Piperidylidene derivatives, their production and pharmaceutical compositions containing them

Claim 2

A compound of formula I wherein n is 2 or 3, R 1 comprises a tricyclic nucleus of formula Z in which X is -S-, -CH 2 - CH 2 -, -CH=CH- or -CH 2 -CO--CH 2 -C (=NOH) - or -CH 2 -CH (OH) - in which the oxo, oxime or hydroxy group is attached to the carbon atom adjacent to a, and A is a fused benzene ring, a fused thiophene ring in which the sulfur atom is adjacent to a, or a fused pyridine ring in which the nitrogen atom is adjacent to b, and R 2 is hydrogen or a physiologically- acceptable and -hydrolysable acid residue,

Claim 3

A compound according to claim 1 of formula I wherein n is 2 or 3, R 1 is an unsubstituted tricyclic nucleus of formula Z as illustrated in claim 1 in which X is -S- and A is a fused benzene or a fused pyridine ring; or X is -CH=CH-or -CH 2 -CH 2 - and A is a fused benzene ring; or X is -CH 2 -CO- and A is a fused thiophene ring, and R 2 is hydrogen.

Claim 4

A compound according to claim 1 selected from the group consisting of - 2-{2-[4-(5H-dibenzo[a,d]cyclohept-5-yliden)piperidin-1-yl]ethoxy} ethanol; - 2-{2-[2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohept-5-yliden)piperidin-1-yl]ethoxy]ethoxy}ethanol; - 2-{2-[4-(10,11-dihydro-5H-dibenzo[a,d]cyclohept-5-yliden)piperidin-1-yl]ethoxy}ethanol; - 2-{2-[4-(1OH-[1]benzothiopyrano[3,2-b]pyridin-10-yliden)piperidin-1-yl]ethoxy} ethanol; - 2-{2-[2-[4-(9H-thioxanthen-9-yliden)piperidin-1-yl] ethoxy]ethoxy}ethanol; and - 2-{2-[4-(9H-thioxanthen-9-yliden)piperidin-1-yl] ethoxy}ethanol.

Claim 5

A compound according to claim 1 which is 4-{1-[2-[2-(2-hydroxy-ethoxy)ethoxy]ethyl]piperidin-4-yliden}-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-(9H)-one.

Claim 6

A compound according to claim 1 which is 2-{2-[2- [4- (5H-dibenzo[a,d]cyclohept―5-yliden)piperidin-1-yl]-ethoxy]ethoxy}ethanol.

Claim 7

A compound according to any one of claims 1 to 5 in acid addition salt form.

Claim 8

Process for the production of a compound of formula I as defined in claim 1, in free base or in acid addition salt form, which comprises a) for the production of a compound of formula I wherein R 2 and n have the meanings given in claim 1 and R 1 comprises a tricyclic nucleus of formula Z 1 in which X 1 has the meaning given for X in claim 1 except that it may not represent -CH 2 -C(=NOH) - or -CH 2 -CH (OH)- and A has the meaning given in claim 1; introducing a group of formula II wherein n has the meaning given in claim 1, into a compound of formula III wherein R' 1 comprises a tricyclic nucleus of formula Z 2 wherein X 2 is i) a group X 1 as defined above or ii) a precursor thereof and A has the meaning given in claim 1, when required converting a precursor group X 2 into a group X 1 and, when required, esterifying a compound thus obtained to obtain a corresponding compound wherein R 2 is a physiologically -acceptable and -hydrolysable acid residue; or b) for the production of a compound of formula I wherein R 2 and n have the meanings given in claim 1 and R 1 comprises a tricyclic nucleus of formula Z 3 in which X 3 is -CH 2 -C(=NOH)- or -CH 2 -CH(OH)- and A has the meaning given in claim 1; converting the keto group in a compound of formula I wherein R 2 is hydrogen, n has the meaning given in claim 1 and R 1 comprises a tricyclic nucleus of formula Z 4 in which A has the meaning given in claim 1, and, when required, esterifying a compound thus obtained to obtain a corresponding compound wherein R 2 is a physiologically-acceptable and -hydrolysable acid residue, and recovering the obtained compound of formula I in free base or acid addition salt form.

Claim 9

A compound according to any one of claims 1 to 5 in free base or in pharmaceutically acceptable acid addition salt form for use as a pharmaceutical.

Claim 10

A compound according to any one of claims 1 to 5 in free base or in pharmaceutically acceptable acid addition salt form for use in the treatment or prophylaxis of asthmatic conditions, in particular allergic asthma, and of other allergic disorders.

Claim 11

A pharmaceutical composition comprising a compound of formula I as defined in any one of claims 1 to 5 in free base or in pharmaceutically acceptable acid addition salt form, together with a pharmaceutically acceptable diluent or carrier therefore.