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Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin

  • US 5,804,585 A
  • Filed: 04/15/1996
  • Issued: 09/08/1998
  • Est. Priority Date: 04/15/1996
  • Status: Expired due to Fees
First Claim
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1. A sulfonamide compound of formula (I) ##STR10## wherein:

  • Ar1, which contains from 1 to 30 carbon atoms, is selected from the group consisting of optionally substituted alkyl groups, aryl groups and heteroaryl groups;

    wherein the aryl and heteroaryl groups include single rings, fused bicyclic or tricyclic rings; and

    the alkyl groups are straight or branched chains or straight or branched chains that include cyclic portions; and

    Ar2 is a group of formula;

    ##STR11## Y is N or O+ ;

    X is S, O, or NR11 in which R11, which is hydrogen or contains up to about 30 carbon atoms, is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R15 and S(O)n R15 in which n is 0-2; and

    R15, which is selected independently from R11, is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl and cycloalkynyl;

    R3, R4 and R5 are selected from (i), (ii), (iii) or (iv);

    (i) R3, R4 and R5 are each selected independently from among H, NHOH, NH2, NO2, N3, halide, pseudohalide, alkyl, alkenyl, alkynyl, alkenyl, alkylaryl, aryloxy, aryl, heteroaryl, alkoxy, alkylamino, alkylthio, alkoxyalkyl, alkylsulfinyl, alkylsulfonyl, aryloxy, arylamino, arylthio, arylsulfinyl, arylsulfonyl, haloalkyl, haloaryl, alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, formyl, amido, where the alkyl, alkenyl, alkynl portions are straight or branched chains of from about 1 up to about 10 carbons, and the aryl portions contain from 3 up to about 10 carbons;

    or, alternatively,(ii) two of R3, R4 and R5 form 1,3-butadienyl, 4-dimethylamino-1,3 butadiene, 1-chloro-1,3-butadiene, 1-aza-1,3-butadienyl or 2-aza-1,3-butadienyl groups or form alkylenedioxy; and

    the other of R3, R4 and R5 is as defined in (i)(iii) two of R3, R4 and R5 are independently selected from alkyl, alkoxy, halide aminoalkyl, dialkylaminoalkyl, in which the alkyl and alkoxy groups contain from 1 to 10, preferably 1 to 6 carbons, and are straight or branched chains and the other is H;

    or(iv) any two of R3, R4 and R5, which are each selected as in (i), form fused carbocyclic or heterocyclic rings and the other is selected as in (i); and

    R7 is hydrogen or contains up to about 50 carbon atoms, generally up to about 30, more generally 20 or fewer, and is selected hydrogen, halide, pseudohalide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aryloxy, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl, OH, CN, C(O)R18, CO2 R18, SH, S(O)n, (CH2)r, (CH2)r R18, S(O)n R18 in which n is 0-2, and r is 0 to 6, HNOH, NR18 R19, NO2, N3, OR18, R19 NCOR18 and CONR19 R18, in which R19 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, alkoxy, aryloxy, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R20, S(O)n R20 in which n is 0-2; and

    R18 and R20 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, heterocycle, alkoxy, aryloxy, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl or cycloalkynyl; and

    any of the groups set forth for R7 is unsubstituted or substituted with any substituents set forth for Z, which is hydrogen, halide, pseudoahlide, alkyl, alkoxy, alkenyl, alkynyl, aryl, aryloxy, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl, OH, CN, C(O)R21, CO2 R21, SH, S(O)n R21 in which n is 0-2, NHOH, NR22 R21, NO2, N3, OR21, R22 NCOR21 and CONR22 R21 ;

    R22 is selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, heterocycle, aralkyl, alkoxy, aralkoxy, cycloalkyl, cycloalkenyl, cycloalkynyl, C(O)R23 and S(O)n R23 in which n is 0-2; and

    R21 and R23 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, alkylaryl, heterocycle, aralkyl, aralkoxy, cycloalkyl, cycloalkenyl or cycloalkynyl.

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