JP4439596B2 - 長期の貯蔵寿命を有する、極性薬物又は極性プロドラッグを含有する医薬組成物、及びその製造方法 - Google Patents
長期の貯蔵寿命を有する、極性薬物又は極性プロドラッグを含有する医薬組成物、及びその製造方法 Download PDFInfo
- Publication number
- JP4439596B2 JP4439596B2 JP50289599A JP50289599A JP4439596B2 JP 4439596 B2 JP4439596 B2 JP 4439596B2 JP 50289599 A JP50289599 A JP 50289599A JP 50289599 A JP50289599 A JP 50289599A JP 4439596 B2 JP4439596 B2 JP 4439596B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphenytoin
- molar amount
- pharmaceutical composition
- cyclodextrin
- less
- 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 - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 43
- 239000000651 prodrug Substances 0.000 title abstract description 66
- 229940002612 prodrug Drugs 0.000 title abstract description 66
- 239000003814 drug Substances 0.000 title description 81
- 229940079593 drug Drugs 0.000 title description 80
- 238000004519 manufacturing process Methods 0.000 title description 21
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 103
- 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 83
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 38
- 239000007857 degradation product Substances 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 5
- 239000008365 aqueous carrier Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000004964 sulfoalkyl group Chemical group 0.000 claims 9
- XWLUWCNOOVRFPX-UHFFFAOYSA-N Fosphenytoin Chemical compound O=C1N(COP(O)(=O)O)C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 XWLUWCNOOVRFPX-UHFFFAOYSA-N 0.000 claims 6
- 229960000693 fosphenytoin Drugs 0.000 claims 6
- 238000004108 freeze drying Methods 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 229940102223 injectable solution Drugs 0.000 claims 1
- 229940097362 cyclodextrins Drugs 0.000 abstract description 18
- 239000013543 active substance Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 81
- 229960002036 phenytoin Drugs 0.000 description 81
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 description 54
- 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 description 23
- 230000015556 catabolic process Effects 0.000 description 15
- 238000006731 degradation reaction Methods 0.000 description 15
- 230000000694 effects Effects 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 9
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000004683 dihydrates Chemical class 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000003708 ampul Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 sulfoalkyl ether Chemical compound 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-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)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 HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 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 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229960004584 methylprednisolone Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000010587 phase diagram Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XWNJMSJGJFSGRY-UHFFFAOYSA-N 2-(benzylamino)-3,7-dihydropurin-6-one Chemical compound N1C=2N=CNC=2C(=O)N=C1NCC1=CC=CC=C1 XWNJMSJGJFSGRY-UHFFFAOYSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- WHGYBXFWUBPSRW-UHFFFAOYSA-N Cycloheptaamylose Natural products O1C(C(C2O)O)C(CO)OC2OC(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 WHGYBXFWUBPSRW-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical class NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 241000178960 Paenibacillus macerans Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930092411 Swietenocoumarin D Natural products 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960002790 phenytoin sodium Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960002800 prednisolone acetate Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- FJPYVLNWWICYDW-UHFFFAOYSA-M sodium;5,5-diphenylimidazolidin-1-ide-2,4-dione Chemical compound [Na+].O=C1[N-]C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FJPYVLNWWICYDW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010591 solubility diagram Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Images
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
- A61K47/36—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5090997P | 1997-06-13 | 1997-06-13 | |
| US60/050,909 | 1997-06-13 | ||
| PCT/US1998/011596 WO1998056422A1 (en) | 1997-06-13 | 1998-06-12 | Polar drug or prodrug compositions with extended shelf-life storage and a method of making thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002511861A JP2002511861A (ja) | 2002-04-16 |
| JP2002511861A5 JP2002511861A5 (enExample) | 2005-12-02 |
| JP4439596B2 true JP4439596B2 (ja) | 2010-03-24 |
Family
ID=21968241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50289599A Expired - Lifetime JP4439596B2 (ja) | 1997-06-13 | 1998-06-12 | 長期の貯蔵寿命を有する、極性薬物又は極性プロドラッグを含有する医薬組成物、及びその製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6133248A (enExample) |
| EP (1) | EP0986403B1 (enExample) |
| JP (1) | JP4439596B2 (enExample) |
| AT (1) | ATE253941T1 (enExample) |
| AU (1) | AU750207B2 (enExample) |
| DE (1) | DE69819721T2 (enExample) |
| ES (1) | ES2210769T3 (enExample) |
| PT (1) | PT986403E (enExample) |
| WO (1) | WO1998056422A1 (enExample) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002011768A1 (en) * | 2000-08-03 | 2002-02-14 | Antares Pharma Ipl Ag | Novel composition for transdermal and/or transmucosal administration of active compounds that ensures adequate therapeutic levels |
| US20040198706A1 (en) * | 2003-03-11 | 2004-10-07 | Carrara Dario Norberto R. | Methods and formulations for transdermal or transmucosal application of active agents |
| US7198801B2 (en) | 2000-08-03 | 2007-04-03 | Antares Pharma Ipl Ag | Formulations for transdermal or transmucosal application |
| US8980290B2 (en) | 2000-08-03 | 2015-03-17 | Antares Pharma Ipl Ag | Transdermal compositions for anticholinergic agents |
| PE20020300A1 (es) * | 2000-08-22 | 2002-05-10 | Pharmacia Corp | Composicion de solucion de un farmaco antibiotico a base de oxazolidinona con mejoramiento de la carga de farmaco |
| AR031135A1 (es) | 2000-10-10 | 2003-09-10 | Upjohn Co | Composiciones de antibiotico topico para el tratamiento de infecciones oculares |
| US6566556B2 (en) * | 2000-12-19 | 2003-05-20 | Nippon Shokubai Co., Ltd. | Method for production of alkanolamine and apparatus therefor |
| WO2003002152A2 (en) * | 2001-06-29 | 2003-01-09 | Maxygen Aps | Stabilized formulations of interferons with sulfoalkyl ether cyclodextrins |
| US7141540B2 (en) * | 2001-11-30 | 2006-11-28 | Genta Salus Llc | Cyclodextrin grafted biocompatible amphilphilic polymer and methods of preparation and use thereof |
| US20030170216A1 (en) * | 2001-12-20 | 2003-09-11 | Schering-Plough Corporation | SYN3 compositions and methods |
| WO2003072081A1 (en) * | 2002-02-22 | 2003-09-04 | Pharmacia Corporation | Ophthalmic formulation with gum system |
| WO2003072141A1 (en) * | 2002-02-22 | 2003-09-04 | Pharmacia Corporation | Ophthalmic antibiotic drug formulations containing a cyclodextrin compound and cetyl pyridinium chloride |
| ATE534373T1 (de) | 2003-10-10 | 2011-12-15 | Antares Pharma Ipl Ag | Transdermale pharmazeutische formulierung zur minimierung von rückständen auf der haut |
| SG185306A1 (en) | 2004-04-15 | 2012-11-29 | Onyx Therapeutics Inc | Compounds for proteasome enzyme inhibition |
| US8198270B2 (en) * | 2004-04-15 | 2012-06-12 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| EP2030981B1 (en) * | 2004-05-10 | 2014-07-09 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| ES2408216T3 (es) * | 2004-12-07 | 2013-06-19 | Onyx Therapeutics, Inc. | Composición para la inhibición del proteasoma |
| WO2007124250A2 (en) | 2006-04-21 | 2007-11-01 | Antares Pharma Ipl Ag | Methods of treating hot flashes with formulations for transdermal or transmucosal application |
| WO2006125642A1 (en) | 2005-05-27 | 2006-11-30 | Antares Pharma Ipl Ag | Methods and apparatus for transdermal or transmucosal application of testosterone |
| ES2415756T3 (es) | 2005-11-09 | 2013-07-26 | Onyx Therapeutics, Inc. | Compuestos para la inhibición de enzimas |
| AU2006315169A1 (en) * | 2005-11-15 | 2007-05-24 | Baxter Healthcare S.A. | Compositions comprising lipoxygenase inhibitors and cyclodextrin |
| US20070135586A1 (en) * | 2005-12-09 | 2007-06-14 | Shreyas Chakravarti | Polyamide blend compositions formed article and process thereof |
| ES2415632T3 (es) | 2006-06-19 | 2013-07-26 | Onyx Therapeutics, Inc. | Epoxicetonas peptídicas para la inhibición del proteosoma |
| US20090239942A1 (en) * | 2006-09-15 | 2009-09-24 | Cloyd James C | Topiramate Compositions and Methods of Making and Using the Same |
| DK2061458T3 (en) * | 2006-09-15 | 2015-03-09 | Univ Minnesota | Topiramate compositions and methods for their use |
| CA2685331C (en) | 2007-04-27 | 2016-07-05 | Cydex Pharmaceuticals, Inc. | Formulations containing clopidogrel and sulfoalkyl ether cyclodextrin and methods of use |
| WO2009018326A2 (en) * | 2007-07-31 | 2009-02-05 | Limerick Biopharma, Inc. | Soluble pyrone analogs methods and compositions |
| EP2207791B2 (en) | 2007-10-04 | 2019-08-07 | Onyx Therapeutics, Inc. | Crystalline peptide epoxy ketone protease inhibitors and the synthesis of amino acid keto-epoxides |
| US7635773B2 (en) | 2008-04-28 | 2009-12-22 | Cydex Pharmaceuticals, Inc. | Sulfoalkyl ether cyclodextrin compositions |
| ES2378373T3 (es) * | 2008-05-19 | 2012-04-11 | Texcontor Etablissement | Composición de fosfenitoína. |
| EA024364B1 (ru) | 2008-10-21 | 2016-09-30 | Оникс Терапьютикс, Инк. | Способ лечения множественной миеломы |
| US10463677B2 (en) | 2008-11-07 | 2019-11-05 | Cydex Pharmaceuticals, Inc. | Composition containing sulfoalkyl ether cyclodextrin and latanoprost |
| TWI504598B (zh) | 2009-03-20 | 2015-10-21 | Onyx Therapeutics Inc | 結晶性三肽環氧酮蛋白酶抑制劑 |
| KR101912709B1 (ko) | 2009-05-13 | 2018-10-30 | 사이덱스 파마슈티칼스, 인크. | 프라수그렐 및 사이클로덱스트린 유도체를 포함하는 약학 조성물 및 그의 제조 및 사용 방법 |
| US11020363B2 (en) | 2009-05-29 | 2021-06-01 | Cydex Pharmaceuticals, Inc. | Injectable nitrogen mustard compositions comprising a cyclodextrin derivative and methods of making and using the same |
| EP2434886B1 (en) | 2009-05-29 | 2019-10-16 | CyDex Pharmaceuticals, Inc. | Injectable melphalan compositions comprising a cyclodextrin derivative and methods of making and using the same |
| HUE033442T2 (en) | 2009-06-25 | 2017-11-28 | Alkermes Pharma Ireland Ltd | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| EP2445343B1 (en) | 2009-06-25 | 2021-08-04 | Alkermes Pharma Ireland Limited | Prodrugs of nh-acidic compounds |
| WO2011060179A1 (en) | 2009-11-13 | 2011-05-19 | Onyx Therapeutics, Inc | Use of peptide epoxyketones for metastasis suppression |
| EP2542238B1 (en) | 2010-03-01 | 2015-08-12 | Onyx Therapeutics, Inc. | Compounds for immunoproteasome inhibition |
| BR112012025264A2 (pt) | 2010-04-07 | 2019-09-24 | Onyx Therapeutics Inc | inibidor de imunoproteassoma de e´poxicetona peptídica cristalina. |
| JP5848761B2 (ja) | 2010-06-24 | 2016-01-27 | アルカーメス ファーマ アイルランド リミテッド | Ｎｈ酸性化合物のプロドラッグ：エステル、カルボネート、カルバメートおよびホスホネートの誘導体 |
| DE102011011028A1 (de) * | 2011-02-11 | 2012-08-16 | Ditter Plastic Gmbh + Co. Kg | Frontplatte mit darin eingespritztem Lichtleiter |
| EP3156056B1 (en) | 2011-03-18 | 2023-12-06 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| EP2758052B9 (en) | 2011-09-18 | 2019-03-27 | Euro-Celtique S.A. | Pharmaceutical composition comprising an HDAC inhibitor and a cyclopolysaccharide |
| JP5952912B2 (ja) | 2011-12-15 | 2016-07-13 | アルカーメス ファーマ アイルランド リミテッド | 二級アミン化合物のプロドラッグ |
| AR092790A1 (es) | 2012-02-01 | 2015-05-06 | Euro Celtique Sa | Derivados bencimidazolicos del acido hidroxamico |
| PT3702374T (pt) | 2012-02-15 | 2022-06-23 | Cydex Pharmaceuticals Inc | Processo de fabrico para derivados de ciclodextrina |
| CN110066351B (zh) | 2012-02-28 | 2022-06-14 | 锡德克斯药物公司 | 烷基化环糊精组合物及其制备和使用方法 |
| AU2013235523B9 (en) | 2012-03-19 | 2018-01-04 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising glycerol esters |
| CA2867121C (en) | 2012-03-19 | 2021-05-25 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| AU2013235526B2 (en) | 2012-03-19 | 2017-11-30 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| UY34897A (es) | 2012-07-09 | 2014-01-31 | Onyx Therapeutics Inc | Profarmacos de inhibidores peptidicos de expoxi cetona proteasa |
| ES2792149T3 (es) | 2012-09-19 | 2020-11-10 | Alkermes Pharma Ireland Ltd | Composiciones farmacéuticas que tienen estabilidad de almacenamiento mejorada |
| JP6557144B2 (ja) | 2012-10-22 | 2019-08-07 | サイデックス・ファーマシューティカルズ・インコーポレイテッド | アルキル化シクロデキストリン組成物ならびにその調製方法および使用方法 |
| AU2015231278B2 (en) | 2014-03-20 | 2020-01-23 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| GB201409471D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| GB201409485D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| GB201409488D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| FI3183295T3 (fi) | 2014-08-22 | 2023-09-25 | Cydex Pharmaceuticals Inc | Fraktioidut alkyloidut syklodekstriinikoostumukset ja menetelmät niiden valmistamiseksi ja käyttämiseksi |
| GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| CA3040155C (en) | 2016-10-11 | 2024-01-16 | Euro-Celtique S.A. | Compound for use in the treatment of hodgkin lymphoma |
| GB201709402D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating t-pll |
| GB201709405D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating ovarian cancer |
| GB201709406D0 (en) | 2017-06-13 | 2017-07-26 | Euro-Cletique S A | Compounds for treating TNBC |
| GB201709403D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating sarcoma |
| CA3092335A1 (en) | 2018-03-05 | 2019-09-12 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| JP2022522928A (ja) | 2018-12-18 | 2022-04-21 | ムンディファーマ・インターナショナル・コーポレーション・リミテッド | 多発性骨髄腫を治療するための化合物 |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
| CN110279664B (zh) * | 2019-07-30 | 2021-09-03 | 四川农业大学 | 一种氟苯尼考包合物冻干粉针剂及其制备方法 |
| EP4010031A1 (en) | 2019-08-06 | 2022-06-15 | L.E.A.F Holdings Group LLC | Processes of preparing polyglutamated antifolates and uses of their compositions |
| JP2023551145A (ja) | 2020-11-18 | 2023-12-07 | ベクソン バイオメディカル，インク． | 医薬化合物の錯化剤塩製剤 |
| CN118161457A (zh) * | 2020-12-04 | 2024-06-11 | 四川科瑞德制药股份有限公司 | 磷苯妥英钠固体组合物、冻干方法、及其用途 |
| AU2020480182B2 (en) | 2020-12-04 | 2025-02-27 | Sichuan Credit Pharmaceutical Co., Ltd | Fosphenytoin sodium solid composition, lyophilization method, and use of fosphenytoin sodium solid composition |
| EP4525916A1 (en) * | 2022-05-18 | 2025-03-26 | Bexson Biomedical, Inc. | Complexing agent salt formulations of pharmaceutical compounds at low stoichiometric ratios |
| WO2024231293A1 (en) | 2023-05-05 | 2024-11-14 | Euro-Celtique S.A. | Combinations for treating cancer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191101B (en) * | 1983-02-14 | 1987-01-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing water-soluble cyclodextrin polymers substituted with ionic groups |
| US4616008A (en) * | 1984-05-02 | 1986-10-07 | Takeda Chemical Industries, Ltd. | Antibacterial solid composition for oral administration |
| JPS61165322A (ja) * | 1985-01-14 | 1986-07-26 | Microbial Chem Res Found | スパガリン類の注射用凍結乾燥製剤 |
| US4728509A (en) * | 1985-08-19 | 1988-03-01 | Takeda Chemical Industries, Ltd. | Aqueous liquid preparation |
| US4925860A (en) * | 1987-08-05 | 1990-05-15 | E. I. Du Pont De Nemours And Company | Stable pharmaceutical composition of 3-(hydroxymethyl)-5,5-diphenylhydantoin disodium phosphate ester |
| DE3938227C1 (en) * | 1989-11-17 | 1991-05-02 | Dolorgiet Gmbh & Co Kg, 5205 St Augustin, De | Oral antiinflammatory and analgetic pharmaceutical compsn. - comprises magnesium ibuprofen dissolved in mixt. of water, propane-1,2-diol and glycerol |
| US5376645A (en) * | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5324718A (en) * | 1992-07-14 | 1994-06-28 | Thorsteinn Loftsson | Cyclodextrin/drug complexation |
| ES2118673T3 (es) * | 1996-10-29 | 2001-04-16 | Staroil Ltd | Composiciones solubles en la boca que contienen n-acetilcisteina y ciclodextrina. |
-
1998
- 1998-06-12 PT PT98928901T patent/PT986403E/pt unknown
- 1998-06-12 ES ES98928901T patent/ES2210769T3/es not_active Expired - Lifetime
- 1998-06-12 AT AT98928901T patent/ATE253941T1/de active
- 1998-06-12 JP JP50289599A patent/JP4439596B2/ja not_active Expired - Lifetime
- 1998-06-12 US US09/096,747 patent/US6133248A/en not_active Expired - Lifetime
- 1998-06-12 DE DE69819721T patent/DE69819721T2/de not_active Expired - Lifetime
- 1998-06-12 EP EP98928901A patent/EP0986403B1/en not_active Expired - Lifetime
- 1998-06-12 AU AU80591/98A patent/AU750207B2/en not_active Expired
- 1998-06-12 WO PCT/US1998/011596 patent/WO1998056422A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU750207B2 (en) | 2002-07-11 |
| EP0986403A1 (en) | 2000-03-22 |
| US6133248A (en) | 2000-10-17 |
| ES2210769T3 (es) | 2004-07-01 |
| EP0986403B1 (en) | 2003-11-12 |
| DE69819721T2 (de) | 2004-09-23 |
| PT986403E (pt) | 2004-04-30 |
| DE69819721D1 (de) | 2003-12-18 |
| JP2002511861A (ja) | 2002-04-16 |
| WO1998056422A1 (en) | 1998-12-17 |
| ATE253941T1 (de) | 2003-11-15 |
| AU8059198A (en) | 1998-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4439596B2 (ja) | 長期の貯蔵寿命を有する、極性薬物又は極性プロドラッグを含有する医薬組成物、及びその製造方法 | |
| Stella et al. | Cyclodextrins: their future in drug formulation and delivery | |
| EP0620828B1 (en) | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof | |
| Mosher et al. | Complexation and cyclodextrins | |
| US5856359A (en) | Thyroxine/cyclodextrin complexes and pharmaceutical compositions containing the same | |
| JP2722277B2 (ja) | 水溶解性の高いシクロデキストリン誘導体組成物及びその用途 | |
| KR100349754B1 (ko) | 제약조성물 | |
| WO2002006349A1 (en) | Gel compositions containing metronidazole | |
| EP1004318A2 (en) | Cyclodextrin composition | |
| WO2004087043A2 (en) | Stable ophthalmic formulation containing an antibiotic and a corticosteroid | |
| KR20030068203A (ko) | 사이클로덱스트린 제제 | |
| JP3007312B2 (ja) | 包接複合体を製造するための塩の選別法 | |
| Ramos-Martínez et al. | Use of cyclodextrins as excipients in pharmaceutical products: why not in extemporaneous preparations? | |
| Narisawa et al. | Increased shelf‐life of fosphenytoin: Solubilization of a degradant, phenytoin, through complexation with (SBE) 7m‐β‐CD | |
| JP3597239B2 (ja) | 安定な点眼剤 | |
| US7259153B2 (en) | Drug formulation and delivery using crystalline methylated cyclodextrins | |
| US20030068340A1 (en) | Parenteral formulations of 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-urea | |
| EP2994109B1 (en) | Aqueous ophthalmic formulations based on azithromycin | |
| JP2805539B2 (ja) | ポリ―γ―シクロデキストリン包接化合物 | |
| KUM et al. | THE CYCLODEXTRINS: A REVIEW |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050404 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050404 |
|
| RD07 | Notification of extinguishment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7427 Effective date: 20070501 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20081125 |
|
| A72 | Notification of change in name of applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20090114 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090224 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090413 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090324 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090511 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090423 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090608 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090522 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090707 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091006 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20091208 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100106 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130115 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130115 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |