WO1997049385B1 - Procedes et compositions utilisant des excipients organiques pour renforcer les proprietes bioadhesives de polymeres - Google Patents
Procedes et compositions utilisant des excipients organiques pour renforcer les proprietes bioadhesives de polymeresInfo
- Publication number
- WO1997049385B1 WO1997049385B1 PCT/US1997/010256 US9710256W WO9749385B1 WO 1997049385 B1 WO1997049385 B1 WO 1997049385B1 US 9710256 W US9710256 W US 9710256W WO 9749385 B1 WO9749385 B1 WO 9749385B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- microsphere
- polymer
- composition
- anhydride
- polymers
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract 36
- 238000000034 method Methods 0.000 title claims abstract 31
- 239000000203 mixture Substances 0.000 title claims abstract 19
- 239000000227 bioadhesive Substances 0.000 title claims abstract 5
- 230000002708 enhancing effect Effects 0.000 title abstract 2
- 239000008012 organic excipient Substances 0.000 title 1
- 239000004005 microsphere Substances 0.000 claims abstract 32
- 150000008064 anhydrides Chemical class 0.000 claims abstract 23
- 229940039227 diagnostic agent Drugs 0.000 claims abstract 9
- 239000000032 diagnostic agent Substances 0.000 claims abstract 9
- 239000003814 drug Substances 0.000 claims abstract 9
- 239000012528 membrane Substances 0.000 claims abstract 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000012377 drug delivery Methods 0.000 claims abstract 4
- 239000000178 monomer Substances 0.000 claims abstract 4
- 150000004676 glycans Chemical class 0.000 claims abstract 3
- 229920001282 polysaccharide Polymers 0.000 claims abstract 3
- 239000005017 polysaccharide Substances 0.000 claims abstract 3
- 102000004169 proteins and genes Human genes 0.000 claims abstract 3
- 108090000623 proteins and genes Proteins 0.000 claims abstract 3
- 230000002496 gastric effect Effects 0.000 claims abstract 2
- 230000000241 respiratory effect Effects 0.000 claims abstract 2
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 210000004379 membrane Anatomy 0.000 claims 6
- -1 polyaryalkylenes Polymers 0.000 claims 6
- 230000001225 therapeutic effect Effects 0.000 claims 5
- 239000007789 gas Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims 2
- 239000004952 Polyamide Substances 0.000 claims 2
- 229920002732 Polyanhydride Polymers 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 235000010980 cellulose Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 239000006185 dispersion Substances 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 2
- 229920002627 poly(phosphazenes) Polymers 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 229920001281 polyalkylene Polymers 0.000 claims 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims 2
- 229920002647 polyamide Polymers 0.000 claims 2
- 229920000515 polycarbonate Polymers 0.000 claims 2
- 239000004417 polycarbonate Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 229920002635 polyurethane Polymers 0.000 claims 2
- 239000004814 polyurethane Substances 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- DFOCUWFSRVQSNI-UHFFFAOYSA-N 3-[4-(2-carboxyethyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(CCC(O)=O)C=C1 DFOCUWFSRVQSNI-UHFFFAOYSA-N 0.000 claims 1
- ITEKDBLBCIMYAT-UHFFFAOYSA-N 4-[(4-carboxyphenoxy)methoxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCOC1=CC=C(C(O)=O)C=C1 ITEKDBLBCIMYAT-UHFFFAOYSA-N 0.000 claims 1
- LFPLRGMCQXEYDO-UHFFFAOYSA-N 4-[1-(4-carboxyphenoxy)propoxy]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1OC(CC)OC1=CC=C(C(O)=O)C=C1 LFPLRGMCQXEYDO-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 210000004400 mucous membrane Anatomy 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 229920000249 biocompatible polymer Polymers 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 230000034659 glycolysis Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 210000005000 reproductive tract Anatomy 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Abstract
La présente invention concerne des procédés et compositions permettant de renforcer les propriétés bioadhésives de polymères utilisés dans les systèmes d'administration de médicaments. En incorporant un oligomère d'anhydride dans le polymère on renforce ses propriétés bioadhésives ce qui fait que ce polymère adhère plus facilement à la surface d'un tissu tel qu'une membrane de muqueuse. Parmi les oligomères d'anhydrides qui renforcent les propriétés bioadhésives d'un polymère, on trouve des oligomères synthétisés à partir de monomères d'acide dicarboxylique, de préférence les monomères que l'on trouve dans le cycle de glycolyse de Krebs, et notamment l'acide fumarique. Ces oligomères peuvent s'incorporer dans une large gamme de polymères, y compris des protéines, des polyosides et des polymères biocompatibles synthétiques. Selon une réalisation, les oligomères d'anhydrides peuvent s'incorporer dans des polymères utilisés pour former ou enrober les systèmes d'administration de médicaments, tels que les microsphères, qui contiennent un médicament ou un agent de diagnostic. De tels polymères, par exemple ceux qui se trouvent sous forme de microsphères, sont plus aptes à adhérer aux membranes des muqueuses. Ils conviennent donc à l'administration d'un médicament ou d'un agent de diagnostic via diverses surfaces de membranes de muqueuses, et notamment celles des voies gastro-intestinales, respiratoires, excrétrices et génitales.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10503153A JP2000513355A (ja) | 1996-06-25 | 1997-06-12 | 有機賦型剤を使用する、ポリマーの生体接着特性を増強するための方法および組成物 |
AT97929973T ATE230978T1 (de) | 1996-06-25 | 1997-06-12 | Verfahren und zubereitungen zum verbessern der bioadhäsiv-eigenschaften von polymeren unter verwendung organischer excipienten |
EP97929973A EP0912166B1 (fr) | 1996-06-25 | 1997-06-12 | Procedes et compositions utilisant des excipients organiques pour renforcer les proprietes bioadhesives de polymeres |
DE69718470T DE69718470T2 (de) | 1996-06-25 | 1997-06-12 | Verfahren und zubereitungen zum verbessern der bioadhäsiv-eigenschaften von polymeren unter verwendung organischer excipienten |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US670,326 | 1996-06-25 | ||
US08/670,326 US5955096A (en) | 1996-06-25 | 1996-06-25 | Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1997049385A1 WO1997049385A1 (fr) | 1997-12-31 |
WO1997049385B1 true WO1997049385B1 (fr) | 1998-02-26 |
Family
ID=24689975
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/010256 WO1997049385A1 (fr) | 1996-06-25 | 1997-06-12 | Procedes et compositions utilisant des excipients organiques pour renforcer les proprietes bioadhesives de polymeres |
Country Status (6)
Country | Link |
---|---|
US (3) | US5955096A (fr) |
EP (1) | EP0912166B1 (fr) |
JP (1) | JP2000513355A (fr) |
AT (1) | ATE230978T1 (fr) |
DE (1) | DE69718470T2 (fr) |
WO (1) | WO1997049385A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9108070B2 (en) | 2006-09-13 | 2015-08-18 | Polymerix Corporation | Active agents and their oligomers and polymers |
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- 1997-06-12 JP JP10503153A patent/JP2000513355A/ja not_active Ceased
- 1997-06-12 EP EP97929973A patent/EP0912166B1/fr not_active Expired - Lifetime
- 1997-06-12 WO PCT/US1997/010256 patent/WO1997049385A1/fr active IP Right Grant
- 1997-06-12 AT AT97929973T patent/ATE230978T1/de not_active IP Right Cessation
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1998
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