IL164977A - Polymeric microemulsions - Google Patents

Info

Publication number

IL164977A

IL164977A IL164977A IL16497704A IL164977A IL 164977 A IL164977 A IL 164977A IL 164977 A IL164977 A IL 164977A IL 16497704 A IL16497704 A IL 16497704A IL 164977 A IL164977 A IL 164977A

Authority

IL

Israel

Prior art keywords

polymer

diblock copolymer

valerolactone

copolymers

polymer block

Prior art date

2002-05-03

Links

• Espacenet
• Global Dossier
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• 239000004530 micro-emulsion Substances 0.000 title description 18
• 229920000642 polymer Polymers 0.000 claims description 103
• 229920000359 diblock copolymer Polymers 0.000 claims description 84
• 239000000203 mixture Substances 0.000 claims description 75
• 239000000243 solution Substances 0.000 claims description 74
• 229920001577 copolymer Polymers 0.000 claims description 71
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
• -1 poly(ethylene glycol) Polymers 0.000 claims description 62
• 239000000178 monomer Substances 0.000 claims description 48
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 45
• OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 39
• 239000007788 liquid Substances 0.000 claims description 33
• 239000002552 dosage form Substances 0.000 claims description 31
• YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 29
• PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 28
• 239000007864 aqueous solution Substances 0.000 claims description 27
• GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 27
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 26
• 239000004480 active ingredient Substances 0.000 claims description 26
• VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 24
• VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 23
• 229960000380 propiolactone Drugs 0.000 claims description 23
• VKSWWACDZPRJAP-UHFFFAOYSA-N 1,3-dioxepan-2-one Chemical compound O=C1OCCCCO1 VKSWWACDZPRJAP-UHFFFAOYSA-N 0.000 claims description 22
• 229920001223 polyethylene glycol Polymers 0.000 claims description 21
• 238000000034 method Methods 0.000 claims description 20
• 229920001477 hydrophilic polymer Polymers 0.000 claims description 18
• 238000002156 mixing Methods 0.000 claims description 11
• 238000003756 stirring Methods 0.000 claims description 11
• 238000007911 parenteral administration Methods 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 8
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
• 239000003814 drug Substances 0.000 description 101
• 229940079593 drug Drugs 0.000 description 100
• 239000000693 micelle Substances 0.000 description 41
• 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 description 23
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 21
• 229960001534 risperidone Drugs 0.000 description 21
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 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 17
• 229960003942 amphotericin b Drugs 0.000 description 17
• 150000001875 compounds Chemical class 0.000 description 16
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 15
• 239000003960 organic solvent Substances 0.000 description 15
• 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 14
• 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 14
• 239000004094 surface-active agent Substances 0.000 description 14
• AOLNDUQWRUPYGE-UHFFFAOYSA-N 1,4-dioxepan-5-one Chemical compound O=C1CCOCCO1 AOLNDUQWRUPYGE-UHFFFAOYSA-N 0.000 description 13
• 206010018910 Haemolysis Diseases 0.000 description 12
• 230000008588 hemolysis Effects 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
• 108020003175 receptors Proteins 0.000 description 11
• 102000005962 receptors Human genes 0.000 description 11
• 230000001965 increasing effect Effects 0.000 description 10
• 238000002835 absorbance Methods 0.000 description 9
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• 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
• 241001465754 Metazoa Species 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 210000004556 brain Anatomy 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 229960000890 hydrocortisone Drugs 0.000 description 7
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• 229930105110 Cyclosporin A Natural products 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
• 206010062767 Hypophysitis Diseases 0.000 description 6
• 239000002202 Polyethylene glycol Substances 0.000 description 6
• 238000013019 agitation Methods 0.000 description 6
• 239000012736 aqueous medium Substances 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 229960001265 ciclosporin Drugs 0.000 description 6
• 229930182912 cyclosporin Natural products 0.000 description 6
• 238000005538 encapsulation Methods 0.000 description 6
• 239000012530 fluid Substances 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 210000001035 gastrointestinal tract Anatomy 0.000 description 6
• 230000002209 hydrophobic effect Effects 0.000 description 6
• 210000001577 neostriatum Anatomy 0.000 description 6
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• 125000006239 protecting group Chemical group 0.000 description 6
• 239000002287 radioligand Substances 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 239000003981 vehicle Substances 0.000 description 6
• 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 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• 101150049660 DRD2 gene Proteins 0.000 description 5
• 229930012538 Paclitaxel Natural products 0.000 description 5
• 229920000469 amphiphilic block copolymer Polymers 0.000 description 5
• 210000004369 blood Anatomy 0.000 description 5
• 239000008280 blood Substances 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 230000009477 glass transition Effects 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
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• 210000005027 intestinal barrier Anatomy 0.000 description 5
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• 229960004125 ketoconazole Drugs 0.000 description 5
• 229960001592 paclitaxel Drugs 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 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
• 238000012360 testing method Methods 0.000 description 5
• 229930182843 D-Lactic acid Natural products 0.000 description 4
• JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 230000000259 anti-tumor effect Effects 0.000 description 4
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• 230000008499 blood brain barrier function Effects 0.000 description 4
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• 238000002474 experimental method Methods 0.000 description 4
• 230000002496 gastric effect Effects 0.000 description 4
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 239000012088 reference solution Substances 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 239000002033 PVDF binder Substances 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 239000000654 additive Substances 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 238000000604 cryogenic transmission electron microscopy Methods 0.000 description 3
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 210000003743 erythrocyte Anatomy 0.000 description 3
• 238000005227 gel permeation chromatography Methods 0.000 description 3
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• 238000002372 labelling Methods 0.000 description 3
• 239000012528 membrane Substances 0.000 description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
• UCBHICFFJKDMMR-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-(2-methyl-4,6-dihydropyrrolo[3,4-c]pyrazol-5-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CC2=NN(C)C=C2C1 UCBHICFFJKDMMR-AWEZNQCLSA-N 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
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• 229920001553 poly(ethylene glycol)-block-polylactide methyl ether Polymers 0.000 description 3
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• KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
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• 229960002555 zidovudine Drugs 0.000 description 3
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
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• 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
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• QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 2
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• 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 2
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
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• XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
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