RU2310450C2 - Новые депо-препараты для инъекций - Google Patents
Новые депо-препараты для инъекций Download PDFInfo
- Publication number
- RU2310450C2 RU2310450C2 RU2005112207/15A RU2005112207A RU2310450C2 RU 2310450 C2 RU2310450 C2 RU 2310450C2 RU 2005112207/15 A RU2005112207/15 A RU 2005112207/15A RU 2005112207 A RU2005112207 A RU 2005112207A RU 2310450 C2 RU2310450 C2 RU 2310450C2
- Authority
- RU
- Russia
- Prior art keywords
- polycaprolactones
- cyclodextrin
- ziprasidone
- depot preparation
- sbecd
- Prior art date
Links
- 239000003405 delayed action preparation Substances 0.000 title claims abstract description 50
- 238000002347 injection Methods 0.000 title claims abstract description 30
- 239000007924 injection Substances 0.000 title claims abstract description 30
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 63
- -1 polyoxypropylene Polymers 0.000 claims abstract description 35
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003814 drug Substances 0.000 claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 11
- 235000021355 Stearic acid Nutrition 0.000 claims abstract description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 10
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000008117 stearic acid Substances 0.000 claims abstract description 10
- 229920002678 cellulose Polymers 0.000 claims abstract description 9
- 239000001913 cellulose Substances 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 9
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 8
- 239000004417 polycarbonate Substances 0.000 claims abstract description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 7
- 238000011282 treatment Methods 0.000 claims abstract description 7
- 229920000954 Polyglycolide Polymers 0.000 claims abstract description 6
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims abstract description 6
- 229920001897 terpolymer Polymers 0.000 claims abstract description 6
- 229920001661 Chitosan Polymers 0.000 claims abstract description 5
- 229920002307 Dextran Polymers 0.000 claims abstract description 5
- 108010010803 Gelatin Proteins 0.000 claims abstract description 5
- 229920000615 alginic acid Polymers 0.000 claims abstract description 5
- 235000010443 alginic acid Nutrition 0.000 claims abstract description 5
- 150000002170 ethers Chemical class 0.000 claims abstract description 5
- 229920000159 gelatin Polymers 0.000 claims abstract description 5
- 239000008273 gelatin Substances 0.000 claims abstract description 5
- 235000019322 gelatine Nutrition 0.000 claims abstract description 5
- 235000011852 gelatine desserts Nutrition 0.000 claims abstract description 5
- 229920001308 poly(aminoacid) Polymers 0.000 claims abstract description 5
- 229920001444 polymaleic acid Polymers 0.000 claims abstract description 5
- 229920000056 polyoxyethylene ether Polymers 0.000 claims abstract description 5
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
- 229920002101 Chitin Polymers 0.000 claims abstract description 4
- 229920002627 poly(phosphazenes) Polymers 0.000 claims abstract description 4
- 229920006324 polyoxymethylene Polymers 0.000 claims abstract description 4
- 150000003890 succinate salts Chemical class 0.000 claims abstract description 4
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 3
- 229920001610 polycaprolactone Polymers 0.000 claims abstract 27
- 229920002635 polyurethane Polymers 0.000 claims abstract 4
- 239000004814 polyurethane Substances 0.000 claims abstract 4
- 229920002732 Polyanhydride Polymers 0.000 claims abstract 3
- 229920002614 Polyether block amide Polymers 0.000 claims abstract 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract 3
- 229930006000 Sucrose Natural products 0.000 claims abstract 3
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims abstract 3
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 claims abstract 3
- 229920000768 polyamine Polymers 0.000 claims abstract 3
- 239000000622 polydioxanone Substances 0.000 claims abstract 3
- 239000005720 sucrose Substances 0.000 claims abstract 3
- 229960000607 ziprasidone Drugs 0.000 claims description 76
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 76
- 229940097346 sulfobutylether-beta-cyclodextrin Drugs 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 17
- WLQZEFFFIUHSJB-UHFFFAOYSA-N ziprasidone mesylate trihydrate Chemical compound O.O.O.CS(O)(=O)=O.C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 WLQZEFFFIUHSJB-UHFFFAOYSA-N 0.000 claims description 17
- 229960004487 ziprasidone mesylate Drugs 0.000 claims description 13
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 7
- 238000010255 intramuscular injection Methods 0.000 claims description 6
- 239000007927 intramuscular injection Substances 0.000 claims description 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 6
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 5
- 239000006184 cosolvent Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 5
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 5
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 239000008180 pharmaceutical surfactant Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 150000004040 pyrrolidinones Chemical class 0.000 claims description 2
- 239000001797 sucrose acetate isobutyrate Substances 0.000 claims description 2
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 claims description 2
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 claims description 2
- 239000001116 FEMA 4028 Substances 0.000 claims 4
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 4
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims 4
- 229960004853 betadex Drugs 0.000 claims 4
- 239000000164 antipsychotic agent Substances 0.000 claims 3
- 229920001710 Polyorthoester Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims 1
- 239000008365 aqueous carrier Substances 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 230000002035 prolonged effect Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 2
- VNDHXHMRJVTMTK-WZVRVNPQSA-H hexasodium 4-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10-(hydroxymethyl)-15,20,25,30,35-pentakis(4-sulfonatobutoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]butane-1-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]1[C@H](O)[C@H]2O VNDHXHMRJVTMTK-WZVRVNPQSA-H 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- 229940097362 cyclodextrins Drugs 0.000 description 13
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 10
- 229920000053 polysorbate 80 Polymers 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 239000007900 aqueous suspension Substances 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 6
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000011269 treatment regimen Methods 0.000 description 5
- 238000010411 cooking Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000008227 sterile water for injection Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960002903 benzyl benzoate Drugs 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- 229940068968 polysorbate 80 Drugs 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 235000011803 sesame oil Nutrition 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000003693 atypical antipsychotic agent Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- PCWPQSDFNIFUPO-VDQKLNDWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-37,39,41,43,45,47,49-heptakis(2-hydroxyethoxy)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol Chemical compound OCCO[C@H]1[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]1O[C@@H]2CO)[C@@H](O)[C@@H]8OCCO)[C@@H](O)[C@@H]7OCCO)[C@@H](O)[C@@H]6OCCO)[C@@H](O)[C@@H]5OCCO)[C@@H](O)[C@@H]4OCCO)[C@@H](O)[C@@H]3OCCO PCWPQSDFNIFUPO-VDQKLNDWSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010012186 Delayed delivery Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- FEILLANYVHIXLR-UHFFFAOYSA-N O=Cl(C1=CC2=CC=CC=C2N1)=O Chemical class O=Cl(C1=CC2=CC=CC=C2N1)=O FEILLANYVHIXLR-UHFFFAOYSA-N 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940124604 anti-psychotic medication Drugs 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229950007655 esilate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229950006327 napsilate Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000012453 solvate 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
- 230000009885 systemic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42147302P | 2002-10-25 | 2002-10-25 | |
| US60/421,473 | 2002-10-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005112207A RU2005112207A (ru) | 2005-09-10 |
| RU2310450C2 true RU2310450C2 (ru) | 2007-11-20 |
Family
ID=32176718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005112207/15A RU2310450C2 (ru) | 2002-10-25 | 2003-10-13 | Новые депо-препараты для инъекций |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20040138237A1 (enExample) |
| EP (1) | EP1575616A2 (enExample) |
| JP (1) | JP2006514923A (enExample) |
| KR (1) | KR20050055781A (enExample) |
| CN (1) | CN1849110A (enExample) |
| AR (1) | AR041722A1 (enExample) |
| AU (1) | AU2003267788A1 (enExample) |
| BR (1) | BR0315568A (enExample) |
| CA (1) | CA2503076A1 (enExample) |
| MX (1) | MXPA05002561A (enExample) |
| NL (1) | NL1024590C2 (enExample) |
| NO (1) | NO20052463L (enExample) |
| PA (1) | PA8586201A1 (enExample) |
| PE (1) | PE20040499A1 (enExample) |
| PL (1) | PL377679A1 (enExample) |
| RU (1) | RU2310450C2 (enExample) |
| TW (1) | TW200423941A (enExample) |
| UY (1) | UY28038A1 (enExample) |
| WO (1) | WO2004037289A2 (enExample) |
| ZA (1) | ZA200501921B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080113025A1 (en) * | 1998-11-02 | 2008-05-15 | Elan Pharma International Limited | Compositions comprising nanoparticulate naproxen and controlled release hydrocodone |
| US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| EP2218448B1 (en) | 2002-12-13 | 2015-09-23 | Durect Corporation | Oral drug delivery system comprising high viscosity liquid carrier materials |
| KR20060115350A (ko) * | 2003-09-02 | 2006-11-08 | 화이자 프로덕츠 인크. | 지프라시돈의 지속 방출형 투여 형태 |
| DK2767292T3 (en) | 2004-09-17 | 2016-12-19 | Durect Corp | RENEWABLE local anesthetic COMPOSITION CONTAINING SAIB |
| EP1855651A4 (en) * | 2005-03-03 | 2011-06-15 | Elan Pharma Int Ltd | NANOPARTICLE COMPOSITIONS OF HETEROCYCLIC AMID DERIVATIVES |
| US20080305161A1 (en) * | 2005-04-13 | 2008-12-11 | Pfizer Inc | Injectable depot formulations and methods for providing sustained release of nanoparticle compositions |
| CA2603189A1 (en) * | 2005-04-13 | 2006-10-19 | Pfizer Products Inc. | Injectable depot formulations and methods for providing sustained release of poorly soluble drugs comprising nanoparticles |
| CA2605153A1 (en) * | 2005-04-13 | 2006-10-19 | Jaymin Chandrakant Shah | Injectable depot formulations and methods for providing sustained release of nanoparticle compositions |
| KR20080024206A (ko) * | 2005-06-20 | 2008-03-17 | 엘란 파마 인터내셔널 리미티드 | 아릴-헤테로시클릭 화합물을 함유하는 나노입자형 조절방출 조성물 |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| US8852638B2 (en) | 2005-09-30 | 2014-10-07 | Durect Corporation | Sustained release small molecule drug formulation |
| KR100908517B1 (ko) * | 2006-07-04 | 2009-07-20 | (주)아모레퍼시픽 | 호흡기계 약제 전달을 위한 서방형 다공성 미세입자 및 그제조 방법 |
| AU2007325918B2 (en) | 2006-11-03 | 2013-10-17 | Durect Corporation | Transdermal delivery systems comprising bupivacaine |
| EP2152315B1 (en) | 2007-05-25 | 2016-01-06 | Indivior UK Limited | Sustained delivery formulations of risperidone compounds |
| EP2067471B1 (en) * | 2007-12-06 | 2018-02-14 | Durect Corporation | Oral pharmaceutical dosage forms |
| EP2303229A1 (en) * | 2008-06-16 | 2011-04-06 | Debiopharm S.A. | Concentrated oxaliplatin solution and its method of preparation |
| US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
| GB2513060B (en) | 2010-06-08 | 2015-01-07 | Rb Pharmaceuticals Ltd | Microparticle buprenorphine suspension |
| US9272044B2 (en) | 2010-06-08 | 2016-03-01 | Indivior Uk Limited | Injectable flowable composition buprenorphine |
| CA2905131A1 (en) | 2013-03-15 | 2014-09-18 | Durect Corporation | Compositions with a rheological modifier to reduce dissolution variability |
| GB201404139D0 (en) | 2014-03-10 | 2014-04-23 | Rb Pharmaceuticals Ltd | Sustained release buprenorphine solution formulations |
| CN104688686A (zh) * | 2015-02-10 | 2015-06-10 | 万全万特制药江苏有限公司 | 一种含有齐拉西酮及其盐的脂肪乳注射剂 |
| CN109475505A (zh) | 2016-07-06 | 2019-03-15 | 度瑞公司 | 具有药物组成物、屏障层及药物层的口服剂型 |
| WO2018015915A1 (en) * | 2016-07-22 | 2018-01-25 | Cadila Healthcare Limited | A parenteral controlled release composition of an atypical antipsychotic agent |
| FR3087107A1 (fr) | 2018-10-15 | 2020-04-17 | Avent Inc. | Compositions, systèmes, kits et méthodes d'ablation neurale |
| WO2021146215A1 (en) | 2020-01-13 | 2021-07-22 | Durect Corporation | Sustained release drug delivery systems with reduced impurities and related methods |
| CA3203561A1 (en) | 2021-01-12 | 2022-07-21 | Adrian Neil Verity | Sustained release drug delivery systems and related methods |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041896A2 (en) * | 1996-05-07 | 1997-11-13 | Pfizer Inc. | Inclusion complexes of aryl-heterocyclic salts |
| WO2000018821A1 (en) * | 1998-10-01 | 2000-04-06 | Macromed, Inc. | Biodegradable low molecular weight triblock polyester polyethylene glycol copolymers having reverse thermal gelation properties |
| US6331311B1 (en) * | 1996-12-20 | 2001-12-18 | Alza Corporation | Injectable depot gel composition and method of preparing the composition |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4029782A (en) * | 1975-04-28 | 1977-06-14 | Eli Lilly And Company | Cefazolin suspension for parenteral administration |
| US4512986A (en) * | 1983-07-26 | 1985-04-23 | Research Triangle Institute | Progrestationally active steroids |
| US6117949A (en) * | 1998-10-01 | 2000-09-12 | Macromed, Inc. | Biodegradable low molecular weight triblock poly (lactide-co-glycolide) polyethylene glycol copolymers having reverse thermal gelation properties |
| AU765603C (en) * | 1998-04-14 | 2004-08-05 | General Hospital Corporation, The | Methods for treating neuropsychiatric disorders |
| IL145950A0 (en) * | 1999-05-27 | 2002-07-25 | Pfizer Prod Inc | Ziprasidone suspension |
| US6753011B2 (en) * | 2000-01-14 | 2004-06-22 | Osmotica Corp | Combined diffusion/osmotic pumping drug delivery system |
| EP1383445A4 (en) * | 2001-03-20 | 2005-04-13 | Cydex Inc | FORMULATIONS WITH PROPOFOL AND A SULFOALKYL ETHER CYCLODEXTRIN |
| EP1269994A3 (en) * | 2001-06-22 | 2003-02-12 | Pfizer Products Inc. | Pharmaceutical compositions comprising drug and concentration-enhancing polymers |
-
2003
- 2003-10-13 EP EP03748483A patent/EP1575616A2/en not_active Withdrawn
- 2003-10-13 PL PL377679A patent/PL377679A1/pl not_active Application Discontinuation
- 2003-10-13 KR KR1020057006986A patent/KR20050055781A/ko not_active Ceased
- 2003-10-13 CA CA002503076A patent/CA2503076A1/en not_active Abandoned
- 2003-10-13 AU AU2003267788A patent/AU2003267788A1/en not_active Abandoned
- 2003-10-13 CN CNA2003801019024A patent/CN1849110A/zh active Pending
- 2003-10-13 JP JP2004546264A patent/JP2006514923A/ja not_active Abandoned
- 2003-10-13 RU RU2005112207/15A patent/RU2310450C2/ru not_active IP Right Cessation
- 2003-10-13 BR BR0315568-4A patent/BR0315568A/pt not_active IP Right Cessation
- 2003-10-13 WO PCT/IB2003/004576 patent/WO2004037289A2/en not_active Ceased
- 2003-10-13 MX MXPA05002561A patent/MXPA05002561A/es unknown
- 2003-10-14 PA PA20038586201A patent/PA8586201A1/es unknown
- 2003-10-21 US US10/690,078 patent/US20040138237A1/en not_active Abandoned
- 2003-10-22 PE PE2003001071A patent/PE20040499A1/es not_active Application Discontinuation
- 2003-10-22 NL NL1024590A patent/NL1024590C2/nl not_active IP Right Cessation
- 2003-10-24 AR ARP030103894A patent/AR041722A1/es not_active Application Discontinuation
- 2003-10-24 TW TW092129568A patent/TW200423941A/zh unknown
- 2003-10-24 UY UY28038A patent/UY28038A1/es not_active Application Discontinuation
-
2005
- 2005-03-07 ZA ZA200501921A patent/ZA200501921B/xx unknown
- 2005-05-23 NO NO20052463A patent/NO20052463L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041896A2 (en) * | 1996-05-07 | 1997-11-13 | Pfizer Inc. | Inclusion complexes of aryl-heterocyclic salts |
| US6331311B1 (en) * | 1996-12-20 | 2001-12-18 | Alza Corporation | Injectable depot gel composition and method of preparing the composition |
| WO2000018821A1 (en) * | 1998-10-01 | 2000-04-06 | Macromed, Inc. | Biodegradable low molecular weight triblock polyester polyethylene glycol copolymers having reverse thermal gelation properties |
Non-Patent Citations (1)
| Title |
|---|
| DANIEL D.G., POTKIN S.G. "Intramuscular (IM) ziprasidone 20 mg is effective in reducing acute agitation associated with psychosis: a double-blind, randomized trial.", Psychopharmacology (Berl). 2001 May; 155(2): 128-34. * |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA05002561A (es) | 2005-05-05 |
| ZA200501921B (en) | 2006-10-25 |
| TW200423941A (en) | 2004-11-16 |
| NL1024590C2 (nl) | 2005-05-23 |
| US20040138237A1 (en) | 2004-07-15 |
| WO2004037289A3 (en) | 2005-12-01 |
| AU2003267788A1 (en) | 2004-05-13 |
| RU2005112207A (ru) | 2005-09-10 |
| PE20040499A1 (es) | 2004-08-18 |
| PL377679A1 (pl) | 2006-02-06 |
| KR20050055781A (ko) | 2005-06-13 |
| CA2503076A1 (en) | 2004-05-06 |
| NL1024590A1 (nl) | 2004-04-27 |
| AR041722A1 (es) | 2005-05-26 |
| UY28038A1 (es) | 2004-05-31 |
| NO20052463L (no) | 2005-05-23 |
| PA8586201A1 (es) | 2004-09-16 |
| JP2006514923A (ja) | 2006-05-18 |
| BR0315568A (pt) | 2005-08-23 |
| CN1849110A (zh) | 2006-10-18 |
| WO2004037289A2 (en) | 2004-05-06 |
| EP1575616A2 (en) | 2005-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL1024590C2 (nl) | Nieuwe injecteerbare depotpreparaten. | |
| KR100917809B1 (ko) | 우수한 저장안정성을 갖는 도세탁셀 함유 주사제 조성물 | |
| CN100335047C (zh) | 阿立哌唑复合制剂和方法 | |
| RU2292207C2 (ru) | Депо-препараты арилгетероциклических активных веществ в виде суспензии | |
| KR101731155B1 (ko) | 안정화된 보리코나졸 조성물 | |
| US20050085446A1 (en) | Fluoroquinolone formulations and methods of making and using the same | |
| JP2009523771A (ja) | 凍結乾燥した個体状タキサン類組成物、前記組成物を生成する方法、前記組成物の医薬調剤、前記組成物の調剤用キット。 | |
| CN107261152A (zh) | 包含环糊精和疏水性药物的可注射药物组合物的防腐方法 | |
| CN101534864A (zh) | 包含匹莫苯与环糊精的复合物的液体制剂 | |
| CN101868232B (zh) | 包含紫杉烷衍生物的具有改进的重构时间的冻干药物组合物及其制备方法 | |
| US20070049552A1 (en) | Fluoroquinolone formulations and methods of making and using the same | |
| WO2012013116A1 (zh) | 含氨基酸稳定剂的替莫唑胺药物组合物及其制备方法 | |
| JP2007519702A (ja) | ニューロキニン受容体拮抗薬及びシクロデキストリンからなる医薬組成物、ならびに注射部位の耐容性を改善するための方法 | |
| US20040202687A1 (en) | Ciprofloxacin formulations and methods of making and using the same | |
| HK1092054A (en) | Novel injectable depot formulations | |
| HK1084321A (en) | Depot formulations of arylheterocyclic active agents in the form of a suspension | |
| WO2011101865A2 (en) | Stable pharmaceutical compositions of clopidogrel for parenteral delivery |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20081014 |