JP2012526047A5 - - Google Patents
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- Publication number
- JP2012526047A5 JP2012526047A5 JP2012508819A JP2012508819A JP2012526047A5 JP 2012526047 A5 JP2012526047 A5 JP 2012526047A5 JP 2012508819 A JP2012508819 A JP 2012508819A JP 2012508819 A JP2012508819 A JP 2012508819A JP 2012526047 A5 JP2012526047 A5 JP 2012526047A5
- Authority
- JP
- Japan
- Prior art keywords
- coating
- opioid analgesic
- pharmaceutical composition
- water
- opioid
- 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.)
- Granted
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- 238000000576 coating method Methods 0.000 claims 80
- 239000011248 coating agent Substances 0.000 claims 79
- 239000008194 pharmaceutical composition Substances 0.000 claims 43
- 229940121367 non-opioid analgesics Drugs 0.000 claims 37
- 239000000014 opioid analgesic Substances 0.000 claims 28
- 229920003176 water-insoluble polymer Polymers 0.000 claims 21
- 238000000034 method Methods 0.000 claims 20
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 16
- 239000011859 microparticle Substances 0.000 claims 15
- 239000002552 dosage form Substances 0.000 claims 13
- 239000002245 particle Substances 0.000 claims 10
- 239000000796 flavoring agent Substances 0.000 claims 8
- 235000019634 flavors Nutrition 0.000 claims 8
- 230000002496 gastric effect Effects 0.000 claims 8
- 229960005489 paracetamol Drugs 0.000 claims 8
- 239000011230 binding agent Substances 0.000 claims 7
- -1 glycerol ester Chemical class 0.000 claims 7
- 229920000642 polymer Polymers 0.000 claims 7
- 239000008187 granular material Substances 0.000 claims 6
- 230000000873 masking effect Effects 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 229920003169 water-soluble polymer Polymers 0.000 claims 6
- 239000001856 Ethyl cellulose Substances 0.000 claims 5
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 5
- 150000001720 carbohydrates Chemical class 0.000 claims 5
- 229920001577 copolymer Polymers 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229920001249 ethyl cellulose Polymers 0.000 claims 5
- 235000019325 ethyl cellulose Nutrition 0.000 claims 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 4
- 229920002284 Cellulose triacetate Polymers 0.000 claims 4
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims 4
- 229920002678 cellulose Polymers 0.000 claims 4
- 229920002301 cellulose acetate Polymers 0.000 claims 4
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims 4
- 229920003086 cellulose ether Polymers 0.000 claims 4
- 239000007884 disintegrant Substances 0.000 claims 4
- 235000003599 food sweetener Nutrition 0.000 claims 4
- 230000007935 neutral effect Effects 0.000 claims 4
- 239000004014 plasticizer Substances 0.000 claims 4
- 229920002689 polyvinyl acetate Polymers 0.000 claims 4
- 239000011118 polyvinyl acetate Substances 0.000 claims 4
- 239000011148 porous material Substances 0.000 claims 4
- 150000005846 sugar alcohols Chemical class 0.000 claims 4
- 239000003765 sweetening agent Substances 0.000 claims 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 3
- 239000002202 Polyethylene glycol Substances 0.000 claims 3
- 239000011575 calcium Substances 0.000 claims 3
- 229910052791 calcium Inorganic materials 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- JMBRWJAVUIITGV-LNNMZZBZSA-N hydrocodone bitartrate Chemical compound [H+].[H+].[H+].[H+].O.O.O.O.O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC JMBRWJAVUIITGV-LNNMZZBZSA-N 0.000 claims 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 3
- 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 claims 3
- 229920001223 polyethylene glycol Polymers 0.000 claims 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 3
- 238000013268 sustained release Methods 0.000 claims 3
- 239000012730 sustained-release form Substances 0.000 claims 3
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-UHFFFAOYSA-N 0.000 claims 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims 2
- 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 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 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims 2
- 229920003149 Eudragit® E 100 Polymers 0.000 claims 2
- 229920003134 Eudragit® polymer Polymers 0.000 claims 2
- 239000005955 Ferric phosphate Substances 0.000 claims 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- 229920001800 Shellac Polymers 0.000 claims 2
- 239000004376 Sucralose Substances 0.000 claims 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 229920003144 amino alkyl methacrylate copolymer Polymers 0.000 claims 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 2
- 239000001506 calcium phosphate Substances 0.000 claims 2
- 229910000389 calcium phosphate Inorganic materials 0.000 claims 2
- 235000011010 calcium phosphates Nutrition 0.000 claims 2
- PBUBJNYXWIDFMU-UHFFFAOYSA-L calcium;butanedioate Chemical compound [Ca+2].[O-]C(=O)CCC([O-])=O PBUBJNYXWIDFMU-UHFFFAOYSA-L 0.000 claims 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 claims 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 claims 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 2
- 229960004887 ferric hydroxide Drugs 0.000 claims 2
- 229940032958 ferric phosphate Drugs 0.000 claims 2
- 239000012530 fluid Substances 0.000 claims 2
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims 2
- 229960000240 hydrocodone Drugs 0.000 claims 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims 2
- 229960002764 hydrocodone bitartrate Drugs 0.000 claims 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims 2
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 claims 2
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 claims 2
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 claims 2
- 229910000399 iron(III) phosphate Inorganic materials 0.000 claims 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 2
- 239000001095 magnesium carbonate Substances 0.000 claims 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 2
- 229960001708 magnesium carbonate Drugs 0.000 claims 2
- 235000014380 magnesium carbonate Nutrition 0.000 claims 2
- 239000004337 magnesium citrate Substances 0.000 claims 2
- 229960005336 magnesium citrate Drugs 0.000 claims 2
- 235000002538 magnesium citrate Nutrition 0.000 claims 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 2
- 239000000347 magnesium hydroxide Substances 0.000 claims 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims 2
- 229960000816 magnesium hydroxide Drugs 0.000 claims 2
- 235000012254 magnesium hydroxide Nutrition 0.000 claims 2
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 claims 2
- 239000004137 magnesium phosphate Substances 0.000 claims 2
- 229910000157 magnesium phosphate Inorganic materials 0.000 claims 2
- 229960002261 magnesium phosphate Drugs 0.000 claims 2
- 235000010994 magnesium phosphates Nutrition 0.000 claims 2
- 239000000845 maltitol Substances 0.000 claims 2
- 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 claims 2
- 235000010449 maltitol Nutrition 0.000 claims 2
- 229940035436 maltitol Drugs 0.000 claims 2
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 claims 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims 2
- 239000004208 shellac Substances 0.000 claims 2
- 229940113147 shellac Drugs 0.000 claims 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims 2
- 235000013874 shellac Nutrition 0.000 claims 2
- 239000000600 sorbitol Substances 0.000 claims 2
- 235000010356 sorbitol Nutrition 0.000 claims 2
- 235000019408 sucralose Nutrition 0.000 claims 2
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 claims 2
- 229920001897 terpolymer Polymers 0.000 claims 2
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims 2
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims 1
- OJHZNMVJJKMFGX-BWCYBWMMSA-N (4r,4ar,7ar,12bs)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC OJHZNMVJJKMFGX-BWCYBWMMSA-N 0.000 claims 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims 1
- WWXUGNUFCNYMFK-UHFFFAOYSA-N Acetyl citrate Chemical compound CC(=O)OC(=O)CC(O)(C(O)=O)CC(O)=O WWXUGNUFCNYMFK-UHFFFAOYSA-N 0.000 claims 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 229920002785 Croscarmellose sodium Polymers 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 claims 1
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims 1
- 229930195725 Mannitol Natural products 0.000 claims 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims 1
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
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2010
- 2010-05-03 RU RU2011145433/15A patent/RU2567032C2/ru not_active IP Right Cessation
- 2010-05-03 WO PCT/US2010/033392 patent/WO2010127346A1/en not_active Ceased
- 2010-05-03 CN CN201080028794.2A patent/CN102458117B/zh not_active Expired - Fee Related
- 2010-05-03 TW TW099114104A patent/TW201041608A/zh unknown
- 2010-05-03 US US12/772,770 patent/US20100330150A1/en not_active Abandoned
- 2010-05-03 JP JP2012508818A patent/JP5845172B2/ja not_active Expired - Fee Related
- 2010-05-03 CN CN2010800285970A patent/CN102458360A/zh active Pending
- 2010-05-03 AU AU2010242749A patent/AU2010242749B2/en not_active Ceased
- 2010-05-03 KR KR1020117028537A patent/KR101752014B1/ko not_active Expired - Fee Related
- 2010-05-03 MX MX2011011480A patent/MX2011011480A/es not_active Application Discontinuation
- 2010-05-03 CA CA2760614A patent/CA2760614A1/en not_active Abandoned
- 2010-05-03 TW TW099114102A patent/TW201041607A/zh unknown
- 2010-05-03 CN CN201610815678.4A patent/CN106390129A/zh active Pending
- 2010-05-03 CA CA2760615A patent/CA2760615A1/en not_active Abandoned
- 2010-05-03 MX MX2011011478A patent/MX345942B/es active IP Right Grant
- 2010-05-03 AR ARP100101499A patent/AR076835A1/es unknown
- 2010-05-03 RU RU2011145432/15A patent/RU2554740C2/ru not_active IP Right Cessation
- 2010-05-03 EP EP10770481A patent/EP2424504A4/en not_active Withdrawn
- 2010-05-03 EP EP10770482A patent/EP2424365A4/en not_active Withdrawn
- 2010-05-03 KR KR1020117028540A patent/KR20120031002A/ko not_active Ceased
- 2010-05-03 AU AU2010242748A patent/AU2010242748B2/en not_active Ceased
- 2010-05-03 WO PCT/US2010/033389 patent/WO2010127345A2/en not_active Ceased
- 2010-05-03 US US12/772,776 patent/US9572781B2/en not_active Expired - Fee Related
- 2010-05-03 BR BRPI1007636-0A patent/BRPI1007636A2/pt not_active IP Right Cessation
- 2010-05-03 JP JP2012508819A patent/JP5845173B2/ja not_active Expired - Fee Related
- 2010-05-03 AR ARP100101500A patent/AR076540A1/es unknown
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2011
- 2011-11-30 ZA ZA2011/08780A patent/ZA201108780B/en unknown
- 2011-11-30 ZA ZA2011/08781A patent/ZA201108781B/en unknown
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