazolyl group Chemical group 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
• 210000004400 mucous membrane Anatomy 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 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
• 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 claims description 12
• 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 claims description 12
• 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 claims description 12
• 239000012190 activator Substances 0.000 claims description 12
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 11
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 10
• 201000004196 common wart Diseases 0.000 claims description 10
• 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
• 239000003814 drug Substances 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 206010061598 Immunodeficiency Diseases 0.000 claims description 7
• 150000003857 carboxamides Chemical class 0.000 claims description 7
• 210000000987 immune system Anatomy 0.000 claims description 7
• 206010059313 Anogenital warts Diseases 0.000 claims description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
• NXWFZLSDGBWCMN-UHFFFAOYSA-N 1,3-oxazol-4-amine Chemical compound NC1=COC=N1 NXWFZLSDGBWCMN-UHFFFAOYSA-N 0.000 claims description 5
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 208000000907 Condylomata Acuminata Diseases 0.000 claims description 5
• 208000009608 Papillomavirus Infections Diseases 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 239000012049 topical pharmaceutical composition Substances 0.000 claims description 5
• 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 group CN1CCC(O)C1 FLVFPAIGVBQGET-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
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 241001631646 Papillomaviridae Species 0.000 claims description 4
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
• SKQVDXYIOKNAMW-UHFFFAOYSA-N difluoromethyl hypochlorite Chemical group FC(F)OCl SKQVDXYIOKNAMW-UHFFFAOYSA-N 0.000 claims description 4
• WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 210000003899 penis Anatomy 0.000 claims description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
• 210000003905 vulva Anatomy 0.000 claims description 4
• 230000004163 JAK-STAT signaling pathway Effects 0.000 claims description 3
• 210000000436 anus Anatomy 0.000 claims description 3
• 210000003679 cervix uteri Anatomy 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 3
• 230000008088 immune pathway Effects 0.000 claims description 3
• 230000003902 lesion Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 210000003300 oropharynx Anatomy 0.000 claims description 3
• 208000017520 skin disease Diseases 0.000 claims description 3
• 206010040882 skin lesion Diseases 0.000 claims description 3
• 231100000444 skin lesion Toxicity 0.000 claims description 3
• 210000001215 vagina Anatomy 0.000 claims description 3
• YVBPNYXAQNAMLH-UHFFFAOYSA-N 1-hydroxy-2-methylpyrrolidine Chemical group CC1CCCN1O YVBPNYXAQNAMLH-UHFFFAOYSA-N 0.000 claims description 2
• ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical group CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims description 2
• 206010065173 Viral skin infection Diseases 0.000 claims description 2
• 208000009621 actinic keratosis Diseases 0.000 claims description 2
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
• 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 65
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 1
• 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 1
• KOOHOBDNKYBBQD-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]imidazolidin-2-one Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1N1CCNC1=O KOOHOBDNKYBBQD-UHFFFAOYSA-N 0.000 claims 1
• MTYSBJGTTWLOPD-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]imidazolidine-2,4-dione Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1N1CC(=O)NC1=O MTYSBJGTTWLOPD-UHFFFAOYSA-N 0.000 claims 1
• FIOBXXPCLYHYPJ-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]pyrrolidin-2-one Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1N1CCCC1=O FIOBXXPCLYHYPJ-UHFFFAOYSA-N 0.000 claims 1
• WDUYIEVHJVPIIO-UHFFFAOYSA-N 1-[[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CN2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=N1 WDUYIEVHJVPIIO-UHFFFAOYSA-N 0.000 claims 1
• SBNVAZIJIYAPPW-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-yl)-6,8-bis(trifluoromethyl)-[1,3]oxazolo[5,4-h]quinoline Chemical compound N=1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2OC=1C1=NN=CO1 SBNVAZIJIYAPPW-UHFFFAOYSA-N 0.000 claims 1
• BLISGSHAFWQYIT-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-yl)-6,8-bis(trifluoromethyl)furo[3,2-h]quinoline Chemical compound O1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=NN=CO1 BLISGSHAFWQYIT-UHFFFAOYSA-N 0.000 claims 1
• LXVZWDSEPJDJNC-UHFFFAOYSA-N 2-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound C1N(C)CCC(C=2NC3=C4N=C(C=C(C4=CC=C3C=2)C(F)(F)F)C(F)(F)F)=C1 LXVZWDSEPJDJNC-UHFFFAOYSA-N 0.000 claims 1
• XXERAWXJZUWPCD-UHFFFAOYSA-N 2-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound C1N(C)CCC=C1C1=CC2=CC=C(C(=CC(=N3)C(F)(F)F)C(F)(F)F)C3=C2N1 XXERAWXJZUWPCD-UHFFFAOYSA-N 0.000 claims 1
• PFFUHRVXNYGXPB-UHFFFAOYSA-N 2-(1-methylpiperidin-3-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound C1N(C)CCCC1C1=CC2=CC=C(C(=CC(=N3)C(F)(F)F)C(F)(F)F)C3=C2N1 PFFUHRVXNYGXPB-UHFFFAOYSA-N 0.000 claims 1
• JUXKERWCKMOTBT-UHFFFAOYSA-N 2-(1-methylpiperidin-4-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound C1CN(C)CCC1C1=CC2=CC=C(C(=CC(=N3)C(F)(F)F)C(F)(F)F)C3=C2N1 JUXKERWCKMOTBT-UHFFFAOYSA-N 0.000 claims 1
• ILFFSXJKKNRCFD-UHFFFAOYSA-N 2-(2-propan-2-yl-4-propan-2-yloxyimidazo[1,2-a][1,8]naphthyridin-8-yl)-1,3,4-oxadiazole Chemical compound CC(C)OC1=CC(C(C)C)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 ILFFSXJKKNRCFD-UHFFFAOYSA-N 0.000 claims 1
• YEJBVDVPRNYIEH-UHFFFAOYSA-N 2-(2-propan-2-yl-4-pyrrolidin-1-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=1N1CCCC1 YEJBVDVPRNYIEH-UHFFFAOYSA-N 0.000 claims 1
• ZLQSJRQIGDOORQ-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyran-4-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=CCOCC1 ZLQSJRQIGDOORQ-UHFFFAOYSA-N 0.000 claims 1
• YCQODIDSIDSIED-UHFFFAOYSA-N 2-(3,6-dihydro-2h-pyran-5-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1=CCCOC1 YCQODIDSIDSIED-UHFFFAOYSA-N 0.000 claims 1
• UOQQNVBXXOBIPQ-UHFFFAOYSA-N 2-(4-cyclobutyl-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=1C1CCC1 UOQQNVBXXOBIPQ-UHFFFAOYSA-N 0.000 claims 1
• BLFHDVYASQMCCA-UHFFFAOYSA-N 2-(4-cyclohexyl-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=1C1CCCCC1 BLFHDVYASQMCCA-UHFFFAOYSA-N 0.000 claims 1
• KZLWXJQGUWCYHK-UHFFFAOYSA-N 2-(4-cyclopentyl-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=1C1CCCC1 KZLWXJQGUWCYHK-UHFFFAOYSA-N 0.000 claims 1
• KCVHGMULFNAICQ-UHFFFAOYSA-N 2-(4-cyclopropyl-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=1C1CC1 KCVHGMULFNAICQ-UHFFFAOYSA-N 0.000 claims 1
• USCFQYUJHYSCFO-UHFFFAOYSA-N 2-(4-ethoxy-2-propan-2-ylimidazo[1,2-a][1,8]naphthyridin-8-yl)-1,3,4-oxadiazole Chemical compound CCOC1=CC(C(C)C)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 USCFQYUJHYSCFO-UHFFFAOYSA-N 0.000 claims 1
• SSOQKFHRKJJXDO-UHFFFAOYSA-N 2-(4-piperidin-1-yl-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=1N1CCCCC1 SSOQKFHRKJJXDO-UHFFFAOYSA-N 0.000 claims 1
• LHQVQJUSAWIFQV-UHFFFAOYSA-N 2-(oxan-3-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1CCCOC1 LHQVQJUSAWIFQV-UHFFFAOYSA-N 0.000 claims 1
• HBPAKCNLWDTLFC-UHFFFAOYSA-N 2-(oxan-4-yl)-6,8-bis(trifluoromethyl)-1h-pyrrolo[3,2-h]quinoline Chemical compound N1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2C=C1C1CCOCC1 HBPAKCNLWDTLFC-UHFFFAOYSA-N 0.000 claims 1
• DKBNJASPFGEQCQ-UHFFFAOYSA-N 2-[2,3-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C=3N=C(C(F)(F)F)C(C(F)(F)F)=CC=3C=CC2=NC=1C1=NN=CO1 DKBNJASPFGEQCQ-UHFFFAOYSA-N 0.000 claims 1
• YMJPQGKQIIDXKZ-UHFFFAOYSA-N 2-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,6]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound N=1C(C(F)(F)F)=CN(C2=C3)C=1C(C(F)(F)F)=CC2=CN=C3C1=NN=CO1 YMJPQGKQIIDXKZ-UHFFFAOYSA-N 0.000 claims 1
• RMASRUOJYAIVDM-UHFFFAOYSA-N 2-[2-(1-methylpiperidin-3-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1N(C)CCCC1C1=CC(C(F)(F)F)=C(C=CC=2N3C=C(N=2)C=2OC=NN=2)C3=N1 RMASRUOJYAIVDM-UHFFFAOYSA-N 0.000 claims 1
• SWNOJVZBGGBDAI-UHFFFAOYSA-N 2-[2-(1-methylpiperidin-4-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1CN(C)CCC1C1=CC(C(F)(F)F)=C(C=CC=2N3C=C(N=2)C=2OC=NN=2)C3=N1 SWNOJVZBGGBDAI-UHFFFAOYSA-N 0.000 claims 1
• BHBZUIWGOSUDKX-UHFFFAOYSA-N 2-[2-(1-methylpyrrolidin-2-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound CN1CCCC1C1=CC(C(F)(F)F)=C(C=CC=2N3C=C(N=2)C=2OC=NN=2)C3=N1 BHBZUIWGOSUDKX-UHFFFAOYSA-N 0.000 claims 1
• QWWIYKSPPJEZQO-UHFFFAOYSA-N 2-[2-(1-methylpyrrolidin-3-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1N(C)CCC1C1=CC(C(F)(F)F)=C(C=CC=2N3C=C(N=2)C=2OC=NN=2)C3=N1 QWWIYKSPPJEZQO-UHFFFAOYSA-N 0.000 claims 1
• YJJOFTWRNIMHCB-UHFFFAOYSA-N 2-[2-(2-methylpropyl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(CC(C)C)=CC(C(F)(F)F)=C3C=CC2=NC=1C1=NN=CO1 YJJOFTWRNIMHCB-UHFFFAOYSA-N 0.000 claims 1
• LUICBNKUMBSMTK-UHFFFAOYSA-N 2-[2-(cyclopentylmethyl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound N=1C(N2C=C(N=C2C=C2)C=3OC=NN=3)=C2C(C(F)(F)F)=CC=1CC1CCCC1 LUICBNKUMBSMTK-UHFFFAOYSA-N 0.000 claims 1
• OGUNETWFMWRARH-UHFFFAOYSA-N 2-[2-(oxan-3-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2COCCC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 OGUNETWFMWRARH-UHFFFAOYSA-N 0.000 claims 1
• KEFLWXWDVGYNJN-UHFFFAOYSA-N 2-[2-(oxan-4-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2CCOCC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 KEFLWXWDVGYNJN-UHFFFAOYSA-N 0.000 claims 1
• HDVNOAPGOZANQJ-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2OCCC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 HDVNOAPGOZANQJ-UHFFFAOYSA-N 0.000 claims 1
• MCXJNRGGSYHSJD-UHFFFAOYSA-N 2-[2-(oxolan-3-yl)-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C1=CC(C2COCC2)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 MCXJNRGGSYHSJD-UHFFFAOYSA-N 0.000 claims 1
• DROZWOBCZYDKIM-UHFFFAOYSA-N 2-[2-propan-2-yl-3-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1=C(C(F)(F)F)C(C(C)C)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 DROZWOBCZYDKIM-UHFFFAOYSA-N 0.000 claims 1
• QBOKHQJEJRLURL-UHFFFAOYSA-N 2-[3,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C=1C(C(F)(F)F)=CN=C(N2C=3)C=1C=CC2=NC=3C1=NN=CO1 QBOKHQJEJRLURL-UHFFFAOYSA-N 0.000 claims 1
• MTZIHVKLVCEOQV-UHFFFAOYSA-N 2-[3-(1-methylpiperidin-4-yl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1CN(C)CCC1C1=CN=C2N3C=C(C=4OC=NN=4)N=C3C=CC2=C1 MTZIHVKLVCEOQV-UHFFFAOYSA-N 0.000 claims 1
• UEIBLNWCBMUJML-UHFFFAOYSA-N 2-[3-(oxolan-3-yl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C1OCCC1C1=CN=C2N3C=C(C=4OC=NN=4)N=C3C=CC2=C1 UEIBLNWCBMUJML-UHFFFAOYSA-N 0.000 claims 1
• QYTZWIWZNKPJEU-UHFFFAOYSA-N 2-[3-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1C(C(F)(F)F)=CN=C(N2C=3)C=1C=CC2=NC=3C1=NN=CO1 QYTZWIWZNKPJEU-UHFFFAOYSA-N 0.000 claims 1
• HYXVOSRUQSBMLY-UHFFFAOYSA-N 2-[3-propan-2-yl-4-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound FC(F)(F)C=1C(C(C)C)=CN=C(N2C=3)C=1C=CC2=NC=3C1=NN=CO1 HYXVOSRUQSBMLY-UHFFFAOYSA-N 0.000 claims 1
• KSJOQRCZTIYJTI-UHFFFAOYSA-N 2-[4-(1h-imidazol-2-yl)-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=NC=CN1 KSJOQRCZTIYJTI-UHFFFAOYSA-N 0.000 claims 1
• QINCCFVZMLWFJC-UHFFFAOYSA-N 2-[4-(1h-imidazol-5-yl)-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=CN=CN1 QINCCFVZMLWFJC-UHFFFAOYSA-N 0.000 claims 1
• SCIGHLYGHKOPOP-UHFFFAOYSA-N 2-[4-(2-methylpropyl)-2-propan-2-ylimidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound CC(C)CC1=CC(C(C)C)=NC(N2C=3)=C1C=CC2=NC=3C1=NN=CO1 SCIGHLYGHKOPOP-UHFFFAOYSA-N 0.000 claims 1
• XUIWXKIMQCIUKJ-UHFFFAOYSA-N 2-[4-(oxolan-2-yl)-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=1C1CCCO1 XUIWXKIMQCIUKJ-UHFFFAOYSA-N 0.000 claims 1
• FDRYFSUYPWYYFD-UHFFFAOYSA-N 2-[4-(oxolan-3-yl)-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=1C1CCOC1 FDRYFSUYPWYYFD-UHFFFAOYSA-N 0.000 claims 1
• YULVOSDBWLYKHF-UHFFFAOYSA-N 2-[5-pyrrolidin-1-yl-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(N3CCCC3)=CC2=NC=1C1=NN=CO1 YULVOSDBWLYKHF-UHFFFAOYSA-N 0.000 claims 1
• NQKMAQAJAIKVHX-UHFFFAOYSA-N 2-[5-pyrrolidin-1-yl-2-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C=1N2C3=NC(C(F)(F)F)=CC=C3C(N3CCCC3)=CC2=NC=1C1=NN=CO1 NQKMAQAJAIKVHX-UHFFFAOYSA-N 0.000 claims 1
• CQGGENGZMJDSOW-UHFFFAOYSA-N 2-[6,8-bis(trifluoromethyl)-[1,3]thiazolo[5,4-h]quinolin-2-yl]-1,3,4-oxadiazole Chemical compound N=1C=2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC=2SC=1C1=NN=CO1 CQGGENGZMJDSOW-UHFFFAOYSA-N 0.000 claims 1
• WFEOFJMBPIGBKR-UHFFFAOYSA-N 2-[6-pyrrolidin-1-yl-2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C12=NC(C=3OC=NN=3)=CN2C2=NC(C(F)(F)F)=CC(C(F)(F)F)=C2C=C1N1CCCC1 WFEOFJMBPIGBKR-UHFFFAOYSA-N 0.000 claims 1
• UUHPZAQGKPYTOZ-UHFFFAOYSA-N 2-[6-pyrrolidin-1-yl-2-(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3,4-oxadiazole Chemical compound C12=NC(C=3OC=NN=3)=CN2C2=NC(C(F)(F)F)=CC=C2C=C1N1CCCC1 UUHPZAQGKPYTOZ-UHFFFAOYSA-N 0.000 claims 1
• NTGKXXXYSATVND-UHFFFAOYSA-N 3-[2,4-bis(trifluoromethyl)imidazo[1,2-a][1,8]naphthyridin-8-yl]-1,3-oxazolidin-2-one Chemical compound C=1N2C3=NC(C(F)(F)F)=CC(C(F)(F)F)=C3C=CC2=NC=1N1CCOC1=O NTGKXXXYSATVND-UHFFFAOYSA-N 0.000 claims 1
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