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Title:
METHOD FOR INTRODUCING DEUTERATED LOWER ALKYL INTO AMINE MOIETY OF COMPOUND CONTAINING SECONDARY AMINE
Document Type and Number:
WIPO Patent Application WO/2020/184670
Kind Code:
A1
Abstract:
The present invention relates to a method for monodeuterated lower alkylating an amine moiety of a compound which contains an amine that is protected by an aralkyl group, wherein a monodeuterated lower alkyl is introduced into the amine by means of a deuterated lower alkylating agent under neutral or basic conditions, and subsequently the aralkyl group is eliminated.

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Inventors:
MIYAKE MASAHIRO (JP)
HAYASHI MASASHI (JP)
NAKAI YUYA (JP)
Application Number:
PCT/JP2020/010873
Publication Date:
September 17, 2020
Filing Date:
March 12, 2020
Export Citation:
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Assignee:
OTSUKA PHARMA CO LTD (JP)
International Classes:
C07B61/00; C07C253/30; C07D205/04; C07D207/09; C07D207/267; C07D209/08; C07D211/46; C07D211/74; C07D215/20; C07D221/20; C07D221/28; C07D223/08; C07D225/02; C07D241/08; C07D241/42; C07D241/44; C07D243/08; C07D295/03; C07D401/04; C07D403/06; C07D451/06; C07D471/04; C07D471/14; C07D487/04; C07D487/10; C07B59/00
Domestic Patent References:
WO2019049918A12019-03-14
WO2008137474A12008-11-13
WO2017088784A12017-06-01
WO1999024433A11999-05-20
WO2015177326A12015-11-26
WO2010128659A12010-11-11
Foreign References:
JP2014520140A2014-08-21
CN108675959A2018-10-19
JP2018536667A2018-12-13
CN110028433A2019-07-19
US20080194529A12008-08-14
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US5229382A1993-07-20
JP2008050307A2008-03-06
CN107698500A2018-02-16
Other References:
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IAN FELLOWS; RICHARD M CARR; NIGEL DE BOECK; STEPHEN MONTGOMERY; IAN WATERHOUSE; DEREK R SUTHERLAND: "Simple methods for the labelling of N-methyl amines using isotopically labelled methyl iodide", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 41, no. 12, 1998, pages 1127 - 1143, XP002474309
HEINKELE, GEORG ET AL.: "Synthesis of [2H3]-dextromethorphan and its major urinary metabolites [2H3]-dxtrorphan and [2H3]-dextrorphan-beta-glucoronide", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 45, no. 13, 2002, pages 1153 - 1158, XP002490642
ARKIVOC, vol. iii, pages 182 - 193
J LABEL COMPD RADIOPHARM, vol. 45, 2002, pages 1153
T. W. GREENEP. G. M. WUTS: "Greene's Protective Groups in Organic Synthesis", 2006, WILEY
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PHYSICAL ORGANIC CHEMISTRY, vol. 11, 1991, pages 1741
TETRAHEDRON LETTERS, vol. 56, 2015, pages 949
JOURNAL OF MEDICINAL CHEMISTRY, vol. 30, 1987, pages 2283
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JOURNAL OF MEDICINAL CHEMISTRY, vol. 59, 2016, pages 4948
See also references of EP 3939954A4
Attorney, Agent or Firm:
YAMAO, Norihito et al. (JP)
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