CA2694497C - Quaternary opioid carboxamides - Google Patents

Quaternary opioid carboxamides Download PDF

Info

Publication number
CA2694497C
CA2694497C CA2694497A CA2694497A CA2694497C CA 2694497 C CA2694497 C CA 2694497C CA 2694497 A CA2694497 A CA 2694497A CA 2694497 A CA2694497 A CA 2694497A CA 2694497 C CA2694497 C CA 2694497C
Authority
CA
Canada
Prior art keywords
compound
compounds
morphine
hydrogen
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2694497A
Other languages
English (en)
French (fr)
Other versions
CA2694497A1 (en
Inventor
Mark P. Wentland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rensselaer Polytechnic Institute
Original Assignee
Rensselaer Polytechnic Institute
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 Rensselaer Polytechnic Institute filed Critical Rensselaer Polytechnic Institute
Publication of CA2694497A1 publication Critical patent/CA2694497A1/en
Application granted granted Critical
Publication of CA2694497C publication Critical patent/CA2694497C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/28—Morphinans
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Hematology (AREA)
  • Anesthesiology (AREA)
  • Otolaryngology (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2694497A 2007-08-09 2008-08-08 Quaternary opioid carboxamides Active CA2694497C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US95496007P 2007-08-09 2007-08-09
US60/954,960 2007-08-09
PCT/US2008/072632 WO2009023567A1 (en) 2007-08-09 2008-08-08 Quaternary opioid carboxamides

Publications (2)

Publication Number Publication Date
CA2694497A1 CA2694497A1 (en) 2009-02-19
CA2694497C true CA2694497C (en) 2016-07-12

Family

ID=39941437

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2694497A Active CA2694497C (en) 2007-08-09 2008-08-08 Quaternary opioid carboxamides

Country Status (14)

Country Link
US (4) US8263807B2 (esLanguage)
EP (1) EP2190819B1 (esLanguage)
JP (1) JP5581211B2 (esLanguage)
KR (1) KR101519682B1 (esLanguage)
CN (1) CN101827819B (esLanguage)
AU (1) AU2008286979B2 (esLanguage)
BR (1) BRPI0815020A2 (esLanguage)
CA (1) CA2694497C (esLanguage)
EA (1) EA020658B1 (esLanguage)
ES (1) ES2586245T3 (esLanguage)
IL (1) IL203459A (esLanguage)
MX (1) MX2010001371A (esLanguage)
NO (1) NO341089B1 (esLanguage)
WO (1) WO2009023567A1 (esLanguage)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103275004A (zh) 2007-11-30 2013-09-04 普渡制药公司 苯并吗啡烷化合物
EP3170395A1 (en) * 2009-03-19 2017-05-24 Alkermes Pharma Ireland Limited Morphinan derivatives with high oral bioavailability
ES2729679T3 (es) 2009-12-04 2019-11-05 Alkermes Pharma Ireland Ltd Derivados de morfinano para el tratamiento de la sobredosis de fármacos
WO2011119605A2 (en) * 2010-03-22 2011-09-29 Rensselaer Polytechnic Institute Carboxamide biosiosteres of opiates
WO2012005795A1 (en) * 2010-07-08 2012-01-12 Alkermes, Inc. Process for the synthesis of substituted morphinans
EP2407469A1 (en) * 2010-07-13 2012-01-18 Chemo Ibérica, S.A. Salt of sitagliptin
ES2705726T3 (es) 2010-08-23 2019-03-26 Alkermes Pharma Ireland Ltd Métodos para tratar el aumento de peso inducido por antipsicóticos
US20120245193A1 (en) * 2011-02-14 2012-09-27 Alkermes, Inc. PERIPHERIALLY ACTING μ OPIOID ANTAGONISTS
MX2013010027A (es) * 2011-03-03 2014-02-11 Cadila Healthcare Ltd Sales novedosas de inhibidor de la dipeptidil peptidasa iv (dpp-iv).
WO2012138888A1 (en) * 2011-04-05 2012-10-11 Alkermes, Inc. Process for the synthesis of quaternary amine compounds
EP2725908B1 (en) 2011-06-29 2017-05-31 Alkermes, Inc. Peripherally acting opioid compounds
US9096606B2 (en) 2011-12-08 2015-08-04 Purdue Pharma, L.P. Quarternized buprenorphine analogs
US9211293B2 (en) 2011-12-15 2015-12-15 Alkermes Pharma Ireland Limited Opioid agonist antagonist combinations
ES2692771T3 (es) 2011-12-15 2018-12-05 Alkermes Pharma Ireland Limited Samidorfano (ALKS 33) en combinación con buprenorfina para el tratamiento de trastornos depresivos
US20140066475A1 (en) 2012-09-04 2014-03-06 Euro-Celtique S.A. Method For Treating Pruritus
JP2016519161A (ja) 2013-05-24 2016-06-30 アルカームス ファーマ アイルランド リミテッド モルファン及びモルフィナン類似物及び使用の方法
EP3003311A2 (en) 2013-05-24 2016-04-13 Alkermes Pharma Ireland Limited Methods for treating depressive symptoms
US20160243112A1 (en) * 2015-02-25 2016-08-25 Alkermes, Inc. Treatments for alzheimer's related diseases and disorders
TW202140009A (zh) * 2020-02-13 2021-11-01 大陸商上海翰森生物醫藥科技有限公司 ３－甲醯胺基－４－羥基納曲酮氘代衍生物、其製備方法及其在醫藥上的應用
EP4243768A1 (en) 2020-11-12 2023-09-20 Alkermes Pharma Ireland Limited Immediate release multilayer tablet
CN115521317B (zh) * 2021-02-02 2025-07-25 山东新时代药业有限公司 一种制备纳呋拉啡中间体的方法
WO2025104754A1 (en) * 2023-11-17 2025-05-22 Msn Laboratories Private Limited, R&D Center A process for the preparation of samidorphan and its intermediates
CN118598813B (zh) * 2024-08-08 2024-10-29 山东齐都药业有限公司 L-苹果酸萨米多芬及其制备方法

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES252980A1 (es) * 1958-10-30 1960-11-01 Boehringer Sohn Ingelheim Procedimiento para la obtencion de nuevas sales cuaternarias, terapéuticamente valiosas, de la normorfina y de sus derivados
DE2254298A1 (de) * 1972-11-06 1974-05-16 Boehringer Sohn Ingelheim Neue (heteroarylmethyl)-normorphine, deren saeureadditionssalze, verfahren zu deren herstellung sowie deren verwendung als arzneimittel
US4032529A (en) * 1974-09-20 1977-06-28 Sterling Drug Inc. Aminomethanobenzazocine intermediates
GB1511319A (en) * 1974-09-20 1978-05-17 Sterling Drug Inc 2,6-methane-3-benzazocine derivatives and their preparation
US4176186A (en) * 1978-07-28 1979-11-27 Boehringer Ingelheim Gmbh Quaternary derivatives of noroxymorphone which relieve intestinal immobility
FR2514644A1 (fr) 1981-10-19 1983-04-22 Sanofi Sa Composition pharmaceutique a action antagoniste peripherique des opiaces
CA1315689C (en) * 1987-09-03 1993-04-06 Leon I. Goldberg Quarternary derivatives of noroxymorphone which relieve nausea and emesis
TR199801348T2 (xx) * 1996-01-10 1998-10-21 Smithkline Beecham S.P.A. Heterosikl-kondanse morfinoid t�revleri(II).
ES2121553B1 (es) * 1996-12-23 1999-06-16 Univ Santiago Compostela Nuevos endoperoxidos morfinicos funcionalizados en posiciones c-6 y c-14 del anillo c y procedimiento para su obtencion.
WO2001014382A1 (en) * 1999-08-23 2001-03-01 Toray Industries, Inc. Analgesics containing as the active ingredient quaternary ammonium salt derivatives of morphinan
WO2001013909A2 (en) * 1999-08-25 2001-03-01 Cooper Barrett R Compositions and methods for treating opiate intolerance
NZ518562A (en) * 1999-11-29 2005-04-29 Adolor Corp Novel methods and compositions involving opioids and antagonists thereof
ES2572332T3 (es) * 2000-10-31 2016-05-31 Rensselaer Polytech Inst 2,6-metano-3-benzazocinas sustituidas en posición 8 y morfinanos sustituidos en posición 3 como ligandos de receptores opioides
US7375082B2 (en) * 2002-02-22 2008-05-20 Shire Llc Abuse-resistant hydrocodone compounds
DE10229842A1 (de) 2002-07-03 2004-02-05 Helmut Prof. Dr. Schmidhammer Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung
BR0314488A (pt) * 2002-09-25 2005-08-02 Euro Celtique Sa Composto, composição farmacêutica e métodos de tratamento
PT1562953E (pt) * 2002-11-08 2009-11-19 Mallinckrodt Inc Processo para a preparação de sais quaternários de n -alquilmorfinano
BRPI0517091B8 (pt) 2004-11-05 2021-05-25 Rensselaer Polytech Inst composto 4-hidroxibenzomorfano substituído na posição-3 por carboxamida ou tiocarboxamida
CN101171010B (zh) 2005-03-07 2014-09-17 芝加哥大学 阿片样物质拮抗剂用于减少内皮细胞增殖和迁移的用途
WO2007014137A2 (en) 2005-07-21 2007-02-01 Rensselaer Polytechnic Institute 8-carboxamido-substituted-2 , 6-methano-3-benzazocines and 3 - carboxamido- substituted morphanes as opioid receptor binding agents
US8163701B2 (en) * 2005-08-19 2012-04-24 Signature Therapeutics, Inc. Prodrugs of active agents

Also Published As

Publication number Publication date
JP2010535814A (ja) 2010-11-25
HK1141295A1 (zh) 2010-11-05
ES2586245T3 (es) 2016-10-13
NO20100289L (no) 2010-03-02
KR20100053627A (ko) 2010-05-20
EA201070237A1 (ru) 2010-10-29
US20090197905A1 (en) 2009-08-06
AU2008286979A1 (en) 2009-02-19
US8263807B2 (en) 2012-09-11
MX2010001371A (es) 2010-03-10
US20140107143A1 (en) 2014-04-17
CN101827819B (zh) 2013-06-12
BRPI0815020A2 (pt) 2015-03-10
IL203459A (en) 2016-02-29
US8563572B2 (en) 2013-10-22
EP2190819A1 (en) 2010-06-02
US20170095469A1 (en) 2017-04-06
CN101827819A (zh) 2010-09-08
EA020658B1 (ru) 2014-12-30
KR101519682B1 (ko) 2015-05-19
JP5581211B2 (ja) 2014-08-27
CA2694497A1 (en) 2009-02-19
WO2009023567A1 (en) 2009-02-19
AU2008286979B2 (en) 2013-03-28
US20120302594A1 (en) 2012-11-29
EP2190819B1 (en) 2016-05-25
NO341089B1 (no) 2017-08-21

Similar Documents

Publication Publication Date Title
CA2694497C (en) Quaternary opioid carboxamides
US6887998B2 (en) Process for 8-carboxamido-2,6-methano-3-benzazocines
JP5964809B2 (ja) オピオイド受容体リガンドとしてのカルボキサミド基を含有するモルヒネ誘導体
JP5727374B2 (ja) 大型置換基を有する非フェノール性アミンオピオイド
AU2008255049A1 (en) Fused-ring heterocycle opioids
CA2615774C (en) Large substituent, non-phenolic opioids
HK1141295B (en) Quaternary opioid carboxamides
HK1181045B (en) Morphinane derivatives containing a carboxamide group as opioid receptor ligands

Legal Events

Date Code Title Description
EEER Examination request