AU2006208627B8 - Alcohol resistant dosage forms - Google Patents
Alcohol resistant dosage forms Download PDFInfo
- Publication number
- AU2006208627B8 AU2006208627B8 AU2006208627A AU2006208627A AU2006208627B8 AU 2006208627 B8 AU2006208627 B8 AU 2006208627B8 AU 2006208627 A AU2006208627 A AU 2006208627A AU 2006208627 A AU2006208627 A AU 2006208627A AU 2006208627 B8 AU2006208627 B8 AU 2006208627B8
- Authority
- AU
- Australia
- Prior art keywords
- dosage form
- opioid
- salt
- less
- controlled release
- 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.)
- Active
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 358
- 239000002552 dosage form Substances 0.000 title claims description 210
- 150000003839 salts Chemical class 0.000 claims description 195
- 239000000203 mixture Substances 0.000 claims description 183
- 238000013270 controlled release Methods 0.000 claims description 178
- 239000011159 matrix material Substances 0.000 claims description 145
- 238000009472 formulation Methods 0.000 claims description 144
- 239000000463 material Substances 0.000 claims description 85
- 238000004090 dissolution Methods 0.000 claims description 82
- 239000000014 opioid analgesic Substances 0.000 claims description 75
- 239000012530 fluid Substances 0.000 claims description 68
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 67
- 230000002496 gastric effect Effects 0.000 claims description 62
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims description 61
- 229920001249 ethyl cellulose Polymers 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000001856 Ethyl cellulose Substances 0.000 claims description 59
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 59
- 238000000338 in vitro Methods 0.000 claims description 57
- 229960001410 hydromorphone Drugs 0.000 claims description 55
- 238000000605 extraction Methods 0.000 claims description 54
- 229960003617 oxycodone hydrochloride Drugs 0.000 claims description 40
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical group FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 claims description 39
- 238000004519 manufacturing process Methods 0.000 claims description 38
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 37
- 229920013820 alkyl cellulose Polymers 0.000 claims description 29
- 229920000193 polymethacrylate Polymers 0.000 claims description 27
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims description 26
- 230000002209 hydrophobic effect Effects 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- DYUTXEVRMPFGTH-UHFFFAOYSA-N 4-(2,5-dimethylphenyl)-5-methyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C(=CC=C(C)C=2)C)=C1C DYUTXEVRMPFGTH-UHFFFAOYSA-N 0.000 claims description 25
- -1 aliphatic alcohols Chemical class 0.000 claims description 25
- 229960002738 hydromorphone hydrochloride Drugs 0.000 claims description 25
- 229960002085 oxycodone Drugs 0.000 claims description 24
- 238000005469 granulation Methods 0.000 claims description 20
- 230000003179 granulation Effects 0.000 claims description 20
- RGPDIGOSVORSAK-STHHAXOLSA-N naloxone hydrochloride Chemical compound Cl.O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C RGPDIGOSVORSAK-STHHAXOLSA-N 0.000 claims description 20
- 229920001169 thermoplastic Polymers 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 239000002245 particle Substances 0.000 claims description 18
- 239000004014 plasticizer Substances 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000012360 testing method Methods 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 17
- 238000001125 extrusion Methods 0.000 claims description 16
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003402 opiate agonist Substances 0.000 claims description 15
- 229940012831 stearyl alcohol Drugs 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 13
- 230000007935 neutral effect Effects 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 10
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 10
- 229960004127 naloxone Drugs 0.000 claims description 9
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004359 castor oil Substances 0.000 claims description 7
- 235000019438 castor oil Nutrition 0.000 claims description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 7
- 229960005250 naloxone hydrochloride Drugs 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 6
- 230000000052 comparative effect Effects 0.000 claims description 6
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004570 mortar (masonry) Substances 0.000 claims description 6
- 239000006187 pill Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229940082500 cetostearyl alcohol Drugs 0.000 claims description 5
- 229960000541 cetyl alcohol Drugs 0.000 claims description 5
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 claims description 5
- UIQMVEYFGZJHCZ-SSTWWWIQSA-N Nalorphine Chemical compound C([C@@H](N(CC1)CC=C)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 UIQMVEYFGZJHCZ-SSTWWWIQSA-N 0.000 claims description 4
- DEXMFYZAHXMZNM-UHFFFAOYSA-N Narceine Chemical compound OC(=O)C1=C(OC)C(OC)=CC=C1C(=O)CC1=C(CCN(C)C)C=C(OCO2)C2=C1OC DEXMFYZAHXMZNM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 229960004126 codeine Drugs 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 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 description 4
- 229960000240 hydrocodone Drugs 0.000 claims description 4
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 4
- 229960005181 morphine Drugs 0.000 claims description 4
- 229960000938 nalorphine Drugs 0.000 claims description 4
- 239000003401 opiate antagonist Chemical class 0.000 claims description 4
- 229960005118 oxymorphone Drugs 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims description 4
- 229940127450 Opioid Agonists Drugs 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 238000005520 cutting process Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- UVITTYOJFDLOGI-UHFFFAOYSA-N (1,2,5-trimethyl-4-phenylpiperidin-4-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CC(C)N(C)CC1C UVITTYOJFDLOGI-UHFFFAOYSA-N 0.000 claims description 2
- LGFMXOTUSSVQJV-NEYUFSEYSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;(4r,4ar,7s,7ar,12bs)-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol;1-[(3,4-dimethoxyphenyl)methyl]-6 Chemical compound Cl.Cl.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 LGFMXOTUSSVQJV-NEYUFSEYSA-N 0.000 claims description 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 2
- IYNWSQDZXMGGGI-NUEKZKHPSA-N 3-hydroxymorphinan Chemical compound C1CCC[C@H]2[C@H]3CC4=CC=C(O)C=C4[C@]21CCN3 IYNWSQDZXMGGGI-NUEKZKHPSA-N 0.000 claims description 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 2
- IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 claims description 2
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 claims description 2
- OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 claims description 2
- ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 claims description 2
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims description 2
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 2
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical group C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 2
- ONBWJWYUHXVEJS-ZTYRTETDSA-N Normorphine Chemical compound C([C@@H](NCC1)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ONBWJWYUHXVEJS-ZTYRTETDSA-N 0.000 claims description 2
- 239000008896 Opium Substances 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 229960001391 alfentanil Drugs 0.000 claims description 2
- KGYFOSCXVAXULR-UHFFFAOYSA-N allylprodine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)CC1CC=C KGYFOSCXVAXULR-UHFFFAOYSA-N 0.000 claims description 2
- 229950004361 allylprodine Drugs 0.000 claims description 2
- 229960001349 alphaprodine Drugs 0.000 claims description 2
- UVAZQQHAVMNMHE-XJKSGUPXSA-N alphaprodine Chemical compound C=1C=CC=CC=1[C@@]1(OC(=O)CC)CCN(C)C[C@@H]1C UVAZQQHAVMNMHE-XJKSGUPXSA-N 0.000 claims description 2
- LKYQLAWMNBFNJT-UHFFFAOYSA-N anileridine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCC1=CC=C(N)C=C1 LKYQLAWMNBFNJT-UHFFFAOYSA-N 0.000 claims description 2
- 229960002512 anileridine Drugs 0.000 claims description 2
- RDJGWRFTDZZXSM-RNWLQCGYSA-N benzylmorphine Chemical compound O([C@@H]1[C@]23CCN([C@H](C4)[C@@H]3C=C[C@@H]1O)C)C1=C2C4=CC=C1OCC1=CC=CC=C1 RDJGWRFTDZZXSM-RNWLQCGYSA-N 0.000 claims description 2
- FLKWNFFCSSJANB-UHFFFAOYSA-N bezitramide Chemical compound O=C1N(C(=O)CC)C2=CC=CC=C2N1C(CC1)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 FLKWNFFCSSJANB-UHFFFAOYSA-N 0.000 claims description 2
- 229960004611 bezitramide Drugs 0.000 claims description 2
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims description 2
- 229960001736 buprenorphine Drugs 0.000 claims description 2
- IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 claims description 2
- 229960001113 butorphanol Drugs 0.000 claims description 2
- GPZLDQAEBHTMPG-UHFFFAOYSA-N clonitazene Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2N(CCN(CC)CC)C=1CC1=CC=C(Cl)C=C1 GPZLDQAEBHTMPG-UHFFFAOYSA-N 0.000 claims description 2
- 229950001604 clonitazene Drugs 0.000 claims description 2
- 229950003851 desomorphine Drugs 0.000 claims description 2
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 claims description 2
- WDEFBBTXULIOBB-WBVHZDCISA-N dextilidine Chemical compound C=1C=CC=CC=1[C@@]1(C(=O)OCC)CCC=C[C@H]1N(C)C WDEFBBTXULIOBB-WBVHZDCISA-N 0.000 claims description 2
- 229960003701 dextromoramide Drugs 0.000 claims description 2
- INUNXTSAACVKJS-OAQYLSRUSA-N dextromoramide Chemical compound C([C@@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-OAQYLSRUSA-N 0.000 claims description 2
- 229960004193 dextropropoxyphene Drugs 0.000 claims description 2
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims description 2
- 229960003461 dezocine Drugs 0.000 claims description 2
- VTMVHDZWSFQSQP-VBNZEHGJSA-N dezocine Chemical compound C1CCCC[C@H]2CC3=CC=C(O)C=C3[C@]1(C)[C@H]2N VTMVHDZWSFQSQP-VBNZEHGJSA-N 0.000 claims description 2
- RXTHKWVSXOIHJS-UHFFFAOYSA-N diampromide Chemical compound C=1C=CC=CC=1N(C(=O)CC)CC(C)N(C)CCC1=CC=CC=C1 RXTHKWVSXOIHJS-UHFFFAOYSA-N 0.000 claims description 2
- 229950001059 diampromide Drugs 0.000 claims description 2
- RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 claims description 2
- 229960000920 dihydrocodeine Drugs 0.000 claims description 2
- BRTSNYPDACNMIP-FAWZKKEFSA-N dihydroetorphine Chemical compound O([C@H]1[C@@]2(OC)CC[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O BRTSNYPDACNMIP-FAWZKKEFSA-N 0.000 claims description 2
- RHUWRJWFHUKVED-UHFFFAOYSA-N dimenoxadol Chemical compound C=1C=CC=CC=1C(C(=O)OCCN(C)C)(OCC)C1=CC=CC=C1 RHUWRJWFHUKVED-UHFFFAOYSA-N 0.000 claims description 2
- 229950011187 dimenoxadol Drugs 0.000 claims description 2
- QIRAYNIFEOXSPW-UHFFFAOYSA-N dimepheptanol Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(O)CC)C1=CC=CC=C1 QIRAYNIFEOXSPW-UHFFFAOYSA-N 0.000 claims description 2
- 229950004655 dimepheptanol Drugs 0.000 claims description 2
- CANBGVXYBPOLRR-UHFFFAOYSA-N dimethylthiambutene Chemical compound C=1C=CSC=1C(=CC(C)N(C)C)C1=CC=CS1 CANBGVXYBPOLRR-UHFFFAOYSA-N 0.000 claims description 2
- 229950005563 dimethylthiambutene Drugs 0.000 claims description 2
- LQGIXNQCOXNCRP-UHFFFAOYSA-N dioxaphetyl butyrate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)CCN1CCOCC1 LQGIXNQCOXNCRP-UHFFFAOYSA-N 0.000 claims description 2
- 229950008972 dioxaphetyl butyrate Drugs 0.000 claims description 2
- SVDHSZFEQYXRDC-UHFFFAOYSA-N dipipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCCCC1 SVDHSZFEQYXRDC-UHFFFAOYSA-N 0.000 claims description 2
- 229960002500 dipipanone Drugs 0.000 claims description 2
- ZOWQTJXNFTWSCS-IAQYHMDHSA-N eptazocine Chemical compound C1N(C)CC[C@@]2(C)C3=CC(O)=CC=C3C[C@@H]1C2 ZOWQTJXNFTWSCS-IAQYHMDHSA-N 0.000 claims description 2
- 229950010920 eptazocine Drugs 0.000 claims description 2
- WGJHHMKQBWSQIY-UHFFFAOYSA-N ethoheptazine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCCN(C)CC1 WGJHHMKQBWSQIY-UHFFFAOYSA-N 0.000 claims description 2
- 229960000569 ethoheptazine Drugs 0.000 claims description 2
- VRPOMBRJOIYWMM-UHFFFAOYSA-N ethyl prop-2-enoate;methyl prop-2-enoate Chemical compound COC(=O)C=C.CCOC(=O)C=C VRPOMBRJOIYWMM-UHFFFAOYSA-N 0.000 claims description 2
- MORSAEFGQPDBKM-UHFFFAOYSA-N ethylmethylthiambutene Chemical compound C=1C=CSC=1C(=CC(C)N(C)CC)C1=CC=CS1 MORSAEFGQPDBKM-UHFFFAOYSA-N 0.000 claims description 2
- 229950006111 ethylmethylthiambutene Drugs 0.000 claims description 2
- 229960004578 ethylmorphine Drugs 0.000 claims description 2
- PXDBZSCGSQSKST-UHFFFAOYSA-N etonitazene Chemical compound C1=CC(OCC)=CC=C1CC1=NC2=CC([N+]([O-])=O)=CC=C2N1CCN(CC)CC PXDBZSCGSQSKST-UHFFFAOYSA-N 0.000 claims description 2
- 229950004538 etonitazene Drugs 0.000 claims description 2
- CAHCBJPUTCKATP-FAWZKKEFSA-N etorphine Chemical compound O([C@H]1[C@@]2(OC)C=C[C@@]34C[C@@H]2[C@](C)(O)CCC)C2=C5[C@]41CCN(C)[C@@H]3CC5=CC=C2O CAHCBJPUTCKATP-FAWZKKEFSA-N 0.000 claims description 2
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Classifications
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- A—HUMAN NECESSITIES
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- 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
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Landscapes
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- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| PCT/GB2005/050014 WO2005079760A1 (en) | 2004-02-12 | 2005-02-11 | Particulates |
| AUPCT/GB2005/050014 | 2005-02-11 | ||
| US67050605P | 2005-04-12 | 2005-04-12 | |
| US60/670,506 | 2005-04-12 | ||
| US73033905P | 2005-10-26 | 2005-10-26 | |
| US60/730,339 | 2005-10-26 | ||
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| RU2241458C2 (ru) | 1997-12-22 | 2004-12-10 | Эро-Селтик, С.А. | Комбинации агонист/антагонист опиоида |
| US6375957B1 (en) | 1997-12-22 | 2002-04-23 | Euro-Celtique, S.A. | Opioid agonist/opioid antagonist/acetaminophen combinations |
| AU2002305559B2 (en) | 2001-05-11 | 2008-04-03 | Mundipharma Pty Limited | Abuse-resistant controlled-release opioid dosage form |
| DE60325567D1 (de) | 2002-04-05 | 2009-02-12 | Euro Celtique Sa | Matrix für die modifizierte freigabe von aktiven substanzen |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
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| TWI350762B (en) * | 2004-02-12 | 2011-10-21 | Euro Celtique Sa | Particulates |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
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- 2006-01-27 WO PCT/EP2006/000727 patent/WO2006079550A2/en not_active Ceased
- 2006-01-27 CA CA002594373A patent/CA2594373A1/en not_active Abandoned
- 2006-01-27 EP EP06703915A patent/EP1771160A2/en not_active Withdrawn
- 2006-01-27 MX MX2007009162A patent/MX2007009162A/es active IP Right Grant
- 2006-01-27 JP JP2007552587A patent/JP5704789B2/ja active Active
- 2006-01-27 EP EP10180425A patent/EP2319499A1/en not_active Withdrawn
- 2006-01-27 GE GEAP200610246A patent/GEP20105052B/en unknown
- 2006-01-27 KR KR1020097004935A patent/KR20090029856A/ko not_active Withdrawn
- 2006-01-27 CN CN2006800033121A patent/CN101132772B/zh active Active
-
2007
- 2007-07-26 IL IL184858A patent/IL184858A/en active IP Right Grant
- 2007-08-27 KR KR1020077019593A patent/KR100905511B1/ko active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5958452A (en) * | 1994-11-04 | 1999-09-28 | Euro-Celtique, S.A. | Extruded orally administrable opioid formulations |
| EP1348429A2 (en) * | 1994-11-04 | 2003-10-01 | Euro-Celtique S.A. | Melt-extruded orally administrable opioid formulations |
| WO2003004009A1 (en) * | 2001-07-02 | 2003-01-16 | Geneva Pharmaceuticals, Inc. | Pharmaceutical composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090029856A (ko) | 2009-03-23 |
| CN101132772B (zh) | 2012-05-09 |
| GEP20105052B (en) | 2010-07-26 |
| MX2007009162A (es) | 2007-10-23 |
| EP2289491A1 (en) | 2011-03-02 |
| CA2594373A1 (en) | 2006-08-03 |
| AU2006208627A1 (en) | 2006-08-03 |
| AP2007004099A0 (en) | 2007-08-31 |
| KR20070104443A (ko) | 2007-10-25 |
| KR100905511B1 (ko) | 2009-07-01 |
| BRPI0606339A2 (pt) | 2009-06-16 |
| EA015615B1 (ru) | 2011-10-31 |
| JP2008528534A (ja) | 2008-07-31 |
| US20070259045A1 (en) | 2007-11-08 |
| EP3228308A1 (en) | 2017-10-11 |
| IL184858A (en) | 2016-03-31 |
| WO2006079550A2 (en) | 2006-08-03 |
| JP5704789B2 (ja) | 2015-04-22 |
| IL184858A0 (en) | 2007-12-03 |
| AP2274A (en) | 2011-08-19 |
| AU2006208627B2 (en) | 2009-08-06 |
| WO2006079550A3 (en) | 2006-12-14 |
| EA200701595A1 (ru) | 2008-02-28 |
| CN101132772A (zh) | 2008-02-27 |
| EP1771160A2 (en) | 2007-04-11 |
| EP2319499A1 (en) | 2011-05-11 |
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