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Substituted alcohols useful in treatment of Alzheimer's disease

  • US 6,982,264 B2
  • Filed: 06/27/2002
  • Issued: 01/03/2006
  • Est. Priority Date: 06/27/2001
  • Status: Expired due to Fees
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Assignment
First Claim
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1. A compound of the formula I:

  • embedded imagewherein X is CR2R3, C1-6 alkylene or alkenyl, O, S, SO, or SO2;

    wherein R1 is (I) C1-C6 alkyl, optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, C1-C7 alkyl (optionally substituted with C1-C3 alkyl and C1-C3 alkoxy), —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, —

    NR1-aR1-b where R1-a and R1-b are independently —

    H or C1-C6 alkyl, and —

    OC═

    O NR1-aR1-b, (II) —

    CH2—

    S(O)0-2—

    (C1-C6 alkyl), (III) —

    CH2—

    CH2—

    S(O)0-2—

    (C1-C6 alkyl), (IV) C2-C6 alkenyl with one or two double bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (V) C2-C6 alkynyl with one or two triple bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (VI) —

    (CH2)n1—

    (R1-aryl) where n1 is zero or one and where R1-aryl is phenyl, 1-naphthyl, 2-naphthyl and indanyl, indenyl, dihydronaphthalyl, or tetralinyl optionally substituted with one, two, three or four of the following substituents on the aryl ring;

    (A) C1-C6 alkyl optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (B) C2-C6 alkenyl with one or two double bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (C) C2-C6 alkynyl with one or two triple bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (D) —

    F, Cl, —

    Br or —

    I, (F) —

    C1-C6 alkoxy optionally substituted with one, two or three of —

    F, (G) —

    NRN-2RN-3 where RN-2 and RN-3 are as defined below, (H) —

    OH, (I) —

    C≡

    N, (J) C3-C7 cycloalkyl, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (K) —

    CO—

    (C1-C4 alkyl), (L) —

    SO2—

    NR1-aR1-b, (M) —

    CO—

    NR1-aR1-b, (N) —

    SO2—

    (C1-C4 alkyl), (VII) —

    (CH2)n1—

    (R1-heteroaryl) where n1 is as defined above and where R1-heteroaryl is selected from the group consisting of;

    pyridinyl, pyrimidinyl, quinolinyl, benzothienyl, indolyl, indolinyl, pryidazinyl, pyrazinyl, isoindolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, imidazolyl, isoxazolyl, pyrazolyl, oxazolyl, thiazolyl, indolizinyl, indazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, furanyl, thienyl, pyrrolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, oxazolopyridinyl, imidazopyridinyl, isothiazolyl, naphthyridinyl, cinnolinyl, carbazolyl, beta-carbolinyl, isochromanyl, chromanyl, tetrahydroisoquinolinyl, isoindolinyl, isobenzotetrahydrofuranyl, isobenzotetrahydrothienyl, isobenzothienyl, benzoxazolyl, pyridopyridinyl, benzotetrahydrofuranyl, benzotetrahydrothienyl, purinyl, benzodioxolyl, triazinyl, phenoxazinyl, phenothiazinyl, pteridinyl, benzothiazolyl, imidazopyridinyl, imidazothiazolyl, dihydrobenzisoxazinyl, benzisoxazinyl, benzoxazinyl, dihydrobenzisothiazinyl, benzopyranyl, benzothiopyranyl, coumarinyl, isocoumarinyl, chromonyl, chromanonyl, pyridinyl-N-oxide, tetrahydroquinolinyl, dihydroquinolinyl, dihydroquinolinonyl, dihydroisoquinolinonyl, dihydrocoumarinyl, dihydroisocoumarinyl,isoindolinonyl, benzodioxanyl, benzoxazolinonyl, pyrrolyl N-oxide, pyrimidinyl N-oxide, pyridazinyl N-oxide, pyrazinyl N-oxide, quinolinyl N-oxide, indolyl N-oxide, indolinyl N-oxide, isoquinolyl N-oxide, quinazolinyl N-oxide, quinoxalinyl N-oxide, phthalazinyl N-oxide, imidazolyl N-oxide, isoxazolyl N-oxide, oxazolyl N-oxide, thiazolyl N-oxide, indolizinyl N-oxide, indazolyl N-oxide, benzothiazolyl N-oxide, benzimidazolyl N-oxide, pyrrolyl N-oxide, oxadiazolyl N-oxide, thiadiazolyl N-oxide, triazolyl N-oxide, tetrazolyl N-oxide, benzothiopyranyl S-oxide, benzothiopyranyl S,S-dioxide, where the R1-heteroaryl group is bonded to —

    (CH2)n1—

    by any ring atom of the parent RN-heteroaryl group substituted by hydrogen such that the new bond to the R1-heteroaryl group replaces the hydrogen atom and its bond, where heteroaryl is optionally substituted with one, two, three or four of;

    (1) C1-C6 alkyl optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (2) C2-C6 alkenyl with one or two double bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (3) C2-C6 alkynyl with one or two triple bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (4) —

    F, Cl, —

    Br or —

    I, (6) —

    C1-C6 alkoxy optionally substituted with one, two, or three of —

    F, (7) —

    NRN-2RN-3 where RN-2 and RN-3 are as defined below, (8) —

    OH, (9) —

    C≡

    N, (10) C3-C7 cycloalkyl, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (11) —

    CO—

    (C1-C4 alkyl), (12) —

    SO2—

    NR1-aR1-b, (13) —

    CO—

    NR1-aR1-b, or (14) —

    SO2—

    (C1-C4 alkyl), with the proviso that when n1 is zero R1-heteroaryl is not bonded to the carbon chain by nitrogen, or (VIII) —

    (CH2)n1—

    (R1-heterocycle) where n1 is as defined above and R1-heterocycle is selected from the group consisting of;

    morpholinyl, thiomorpholinyl, thiomorpholinyl S-oxide, thiomorpholinyl S,S-dioxide, piperazinyl, homopiperazinyl, pyrrolidinyl, pyrrolinyl, tetrahydropyranyl, piperidinyl, tetrahydrofuranyl, tetrahydrothienyl, homopiperidinyl, homomorpholinyl, homomorpholinyl S-oxide, homothiomorpholinyl S,S-dioxide, oxazolidinonyl, dihydropyrazolyl, dihydropyrrolyl dihydropyrazinyl dihydropyridinyl dihydropyrimidinyl, dihydrofuryl, dihydropyranyl, tetrahydrothienyl S-oxide, tetrahydrothienyl S,S-dioxide, homothiomorpholinyl S-oxide, 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 optionally substituted with one, two, three or four;

    (1) C1-C6 alkyl optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (2) C2-C6 alkenyl with one or two double bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    N1-aR1-b, (3) C2-C6 alkynyl with one or two triple bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (4) —

    F, Cl, —

    Br, or —

    I, (5) C1-C6 alkoxy, (6) —

    C1-C6 alkoxy optionally substituted with one, two, or three —

    F, (7) —

    NRN-2RN-3 where RN-2 and RN-3 are as defined below, (8) —

    OH, (9) —

    C≡

    N, (10) C3-C7 cycloalkyl, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (11) —

    CO—

    (C1-C4 alkyl), (12) —

    SO2—

    NR1-aR1-b, (13) —

    CO—

    NR1-aR1-b, (14) —

    SO2—

    (C1-C4 alkyl), (15) ═

    O, with the proviso that when n1 is zero R1-heterocycle is not bonded to the carbon chain by nitrogen;

    wherein R2 is (I) —

    H, (II) C1-C6 alkyl, optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (III) —

    (CH2)0-4—

    R2-1 where R2-1 is R1-aryl or R1-heteroaryl;

    (IV) C2-C6 alkenyl with one or two double bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (V) C2-C6 alkynyl with one or two triple bonds, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (VI) —

    (CH2)0-4—

    C3-C7 cycloalkyl, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b;

    wherein R3 is (I) —

    H, (II) C1-C6 alkyl, optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (III) —

    (CH2)0-4—

    R2-1 where R2-1 is R1--aryl or R1-heteroaryl;

    (IV) C2-C6 alkenyl with one or two double bonds, (V) C2-C6 alkynyl with one or two triple bonds, or (VI) —

    (CH2)0-4—

    C3-C7 cycloalkyl, optionally substituted with one, two or three substituents selected from the group consisting of —

    F, —

    Cl, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, and where R2 and R3 are taken together with the carbon to which they are attached to form a carbocycle of three, four, five, six, or seven carbon atoms, optionally where one carbon atom is replaced by a heteroatom selected from the group consisting of —

    O—

    , —

    S—

    , —

    SO2—

    , and —

    NRN-2—

    , where RN-2 is as defined below;

    wherein RN is (I) RN-1—

    XN—

    where XN is selected from the group consisting of;

    (A) —

    CO—

    , (B) —

    SO2—

    , (C) —

    (CR′

    R″

    )1-6 where R′ and

    R″

    are the same or different and are —

    H and C1-C4 alkyl, (D) —

    CO—

    (CR′

    R″

    )1-6—

    XN-1 where XN-1 is selected from the group consisting of —

    O—

    , —

    S— and

    —

    NR′

    — and

    where R′ and

    R″

    are as defined above, or (E) a single bond;

    where RN-1 is selected from the group consisting of;

    (A) RN-aryl where RN-aryl is phenyl, 1-naphthyl, 2-naphthyl, tetralinyl, indanyl, or 6,7,8,9-tetrahydro-5H-benzo[a]cycloheptenyl, optionally substituted with one, two or three of the following substituents which can be the same or different and are;

    (1) C1-C6 alkyl, optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (2) —

    OH, (3) —

    NO2, (4) —

    F, —

    Cl, —

    Br, or —

    I, (5) —

    CO—

    OH, (6) —

    C≡

    N, (7) (CH2)0-4—

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different and are selected from the group consisting of;

    (a) —

    H, (b) —

    C1-C6 alkyl optionally substituted with one substitutent selected from the group consisting of;

    (i) —

    OH, and (ii) —

    NH2, (c) —

    C1-C6 alkyl optionally substituted with one, two, or 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) —

    C2-C6 alkenyl with one or two double bonds, (h) —

    C2-C6 alkynyl with one or two triple bonds, (i) —

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

    R1-aryl, and (k) —

    R1-heteroaryl, (8) —

    (CH2)0-4—

    CO—

    (C1-C12 alkyl), (9) —

    (CH2)0-4—

    CO—

    (C2-C12 alkenyl with one, two or three double bonds), (10) —

    (CH2)0-4—

    CO—

    (C2-C12 alkynyl with one, two or three triple bonds), (11) —

    (CH2)0-4—

    CO—

    (C3-C7 cycloalkyl), (12) —

    (CH2)0-4—

    CO—

    R1-aryl, (13) —

    (CH2)0-4—

    CO—

    R1-heteroaryl, (14) —

    (CH2)0-4—

    CO—

    R1-heterocycle, (15) (CH2)0-4—

    CO—

    RN-4 where RN-4 is selected from the group consisting of morpholinyl, thiomorpholinyl, piperazinyl, piperidinyl, homomorpholinyl, homothiomorpholinyl, homomorpholinyl S-oxide, homothiomorpholinyl S,S-dioxide, pyrrolinyl and pyrrolidinyl where each group is optionally substituted with one, two, three, or four of C1-C6 alkyl, (16) —

    (CH2)0-4—

    CO—

    O—

    RN-5 where RN-5 is selected from the group consisting of;

    (a) C1-C6 alkyl, (b) —

    (CH2)0-2—

    (R1-aryl), (c) C2-C6 alkenyl containing one or two double bonds, (d) C2-C6 alkynyl containing one or two triple bonds, (e) C3-C7 cycloalkyl, and (f) —

    (CH2)0-2—

    (R1-heteroaryl), (17) —

    (CH2)0-4—

    SO2—

    NRN-2RN-3, (18) —

    (CH2)0-4—

    SO—

    (C1-C8 alkyl), (19) —

    (CH2)0-4—

    SO2—

    (C1-C12 alkyl), (20) —

    (CH2)0-4—

    SO2—

    (C3-C7 cycloalkyl), (21) —

    (CH2)0-4—

    N(H or RN-5)—

    CO—

    O—

    RN-5 where RN-5 can be the same or different, (22) —

    (CH2)0-4—

    N(H or RN-5)—

    CO—

    N(RN-5)2, where RN-5 can be the same or different, (23) —

    (CH2)0-4—

    N—

    CS—

    N(RN-5)2, where RN-5 can be the same or different, (24) —

    (CH2)0-4—

    N(—

    H or RN-5)—

    CO—

    RN-2 where RN-5 and RN-2 can be the same or different, (25) —

    (CH2)0-4—

    NRN-2RN-3 where RN-2 and RN-3 can be the same or different, (26) (CH2)0-4—

    RN-4, (27) —

    (CH2)0-4—

    O—

    CO—

    (C1-C6 alkyl), (28) —

    (CH2)0-4—

    P(O)—

    (ORN-aryl-1)2 where RN-aryl-1 is —

    H or C1-C4 alkyl, (29) —

    (CH2)0-4—

    O—

    CO—

    N(RN-5)2, (30) —

    (CH2)0-4—

    O—

    CS—

    N(RN-5)2, (31) —

    (CH2)0-4—

    O—

    (RN-5)2, (32) —

    (CH2)0-4—

    O—

    (RN-5)2—

    COOH, (33) —

    (CH2)0-4—

    S—

    (RN-5)2, (34) —

    (CH2)0-4—

    O—

    (C1-C6 alkyl optionally substituted with one, two, three, four, or five of —

    F), (35) C3-C7 cycloalkyl, (36) C2-C6 alkenyl with one or two double bonds optionally substituted with C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, or —

    NR1-aR1-b, (37) C2-C6 alkynyl with one or two triple bonds optionally substituted with C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, or —

    NR1-aR1-b, (38) —

    (CH2)0-4—

    N(—

    H or RN-5)—

    SO2—

    RN-2 where RN-5 and RN-2 can be the same of different, or (39) —

    (CH2)0-4—

    C3-C7 cycloalkyl, (B) —

    RN-heteroaryl where RN-heteroaryl is selected from the group consisting of;

    pyridinyl, pyrimidinyl, quinolinyl, benzothienyl, indolyl, indolinyl, pryidazinyl, pyrazinyl, isoindolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, imidazolyl, isoxazolyl, pyrazolyl, oxazolyl, thiazolyl, indolizinyl, indazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, furanyl, thienyl, pyrrolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, oxazolopyridinyl, imidazopyridinyl, isothiazolyl, naphthyridinyl, cinnolinyl, carbazolyl, beta-carbolinyl, isochromanyl, chromanyl, tetrahydroisoquinolinyl, isoindolinyl, isobenzotetrahydrofuranyl, isobenzotetrahydrothienyl, isobenzothienyl, benzoxazolyl, pyridopyridinyl, benzotetrahydrofuranyl, benzotetrahydrothienyl, purinyl, benzodioxolyl, triazinyl, phenoxazinyl, phenothiazinyl, pteridinyl, benzothiazolyl, imidazopyridinyl, imidazothiazolyl, dihydrobenzisoxazinyl, benzisoxazinyl, benzoxazinyl, dihydrobenzisothiazinyl, benzopyranyl, benzothiopyranyl, coumarinyl, isocoumarinyl, chromonyl, chromanonyl, pyridinyl-N-oxide, where the RN-heteroaryl group is bonded by any atom of the parent RN-heteroaryl group substituted by hydrogen such that the new bond to the RN-heteroaryl group replaces the hydrogen atom and its bond, where heteroaryl is optionally substituted with one, two, three, or four of;

    (1) C1-C6 alkyl, optionally substituted with one, two or three substituents selected from the group consisting of C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, and —

    NR1-aR1-b, (2) —

    OH, (3) —

    NO2, (4) —

    F, —

    Cl, —

    Br, or —

    I, (5) —

    CO—

    OH, (6) —

    C≡

    N, (7) —

    (CH2)0-4—

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different and are selected from the group consisting of;

    (a) —

    H, (b) —

    C1-C6 alkyl optionally substituted with one substitutent selected from the group consisting of;

    (i) —

    OH, and (ii) —

    NH2, (c) —

    C1-C6 alkyl optionally substituted with one, two, or 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) —

    C2-C6 alkenyl with one or two double bonds, (h) —

    C2-C6 alkynyl with one or two triple bonds, (i) —

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

    R1-aryl, and (k) —

    R1-heteroaryl, (8) —

    (CH2)0-4—

    CO—

    (C1-C12 alkyl), (9) —

    (CH2)0-4—

    CO—

    (C2-C12 alkenyl with one, two or three double bonds), (10) —

    (CH2)0-4—

    CO—

    (C2-C12 alkynyl with one, two or three triple bonds), (11) —

    (CH2)0-4—

    CO—

    (C3-C7 cycloalkyl), (12) —

    (CH2)0-4—

    CO—

    R1-aryl, (13) —

    (CH2)0-4—

    CO—

    R1-heteroaryl, (14) —

    (CH2)0-4—

    CO—

    R1-heterocycle, (15) —

    (CH2)0-4—

    CO—

    RN-4 where RN-4 is selected from the group consisting of morpholinyl, thiomorpholinyl, piperazinyl, piperidinyl, homomorpholinyl, homothiomorpholinyl, homomorpholinyl S-oxide, homothiomorpholinyl S,S-dioxide, pyrrolinyl and pyrrolidinyl where each group is optionally substituted with one, two, three, or four of C1-C6 alkyl, (16) —

    (CH2)0-4—

    CO—

    O—

    RN-5 where RN-5 is selected from the group consisting of;

    (a) C1-C6 alkyl, (b) —

    (CH2)0-2—

    (R1-aryl), (c) C2-C6 alkenyl containing one or two double bonds, (d) C2-C6 alkynyl containing one or two triple bonds, (e) C3-C7 cycloalkyl, and (f) —

    (CH2)0-2—

    (R1-heteroaryl), (17) —

    (CH2)0-4—

    SO2—

    NRN-2RN-3, (18) —

    (CH2)0-4—

    SO—

    (C1-C8 alkyl), (19) —

    (CH2)0-4—

    SO2—

    (C1-C12 alkyl), (20) —

    (CH2)0-4—

    SO2—

    (C3-C7 cycloalkyl), (21) —

    (CH2)0-4—

    N(H or RN-5)—

    CO—

    O—

    RN-5 where RN-5 can be the same or different, (22) —

    (CH2)0-4—

    N(H or RN-5)—

    CO—

    N(RN-5)2, where RN-5 can be the same or different, (23) —

    (CH2)0-4—

    N—

    CS—

    N(RN-5)2, where RN-5 can be the same or different, (24) —

    (CH2)0-4—

    N(—

    H or RN-5)—

    CO—

    RN-2 where RN-5 and RN-2 can be the same or different, (25) —

    (CH2)0-4—

    NRN-2RN-3 where RN-2 and RN-3 can be the same or different, (26) —

    (CH2)0-4—

    RN-4, (27) —

    (CH2)0-4—

    O—

    CO—

    (C1-C6 alkyl), (28) —

    (CH2)0-4—

    O—

    P(O)—

    (ORN-aryl-1)2 where RN-aryl-1 is —

    H or C1-C4 alkyl, (29) —

    (CH2)0-4—

    O—

    CO—

    N(RN-5)2, (30) —

    (CH2)0-4—

    O—

    CS—

    N(RN-5)2, (31) —

    (CH2)0-4—

    O—

    (RN-5)2, (32) —

    (CH2)0-4—

    O—

    (RN-5)2—

    COOH, (33) —

    (CH2)0-4—

    S—

    (RN-5)2, (34) —

    (CH2)0-4—

    O—

    (C1-C6 alkyl optionally substituted with one, two, three, four, or five of —

    F), (35) C3-C7 cycloalkyl, (36) C2-C6 alkenyl with one or two double bonds optionally substituted with C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, or —

    NR1-aR1-b, (37) C2-C6 alkynyl with one or two triple bonds optionally substituted with C1-C3 alkyl, —

    F, —

    Cl, —

    Br, —

    I, —

    OH, —

    SH, —

    C≡

    N, —

    CF3, C1-C3 alkoxy, or —

    NR1-aR1-b, (38) —

    (CH2)0-4—

    N(—

    H or RN-5)—

    SO2—

    RN-2 where RN-5 and RN-2 can be the same of different, (39) —

    (CH2)0-4—

    C3-C7 cycloalkyl, (C) RN-aryl—

    W—

    RN-aryl, (D) RN-aryl—

    W—

    RN-heteroaryl, (E) RN-aryl—

    W—

    RN-1-heterocycle, where RN-1-heterocycle is the same as R1-heterocycle, (F) RN-heteroaryl—

    W—

    RN-aryl, (G) RN-heteroaryl—

    W—

    RN-heteroaryl, (H) RN-heteroaryl—

    W—

    RN-heterocycle, (I) RN-heterocycle—

    W—

    RN-aryl, where RN-heterocycle is the same as R1-heterocycle, (J) RN-heterocycle—

    W—

    RN-heteroaryl, (K) RN-heterocycle—

    W—

    RN-1-heterocycle, where W is (1) —

    (CH2)0-4—

    , (2) —

    O—

    , (3) —

    S(O)0-2—

    , (4) —

    N(RN-5)—

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

    CO—

    ;

    (II) —

    CO—

    (C1-C10 alkyl) where alkyl is optionally substituted with one three substitutents selected from the group consisting of;

    (A) —

    OH, (B) —

    C1-C6 alkoxy, (C) —

    C1-C6 thioalkoxy, (D) —

    CO—

    O—

    RN-8 where RN-8 is —

    H, C1-C6 alkyl or -phenyl, (E) —

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (F) —

    CO—

    RN-4 where RN-4, (G) —

    SO2—

    (C1-C8 alkyl), (H) —

    SO2—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (I) —

    NH—

    CO—

    (C1-C6 alkyl), (J) —

    NH—

    CO—

    O—

    RN-8 where RN-8, (K) —

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (L) —

    RN-4, (M) —

    O—

    CO—

    (C1-C6 alkyl), (N) —

    O—

    CO—

    NRN-8RN-8 where the RN-8s are the same or different, (O) —

    O—

    (C1-C5 alkyl)-COOH, (P) —

    O—

    (C1-C6 alkyl optionally substitued with one, two, or three of —

    F, —

    CI, —

    Br, or —

    I), (Q) —

    NH—

    SO2—

    (C1-C6 alkyl), and (R) —

    F, —

    Cl, (III) —

    CO—

    (C1-C6 alkyl)-O—

    (C1-C6 alkyl) where alkyl is optionally substituted with one, two, or three substitutents selected from the group consisting of (A) —

    OH, (B) —

    C1-C6 alkoxy, (C) —

    C1-C6 thioalkoxy, (D) —

    CO—

    O—

    RN-8 where RN-8 is —

    H, C1-C6 alkyl or -φ

    , (E) —

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (F) —

    CO—

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

    SO2—

    (C1-C8 alkyl), (H) —

    SO2—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (I) —

    NH—

    CO—

    (C1-C6 alkyl), (J) —

    NH—

    CO—

    O—

    RN-8 where RN-8, (K) —

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (L) —

    RN-4, (M) —

    O—

    CO—

    (C1-C6 alkyl), (N) —

    O—

    CO—

    NRN-8RN-8 where RN-8 are the same or different, (O) —

    O—

    (C1-C5 alkyl)-COOH, (P) —

    O—

    (C1-C6 alkyl optionally substitued with one, two, or three of —

    F, —

    CI, —

    Br, or —

    I), (Q) —

    NH—

    SO2—

    (C1-C6 alkyl), and (R) —

    F, or —

    Cl, (IV) —

    CO—

    (C1-C6 alkyl)-S—

    (C1-C6 alkyl) where alkyl is optionally substituted with one, two, or three of substitutents selected from the group consisting of (A) —

    OH, (B) —

    C1-C6 alkoxy, (C) —

    C1-C6 thioalkoxy, (D) —

    CO—

    O—

    RN-8, (E) —

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (F) —

    CO—

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

    SO2—

    (C1-C8 alkyl), (H) —

    SO2—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (I) —

    NH—

    CO—

    (C1-C6 alkyl), (J) —

    NH—

    CO—

    O—

    RN-8 where RN-8 is as defined above, (K) —

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (L) —

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

    O—

    CO—

    (C1-C6 alkyl), (N) —

    O—

    CO—

    NRN-8RN-8 where the RN-8s are the same or different, (O) —

    O—

    (C1-C5 alkyl)-COOH, (P) —

    O—

    (C1-C6 alkyl optionally substitued with one, two, or three of —

    F, —

    Cl, —

    Br, or —

    I), (Q) —

    NH—

    SO2—

    (C1-C6 alkyl), and (R) —

    F, or —

    Cl, (V) —

    CO—

    CH(—

    (CH2)0-2—

    O—

    RN-10)—

    (CH2)0-2—

    RN-aryl/RN-heteroaryl), where RN-10 is selected from the group consisting of;

    (A) —

    H, (B) C1-C6 alkyl, (C) C3-C7 cycloalkyl, (D) C2-C6 alkenyl with one double bond, (E) C2-C6 alkynyl with one triple bond, (F) R1-aryl, and (G) RN-heteroaryl, or (VI) —

    CO—

    (C3-C8 cycloalkyl) where alkyl is optionally substituted with one or two substitutents selected from the group consisting of;

    (A) —

    (CH2)0-4—

    OH, (B) —

    (CH2)0-4—

    C1-C6 alkoxy, (C) —

    (CH2)0-4—

    C1-C6 thioalkoxy, (D) —

    (CH2)0-4—

    CO—

    O—

    RN-8 where RN-8 is —

    H, C1-C6 alkyl or -phenyl, (E) —

    (CH2)0-4—

    CO—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (F) —

    (CH2)0-4—

    CO—

    RN-4, (G) —

    (CH2)0-4—

    SO2—

    (C1-C8 alkyl), (H) —

    (CH2)0-4—

    SO2—

    NRN-2RN-3 where RN-2 and RN-3 are the same or different, (I) —

    (CH2)0-4—

    NH—

    CO—

    (C1-C6 alkyl), (J) —

    NH—

    CO—

    O—

    RN-8, (K) —

    (CH2)0-4-NRN-2RN-3 where RN-2 and RN-3 are the same or different, (L) —

    (CH2)0-4—

    RN-4, (M) —

    O—

    CO—

    (C1-C6 alkyl), (N) —

    O—

    CO—

    NRN-8RN-8 where RN-8 are the same or different, (O) —

    O—

    (C1-C5 alkyl)-COOH, (P) —

    O—

    (C1-C6 alkyl optionally substitued with one, two, or three of —

    F, —

    Cl, —

    Br, or —

    I), (Q) —

    NH—

    SO2—

    (C1-C6 alkyl), and (R) —

    F, or —

    Cl, wherein RC is;

    (IV) RC-heteroaryl where RC-heteroaryl is imidazolyl optionally substituted as defined above for RN-heteroaryl; and

    wherein R20 is H or C1-6 alkyl or alkenyl.

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