Imperial Chemical Industries Limited

Zeneca Limited

David M Martin

Andrew Peter Thomas

Lyn Powell

Stanley A Lee

Philip N Edwards

The invention provides a novel chemical process for the manufacture of quinoline, pyridine and imidazole derivatives of the formula IV wherein Q, Y.sup.1 and Y.sup.2 have the various meanings defined herein, and their non-toxic salts, which are angiotensin II inhibitors. The process involves the removal of an electron-deficient phenyl group or a pyridyl or pyrimidyl group from a compound of the formula VI as defined herein. Certain of the intermediates are novel and are provided as a further feature of the invention.

Biphenyl-tetrazole intermediate compounds

The invention provides a novel chemical process for the manufacture of certain imidazo[4,5-b]pyridine derivatives of the formula I wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the various meanings defined herein, and their non-toxic salts, which are angiotensin II inhibitors. The process involves the removal of an electron-deficient phenyl group or a pyridyl or pyrimidyl group from a compound of the formula II as defined herein. Certain of the intermediates are novel and are provided as a further feature of the invention.

Chemical process and intermediates used therein

The invention provides a novel chemical process for the manufacture of quinoline, pyridine and imidazole derivatives of the formula IV wherein Q, Y.sup.1 and Y.sup.2 have the various meanings defined herein, and their non-toxic salts, which are angiotensin II inhibitors. The process involves the removal of an electron-deficient phenyl group or a pyridyl or pyrimidyl group from a compound of the formula VI as defined herein.

Chemical process for making angiotesin II antagonist compounds

The invention concerns novel boron compounds of the formula IV, in which Q, Y.sup.1, G.sup.1 and G.sup.2 have the various meanings defined herein, and their acid and base addition salts. The said compounds are useful in the manufacture of certain quinoline, pyridine and imidazole derivatives which have angiotensin II inhibitory activity. The invention also provides novel processes for the production of the quinoline, pyridine and imidazole derivatives. ##STR1##

Heterocyclic boron compounds as intermediates for angiotensin II

The invention is concerned with novel dioxolane derivatives of the formula: ##STR1## in which R.sub.a is hydrogen or (1-4C)alkyl and R.sub.b is (1-4C)alkyl or phenyl optionally bearing a halogeno substituent; their production; and their use for the manufacture of certain known anti-arthritic acids of the formula: ##STR2## and, in particular, those acids in which R.sub.a =R.sub.b =methyl or R.sub.a =ethyl and R.sub.b =phenyl, by a novel reduction process. The preferred reduction procedures involve the use of an alkali metal borohydride or cyanoborohydride in the presence of a noble metal catalyst, or the use of an .alpha.-branched alkyl or cycloalkyl Grignard agent. The use of the derivatives of formula I avoids the need for potentially toxic reagents and reactive intermediates in the previously known processes for the production of the acids of formula V.

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Stockport, United Kingdom

David M Martin