BR0016063A - Métodos para a sìntese de alfentanila, sufentanila e remifentanila - Google Patents

Métodos para a sìntese de alfentanila, sufentanila e remifentanila

Info

Publication number
BR0016063A
BR0016063A BR0016063-6A BR0016063A BR0016063A BR 0016063 A BR0016063 A BR 0016063A BR 0016063 A BR0016063 A BR 0016063A BR 0016063 A BR0016063 A BR 0016063A
Authority
BR
Brazil
Prior art keywords
remifentanil
alfentanil
sufentanil
methods
synthesis
Prior art date
Application number
BR0016063-6A
Other languages
English (en)
Inventor
Mathew Jacob
J Kendall Killgore
Original Assignee
Mallinckrodt Inc
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.)
Filing date
Publication date
Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc
Publication of BR0016063A publication Critical patent/BR0016063A/pt

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

"MéTODOS PARA A SìNTESE DE ALFENTANILA, SUFENTANILA E REMIFENTANILA". São descritos atalhos sintéticos para a sintetização de derivados ou análogos da fentanila. São estabelecidos de forma específica os caminhos para a sintetização de alfentanila, sufentanila e remifentanila. Os métodos descritos necessitam de menos etapas e produzem um grande rendimento do produtos do que os métodos relatados na técnica anterior. Os caminhos para todos esses compostos começam com um caminho comum da condensação de uma piperidona com uma amina primária de modo a formar uma 4-amino-4-carboxiamino-piperidina, em que o N da referida piperidona é um -N-COO-(CH~ 2~ )~ n~CH~ 3~, alquilando um N da referida amina primária que foi condensada com a referida piperidona, produzindo por esse motivo uma Nalquil-anilida, e hidrolisando o referido grupo -COO-(CH~ 2~ )~ N~CH~ 3~ da referida 4amino-4-carboxiamino-piperadina seguido por condensação de modo a formar um produto da hidrólise da piperidina. Esse produto pode em seguida ser convertido para a remifentanila em uma reação de 4 etapas. Também, este produto da hidrólise pode ser tratado com um hidreto para dar uma 4hidroximetil-piperidina a qual pode ser convertida para alfentanila em mais três etapas, para sufentanila em mais 3 etapas ou para uma variedade de análogos da remifentanila em duas etapas.
BR0016063-6A 1999-12-06 2000-12-04 Métodos para a sìntese de alfentanila, sufentanila e remifentanila BR0016063A (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16873999P 1999-12-06 1999-12-06
PCT/US2000/032882 WO2001040184A2 (en) 1999-12-06 2000-12-04 Methods for the syntheses of alfentanil, sufentanil and remifentanil

Publications (1)

Publication Number Publication Date
BR0016063A true BR0016063A (pt) 2002-08-06

Family

ID=22612741

Family Applications (1)

Application Number Title Priority Date Filing Date
BR0016063-6A BR0016063A (pt) 1999-12-06 2000-12-04 Métodos para a sìntese de alfentanila, sufentanila e remifentanila

Country Status (10)

Country Link
US (2) US7074935B2 (pt)
EP (1) EP1246801B1 (pt)
JP (1) JP2003515588A (pt)
AT (1) ATE340159T1 (pt)
AU (1) AU2427201A (pt)
BR (1) BR0016063A (pt)
CA (1) CA2393559C (pt)
DE (1) DE60030883T2 (pt)
ES (1) ES2272354T3 (pt)
WO (1) WO2001040184A2 (pt)

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DE10141650C1 (de) 2001-08-24 2002-11-28 Lohmann Therapie Syst Lts Transdermales Therapeutisches System mit Fentanyl bzw. verwandten Substanzen
DE602004018674D1 (de) * 2003-10-29 2009-02-05 Mallinckrodt Inc Grosstechnisches verfahren zur abtrennung und aufreinigung von fentanyl durch präparative umkehrphasenchromatographie
CA2581863A1 (en) * 2004-11-10 2006-05-26 Boehringer Ingelheim Chemicals, Inc. Process of making fentanyl intermediates
GB0509276D0 (en) * 2005-05-06 2005-06-15 Univ Cranfield Synthetic receptor
EP1966140A1 (en) * 2005-11-17 2008-09-10 Mallinckrodt, Inc. Process for synthesizing remifentanil
US8753308B2 (en) 2006-01-06 2014-06-17 Acelrx Pharmaceuticals, Inc. Methods for administering small volume oral transmucosal dosage forms using a dispensing device
US8865743B2 (en) 2006-01-06 2014-10-21 Acelrx Pharmaceuticals, Inc. Small volume oral transmucosal dosage forms containing sufentanil for treatment of pain
US9289583B2 (en) 2006-01-06 2016-03-22 Acelrx Pharmaceuticals, Inc. Methods for administering small volume oral transmucosal dosage forms using a dispensing device
US8535714B2 (en) 2006-01-06 2013-09-17 Acelrx Pharmaceuticals, Inc. Small volume oral transmucosal dosage forms containing sufentanil for treatment of pain
US8357114B2 (en) 2006-01-06 2013-01-22 Acelrx Pharmaceuticals, Inc. Drug dispensing device with flexible push rod
US9066847B2 (en) * 2007-01-05 2015-06-30 Aceirx Pharmaceuticals, Inc. Storage and dispensing devices for administration of oral transmucosal dosage forms
US8252329B2 (en) 2007-01-05 2012-08-28 Acelrx Pharmaceuticals, Inc. Bioadhesive drug formulations for oral transmucosal delivery
US8252328B2 (en) * 2006-01-06 2012-08-28 Acelrx Pharmaceuticals, Inc. Bioadhesive drug formulations for oral transmucosal delivery
US8202535B2 (en) 2006-01-06 2012-06-19 Acelrx Pharmaceuticals, Inc. Small-volume oral transmucosal dosage forms
JP2009525329A (ja) * 2006-02-03 2009-07-09 マリンクロッド・インコーポレイテッド レミフェンタニル塩酸塩の結晶形
US20070260491A1 (en) * 2006-05-08 2007-11-08 Pamela Palmer System for delivery and monitoring of administration of controlled substances
EP1867635A1 (en) * 2006-06-15 2007-12-19 Kern Pharma, S.L. Process for preparing remifentanil, intermediates thereof, use of said intermediates and processes for their preparation
US20070299687A1 (en) * 2006-06-23 2007-12-27 Pamela Palmer Inpatient system for patient-controlled delivery of oral transmucosal medications dosed as needed
US20100099880A1 (en) * 2006-10-05 2010-04-22 Brian Cheng Alternate Process for Remifentanil Preparation
US20100048908A1 (en) * 2006-11-29 2010-02-25 Brian Kai-Ming Cheng Process for Remifentanil Synthesis
US20110144346A1 (en) * 2008-07-03 2011-06-16 Cilag Ag Method for producing n-phenyl-n-(4-piperidinyl) amide salts
US20100056574A1 (en) * 2008-09-04 2010-03-04 Mallinckrodt Inc. Crystalline Forms of Sufentanil
WO2010053944A1 (en) * 2008-11-04 2010-05-14 Cambrex Charles City, Inc. Improved method of making piperidine derivatives
US8945592B2 (en) * 2008-11-21 2015-02-03 Acelrx Pharmaceuticals, Inc. Sufentanil solid dosage forms comprising oxygen scavengers and methods of using the same
WO2012037309A2 (en) * 2010-09-17 2012-03-22 Mallinckrodt Llc Improved process for the preparation of sufentanil base and related compounds
EP2455377B1 (de) 2010-11-11 2014-07-09 hameln rds gmbh Synthese von Fentanyl Analoga
CN102060753B (zh) * 2010-12-29 2013-01-09 宜昌人福药业有限责任公司 一种4-苯胺基哌啶类镇痛药的精制方法
CN103044398B (zh) * 2012-12-12 2015-09-16 宜昌人福药业有限责任公司 一种盐酸阿芬太尼的晶型
US8742111B1 (en) * 2013-02-21 2014-06-03 The United States Of America As Represented By The Secretary Of The Army Synthesis of intermediate anilino methyl esters used in the production of synthetic opioid analgesics
US9765027B2 (en) * 2014-08-22 2017-09-19 Arizona Board Of Regents On Behalf Of The University Of Arizona Substituted 1-arylethyl-4-acylaminopiperidine derivatives as opioid/alpha-adrenoreceptor modulators and method of their preparation
EP3233077A4 (en) 2014-12-19 2018-08-08 The Broad Institute Inc. Dopamine d2 receptor ligands
EP3233799B1 (en) 2014-12-19 2021-05-19 The Broad Institute, Inc. Dopamine d2 receptor ligands
BR112017025115B1 (pt) 2015-05-27 2023-03-14 Mallinckrodt Llc Processo para formar citrato de sufentanila a partir de base de sufentanila
ES2699636T3 (es) 2016-01-29 2019-02-12 Bioka S R O Nuevo procedimiento para la preparación de derivados de N-fenil-N-(4-piperidinil) amida, como remifentanilo y carfentanilo
US10766925B2 (en) * 2016-04-11 2020-09-08 Arizona Board Of Regents On Behalf Of The University Of Arizona Opioid receptor modulators
US9650338B1 (en) 2016-07-29 2017-05-16 VDM Biochemicals, Inc. Opioid antagonist compounds and methods of making and using
WO2022195497A1 (en) * 2021-03-16 2022-09-22 Ami Organics Ltd. A process for the preparation of 4-piperidone hcl hydrate

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US3161644A (en) 1962-06-22 1964-12-15 Res Lab Dr C Janssen N V 1-benzyl-4-substituted piperidines
US3998834A (en) * 1975-03-14 1976-12-21 Janssen Pharmaceutica N.V. N-(4-piperidinyl)-n-phenylamides and -carbamates
FR2389622B1 (pt) * 1977-05-05 1982-05-21 Janssen Pharmaceutica Nv
US4167574A (en) 1978-03-13 1979-09-11 Janssen Pharmaceutica, N.V. N-phenyl-N-(4-piperidinyl)amides
US5019583A (en) 1989-02-15 1991-05-28 Glaxo Inc. N-phenyl-N-(4-piperidinyl)amides useful as analgesics
US5461147A (en) 1993-09-27 1995-10-24 Schering Corporation Process for preparing benzazepine intermediates for the synthesis of D1 antagonists
US5489689A (en) * 1993-09-30 1996-02-06 Mallinckrodt Chemical, Inc. Preparation of piperidine derivatives

Also Published As

Publication number Publication date
JP2003515588A (ja) 2003-05-07
US20060149071A1 (en) 2006-07-06
US7208604B2 (en) 2007-04-24
AU2427201A (en) 2001-06-12
ES2272354T3 (es) 2007-05-01
ATE340159T1 (de) 2006-10-15
WO2001040184A2 (en) 2001-06-07
US7074935B2 (en) 2006-07-11
DE60030883T2 (de) 2007-09-06
WO2001040184B1 (en) 2002-01-31
DE60030883D1 (de) 2006-11-02
WO2001040184A3 (en) 2002-01-03
US20040138461A1 (en) 2004-07-15
EP1246801B1 (en) 2006-09-20
EP1246801A2 (en) 2002-10-09
CA2393559C (en) 2009-05-26
CA2393559A1 (en) 2001-06-07

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Legal Events

Date Code Title Description
B07A Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]
B09B Patent application refused [chapter 9.2 patent gazette]

Free format text: INDEFIRO O PEDIDO DE ACORDO COM O(S) ARTIGO(S) 8O, 13 E 25 DA LPI

B09B Patent application refused [chapter 9.2 patent gazette]

Free format text: MANTIDO O INDEFERIMENTO UMA VEZ QUE NAO FOI APRESENTADO RECURSO DENTRO DO PRAZO LEGAL.