IL111742A - Oral sustained release formulations of an opioid analgesic and method for their preparation - Google Patents

Oral sustained release formulations of an opioid analgesic and method for their preparation

Info

Publication number: IL111742A
Authority: IL; Israel
Prior art keywords: opioid; sustained release; hours; administration; dosage form
Prior art date: 1993-11-23

Application number

IL11174294A

Other languages

English (en)

Other versions

IL111742A0 (en

Original Assignee

Euro Celtique Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-11-23

Filing date

1994-11-23

Publication date

2004-02-19

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22559696&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL111742(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-11-23 Application filed by Euro Celtique Sa filed Critical Euro Celtique Sa

1995-01-24 Publication of IL111742A0 publication Critical patent/IL111742A0/xx

2004-02-19 Publication of IL111742A publication Critical patent/IL111742A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 171
238000009472 formulation Methods 0.000 title claims abstract description 139
239000000014 opioid analgesic Substances 0.000 title claims abstract description 85
239000012730 sustained-release form Substances 0.000 title claims description 166
238000013268 sustained release Methods 0.000 title claims description 165
238000000034 method Methods 0.000 title claims description 38
238000002360 preparation method Methods 0.000 title description 7
230000036470 plasma concentration Effects 0.000 claims abstract description 69
238000010521 absorption reaction Methods 0.000 claims abstract description 34
239000000463 material Substances 0.000 claims abstract description 34
230000000202 analgesic effect Effects 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 17
241000282414 Homo sapiens Species 0.000 claims abstract description 13
241000282412 Homo Species 0.000 claims abstract description 3
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 162
239000011324 bead Substances 0.000 claims description 80
229960005181 morphine Drugs 0.000 claims description 80
239000002552 dosage form Substances 0.000 claims description 77
238000000576 coating method Methods 0.000 claims description 65
239000011248 coating agent Substances 0.000 claims description 58
GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 claims description 42
229960004715 morphine sulfate Drugs 0.000 claims description 41
-1 dimehoxadol Chemical compound 0.000 claims description 32
208000002193 Pain Diseases 0.000 claims description 31
230000036407 pain Effects 0.000 claims description 30
238000011282 treatment Methods 0.000 claims description 30
239000012729 immediate-release (IR) formulation Substances 0.000 claims description 26
239000000758 substrate Substances 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 23
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 22
229940079593 drug Drugs 0.000 claims description 22
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 20
229960001410 hydromorphone Drugs 0.000 claims description 19
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 17
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 16
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XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 13
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 12
229920000058 polyacrylate Polymers 0.000 claims description 12
229960004126 codeine Drugs 0.000 claims description 11
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 9
229960001736 buprenorphine Drugs 0.000 claims description 9
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 9
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 7
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 7
229960000920 dihydrocodeine Drugs 0.000 claims description 7
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 7
229960001797 methadone Drugs 0.000 claims description 7
229960004380 tramadol Drugs 0.000 claims description 7
TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 7
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 6
GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 6
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 6
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 6
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 6
239000008896 Opium Substances 0.000 claims description 6
229960004193 dextropropoxyphene Drugs 0.000 claims description 6
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 6
229960002069 diamorphine Drugs 0.000 claims description 6
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 6
229950008972 dioxaphetyl butyrate Drugs 0.000 claims description 6
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 6
229950010920 eptazocine Drugs 0.000 claims description 6
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 6
229950004538 etonitazene Drugs 0.000 claims description 6
229960002428 fentanyl Drugs 0.000 claims description 6
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 6
229960000240 hydrocodone Drugs 0.000 claims description 6
WTJBNMUWRKPFRS-UHFFFAOYSA-N hydroxypethidine Chemical compound C=1C=CC(O)=CC=1C1(C(=O)OCC)CCN(C)CC1 WTJBNMUWRKPFRS-UHFFFAOYSA-N 0.000 claims description 6
IFKPLJWIEQBPGG-UHFFFAOYSA-N isomethadone Chemical compound C=1C=CC=CC=1C(C(C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-UHFFFAOYSA-N 0.000 claims description 6
229950009272 isomethadone Drugs 0.000 claims description 6
229960003029 ketobemidone Drugs 0.000 claims description 6
229960003406 levorphanol Drugs 0.000 claims description 6
229950010274 lofentanil Drugs 0.000 claims description 6
IMYHGORQCPYVBZ-NLFFAJNJSA-N lofentanil Chemical compound CCC(=O)N([C@@]1([C@@H](CN(CCC=2C=CC=CC=2)CC1)C)C(=O)OC)C1=CC=CC=C1 IMYHGORQCPYVBZ-NLFFAJNJSA-N 0.000 claims description 6
229960000365 meptazinol Drugs 0.000 claims description 6
JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 claims description 6
229950009131 metazocine Drugs 0.000 claims description 6
YGSVZRIZCHZUHB-COLVAYQJSA-N metazocine Chemical compound C1C2=CC=C(O)C=C2[C@]2(C)CCN(C)[C@@]1([H])[C@@H]2C YGSVZRIZCHZUHB-COLVAYQJSA-N 0.000 claims description 6
GODGZZGKTZQSAL-VXFFQEMOSA-N myrophine Chemical compound C([C@@H]1[C@@H]2C=C[C@@H]([C@@H]3OC4=C5[C@]23CCN1C)OC(=O)CCCCCCCCCCCCC)C5=CC=C4OCC1=CC=CC=C1 GODGZZGKTZQSAL-VXFFQEMOSA-N 0.000 claims description 6
229950007471 myrophine Drugs 0.000 claims description 6
229960000805 nalbuphine Drugs 0.000 claims description 6
NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims description 6
229960001027 opium Drugs 0.000 claims description 6
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims description 6
229960005301 pentazocine Drugs 0.000 claims description 6
229960000482 pethidine Drugs 0.000 claims description 6
LOXCOAXRHYDLOW-UHFFFAOYSA-N phenadoxone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CC(C)N1CCOCC1 LOXCOAXRHYDLOW-UHFFFAOYSA-N 0.000 claims description 6
229950004540 phenadoxone Drugs 0.000 claims description 6
ZQHYKVKNPWDQSL-KNXBSLHKSA-N phenazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CCC1=CC=CC=C1 ZQHYKVKNPWDQSL-KNXBSLHKSA-N 0.000 claims description 6
229960000897 phenazocine Drugs 0.000 claims description 6
PXXKIYPSXYFATG-UHFFFAOYSA-N piminodine Chemical compound C1CC(C(=O)OCC)(C=2C=CC=CC=2)CCN1CCCNC1=CC=CC=C1 PXXKIYPSXYFATG-UHFFFAOYSA-N 0.000 claims description 6
229950006445 piminodine Drugs 0.000 claims description 6
ZXWAUWBYASJEOE-UHFFFAOYSA-N proheptazine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCCN(C)CC1C ZXWAUWBYASJEOE-UHFFFAOYSA-N 0.000 claims description 6
XJKQCILVUHXVIQ-UHFFFAOYSA-N properidine Chemical compound C=1C=CC=CC=1C1(C(=O)OC(C)C)CCN(C)CC1 XJKQCILVUHXVIQ-UHFFFAOYSA-N 0.000 claims description 6
229950004345 properidine Drugs 0.000 claims description 6
GGCSSNBKKAUURC-UHFFFAOYSA-N sufentanil Chemical compound C1CN(CCC=2SC=CC=2)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 GGCSSNBKKAUURC-UHFFFAOYSA-N 0.000 claims description 6
229960004739 sufentanil Drugs 0.000 claims description 6
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims description 6
YQYVFVRQLZMJKJ-JBBXEZCESA-N (+)-cyclazocine Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@@H]2[C@@H]1C)CN2CC1CC1 YQYVFVRQLZMJKJ-JBBXEZCESA-N 0.000 claims description 5
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 5
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 5
OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 claims description 5
IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 5
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 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
229960001391 alfentanil Drugs 0.000 claims description 5
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 5
229950004361 allylprodine Drugs 0.000 claims description 5
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 5
229960004611 bezitramide Drugs 0.000 claims description 5
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 5
229960001113 butorphanol Drugs 0.000 claims description 5
239000004359 castor oil Substances 0.000 claims description 5
235000019438 castor oil Nutrition 0.000 claims description 5
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 5
229950001604 clonitazene Drugs 0.000 claims description 5
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229960003701 dextromoramide Drugs 0.000 claims description 5
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 5
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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 5
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 5
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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 5
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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 5
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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 5
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WGJHHMKQBWSQIY-UHFFFAOYSA-N ethoheptazine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCCN(C)CC1 WGJHHMKQBWSQIY-UHFFFAOYSA-N 0.000 claims description 5
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229950006080 metopon Drugs 0.000 claims description 5
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WCDSHELZWCOTMI-UHFFFAOYSA-N norpipanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)CC)CCN1CCCCC1 WCDSHELZWCOTMI-UHFFFAOYSA-N 0.000 claims description 5
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CFBQYWXPZVQQTN-QPTUXGOLSA-N phenomorphan Chemical compound C([C@]12CCCC[C@H]1[C@H]1CC3=CC=C(C=C32)O)CN1CCC1=CC=CC=C1 CFBQYWXPZVQQTN-QPTUXGOLSA-N 0.000 claims description 5
229950011496 phenomorphan Drugs 0.000 claims description 5
IHEHEFLXQFOQJO-UHFFFAOYSA-N piritramide Chemical compound C1CC(C(=O)N)(N2CCCCC2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 IHEHEFLXQFOQJO-UHFFFAOYSA-N 0.000 claims description 5
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ZBAFFZBKCMWUHM-UHFFFAOYSA-N propiram Chemical compound C=1C=CC=NC=1N(C(=O)CC)C(C)CN1CCCCC1 ZBAFFZBKCMWUHM-UHFFFAOYSA-N 0.000 claims description 5
229950003779 propiram Drugs 0.000 claims description 5
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Medicines Containing Material From Animals Or Micro-Organisms (AREA)
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IL11174294A 1993-11-23 1994-11-23 Oral sustained release formulations of an opioid analgesic and method for their preparation IL111742A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/156,468 US5478577A (en)	1993-11-23	1993-11-23	Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level

Publications (2)

Publication Number	Publication Date
IL111742A0 IL111742A0 (en)	1995-01-24
IL111742A true IL111742A (en)	2004-02-19

Family

ID=22559696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11174294A IL111742A (en)	1993-11-23	1994-11-23	Oral sustained release formulations of an opioid analgesic and method for their preparation

Country Status (22)

Country	Link
US (10)	US5478577A (de)
EP (4)	EP0731694B2 (de)
JP (5)	JPH09505602A (de)
KR (1)	KR100201767B1 (de)
CN (1)	CN1134253C (de)
AT (3)	ATE350022T1 (de)
AU (1)	AU693134B2 (de)
BG (1)	BG63269B1 (de)
CZ (1)	CZ292936B6 (de)
DE (3)	DE69434752T2 (de)
DK (3)	DK1470815T3 (de)
ES (3)	ES2279742T3 (de)
FI (1)	FI121588B (de)
HU (1)	HUT73976A (de)
IL (1)	IL111742A (de)
NO (1)	NO315147B1 (de)
NZ (3)	NZ277917A (de)
PL (1)	PL312587A1 (de)
PT (3)	PT1023896E (de)
SK (1)	SK283544B6 (de)
TW (1)	TW420617B (de)
WO (1)	WO1995014460A1 (de)

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US5460972A (en) *	1991-04-08	1995-10-24	Research Foundation Of The State University Of New York	Ionized magnesium2+ concentrations in biological samples
US5266331A (en) *	1991-11-27	1993-11-30	Euroceltique, S.A.	Controlled release oxycodone compositions
US5968551A (en) *	1991-12-24	1999-10-19	Purdue Pharma L.P.	Orally administrable opioid formulations having extended duration of effect
US5681585A (en) *	1991-12-24	1997-10-28	Euro-Celtique, S.A.	Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer
US5478577A (en) †	1993-11-23	1995-12-26	Euroceltique, S.A.	Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level
ATE150004T1 (de) *	1992-10-26	1997-03-15	Goedecke Ag	Tilidin-dihydrogenorthophosphat, verfahren zu dessen herstellung und dieses enthaltende pharmazeutische zubereitungen
US20080075781A1 (en) *	1992-11-25	2008-03-27	Purdue Pharma Lp	Controlled release oxycodone compositions
SE9301057L (sv) †	1993-03-30	1994-10-01	Pharmacia Ab	Beredning med kontrollerad frisättning
NZ260408A (en) *	1993-05-10	1996-05-28	Euro Celtique Sa	Controlled release preparation comprising tramadol
US20070275062A1 (en) *	1993-06-18	2007-11-29	Benjamin Oshlack	Controlled release oxycodone compositions
US7740881B1 (en) *	1993-07-01	2010-06-22	Purdue Pharma Lp	Method of treating humans with opioid formulations having extended controlled release
IL110014A (en) *	1993-07-01	1999-11-30	Euro Celtique Sa	Solid controlled-release oral dosage forms of opioid analgesics
US5879705A (en) *	1993-07-27	1999-03-09	Euro-Celtique S.A.	Sustained release compositions of morphine and a method of preparing pharmaceutical compositions
US5843480A (en) *	1994-03-14	1998-12-01	Euro-Celtique, S.A.	Controlled release diamorphine formulation
EP0672416A1 (de) *	1994-03-14	1995-09-20	Euro-Celtique S.A.	Diamorphin enthaltendes Arzneimittel
US5411745A (en) *	1994-05-25	1995-05-02	Euro-Celtique, S.A.	Powder-layered morphine sulfate formulations
US7060293B1 (en)	1994-05-25	2006-06-13	Purdue Pharma	Powder-layered oral dosage forms
US6077533A (en) *	1994-05-25	2000-06-20	Purdue Pharma L.P.	Powder-layered oral dosage forms
US5914131A (en) *	1994-07-07	1999-06-22	Alza Corporation	Hydromorphone therapy
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KR20000011247A (ko) *	1998-07-23	2000-02-25	김윤	다당류를이용한대장선택성약물전달조성물및약학제제
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CN1610551A (zh) *	2001-07-06	2005-04-27	恩德制药公司	用作止痛剂的6－羟基羟吗啡酮的肠胃外给药
KR20030048026A (ko) *	2001-07-06	2003-06-18	펜웨스트 파머슈티칼즈 컴파니	옥시모르폰의 서방형 제제
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1993
- 1993-11-23 US US08/156,468 patent/US5478577A/en not_active Expired - Lifetime
1994
- 1994-11-22 DE DE69434752T patent/DE69434752T2/de not_active Expired - Lifetime
- 1994-11-22 AU AU13313/95A patent/AU693134B2/en not_active Withdrawn - After Issue
- 1994-11-22 ES ES00107670T patent/ES2279742T3/es not_active Expired - Lifetime
- 1994-11-22 NZ NZ277917A patent/NZ277917A/en not_active IP Right Cessation
- 1994-11-22 DK DK04009845T patent/DK1470815T3/da active
- 1994-11-22 NZ NZ508526A patent/NZ508526A/xx not_active IP Right Cessation
- 1994-11-22 EP EP95904755A patent/EP0731694B2/de not_active Expired - Lifetime
- 1994-11-22 PT PT00107670T patent/PT1023896E/pt unknown
- 1994-11-22 EP EP06026995A patent/EP1776950A1/de not_active Ceased
- 1994-11-22 PL PL94312587A patent/PL312587A1/xx unknown
- 1994-11-22 AT AT00107670T patent/ATE350022T1/de not_active IP Right Cessation
- 1994-11-22 DK DK00107670T patent/DK1023896T3/da active
- 1994-11-22 ES ES95904755T patent/ES2170136T5/es not_active Expired - Lifetime
- 1994-11-22 HU HU9503468A patent/HUT73976A/hu active IP Right Revival
- 1994-11-22 AT AT04009845T patent/ATE327739T1/de not_active IP Right Cessation
- 1994-11-22 PT PT04009845T patent/PT1470815E/pt unknown
- 1994-11-22 EP EP04009845A patent/EP1470815B1/de not_active Expired - Lifetime
- 1994-11-22 KR KR1019950705603A patent/KR100201767B1/ko not_active Expired - Fee Related
- 1994-11-22 DE DE69434911T patent/DE69434911T2/de not_active Expired - Lifetime
- 1994-11-22 CZ CZ19953217A patent/CZ292936B6/cs not_active IP Right Cessation
- 1994-11-22 ES ES04009845T patent/ES2266951T3/es not_active Expired - Lifetime
- 1994-11-22 JP JP7515254A patent/JPH09505602A/ja active Pending
- 1994-11-22 AT AT95904755T patent/ATE212831T1/de not_active IP Right Cessation
- 1994-11-22 EP EP00107670A patent/EP1023896B1/de not_active Expired - Lifetime
- 1994-11-22 WO PCT/US1994/013606 patent/WO1995014460A1/en not_active Ceased
- 1994-11-22 CN CNB941927237A patent/CN1134253C/zh not_active Expired - Fee Related
- 1994-11-22 PT PT95904755T patent/PT731694E/pt unknown
- 1994-11-22 DK DK95904755T patent/DK0731694T4/da active
- 1994-11-22 NZ NZ336055A patent/NZ336055A/xx not_active IP Right Cessation
- 1994-11-22 US US08/578,688 patent/US5672360A/en not_active Expired - Lifetime
- 1994-11-22 DE DE69429826T patent/DE69429826T3/de not_active Expired - Lifetime
- 1994-11-22 SK SK1538-95A patent/SK283544B6/sk unknown
- 1994-11-23 IL IL11174294A patent/IL111742A/en not_active IP Right Cessation
- 1994-12-21 TW TW083111985A patent/TW420617B/zh active
1995
- 1995-12-01 FI FI955782A patent/FI121588B/fi not_active IP Right Cessation
- 1995-12-05 NO NO19954925A patent/NO315147B1/no not_active IP Right Cessation
1996
- 1996-02-09 BG BG100346A patent/BG63269B1/bg unknown
1997
- 1997-09-26 US US08/938,898 patent/US20020058050A1/en not_active Abandoned
2002
- 2002-06-04 US US10/162,132 patent/US20030035837A1/en not_active Abandoned
- 2002-06-11 JP JP2002169943A patent/JP4368562B2/ja not_active Expired - Lifetime
2004
- 2004-08-27 JP JP2004248207A patent/JP4425093B2/ja not_active Expired - Lifetime
2006
- 2006-06-28 JP JP2006178333A patent/JP4767772B2/ja not_active Expired - Lifetime
- 2006-08-08 US US11/501,661 patent/US20060269604A1/en not_active Abandoned
2007
- 2007-06-08 US US11/760,349 patent/US20070237832A1/en not_active Abandoned
- 2007-06-08 US US11/760,393 patent/US20070237833A1/en not_active Abandoned
- 2007-06-08 US US11/760,316 patent/US20080031963A1/en not_active Abandoned
2009
- 2009-01-05 JP JP2009000357A patent/JP4908527B2/ja not_active Expired - Lifetime
- 2009-12-08 US US12/653,109 patent/US20100209351A1/en not_active Abandoned
- 2009-12-08 US US12/653,116 patent/US20100209514A1/en not_active Abandoned

Also Published As

Publication number	Publication date
ATE327739T1 (de)	2006-06-15
IL111742A0 (en)	1995-01-24
US20070237832A1 (en)	2007-10-11
AU1331395A (en)	1995-06-13
AU693134B2 (en)	1998-06-25
JP4767772B2 (ja)	2011-09-07
DE69434752T2 (de)	2007-05-16
FI955782L (fi)	1996-01-30
HK1029927A1 (en)	2001-04-20
PL312587A1 (en)	1996-04-29
ES2170136T5 (es)	2006-04-01
DE69434911T2 (de)	2007-08-30
JP4425093B2 (ja)	2010-03-03
KR100201767B1 (ko)	1999-06-15
US5672360A (en)	1997-09-30
ES2279742T3 (es)	2007-09-01
NO315147B1 (no)	2003-07-21
US5478577A (en)	1995-12-26
WO1995014460A1 (en)	1995-06-01
JP2002371015A (ja)	2002-12-26
US20030035837A1 (en)	2003-02-20
JP2006290901A (ja)	2006-10-26
EP1023896A9 (de)	2007-05-23
DE69434752D1 (de)	2006-07-06
FI955782A0 (fi)	1995-12-01
FI121588B (fi)	2011-01-31
BG100346A (bg)	1996-07-31
EP1776950A1 (de)	2007-04-25
CZ321795A3 (en)	1996-07-17
CN1130352A (zh)	1996-09-04
NZ508526A (en)	2004-12-24
EP0731694A4 (de)	1996-10-02
HUT73976A (en)	1996-10-28
US20100209514A1 (en)	2010-08-19
US20100209351A1 (en)	2010-08-19
BG63269B1 (bg)	2001-08-31
DE69429826T2 (de)	2002-09-05
JP2004323536A (ja)	2004-11-18
SK283544B6 (sk)	2003-09-11
ES2266951T3 (es)	2007-03-01
DE69429826T3 (de)	2006-08-03
SK153895A3 (en)	1996-06-05
KR960703004A (ko)	1996-06-19
PT1470815E (pt)	2006-09-29
EP0731694A1 (de)	1996-09-18
US20020058050A1 (en)	2002-05-16
CZ292936B6 (cs)	2004-01-14
NO954925L (no)	1996-05-23
EP1470815B1 (de)	2006-05-31
EP1470815A1 (de)	2004-10-27
DE69429826D1 (de)	2002-03-21
JP4908527B2 (ja)	2012-04-04
TW420617B (en)	2001-02-01
JP2009102376A (ja)	2009-05-14
DK0731694T3 (da)	2002-05-13
DK0731694T4 (da)	2005-12-19
NZ336055A (en)	2001-01-26
EP0731694B2 (de)	2005-09-07
EP1023896A2 (de)	2000-08-02
ATE212831T1 (de)	2002-02-15
JPH09505602A (ja)	1997-06-03
CN1134253C (zh)	2004-01-14
US20070237833A1 (en)	2007-10-11
HU9503468D0 (en)	1996-01-29
DE69434911D1 (de)	2007-02-15
DK1470815T3 (da)	2006-10-02
EP1023896B1 (de)	2007-01-03
NO954925D0 (no)	1995-12-05
US20060269604A1 (en)	2006-11-30
PT731694E (pt)	2002-06-28
ES2170136T3 (es)	2002-08-01
JP4368562B2 (ja)	2009-11-18
US20080031963A1 (en)	2008-02-07
EP0731694B1 (de)	2002-02-06
DK1023896T3 (da)	2007-05-14
NZ277917A (en)	1998-04-27
PT1023896E (pt)	2007-03-30
EP1023896A3 (de)	2003-05-02
ATE350022T1 (de)	2007-01-15

Legal Events

Date	Code	Title
2004-07-25	FF	Patent granted
2005-02-20	KB	Patent renewed
2009-06-15	KB	Patent renewed
2012-11-29	KB	Patent renewed
2015-06-30	EXP	Patent expired

Publication	Publication Date	Title
US5672360A (en)	1997-09-30	Method of treating pain by administering 24 hour oral opioid formulations
AU2006200783B2 (en)	2009-09-10	Opioid formulations for treating pain
AU735113B2 (en)	2001-06-28	Opioid formulations for treating pain
NZ329908A (en)	1999-10-28	Sustained release formulations for opioid medicaments
HK1070295B (en)	2006-12-22	Opiod formulations for treating pain
HK1070295A1 (en)	2005-06-17	Opiod formulations for treating pain
HK1100321A (en)	2007-09-14	Opioid formulations for treating pain
HK1029927B (en)	2007-06-22	Opioid formulations for treating pain