JP2009530447A5 - - Google Patents
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- JP2009530447A5 JP2009530447A5 JP2009500678A JP2009500678A JP2009530447A5 JP 2009530447 A5 JP2009530447 A5 JP 2009530447A5 JP 2009500678 A JP2009500678 A JP 2009500678A JP 2009500678 A JP2009500678 A JP 2009500678A JP 2009530447 A5 JP2009530447 A5 JP 2009530447A5
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- Japan
- Prior art keywords
- alkyl
- compound
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- integer
- Prior art date
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- 239000000693 micelle Substances 0.000 claims description 29
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 28
- 229940079593 drug Drugs 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 229960004679 doxorubicin Drugs 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 7
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 7
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 6
- 229960003942 amphotericin b Drugs 0.000 claims description 6
- 229960000485 methotrexate Drugs 0.000 claims description 6
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
- 108010036949 Cyclosporine Proteins 0.000 claims description 5
- 229930012538 Paclitaxel Natural products 0.000 claims description 4
- 229960001592 paclitaxel Drugs 0.000 claims description 4
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 4
- 229930105110 Cyclosporin A Natural products 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000005538 encapsulation Methods 0.000 claims description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 2
- -1 rapamycine Chemical compound 0.000 claims description 2
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 2
- 229960002930 sirolimus Drugs 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 24
- 239000012867 bioactive agent Substances 0.000 claims 12
- 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 12
- 125000003118 aryl group Chemical group 0.000 claims 8
- 235000012000 cholesterol Nutrition 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229960002568 ethinylestradiol Drugs 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 2
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 2
- 108020004414 DNA Proteins 0.000 claims 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims 2
- 108091034117 Oligonucleotide Proteins 0.000 claims 2
- YJDYDFNKCBANTM-QCWCSKBGSA-N SDZ PSC 833 Chemical compound C\C=C\C[C@@H](C)C(=O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](C(C)C)NC1=O YJDYDFNKCBANTM-QCWCSKBGSA-N 0.000 claims 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 2
- 229930003316 Vitamin D Natural products 0.000 claims 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 2
- IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 claims 2
- 229960005260 amiodarone Drugs 0.000 claims 2
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 2
- 229940127093 camptothecin Drugs 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229960001265 ciclosporin Drugs 0.000 claims 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
- 229960004316 cisplatin Drugs 0.000 claims 2
- 229930182912 cyclosporin Natural products 0.000 claims 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 2
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims 2
- 229940011871 estrogen Drugs 0.000 claims 2
- 239000000262 estrogen Substances 0.000 claims 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 2
- 229960005420 etoposide Drugs 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 239000000583 progesterone congener Substances 0.000 claims 2
- 229950010938 valspodar Drugs 0.000 claims 2
- 108010082372 valspodar Proteins 0.000 claims 2
- 235000019166 vitamin D Nutrition 0.000 claims 2
- 239000011710 vitamin D Substances 0.000 claims 2
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 2
- 229940046008 vitamin d Drugs 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000001272 (C1-C4)-alkylene-phenyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 229960004495 beclometasone Drugs 0.000 claims 1
- 229940092705 beclomethasone Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 claims 1
- 229960000452 diethylstilbestrol Drugs 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 229960004618 prednisone Drugs 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 229960003604 testosterone Drugs 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 description 12
- 238000012377 drug delivery Methods 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 238000012512 characterization method Methods 0.000 description 6
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- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
- 238000012552 review Methods 0.000 description 4
- 102000004895 Lipoproteins Human genes 0.000 description 3
- 108090001030 Lipoproteins Proteins 0.000 description 3
- 238000012382 advanced drug delivery Methods 0.000 description 3
- 239000012620 biological material Substances 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000007928 solubilization Effects 0.000 description 3
- 238000005063 solubilization Methods 0.000 description 3
- DSLBDPPHINVUID-REOHCLBHSA-N (2s)-2-aminobutanediamide Chemical compound NC(=O)[C@@H](N)CC(N)=O DSLBDPPHINVUID-REOHCLBHSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
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| PCT/CA2007/000451 WO2007106997A1 (en) | 2006-03-21 | 2007-03-21 | Novel poly(ethylene oxide)-block-poly(ester) block copolymers |
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| US20100137206A1 (en) * | 2006-12-15 | 2010-06-03 | The Governors Of The University Of Alberta | Novel ligand guided block copolymers for targeted drug delivery |
| US8524784B2 (en) | 2009-04-30 | 2013-09-03 | Intezyne Technologies, Incorporated | Polymer micelles containing anthracylines for the treatment of cancer |
| US8524783B2 (en) | 2009-04-30 | 2013-09-03 | Intezyne Technologies, Incorporated | Polymer micelles containing anthracylines for the treatment of cancer |
| US8361495B2 (en) * | 2009-12-23 | 2013-01-29 | International Business Machines Corporation | Antimicrobial polymers and methods of manufacture thereof |
| US8470891B2 (en) * | 2009-12-23 | 2013-06-25 | International Business Machines Corporation | Biodegradable block polymers for drug delivery, and methods related thereto |
| CA2974195A1 (en) * | 2014-10-15 | 2016-04-21 | University Of Connecticut | Bio-reducible self-assembled liquid crystalline block copolymer for drug delivery |
| US10828371B2 (en) | 2017-11-08 | 2020-11-10 | International Business Machines Corporation | Multifunctionalized bioactive polycaprolactone |
| US20210085801A1 (en) * | 2017-12-12 | 2021-03-25 | Cardiol Therapeutics Inc. | Amphiphilic block copolymers, micelles, and methods for treating or preventing heart failure |
| EP3699175B1 (en) | 2019-02-19 | 2022-05-04 | Kemijski Institut | Functionalized aliphatic polyesters and process for producing the same |
| FI129022B (en) * | 2019-09-10 | 2021-05-14 | Aabo Akademi Univ | Polymer and composition made from a renewable source |
| JP7641003B2 (ja) * | 2021-06-02 | 2025-03-06 | 国立大学法人金沢大学 | 蛍光プローブ、液相の極性及び粘性を評価する方法、並びに化合物 |
| KR102663816B1 (ko) * | 2021-10-26 | 2024-05-14 | 전북대학교산학협력단 | 중합 후 변성법을 이용한 기능성 폴리에틸렌글리콜의 합성방법 |
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| US5801224A (en) * | 1996-04-26 | 1998-09-01 | Board Of Trustees Operating Michigan State University | Bulk reactive extrusion polymerization process producing aliphatic ester polymer compositions |
| US5936127A (en) * | 1997-01-13 | 1999-08-10 | The Penn State Research Foundation | Asymmetric synthesis and catalysis with chiral heterocyclic compounds |
| GB9809116D0 (en) * | 1998-04-29 | 1998-07-01 | Zeneca Ltd | Ether/ester dispersants |
| JP2000004892A (ja) * | 1998-06-29 | 2000-01-11 | Toyo Ink Mfg Co Ltd | ポリエステル−ポリエーテルブロック共重合体の製造方法 |
| US6469132B1 (en) * | 1999-05-05 | 2002-10-22 | Mcgill University | Diblock copolymer and use thereof in a micellar drug delivery system |
| JP4912557B2 (ja) * | 2000-03-10 | 2012-04-11 | 株式会社ダイセル | マンガン触媒等を用いた有機化合物の製造法 |
| JP2002351066A (ja) | 2001-05-30 | 2002-12-04 | Fuji Photo Film Co Ltd | 赤外線レーザー用ポジ型平版印刷版材料及び処理方法 |
| AU2003265905B2 (en) * | 2002-09-05 | 2008-01-31 | Vocfree, Inc. | Fast drying coatings |
| WO2004078738A1 (en) * | 2003-03-04 | 2004-09-16 | Firmenich Sa | Process for the preparation of lactones or epoxides |
| WO2005035606A1 (en) * | 2003-10-10 | 2005-04-21 | Samyang Corporation | Amphiphilic block copolymer and polymeric composition comprising the same for drug delivery |
| JP2005139068A (ja) * | 2003-11-04 | 2005-06-02 | Sumitomo Chemical Co Ltd | α―アセチル−γ―ブチロラクトン誘導体の製造方法 |
| WO2005058376A1 (en) * | 2003-12-17 | 2005-06-30 | Smithkline Beecham Corporation | Polymeric micellar complexes and drug delivery vehicles thereof |
| AU2005210668A1 (en) * | 2004-01-30 | 2005-08-18 | Angiotech International Ag | Compositions and methods for treating contracture |
| CA2580305A1 (en) * | 2004-06-02 | 2005-12-15 | The Governors Of The University Of Alberta | Polymer based nano-carriers for the solubilization and delivery of hydrophobic drugs |
| JP4553374B2 (ja) * | 2004-06-11 | 2010-09-29 | キヤノン株式会社 | スルホン酸基を有するポリヒドロキシアルカノエート並びにその製造方法 |
| US20080124400A1 (en) * | 2004-06-24 | 2008-05-29 | Angiotech International Ag | Microparticles With High Loadings Of A Bioactive Agent |
| US20100137206A1 (en) * | 2006-12-15 | 2010-06-03 | The Governors Of The University Of Alberta | Novel ligand guided block copolymers for targeted drug delivery |
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- 2007-03-21 CA CA2646425A patent/CA2646425C/en active Active
- 2007-03-21 CA CA2857023A patent/CA2857023C/en active Active
- 2007-03-21 EP EP07710774.6A patent/EP1994081B1/en active Active
- 2007-03-21 WO PCT/CA2007/000451 patent/WO2007106997A1/en not_active Ceased
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