C.sub.14 Phenyl-substituted derivatives of prostaglandin analogu

Details C.sub.14 Phenyl-substituted derivatives of prostaglandin analogu C.sub.14 Phenyl-substituted derivatives of prostaglandin analogu

1977-06-24

1979-04-10

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

560 55, 562463, 424308, C07C17700

Patent

active

041490070

ABSTRACT:
Analogues of prostaglandins A, E and F in which a phenyl moiety is attached to the C.sub.14 carbon atom are disclosed. Also disclosed are methods of preparing the analogues and starting materials. The compounds have the structural formula: ##STR1## in which J is methylene, R or S-hydroxymethylene or methine; L is methylene or methine and can be methine only when J is methine; M is carbonyl, R or S-hydroxymethylene; Q is ethylene, Z-vinylene or inter-phenylene; T is an alkoxy-carbonyl having from 2 to 3 carbon atoms inclusive, or carboxyl; and B is a loweralkyl of from 1 to 5 carbon atoms.
The prostaglandin analogues of the present invention exhibit a separation of pharmacological activity. The analogues can be used for platelet aggregation (and Methyl 14-Phenyl-11.alpha.,15S-dihydroxy-9-oxoprost-13E-en-1-oate can be used for antagonism for smooth muscle stimulation) without the accompanying undesirable side effects of natural prostaglandins, e.g., flush, headache, abdominal cramps and nausea.

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