USRE43799E1 - Controlled release and taste masking oral pharmaceutical composition - Google Patents
Controlled release and taste masking oral pharmaceutical composition Download PDFInfo
- Publication number
- USRE43799E1 USRE43799E1 US13/477,592 US201213477592A USRE43799E US RE43799 E1 USRE43799 E1 US RE43799E1 US 201213477592 A US201213477592 A US 201213477592A US RE43799 E USRE43799 E US RE43799E
- Authority
- US
- United States
- Prior art keywords
- matrix
- active ingredient
- lipophilic
- composition according
- amphiphilic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 238000013270 controlled release Methods 0.000 title claims abstract description 9
- 239000008203 oral pharmaceutical composition Substances 0.000 title claims description 4
- 230000000873 masking effect Effects 0.000 title abstract description 6
- 239000011159 matrix material Substances 0.000 claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 239000004480 active ingredient Substances 0.000 claims abstract description 57
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 6
- 239000003826 tablet Substances 0.000 claims description 44
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 13
- 229960004436 budesonide Drugs 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 229920002678 cellulose Polymers 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 235000010980 cellulose Nutrition 0.000 claims description 7
- -1 glycol alkyl ethers Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002634 lipophilic molecules Chemical class 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000000017 hydrogel Substances 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- 239000004375 Dextrin Substances 0.000 claims description 4
- 229920001353 Dextrin Polymers 0.000 claims description 4
- 239000000783 alginic acid Substances 0.000 claims description 4
- 235000010443 alginic acid Nutrition 0.000 claims description 4
- 229920000615 alginic acid Polymers 0.000 claims description 4
- 229960001126 alginic acid Drugs 0.000 claims description 4
- 150000004781 alginic acids Chemical class 0.000 claims description 4
- 229940106189 ceramide Drugs 0.000 claims description 4
- 150000001783 ceramides Chemical class 0.000 claims description 4
- 235000019425 dextrin Nutrition 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 150000001841 cholesterols Chemical class 0.000 claims description 3
- 239000008185 minitablet Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003626 triacylglycerols Chemical class 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000000227 bioadhesive Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001277 pectin Polymers 0.000 claims description 2
- 239000001814 pectin Substances 0.000 claims description 2
- 235000010987 pectin Nutrition 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 150000004804 polysaccharides Chemical class 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 238000004090 dissolution Methods 0.000 abstract description 17
- 239000013060 biological fluid Substances 0.000 abstract description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 34
- 239000008187 granular material Substances 0.000 description 21
- 235000019359 magnesium stearate Nutrition 0.000 description 17
- 239000000546 pharmaceutical excipient Substances 0.000 description 17
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 14
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 235000021355 Stearic acid Nutrition 0.000 description 12
- 238000007922 dissolution test Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- 239000008117 stearic acid Substances 0.000 description 12
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 10
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
- 239000008108 microcrystalline cellulose Substances 0.000 description 10
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 10
- 229940016286 microcrystalline cellulose Drugs 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 9
- 230000035515 penetration Effects 0.000 description 9
- 239000008119 colloidal silica Substances 0.000 description 8
- 239000004203 carnauba wax Substances 0.000 description 7
- 235000013869 carnauba wax Nutrition 0.000 description 7
- 238000005469 granulation Methods 0.000 description 7
- 230000003179 granulation Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 6
- 238000004898 kneading Methods 0.000 description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- 108010011485 Aspartame Proteins 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920002774 Maltodextrin Polymers 0.000 description 5
- 239000000605 aspartame Substances 0.000 description 5
- 235000010357 aspartame Nutrition 0.000 description 5
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 5
- 229960003438 aspartame Drugs 0.000 description 5
- 229960000541 cetyl alcohol Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 239000000787 lecithin Substances 0.000 description 5
- 235000010445 lecithin Nutrition 0.000 description 5
- 229940067606 lecithin Drugs 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 4
- 239000007970 homogeneous dispersion Substances 0.000 description 4
- 230000000622 irritating effect Effects 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229960001375 lactose Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- 229960000965 nimesulide Drugs 0.000 description 4
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000000750 progressive effect Effects 0.000 description 4
- 239000008347 soybean phospholipid Substances 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- 229960002675 xylitol Drugs 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000003628 erosive effect Effects 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 150000002433 hydrophilic molecules Chemical class 0.000 description 3
- 229920001477 hydrophilic polymer Polymers 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000008366 buffered solution Substances 0.000 description 2
- 229960004205 carbidopa Drugs 0.000 description 2
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960002870 gabapentin Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VWZPIJGXYWHBOW-UHFFFAOYSA-N otilonium bromide Chemical compound [Br-].CCCCCCCCOC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)OCC[N+](C)(CC)CC)C=C1 VWZPIJGXYWHBOW-UHFFFAOYSA-N 0.000 description 2
- 229960000426 otilonium bromide Drugs 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- JVTIXNMXDLQEJE-UHFFFAOYSA-N 2-decanoyloxypropyl decanoate 2-octanoyloxypropyl octanoate Chemical compound C(CCCCCCC)(=O)OCC(C)OC(CCCCCCC)=O.C(=O)(CCCCCCCCC)OCC(C)OC(=O)CCCCCCCCC JVTIXNMXDLQEJE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 229920003139 Eudragit® L 100 Polymers 0.000 description 1
- 229920003141 Eudragit® S 100 Polymers 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 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
- UFAHZIUFPNSHSL-UHFFFAOYSA-N O-propanoylcarnitine Chemical compound CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C UFAHZIUFPNSHSL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XTEBISFIAYHLQY-UHFFFAOYSA-N ethene;2-(2-hydroxyethoxy)ethanol Chemical group C=C.OCCOCCO XTEBISFIAYHLQY-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 229920003113 low viscosity grade hydroxypropyl cellulose Polymers 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 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 1
- 239000007787 solid Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- 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
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2813—Inorganic compounds
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/282—Organic compounds, e.g. fats
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
- A61K9/2846—Poly(meth)acrylates
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Definitions
- the present invention relates to controlled release and taste masking compositions containing budesonide as active ingredient incorporated in a three-component matrix structure, i.e. a structure formed by successive amphiphilic, lipophilic or inert matrices and finally incorporated or dispersed in hydrophilic matrices.
- a three-component matrix structure i.e. a structure formed by successive amphiphilic, lipophilic or inert matrices and finally incorporated or dispersed in hydrophilic matrices.
- the use of a plurality of systems mechanism for the control of the dissolution of the active ingredient modulates the dissolution rate of the active ingredient in aqueous and/or biological fluids, thereby controlling the release kinetics in the gastrointestinal tract, and it also allows the oral administration of active principles having unfavourable taste characteristics or irritating action on the mucosae of the administration site, particularly in the buccal or gastric area.
- compositions of the invention are suitable to the oral administration or the efficaciously deliver the active ingredient acting topically at some areas of the gastrointestinal tract.
- inert matrices in which the main component of the matrix structure opposes some resistance to the penetration of the solvent due to the poor affinity towards aqueous fluids; such property being known as lipophilia.
- hydrophilic matrices in which the main component of the matrix structure opposes high resistance to the progress of the solvent, in that the presence of strongly hydrophilic groups in its chains, mainly branched, remarkably increases viscosity inside the hydrated layer.
- bioerodible matrices which are capable of being degraded by the anzimes of some biological compartment.
- Inert matrices for example, generally entail non-linear, but exponential, release of the active ingredient.
- Hydrophilic matrices have a linear behaviour until a certain fraction of active ingredient has been released, then significantly deviate from linear release.
- Bioerodible matrices are ideal to carry out the so-called “sire-release”, but they involve the problem of finding the suitable enzyme or reactive to degradation. Furthermore, they frequently release in situ metabolites that are not wholly toxicologically inert.
- the inert carrier is kneaded with the solution containing the inert polymer and the active ingredient, then the organic solvent used for the their dissolution is evaporated off to obtain a solid residue.
- the resulting structure is a “reservoir”, i.e. is not macroscopically homogeneous along all the symmetry axis of the final form.
- the same “reservoir” structure is also described in Chem. Pharm. Bull. 46 (3), 531-533, (1998) which improves the application through an annealing technique of the inert polymer layer which is deposited on the surface of the pellets.
- WO 93/00889 discloses a process for the preparation of pellets in hydrophilic matrix which comprises: —dissolution of the active ingredient with gastro resistant hydrophilic polymers in organic solvents; —dying of said suspension; —subsequent kneading and formulation of the pellets in a hydrophilic or lipophilic matrix without distinction of effectiveness between the two types of application.
- EP 0 453 001 discloses a multiparticulate with “reservoir” structure inserted in a hydrophilic matrix.
- the basic multiparticulate utilizes two coating membranes to decrease the release rate of the active ingredient, a pH-dependent membrane with the purpose of gastric protection and a pH-independent methacrylic membrane with the purpose of slowing down the penetration of the aqueous fluid.
- WO 95/16451 discloses a composition only formed by a hydrophilic matrix coated with a gastro-resistant film for controlling the dissolution rate of the active ingredient.
- compositions of the invention are characterized by the absence of a first phase in which the medicament superficially present on the matrix is quickly solubilized, and by the fact the amphiphilic layer compensate the lack of affinity of the aqueous solvent with the lipophilic compounds forming the inner inert matrix.
- the invention provides controlled release and taste masking oral pharmaceutical compositions containing as active ingredient budesonide comprising:
- a particular aspect of the invention consists of controlled release oral compositions containing as active ingredient budesonide comprising:
- a further aspect of the invention provides taste masking oral pharmaceutical compositions budesonide containing comprising:
- an inert or lipophilic matrix consisting of C6-C20 alcohols or C8-C20 fatty acids or esters of fatty acids with glycerol or sorbitol or other polyalcohols with carbon atom chain not higher than six:
- amphiphilic matrix consisting of polar lipids of type I or II or glycols partially etherified with C1-C4 alkyl chains;
- an outer hydrophilic matrix containing the above matrices mainly formed by saccharide, dextrin, polyalcohol or cellulose compounds or by hydrogels or their mixtures;
- compositions of the invention can be prepared by a method comprising the following steps:
- the active ingredient represented by budesonide
- a matrix or coating consisting of compounds having amphiphilic properties, which will be further specified below.
- the active ingredient can be mixed with the amphiphilic compounds without the aid of solvents or with small amounts of water-alcoholic solvents.
- the matrix obtained as specified under a) is incorporated in a low melting lipophilic excipient or mixture of excipients, if necessary while heating to soften and/or melt the excipient itself, which thereby incorporates the active ingredient by simple dispersion forming an inert matrix which can be reduced in size to obtain inert matrix granules containing the active ingredient particles.
- the inert matrix granules are subsequently mixed together with one or more hydrophilic water-swellable excipients.
- the mixture is then subjected to compression or tabletting. This way, when the tablet is contacted with biological fluids, a high viscosity swollen layer is formed, which coordinates the solvent molecules and acts as a barrier to penetration of the aqueous fluid itself inside the new structure. Said barrier antagonizes the starting “burst effect” caused by the dissolution of the medicament inglobated inside the inert matrix, which is in its turn inside the hydrophilic matrix.
- amphiphilic compounds which can be used according to the invention comprise polar lipids of type I or II (lecithin, phosphatidylcholine, phosphatidylethanolainine), ceramides, glycol alkyl ethers such as diethylene glycol monomethyl ether (Transcutol®)
- the lipophilic matrix consists of substances selected from unsaturated or hydrogenated alcohols or fatty acids, salts, esters or amides thereof, fatty acids mono-, di- or triglycerides, the polyethoxylated derivatives thereof, waxes, ceramides, cholesterol derivatives or mixtures thereof having melting point within the range of 40 to 90° C., preferably from 60 to 70 C.
- a fatty acid calcium salt may be incorporated in the lipophilic matrix which is subsequently dispersed in a hydrophilic matrix prepared with alginic acid, thus remarkably increasing the hydrophilic matrix viscosity following penetration of the solvent front until contact with the lipophilic matrix granules dispersed inside.
- amphiphilic matrix with high content in active ingredient is first prepared by dispersing the active ingredient in a mixture of amphiphilic compounds, such as lecithin, other type II polar lipids, surfactants, or in diethylene glycol monoethyl ether; the resulting amphiphilic matrix is then mixed or kneaded, usually while hot, with lipophilic compounds suitable to form an inert matrix, such as saturated or unsaturated fatty acids, such as palmitic, stearic, myristic, lauric, laurylic, or oleic acids or mixtures thereof with other fatty acids with shorter chain, or salts or alcohols or derivatives of the cited fatty acids, such as mono-, di-, or triglycerides or esters with polyethylene glycols, alone or in combination with waxes, ceramides, cholesterol derivatives or other apolar lipids in various ratios so that the melting or softening
- amphiphilic compounds such as lecithin, other type II polar
- the order of formation of the inert and amphiphilic matrices can be reversed, incorporating the inert matrix inside the amphiphilic compounds.
- the resulting inert lipophilic matrix is reduced into granules by an extrusion and/or granulation process, or any other known processes which retain the homogeneous dispersion and matrix structure of the starting mixture.
- the hydrophilic matrix consists of excipients known as hydrogels, i.e. substances which when passing from the dry state to the hydrated one, undergo the so-called “molecular relaxation”, namely a remarkable increase in mass and weight following the coordination of a large number of water molecules by the polar groups present in the polymeric chains of the excipients themselves.
- hydrogels which can be used according to the invention are compounds selected from acrylic or methacrylic acid polymers or copolymers, alkylvinyl polymers, hydroxyalkyl celluloses, carboxyalkyl celluloses, polysaccharides, dextrins, pectins, starches and derivatives, natural or synthetic gums, alginic acid.
- polyalcohols such as xylitol, maltitol and mannitol as hydrophilic compounds can also be advantageous.
- the lipophilic matrix granules containing the active ingredient are mixed with the hydrophilic compounds cited above in a weight ratio typically ranging from 100:0.5 to 100:50 (lipophilic matrix: hydrophilic matrix).
- Part of the active ingredient can optionally be mixed with hydrophilic substances to provide compositions in which the active ingredient is dispersed both in the lipophilic and the hydrophilic matrix, said compositions being preferably in the form of tablets, capsules and/or minitablets.
- the compression of the mixture of lipophilic and/or amphiphilic matrix, hydrogel-forming compound and, optionally, active ingredient not inglobated in the lipophilic matrix yields a macroscopically homogeneous structure in all its volume, namely a matrix containing a dispersion of the lipophilic granules in a hydrophilic matrix.
- a similar result can also be obtained by coating the lipophilic matrix granules with a hydrophilic polymer coating.
- the tablets obtainable according to the invention are subjected to known coating processes with a gastro-resistant film, consisting of, for example, acrylic and methacrylic acids polymers (Eudragit®) or copolymer or cellulose derivatives, such as cellulose acetophthalate.
- the composition of the invention can further contain conventional excipients, for example bioadhesive excipients such as chitosans, polyacrylamides, natural or synthetic gums, acrylic acid polymers.
- compositions of the invention are preferably in the form of tablets, capsules or minitablets.
- contact with water or aqueous fluids causes the immediate penetration of water inside the more superficial layer of the matrix which, thanks to the presence of the aqueous solvent, swells due to the distension of the polymeric chains of the hydrogels, giving rise to a high viscosity hydrated front which prevents the further penetration of the solvent itself linearly slowing down the dissolution process to a well determined point which can be located at about half the thickness, until the further penetration of water would cause the disintegration of the hydrophilic layer and therefore the release of the content which, consisting of inert matrix granules, however induces the diffusion mechanism typical of these structures and therefore further slows down the dissolution profile of the active ingredient.
- amphiphilic matrix inside the lipophilic matrix inert allows to prevent any unevenness of the release profile of the active ingredient.
- the surfactants present in the amphiphilic portion promote wettability of the porous canaliculuses which cross the inert matrix preventing or reducing resistance to penetration of the solvent inside the inert matrix.
- the components of the hydrophilic matrix are carefully selected to minimize the active substance release time through penetration accelerated by the canalization induced by the hydrophilic compound.
- dissolution Test Method To test the effective ability of the formulations of the invention to modify the release rate and extent of the active ingredient from the dosage form suitable for the drug administration, before any pharmacokinetic study on patients or volunteers, the dissolution test is taken as monitoring and discriminating tool. Dissolution Test Method.
- Tablets according to the present invention undergo to dissolution test to verify the formulation capacity in modulating and controlling the rate by which the active ingredient is leaked by the device or dosage form in the environmental medium, generally a buffered solution simulating gastric or intestinal juices.
- pH 1, 6.4 and 7.2 are the pH condition generally used in this test applications
- the tablets according to the present invention when designed to be used to treat inflammatory bowel disease, in principle have to show a good resistance, thanks to the polymeric film resistant to the low pH conditions (intended as ⁇ 5 to simulate the gastric environment) applied to cover the tablet surface, resistance which last at least for two hours; to target the large intestinal sectors, also the pH condition of 6.4 shown unsuitability to determine a drug leakage from the administration device for a short exposition time and only mediums at pH 7.2 have been able to determine an active ingredient dissolution at a progressive and quite constant rate during a timeframe from 6 to 12 hours; the dissolution percentage obtained with this tablet formulation were below 15% at first hour sampling, below 25% at second hour sampling, then values were in the range 25% to 55% at fourth hour and a dissolution greater than 80% was achieved at 8 hour sampling.
- 2.7 kg of budesonide, 3.0 kg of lecithin (amphiphilic matrix forming material) and 3.0 kg of stearic acid (lipophilic matrix forming material) are mixing after sieving till an homogeneous mixture is obtained; then add 39.0 kg of inert, functional excipients and 9.0 kg of low viscosity hydroxypropylcellulose (binder) and mix for 10 minutes before adding purified water and kneading to a suitable consistence. Then pass the granulate through a rotating granulator equipped with the suitable screen and transfer the granulate to the fluid bed drier to lower the residual moisture content under 3%.
- the granulate is added of 9.0 kg of hydroxypropylcellulose (hydrophilic matrix forming material) and the suitable amount of functional excipients (in particular, microcrystalline cellulose, lactose and silicon dioxide) and, after 15 minutes of mixing, magnesium stearate in a suitable quantity to act as lubricant is added.
- hydroxypropylcellulose hydrophilic matrix forming material
- functional excipients in particular, microcrystalline cellulose, lactose and silicon dioxide
- the core are then subjected to be coated with a suspension obtained introducing into a stainless steel container 5.8 kg of EudragitTM (methacrylate copolymers), 0.6 kg of triethylcitrate and 3.0 kg of dyes and talc, using alcohol as solvent.
- the mean dissolution percentage (as average of six or more tablets) obtained with this tablet formulation were around 10-20% at second hour sampling, in the range 25% to 65% at fourth hour and a dissolution greater than 80% was achieved at 8 hour sampling.
- coated tablets individually weighing about 220 mg are obtained.
- Budesonide (3.0 kg) is mixed with soybean Lecithin (5.0 kg) till an homogeneous mixture is obtained. Then carnauba wax (2.0 kg) and stearic acid (2.0 kg) sieved through a fine screen are added. After mixing, the powders are added with other functional excipients and kneaded with a binder solution obtained by dissolving medium viscosity polyvinylpyrrolidone in water. After drying in a fluid bed and milling throughout a suitable screen, hydroxypropylmethylcellulose (35.0 kg) and other excipients, including magnesium stearate as lubricant, in a suitable quantity are added and the mixture is blended till an homogeneous powder dispersion is obtained.
- the powder mixture is subjected to compression in a rotating tabletting machine and the tablets so obtained are coated in a pan coat with a gastroresistant composition containing EudragitTM, plasticizers, dyes and pigments.
- coated tablets individually weighing around 105 mg are obtained.
- a suitable mixer is loaded with the matrix granules prepared as above and the following amounts of hydrophilic excipients: 1500 g of hydroxypropyl methylcellulose and 500 g of PolicarbophilTM are added. The components are mixed until homogeneous dispersion of the matrices, then added with 2450 g of microcrystalline cellulose, 400 g of lactose, 100 g of colloidal silica and 50 g of magnesium stearate. After further 5 minute mixing, the mix is tableted to unitary weight of 250 mg/tablet.
- Tablets are then subjected to coating using a suspension n containing polyacrylate and poly methacrylate copolymers in addition to other dyes, plasticizers and colouring agents in solvent (ethylic alcohol).
- solvent ethylic alcohol
- the inert matrix granules are loaded into a mixer in which 30 g of carbopol 971 P and 65 g of hydroxypropyl methylcellulose “are sequentially added.” After a first mixing step for homogeneously dispersing the powders, 60 g of microcrystalline cellulose and 5 g of magnesium stearate are added. After mixing, the final mixture is tabletted to unitary weight of 760 mg/tablet. The resulting tablets are film-coated with cellulose acetophthalate or polymethacrylates and a plasticizer to provide gastric resistance and prevent the early release of product in the stomach.
- the resulting tablets when subjected to dissolution test in simulated enteric juice, have shown a release of the active principles having the following profile: after 60 minutes no more than 30%, after 180 minutes no more than 60%, after 5 hours no more than 80%.
- a suitable mixer is loaded with the matrix granules prepared as above and the following amounts of hydrophilic excipients: 1500 g of hydroxypropyl methylcellulose and 500 g of policarbophil.
- the components are mixed until homogeneous dispersion of the matrices, then added with 2450 g of microcrystalline cellulose, 400 g of lactose, 100 g of colloidal silica and 50 g of magnesium stearate. After further 5 minute mixing, the mix is tabletted to unitary weight of 250 mg/tablet.
- metformin 850 g of metformin are dispersed in a granulator/kneader with 35 g of diethylene glycol monoethyl ether previously melted with 100 g of stearic acid and 55 g of carnauba wax.
- the system is heated to carry out the granulation of the active ingredient in the inert matrix.
- the resulting 1040 g of formulation are added with 110 g of hydroxypropyl methylcellulose and 20 g of magnesium stearate.
- the final mixture is tabletted to unitary weight of 1170 mg/tablet equivalent to 850 mg of active ingredient.
- the resulting tablets when subjected to dissolution test in simulated enteric juice, have shown a release of the active principles having the following profile: after 60 minutes no more than 35%, after 180 minutes no more than 60%, after 5 hours no more than 80%.
- 120 g of octylonium bromide are dispersed in a granulator/kneader with 30 g of stearic acid and 15 g of beeswax in which 10 g of diethylene glycol monoethylene had previously been melted.
- the system is heated to carry out the granulation of the active ingredient in the inert matrix.
- the resulting 10 g of formulation are added with 5 g of hydroxypropyl methylcellulose and 5 g of policarbophyl, 2 g of magnesium stearate and 3 g of microcrystalline cellulose.
- the final mixture is tabletted to unitary weight of 200 mg/tablet equivalent to 120 mg of active ingredient.
- the resulting tablets when subjected to dissolution test in simulated enteric juice, have shown a release of the active principles having the following profile: after 60 minutes no more than 25%; after 180 minutes no more than 50%; after 5 hours no more than 70%.
- the system is heated to carry out the granulation of the active ingredient in the inert matrix.
- the resulting 340 g (170 g) of formulation are added with 20 g (10 g) of hydroxypropyl methylcellulose, 10 g (5 g) of xantangum, 16 g (8 g) of microcrystalline cellulose, 4 g (2 g) of magnesium stearate.
- the final mixture is tabletted to unitary weight of 400 (200) mg/tablet equivalent to 50 (25) mg of carbidopa and 200 ( ⁇ 100) mg di levodopa.
- Nimesulide 4 g are solubilised in 50 g of diethylene glycol monoethyl ether, then 100 g of microcrystalline cellulose are added to obtain a homogeneous mixture.
- the resulting mixture is added in a granulator/kneader with 196 g of Nimesulide, 50 g of stearic acid and 25 g of carnauba wax.
- the system is heated to carry out the granulation of the active ingredient in the inert and amphiphilic matrix system.
- the final mixture is tabletted to unitary weight of 500 mg/tablet equivalent to 200 mg of active ingredient.
- the resulting tablets when subjected to dissolution test in simulated enteric juice, have shown a release of the active principles having the following profile: after 1 hour no more than 25%, after 2 hours no more than 40%, after 4 hours no more than 60%, after 8 hours no more than 90%.
- propionyl carnitine 500 g are dispersed in a granulator/kneader with 90 g of stearic acid and 40 g of carnauba wax, in which 20 g of diethylene glycol monoethyl ether had previously been melted.
- the system is heated to carry out the granulation of the active ingredient in the inert/amphiphilic matrix.
- the resulting 650 g of formulation are added with 60 g of hydroxypropyl methylcellulose and 10 g of magnesium stearate.
- the final mixture is tabletted to unitary weight of 720 mg/tablet equivalent to 500 mg of active ingredient.
- the resulting tablets when subjected to dissolution test in simulated enteric juice, have shown a release of the active principles having the following profile: after 60 minutes no more than 40%, after 180 minutes no more than 60%, after 4 hours no more than 80%, after 8 hours no more than 90%.
- Nimesulide is placed in a high rate granulator, pre-heated to about 70°, together with 200 g of cetyl alcohol and 25 g of glycerol palmitostearate the mixture is kneaded for about 15 minutes and stirred while decreasing temperature to about 30° C.
- the resulting inert matrix is added, keeping stirring and kneading during cooling, with 50 g of soy lecithin and 50 g of ethylene glycol monoethyl ether.
- the granulate is extruded through a metallic screen of suitable size and mixed with 50 g of hydroxypropyl methylcellulose, 1320 kg of maltodextrins, 2 kg of lactose-cellulose mixture, 50 g of colloidal silica, 40 g of aspartame, 150 g of citric acid, 75 g of flavour and 65 g of magnesium stearate.
- the final mixture is tabletted to unitary weight of about 500 mg, having hardness suitable for being dissolved in the mouth and a pleasant taste.
- chewable tablets are prepared replacing dextrin with mannitol and the lactose-cellulose mixture with xylitol.
- the resulting tablets have pleasant taste and give upon chewing a sensation of freshness enhancing the flavour.
- active ingredient ibuprofen mg 100 lipophilic/inert matrix component: cetyl alcohol mg 15 amphiphilic matrix component: soy lecithin mg 8 hydrophilic matrix components: mannitol mg 167 maltodextrins mg 150 methylhydroxypropylcellulose mg 30 adjuvants: aspartame mg 15 flavour mg 5 colloidal silica mg 5 magnesium stearate mg 5
- 500 mg unitary weight tablets are obtained, which undergo progressive erosion upon buccal administration, and effectively mask the bitter, irritating taste of the active ingredient.
- active ingredient diclofenac sodium mg 25 lipophilic/inert matrix component: cetyl alcohol mg 5 glycerol palmitostearate mg 5 amphiphilic matrix component: soy lecithin mg 7 hydrophilic matrix components: xylitol mg 168 maltodextrins mg 150 hydroxypropylmethylcellulose mg 20 adjuvants: aspartame mg 5 flavour mg 5 colloidal silica mg 5 magnesium stearate mg 5
- 400 mg unitary weight tablets are obtained, which undergo progressive erosion upon buccal administration, and effectively mask the irritating taste of the active ingredient.
- active ingredient chlorhexidine mg
- lipophilic/inert matrix component cetyl alcohol mg
- 0.5 glycerol palmitostearate mg
- amphiphilic matrix component mg 0.3 diethylene glycol monoethyl ether hydrophilic mg
- matrix components xylitol maltodextrins mg 96 hydroxypropyl methylcellulose mg
- adjuvants aspartame mg 3
- 150 mg unitary weight tablets are obtained, which undergo progressive erosion upon buccal administration, and effectively mask the irritating taste of the active ingredient.
- Nimesulide is placed in a high rate granulator, pre-heated to about 70°, together with g 125 of cetyl alcohol: the mixture is kneaded for about 15 minutes and stirred while decreasing temperature to about 30° C., then added with g 30 of lecithin.
- the resulting matrix is then extruded through a metallic screen of suitable size and mixed with 2.415 kg of lactose, 1.0 kg of maltodextrins, 50 g of hydroxypropyl methylcellulose, 50 g of colloidal silica, 40 g of aspartame, 150 g of citric acid, 75 g of flavour and 65 g of magnesium stearate.
- the final mixture is tabletted to about 500 mg tablets, having hardness suitable for being dissolved in the mouth and pleasant taste.
Abstract
Description
3. The use of bioerodible matrices, which are capable of being degraded by the anzimes of some biological compartment.
b) the matrix obtained as specified under a) is incorporated in a low melting lipophilic excipient or mixture of excipients, if necessary while heating to soften and/or melt the excipient itself, which thereby incorporates the active ingredient by simple dispersion forming an inert matrix which can be reduced in size to obtain inert matrix granules containing the active ingredient particles.
c) the inert matrix granules are subsequently mixed together with one or more hydrophilic water-swellable excipients. The mixture is then subjected to compression or tabletting. This way, when the tablet is contacted with biological fluids, a high viscosity swollen layer is formed, which coordinates the solvent molecules and acts as a barrier to penetration of the aqueous fluid itself inside the new structure. Said barrier antagonizes the starting “burst effect” caused by the dissolution of the medicament inglobated inside the inert matrix, which is in its turn inside the hydrophilic matrix. The amphiphilic compounds which can be used according to the invention comprise polar lipids of type I or II (lecithin, phosphatidylcholine, phosphatidylethanolainine), ceramides, glycol alkyl ethers such as diethylene glycol monomethyl ether (Transcutol®) The lipophilic matrix consists of substances selected from unsaturated or hydrogenated alcohols or fatty acids, salts, esters or amides thereof, fatty acids mono-, di- or triglycerides, the polyethoxylated derivatives thereof, waxes, ceramides, cholesterol derivatives or mixtures thereof having melting point within the range of 40 to 90° C., preferably from 60 to 70 C. If desired, a fatty acid calcium salt may be incorporated in the lipophilic matrix which is subsequently dispersed in a hydrophilic matrix prepared with alginic acid, thus remarkably increasing the hydrophilic matrix viscosity following penetration of the solvent front until contact with the lipophilic matrix granules dispersed inside. An amphiphilic matrix with high content in active ingredient, typically from 5 to 95% w/w, in particular from 20 to 70%, is first prepared by dispersing the active ingredient in a mixture of amphiphilic compounds, such as lecithin, other type II polar lipids, surfactants, or in diethylene glycol monoethyl ether; the resulting amphiphilic matrix is then mixed or kneaded, usually while hot, with lipophilic compounds suitable to form an inert matrix, such as saturated or unsaturated fatty acids, such as palmitic, stearic, myristic, lauric, laurylic, or oleic acids or mixtures thereof with other fatty acids with shorter chain, or salts or alcohols or derivatives of the cited fatty acids, such as mono-, di-, or triglycerides or esters with polyethylene glycols, alone or in combination with waxes, ceramides, cholesterol derivatives or other apolar lipids in various ratios so that the melting or softening points of the lipophilic compounds mixtures is within the range of 40 to 90 C, preferably from 60 to 70 C. Alternatively, the order of formation of the inert and amphiphilic matrices can be reversed, incorporating the inert matrix inside the amphiphilic compounds. The resulting inert lipophilic matrix is reduced into granules by an extrusion and/or granulation process, or any other known processes which retain the homogeneous dispersion and matrix structure of the starting mixture. The hydrophilic matrix consists of excipients known as hydrogels, i.e. substances which when passing from the dry state to the hydrated one, undergo the so-called “molecular relaxation”, namely a remarkable increase in mass and weight following the coordination of a large number of water molecules by the polar groups present in the polymeric chains of the excipients themselves. Examples of hydrogels which can be used according to the invention are compounds selected from acrylic or methacrylic acid polymers or copolymers, alkylvinyl polymers, hydroxyalkyl celluloses, carboxyalkyl celluloses, polysaccharides, dextrins, pectins, starches and derivatives, natural or synthetic gums, alginic acid. In case of taste-masking formulations, the use of polyalcohols such as xylitol, maltitol and mannitol as hydrophilic compounds can also be advantageous. The lipophilic matrix granules containing the active ingredient are mixed with the hydrophilic compounds cited above in a weight ratio typically ranging from 100:0.5 to 100:50 (lipophilic matrix: hydrophilic matrix). Part of the active ingredient can optionally be mixed with hydrophilic substances to provide compositions in which the active ingredient is dispersed both in the lipophilic and the hydrophilic matrix, said compositions being preferably in the form of tablets, capsules and/or minitablets. The compression of the mixture of lipophilic and/or amphiphilic matrix, hydrogel-forming compound and, optionally, active ingredient not inglobated in the lipophilic matrix, yields a macroscopically homogeneous structure in all its volume, namely a matrix containing a dispersion of the lipophilic granules in a hydrophilic matrix. A similar result can also be obtained by coating the lipophilic matrix granules with a hydrophilic polymer coating. The tablets obtainable according to the invention are subjected to known coating processes with a gastro-resistant film, consisting of, for example, acrylic and methacrylic acids polymers (Eudragit®) or copolymer or cellulose derivatives, such as cellulose acetophthalate. The composition of the invention can further contain conventional excipients, for example bioadhesive excipients such as chitosans, polyacrylamides, natural or synthetic gums, acrylic acid polymers.
Component mg/tablet |
Tablet | ||
Budesonide | 9.0 | |
Stearic Acid | 10.0 | |
Lecithin | 10.0 | |
Microcristalline cellulose | 156.0 | |
Hydroxypropylcellulose | 60.0 | |
Lactose monohydrate | 50.0 | |
Silicon dioxide | 2.0 | |
Magnesium stearate | 3.0 | |
Coating materials | ||
Eudragit L100 | 14.0 | |
Eudragit S100 | 12.0 | |
Talc | 7.9 | |
Titanium dioxiede | 4.5 | |
Triethylcitrate | 1.6 | |
Alcohol | q.s. | |
after 2 hours at pH 1 | resistant (<5%) | |
after 1 hour at pH 6.4 | resistant (<5%) | |
after 2 hours at pH 7.2 | 15% | |
after 4 hours at pH 7.2 | 37% | |
after 8 hours at pH 7.2 | 91% | |
after 2 hours at pH 1 | (<5%) resistant | |
after 1 hour at pH 6.4 | (<5%) resistant | |
after 2 hours at pH 7.2 | 9% | |
after 4 hours at pH 7.2 | 28% | |
after 8 hours at pH 7.2 | 86% | |
after 2 hours at pH 1 | (<5%) resistant | |
after 1 hour at pH 6.4 | (<5%) resistant | |
after 2 hours at pH 7.2 | 11% | |
after 4 hours at pH 7.2 | 32% | |
after 8 hours at pH 7.2 | 76% | |
active ingredient: ibuprofen | mg | 100 | |
lipophilic/inert matrix component: cetyl alcohol | mg | 15 | |
amphiphilic matrix component: soy lecithin | mg | 8 | |
hydrophilic matrix components: mannitol | mg | 167 | |
maltodextrins | mg | 150 | |
methylhydroxypropylcellulose | mg | 30 | |
adjuvants: aspartame | mg | 15 | |
flavour | mg | 5 | |
colloidal silica | mg | 5 | |
magnesium stearate | mg | 5 | |
active ingredient: diclofenac sodium | mg | 25 | |
lipophilic/inert matrix component: cetyl alcohol | mg | 5 | |
glycerol palmitostearate | mg | 5 | |
amphiphilic matrix component: soy lecithin | mg | 7 | |
hydrophilic matrix components: xylitol | mg | 168 | |
maltodextrins | mg | 150 | |
hydroxypropylmethylcellulose | mg | 20 | |
adjuvants: aspartame | mg | 5 | |
flavour | mg | 5 | |
colloidal silica | mg | 5 | |
magnesium stearate | mg | 5 | |
active ingredient: chlorhexidine | mg | 2.5 | |
lipophilic/inert matrix component: cetyl alcohol | mg | 0.5 | |
glycerol palmitostearate | mg | 0.5 | |
amphiphilic matrix component: | mg | 0.3 | |
diethylene glycol monoethyl ether hydrophilic | mg | 38 | |
matrix components: xylitol | |||
maltodextrins | mg | 96 | |
hydroxypropyl methylcellulose | mg | 10 | |
adjuvants: aspartame | mg | 3 | |
flavour | mg | 5 | |
colloidal silica | mg | 2 | |
magnesium stearate | mg | 2 | |
Claims (11)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/477,592 USRE43799E1 (en) | 1999-06-14 | 2012-05-22 | Controlled release and taste masking oral pharmaceutical composition |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1999MI001317A ITMI991317A1 (en) | 1999-06-14 | 1999-06-14 | THERAPEUTIC SYSTEMS WITH MODIFIED RELEASE FOR ORAL PHARMACEUTICAL FORM |
ITMI99A1317 | 1999-06-14 | ||
ITMI2000A0422 | 2000-03-03 | ||
IT2000MI000422A IT1317871B1 (en) | 2000-03-03 | 2000-03-03 | Controlled release and taste masking oral compositions comprising active ingredient incorporated in a matrix structure |
PCT/EP2000/005356 WO2000076478A1 (en) | 1999-06-14 | 2000-06-09 | Controlled release and taste masking oral pharmaceutical compositions |
US953201A | 2001-12-12 | 2001-12-12 | |
US12/210,969 US8029823B2 (en) | 1999-06-14 | 2008-09-15 | Controlled release and taste masking oral pharmaceutical composition |
US13/477,592 USRE43799E1 (en) | 1999-06-14 | 2012-05-22 | Controlled release and taste masking oral pharmaceutical composition |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/210,969 Reissue US8029823B2 (en) | 1999-06-14 | 2008-09-15 | Controlled release and taste masking oral pharmaceutical composition |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE43799E1 true USRE43799E1 (en) | 2012-11-13 |
Family
ID=26331662
Family Applications (20)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/009,532 Expired - Lifetime US7431943B1 (en) | 1999-06-14 | 2000-06-09 | Controlled release and taste masking oral pharmaceutical compositions |
US11/268,500 Expired - Lifetime US7410651B2 (en) | 1999-06-14 | 2005-11-08 | Controlled release and taste masking oral pharmaceutical composition |
US11/378,378 Expired - Lifetime US7410652B2 (en) | 1999-06-14 | 2006-03-20 | Controlled release and taste masking oral pharmaceutical composition |
US12/210,969 Ceased US8029823B2 (en) | 1999-06-14 | 2008-09-15 | Controlled release and taste masking oral pharmaceutical composition |
US13/249,839 Abandoned US20120021053A1 (en) | 1999-06-14 | 2011-09-30 | Controlled release and taste-masking oral pharmaceutical composition |
US13/462,430 Abandoned US20120220559A1 (en) | 1999-06-14 | 2012-05-02 | Controlled Release and Taste Masking Oral Pharmaceutical Composition |
US13/462,409 Expired - Lifetime US8293273B2 (en) | 1999-06-14 | 2012-05-02 | Controlled release and taste masking oral pharmaceutical composition |
US13/477,592 Expired - Fee Related USRE43799E1 (en) | 1999-06-14 | 2012-05-22 | Controlled release and taste masking oral pharmaceutical composition |
US13/597,867 Abandoned US20120321710A1 (en) | 1999-06-14 | 2012-08-29 | Controlled Release and Taste Masking Oral Pharmaceutical Composition |
US13/617,138 Expired - Fee Related US8784888B2 (en) | 1999-06-14 | 2012-09-14 | Controlled release and taste masking oral pharmaceutical composition |
US13/660,308 Abandoned US20130053360A1 (en) | 1999-06-14 | 2012-10-25 | Controlled release and taste masking oral pharmaceutical composition |
US14/308,279 Expired - Lifetime US9320716B2 (en) | 1999-06-14 | 2014-06-18 | Controlled release and taste masking oral pharmaceutical compositions |
US14/308,305 Expired - Fee Related US9532954B2 (en) | 1999-06-14 | 2014-06-18 | Controlled release and taste masking oral pharmaceutical compositions |
US14/514,967 Abandoned US20150056279A1 (en) | 1999-06-14 | 2014-10-15 | Controlled Release and Taste Masking Oral Pharmaceutical Compositions |
US15/369,296 Expired - Fee Related US10064878B2 (en) | 1999-06-14 | 2016-12-05 | Controlled release and taste masking oral pharmaceutical compositions |
US15/646,330 Expired - Fee Related US10143698B2 (en) | 1999-06-14 | 2017-07-11 | Controlled release and taste masking oral pharmaceutical compositions |
US15/646,538 Expired - Fee Related US10105374B2 (en) | 1999-06-14 | 2017-07-11 | Controlled release and taste masking oral pharmaceutical compositions |
US16/132,718 Abandoned US20190015428A1 (en) | 1999-06-14 | 2018-09-17 | Controlled release and taste masking oral pharmaceutical compositions |
US16/139,672 Abandoned US20190022112A1 (en) | 1999-06-14 | 2018-09-24 | Controlled release and taste masking oral pharmaceutical compositions |
US16/234,951 Abandoned US20190134061A1 (en) | 1999-06-14 | 2018-12-28 | Controlled release and taste masking oral pharmaceutical compositions |
Family Applications Before (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/009,532 Expired - Lifetime US7431943B1 (en) | 1999-06-14 | 2000-06-09 | Controlled release and taste masking oral pharmaceutical compositions |
US11/268,500 Expired - Lifetime US7410651B2 (en) | 1999-06-14 | 2005-11-08 | Controlled release and taste masking oral pharmaceutical composition |
US11/378,378 Expired - Lifetime US7410652B2 (en) | 1999-06-14 | 2006-03-20 | Controlled release and taste masking oral pharmaceutical composition |
US12/210,969 Ceased US8029823B2 (en) | 1999-06-14 | 2008-09-15 | Controlled release and taste masking oral pharmaceutical composition |
US13/249,839 Abandoned US20120021053A1 (en) | 1999-06-14 | 2011-09-30 | Controlled release and taste-masking oral pharmaceutical composition |
US13/462,430 Abandoned US20120220559A1 (en) | 1999-06-14 | 2012-05-02 | Controlled Release and Taste Masking Oral Pharmaceutical Composition |
US13/462,409 Expired - Lifetime US8293273B2 (en) | 1999-06-14 | 2012-05-02 | Controlled release and taste masking oral pharmaceutical composition |
Family Applications After (12)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/597,867 Abandoned US20120321710A1 (en) | 1999-06-14 | 2012-08-29 | Controlled Release and Taste Masking Oral Pharmaceutical Composition |
US13/617,138 Expired - Fee Related US8784888B2 (en) | 1999-06-14 | 2012-09-14 | Controlled release and taste masking oral pharmaceutical composition |
US13/660,308 Abandoned US20130053360A1 (en) | 1999-06-14 | 2012-10-25 | Controlled release and taste masking oral pharmaceutical composition |
US14/308,279 Expired - Lifetime US9320716B2 (en) | 1999-06-14 | 2014-06-18 | Controlled release and taste masking oral pharmaceutical compositions |
US14/308,305 Expired - Fee Related US9532954B2 (en) | 1999-06-14 | 2014-06-18 | Controlled release and taste masking oral pharmaceutical compositions |
US14/514,967 Abandoned US20150056279A1 (en) | 1999-06-14 | 2014-10-15 | Controlled Release and Taste Masking Oral Pharmaceutical Compositions |
US15/369,296 Expired - Fee Related US10064878B2 (en) | 1999-06-14 | 2016-12-05 | Controlled release and taste masking oral pharmaceutical compositions |
US15/646,330 Expired - Fee Related US10143698B2 (en) | 1999-06-14 | 2017-07-11 | Controlled release and taste masking oral pharmaceutical compositions |
US15/646,538 Expired - Fee Related US10105374B2 (en) | 1999-06-14 | 2017-07-11 | Controlled release and taste masking oral pharmaceutical compositions |
US16/132,718 Abandoned US20190015428A1 (en) | 1999-06-14 | 2018-09-17 | Controlled release and taste masking oral pharmaceutical compositions |
US16/139,672 Abandoned US20190022112A1 (en) | 1999-06-14 | 2018-09-24 | Controlled release and taste masking oral pharmaceutical compositions |
US16/234,951 Abandoned US20190134061A1 (en) | 1999-06-14 | 2018-12-28 | Controlled release and taste masking oral pharmaceutical compositions |
Country Status (17)
Country | Link |
---|---|
US (20) | US7431943B1 (en) |
EP (1) | EP1183014B1 (en) |
JP (3) | JP4790950B2 (en) |
CN (1) | CN1173695C (en) |
AT (1) | ATE251449T1 (en) |
AU (1) | AU5680100A (en) |
CA (1) | CA2377301C (en) |
DE (1) | DE60005819T2 (en) |
DK (1) | DK1183014T3 (en) |
ES (1) | ES2208349T3 (en) |
HK (1) | HK1046244B (en) |
MX (1) | MXPA01012889A (en) |
NO (1) | NO331642B1 (en) |
PT (1) | PT1183014E (en) |
RU (1) | RU2246293C2 (en) |
TR (1) | TR200200562T2 (en) |
WO (1) | WO2000076478A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013120881A1 (en) | 2012-02-13 | 2013-08-22 | Cosmo Technologies Limited | Method for treating intestinal diseases presenting at least one inflammatory component |
WO2015071812A1 (en) | 2013-11-18 | 2015-05-21 | Wockhardt Limited | Solid oral modified-release composition comprising budesonide or salt thereof |
US9907755B2 (en) | 2013-03-14 | 2018-03-06 | Therabiome, Llc | Targeted gastrointestinal tract delivery of probiotic organisms and/or therapeutic agents |
US10588857B2 (en) | 2012-03-29 | 2020-03-17 | Therabiome, Llc | Gastrointestinal site-specific oral vaccination formulations active on the ileum and appendix |
US11344562B2 (en) | 2017-08-15 | 2022-05-31 | Nephron Pharmaceuticals Corporation | Aqueous nebulization composition |
Families Citing this family (88)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK1183014T3 (en) * | 1999-06-14 | 2004-02-09 | Cosmo Spa | Flavored controlled release oral pharmaceutical compositions |
ITMI991316A1 (en) * | 1999-06-14 | 2000-12-14 | Cip Ninety Two 92 S A | ORAL PHARMACEUTICAL COMPOSITIONS WITH MODIFIED RELEASE OF MESALAZINE |
US8895064B2 (en) | 1999-06-14 | 2014-11-25 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
CA2359812C (en) | 2000-11-20 | 2004-02-10 | The Procter & Gamble Company | Pharmaceutical dosage form with multiple coatings for reduced impact of coating fractures |
ITMI20011337A1 (en) | 2001-06-26 | 2002-12-26 | Farmatron Ltd | ORAL PHARMACEUTICAL COMPOSITIONS WITH MODIFIED RELEASE OF THE ACTIVE SUBSTANCE |
TWI312285B (en) | 2001-10-25 | 2009-07-21 | Depomed Inc | Methods of treatment using a gastric retained gabapentin dosage |
US7612112B2 (en) | 2001-10-25 | 2009-11-03 | Depomed, Inc. | Methods of treatment using a gastric retained gabapentin dosage |
ITMI20012366A1 (en) * | 2001-11-09 | 2003-05-09 | Farmatron Ltd | THERAPEUTIC SYSTEMS STABILIZED WITH IMMEDIATE RELEASE AND / OR MODIFIED FOR THE ORAL ADMINISTRATION OF ACTIVE AND / OR EXCIPIENT PRINCIPLES AND / OR WINGS |
TWI252111B (en) * | 2001-12-14 | 2006-04-01 | Solvay Pharm Gmbh | Matrix film tablet with controlled release of a natural mixture of conjugated estrogens |
FR2838349B1 (en) * | 2002-04-15 | 2004-06-25 | Laurence Paris | LIQUID COMPOSITIONS FOR SUSTAINED RELEASE SOFT CAPSULES AND PROCESS FOR PRODUCING THE SAME |
CN1668284A (en) * | 2002-06-07 | 2005-09-14 | 兰贝克赛实验室有限公司 | Sustained release oral dosage forms of gabapentin |
US20040086566A1 (en) * | 2002-11-04 | 2004-05-06 | Alpharma, Inc. | Waxy matrix dosage forms |
FR2852843B1 (en) * | 2003-03-24 | 2008-05-23 | Karim Ioualalen | GALENIC SYSTEM FOR MASKING TASTE |
WO2005009432A1 (en) * | 2003-07-29 | 2005-02-03 | Ranbaxy Laboratories Limited | New dosage regimen in case of concurrent intake of gabapentin with food and an increased oral bioavailability therewith |
WO2005072717A1 (en) * | 2004-01-29 | 2005-08-11 | Dainippon Sumitomo Pharma Co., Ltd. | Biguanide preparation for internal use |
ITMI20040187A1 (en) * | 2004-02-06 | 2004-05-06 | Cosmo Spa | PHARMACEUTICAL OR DIETETIC COMPOSITIONS BASED ON SHORT CHAIN FATTY ACIDS AND COMPLEX SUGARS FOR INTESTINAL DYSFUNCTIONS |
ITMI20041295A1 (en) * | 2004-06-25 | 2004-09-25 | Cosmo Spa | ORAL ANTI-MICROBIAL PHARMACEUTICAL COMPOSITIONS |
US8497258B2 (en) | 2005-11-12 | 2013-07-30 | The Regents Of The University Of California | Viscous budesonide for the treatment of inflammatory diseases of the gastrointestinal tract |
US20090176882A1 (en) | 2008-12-09 | 2009-07-09 | Depomed, Inc. | Gastric retentive gabapentin dosage forms and methods for using same |
ES2288117B1 (en) * | 2006-05-08 | 2008-12-01 | Combino Pharm, S.L. | SOLID PHARMACEUTICAL COMPOSITION OF GABAPENTINA. |
CN102988373A (en) * | 2006-07-19 | 2013-03-27 | 德克萨斯大学系统董事会 | Preparations of phospholipids and pharmaceuticals containing 5-amino salicylic acid for the treatment of inflammatory bowel disease |
EP2081555A2 (en) * | 2006-09-12 | 2009-07-29 | Cosmo Technologies Ltd. | Pharmaceutical compositions for the oral or rectal administration of protein substances |
FR2913884A1 (en) * | 2007-03-21 | 2008-09-26 | Oralance Pharma Sa | NON-IONIZABLE HYDROPHOBIC GALENIC SYSTEM |
DE102007041588A1 (en) * | 2007-09-01 | 2009-03-05 | Lts Lohmann Therapie-Systeme Ag | Medicament, useful for controlled, continuous or sudden release of medicinal substances in the medicament, comprises harmless, alcoholic fermentation enabled yeast, carbohydrates and water in a separate compartment |
CN102065858B (en) * | 2008-04-29 | 2014-07-02 | 法奈科斯公司 | Combination compositions for treating alzheimer disease and related disorders with zonisamide and acamprosate |
MX2011001864A (en) | 2008-08-20 | 2011-06-20 | Univ Texas | Hot-melt extrusion of modified release multi-particulates. |
CA2638240C (en) * | 2008-08-29 | 2010-02-02 | Alexander Macgregor | Method of treating dysglycemia and glucose excursions |
AU2008243202B2 (en) * | 2008-11-11 | 2015-08-20 | Cosmo Technologies Ltd | Oral antimicrobial pharmaceutical compositions |
US20150224081A1 (en) * | 2009-01-12 | 2015-08-13 | Biokier, Inc. | Composition and method for treatment of diabetes |
CN102355896A (en) * | 2009-01-12 | 2012-02-15 | 拜奥基尔公司 | Composition and method for treatment of diabetes |
US9006288B2 (en) | 2009-01-12 | 2015-04-14 | Biokier, Inc. | Composition and method for treatment of diabetes |
US9314444B2 (en) | 2009-01-12 | 2016-04-19 | Biokier, Inc. | Composition and method for treatment of NASH |
US8945615B2 (en) | 2009-02-17 | 2015-02-03 | Mylan Pharmaceuticals Inc. | Controlled release budesonide minitablets |
US8945616B2 (en) * | 2009-02-17 | 2015-02-03 | Mylan Pharmaceuticals Inc. | Controlled release budesonide minitablets |
DE102009012788A1 (en) * | 2009-03-13 | 2010-09-30 | J. Rettenmaier & Söhne Gmbh + Co. Kg | Compressible tablet material with oily agent, tablet and method and apparatus for their preparation |
JP5640079B2 (en) | 2009-05-18 | 2014-12-10 | シグモイド・ファーマ・リミテッドSigmoid Pharma Limited | Oil droplet-containing composition |
GB0909680D0 (en) | 2009-06-05 | 2009-07-22 | Euro Celtique Sa | Dosage form |
CA2765033C (en) | 2009-06-12 | 2020-07-14 | Meritage Pharma, Inc. | Methods for treating gastrointestinal disorders |
ES2736155T3 (en) * | 2009-08-24 | 2019-12-26 | Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi | Otilonium tablets by direct compression |
AU2010298303A1 (en) | 2009-09-23 | 2012-04-12 | Biokier, Inc. | Composition and method for treatment of diabetes |
US9463163B2 (en) | 2009-10-16 | 2016-10-11 | Sun Pharmaceutical Industries Limited | Delayed release pharmaceutical composition of mesalamine |
WO2011057131A1 (en) | 2009-11-09 | 2011-05-12 | Spotlight Technology Partners Llc | Polysaccharide based hydrogels |
EP2498764B1 (en) | 2009-11-09 | 2017-09-06 | Spotlight Technology Partners LLC | Fragmented hydrogels |
IT1398643B1 (en) | 2010-03-04 | 2013-03-08 | Cosmo Technologies Ltd | SOLID COMPOSITION FOR ORAL ADMINISTRATION OF DYES, AND DIAGNOSTIC USE OF THE SAME |
CN109593814A (en) | 2010-05-12 | 2019-04-09 | 哥伦比亚大学纽约管理委员会 | Screening analysis, the method and pharmaceutical composition for identifying medicament |
WO2011154975A2 (en) | 2010-06-08 | 2011-12-15 | Cadila Healthcare Limited | Pharmaceutical compositions of metformin |
CA2805445C (en) | 2010-07-29 | 2018-05-01 | Cosmo Technologies Ltd. | Pharmaceutical and/or dietary compositions based on short chain fatty acids |
IT1402047B1 (en) * | 2010-10-19 | 2013-08-28 | Cross Pharma Sa | USE OF MEXIPROSTIL IN THE TREATMENT OF INTESTINAL INFLAMMATORY DISEASES |
US8895536B2 (en) | 2010-10-29 | 2014-11-25 | Infirst Healthcare Ltd. | Compositions and methods for treating chronic inflammation and inflammatory diseases |
US10695431B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
US11224659B2 (en) | 2010-10-29 | 2022-01-18 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
EP2446877A1 (en) * | 2010-10-29 | 2012-05-02 | Roquette Frères | Modified starch derivative-based matrix for colon targeting |
US9271950B2 (en) | 2010-10-29 | 2016-03-01 | Infirst Healthcare Limited | Compositions for treating chronic inflammation and inflammatory diseases |
US11202831B2 (en) | 2010-10-29 | 2021-12-21 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
US10695432B2 (en) | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in severe pain |
US11730709B2 (en) | 2010-10-29 | 2023-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
US9308213B2 (en) | 2010-10-29 | 2016-04-12 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
US9744132B2 (en) | 2010-10-29 | 2017-08-29 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
US9504664B2 (en) | 2010-10-29 | 2016-11-29 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
US9737500B2 (en) | 2010-10-29 | 2017-08-22 | Infirst Healthcare Limited | Compositions and methods for treating severe pain |
MX2013012720A (en) * | 2011-05-02 | 2013-12-06 | Biokier Inc | Composition and method for treatment of diabetes. |
AT511581A1 (en) * | 2011-05-26 | 2012-12-15 | G L Pharma Gmbh | ORAL RETARDANT FORMULATION |
US10154964B2 (en) | 2011-09-07 | 2018-12-18 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
AU2011248587A1 (en) * | 2011-11-09 | 2013-05-23 | Cosmo Technologies Ltd | Controlled release and taste masking oral pharmaceutical composition |
MX351453B (en) * | 2011-12-02 | 2017-10-16 | Pegasus Laboratories Inc | Amphipathic lipid-based sustained release compositions. |
US10722458B2 (en) * | 2011-12-02 | 2020-07-28 | Pegasus Laboratories, Inc. | Amphipathic lipid-based sustained release compositions |
EP2722058A1 (en) | 2012-10-19 | 2014-04-23 | Cosmo Technologies Ltd | Solid oral composition containing dyes for use in endoscopic diagnosis |
BR112015015898B1 (en) * | 2013-01-14 | 2022-04-12 | Infirst Healthcare Limited | Solid solution pharmaceutical composition, and use of a pharmaceutical composition |
MX2015009045A (en) * | 2013-01-14 | 2015-12-17 | Infirst Healthcare Ltd | Compositions and methods for treating severe pain. |
CA2898017A1 (en) * | 2013-02-04 | 2014-08-07 | Infirst Healthcare Limited | Compositions and methods for treating chronic inflammation and inflammatory diseases |
US9240075B2 (en) | 2013-03-15 | 2016-01-19 | Daqri, Llc | Campaign optimization for experience content dataset |
CN103417507B (en) * | 2013-08-23 | 2015-12-02 | 王显著 | Budesonide pharmaceutical composition |
US20150073057A1 (en) | 2013-09-06 | 2015-03-12 | Biokier, Inc. | Composition and method for treatment of diabetes |
ITMI20131578A1 (en) * | 2013-09-25 | 2015-03-26 | Giellepi S P A | SUBSTANCE AND FORMULATION FOR THE TREATMENT OF CHRONIC INTESTINAL INFLAMMATORY DISEASES |
IN2013MU03373A (en) * | 2013-10-25 | 2015-07-17 | Cadila Healthcare Ltd | |
GB2525227B (en) | 2014-04-16 | 2016-09-14 | Jaguar Land Rover Ltd | Bumper assembly method and apparatus |
EP3160503B1 (en) | 2014-06-26 | 2021-02-17 | The Trustees of Columbia University in the City of New York | Inhibition of serotonin expression in gut enteroendocrine cells results in conversion to insulin-positive cells |
EP3006453A1 (en) * | 2014-10-08 | 2016-04-13 | Cosmo Technologies Ltd. | 17alpha-monoesters and 17alpha,21-diesters of cortexolone for use in the treatment of tumors |
CN104523717A (en) * | 2015-01-06 | 2015-04-22 | 西南大学 | Simethicone otilonium bromide chewable tablets and preparing method thereof |
WO2017058881A1 (en) | 2015-09-28 | 2017-04-06 | The Trustees Of Columbia University In The City Of New York | Use of pentoxifylline with immune checkpoint-blockade therapies for the treatment of melanoma |
CA3043451A1 (en) | 2016-11-28 | 2018-05-31 | Cosmo Technologies Ltd. | Solid oral composition containing dyes |
WO2018129079A1 (en) * | 2017-01-03 | 2018-07-12 | Thermolife International, Llc | Method of isolating theacrine and composition comprising theacrine |
AU2018364617A1 (en) | 2017-11-10 | 2020-05-07 | Cosmo Technologies Ltd. | Oral rifamycin SV compositions |
EP3501503A1 (en) * | 2017-12-22 | 2019-06-26 | Cosmo Technologies Ltd. | Solid delivery composition |
EP3613414A1 (en) | 2018-08-24 | 2020-02-26 | Dr. Falk Pharma Gmbh | Pellets with multilayer structure for delayed release of the drug in the distal colon |
CN110585164A (en) * | 2019-10-08 | 2019-12-20 | 苏州弘森药业股份有限公司 | Method for preparing esomeprazole magnesium sodium bicarbonate capsule |
WO2022254456A1 (en) * | 2021-06-01 | 2022-12-08 | Nbi Biosciences Pvt Ltd | Microbial-triggered oral intestinal drug delivery formulation and method of preparation thereof |
US11896719B2 (en) | 2022-01-24 | 2024-02-13 | Calliditas Therapeutics Ab | Pharmaceutical compositions |
Citations (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB935639A (en) | 1961-06-16 | 1963-09-04 | Hoffmann La Roche | Pharmaceutical compositions comprising drug/resin adsorbates |
JPS6348226A (en) | 1986-08-14 | 1988-02-29 | Ono Pharmaceut Co Ltd | Slowly releasing solid preparation for oral administration |
EP0482576A1 (en) | 1990-10-23 | 1992-04-29 | Freund Industrial Co., Ltd. | Prolonged release dosage form of drug and method for producing the same |
EP0514008A1 (en) | 1991-04-19 | 1992-11-19 | Takeda Chemical Industries, Ltd. | Pharmaceutical preparations based on gastrointestinal mucosa-adherent matrixes or coatings |
DE4131562A1 (en) | 1991-09-18 | 1993-03-25 | Medac Klinische Spezialpraep | SOLID LIPID PARTICLE SOLID LIPID NANOSPHERES (SLN) |
US5320848A (en) | 1991-05-28 | 1994-06-14 | Affinity Biotech, Inc. | Chewable drug-delivery composition |
US5342625A (en) * | 1988-09-16 | 1994-08-30 | Sandoz Ltd. | Pharmaceutical compositions comprising cyclosporins |
JPH08503482A (en) | 1992-11-27 | 1996-04-16 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Cimetidine granules coated with partially hydrogenated vegetable oil |
WO1996013273A1 (en) | 1994-10-26 | 1996-05-09 | Novartis Ag | Pharmaceutical compositions |
US5534501A (en) | 1991-06-04 | 1996-07-09 | A Et S Biovecteurs | Particle for use as a milk fat globule substitute, composition containing same and process for the preparation of said particle |
US5643602A (en) * | 1989-11-22 | 1997-07-01 | Astra Aktiebolag | Oral composition for the treatment of inflammatory bowel disease |
US5681584A (en) | 1993-04-23 | 1997-10-28 | Ciba-Geigy Corporation | Controlled release drug delivery device |
WO1998000169A1 (en) | 1996-07-02 | 1998-01-08 | Cortecs (Uk) Limited) | Hydrophobic preparations containing medium chain monoglycerides |
US5811388A (en) | 1995-06-07 | 1998-09-22 | Cibus Pharmaceutical, Inc. | Delivery of drugs to the lower GI tract |
US5840332A (en) | 1996-01-18 | 1998-11-24 | Perio Products Ltd. | Gastrointestinal drug delivery system |
WO1999011245A1 (en) | 1997-08-29 | 1999-03-11 | Pharmacia & Upjohn Company | A pharmaceutical composition having two coating layers |
WO1999017752A1 (en) | 1997-10-07 | 1999-04-15 | Fuisz Technologies Ltd. | Improved dosage units |
US5908833A (en) | 1993-01-08 | 1999-06-01 | Aktiebolaget Astra | Colon or ileum-specific steroid derivatives |
US6190692B1 (en) | 1997-01-29 | 2001-02-20 | Cesare Busetti | Time-specific controlled release capsule formulations and method of preparing same |
US6562363B1 (en) | 1997-09-26 | 2003-05-13 | Noven Pharmaceuticals, Inc. | Bioadhesive compositions and methods for topical administration of active agents |
US7410651B2 (en) | 1999-06-14 | 2008-08-12 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
JP4159217B2 (en) | 1999-12-15 | 2008-10-01 | 花王株式会社 | Topical skin preparation |
US20120021052A1 (en) | 1999-06-14 | 2012-01-26 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133863A (en) | 1961-03-10 | 1964-05-19 | Strong Cobb Arner Inc | Sustained release therapeutic tablet compositions comprising organic solvent-gelled gums |
US3800051A (en) | 1970-09-21 | 1974-03-26 | Dow Chemical Co | Reducing serum cholesterol with certain substituted phenols |
US3965256A (en) | 1972-05-16 | 1976-06-22 | Synergistics | Slow release pharmaceutical compositions |
ZA825384B (en) | 1981-07-31 | 1983-05-25 | Tillott J B Ltd | Orally administrable pharmaceutical compositions |
AU571312B2 (en) | 1984-02-10 | 1988-04-14 | Nycomed Danmark A/S | Diffusion coated multiple-units dosage form |
US4608248A (en) | 1985-11-08 | 1986-08-26 | Warner-Lambert Company | Process for time-controlled release of active ingredients |
IL92343A0 (en) | 1988-12-20 | 1990-07-26 | Gist Brocades Nv | Granulate for multiparticulate controlled release oral compositions,their preparation and oral pharmaceutical compositions containing them |
IT1246382B (en) | 1990-04-17 | 1994-11-18 | Eurand Int | METHOD FOR THE TARGETED AND CONTROLLED DELIVERY OF DRUGS IN THE INTESTINE AND PARTICULARLY IN THE COLON |
US5183815A (en) | 1991-01-22 | 1993-02-02 | Merck & Co., Inc. | Bone acting agents |
WO1992016214A1 (en) | 1991-03-15 | 1992-10-01 | Norwich Eaton Pharmaceuticals Inc. | The use of 5-aminosalicylic acid in the treatment of irritable bowel syndrome - diarrheal phase or type (ibs-d) |
US5874063A (en) | 1991-04-11 | 1999-02-23 | Astra Aktiebolag | Pharmaceutical formulation |
IT1250654B (en) | 1991-07-08 | 1995-04-21 | Farcon Ag | METHOD FOR THE PREPARATION OF ORAL PHARMACEUTICAL FORMS WITH EXTENDED RELEASE CONTAINING ACTIVE SUBSTANCES SOLUBILITY DEPENDENT ON THE PH VALUE. |
WO1995016451A1 (en) | 1992-06-22 | 1995-06-22 | Franck Arno Gouchet | Tablets for the controlled release of 4-asa |
US5472711A (en) | 1992-07-30 | 1995-12-05 | Edward Mendell Co., Inc. | Agglomerated hydrophilic complexes with multi-phasic release characteristics |
US5686105A (en) * | 1993-10-19 | 1997-11-11 | The Procter & Gamble Company | Pharmaceutical dosage form with multiple enteric polymer coatings for colonic delivery |
AU685262B2 (en) * | 1994-03-30 | 1998-01-15 | Gs Development Ab | Use of fatty acid esters as bioadhesive substances |
US5447729A (en) | 1994-04-07 | 1995-09-05 | Pharmavene, Inc. | Multilamellar drug delivery systems |
DE69535432T2 (en) | 1994-04-22 | 2007-12-06 | Astellas Pharma Inc. | Colon-specific drug delivery system |
WO1995030674A1 (en) * | 1994-05-05 | 1995-11-16 | Merck Sharp & Dohme Limited | Morpholine derivatives and their use as antagonists of tachikinins |
US5849327A (en) | 1994-07-29 | 1998-12-15 | Advanced Polymer Systems, Inc. | Delivery of drugs to the lower gastrointestinal tract |
IL139728A (en) | 1995-01-09 | 2003-06-24 | Penwest Pharmaceuticals Compan | Aqueous slurry composition containing microcrystalline cellulose for preparing a pharmaceutical excipient |
SI9500173B (en) | 1995-05-19 | 2002-02-28 | Lek, | Three-phase pharmaceutical form with constant and controlled release of amorphous active ingredient for single daily application |
US5863910A (en) | 1996-01-12 | 1999-01-26 | Bolonick; Joel | Treatment of chronic inflammatory disorders of the gastrointestinal tract |
EP0919228A4 (en) | 1996-08-02 | 2001-12-12 | Hisamitsu Pharmaceutical Co | Capsules for oral preparations and capsule preparations for oral administration |
ES2203963T3 (en) | 1997-05-30 | 2004-04-16 | Osmotica Corp. | MULTI-PATH OSMOTIC DEVICE. |
DE29717252U1 (en) | 1997-09-26 | 1998-02-19 | Falk Pharma Gmbh | Drug kit consisting of a budesonide-containing and an ursodeoxycholic acid-containing drug for the treatment of cholestatic liver diseases |
US6607751B1 (en) | 1997-10-10 | 2003-08-19 | Intellipharamaceutics Corp. | Controlled release delivery device for pharmaceutical agents incorporating microbial polysaccharide gum |
IT1298575B1 (en) | 1998-02-06 | 2000-01-12 | Vectorpharma Int | PHARMACEUTICAL COMPOSITIONS IN THE FORM OF NANOPARTICLES INCLUDING LIPID SUBSTANCES AND ANTIPHILIC SUBSTANCES AND RELATED PROCESS OF |
US6239120B1 (en) * | 1998-03-17 | 2001-05-29 | Pharmalink Ab | Method and means for treating glomerulonephritis |
CA2274943A1 (en) | 1998-06-17 | 1999-12-17 | Stephen L. Wolman | Compositions for the treatment and prevention of inflammatory diseases of the gastrointestinal tract and methods and uses thereof |
DE19849737A1 (en) | 1998-10-28 | 2000-05-04 | Falk Pharma Gmbh | Combination agent for the treatment of inflammatory bowel disease |
ITMI991316A1 (en) | 1999-06-14 | 2000-12-14 | Cip Ninety Two 92 S A | ORAL PHARMACEUTICAL COMPOSITIONS WITH MODIFIED RELEASE OF MESALAZINE |
US6363635B1 (en) | 1999-10-22 | 2002-04-02 | Superior Bronze Corporation Of America | Memorial markers and method for producing the same |
ITMI20012599A1 (en) | 2001-12-11 | 2003-06-11 | Cosmo Spa | PHARMACEUTICAL COMPOSITIONS FOR THE ORAL ADMINISTRATION OF HEPARINE OR DERIVATIVES, USEFUL FOR THERAPY OF INFLAMMATORY DISEASES OF THE INT |
DE10214002A1 (en) | 2002-03-27 | 2003-10-09 | Roehm Gmbh | Pharmaceutical formulation for the active substance budesonide |
GB0222612D0 (en) * | 2002-09-30 | 2002-11-06 | Univ Gent | Controlled delivery system for bioactive substances |
EP1607087A1 (en) | 2003-03-27 | 2005-12-21 | Hisamitsu Pharmaceutical Co., Inc. | Medicinal oral preparations for colon delivery, medicinal oral preparations for treating colon cancer and medicinal oral preparations for treating colitis |
DE102004043863A1 (en) | 2004-09-10 | 2006-03-16 | Nitec Pharma Ag | Tablets with local and time-controlled drug release in the gastrointestinal tract |
US7715806B2 (en) | 2004-10-06 | 2010-05-11 | Broadcom Corporation | Method and system for diversity processing including using dedicated pilot method for closed loop |
AU2006348180A1 (en) | 2006-09-13 | 2008-03-20 | Warner Chilcott Company, Llc | Methods of treatment for ulcerative colitis |
JP5132416B2 (en) | 2008-05-08 | 2013-01-30 | キヤノン株式会社 | Image processing apparatus and control method thereof |
ME01256B (en) | 2008-07-21 | 2013-06-20 | Dr Falk Pharma Gmbh | Pharmaceutical formulation for treating the upper digestive tract |
EP2298321A1 (en) | 2009-08-26 | 2011-03-23 | Nordic Pharma | Novel pharmaceutical compositions for treating IBD |
IT1398643B1 (en) | 2010-03-04 | 2013-03-08 | Cosmo Technologies Ltd | SOLID COMPOSITION FOR ORAL ADMINISTRATION OF DYES, AND DIAGNOSTIC USE OF THE SAME |
US8787888B2 (en) * | 2012-08-29 | 2014-07-22 | Facebook, Inc. | Sharing location information during a communication session |
-
2000
- 2000-06-09 DK DK00942044T patent/DK1183014T3/en active
- 2000-06-09 CA CA002377301A patent/CA2377301C/en not_active Expired - Lifetime
- 2000-06-09 EP EP00942044A patent/EP1183014B1/en not_active Expired - Lifetime
- 2000-06-09 ES ES00942044T patent/ES2208349T3/en not_active Expired - Lifetime
- 2000-06-09 US US10/009,532 patent/US7431943B1/en not_active Expired - Lifetime
- 2000-06-09 MX MXPA01012889A patent/MXPA01012889A/en active IP Right Grant
- 2000-06-09 WO PCT/EP2000/005356 patent/WO2000076478A1/en active IP Right Grant
- 2000-06-09 JP JP2001502812A patent/JP4790950B2/en not_active Expired - Lifetime
- 2000-06-09 AT AT00942044T patent/ATE251449T1/en active
- 2000-06-09 DE DE60005819T patent/DE60005819T2/en not_active Expired - Lifetime
- 2000-06-09 RU RU2002100367/15A patent/RU2246293C2/en active
- 2000-06-09 TR TR2002/00562T patent/TR200200562T2/en unknown
- 2000-06-09 AU AU56801/00A patent/AU5680100A/en not_active Abandoned
- 2000-06-09 CN CNB008088942A patent/CN1173695C/en not_active Expired - Lifetime
- 2000-06-09 PT PT00942044T patent/PT1183014E/en unknown
-
2001
- 2001-12-14 NO NO20016108A patent/NO331642B1/en not_active IP Right Cessation
-
2002
- 2002-10-30 HK HK02107843.2A patent/HK1046244B/en not_active IP Right Cessation
-
2005
- 2005-11-08 US US11/268,500 patent/US7410651B2/en not_active Expired - Lifetime
-
2006
- 2006-03-20 US US11/378,378 patent/US7410652B2/en not_active Expired - Lifetime
-
2008
- 2008-09-15 US US12/210,969 patent/US8029823B2/en not_active Ceased
-
2011
- 2011-01-04 JP JP2011000092A patent/JP5279851B2/en not_active Expired - Lifetime
- 2011-01-04 JP JP2011000091A patent/JP5279850B2/en not_active Expired - Lifetime
- 2011-09-30 US US13/249,839 patent/US20120021053A1/en not_active Abandoned
-
2012
- 2012-05-02 US US13/462,430 patent/US20120220559A1/en not_active Abandoned
- 2012-05-02 US US13/462,409 patent/US8293273B2/en not_active Expired - Lifetime
- 2012-05-22 US US13/477,592 patent/USRE43799E1/en not_active Expired - Fee Related
- 2012-08-29 US US13/597,867 patent/US20120321710A1/en not_active Abandoned
- 2012-09-14 US US13/617,138 patent/US8784888B2/en not_active Expired - Fee Related
- 2012-10-25 US US13/660,308 patent/US20130053360A1/en not_active Abandoned
-
2014
- 2014-06-18 US US14/308,279 patent/US9320716B2/en not_active Expired - Lifetime
- 2014-06-18 US US14/308,305 patent/US9532954B2/en not_active Expired - Fee Related
- 2014-10-15 US US14/514,967 patent/US20150056279A1/en not_active Abandoned
-
2016
- 2016-12-05 US US15/369,296 patent/US10064878B2/en not_active Expired - Fee Related
-
2017
- 2017-07-11 US US15/646,330 patent/US10143698B2/en not_active Expired - Fee Related
- 2017-07-11 US US15/646,538 patent/US10105374B2/en not_active Expired - Fee Related
-
2018
- 2018-09-17 US US16/132,718 patent/US20190015428A1/en not_active Abandoned
- 2018-09-24 US US16/139,672 patent/US20190022112A1/en not_active Abandoned
- 2018-12-28 US US16/234,951 patent/US20190134061A1/en not_active Abandoned
Patent Citations (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB935639A (en) | 1961-06-16 | 1963-09-04 | Hoffmann La Roche | Pharmaceutical compositions comprising drug/resin adsorbates |
JPS6348226A (en) | 1986-08-14 | 1988-02-29 | Ono Pharmaceut Co Ltd | Slowly releasing solid preparation for oral administration |
US5342625A (en) * | 1988-09-16 | 1994-08-30 | Sandoz Ltd. | Pharmaceutical compositions comprising cyclosporins |
US5643602A (en) * | 1989-11-22 | 1997-07-01 | Astra Aktiebolag | Oral composition for the treatment of inflammatory bowel disease |
EP0482576A1 (en) | 1990-10-23 | 1992-04-29 | Freund Industrial Co., Ltd. | Prolonged release dosage form of drug and method for producing the same |
JPH04159217A (en) | 1990-10-23 | 1992-06-02 | Freunt Ind Co Ltd | Sustained release preparation and production thereof |
EP0514008A1 (en) | 1991-04-19 | 1992-11-19 | Takeda Chemical Industries, Ltd. | Pharmaceutical preparations based on gastrointestinal mucosa-adherent matrixes or coatings |
US6368635B1 (en) | 1991-04-19 | 2002-04-09 | Takeda Chemical Industries, Ltd. | Gastrointestinal mucosa-adherent matrixes pharmaceutical preparations and a coating composition |
JPH05132416A (en) | 1991-04-19 | 1993-05-28 | Takeda Chem Ind Ltd | Matrix adherent to mucosa of alimentary tract, preparation and coating agent |
US5320848A (en) | 1991-05-28 | 1994-06-14 | Affinity Biotech, Inc. | Chewable drug-delivery composition |
JPH06511478A (en) | 1991-05-28 | 1994-12-22 | マクニール―ピーピーシー・インコーポレーテツド | Chewable drug administration composition |
US5534501A (en) | 1991-06-04 | 1996-07-09 | A Et S Biovecteurs | Particle for use as a milk fat globule substitute, composition containing same and process for the preparation of said particle |
JPH06510772A (en) | 1991-09-18 | 1994-12-01 | メダク・ゲゼルシャフト・ヒューア・クリーニシェ・スペツィアルプレパラーテ・ミット・ベシュレンクター・ハフツング | Pharmaceutical carrier made of solid lipid microparticles (solid lipid nanospheres) |
CA2119253A1 (en) | 1991-09-18 | 1993-04-01 | Stefan Lucks | Medication Vehicles Made of Solid Lipid Particles (Solid Lipid Nanospheres-SLN) |
DE4131562A1 (en) | 1991-09-18 | 1993-03-25 | Medac Klinische Spezialpraep | SOLID LIPID PARTICLE SOLID LIPID NANOSPHERES (SLN) |
JPH08503482A (en) | 1992-11-27 | 1996-04-16 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Cimetidine granules coated with partially hydrogenated vegetable oil |
US5597844A (en) | 1992-11-27 | 1997-01-28 | Chauhan; Sushil | Cimetidine granules coated with a partially hydrogenated vegetable oil |
US5908833A (en) | 1993-01-08 | 1999-06-01 | Aktiebolaget Astra | Colon or ileum-specific steroid derivatives |
US6140308A (en) | 1993-01-08 | 2000-10-31 | Aktiebolaget Astra | Colon or ileum-specific glucocorticosteroid derivatives |
US5681584A (en) | 1993-04-23 | 1997-10-28 | Ciba-Geigy Corporation | Controlled release drug delivery device |
WO1996013273A1 (en) | 1994-10-26 | 1996-05-09 | Novartis Ag | Pharmaceutical compositions |
US5811388A (en) | 1995-06-07 | 1998-09-22 | Cibus Pharmaceutical, Inc. | Delivery of drugs to the lower GI tract |
US5840332A (en) | 1996-01-18 | 1998-11-24 | Perio Products Ltd. | Gastrointestinal drug delivery system |
WO1998000169A1 (en) | 1996-07-02 | 1998-01-08 | Cortecs (Uk) Limited) | Hydrophobic preparations containing medium chain monoglycerides |
JP2000515130A (en) | 1996-07-02 | 2000-11-14 | コーテックス(ユーケー)リミテッド | Hydrophobic preparations containing medium-chain monoglycerides |
US6258377B1 (en) | 1996-07-02 | 2001-07-10 | Provalis Uk Limited | Hydrophobic preparations containing medium chain monoglycerides |
US6190692B1 (en) | 1997-01-29 | 2001-02-20 | Cesare Busetti | Time-specific controlled release capsule formulations and method of preparing same |
WO1999011245A1 (en) | 1997-08-29 | 1999-03-11 | Pharmacia & Upjohn Company | A pharmaceutical composition having two coating layers |
US6562363B1 (en) | 1997-09-26 | 2003-05-13 | Noven Pharmaceuticals, Inc. | Bioadhesive compositions and methods for topical administration of active agents |
WO1999017752A1 (en) | 1997-10-07 | 1999-04-15 | Fuisz Technologies Ltd. | Improved dosage units |
JP2000510488A (en) | 1997-10-07 | 2000-08-15 | フイズ テクノロジーズ リミテッド | Improved dosing unit |
US5965167A (en) | 1997-10-07 | 1999-10-12 | Sanghvi; Pradeepkumar P. | Dosage units |
US7410651B2 (en) | 1999-06-14 | 2008-08-12 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
US7410652B2 (en) | 1999-06-14 | 2008-08-12 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
US7431943B1 (en) | 1999-06-14 | 2008-10-07 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical compositions |
US8029823B2 (en) | 1999-06-14 | 2011-10-04 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
US20120021053A1 (en) | 1999-06-14 | 2012-01-26 | Cosmo Technologies Limited | Controlled release and taste-masking oral pharmaceutical composition |
US20120021052A1 (en) | 1999-06-14 | 2012-01-26 | Cosmo Technologies Limited | Controlled release and taste masking oral pharmaceutical composition |
JP4159217B2 (en) | 1999-12-15 | 2008-10-01 | 花王株式会社 | Topical skin preparation |
Non-Patent Citations (22)
Title |
---|
"Budesonide"-Wikipedia, the free encyclopedia, (http://en.wikipedia.org/wiki/Budesonide); pp. 1-3. |
Angelucci et al., "Budesonide for Inflammatory Bowel Disease Treatment," Current Medicinal Chemistry, 2008, vol. 15, No. 14, pp. 2-9. |
Brunner, M. et al., "Gastrointestinal Transit and 5-ASA Release From a New Mesalazine Extended-Release Formulation," Alimentary Pharmacology and Therapeutics, vol. 17, pp. 395-402, copyright 2003 Blackwell Publishing Ltd., 8 pages. |
Brunner, M. et al., "Gastrointestinal Transit, Release and Plasma Pharmacokinetics of a New Oral Budesonide Formulation," British Journal of Clinical Pharmacology, DOI:10.1111/j.1365-2125.2005.02517.x, pp. 1-8, copyright 2005 Blackwell Publishing Ltd., 8 pages. |
D'Haens, G.R. et al., "Budesonide MMX(TM) Is Active and Safe In Patients With Active Left-Sided Ulcerative Colitis," Br J Clinic Pharmacol., 2005, vol. 61, 3 pages. |
D'Haens, G.R. et al., "Budesonide MMX™ Is Active and Safe In Patients With Active Left-Sided Ulcerative Colitis," Br J Clinic Pharmacol., 2005, vol. 61, 3 pages. |
D'Haens, G.R., et al., "Clinical Trial: Preliminary Efficacy and Safety Study of a New Budesonide-MMX® 9 mg Extended-Release Tablets in Patients With Active Left-Sided Ulcerative Colitis," Journal of Crohn's and Colitis, 2010, vol. 4, pp. 153-160, © copyright 2009 European Crohn's and Colitis Organisation. |
Ferraboschi, P. et al., "Estimation and Characterisation of Budesonide Tablets Impurities," Journal of Pharmaceutical and Biomedical Analysis, 2008, vol. 47, pp. 636-640, © 2008 Elsevier B.V. |
Fiorino, G. et al., "New Drug Delivery Systems in Inflammatory Bowel Disease: MMX(TM) and Tailored Delivery to the Gut," Current Medicinal Chemistry, 2010, vol. 17, pp. 1851-1857, © 2010 Bentham Science Publishers Ltd. |
Fiorino, G. et al., "New Drug Delivery Systems in Inflammatory Bowel Disease: MMX™ and Tailored Delivery to the Gut," Current Medicinal Chemistry, 2010, vol. 17, pp. 1851-1857, © 2010 Bentham Science Publishers Ltd. |
Flanders, P. et al., The Control of Drug Release From Conventional Melt Granulation Matrices, Drug Development and Industrial Pharmacy, 1987, vol. 13, No. 6, pp. 1001-1022, © 1987 Marcel Dekker, Inc. |
Jantzen, G.M. et al. "Sustained- and Controlled-Release Drug Delivery Systems," Modern Pharmaceutics, 3rd Edition, Revised and Expanded, pp. 575-609, © 1996 by Marcel Dekker, Inc., 37 pages. |
JP Office Action dated May 6, 2010 from corresponding JP2001-502812, English translation included. |
JP Office Action dated May 6, 2010 from corresponding JP2001-502812-English translation included. |
Koutroubakis, I., "Recent Advances in the Management of Distal Ulcerative Colitis," World Journal of Gastrointestinal Pharmacology and Therapeutics, 2010, vol. 1, No. 2, pp. 43-50, © 2010 Baishideng. |
Maejima, T., "Application of Tumbling Melt Granulation Method to Prepare Controlled-Release Beads by Coating with Mixture of Functional Non-Meltable and Meltable Materials," Chem. Pharm. Bull., 1998, vol. 46, No. 3, pp. 531-533, © 1998 Pharmaceutical Society of Japan. |
Moro et al., "Drug Delivery Systems: Diffusion Controlled Systems," II Prodotto Chimico & Aerosol Selezione (The Chemical & Aerosol Selection), Apr. 1985, pp. 16-24, Partial relevant English translation of pp. 20 and 22 included. |
Moro, et al., "Drug Delivery Systems: Diffusion Controlled Systems", II Prodotto Chimico & Aerosol Selezione (The Chemical & Aerosol Selection), Apr. 1985, pp. 16-24, Partial relevant English translation of pp. 20 and 22 included. |
Physical Pharmacy, Chapter 19: Drug Product Design, Oct. 1993, pp. 515-519. |
Sandborn, W.J. et al., "Budesonide MXX® 9 mg For The Induction of Remission of Mild-to-Moderate Ulcerative Colitis (UC): Data From a Multicenter, Randomized, Double-Blind Placebo-Controlled Study in North America and India," Presentation at DDW 2011, Poster, 1 page. |
Steward, "Review of Pharmaceutical Controlled Release Methods and Devices," 1995, pp. 1-9. |
Steward, P., "Review of Pharmaceutical Controlled Release Methods and Devices", 1995, pp. 1-9. |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013120881A1 (en) | 2012-02-13 | 2013-08-22 | Cosmo Technologies Limited | Method for treating intestinal diseases presenting at least one inflammatory component |
US10588857B2 (en) | 2012-03-29 | 2020-03-17 | Therabiome, Llc | Gastrointestinal site-specific oral vaccination formulations active on the ileum and appendix |
US9907755B2 (en) | 2013-03-14 | 2018-03-06 | Therabiome, Llc | Targeted gastrointestinal tract delivery of probiotic organisms and/or therapeutic agents |
US10369111B2 (en) | 2013-03-14 | 2019-08-06 | Therabiome, Llc | Targeted gastrointestinal tract delivery of probiotic organisms and/or therapeutic agents |
US11590083B2 (en) | 2013-03-14 | 2023-02-28 | Therabiome, Llc | Targeted gastrointestinal tract delivery of probiotic organisms and/or therapeutic agents |
WO2015071812A1 (en) | 2013-11-18 | 2015-05-21 | Wockhardt Limited | Solid oral modified-release composition comprising budesonide or salt thereof |
US11344562B2 (en) | 2017-08-15 | 2022-05-31 | Nephron Pharmaceuticals Corporation | Aqueous nebulization composition |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
USRE43799E1 (en) | Controlled release and taste masking oral pharmaceutical composition | |
US10052286B2 (en) | Controlled release and taste masking oral pharmaceutical composition | |
US10660858B2 (en) | Controlled release and taste masking oral pharmaceutical composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FPAY | Fee payment |
Year of fee payment: 4 |
|
AS | Assignment |
Owner name: COSMO TECHNOLOGIES LIMITED, IRELAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:VILLA, ROBERTO;PEDRANI, MASSIMO;AJANI, MAURO;AND OTHERS;REEL/FRAME:039671/0574 Effective date: 20110622 Owner name: COSMO TECHNOLOGIES LIMITED, IRELAND Free format text: ASSIGNEE ADDRESS CHANGE;ASSIGNOR:COSMO TECHNOLOGIES LIMITED;REEL/FRAME:039951/0499 Effective date: 20151109 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1552); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 8 |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
LAPS | Lapse for failure to pay maintenance fees |
Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |