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Piperidine compounds

  • US 6,849,621 B2
  • Filed: 03/11/2002
  • Issued: 02/01/2005
  • Est. Priority Date: 03/13/2001
  • Status: Expired due to Fees
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Petitions
31
Forward Citations
3
Assignments
First Claim
Patent Images

1. A compound of the formula:

  • embedded imageor a pharmaceutically acceptable salt or solvate thereof, wherein;

    (A) R1 is selected from;

    (1) aryl;

    (2) heteroaryl;

    (3) heterocycloalkyl (4) alkyl;

    (5) —

    C(O)N(R4B)2;

    (6) cycloalkyl;

    (7) arylalkyl;

    (8) heteroarylheteroaryl;

    or (9) a group selected from;

    embedded image 

    said aryl, heteroaryl, aryl portion of arylalkyl, phenyl ring of formula II, phenyl ring of formula III, phenyl rings of formula IVB, or phenyl rings of formula IVD are optionally substituted with 1 to 3 substituents independently selected from;

    (1) halogen;

    (2) hydroxyl;

    (3) lower alkoxy;

    (4) —

    Oaryl;

    (5) —

    SR22;

    (6) —

    CF3;

    (7) —

    OCF3;

    (8) —

    OCHF2;

    (9) —

    NR4R5;

    (10) phenyl;

    (11) NO2, (12) —

    CO2R4;

    (13) —

    CON(R4)2 wherein each R4 is the same or different;

    (14) —

    S(O)2R22;

    (15) —

    S(O)2N(R20)2 wherein each R20 is the same or different;

    (16) —

    N(R24)S(O)2R22;

    (17) —

    CN;

    (18) —

    CH2OH;

    (19) —

    OCH2CH2OR22;

    (20) alkyl;

    (21) substituted phenyl wherein said phenyl has 1 to 3 substituents independently selected from alkyl, halogen, —

    CN, —

    NO2, —

    OCHF2, —

    Oalkyl;

    (22) —

    Oalkylaryl wherein said aryl group is optionally substituted with 1 to 3 independently selected halogens;

    or (23) phenyl;

    (B) X is selected from alkyl or —

    S(O)2—

    ;

    (C) Y is selected from —

    C(O)—

    , —

    C(S)—

    , —

    (CH2)q—

    , or —

    NR4C(O)—

    ;

    with the proviso that;

    when M1 is N, then Y is not —

    NR4C(O)—

    ;

    (D) M1 is C or N and M2 is C;

    (E) Z is selected from;

    C1-C6 alkyl, —

    SO2—

    , —

    C(O)—

    or —

    C(O)NR4—

    ;

    (F) R2 is selected from;

    (1) a six-membered heteroaryl ring having 1 or 2 heteroatoms independently selected from N or N—

    O, with the remaining ring atoms being carbon;

    (2) a five-membered heteroaryl ring having 1 to 3 heteroatoms selected from nitrogen, oxygen, or sulfur with the remaining ring atoms being carbon;

    or (3) an alkyl group;

    (4) phenyl or substituted phenyl wherein said substituted phenyl is substituted with 1 to 3 substituents independently selected from;

    halogen, —

    Oalkyl, —

    OCF3, —

    CF3, —

    CN, —

    NO2, —

    NHC(O)CH3, or —

    O(CH2)qN(R10A)2;

    (5) —

    N(R11A)2 wherein each R11A is independently selected from;

    H, alkyl or aryl;

    (6) a group of the formula;

    embedded image(7) a heteroarylheteroaryl group;

    said five membered heteroaryl ring ((F)(2) above) or six-membered heteroaryl ring ((F)(1) above) is optionally substituted with 1 to 3 substituents selected from;

    (a) halogen;

    (b) hydroxyl;

    (c) lower alkyl;

    (d) lower alkoxy;

    (e) —

    CF3;

    (f) —

    NR4R5;

    (g) phenyl;

    (h) —

    NO2;

    (i) —

    C(O)N(R4)2 (wherein each R4 is the same or different);

    (j) —

    C(O)2R4;

    or (k) phenyl substituted with 1 to 3 substituents independently selected from;

    halogen, —

    Oalkyl, —

    OCF3, —

    CF3, —

    CN, —

    NO2 or —

    O(CH2)qN(R10A)2;

    provided that when M1 is N and X is —

    S(O)2—

    , R2 is a six-membered heteroaryl ring substituted with —

    NR4R5;

    (G) R3 is is selected from;

    (1) aryl;

    (2) heteroaryl;

    (3) heterocycloalkyl (4) alkyl;

    or (5) cycloalkyl;

    wherein said aryl or heteroaryl R3 groups is optionally substituted with 1 to 3 substituents independently selected from;

    (a) halogen;

    (b) hydroxyl;

    (c) lower alkoxy;

    (d) —

    Oaryl;

    (e) —

    SR22;

    (f) —

    CF3;

    (g) —

    OCF3;

    (h) —

    OCHF2;

    (i) —

    NR4R5;

    (j) phenyl;

    (k) —

    NO2, (l) —

    CO2R4;

    (m) —

    CON(R4)2 wherein each R4 is the same or different;

    (n) —

    S(O)2R22;

    (o) —

    S(O)2N(R20)2 wherein each R20 is the same or different;

    (p) —

    N(R24)S(O)2R22;

    (q) —

    CN;

    (r) —

    CH2OH;

    (s) —

    OCH2CH2OR22;

    or (t) alkyl;

    (H) R4 is selected from;

    (1) hydrogen;

    (2) C1-C6 alkyl;

    (3) cycloalkyl;

    (4) cycloalkylalkyl;

    (5) heterocycloalkylalky;

    (6) bridged bicyclic cycloalkyl ring;

    (7) aryl having a fused heterocycloalkyl ring bound to said aryl ring;

    (8) aryl;

    (9) arylalkyl;

    (10) alkylaryl;

    (11) —

    (CH2)dCH(R12A)2 wherein d is 1 to 3, and each R12A is independently selected from phenyl or substituted phenyl, said substituted phenyl being substituted with 1 to 3 substituents independently selected from;

    halogen, —

    Oalkyl, —

    OCF3, —

    CF3, —

    CN, or —

    NO2;

    (12) heterocycloalkylheteroaryl;

    or (13) —

    (C1 to C6)alkylene-O—

    R22;

    wherein the aryl R4 group, the aryl portion of the arylalkyl R4 group, or the aryl portion of the alkylaryl R4 group is optionally substituted with 1 to 3 substituents independently selected from;

    (a) halogen;

    (b) hydroxyl;

    (c) lower alkyl;

    (d) lower alkoxy;

    (e) —

    CF3;

    (f) —

    N(R20)(R24), (g) phenyl;

    (h) —

    NO2;

    (i) —

    C(O)N(R20)2 (wherein each R20 is the same or different), (j) —

    C(O)R22;

    (i) —

    (CH2)k-cycloalkyl;

    (j) —

    (CH 2)q-aryl;

    or (k) —

    (CH2)m—

    OR22;

    (I) each R4B is independently selected from;

    H, heteroaryl, alkyl, alkenyl, a group of the formula embedded image 

    arylalkyl, or arylalkyl wherein the aryl moiety is substitued with 1-3 substituents independently selected from;

    halogen;

    (J) R5 is selected from;

    hydrogen, C1-C6 alkyl, —

    C(O)R20, —

    C(O)2R20, —

    C(O)N(R20)2 (wherein each R20 is the same or different);

    (K) each R10A is independently selected from H or C1 to C6 alkyl, or each R10A, taken together with the nitrogen atom to which they are bound, forms a 4 to 7 membered heterocycloalkyl ring;

    (L) R12 is (1) selected from alkyl, hydroxyl, alkoxy, or fluoro, provided that when R12 is hydroxy or fluoro then R12 is not bound to a carbon adjacent to a nitrogen;

    or (2) R12 forms an alkyl bridge from one ring carbon to another ring carbon;

    (M) R13 is (1) selected from alkyl, hydroxyl, alkoxy, or fluoro, provided that when R13 is hydroxy or fluoro then R13 is not bound to a carbon adjacent to a nitrogen;

    or (2) R13 forms an alkyl bridge from one ring carbon to another ring carbon;

    (N) R20 is selected from hydrogen, alkyl, or aryl, wherein said aryl group is optionally substituted with from 1 to 3 groups independently selected from;

    halogen, —

    CF3, —

    OCF3, hydroxyl, or methoxy;

    or when two R20 groups are present, said two R20 groups taken together with the nitrogen to which they are bound form a five or six membered heterocyclic ring;

    (O) R22 is selected from;

    heterocycloalkyl, alkyl or aryl, wherein said aryl group is optionally substituted with 1 to 3 groups independently selected from halogen, —

    CF3, —

    OCF3, hydroxyl, or methoxy;

    (P) R24 is selected from;

    hydrogen, alkyl, —

    SO2R22, or aryl, wherein said aryl group is optionally substituted with 1 to 3 groups independently selected from halogen, —

    CF3, —

    OCF3, hydroxyl, or methoxy;

    (Q) a is 0 to 2;

    (R) b is 0 to 2;

    (S) k is 1 to 5;

    (T) m is 2 to 5;

    (U) n is 1, 2 or 3 with the proviso that when M1 is N, then n is not 1;

    (V) p is 2;

    (W) q is 1 to 5; and

    (X) r is 1.

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