Bicyclo 2,2,2!octane derivatives

A compound of the formula ##STR20## wherein W is a carbonyl, sulphonyl or sulphinyl group, or, W is H when Z is absent and X is a carbonyl, sulphonyl or sulphinyl group or --C(O)--CH.sub.2 -- (in which the carbonyl group is bonded to Y), provided that at least one of W and X contains carbonyl,

• Y is R.sub.7 --O-- or R.sub.7 --N(R.sub.8)-- (wherein R.sub.7 is H or C.sub.1 to C.sub.15 hydrocarbyl, up to two carbon atoms of the hydrocarbyl moiety optionally being replaced by a nitrogen, oxygen or sulphur atom provided that Y does not contain a --O--O-- group, and R.sub.8 is H, C.sub.1 to C.sub.3 alkyl, carboxymethyl or esterified carboxymethyl),
• Z is selected from
• i) --O--R.sub.9
• wherein R.sub.9 is H, C.sub.1 to C.sub.5 alkyl, phenyl, substituted phenyl, benzyl or substituted benzyl;
• ii) ##STR21## wherein Q is H, C.sub.1 to C.sub.5 hydrocarbyl, or --R.sub.10 --U, wherein R.sub.10 is a bond or C.sub.1 to C.sub.3 alkylene and U is aryl, substituted aryl, heterocyclic, substituted heterocyclic or cycloalkyl;
• ##STR22## iii) wherein a is 0 or 1 and b is from 0 to 3,
• R.sub.11 is H or methyl,
• R.sub.12 is H or C.sub.1 to C.sub.3 alkyl;
• or R.sub.12 is CH.sub.2 .dbd. and Q' is absent;
• or R.sub.11 and R.sub.12 are linked to form a 3- to 7-membered ring,
• R.sub.13 is a bond or C.sub.1 to C.sub.5 hydrocarbylene,
• G is a bond, --CHOH-- or --C(O)--
• Q' is as recited above for Q or --R.sub.10 --(C(O)).sub.d --L--(C(O)).sub.e --R.sub.9 (wherein R.sub.9 and R.sub.10 are as defined above, L is O, S or --N(R.sub.14)--, in which R.sub.14 is as defined above for R.sub.8, and d and e are 0 or 1, provided that d+e<2);
• or Q'and R.sub.12, together with the carbon atom to which they are attached, form a 3- to 7-membered ring,
• Q is as defined above;
• or Q and R.sub.12 together form a group of the formula --(CH.sub.2).sub.f --V--(CH.sub.2).sub.g -- wherein V is --S--, --S(O)--, --S(O).sub.2 --, --CH.sub.2 --, or --C(O)--, f is from 0 to 2 and g is from 0 to 3;
• or, when Q' is --R.sub.10 --U and U is an aromatic group, Q may additionally represent a methylene link to U, which link is ortho to the R.sub.10 link to U,
• T is H, cyano, C.sub.1 to C.sub.4 alkyl, --CH.sub.2 OH, carboxy, esterified carboxy or amidated carboxy;
• or
• iv) ##STR23## wherein A and B are independently a bond or C.sub.1 to C.sub.3 alkylene, provided that A and B together provide from 2 to 4 carbon atoms in the ring, R.sub.9 and R.sub.10 are as defined above, and R.sub.15 is as defined above for R.sub.8
• or Z is absent and W is H,
• R.sub.1 is H, methyl, halo, carboxy, esterified carboxy, amidated carboxy, carboxymethyl, esterified carboxymethyl or amidated carboxymethyl,
• R.sub.2 is selected from the groups recited above for R.sub.1 ;
• or, when Z is absent and W is H, R.sub.2 may additionally represent --C(O)--Z' wherein Z' is selected from the groups recited above for Z;
• or R.sub.1 and R.sub.2 together form a second bond between the carbon atoms to which they are attached,
• R.sub.3 and R.sub.4 (or each R.sub.3 and R.sub.4 group, when m or n is 2 or more) are independently selected from halo, amino, nitro, cyano, sulphamoyl, sulphonyl, trifluoromethyl, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 alkoxy, hydroxy, C.sub.1 to C.sub.3 hydroxyalkyl, C.sub.1 to C.sub.3 alkylcarboxyamino, carboxy, esterified carboxy and amidated carboxy,
• R.sub.5 and R.sub.6 are independently selected from H and the groups recited above for R.sub.3
• m is from 0 to 4, provided that m is not more than 2 unless R.sub.1 is exclusively halo,
• n is from 0 to 4, provided that n is not more than 2 unless R.sub.4 is exclusively halo,
• or a pharmaceutically acceptable salt thereof, provided that
• if one (but only one) of R.sub.1 and R.sub.2 is methyl, m and n are not both 0,
• Z is not hydroxy or methoxy when Y is hydroxy or methoxy,
• Z and Y are not trans to each other when Z is R.sub.8 --O-- and Y is R.sub.7 --O--,
• --X--Y is not equal to --W--Z when R.sub.1 .dbd.R.sub.2 .dbd.H and m.dbd.n.dbd.0, and
• if Z is absent and R.sub.1 and R.sub.2 are both H or form part of a double bond, Y is not R.sub.7 --O--,
• and further provided that said compound is not 7-(N,N-dimethylaminocarbonyl)-8-methyl-2,3,5,6-dibenzobicyclo 2.2.2!octane or 7-(N-methyl-N-phenylaminocarbonyl)-8-methyl-2,3,5,6-dibenzobicyclo 2.2.2!o ctane.