IL137955A - High cross-linked amylose with functional groups as a matrix for delayed release of pharmacological agents - Google Patents

High cross-linked amylose with functional groups as a matrix for delayed release of pharmacological agents

Info

Publication number: IL137955A
Authority: IL; Israel
Prior art keywords: cross; high amylose; amylose starch; linking agent; linked
Prior art date: 1998-02-24

Application number

IL13795599A

Other languages

English (en)

Hebrew (he)

Other versions

IL137955A0 (en

Original Assignee

Chouinard Francois

Matescu Mircea A

Pompilia Ispas Szabo

Vincent Lenaerts

Priority date (The priority date 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 date listed.)

1998-02-24

Filing date

1999-02-24

Publication date

2005-12-18

1999-02-24 Application filed by Chouinard Francois, Matescu Mircea A, Pompilia Ispas Szabo, Vincent Lenaerts filed Critical Chouinard Francois

2001-10-31 Publication of IL137955A0 publication Critical patent/IL137955A0/xx

2005-12-18 Publication of IL137955A publication Critical patent/IL137955A/en

Links

229920001685 Amylomaize Polymers 0.000 title claims abstract description 94
125000000524 functional group Chemical group 0.000 title claims description 14
239000008177 pharmaceutical agent Substances 0.000 title description 18
239000011159 matrix material Substances 0.000 title description 9
239000003431 cross linking reagent Substances 0.000 claims abstract description 49
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 30
229940127557 pharmaceutical product Drugs 0.000 claims abstract description 30
238000004132 cross linking Methods 0.000 claims abstract description 26
239000007787 solid Substances 0.000 claims abstract description 23
239000004382 Amylase Substances 0.000 claims abstract description 20
229920001282 polysaccharide Polymers 0.000 claims abstract description 18
239000005017 polysaccharide Substances 0.000 claims abstract description 18
102000013142 Amylases Human genes 0.000 claims abstract description 17
108010065511 Amylases Proteins 0.000 claims abstract description 17
229920005862 polyol Polymers 0.000 claims abstract description 16
150000003077 polyols Chemical class 0.000 claims abstract description 16
235000019418 amylase Nutrition 0.000 claims abstract description 14
150000004676 glycans Chemical class 0.000 claims abstract 15
229920000856 Amylose Polymers 0.000 claims description 63
239000000843 powder Substances 0.000 claims description 35
238000000034 method Methods 0.000 claims description 32
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 31
238000013270 controlled release Methods 0.000 claims description 26
239000004372 Polyvinyl alcohol Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 24
229920002451 polyvinyl alcohol Polymers 0.000 claims description 24
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 19
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 19
UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 claims description 19
229960005489 paracetamol Drugs 0.000 claims description 16
239000003153 chemical reaction reagent Substances 0.000 claims description 15
229920000945 Amylopectin Polymers 0.000 claims description 14
238000013268 sustained release Methods 0.000 claims description 14
239000012730 sustained-release form Substances 0.000 claims description 14
150000001735 carboxylic acids Chemical class 0.000 claims description 12
238000002156 mixing Methods 0.000 claims description 12
230000015556 catabolic process Effects 0.000 claims description 10
238000006731 degradation reaction Methods 0.000 claims description 10
ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 claims description 8
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 6
QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical group OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 claims description 5
229920002907 Guar gum Polymers 0.000 claims description 5
239000000665 guar gum Substances 0.000 claims description 5
235000010417 guar gum Nutrition 0.000 claims description 5
229960002154 guar gum Drugs 0.000 claims description 5
229920001285 xanthan gum Polymers 0.000 claims description 5
239000000230 xanthan gum Substances 0.000 claims description 5
235000010493 xanthan gum Nutrition 0.000 claims description 5
229940082509 xanthan gum Drugs 0.000 claims description 5
239000004135 Bone phosphate Substances 0.000 claims description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 4
WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
150000002357 guanidines Chemical class 0.000 claims description 4
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 4
150000007928 imidazolide derivatives Chemical class 0.000 claims description 4
150000004693 imidazolium salts Chemical class 0.000 claims description 4
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
235000019260 propionic acid Nutrition 0.000 claims description 4
235000019832 sodium triphosphate Nutrition 0.000 claims description 4
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 claims description 4
239000011837 N,N-methylenebisacrylamide Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical group [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 claims description 3
229960003447 pseudoephedrine hydrochloride Drugs 0.000 claims description 3
239000005057 Hexamethylene diisocyanate Substances 0.000 claims 3
229920000161 Locust bean gum Polymers 0.000 claims 3
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 3
239000000711 locust bean gum Substances 0.000 claims 3
235000010420 locust bean gum Nutrition 0.000 claims 3
FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 claims 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 46
239000003826 tablet Substances 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
238000003756 stirring Methods 0.000 description 30
239000000725 suspension Substances 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
229920002472 Starch Polymers 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 20
229920000642 polymer Polymers 0.000 description 20
239000008107 starch Substances 0.000 description 20
235000019698 starch Nutrition 0.000 description 20
239000012153 distilled water Substances 0.000 description 19
229940079593 drug Drugs 0.000 description 18
239000003814 drug Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 13
238000004090 dissolution Methods 0.000 description 11
230000008961 swelling Effects 0.000 description 9
238000005406 washing Methods 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000008363 phosphate buffer Substances 0.000 description 8
239000012429 reaction media Substances 0.000 description 8
229960001193 diclofenac sodium Drugs 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
-1 polyethylene Polymers 0.000 description 7
150000004804 polysaccharides Chemical class 0.000 description 7
JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 5
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000000758 substrate Substances 0.000 description 5
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
241000030538 Thecla Species 0.000 description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000012377 drug delivery Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000000265 homogenisation Methods 0.000 description 4
230000036571 hydration Effects 0.000 description 4
238000006703 hydration reaction Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
108090000637 alpha-Amylases Proteins 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
238000001035 drying Methods 0.000 description 3
210000001198 duodenum Anatomy 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 3
229960003908 pseudoephedrine Drugs 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000001694 spray drying Methods 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
102000004139 alpha-Amylases Human genes 0.000 description 2
229940024171 alpha-amylase Drugs 0.000 description 2
150000007942 carboxylates Chemical group 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
229940124447 delivery agent Drugs 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
238000007907 direct compression Methods 0.000 description 2
229940088598 enzyme Drugs 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000012729 immediate-release (IR) formulation Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000000877 morphologic effect Effects 0.000 description 2
CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
229920002689 polyvinyl acetate Polymers 0.000 description 2
229940075065 polyvinyl acetate Drugs 0.000 description 2
239000011118 polyvinyl acetate Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
238000003918 potentiometric titration Methods 0.000 description 2
239000000700 radioactive tracer Substances 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000010998 test method Methods 0.000 description 2
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 description 1
TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
WDMUXYQIMRDWRC-UHFFFAOYSA-N 2-hydroxy-3,4-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O WDMUXYQIMRDWRC-UHFFFAOYSA-N 0.000 description 1
ZRVIYEJYXIDATJ-UHFFFAOYSA-N 4-Heptyloxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1 ZRVIYEJYXIDATJ-UHFFFAOYSA-N 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
102100026367 Pancreatic alpha-amylase Human genes 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
PWACSDKDOHSSQD-IUTFFREVSA-N acrivastine Chemical compound C1=CC(C)=CC=C1C(\C=1N=C(\C=C\C(O)=O)C=CC=1)=C/CN1CCCC1 PWACSDKDOHSSQD-IUTFFREVSA-N 0.000 description 1
229960003792 acrivastine Drugs 0.000 description 1
229920006243 acrylic copolymer Polymers 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000003625 amylolytic effect Effects 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
229960000074 biopharmaceutical Drugs 0.000 description 1
229920001222 biopolymer Polymers 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000112 colonic effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
239000011243 crosslinked material Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229960001985 dextromethorphan Drugs 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
229960001259 diclofenac Drugs 0.000 description 1
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229960003580 felodipine Drugs 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
229960001381 glipizide Drugs 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229960004125 ketoconazole Drugs 0.000 description 1
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
229960000991 ketoprofen Drugs 0.000 description 1
229960004752 ketorolac Drugs 0.000 description 1
OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
229960005249 misoprostol Drugs 0.000 description 1
229940045641 monobasic sodium phosphate Drugs 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000005445 natural material Substances 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
230000008520 organization Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960003893 phenacetin Drugs 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229960002702 piroxicam Drugs 0.000 description 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229960000894 sulindac Drugs 0.000 description 1
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
229960001017 tolmetin Drugs 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
229960004380 tramadol Drugs 0.000 description 1
TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
229920001221 xylan Polymers 0.000 description 1
150000004823 xylans Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Preparation (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL13795599A 1998-02-24 1999-02-24 High cross-linked amylose with functional groups as a matrix for delayed release of pharmacological agents IL137955A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/028,385 US6284273B1 (en)	1998-02-24	1998-02-24	Cross-linked high amylose starch resistant to amylase as a matrix for the slow release of biologically active compounds
PCT/CA1999/000169 WO1999043305A1 (en)	1998-02-24	1999-02-24	Cross-linked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents

Publications (2)

Publication Number	Publication Date
IL137955A0 IL137955A0 (en)	2001-10-31
IL137955A true IL137955A (en)	2005-12-18

Family

ID=21843160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13795599A IL137955A (en)	1998-02-24	1999-02-24	High cross-linked amylose with functional groups as a matrix for delayed release of pharmacological agents

Country Status (19)

Country	Link
US (2)	US6284273B1 (de)
EP (1)	EP1059915B1 (de)
JP (1)	JP2002504508A (de)
KR (1)	KR100713702B1 (de)
CN (1)	CN1298297A (de)
AT (1)	ATE277604T1 (de)
AU (1)	AU755069B2 (de)
BR (1)	BR9908187A (de)
CA (1)	CA2321461C (de)
CZ (1)	CZ301010B6 (de)
DE (1)	DE69920669T2 (de)
HU (1)	HU225045B1 (de)
IL (1)	IL137955A (de)
NO (1)	NO329257B1 (de)
NZ (1)	NZ506437A (de)
PL (1)	PL192468B1 (de)
PT (1)	PT1059915E (de)
TR (1)	TR200003014T2 (de)
WO (1)	WO1999043305A1 (de)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100389752C (zh) *	1978-04-21	2008-05-28	莱博法姆公司	控释组合物
IL119660A (en)	1993-05-10	2002-09-12	Euro Celtique Sa	Controlled release formulation comprising tramadol
US7022683B1 (en)	1998-05-13	2006-04-04	Carrington Laboratories, Inc.	Pharmacological compositions comprising pectins having high molecular weights and low degrees of methoxylation
DE19927688A1 (de) *	1999-06-17	2000-12-21	Gruenenthal Gmbh	Mehrschichttablette zur Verabreichung einer fixen Kombination von Tramadol und Diclofenac
US6607748B1 (en) *	2000-06-29	2003-08-19	Vincent Lenaerts	Cross-linked high amylose starch for use in controlled-release pharmaceutical formulations and processes for its manufacture
US6777000B2 (en)	2001-02-28	2004-08-17	Carrington Laboratories, Inc.	In-situ gel formation of pectin
US7494669B2 (en)	2001-02-28	2009-02-24	Carrington Laboratories, Inc.	Delivery of physiological agents with in-situ gels comprising anionic polysaccharides
WO2002088331A1 (en) *	2001-05-01	2002-11-07	Universite Du Quebec A Montreal	Tridimensional biocompatible support structure for bioartificial organs and uses thereof
US8487002B2 (en) *	2002-10-25	2013-07-16	Paladin Labs Inc.	Controlled-release compositions
TWI319713B (en) *	2002-10-25	2010-01-21		Sustained-release tramadol formulations with 24-hour efficacy
PT1558935E (pt) *	2002-10-25	2008-10-16	Labopharm Inc	Composições de libertação controlada
US20060172006A1 (en) *	2003-10-10	2006-08-03	Vincent Lenaerts	Sustained-release tramadol formulations with 24-hour clinical efficacy
CA2547843A1 (en) *	2004-02-09	2005-08-18	Transfert Plus Societe En Commandite	Composition comprising polymeric material and uses thereof
CA2491665A1 (fr) *	2004-12-24	2006-06-24	Louis Cartilier	Formulation de comprime pour liberation soutenue de principe actif
ES2620293T3 (es) *	2005-09-09	2017-06-28	Paladin Labs Inc.	Composición de liberación sostenida de fármacos
CN101252932B (zh)	2005-09-09	2012-10-03	安吉利尼莱博法姆有限责任公司	用于一天给药一次的曲唑酮组合物
ATE543522T1 (de) *	2005-09-21	2012-02-15	Surmodics Inc	In vivo geformte matrizen mit natürlichen biologisch abbaubaren polysacchariden und ihre ophthalmischen verwendungen
CN101309709A (zh) *	2005-09-21	2008-11-19	苏尔莫迪克斯公司	包含天然生物可降解的多糖的涂层和物品
WO2007105719A1 (ja) *	2006-03-14	2007-09-20	National University Corporation NARA Institute of Science and Technology	新規なヘパリン代替材料およびその製造方法
CA2590821A1 (en) *	2007-06-07	2008-12-07	Universite De Montreal	High-amylose sodium carboxymethyl starch sustained release excipient and process for preparing the same
CA2678092C (en) *	2007-10-16	2013-07-30	Labopharm Inc.	Bilayer composition for the sustained release of acetaminophen and tramadol
CN101161684B (zh) *	2007-11-23	2010-05-19	华南理工大学	交联羧甲基淀粉的红外线合成方法
CA2707980C (en) *	2007-12-17	2015-05-12	Labopharm Inc.	Misuse preventative, controlled release formulation
RU2491301C2 (ru) *	2007-12-21	2013-08-27	Акцо Нобель Н.В.	Термореактивные полимеры
JP5763525B2 (ja)	2008-05-07	2015-08-12	サーモディクス，インコーポレイティド	粒子からの核酸複合体の送達
EP2331629B1 (de) *	2008-09-15	2016-06-22	Paladin Labs Inc.	Auf stärke basierende mikropartikel zur freisetzung von darin enthaltenen wirkstoffen
EP2367541B1 (de)	2008-12-16	2014-07-16	Paladin Labs Inc.	Formulierung mit gesteuerter freisetzung und missbrauchsschutz
EP2590636A1 (de)	2010-07-06	2013-05-15	Grünenthal GmbH	Neue gastroretentive dosierungsformen mit einem gaba-analog und einem opioid
US8901092B2 (en)	2010-12-29	2014-12-02	Surmodics, Inc.	Functionalized polysaccharides for active agent delivery
WO2012116434A1 (en) *	2011-03-01	2012-09-07	4413261 Canada Inc. (Spencer Canada)	Two speed monolithic system for controlled release of drugs
JP6605508B2 (ja) *	2014-02-27	2019-11-13	ビー‐オーガニックフィルムスコーポレイション	一重らせんｖ構造を有する官能化デンプン中に含まれる生物活性剤
KR20170093243A (ko)	2014-12-19	2017-08-14	백스터 인터내셔널 인코포레이티드	유동성 지혈 조성물
CN104784738B (zh) *	2015-04-03	2016-12-07	四川大学	一种天然缓释多效医用海绵
CN106279453B (zh) *	2015-05-28	2019-12-10	易媛	交联的高分子化合物及其制备方法、水凝胶、水基压裂液和用途
CN105536058A (zh) *	2016-01-22	2016-05-04	青岛中腾生物技术有限公司	一种医用淀粉海绵及其制备方法和用途
GB2567493B (en)	2017-10-13	2019-12-18	Altus Formulation Inc	Starch-based release modifying excipients and pharmaceutical compositions derived therefrom
CN111072791A (zh) *	2019-12-27	2020-04-28	河南新孚望新材料科技有限公司	一种包膜剂用高直链淀粉的制备方法
JP7125216B1 (ja)	2021-03-31	2022-08-24	長瀬産業株式会社	水溶性ポリマーの製造方法、および吸水性樹脂の製造方法
AU2022251740B2 (en) *	2021-03-31	2026-02-26	Nagase & Co., Ltd.	Method for producing water-soluble polymer and method for producing water-absorbing resin
WO2025194276A1 (en) *	2024-03-21	2025-09-25	Eric Therasse	Pharmaceutical composition comprising microparticles for high drug loading
CN119264282A (zh) *	2024-10-18	2025-01-07	华南理工大学	一种高空腔纳米淀粉及基于其的高耐老化橡胶材料与制备

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4072535A (en) *	1970-12-28	1978-02-07	A. E. Staley Manufacturing Company	Precompacted-starch binder-disintegrant-filler material for direct compression tablets and dry dosage capsules
US4369308A (en) *	1981-07-24	1983-01-18	National Starch And Chemical Corporation	Low swelling starches as tablet disintegrants
JPH0791240B2 (ja) *	1987-04-01	1995-10-04	株式会社日本触媒	２−ハロエチルアミンハロゲン化水素酸塩の製造方法
CA2041774C (en) *	1990-11-27	1994-04-19	Mircea A. Mateescu	Use of cross-linked amylose as a matrix for the slow release of biologically active compounds
JPH06271704A (ja) *	1993-03-22	1994-09-27	Asahi Chem Ind Co Ltd	水性易燃性組成物
US5616343A (en) *	1993-03-25	1997-04-01	Labopharm, Inc.	Cross-linked amylose as a binder/disintegrant in tablets
CN1150218C (zh) *	1994-04-11	2004-05-19	赫希斯特人造丝公司	超吸收性聚合物及其制品
US5830884A (en) *	1995-01-18	1998-11-03	National Starch And Chemical Investment Holding Corporation	Pharmaceutical products containing thermally-inhibited starches
US5593503A (en) *	1995-06-07	1997-01-14	National Starch And Chemical Investment Holding Corporation	Process for producing amylase resistant granular starch
US5667637A (en) *	1995-11-03	1997-09-16	Weyerhaeuser Company	Paper and paper-like products including water insoluble fibrous carboxyalkyl cellulose
CA2173818A1 (fr) *	1996-04-10	1997-10-11	Francois Chouinard	Comprime pharmaceutique a liberation controlee contenant un support a base d'amylose reticule et d'hydroxypropylmethylcellulose
US5879707A (en) *	1996-10-30	1999-03-09	Universite De Montreal	Substituted amylose as a matrix for sustained drug release
US5807575A (en) *	1997-02-14	1998-09-15	Rougier Inc.	Manufacture of cross-linked amylose useful as a excipient for control release of active compounds

1998
- 1998-02-24 US US09/028,385 patent/US6284273B1/en not_active Expired - Lifetime
1999
- 1999-02-24 KR KR1020007009278A patent/KR100713702B1/ko not_active Expired - Fee Related
- 1999-02-24 EP EP99936029A patent/EP1059915B1/de not_active Expired - Lifetime
- 1999-02-24 WO PCT/CA1999/000169 patent/WO1999043305A1/en not_active Ceased
- 1999-02-24 TR TR2000/03014T patent/TR200003014T2/xx unknown
- 1999-02-24 PL PL342596A patent/PL192468B1/pl not_active IP Right Cessation
- 1999-02-24 BR BR9908187-3A patent/BR9908187A/pt not_active Application Discontinuation
- 1999-02-24 US US09/257,090 patent/US6419957B1/en not_active Expired - Fee Related
- 1999-02-24 JP JP2000533104A patent/JP2002504508A/ja active Pending
- 1999-02-24 CN CN99805447A patent/CN1298297A/zh active Pending
- 1999-02-24 AU AU32420/99A patent/AU755069B2/en not_active Ceased
- 1999-02-24 CA CA002321461A patent/CA2321461C/en not_active Expired - Fee Related
- 1999-02-24 PT PT99936029T patent/PT1059915E/pt unknown
- 1999-02-24 NZ NZ506437A patent/NZ506437A/xx unknown
- 1999-02-24 CZ CZ20003097A patent/CZ301010B6/cs not_active IP Right Cessation
- 1999-02-24 IL IL13795599A patent/IL137955A/en not_active IP Right Cessation
- 1999-02-24 HU HU0100818A patent/HU225045B1/hu not_active IP Right Cessation
- 1999-02-24 AT AT99936029T patent/ATE277604T1/de not_active IP Right Cessation
- 1999-02-24 DE DE69920669T patent/DE69920669T2/de not_active Expired - Lifetime
2000
- 2000-08-23 NO NO20004208A patent/NO329257B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ506437A (en)	2003-03-28
KR100713702B1 (ko)	2007-05-02
HUP0100818A2 (hu)	2001-08-28
KR20010034531A (ko)	2001-04-25
US6419957B1 (en)	2002-07-16
HUP0100818A3 (en)	2001-12-28
PL192468B1 (pl)	2006-10-31
EP1059915A1 (de)	2000-12-20
JP2002504508A (ja)	2002-02-12
US6284273B1 (en)	2001-09-04
DE69920669T2 (de)	2005-11-03
CN1298297A (zh)	2001-06-06
HU225045B1 (en)	2006-05-29
CZ20003097A3 (en)	2001-06-13
CA2321461C (en)	2008-04-29
WO1999043305A1 (en)	1999-09-02
CZ301010B6 (cs)	2009-10-14
TR200003014T2 (tr)	2001-02-21
AU755069B2 (en)	2002-12-05
NO20004208D0 (no)	2000-08-23
DE69920669D1 (de)	2004-11-04
ATE277604T1 (de)	2004-10-15
NO20004208L (no)	2000-08-23
PT1059915E (pt)	2005-02-28
EP1059915B1 (de)	2004-09-29
BR9908187A (pt)	2000-10-31
PL342596A1 (en)	2001-06-18
CA2321461A1 (en)	1999-09-02
AU3242099A (en)	1999-09-15
IL137955A0 (en)	2001-10-31
NO329257B1 (no)	2010-09-20

Legal Events

Date	Code	Title
2006-07-05	FF	Patent granted
2009-07-27	KB	Patent renewed
2013-10-31	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
AU755069B2 (en)	2002-12-05	Cross-linked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents
JP5025066B2 (ja)	2012-09-12	徐放性医薬製剤に利用する架橋高アミローススターチとその製造方法
Kamel et al.	2008	Pharmaceutical significance of cellulose: A review
AU2001271481A1 (en)	2002-04-11	Cross-linked high amylose starch for use in controlled-release pharmaceutical formulations and processes for its manufacture
WO1999009066A1 (en)	1999-02-25	Preparation of pregelatinized high amylose starch and debranched starch useful as an excipient for controlled release of active agents
JP2008525322A (ja)	2008-07-17	薬物の徐放のための錠剤
Aguilar‐de‐Leyva et al.	2015	Critical points and phase transitions in polymeric matrices for controlled drug release
MXPA00008227A (en)	2002-05-09	Cross-linked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents
SK1795A3 (en)	1995-09-13	Drug delivery device and method of this production
Nandi	2023	Plant polysaccharides in pharmaceutical tablets
HK1037912A (en)	2002-02-22	Cross-linked high amylose starch having functional groups as a matrix for the slow release of pharmaceutical agents
Steendam	2005	Amylodextrin and poly (DL-lactide) oral controlled release matrix tablets. Concepts for understanding their release mechanisms
HK1059574B (en)	2008-06-27	Cross-linked high amylose starch for use in controlled-release pharmaceutical formulations and processes for its manufacture