JP2008508388A5 - - Google Patents
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- JP2008508388A5 JP2008508388A5 JP2007523128A JP2007523128A JP2008508388A5 JP 2008508388 A5 JP2008508388 A5 JP 2008508388A5 JP 2007523128 A JP2007523128 A JP 2007523128A JP 2007523128 A JP2007523128 A JP 2007523128A JP 2008508388 A5 JP2008508388 A5 JP 2008508388A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- polyamino
- acid
- pharmaceutical composition
- amino acid
- 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.)
- Granted
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- 239000002253 acid Substances 0.000 claims description 30
- 102000004169 proteins and genes Human genes 0.000 claims description 14
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 12
- 125000001165 hydrophobic group Chemical group 0.000 claims description 12
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 229940049906 glutamate Drugs 0.000 claims description 11
- 229930195712 glutamate Natural products 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229940024606 amino acid Drugs 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000007920 subcutaneous administration Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 238000007918 intramuscular administration Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 108091034117 Oligonucleotide Proteins 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 238000007912 intraperitoneal administration Methods 0.000 claims description 6
- 239000002537 cosmetic Substances 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
- 108091033319 polynucleotide Proteins 0.000 claims description 5
- 239000002157 polynucleotide Substances 0.000 claims description 5
- 102000040430 polynucleotide Human genes 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 102000003886 Glycoproteins Human genes 0.000 claims description 4
- 108090000288 Glycoproteins Proteins 0.000 claims description 4
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- 229940009098 aspartate Drugs 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- -1 hydroxy alcohol Chemical compound 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000003509 long acting drug Substances 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 150000008163 sugars Chemical class 0.000 claims description 3
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000000693 micelle Substances 0.000 claims description 2
- 239000002105 nanoparticle Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 229940043131 pyroglutamate Drugs 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 2
- 125000003827 glycol group Chemical group 0.000 claims 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims 1
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims 1
- 241001061127 Thione Species 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 229940107161 cholesterol Drugs 0.000 claims 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims 1
- 229940055577 oleyl alcohol Drugs 0.000 claims 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 229960001295 tocopherol Drugs 0.000 claims 1
- 229930003799 tocopherol Natural products 0.000 claims 1
- 235000010384 tocopherol Nutrition 0.000 claims 1
- 239000011732 tocopherol Substances 0.000 claims 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 15
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 12
- 235000018102 proteins Nutrition 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 229960005261 aspartic acid Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 108010020346 Polyglutamic Acid Proteins 0.000 description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
- FORGMRSGVSYZQR-YFKPBYRVSA-N L-leucinamide Chemical compound CC(C)C[C@H](N)C(N)=O FORGMRSGVSYZQR-YFKPBYRVSA-N 0.000 description 4
- 229960002989 glutamic acid Drugs 0.000 description 4
- 125000003275 alpha amino acid group Chemical group 0.000 description 3
- 235000003704 aspartic acid Nutrition 0.000 description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 108010064470 polyaspartate Proteins 0.000 description 2
- 108010050934 polyleucine Proteins 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004720 cerebrum Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- HERPVHLYIHBEFW-ZETCQYMHSA-N diethyl (2s)-2-aminopentanedioate Chemical compound CCOC(=O)CC[C@H](N)C(=O)OCC HERPVHLYIHBEFW-ZETCQYMHSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003520 lipogenic effect Effects 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0408477 | 2004-07-30 | ||
| FR0408477A FR2873703B1 (fr) | 2004-07-30 | 2004-07-30 | Polyaminoacides branches, fonctionnalises par des groupements hydrophobes et leurs applications notamment therapeutiques |
| PCT/FR2005/050594 WO2006021706A1 (fr) | 2004-07-30 | 2005-07-19 | Polyaminoacides branches, fonctionnalises par des groupements hydrophobes et leurs applications notamment therapeutiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008508388A JP2008508388A (ja) | 2008-03-21 |
| JP2008508388A5 true JP2008508388A5 (https=) | 2011-07-07 |
| JP4871867B2 JP4871867B2 (ja) | 2012-02-08 |
Family
ID=34949824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007523128A Expired - Fee Related JP4871867B2 (ja) | 2004-07-30 | 2005-07-19 | 疎水性基で官能基化された分岐鎖ポリアミノ酸、及びその応用、特に治療への応用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8206744B2 (https=) |
| EP (1) | EP1771498B1 (https=) |
| JP (1) | JP4871867B2 (https=) |
| AT (1) | ATE449125T1 (https=) |
| CA (1) | CA2573791A1 (https=) |
| DE (1) | DE602005017787D1 (https=) |
| ES (1) | ES2336688T3 (https=) |
| FR (1) | FR2873703B1 (https=) |
| WO (1) | WO2006021706A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2873704B1 (fr) * | 2004-07-30 | 2006-12-08 | Flamel Technologies Sa | Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques |
| CA2656077C (en) * | 2006-06-15 | 2014-12-09 | Marc Mckennon | A process for the preparation of poly-alpha-glutamic acid and derivatives thereof |
| JP5258189B2 (ja) * | 2006-11-09 | 2013-08-07 | 学校法人 関西大学 | 柔軟性生分解性ポリマー |
| FR2915748B1 (fr) * | 2007-05-03 | 2012-10-19 | Flamel Tech Sa | Acides polyglutamiques fonctionnalises par des groupes cationiques et des groupements hydrophobes et leurs applications, notamment therapeutiques |
| TWI448485B (zh) * | 2010-08-03 | 2014-08-11 | Univ Nat Taiwan Normal | 半互穿網絡型水膠聚合物、其製造方法及包含其之水泥組成物 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351337A (en) | 1973-05-17 | 1982-09-28 | Arthur D. Little, Inc. | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
| JPS60100516A (ja) | 1983-11-04 | 1985-06-04 | Takeda Chem Ind Ltd | 徐放型マイクロカプセルの製造法 |
| ATE60340T1 (de) | 1984-10-19 | 1991-02-15 | Battelle Memorial Institute | Durch mikroorganismen abbaubares polypeptid und seine verwendung fuer die fortschreitende abgabe von medikamenten. |
| CH667874A5 (fr) | 1985-12-19 | 1988-11-15 | Battelle Memorial Institute | Polypeptide synthetique biodegradable et son utilisation pour la preparation de medicaments. |
| KR940003548U (ko) | 1992-08-14 | 1994-02-21 | 김형술 | 세탁물 건조기 |
| US6153193A (en) | 1993-04-28 | 2000-11-28 | Supratek Pharma Inc. | Compositions for targeting biological agents |
| FR2732218B1 (fr) | 1995-03-28 | 1997-08-01 | Flamel Tech Sa | Particules a base de polyaminoacide(s) et susceptibles d'etre utilisees comme vecteurs de principe(s) actif(s) et leurs procedes de preparation |
| US6331289B1 (en) * | 1996-10-28 | 2001-12-18 | Nycomed Imaging As | Targeted diagnostic/therapeutic agents having more than one different vectors |
| GB9811059D0 (en) | 1998-05-23 | 1998-07-22 | Univ Strathclyde | Polyamino acid vesicles |
| FR2786098B1 (fr) | 1998-11-20 | 2003-05-30 | Flamel Tech Sa | Particules a base de polyaminoacide(s) et susceptibles d'etre utilisees comme vecteurs de principe(s) actif(s), suspension colloidale les comprenant et leurs procedes de fabrication |
| FR2801226B1 (fr) | 1999-11-23 | 2002-01-25 | Flamel Tech Sa | Suspension colloidale de particules submicroniques de vectorisation de principes actifs et son mode de preparation |
| FR2840614B1 (fr) | 2002-06-07 | 2004-08-27 | Flamel Tech Sa | Polyaminoacides fonctionnalises par de l'alpha-tocopherol et leurs applications notamment therapeutiques |
| FR2843117B1 (fr) | 2002-07-30 | 2004-10-15 | Flamel Tech Sa | Polyaminoacides fonctionnalises par au moins un groupement hydrophobe et leurs applications notamment therapeutiques |
| WO2004060968A1 (fr) | 2002-12-04 | 2004-07-22 | Flamel Technologies | Polyaminoacides fonctionnalises par au moins un groupement (oligo)aminoacide et leurs applications notamment therapeutiques |
| JP2006050312A (ja) * | 2004-08-05 | 2006-02-16 | Canon Inc | プリンタサーバ装置及びデータ処理方法 |
-
2004
- 2004-07-30 FR FR0408477A patent/FR2873703B1/fr not_active Expired - Fee Related
-
2005
- 2005-07-19 WO PCT/FR2005/050594 patent/WO2006021706A1/fr not_active Ceased
- 2005-07-19 US US11/658,875 patent/US8206744B2/en not_active Expired - Fee Related
- 2005-07-19 EP EP05791929A patent/EP1771498B1/fr not_active Expired - Lifetime
- 2005-07-19 AT AT05791929T patent/ATE449125T1/de not_active IP Right Cessation
- 2005-07-19 JP JP2007523128A patent/JP4871867B2/ja not_active Expired - Fee Related
- 2005-07-19 DE DE602005017787T patent/DE602005017787D1/de not_active Expired - Lifetime
- 2005-07-19 ES ES05791929T patent/ES2336688T3/es not_active Expired - Lifetime
- 2005-07-19 CA CA002573791A patent/CA2573791A1/fr not_active Abandoned
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