CA2605652C - Polylactide compositions and uses thereof - Google Patents
Polylactide compositions and uses thereof Download PDFInfo
- Publication number
- CA2605652C CA2605652C CA2605652A CA2605652A CA2605652C CA 2605652 C CA2605652 C CA 2605652C CA 2605652 A CA2605652 A CA 2605652A CA 2605652 A CA2605652 A CA 2605652A CA 2605652 C CA2605652 C CA 2605652C
- Authority
- CA
- Canada
- Prior art keywords
- administration
- pharmaceutical preparation
- compound
- alkyl
- dione
- 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.)
- Expired - Fee Related
Links
- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 221
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 125
- 238000006243 chemical reaction Methods 0.000 claims description 118
- 239000003054 catalyst Substances 0.000 claims description 89
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 72
- -1 poly(ethylene glycol) Polymers 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 239000003814 drug Substances 0.000 claims description 58
- 229940079593 drug Drugs 0.000 claims description 57
- 239000003999 initiator Substances 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 43
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 35
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 229920001223 polyethylene glycol Polymers 0.000 claims description 28
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 238000004132 cross linking Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical group [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000443 aerosol Substances 0.000 claims description 11
- 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 claims description 10
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 238000007911 parenteral administration Methods 0.000 claims description 8
- 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 7
- 230000000699 topical effect Effects 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 6
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical group O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 6
- 238000007920 subcutaneous administration Methods 0.000 claims description 6
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000007918 intramuscular administration Methods 0.000 claims description 5
- 238000007912 intraperitoneal administration Methods 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
- 238000011200 topical administration Methods 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 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 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 4
- VSORDMNKDOKERL-UHFFFAOYSA-N 3,6-dihexyl-1,4-dioxane-2,5-dione Chemical compound CCCCCCC1OC(=O)C(CCCCCC)OC1=O VSORDMNKDOKERL-UHFFFAOYSA-N 0.000 claims 4
- 238000001361 intraarterial administration Methods 0.000 claims 4
- 238000007913 intrathecal administration Methods 0.000 claims 4
- 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 3
- 238000012377 drug delivery Methods 0.000 abstract description 35
- 229920000642 polymer Polymers 0.000 description 148
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical class CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 106
- 238000006116 polymerization reaction Methods 0.000 description 87
- 239000000178 monomer Substances 0.000 description 85
- 239000004626 polylactic acid Substances 0.000 description 77
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 59
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 57
- 238000003786 synthesis reaction Methods 0.000 description 56
- 238000006731 degradation reaction Methods 0.000 description 55
- 230000015556 catabolic process Effects 0.000 description 53
- 239000000693 micelle Substances 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 229920001577 copolymer Polymers 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 230000002209 hydrophobic effect Effects 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- 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 36
- 239000000463 material Substances 0.000 description 35
- 235000019441 ethanol Nutrition 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 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 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 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
- 150000002632 lipids Chemical class 0.000 description 23
- 230000037396 body weight Effects 0.000 description 22
- 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 20
- 230000009477 glass transition Effects 0.000 description 20
- 230000007246 mechanism Effects 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000002202 Polyethylene glycol Substances 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 235000019445 benzyl alcohol Nutrition 0.000 description 18
- 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
- 238000002360 preparation method Methods 0.000 description 17
- 101150041968 CDC13 gene Proteins 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000012512 characterization method Methods 0.000 description 15
- 238000005227 gel permeation chromatography Methods 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 14
- 239000003643 water by type Substances 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- NAKFRQULMGLXBT-UHFFFAOYSA-N 6-methoxyquinolin-8-ol Chemical compound N1=CC=CC2=CC(OC)=CC(O)=C21 NAKFRQULMGLXBT-UHFFFAOYSA-N 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 229920001400 block copolymer Polymers 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 229920001710 Polyorthoester Polymers 0.000 description 9
- 239000004098 Tetracycline Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000008363 phosphate buffer Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011550 stock solution Substances 0.000 description 9
- 229960002180 tetracycline Drugs 0.000 description 9
- 229930101283 tetracycline Natural products 0.000 description 9
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- 238000001556 precipitation Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- 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
- 238000002474 experimental method Methods 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 230000000977 initiatory effect Effects 0.000 description 7
- 238000011835 investigation Methods 0.000 description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
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- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 6
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- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- MZMWDTBBVARORD-UHFFFAOYSA-N 2-(2-bromopropanoyloxy)octanoic acid Chemical compound CCCCCCC(C(O)=O)OC(=O)C(C)Br MZMWDTBBVARORD-UHFFFAOYSA-N 0.000 description 5
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920003179 starch-based polymer Polymers 0.000 description 1
- 239000004628 starch-based polymer Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 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
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000002511 suppository base Substances 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
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 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
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dermatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Neurosurgery (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67410305P | 2005-04-22 | 2005-04-22 | |
| US60/674,103 | 2005-04-22 | ||
| US75014105P | 2005-12-14 | 2005-12-14 | |
| US60/750,141 | 2005-12-14 | ||
| PCT/IB2006/002849 WO2007012979A2 (en) | 2005-04-22 | 2006-04-21 | Polylactide compositions and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2605652A1 CA2605652A1 (en) | 2007-02-01 |
| CA2605652C true CA2605652C (en) | 2016-05-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2605652A Expired - Fee Related CA2605652C (en) | 2005-04-22 | 2006-04-21 | Polylactide compositions and uses thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US8466133B2 (https=) |
| EP (2) | EP3339348B1 (https=) |
| JP (5) | JP5749881B2 (https=) |
| CA (1) | CA2605652C (https=) |
| DK (1) | DK1883665T3 (https=) |
| ES (1) | ES2646141T3 (https=) |
| PL (1) | PL1883665T3 (https=) |
| PT (1) | PT1883665T (https=) |
| WO (1) | WO2007012979A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8466133B2 (en) * | 2005-04-22 | 2013-06-18 | University Of Geneva | Polylactides compositions and uses thereof |
| WO2008121702A2 (en) * | 2007-03-28 | 2008-10-09 | Boston Scientific Scimed, Inc. | Medical devices having bioerodable layers for the release of therapeutic agents |
| US20100159011A1 (en) * | 2007-08-03 | 2010-06-24 | University Of Massachusetts Medical School | Compositions For Biomedical 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 |
| WO2011082479A1 (en) * | 2010-01-08 | 2011-07-14 | University Of Prince Edward Island | Star polymers having controlled tacticity and methods of making same |
| DK2598553T3 (da) | 2010-07-26 | 2016-08-01 | Univ Geneve | Sammensætninger omfattende polymerer fremstillede af 2-hydroxyalkylsyrer |
| BR112013021732B1 (pt) | 2011-02-25 | 2021-11-30 | South Dakota State University | Micela estável e utilização da micela estável |
| US20140335135A1 (en) * | 2011-12-05 | 2014-11-13 | Ferring Bv | Pharmaceutical composition |
| JP6184982B2 (ja) * | 2012-02-02 | 2017-08-23 | エスバテック − ア ノバルティス カンパニー エルエルシー | 点眼用抗体含有徐放性製剤 |
| AR092821A1 (es) * | 2012-04-20 | 2015-05-06 | Sucampo Ag | Conjugado de derivado de acido graso-polimero |
| AR090736A1 (es) * | 2012-04-20 | 2014-12-03 | Sucampo Ag | Conjugado de compuesto triciclo-polimero |
| WO2014122294A1 (en) * | 2013-02-08 | 2014-08-14 | Total Research & Technology Feluy | Process for preparing cyclic esters and cyclic amides |
| US9080012B2 (en) * | 2013-07-10 | 2015-07-14 | Xerox Corporation | One-pot, neat ring opening polymerization to prepare resin |
| US8975344B2 (en) * | 2013-07-10 | 2015-03-10 | Xerox Corporation | Polyester/polycarbonate block copolymers via one-pot, neat ring opening polymerization |
| DE102013018193A1 (de) | 2013-10-30 | 2015-05-13 | Martin-Luther-Universität Halle-Wittenberg, Körperschaft des öffentlichen Rechts | Injizierbare Depotformulierungen zur kontrollierten Wirkstofffreisetzung |
| US9999704B2 (en) * | 2014-02-26 | 2018-06-19 | University Of Massachusetts | 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 |
| JP6557722B2 (ja) | 2014-05-30 | 2019-08-07 | シャイアー ヒューマン ジェネティック セラピーズ インコーポレイテッド | 核酸の送達のための生分解性脂質 |
| WO2016079416A1 (fr) * | 2014-11-17 | 2016-05-26 | Roquette Freres | Composition à base d'amidon thermoplastique et de polyester aliphatique |
| US9603975B2 (en) * | 2014-12-16 | 2017-03-28 | Boston Scientific Scimed, Inc. | Bioerodible polymer compositions |
| 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 |
| US10035877B1 (en) | 2017-03-08 | 2018-07-31 | International Business Machines Corporation | Matrix-bondable lactide monomors for polylactide synthesis |
| US10072121B1 (en) | 2017-03-08 | 2018-09-11 | International Business Machines Corporation | Bottlebrush polymers derived from poly(methylidenelactide) |
| US10570252B2 (en) | 2017-03-08 | 2020-02-25 | International Business Machines Corporation | Flame retardant lactide monomors for polylactide synthesis |
| US10202489B2 (en) | 2017-03-08 | 2019-02-12 | International Business Machines Corporation | Lactide copolymers and ring-opened lactide copolymers |
| 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 |
| WO1993000077A1 (en) | 1991-06-21 | 1993-01-07 | University Of Cincinnati | Orally administrable therapeutic proteins and method of making |
| 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 |
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| 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 |
| US6469133B2 (en) * | 1999-12-13 | 2002-10-22 | Board Of Trustees Of 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 |
| DE60333566D1 (de) * | 2002-08-13 | 2010-09-09 | Medtronic Inc | Medizinische vorrichtung mit verbesserter haftung zwischen einem polymeren berzug und einem substrat |
| KR20050084599A (ko) * | 2002-09-26 | 2005-08-26 | 안지오테크 인터내셔날 아게 | 혈관주위 랩 |
| US7533176B2 (en) | 2004-07-14 | 2009-05-12 | International Business Machines Corporation | Method for supporting connection establishment in an offload of network protocol processing |
| US8466133B2 (en) * | 2005-04-22 | 2013-06-18 | University Of Geneva | Polylactides compositions and uses thereof |
-
2006
- 2006-04-21 US US11/912,102 patent/US8466133B2/en not_active Expired - Fee Related
- 2006-04-21 DK DK06809004.2T patent/DK1883665T3/da active
- 2006-04-21 JP JP2008507201A patent/JP5749881B2/ja not_active Expired - Fee Related
- 2006-04-21 CA CA2605652A patent/CA2605652C/en not_active Expired - Fee Related
- 2006-04-21 ES ES06809004.2T patent/ES2646141T3/es not_active Expired - Lifetime
- 2006-04-21 EP EP17195684.0A patent/EP3339348B1/en not_active Expired - Lifetime
- 2006-04-21 EP EP06809004.2A patent/EP1883665B1/en not_active Expired - Lifetime
- 2006-04-21 WO PCT/IB2006/002849 patent/WO2007012979A2/en not_active Ceased
- 2006-04-21 PL PL06809004T patent/PL1883665T3/pl unknown
- 2006-04-21 PT PT68090042T patent/PT1883665T/pt unknown
-
2013
- 2013-02-26 US US13/778,038 patent/US8741877B2/en not_active Expired - Fee Related
- 2013-11-26 JP JP2013243625A patent/JP2014065722A/ja active Pending
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2014
- 2014-04-22 US US14/258,357 patent/US9375482B2/en not_active Expired - Fee Related
- 2014-10-08 JP JP2014207007A patent/JP6346540B2/ja not_active Expired - Fee Related
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2016
- 2016-03-16 JP JP2016051888A patent/JP6491614B2/ja not_active Expired - Fee Related
- 2016-05-27 US US15/166,801 patent/US9925267B2/en not_active Expired - Fee Related
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2017
- 2017-09-14 JP JP2017176282A patent/JP6559198B2/ja not_active Expired - Fee Related
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2018
- 2018-02-14 US US15/896,275 patent/US10314913B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP3339348B1 (en) | 2019-12-04 |
| JP2008538589A (ja) | 2008-10-30 |
| US9375482B2 (en) | 2016-06-28 |
| WO2007012979A3 (en) | 2007-05-03 |
| JP2016128506A (ja) | 2016-07-14 |
| US8741877B2 (en) | 2014-06-03 |
| JP6491614B2 (ja) | 2019-03-27 |
| JP6559198B2 (ja) | 2019-08-14 |
| US20150073060A1 (en) | 2015-03-12 |
| JP2015038121A (ja) | 2015-02-26 |
| US20180271984A1 (en) | 2018-09-27 |
| ES2646141T3 (es) | 2017-12-12 |
| CA2605652A1 (en) | 2007-02-01 |
| PL1883665T3 (pl) | 2018-05-30 |
| US8466133B2 (en) | 2013-06-18 |
| DK1883665T3 (da) | 2017-11-13 |
| JP5749881B2 (ja) | 2015-07-15 |
| US9925267B2 (en) | 2018-03-27 |
| US20130331464A1 (en) | 2013-12-12 |
| JP2014065722A (ja) | 2014-04-17 |
| JP6346540B2 (ja) | 2018-06-20 |
| US20090281068A1 (en) | 2009-11-12 |
| EP1883665A2 (en) | 2008-02-06 |
| EP1883665B1 (en) | 2017-10-11 |
| US20160367680A1 (en) | 2016-12-22 |
| WO2007012979A2 (en) | 2007-02-01 |
| PT1883665T (pt) | 2017-11-14 |
| EP3339348A1 (en) | 2018-06-27 |
| JP2017222712A (ja) | 2017-12-21 |
| US10314913B2 (en) | 2019-06-11 |
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|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210421 |