JP2006521361A5 - - Google Patents
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- JP2006521361A5 JP2006521361A5 JP2006507484A JP2006507484A JP2006521361A5 JP 2006521361 A5 JP2006521361 A5 JP 2006521361A5 JP 2006507484 A JP2006507484 A JP 2006507484A JP 2006507484 A JP2006507484 A JP 2006507484A JP 2006521361 A5 JP2006521361 A5 JP 2006521361A5
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- Prior art keywords
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- complex
- alkyl
- phe
- compound
- Prior art date
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- 229910052757 nitrogen Inorganic materials 0.000 claims 81
- 229910052739 hydrogen Inorganic materials 0.000 claims 76
- 229910052740 iodine Inorganic materials 0.000 claims 70
- 229910052700 potassium Inorganic materials 0.000 claims 59
- 235000001014 amino acid Nutrition 0.000 claims 46
- 150000001413 amino acids Chemical class 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 46
- 108090000765 processed proteins & peptides Proteins 0.000 claims 42
- 229910052717 sulfur Inorganic materials 0.000 claims 35
- -1 acyloxymethyl ketone Chemical class 0.000 claims 32
- 235000018102 proteins Nutrition 0.000 claims 29
- 102000004169 proteins and genes Human genes 0.000 claims 29
- 108090000623 proteins and genes Proteins 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000005647 linker group Chemical group 0.000 claims 27
- 102000009027 Albumins Human genes 0.000 claims 24
- 108010088751 Albumins Proteins 0.000 claims 24
- 238000000034 method Methods 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 17
- 230000000840 anti-viral effect Effects 0.000 claims 14
- 229910052698 phosphorus Inorganic materials 0.000 claims 14
- 229910052722 tritium Inorganic materials 0.000 claims 12
- 208000036142 Viral infection Diseases 0.000 claims 11
- 239000002461 renin inhibitor Substances 0.000 claims 11
- 230000009385 viral infection Effects 0.000 claims 11
- 229940086526 renin-inhibitors Drugs 0.000 claims 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 102000008100 Human Serum Albumin Human genes 0.000 claims 7
- 108091006905 Human Serum Albumin Proteins 0.000 claims 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- 125000000524 functional group Chemical group 0.000 claims 6
- 230000007704 transition Effects 0.000 claims 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 5
- 102100028255 Renin Human genes 0.000 claims 5
- 108090000783 Renin Proteins 0.000 claims 5
- 239000012503 blood component Substances 0.000 claims 5
- 238000001727 in vivo Methods 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- XIZSMQBWVQNHCA-NIRMQQKASA-N (2s)-6-amino-2-[[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]pro Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)CN[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(O)=O)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NCCC1)C1=CN=CN1 XIZSMQBWVQNHCA-NIRMQQKASA-N 0.000 claims 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims 4
- ZYJSTSMEUKNCEV-UHFFFAOYSA-N 3-diazo-1-diazonioprop-1-en-2-olate Chemical compound [N-]=[N+]=CC(=O)C=[N+]=[N-] ZYJSTSMEUKNCEV-UHFFFAOYSA-N 0.000 claims 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 4
- 150000001299 aldehydes Chemical class 0.000 claims 4
- 150000001350 alkyl halides Chemical class 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 150000008064 anhydrides Chemical class 0.000 claims 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims 4
- 210000004369 blood Anatomy 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 4
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 claims 4
- 238000004132 cross linking Methods 0.000 claims 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims 4
- 150000002118 epoxides Chemical class 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- 150000002902 organometallic compounds Chemical class 0.000 claims 4
- 150000007659 semicarbazones Chemical class 0.000 claims 4
- 210000002966 serum Anatomy 0.000 claims 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 4
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 claims 4
- 150000004799 α-ketoamides Chemical class 0.000 claims 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 3
- 241000725303 Human immunodeficiency virus Species 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 3
- PVGATNRYUYNBHO-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(2,5-dioxopyrrol-1-yl)butanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCCN1C(=O)C=CC1=O PVGATNRYUYNBHO-UHFFFAOYSA-N 0.000 claims 2
- BQWBEDSJTMWJAE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-iodoacetyl)amino]benzoate Chemical compound C1=CC(NC(=O)CI)=CC=C1C(=O)ON1C(=O)CCC1=O BQWBEDSJTMWJAE-UHFFFAOYSA-N 0.000 claims 2
- NPYRCTHITOIVLV-VEUFVCKOSA-N (2r)-1-[(2s)-2-acetamido-3-(1h-imidazol-5-yl)propanoyl]-n-[(2s)-1-[[(2s)-1-[[(2s,3s)-5-[[(2s)-1-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-cyclohexyl-3-hydroxy-5-oxopentan-2-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropa Chemical compound C([C@@H]([C@@H](O)CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H]1N(CCC1)C(=O)[C@H](CC=1N=CNC=1)NC(C)=O)C1CCCCC1 NPYRCTHITOIVLV-VEUFVCKOSA-N 0.000 claims 2
- YLFGKFNAVPVWDW-AJEFLBOZSA-N (2s)-1-[(2s)-2-[[(2s)-2-amino-2-methylbutanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]-n-[(2s)-1-[[(2s)-1-[[1-[[(2s)-1-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-6-methyl-1-oxoheptan-4-yl]amino]-3-(1h-imidazol Chemical compound C([C@H](NC(=O)[C@@](C)(N)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)NC(CC(C)C)C(O)CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CNC=N1 YLFGKFNAVPVWDW-AJEFLBOZSA-N 0.000 claims 2
- TVKUVJQHSALMJM-SSBFDGESSA-N (2s)-1-[(2s)-2-acetamido-3-(1h-indol-3-yl)propanoyl]-n-[(2s)-1-[[(2s)-1-[[(4s)-1-[[(2s,3s)-1-amino-3-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-6-methyl-1-oxoheptan-4-yl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidi Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)CC(=O)N[C@@H]([C@@H](C)CC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)C1=CNC=N1 TVKUVJQHSALMJM-SSBFDGESSA-N 0.000 claims 2
- AIRMFERKNRDUKD-PVGXKDMPSA-N (2s)-6-amino-2-[[(2s)-3-(4-hydroxyphenyl)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]propano Chemical compound C([C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCCN)C(O)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NCCC1)C1=CC=CC=C1 AIRMFERKNRDUKD-PVGXKDMPSA-N 0.000 claims 2
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 claims 2
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 claims 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 108060003951 Immunoglobulin Proteins 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 2
- VADLTGVIOIOKGM-BZSNNMDCSA-N Phe-His-Leu Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CN=CN1 VADLTGVIOIOKGM-BZSNNMDCSA-N 0.000 claims 2
- 102000007562 Serum Albumin Human genes 0.000 claims 2
- 108010071390 Serum Albumin Proteins 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 108090000901 Transferrin Proteins 0.000 claims 2
- 102000004338 Transferrin Human genes 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 150000001541 aziridines Chemical class 0.000 claims 2
- NXVYSVARUKNFNF-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) 2,3-dihydroxybutanedioate Chemical compound O=C1CCC(=O)N1OC(=O)C(O)C(O)C(=O)ON1C(=O)CCC1=O NXVYSVARUKNFNF-UHFFFAOYSA-N 0.000 claims 2
- VYLDEYYOISNGST-UHFFFAOYSA-N bissulfosuccinimidyl suberate Chemical compound O=C1C(S(=O)(=O)O)CC(=O)N1OC(=O)CCCCCCC(=O)ON1C(=O)C(S(O)(=O)=O)CC1=O VYLDEYYOISNGST-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 210000004899 c-terminal region Anatomy 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 150000001718 carbodiimides Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- ZLFRJHOBQVVTOJ-UHFFFAOYSA-N dimethyl hexanediimidate Chemical compound COC(=N)CCCCC(=N)OC ZLFRJHOBQVVTOJ-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000000839 emulsion Substances 0.000 claims 2
- 210000003743 erythrocyte Anatomy 0.000 claims 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 102000018358 immunoglobulin Human genes 0.000 claims 2
- 229940072221 immunoglobulins Drugs 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 235000014666 liquid concentrate Nutrition 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- DLAHCJHYEAZDLE-VRYQDWSQSA-N methyl (2s)-2-[[(2s)-2-[[(2s,3s)-2-[[(3s,4s)-4-[[(2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-5-(diaminomethylideneamino)-2-[[(2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino] Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)[C@@H](O)CC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)OCC=1C=CC=CC=1)C1=CN=CN1 DLAHCJHYEAZDLE-VRYQDWSQSA-N 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- QGOKIEUFWNCGFO-UHFFFAOYSA-N propanoic acid;pyrrole-2,5-dione Chemical compound CCC(O)=O.O=C1NC(=O)C=C1 QGOKIEUFWNCGFO-UHFFFAOYSA-N 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 229940080818 propionamide Drugs 0.000 claims 2
- 108010026906 renin inhibitory peptide Proteins 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229960002317 succinimide Drugs 0.000 claims 2
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- IFVRMXRXQKVDCE-BTQAAEOHSA-N tert-butyl (2s)-2-[[(2s)-1-[[(2s)-1-[[4-amino-5-hydroxy-2-methyl-7-[[(2s,3s)-3-methyl-1-oxo-1-(pyridin-2-ylmethylamino)pentan-2-yl]amino]-7-oxoheptyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidine-1-car Chemical compound C([C@@H](C(=O)NCC(C)CC(N)C(O)CC(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC=1N=CC=CC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H]1N(CCC1)C(=O)OC(C)(C)C)C1=CNC=N1 IFVRMXRXQKVDCE-BTQAAEOHSA-N 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 150000007970 thio esters Chemical class 0.000 claims 2
- 239000012581 transferrin Substances 0.000 claims 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 102100033312 Alpha-2-macroglobulin Human genes 0.000 claims 1
- 102000008857 Ferritin Human genes 0.000 claims 1
- 108050000784 Ferritin Proteins 0.000 claims 1
- 238000008416 Ferritin Methods 0.000 claims 1
- 102100022086 GRB2-related adapter protein 2 Human genes 0.000 claims 1
- 101710181935 Phosphate-binding protein PstS 1 Proteins 0.000 claims 1
- 108010015078 Pregnancy-Associated alpha 2-Macroglobulins Proteins 0.000 claims 1
- 102000009488 Thyroxine-Binding Proteins Human genes 0.000 claims 1
- 108010048889 Thyroxine-Binding Proteins Proteins 0.000 claims 1
- 101800001690 Transmembrane protein gp41 Proteins 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 108020001507 fusion proteins Proteins 0.000 claims 1
- 102000037865 fusion proteins Human genes 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 108010037251 peptide T1249 Proteins 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 102000005963 steroid binding proteins Human genes 0.000 claims 1
- 108020003178 steroid binding proteins Proteins 0.000 claims 1
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 claims 1
- ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 claims 1
- 0 CN[C@](*)C(C(*=C)=O)=O Chemical compound CN[C@](*)C(C(*=C)=O)=O 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45647203P | 2003-03-24 | 2003-03-24 | |
| US45695203P | 2003-03-25 | 2003-03-25 | |
| US51889203P | 2003-11-10 | 2003-11-10 | |
| PCT/US2004/008847 WO2004085505A2 (en) | 2003-03-24 | 2004-03-24 | Long acting biologically active conjugates |
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| US6887674B1 (en) | 1998-04-13 | 2005-05-03 | California Institute Of Technology | Artery- and vein-specific proteins and uses therefor |
| US7381410B2 (en) * | 2003-03-12 | 2008-06-03 | Vasgene Therapeutics, Inc. | Polypeptide compounds for inhibiting angiogenesis and tumor growth |
| EP1606305A4 (en) * | 2003-03-12 | 2009-06-24 | Vasgene Therapeutics Inc | NUCLEIC ACID COMPOUNDS FOR THE INHIBITION OF ANGIOGENESIS AND TUMOR GROWTH |
| DK1730196T3 (da) | 2004-03-12 | 2011-03-28 | Vasgene Therapeutics Inc | EphB4-bindende antistoffer til inhibering af antiogenese og tumorvækst |
| CN101072797B (zh) * | 2004-03-12 | 2012-05-09 | 瓦斯基因治疗公司 | 结合ephb4、抑制血管发生和肿瘤生长的抗体 |
| CA2581423A1 (en) * | 2004-09-23 | 2006-03-30 | Vasgene Therapeutics, Inc. | Polipeptide compounds for inhibiting angiogenesis and tumor growth |
| ES2336245T3 (es) * | 2005-04-08 | 2010-04-09 | Lonza Ag | Sintesis peptidica de helices alfa sobre resina de peg. |
| TW200817438A (en) | 2006-08-17 | 2008-04-16 | Hoffmann La Roche | A conjugate of an antibody against CCR5 and an antifusogenic peptide |
| CL2008002092A1 (es) | 2007-07-20 | 2009-05-29 | Hoffmann La Roche | Conjugado que contiene dos o mas peptidos antifusogenicos y un anticuerpo anti-cd-4; metodo de produccion; composicion farmaceutica que lo comprende; polipeptidos antifusogenicos y uso del conjugado para tratar infecciones viricas. |
| JP2010538979A (ja) * | 2007-09-11 | 2010-12-16 | モンドバイオテック ラボラトリーズ アクチエンゲゼルシャフト | Ｓ．Ｐｎｅｕｍｏｎｉａｅの感染等を処置するための治療剤としての、ＲＧＤＳＰＡＳＳＫＰ、および随意的なアンギオテンシンＩＩの使用 |
| GB201006038D0 (en) | 2010-04-12 | 2010-05-26 | Unilever Plc | Improvements relating to antiviral compositions |
| EP2558491B1 (en) * | 2010-04-13 | 2018-07-04 | Bristol-Myers Squibb Company | Fibronectin based scaffold domain proteins that bind pcsk9 |
| AU2011292044A1 (en) | 2010-08-18 | 2013-04-04 | Del Mar Pharmaceuticals | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dianhydrogalactitol and diacetyldianhydrogalactitol |
| EP3795145A3 (en) | 2011-08-17 | 2021-06-09 | Dennis M. Brown | Compositions and methods to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dibromodulcitol |
| EP2804602B1 (en) | 2012-01-20 | 2024-12-04 | Del Mar Pharmaceuticals | Use of substituted hexitols including dianhydrogalactitol and analogs to treat neoplastic disease and cancer stem cells including glioblastoma multforme and medulloblastoma |
| CA2868302A1 (en) | 2012-03-23 | 2013-09-26 | Dennis M. Brown | Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo |
| WO2013169600A1 (en) | 2012-05-09 | 2013-11-14 | Delmar Pharmaceuticals | Veterinary use of dianhydrogalactitol, diacetyldianhydrogalactitol, and dibromodulcitol to treat malignancies |
| JP6280546B2 (ja) | 2012-06-26 | 2018-02-14 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法 |
| KR20160061911A (ko) | 2013-04-08 | 2016-06-01 | 데니스 엠. 브라운 | 최적하 투여된 화학 화합물의 치료 효과 |
| CN112472699A (zh) | 2013-07-26 | 2021-03-12 | 种族肿瘤学公司 | 改善比生群及衍生物的治疗益处的组合方法 |
| SG11201608303QA (en) | 2014-04-04 | 2016-11-29 | Del Mar Pharmaceuticals | Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer |
| JP6886917B2 (ja) | 2014-08-22 | 2021-06-16 | 國立成功大學Ｎａｔｉｏｎａｌ Ｃｈｅｎｇ Ｋｕｎｇ Ｕｎｉｖｅｒｓｉｔｙ | ロドストミンバリアント、ロドストミンバリアントをコードするポリヌクレオチド、当該ポリヌクレオチドを含む組換え宿主細胞、及びロドストミンバリアントを含む医薬組成物 |
| EP3661543A4 (en) | 2017-07-31 | 2021-09-22 | The Trustees of Indiana University | MODIFIED DDAH POLYPEPTIDES INCLUDING A PHARMACOKINETIC ENHANCEMENT, PHARMACOLOGY ENHANCED FRAGMENT AND THEIR USES |
| JP2022548026A (ja) | 2019-09-13 | 2022-11-16 | ザ・トラスティーズ・オブ・インディアナ・ユニバーシティー | 血液中のａｄｍａを調節するデバイスおよび方法 |
| CN111053892B (zh) * | 2019-12-24 | 2023-11-17 | 山西锦波生物医药股份有限公司 | 一种广谱抗肠道病毒的蛋白类药物及其应用 |
| CN117186187B (zh) * | 2023-07-12 | 2024-05-31 | 中国医学科学院病原生物学研究所 | 一种抗呼吸道合胞病毒膜融合抑制剂及其药物用途 |
| CN118409027B (zh) * | 2024-07-02 | 2024-09-10 | 成都市食品检验研究院 | 一种食品中1-脱氧野尻霉素的含量检测方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1164239B (it) * | 1983-05-25 | 1987-04-08 | Anic Spa | Un retro-inverso analogo del decapeptide (5-14)dell'angiotensinogeno equino inibitore specifico della renina con elevata resistenza all'idrolisi enzimatica |
| IE873186L (en) * | 1986-12-23 | 1988-06-23 | Harvard College | Renin inhibitors iv |
| WO1989003841A1 (en) * | 1987-10-26 | 1989-05-05 | Warner-Lambert Company | Renin inhibitors, processes for preparing them, methods for using them, and compositions containing them |
| US5541297A (en) * | 1988-04-01 | 1996-07-30 | Immunomedics, Inc. | Therapeutic conjugates of toxins and drugs |
| FR2650598B1 (fr) * | 1989-08-03 | 1994-06-03 | Rhone Poulenc Sante | Derives de l'albumine a fonction therapeutique |
| US6479055B1 (en) * | 1993-06-07 | 2002-11-12 | Trimeris, Inc. | Methods for inhibition of membrane fusion-associated events, including respiratory syncytial virus transmission |
| US5464933A (en) * | 1993-06-07 | 1995-11-07 | Duke University | Synthetic peptide inhibitors of HIV transmission |
| DE19926475A1 (de) * | 1999-06-10 | 2000-12-14 | Ktb Tumorforschungs Gmbh | Träger-Pharmaka-Konjugate |
| BR0115257A (pt) * | 2000-11-10 | 2003-08-12 | Proteopharma Aps | Análogos de apolipoproteìna |
| DE10121982B4 (de) * | 2001-05-05 | 2008-01-24 | Lts Lohmann Therapie-Systeme Ag | Nanopartikel aus Protein mit gekoppeltem Apolipoprotein E zur Überwindung der Blut-Hirn-Schranke und Verfahren zu ihrer Herstellung |
| ATE295370T1 (de) * | 2001-05-31 | 2005-05-15 | Conjuchem Inc | Langwirkende fusionspeptid-inhibitoren für hiv- infektion |
-
2004
- 2004-03-24 NZ NZ567952A patent/NZ567952A/en not_active IP Right Cessation
- 2004-03-24 WO PCT/US2004/008847 patent/WO2004085505A2/en not_active Ceased
- 2004-03-24 EP EP04758058A patent/EP1620120A4/en not_active Withdrawn
- 2004-03-24 US US10/550,715 patent/US20070207952A1/en not_active Abandoned
- 2004-03-24 JP JP2006507484A patent/JP2006521361A/ja active Pending
- 2004-03-24 KR KR1020057017965A patent/KR20050120663A/ko not_active Withdrawn
- 2004-03-24 AU AU2004223829A patent/AU2004223829A1/en not_active Abandoned
- 2004-03-24 NZ NZ543122A patent/NZ543122A/en not_active IP Right Cessation
- 2004-03-24 CA CA002520257A patent/CA2520257A1/en not_active Abandoned
-
2010
- 2010-07-05 JP JP2010153334A patent/JP2011006419A/ja active Pending
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