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Src kinase inhibitor compounds

  • US 6,498,165 B1
  • Filed: 06/26/2000
  • Issued: 12/24/2002
  • Est. Priority Date: 06/30/1999
  • Status: Expired due to Fees
First Claim
Patent Images

1. The compound of Formula I embedded imageor pharmaceutically acceptable salts, hydrates, solvates, crystal forms or diastereomers thereof, whereinR1 and R2 are independently:

  • a) H, b) halo (Br, Cl, I or F) c) OH, d) SH, e) CN, f) NO2, g) R11, h) OR11, i) OC(═

    O)R11, j) OC(═

    O)OR 11, k) OC(═

    O)NHR11, l) OC(═

    O)NR 11R12, m) SR11, n) SOR11, o) SO2R11, p) C(═

    O)R11, q) C(═

    O)OR 11, r) C(═

    O)NHR11, s) C(═

    O)NR 11R12, t) NH2, u) NHR11, v) NR11R12, w) NHC(═

    O)R11, x) NR11C(═

    O)R12, y) NR11C(═

    O)NHR12, z) NR11C(═

    O)NR12R13, aa) SO2NHR11, ab) SO2NR11R12, ac) NHSO2R11, ad) NR11SO2R12, R3 and R5 independently are;

    a) H, b) C1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from oxo, X′

    , Y′ and

    Z′

    , c) aryl, wherein aryl is defined as phenyl or naphthyl unsubstituted or substituted with one, two or three substituents selected from;

    X′

    , Y′ and

    Z′

    , or d) R3 and R5 taken together can represent ═

    O;

    e) R3 or R5 can represent a 2 or 3 carbon methylene bridge forming a ring of 5 to 8 atoms fused to the A ring;

    R4 is;

    a) H, or b) C1-C6-alkyl, or c) C1-C6-alkoxyl;

    X5 and X6 are independently CRa or N;

    Ra is;

    H, or C1-C6-alkyl;

    n is 0, 1 or 2;



    X1

    X2

    X3

    X4

    is;

    a) —

    CR6

    CR6

    CR6a

    CR6

    , b) —

    CR6a

    CR6

    CR6

    CR6

    , c) —

    CR6

    CR6a

    CR6

    CR6

    , d) —

    CR6

    CR6

    CR6

    CR6a

    , e) —

    N═

    CR6

    CR6

    CR6

    , f) —

    CR6

    N—

    CR6

    CR6

    , g) —

    CR6

    CR6

    N═

    CR6

    , h) —

    CR6

    CR6

    CR6

    N—

    , i) —

    N═

    CR6

    N═

    CR6

    , j) —

    CR6

    N—

    CR6

    N—

    , k) —

    CR6

    N—

    N═

    CR6

    , or l) —

    N═

    CR6

    CR6

    N—

    ;

    R6 and R6a are independently;

    a) H, b) halo(Br, Cl, I, or F) c) OH, d) SH, e) CN, f) NO2, g) N3, h) N2+BF4

    , i) R11, j) OR11, k) OC(═

    O)R11, l) OC(═

    O)OR11, m) OC(═

    O)NHR11, n) OC(═

    O)NR11R12, o) SR11, p) SOR11, q) SO2R11, r) C1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from R11,R12, and R13, s) C(═

    O)R11, t) C(═

    O)OR11, u) C(═

    O)NHR11, v) C(═

    O)NR11R12, w) C(═

    O)N(OR11)R12, x) NH2, y) NHR11, z) NHC1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from R11,R12, and R13, aa) NR11R12, ab) NHC(═

    O)R11, ac) NR11C(═

    O)R12, ad) NHC(═

    O)NHR11, ae) NR11C(═

    O)NHR12, af) NR11C(═

    O)NR12R13, ag) SO2NH2, ah) SO2NHR11, ai) SO2NR11R12, aj) NHSO2R11, ak) NR11SO2R12, al) NHP(═

    O)(OC1-C6-alkyl)2, or am) R6 and R6a when on adjacent carbons can be joined to form a 5- or 6-membered ring having the following bridging atoms;

    i) —

    CH═

    CH—

    CH═

    CH—

    , ii) —

    OCH2O—

    , iii) —

    C(O)N(R11)C(O)—

    , iv) —

    CH2N(R11)CH2

    , v) —

    N═

    CHNHC(O)—

    , vi) —

    C(O)NHCH═

    N—

    , vii) —

    C(O)OC(O)—

    , viii) —

    NHC(O)NHC(O)—

    , ix) —

    C(O)NHC(O)NH—

    , x) —

    N═

    CHNH—

    , xi) —

    NHCH═

    N—

    , xii) —

    N═

    CHNR11, xiii) —

    NR11CH═

    N—

    , xiv) embedded imagexv) embedded image

    represents;

    a) phenyl, b) naphthyl, c) pyridyl, d) pyrazinyl, e) pyrimidinyl, f) pyrrolyl, g) thienyl, h) oxazolyl, i) isoxazolyl, j) thiazolyl, k) pyrazolyl, l) triazolyl, m) tetrazolyl, n) furanyl, o) benzothienyl, p) benzofuranyl, q) indolyl, r) imidazolyl, s) benzimidazolyl, or t) thiadiazolyl, R7, R8, R9, and R10 independently are selected from;

    a) H, b) halo(Br, Cl, I, or F) c) OH, d) SH, e) CN, f) NO2, g) N3 h) N2+BF4

    i) R11, j) OR11, k) SR11, l) SOR11, m) SO2R11, n) C1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from R11R12, and R13, o) C1-C6-perfluoroalkyl, p) C(═

    O)R11, q) C(═

    O)OR11, r) C(═

    O)NHR11, s) C(═

    O)NR11R12, t) NH2, u) NHR11, v) NHC1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from R11,R12, and R13, w) NR11R12, x) NHC(═

    O)R11, y) NR11C(═

    O)R12, z) NR11C(═

    O)NHR12, aa) NR11C(═

    O)NR12R13, ab) SO2NHR11, ac) SO2NR11R12, ad) NHSO2R11, ae) NR11SO2R12, or af) two of R7, R8, R9, and R10 when on adjacent carbons join together to form a methylenedioxy bridge;

    R11, R12, and R13 independently are selected from;

    a) C1-C6-perfluoroalkyl, b) C1-C6-alkyl, unsubstituted or substituted with one, two, or three substituents selected from oxo, X′

    , Y′ and

    Z′

    , c) C2-C6-alkenyl, unsubstituted or substituted with one, two, or three substituents selected from oxo, X′

    , Y′ and

    Z′

    , d) C2-C6-alkynyl, unsubstituted or substituted with one, two, or three substituents selected from oxo, X′

    , Y′ and

    Z′

    , e) aryl, wherein aryl is defined as phenyl or naphthyl, unsubstituted or substituted with one, two, or three substituents selected from X′

    , Y′ and

    Z′

    , f) heterocyclyl, wherein the heterocyclyl is unsubstituted or substituted with one, two, three or four substituents selected from oxo, X′

    , Y′

    , and Z′

    , or g) C3-C6-cycloalkyl, unsubstituted or substituted with one, two, or three substituents selected from oxo, X′

    , Y′ and

    Z′

    ;

    X′

    , Y′ and

    Z′

    independently are selected from;

    a) H, b) halo, c) CN, d) NO2, e) hydroxy, f) C1-C6-perfluoroalkyl, g) C1-C6-alkoxyl, alkoxyl unsubstituted or substituted with aryl, wherein aryl is defined as phenyl or naphthyl, h) (C═

    O)(C1-C6-alkyl), alkyl unsubstituted or substituted with aryl, wherein aryl is defined as phenyl or naphthyl, i) (C═

    O)O(C1-C6-alkyl), alkyl unsubstituted or substituted with aryl, wherein aryl is defined as phenyl or naphthyl, j) (C═

    O)NH(C1-C6-alkyl), k) (C═

    O)N(C1-C6-alkyl)2, l) NH2, m) NHC1-C6-alkyl, wherein alkyl is unsubstituted or substituted with aryl or NH2, n) N(C1-C6-alkyl)2, o) NHaryl, wherein aryl is defined as phenyl or naphthyl, unsubstituted or substituted with one, two, or three substituents selected from halo, phenyl, CN, NO2,hydroxy, C1-C6-alkyl, C1-C6-alkoxyl, NH2,NHC1-C6-alkyl, N(C1-C6-alkyl)2, (C═

    O)(C1-C6-alkyl), (C═

    O)O(C1-C6-alkyl), (C═

    O)NH(C1-C6-alkyl), (C═

    O)N(C1-C6-alkyl)2, NH(C═

    O)(C1-C6-alkyl), p) NHheterocyclyl, wherein heterocyclyl is unsubstituted or substituted with one, two or three substituents selected from halo, phenyl, oxo, CN, NO2, hydroxy, C1-C6-alkyl, C1-C6-alkyl substituted with C3-C7-cycloalkyl, C1-C6-alkoxyl, NH2, NHC1-C6-alkyl, N(C1-C6-alkyl)2, (C═

    O)(C1-C6-alkyl), (C═

    O)O(C1-C6-alkyl), (C═

    O)OCH2phenyl, (C═

    O)NH(C1-C6-alkyl), (C═

    O)N(C1-C6-alkyl)2, NH(C═

    O)(C1-C6-alkyl), q) NHCHO, r) NH(C═

    O)(C1-C6-alkyl), s) NH(C═

    O)(OC1-C6-alkyl), t) aryl, wherein aryl is as defined above in o, u) C1-C6-alkyl, wherein alkyl is unsubstituted or substituted with hydroxy, C3-C7-cycloalkyl, aryl or heterocyclyl, wherein aryl is defined as above in o and heterocyclyl is as defined above in p, v) heterocyclyl, wherein heterocyclyl is as defined above in p, w) when two of X′

    , Y′ and

    Z′

    are on adjacent carbons they can join to form a methylenedioxy bridge, x) NH(C═

    O)aryl, y) —

    NR14NHR15, z) —

    S(O)x C1-C6-alkyl, aa) SO2NH C1-C6-alkyl, or ab) CO2H;

    R14 and R15 are independently;

    H, C1-C6-alkyl, aryl or C1-C6-alkylaryl;

    or x is 0, 1 or 2.

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