×

Certain aminoguanidine compounds, pharmaceutical compositions containing them and their use in treating gastrointestinal motility disorders and disorders associated with cephalic pain

  • US 5,510,353 A
  • Filed: 01/09/1995
  • Issued: 04/23/1996
  • Est. Priority Date: 03/22/1991
  • Status: Expired due to Term
First Claim
Patent Images

1. A compound of the formula ##STR27## wherein R1 hydrogen;

  • C1-6 alkyl;

    (C1-6 alkyl)carbonyl;

    or benzoyl;

    R5 is hydrogen;

    halo;

    C1-6 alkyl;

    hydroxy;

    nitro;

    amino;

    C1-4 alkylamino;

    C1-10 alkylcarbonylamino;

    C2-6 alkoxy-carbonyl;

    SO2 NRa Rb ;

    cyano;

    trimethylsilyl;

    C1-6 alkyl monosubstituted by --SO2 -(C1-6 alkyl), --SO2 NRa Rb, --CONRa Rb, --NH--SO2 --(C1-6 alkyl), --N (C1-6 alkyl)--SO2 --(C1-6 alkyl), --NRa Rb, C2-6 alkoxycarbonyl or --PO(C1-4 alkyl)2 ;

    carboxy;

    CONRa Rb ;

    --PO(C1-4 alkyl)2 ;

    --OCONRc Rd ;

    C1-6 alkoxy;

    C1-6 alkoxy monosubstitutedby hydroxy, C1-4 alkoxy, NRa R'"'"'b, CONRa Rb, CSNRa Rb,(C1-6 alkyl)carbonyloxy or benzoyloxy;

    C2-6 alkenyloxy;

    pyridyl-carbonyloxy;

    (C1-6 alkyl)carbonyloxy;

    or benzoyloxy;

    and wherever they appear in the above definition ofR5, each of Ra and Rb, independently, is hydrogen or C1-6 alkyl;

    R'"'"'b is hydrogen or C1-6 alkyl; and

    each of Rc and Rd, independently, is C1-6 alkyl;

    R7 is hydrogen, halo, C1-6 alkyl or C1-6 alkoxy;

    X--Y is --CR8

    N-- or---H(R8)--NH-- where R8 is hydrogen or C1-6 alkyl; and

    B is a radical of formula (a) or (b), ##STR28## where n is 1 or 2;

    A1 is C═

    O or CH2 ;

    X1 is S;

    NR11 where R11 is hydrogen;

    or CR12 R13 where each of R12 and R13, independently, is hydrogen or C1-4 alkyl;

    R10 is hydrogen;

    C1-12 alkyl;

    C1-6 alkyl monosubstituted by hydroxy, aryl, aryloxy, adamantyl, a heterocyclic radical, --NH--SO2 -aryl or --NR15 --COR16 where R15 is hydrogen or C1-4 alkyl and R16 is C1-6 alkyl, C5-7 cycloalkyl, C5-7 cycloalkyl-C1-4 alkyl, aryl or aryl(C1-4 alkyl);

    C5-7 cycloalkyl;

    adamantyl;

    (C1-10 alkyl)-carbonyl;

    benzoyl;

    phenyl(C1-4 alkyl)carbonyl;

    or --CONHR14 where R14 is C1-10 alkyl or C5-7 cycloalkyl;

    and wherever "aryl" appears as is or in the significances "aryloxy", "--NH--SO2 -aryl" or "aryl(C1-4 alkyl)" in the above definition, it is phenyl or phenyl mono- or disubstituted by fluoro, chloro, methyl or methoxy; and

    wherever the term "a heterocyclic radical" appears in the above definition, it is pyridyl, imidazolyl, benzimidazolyl, pyrrolidinyl, piperidino, pyrazinyl, perhydroindolyl or a radical of formula (d) ##STR29## where E is --CH2 CH2 --,--CH2 N(R17)-- where R17 is hydrogen or C1-4 alkyl;

    or --(CH2)3 --where one or two hydrogens therein can be replaced by C1-6 alkyl; and

    E1 is --CO--or --CH2 --;

    andX2 is --SR20 where R20 is C1-6 alkyl;

    or --NR3 R'"'"'10 where either R3 is hydrogen or C1-6 alkyl and R'"'"'10 has one of the significances indicated above for R10 ;

    or R3 andR'"'"'10 together with the nitrogen atom to which they are attached form a heterocyclic radical as defined above;

    with the proviso that where B is a radical of formula (b), only one of R10 and R'"'"'10 can be other than hydrogen and X2 can be --SR20 only when R10 is hydrogen;

    which compound is in free base or pharmaceutically acceptable salt form.

View all claims
  • 2 Assignments
Timeline View
Assignment View
    ×
    ×