CA2919501A1 - Cyclodextrin - Google Patents
Cyclodextrin Download PDFInfo
- Publication number
- CA2919501A1 CA2919501A1 CA2919501A CA2919501A CA2919501A1 CA 2919501 A1 CA2919501 A1 CA 2919501A1 CA 2919501 A CA2919501 A CA 2919501A CA 2919501 A CA2919501 A CA 2919501A CA 2919501 A1 CA2919501 A1 CA 2919501A1
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- beta
- substitution
- sbe
- reaction
- 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.)
- Abandoned
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 168
- 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 60
- 238000000034 method Methods 0.000 claims abstract description 142
- 238000006243 chemical reaction Methods 0.000 claims abstract description 86
- -1 alkyl sultone Chemical class 0.000 claims abstract description 26
- 230000004913 activation Effects 0.000 claims abstract description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 238
- 238000006467 substitution reaction Methods 0.000 claims description 139
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 claims description 66
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 25
- 238000010923 batch production Methods 0.000 claims description 20
- 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 description 17
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 15
- 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 claims description 14
- 150000008053 sultones Chemical class 0.000 claims description 9
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000012377 drug delivery Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 claims description 3
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 3
- BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims description 3
- 108010021331 carfilzomib Proteins 0.000 claims description 3
- 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 3
- OMPCVMLFFSQFIX-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(5-tert-butyl-2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 OMPCVMLFFSQFIX-CONSDPRKSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229960005260 amiodarone Drugs 0.000 claims description 2
- 229960004372 aripiprazole Drugs 0.000 claims description 2
- 229960002438 carfilzomib Drugs 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229960002505 maropitant Drugs 0.000 claims description 2
- 231100000957 no side effect Toxicity 0.000 claims description 2
- 230000008663 renal system process Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 229960000607 ziprasidone Drugs 0.000 claims description 2
- 229960004853 betadex Drugs 0.000 abstract description 8
- 239000001116 FEMA 4028 Substances 0.000 abstract description 7
- 235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 7
- 238000001962 electrophoresis Methods 0.000 description 48
- 239000000243 solution Substances 0.000 description 40
- 230000008569 process Effects 0.000 description 37
- 238000004519 manufacturing process Methods 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 238000001994 activation Methods 0.000 description 22
- 239000000463 material Substances 0.000 description 22
- 238000005112 continuous flow technique Methods 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 241000862969 Stella Species 0.000 description 14
- 241000894007 species Species 0.000 description 13
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 11
- 229960004740 voriconazole Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 9
- 238000000105 evaporative light scattering detection Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229940097362 cyclodextrins Drugs 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 229940090044 injection Drugs 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000013508 migration Methods 0.000 description 5
- 230000005012 migration Effects 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 238000011143 downstream manufacturing Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012847 fine chemical Substances 0.000 description 4
- 238000005111 flow chemistry technique Methods 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 238000005251 capillar electrophoresis Methods 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101000701286 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) Alkanesulfonate monooxygenase Proteins 0.000 description 2
- 101000983349 Solanum commersonii Osmotin-like protein OSML13 Proteins 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000012505 colouration Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000011082 depyrogenation Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229940126534 drug product Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 2
- PGVSXRHFXJOMGW-YBZGWEFGSA-N (2s,3s)-2-benzhydryl-n-[(5-tert-butyl-2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine;2-hydroxypropane-1,2,3-tricarboxylic acid;hydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O.COC1=CC=C(C(C)(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 PGVSXRHFXJOMGW-YBZGWEFGSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- VMSUVWZFCQSDRU-UHFFFAOYSA-N 3-(3-sulfopropoxy)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOCCCS(O)(=O)=O VMSUVWZFCQSDRU-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 229940056213 abilify Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940069233 cerenia Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012412 chemical coupling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- KPHWPUGNDIVLNH-UHFFFAOYSA-M diclofenac sodium Chemical compound [Na+].[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl KPHWPUGNDIVLNH-UHFFFAOYSA-M 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229940003380 geodon Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 229940000764 kyprolis Drugs 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 231100000381 nephrotoxic Toxicity 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 229940057462 nexterone Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002477 vacuolizing effect Effects 0.000 description 1
- 229940063674 voltaren Drugs 0.000 description 1
- 229940082636 voriconazole injection Drugs 0.000 description 1
- 230000003313 weakening effect Effects 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
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Otolaryngology (AREA)
- Psychiatry (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361847509P | 2013-07-17 | 2013-07-17 | |
| GB1312737.8 | 2013-07-17 | ||
| US61/847,509 | 2013-07-17 | ||
| GBGB1312737.8A GB201312737D0 (en) | 2013-07-17 | 2013-07-17 | Cyclodextrin |
| PCT/GB2014/052173 WO2015008066A1 (en) | 2013-07-17 | 2014-07-16 | Cyclodextrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2919501A1 true CA2919501A1 (en) | 2015-01-22 |
Family
ID=49081370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2919501A Abandoned CA2919501A1 (en) | 2013-07-17 | 2014-07-16 | Cyclodextrin |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US11117978B2 (enExample) |
| EP (1) | EP3022231B1 (enExample) |
| JP (1) | JP2016525600A (enExample) |
| KR (1) | KR20160031019A (enExample) |
| CN (1) | CN105431458A (enExample) |
| AP (1) | AP2016008975A0 (enExample) |
| AU (1) | AU2014291800A1 (enExample) |
| CA (1) | CA2919501A1 (enExample) |
| CL (1) | CL2016000082A1 (enExample) |
| GB (3) | GB201312737D0 (enExample) |
| HU (1) | HUE038911T2 (enExample) |
| MX (1) | MX2016000553A (enExample) |
| PT (1) | PT3022231T (enExample) |
| WO (1) | WO2015008066A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10532102B2 (en) | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
| US11118217B2 (en) | 2017-01-30 | 2021-09-14 | Bio-Rad Laboratories, Inc. | Emulsion compositions and methods of their use |
| US11274164B2 (en) | 2017-02-07 | 2022-03-15 | Biophore India Pharmaceuticals Pvt. Ltd. | Method for the preparation of sulfobutylether beta cyclodextrin sodium |
| CN112557541B (zh) * | 2020-12-08 | 2022-07-12 | 河北科技大学 | 一种枸橼酸马罗匹坦及其有关物质的检测方法 |
| CN112370451A (zh) * | 2020-12-08 | 2021-02-19 | 河北科技大学 | 一种枸橼酸马罗匹坦包合物、注射液及制备方法 |
| CN114369177A (zh) * | 2021-12-31 | 2022-04-19 | 贵州省欣紫鸿药用辅料有限公司 | 一种采用管道反应器制备磺丁基醚-β-环糊精的方法 |
| WO2025229196A1 (en) | 2024-05-03 | 2025-11-06 | Aalborg Universitet | Primary side modified sulfoalkyl ether- and hydroxypropyl-cyclodextrins, synthesis and use thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5874418A (en) * | 1997-05-05 | 1999-02-23 | Cydex, Inc. | Sulfoalkyl ether cyclodextrin based solid pharmaceutical formulations and their use |
| GB9713149D0 (en) | 1997-06-21 | 1997-08-27 | Pfizer Ltd | Pharmaceutical formulations |
| ATE323110T1 (de) * | 1997-07-01 | 2006-04-15 | Pfizer Prod Inc | Verfahren zur herstellung von einem cyclodextrin |
| US6337380B1 (en) * | 1998-12-01 | 2002-01-08 | Fuji Photo Film Co., Ltd. | Polymer having sulfonic acid group and silver halide photographic photosensitive material using the polymer |
| US6869939B2 (en) | 2002-05-04 | 2005-03-22 | Cydex, Inc. | Formulations containing amiodarone and sulfoalkyl ether cyclodextrin |
| CN100503647C (zh) | 2005-11-02 | 2009-06-24 | 南京师范大学 | 羟丙基-磺丁基-β-环糊精及其制备方法、分析方法以及在药学上的应用 |
| RU2470636C2 (ru) * | 2007-04-27 | 2012-12-27 | Сайдекс Фамэсьютиклз, Инк. | Композиция клопидогреля и сульфоалкилового эфира циклодекстрина (варианты) и способы лечения заболеваний посредством названной композиции (варианты) |
| US7635773B2 (en) * | 2008-04-28 | 2009-12-22 | Cydex Pharmaceuticals, Inc. | Sulfoalkyl ether cyclodextrin compositions |
| US9751957B2 (en) | 2012-02-15 | 2017-09-05 | Cydex Pharmaceuticals, Inc. | Manufacturing process for cyclodextrin derivatives |
| BR112012028726B1 (pt) | 2012-05-08 | 2021-07-13 | Onyx Therapeutics, Inc. | Método para preparar uma composição farmacêutica com baixo teor de cloreto |
-
2013
- 2013-07-17 GB GBGB1312737.8A patent/GB201312737D0/en not_active Ceased
-
2014
- 2014-07-16 WO PCT/GB2014/052173 patent/WO2015008066A1/en not_active Ceased
- 2014-07-16 PT PT147423222T patent/PT3022231T/pt unknown
- 2014-07-16 AP AP2016008975A patent/AP2016008975A0/xx unknown
- 2014-07-16 EP EP14742322.2A patent/EP3022231B1/en active Active
- 2014-07-16 US US14/333,417 patent/US11117978B2/en active Active
- 2014-07-16 CN CN201480040709.2A patent/CN105431458A/zh active Pending
- 2014-07-16 GB GB2015609.7A patent/GB2586104B/en active Active
- 2014-07-16 KR KR1020167003973A patent/KR20160031019A/ko not_active Withdrawn
- 2014-07-16 JP JP2016526700A patent/JP2016525600A/ja active Pending
- 2014-07-16 GB GB1412644.5A patent/GB2519832B/en active Active
- 2014-07-16 MX MX2016000553A patent/MX2016000553A/es unknown
- 2014-07-16 HU HUE14742322A patent/HUE038911T2/hu unknown
- 2014-07-16 AU AU2014291800A patent/AU2014291800A1/en not_active Abandoned
- 2014-07-16 CA CA2919501A patent/CA2919501A1/en not_active Abandoned
-
2015
- 2015-09-30 US US14/871,649 patent/US10239961B2/en active Active
-
2016
- 2016-01-14 CL CL2016000082A patent/CL2016000082A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3022231B1 (en) | 2018-04-18 |
| US11117978B2 (en) | 2021-09-14 |
| KR20160031019A (ko) | 2016-03-21 |
| GB2586104B (en) | 2021-03-31 |
| MX2016000553A (es) | 2016-08-01 |
| GB201412644D0 (en) | 2014-08-27 |
| GB2519832A (en) | 2015-05-06 |
| GB201312737D0 (en) | 2013-08-28 |
| WO2015008066A1 (en) | 2015-01-22 |
| HUE038911T2 (hu) | 2018-12-28 |
| CN105431458A (zh) | 2016-03-23 |
| JP2016525600A (ja) | 2016-08-25 |
| EP3022231A1 (en) | 2016-05-25 |
| PT3022231T (pt) | 2018-06-11 |
| AP2016008975A0 (en) | 2016-01-31 |
| GB202015609D0 (en) | 2020-11-18 |
| AU2014291800A1 (en) | 2016-02-11 |
| GB2586104A (en) | 2021-02-03 |
| US20160024229A1 (en) | 2016-01-28 |
| CL2016000082A1 (es) | 2016-09-23 |
| US10239961B2 (en) | 2019-03-26 |
| US20150025023A1 (en) | 2015-01-22 |
| GB2519832B (en) | 2021-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10239961B2 (en) | Cyclodextrin | |
| Sarabia-Vallejo et al. | Cyclodextrin inclusion complexes for improved drug bioavailability and activity: synthetic and analytical aspects | |
| Zou et al. | Experimental and simulation study of the solvent effects on the intrinsic properties of spherical lignin nanoparticles | |
| JP6956767B2 (ja) | シクロデキストリン誘導体のための製造方法 | |
| Gereniu et al. | Recovery of carrageenan from Solomon Islands red seaweed using ionic liquid-assisted subcritical water extraction | |
| Galan et al. | Recent developments of ionic liquids in oligosaccharide synthesis: the sweet side of ionic liquids | |
| Ioan et al. | Structure properties of dextran. 2. Dilute solution | |
| JP6389470B2 (ja) | ポリα−１，３−グルカンエーテルの調製 | |
| Su et al. | Synthesis and characterization of Schiff base contained dextran microgels in water-in-oil inverse microemulsion | |
| Chooi et al. | Physical characterisation and long-term stability studies on quaternary ammonium palmitoyl glycol chitosan (GCPQ)—A new drug delivery polymer | |
| Bo et al. | Sulfation and biological activities of konjac glucomannan | |
| WO2015200590A1 (en) | Poly alpha-1,3-glucan solution compositions | |
| CN1798754A (zh) | 高分子量铁－糖络合物的合成方法 | |
| Becker et al. | Multifunctional poly (phosphoester) s for reversible Diels–Alder postmodification to tune the LCST in water | |
| CN104548109B (zh) | 生物医学组合物 | |
| Adam et al. | Molecular recognition of isovanillin crosslinked carrageenan biocomposite for drug delivery application | |
| Behnke et al. | Ethoxy acetalated dextran nanoparticles for drug delivery: A comparative study of formulation methods | |
| CN100571781C (zh) | 生物素化普鲁兰多糖纳米微粒及其制备方法 | |
| CN107574198B (zh) | 一种采用醇沉分级制备螺旋糊精包结络合载体的方法 | |
| Jia et al. | Enhanced dissolution of galactomannan and highly efficient selenium functionalization using ionic liquids with dual roles as solvents and catalysts | |
| CN102139113A (zh) | 新的药物增溶载体及其制备方法和应用 | |
| Fan et al. | Synthesis and properties of functional glycomimetics through click grafting of fucose onto chondroitin sulfates | |
| Chen et al. | Construction of enzymatic nanoreactors with high catalytic activity in millifluidic systems for cancer therapy | |
| CN103687652B (zh) | 从纤维素醚中除去邻亚烷卤醇的方法 | |
| JP2023156995A (ja) | ポリマー、ポリマーの製造方法及びドロプレット |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180717 |