Indoline compound and process for producing the same

Details Indoline compound and process for producing the same Indoline compound and process for producing the same

2007-04-16

2010-11-16

Saeed, Kamal A (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07834193

ABSTRACT:
The present invention provides an industrial method production of silodosin, which is useful for a therapeutic agent for dysuria associated with benign prostatic hyperplasia. The production of silodosine is characterized by mixing 3-{7-cyano-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl}amino]propyl]-2,3-dihydro-1H-indol-1-yl}-propyl benzoate and oxalic acid to yield the oxalate, subsequently hydrolyzing the oxalate salt to yield 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino]propyl]-2,3-dihydro-1H-indole-7-carbonitrile and hydrolyzing the same, and manufacturing intermediates used therefore.

REFERENCES:
patent: 5387603 (1995-02-01), Kitazawa et al.
patent: 6310086 (2001-10-01), Kitazawa et al.
patent: 07-165684 (1995-06-01), None
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Greene et al. Protective Groups in Organic Synthesis, Chapter 2, “Protection for the Hydroxyl Group, Including 1,2- and 1,3-Dols,” Third Edition, 1999, p. 17-21, 76-79 and 176.
Kato et al., Machine translation of JP 2006-188470. Obtained on Aug. 5, 2010 from AIPN website. <http://dossier.ipdl.inpit.go.jp/text—trans.html>.

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