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US 3,948,973 AGranted
Halocyclopropyl substituted phenoxyalkanoic acids
AssigneeSterling Drug Inc.
InventorDonald K. Phillips
Life of this patent
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Abstract
Halocyclopropyl substituted phenoxyalkanoic acids and esters thereof, having hypocholesteremic activity are prepared via several alternative synthetic approaches, involving as the key reactions interaction of a substituted phenylalkene with a carbene source to introduce the halocyclopropyl moiety, and reaction of a substituted phenol with chloroform and a lower-alkanone in the presence of base, or with a lower-alkyl .alpha.-bromo-alkanoate, to form the phenoxyalkanoic acid moiety.
Claims11
A compound of the formula ##SPC19##
- wherein:
- R is hydrogen or alkyl of 1-6 carbon atoms;
- A and A' are alkyl of 1-3 carbon atoms;
- Q is hydrogen, halogen or alkyl of 1-3 carbon atoms;
- R.sup.1 is hydrogen, alkyl of 1-3 carbon atoms or phenyl;
- R.sup.2 is hydrogen or halogen;
- R.sup.2.sup.' is hydrogen or halogen, at least one of R.sup.2 and R.sup.2.sup.' being halogen;
- R.sup.3 is hydrogen, alkyl of 1-3 carbon atoms or phenyl;
- R.sup.3.sup.' is hydrogen or alkyl of 1-3 carbon atoms;
- n is 0 or 1;
- a compound of the above formula where Q and R.sup.3 together form an ethylene bridge and (CH.sub.2).sub.n is a single bond to the benzene ring ortho to Q, thereby forming the six-membered non-aromatic carbocyclic ring of a 2,3-dihydro-1H-cyclopropa[ a]-naphthalene ring system;
- or a pharmacologically acceptable salt of a compound of the above formula where R is hydrogen.
9 more elements
Dependencies are inferred from the claim text.