Anti-allergic thiadiazolo [4,3-a]pyridine derivatives

Details Anti-allergic thiadiazolo [4,3-a]pyridine derivatives Anti-allergic thiadiazolo [4,3-a]pyridine derivatives

1994-03-18

1995-09-05

Dentz, Bernard

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514293, 514301, 544331, 546 83, 546114, A61K 31435, C07D51304

Patent

active

054479347

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP 92/02142.
The subject of the present invention are thiadiazolo[4,3-a]pyridine derivatives, processes for their preparation and medicaments which contain these compounds.
The invention concerns thiadiazolo[4,3-a]pyridine derivatives of the general formula I ##STR2## in which X.sup.1 and X.sup.2 the same or different, signify hydrogen, a C.sub.1 - to C.sub.6 -alkyl radical or a halogen atom or, insofar as they stand in neighbouring positions, together with the carbon atoms carrying them, form a condensed-on phenyl ring and R signifies a phenyl, cyclohexyl, cyclopentyl, pyridyl, piperidinyl, pyrimidinyl, pyrrolidinyl, isoxazolyl, oxazolyl, thiazolyl, thiazolinyl, thiazolyl or tetrazolyl radical which, if desired, can be substituted one or more times by halogen, cyano, nitro, C.sub.1 - to C.sub.6 -alkyl, C.sub.1 - to C.sub.6 -haloalkyl, hydroxyl, C.sub.1 - to C.sub.6 -alkoxy, methylenedioxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 - to C.sub.6 -haloalkylthio, amino, C.sub.1 - to C.sub.6 -alkylamino, C.sub.2 - to C.sub.12 -dialkylamino, pyrrolyl, carboxy, carbamoyl, benzyl, C.sub.1 to C.sub.6 -hydroxyalkyl, C.sub.2 - to C.sub.7 -carboxyalkyl, C.sub.2 - to C.sub.7 -alkoxycarbonyl-C.sub.1 -to C.sub.6 -alkyl, carbamoyl.sub.1 - to C.sub.6 -alkyl, N-hydroxy-N-C.sub.1 - to C.sub.6 -carbamoyl-C.sub.1 - to C.sub.6 -alkyl or C.sub.2 -to C.sub.6 -alkenyl, as well as their physiologically compatible salts, with the proviso that R cannot signify phenyl, 2,5-dichlorophenyl or 2-pyridinyl when X.sup.1 and X.sup.2 are simultaneously hydrogen or R cannot signify 3,4-dichlorophenyl when X.sup.1 or X.sup.2 represent methyl or R cannot signify 2-pyridinyl when X.sup.1 or X.sup.2 represents bromine.
Surprisingly, it was found that the compounds of the 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.
Furthermore, they can prevent the lethality of an endotoxic shock and area therefore, suitable for the treatment of inflammatory processes brought about by monokines, as well as of septic shock, autoimmune diseases, graft-versus-host reactions and host-versus-graft diseases.
In J. Org. Chem. 35, 1965 (1970) is described inter alia the compound 3-(2-pyridinylimino)-3H-[1,2,4]-thiadiazolo[4,3-a]pyridine, in J. Org. Chem. 36, 1846 (1971) the compounds 3-phenylimino-3H-[1,2,4]thiadiazolo[4,3-a]pyridine and 3-(4-methylphenylimino)-3H-[1,2,4]-thiadiazolo4,3-a]pyridine but without statement of a pharmacological effectiveness. These compounds are also usable as medicaments and are the subject of the invention.
The alkyl radicals in the said alkyl, alkoxy, alkylthio and (di)alkylamino groups, as well as the alkenyl radicals, can be straight-chained or branched. Preferred alkyl radicals in these groups are the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.-butyl, n-pentyl and 3-pentyl radical, preferred alkenyl radicals the vinyl and the allyl radical.
A C.sub.1 -C.sub.6 -haloalkyl radical is preferably trifluormethyl.
As halogen atoms, there come into question fluorine, chlorine and bromine.
Carbocyclic radicals are preferably the phenyl, cyclohexyl and cyclopentyl radical. As heterocyclic radicals, there come into question especially pyridyl, piperidinyl, pyrimidinyl, pyrrolidinyl, isoxazolyl, oxazolyl, thiazolyl, thiazolinyl, triazolyl and tetrazolyl radicals.
Preferred compounds of the formula I are compounds in which X.sup.1 represents hydrogen, methyl or chlorine, X.sup.2 hydrogen or X.sup.1 and X.sup.2 together form a condensed-on phenyl ring and R a phenyl ring which can be substituted once or twice by fluorine, chlorine, methyl, methoxy, tert.-butyl, isopropoxy, trifluoromethyl, trifluoromethylthio, hydroxyl, nitrile, nitro, hydroxymethyl, methylenedioxy, diethylamino, methylthio, pyrrolyl, methoxycarbonylmethyl, carboxymethyl, N-hydroxy-N-methylcarb

REFERENCES:
Potts et al. (I), J. Org. Chem. 35(6), pp. 1965-1968 (1970).
Potts, et al. (II) J. Org. Chem. 36(13), pp. 1846-1848 (1971).

Affiliated with

Also associated with

Rating

Anti-allergic thiadiazolo [4,3-a]pyridine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Anti-allergic thiadiazolo [4,3-a]pyridine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anti-allergic thiadiazolo [4,3-a]pyridine derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-472929