WO2013112163A1 - Dérivés d'isoquinuclidène fusionnés à de l'indole et du benzofurane et procédés de préparation de ceux-ci - Google Patents

Dérivés d'isoquinuclidène fusionnés à de l'indole et du benzofurane et procédés de préparation de ceux-ci Download PDF

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Publication number
WO2013112163A1
WO2013112163A1 PCT/US2012/022787 US2012022787W WO2013112163A1 WO 2013112163 A1 WO2013112163 A1 WO 2013112163A1 US 2012022787 W US2012022787 W US 2012022787W WO 2013112163 A1 WO2013112163 A1 WO 2013112163A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
alkyl
formula
optionally substituted
Prior art date
Application number
PCT/US2012/022787
Other languages
English (en)
Inventor
Robert M. Moriarty
Original Assignee
Demerx, 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 Demerx, Inc. filed Critical Demerx, Inc.
Priority to PCT/US2013/023017 priority Critical patent/WO2013112757A1/fr
Priority to EP13741381.1A priority patent/EP2807167A4/fr
Priority to CA2858105A priority patent/CA2858105A1/fr
Publication of WO2013112163A1 publication Critical patent/WO2013112163A1/fr

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Classifications

    • 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
    • C07D487/04—Ortho-condensed 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
    • 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

Definitions

  • Noribogaine is a well known compound whose structure combines the features, for example, of tyrptamine, and isoquinuclidene.
  • the naturally occurring enantiomer of noribo aine can be depicted by the following formula:
  • ((S)-binol) refers to the (S)-enantiomer of 1 , 1 '-bi-2- naphthol
  • ((R)-binol) refers to the (R)-enantiomer of l,l'-bi-2-naphthol.
  • the compound of Formula (I) is of Formula (I A) or (IB):
  • the reaction is carried out for a period of time sufficient to provide a substantial amount of the product, which can be ascertained by using routine methods such as thin layer chromatography, NMR spectroscopy, and the likes.
  • the product can be isolated and optionally purified using standard purification techniques, such as liquid chromatography, crystallization, and precipitation, or the products may be used for a subsequent reaction without further purification.
  • this invention provides a process for preparing a compound of formula:
  • this invention provides a process for preparing a compound of formula:
  • the process further comprises subjecting the keto ibogaine derivative:
  • this invention provides (-) noribogaine and (+)noribogaine, and intermediates thereto, preferably in substantially enantiomerically pure forms, prepared according to the processes provided herein.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des dérivés d'isoquinuclidène fusionnés à de l'indole et du benzofurane. Elle porte également sur des procédés, de préférence des procédés énantiosélectifs, pour la préparation de ces dérivés, y compris des procédés de préparation de noribogaine (-) et (+) ou d'un sel de celle-ci, sous des formes pratiquement pures du point de vue énantiomérique.
PCT/US2012/022787 2012-01-25 2012-01-26 Dérivés d'isoquinuclidène fusionnés à de l'indole et du benzofurane et procédés de préparation de ceux-ci WO2013112163A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/US2013/023017 WO2013112757A1 (fr) 2012-01-25 2013-01-24 Dérivés d'isoquinuclidène réunis par fusion à de l'indole et du benzofurane et leurs procédés de préparation
EP13741381.1A EP2807167A4 (fr) 2012-01-25 2013-01-24 Dérivés d'isoquinuclidène réunis par fusion à de l'indole et du benzofurane et leurs procédés de préparation
CA2858105A CA2858105A1 (fr) 2012-01-25 2013-01-24 Derives d'isoquinuclidene reunis par fusion a de l'indole et du benzofurane et leurs procedes de preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261590740P 2012-01-25 2012-01-25
US61/590,740 2012-01-25

Publications (1)

Publication Number Publication Date
WO2013112163A1 true WO2013112163A1 (fr) 2013-08-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2012/022787 WO2013112163A1 (fr) 2012-01-25 2012-01-26 Dérivés d'isoquinuclidène fusionnés à de l'indole et du benzofurane et procédés de préparation de ceux-ci

Country Status (1)

Country Link
WO (1) WO2013112163A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105503907A (zh) * 2016-01-18 2016-04-20 北京大学 对映选择性合成Vinca类生物碱的方法
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996003127A1 (fr) * 1994-07-25 1996-02-08 Nda International, Inc. Procede et composition de traitement de la dependance chimique chez les mammiferes
WO1997020847A1 (fr) * 1995-12-04 1997-06-12 Regents Of The University Of Minnesota Analogues d'ibogaine tricycliques, leur preparation et leur utilisation pour traiter la toxicomanie
US7220737B1 (en) * 1997-09-04 2007-05-22 Novoneuron, Inc Noribogaine in the treatment of pain and drug addiction
WO2012012764A1 (fr) * 2010-07-23 2012-01-26 Demerx, Inc. Compositions de noribogaïne

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996003127A1 (fr) * 1994-07-25 1996-02-08 Nda International, Inc. Procede et composition de traitement de la dependance chimique chez les mammiferes
WO1997020847A1 (fr) * 1995-12-04 1997-06-12 Regents Of The University Of Minnesota Analogues d'ibogaine tricycliques, leur preparation et leur utilisation pour traiter la toxicomanie
US7220737B1 (en) * 1997-09-04 2007-05-22 Novoneuron, Inc Noribogaine in the treatment of pain and drug addiction
WO2012012764A1 (fr) * 2010-07-23 2012-01-26 Demerx, Inc. Compositions de noribogaïne

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KUBILIENE, A. ET AL.: "Acute toxicity of ibogaine and noribogaine", MEDICINA(KAUNAS), vol. 44, no. 12, 2008, pages 984 - 988, XP055078318 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105503907A (zh) * 2016-01-18 2016-04-20 北京大学 对映选择性合成Vinca类生物碱的方法
US11447510B2 (en) 2017-10-09 2022-09-20 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10947257B2 (en) 2017-10-09 2021-03-16 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10954259B1 (en) 2017-10-09 2021-03-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11149044B2 (en) 2017-10-09 2021-10-19 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11180517B2 (en) 2017-10-09 2021-11-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11505564B2 (en) 2017-10-09 2022-11-22 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11629159B2 (en) 2017-10-09 2023-04-18 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11851451B2 (en) 2017-10-09 2023-12-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11939346B2 (en) 2017-10-09 2024-03-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US11738035B2 (en) 2019-04-17 2023-08-29 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin

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