DE69819721T2 - Zusammensetzung mit erhöhter lagerstabilität enthaltend cyclodextrin und wirkstoffe oder wirkstoff-vorstufen, die in wasserunlösliche komponenten zersetzt werden - Google Patents
Zusammensetzung mit erhöhter lagerstabilität enthaltend cyclodextrin und wirkstoffe oder wirkstoff-vorstufen, die in wasserunlösliche komponenten zersetzt werden Download PDFInfo
- Publication number
- DE69819721T2 DE69819721T2 DE69819721T DE69819721T DE69819721T2 DE 69819721 T2 DE69819721 T2 DE 69819721T2 DE 69819721 T DE69819721 T DE 69819721T DE 69819721 T DE69819721 T DE 69819721T DE 69819721 T2 DE69819721 T2 DE 69819721T2
- Authority
- DE
- Germany
- Prior art keywords
- cyclodextrin
- prodrug
- pharmaceutical preparation
- drug
- water
- 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
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 104
- 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 title claims abstract description 65
- 238000003860 storage Methods 0.000 title claims description 18
- 239000013543 active substance Substances 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 title description 3
- 239000000126 substance Substances 0.000 title description 3
- 239000000651 prodrug Substances 0.000 claims abstract description 73
- 229940002612 prodrug Drugs 0.000 claims abstract description 73
- 229940097362 cyclodextrins Drugs 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims description 90
- 229940079593 drug Drugs 0.000 claims description 87
- 229960000693 fosphenytoin Drugs 0.000 claims description 80
- 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 description 77
- 238000000354 decomposition reaction Methods 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 42
- 239000000047 product Substances 0.000 claims description 38
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 23
- -1 sulfoalkyl ether Chemical compound 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000008365 aqueous carrier Substances 0.000 claims description 5
- 239000007857 degradation product Substances 0.000 claims description 5
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 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 claims description 3
- 229960005091 chloramphenicol Drugs 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition 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 70
- 229960002036 phenytoin Drugs 0.000 description 70
- 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
- 230000000694 effects Effects 0.000 description 15
- 230000015556 catabolic process Effects 0.000 description 10
- 238000006731 degradation reaction Methods 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 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 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009918 complex formation Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000013618 particulate matter Substances 0.000 description 3
- 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
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 238000002474 experimental method 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
- 238000004128 high performance liquid chromatography Methods 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
- 230000006911 nucleation Effects 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 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 2
- 238000010591 solubility diagram Methods 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- FEJIIZAOQRTGPC-UHFFFAOYSA-N 5,5-diphenylimidazolidin-4-one Chemical compound O=C1NCNC1(C=1C=CC=CC=1)C1=CC=CC=C1 FEJIIZAOQRTGPC-UHFFFAOYSA-N 0.000 description 1
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound 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)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-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 group 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
- KRWMERLEINMZFT-UHFFFAOYSA-N O6-benzylguanine Chemical compound C=12NC=NC2=NC(N)=NC=1OCC1=CC=CC=C1 KRWMERLEINMZFT-UHFFFAOYSA-N 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
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 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
- 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 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000000593 degrading 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
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 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
- 239000012535 impurity Substances 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 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
- 230000009257 reactivity Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—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 | |
| US50909P | 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69819721D1 DE69819721D1 (de) | 2003-12-18 |
| DE69819721T2 true DE69819721T2 (de) | 2004-09-23 |
Family
ID=21968241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69819721T Expired - Lifetime DE69819721T2 (de) | 1997-06-13 | 1998-06-12 | Zusammensetzung mit erhöhter lagerstabilität enthaltend cyclodextrin und wirkstoffe oder wirkstoff-vorstufen, die in wasserunlösliche komponenten zersetzt werden |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6133248A (https=) |
| EP (1) | EP0986403B1 (https=) |
| JP (1) | JP4439596B2 (https=) |
| AT (1) | ATE253941T1 (https=) |
| AU (1) | AU750207B2 (https=) |
| DE (1) | DE69819721T2 (https=) |
| ES (1) | ES2210769T3 (https=) |
| PT (1) | PT986403E (https=) |
| WO (1) | WO1998056422A1 (https=) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8980290B2 (en) | 2000-08-03 | 2015-03-17 | Antares Pharma Ipl Ag | Transdermal compositions for anticholinergic agents |
| US20040198706A1 (en) * | 2003-03-11 | 2004-10-07 | Carrara Dario Norberto R. | Methods and formulations for transdermal or transmucosal application of active agents |
| ATE355854T1 (de) * | 2000-08-03 | 2007-03-15 | Antares Pharma Ipl Ag | Neue zusammensetzung zur transdermalen und/oder transmukosalen wirkstoffanwendung mit geeignetem therapeutischen spiegel |
| US7198801B2 (en) | 2000-08-03 | 2007-04-03 | Antares Pharma Ipl Ag | Formulations for transdermal or transmucosal application |
| 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 |
| PE20020578A1 (es) | 2000-10-10 | 2002-08-14 | Upjohn Co | Una composicion 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 |
| JP2004522803A (ja) * | 2001-06-29 | 2004-07-29 | マキシゲン・エイピーエス | インターフェロン製剤 |
| US7141540B2 (en) * | 2001-11-30 | 2006-11-28 | Genta Salus Llc | Cyclodextrin grafted biocompatible amphilphilic polymer and methods of preparation and use thereof |
| ES2745068T3 (es) * | 2001-12-20 | 2020-02-27 | Merck Sharp & Dohme | Composiciones de SYN3 y métodos |
| BR0307898A (pt) * | 2002-02-22 | 2004-12-07 | Pharmacia Corp | Formulações de droga antibiótica oftálmica contendo um composto de ciclodextrina e cloreto de cetil piridìnio |
| EP1476135A1 (en) * | 2002-02-22 | 2004-11-17 | Pharmacia Corporation | Ophthalmic formulation with gum system |
| DK1670433T3 (da) | 2003-10-10 | 2012-03-12 | Ferring Bv | Transdermal farmaceutisk formulering til mindskelse af hudrester |
| WO2005105827A2 (en) | 2004-04-15 | 2005-11-10 | Proteolix, Inc. | Compounds for proteasome enzyme inhibition |
| US8198270B2 (en) * | 2004-04-15 | 2012-06-12 | Onyx Therapeutics, Inc. | Compounds for proteasome enzyme inhibition |
| US8088741B2 (en) * | 2004-05-10 | 2012-01-03 | Onyx Therapeutics, Inc. | Compounds for enzyme inhibition |
| HUE027850T2 (en) * | 2004-12-07 | 2016-11-28 | Onyx Therapeutics Inc | Preparation for proteasome inhibition |
| WO2006125642A1 (en) | 2005-05-27 | 2006-11-30 | Antares Pharma Ipl Ag | Methods and apparatus for transdermal or transmucosal application of testosterone |
| RU2453556C2 (ru) | 2005-11-09 | 2012-06-20 | Протеоликс, Инк. | Соединения для ингибирования фермента |
| WO2007059507A2 (en) * | 2005-11-15 | 2007-05-24 | Baxter International, Inc. | Compositions comprising lipoxygenase inhibitors and cyclodextrin |
| US20070135586A1 (en) * | 2005-12-09 | 2007-06-14 | Shreyas Chakravarti | Polyamide blend compositions formed article and process thereof |
| CA2646667C (en) | 2006-04-21 | 2014-03-11 | Antares Pharma Ipl Ag | Methods of treating hot flashes with formulations for transdermal or transmucosal application |
| RU2450016C2 (ru) | 2006-06-19 | 2012-05-10 | Протеоликс, Инк. | Пептидные эпоксикетоны для ингибирования протеасомы |
| EP2061458B1 (en) * | 2006-09-15 | 2014-12-10 | Regents of the University of Minnesota | Topiramate compositions and methods for their use |
| US20090239942A1 (en) | 2006-09-15 | 2009-09-24 | Cloyd James C | Topiramate Compositions and Methods of Making and Using the Same |
| CN101686681B (zh) | 2007-04-27 | 2015-04-01 | 锡德克斯药物公司 | 包含氯吡格雷和磺基烷基醚环糊精的制剂和其使用方法 |
| WO2009018326A2 (en) * | 2007-07-31 | 2009-02-05 | Limerick Biopharma, Inc. | Soluble pyrone analogs methods and compositions |
| KR20170040374A (ko) | 2007-10-04 | 2017-04-12 | 오닉스 세라퓨틱스, 인크. | 결정형 펩티드 에폭시 케톤 프로테아제 저해제 및 아미노산 케토-에폭시드의 합성 |
| US7635773B2 (en) | 2008-04-28 | 2009-12-22 | Cydex Pharmaceuticals, Inc. | Sulfoalkyl ether cyclodextrin compositions |
| CA2762321A1 (en) * | 2008-05-19 | 2009-11-26 | Texcontor Etablissement | Fosphenytoin composition |
| AU2009308516B2 (en) | 2008-10-21 | 2016-08-25 | Onyx Therapeutics, Inc. | Combination therapy with peptide epoxyketones |
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| 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 |
| KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) * | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| 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 WO PCT/US1998/011596 patent/WO1998056422A1/en not_active Ceased
- 1998-06-12 AU AU80591/98A patent/AU750207B2/en not_active Expired
- 1998-06-12 US US09/096,747 patent/US6133248A/en not_active Expired - Lifetime
- 1998-06-12 AT AT98928901T patent/ATE253941T1/de active
- 1998-06-12 ES ES98928901T patent/ES2210769T3/es not_active Expired - Lifetime
- 1998-06-12 EP EP98928901A patent/EP0986403B1/en not_active Expired - Lifetime
- 1998-06-12 JP JP50289599A patent/JP4439596B2/ja not_active Expired - Lifetime
- 1998-06-12 DE DE69819721T patent/DE69819721T2/de not_active Expired - Lifetime
- 1998-06-12 PT PT98928901T patent/PT986403E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69819721D1 (de) | 2003-12-18 |
| US6133248A (en) | 2000-10-17 |
| EP0986403B1 (en) | 2003-11-12 |
| WO1998056422A1 (en) | 1998-12-17 |
| AU8059198A (en) | 1998-12-30 |
| ES2210769T3 (es) | 2004-07-01 |
| EP0986403A1 (en) | 2000-03-22 |
| AU750207B2 (en) | 2002-07-11 |
| PT986403E (pt) | 2004-04-30 |
| JP4439596B2 (ja) | 2010-03-24 |
| ATE253941T1 (de) | 2003-11-15 |
| JP2002511861A (ja) | 2002-04-16 |
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