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US 6,083,951 AGranted
Aryl-substituted pyrimidine sulphonamide compounds as endothelin antagonists
AssigneeZeneca Limited
InventorRobert Hugh Bradbury
Life of this patent
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Abstract
Pyrimidine sulphonamide compounds of the following formula, ##STR1## wherein Q is a naphthyl or biphenyl group either unsubstituted or substituted with A.sup.1, and where A.sup.1, R.sup.1 and R.sup.2 are a variety of alkyl, aryl and cyclic moieties, as described in the specification hereof, which compounds are useful for the treatment of diseases or medical conditions such as hypertension, pulmonary hypertension, cardiac or cerebral circulatory disease and renal disease.
Claims13
A compound having the formula VII;
- wherein:
- Q is a naphthyl or biphenyl group which is either unsubstituted or is substituted at one, two, or three positions with A.sup.1 ;
- A.sup.1 and R.sup.2 are independently selected at each occurrence from hydrogen, C.sub.1 -C.sub.6 -alkoxy, di-halogeno-C.sub.1 -C.sub.6 -alkoxy, tri-halogeno-C.sub.1 -C.sub.6 -alkoxy, phenyl, phenoxy, phenyl-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkyl, amino-C.sub.1 -C.sub.6 -alkyl, hydroxy-C.sub.1 -C.sub.6 -alkyl, N-[C.sub.1 -C.sub.4 -alkyl]amino-C.sub.1 -C.sub.6 -alkyl, N,N-[di-C.sub.1 -C.sub.4 -alkyl]amino-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, halogeno-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylsulphonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylsulphonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.1 -C.sub.6 -alkyl, halogeno, hydroxy, mercapto, cyano, nitro, carboxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.2 -C.sub.6 -alkenyloxycarbonyl, phenyloxycarbonyl, phenyl-C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkanoyl, benzoyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, C.sub.1 -C.sub.6 -alkanoylamino, trifluoroacetyl, trifluoroacetamido, N-[C.sub.1 -C.sub.4 -alkyl]trifluoroacetamido, benzamido, N-[C.sub.1 -C.sub.4 -alkyl]benzamido, carbamoyl, C.sub.1 -C.sub.4 -alkylcarbamoyl, di-C.sub.1 -C.sub.4 -alkylcarbamoyl, phenylcarbamoyl, sulphamoyl, N-C.sub.1 -C.sub.4 -alkylsulphamoyl, N,N-di-C.sub.1 -C.sub.4 -alkylsulphamoyl, N-phenylsulphamoyl, C.sub.1 -C.sub.6 -alkanesulphonamido, benezenesulphonamido, ureido, 3-C.sub.1 -C.sub.6 -alkylureido, 3-phenylureido, thioureido, 3-C.sub.1 -C.sub.6 -alkylthioureido and 3-phenylthioureido;
- or
- A.sup.1 and R.sup.2 independently are a group --NRaRb, in which Ra and Rb are independently selected from hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.6 -alkyl bearing a carboxy or C.sub.1 -C.sub.4 -alkoxycarbonyl group;
- or
- A.sup.1 and R.sup.2 independently are a group --NRaRb in which Ra and Rb taken together complete a 1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 1-piperidinyl or 2-oxo-1-piperidinyl ring;
- R.sup.1 is selected from 2-[C.sub.1 -C.sub.6 -alkoxycarbonyl]ethenyl, 2-phenylethenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkoxycarbonylethynyl, phenylethynyl, C.sub.1 -C.sub.3 -alkoxy, dihalogeno-C.sub.1 -C.sub.3 -alkoxy, trihalogeno-C.sub.1 -C.sub.3 -alkoxy, phenyl-C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.6 -alkyl, amino-C.sub.1 -C.sub.6 -alkyl, hydroxy-C.sub.1 -C.sub.6 -alkyl, N-[C.sub.1 -C.sub.4 -alkyl]amino-C.sub.1 -C.sub.6 -alkyl, N,N-[di-C.sub.1 -C.sub.6 -alkyl]amino-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, halogeno-C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyloxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylsulphinyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkylsulphonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.1 -C.sub.6 -alkyl, halogeno, hydroxy, mercapto, cyano, nitro, carboxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.2 -C.sub.6 -alkenyloxycarbonyl, phenyloxycarbonyl, phenyl-C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkanoyl, benzoyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulphinyl, C.sub.1 -C.sub.6 -alkylsulphonyl, phenylthio, phenylsulphinyl, phenylsulphonyl, C.sub.1 -C.sub.6 -alkanoylamino, trifluoroacetyl, trifluoroacetamido, N-[C.sub.1 -C.sub.4 -alkyl]trifluoroacetamido, benzaamido, N-[C.sub.1 -C.sub.4 -alkyl]benzamido, carbamoyl, C.sub.1 -C.sub.4 -alkylcarbamoyl, di-C.sub.1 -C.sub.4 -alkylcarbamoyl, phenylcarbamoyl, sulphamoyl, N-C.sub.1 -C.sub.4 -alkylsulphamoyl, N,N-di-C.sub.1 -C.sub.4 -alkylsulphamoyl, N-phenylsulphamoyl, C.sub.1 -C.sub.6 -alkanesulphonamido, benezenesulphonamido, ureido, 3-C.sub.1 -C.sub.6 -alkylureido, 3-phenylureido, thioureido, 3-C.sub.1 -C.sub.6 -alkylthioureido and 3-phenylthioureido;
- or
- R.sup.1 is a group --NRaRb, in which Ra and Rb are independently selected from hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl-C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.6 -alkyl bearing a carboxy or C.sub.1 -C.sub.4 -alkoxycarbonyl group;
- or
- R.sup.1 is the group --NRaRb in which Ra and Rb taken together complete a 1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 1-piperidinyl or 2-oxo-1-piperidinyl ring;
- where any phenyl, naphthyl or benzene moiety of A.sup.1, R.sup.1 or R.sup.2 is either unsubstituted or is substituted at one or two positions, with substituents independently selected at each occurrence from C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogeno, cyano and trifluoromethyl;
- or
- a pharmaceutically-acceptable salt of any foregoing compound.
12 more elements
Dependencies are inferred from the claim text.