NZ336903A - Medicinal formulations comprising biocompatible polymers of the formula -[X-R-C(O)]- for pharmaceutical drug delivery systems - Google Patents
Medicinal formulations comprising biocompatible polymers of the formula -[X-R-C(O)]- for pharmaceutical drug delivery systemsInfo
- Publication number
- NZ336903A NZ336903A NZ336903A NZ33690398A NZ336903A NZ 336903 A NZ336903 A NZ 336903A NZ 336903 A NZ336903 A NZ 336903A NZ 33690398 A NZ33690398 A NZ 33690398A NZ 336903 A NZ336903 A NZ 336903A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formulation
- drug
- polymer
- biocompatible polymer
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 258
- 229940079593 drug Drugs 0.000 title claims abstract description 221
- 238000009472 formulation Methods 0.000 title claims abstract description 182
- 229920000249 biocompatible polymer Polymers 0.000 title claims abstract description 131
- 238000012377 drug delivery Methods 0.000 title description 17
- 239000003814 drug Substances 0.000 claims abstract description 219
- 229920000642 polymer Polymers 0.000 claims abstract description 190
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 80
- 238000013268 sustained release Methods 0.000 claims abstract description 62
- 239000012730 sustained-release form Substances 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 21
- 125000000962 organic group Chemical group 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004005 microsphere Substances 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 67
- 241001070944 Mimosa Species 0.000 claims description 67
- 239000000443 aerosol Substances 0.000 claims description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000003380 propellant Substances 0.000 claims description 44
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 239000012530 fluid Substances 0.000 claims description 34
- 229920002988 biodegradable polymer Polymers 0.000 claims description 32
- 239000004621 biodegradable polymer Substances 0.000 claims description 30
- -1 isoethionate Chemical compound 0.000 claims description 29
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 27
- 239000011159 matrix material Substances 0.000 claims description 21
- 229940071648 metered dose inhaler Drugs 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 21
- 239000002243 precursor Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 230000015556 catabolic process Effects 0.000 claims description 17
- 238000006731 degradation reaction Methods 0.000 claims description 17
- 239000000725 suspension Substances 0.000 claims description 17
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 15
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims description 14
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 14
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 13
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 12
- 229960004194 lidocaine Drugs 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- 235000014655 lactic acid Nutrition 0.000 claims description 11
- 239000004098 Tetracycline Substances 0.000 claims description 10
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 10
- 150000007942 carboxylates Chemical group 0.000 claims description 10
- 150000001261 hydroxy acids Chemical class 0.000 claims description 10
- 239000004310 lactic acid Substances 0.000 claims description 10
- 229960002052 salbutamol Drugs 0.000 claims description 10
- 229960002180 tetracycline Drugs 0.000 claims description 10
- 229930101283 tetracycline Natural products 0.000 claims description 10
- 235000019364 tetracycline Nutrition 0.000 claims description 10
- 150000003522 tetracyclines Chemical class 0.000 claims description 10
- 239000011859 microparticle Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 208000037534 Progressive hemifacial atrophy Diseases 0.000 claims description 8
- CDKNUFNIFGPFSF-AYVLZSQQSA-N [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-10,13-dimethyl-3-oxo-17-(2-propanoylsulfanylacetyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] butanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)CC)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O CDKNUFNIFGPFSF-AYVLZSQQSA-N 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical compound O=C1COCCO1 VPVXHAANQNHFSF-UHFFFAOYSA-N 0.000 claims description 7
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 7
- 238000012017 passive hemagglutination assay Methods 0.000 claims description 7
- 229920000903 polyhydroxyalkanoate Polymers 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 5
- 229960004436 budesonide Drugs 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 4
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 3
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 3
- 229960002714 fluticasone Drugs 0.000 claims description 3
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 3
- 229960005414 pirbuterol Drugs 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims description 2
- 229930182837 (R)-adrenaline Natural products 0.000 claims description 2
- YLBOOZRFNPXAAQ-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-phenylurea Chemical compound CCC(CC)N(O)C(=O)NC1=CC=CC=C1 YLBOOZRFNPXAAQ-UHFFFAOYSA-N 0.000 claims description 2
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical class CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 2
- 229930003347 Atropine Natural products 0.000 claims description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 2
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 2
- 229960000396 atropine Drugs 0.000 claims description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 2
- 229960002881 clemastine Drugs 0.000 claims description 2
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims description 2
- 229960000265 cromoglicic acid Drugs 0.000 claims description 2
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 2
- 229960002179 ephedrine Drugs 0.000 claims description 2
- 229960005139 epinephrine Drugs 0.000 claims description 2
- 229960002428 fentanyl Drugs 0.000 claims description 2
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002848 formoterol Drugs 0.000 claims description 2
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 2
- 229960001361 ipratropium bromide Drugs 0.000 claims description 2
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims description 2
- 229940039009 isoproterenol Drugs 0.000 claims description 2
- 229960005181 morphine Drugs 0.000 claims description 2
- 229960004398 nedocromil Drugs 0.000 claims description 2
- RQTOOFIXOKYGAN-UHFFFAOYSA-N nedocromil Chemical compound CCN1C(C(O)=O)=CC(=O)C2=C1C(CCC)=C1OC(C(O)=O)=CC(=O)C1=C2 RQTOOFIXOKYGAN-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 claims description 2
- 229960004448 pentamidine Drugs 0.000 claims description 2
- 229960004017 salmeterol Drugs 0.000 claims description 2
- 229960000195 terbutaline Drugs 0.000 claims description 2
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 claims 1
- 229960000676 flunisolide Drugs 0.000 claims 1
- 229960004618 prednisone Drugs 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 53
- 239000007787 solid Substances 0.000 abstract description 18
- 230000003381 solubilizing effect Effects 0.000 abstract description 10
- 239000000843 powder Substances 0.000 abstract description 8
- 230000000699 topical effect Effects 0.000 abstract description 8
- 238000002513 implantation Methods 0.000 abstract description 6
- 239000007924 injection Substances 0.000 abstract description 6
- 238000002347 injection Methods 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 146
- 229920000747 poly(lactic acid) Polymers 0.000 description 99
- 239000004626 polylactic acid Substances 0.000 description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- 239000002904 solvent Substances 0.000 description 45
- 229920001432 poly(L-lactide) Polymers 0.000 description 41
- 238000009826 distribution Methods 0.000 description 36
- 238000004821 distillation Methods 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 210000004072 lung Anatomy 0.000 description 27
- 239000011521 glass Substances 0.000 description 25
- 239000006184 cosolvent Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 238000005194 fractionation Methods 0.000 description 17
- 229960000448 lactic acid Drugs 0.000 description 17
- 238000002390 rotary evaporation Methods 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000008279 sol Substances 0.000 description 15
- 238000006065 biodegradation reaction Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000011552 falling film Substances 0.000 description 14
- 239000013580 millipore water Substances 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000010926 purge Methods 0.000 description 13
- 210000002966 serum Anatomy 0.000 description 13
- 238000004808 supercritical fluid chromatography Methods 0.000 description 13
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000000546 pharmaceutical excipient Substances 0.000 description 11
- 239000007943 implant Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- 235000011089 carbon dioxide Nutrition 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000002685 pulmonary effect Effects 0.000 description 8
- 230000000087 stabilizing effect Effects 0.000 description 8
- 102000003390 tumor necrosis factor Human genes 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229960004275 glycolic acid Drugs 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 230000007928 solubilization Effects 0.000 description 7
- 238000005063 solubilization Methods 0.000 description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 229940057282 albuterol sulfate Drugs 0.000 description 5
- BNPSSFBOAGDEEL-UHFFFAOYSA-N albuterol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1.CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 BNPSSFBOAGDEEL-UHFFFAOYSA-N 0.000 description 5
- 125000004450 alkenylene group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- YCIHPQHVWDULOY-FMZCEJRJSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC=C2[C@](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 YCIHPQHVWDULOY-FMZCEJRJSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001408 amides Chemical group 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229960003260 chlorhexidine Drugs 0.000 description 4
- 230000000593 degrading effect Effects 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 231100000824 inhalation exposure Toxicity 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
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- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- 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
- A61K9/12—Aerosols; Foams
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/593—Polyesters, e.g. PLGA or polylactide-co-glycolide
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/797,803 US6126919A (en) | 1997-02-07 | 1997-02-07 | Biocompatible compounds for pharmaceutical drug delivery systems |
| PCT/US1998/000074 WO1998034596A2 (en) | 1997-02-07 | 1998-02-04 | Biocompatible compounds for pharmaceutical drug delivery systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ336903A true NZ336903A (en) | 2001-08-31 |
Family
ID=25171845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ336903A NZ336903A (en) | 1997-02-07 | 1998-02-04 | Medicinal formulations comprising biocompatible polymers of the formula -[X-R-C(O)]- for pharmaceutical drug delivery systems |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US6126919A (enExample) |
| EP (2) | EP1014944B1 (enExample) |
| JP (1) | JP2001511179A (enExample) |
| KR (1) | KR100564130B1 (enExample) |
| CN (1) | CN1114400C (enExample) |
| AT (1) | ATE359062T1 (enExample) |
| AU (1) | AU724765B2 (enExample) |
| CA (1) | CA2279522C (enExample) |
| DE (1) | DE69837549T2 (enExample) |
| HU (1) | HUP0001914A3 (enExample) |
| IL (1) | IL130993A0 (enExample) |
| NZ (1) | NZ336903A (enExample) |
| PL (1) | PL196261B1 (enExample) |
| WO (1) | WO1998034596A2 (enExample) |
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|---|---|---|---|---|
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| US7833543B2 (en) * | 1995-06-07 | 2010-11-16 | Durect Corporation | High viscosity liquid controlled delivery system and medical or surgical device |
| GB9616237D0 (en) | 1996-08-01 | 1996-09-11 | Norton Healthcare Ltd | Aerosol formulations |
| US6126919A (en) * | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| US20010031244A1 (en) | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| US6598603B1 (en) * | 1997-12-31 | 2003-07-29 | Astra Aktiebolag | Method for treating respiratory diseases |
| SE9804001D0 (sv) * | 1998-11-23 | 1998-11-23 | Astra Ab | New process |
| DZ2947A1 (fr) | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Inhalateur à compteur de dose sous pression. |
| IT1303788B1 (it) * | 1998-11-25 | 2001-02-23 | Chiesi Farma Spa | Formulazioni di aerosol medicinali. |
| US6319521B1 (en) * | 1999-02-10 | 2001-11-20 | University Technology Corporation | Microparticles of lactide-co-glycolide copolymers and methods of making and using the same |
| JP4548623B2 (ja) * | 1999-02-24 | 2010-09-22 | 多木化学株式会社 | 生体材料 |
| HUP0201626A3 (en) * | 1999-06-04 | 2004-05-28 | Alza Corp Mountain View | Implantable gel compositions and method of manufacture |
| US6315985B1 (en) * | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| IT1313553B1 (it) | 1999-07-23 | 2002-09-09 | Chiesi Farma Spa | Formulazioni ottimizzate costituite da soluzioni di steroidi dasomministrare per inalazione. |
| EP1498089A1 (de) * | 1999-12-15 | 2005-01-19 | Zimmer GmbH | Präparat für die Reparatur von Knorpel- oder Knorpel/Knochen-Defekten in menschlichen oder tierischen Gelenken |
| US6651655B1 (en) * | 2000-01-18 | 2003-11-25 | Quadrant Technologies Limited | Inhaled vaccines |
| IT1317846B1 (it) | 2000-02-22 | 2003-07-15 | Chiesi Farma Spa | Formulazioni contenenti un farmaco anticolinergico per il trattamentodella broncopneumopatia cronica ostruttiva. |
| UA73986C2 (uk) * | 2000-05-22 | 2005-10-17 | К'Єзі Фармачеутічі С.П.А. | АЕРОЗОЛЬНА КОМПОЗИЦІЯ, ЩО МІСТИТЬ <font face="Symbol">b</font>2-АДРЕНЕРГІЧНИЙ АГОНІСТ ТРИВАЛОЇ ДІЇ, ДОЗУЮЧИЙ ІНГАЛЯТОР ПІД ТИСКОМ ТА СПОСІБ ЙОГО ЗАПОВНЕННЯ |
| KR20080053423A (ko) | 2000-07-31 | 2008-06-12 | 니코메드 댄마크 에이에스 | 코 투여용 펜타닐 조성물 |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6777400B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| AU7576001A (en) | 2000-08-05 | 2002-02-18 | Glaxo Group Ltd | 6.alpha., 9.alpha.-difluoro-17.alpha.-`(2-furanylcarboxyl) oxy]-11.beta.-hydroxy-16.alpha.-methyl-3-oxo-androst-1,4,-diene-17-carbothioic acid s-fluoromethyl ester as an anti-inflammatory agent |
| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| US6787532B2 (en) | 2000-08-05 | 2004-09-07 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivatives |
| GB0019172D0 (en) | 2000-08-05 | 2000-09-27 | Glaxo Group Ltd | Novel compounds |
| US6858593B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| DE10058829B4 (de) * | 2000-11-27 | 2004-08-26 | 3M Espe Ag | Verwendung von Polysäuren mit enger Molmassenverteilung |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| US6667344B2 (en) | 2001-04-17 | 2003-12-23 | Dey, L.P. | Bronchodilating compositions and methods |
| US20030055026A1 (en) | 2001-04-17 | 2003-03-20 | Dey L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
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| WO2002088167A1 (en) | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Anti-inflammatory 17.beta.-carbothioate ester derivatives of androstane with a cyclic ester group in position 17.alpha |
| US20030051728A1 (en) * | 2001-06-05 | 2003-03-20 | Lloyd Peter M. | Method and device for delivering a physiologically active compound |
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| US7718162B2 (en) * | 2001-12-21 | 2010-05-18 | 3M Innovative Properties Company | Medicinal aerosol compositions with a functionalized polyethyleneglycol excipient |
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-
1997
- 1997-02-07 US US08/797,803 patent/US6126919A/en not_active Expired - Lifetime
-
1998
- 1998-02-04 HU HU0001914A patent/HUP0001914A3/hu unknown
- 1998-02-04 AT AT98904525T patent/ATE359062T1/de not_active IP Right Cessation
- 1998-02-04 CA CA002279522A patent/CA2279522C/en not_active Expired - Fee Related
- 1998-02-04 EP EP98904525A patent/EP1014944B1/en not_active Expired - Lifetime
- 1998-02-04 NZ NZ336903A patent/NZ336903A/en unknown
- 1998-02-04 DE DE69837549T patent/DE69837549T2/de not_active Expired - Lifetime
- 1998-02-04 KR KR1019997007128A patent/KR100564130B1/ko not_active Expired - Fee Related
- 1998-02-04 IL IL13099398A patent/IL130993A0/xx not_active IP Right Cessation
- 1998-02-04 CN CN98802390A patent/CN1114400C/zh not_active Expired - Fee Related
- 1998-02-04 WO PCT/US1998/000074 patent/WO1998034596A2/en not_active Ceased
- 1998-02-04 AU AU62384/98A patent/AU724765B2/en not_active Ceased
- 1998-02-04 PL PL335020A patent/PL196261B1/pl not_active IP Right Cessation
- 1998-02-04 JP JP53440498A patent/JP2001511179A/ja not_active Ceased
- 1998-02-04 EP EP07105868A patent/EP1815845A3/en not_active Withdrawn
-
2000
- 2000-08-09 US US09/634,406 patent/US6416742B1/en not_active Expired - Fee Related
-
2002
- 2002-02-18 US US10/078,805 patent/US7687054B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL335020A1 (en) | 2000-03-27 |
| HUP0001914A3 (en) | 2001-12-28 |
| CA2279522C (en) | 2008-01-15 |
| DE69837549T2 (de) | 2007-12-20 |
| JP2001511179A (ja) | 2001-08-07 |
| EP1815845A2 (en) | 2007-08-08 |
| EP1014944B1 (en) | 2007-04-11 |
| KR100564130B1 (ko) | 2006-03-27 |
| IL130993A0 (en) | 2001-01-28 |
| HK1030357A1 (en) | 2001-05-04 |
| WO1998034596A3 (en) | 1998-11-05 |
| ATE359062T1 (de) | 2007-05-15 |
| EP1014944A2 (en) | 2000-07-05 |
| EP1815845A3 (en) | 2008-08-06 |
| CA2279522A1 (en) | 1998-08-13 |
| KR20000070863A (ko) | 2000-11-25 |
| PL196261B1 (pl) | 2007-12-31 |
| US7687054B2 (en) | 2010-03-30 |
| WO1998034596A2 (en) | 1998-08-13 |
| AU6238498A (en) | 1998-08-26 |
| DE69837549D1 (de) | 2007-05-24 |
| CN1246790A (zh) | 2000-03-08 |
| AU724765B2 (en) | 2000-09-28 |
| US6126919A (en) | 2000-10-03 |
| US20020164290A1 (en) | 2002-11-07 |
| CN1114400C (zh) | 2003-07-16 |
| HUP0001914A2 (hu) | 2000-10-28 |
| US6416742B1 (en) | 2002-07-09 |
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