Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
2006-06-27
2006-06-27
Badio, Barbara P. (Department: 1616)
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
C568S030000
Reexamination Certificate
active
07067683
ABSTRACT:
This invention describes a safe method for the production of sulfamoyl chloride from chlorosulfonyl isocyanate and formic acid in the presence of a amide catalyst, taming the hazardous nature of this reaction by circumventing heat accumulation processes, as well as the sulfamoylation of alcohols and phenols with the resulting sulfamoyl chloride in N,N-dimethyl acetamide or N-methyl pyrrolidone thereby avoiding the formation of side-products which were inevitable with the methods of the prior art using dimethyl formamide or dichloromethane as a solvent. The current invention allows industrial scale applications and describes as an example the process of manufacture of the biologically active compound 17β-Hydroxyestra-1,3,5(10)-triene-3-yl sulfamate.
REFERENCES:
patent: 0403185 (1990-12-01), None
patent: WO 0066095 (2000-11-01), None
patent: WO 2003/053992 (2003-07-01), None
Okada et al. “Efficient general method for sulfamoylation of a hydroxyl group.”, Tetrahedron Letts., vol. 41, pp. 7047-7051, 2000.
Schwarz et al., “Synthesis of estrogen sulfamates: Compounds with a novel endocrinological profile.”, Steroids, vol. 61, pp. 710-717, 1996.
Makoto Okada et al., “Efficient General Method for Sulfamoylation of A Hydroxyl Group,” Tetrahedron Letters 41, (2000), pp. 7047-7051.
M. Okada, et al., “Efficient general method for sulphamoylation of a hyroxyl group,” Tetrahedron Letters, Sep. 2000, pp. 7047-7051, vol. 41, No. 36, XP004208258, ISSN: 0040-4039 cited in the application, the whole document, Elsevier Science Publishers, Amsterdam, NL.
S. Schwarz, et al., “Synthesis of oestrogen sulphamates: compounds with a novel endocrinological profile,” Steroids, Dec. 1, 1996, pp. 710-717, vol. 61, No. 12, XP004016631, ISSN: 0039-128X, p. 712, right-hand column, paragraph 2; table 3, Elsevier Science Publishers, New York, NY, US., to the extent discussed in specification.
J. Romer, et al., “Preparation and characterisation of the sulphamates of oestra-3, 17xi-diols. Rapid conversion of 16alpha-fluoro-oestradiol into 16alpha-fluoro-oestradiol-3, 17beta-disulphamate,” Journal For Praktische Chemie, 1999, pp. 574-583, vol. 341, No. 6, XP002182695, ISSN: 1436-9966, cited in the application, p. 575, left-hand column, last paragraph, Wiley VCH, Weinhelm, DE., to the extent discussed in specification.
Geisler Jens
Lopez Holguin Fernando
Lovis Kai
Schneider Frank
Badio Barbara P.
Millen White Zelano & Branigan P.C.
Schering AG
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