Preparation of 15-deoxy-16-hydroxyprostaglandins

Abstract

Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R.sub.5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R.sub.5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R.sub.4 forms a cycloalkyl as defined above; and R.sub.6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge.sub.1 ester analogues of the above formula, limited to the structures wherein two of R.sub.2, R.sub.3 R.sub.4 and R.sub.5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.

Dependencies are inferred from the claim text.