WO2013026852A3 - Derivatives of mecamylamine - Google Patents

Derivatives of mecamylamine Download PDF

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Publication number
WO2013026852A3
WO2013026852A3 PCT/EP2012/066285 EP2012066285W WO2013026852A3 WO 2013026852 A3 WO2013026852 A3 WO 2013026852A3 EP 2012066285 W EP2012066285 W EP 2012066285W WO 2013026852 A3 WO2013026852 A3 WO 2013026852A3
Authority
WO
WIPO (PCT)
Prior art keywords
mecamylamine
derivatives
hypertensive
demise
nachr
Prior art date
Application number
PCT/EP2012/066285
Other languages
French (fr)
Other versions
WO2013026852A2 (en
Inventor
Michael Southern
David MANGAN
Original Assignee
The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin
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 The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin filed Critical The Provost, Fellows, Foundation Scholars, And The Other Members Of Board, Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin
Publication of WO2013026852A2 publication Critical patent/WO2013026852A2/en
Publication of WO2013026852A3 publication Critical patent/WO2013026852A3/en

Links

Classifications

    • 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
    • A61K31/13—Amines
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Mecamylamine is a general nicotinic acetylcholine receptor (nAChR) antagonist that was one of the first anti-hypertensive agents. Since its demise as an anti-hypertensive drug, mecamylamine has been shown to aid smoking cessation (in humans), reduce cue induced craving in human cocaine addicts and heavy drinkers. The present invention provides for novel derivatives of mecamylamine and inventive synthetic routes to these compounds.
PCT/EP2012/066285 2011-08-22 2012-08-21 Derivatives of mecamylamine WO2013026852A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11178258 2011-08-22
EP11178258.7 2011-08-22

Publications (2)

Publication Number Publication Date
WO2013026852A2 WO2013026852A2 (en) 2013-02-28
WO2013026852A3 true WO2013026852A3 (en) 2013-04-11

Family

ID=46704684

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/066285 WO2013026852A2 (en) 2011-08-22 2012-08-21 Derivatives of mecamylamine

Country Status (1)

Country Link
WO (1) WO2013026852A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2576496T3 (en) 2010-05-27 2017-08-31 Catalyst Biosciences, Inc. Nicotinic receptor non-competitive antagonists
WO2012094437A2 (en) * 2011-01-07 2012-07-12 Targacept, Inc. Nicotinic receptor non-competitive antagonists
WO2014004417A1 (en) * 2012-06-26 2014-01-03 Targacept, Inc. Nicotinic receptor non-competitive antagonists
WO2022140677A1 (en) 2020-12-23 2022-06-30 The Broad Institute, Inc. Compositions and methods related to di-substituted bicyclo[2.2.1] heptanamine-containing compounds
GB202203728D0 (en) 2022-03-17 2022-05-04 Univ Oxford Innovation Ltd Treatments and methods for increasing dopamine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015492A1 (en) * 1997-09-23 1999-04-01 Poli Industria Chimica S.P.A. Method for preparing bicycloheptan-amine compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US804879A (en) 1904-03-08 1905-11-21 William A Parrish Detachable link.
US2831027A (en) 1955-06-06 1958-04-15 Merck & Co Inc Isocamphane compounds and processes for preparing the same
GB804879A (en) 1955-06-06 1958-11-26 Merck & Co Inc Isocamphane compounds and processes for preparing them
US2885428A (en) 1958-01-08 1959-05-05 Rohm & Haas 2-isothiocyanatoisocamphane
WO2005067909A1 (en) 2004-01-06 2005-07-28 Yale University Combination therapy with mecamylamine for the treatment of mood disorders

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015492A1 (en) * 1997-09-23 1999-04-01 Poli Industria Chimica S.P.A. Method for preparing bicycloheptan-amine compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ERICH DWORAN ET AL: "Eine neue Totalsynthese von Epifenchon und Dehydrocamphenilon", CHEMISCHE BERICHTE, vol. 114, no. 6, 1 June 1981 (1981-06-01), pages 2357 - 2359, XP055042078, ISSN: 0009-2940, DOI: 10.1002/cber.19811140632 *
SUCHOCKI J A ET AL: "Synthesis of 2-exo- and 2-endo-mecamylamine analogs. Structure-activity relationships for nicotinic antagonism in the central nervous system", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 34, 1 January 1991 (1991-01-01), pages 1003 - 1010, XP002218706, ISSN: 0022-2623, DOI: 10.1021/JM00107A019 *

Also Published As

Publication number Publication date
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