JP2009544708A5 - - Google Patents
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- Publication number
- 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 (enExample) | 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 (enExample) |
| EP (1) | EP2069356A1 (enExample) |
| JP (1) | JP2009544708A (enExample) |
| AU (1) | AU2007277253A1 (enExample) |
| CA (1) | CA2658545A1 (enExample) |
| WO (1) | WO2008013834A1 (enExample) |
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 |
| 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 |
| FR2945534B1 (fr) | 2009-05-12 | 2012-11-16 | Sanofi Aventis | DERIVES DE CYCLOPENTAL[c]PYRROLE-2-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 |
| AU2010313085A1 (en) * | 2009-10-30 | 2012-05-31 | 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 |
| US9220710B2 (en) * | 2013-01-09 | 2015-12-29 | Gilead Sciences, Inc. | Therapeutic compounds |
| EP3142659B1 (en) * | 2014-05-16 | 2021-03-24 | Purdue Research Foundation | Hiv-1 protease inhibitors and uses thereof |
| WO2016039403A1 (ja) * | 2014-09-11 | 2016-03-17 | 塩野義製薬株式会社 | 持続性ｈｉｖプロテアーゼ阻害剤 |
| CN118286245A (zh) | 2014-12-26 | 2024-07-05 | 埃莫里大学 | N4-羟基胞苷和衍生物及与其相关的抗病毒用途 |
| 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 |
| DK3337567T3 (da) | 2015-08-17 | 2021-12-06 | Purdue Research Foundation | Hiv-1-proteasehæmmere og anvendelser deraf |
| 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 |
| US11331331B2 (en) | 2017-12-07 | 2022-05-17 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US20230136594A1 (en) * | 2020-03-18 | 2023-05-04 | Purdue Research Foundation | Tricyclic p2-ligand containing potent hiv-protease inhibitors |
| 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 |
| 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 |
| ATE500823T1 (de) * | 1998-06-23 | 2011-03-15 | Us Of America Represented By The Secretary Dept Of Health And Human Services | Arzneimittel zur behandlung von hiv-infizierten säugetieren |
| 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 |
| CA2386850C (en) * | 1999-10-06 | 2010-03-30 | Piet Tom Bert Paul Wigerinck | 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 |
| JP4942915B2 (ja) * | 2002-04-26 | 2012-05-30 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖプロテアーゼ阻害剤化合物のホスホネートアナログの細胞蓄積 |
-
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 US US12/307,634 patent/US20090312318A1/en not_active Abandoned
- 2007-07-24 JP JP2009521811A patent/JP2009544708A/ja active Pending
- 2007-07-24 AU AU2007277253A patent/AU2007277253A1/en not_active Abandoned
- 2007-07-24 EP EP07836224A patent/EP2069356A1/en not_active Withdrawn
- 2007-07-24 CA CA002658545A patent/CA2658545A1/en not_active Abandoned
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