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 (enExample) | 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 (enExample) |
| EP (2) | EP1902017B1 (enExample) |
| JP (2) | JP5373392B2 (enExample) |
| KR (2) | KR101419327B1 (enExample) |
| CN (2) | CN103274970B (enExample) |
| AU (1) | AU2006261593B2 (enExample) |
| BR (2) | BRPI0612309B8 (enExample) |
| CA (1) | CA2612403C (enExample) |
| DK (2) | DK2826770T3 (enExample) |
| ES (2) | ES2710662T3 (enExample) |
| NZ (3) | NZ564398A (enExample) |
| PL (2) | PL2826770T3 (enExample) |
| PT (2) | PT2826770T (enExample) |
| SG (1) | SG163517A1 (enExample) |
| WO (1) | WO2006135978A1 (enExample) |
| ZA (1) | ZA200800256B (enExample) |
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| NZ544671A (en) * | 2003-06-26 | 2009-02-28 | Biotron Ltd | Antiviral compounds and methods |
| KR101419327B1 (ko) * | 2005-06-24 | 2014-07-14 | 바이오트론 리미티드 | 항바이러스 화합물 및 방법 |
| CN101743008A (zh) * | 2007-05-23 | 2010-06-16 | 西佳技术公司 | 用于治疗或预防登革热感染的抗病毒药 |
| AU2013219202B2 (en) * | 2007-08-03 | 2016-12-08 | Biotron Limited | Hepatitis C antiviral compositions and methods |
| PL2194976T3 (pl) * | 2007-08-03 | 2016-06-30 | Biotron Ltd | Kompozycje antywirusowe przeciwko zapaleniu wątroby typu C zawierające 5-(1-metylopirazol-4-ilo)-2-naftoiloguanidynę i 2'-C-metyloadenozynę lub 2'-C-metylocytydynę |
| JP5569857B2 (ja) * | 2007-08-10 | 2014-08-13 | アステラス製薬株式会社 | 二環式アシルグアニジン誘導体 |
| US20110306621A1 (en) * | 2009-02-09 | 2011-12-15 | Isao Kinoyama | Acylguanidine derivatives |
| WO2010090305A1 (ja) * | 2009-02-09 | 2010-08-12 | アステラス製薬株式会社 | 置換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 |
| SI2595980T1 (sl) | 2010-07-22 | 2014-11-28 | Gilead Sciences, Inc. | Postopki in sestavki za zdravljenje paramyxoviridae virusnih infekcij |
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| MX2013006951A (es) * | 2010-12-16 | 2013-10-03 | Abbvie Inc | Compuestos antivirales. |
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| 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 |
| DE19606355A1 (de) | 1996-02-12 | 1997-08-14 | Schering Ag | Kontrazeptive Freisetzungssysteme mit antiviraler und/oder antibakterieller Wirkung |
| 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 |
| WO2004056181A1 (en) | 2002-12-23 | 2004-07-08 | Global Cardiac Solutions Pty Ltd | Organ preconditioning, arrest, protection, preservation and recovery (2) |
| CA2520957C (en) * | 2003-03-31 | 2013-08-06 | Sucampo Ag | Method for treating vascular hyperpermeable disease |
| NZ544671A (en) * | 2003-06-26 | 2009-02-28 | Biotron Ltd | Antiviral compounds and methods |
| US20070099968A1 (en) | 2004-06-26 | 2007-05-03 | Biotron Limited | Antiviral compounds and methods |
| KR101419327B1 (ko) * | 2005-06-24 | 2014-07-14 | 바이오트론 리미티드 | 항바이러스 화합물 및 방법 |
| CN101287702A (zh) * | 2005-10-19 | 2008-10-15 | 弗·哈夫曼-拉罗切有限公司 | N-苯基苯乙酰胺非核苷逆转录酶抑制剂 |
| 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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- 2006-06-23 CN CN2006800226410A patent/CN101208297B/zh active Active
- 2006-06-23 EP EP06741271.8A patent/EP1902017B1/en active Active
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- 2006-06-23 DK DK06741271.8T patent/DK1902017T3/da active
- 2006-06-23 WO PCT/AU2006/000880 patent/WO2006135978A1/en not_active Ceased
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