ES2646141T3 - Composiciones de poliláctido y usos de las mismas - Google Patents
Composiciones de poliláctido y usos de las mismas Download PDFInfo
- Publication number
- ES2646141T3 ES2646141T3 ES06809004.2T ES06809004T ES2646141T3 ES 2646141 T3 ES2646141 T3 ES 2646141T3 ES 06809004 T ES06809004 T ES 06809004T ES 2646141 T3 ES2646141 T3 ES 2646141T3
- Authority
- ES
- Spain
- Prior art keywords
- pharmaceutical preparation
- substituted
- lactide
- rop
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
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Links
- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 215
- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 105
- 239000003814 drug Substances 0.000 claims abstract description 66
- 229940079593 drug Drugs 0.000 claims abstract description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 44
- 239000002904 solvent Substances 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 24
- 230000009477 glass transition Effects 0.000 claims abstract description 23
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 238000004132 cross linking Methods 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 6
- 229910052738 indium Inorganic materials 0.000 claims abstract description 6
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract 5
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 119
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 114
- 239000003054 catalyst Substances 0.000 claims description 86
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 52
- 239000003999 initiator Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 45
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 36
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 29
- 229920001223 polyethylene glycol Polymers 0.000 claims description 29
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 15
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 14
- BSDLHDSKWLPXIW-UHFFFAOYSA-N 3-hexyl-6-methyl-1,4-dioxane-2,5-dione Chemical compound CCCCCCC1OC(=O)C(C)OC1=O BSDLHDSKWLPXIW-UHFFFAOYSA-N 0.000 claims description 12
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000443 aerosol Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- YERALMNRPJTTGO-UHFFFAOYSA-N 3-methyl-6-propan-2-yl-1,4-dioxane-2,5-dione Chemical compound CC(C)C1OC(=O)C(C)OC1=O YERALMNRPJTTGO-UHFFFAOYSA-N 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
- DFYKCOWGIBSJOD-UHFFFAOYSA-N 3-benzyl-6-methyl-1,4-dioxane-2,5-dione Chemical compound O1C(=O)C(C)OC(=O)C1CC1=CC=CC=C1 DFYKCOWGIBSJOD-UHFFFAOYSA-N 0.000 claims description 7
- IRUSWOTYMUKTJX-UHFFFAOYSA-N 3-butyl-6-methyl-1,4-dioxane-2,5-dione Chemical compound CCCCC1OC(=O)C(C)OC1=O IRUSWOTYMUKTJX-UHFFFAOYSA-N 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 3
- 229940012356 eye drops Drugs 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 112
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical class CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 109
- 238000006116 polymerization reaction Methods 0.000 description 94
- 239000000178 monomer Substances 0.000 description 87
- 239000004626 polylactic acid Substances 0.000 description 82
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 71
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 58
- 238000006731 degradation reaction Methods 0.000 description 57
- 230000015556 catabolic process Effects 0.000 description 55
- 238000003786 synthesis reaction Methods 0.000 description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 235000019441 ethanol Nutrition 0.000 description 51
- 239000000693 micelle Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 229920001577 copolymer Polymers 0.000 description 44
- 239000000243 solution Substances 0.000 description 42
- 230000002209 hydrophobic effect Effects 0.000 description 41
- -1 benzyl ester Chemical class 0.000 description 39
- 239000000463 material Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
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- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 29
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 28
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 24
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 24
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 24
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 24
- 229960002867 griseofulvin Drugs 0.000 description 24
- 230000037396 body weight Effects 0.000 description 22
- 150000002632 lipids Chemical class 0.000 description 22
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 22
- 239000011159 matrix material Substances 0.000 description 20
- 230000007246 mechanism Effects 0.000 description 20
- 239000002202 Polyethylene glycol Substances 0.000 description 18
- RBGLVWCAGPITBS-UHFFFAOYSA-L bis(trifluoromethylsulfonyloxy)tin Chemical compound [Sn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F RBGLVWCAGPITBS-UHFFFAOYSA-L 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000003981 vehicle Substances 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
- 230000007423 decrease Effects 0.000 description 16
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000012512 characterization method Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000005227 gel permeation chromatography Methods 0.000 description 14
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 14
- 239000003643 water by type Substances 0.000 description 14
- NAKFRQULMGLXBT-UHFFFAOYSA-N 6-methoxyquinolin-8-ol Chemical compound N1=CC=CC2=CC(OC)=CC(O)=C21 NAKFRQULMGLXBT-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 235000013305 food Nutrition 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- 230000035484 reaction time Effects 0.000 description 13
- TYKJTLOUDJNYRH-UHFFFAOYSA-N 3,3,6-trimethyl-1,4-dioxane-2,5-dione Chemical compound CC1OC(=O)C(C)(C)OC1=O TYKJTLOUDJNYRH-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 12
- 238000001647 drug administration Methods 0.000 description 12
- 238000012377 drug delivery Methods 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 241000282414 Homo sapiens Species 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
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- 230000000704 physical effect Effects 0.000 description 11
- NWXMGUDVXFXRIG-NAOJVREFSA-N (4s,4as,5as,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2C(O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-NAOJVREFSA-N 0.000 description 10
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- 239000000047 product Substances 0.000 description 9
- 229960002180 tetracycline Drugs 0.000 description 9
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- 235000019364 tetracycline Nutrition 0.000 description 9
- 150000003522 tetracyclines Chemical class 0.000 description 9
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- HIAIVILTZQDDNY-UHFFFAOYSA-J tin(4+);trifluoromethanesulfonate Chemical compound [Sn+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HIAIVILTZQDDNY-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical class Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biomedical Technology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67410305P | 2005-04-22 | 2005-04-22 | |
| US674103P | 2005-04-22 | ||
| US75014105P | 2005-12-14 | 2005-12-14 | |
| US750141P | 2005-12-14 | ||
| PCT/IB2006/002849 WO2007012979A2 (en) | 2005-04-22 | 2006-04-21 | Polylactide compositions and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2646141T3 true ES2646141T3 (es) | 2017-12-12 |
Family
ID=37603048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06809004.2T Active ES2646141T3 (es) | 2005-04-22 | 2006-04-21 | Composiciones de poliláctido y usos de las mismas |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US8466133B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP3339348B1 (cg-RX-API-DMAC7.html) |
| JP (5) | JP5749881B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2605652C (cg-RX-API-DMAC7.html) |
| DK (1) | DK1883665T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2646141T3 (cg-RX-API-DMAC7.html) |
| PL (1) | PL1883665T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT1883665T (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007012979A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| PL1883665T3 (pl) * | 2005-04-22 | 2018-05-30 | Universite De Geneve | Kompozycje polilaktydowe i ich zastosowania |
| US20090074838A1 (en) * | 2007-03-28 | 2009-03-19 | Boston Scientific Scimed, Inc. | Medical devices having bioerodable layers for the release of therapeutic agents |
| EP2178936A4 (en) * | 2007-08-03 | 2012-12-12 | Univ Massachusetts Medical | POLYMERIC COMPOSITIONS FOR BIOMEDICAL AND MATERIAL APPLICATIONS |
| US8697098B2 (en) * | 2011-02-25 | 2014-04-15 | South Dakota State University | Polymer conjugated protein micelles |
| CN101665566B (zh) * | 2008-09-01 | 2012-01-04 | 南京工业大学 | 一种利用双螺杆挤出机制备聚乳酸及其制品的方法 |
| FR2942800B1 (fr) * | 2009-03-06 | 2012-04-20 | Minasolve | Procede de polymerisation par voie catalytique de 1,4-dioxanes-2,5 diones et les polymeres correspondants |
| CA2824250A1 (en) * | 2010-01-08 | 2011-07-14 | University Of Prince Edward Island | Star polymers having controlled tacticity and methods of making same |
| CA2806351C (en) * | 2010-07-26 | 2017-12-12 | Universite De Geneve | Compositions comprising polymers prepared from 2-hydroxyalkyl acids |
| AU2012222142B2 (en) | 2011-02-25 | 2017-01-12 | South Dakota State University | Polymer conjugated protein micelles |
| WO2013083605A1 (en) * | 2011-12-05 | 2013-06-13 | Ferring Bv | Triptorelin pharmaceutical composition |
| EP2809344B1 (en) | 2012-02-02 | 2016-08-24 | ESBATech - a Novartis Company LLC | Antibody-containing sustained-release formulation for ocular administration |
| AR090736A1 (es) * | 2012-04-20 | 2014-12-03 | Sucampo Ag | Conjugado de compuesto triciclo-polimero |
| AR092821A1 (es) * | 2012-04-20 | 2015-05-06 | Sucampo Ag | Conjugado de derivado de acido graso-polimero |
| US9573924B2 (en) | 2013-02-08 | 2017-02-21 | Total Research & Technology Feluy | Process for preparing cyclic esters and cyclic amides |
| US8975344B2 (en) * | 2013-07-10 | 2015-03-10 | Xerox Corporation | Polyester/polycarbonate block copolymers via one-pot, neat ring opening polymerization |
| US9080012B2 (en) * | 2013-07-10 | 2015-07-14 | Xerox Corporation | One-pot, neat ring opening polymerization to prepare resin |
| DE102013018193A1 (de) | 2013-10-30 | 2015-05-13 | Martin-Luther-Universität Halle-Wittenberg, Körperschaft des öffentlichen Rechts | Injizierbare Depotformulierungen zur kontrollierten Wirkstofffreisetzung |
| WO2015130877A1 (en) * | 2014-02-26 | 2015-09-03 | University Of Massachusetts Medical School | Amphiphilic degradable polymers for immobilization and sustained delivery of biomolecules |
| DE102014005782A1 (de) | 2014-04-23 | 2015-10-29 | Martin-Luther-Universität Halle-Wittenberg | lnjizierbare und implantierbare Trägersysteme auf Basis von modifizierten Poly(dikarbonsäure-multiol estern) zur kontrollierten Wirkstofffreisetzung |
| CN106659731A (zh) * | 2014-05-30 | 2017-05-10 | 夏尔人类遗传性治疗公司 | 用于递送核酸的可生物降解脂质 |
| US20180327588A1 (en) * | 2014-11-17 | 2018-11-15 | Roquette Freres | Composition comprising thermoplastic starch and aliphatic polyester |
| JP2017535645A (ja) * | 2014-12-16 | 2017-11-30 | ボストン サイエンティフィック サイムド，インコーポレイテッドＢｏｓｔｏｎ Ｓｃｉｅｎｔｉｆｉｃ Ｓｃｉｍｅｄ，Ｉｎｃ． | 生分解性ポリマー組成物 |
| US9260550B1 (en) * | 2015-01-27 | 2016-02-16 | International Business Machines Corporation | Lactide-based acrylate polymers |
| JP6148701B2 (ja) * | 2015-07-31 | 2017-06-14 | ユニベルシテ ドゥ ジュネーブ | ２−ヒドロキシアルキル酸から調製されたポリマーを含む組成物 |
| US10202489B2 (en) | 2017-03-08 | 2019-02-12 | International Business Machines Corporation | Lactide copolymers and ring-opened lactide copolymers |
| US10570252B2 (en) | 2017-03-08 | 2020-02-25 | International Business Machines Corporation | Flame retardant lactide monomors for polylactide synthesis |
| US10072121B1 (en) | 2017-03-08 | 2018-09-11 | International Business Machines Corporation | Bottlebrush polymers derived from poly(methylidenelactide) |
| US10035877B1 (en) | 2017-03-08 | 2018-07-31 | International Business Machines Corporation | Matrix-bondable lactide monomors for polylactide synthesis |
| EP3743041A1 (en) | 2018-01-26 | 2020-12-02 | Apidel SA | New spironolactone formulations and their use |
| CA2994005A1 (fr) * | 2018-02-05 | 2019-08-05 | Hydro-Quebec | Copolymeres d'unites ester et ether, leurs procedes de fabrication et leurs utilisations |
| EP3656378A1 (en) * | 2018-11-26 | 2020-05-27 | ValMeyer Sàrl | New composition of amide and ester local anesthetics and uses thereof |
| US11407855B2 (en) | 2019-08-23 | 2022-08-09 | The Board Of Trustees Of The University Of Illinois | Ring opening polymerization in an aqueous dispersion |
| CN116217900B (zh) * | 2021-12-02 | 2025-12-30 | 惠生工程（中国）有限公司 | 一种乙交酯、丙交酯开环共聚合制备pgla的装置及工艺 |
| WO2024064758A2 (en) * | 2022-09-21 | 2024-03-28 | Hercules Llc | Coating composition comprising a bioresorbable copolymer and an anti-microbial agent |
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| CA1098443A (en) * | 1977-05-20 | 1981-03-31 | Namassivaya Doddi | Absorbable p-dioxanone polymer-drug compositions |
| US5725871A (en) | 1989-08-18 | 1998-03-10 | Danbiosyst Uk Limited | Drug delivery compositions comprising lysophosphoglycerolipid |
| US5707644A (en) | 1989-11-04 | 1998-01-13 | Danbiosyst Uk Limited | Small particle compositions for intranasal drug delivery |
| US5466468A (en) | 1990-04-03 | 1995-11-14 | Ciba-Geigy Corporation | Parenterally administrable liposome formulation comprising synthetic lipids |
| 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 |
| US5399363A (en) | 1991-01-25 | 1995-03-21 | Eastman Kodak Company | Surface modified anticancer nanoparticles |
| ATE158180T1 (de) | 1991-06-21 | 1997-10-15 | Univ Cincinnati | Oral verabreichbare therapeutische proteine und herstellungsverfahren |
| US5756353A (en) | 1991-12-17 | 1998-05-26 | The Regents Of The University Of California | Expression of cloned genes in the lung by aerosol-and liposome-based delivery |
| CA2087125A1 (en) * | 1992-01-23 | 1993-07-24 | Mridula Nair | Chemically fixed micelles |
| US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
| US5686630A (en) * | 1993-09-29 | 1997-11-11 | Chronopol, Inc. | Purifying cyclic esters by aqueous solvent extraction |
| ES2105262T3 (es) | 1992-05-18 | 1997-10-16 | Minnesota Mining & Mfg | Dispositivo de suministro de farmaco a traves de las mucosas. |
| US5792451A (en) | 1994-03-02 | 1998-08-11 | Emisphere Technologies, Inc. | Oral drug delivery compositions and methods |
| KR970002523B1 (en) * | 1993-04-24 | 1997-03-05 | Korea Inst Sci & Tech | Biodegradable polylactic acid having improved properties and method for manufacturing the same |
| US5543158A (en) | 1993-07-23 | 1996-08-06 | Massachusetts Institute Of Technology | Biodegradable injectable nanoparticles |
| US6007845A (en) * | 1994-07-22 | 1999-12-28 | Massachusetts Institute Of Technology | Nanoparticles and microparticles of non-linear hydrophilic-hydrophobic multiblock copolymers |
| US5580579A (en) | 1995-02-15 | 1996-12-03 | Nano Systems L.L.C. | Site-specific adhesion within the GI tract using nanoparticles stabilized by high molecular weight, linear poly (ethylene oxide) polymers |
| IE80468B1 (en) | 1995-04-04 | 1998-07-29 | Elan Corp Plc | Controlled release biodegradable nanoparticles containing insulin |
| US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| US6451346B1 (en) * | 1998-12-23 | 2002-09-17 | Amgen Inc | Biodegradable pH/thermosensitive hydrogels for sustained delivery of biologically active agents |
| AU2098901A (en) * | 1999-12-13 | 2001-06-18 | Michigan State University | Process for the preparation of polymers of dimeric cyclic esters |
| US6613308B2 (en) | 2000-09-19 | 2003-09-02 | Advanced Inhalation Research, Inc. | Pulmonary delivery in treating disorders of the central nervous system |
| KR100484371B1 (ko) | 2001-10-25 | 2005-04-20 | 가부시키가이샤 아텍스 | 히터선부착 시트체의 제조방법 |
| AU2003258230A1 (en) * | 2002-08-13 | 2004-02-25 | Medtronic, Inc | Medical device exhibiting improved adhesion between polymeric coating and substrate |
| ATE416795T1 (de) * | 2002-09-26 | 2008-12-15 | Angiotech Int Ag | Perivaskuläre hüllen |
| US7533176B2 (en) | 2004-07-14 | 2009-05-12 | International Business Machines Corporation | Method for supporting connection establishment in an offload of network protocol processing |
| PL1883665T3 (pl) * | 2005-04-22 | 2018-05-30 | Universite De Geneve | Kompozycje polilaktydowe i ich zastosowania |
-
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- 2006-04-21 WO PCT/IB2006/002849 patent/WO2007012979A2/en not_active Ceased
- 2006-04-21 PT PT68090042T patent/PT1883665T/pt unknown
- 2006-04-21 JP JP2008507201A patent/JP5749881B2/ja not_active Expired - Fee Related
- 2006-04-21 ES ES06809004.2T patent/ES2646141T3/es active Active
- 2006-04-21 CA CA2605652A patent/CA2605652C/en not_active Expired - Fee Related
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- 2006-04-21 US US11/912,102 patent/US8466133B2/en not_active Expired - Fee Related
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- 2006-04-21 EP EP06809004.2A patent/EP1883665B1/en not_active Not-in-force
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2013
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- 2013-11-26 JP JP2013243625A patent/JP2014065722A/ja active Pending
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- 2016-05-27 US US15/166,801 patent/US9925267B2/en not_active Expired - Fee Related
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2018
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2017222712A (ja) | 2017-12-21 |
| JP2008538589A (ja) | 2008-10-30 |
| US8466133B2 (en) | 2013-06-18 |
| JP2016128506A (ja) | 2016-07-14 |
| US8741877B2 (en) | 2014-06-03 |
| JP2015038121A (ja) | 2015-02-26 |
| WO2007012979A3 (en) | 2007-05-03 |
| WO2007012979A2 (en) | 2007-02-01 |
| EP1883665A2 (en) | 2008-02-06 |
| US20090281068A1 (en) | 2009-11-12 |
| US20130331464A1 (en) | 2013-12-12 |
| DK1883665T3 (da) | 2017-11-13 |
| US9375482B2 (en) | 2016-06-28 |
| JP6346540B2 (ja) | 2018-06-20 |
| CA2605652C (en) | 2016-05-24 |
| US20180271984A1 (en) | 2018-09-27 |
| JP6559198B2 (ja) | 2019-08-14 |
| US9925267B2 (en) | 2018-03-27 |
| EP3339348A1 (en) | 2018-06-27 |
| PT1883665T (pt) | 2017-11-14 |
| CA2605652A1 (en) | 2007-02-01 |
| EP1883665B1 (en) | 2017-10-11 |
| US20160367680A1 (en) | 2016-12-22 |
| JP6491614B2 (ja) | 2019-03-27 |
| US10314913B2 (en) | 2019-06-11 |
| EP3339348B1 (en) | 2019-12-04 |
| JP5749881B2 (ja) | 2015-07-15 |
| JP2014065722A (ja) | 2014-04-17 |
| US20150073060A1 (en) | 2015-03-12 |
| PL1883665T3 (pl) | 2018-05-30 |
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