HRP20110078T1 - Postupak reduciranja alfa, beta nezasićenih ketona u opioidnim sastavima - Google Patents
Postupak reduciranja alfa, beta nezasićenih ketona u opioidnim sastavima Download PDFInfo
- Publication number
- HRP20110078T1 HRP20110078T1 HR20110078T HRP20110078T HRP20110078T1 HR P20110078 T1 HRP20110078 T1 HR P20110078T1 HR 20110078 T HR20110078 T HR 20110078T HR P20110078 T HRP20110078 T HR P20110078T HR P20110078 T1 HRP20110078 T1 HR P20110078T1
- Authority
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- Prior art keywords
- alkyl
- group
- opioid analgesic
- phenyl
- cycloalkyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract 15
- 238000000034 method Methods 0.000 title claims abstract 11
- 150000002576 ketones Chemical class 0.000 title claims abstract 10
- 239000000014 opioid analgesic Substances 0.000 claims abstract 13
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910000071 diazene Inorganic materials 0.000 claims abstract 7
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 238000005984 hydrogenation reaction Methods 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 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 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 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 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 230000008929 regeneration Effects 0.000 claims 2
- 238000011069 regeneration method Methods 0.000 claims 2
- 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 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 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 1
- 229960001736 buprenorphine Drugs 0.000 claims 1
- 229960004126 codeine Drugs 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229960000240 hydrocodone Drugs 0.000 claims 1
- 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 1
- 229960001410 hydromorphone Drugs 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 229960002085 oxycodone Drugs 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims 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
- A61K31/33—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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
Abstract
Postupak reduciranja količine α,?-nezasićenog ketona u sastavu opioidnog analgetika, koji sadrži hidrogeniranje početnog sastava opioidnog analgetika koji ima α,?-nezasićeni keton s primjesama diimida, preteču diimida, ili njihovu kombinaciju u odgovarajućem otapalu, kako bi se proizveo rezultantni sastav opioidnog analgetika koja ima manji sadržaj α,?-nezasićenog ketona nego početni sastav, gdje je opioidni analgetik spoj formule (III): gdje R je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cikloalkila; (C3-6)cikloalkil(C1-3) alkila; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano; R1 je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cilkoalkila; C1-8 alkoksija; C3-6 cikloalkoksija; 2-(4-morfolinil)etila; benziloksikarbonila; (R8)3C(O)-; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano; R2 je odabran iz skupine koja se sastoji od vodika; okso; hidroksila; C1-8 alkila; C1-8 alkoksija; C3-6 cikloalkila; C3-6 cikloalkoksija; i R4 je vodik; hidroksil; alkoksi; C1-8 alkil supstituiran s 1-3 člana skupine koja se sastoji od C1-8 alkila, hidroksila, cijano, nitro i dialkilamino; svaki R8 je neovisno vodik, C1-4 alkil, C3-6 cikloalkil, fenil ili benzil; ili njegova farmaceutski prihvatljiva sol. Patent sadrži još 8 patentnih zahtjeva.
Claims (9)
1. Postupak reduciranja količine α,β-nezasićenog ketona u sastavu opioidnog analgetika, koji sadrži hidrogeniranje početnog sastava opioidnog analgetika koji ima α,β-nezasićeni keton s primjesama diimida, preteču diimida, ili njihovu kombinaciju u odgovarajućem otapalu, kako bi se proizveo rezultantni sastav opioidnog analgetika koja ima manji sadržaj α,β-nezasićenog ketona nego početni sastav, gdje je opioidni analgetik spoj formule (III):
[image]
gdje
R je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cikloalkila; (C3-6)cikloalkil(C1-3) alkila; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano;
R1 je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cilkoalkila; C1-8 alkoksija; C3-6 cikloalkoksija; 2-(4-morfolinil)etila; benziloksikarbonila; (R8)3C(O)-; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano;
R2 je odabran iz skupine koja se sastoji od vodika; okso; hidroksila; C1-8 alkila; C1-8 alkoksija; C3-6 cikloalkila; C3-6 cikloalkoksija; i
R4 je vodik; hidroksil; alkoksi; C1-8 alkil supstituiran s 1-3 člana skupine koja se sastoji od C1-8 alkila, hidroksila, cijano, nitro i dialkilamino;
svaki R8 je neovisno vodik, C1-4 alkil, C3-6 cikloalkil, fenil ili benzil; ili njegova farmaceutski prihvatljiva sol.
2. Postupak prema zahtjevu 1, naznačen time da je preteča diimida dikalijev azodikarboksilat.
3. Postupak prema zahtjevu 1, naznačen time da je navedeno hidrogeniranje provedeno pod refluksom.
4. Postupak prema zahtjevu 1, naznačen time da je otapalo alkohol, poželjno odabrano iz skupine koja se sastoji od metanola, etanola i izopropanola.
5. Postupak prema zahtjevu 1, naznačen time da nadalje sadrži regeneraciju sastava opioidnog analgetika nakon hidrogeniranja, poželjno gdje korak regeneracije sadrži kristalizaciju sastava opioidnog analgetika.
6. Postupak prema zahtjevu 1, naznačen time da je opioidni analgetik odabran iz skupine koja se sastoji od hidrokodona ili kodeina, njihovih farmaceutski prihvatljivih soli i njihovih smjesa.
7. Postupak prema zahtjevu 1, naznačen time da hidrogeniranje proizvodi sastav opioidnog analgetika koji ima sadržaj α, β- nezasićenog ketona manji od 25 ppm, manji od 15 ppm, manji od 10 ppm, ili manji od 5 ppm.
8. Postupak prema zahtjevu 1, naznačen time da je α, β-nezasićeni keton spoj formule (II):
[image]
gdje:
R je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cikloalkila; (C3-6)cikloalkil(C1-3) alkila; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano;
R1 je odabran iz skupine koja se sastoji od vodika; C1-8 alkila; C3-6 cilkoalkila; C1-8 alkoksija; C3-6 cikloalkoksija; 2-(4-morfolinil)etila; benziloksikarbonila; (R8)3C(O)-; fenil(C1-3)alkila; i fenil(C1-3)alkila supstituiranog s 1-3 člana skupine koja se sastoji od C1-8 alkila, trifluorometila, nitro, dialkilamino i cijano;
R3 je vodik, hidroksil ili alkoksi;
svaki R8 je neovisno vodik, C1-4 alkil, C3-6 cikloalkil, fenil ili benzil
ili njegova farmaceutski prihvatljiva sol.
9. Postupak reduciranja količine α, β-nezasićenog ketona u sastavu opioidnog analgetika koji sadrži hidrogeniranje početnog sastava opioidnog analgetika koji ima α, β-nezasićeni keton s primjesama diimida, preteču diimida, ili njihovu kombinaciju u odgovarajućem otapalu, kako bi se proizveo rezultantni sastav opioidnog analgetika koja ima manji sadržaj α, β-nezasićenog ketona nego početni sastav, gdje je opioidni analgetik, oksikodon, hidromorfon, morfij, buprenorfin, ili njihove farmaceutski prihvatljive soli i njihove smjese.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65879105P | 2005-03-04 | 2005-03-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110078T1 true HRP20110078T1 (hr) | 2011-03-31 |
Family
ID=36301669
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090387T HRP20090387T1 (hr) | 2005-03-04 | 2009-07-07 | Postupak reduciranja alfa, beta nezasićenih ketona u opioidnim sastavima |
| HR20110078T HRP20110078T1 (hr) | 2005-03-04 | 2011-02-01 | Postupak reduciranja alfa, beta nezasićenih ketona u opioidnim sastavima |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090387T HRP20090387T1 (hr) | 2005-03-04 | 2009-07-07 | Postupak reduciranja alfa, beta nezasićenih ketona u opioidnim sastavima |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7939543B2 (hr) |
| EP (2) | EP2112153B1 (hr) |
| JP (1) | JP5314894B2 (hr) |
| KR (1) | KR100941761B1 (hr) |
| CN (1) | CN101133062B (hr) |
| AT (2) | ATE487722T1 (hr) |
| CA (1) | CA2598774C (hr) |
| CY (2) | CY1109262T1 (hr) |
| DE (2) | DE602006018208D1 (hr) |
| DK (2) | DK2112153T3 (hr) |
| ES (2) | ES2355870T3 (hr) |
| HK (2) | HK1111695A1 (hr) |
| HR (2) | HRP20090387T1 (hr) |
| ME (2) | ME01594B (hr) |
| PL (2) | PL2112153T3 (hr) |
| PT (2) | PT2112153E (hr) |
| RS (2) | RS51131B (hr) |
| SI (2) | SI1861405T1 (hr) |
| WO (1) | WO2006094672A1 (hr) |
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| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| MXPA06001452A (es) * | 2003-08-06 | 2007-04-02 | Gruenenthal Chemie | Forma de administracion a prueba de abuso. |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| TWI483944B (zh) | 2004-03-30 | 2015-05-11 | Euro Celtique Sa | 含有小於２５ｐｐｍ１４-羥可待因酮之羥可酮鹽酸鹽組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
| 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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| EP3003283A1 (en) | 2013-05-29 | 2016-04-13 | Grünenthal GmbH | Tamper resistant dosage form with bimodal release profile |
| JP6449871B2 (ja) | 2013-07-12 | 2019-01-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | エチレン−酢酸ビニルポリマーを含有する改変防止剤形 |
| WO2015078891A1 (en) | 2013-11-26 | 2015-06-04 | Farmaceutici Formenti S.P.A. | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
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| US10227354B2 (en) | 2013-12-18 | 2019-03-12 | Cody Laboratories, Inc. | Conversion of oxycodone base to oxycodone hydrochloride |
| CN106572980A (zh) | 2014-05-12 | 2017-04-19 | 格吕伦塔尔有限公司 | 包含他喷他多的防篡改即释胶囊制剂 |
| EP3148512A1 (en) | 2014-05-26 | 2017-04-05 | Grünenthal GmbH | Multiparticles safeguarded against ethanolic dose-dumping |
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| US3812312A (en) * | 1971-11-15 | 1974-05-21 | Chrysler Corp | Impact velocity sensor switch with linearly movable controller |
| US5869669A (en) * | 1996-07-26 | 1999-02-09 | Penick Corporation | Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates |
| GB9713703D0 (en) | 1997-06-30 | 1997-09-03 | Johnson Matthey Plc | Preparation of opiates |
| US6177567B1 (en) * | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| TWI483944B (zh) * | 2004-03-30 | 2015-05-11 | Euro Celtique Sa | 含有小於２５ｐｐｍ１４-羥可待因酮之羥可酮鹽酸鹽組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
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