SI9620107A - Blok polimer, ki ima funkcionalne skupine na obeh svojih koncih - Google Patents

Blok polimer, ki ima funkcionalne skupine na obeh svojih koncih Download PDF

Info

Publication number: SI9620107A
Authority: SI; Slovenia
Prior art keywords: group; carbon atoms; amino; alkyl; blocked
Prior art date: 1995-08-10

Application number

SI9620107A

Other languages

English (en)

Slovenian (sl)

Inventor

Kazunori Kataoka

Masao Kato

Yukio Nagasaki

Teruo Okano

Original Assignee

Kazunori Kataoka

Priority date (The priority date 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 date listed.)

1995-08-10

Filing date

1996-08-05

Publication date

1998-10-31

1996-08-05 Application filed by Kazunori Kataoka filed Critical Kazunori Kataoka

1998-10-31 Publication of SI9620107A publication Critical patent/SI9620107A/sl

Links

229920000642 polymer Polymers 0.000 title claims abstract description 114
125000000524 functional group Chemical group 0.000 title claims abstract description 29
-1 amino, carboxy Chemical group 0.000 claims abstract description 103
125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 30
125000000217 alkyl group Chemical group 0.000 claims description 45
125000004432 carbon atom Chemical group C* 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
125000003277 amino group Chemical group 0.000 claims description 26
125000006239 protecting group Chemical group 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
229910052700 potassium Inorganic materials 0.000 claims description 10
239000011591 potassium Substances 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000012039 electrophile Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
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 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
125000004036 acetal group Chemical group 0.000 claims description 3
229910052792 caesium Inorganic materials 0.000 claims description 3
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
239000012434 nucleophilic reagent Substances 0.000 claims description 3
230000000306 recurrent effect Effects 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
229920003171 Poly (ethylene oxide) Polymers 0.000 abstract description 21
230000002209 hydrophobic effect Effects 0.000 abstract description 11
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 abstract description 11
150000002596 lactones Chemical class 0.000 abstract description 7
239000000693 micelle Substances 0.000 abstract description 4
239000000560 biocompatible material Substances 0.000 abstract description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
150000001299 aldehydes Chemical class 0.000 abstract 1
229920002554 vinyl polymer Polymers 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
238000002360 preparation method Methods 0.000 description 17
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
229920000747 poly(lactic acid) Polymers 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
238000004108 freeze drying Methods 0.000 description 9
238000005227 gel permeation chromatography Methods 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000012300 argon atmosphere Substances 0.000 description 8
IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
239000003999 initiator Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000178 monomer Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
150000003112 potassium compounds Chemical class 0.000 description 6
238000000926 separation method Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
238000009826 distribution Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000002077 nanosphere Substances 0.000 description 4
238000012916 structural analysis Methods 0.000 description 4
238000011282 treatment Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229920001400 block copolymer Polymers 0.000 description 3
238000002296 dynamic light scattering Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000002245 particle Substances 0.000 description 3
229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
239000008366 buffered solution Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
125000000422 delta-lactone group Chemical group 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
238000001647 drug administration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
125000000457 gamma-lactone group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229920001477 hydrophilic polymer Polymers 0.000 description 2
229920001600 hydrophobic polymer Polymers 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000012038 nucleophile Substances 0.000 description 2
125000006353 oxyethylene group Chemical group 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 2
238000009210 therapy by ultrasound Methods 0.000 description 2
UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 1
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
FXLJHFCTYDFUER-UHFFFAOYSA-N 1-bromoprop-2-enylbenzene Chemical compound C=CC(Br)C1=CC=CC=C1 FXLJHFCTYDFUER-UHFFFAOYSA-N 0.000 description 1
SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 1
ODZZAIFAQLODKN-UHFFFAOYSA-N 3-bromo-1,1-dimethoxypropane Chemical compound COC(OC)CCBr ODZZAIFAQLODKN-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
NZOCBALFURHRNV-UHFFFAOYSA-N C(C)(C)(C)OC(=O)C([O-])C.[K+] Chemical compound C(C)(C)(C)OC(=O)C([O-])C.[K+] NZOCBALFURHRNV-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229940061720 alpha hydroxy acid Drugs 0.000 description 1
150000001280 alpha hydroxy acids Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
238000007336 electrophilic substitution reaction Methods 0.000 description 1
JEAVBVKAYUCPAQ-UHFFFAOYSA-N ethyl 2-chloropropanoate Chemical compound CCOC(=O)C(C)Cl JEAVBVKAYUCPAQ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010550 living polymerization reaction Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229950008885 polyglycolic acid Drugs 0.000 description 1
239000004633 polyglycolic acid Substances 0.000 description 1
ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
JLSPRTCKFYWUMC-UHFFFAOYSA-M potassium;phenylmethanethiolate Chemical compound [K+].[S-]CC1=CC=CC=C1 JLSPRTCKFYWUMC-UHFFFAOYSA-M 0.000 description 1
ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
QGYRCRFFCMLBRN-UHFFFAOYSA-N sodium;2-aminoethanolate Chemical compound [Na+].NCC[O-] QGYRCRFFCMLBRN-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/51—Nanocapsules; Nanoparticles
- A61K9/5107—Excipients; Inactive ingredients
- A61K9/513—Organic macromolecular compounds; Dendrimers
- A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
- A61K9/5153—Polyesters, e.g. poly(lactide-co-glycolide)
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2627—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aromatic or arylaliphatic amine groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Dispersion Chemistry (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Nanotechnology (AREA)
Optics & Photonics (AREA)
Biophysics (AREA)
Inorganic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Graft Or Block Polymers (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Medicinal Preparation (AREA)
Materials For Medical Uses (AREA)
Polyethers (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

SI9620107A 1995-08-10 1996-08-05 Blok polimer, ki ima funkcionalne skupine na obeh svojih koncih SI9620107A (sl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP20454795		1995-08-10
PCT/JP1996/002200 WO1997006202A1 (fr)	1995-08-10	1996-08-05	Polymere sequence pourvu de groupes fonctionnels aux deux extremites

Publications (1)

Publication Number	Publication Date
SI9620107A true SI9620107A (sl)	1998-10-31

Family

ID=16492323

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9620107A SI9620107A (sl)	1995-08-10	1996-08-05	Blok polimer, ki ima funkcionalne skupine na obeh svojih koncih

Country Status (17)

Country	Link
US (1)	US5929177A (fr)
EP (1)	EP0844269B1 (fr)
JP (1)	JP3711288B2 (fr)
KR (1)	KR19990014879A (fr)
CN (1)	CN1087317C (fr)
AT (1)	ATE226604T1 (fr)
AU (1)	AU726749B2 (fr)
BR (1)	BR9610053A (fr)
CA (1)	CA2229068A1 (fr)
DE (1)	DE69624488T2 (fr)
HU (1)	HUP9900662A3 (fr)
IL (1)	IL122021A0 (fr)
NO (1)	NO314589B1 (fr)
NZ (1)	NZ313769A (fr)
RU (1)	RU2174989C2 (fr)
SI (1)	SI9620107A (fr)
WO (1)	WO1997006202A1 (fr)

Families Citing this family (83)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9524475D0 (en) *	1995-11-30	1996-01-31	Zeneca Ltd	Compound preparation and use
JP4581248B2 (ja) *	1998-05-07	2010-11-17	日油株式会社	片末端に保護されていてもよいアミノ基を有するポリオキシエチレン誘導体及びその製造方法
DE19930729A1 (de) *	1999-07-05	2001-01-11	Achim Goepferich	Blockcopolymere zur Herstellung biomimetischer Oberflächen
JP2001048978A (ja)	1999-08-04	2001-02-20	Nano Career Kk	オキサゾリン由来のポリマーセグメントを有するブロックコポリマー
JP2001131271A (ja) *	1999-11-04	2001-05-15	Kazunori Kataoka	ポリマーミセルの層の積層した表面およびその作成方法
CA2389917A1 (fr)	1999-11-04	2001-05-10	Kazunori Kataoka	Micelle polymere comme monocouche ou surface a couches stratifiees
JP4659937B2 (ja) *	1999-11-19	2011-03-30	ナノキャリア株式会社	コア−シェル構造のポリイオンコンプレックスミセル
JP2001208754A (ja) *	2000-01-26	2001-08-03	Kazunori Kataoka	生物学的な被検体を検出するための組成物
AU5667901A (en) *	2000-05-11	2001-11-20	Center For Advanced Science And Technology Incubation, Ltd.	Polymer composition for forming surface of biosensor
US7217770B2 (en) *	2000-05-17	2007-05-15	Samyang Corporation	Stable polymeric micelle-type drug composition and method for the preparation thereof
US20050059031A1 (en) *	2000-10-06	2005-03-17	Quantum Dot Corporation	Method for enhancing transport of semiconductor nanocrystals across biological membranes
EP2085781B2 (fr) *	2000-10-06	2020-03-11	Life Technologies Corporation	Cellules dotées d'une signature spectrale et leurs procédés de préparation et leur utilisation
DE10101387A1 (de)	2001-01-13	2002-07-18	Merck Patent Gmbh	Polyester mit Methacrylatendgruppen
US6939564B2 (en) *	2001-06-08	2005-09-06	Labopharm, Inc.	Water-soluble stabilized self-assembled polyelectrolytes
US7094810B2 (en) *	2001-06-08	2006-08-22	Labopharm, Inc.	pH-sensitive block copolymers for pharmaceutical compositions
KR100566911B1 (ko)	2001-06-25	2006-04-03	주식회사 삼양사	약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체
CA2450949C (fr) *	2001-06-28	2009-04-28	John Samuel	Procedes et compositions d'antibiotiques de la famille des polyenes a toxicite reduite
US7009033B2 (en) *	2001-07-02	2006-03-07	Polymer Source Inc.	Heterofunctional polyethylene glycol and polyethylene oxide, process for their manufacture
JP4063510B2 (ja) *	2001-07-13	2008-03-19	ナノキャリア株式会社	薬物含有高分子ミセルの凍結乾燥用組成物およびその凍結乾燥製剤
KR100527291B1 (ko) *	2001-07-14	2005-11-09	주식회사 삼양사	약물 전달체용 양이온기-함유 양친성 블록 공중합체 및그의 음이온성 약물과의 복합체
ATE406436T1 (de)	2001-07-26	2008-09-15	Transparent Inc	Konstrukt aus kultivierten zellen mit spheroiden von kultivierten tierzellen und verwendung davon
US6592899B2 (en)	2001-10-03	2003-07-15	Macromed Incorporated	PLA/PLGA oligomers combined with block copolymers for enhancing solubility of a drug in water
CA2463517C (fr) *	2001-10-18	2010-03-16	Samyang Corporation	Derives d'acide polylactique biodegradables sensibles au ph formant des micelles polymeres et utilisations de ceux-ci pour l'administration de medicaments faiblement hydrosolubles
KR100492805B1 (ko) *	2001-10-18	2005-06-07	주식회사 삼양사	안정성이 향상된 고분자 미셀 조성물
KR100531269B1 (ko) *	2001-12-04	2005-11-28	주식회사 삼양사	수용액에서 안정한 미셀 또는 나노 파티클을 형성하는고분자 조성물
EP1489415A4 (fr) *	2002-03-11	2006-02-22	Toudai Tlo Ltd	Surface en poly(ethylene oxyde) a structure de type pinceau presentant une densite elevee
US20040005351A1 (en) *	2002-03-29	2004-01-08	Kwon Glen S.	Polymeric micelle formulations of hydrophobic compounds and methods
KR100502840B1 (ko) *	2002-09-04	2005-07-21	학교법인 포항공과대학교	약물 담지능력이 우수한 블록 공중합체 미셀 조성물
US20040116360A1 (en) *	2002-10-15	2004-06-17	Kwon Glen S.	Encapsulation and deaggregation of polyene antibiotics using poly(ethylene glycol)-phospholipid micelles
WO2004035013A2 (fr) *	2002-10-21	2004-04-29	L'oreal	Procede de dissolution de composes lipophiles dans une solution aqueuse avec des copolymeres sequences amphiphiles, et compositions cosmetiques
KR20050054129A (ko) *	2003-12-04	2005-06-10	주식회사 삼양사	고분자 미셀을 형성하는 생분해성 분지형 폴리락트산유도체, 및 그의 제조방법 및 용도
CA2549524A1 (fr) *	2004-01-02	2005-07-28	Wisconsin Alumni Research Foundation	Encapsulation de composes chimiques dans des micelles a noyau fluoritique et a enveloppe interne fluoree realises a partir de copolymeres sequences semi-fluores ou fluores
WO2005073370A1 (fr) *	2004-01-31	2005-08-11	Transparent Inc.	Compose enzymatique
EP1796690A4 (fr) *	2004-09-22	2011-08-03	Cartilix Inc	Dispositif de remplissage de cartilage
EP2067801A1 (fr) *	2005-01-04	2009-06-10	Intezyne Technologies Incorporated	Synthèse de copolymères hybrides à blocs
US20110124840A1 (en) *	2005-02-11	2011-05-26	Kurt Breitenkamp	Synthesis of Homopolymers and Block Copolymers
DK2656840T3 (en)	2005-06-09	2015-11-02	Nanocarrier Co Ltd	Process for preparing polymerized platinum complex coordination compounds
DE102005033101A1 (de) *	2005-07-15	2007-01-25	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Resorbierbare Polyetherester und ihre Verwendung zur Herstellung von medizinischen Implantaten
CN1304451C (zh) *	2005-09-13	2007-03-14	华东师范大学	端醛基聚氧乙烯－二乙三胺五乙酸嵌段聚合物及其合成方法
WO2007099660A1 (fr)	2006-03-01	2007-09-07	The University Of Tokyo	complexe de micelles polymeres contenant de l'acide nucleique
JPWO2007102608A1 (ja) *	2006-03-06	2009-07-23	ナノキャリア株式会社	疎水性化合物の安定化剤
CA2650422A1 (fr) *	2006-04-24	2007-11-08	Nanocarrier Co., Ltd.	Procede de production de micelles polymeriques encapsulant des medicaments a faible poids moleculaire
CN101489574A (zh)	2006-07-18	2009-07-22	那野伽利阿株式会社	内包生理活性多肽或蛋白质的高分子聚合物胶束及其制造方法
MX2009003092A (es) *	2006-09-22	2009-05-08	Labopharm Inc	Composiciones y metodos para suministro de farmaco dirigido a ph.
JP5277599B2 (ja) *	2006-09-29	2013-08-28	日油株式会社	生分解性ポリオキシアルキレン誘導体の製造方法
WO2008062909A1 (fr)	2006-11-22	2008-05-29	The University Of Tokyo	Support d'arnsi sensible à l'environnement utilisant une micelle polymérique à pont disulfure
WO2008070490A2 (fr) *	2006-11-28	2008-06-12	Wisconsin Alumni Research Foundation	Émulsions à base fluoropolymère pour l'administration intraveineuse d'anesthésiant volatil fluoré
WO2008071009A1 (fr) *	2006-12-15	2008-06-19	The Governors Of The University Of Alberta	Nouveaux copolymères séquencés guidés à ligands pour administration de médicaments ciblée
US8900562B2 (en) *	2007-01-12	2014-12-02	Wisconsin Alumni Research Foundation	Semi-fluorinated block copolymers for delivery of therapeutic agents
US20100178316A1 (en) *	2007-05-30	2010-07-15	Anuj Chauhan	Extended release of bioactive molecules from silicone hydrogels
US8075909B2 (en) *	2007-09-04	2011-12-13	University Of Florida Research Foundation, Incorporated	Contact lens based bioactive agent delivery system
US20110060123A1 (en)	2008-04-30	2011-03-10	Kazunori Kataoka	Charge conversional ternary polyplex
JP5737705B2 (ja) *	2008-05-02	2015-06-17	国立大学法人筑波大学	高分子化環状ニトロキシドラジカル化合物およびその使用
DK2305275T3 (da)	2008-06-24	2013-10-07	Nanocarrier Co Ltd	Væskesammensætning omfattende cisplatinkoordinerende forbindelse
CA2728960C (fr)	2008-06-26	2016-04-12	Japan Science And Technology Agency	Composite polymere/complexe metallique ayant une capacite de contraste en irm et contraste irm et/ou composition antitumorale l'utilisant
JP5327800B2 (ja) *	2009-07-31	2013-10-30	独立行政法人国立高等専門学校機構	カルボキシル基を末端基とするポリオキシアルキレン誘導体の製造
JP5522361B2 (ja) *	2009-09-18	2014-06-18	国立大学法人筑波大学	ガンの中性子捕捉療法を可能とする架橋型ホウ素内包ミセル
US20110081293A1 (en) *	2009-10-07	2011-04-07	Sanford-Burnham Medical Research Institute	Methods and compositions related to clot-binding lipid compounds
JP4829351B2 (ja)	2010-02-05	2011-12-07	ナノキャリア株式会社	易崩壊型ポリマーミセル組成物
WO2011127405A1 (fr)	2010-04-08	2011-10-13	Sanford-Burnham Medical Research Institute	Méthodes et compositions pour une administration améliorée de composés
EP2572780B1 (fr)	2010-05-21	2018-07-11	Japan Science And Technology Agency	Vésicules à substance encapsulée et leur procédé de fabrication
EP2591792B1 (fr)	2010-07-09	2016-12-21	The University of Tokyo	Composition d'administration d'acides nucléiques, composition d'excipient, composition pharmaceutique contenant la composition d'administration d'acides nucléiques ou la composition d'excipient et méthode d'administration d'acides nucléiques
CN103328038A (zh)	2010-12-01	2013-09-25	史拜诺莫度雷森公司	向神经解剖结构直接递送药剂
WO2012118778A1 (fr)	2011-02-28	2012-09-07	Sanford-Burnham Medical Research Institute	Peptides car tronqués, procédés et compositions les utilisant
US10166295B2 (en)	2011-06-02	2019-01-01	Opko Biologics Ltd.	Pegylated OXM variants
US10179801B2 (en)	2011-08-26	2019-01-15	Sanford-Burnham Medical Research Institute	Truncated LYP-1 peptides and methods and compositions using truncated LYP-1 peptides
KR101286854B1 (ko) *	2011-09-29	2013-07-17	중앙대학교 산학협력단	폴리락트산（ａ）과 폴리에틸렌글리콜（ｂ）로 이루어진 ｂａｂ형 삼중 블록 공중합체, 이의 제조방법 및 이를 이용한 약물전달체
MX362432B (es)	2012-06-04	2019-01-17	Opko Biologics Ltd	Variantes de oxm pegilada.
CN103059289A (zh) *	2013-01-08	2013-04-24	东南大学	一种聚乙二醇修饰的d-氨基葡萄糖及其合成和应用
CN109663550B (zh)	2013-03-01	2021-08-06	国立研究开发法人科学技术振兴机构	物质包封微囊及其制备方法
CN105377302B (zh)	2013-05-17	2018-05-11	那野伽利阿株式会社	聚合物胶束医药组合物
JP2015046867A (ja)	2013-07-31	2015-03-12	株式会社リコー	撮像装置
WO2015020026A1 (fr)	2013-08-06	2015-02-12	独立行政法人科学技術振興機構	Complexe de micelles polymères contenant de l'acide nucléique, et procédé de fabrication de celui-ci
EP3037107B1 (fr)	2013-08-23	2019-10-09	The University of Tokyo	Composite de nanoparticule polymère et composition pour imagerie irm le comprenant
JP5971264B2 (ja)	2014-01-10	2016-08-17	Ｊｆｅスチール株式会社	極厚肉油井管用ねじ継手
US10500246B2 (en)	2015-06-25	2019-12-10	Sanford Burnham Prebys Medical Discovery Institute	Compositions for delivery to and treatment of atherosclerotic plaques
US20170044316A1 (en)	2015-08-10	2017-02-16	Gelest Technologies, Inc.	Bifunctional Poly(alkyleneoxides) with Aminoalkyl and Unsaturated Termini and Derivatives Thereof
JP7067959B2 (ja) *	2017-03-08	2022-05-16	三洋化成工業株式会社	環状化合物組成物及びその製造方法
WO2018204392A1 (fr)	2017-05-02	2018-11-08	Stanford Burnham Prebys Medical Discovery Institute	Peptide liant des monocytes/macrophages associés à une tumeur et procédés d'utilisation associés
KR20190119433A (ko) *	2018-04-12	2019-10-22	삼성전자주식회사	양자점 소자 및 전자 장치
US12441776B2 (en)	2018-11-30	2025-10-14	Eirgen Pharma Ltd.	Oxyntomodulin peptide analog formulations
CN117159491A (zh) *	2018-12-17	2023-12-05	吉爱希公司	包含亲水性第一嵌段、疏水性第二嵌段和能够与硫醇特异性结合的官能团的嵌段共聚物
WO2020161602A1 (fr)	2019-02-04	2020-08-13	University Of Tartu	Peptides de liaison à la matrice extracellulaire bi-spécifiques et procédés d'utilisation de ceux-ci

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL75315A (en) *	1984-05-25	1991-07-18	Vestar Inc	Method for stabilization of vesicles
US5008109A (en) *	1984-05-25	1991-04-16	Vestar, Inc.	Vesicle stabilization
JPH02224822A (ja) *	1989-02-27	1990-09-06	Rikio Atobe	ベンダー用金型装置
JPH02242822A (ja) *	1989-03-16	1990-09-27	Hodogaya Chem Co Ltd	ポリオキシアルキレン誘導体の製法
JP2626654B2 (ja) *	1990-03-31	1997-07-02	科学技術振興事業団	標的指向性高分子医薬化合物及びその中間体
JPH0499731A (ja) *	1990-08-15	1992-03-31	Yoshiyuki Koyama	高分子キヤリアーおよびそれを用いた複合体
US5410016A (en) *	1990-10-15	1995-04-25	Board Of Regents, The University Of Texas System	Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
FR2678168B1 (fr) *	1991-06-28	1993-09-03	Rhone Poulenc Rorer Sa	Nanoparticules ayant un temps de capture par le dysteme reticulo endothelial allonge.
JPH05117385A (ja) *	1991-10-31	1993-05-14	Res Dev Corp Of Japan	ブロツク共重合体の製造法、ブロツク共重合体及び水溶性高分子抗癌剤
KR940003548U (ko) *	1992-08-14	1994-02-21	김형술	세탁물 건조기
WO1994022053A1 (fr) *	1993-03-18	1994-09-29	The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon	Changement de la fonctionnalite chimique des polymeres
KR0148704B1 (ko) *	1994-01-10	1998-08-17	김상응	생체분해성 약물전달용 고분자
JPH07247355A (ja) *	1994-03-10	1995-09-26	Nippon Oil & Fats Co Ltd	オリゴオキシアルキレン誘導体および生体適合性材料
JP3481318B2 (ja) *	1994-09-30	2003-12-22	剛遠藤	リビングポリマーの生長末端の変換とブロック共重合体の製造方法
JP3485404B2 (ja) *	1994-11-24	2004-01-13	竹本油脂株式会社	ポリオレフィン系繊維用耐久親水処理剤及びこれを用いるポリオレフィン系繊維への耐久親水性付与方法

1996
- 1996-08-05 AU AU66310/96A patent/AU726749B2/en not_active Expired
- 1996-08-05 RU RU98104071/04A patent/RU2174989C2/ru not_active IP Right Cessation
- 1996-08-05 EP EP96925998A patent/EP0844269B1/fr not_active Expired - Lifetime
- 1996-08-05 SI SI9620107A patent/SI9620107A/sl not_active IP Right Cessation
- 1996-08-05 CN CN96196186A patent/CN1087317C/zh not_active Expired - Lifetime
- 1996-08-05 US US09/011,329 patent/US5929177A/en not_active Expired - Lifetime
- 1996-08-05 KR KR1019970708224A patent/KR19990014879A/ko not_active Abandoned
- 1996-08-05 NZ NZ313769A patent/NZ313769A/en not_active IP Right Cessation
- 1996-08-05 AT AT96925998T patent/ATE226604T1/de not_active IP Right Cessation
- 1996-08-05 WO PCT/JP1996/002200 patent/WO1997006202A1/fr not_active Ceased
- 1996-08-05 CA CA002229068A patent/CA2229068A1/fr not_active Abandoned
- 1996-08-05 JP JP50831597A patent/JP3711288B2/ja not_active Expired - Lifetime
- 1996-08-05 HU HU9900662A patent/HUP9900662A3/hu unknown
- 1996-08-05 DE DE69624488T patent/DE69624488T2/de not_active Expired - Lifetime
- 1996-08-05 BR BR9610053A patent/BR9610053A/pt not_active IP Right Cessation
1997
- 1997-08-05 IL IL12202197A patent/IL122021A0/xx unknown
- 1997-12-03 NO NO19975584A patent/NO314589B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE226604T1 (de)	2002-11-15
DE69624488D1 (de)	2002-11-28
AU6631096A (en)	1997-03-05
US5929177A (en)	1999-07-27
NZ313769A (en)	2000-02-28
NO975584L (no)	1997-12-03
EP0844269B1 (fr)	2002-10-23
HUP9900662A3 (en)	2006-04-28
EP0844269A1 (fr)	1998-05-27
CN1087317C (zh)	2002-07-10
RU2174989C2 (ru)	2001-10-20
AU726749B2 (en)	2000-11-16
IL122021A0 (en)	1998-03-10
HUP9900662A2 (hu)	1999-06-28
JP3711288B2 (ja)	2005-11-02
NO975584D0 (no)	1997-12-03
CA2229068A1 (fr)	1997-02-20
WO1997006202A1 (fr)	1997-02-20
DE69624488T2 (de)	2003-06-26
EP0844269A4 (fr)	1999-01-27
KR19990014879A (ko)	1999-02-25
CN1192759A (zh)	1998-09-09
NO314589B1 (no)	2003-04-14
BR9610053A (pt)	1999-07-06

Legal Events

Date	Code	Title	Description
2005-01-10	IF	Valid on the event date
2006-10-31	KO00	Lapse of patent	Effective date: 20060912

Publication	Publication Date	Title
SI9620107A (sl)	1998-10-31	Blok polimer, ki ima funkcionalne skupine na obeh svojih koncih
CN115515924B (zh)	2023-10-20	一种阳离子脂质、含该阳离子脂质的脂质体、含该脂质体的核酸药物组合物及其制剂和应用
Toncheva et al.	1998	Novel vectors for gene delivery formed by self-assembly of DNA with poly (L-lysine) grafted with hydrophilic polymers
Neu et al.	2007	Bioreversibly crosslinked polyplexes of PEI and high molecular weight PEG show extended circulation times in vivo
Cammas et al.	1995	Heterobifunctional Poly (ethylene oxide): Synthesis of. alpha.-Methoxy-. omega.-amino and. alpha.-Hydroxy-. omega.-amino PEOs with the Same Molecular Weights
JP5191233B2 (ja)	2013-05-08	生分解性カチオン性ポリマー
US5919442A (en)	1999-07-06	Hyper comb-branched polymer conjugates
US11103588B2 (en)	2021-08-31	Methods and compositions relating to carnitine-derived materials
JPWO1997006202A1 (ja)	1998-09-08	両末端に官能基を有するブロックポリマー
Wu et al.	2015	Comb-like poly (L-cysteine) derivatives with different side groups: synthesis via photochemistry and click chemistry, multi-responsive nanostructures, triggered drug release and cytotoxicity
EP2035488A1 (fr)	2009-03-18	Micelles pour une administration de médicament
US20250288531A1 (en)	2025-09-18	Amino acid-based cationic lipid containing unsaturated bonds
Yuan et al.	2012	PEG‐b‐PtBA‐b‐PHEMA well‐defined amphiphilic triblock copolymer: Synthesis, self‐assembly, and application in drug delivery
US20230135432A1 (en)	2023-05-04	Polymeric nanoparticles and derivatives thereof for nucleic acid binding and delivery
Lai et al.	2014	PEGylated block copolymers containing tertiary amine side-chains cleavable via acid-labile ortho ester linkages for pH-triggered release of DNA
US20060014695A1 (en)	2006-01-19	Hpma-polyamine conjugates and uses therefore
Xu et al.	2008	Novel poly (ethylene imine) biscarbamate conjugate as an efficient and nontoxic gene delivery system
JP5522361B2 (ja)	2014-06-18	ガンの中性子捕捉療法を可能とする架橋型ホウ素内包ミセル
Bayó-Puxan et al.	2011	Preparation of polyion complex micelles from poly (ethylene glycol)-block-polyions
CN113214419B (zh)	2022-10-25	一种乳糖酸修饰的聚2-溴乙基丙烯酸酯及其制备方法与应用
CN117531019A (zh)	2024-02-09	一种聚合物多酚载药纳米体系制备方法及其应用
JP3832633B2 (ja)	2006-10-11	アミノ基含有ポリマーセグメントを有するブロックコポリマー
JP2017132746A (ja)	2017-08-03	ポリイオンコンプレックスを有効成分とするドライアイ処置用組成物
CN104069501A (zh)	2014-10-01	一种基于pamam的靶向给药载体及其制备方法
KR102838376B1 (ko)	2025-07-24	소교세포 표적 화합물 및 약물 전달체