JP2009517412A5 - - Google Patents
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- JP2009517412A5 JP2009517412A5 JP2008542573A JP2008542573A JP2009517412A5 JP 2009517412 A5 JP2009517412 A5 JP 2009517412A5 JP 2008542573 A JP2008542573 A JP 2008542573A JP 2008542573 A JP2008542573 A JP 2008542573A JP 2009517412 A5 JP2009517412 A5 JP 2009517412A5
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- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- alkyl group
- formula
- compound
- 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.)
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- 125000004432 carbon atom Chemical group C* 0.000 claims 72
- 125000000217 alkyl group Chemical group 0.000 claims 60
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- -1 tetrahydro-3-furanyloxy Chemical group 0.000 claims 16
- 238000000034 method Methods 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 150000001413 amino acids Chemical class 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 229910052740 iodine Inorganic materials 0.000 claims 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 230000010933 acylation Effects 0.000 claims 4
- 238000005917 acylation reaction Methods 0.000 claims 4
- 239000000010 aprotic solvent Substances 0.000 claims 4
- 239000008346 aqueous phase Substances 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- 238000001308 synthesis method Methods 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 230000000865 phosphorylative effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 0 CC([C@@](*)N*)=O Chemical compound CC([C@@](*)N*)=O 0.000 description 2
- XEYUEIQAEAQUAK-UHFFFAOYSA-N CC(C)CN(C(CCCCN)COP(O)(O)=O)S(c(cc1)cc(F)c1N)(=O)=O Chemical compound CC(C)CN(C(CCCCN)COP(O)(O)=O)S(c(cc1)cc(F)c1N)(=O)=O XEYUEIQAEAQUAK-UHFFFAOYSA-N 0.000 description 1
- ZMXIYERNXPIYFR-UHFFFAOYSA-N CCc1c(cccc2)c2ccc1 Chemical compound CCc1c(cccc2)c2ccc1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74064205P | 2005-11-30 | 2005-11-30 | |
| PCT/CA2006/001963 WO2007062526A1 (en) | 2005-11-30 | 2006-11-30 | Lysine-based prodrugs of aspartyl protease inhibitors and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009517412A JP2009517412A (ja) | 2009-04-30 |
| JP2009517412A5 true JP2009517412A5 (enExample) | 2009-12-17 |
Family
ID=38091843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008542573A Pending JP2009517412A (ja) | 2005-11-30 | 2006-11-30 | アスパルチルプロテアーゼ阻害物質のリジンベースのプロドラッグ及びその調製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8227450B2 (enExample) |
| EP (1) | EP1971615B1 (enExample) |
| JP (1) | JP2009517412A (enExample) |
| CN (1) | CN101405293B (enExample) |
| AU (1) | AU2006319716B2 (enExample) |
| CA (1) | CA2632095A1 (enExample) |
| ES (1) | ES2452718T3 (enExample) |
| WO (1) | WO2007062526A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10149030A1 (de) | 2001-10-05 | 2003-04-10 | Viscum Ag | Stabile galenische gefriergetrocknete Arzneimittelzubereitung von rViscumin |
| US7388008B2 (en) | 2004-08-02 | 2008-06-17 | Ambrilia Biopharma Inc. | Lysine based compounds |
| JP2009517412A (ja) | 2005-11-30 | 2009-04-30 | アンブリリア バイオファーマ インコーポレイテッド | アスパルチルプロテアーゼ阻害物質のリジンベースのプロドラッグ及びその調製方法 |
| AU2007287353A1 (en) * | 2006-07-17 | 2008-02-28 | Ambrilia Biopharma Inc. | Method for improving pharmacokinetics |
| AU2007337830A1 (en) | 2006-09-21 | 2008-07-03 | Ambrilia Biopharma Inc. | Benzenesulfonamide derivatives as HIV protease inhibitors |
| WO2009148600A2 (en) * | 2008-06-06 | 2009-12-10 | Concert Pharmaceuticals, Inc. | Deuterated lysine-based compounds |
| CA2762582A1 (en) | 2009-05-27 | 2010-12-02 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| WO2012055031A1 (en) | 2010-10-28 | 2012-05-03 | Merck Canada Inc. | Hiv protease inhibitors |
| EP2771332B1 (en) | 2011-10-26 | 2016-06-29 | Merck Canada Inc. | Thiophen and thiazol sulfonamid derivatives as HIV protease inhibitors for the treatment of AIDS |
| US10588980B2 (en) | 2014-06-23 | 2020-03-17 | Novartis Ag | Fatty acids and their use in conjugation to biomolecules |
| US10369129B2 (en) | 2016-05-31 | 2019-08-06 | Taimed Biologics, Inc. | Long acting pharmaceutical composition of protease inhibitor |
| WO2017209732A1 (en) * | 2016-05-31 | 2017-12-07 | Taimed Biologics, Inc. | A long acting pharmaceutical composition of protease inhibitor |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013861A (en) | 1985-02-28 | 1991-05-07 | E. R. Squibb & Sons, Inc. | Ester substituted aminoalkanoylureido amino and imino acid and ester compounds |
| JPH06501950A (ja) | 1990-10-11 | 1994-03-03 | ベーリンガー インゲルハイム コマンディトゲゼルシャフト | 環状ペプチド、その調製法およびその薬理組成物としての使用 |
| US5614522A (en) | 1990-11-19 | 1997-03-25 | G.D. Searle & Co. | Retroviral protease inhibitors |
| EP0532466A3 (en) | 1991-09-12 | 1993-06-16 | Ciba-Geigy Ag | Derivatives of 5-amino-4-hydroxy-hexanoic acid and their therapeutical use |
| EP0656888B1 (en) | 1992-08-25 | 1998-01-07 | G.D. Searle & Co. | Sulfonylalkanoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US6022994A (en) | 1992-08-25 | 2000-02-08 | G. D. Searle &. Co. | Succinoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US5463104A (en) | 1992-08-25 | 1995-10-31 | G. D. Searle & Co. | Succinoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| JPH06321950A (ja) | 1993-05-14 | 1994-11-22 | Takeda Chem Ind Ltd | 水溶性ランカシジン誘導体 |
| WO1995006998A1 (en) | 1993-08-31 | 1995-03-09 | Stanley Kugell | Telephone billing method |
| WO1995024385A1 (en) | 1994-03-07 | 1995-09-14 | Vertex Pharmaceuticals Incorporated | Sulphonamide derivatives as aspartyl protease inhibitors |
| US5527829A (en) | 1994-05-23 | 1996-06-18 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors |
| ES2303337T3 (es) | 1995-01-20 | 2008-08-01 | G.D. Searle Llc | Inhibidores de la proteasa retroviral de bis-hidroxietilamino sulfonamida. |
| US5985870A (en) | 1995-03-10 | 1999-11-16 | G.D. Searle & Co. | Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5776718A (en) | 1995-03-24 | 1998-07-07 | Arris Pharmaceutical Corporation | Reversible protease inhibitors |
| US6037157A (en) | 1995-06-29 | 2000-03-14 | Abbott Laboratories | Method for improving pharmacokinetics |
| JP2000501111A (ja) | 1996-01-26 | 2000-02-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | アスパルチルプロテアーゼインヒビター |
| AU720615B2 (en) | 1997-01-17 | 2000-06-08 | Pharmacia & Upjohn Company | Bis-sulfonomides hydroxamic acids as MMP inhibitors |
| PT877019E (pt) | 1997-05-09 | 2002-05-31 | Hoechst Ag | Acidos diaminocarboxilicos substituidos |
| US6436989B1 (en) | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| EE200000386A (et) * | 1997-12-24 | 2001-12-17 | Vertex Pharmaceuticals Incorporated | Aspartüülproteaasi inhibiitorite eelravimid |
| US5986102A (en) | 1998-04-29 | 1999-11-16 | Pharmacopeia, Inc. | Hydroxypropylamide peptidomimetics as inhibitors of aspartyl proteases |
| ATE311391T1 (de) | 1999-02-12 | 2005-12-15 | Vertex Pharma | Aspartyl-protease-inhibitoren |
| 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 |
| US6656968B1 (en) * | 1999-06-16 | 2003-12-02 | Temple University - Of The Commonwealth System Of Higher Education | (Z)-styryl acetoxyphenyl sulfides as cyclooxygenase inhibitors |
| US6455587B1 (en) * | 2000-03-15 | 2002-09-24 | Pharmacor Inc. | Amino acid derivatives as HIV aspartyl protease inhibitors |
| US6506786B2 (en) | 2001-02-13 | 2003-01-14 | Pharmacor Inc. | HIV protease inhibitors based on amino acid derivatives |
| EP1480941B1 (en) | 2002-03-04 | 2011-01-26 | Ambrilia Biopharma Inc. | Urea derivatives as hiv aspartyl protease inhibitors |
| CA2374362C (en) | 2002-03-04 | 2008-01-22 | Brent Richard Stranix | Urea derivatives as hiv aspartyl protease inhibitors |
| PL376900A1 (pl) | 2002-12-16 | 2006-01-09 | Boehringer Ingelheim International Gmbh | Zastosowanie kombinacji zawierającej nienukleozydowy inhibitor odwrotnej transkryptazy (NNRTI) i inhibitor cytochromu P450, taki jak inhibitor proteazy |
| US6632816B1 (en) * | 2002-12-23 | 2003-10-14 | Pharmacor Inc. | Aromatic derivatives as HIV aspartyl protease inhibitors |
| AU2004312284B2 (en) | 2004-01-08 | 2010-08-05 | Medivir Ab | Non-nucleotide reverse transcriptase inhibitors |
| US7388008B2 (en) | 2004-08-02 | 2008-06-17 | Ambrilia Biopharma Inc. | Lysine based compounds |
| ATE417823T1 (de) | 2004-08-02 | 2009-01-15 | Ambrilia Biopharma Inc | Verbindungen auf lysinbasis |
| EP1877091B1 (en) | 2005-04-27 | 2015-03-25 | TaiMed Biologics, Inc. | Method for improving pharmacokinetics of protease inhibitors and protease inhibitor precursors |
| JP2009517412A (ja) | 2005-11-30 | 2009-04-30 | アンブリリア バイオファーマ インコーポレイテッド | アスパルチルプロテアーゼ阻害物質のリジンベースのプロドラッグ及びその調製方法 |
| AU2007287353A1 (en) | 2006-07-17 | 2008-02-28 | Ambrilia Biopharma Inc. | Method for improving pharmacokinetics |
| AU2007337830A1 (en) | 2006-09-21 | 2008-07-03 | Ambrilia Biopharma Inc. | Benzenesulfonamide derivatives as HIV protease inhibitors |
-
2006
- 2006-11-30 JP JP2008542573A patent/JP2009517412A/ja active Pending
- 2006-11-30 WO PCT/CA2006/001963 patent/WO2007062526A1/en not_active Ceased
- 2006-11-30 CA CA002632095A patent/CA2632095A1/en not_active Abandoned
- 2006-11-30 EP EP06817683.3A patent/EP1971615B1/en active Active
- 2006-11-30 AU AU2006319716A patent/AU2006319716B2/en not_active Ceased
- 2006-11-30 ES ES06817683.3T patent/ES2452718T3/es active Active
- 2006-11-30 CN CN200680051907.4A patent/CN101405293B/zh not_active Expired - Fee Related
- 2006-11-30 US US12/086,184 patent/US8227450B2/en not_active Expired - Fee Related
-
2008
- 2008-06-19 US US12/214,995 patent/US8580995B2/en not_active Expired - Fee Related
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