Imidazo [1,5-1] quinolines for treatment of anxiety and sleep disorders

Imidazo [1,5-1] quinolines for treatment of anxiety and sleep disorders

  • CN 1,135,753 A
  • Filed: 10/27/1994
  • Published: 11/13/1996
  • Est. Priority Date: 11/19/1993
  • Status: Abandoned Application
First Claim
Patent Images

1. , the imidazo of formula (I) [1,5-a] quinoline and pharmaceutically acceptable salt thereof, Wherein (I) R 3For (A)-CO-R 3-1, R wherein 3-1For (1)-H,

  • (2) C 1-C 6Alkyl, (3) C 3-C 7Cycloalkyl, (4)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (5)-(CH 2) n-CF 3, wherein n is 0-4, (6)-(CH 2) n-CHF 2, wherein n as above defines, (7)-(CH 2) n-CH 2F, wherein n as above defines, (8) phenyl that is replaced by one or two following radicals arbitrarily(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 3-2R 3-3, R wherein 3-2And R 3-3Identical or different, and be selected from following radicals (i)-H,

    (ii) C 1-C 6Alkyl, (iii) C 3-C 7Cycloalkyl, (iv)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl reaches wherein R 3-2And R 3-3Form with the nitrogen-atoms that connects and to be selected from pyrrolidyl, morpholinyl, the heterocyclic moiety of piperazinyl and piperidyl, (B)-CO-R 3-5, R wherein 3-5For (1)-H,

    (2) C 1-C 6Alkyl, (3) phenyl that is replaced by one or two following radicals arbitrarily(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 3-2R 3-3, R wherein 3-2And R 3-3As above definition, (C) aryl, wherein aryl is(1) phenyl Wherein w is 1 or 2 and R wherein 3-6For (a)-H,

    (b)-F,

    (c)-Cl,

    (d)-Br,

    (e)-I,

    (f)-CN,

    (g)-NO 2

    (h)-O-CO-R 3-1, R wherein 3-1As above definition, (i)-(CH 2) n-CF 3, wherein n as above defines (j) C 1-C 6Alkyl, (k) C 3-C 7Cycloalkyl, (l)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl, (m)-NR 3-2R 3-3, R wherein 3-2And R 3-3As above definition, (n)-(CH 2) n-O-R 3-1, R wherein 3-1As above define with n, (o)-(CH 2) n-S-R 3-1, R wherein 3-1As above define with n, (p)-(CH 2) n-CO-O-R 3-1, R wherein 3-1As above define with n, (q)-NR 3-1-CO-R 3-1, two R wherein 3-1Identical or different and as above the definition, (r)-SO 2-NR 3-2R 3-3, R wherein 3-2And R 3-3As above definition, (s)-CO-R 3-5, R wherein 3-5As above definition, (t)-NH-SO 2-CH 3

    (u)-CO-N (R 3-4) 2, R wherein 3-4Can be identical or different and be-H or C 1-C 3Alkyl, (2) 1,2 of the 5-replacement, 4-oxadiazole-3-base R wherein 3-6As above definition, (3) 1,2 of the 3-replacement, 4-oxadiazole-5-base R wherein 3-6As above definition, (4) 4-or 5-replace the De isoxazole-3-base Wherein w and R 3-6As above definition, (5) 3-or 4-replace the De isoxazole-5-base Wherein w and R 3-6As above definition;

    (II) R 4For (A)-H,

    (B) C 1-C 4Alkyl, (C)-CF 3, (III) R 5For (A) C 1-C 6Alkyl, (B) arbitrarily by one or two phenyl that following radicals replaces(1)-F,

    (2)-Cl,

    (3)-Br,

    (4)-I,

    (5)-CN,

    (6)-NO 2(7)-O-CO-R 5-1, R wherein 5-1For (a)-H,

    (b) C 1-C 6Alkyl, (c) C 3-C 7Cycloalkyl, (d)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (e)-(CH 2) b-CF 3, wherein b is 0-4, (f)-(CH 2) b-CHF 2, wherein b as above defines, (g)-(CH 2) b-CH 2F, wherein b as above defines, (8)-(CH 2) b-CF 3, wherein b as above defines, (9) C 1-C 6Alkyl, (10) C 3-C 7Cycloalkyl, (11)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl, (12)-NR 5-2R 5-3, R wherein 5-2And R 5-3Identical or different and as above the definition, (13)-(CH 2) b-O-R 5-1, R wherein 5-1With b and last definition, (14)-(CH 2) b-S-R 5-1, R wherein 5-1As above define with b, (15)-(CH 2) b-CO-O-R 5-1, R wherein 5-1As above define with b, (16)-NR 5-1-CO-R 5-1, two R wherein 5-1Identical or different and as above the definition, (17)-SO 2-NR 5-2R 5-3, R wherein 5-2And R 5-3As above definition, (18)-CO-R 5-4, R wherein 5-4For (a)-H,

    (b) C 1-C 6Alkyl, (c)-N (R 5-1) 2, two R wherein 5-1Identical or different and as above the definition, (C)-O-R 5-5, R wherein 5-5For (1)-H,

    (2) C 1-C 6Alkyl, (3) C 3-C 7Cycloalkyl, (4)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (5)-(CH 2) b-CF 3, wherein b as above defines, (6)-(CH 2) b-CHF 2, wherein b as above defines, (7)-(CH 2) b-CH 2F, wherein b as above defines, (8) arbitrarily by one or two phenyl that following radicals replaces(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 5-2R 5-3, R wherein 5-2And R 5-3As above definition, (D)-NR 5-6R 5-7, R wherein 5-6And R 5-7Identical or different and be selected from (1)-H,

    (2) C 1-C 6Alkyl, (3) C 3-C 7Cycloalkyl, (4)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl, wherein R 5-6And R 5-7Form with the nitrogen-atoms that connects and to be selected from following heterocyclic moiety (a) Wherein m is 1-4, and p is 0-4, R 5-8Be selected from following group (i)-H,

    (ii) C 1-C 6Alkyl, (iii) C 3-C 7Cycloalkyl, (iv)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (v)-(CH 2) b-CF 3, wherein b as above defines, (vi)-(CH 2) b-CHF 2, wherein b as above defines, (vii)-(CH 2) b-CH 2F, wherein b as above defines, (viii) arbitrarily by one or two phenyl that following radicals replaces(I)-F,

    (II)-Cl,

    (III)-Br,

    (IV)-I,

    (V) C 1-C 4Alkyl, (VI)-NH 2

    (VII)-CO-NH 2

    (VIII)-SO 2-NH 2

    (IX)-NH-SO 2-CH 3, (b) Wherein m and R 5-8As above definition, (c) Wherein q is 1 or 2, p and R 5-8As above definition, R 5-9Be (A)-H, (B) C 1-C 6Alkyl, (C) C 3-C 7Cycloalkyl, (D)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (E)-(CH 2) b-CF 3, wherein b as above defines, (F)-and (CH 2) b-CHF 2, wherein b as above defines, (G)-and (CH 2) b-CH 2F, wherein b as above defines, (H) arbitrarily by one or two phenyl that following radicals replaces (1)-F,

    (2)-Cl,

    (3)-Br,

    (4)-I,

    (5) C 1-C 4Alkyl, (6)-NH 2

    (d) M wherein, q, R 5-8And R 5-9As above definition, (e) R wherein 5-8And R 5-9As above definition, (f) M wherein, R 5-8And R 5-9As above definition, (IV) R 6For (A)-H,

    (B)-F,

    (C)-Br,

    (D)-I,

    (E) C 1-C 4Alkyl, (F)-CN,

    (G)-NO 2(H)-(CH 2) g-CF 3, wherein g is 0-4, (I)-(CH 2) g-OR 6-1, R 6-1For (1)-H,

    (2) C 1-C 6Alkyl, (3) arbitrarily by one or two phenyl that following radicals replaces(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 6-2R 6-3, R wherein 6-2And R 6-3Identical or different and be selected from (i)-H,

    (ii) C 1-C 6Alkyl, (iii) C 3-C 7Cycloalkyl, (iv)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl, wherein R 6-2And R 6-3Form the heterocyclic moiety that is selected from pyrrolidyl, morpholinyl, piperazinyl, piperidyl with the nitrogen-atoms that connects, (J)-CO-O-R 6-4, R wherein 6-4For (1)-H,

    (2) C 1-C 6Alkyl, (3) C 3-C 7Cycloalkyl, (4)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (5)-(CH 2) g-CF 3, wherein g as above defines, (6)-(CH 2) g-CHF 2, wherein g as above defines, (7)-(CH 2) g-CH 2F, wherein g as above defines, (8) phenyl that is replaced by one or two following radicals arbitrarily(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 6-2R 6-3, R wherein 6-2And R 6-3As above definition, (K)-CO-NR 6-2R 6-3, R wherein 6-2And R 6-3As above definition, (L)-(CH 2) g-NR 6-2R 6-3, g wherein, R 6-2And R 6-3As above definition, (M)-NH-CO-R 6-4, R wherein 6-4As above definition, (N)-SO 2-NR 6-2R 6-3, R wherein 6-2And R 6-3As above definition, (O)-N 3(V) R 7For (A)-H,

    (B)-F,

    (C)-Br,

    (C)-I,

    (E) C 1-C 4Alkyl, (F)-CN,

    (G)-NO 2

    (H)-(CH 2) g-CF 3, wherein g is 0-4, (I)-(CH 2) g-OR 7-1, R 7-1For (1)-H,

    (2) C 1-C 6Alkyl, (3) arbitrarily by one or two phenyl that following radicals replaces(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 7-2R 7-3, R wherein 7-2And R 7-3Identical or different and be selected from (i)-H,

    (ii) C 1-C 6Alkyl, (iii) C 3-C 7Cycloalkyl, (iv)-(C 1-C 4Alkyl)-C 3-C 7Cycloalkyl, wherein R 6-2And R 7-3Form the heterocyclic moiety that is selected from pyrrolidyl, morpholinyl, piperazinyl, piperidyl with the nitrogen-atoms that connects, (J)-CO-O-R 7-4, R wherein 7-4For (1)-H,

    (2) C 1-C 6Alkyl, (3) C 3-C 7Cycloalkyl, (4)-(C 1-C 6Alkyl)-C 3-C 7Cycloalkyl, (5)-(CH 2) g-CF 3, wherein g as above defines, (6)-(CH 2) g-CHF 2, wherein g as above defines, (7)-(CH 2) g-CH 2F, wherein g as above defines, (8) arbitrarily by one or two phenyl that following radicals replaces(a)-F,

    (b)-Cl,

    (c)-Br,

    (d)-I,

    (e) C 1-C 4Alkyl, (f)-NR 7-2R 7-3, R wherein 7-2And R 7-3As above definition, (K)-CO-NR 7-2R 7-3, R wherein 7-2And R 7-3As above definition, (L)-(CH 2) g-NR 7-2R 7-3, g wherein, R 7-2And R 7-3As above definition, (M)-NH-CO-R 7-4, R wherein 7-4As above definition, (N)-SO 2-NR 7-2R 7-3, R wherein 7-2And R 7-3As above definition, (O)-N 3

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