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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.

Inventors:
MIYAKE MASAHIRO (JP)
HAYASHI MASASHI (JP)
NAKAI YUYA (JP)
Application Number:
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
Foreign References:
JP2014520140A2014-08-21
CN108675959A2018-10-19
JP2018536667A2018-12-13
CN110028433A2019-07-19
Other References:
HEDVIG BÖLCSKEI; MÁK MARIANNA; DRAVECZ FERENCZ; DOMÁNY GYÖRGY: "Synthesis of deuterated dextromethorphan derivatives", ARKIVOC, 2008, pages 182 - 193, XP055518256
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
Attorney, Agent or Firm:
YAMAO, Norihito et al. (JP)
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