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Compounds to treat Alzheimer's disease

  • US 6,737,420 B2
  • Filed: 03/23/2001
  • Issued: 05/18/2004
  • Est. Priority Date: 03/23/2000
  • Status: Expired due to Fees
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Forward Citations
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Assignment
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 substituted 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-C7 cycloalkyl), (f) —

    (C1-C6 alkyl)—

    O—

    (C1-C3 alkyl), (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 replaces the hydrogen atom and its bond, where heterocycle is unsubstituted or substituted with one or two ═

    O, Cl-C3 alkyl, —

    CF3, —

    F, Cl, —

    Br, —

    I, C1-C3 alkoxy, —

    OCF3, —

    NH2, —

    OH, or —

    C≡

    N, (12) —

    CO—

    RNN-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-4 where RN-5 is;

    (a) C1-C6 alkyl, or (b) —

    (CH2)0-2—

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

    SO2—

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

    SO—

    (C1-C8 alkyl), (16) —

    SO2—

    (C3-C12 alkyl), (17) —

    NH—

    CO—

    O—

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

    NH—

    CO—

    N(C1-C3 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 unsubstituted or substituted with 1, 2, 3, 4, or 5 —

    F, or (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;

    —

    (C1-C10)alkyl-K1-3 in which;

    (A) the alkyl chain is unsubstituted or substituted with one —

    OH, (B) the alkyl chain is unsubstituted or substituted with one C1-C6 alkoxy unsubstituted or substituted with 1-5 —

    F, (D) the alkyl chain is unsubstituted or substituted with 1-5 —

    F, (F) each K is;

    (1) H, (2) C1-C3 alkyl, (3) C1-C3 alkoxy, (4) C1-C3 alkylthioxy, (5) C1-C6 alkylacylamino, (6) C1-C6 alkylacyloxy, (7) amino (8) C1-C6 alkylamino (9) phenylamino, (10) carbamyl (11) carboxyl (12) carboxy(C2-C5)alkoxy, (13) carboxy(C2-C5)alkylthioxy, (16) amino unsubstituted or substituted with C1-C6 alkyl, (17) hydroxyl, or (18) carboxyl methyl ester.

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