JP2009544708A5 - - Google Patents
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- JP2009544708A5 JP2009544708A5 JP2009521811A JP2009521811A JP2009544708A5 JP 2009544708 A5 JP2009544708 A5 JP 2009544708A5 JP 2009521811 A JP2009521811 A JP 2009521811A JP 2009521811 A JP2009521811 A JP 2009521811A JP 2009544708 A5 JP2009544708 A5 JP 2009544708A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- item
- compound according
- alkyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- -1 phosphate ester Chemical class 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 108091005804 Peptidases Proteins 0.000 claims description 4
- 239000004365 Protease Substances 0.000 claims description 4
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 108700022715 Viral Proteases Proteins 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 description 21
- 125000001769 aryl amino group Chemical group 0.000 description 20
- 125000005110 aryl thio group Chemical group 0.000 description 20
- 125000005236 alkanoylamino group Chemical group 0.000 description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 125000004475 heteroaralkyl group Chemical group 0.000 description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 5
- 125000005241 heteroarylamino group Chemical group 0.000 description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 description 5
- 125000005368 heteroarylthio group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000001717 pathogenic effect Effects 0.000 description 5
- 206010059866 Drug resistance Diseases 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 125000005128 aryl amino alkyl group Chemical group 0.000 description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 description 4
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83288206P | 2006-07-24 | 2006-07-24 | |
| PCT/US2007/016691 WO2008013834A1 (en) | 2006-07-24 | 2007-07-24 | Bisfuranyl protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009544708A JP2009544708A (ja) | 2009-12-17 |
| JP2009544708A5 true JP2009544708A5 (https=) | 2010-09-09 |
Family
ID=38739458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009521811A Pending JP2009544708A (ja) | 2006-07-24 | 2007-07-24 | ビスフラニルプロテアーゼ阻害剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20080070910A1 (https=) |
| EP (1) | EP2069356A1 (https=) |
| JP (1) | JP2009544708A (https=) |
| AU (1) | AU2007277253A1 (https=) |
| CA (1) | CA2658545A1 (https=) |
| WO (1) | WO2008013834A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8592487B2 (en) | 2007-10-26 | 2013-11-26 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| FR2941696B1 (fr) | 2009-02-05 | 2011-04-15 | Sanofi Aventis | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
| FR2945534B1 (fr) | 2009-05-12 | 2012-11-16 | Sanofi Aventis | DERIVES DE CYCLOPENTAL[c]PYRROLE-2-CARBOXYLATES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| FR2945531A1 (fr) | 2009-05-12 | 2010-11-19 | Sanofi Aventis | Derives de 7-aza-spiro°3,5!nonane-7-carboxylates, leur preparation et leur application en therapeutique |
| FR2945533B1 (fr) | 2009-05-12 | 2011-05-27 | Sanofi Aventis | Derives de cyclopenta°c!pyrrolyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
| WO2011051978A2 (en) * | 2009-10-30 | 2011-05-05 | Lupin Limited | A novel process for preparation of darunavir and darunavir ethanolate of fine particle size |
| WO2011061590A1 (en) | 2009-11-17 | 2011-05-26 | Hetero Research Foundation | Novel carboxamide derivatives as hiv inhibitors |
| CA2896244C (en) * | 2013-01-09 | 2017-07-04 | Gilead Sciences, Inc. | 5-membered heteroaryls and their use as antiviral agents |
| JP6622290B2 (ja) * | 2014-05-16 | 2019-12-18 | パーデュー・リサーチ・ファウンデーションＰｕｒｄｕｅ Ｒｅｓｅａｒｃｈ Ｆｏｕｎｄａｔｉｏｎ | Ｈｉｖ−１プロテアーゼ阻害剤およびその用途 |
| JPWO2016039403A1 (ja) * | 2014-09-11 | 2017-06-29 | 塩野義製薬株式会社 | 持続性ｈｉｖプロテアーゼ阻害剤 |
| DK3236972T3 (en) | 2014-12-26 | 2021-10-04 | Univ Emory | Antivirale N4-hydroxycytidin-derivativer |
| CN104910103A (zh) * | 2015-04-23 | 2015-09-16 | 上海应用技术学院 | 一种地瑞那韦中间体的制备方法 |
| US10472372B2 (en) | 2015-08-17 | 2019-11-12 | Purdue Research Foundation | HIV-1 protease inhibitors and uses thereof |
| CN105439997B (zh) * | 2015-11-13 | 2018-03-27 | 新疆农垦科学院 | 一种克百威氨基化半抗原的合成方法及应用 |
| CN105399711B (zh) * | 2015-11-13 | 2018-03-27 | 新疆农垦科学院 | 一种克百威羧基化半抗原的合成方法 |
| JP6804790B1 (ja) | 2017-12-07 | 2020-12-23 | エモリー ユニバーシティー | Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途 |
| JP7702424B2 (ja) * | 2020-03-18 | 2025-07-03 | パーデュー・リサーチ・ファウンデーション | 三環式ｐ２リガンドを含有する強力なｈｉｖプロテアーゼ阻害剤 |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728718A (en) * | 1994-12-20 | 1998-03-17 | The United States Of America As Represented By The Department Of Health And Human Services | 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same |
| PT2336134T (pt) * | 1998-06-23 | 2016-10-19 | The Board Of Trustees Of The Univ Of Illionis | Ensaio de aptidão e métodos para reduzir a resistência do hiv à terapia |
| WO1999067254A2 (en) * | 1998-06-23 | 1999-12-29 | The United States Of America Represented By The Secretary, Department Of Health And Human Services | Multi-drug resistant retroviral protease inhibitors and use thereof |
| AR031520A1 (es) * | 1999-06-11 | 2003-09-24 | Vertex Pharma | Un compuesto inhibidor de aspartilo proteasa, una composicion que lo comprende y un metodo para tratar un paciente con dicha composicion |
| EP1222192B8 (en) * | 1999-10-06 | 2008-10-01 | Tibotec Pharmaceuticals Ltd. | Hexahydrofuro¬2,3-b furan-3-yl-n- 3-¬(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino -1-benzyl-2-hydroxypropyl carbamate as retroviral protease inhibitor |
| US7157489B2 (en) * | 2002-03-12 | 2007-01-02 | The Board Of Trustees Of The University Of Illinois | HIV protease inhibitors |
| AU2003231765B9 (en) * | 2002-04-26 | 2010-01-28 | Gilead Sciences, Inc. | Cellular accumulation of phosphonate analogs of HIV protease inhibitor compounds and the compounds as such |
-
2007
- 2007-07-24 US US11/880,743 patent/US20080070910A1/en not_active Abandoned
- 2007-07-24 WO PCT/US2007/016691 patent/WO2008013834A1/en not_active Ceased
- 2007-07-24 EP EP07836224A patent/EP2069356A1/en not_active Withdrawn
- 2007-07-24 CA CA002658545A patent/CA2658545A1/en not_active Abandoned
- 2007-07-24 US US12/307,634 patent/US20090312318A1/en not_active Abandoned
- 2007-07-24 AU AU2007277253A patent/AU2007277253A1/en not_active Abandoned
- 2007-07-24 JP JP2009521811A patent/JP2009544708A/ja active Pending
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