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Compounds to treat Alzheimer's disease

  • US 6,992,081 B2
  • Filed: 09/21/2001
  • Issued: 01/31/2006
  • Est. Priority Date: 03/23/2000
  • Status: Expired due to Fees
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Assignments
First Claim
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1. A compound of the formula embedded imageor a pharmaceutically acceptable salt thereof whereinR1 is:

  • (I) C1-C6 alkyl, unsubstituted or unsubstituted with one, two or three C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    NH2, —

    C≡

    N, —

    CF3, or —

    N3, (II) —

    (CH2)1-2—

    S—

    CH3, (III) —

    CH2—

    CH2—

    S—

    CH3, (IV) —

    CH2—

    (C2-C6 alkenyl) unsubstituted or substituted by one —

    F, (V) —

    (CH2)0-3—

    (R1-aryl) where R1-aryl is phenyl, 1-naphthyl, 2-naphthyl, indanyl, indenyl, dihydronaphthyl, tetralinyl unsubstituted or independently substituted on the aryl ring with one or two of C1-C3 alkyl, —

    CF3, —

    F, Cl, —

    Br, —

    I, C1-C3 alkoxy, —

    O—

    CF3, —

    NH2, —

    OH, or —

    C≡

    N;

    R2 is;

    (I) —

    H, (II) C1-C6 alkyl, or (III) —

    (CH2)0-4—

    R2-1 where R2-1 is (C3-C6)cycloalkyl, R1-aryl where R1-aryl is optionally substituted with R100, where R100 is (1) C1-C6 alkyl, (2) —

    F, —

    Cl, —

    Br, or —

    I, (3) —

    OH, (4) —

    NO2, (5) —

    CO—

    OH, (6) —

    C≡

    N, (7) —

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different and are;

    (a) —

    H, (b) —

    C1-C6 alkyl unsubstituted or substituted with one —

    OH or —

    NH2, (c) —

    C1-C6 alkyl unsubstituted or substituted with one to three —

    F, —

    Cl, —

    Br, or —

    I, (d) —

    C3-C7 cycloalkyl, (e) —

    C1-C2 alkyl)-(C3-C7cycloalkyl), (f) —

    (C1-C6 alkyl)-O—

    (C1-C3alkyl), (g) —

    C1-C6 alkenyl with one or two double bonds, (h) —

    C1-C6 alkynyl with one or two triple bonds, (i) —

    C1-C6 alkyl chain with one double bond and one triple bond, (8) —

    CO—

    (C3-C12 alkyl), (9) —

    CO—

    (C3-C6 cycloalkyl), (11) —

    CO—

    R1-heterocycle where R1-heterocycle is morpholinyl, thiomorpholinyl, thiomorpholinyl S-oxide, thiomorpholinyl S,S-dioxide, piperazinyl, homopiperazinyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl, piperidinyl, tetrahydrofuranyl, or tetrahydrothiophenyl, where the R1-heterocycle group is bonded by any atom of the parent R1-heterocycle group substituted by hydrogen such that the new bond to the R1-heterocycle group replace the hydrogen atom and its bond, where heterecycle is unsubstituted or substituted with one or two ═

    O, C1-C3 alkyl, —

    CF3, —

    F, Cl, —

    Br, —

    I, C1—

    C3 alkoxy, —

    OCF3, —

    NH2, —

    OH, or —

    C≡

    N, (12) —

    C-O—

    RN-4 where RN-4 is morpholinyl, thiomorpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl, where each group is unsubstituted or substituted with one or two C1-C3 alkyl, (13) —

    CO—

    O—

    RN-5 where RN-5 is;

    (a) C1-C6 alkyl, or (b) —

    (CH2)0-2—

    (R1-aryl) where R1-aryl is as defined above, (14) —

    SO2—

    NRN-2RN-3 where RN-2 and RN-3 are as defined above, (15) —

    SO—

    (C1-C6 alkyl), (16) —

    SO2—

    (C3-C12 alkyl), (17) —

    NH—

    CO—

    O—

    RN-5 where RN-5 is as defined above, (18) —

    NH—

    CO—

    N(C2-C6 alkyl)2, (19) —

    N—

    CS—

    N(C1-C3 alkyl)2, (20) —

    N(C1-C3 alkyl)—

    CO—

    RN-5 where RN-5 is as defined above, (21) —

    NRN-2RN-3 where RN-2 and RN-3 can be the same or different and are as defined above, (22) —

    RN-4 where RN-4 is as defined above, (23) —

    O—

    CO—

    (C1-C6 alkyl), (24) —

    O—

    CO—

    N(C1-C3 alkyl)2, (25) —

    O—

    CS—

    N(C1-C3 alkyl)2, (26) —

    O—

    (C1-C6 alkyl), (27) —

    O—

    (C2-C5 alkyl)—

    COOH, (28) —

    S—

    (C1-C6 alkyl), (29) C1-C6 alkyl unsubustituted or substituted with 1, 2, 3, 4, or 5 —

    F, (30) —

    O—

    (C1-C6 alkyl unsubstituted or substituted with 1, 2, 3, 4, or 5 —

    F, or (31) —

    O-φ

    , RN-1 is phenyl that is independently substituted with one, two, three or four of R100;

    Ra is hydrogen or C1-C6 alkyl;

    RC is RCH where RCH is morpholinyl, thiomorpholinyl, thiomorpholinyl S-oxide, thiomorpholinyl S,S-dioxide, piperazinyl, homopiperazinyl, pyrrolidinyl;

    pyrrolinyl, tetrahydropyranyl, piperidinyl, tetrahydrofuranyl, or tetrahydrothiophenyl, each of which is optionally substituted with oxo, C1-C3 alkyl, —

    CF3, —

    F, Cl, —

    Br or —

    I, C1-C3 alkoxy, —

    O—

    CF3, —

    NH2, —

    OH, or —

    C≡

    N;

    RCY where RCY is pyridinyl, pyrimidinyl, quinolinyl, indenyl, indanyl, benzothiophenyl, indolyl, indolinyl, pyridazinyl, pyrazinyl, isoindolyl, isoquinolyl, quinazolinyl, quinoxalinyl, isoxazolyl, pyrazolyl, oxazolyl, thiazolyl, indolizinyl, indazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, furanyl, thienyl, pyrrolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, 1,4-benzodioxanyl, purinyl, oxazolopyridinyl, imidazopyridinyl, isothiazolyl, naphthyridinyl, cinnolinyl, carbazolyl, β

    -carbolinyl, isochromanyl, chromanyl, furazanyl, tetrahydroisoquinoline, isoindolinyl, isobenzotetrahydrofuranyl, isobenzotetrahydrothienyl, isobenzothiophenyl, benzoxazolyl, or pyridopyridinyl, each of which is optionally substituted with C1-C3 alkyl, —

    CF3, —

    F, Cl, —

    Br, or I, C1-C3 alkoxy, —

    O—

    CF3, —

    NH2, —

    OH, or —

    C≡

    N;

    —

    (C1-C10)alkyl-RCH;

    or —

    (C1-C10)alkyl-RCY.

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