AR036882A1 - Sintesis de (4-bromofenil)(4-piperidil)metanona-(z)-o-etiloxima y sales - Google Patents
Sintesis de (4-bromofenil)(4-piperidil)metanona-(z)-o-etiloxima y salesInfo
- Publication number
- AR036882A1 AR036882A1 ARP020103833A ARP020103833A AR036882A1 AR 036882 A1 AR036882 A1 AR 036882A1 AR P020103833 A ARP020103833 A AR P020103833A AR P020103833 A ARP020103833 A AR P020103833A AR 036882 A1 AR036882 A1 AR 036882A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- acid
- isomer
- halogen
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 239000002253 acid Chemical class 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- NVVGGZMQGPFVTJ-SAPNQHFASA-N (z)-1-(4-bromophenyl)-n-ethoxy-1-piperidin-4-ylmethanimine Chemical class C=1C=C(Br)C=CC=1C(=N/OCC)\C1CCNCC1 NVVGGZMQGPFVTJ-SAPNQHFASA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 125000005262 alkoxyamine group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000005171 halobenzenes Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
En una realización, la presente describe la síntesis de (4-bromofenill)(4-piperidil)metanona-(Z)-O-etiloxima y sus sales de ácido y compuestos similares, en alta pureza estereoquímica. Reivindicación 1: Un proceso para la preparación de un compuesto de fórmula (1) donde X = halógeno, en donde dicho compuesto está en su forma de isómero Z en por lo menos aproximadamente 90% de pureza estereoquímica, y "Acido" se refiere a sal de ácido; dicho proceso comprende: (a) convertir ácido isonipecótico (fórmula 2) en su derivado N-protegido (fórmula 3), donde Y es un grupo protector; (b) convertir el compuesto de fórmula (3) en su haluro ácido (fórmula 4) donde G = halógeno; (c) hacer reaccionar dicho compuesto de fórmula (4) con un halobenceno adecuado en presencia de un catalizador de Friedel-Crafts adecuado, para producir el compuesto de Fórmula (5) donde X es un halógeno; (d) hacer reaccionar el compuesto de fórmula (5) con una alcoxiamina y un ácido para proporcionar el compuesto de fórmula (6) como una mezcla de los isómeros Z y E; y (e) isomerizar el compuesto de fórmula (6) mediante el tratamiento con un ácido fuerte, y en forma simultánea convertir en la sal de ácido deseada de fórmula (1) enriquecida con un isómero Z, en donde el isómero Z predomina sobre el isómero E por lo menos por una relación de 90:10.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32956201P | 2001-10-15 | 2001-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR036882A1 true AR036882A1 (es) | 2004-10-13 |
Family
ID=23285983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020103833A AR036882A1 (es) | 2001-10-15 | 2002-10-11 | Sintesis de (4-bromofenil)(4-piperidil)metanona-(z)-o-etiloxima y sales |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6914142B2 (es) |
| EP (1) | EP1436262A1 (es) |
| JP (2) | JP2005506355A (es) |
| CN (1) | CN1308308C (es) |
| AR (1) | AR036882A1 (es) |
| CA (1) | CA2463506C (es) |
| MX (1) | MXPA04003478A (es) |
| WO (1) | WO2003033465A1 (es) |
| ZA (1) | ZA200402068B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036882A1 (es) * | 2001-10-15 | 2004-10-13 | Schering Corp | Sintesis de (4-bromofenil)(4-piperidil)metanona-(z)-o-etiloxima y sales |
| WO2018147368A1 (ja) * | 2017-02-08 | 2018-08-16 | 日産化学株式会社 | オキシイミノ化合物の幾何異性体の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4408054A (en) | 1981-11-12 | 1983-10-04 | Hoechst-Roussel Pharmaceuticals Inc. | Oximes of 4-benzoyl-piperidines |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| PL203117B1 (pl) | 1999-05-04 | 2009-08-31 | Schering Corp | Piperydynopiperydynowa pochodna użyteczna jako antagonista CCR5, zawierająca ją kompozycja farmaceutyczna i jej zastosowanie |
| AR036882A1 (es) * | 2001-10-15 | 2004-10-13 | Schering Corp | Sintesis de (4-bromofenil)(4-piperidil)metanona-(z)-o-etiloxima y sales |
| US6642385B2 (en) * | 2001-10-15 | 2003-11-04 | Schering Corporation | Synthesis of 4-(piperidyl)(2-pyridyl)methanone-(E)-O-methyloxime and salts |
-
2002
- 2002-10-11 AR ARP020103833A patent/AR036882A1/es unknown
- 2002-10-11 US US10/269,803 patent/US6914142B2/en not_active Expired - Fee Related
- 2002-10-15 EP EP02801697A patent/EP1436262A1/en not_active Withdrawn
- 2002-10-15 CN CNB028203720A patent/CN1308308C/zh not_active Expired - Fee Related
- 2002-10-15 WO PCT/US2002/032761 patent/WO2003033465A1/en not_active Ceased
- 2002-10-15 CA CA2463506A patent/CA2463506C/en not_active Expired - Fee Related
- 2002-10-15 MX MXPA04003478A patent/MXPA04003478A/es active IP Right Grant
- 2002-10-15 JP JP2003536205A patent/JP2005506355A/ja active Pending
-
2004
- 2004-03-15 ZA ZA200402068A patent/ZA200402068B/en unknown
-
2005
- 2005-04-04 US US11/098,642 patent/US7524963B2/en not_active Expired - Fee Related
-
2009
- 2009-05-15 JP JP2009119322A patent/JP2009173688A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US7524963B2 (en) | 2009-04-28 |
| MXPA04003478A (es) | 2004-07-30 |
| JP2009173688A (ja) | 2009-08-06 |
| CA2463506A1 (en) | 2003-04-24 |
| ZA200402068B (en) | 2005-04-28 |
| WO2003033465A1 (en) | 2003-04-24 |
| US6914142B2 (en) | 2005-07-05 |
| CN1308308C (zh) | 2007-04-04 |
| US20050171159A1 (en) | 2005-08-04 |
| JP2005506355A (ja) | 2005-03-03 |
| CN1571768A (zh) | 2005-01-26 |
| EP1436262A1 (en) | 2004-07-14 |
| US20030092731A1 (en) | 2003-05-15 |
| CA2463506C (en) | 2011-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |