Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-03-07
2006-03-07
Morris, Patricia L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07009057
ABSTRACT:
A method for obtaining antidiabetic of formula (I), wherein the method comprises condensing of a 4-derivatized phenol or phenolate of general formula (II), wherein R is an amino group-containing organic residue, selected from the group comprising a residue of the following formula —NHR3, wherein R3is hydrogen or a protecting group, which is removed before further treatment, and a residue of general formula (A), wherein Rbrepresents a carboxy group either in the free acid form or in the form of a salt or ester or another functional derivative or the nitrile group CN, and M represents a hydrogen or alkali metal atom, with a pyridine base of general formula (III, wherein Z is a leaving group other than a halogen, wherein, before or after carrying out the condensation, the following operations are carried out: (a) diazotizing the amino group present in organic residue R; (b) converting the diazotised residue R into a derivative of 2-halopropionate or 2-halopropionitrile of formula (B), wherein Rbis as defined above and X is a halogen; (c) cyclizing the derivative of 2-halopropionate or 2-halopropionitrile with thiourea; (d) hydrolysing the resulting imine thus giving pioglitazone of formula (I)
REFERENCES:
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Halama Ale{hacek over (s)}
Hejtmánková Ludmila
Jirman Josef
Lustig Petr
Richter Jind{hacek over (r)}ich
Morris Patricia L.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Zentiva A.S.
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