MX2014009353A - Procedimiento para la preparacion de analogos de morfina mediante la reaccion de reactivos organometalicos con una oxazolidina derivada a partir de morfinanos. - Google Patents
Procedimiento para la preparacion de analogos de morfina mediante la reaccion de reactivos organometalicos con una oxazolidina derivada a partir de morfinanos.Info
- Publication number
- MX2014009353A MX2014009353A MX2014009353A MX2014009353A MX2014009353A MX 2014009353 A MX2014009353 A MX 2014009353A MX 2014009353 A MX2014009353 A MX 2014009353A MX 2014009353 A MX2014009353 A MX 2014009353A MX 2014009353 A MX2014009353 A MX 2014009353A
- Authority
- MX
- Mexico
- Prior art keywords
- reaction
- oxazolidine
- morphinans
- preparation
- organometallic reagents
- Prior art date
Links
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 title abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 title abstract 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class 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 title abstract 2
- 125000002524 organometallic group Chemical group 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical class C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 title 1
- YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 abstract 2
- VANAVLBJMFLURS-MBPVOVBZSA-N (4r,4as,7ar,12bs)-3-(cyclobutylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CCC1 VANAVLBJMFLURS-MBPVOVBZSA-N 0.000 abstract 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 abstract 1
- 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 abstract 1
- 229960000805 nalbuphine Drugs 0.000 abstract 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 abstract 1
- 229960004127 naloxone Drugs 0.000 abstract 1
- DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 abstract 1
- 229960003086 naltrexone Drugs 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 229960005118 oxymorphone Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- 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:
- C07D489/06—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 a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La oxazolidina derivada a partir de la reacción de oximorfona con el reactivo de Burgess, temporalmente protegida en 0-3 y C-6, reacciona con el reactivo de Grignard u otros reactivos metálicos u organometálicos apropiados para proveer directamente, por ejemplo, derivados N-alilo, N-metilciclopropilo y N-metilciclobutilo que se convierten adicionalmente en naltrexona, naloxona, nalbufona y nalbufina con rendimientos excelentes. Estos análogos de morfina se pueden preparar a partir de la oxazolidina en una síntesis en un solo recipiente.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261594678P | 2012-02-03 | 2012-02-03 | |
| PCT/CA2013/050072 WO2013113120A1 (en) | 2012-02-03 | 2013-01-30 | Process for the preparation of morphine analogs via the reaction of organometallic reagents with an oxazolidine derived from morphinans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2014009353A true MX2014009353A (es) | 2015-11-06 |
Family
ID=48904344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014009353A MX2014009353A (es) | 2012-02-03 | 2013-01-30 | Procedimiento para la preparacion de analogos de morfina mediante la reaccion de reactivos organometalicos con una oxazolidina derivada a partir de morfinanos. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8981098B2 (es) |
| EP (1) | EP2809674A4 (es) |
| JP (1) | JP2015506952A (es) |
| CN (1) | CN104520302A (es) |
| AU (1) | AU2013214667A1 (es) |
| CA (1) | CA2863242A1 (es) |
| IN (1) | IN2014DN07315A (es) |
| MX (1) | MX2014009353A (es) |
| WO (1) | WO2013113120A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9701687B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
| US9701688B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60152447A (ja) * | 1984-01-19 | 1985-08-10 | Toyobo Co Ltd | ２−ν，νジ置換アミノ−２−置換−１，３−プロパンジオ−ルの合成法 |
| DE10229842A1 (de) | 2002-07-03 | 2004-02-05 | Helmut Prof. Dr. Schmidhammer | Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung |
| HUE034668T2 (hu) * | 2003-09-22 | 2018-02-28 | Glaxosmithkline Australia Pty Ltd | Eljárás morfinán-származékok szintézisére és azok intermedierjei |
| CA2670342A1 (en) * | 2006-11-22 | 2008-06-12 | Progenics Pharmaceuticals, Inc. | N-oxides of 4,5-epoxy-morphinanium analogs |
| WO2009067275A1 (en) | 2007-11-21 | 2009-05-28 | Progenics Pharmaceuticals, Inc | N-oxides of 4,5-epoxy-morphinanium analogs |
| CN102227433B (zh) * | 2008-09-30 | 2015-01-07 | 马林克罗特有限公司 | 烷基化吗啡喃衍生物的仲胺基团的方法 |
| AU2010239059B2 (en) | 2009-04-24 | 2016-06-09 | Brock University | Processes for the preparation of morphinane and morphinone compounds |
| WO2011154827A2 (en) * | 2010-06-11 | 2011-12-15 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
| WO2011154826A1 (en) * | 2010-06-11 | 2011-12-15 | Rhodes Technologies | Process for n-dealkylation of tertiary amines |
| WO2012149633A1 (en) * | 2011-05-02 | 2012-11-08 | Brock University | Processes and intermediates in the preparation of morphine analogs via n-demethylation of n-oxides using cyclodehydration reagents |
-
2013
- 2013-01-30 MX MX2014009353A patent/MX2014009353A/es unknown
- 2013-01-30 JP JP2014555049A patent/JP2015506952A/ja not_active Ceased
- 2013-01-30 US US14/374,397 patent/US8981098B2/en not_active Expired - Fee Related
- 2013-01-30 IN IN7315DEN2014 patent/IN2014DN07315A/en unknown
- 2013-01-30 WO PCT/CA2013/050072 patent/WO2013113120A1/en not_active Ceased
- 2013-01-30 CA CA2863242A patent/CA2863242A1/en not_active Abandoned
- 2013-01-30 AU AU2013214667A patent/AU2013214667A1/en not_active Abandoned
- 2013-01-30 EP EP13743449.4A patent/EP2809674A4/en not_active Withdrawn
- 2013-01-30 CN CN201380017946.2A patent/CN104520302A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013113120A1 (en) | 2013-08-08 |
| US8981098B2 (en) | 2015-03-17 |
| EP2809674A1 (en) | 2014-12-10 |
| AU2013214667A1 (en) | 2014-09-25 |
| IN2014DN07315A (es) | 2015-04-24 |
| EP2809674A4 (en) | 2015-09-02 |
| JP2015506952A (ja) | 2015-03-05 |
| CN104520302A (zh) | 2015-04-15 |
| US20140371458A1 (en) | 2014-12-18 |
| CA2863242A1 (en) | 2013-08-08 |
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