Aryl- and hetaryl-sulfonamide derivatives, their preparation and

Details Aryl- and hetaryl-sulfonamide derivatives, their preparation and Aryl- and hetaryl-sulfonamide derivatives, their preparation and

1997-08-18

1999-10-05

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544131, 544148, 544159, 544316, 544364, 544365, 544377, 544388, 546194, 546226, 546261, 546265, 5462837, 546293, 546309, 546324, 546337, 548252, 549414, 549416, 549438, C07C31121, C07C31129, C07D21346, C07D40512

Patent

active

059626828

DESCRIPTION:

BRIEF SUMMARY
The present invention is concerned with novel sulphonamides and their use as medicaments. In particular, the invention is concerned with novel compounds of formula I ##STR2## wherein R.sup.1 signifies phenyl, substituted phenyl or heterocyclyl; carboxy, phenyl, substituted phenyl, heterocyclyl or a residue --CONR.sup.5 R.sup.6 or --NR.sup.5 COR.sup.7 ; heterocyclic residue; lower-alkyl, cyano-lower-alkyl, hydroxy-lower-alkyl, di-lower-alkylamino-lower-alkyl, carboxy-lower-alkyl, lower-alkoxycarbonyl-lower-alkyl, lower-alkoxycarbonylamino-lower-alkyl or phenyl-lower-alkoxycarbonyl; --OC(O)OR.sup.8, --NHC(O)NHR.sup.8 or --NHC(O)OR.sup.8 ;
Examples of heterocyclyl residues are mono- or bicyclic 5- and 6-membered heterocyclic residues having oxygen, nitrogen or sulphur as the hetero atom, such as 2- and 3-furyl, pyrimidinyl, 2-, 3- and 4-pyridyl and pyridyl N-oxide, 5-tetrazolyl, 2-tetrazol-5-yl-4-pyridyl, 1,2- and 1,4-diazinyl, morpholino, 2- and 3-thienyl, isoxazolyl, oxazolyl, thiazolyl, imidazolyl, pyrrolyl, benzofuranyl, benzothienyl, indolyl, purinyl, quinolyl, isoquinolyl and quinazolyl, which can be substituted e.g. by lower-alkyl, lower-alkanoyl, hydroxy, lower-alkanoyloxy, lower-alkoxy, lower-alkoxycarbonyl, formyl, amino, mono- or di-lower-alkylamino or halogen. Phenyl residues can be substituted by lower-alkyl, lower alkoxy, hydroxy-lower alkyl; carboxy, lower-alkylenedioxy such as methylenedioxy or ethylenedioxy, lower-alkanoyl, hydroxy, amino, mono- or di-lower-alkylamino, phenyl and/or halogen. The term "lower" used here denotes groups with 1-7 C atoms, preferably 1-4 C atoms. Alkyl, alkoxy and alkylthio groups as well as alkyl groups as constituents of alkancyl groups can be straight-chain or branched. Methyl, ethyl, propyl, isopropyl, butyl, sec. and tert.butyl are examples of such alkyl groups. Halogen denotes fluorine, chlorine, bromine and iodine, with chlorine being preferred. Lower-alkoxycarbonyl, aryloxycarbonyl (especially phenoxycarbonyl) and aralkoxycarbonyl (especially benzyl- and phenethyloxycarbonyl) groups are examples of esterified carboxy groups. N-Heterocyclic residues formed with R.sup.5 and R.sup.6 are preferably monocyclic 6-membered heterocyclyl residues which can contain a further oxygen or nitrogen atom, such as morpholino, 2,6-dimethylmorpholino, piperidino, piperazino or piperazino N.sup.4 -substituted by lower-alkyl, formyl or lower-alkoxycarbonyl.
In EP-A-0 658 542, WO-A-95/26957, EP-A-0 526 708, EP-A-0 601 386 and Nature, Vol. 365, Oct. 21, 1993, p. 759-761 there are disclosed sulfonamide compounds with different chemical structures and an unspecific endothelin activity.
The U.S. Pat. No. 4,902,698 discloses benzenesulfonamidopyridyl compounds which are useful as thrombaxane A.sub.2 antagonists.
In the EP-A-0 472 053 there are disclosed sulfonamide derivatives with an antitumor activity.
In Arzneimittel-Forschung, Vol. 15, 15. November 1965. p. 1309-1317, there are disclosed sulfanilamidopyrimidines which have an antibacterial activity.
In Biochemical and Biophysical Research Communications, Vol. 201, No. 1, 1994, p. 228-234 there are disclosed sulfonamides with a 5 or 6 membered heteroaryl system with two heteroatoms wherein at least one atom is nitrogen and the other one is nitrogen, oxygen or sulfur. These compounds have an ET.sub.A selective endothelin activity.
Preferred residues R.sup.1 are phenyl and monocyclylic heterocyclyl residues containing a nitrogen atom, such as pyridyl, especially 2-pyridyl, which can be substituted, preferably mono-substituted. Examples of preferred residues R.sup.1 are especially lower-alkylphenyl, lower-alkoxyphenyl, lower-alkylthiophenyl, trifluoromethy)phenyl, lower-alkylenedioxyphenyl and lower-alkylpyridyl. Preferred residues R.sup.2 are phenyl substituted by lower-alkoxy and/or halogen. Preferred residues R.sup.3 are hydrogen, cyano, phenyl, 5-tetrazolyl, carboxy, lower-alkoxycarbonyl and --CONR.sup.5 R.sup.6, in which R.sup.5 is hydrogen and R.sup.6 is phenyl, phenyl substituted by lower-alkoxy, hydroxy, hydroxy-lower-alkyl,

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Clozel, et al. Nature (1993) 365, pp. 759-761.
Biochem. Biophys. Res. Commun (1994) 201, pp. 228-234--Chan M.F. et al.
Arznemittel-Forschung, vol. 15, No. 11 (Nov., 1965) pp. 1309-1317--Kruger-Thiemer, et al. `Die antibakterielle Wirkung des nicht eiweissgebundenen Anteils der Sulfanilamide im menschlichen Plasmawasser` (English translation).
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