×

Isothiazole derivatives useful as anticancer agents

  • US 6,235,764 B1
  • Filed: 05/21/1999
  • Issued: 05/22/2001
  • Est. Priority Date: 06/04/1998
  • Status: Expired due to Term
0
Associated Cases
0
Associated Defendants
0
Product Citations
0
Petitions
95
Forward Citations
1
Assignment
First Claim
Patent Images

1. A compound of the formula or a pharmaceutically acceptable salt, prodrug or solvate thereof, wherein,X1 is O or S;

  • R1 is —

    (CH2)t(4-5 membered heterocyclic), wherein t is an integer from 0 to 5;

    said heterocyclic group is optionally fused to a C6-C10aryl group, a C5-C8 saturated cyclic group, or a 5-10 membered heterocyclic group; and

    said R1 group, including the optionally fused portions of said R1 group, is optionally substituted by 1 or 2 substituents independently selected from C1-C4 alkyl, hydroxy and hydroxymethyl;

    R2 is H;

    R3 is H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, —

    (CH2)t(C6-C10 aryl), or —

    (CH2)t(5-10 membered heterocyclic), wherein t is an integer from 0 to 5;

    said alkyl group optionally include 1 or 2 hetero moieties selected from O, S and —

    N(R6)—

    with the proviso that two O atoms, two S atoms, or an O and S atom are not attached directly to each other;

    said aryl and heterocyclic R3 groups are optionally fused to a C6-C10 aryl group, a C5-C8 saturated cyclic group, or a 5-10 membered heterocyclic group;

    1 or 2 carbon atoms in the foregoing heterocyclic moieties are optionally substituted by an oxo (═

    O) moiety;

    the —

    (CH2)t—

    moieties of the foregoing R3 groups optionally include a carbon-carbon double or triple bond where t is an integer from 2 to 5, and the foregoing R3 groups are optionally substituted by 1 to 5 R4 groups;

    each R4 is independently selected from C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, halo, cyano, nitro, trifluoromethyl, trifluoromethoxy, azido, —

    OR5, —

    C(O)R5, —

    C(O)OR5, —

    NR6C(O)OR5, —

    OC(O)R5, —

    NR6SO2R5, —

    SO2NR5R6, —

    NR6C(O)R5, —

    C(O)NR5R6, —

    NR5R6, —

    S(O)jR7 wherein j is an integer ranging from 0 to 2, —

    SO3H, —

    NR5(CR6R7)tOR6, —

    (CH2)t(C6-C10 aryl), —

    SO2(CH2)t(C6-C10 aryl), —

    S(CH2)t(C6-C10 aryl), —

    O(CH2)t(C6-C10 aryl), —

    (CH2)t(5-10 membered heterocyclic), and —

    (CR6R7)mOR6, wherein m is an integer from 1 to 5 and t is an integer from 0 to 5;

    said alkyl group optionally contains 1 or 2 hetero moieties selected from O, S and —

    N(R6)—

    with the proviso that two O atoms, two S atoms, or an O and S atom are not attached directly to each other;

    said aryl and heterocyclic R4 groups are optionally fused to a C6-C10 aryl group, a C5-C8 saturated cyclic group, or a 5-10 membered heterocyclic group;

    1 or 2 carbon atoms in the foregoing heterocyclic moieties are optionally substituted by an oxo (═

    O) moiety; and

    the alkyl, aryl and heterocyclic moieties of the foregoing R4 groups are optionally substituted by 1 to 3 substituents independently selected from halo, cyano, nitro, trifluoromethyl, trifluoromethoxy, azido, —

    NR6SO2R5, —

    SO2NR5R6, —

    C(O)R5, —

    C(O)OR5, —

    OC(O)R5, —

    NR6C(O)R5, —

    C(O)NR5R6, —

    NR5R6, —

    (CR6R7)mOR6 wherein m is an integer from 1 to 5, —

    OR5 and the substituents listed in the definition of R5;

    each R5 is independently selected from H, C1-C10 alkyl, —

    (CH2)t(C6-C10 aryl), and —

    (CH2)t(5-10 membered heterocyclic), wherein t is an integer from 0 to 5;

    said alkyl group optionally includes 1 or 2 hetero moieties selected from O, S and —

    N(R6)—

    with the proviso that two O atoms, two S atoms, or an O and S atom are not attached directly to each other;

    said aryl and heterocyclic R5 groups are optionally fused to a C6-C10 aryl group, a C5-C8 saturated cyclic group, or a 5-10 membered heterocyclic group; and

    the foregoing R5 subsituents, except H, are optionally substituted by 1 to 3 substituents independently selected from halo, cyano, nitro, trifluoromethyl, trifluoromethoxy, azido, —

    C(O)R6, —

    C(O)OR6, —

    CO(O)R6, —

    NR6C(O)R7, —

    C(O)NR6R7, —

    NR6R7, hydroxy, C1-C6 alkyl, and C1-C6 alkoxy; and

    each R6 and R7 is independently H or C1-C6 alkyl.

View all claims
  • 1 Assignment
Timeline View
Assignment View
    ×
    ×