Tricyclic compounds and their use in medicine process for their preparation and pharmaceutical compositions containing them
Novel β-aryl-α-oxysubstituted alkylcarboxylic acids of the formula (I) and compositions containing them. The compounds have hypolipidemic, antihyperglycemic uses.
1. A compound of formula (If)
where Ar represents a divalent single or fused aromatic group, R 5 represents hydrogen, hydroxy, alkoxy, halogen or lower alkyl, or optionally substituted aralkyl group or forms a bond together with the adjacent group R 6 ; R 6 represents hydrogen, hydroxy, alkoxy, halogen or lower alkyl group, optionally substituted aralkyl or R 6 forms a bond together with R 5 ; R 7 represents hydrogen or an optionally substituted group selected from alkyl, cycloalkyl, aryl, aralkyl, alkoxyalkyl, alkoxycarbonyl, aryloxycarbonyl, alkylaminocarbonyl, arylaminocarbonyl, acyl, heterocyclyl, or heteroaralkyl groups; R 8 represents hydrogen or an optionally substituted group selected from alkyl, cycloxlkyl, aryl, aralkyl, heterocyclyl, or heteroaralkyl groups; n is an integer ranging from 1-4 and m is 1 and L 1 is a leaving group; and stereoisomers and salts thereof.
2. A compound according to claim 1 wherein Ar represents divalent phenylene or naphthylene.
3. A compound selected from:
Ethyl (E/Z) 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropenoate,
Ethyl (E) 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropenoate, or
Ethyl (Z) 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropenoate.
4. Ethyl 3-[4-(2-bromoethoxy) phenyl]-2-ethoxypropanoate;
(+) Ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate; and
(−) Ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate.
5. A process for the preparation of compound of formula (If) as defined in claim 1 , which comprises:
a) reacting a compound of formula (Ic)
where R 5 , R 6 , R 7 , R 8 and Ar are as defined in claim 1 , with a compound of formula (IV)
L 1 —(CH 2 ) n —L 2 (IV)
where L 1 and L 2 are the same or different and represent leaving groups or L 2 may also represent a hydroxy or a protected hydroxy group which may be further converted to a leaving group, n represents an integer 1-4; or
b) reacting a compound of formula (V)
L 1 —(CH 2 ) n —(O) m —Ar—CHO (V)
where L 1 represent a leaving group, m is 1 and all other symbols are as defined earlier, with a compound of formula (IIIb)
where R 11 is a lower alkyl group and R 7 and R 8 are as defined in claim 1 , to yield a compound of formula (IIf)
where all symbols are as defined above and L 1 is a leaving group, which is further reduced to yield a compound of formula (If).