8-aza-11-deoxy prostaglandin analogues

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S543000

Reexamination Certificate

active

06900336

ABSTRACT:
This invention relates to compounds which are generally EP4receptor agonists and which are represented by Formula I:wherein A is a —CH2—CH2—, or —CH═CH—; B is absent, an aryl, or heteroaryl group; R1is alkyl, alkenyl, alkynyl, cycloalkylalkyl, heterocyclylalkyl, aryl, arylalkyl or heteroaryl, when B is aryl or heteroaryl and R3, R4, R5and R6are not simultaneously hydrogen, or R1is heterocyclylalkyl, aryl, or heteroaryl when B is absent and R3, R4, R5and R6are simultaneously hydrogen; and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

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Zoretic et al., “Synthesis of (E)-7-[[2-[4(m-Trifluoromethylphenoxy)-3α and 3β—Hydroxy-1-butenyl]-5-oxo-1-pyrrolidinyl]]heptanoic Acids”,J. Heterocyclic Chem., Mar.-Apr. 1983, pp. 465-466, 20.
Saijo, et al., “Heterocyclic prostaglandins. IV. Synthesis of 8-aza-11-deoxyprostaglandin E, and its related compounds,”Yakugaku Zashi, 1980, pp. 3890-3895, 100(4), ABSTRACT.
Suda, et al., “Prostaglandin E Receptor Subtypes in Mouse Osteoblastic Cell Line,”Endocrinology, 1996, pp. 1698-1705, 137, No. 5.
Suzawa, et al., “The Role of Prostaglandin E Receptor Subtypes (EP1, EP2, EP3, and EP4) in Bone Resorption: An Analysis Using Sepcific Agonists for the Respective EPs,”Endocrinology, 2000, pp. 1554-1559, 141(4).
Ono, et al., Important role of EP4, a subtype of prostaglandin (PG) E receptor, in osteoclast-like cell formation from mouse bone marrow cells induced by PGE2,Journal of Endocrinology, 1998, pp. R1-R5, 158.

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