Process for preparing an antifungal azole with hydrazino and amidrazone intermediates
AssigneeZeneca Limited
InventorsElwyn Peter Davies, John David Pittam, Keith Blakeney Mallion, Nigel Philip Taylor
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Abstract
A process for preparing an antifungal azole compound of formula (I) by reacting an epoxide with hydrazine to from a hydrazino compound which is subsequently reacted with an iminoether. The amidrazone product is subsequently reacted with an orthoformate to provide the antifungal azole. The azole, known as ZD0870, shows good activity against human fungal infections including Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus.
Claims12
A process for preparing a compound of the formula (I):
- ##STR12## or a pharmaceutically acceptable salt thereof, which comprises:
- i) reacting a compound of the formula (C) ##STR13## with hydrazine to form a compound of the formula (II):
- ##STR14## ii) reacting the compound of the formula (II) with an iminoether of the formula (III):
- ##STR15## wherein R.sup.1 is C.sub.1-6 alkyl or optionally substituted phenyl;
- to form a compound of the formula (IV):
- ##STR16## iii) reacting the compound of the formula (IV) with a compound of the formula (V):
- (R.sup.2 O).sub.3 CH (V)
- wherein R.sup.2 is C.sub.1-6 alkyl or optionally substituted phenyl;
- to form a compound of the formula (I);
- and
- iv) if necessary, forming a pharmaceutically acceptable salt.
A compound of the formula (IV):
- ##STR18##
A compound of the formula (II):
- ##STR19##
A process for the preparation of a compound of the formula (I):
- ##STR20## or a pharmaceutically acceptable salt thereof which comprises reacting a compound of the formula (IV):
- ##STR21## with a compound of the formula (V):
- (R.sub.2 O).sub.3 CH (V)
- wherein R.sup.2 is C.sub.1-6 alkyl or optionally substituted phenyl;
- and, if necessary, forming a pharmaceutically acceptable salt.
Dependencies are inferred from the claim text.