JP4579970B2 - リシンをベースにした化合物類 - Google Patents
リシンをベースにした化合物類 Download PDFInfo
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- JP4579970B2 JP4579970B2 JP2007501073A JP2007501073A JP4579970B2 JP 4579970 B2 JP4579970 B2 JP 4579970B2 JP 2007501073 A JP2007501073 A JP 2007501073A JP 2007501073 A JP2007501073 A JP 2007501073A JP 4579970 B2 JP4579970 B2 JP 4579970B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 255
- 239000004472 Lysine Substances 0.000 title claims abstract description 12
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 33
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 18
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 11
- -1 tetrahydro-3-furanyloxy group Chemical group 0.000 claims description 121
- 125000004432 carbon atom Chemical group C* 0.000 claims description 88
- 150000003839 salts Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 20
- 229910052727 yttrium Inorganic materials 0.000 claims description 18
- 208000031886 HIV Infections Diseases 0.000 claims description 17
- 208000037357 HIV infectious disease Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 15
- 229940079593 drug Drugs 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 12
- 101150065749 Churc1 gene Proteins 0.000 claims description 12
- 102100038239 Protein Churchill Human genes 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 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 description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- KHASNRBNVBIREH-IZEXYCQBSA-N methyl n-[(2s)-1-[[(5s)-5-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-6-phosphonooxyhexyl]amino]-1-oxo-3,3-diphenylpropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C([C@H](NC(=O)OC)C(=O)NCCCC[C@@H](COP(O)(O)=O)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C1=CC=CC=C1 KHASNRBNVBIREH-IZEXYCQBSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- RSJAAVKNQYKXBN-QCDSWUKFSA-N CC(C)CN([C@@H](CCCCNC(=O)[C@H](C(C1=CC=CC=C1)C2=CC=CC=C2)NC(=O)O)COP(=O)(O)O)S(=O)(=O)C3=CC(=C(C=C3)N)F Chemical compound CC(C)CN([C@@H](CCCCNC(=O)[C@H](C(C1=CC=CC=C1)C2=CC=CC=C2)NC(=O)O)COP(=O)(O)O)S(=O)(=O)C3=CC(=C(C=C3)N)F RSJAAVKNQYKXBN-QCDSWUKFSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229920001577 copolymer Chemical group 0.000 claims 2
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 37
- 239000003443 antiviral agent Substances 0.000 abstract description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 230000015572 biosynthetic process Effects 0.000 description 57
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- 238000005481 NMR spectroscopy Methods 0.000 description 40
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
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- 235000019439 ethyl acetate Nutrition 0.000 description 26
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- 108091005502 Aspartic proteases Proteins 0.000 description 22
- 102000035101 Aspartic proteases Human genes 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
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- 239000000047 product Substances 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
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- 241000700605 Viruses Species 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- QAHLFXYLXBBCPS-IZEXYCQBSA-N methyl n-[(2s)-1-[[(5s)-5-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-6-hydroxyhexyl]amino]-1-oxo-3,3-diphenylpropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C([C@H](NC(=O)OC)C(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C1=CC=CC=C1 QAHLFXYLXBBCPS-IZEXYCQBSA-N 0.000 description 13
- RSZHUYJAGSXWNM-NRFANRHFSA-N tert-butyl n-[4-[[(2s)-1-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexan-2-yl]-(2-methylpropyl)sulfamoyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1 RSZHUYJAGSXWNM-NRFANRHFSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- 239000004030 hiv protease inhibitor Substances 0.000 description 12
- SCWIUHICGSPBKM-VIFPVBQESA-N (3s)-3-(2-methylpropylamino)azepan-2-one Chemical compound CC(C)CN[C@H]1CCCCNC1=O SCWIUHICGSPBKM-VIFPVBQESA-N 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
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- 239000003696 aspartic proteinase inhibitor Substances 0.000 description 10
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- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 9
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- 239000012467 final product Substances 0.000 description 9
- 235000018977 lysine Nutrition 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 8
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- 229940122440 HIV protease inhibitor Drugs 0.000 description 7
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 7
- 239000002671 adjuvant Substances 0.000 description 7
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- MLDFGFYWCJHWLS-VWLOTQADSA-N tert-butyl n-[4-[[(2s)-1-diethoxyphosphoryloxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexan-2-yl]-(2-methylpropyl)sulfamoyl]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC[C@@H](COP(=O)(OCC)OCC)N(CC(C)C)S(=O)(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1 MLDFGFYWCJHWLS-VWLOTQADSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/41—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CA2004/001440 WO2006012725A1 (en) | 2004-08-02 | 2004-08-02 | Lysine based compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007525527A JP2007525527A (ja) | 2007-09-06 |
| JP2007525527A5 JP2007525527A5 (enExample) | 2009-08-20 |
| JP4579970B2 true JP4579970B2 (ja) | 2010-11-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007501073A Expired - Fee Related JP4579970B2 (ja) | 2004-08-02 | 2004-08-02 | リシンをベースにした化合物類 |
Country Status (14)
| Country | Link |
|---|---|
| EP (2) | EP1773763B1 (enExample) |
| JP (1) | JP4579970B2 (enExample) |
| CN (1) | CN1942436B (enExample) |
| AT (1) | ATE417823T1 (enExample) |
| AU (2) | AU2004322123B2 (enExample) |
| BR (1) | BRPI0418651A (enExample) |
| CA (1) | CA2560071C (enExample) |
| DE (1) | DE602004018548D1 (enExample) |
| ES (2) | ES2575871T3 (enExample) |
| IL (1) | IL180958A0 (enExample) |
| MX (1) | MX2007001278A (enExample) |
| NO (1) | NO20071152L (enExample) |
| RU (1) | RU2009139259A (enExample) |
| WO (1) | WO2006012725A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7388008B2 (en) | 2004-08-02 | 2008-06-17 | Ambrilia Biopharma Inc. | Lysine based compounds |
| ES2575871T3 (es) | 2004-08-02 | 2016-07-01 | Ambrilia Biopharma Inc. | Composiciones farmacéuticas que comprende un compuesto a base de lisina y un agente antiviral o antirretroviral VIH |
| JP2010502569A (ja) * | 2006-07-17 | 2010-01-28 | アンブリリア バイオファーマ インコーポレイテッド | 薬物動態学の改善方法 |
| EP2064177B1 (en) | 2006-09-21 | 2017-04-05 | TaiMed Biologics, Inc. | Protease inhibitors |
| WO2009148600A2 (en) * | 2008-06-06 | 2009-12-10 | Concert Pharmaceuticals, Inc. | Deuterated lysine-based compounds |
| EP2435037B1 (en) | 2009-05-27 | 2014-11-12 | Merck Sharp & Dohme Corp. | Hiv protease inhibitors |
| US9079834B2 (en) | 2010-10-28 | 2015-07-14 | Merck Canada Inc. | HIV protease inhibitors |
| EP2632908B1 (en) | 2010-10-29 | 2016-05-25 | Merck Canada Inc. | Sulfonamides as hiv protease inhibitors |
| US9133157B2 (en) | 2011-10-26 | 2015-09-15 | Merck Canada Inc. | HIV protease inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436989B1 (en) * | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| CA2405151A1 (en) * | 2000-04-07 | 2001-10-18 | University Of Maryland, Baltimore | Bile acid containing prodrugs with enhanced bioavailability |
| US6617310B2 (en) * | 2000-07-19 | 2003-09-09 | Bristol-Myers Squibb Pharma Company | Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines |
| JP2004517045A (ja) * | 2000-08-18 | 2004-06-10 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシティ オブ イリノイ | 癌およびｈｉｖの治療用ベツリン酸誘導体のプロドラッグ |
| US6506786B2 (en) * | 2001-02-13 | 2003-01-14 | Pharmacor Inc. | HIV protease inhibitors based on amino acid derivatives |
| US6632816B1 (en) * | 2002-12-23 | 2003-10-14 | Pharmacor Inc. | Aromatic derivatives as HIV aspartyl protease inhibitors |
| ES2575871T3 (es) | 2004-08-02 | 2016-07-01 | Ambrilia Biopharma Inc. | Composiciones farmacéuticas que comprende un compuesto a base de lisina y un agente antiviral o antirretroviral VIH |
-
2004
- 2004-08-02 ES ES08021798.7T patent/ES2575871T3/es not_active Expired - Lifetime
- 2004-08-02 MX MX2007001278A patent/MX2007001278A/es active IP Right Grant
- 2004-08-02 BR BRPI0418651-6A patent/BRPI0418651A/pt not_active IP Right Cessation
- 2004-08-02 WO PCT/CA2004/001440 patent/WO2006012725A1/en not_active Ceased
- 2004-08-02 EP EP04761606A patent/EP1773763B1/en not_active Expired - Lifetime
- 2004-08-02 CA CA2560071A patent/CA2560071C/en not_active Expired - Fee Related
- 2004-08-02 ES ES04761606T patent/ES2319996T3/es not_active Expired - Lifetime
- 2004-08-02 EP EP08021798.7A patent/EP2165709B1/en not_active Expired - Lifetime
- 2004-08-02 JP JP2007501073A patent/JP4579970B2/ja not_active Expired - Fee Related
- 2004-08-02 AU AU2004322123A patent/AU2004322123B2/en not_active Ceased
- 2004-08-02 AT AT04761606T patent/ATE417823T1/de not_active IP Right Cessation
- 2004-08-02 DE DE602004018548T patent/DE602004018548D1/de not_active Expired - Lifetime
- 2004-08-02 CN CN2004800427980A patent/CN1942436B/zh not_active Expired - Fee Related
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2007
- 2007-01-25 IL IL180958A patent/IL180958A0/en unknown
- 2007-03-01 NO NO20071152A patent/NO20071152L/no not_active Application Discontinuation
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2009
- 2009-10-23 RU RU2009139259/04A patent/RU2009139259A/ru not_active Application Discontinuation
- 2009-10-28 AU AU2009230800A patent/AU2009230800A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2165709B1 (en) | 2016-03-16 |
| CA2560071C (en) | 2012-09-25 |
| NO20071152L (no) | 2007-03-01 |
| CA2560071A1 (en) | 2006-02-09 |
| EP1773763A4 (en) | 2007-08-08 |
| EP2165709A2 (en) | 2010-03-24 |
| IL180958A0 (en) | 2007-07-04 |
| EP1773763B1 (en) | 2008-12-17 |
| MX2007001278A (es) | 2007-09-14 |
| CN1942436B (zh) | 2011-03-23 |
| EP2165709A3 (en) | 2010-06-23 |
| DE602004018548D1 (de) | 2009-01-29 |
| RU2009139259A (ru) | 2011-04-27 |
| AU2004322123A1 (en) | 2006-02-09 |
| BRPI0418651A (pt) | 2007-05-29 |
| EP1773763A1 (en) | 2007-04-18 |
| AU2009230800A1 (en) | 2009-11-19 |
| WO2006012725A1 (en) | 2006-02-09 |
| AU2004322123B2 (en) | 2009-08-13 |
| CN1942436A (zh) | 2007-04-04 |
| HK1105406A1 (en) | 2008-02-15 |
| ES2575871T3 (es) | 2016-07-01 |
| ATE417823T1 (de) | 2009-01-15 |
| JP2007525527A (ja) | 2007-09-06 |
| ES2319996T3 (es) | 2009-05-18 |
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