Prostaglandins fluoro

Amino-3-fluorobenzoic acid is an important intermediate in the synthesis of derivatives of indole, such as the potent and selective thromboxane/prostaglandin endoperoxide receptor antagonist L-670,596 or the anti-inflammatory agent Etodolac. Compounds of this type have therapeutic applications. 2-Amino-3-fluoro-benzoic add is aiso an important precursor for the synthesis of fluoroacridines, which can be converted to interesting tridentate ligands, such as Acriphos. ... 

Travoprost is an ester that acts as a pro-drug of a fluoro analogue of prostaglandin PGF200 which is a full agonist of the prostaglandin F (FP) receptor. It is marketed for the topical treatment of intra-ocular hypertension and glaucoma (Fig. 72) [167]. 

Fluorination of bicyclic derivatives, which has been used in prostaglandin synthesis from nor-bornadicne, gives a 1 1 mixture of two isomeric ot-fluoro esters, e.g. 3.18 The reaction is performed in tetrahydrofuran at — 78 °C, while a violent explosion occurs if the reaction is performed at — 40 C (upon quenching the reaction with water). 

Fluoro prostaglandin, (IV), PGF2a analogs effective as thromboxane A2 receptor agonists were prepared by Klimko (3) and used in the treatment of glaucoma and ocular hypertension. 

Muchowski and co-workers have described the synthesis and bronchodilator activity of a series of ring halogenated prostaglandins. Several of these compounds showed excellent activity in the Konzett assay (ys. histamine) on intravenous or aerosol administration (Table X). Phase I evaluation of the most potent member of the series, 9-deoxy-9p-fluoro-PGE2 (IX), however, revealed a cough liability which precluded further clinical investigation (126,130). 

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