Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2001-06-08
2003-03-25
Balasubramanian, Venkataraman (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S170000, C548S215000
Reexamination Certificate
active
06538134
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to 4-benzyl-2-hydroxy-1,4-oxazin-3-one which is useful as an intermediate in the preparation of certain therapeutic agents. In particular, the present invention provides 4-benzyl-2-hydroxy-1,4-oxazin-3-one which is an intermediate in the synthesis of pharmaceutical compounds which are substance P (neurokinin-1) receptor antagonists.
General processes are disclosed in the art for the preparation of compounds related to 4-benzyl-2-hydroxy-1,4-oxazin-3-one, but these result in relatively low and inconsistent yields of the desired product (A. Le Rouzic-Bleeevre,
Fr. C. R. Hebd. Seances Acad. Sci., Ser. C
., 282 (6) 307-310 (1976); T. Mancilla, et al.,
Heteroatom. Chem
., 6(6) 605-609 (1995)). In contrast to the previously known processes, the present invention provides effective methodology for the preparation of 4-benzyl-2-hydroxy-1,4-oxazin-3-one in relatively high yield and purity.
It will be appreciated that 4-benzyl-2-hydroxy-1,4-oxazin-3-one is an important intermediate for a particularly useful class of therapeutic agents. As such, there is a need for the development of a process for the preparation of 4-benzyl-2-hydroxy-1,4-oxazin-3-one which is readily amenable to scale-up, uses cost-effective and readily available reagents and which is therefore capable of practical application to large scale manufacture.
Accordingly, the subject invention provides 4-benzyl-2-hydroxy-1,4-oxazin-3-one via a very simple, short, relatively inexpensive and highly efficient synthesis.
SUMMARY OF THE INVENTION
This invention is directed to the compound 4-benzyl-2-hydroxy-1,4-oxazin-3-one of the formula:
This compound is an intermediate in the synthesis of compounds which possess pharmacological activity. In particular, such compounds are substance P (neurokinin-1) receptor antagonists which are useful e.g., in the treatment of psychiatric disorders, inflammatory diseases, and emesis.
REFERENCES:
Perrone et al. Synthesis 598-600, 1976.*
Le Rouzic-Bellevre, C. R. Hebd. Seances Acad. Sci., Ser. C, 282(6), 307-310, 1976.
Brands Karel M. Jos
Crocker Louis S.
Nelson Todd D.
Pye Philip J.
Rosen Jonathan D.
Balasubramanian Venkataraman
Merck & Co. , Inc.
Thies J. Eric
Winokur Melvin
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