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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| EP2617709B8 (en) | 2003-06-26 | 2022-12-21 | Biotron Limited | Guanidine derivatives as antiviral agents |
| US7745442B2 (en) * | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
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| GB0526240D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| ES2563477T3 (es) * | 2007-08-03 | 2016-03-15 | Biotron Limited | Composiciones antivirales para tratar la hepatitis C a base de 5-(1-metilpirazol-4-il)2-naftoilguanidina y 2'-C-metiladenosina o 2'-C-metilcitidina |
| AU2013219202B2 (en) * | 2007-08-03 | 2016-12-08 | Biotron Limited | Hepatitis C antiviral compositions and methods |
| WO2010039195A2 (en) * | 2008-09-23 | 2010-04-08 | The Board Of Trustees Of The Leland Stanford Junior University | Screening for inhibitors of hcv amphipathic helix (ah) function |
| BR122020020745B8 (pt) | 2010-07-22 | 2023-10-31 | Gilead Sciences Inc | Composto antiviral para o tratamento de infecções por paramyxoviridae e composição farmacêutica que o compreende |
| TWI767201B (zh) | 2014-10-29 | 2022-06-11 | 美商基利科學股份有限公司 | 絲狀病毒科病毒感染之治療 |
| SI3349758T1 (sl) | 2015-09-16 | 2022-08-31 | Gilead Sciences, Inc. | Postopki za zdravljenje okužb z virusom arenaviridae |
| WO2018081863A1 (en) * | 2016-11-04 | 2018-05-11 | University Of Wollongong | 6-SUBSTITUTED DERIVATIVES OF HEXAMETHYLENE AMILORIDE AS INHIBITORS OF uPA AND USES THEREOF |
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| WO2019014247A1 (en) | 2017-07-11 | 2019-01-17 | Gilead Sciences, Inc. | COMPOSITIONS COMPRISING POLYMERASE RNA INHIBITOR AND CYCLODEXTRIN FOR THE TREATMENT OF VIRAL INFECTIONS |
| US11660307B2 (en) | 2020-01-27 | 2023-05-30 | Gilead Sciences, Inc. | Methods for treating SARS CoV-2 infections |
| JP2021138619A (ja) * | 2020-03-02 | 2021-09-16 | フマキラー株式会社 | 抗コロナウイルス剤 |
| JP7554841B2 (ja) | 2020-03-12 | 2024-09-20 | ギリアード サイエンシーズ， インコーポレイテッド | １’－シアノヌクレオシドを調製する方法 |
| WO2021202550A1 (en) * | 2020-03-30 | 2021-10-07 | Thomas Jefferson University | Compounds, compositions, and methods for treating, ameliorating, or preventing viral infections |
| WO2021207049A1 (en) | 2020-04-06 | 2021-10-14 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| CA3179226A1 (en) | 2020-05-29 | 2021-12-02 | Tomas Cihlar | Remdesivir treatment methods |
| AU2021296841B2 (en) | 2020-06-24 | 2025-01-23 | 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 |
| AU2021330835B2 (en) | 2020-08-24 | 2023-12-14 | Gilead Sciences, Inc. | Phospholipid compounds and uses thereof |
| EP3960165A1 (en) * | 2020-08-25 | 2022-03-02 | Fondation EspeRare | Nhe-1 inhibitors for the treatment of coronavirus infections |
| SI4204421T1 (sl) | 2020-08-27 | 2024-07-31 | Gilead Sciences, Inc., | Spojine in postopki za zdravljenje virusnih okužb |
| TW202344257A (zh) | 2020-10-16 | 2023-11-16 | 美商基利科學股份有限公司 | 磷脂化合物及其用途 |
| EP4346772B1 (en) | 2021-05-26 | 2026-04-01 | Gilead Sciences, Inc. | Phospholipid formulations of 1'-cyano substituted carba-nucleoside analogs |
| WO2023012329A1 (en) | 2021-08-06 | 2023-02-09 | Intervet International B.V. | Method of treating veterinary viral diseases |
| AU2022328698B2 (en) | 2021-08-18 | 2025-02-20 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| KR20240154646A (ko) | 2022-03-02 | 2024-10-25 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
| IL315102A (en) | 2022-03-02 | 2024-10-01 | Gilead Sciences Inc | COMPOSITIONS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS |
| WO2023167055A1 (ja) * | 2022-03-03 | 2023-09-07 | 日本曹達株式会社 | 抗ウイルス剤 |
| PE20250419A1 (es) | 2022-03-03 | 2025-02-14 | Gilead Sciences Inc | Compuestos antivirales y metodos de elaboracion y uso de los mismos |
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| JP2025519390A (ja) | 2022-06-06 | 2025-06-26 | ギリアード サイエンシーズ， インコーポレイテッド | Ｓａｒｓ－ｃｏｖ－２を含むウイルス感染の治療方法 |
| WO2024006376A1 (en) | 2022-06-29 | 2024-01-04 | Gilead Sciences, Inc. | Solid forms of a nucleoside analogue and uses thereof |
| EP4547665A1 (en) | 2022-06-30 | 2025-05-07 | Gilead Sciences, Inc. | Solid forms of a nucleoside analogue and uses thereof |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
| WO2024112712A1 (en) * | 2022-11-21 | 2024-05-30 | Henderson Theodore | Treatment using an antiviral compound and spironolactone |
| WO2024173458A1 (en) | 2023-02-16 | 2024-08-22 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| IL326322A (en) | 2023-08-31 | 2026-04-01 | Gilead Sciences Inc | Antiviral compounds and methods for their production and use |
| US20250090537A1 (en) | 2023-08-31 | 2025-03-20 | Gilead Sciences, Inc. | Antiviral compounds and methods of making and using the same |
| US20250099476A1 (en) | 2023-09-06 | 2025-03-27 | Gilead Sciences, Inc. | Solid forms of a nucleoside analogue and uses thereof |
| US20250109157A1 (en) | 2023-09-28 | 2025-04-03 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734904A (en) * | 1956-02-14 | Xcxnhxc-nh | ||
| BE639386A (https=) | 1962-10-30 | |||
| FR1435379A (fr) * | 1964-07-30 | 1966-04-15 | American Cyanamid Co | Procédé pour stabiliser le chlorure de polyvinyle rigide contre les effets de la lumière |
| US3527758A (en) * | 1967-04-13 | 1970-09-08 | Merck & Co Inc | Process for the preparation of pyrazinoylguanidines from a pyrazinoic azide and a guanidine |
| DE2006186A1 (de) | 1970-02-11 | 1971-08-19 | Huebner Vamag | Verfahren zum Einsetzen eines Sitz ringes fur den Absperrkorper einer Armatur |
| DE2531343A1 (de) * | 1975-07-14 | 1977-02-10 | Henkel & Cie Gmbh | Antimikrobielle mittel |
| DD200618A1 (de) * | 1981-10-05 | 1983-05-25 | Manfred Augustin | Verfahren zur herstellung von neuen n-aroyl-und hetaroylimiden |
| US4496573A (en) * | 1982-08-24 | 1985-01-29 | William H. Rorer, Inc. | 1-Pyridylmethyl-3-acyl guanidines |
| US4894376A (en) * | 1988-02-26 | 1990-01-16 | Trustees Of The University Of Pennsylvania | Methods of treating diseases characterized by hyperexcitability of neurons |
| JPH0789859A (ja) * | 1990-04-05 | 1995-04-04 | Celtrix Pharmaceut Inc | ピラジン誘導体を含む薬剤学的組成物と眼の新血管新生を阻止する治療法 |
| IN177137B (https=) * | 1992-12-11 | 1996-11-16 | Hoechst India | |
| DE4301739A1 (de) * | 1993-01-22 | 1994-07-28 | Sauer Professor Dr Gerhard | Guanidin-Derivate zur Behandlung von Primär-Tumoren und viralen Erkrankungen |
| JPH0725768A (ja) * | 1993-07-09 | 1995-01-27 | Mitsubishi Chem Corp | 血管内膜肥厚抑制剤 |
| DE4325822A1 (de) * | 1993-07-31 | 1995-02-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| TW415937B (en) * | 1994-01-25 | 2000-12-21 | Hoechst Ag | Phenyl-substituted alkylcarboxylic acid guanidides bearing perfluoroalkyl groups, process for their preparation, their use as a medicament or diagnostic, and medicament containing them |
| DE4415873A1 (de) * | 1994-05-05 | 1995-11-09 | Hoechst Ag | Substituierte bizyklische Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JPH08225513A (ja) * | 1994-12-21 | 1996-09-03 | Kanebo Ltd | ナフトイルグアニジン誘導体 |
| AT408330B (de) | 1995-01-27 | 2001-10-25 | Colop Stempelerzeugung Skopek | Selbstfärbestempel |
| DK0738712T3 (da) * | 1995-04-18 | 2000-03-06 | Hoechst Ag | Substituerede indenoylguanidiner med antiarytmetisk kardioprotektiv virkning |
| DE19518796A1 (de) * | 1995-05-22 | 1996-11-28 | Hoechst Ag | Fluorphenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19527305A1 (de) * | 1995-07-26 | 1997-01-30 | Hoechst Ag | Substituierte Zimtsäureguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US5628984A (en) * | 1995-07-31 | 1997-05-13 | University Of North Carolina At Chapel Hill | Method of detecting lung disease |
| JPH0967332A (ja) * | 1995-08-29 | 1997-03-11 | Yamanouchi Pharmaceut Co Ltd | Ｎ−（２−プロペノイル）グアニジン誘導体 |
| DE19621482A1 (de) * | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 1-Naphthoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19622222A1 (de) * | 1996-06-03 | 1997-12-04 | Hoechst Ag | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikament zur Normalisierung der Serumlipide |
| AUPO545297A0 (en) * | 1997-03-04 | 1997-03-27 | Fujisawa Pharmaceutical Co., Ltd. | Guanidine derivatives |
| IL126276A0 (en) * | 1997-09-24 | 1999-05-09 | Hoechst Marion Roussel De Gmbh | The use of an inhibitor of the na+/H+ exchanger for the production of a medicament for the treatment or prophylaxis of disorders of the central nervous system |
| EP1032556B1 (en) * | 1997-10-21 | 2007-12-19 | Wyeth a Corporation of the State of Delaware | Pharmaceutically active compounds and methods of use |
| US7041702B1 (en) * | 1997-10-21 | 2006-05-09 | Scion Pharmaceuticals, Inc. | Pharmaceutically active compounds and methods of use |
| JP2002508507A (ja) * | 1997-12-18 | 2002-03-19 | セプラコア インコーポレーテッド | 新規な生物学的標的および創薬リード構造体の同時同定方法 |
| US6011059A (en) * | 1997-12-24 | 2000-01-04 | Bristol-Myers Squibb Company | Acyl guanidine sodium/proton exchange inhibitors and method |
| AUPP646498A0 (en) | 1998-10-12 | 1998-11-05 | Australian National University, The | A method of modulating ion channel functional activity |
| DE19849722A1 (de) * | 1998-10-28 | 2000-05-04 | Aventis Pharma Gmbh | Substituierte Phenyl-alkenoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19859727A1 (de) * | 1998-12-23 | 2000-06-29 | Aventis Pharma Gmbh | Die Verwendung von Hemmern des Natrium-Wasserstoff-Austauschers zur Herstellung eines Medikaments zur Verhinderung von altersbedingten Organ-Dysfunktionen, altersbedingten Erkrankungen zur Lebensverlängerung |
| AUPQ223999A0 (en) * | 1999-08-16 | 1999-09-09 | University Of Sydney, The | Intracellular feedback controls in the diagnosis and treatment of human disease |
| AUPS022802A0 (en) * | 2002-01-31 | 2002-02-21 | Macfarlane Burnet Institute For Medical Research And Public Health Limited, The | Anti-viral compounds |
| EP2617709B8 (en) | 2003-06-26 | 2022-12-21 | Biotron Limited | Guanidine derivatives as antiviral agents |
| NZ596107A (en) * | 2005-06-24 | 2013-09-27 | Biotron Ltd | Antiviral compounds and methods |
-
2004
- 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 BR BRPI0411900A patent/BRPI0411900B8/pt not_active IP Right Cessation
- 2004-06-26 WO PCT/AU2004/000866 patent/WO2004112687A2/en not_active Ceased
- 2004-06-26 JP JP2006515560A patent/JP5030587B2/ja not_active Expired - Lifetime
- 2004-06-26 EP EP04737487A patent/EP1646371A4/en not_active Withdrawn
- 2004-06-26 CA CA2529949A patent/CA2529949C/en not_active Expired - Lifetime
- 2004-06-26 NZ NZ544671A patent/NZ544671A/en not_active IP Right Cessation
-
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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