EA008244B1 - Полимерные микроэмульсии - Google Patents

Info

Publication number

EA008244B1

EA008244B1 EA200401465A EA200401465A EA008244B1 EA 008244 B1 EA008244 B1 EA 008244B1 EA 200401465 A EA200401465 A EA 200401465A EA 200401465 A EA200401465 A EA 200401465A EA 008244 B1 EA008244 B1 EA 008244B1

Authority

EA

Eurasian Patent Office

Prior art keywords

polymer

diblock copolymer

valerolactone

copolymers

diblock

Prior art date

2002-05-03

Links

• Espacenet
• Global Dossier
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• 239000004530 micro-emulsion Substances 0.000 title description 16
• 229920000359 diblock copolymer Polymers 0.000 claims abstract description 89
• 239000000203 mixture Substances 0.000 claims abstract description 81
• 239000007788 liquid Substances 0.000 claims abstract description 35
• 239000004480 active ingredient Substances 0.000 claims abstract description 27
• 229920000642 polymer Polymers 0.000 claims description 113
• 239000000243 solution Substances 0.000 claims description 79
• 229920001577 copolymer Polymers 0.000 claims description 70
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
• -1 ε-lactone Chemical compound 0.000 claims description 54
• 239000000178 monomer Substances 0.000 claims description 45
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 39
• OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 38
• 239000002552 dosage form Substances 0.000 claims description 32
• YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 30
• GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 27
• 239000007864 aqueous solution Substances 0.000 claims description 26
• PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 26
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 22
• 238000000034 method Methods 0.000 claims description 21
• 229920001223 polyethylene glycol Polymers 0.000 claims description 21
• VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 20
• 229920001477 hydrophilic polymer Polymers 0.000 claims description 20
• VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims description 19
• VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 19
• 229960000380 propiolactone Drugs 0.000 claims description 19
• 238000003756 stirring Methods 0.000 claims description 15
• AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 12
• 238000002156 mixing Methods 0.000 claims description 10
• 238000007911 parenteral administration Methods 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 3
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• 239000000693 micelle Substances 0.000 description 43
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• 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 description 18
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• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 16
• 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 16
• 102000005962 receptors Human genes 0.000 description 16
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• 206010018910 Haemolysis Diseases 0.000 description 12
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• 125000000217 alkyl group Chemical group 0.000 description 11
• 150000001875 compounds Chemical class 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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• XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
• 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 description 8
• 108010036949 Cyclosporine Proteins 0.000 description 8
• 229960001265 ciclosporin Drugs 0.000 description 8
• 229960000890 hydrocortisone Drugs 0.000 description 8
• 229960000905 indomethacin Drugs 0.000 description 8
• 229960004125 ketoconazole Drugs 0.000 description 8
• 239000000523 sample Substances 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 206010062767 Hypophysitis Diseases 0.000 description 7
• 239000012736 aqueous medium Substances 0.000 description 7
• 210000004556 brain Anatomy 0.000 description 7
• 229930182912 cyclosporin Natural products 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 7
• 210000003635 pituitary gland Anatomy 0.000 description 7
• KDKUVYLMPJIGKA-UHFFFAOYSA-N 4-[[5-amino-1-[(2,6-difluorophenyl)-oxomethyl]-1,2,4-triazol-3-yl]amino]benzenesulfonamide Chemical compound N=1N(C(=O)C=2C(=CC=CC=2F)F)C(N)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 KDKUVYLMPJIGKA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 229920000469 amphiphilic block copolymer Polymers 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
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• 238000005538 encapsulation Methods 0.000 description 6
• 210000001035 gastrointestinal tract Anatomy 0.000 description 6
• 230000002209 hydrophobic effect Effects 0.000 description 6
• 238000011534 incubation Methods 0.000 description 6
• 239000003999 initiator Substances 0.000 description 6
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• 239000002287 radioligand Substances 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• 229930012538 Paclitaxel Natural products 0.000 description 5
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• 238000010521 absorption reaction Methods 0.000 description 5
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• 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 description 5
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• YIBOMRUWOWDFLG-UHFFFAOYSA-N 4-[[4-[4-(2-cyanoethenyl)-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C=CC#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-UHFFFAOYSA-N 0.000 description 4
• ZCFXFIHRHWRKAY-UHFFFAOYSA-N 5-[[3-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)-4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C(=CC=1)OC(F)(F)F)=CC=1C=C1SC(=O)NC1=O ZCFXFIHRHWRKAY-UHFFFAOYSA-N 0.000 description 4
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• WQUZPRFCWILZJO-AREMUKBSSA-N (3r)-3-(2,3-dihydro-1-benzofuran-5-yl)-2-(5-pyridin-2-ylpyrimidin-2-yl)-3,4-dihydro-1h-pyrrolo[3,4-b]quinolin-9-one Chemical compound C1([C@H]2C=3C=C4CCOC4=CC=3)=NC3=CC=CC=C3C(O)=C1CN2C(N=C1)=NC=C1C1=CC=CC=N1 WQUZPRFCWILZJO-AREMUKBSSA-N 0.000 description 3
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• JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 3
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• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
• WQUZPRFCWILZJO-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-5-yl)-2-(5-pyridin-2-ylpyrimidin-2-yl)-3,4-dihydro-1h-pyrrolo[3,4-b]quinolin-9-one Chemical compound C=1C=C2OCCC2=CC=1C1C2=NC3=CC=CC=C3C(O)=C2CN1C(N=C1)=NC=C1C1=CC=CC=N1 WQUZPRFCWILZJO-UHFFFAOYSA-N 0.000 description 2
• UCNOTTVNPRSTFW-LDADJPATSA-N 3-[[4-[(e)-3-(4-fluorophenyl)-2-methylprop-2-enyl]piperazin-1-yl]methyl]-7,8-dimethoxy-3a,4-dihydro-3h-chromeno[4,3-c][1,2]oxazole Chemical compound O1N=C2C=3C=C(OC)C(OC)=CC=3OCC2C1CN(CC1)CCN1C\C(C)=C\C1=CC=C(F)C=C1 UCNOTTVNPRSTFW-LDADJPATSA-N 0.000 description 2
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