JP2007508234A5 - - Google Patents
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- Publication number
- JP2007508234A5 JP2007508234A5 JP2006515560A JP2006515560A JP2007508234A5 JP 2007508234 A5 JP2007508234 A5 JP 2007508234A5 JP 2006515560 A JP2006515560 A JP 2006515560A JP 2006515560 A JP2006515560 A JP 2006515560A JP 2007508234 A5 JP2007508234 A5 JP 2007508234A5
- Authority
- JP
- Japan
- Prior art keywords
- guanidine
- coronavirus
- strain
- virus
- cinnamoylguanidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 full Eniru Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 230000000840 anti-viral effect Effects 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- DMRPQMZUZKCGFD-VOTSOKGWSA-N (e)-n-(diaminomethylidene)-3-phenylprop-2-enamide Chemical compound NC(N)=NC(=O)\C=C\C1=CC=CC=C1 DMRPQMZUZKCGFD-VOTSOKGWSA-N 0.000 claims 79
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 58
- 241000711450 Infectious bronchitis virus Species 0.000 claims 52
- 241000711573 Coronaviridae Species 0.000 claims 47
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 32
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 30
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 30
- 229960004198 guanidine Drugs 0.000 claims 30
- 241000711443 Bovine coronavirus Species 0.000 claims 28
- 241000700605 Viruses Species 0.000 claims 26
- ALCCFQJJLCFYEK-CMDGGOBGSA-N (e)-n-(diaminomethylidene)-3-naphthalen-1-ylprop-2-enamide Chemical compound C1=CC=C2C(/C=C/C(=O)NC(=N)N)=CC=CC2=C1 ALCCFQJJLCFYEK-CMDGGOBGSA-N 0.000 claims 19
- 241000711466 Murine hepatitis virus Species 0.000 claims 18
- OKOXJPLBLDXQNV-DTWKUNHWSA-N (1r,2r)-n-(diaminomethylidene)-2-phenylcyclopropane-1-carboxamide Chemical compound NC(=N)NC(=O)[C@@H]1C[C@H]1C1=CC=CC=C1 OKOXJPLBLDXQNV-DTWKUNHWSA-N 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 17
- FYOXCRMHHBYILR-UHFFFAOYSA-N n-(diaminomethylidene)-5-phenylpenta-2,4-dienamide Chemical compound NC(=N)NC(=O)C=CC=CC1=CC=CC=C1 FYOXCRMHHBYILR-UHFFFAOYSA-N 0.000 claims 17
- OBEJPGOVZUDGAY-UHFFFAOYSA-N n-[amino(anilino)methylidene]-3-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=N)NC(=O)CCC1=CC=CC=C1 OBEJPGOVZUDGAY-UHFFFAOYSA-N 0.000 claims 15
- 208000015181 infectious disease Diseases 0.000 claims 14
- PZNOJKMDUBWCBQ-UHFFFAOYSA-N n-(diaminomethylidene)-3-(3-methylphenyl)prop-2-enamide Chemical compound CC1=CC=CC(C=CC(=O)N=C(N)N)=C1 PZNOJKMDUBWCBQ-UHFFFAOYSA-N 0.000 claims 14
- 102000004310 Ion Channels Human genes 0.000 claims 13
- 239000012528 membrane Substances 0.000 claims 13
- DHUGRAINHFHLBE-UHFFFAOYSA-N n-(diaminomethylidene)-4-phenylbenzamide Chemical compound C1=CC(C(=O)NC(=N)N)=CC=C1C1=CC=CC=C1 DHUGRAINHFHLBE-UHFFFAOYSA-N 0.000 claims 13
- 241000315672 SARS coronavirus Species 0.000 claims 12
- 230000002458 infectious effect Effects 0.000 claims 12
- 230000000968 intestinal effect Effects 0.000 claims 12
- PISVGNWQIULYBS-UHFFFAOYSA-N n-(diaminomethylidene)-3-(4-propan-2-ylphenyl)prop-2-enamide Chemical compound CC(C)C1=CC=C(C=CC(=O)N=C(N)N)C=C1 PISVGNWQIULYBS-UHFFFAOYSA-N 0.000 claims 12
- DXFJUUOQFIHODP-UHFFFAOYSA-N n-(diaminomethylidene)-3-(4-hydroxyphenyl)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=C(O)C=C1 DXFJUUOQFIHODP-UHFFFAOYSA-N 0.000 claims 11
- VDYFICUZUMSCMU-UHFFFAOYSA-N n-(diaminomethylidene)-4-phenoxybenzamide Chemical compound C1=CC(C(=O)NC(=N)N)=CC=C1OC1=CC=CC=C1 VDYFICUZUMSCMU-UHFFFAOYSA-N 0.000 claims 11
- LTGYAZVREDUARQ-UHFFFAOYSA-N 3-(2-cyclohexylphenyl)-n-(diaminomethylidene)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC=C1C1CCCCC1 LTGYAZVREDUARQ-UHFFFAOYSA-N 0.000 claims 10
- ZLHBIWZXHDEOFT-UHFFFAOYSA-N 3-(2-tert-butylphenyl)-n-(diaminomethylidene)prop-2-enamide Chemical compound CC(C)(C)C1=CC=CC=C1C=CC(=O)N=C(N)N ZLHBIWZXHDEOFT-UHFFFAOYSA-N 0.000 claims 10
- HRKGSHPEYGOZHJ-UHFFFAOYSA-N 3-(3-tert-butylphenyl)-n-(diaminomethylidene)prop-2-enamide Chemical compound CC(C)(C)C1=CC=CC(C=CC(=O)N=C(N)N)=C1 HRKGSHPEYGOZHJ-UHFFFAOYSA-N 0.000 claims 10
- MYIAILVVWSAAHT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-n-(diaminomethylidene)prop-2-enamide Chemical compound CC(C)(C)C1=CC=C(C=CC(=O)N=C(N)N)C=C1 MYIAILVVWSAAHT-UHFFFAOYSA-N 0.000 claims 10
- BAANTXNFSRCMCP-UHFFFAOYSA-N 5-(3-bromophenyl)-n-(diaminomethylidene)penta-2,4-dienamide Chemical compound NC(=N)NC(=O)C=CC=CC1=CC=CC(Br)=C1 BAANTXNFSRCMCP-UHFFFAOYSA-N 0.000 claims 10
- 208000005577 Gastroenteritis Diseases 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- LKKDZBGWPNQPOP-UHFFFAOYSA-N n-(diaminomethylidene)-2-naphthalen-1-ylacetamide Chemical compound C1=CC=C2C(CC(=O)NC(=N)N)=CC=CC2=C1 LKKDZBGWPNQPOP-UHFFFAOYSA-N 0.000 claims 10
- YHGKUFXGCRISMT-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2,3,5,6-tetramethylphenyl)prop-2-enamide Chemical compound CC1=CC(C)=C(C)C(C=CC(=O)N=C(N)N)=C1C YHGKUFXGCRISMT-UHFFFAOYSA-N 0.000 claims 10
- JBLYNJINPOWRFG-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2,5-dimethylphenyl)prop-2-enamide Chemical compound CC1=CC=C(C)C(C=CC(=O)N=C(N)N)=C1 JBLYNJINPOWRFG-UHFFFAOYSA-N 0.000 claims 10
- MMVUASXGHTWYSF-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2-methylphenyl)prop-2-enamide Chemical compound CC1=CC=CC=C1C=CC(=O)N=C(N)N MMVUASXGHTWYSF-UHFFFAOYSA-N 0.000 claims 10
- MHTGKDXWKXQUAQ-UHFFFAOYSA-N n-(diaminomethylidene)-3-(3-nitrophenyl)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1 MHTGKDXWKXQUAQ-UHFFFAOYSA-N 0.000 claims 10
- DRIQBBXJVJVPGI-UHFFFAOYSA-N n-(diaminomethylidene)-3-(3-phenylphenyl)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC(C=2C=CC=CC=2)=C1 DRIQBBXJVJVPGI-UHFFFAOYSA-N 0.000 claims 10
- RXEFMYMSKWTKRU-UHFFFAOYSA-N n-(diaminomethylidene)-3-(4-methylphenyl)prop-2-enamide Chemical compound CC1=CC=C(C=CC(=O)N=C(N)N)C=C1 RXEFMYMSKWTKRU-UHFFFAOYSA-N 0.000 claims 10
- NCAPVVSGOJRHLA-UHFFFAOYSA-N n-(diaminomethylidene)-3-naphthalen-2-ylprop-2-enamide Chemical compound C1=CC=CC2=CC(C=CC(=O)NC(=N)N)=CC=C21 NCAPVVSGOJRHLA-UHFFFAOYSA-N 0.000 claims 10
- WJOUCPOCQUVRJW-UHFFFAOYSA-N 3-phenyl-n-[n-phenyl-n'-(3-phenylpropanoyl)carbamimidoyl]propanamide Chemical compound C=1C=CC=CC=1CCC(=O)NC(=NC=1C=CC=CC=1)NC(=O)CCC1=CC=CC=C1 WJOUCPOCQUVRJW-UHFFFAOYSA-N 0.000 claims 9
- VDBNVLGNOVEOPB-UHFFFAOYSA-N n-(diaminomethylidene)-3-phenylpropanamide Chemical compound NC(=N)NC(=O)CCC1=CC=CC=C1 VDBNVLGNOVEOPB-UHFFFAOYSA-N 0.000 claims 9
- WTQIOSFOBLCCFK-UHFFFAOYSA-N n-[amino(anilino)methylidene]-3-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1C=CC(=O)N=C(N)NC1=CC=CC=C1 WTQIOSFOBLCCFK-UHFFFAOYSA-N 0.000 claims 9
- 241000725303 Human immunodeficiency virus Species 0.000 claims 8
- 241000711508 Turkey coronavirus Species 0.000 claims 8
- WYZGHFCGQGCOPZ-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2,3-dimethylphenyl)prop-2-enamide Chemical compound CC1=CC=CC(C=CC(=O)N=C(N)N)=C1C WYZGHFCGQGCOPZ-UHFFFAOYSA-N 0.000 claims 8
- HYBPCGHPOGXYLO-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2-ethylphenyl)prop-2-enamide Chemical compound CCC1=CC=CC=C1C=CC(=O)N=C(N)N HYBPCGHPOGXYLO-UHFFFAOYSA-N 0.000 claims 8
- MASFCCGAEYGKRN-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2-phenylphenyl)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC=C1C1=CC=CC=C1 MASFCCGAEYGKRN-UHFFFAOYSA-N 0.000 claims 8
- FMKRDNDKDWJOFK-UHFFFAOYSA-N n-(diaminomethylidene)-3-(furan-2-yl)prop-2-enamide Chemical compound NC(=N)NC(=O)C=CC1=CC=CO1 FMKRDNDKDWJOFK-UHFFFAOYSA-N 0.000 claims 8
- 241000894007 species Species 0.000 claims 8
- FMKRDNDKDWJOFK-ONEGZZNKSA-N (e)-n-(diaminomethylidene)-3-(furan-2-yl)prop-2-enamide Chemical compound NC(=N)NC(=O)\C=C\C1=CC=CO1 FMKRDNDKDWJOFK-ONEGZZNKSA-N 0.000 claims 7
- JDOUMVFXQGCGRI-UHFFFAOYSA-N 2-n,6-n-bis(diaminomethylidene)naphthalene-2,6-dicarboxamide Chemical compound C1=C(C(=O)NC(N)=N)C=CC2=CC(C(=O)NC(=N)N)=CC=C21 JDOUMVFXQGCGRI-UHFFFAOYSA-N 0.000 claims 7
- UCXHYERTWMEXOK-UHFFFAOYSA-N 3-phenyl-n-[n'-(3-phenylpropanoyl)carbamimidoyl]propanamide Chemical compound C=1C=CC=CC=1CCC(=O)NC(=N)NC(=O)CCC1=CC=CC=C1 UCXHYERTWMEXOK-UHFFFAOYSA-N 0.000 claims 7
- UGJNJXYDMZXDLY-UHFFFAOYSA-N n-(diaminomethylidene)-3-(4-phenylphenyl)prop-2-enamide Chemical compound C1=CC(C=CC(=O)N=C(N)N)=CC=C1C1=CC=CC=C1 UGJNJXYDMZXDLY-UHFFFAOYSA-N 0.000 claims 7
- GAOPLAYGZREQBS-UHFFFAOYSA-N n-[amino(anilino)methylidene]-6-hydroxynaphthalene-2-carboxamide Chemical compound C1=CC2=CC(O)=CC=C2C=C1C(=O)NC(=N)NC1=CC=CC=C1 GAOPLAYGZREQBS-UHFFFAOYSA-N 0.000 claims 7
- 241001135549 Porcine epidemic diarrhea virus Species 0.000 claims 6
- 241000156302 Porcine hemagglutinating encephalomyelitis virus Species 0.000 claims 6
- 241001428933 Rat coronavirus Species 0.000 claims 6
- 241000282898 Sus scrofa Species 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 6
- AUQMQBNHIQLGRP-UHFFFAOYSA-N n-(diaminomethylidene)-2-naphthalen-2-ylacetamide Chemical compound C1=CC=CC2=CC(CC(=O)NC(=N)N)=CC=C21 AUQMQBNHIQLGRP-UHFFFAOYSA-N 0.000 claims 6
- CHKULGQCBATXKS-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2,4,6-trimethylphenyl)prop-2-enamide Chemical compound CC1=CC(C)=C(C=CC(=O)N=C(N)N)C(C)=C1 CHKULGQCBATXKS-UHFFFAOYSA-N 0.000 claims 6
- LCRHPQDZNWNTDJ-UHFFFAOYSA-N n-(diaminomethylidene)-3-(2-nitrophenyl)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC=C1[N+]([O-])=O LCRHPQDZNWNTDJ-UHFFFAOYSA-N 0.000 claims 6
- AIUWTTOLGFMCEE-UHFFFAOYSA-N n-(diaminomethylidene)-3-phenylprop-2-enamide;hydrochloride Chemical compound Cl.NC(N)=NC(=O)C=CC1=CC=CC=C1 AIUWTTOLGFMCEE-UHFFFAOYSA-N 0.000 claims 6
- DVIHQDDVFWZYQL-CMDGGOBGSA-N (e)-n-(diaminomethylidene)-3-[4-(dimethylamino)phenyl]-2-methylprop-2-enamide Chemical compound CN(C)C1=CC=C(\C=C(/C)C(=O)NC(N)=N)C=C1 DVIHQDDVFWZYQL-CMDGGOBGSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- ORAVVJNVOXLQIT-UHFFFAOYSA-N n-(diaminomethylidene)-2-phenylacetamide Chemical compound NC(=N)NC(=O)CC1=CC=CC=C1 ORAVVJNVOXLQIT-UHFFFAOYSA-N 0.000 claims 5
- OLXNOYLRZRHHKP-UHFFFAOYSA-N n-(diaminomethylidene)-3-pyridin-3-ylprop-2-enamide Chemical compound NC(=N)NC(=O)C=CC1=CC=CN=C1 OLXNOYLRZRHHKP-UHFFFAOYSA-N 0.000 claims 5
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims 5
- BCDKGQNGEDRCKI-UHFFFAOYSA-N n-(diaminomethylidene)quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)NC(=N)N)=CC=C21 BCDKGQNGEDRCKI-UHFFFAOYSA-N 0.000 claims 5
- PCEORBLTWJVJHN-UHFFFAOYSA-N n-[amino-(3-phenylprop-2-enoylamino)methylidene]benzamide Chemical compound C=1C=CC=CC=1C(=O)N=C(N)NC(=O)C=CC1=CC=CC=C1 PCEORBLTWJVJHN-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- LVYUDSCQJGQXBI-UHFFFAOYSA-N 2-naphthalen-2-ylacetamide Chemical compound C1=CC=CC2=CC(CC(=O)N)=CC=C21 LVYUDSCQJGQXBI-UHFFFAOYSA-N 0.000 claims 4
- 241000282465 Canis Species 0.000 claims 4
- 241000711475 Feline infectious peritonitis virus Species 0.000 claims 4
- 241000711467 Human coronavirus 229E Species 0.000 claims 4
- 241001428935 Human coronavirus OC43 Species 0.000 claims 4
- 241000713666 Lentivirus Species 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 241000711493 Porcine respiratory coronavirus Species 0.000 claims 4
- 229960000789 guanidine hydrochloride Drugs 0.000 claims 4
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims 4
- DFHWZOGNQXSCSX-UHFFFAOYSA-N n-[amino(dimethylamino)methylidene]-3-phenylprop-2-enamide Chemical compound CN(C)C(N)=NC(=O)C=CC1=CC=CC=C1 DFHWZOGNQXSCSX-UHFFFAOYSA-N 0.000 claims 4
- 230000000241 respiratory effect Effects 0.000 claims 4
- OPGLKSXECNCJHX-UHFFFAOYSA-N 3-phenyl-n-[n-phenyl-n'-(3-phenylprop-2-enoyl)carbamimidoyl]prop-2-enamide Chemical compound C=1C=CC=CC=1C=CC(=O)NC(=NC(=O)C=CC=1C=CC=CC=1)NC1=CC=CC=C1 OPGLKSXECNCJHX-UHFFFAOYSA-N 0.000 claims 3
- 206010003230 arteritis Diseases 0.000 claims 3
- UWICDWBEVIDNNJ-UHFFFAOYSA-N n-(diaminomethylidene)prop-2-enamide Chemical compound NC(=N)NC(=O)C=C UWICDWBEVIDNNJ-UHFFFAOYSA-N 0.000 claims 3
- 125000002710 (E)-3-(trifluoromethyl)cinnamoyl group Chemical group 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims 2
- GUSUDQLCQAYCDU-UHFFFAOYSA-N 5-(2-bromophenyl)-n-(diaminomethylidene)penta-2,4-dienamide Chemical compound NC(=N)NC(=O)C=CC=CC1=CC=CC=C1Br GUSUDQLCQAYCDU-UHFFFAOYSA-N 0.000 claims 2
- 241000271566 Aves Species 0.000 claims 2
- 241000283690 Bos taurus Species 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 241000711506 Canine coronavirus Species 0.000 claims 2
- 241001594994 Canine respiratory coronavirus Species 0.000 claims 2
- 101710204837 Envelope small membrane protein Proteins 0.000 claims 2
- 241000963676 Equine coronavirus Species 0.000 claims 2
- 241001166747 Equine coronavirus NC99 Species 0.000 claims 2
- 241000283073 Equus caballus Species 0.000 claims 2
- 241000725579 Feline coronavirus Species 0.000 claims 2
- 241000282324 Felis Species 0.000 claims 2
- 241000287828 Gallus gallus Species 0.000 claims 2
- 241000711549 Hepacivirus C Species 0.000 claims 2
- 108700029057 Hepatitis C virus p7 Proteins 0.000 claims 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 2
- 101710145006 Lysis protein Proteins 0.000 claims 2
- 241000699666 Mus <mouse, genus> Species 0.000 claims 2
- 241000288906 Primates Species 0.000 claims 2
- 241000319426 SARS coronavirus BJ01 Species 0.000 claims 2
- 241000319424 SARS coronavirus BJ02 Species 0.000 claims 2
- 241000319442 SARS coronavirus BJ03 Species 0.000 claims 2
- 241000331209 SARS coronavirus BJ04 Species 0.000 claims 2
- 241000335418 SARS coronavirus CUHK-Su10 Species 0.000 claims 2
- 241000319449 SARS coronavirus CUHK-W1 Species 0.000 claims 2
- 241000346161 SARS coronavirus Frankfurt 1 Species 0.000 claims 2
- 241000319420 SARS coronavirus HKU-39849 Species 0.000 claims 2
- 241000651068 SARS coronavirus HSR 1 Species 0.000 claims 2
- 241000316209 SARS coronavirus Hong Kong/03/2003 Species 0.000 claims 2
- 241000651110 SARS coronavirus Shanhgai LY Species 0.000 claims 2
- 241000649112 SARS coronavirus Sin2500 Species 0.000 claims 2
- 241000649111 SARS coronavirus Sin2677 Species 0.000 claims 2
- 241000649110 SARS coronavirus Sin2679 Species 0.000 claims 2
- 241000649109 SARS coronavirus Sin2748 Species 0.000 claims 2
- 241000649108 SARS coronavirus Sin2774 Species 0.000 claims 2
- 241000346162 SARS coronavirus TW1 Species 0.000 claims 2
- 241000632404 SARS coronavirus TWC Species 0.000 claims 2
- 241000315688 SARS coronavirus Taiwan Species 0.000 claims 2
- 241000582842 SARS coronavirus Taiwan JC-2003 Species 0.000 claims 2
- 241000675940 SARS coronavirus Taiwan TC1 Species 0.000 claims 2
- 241000675962 SARS coronavirus Taiwan TC2 Species 0.000 claims 2
- 241000316168 SARS coronavirus Tor2 Species 0.000 claims 2
- 241000319366 SARS coronavirus Urbani Species 0.000 claims 2
- 241000315703 SARS coronavirus Vietnam Species 0.000 claims 2
- 241000582368 SARS coronavirus ZJ01 Species 0.000 claims 2
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 claims 2
- 206010044302 Tracheitis Diseases 0.000 claims 2
- 230000005714 functional activity Effects 0.000 claims 2
- 125000005456 glyceride group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- FAJIOICCLPXHDD-UHFFFAOYSA-N n-(diaminomethylidene)-6-methoxynaphthalene-2-carboxamide Chemical compound C1=C(C(=O)NC(N)=N)C=CC2=CC(OC)=CC=C21 FAJIOICCLPXHDD-UHFFFAOYSA-N 0.000 claims 2
- GAFVWCXCRDVUQZ-UHFFFAOYSA-N n-[amino(anilino)methylidene]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(=N)NC1=CC=CC=C1 GAFVWCXCRDVUQZ-UHFFFAOYSA-N 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 229960005486 vaccine Drugs 0.000 claims 2
- 241000725619 Dengue virus Species 0.000 claims 1
- PDZDLAOASBJMMO-UHFFFAOYSA-N NC(N)=NOC(=O)C=C Chemical compound NC(N)=NOC(=O)C=C PDZDLAOASBJMMO-UHFFFAOYSA-N 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000002222 downregulating effect Effects 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- 210000004962 mammalian cell Anatomy 0.000 claims 1
- PQZIOEUUUCRAFA-UHFFFAOYSA-N n-(dianilinomethylidene)-3-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1NC(NC=1C=CC=CC=1)=NC(=O)C=CC1=CC=CC=C1 PQZIOEUUUCRAFA-UHFFFAOYSA-N 0.000 claims 1
- LAJYPQZULXFTFW-UHFFFAOYSA-N n-[n'-(naphthalene-1-carbonyl)carbamimidoyl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NC(NC(=O)C=3C4=CC=CC=C4C=CC=3)=N)=CC=CC2=C1 LAJYPQZULXFTFW-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 241000633899 unclassified coronaviruses Species 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003903251 | 2003-06-26 | ||
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| US7745442B2 (en) * | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
| US8669280B2 (en) | 2005-06-24 | 2014-03-11 | Biotron Limited | Antiviral compounds and methods |
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| ES2614269T3 (es) * | 2007-08-03 | 2017-05-30 | Biotron Limited | Procedimientos y composiciones antivíricas frente a la hepatitis C |
| AU2013219202B2 (en) * | 2007-08-03 | 2016-12-08 | Biotron Limited | Hepatitis C antiviral compositions and methods |
| US20110217265A1 (en) * | 2008-09-23 | 2011-09-08 | Glenn Jeffrey S | Screening for Inhibitors of HCV Amphipathic Helix (AH) Function |
| PT2595980E (pt) | 2010-07-22 | 2014-11-27 | Gilead Sciences Inc | Métodos e compostos para tratar infeções pelo vírus da família paramyxoviridae |
| TWI698444B (zh) | 2014-10-29 | 2020-07-11 | 美商基利科學股份有限公司 | 製備核糖苷的方法 |
| DK3349758T3 (da) | 2015-09-16 | 2022-06-13 | Gilead Sciences Inc | Fremgangsmåder til behandling af arenaviridae-virusinfektioner |
| WO2018081863A1 (en) * | 2016-11-04 | 2018-05-11 | University Of Wollongong | 6-SUBSTITUTED DERIVATIVES OF HEXAMETHYLENE AMILORIDE AS INHIBITORS OF uPA AND USES THEREOF |
| CN110869028B (zh) | 2017-03-14 | 2023-01-20 | 吉利德科学公司 | 治疗猫冠状病毒感染的方法 |
| EP4219513A1 (en) | 2017-05-01 | 2023-08-02 | Gilead Sciences, Inc. | Crystalline form of (s)-2-ethylbutyl 2-(((s)-(((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran2-yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| CN111093627B (zh) | 2017-07-11 | 2024-03-08 | 吉利德科学公司 | 用于治疗病毒感染的包含rna聚合酶抑制剂和环糊精的组合物 |
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| EP4126011A4 (en) | 2020-03-30 | 2024-07-24 | Thomas Jefferson University | METHODS FOR TREATING, MITIGATING OR PREVENTING VIRUS INFECTIONS |
| JP7482250B2 (ja) | 2020-04-06 | 2024-05-13 | ギリアード サイエンシーズ， インコーポレイテッド | １’－シアノ置換カルバヌクレオシド類似体の吸入製剤 |
| EP4157272B1 (en) | 2020-05-29 | 2025-07-02 | Gilead Sciences, Inc. | Remdesivir for the treatment of viral infections |
| IL299202A (en) | 2020-06-24 | 2023-02-01 | Gilead Sciences Inc | 1'-cyano nucleoside analogs and uses thereof |
| US20220054575A1 (en) * | 2020-08-19 | 2022-02-24 | Natreon, Inc. | Protection against coronavirus infection by extracts and extract components |
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| US11926645B2 (en) | 2020-08-27 | 2024-03-12 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
| TWI925033B (zh) | 2020-10-16 | 2026-05-11 | 美商基利科學股份有限公司 | 磷脂化合物及其用途 |
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| WO2023012329A1 (en) | 2021-08-06 | 2023-02-09 | Intervet International B.V. | Method of treating veterinary viral diseases |
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| KR20240154647A (ko) | 2022-03-02 | 2024-10-25 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
| JP2025508943A (ja) | 2022-03-02 | 2025-04-10 | ギリアード サイエンシーズ， インコーポレイテッド | ウイルス感染症の治療のための化合物及び方法 |
| US20230382940A1 (en) | 2022-03-03 | 2023-11-30 | Gilead Sciences, Inc. | Antiviral compounds and methods of making and using the same |
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| JPWO2023167055A1 (enExample) * | 2022-03-03 | 2023-09-07 | ||
| WO2023239665A1 (en) | 2022-06-06 | 2023-12-14 | Gilead Sciences, Inc. | Methods for treatment of viral infections including sars-cov-2 |
| EP4547334A1 (en) | 2022-06-29 | 2025-05-07 | Gilead Sciences, Inc. | Solid forms of a nucleoside analogue and uses thereof |
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| WO2024173458A1 (en) | 2023-02-16 | 2024-08-22 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| WO2025049699A1 (en) | 2023-08-31 | 2025-03-06 | Gilead Sciences, Inc. | Antiviral compounds and methods of making and using the same |
| US20250084088A1 (en) | 2023-08-31 | 2025-03-13 | Gilead Sciences, Inc. | Antiviral compounds and methods of making and using the same |
| EP4774275A1 (en) | 2023-09-06 | 2026-07-15 | Gilead Sciences, LLC | Solid forms of a nucleoside analogue and uses thereof |
| KR20260079626A (ko) | 2023-09-28 | 2026-06-02 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
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-
2004
- 2004-06-26 EP EP04737487A patent/EP1646371A4/en not_active Withdrawn
- 2004-06-26 NZ NZ544671A patent/NZ544671A/en not_active IP Right Cessation
- 2004-06-26 CA CA2529949A patent/CA2529949C/en not_active Expired - Lifetime
- 2004-06-26 BR BRPI0411900A patent/BRPI0411900B8/pt not_active IP Right Cessation
- 2004-06-26 JP JP2006515560A patent/JP5030587B2/ja not_active Expired - Lifetime
- 2004-06-26 EP EP13164504.6A patent/EP2617709B8/en not_active Expired - Lifetime
- 2004-06-26 KR KR1020057024860A patent/KR101153254B1/ko not_active Expired - Fee Related
- 2004-06-26 WO PCT/AU2004/000866 patent/WO2004112687A2/en not_active Ceased
-
2012
- 2012-07-19 US US13/553,239 patent/US20130035328A1/en not_active Abandoned
-
2015
- 2015-02-06 US US14/615,616 patent/US20150313909A1/en not_active Abandoned
-
2017
- 2017-05-23 US US15/602,526 patent/US10472332B2/en not_active Expired - Lifetime
-
2019
- 2019-08-29 US US16/554,990 patent/US11192863B2/en not_active Expired - Fee Related
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