IL126422A - Biodegradable acidic polylactic polymers and methods for their preparation - Google Patents
Biodegradable acidic polylactic polymers and methods for their preparationInfo
- Publication number
- IL126422A IL126422A IL12642297A IL12642297A IL126422A IL 126422 A IL126422 A IL 126422A IL 12642297 A IL12642297 A IL 12642297A IL 12642297 A IL12642297 A IL 12642297A IL 126422 A IL126422 A IL 126422A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- units
- polyester
- anhydride
- biodegradable polyester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 41
- 229920000642 polymer Polymers 0.000 title description 11
- 230000002378 acidificating effect Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 74
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 33
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical group OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920000229 biodegradable polyester Polymers 0.000 claims abstract description 24
- 239000004622 biodegradable polyester Substances 0.000 claims abstract description 24
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 16
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011975 tartaric acid Substances 0.000 claims abstract description 6
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 6
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 pamoic acid ester Chemical class 0.000 claims abstract 3
- 150000003899 tartaric acid esters Chemical class 0.000 claims abstract 3
- 229920000728 polyester Polymers 0.000 claims description 35
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 30
- 150000008064 anhydrides Chemical class 0.000 claims description 21
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 19
- 239000001384 succinic acid Substances 0.000 claims description 16
- 150000003077 polyols Chemical group 0.000 claims description 13
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical group ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 12
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 229940014800 succinic anhydride Drugs 0.000 claims description 12
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000004310 lactic acid Substances 0.000 claims description 9
- 235000014655 lactic acid Nutrition 0.000 claims description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical group C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 6
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 235000013772 propylene glycol Nutrition 0.000 claims description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical group OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000174 gluconic acid Substances 0.000 claims description 3
- 235000012208 gluconic acid Nutrition 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- NHDLVKOYPQPGNT-UHFFFAOYSA-N benzene-1,2,3,5-tetracarboxylic acid Chemical group OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1 NHDLVKOYPQPGNT-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 14
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 13
- 239000011521 glass Substances 0.000 description 13
- 238000006068 polycondensation reaction Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 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 4
- 238000004448 titration Methods 0.000 description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- 239000001358 L(+)-tartaric acid Substances 0.000 description 2
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 229940022769 d- lactic acid Drugs 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002394 hexacarboxylic acid derivatives Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IE1997/000031 WO1997040085A2 (en) | 1996-04-23 | 1997-04-22 | Acidic polylactic polymers |
| IE960307A IE960307A1 (en) | 1996-04-23 | 1998-10-07 | Acidic polylactic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL126422A0 IL126422A0 (en) | 1999-05-09 |
| IL126422A true IL126422A (en) | 2004-02-19 |
Family
ID=11041149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12642297A IL126422A (en) | 1996-04-23 | 1997-04-22 | Biodegradable acidic polylactic polymers and methods for their preparation |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6111033A (da) |
| EP (3) | EP1479707A3 (da) |
| JP (2) | JP3155013B2 (da) |
| AT (1) | ATE282653T1 (da) |
| AU (1) | AU727340C (da) |
| CA (1) | CA2250981C (da) |
| CZ (1) | CZ299398A3 (da) |
| DE (2) | DE69731623T4 (da) |
| DK (1) | DK0895517T3 (da) |
| ES (1) | ES2234014T3 (da) |
| HU (1) | HUP0000732A3 (da) |
| IE (1) | IE960307A1 (da) |
| IL (1) | IL126422A (da) |
| NO (1) | NO984923L (da) |
| NZ (1) | NZ332018A (da) |
| PL (1) | PL329598A1 (da) |
| RU (1) | RU2165942C2 (da) |
| WO (1) | WO1997040085A2 (da) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6221958B1 (en) * | 1993-01-06 | 2001-04-24 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
| IE960308A1 (en) | 1996-04-23 | 1997-11-05 | Kinerton Ltd | Sustained release ionic conjugate |
| DE19640269A1 (de) * | 1996-09-30 | 1998-04-02 | Basf Ag | Verwendung einer wäßrigen Dispersion eines biologisch abbaubaren Polyesters zur Umhüllung von Düngemittelgranulaten |
| US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| UA54505C2 (uk) | 1997-04-03 | 2003-03-17 | Гілфорд Фармасьютікалз Інк. | Полімери, що біологічно розкладаються, зшиті фосфатами, композиції, вироби і способи для їх виготовлення і використання |
| BR9809064A (pt) | 1997-04-03 | 2002-01-02 | Guilford Pharm Inc | Polìmeros biodegradáveis de poliéster de tereftalato-polifosfato, composições, artigos e métodos para fazer e usar os mesmos |
| US6867181B1 (en) | 1997-06-02 | 2005-03-15 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
| EP1035158A4 (en) * | 1997-10-29 | 2002-01-30 | Kanebo Ltd | RESIN COUPLING WITH BIODEGRADABILITY AND FOAMABILITY |
| US6548302B1 (en) | 1998-06-18 | 2003-04-15 | Johns Hopkins University School Of Medicine | Polymers for delivery of nucleic acids |
| US6419709B1 (en) | 1998-10-02 | 2002-07-16 | Guilford Pharmaceuticals, Inc. | Biodegradable terephthalate polyester-poly(Phosphite) compositions, articles, and methods of using the same |
| US6153212A (en) * | 1998-10-02 | 2000-11-28 | Guilford Pharmaceuticals Inc. | Biodegradable terephthalate polyester-poly (phosphonate) compositions, articles, and methods of using the same |
| US6350464B1 (en) | 1999-01-11 | 2002-02-26 | Guilford Pharmaceuticals, Inc. | Methods for treating ovarian cancer, poly (phosphoester) compositions, and biodegradable articles for same |
| US6537585B1 (en) | 1999-03-26 | 2003-03-25 | Guilford Pharmaceuticals, Inc. | Methods and compositions for treating solid tumors |
| AU767837B2 (en) * | 1999-08-18 | 2003-11-27 | Ipsen Pharma S.A.S. | Sustained release formulation of a peptide |
| EP1348444B1 (en) * | 1999-08-18 | 2006-04-12 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Sustained release formulation of a peptide complexed with a polymer |
| US7109166B1 (en) | 1999-08-18 | 2006-09-19 | Societe De Conseils De Recherches Et D'applications Scientifiques, Sas | Sustained release formulation of a peptide |
| JP4565290B2 (ja) * | 1999-12-01 | 2010-10-20 | 東洋紡績株式会社 | 高水酸基濃度を有するオキシ酸系脂肪族ポリエステルおよびオキシ酸系脂肪族ポリエステル組成物 |
| JP3450810B2 (ja) | 2000-01-31 | 2003-09-29 | キヤノン株式会社 | 脂肪族ポリエステル、脂肪族ポリエステルの製造方法およびセルロースの再資源化方法 |
| FR2821360B1 (fr) * | 2001-02-27 | 2003-05-30 | Sod Conseils Rech Applic | Procede de preparation de polyesters avec des fonctions acides libres intracatenaires |
| US20030045798A1 (en) * | 2001-09-04 | 2003-03-06 | Richard Hular | Multisensor probe for tissue identification |
| WO2003080629A2 (en) | 2002-02-25 | 2003-10-02 | Guilford Pharmaceuticals, Inc. | Phosphorus-containing compounds with polymeric chains, and methods of making and using the same |
| EP1911763B1 (en) | 2003-01-28 | 2010-08-11 | Ironwood Pharmaceuticals, Inc. | Compositions for the treatment of gastrointestinal disorders |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| CA2544678C (en) | 2003-11-05 | 2013-12-31 | Sunesis Pharmaceuticals, Inc. | Modulators of cellular adhesion |
| KR20050054129A (ko) * | 2003-12-04 | 2005-06-10 | 주식회사 삼양사 | 고분자 미셀을 형성하는 생분해성 분지형 폴리락트산유도체, 및 그의 제조방법 및 용도 |
| DE602004032265D1 (de) * | 2003-12-30 | 2011-05-26 | 3M Innovative Properties Co | Herstellungsverfahren von medizinischen zusammensetzungen |
| DK2444079T3 (da) | 2005-05-17 | 2017-01-30 | Sarcode Bioscience Inc | Sammensætninger og fremgangsmåder til behandling af øjensygdomme |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2830024T3 (es) | 2007-10-19 | 2021-06-02 | Novartis Ag | Composiciones y métodos para el tratamiento del edema macular |
| WO2009139817A2 (en) | 2008-04-15 | 2009-11-19 | Sarcode Corporation | Crystalline pharmaceutical and methods of preparation and use thereof |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| WO2011050175A1 (en) | 2009-10-21 | 2011-04-28 | Sarcode Corporation | Crystalline pharmaceutical and methods of preparation and use thereof |
| WO2011096968A1 (en) * | 2010-02-08 | 2011-08-11 | Danimer Scientific, Llc | Degradable polymers for hydrocarbon extraction |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| WO2012151343A1 (en) | 2011-05-04 | 2012-11-08 | Balance Therapeutics, Inc. | Pentylenetetrazole derivatives |
| WO2013042677A1 (ja) * | 2011-09-20 | 2013-03-28 | 東洋紡株式会社 | ポリ乳酸系ポリエステル樹脂、ポリ乳酸系ポリエステル樹脂水分散体、水性接着剤、及びポリ乳酸系ポリエステル樹脂水分散体の製造方法 |
| RU2467029C1 (ru) * | 2011-10-25 | 2012-11-20 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Способ получения биоразлагаемых полиэфиров |
| US9670311B2 (en) * | 2012-02-17 | 2017-06-06 | Toyobo Co., Ltd | Polylactic polyester resin, aqueous polylactic polyester resin dispersion, and production method for aqueous polylactic polyester resin dispersion |
| JP6133847B2 (ja) | 2012-04-27 | 2017-05-24 | 株式会社クレハ | ポリエステル樹脂組成物およびその成形体 |
| US10675376B2 (en) * | 2012-05-24 | 2020-06-09 | Ethicon Llc | Mechanically strong absorbable polymeric blend compositions of precisely controllable absorption rates, processing methods, and products therefrom |
| KR20200108932A (ko) | 2012-07-25 | 2020-09-21 | 에스에이알코드 바이오사이언스 인코포레이티드 | Lfa-1 저해제 및 그의 다형체 |
| KR101548314B1 (ko) * | 2012-12-17 | 2015-08-28 | 주식회사 엘지화학 | 폴리락타이드 수지의 제조방법 |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| AU2014235215A1 (en) | 2013-03-15 | 2015-10-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US20140274820A1 (en) * | 2013-03-15 | 2014-09-18 | Danimer Scientific, Llc | Degradable polymers and method for fracking applications |
| JP6661531B2 (ja) | 2013-10-10 | 2020-03-11 | シナジー ファーマシューティカルズ インコーポレイテッド | オピオイド誘発性機能障害の治療に有用なグアニル酸シクラーゼのアゴニスト |
| US10653744B2 (en) | 2016-01-11 | 2020-05-19 | Bausch Health Ireland Limited | Formulations and methods for treating ulcerative colitis |
| RU2715383C1 (ru) * | 2019-06-20 | 2020-02-27 | Общество с ограниченной ответственностью "ТВС" | Способ получения (со)полимера гликолида и/или лактида для изготовления рассасывающихся хирургических изделий |
| CN114940746B (zh) * | 2022-06-17 | 2024-04-26 | 山东采采医疗科技有限公司 | 星型丙交酯乙交酯共聚物及作为药物缓释载体的用途 |
| WO2026050206A1 (en) | 2024-08-27 | 2026-03-05 | Ironwood Pharmaceuticals, Inc. | Combinations of glp-1 and guanylate cyclase c (gc-c) receptor agonists |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) * | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| IE52535B1 (en) * | 1981-02-16 | 1987-12-09 | Ici Plc | Continuous release pharmaceutical compositions |
| US4523591A (en) * | 1982-10-22 | 1985-06-18 | Kaplan Donald S | Polymers for injection molding of absorbable surgical devices |
| DE3936191C2 (de) * | 1989-10-31 | 1996-10-17 | Boehringer Ingelheim Kg | Neue Copolymere aus Milchsäure und Weinsäure, ihre Herstellung sowie ihre Verwendung |
| JPH0665230A (ja) * | 1992-08-19 | 1994-03-08 | Showa Denko Kk | ラクチドの製造方法 |
| DK0678018T3 (da) * | 1993-01-06 | 2003-04-28 | Kinerton Ltd | Ion molekylærkonjugater af bionedbrydelige polyestere og bioaktive polypeptider |
| US5672659A (en) * | 1993-01-06 | 1997-09-30 | Kinerton Limited | Ionic molecular conjugates of biodegradable polyesters and bioactive polypeptides |
| AU706434B2 (en) * | 1994-10-18 | 1999-06-17 | Ethicon Inc. | Injectable liquid copolymers for soft tissue repair and augmentation |
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1997
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- 1997-04-22 CA CA002250981A patent/CA2250981C/en not_active Expired - Fee Related
- 1997-04-22 DE DE69731623T patent/DE69731623T4/de not_active Expired - Lifetime
- 1997-04-22 AU AU25752/97A patent/AU727340C/en not_active Ceased
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- 1997-04-22 DE DE69731623A patent/DE69731623D1/de not_active Expired - Fee Related
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| EP1479708A3 (en) | 2005-05-25 |
| NO984923D0 (no) | 1998-10-22 |
| HUP0000732A3 (en) | 2000-11-28 |
| NO984923L (no) | 1998-10-22 |
| HUP0000732A2 (en) | 2000-07-28 |
| DK0895517T3 (da) | 2005-01-17 |
| AU727340C (en) | 2001-11-08 |
| ES2234014T3 (es) | 2005-06-16 |
| WO1997040085A2 (en) | 1997-10-30 |
| DE69731623T4 (de) | 2006-08-31 |
| WO1997040085A3 (en) | 1998-01-22 |
| CZ299398A3 (cs) | 1999-01-13 |
| EP1479707A2 (en) | 2004-11-24 |
| PL329598A1 (en) | 1999-03-29 |
| AU727340B2 (en) | 2000-12-07 |
| AU2575297A (en) | 1997-11-12 |
| JP2001181378A (ja) | 2001-07-03 |
| US6111033A (en) | 2000-08-29 |
| JP3335995B2 (ja) | 2002-10-21 |
| DE69731623T2 (de) | 2005-10-06 |
| IL126422A0 (en) | 1999-05-09 |
| EP1479708A2 (en) | 2004-11-24 |
| CA2250981C (en) | 2002-07-02 |
| DE69731623D1 (de) | 2004-12-23 |
| JP3155013B2 (ja) | 2001-04-09 |
| EP1479707A3 (en) | 2005-05-18 |
| IE960307A1 (en) | 1997-11-05 |
| NZ332018A (en) | 2000-06-23 |
| EP0895517A2 (en) | 1999-02-10 |
| RU2165942C2 (ru) | 2001-04-27 |
| ATE282653T1 (de) | 2004-12-15 |
| EP0895517B1 (en) | 2004-11-17 |
| JPH11508640A (ja) | 1999-07-27 |
| CA2250981A1 (en) | 1997-10-30 |
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