C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/235.03
C07C 405/00 (2006.01) C07D 307/935 (2006.01) C07D 309/12 (2006.01)
Patent
CA 1098126
A B S T R A C T New therapeutically useful prostaglandins which are optically active or racemic compounds of the following general formula (I) Image (I) wherein R is a hydrogen atom, a C1-C12 alkyl group or a cation of a pharma- ceutically acceptable base; the symbol Image represents a single or a double bond, wherein when the symbol Image is a double bond, R1 is a hydrogen atom and R2 and R3 together form an oxo group, while when the symbol Image is a single bond, R1 is hydroxy and one of R2 and R3 is hydrogen, and the other is hydroxy or R2 and R3 together form an oxo group; one of R4 and R5 is a hydro- gen atom and the other is hydroxy; one of R6 and R7 is hydrogen, and the other is a 16(S) or 16(R) C1-C4 alkyl; n is an integer of 3 to 6; and wherein the chains bound to the carbon atoms in the 8- and 12- positions have a trans- configuration. Also described is an improved process for the preparation of 9.alpha.,11.alpha.,15(S or R)-trihydroxy-13,14-dehydro-prostaglandins of the natural series and 9.beta.,11.alpha.,15(S or R)-trihydroxy-13,14-dehydro-prostaglandins of the enantio series, said method comprising the reaction of an optically active or racemic lactol of formula (A) Image (A) wherein Y is hydroxy or a known protecting group bound to the ring through an ethereal oxygen atom, one of Ra and Rb is hydrogen and the other is hydroxy or a known protecting group bound to the chain through an ethereal oxygen atom, X is bromine or iodine, and Z is a generic residue of the side chain, with a Wittig reagent containing the desired substituents, the subsequent optional deetherification, saponification, re-esterification, and/or salification of the obtained compound.
234430
Doria Gianfederico
Gandolfi Carmelo
Pellegata Renato
Usardi Maria M.
Farmitalia Carlo Erba S.p.a.
Fetherstonhaugh & Co.
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