Synthesis of thiazolium compounds

Details Synthesis of thiazolium compounds Synthesis of thiazolium compounds

2001-03-29

2003-01-14

McKane, Joseph K. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S204000

Reexamination Certificate

active

06506902

ABSTRACT:

The present invention relates to methods of synthesizing certain thiazolium compounds.
In U.S. Pat. Nos. 5,656,261; 5,853,703; and 6,007,865 compounds were disclosed that are promising agents that can be used in compositions and methods useful in treating a number of indications. One mechanism of action contributing to these treatments is believed to be inhibition and reversal of nonenzymatic cross-linking (protein aging). These compounds can be used in therapeutic applications where proteins in the body deteriorate with age and as a consequence of diabetes.
Efficient syntheses for these compounds are desirable. Described herein is a surprisingly effective synthesis of a certain class of these compounds.
SUMMARY OF THE INVENTION
In one embodiment, the invention provides a method of synthesizing a compound of formula I,
comprising: reacting a compound of formula II
wherein R
1
and R
2
are independently hydrogen, hydroxy(C
1
-C
2
)alkyl, or (C
1
-C
2
)alkyl with, a compound of the formula III
wherein R
3
, R
4
, and R
5
are each independently of each other hydrogen, (C
1
-C
3
)alkyl, (C
1
-C
3
)alkoxy, or halogen; and X is a leaving group. The reaction is preferably conducted in a solvent having a dielectric constant at 20° C. of at least 30 but no more than 40
In another embodiment, the invention provides a method of synthesizing a 4,5-dimethyl-3-(2-oxo-2-phenylethyl)-thiazolium salt comprising: reacting 4,5-dimethylthiazole with (IV), wherein X is a leaving group.


REFERENCES:
patent: 5656261 (1997-08-01), Cerami et al.
patent: 5853703 (1998-12-01), Cerami et al.

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