Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-10-25
2005-10-25
Saeed, Kamal A. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S379700
Reexamination Certificate
active
06958403
ABSTRACT:
Procedure for preparation of compounds with the general formula 1, which include the racemic mixtures (±)-1, and the enantiomerically pure compounds (−)-1 and (+)-1, wherein R1and R3, like or different, represent an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl or methoxy group; R2represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group; R4represents an atom of hydrogen, chlorine, fluorine, a methyl, trifluoromethyl, methoxy, trifluoromethoxy, methylsulphonyl or aminosulphonyl group, with the condition that one of the substituents R2or R4is a methylsulphonyl or aminosulphonyl group; which involves obtaining the racemic mixture with the general formula (±)-1 by reacting an (E)-1,1,1-trifluoro-4-aryl-3-buten-2-one with a phenylhydrazine, followed by a treatment with chlorosulphonic acid, or by reacting with chlorosulphonic acid followed by a reaction with sodium hydroxide and, finally, with thionyl chloride. The product obtained by either of these methods is made to react with ammonium carbonate or ammonia, or with sodium sulphite and methyl iodide or methyl sulphate. In addition, to obtain the enantiomerically pure compounds with the general formula 1 by resolving the racemic mixture with the general formula (±)-1, a reaction is effected with optically active ephedrine, followed by formation of the sodium salt of each enantiomer, reaction with thionyl chloride and ammonium carbonate or ammonia, or instead with thionyl chloride followed by sodium sulphite and methyl iodide or methyl sulphate to thereby obtain separately the enantiomerically pure compounds with the general formulae (−)-1 and (±)-1.
REFERENCES:
patent: 3865816 (1975-02-01), Mengler
patent: WO 99/62884 (1999-12-01), None
patent: WO 00/76503 (2000-12-01), None
M. Mukai, et al. “On the Syntheses and the Optical Properties of Optically Active 2-Pyrazoline Compounds”,Canadian J. of Chemistry(1979), 57(3), pp. 360.
J. Jacques, et al. “Enantiomers, Racemates and Resolutions”, 1991,Krieger Publishing Company, Florida, U.S.A, pp. 258-259.
Leonardo et al.,Chirality(2004), 16(6), pp. 302-308 (CAS Abstract).
Alcon-Marrugat Montserrat
Cuberes-Altisen Maria Rosa
Frigola-Constansa Jordi
Pericas-Brondo Miguel Angel
Laboratorios del Dr. Esteve S.A.
Ostrolenk Faber Gerb & Soffen, LLP
Saeed Kamal A.
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