JP2008543886A5 - - Google Patents
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- Publication number
- JP2008543886A5 JP2008543886A5 JP2008517277A JP2008517277A JP2008543886A5 JP 2008543886 A5 JP2008543886 A5 JP 2008543886A5 JP 2008517277 A JP2008517277 A JP 2008517277A JP 2008517277 A JP2008517277 A JP 2008517277A JP 2008543886 A5 JP2008543886 A5 JP 2008543886A5
- Authority
- JP
- Japan
- Prior art keywords
- naphthoyl
- guanidine
- virus
- pharmaceutical composition
- phenyl
- 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
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- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 241000700605 Viruses Species 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000011321 prophylaxis Methods 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- -1 6- (1-methylpyrazol-4-yl) -2-naphthoyl Chemical group 0.000 claims 2
- 241000725619 Dengue virus Species 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 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 1
- LXUATLNOCQKJFA-UHFFFAOYSA-N 3-(1,3-benzodioxol-4-yl)-n-(diaminomethylidene)prop-2-enamide Chemical compound NC(N)=NC(=O)C=CC1=CC=CC2=C1OCO2 LXUATLNOCQKJFA-UHFFFAOYSA-N 0.000 claims 1
- FYDIBGZNOMZHLV-UHFFFAOYSA-N 5-(2-chlorophenyl)-n-(diaminomethylidene)naphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)N=C(N)N)=CC=C2C=1C1=CC=CC=C1Cl FYDIBGZNOMZHLV-UHFFFAOYSA-N 0.000 claims 1
- BTUCDQHQLQMIEA-UHFFFAOYSA-N 5-(4-acetamidophenyl)-n-(diaminomethylidene)naphthalene-2-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C12 BTUCDQHQLQMIEA-UHFFFAOYSA-N 0.000 claims 1
- KQIDMHBKOXRMGB-UHFFFAOYSA-N 5-bromo-n-(diaminomethylidene)-6-methoxynaphthalene-2-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=CC2=C(Br)C(OC)=CC=C21 KQIDMHBKOXRMGB-UHFFFAOYSA-N 0.000 claims 1
- KQXDTPSECLJQKP-UHFFFAOYSA-N 5-bromo-n-(diaminomethylidene)naphthalene-2-carboxamide Chemical compound BrC1=CC=CC2=CC(C(=O)NC(=N)N)=CC=C21 KQXDTPSECLJQKP-UHFFFAOYSA-N 0.000 claims 1
- FSIWSRBQPDSXSX-UHFFFAOYSA-N 5-chloro-n-(diaminomethylidene)naphthalene-2-carboxamide Chemical compound ClC1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C21 FSIWSRBQPDSXSX-UHFFFAOYSA-N 0.000 claims 1
- NDVCYMRYZRRTIV-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)naphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)N=C(N)N)=CC=C2C=1C1CC1 NDVCYMRYZRRTIV-UHFFFAOYSA-N 0.000 claims 1
- 241000710781 Flaviviridae Species 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 241000288906 Primates Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000010171 animal model Methods 0.000 claims 1
- WVROWPPEIMRGAB-UHFFFAOYSA-N bit225 Chemical compound C1=NN(C)C=C1C1=CC=CC2=CC(C(=O)NC(N)=N)=CC=C12 WVROWPPEIMRGAB-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000879 imine group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- CVGVEMBAUCGNJO-UHFFFAOYSA-N n-(diaminomethylidene)-1,4-dimethoxynaphthalene-2-carboxamide Chemical compound C1=CC=C2C(OC)=CC(C(=O)N=C(N)N)=C(OC)C2=C1 CVGVEMBAUCGNJO-UHFFFAOYSA-N 0.000 claims 1
- LKUKOJXFZJCVFN-UHFFFAOYSA-N n-(diaminomethylidene)-1-methoxynaphthalene-2-carboxamide Chemical compound C1=CC=C2C(OC)=C(C(=O)N=C(N)N)C=CC2=C1 LKUKOJXFZJCVFN-UHFFFAOYSA-N 0.000 claims 1
- GYZMMUIXLCSNCG-UHFFFAOYSA-N n-(diaminomethylidene)-3-methoxynaphthalene-2-carboxamide Chemical compound C1=CC=C2C=C(C(=O)N=C(N)N)C(OC)=CC2=C1 GYZMMUIXLCSNCG-UHFFFAOYSA-N 0.000 claims 1
- QXDUDOUKGNWZJY-UHFFFAOYSA-N n-(diaminomethylidene)-5-(1,3,5-trimethylpyrazol-4-yl)naphthalene-2-carboxamide Chemical compound CC1=NN(C)C(C)=C1C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C12 QXDUDOUKGNWZJY-UHFFFAOYSA-N 0.000 claims 1
- ZKWIWAZERCVSEO-UHFFFAOYSA-N n-(diaminomethylidene)-5-(2,6-dimethoxypyridin-3-yl)naphthalene-2-carboxamide Chemical compound COC1=NC(OC)=CC=C1C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C12 ZKWIWAZERCVSEO-UHFFFAOYSA-N 0.000 claims 1
- TYSQSZSPRJYMPE-UHFFFAOYSA-N n-(diaminomethylidene)-5-(furan-3-yl)naphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)N=C(N)N)=CC=C2C=1C=1C=COC=1 TYSQSZSPRJYMPE-UHFFFAOYSA-N 0.000 claims 1
- ACGSCAJYUCGIPJ-UHFFFAOYSA-N n-(diaminomethylidene)-5-[1-(2-methylpropyl)pyrazol-4-yl]naphthalene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C12 ACGSCAJYUCGIPJ-UHFFFAOYSA-N 0.000 claims 1
- RXNDSIIGHZKXOG-UHFFFAOYSA-N n-(diaminomethylidene)-5-[4-(methanesulfonamido)phenyl]naphthalene-2-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C12 RXNDSIIGHZKXOG-UHFFFAOYSA-N 0.000 claims 1
- OVTIDDSSSPMFHP-UHFFFAOYSA-N n-(diaminomethylidene)-5-methylnaphthalene-2-carboxamide Chemical compound NC(=N)NC(=O)C1=CC=C2C(C)=CC=CC2=C1 OVTIDDSSSPMFHP-UHFFFAOYSA-N 0.000 claims 1
- SNBQWRKYKNFEGB-UHFFFAOYSA-N n-(diaminomethylidene)-5-phenylnaphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)N=C(N)N)=CC=C2C=1C1=CC=CC=C1 SNBQWRKYKNFEGB-UHFFFAOYSA-N 0.000 claims 1
- YXHNUCHTQQMPDD-UHFFFAOYSA-N n-(diaminomethylidene)-5-thiophen-2-ylnaphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)N=C(N)N)=CC=C2C=1C1=CC=CS1 YXHNUCHTQQMPDD-UHFFFAOYSA-N 0.000 claims 1
- DOPRKYPOGMWVJH-UHFFFAOYSA-N n-(diaminomethylidene)-5-thiophen-3-ylnaphthalene-2-carboxamide Chemical compound C=1C=CC2=CC(C(=O)NC(=N)N)=CC=C2C=1C=1C=CSC=1 DOPRKYPOGMWVJH-UHFFFAOYSA-N 0.000 claims 1
- JQTZRJXLFLYCHQ-UHFFFAOYSA-N n-(diaminomethylidene)-6-methylnaphthalene-2-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=CC2=CC(C)=CC=C21 JQTZRJXLFLYCHQ-UHFFFAOYSA-N 0.000 claims 1
- YECBDTOLBGWBGB-UHFFFAOYSA-N n-(diaminomethylidene)-6-thiophen-3-ylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC(C(=O)N=C(N)N)=CC=C2C=C1C=1C=CSC=1 YECBDTOLBGWBGB-UHFFFAOYSA-N 0.000 claims 1
- GXODLTCXRKLWHR-UHFFFAOYSA-N n-carbamimidoyl-n-(2,3-dihydro-1h-inden-4-yl)prop-2-enamide Chemical compound C=CC(=O)N(C(=N)N)C1=CC=CC2=C1CCC2 GXODLTCXRKLWHR-UHFFFAOYSA-N 0.000 claims 1
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2005903360A AU2005903360A0 (en) | 2005-06-24 | Anti-viral compounds and methods | |
| AU2005903360 | 2005-06-24 | ||
| PCT/AU2006/000880 WO2006135978A1 (en) | 2005-06-24 | 2006-06-23 | Antiviral compounds and methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012209126A Division JP5616410B2 (ja) | 2005-06-24 | 2012-09-24 | 抗ウイルス化合物および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008543886A JP2008543886A (ja) | 2008-12-04 |
| JP2008543886A5 true JP2008543886A5 (https=) | 2010-09-02 |
| JP5373392B2 JP5373392B2 (ja) | 2013-12-18 |
Family
ID=37570036
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008517277A Active JP5373392B2 (ja) | 2005-06-24 | 2006-06-23 | 抗ウイルス化合物および方法 |
| JP2012209126A Expired - Fee Related JP5616410B2 (ja) | 2005-06-24 | 2012-09-24 | 抗ウイルス化合物および方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012209126A Expired - Fee Related JP5616410B2 (ja) | 2005-06-24 | 2012-09-24 | 抗ウイルス化合物および方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US8669280B2 (https=) |
| EP (2) | EP1902017B1 (https=) |
| JP (2) | JP5373392B2 (https=) |
| KR (2) | KR20140072101A (https=) |
| CN (2) | CN103274970B (https=) |
| AU (1) | AU2006261593B2 (https=) |
| BR (2) | BR122020006906B8 (https=) |
| CA (1) | CA2612403C (https=) |
| DK (2) | DK2826770T3 (https=) |
| ES (2) | ES2491217T3 (https=) |
| NZ (3) | NZ596107A (https=) |
| PL (2) | PL2826770T3 (https=) |
| PT (2) | PT2826770T (https=) |
| SG (1) | SG163517A1 (https=) |
| WO (1) | WO2006135978A1 (https=) |
| ZA (1) | ZA200800256B (https=) |
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| 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 |
| JP2010528051A (ja) | 2007-05-23 | 2010-08-19 | シガ・テクノロジーズ・インコーポレーテッド | デング感染症の治療または予防のための抗ウイルス薬 |
| 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 |
| US20110207729A1 (en) * | 2007-08-10 | 2011-08-25 | Astellas Pharma Inc. | Bicyclic acylguanidine derivative |
| EP2394988A4 (en) * | 2009-02-09 | 2012-09-05 | Astellas Pharma Inc | SUBSTITUTED ACYLGUANIDINE DERIVATIVE |
| WO2010090304A1 (ja) * | 2009-02-09 | 2010-08-12 | アステラス製薬株式会社 | アシルグアニジン誘導体 |
| TW201116281A (en) | 2009-08-06 | 2011-05-16 | Astellas Pharma Inc | N atom containing ring acylguanidine derivatives |
| 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 |
| US9126106B1 (en) | 2010-11-05 | 2015-09-08 | Wms Gaming, Inc. | Promotional content coordination in wagering game machines |
| MX2013006951A (es) * | 2010-12-16 | 2013-10-03 | Abbvie Inc | Compuestos antivirales. |
| 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 |
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| SG11201907034PA (en) * | 2017-02-08 | 2019-08-27 | Biotron Ltd | Methods of treating influenza |
| US10682368B2 (en) | 2017-03-14 | 2020-06-16 | Gilead Sciences, Inc. | Methods of treating feline coronavirus infections |
| AU2018262501B2 (en) | 2017-05-01 | 2020-12-10 | Gilead Sciences, Inc. | Crystalline forms 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-dihydroxytetrahydrofuran-2 yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| WO2019014247A1 (en) | 2017-07-11 | 2019-01-17 | Gilead Sciences, Inc. | COMPOSITIONS COMPRISING POLYMERASE RNA INHIBITOR AND CYCLODEXTRIN FOR THE TREATMENT OF VIRAL INFECTIONS |
| US20220409587A1 (en) * | 2019-11-26 | 2022-12-29 | Biotron Limited | Methods of treating hiv-1 infection |
| US11660307B2 (en) | 2020-01-27 | 2023-05-30 | Gilead Sciences, Inc. | Methods for treating SARS CoV-2 infections |
| 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 |
| 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 |
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| KR20240154646A (ko) | 2022-03-02 | 2024-10-25 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
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| DE19621483A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| AUPO545297A0 (en) | 1997-03-04 | 1997-03-27 | Fujisawa Pharmaceutical Co., Ltd. | Guanidine derivatives |
| US20030113352A1 (en) | 2001-12-14 | 2003-06-19 | The Regents Of The University Of California | Neutralization of stratum corneum to treat hyperkeratotic skin lesions |
| CA2551169A1 (en) * | 2002-12-23 | 2004-07-08 | Global Cardiac Solutions Pty Ltd | Organ preconditioning, arrest, protection, preservation and recovery |
| JP4758337B2 (ja) * | 2003-03-31 | 2011-08-24 | 株式会社アールテック・ウエノ | 血管透過性亢進疾患を治療する方法 |
| EP2617709B8 (en) * | 2003-06-26 | 2022-12-21 | Biotron Limited | Guanidine derivatives as antiviral agents |
| US20070099968A1 (en) | 2004-06-26 | 2007-05-03 | Biotron Limited | Antiviral compounds and methods |
| NZ596107A (en) * | 2005-06-24 | 2013-09-27 | Biotron Ltd | Antiviral compounds and methods |
| AU2006303367A1 (en) * | 2005-10-19 | 2007-04-26 | F. Hoffmann-La Roche Ag | N-phenyl phenylacetamide non-nucleoside reverse transcriptase inihibitors |
| JP5727842B2 (ja) | 2011-04-12 | 2015-06-03 | 日野自動車株式会社 | 車両のインストルメントパネル構造 |
| KR101331921B1 (ko) * | 2013-01-16 | 2013-11-21 | 에스케이플래닛 주식회사 | 영유아의 안전을 위한 스마트 인터랙션 서비스를 제공하는 장치 및 방법, 이를 이용한 시스템 |
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2006
- 2006-06-23 NZ NZ596107A patent/NZ596107A/xx not_active IP Right Cessation
- 2006-06-23 PL PL13197255T patent/PL2826770T3/pl unknown
- 2006-06-23 DK DK13197255.6T patent/DK2826770T3/en active
- 2006-06-23 PL PL06741271T patent/PL1902017T3/pl unknown
- 2006-06-23 CN CN201310097430.5A patent/CN103274970B/zh not_active Expired - Fee Related
- 2006-06-23 PT PT13197255T patent/PT2826770T/pt unknown
- 2006-06-23 CN CN2006800226410A patent/CN101208297B/zh active Active
- 2006-06-23 SG SG201004454-3A patent/SG163517A1/en unknown
- 2006-06-23 KR KR1020147010199A patent/KR20140072101A/ko not_active Ceased
- 2006-06-23 WO PCT/AU2006/000880 patent/WO2006135978A1/en not_active Ceased
- 2006-06-23 EP EP06741271.8A patent/EP1902017B1/en active Active
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- 2006-06-23 JP JP2008517277A patent/JP5373392B2/ja active Active
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- 2006-06-23 KR KR1020087001886A patent/KR101419327B1/ko active Active
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