TW201333003A - 用於增進先天性免疫反應之化合物及方法 - Google Patents
用於增進先天性免疫反應之化合物及方法 Download PDFInfo
- Publication number
- TW201333003A TW201333003A TW101138997A TW101138997A TW201333003A TW 201333003 A TW201333003 A TW 201333003A TW 101138997 A TW101138997 A TW 101138997A TW 101138997 A TW101138997 A TW 101138997A TW 201333003 A TW201333003 A TW 201333003A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- trifluoromethyl
- hydrogen
- methyl
- imidazo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 205
- 230000002708 enhancing effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 title abstract description 70
- 230000015788 innate immune response Effects 0.000 title description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 90
- 230000009385 viral infection Effects 0.000 claims abstract description 73
- 208000036142 Viral infection Diseases 0.000 claims abstract description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 376
- 229910052739 hydrogen Inorganic materials 0.000 claims description 376
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 319
- -1 -R 12 Chemical compound 0.000 claims description 313
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 218
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 216
- 150000002825 nitriles Chemical class 0.000 claims description 199
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 189
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 181
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 166
- 150000002431 hydrogen Chemical class 0.000 claims description 158
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 144
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 119
- 125000001072 heteroaryl group Chemical group 0.000 claims description 112
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 110
- 125000000623 heterocyclic group Chemical group 0.000 claims description 107
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 103
- 239000011737 fluorine Substances 0.000 claims description 103
- 229910052731 fluorine Inorganic materials 0.000 claims description 103
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 102
- 239000000460 chlorine Substances 0.000 claims description 101
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 100
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 100
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 100
- 229910052794 bromium Inorganic materials 0.000 claims description 100
- 229910052801 chlorine Inorganic materials 0.000 claims description 100
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 99
- 125000002757 morpholinyl group Chemical group 0.000 claims description 95
- 229910052757 nitrogen Inorganic materials 0.000 claims description 90
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 84
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 83
- 125000005843 halogen group Chemical group 0.000 claims description 79
- 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 77
- 125000003386 piperidinyl group Chemical group 0.000 claims description 74
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 71
- 125000002883 imidazolyl group Chemical group 0.000 claims description 69
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 67
- 125000002541 furyl group Chemical group 0.000 claims description 67
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 66
- 241000700605 Viruses Species 0.000 claims description 65
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 63
- 125000004076 pyridyl group Chemical group 0.000 claims description 62
- 125000001544 thienyl group Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 54
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 47
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 47
- 125000001153 fluoro group Chemical group F* 0.000 claims description 44
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 43
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 43
- 125000001246 bromo group Chemical group Br* 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 41
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 36
- 229940124530 sulfonamide Drugs 0.000 claims description 35
- 150000003456 sulfonamides Chemical class 0.000 claims description 35
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 33
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 32
- 125000002971 oxazolyl group Chemical group 0.000 claims description 30
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 22
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 21
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 206010036790 Productive cough Diseases 0.000 claims description 19
- 210000003802 sputum Anatomy 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 208000024794 sputum Diseases 0.000 claims description 18
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 241000701806 Human papillomavirus Species 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 125000003277 amino group Chemical group 0.000 claims description 12
- 230000028993 immune response Effects 0.000 claims description 12
- 101000617830 Homo sapiens Sterol O-acyltransferase 1 Proteins 0.000 claims description 11
- 102100021993 Sterol O-acyltransferase 1 Human genes 0.000 claims description 11
- 101000697584 Streptomyces lavendulae Streptothricin acetyltransferase Proteins 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 201000010153 skin papilloma Diseases 0.000 claims description 11
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 10
- 206010061598 Immunodeficiency Diseases 0.000 claims description 9
- 239000012190 activator Substances 0.000 claims description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- 210000004877 mucosa Anatomy 0.000 claims description 8
- HWJRQTQRAADPIC-UHFFFAOYSA-N n-cyanoformamide Chemical compound O=CNC#N HWJRQTQRAADPIC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 210000004400 mucous membrane Anatomy 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
- 210000000987 immune system Anatomy 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 208000009608 Papillomavirus Infections Diseases 0.000 claims description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
- 239000012049 topical pharmaceutical composition Substances 0.000 claims description 5
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 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
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-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
- 206010059313 Anogenital warts Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000000907 Condylomata Acuminata Diseases 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 208000021145 human papilloma virus infection Diseases 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 230000004163 JAK-STAT signaling pathway Effects 0.000 claims description 3
- 208000000260 Warts Diseases 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000003902 lesion Effects 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- YVBPNYXAQNAMLH-UHFFFAOYSA-N 1-hydroxy-2-methylpyrrolidine Chemical compound CC1CCCN1O YVBPNYXAQNAMLH-UHFFFAOYSA-N 0.000 claims description 2
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000029836 Inguinal Hernia Diseases 0.000 claims description 2
- 210000000436 anus Anatomy 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 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
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
- 230000008088 immune pathway Effects 0.000 claims description 2
- 210000003300 oropharynx Anatomy 0.000 claims description 2
- 210000003899 penis Anatomy 0.000 claims description 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 210000001215 vagina Anatomy 0.000 claims description 2
- 210000003905 vulva Anatomy 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 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 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
- 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
- PAXQXJDYVORMOO-UHFFFAOYSA-N 2-methyl-4-(trifluoromethyl)aniline Chemical group CC1=CC(C(F)(F)F)=CC=C1N PAXQXJDYVORMOO-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
- 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
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000005475 oxolanyl group Chemical group 0.000 claims 2
- 206010040882 skin lesion Diseases 0.000 claims 2
- 231100000444 skin lesion Toxicity 0.000 claims 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 1
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-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
- 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
- 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
- 241000156724 Antirhea Species 0.000 claims 1
- 241000587155 Athene Species 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 206010065173 Viral skin infection Diseases 0.000 claims 1
- 208000009621 actinic keratosis Diseases 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000002720 diazolyl group Chemical group 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 125000000466 oxiranyl group Chemical group 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000002585 base Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 19
- 210000003491 skin Anatomy 0.000 description 16
- 208000015181 infectious disease Diseases 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 8
- GUQMDNQYMMRJPY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazolidine Chemical group CC1(C)COCN1 GUQMDNQYMMRJPY-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 239000012453 solvate Substances 0.000 description 7
- 241000711549 Hepacivirus C Species 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000003443 antiviral agent Substances 0.000 description 6
- 230000034994 death Effects 0.000 description 6
- 231100000517 death Toxicity 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000036737 immune function Effects 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 230000003612 virological effect Effects 0.000 description 6
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 5
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- BTSVMLPWCFPJJL-UHFFFAOYSA-N ethoxy-methoxy-propoxy-lambda3-chlorane Chemical compound CCCOCl(OC)OCC BTSVMLPWCFPJJL-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000006574 non-aromatic ring group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000007123 defense Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 210000004392 genitalia Anatomy 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- 230000002458 infectious effect Effects 0.000 description 4
- 229940079322 interferon Drugs 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000010076 replication Effects 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 206010008342 Cervix carcinoma Diseases 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- 108010047761 Interferon-alpha Proteins 0.000 description 3
- 102000006992 Interferon-alpha Human genes 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 241000709664 Picornaviridae Species 0.000 description 3
- 241001505332 Polyomavirus sp. Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 102000002689 Toll-like receptor Human genes 0.000 description 3
- 108020000411 Toll-like receptor Proteins 0.000 description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 3
- 241000700647 Variola virus Species 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 201000010881 cervical cancer Diseases 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 206010022000 influenza Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 241001529453 unidentified herpesvirus Species 0.000 description 3
- 206010046885 vaginal cancer Diseases 0.000 description 3
- 208000013139 vaginal neoplasm Diseases 0.000 description 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 206010061424 Anal cancer Diseases 0.000 description 2
- 208000007860 Anus Neoplasms Diseases 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 241000605059 Bacteroidetes Species 0.000 description 2
- 241000337692 Bunia Species 0.000 description 2
- 235000013049 Bunias Nutrition 0.000 description 2
- 208000001490 Dengue Diseases 0.000 description 2
- 206010012310 Dengue fever Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- 241000709661 Enterovirus Species 0.000 description 2
- 241000710831 Flavivirus Species 0.000 description 2
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 101000959820 Homo sapiens Interferon alpha-1/13 Proteins 0.000 description 2
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 102100040019 Interferon alpha-1/13 Human genes 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000710842 Japanese encephalitis virus Species 0.000 description 2
- 208000032271 Malignant tumor of penis Diseases 0.000 description 2
- 201000005505 Measles Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 208000002471 Penile Neoplasms Diseases 0.000 description 2
- 206010034299 Penile cancer Diseases 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000710772 Yellow fever virus Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 201000011165 anus cancer Diseases 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 2
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 2
- 229940095758 cantharidin Drugs 0.000 description 2
- 229930008397 cantharidin Natural products 0.000 description 2
- DHZBEENLJMYSHQ-UHFFFAOYSA-N cantharidine Natural products O1C2CCC1C1(C)C2(C)C(=O)OC1=O DHZBEENLJMYSHQ-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 208000025729 dengue disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 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 description 2
- 230000008076 immune mechanism Effects 0.000 description 2
- 210000002510 keratinocyte Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 201000009240 nasopharyngitis Diseases 0.000 description 2
- 230000009826 neoplastic cell growth Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 102000007863 pattern recognition receptors Human genes 0.000 description 2
- 108010089193 pattern recognition receptors Proteins 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000010472 type I IFN response Effects 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940051021 yellow-fever virus Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-M (R)-lactate Chemical compound C[C@@H](O)C([O-])=O JVTAAEKCZFNVCJ-UWTATZPHSA-M 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- CBKDCOKSXCTDAA-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzothiophene Chemical compound C1CCCC2=C1C=CS2 CBKDCOKSXCTDAA-UHFFFAOYSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000711404 Avian avulavirus 1 Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 102000000844 Cell Surface Receptors Human genes 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 241001502567 Chikungunya virus Species 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000709687 Coxsackievirus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 241000725619 Dengue virus Species 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 241000710945 Eastern equine encephalitis virus Species 0.000 description 1
- 241001115402 Ebolavirus Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 241000711950 Filoviridae Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 241000709721 Hepatovirus A Species 0.000 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 241000701024 Human betaherpesvirus 5 Species 0.000 description 1
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 1
- 241000829111 Human polyomavirus 1 Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 102000002227 Interferon Type I Human genes 0.000 description 1
- 108010014726 Interferon Type I Proteins 0.000 description 1
- 102000042838 JAK family Human genes 0.000 description 1
- 108091082332 JAK family Proteins 0.000 description 1
- 241000701460 JC polyomavirus Species 0.000 description 1
- 108010024121 Janus Kinases Proteins 0.000 description 1
- 102000015617 Janus Kinases Human genes 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001115401 Marburgvirus Species 0.000 description 1
- 241000712079 Measles morbillivirus Species 0.000 description 1
- 241000351643 Metapneumovirus Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000700627 Monkeypox virus Species 0.000 description 1
- 241000711386 Mumps virus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000526636 Nipah henipavirus Species 0.000 description 1
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 description 1
- 241001263478 Norovirus Species 0.000 description 1
- 206010031096 Oropharyngeal cancer Diseases 0.000 description 1
- 206010057444 Oropharyngeal neoplasm Diseases 0.000 description 1
- 241000713112 Orthobunyavirus Species 0.000 description 1
- 241000150452 Orthohantavirus Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 206010033372 Pain and discomfort Diseases 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 241000713137 Phlebovirus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000725643 Respiratory syncytial virus Species 0.000 description 1
- 241000710942 Ross River virus Species 0.000 description 1
- 241000702670 Rotavirus Species 0.000 description 1
- 102000014400 SH2 domains Human genes 0.000 description 1
- 108050003452 SH2 domains Proteins 0.000 description 1
- 108010044012 STAT1 Transcription Factor Proteins 0.000 description 1
- 208000019802 Sexually transmitted disease Diseases 0.000 description 1
- 102100029904 Signal transducer and activator of transcription 1-alpha/beta Human genes 0.000 description 1
- 241000710960 Sindbis virus Species 0.000 description 1
- 241000710888 St. Louis encephalitis virus Species 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 241000710771 Tick-borne encephalitis virus Species 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- 241000710959 Venezuelan equine encephalitis virus Species 0.000 description 1
- 241000710886 West Nile virus Species 0.000 description 1
- 241000710951 Western equine encephalitis virus Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 208000002029 allergic contact dermatitis Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 208000007951 cervical intraepithelial neoplasia Diseases 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 201000004196 common wart Diseases 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000000315 cryotherapy Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 230000005860 defense response to virus Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940110377 dl- arginine Drugs 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000005007 innate immune system Anatomy 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 208000020082 intraepithelial neoplasia Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 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 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000005871 monkeypox Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 201000006958 oropharynx cancer Diseases 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000005026 transcription initiation Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 238000011277 treatment modality Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 description 1
- 229960001028 zanamivir Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161549784P | 2011-10-21 | 2011-10-21 | |
| US201261692431P | 2012-08-23 | 2012-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201333003A true TW201333003A (zh) | 2013-08-16 |
Family
ID=48141628
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104126180A TW201542567A (zh) | 2011-10-21 | 2012-10-22 | 用於增進先天性免疫反應之化合物及方法 |
| TW101138997A TW201333003A (zh) | 2011-10-21 | 2012-10-22 | 用於增進先天性免疫反應之化合物及方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104126180A TW201542567A (zh) | 2011-10-21 | 2012-10-22 | 用於增進先天性免疫反應之化合物及方法 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US20140249143A1 (enExample) |
| EP (1) | EP2768506A4 (enExample) |
| JP (1) | JP2014532626A (enExample) |
| KR (1) | KR20140094559A (enExample) |
| CN (1) | CN103957910A (enExample) |
| AR (1) | AR088793A1 (enExample) |
| AU (1) | AU2012325971B2 (enExample) |
| BR (1) | BR112014008727A2 (enExample) |
| CA (1) | CA2851801A1 (enExample) |
| CL (1) | CL2014001016A1 (enExample) |
| CO (1) | CO6910198A2 (enExample) |
| CR (1) | CR20140175A (enExample) |
| DO (1) | DOP2014000081A (enExample) |
| EA (1) | EA201490610A1 (enExample) |
| IL (1) | IL231894A0 (enExample) |
| MX (1) | MX2014004814A (enExample) |
| PE (1) | PE20141359A1 (enExample) |
| PH (1) | PH12014500865A1 (enExample) |
| SG (2) | SG11201400988SA (enExample) |
| TW (2) | TW201542567A (enExample) |
| UY (1) | UY34406A (enExample) |
| WO (1) | WO2013059559A2 (enExample) |
| ZA (1) | ZA201402392B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103333168B (zh) * | 2013-07-23 | 2015-08-05 | 清华大学 | 一种酰胺类化合物及其制备方法与应用 |
| US9758518B2 (en) | 2015-03-04 | 2017-09-12 | Pimera, Inc. | Compositions, uses and methods for making them |
| JP2017531631A (ja) | 2014-09-29 | 2017-10-26 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | 伝染性軟属腫ウイルスに対する抗ウイルス薬 |
| 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 |
| EP3601286A4 (en) | 2017-03-28 | 2020-09-23 | Pimera, Inc. | NEW CRYSTALLINE FORMS OF A POL1 INHIBITOR |
| CA3114551A1 (en) | 2018-10-23 | 2020-04-30 | Basf Se | Tricyclic pesticidal compounds |
| CN114732822B (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 |
| WO2021209265A1 (en) | 2020-04-14 | 2021-10-21 | Basf Se | Tricyclic pesticidal compounds |
| WO2022049521A1 (en) * | 2020-09-03 | 2022-03-10 | Glaxosmithkline Intellectual Property Development Limited | Imidazonaphthyridines and imidazopyridopyrimidines as ifnar2 agonists for treating sars-cov-2 infections |
| WO2022175425A1 (en) | 2021-02-22 | 2022-08-25 | Glaxosmithkline Intellectual Property Development Limited | Inhaled mtor kinase inhibitors for use in the treatment or the prevention of a respiratory rna virus infection |
| US12030883B2 (en) | 2021-09-21 | 2024-07-09 | Incyte Corporation | Hetero-tricyclic compounds as inhibitors of KRAS |
| JP2024537824A (ja) | 2021-10-01 | 2024-10-16 | インサイト・コーポレイション | ピラゾロキノリンｋｒａｓ阻害剤 |
| MX2024004444A (es) | 2021-10-14 | 2024-05-08 | Incyte Corp | Compuestos de quinolina como inhibidores de la proteina del virus de sarcoma de rata kirsten (kras). |
| WO2023244672A1 (en) | 2022-06-14 | 2023-12-21 | Assembly Biosciences, Inc. | 2-(imidazo[1, 2-a]1,8-naphthyridin-8-yl)-1,3,4-oxadiazole derivatives as enhancers of innate immune response for the treatment of viral infections |
| AU2024252826A1 (en) * | 2023-04-14 | 2025-10-16 | HUMANWELL PHARMACEUTICAL US, Inc. | Monoacylglycerol lipase (magl) inhibitors for the treatment of pain and related medical disorders |
| WO2025089372A1 (ja) * | 2023-10-26 | 2025-05-01 | 国立研究開発法人理化学研究所 | イソインドリン誘導体 |
| WO2025128898A1 (en) | 2023-12-13 | 2025-06-19 | Assembly Biosciences, Inc. | Imidazo[1,2-a][1,8]naphthyridine derivatives as enhancers of innate immune response for the treatment of viral infections |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59104A (en) * | 1979-02-09 | 1984-02-29 | Roussel Uclaf | Heterotricyclic derivatives,process for their preparation and pharmaceutical compositions incorporating them |
| 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 |
| US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| JP2006503802A (ja) * | 2002-04-03 | 2006-02-02 | エフ．ホフマン−ラ ロシュ アーゲー | イミダゾ縮合化合物 |
| 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 |
-
2012
- 2012-10-19 JP JP2014537274A patent/JP2014532626A/ja active Pending
- 2012-10-19 US US14/353,067 patent/US20140249143A1/en not_active Abandoned
- 2012-10-19 BR BR112014008727A patent/BR112014008727A2/pt not_active IP Right Cessation
- 2012-10-19 CA CA2851801A patent/CA2851801A1/en not_active Abandoned
- 2012-10-19 WO PCT/US2012/060971 patent/WO2013059559A2/en not_active Ceased
- 2012-10-19 KR KR1020147013668A patent/KR20140094559A/ko not_active Withdrawn
- 2012-10-19 EP EP12840986.9A patent/EP2768506A4/en not_active Withdrawn
- 2012-10-19 EA EA201490610A patent/EA201490610A1/ru unknown
- 2012-10-19 SG SG11201400988SA patent/SG11201400988SA/en unknown
- 2012-10-19 PE PE2014000559A patent/PE20141359A1/es not_active Application Discontinuation
- 2012-10-19 AU AU2012325971A patent/AU2012325971B2/en not_active Ceased
- 2012-10-19 SG SG10201505664WA patent/SG10201505664WA/en unknown
- 2012-10-19 PH PH1/2014/500865A patent/PH12014500865A1/en unknown
- 2012-10-19 MX MX2014004814A patent/MX2014004814A/es unknown
- 2012-10-19 CN CN201280051347.8A patent/CN103957910A/zh active Pending
- 2012-10-22 AR ARP120103945A patent/AR088793A1/es unknown
- 2012-10-22 UY UY0001034406A patent/UY34406A/es not_active Application Discontinuation
- 2012-10-22 TW TW104126180A patent/TW201542567A/zh unknown
- 2012-10-22 TW TW101138997A patent/TW201333003A/zh unknown
-
2014
- 2014-03-18 CO CO14058151A patent/CO6910198A2/es unknown
- 2014-03-31 ZA ZA2014/02392A patent/ZA201402392B/en unknown
- 2014-04-03 IL IL231894A patent/IL231894A0/en unknown
- 2014-04-21 CL CL2014001016A patent/CL2014001016A1/es unknown
- 2014-04-21 CR CR20140175A patent/CR20140175A/es unknown
- 2014-04-21 DO DO2014000081A patent/DOP2014000081A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013059559A3 (en) | 2013-11-14 |
| CL2014001016A1 (es) | 2015-01-16 |
| UY34406A (es) | 2013-05-31 |
| SG11201400988SA (en) | 2014-07-30 |
| PE20141359A1 (es) | 2014-10-13 |
| BR112014008727A2 (pt) | 2017-04-25 |
| CN103957910A (zh) | 2014-07-30 |
| AR088793A1 (es) | 2014-07-10 |
| WO2013059559A2 (en) | 2013-04-25 |
| CA2851801A1 (en) | 2013-04-25 |
| ZA201402392B (en) | 2017-09-27 |
| KR20140094559A (ko) | 2014-07-30 |
| EP2768506A2 (en) | 2014-08-27 |
| CO6910198A2 (es) | 2014-03-31 |
| DOP2014000081A (es) | 2014-07-15 |
| SG10201505664WA (en) | 2015-09-29 |
| TW201542567A (zh) | 2015-11-16 |
| IL231894A0 (en) | 2014-05-28 |
| MX2014004814A (es) | 2014-05-27 |
| PH12014500865A1 (en) | 2014-05-26 |
| AU2012325971B2 (en) | 2016-03-31 |
| EP2768506A4 (en) | 2015-08-19 |
| JP2014532626A (ja) | 2014-12-08 |
| AU2012325971A1 (en) | 2014-04-17 |
| US20140249143A1 (en) | 2014-09-04 |
| CR20140175A (es) | 2014-06-03 |
| EA201490610A1 (ru) | 2014-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201333003A (zh) | 用於增進先天性免疫反應之化合物及方法 | |
| JP4970048B2 (ja) | イミダゾ［４，５−ｃ］ピリジン化合物および抗ウイルス治療の方法 | |
| US10988484B2 (en) | Glucose uptake inhibitors | |
| AU2012314498B2 (en) | Viral replication inhibitors | |
| US20170226129A1 (en) | Heterocyclic compounds as rsv inhibitors | |
| CA3045371C (en) | Inhibitors of influenza virus replication and uses thereof | |
| TW201141857A (en) | Analogues for the treatment or prevention of flavivirus infections | |
| JP5411393B2 (ja) | ピラゾロキノリン類 | |
| AU2016368317A1 (en) | Inhibitors of influenza virus replication, application methods and uses thereof | |
| WO2018183586A1 (en) | Inhibitors of kinase networks and uses thereof | |
| JP2005516916A (ja) | 抗ヘルペス薬としてのピラゾロ−ピリジン誘導体 | |
| EP2953461B1 (en) | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of hepatitis c | |
| TWI894448B (zh) | Ctla-4小分子降解劑及其應用 | |
| WO2023244672A1 (en) | 2-(imidazo[1, 2-a]1,8-naphthyridin-8-yl)-1,3,4-oxadiazole derivatives as enhancers of innate immune response for the treatment of viral infections | |
| CN101538267B (zh) | 咪唑并[4,5-c]吡啶化合物和抗病毒治疗的方法 | |
| CA3005921C (en) | Substituted-(pyrrolo[2,3-b]pyridin-3-yl)-pyrimidin derivatives and use thereof as inhibitors of influenza virus replication | |
| WO2025128898A1 (en) | Imidazo[1,2-a][1,8]naphthyridine derivatives as enhancers of innate immune response for the treatment of viral infections | |
| TW202532074A (zh) | Ｓａｒｓ－ｃｏｖ２主要蛋白酶抑制劑 |