DE19505263A1 - Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten - Google Patents
Verfahren zur Reinigung von wasserlöslichen CyclodextrinderivatenInfo
- Publication number
- DE19505263A1 DE19505263A1 DE19505263A DE19505263A DE19505263A1 DE 19505263 A1 DE19505263 A1 DE 19505263A1 DE 19505263 A DE19505263 A DE 19505263A DE 19505263 A DE19505263 A DE 19505263A DE 19505263 A1 DE19505263 A1 DE 19505263A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclodextrin
- reverse osmosis
- water
- solution
- purification
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000000746 purification Methods 0.000 title claims description 17
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class 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 description 13
- 238000001223 reverse osmosis Methods 0.000 claims description 39
- 239000012528 membrane Substances 0.000 claims description 38
- 229920000858 Cyclodextrin Polymers 0.000 claims description 23
- 238000000926 separation method Methods 0.000 claims description 11
- 238000009792 diffusion process Methods 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 235000002639 sodium chloride Nutrition 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000008186 active pharmaceutical agent Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 17
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 15
- 230000033228 biological regulation Effects 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 238000000108 ultra-filtration Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 238000009295 crossflow filtration Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 239000012466 permeate Substances 0.000 description 11
- 239000012465 retentate Substances 0.000 description 11
- 239000001116 FEMA 4028 Substances 0.000 description 10
- 229960004853 betadex Drugs 0.000 description 10
- 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 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- YZOUYRAONFXZSI-SBHWVFSVSA-N (1S,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-37,39,40,41,42,43,44,45,46,47,48,49-dodecamethoxy-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-diol Chemical compound O([C@@H]([C@H]([C@@H]1OC)OC)O[C@H]2[C@@H](O)[C@@H]([C@@H](O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3O)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O3)O[C@@H]2CO)OC)[C@H](CO)[C@H]1O[C@@H]1[C@@H](OC)[C@H](OC)[C@H]3[C@@H](CO)O1 YZOUYRAONFXZSI-SBHWVFSVSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- CUJVBAPGYBSBHJ-YWBSARSQSA-N 2-[[(1R,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,38,40,42-tetrakis(carboxymethoxy)-10,15-bis(carboxymethoxymethyl)-37,39,41,43,44,45,46,47,48,49-decahydroxy-20,25,30,35-tetrakis(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]nonatetracontan-5-yl]methoxy]acetic acid Chemical compound OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]1[C@H](OCC(O)=O)[C@H]2O)[C@H](O)[C@H]5OCC(O)=O)[C@H](O)[C@H]4OCC(O)=O)[C@H](O)[C@H]3OCC(O)=O CUJVBAPGYBSBHJ-YWBSARSQSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 238000000502 dialysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- -1 β-CD Ion Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102220605057 Histone H4-like protein type G_R75A_mutation Human genes 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical class CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 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 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19505263A DE19505263A1 (de) | 1995-02-16 | 1995-02-16 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
| US08/454,940 US5831081A (en) | 1995-02-16 | 1995-05-31 | Process for the purification of water-soluble cyclodextrin derivatives |
| JP8026674A JP2886127B2 (ja) | 1995-02-16 | 1996-02-14 | 水溶性シクロデキストリン誘導体の浄化方法 |
| EP96102245A EP0727440B2 (de) | 1995-02-16 | 1996-02-15 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
| DE59605527T DE59605527D1 (de) | 1995-02-16 | 1996-02-15 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19505263A DE19505263A1 (de) | 1995-02-16 | 1995-02-16 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19505263A1 true DE19505263A1 (de) | 1996-08-22 |
Family
ID=7754169
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19505263A Ceased DE19505263A1 (de) | 1995-02-16 | 1995-02-16 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
| DE59605527T Expired - Lifetime DE59605527D1 (de) | 1995-02-16 | 1996-02-15 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59605527T Expired - Lifetime DE59605527D1 (de) | 1995-02-16 | 1996-02-15 | Verfahren zur Reinigung von wasserlöslichen Cyclodextrinderivaten |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5831081A (enExample) |
| EP (1) | EP0727440B2 (enExample) |
| JP (1) | JP2886127B2 (enExample) |
| DE (2) | DE19505263A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19605683A1 (de) * | 1996-02-16 | 1997-09-11 | Forschungszentrum Juelich Gmbh | Verfahren zur Trennung von Substanzen mittels einer geeigneten Membran |
| DE60032388T2 (de) * | 1999-11-12 | 2008-01-10 | Frères Roquette | Kristalline mischungen aus teilmethylethern des beta-cyclodextrins und verwandten verbindungen |
| US6527887B1 (en) | 2002-01-18 | 2003-03-04 | Mach I, Inc. | Polymeric cyclodextrin nitrate esters |
| EP2623113B1 (en) | 2005-11-09 | 2017-05-31 | Onyx Therapeutics, Inc. | Compound for enzyme inhibition |
| NZ597545A (en) | 2006-06-19 | 2013-07-26 | Proteolix Inc | Peptide epoxyketones for proteasome inhibition |
| CA2701778C (en) | 2007-10-04 | 2018-09-11 | 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 |
| JP5675629B2 (ja) * | 2008-10-21 | 2015-02-25 | オニキス セラピューティクス， インク．Ｏｎｙｘ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | ペプチドエポキシケトンを用いた併用療法 |
| AR075899A1 (es) | 2009-03-20 | 2011-05-04 | Onyx Therapeutics Inc | Tripeptidos epoxicetonas cristalinos inhibidores de proteasa |
| WO2011060179A1 (en) | 2009-11-13 | 2011-05-19 | Onyx Therapeutics, Inc | Use of peptide epoxyketones for metastasis suppression |
| AU2011223795B2 (en) | 2010-03-01 | 2015-11-05 | Onyx Therapeutics, Inc. | Compounds for immunoproteasome inhibition |
| CA2795559A1 (en) | 2010-04-07 | 2011-11-03 | Onyx Therapeutics, Inc. | Crystalline peptide epoxyketone immunoproteasome inhibitor |
| HUE058834T2 (hu) | 2012-02-15 | 2022-09-28 | Cydex Pharmaceuticals Inc | Elõállítási eljárás ciklodextrin-származékokhoz |
| MX353603B (es) | 2012-02-28 | 2018-01-19 | Cydex Pharmaceuticals Inc | Composiciones de ciclodextrina alquilada y procesos para preparar y utilizar las mismas. |
| AU2013259573B2 (en) | 2012-05-08 | 2018-02-15 | Onyx Therapeutics, Inc. | Cyclodextrin complexation Methods for Formulating Peptide Proteasome Inhibitors |
| WO2014011695A2 (en) | 2012-07-09 | 2014-01-16 | Onyx Therapeutics, Inc. | Prodrugs of peptide epoxy ketone protease inhibitors |
| WO2014066274A1 (en) | 2012-10-22 | 2014-05-01 | Cydex Pharmaceuticals, Inc. | Alkylated cyclodextrin compositions and processes for preparing and using the same |
| HUE063851T2 (hu) | 2014-08-22 | 2024-02-28 | Cydex Pharmaceuticals Inc | Frakcionált alkilezett ciklodextrin készítmények és eljárás ezek elõállítására és alkalmazására |
| US12522670B2 (en) * | 2018-06-29 | 2026-01-13 | Roquette Freres | Hydroxypropyl-beta-cyclodextrin and process for the production thereof |
| CN112142875A (zh) * | 2019-06-27 | 2020-12-29 | 广东东阳光药业有限公司 | 一种舒更葡糖钠的精制方法 |
| CN115038723A (zh) | 2019-11-18 | 2022-09-09 | 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 |
| US12698348B2 (en) | 2020-09-24 | 2026-08-04 | Cydex Pharmaceuticals, Inc. | Alkylated cyclodextrin compositions and processes for preparing and using the same |
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| US3453257A (en) * | 1967-02-13 | 1969-07-01 | Corn Products Co | Cyclodextrin with cationic properties |
| DE2357731A1 (de) * | 1973-11-20 | 1975-05-22 | Merck Patent Gmbh | Verfahren zum austausch von ionischen bestandteilen organischer verbindungen |
| DE2700011A1 (de) * | 1977-01-03 | 1978-07-06 | Hideo Omoto | Hydroxyaethylstaerke, verfahren zu ihrer herstellung und sie enthaltender plasmaersatz |
| JPS6013678B2 (ja) * | 1981-06-08 | 1985-04-09 | 農林水産省食品総合研究所長 | サイクロデキストリンの製造方法 |
| US4870060A (en) * | 1985-03-15 | 1989-09-26 | Janssen Pharmaceutica | Derivatives of γ-cylodextrin |
| JPS62104590A (ja) * | 1985-11-01 | 1987-05-15 | Ensuikou Seito Kk | サイクロデキストリンの製造法 |
| JPS6327440A (ja) † | 1986-07-18 | 1988-02-05 | Sanraku Inc | グルコシル化分岐シクロデキストリン含有組成物 |
| JPS63229109A (ja) * | 1987-03-17 | 1988-09-26 | Asahi Chem Ind Co Ltd | スルホン化ポリフエニレンオキサイド複合半透膜の製造方法 |
| WO1990012035A1 (en) * | 1989-04-03 | 1990-10-18 | Janssen Pharmaceutica N.V. | Regioselective substitutions in cyclodextrins |
| KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| JP2905573B2 (ja) * | 1990-06-28 | 1999-06-14 | 日本食品化工株式会社 | ヒドロキシアルキル化シクロデキストリン精製物及びその製造法 |
| US5041227A (en) * | 1990-10-09 | 1991-08-20 | Bend Research, Inc. | Selective aqueous extraction of organics coupled with trapping by membrane separation |
| FR2668163B1 (fr) * | 1990-10-18 | 1993-01-15 | Orsan | Procede de fabrication de beta-cyclodextrine. |
| US5221485A (en) † | 1991-12-03 | 1993-06-22 | Mallinckrodt Medical, Inc. | Purification of X-ray contrast agent, magnetic resonance imaging agent, or radiopharmaceuticals using reverse osmosis |
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1995
- 1995-02-16 DE DE19505263A patent/DE19505263A1/de not_active Ceased
- 1995-05-31 US US08/454,940 patent/US5831081A/en not_active Expired - Lifetime
-
1996
- 1996-02-14 JP JP8026674A patent/JP2886127B2/ja not_active Expired - Lifetime
- 1996-02-15 EP EP96102245A patent/EP0727440B2/de not_active Expired - Lifetime
- 1996-02-15 DE DE59605527T patent/DE59605527D1/de not_active Expired - Lifetime
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| CA, 1987, 107, 174810 * |
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| CA, 1993, 98, 141869 * |
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| Derwent 88-073 862/11 (= JP 63027440 A) * |
| Derwent 92-111 446/14 (= JP 04057801 A) * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0727440A2 (de) | 1996-08-21 |
| US5831081A (en) | 1998-11-03 |
| JPH08259605A (ja) | 1996-10-08 |
| JP2886127B2 (ja) | 1999-04-26 |
| DE59605527D1 (de) | 2000-08-10 |
| EP0727440B1 (de) | 2000-07-05 |
| EP0727440B2 (de) | 2003-11-26 |
| EP0727440A3 (enExample) | 1996-08-28 |
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