Pyridazine compounds

Details Pyridazine compounds Pyridazine compounds

1997-09-05

1999-08-10

Dees, Jose' G.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514252, 544234, 544244, 544250, C07D47104, A61K 3150

Patent

active

059359560

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to fused pyridazine compounds, in particular derivatives, their use as medicaments and pharmaceutical compositions comprising them.
EPA 0 351 435 discloses a series of fused pyridazine compounds which are said to be useful for the treatment of various diseases associated with immune function deficiency. A series of structurally distinct compounds have now been discovered and surprisingly found to possess anti-allergic and anti-inflammatory activity.
In a first aspect the invention therefore provides a compound of formula I: ##STR1## wherein X is (CH.sub.2).sub.n or CH.dbd.CH; and 2-benzothiazolyl, 2- or 3-quinolyl or 2-quinoxalinyl (all of which are optionally substituted by one or more substituents selected from halo, nitro, cyano, phenyl, phenylsulfonyl, C.sub.1-6 alkyl,C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfinyl, COOH, COO(C.sub.1-6 alkyl), CONH.sub.2, C.sub.1-6 alkyl substituted by phenyl, or phenyl, in which any alkyl, alkoxy, alkylthio and alkylsulfinyl groups may optionally be substituted by one or more fluorine atoms; represent a bond; and pharmaceutically acceptable derivatives thereof.
Alkyl groups, whether alone or as part of another group, can be linear or branched.
Pharmaceutically acceptable derivatives include solvates, N-oxides and salts. For example the compounds of the formula (I) can form acid addition salts with acids, such as conventional pharmaceutically acceptable acids, for example maleic, hydrochloric, hydrobromic, phosphoric, acetic, fumaric, salicylic, citric, lactic, mandelic, tartaric and methanesulphonic acids.
Suitably X is (CH.sub.2).sub.n or CH.dbd.CH, preferably X is (CH.sub.2).sub.n preferably where n is 2.
Suitably R.sup.1 is hydrogen or together with R.sup.2 is a bond. Preferably R.sup.1 is hydrogen.
Suitably R.sup.2 is hydrogen, C.sub.1-6 alkyl or together with R.sup.1 is a bond. Preferably R.sup.2 is hydrogen.
Suitably Ar.sup.1 represents thiazolyl, phenyl, pyridyl, pyrimidinyl, 2-benzothiazolyl, 2- or 3-quinolyl or 2-quinoxalinyl (all of which are optionally substituted by one or more substituents selected from halo, nitro, cyano, phenyl, phenylsulfonyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfinyl, COOH, COO(C.sub.1-6 alkyl), CONH.sub.2, C.sub.1-6 alkyl substituted by phenyl, or phenyl, in which any alkyl, alkoxy, alkylthio and alkylsulfinyl groups may optionally be substituted by one or more fluorine atoms. Preferably Ar.sup.1 is phenyl optionally substituted by one or more substituents selected from C.sub.1-6 alkyl, halogen, nitro, cyano or CF.sub.3. Most preferably Ar.sup.1 is phenyl optionally substituted by one or two substituents selected from halogen, methyl or trifluoromethyl, particularly trifluoromethyl.
Suitably Y is CH.sub.2 or C.dbd.O, preferably Y is C.dbd.O.
The nitrogen atom in the left ring of the compounds of formula (I) can be in any position. Preferably, when X forms part of a 6-membered ring, the nitrogen atom is in the 7- or 9-position.
The compounds of formula I may exhibit tautomerism. All tautomeric forms and mixtures thereof are included within the scope of the invention. The compounds of formula I may also contain one or more asymmetric carbon atoms and may therefore exhibit optical and/or diastereoisomerism. All diastereoisomers may be separated using conventional techniques, eg. chromatography or fractional crystallisation. The various optical isomers may be isolated by separation of a racemic or other mixture of the compounds using conventional, eg. fractional crystallisation or HPLC, techniques. Alternatively the desired optical isomers may be made by reaction of the appropriate optically active starting materials under conditions which will not cause racemisation, or by derivatisation, for example with a homochiral acid followed by separation of the diastereomeric esters by conventional means (eg. HPLC, chromatography over silica). All stereoisomers are included within the scope of the invention.
Particularly preferred compounds of the invention includ

REFERENCES:
patent: 5340808 (1994-08-01), Jean et al.
patent: 5597918 (1997-01-01), Nakao et al.

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