Pyridine compounds which have useful pharmaceutical activity

Details Pyridine compounds which have useful pharmaceutical activity Pyridine compounds which have useful pharmaceutical activity

1993-06-14

1995-03-21

Ivy, C. Warren

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514344, 514357, 546276, 546286, 546330, 546333, 546334, 546335, 546336, C07D21354, A61K 3144

Patent

active

053995759

DESCRIPTION:

BRIEF SUMMARY
The present invention concerns new pyridine derivatives of the general formula I ##STR2## in which A signifies an alkylene radical with 1 to 3 carbon atoms or a group --CH.dbd.CH--, B an oxygen atom or a valency bond, m a whole number from 0 to 5, n the number 0 or 1, X a valency bond, an oxygen atom or a sulphur atom, Y a valency bond, a phenylene radical substituted, if desired, one or more times by C.sub.1 - to C.sub.6 -alkyl, C.sub.1 - to C.sub.6 -alkoxy, halogen, hydroxyl or aminocarbonyl, Z hydrogen, halogen or C.sub.1 - to C.sub.6 -alkyl or cyano and R a group CN, COOH, COOC.sub.1 - to C.sub.6 -alkyl, CONH-tetrazolyl, --CON(OH)(C.sub.1 -C.sub.6 -alkyl) or 5-(1H)-tetrazolyl, as well as for the case that Y represents a phenylene radical also hydrogen, with the exception of the compound 4-[2-(4)-pyridinovinyl]-carboxymethoxybenzene, their physiologically compatible salts and processes for their preparation, as well as medicaments containing these compounds.
Compounds of the formula I, in which A=an alkylene chain, B=an oxygen atom or a valency, m=a whole number from 0 to 5, n=0, X=valency and Y=valency, Z=hydrogen or alkyl, R=CN, COOH and COOalk are, in part, described in DE-A-2 951 786 as thromboxane synthebase inhibitors. In DE-A-3 641 024 the compound 4-[2-(4)-pyridinovinyl]-carboxymethoxybenzene is mentioned by name which finds use as liquid crystal component.
The new compounds of the general formula I display valuable pharmacological properties, in particular they can inhibit the antigen-caused contraction of lung tissue strips. Therefore, they are suitable for the treatment of allergic diseases, as well as of inflammation-caused bronchospastic and bronchoconstrictory reactions.
The alkyl radical in the mentioned groups can be straight-chained or branched. Preferred alkyl radicals are the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.-butyl, n-pentyl and 3-pentyl radical.
Halogen atoms are especially flourine, chlorine and bromine.
The bonding of the radical A can take place in 2-, 3- or 4-position of the pyridine, of the radical B in 2-, 3- or 4-position of the phenyl ring.
Especially preferred are compounds of the formula I in which A, B, m, n, X, Y and Z have the given meaning and R signifies a group CO-NH-tetrazolyl, --CON(OH)(C.sub.1 -C.sub.6 -alkyl) or 5-(1H)-tetrazolyl.
Furthermore, compounds of the formula I are preferred in which A, B, m, n, Y, Z and R have the given meaning and Y represents a phenylene radical substituted if desired.
Apart from the compounds mentioned in the Examples, the subject of the present invention are, in particular, all substances which display every possible combination of the substituents mentioned in the examples.
The process according to the invention for the preparation of the compounds of formula I is characterised in that, in per se known manner, one either
a) reacts a compound of the general formula II ##STR3## in which A, Z and n have the given meaning and B' signifies an oxygen atom, with a compound of the general formula III radical, or
b) reacts a compound of the general formula IV ##STR4## in which A, B, G, Z, m and n have the given meaning, with a compound of the general formula V
c) for the case that A signifies the group --CH.dbd.CH--, reacts a compound of the general formula VI ##STR5## in which Z and n have the given meaning, with a compound of the general formula VII ##STR6## in which B, X, Y, R and m have the given meaning and L represents a formyl group or a reactive derivative hereof, and subsequently, if desired, converts a substituent R into another substituent R given by the definition or a group A into another group A given by the definition or oxidises the pyridine nitrogen and, if desired, converts the compound obtained of the formula I into a salt by reaction with physiologically compatible acids or bases.
As reactive residues G, there come into question chlorine, bromine, mesyloxy or tosyloxy. A conversion of the radical R into another radical R defined by the claim takes place, for example, by reaction of a compound of

REFERENCES:
patent: 4271170 (1981-06-01), Tanouchi et al.
patent: 4317828 (1982-03-01), Tanouchi et al.
patent: 4427682 (1984-01-01), Tanouchi et al.
Honma et al, J. of Med. Chem, vol. 27, pp. 125-128, 1934.

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