US2023142119A1PendingUtilityA1
Tetracyclic compound
Assignee: CHUGAI PHARMACEUTICAL CO LTDPriority: Jun 10, 2009Filed: Jul 8, 2022Published: May 11, 2023
Est. expiryJun 10, 2029(~2.9 yrs left)· nominal 20-yr term from priority
Inventors:Kazutomo KinoshitaKohsuke AsohNoriyuki FuruichiToshiya ItoHatsuo KawadaNobuya IshiiHiroshi SakamotoWoosang HongMinjeong ParkYoshiyuki OnoYasuharu KatoKenji MorikamiTakashi EmuraNobuhiro Oikawa
A61K 31/496C07D 403/04A61K 31/5377C07D 333/76C07D 307/92C07D 409/12C07D 405/14A61P 43/00A61P 25/00C07D 405/12C07D 307/77A61P 35/00C07D 471/10A61K 31/4178A61K 31/404C07D 209/56A61P 35/04C07D 401/12A61K 31/4439C07D 413/14A61P 25/24C07D 209/88C07D 471/04C07D 307/78C07D 401/06C07D 401/14C07D 403/12C07H 15/26C07D 333/52C07D 401/04A61K 31/454C07D 491/107C07F 7/0834A61P 35/02A61K 31/343A61K 31/403A61K 31/7056A61K 31/506A61K 31/541C07D 209/58A61P 25/28C07D 333/50
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Claims
Abstract
A compound represented by the general Formula (I) below, or a salt or solvate thereof, which is useful as an ALK inhibitor, and is useful for prophylaxis or treatment of a disease accompanied by abnormality in ALK, for example, cancer, cancer metastasis, depression or cognitive function disorder:(meanings of the symbols that are included in the formula are as given in the specification).
Claims
exact text as granted — not AI-modified1 .- 16 . (canceled)
17 . A compound or salt or solvate thereof represented by Formula (I):
wherein,
A 1 , A 2 , A 3 , A 4 , A 7 , A 8 , A 9 and A 10 all represent C, or any one of A 2 , A 3 , A 4 , A 7 , A 8 and A 9 represents N (with the proviso that, when it represents N, no substituent group exists therefor) and remaining ones represent C;
A 5 is selected from NR 5 , O and S;
R 1 and R 10 each independently represent [1] a hydrogen atom, [2] a cyano group, [3] a halogen atom or [4] a 4- to 10-membered heterocycloalkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s);
R 2 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group,
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a cyano group,
(6) a halogen atom,
(7) a (C 1-8 alkyl) m2 -amino group which may be substituted by C 1-8 alkylsulfonyl group(s),
m2: 0˜2, and
(8) a nitro group;
R 3 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by [1] halogen atom(s), [2] hydroxy group(s) or [3] C 1-8 alkoxy group(s),
(3) a C 6-10 aryl group,
(4) a cyano group,
(5) a C 1-8 alkanoyl group which may be substituted by C 6-10 aryl group(s),
(6) a (C 1-8 alkyl) m3a -aminocarbonyl group which may be substituted by one or more R 3A ,
R 3A : [1] a C 6-10 aryl group, [2] a C 1-8 alkoxy group, [3] a 5- to 14-membered heteroaryl group, or [4] a C 6-10 arylsulfonyl group,
m3a: 0˜2,
(7) a hydroxycarbonyl group,
(8) a C 1-8 alkoxycarbonyl group which may be substituted by [1] hydroxy group(s) or [2]C 1-8 alkoxy group(s),
(9) a halogen atom,
(10) a (C 1-8 alkyl) m3b -amino group which may be substituted by C 6-10 aryl group(s),
m3b: 0˜2,
(11) a C 1-8 alkylcarbonyl (C 0-8 alkyl) amino group which may be substituted by [1] C 6-10 aryl group(s) or [2] C 6-10 aryloxy group(s),
(12) a C 6-10 arylcarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s),
(13) a (C 1-8 alkyl) m3c -aminocarbonyl (C 0-8 alkyl) amino group which may be substituted by C 6-10 aryl group(s),
m3c: 0˜2,
(14) a nitro group,
(15) a hydroxy group,
(16) a C 1-8 alkoxy group which may be substituted by one or more R 3B ,
R 3B : [1] a hydroxy group, [2] a C 1-8 alkoxy group, [3] a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl group, [4] a (C 1-8 alkyl) m3d -amino group, or [5] a halogen atom,
m3d: 0˜2,
(17) a 4- to 10-membered heterocycloalkyloxy group,
(18) a 5- to 14-membered heteroaryloxy group,
(19) a (C 1-8 alkyl) m3e -aminocarbonyloxy group which may be substituted by C 6-10 aryl group(s)
m3e: 0˜2,
(20) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group,
(21) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s),
(22) a C 1-8 alkylthio group,
(23) a C 1-8 alkylsulfonyl group which may be substituted by C 6-10 aryl group(s),
(24) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by C 1-8 alkoxy group(s),
(25) a C 1-8 alkoxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkoxy group(s),
(26) a C 6-10 aryloxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s),
(27) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl (C 0-8 alkyl) amino group which may be substituted by one or more R 3C ,
R 3C : [1] a C 1-8 alkyl group which may be substituted by halogen atom(s), or [2] a C 1-8 alkoxy group,
(28) a C 3-8 cycloalkyl (C 0-8 alkyl) aminocarbonyloxy group, and
(29) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyloxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkyl group and [2] a C 1-8 alkoxy group;
R 4 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by halogen atom(s),
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a C 3-8 cycloalkyl group,
(6) a cyano group,
(7) an aminocarbonyl group,
(8) a (C 1-8 alkyl) m4a -aminocarbonyl group,
m4a: 1˜2,
(9) a hydroxycarbonyl group,
(10) a C 1-8 alkoxycarbonyl group,
(11) a halogen atom,
(12) a (C 1-8 alkyl) m4b -amino group,
m4b: 0˜2,
(13) a hydroxy group, and
(14) a C 1-8 alkoxy group which may be substituted by hydroxy group(s);
R 5 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 5A ,
R 5A : [1] a hydroxycarbonyl group, [2] a C 1-8 alkoxycarbonyl group, [3] a hydroxy group, [4] a C 1-8 alkoxy group, [5] a (C 1-8 alkyl)m5-amino group, [6] a C 6-10 aryl group, or [7] a C 1-8 alkylthio group,
m5: 0˜2,
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a C 3-8 cycloalkyl group, and
(6) a C 1-8 alkylsulfonyl group;
R 6 and R 6′ are each independently selected from the group consisting of:
(1) a C 1-8 alkyl group which may be substituted by halogen atom(s),
(2) a C 2-8 alkenyl group, and
(3) a C 2-8 alkynyl group; or
R 6 and R 6′ are taken together with the carbon atoms to which they are bound to form:
(4) a C 3-8 cycloalkyl group, or
(5) a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl C 6-10 aryl sulfonyl group(s) which may be substituted by C 1-8 alkyl group(s);
R 7 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a halogen atom,
(3) a C 1-8 alkoxy group which may be substituted by one or more R 7A ,
R 7A : [1] a (C 1-8 alkyl) m7a -amino group, [2] a hydroxy, [3] a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl group(s),
m7a: 0˜2,
(4) a C 1-8 alkylsulfonyl group,
(5) a nitro group, and
(6) a hydroxyl group;
R 8 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 8A ,
R 8A : [1] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R8A 1 , [2] a (C 1-8 alkyl) m8a -amino group which may be substituted by a halogen atom, or [3] a hydroxy group,
m8a: 0˜2,
R 8A1 : [1] a C 1-8 alkyl group, [2] a C 1-8 alkylsulfonyl group, [3] a (C 1-8 alkyl) m8b -aminosulfonyl group, [4] an oxo group, [5] a C 1-8 alkoxycarbonyl, or [6] a C 1-8 alkoxycarbonyl (C 0-8 alkyl) aminosulfonyl,
m8b: 0˜2,
(3) a C 2-8 alkenyl group,
(4) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B ,
R 8B :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8B1 ,
<2> a C 2-8 alkynyl group,
<3> a C 2-8 alkynyl group,
<4> a C 3-8 cycloalkyl group which may be substituted by [1] cyano group(s) or [2] C 1-8 alkyl group(s),
<5> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B2 ,
<6> a C 1-8 alkoxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkoxy group and [2] a C 3-8 cycloalkyl group,
<7> a C 1-8 alkoxycarbonyl group,
<8> a C 1-8 alkylsulfonyl group,
<9> a 5- to 14-membered heteroarylsulfonyl group,
<10> an oxo group,
<11> a cyano group,
<12> a C 1-8 alkanoyl group which may be substituted by one or more R 8B3 ,
<13> a C 3-8 cycloalkylcarbonyl group,
<14> a (C 1-8 alkyl) m8c -aminosulfonyl group,
<15> a C 1-8 alkylsulfonyl (C 0-8 alkyl) amino group,
<16> a (C 1-8 alkyl) m8a -amino group which may be substituted by one or more R 8B4 ,
<17> a hydroxy group,
<18> a (C 1-8 alkyl) m8e -aminocarbonyl group, or
<19> a C 1-8 alkoxycarbonyl (C 0-8 alkyl) amino group
m8c: 0˜2
m8d: 0˜2
m8e: 0˜2
R 8B1 : [1] a C 3-8 cycloalkyl group, [2] a hydroxy group, or [3] a C 1-8 alkoxy group(s),
R 8B2 : [1] a halogen atom, [2] a C 1-8 alkyl group, [3] an oxo group, [4] a hydroxy group, or [5] a deuterium atom,
R 8B3 : a (C 1-8 alkyl) m8f -amino group,
m8f: 0˜2,
R 8B4 : [1] a C 3-8 cycloalkyl group, or [2] a hydroxy group,
(5) a 5- to 14-membered heteroaryl group which may be substituted by a C 1-8 alkyl group,
(6) a (C 1-8 alkyl) m8g -aminocarbonyl group which may be substituted by one or more R 8C ,
m8g: 0˜2,
R 8C : [1] a hydroxy group, [2] a (C 1-8 alkyl) m8h -amino group which may be substituted by substituent(s) selected from the group consisting of <1> a (C 1-8 alkyl) m8i -aminosulfonyl group,
<2> a C 1-8 alkylsulfonyl group, <3> a C 1-8 alkoxycarbonyl group and <4> a C 1-8 alkoxycarbonyl(C 0-8 alkyl) aminosulfonyl group, [3] a C 1-8 alkylsulfonyl group, or [4] a C 1-8 alkoxy group which may be substituted by a hydroxy group,
m8h: 0˜2,
m8i: 0˜2,
(7) a 4- to 10-membered heterocycloalkyl (C 0-8 alkyl) aminocarbonyl group which may be substituted by oxo group(s),
(8) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8D ,
R 8D : [1] a C 1-8 alkyl group which may be substituted by one or more R 8D1 , [2] a hydroxy group, [3] a C 1-8 alkylsulfonyl group, or [4] a C 1-8 alkoxycarbonyl group,
R 8D1 : [1] a hydroxy group, or [2] a C 1-8 alkoxy group,
(9) a hydroxycarbonyl group,
(10) a C 0-8 alkoxy (C 0-8 alkyl) aminocarbonyl group which may be substituted by hydroxy group(s),
(11) a halogen atom,
(12) a (C 1-8 alkyl) m8j -amino group which may be substituted by one or more R 8H ,
m8j: 0˜2,
R 8H : [1] a hydroxy group, or [2] a 4- to 10-membered heterocycloalkyl group,
(13) a hydroxyl group,
(14) a C 1-8 alkoxy group which may be substituted by one or more R 8E ,
R 8E :
<1> a hydroxy group,
<2> halogen atom,
<3> a hydroxycarbonyl group,
<4> a C 1-8 alkoxycarbonyl group,
<5> a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8E1 ,
<6> a (C 1-8 alkyl) m8k1 -amino group which may be substituted by one or more R 8E2 ,
m8k1: 0˜2,
<7> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8E3 ,
<8> a 5- to 14-membered heteroaryl group,
<9> a (C 1-8 alkyl) m8k2 -aminocarbonyl group which may be substituted by one or more R 8E6 ,
m8k2: 0˜2,
<10> a C 1-8 alkoxy group which may be substituted by one or more R 8E7 ,
<11> a C 1-8 alkylthio group,
<12> a C 1-8 alkylsulfinyl group,
<13> a C 1-8 alkylsulfonyl group,
R 8E1 :
<1> a C 1-8 alkoxycarbonyl group,
<2> a C 1-8 alkanoyl group,
<3> a C 1-8 alkylsulfonyl group,
<4> a (C 1-8 alkyl) m8k3 -aminosulfonyl group,
m8k3: 0˜2, or
<5> a 4- to 10-membered heterocycloalkyl group,
R 8E2 :
<1> a hydroxy group,
<2> a C 1-8 alkoxycarbonyl group which may be substituted by halogen atom(s),
<3> a C 3-8 cycloalkyl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by hydroxy group(s),
<4> a C 1-8 alkanoyl group which may be substituted by substituent(s) selected from the group consisting of [1] a (C 1-8 alkyl) m8k4 -amino group and [2] a halogen atom(s),
m8k4: 0˜2,
<5> a (C 1-8 alkyl) m8k5 -aminocarbonyl group,
m8k5: 0˜2,
<6> a C 1-8 alkylsulfonyl group,
<7> a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s),
<8> a (C 1-8 alkyl) m8k6 -aminosulfonyl group which may be substituted by C 1-8 alkoxycarbonyl group(s),
m8k6: 0˜2, or
R 8E3 :
<1> a C 1-8 alkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a hydroxy group and [2] a C 1-8 alkylcarbonyloxy group,
<2> a C 1-8 alkylcarbonyloxy group,
<3> a hydroxy group,
<4> a C 3-8 cycloalkyl group,
<5> a C 1-8 alkoxy group,
<6> a C 1-8 alkoxycarbonyl group,
<7> a C 1-8 alkylsulfonyl group,
<8> a (C 1-8 alkyl) m8k8 -aminocarbonyl group
m8k8: 0˜2,
<9> a C 1-8 alkanoyl group which may be substituted by hydroxy group(s),
<10> an oxo group, or
<11> a 4- to 10-membered heterocycloalkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkanoyl group, [2] a C 1-8 alkoxycarbonyl group and [3] a C 1-8 alkylsulfonyl group,
R 8E6 :
<1> a C 2-8 alkenylcarbonyloxy group,
<2> a hydroxy group,
<3> a cyano group,
<4> a (C 1-8 alkyl) m8k9 -amino group which may be substituted by hydroxy group(s)
m8k9: 0˜2,
<5> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
<6> a C 1-8 alkylcarbonyloxy group,
<7> a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl group(s), or
<8> a 5- to 14-membered heteroaryl group,
R 8E7 :
<1> a hydroxy group, or
<2> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
(15) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by one or more R 8F ,
R 8F :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8F1 ,
<2> a C 3-8 cycloalkyl group,
<3> a C 1-8 alkanoyl group which may be substituted by halogen atom(s),
<4> a C 1-8 alkylcarbonyloxy group,
<5> a C 1-8 alkoxycarbonyl group,
<6> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8F2 ,
<7> a C 1-8 alkyl sulfonyl group,
<8> a hydroxy group, or
[9] a C 6-10 aryl group,
R 8F1 : [1] a hydroxy group, [2] a C 1-8 alkoxy group, or [3] a halogen atom,
R 8F2 : [1] a 4- to 10-membered heterocycloalkyl group, [2] a C 1-8 alkoxycarbonyl group, or [3] a C 1-8 alkylsulfonyl group,
(16) a 5- to 14-membered heteroaryloxy group,
(17) a 4- to 10-membered heterocycloalkylcarbonyloxy group,
(18) a (C 1-8 alkyl) m8l1 -aminosulfonyloxy group,
m8l1: 0˜2,
(19) a C 1-8 alkyl thio group which may be substituted by [1] (C 1-8 alkyl) m8l2 -amino group(s), [2] hydroxy group(s) or [3] hydroxycarbonyl group(s),
m8l2: 0˜2,
(20) a C 1-8 alkylsulfonyl group which may be substituted by one or more R 8G ,
R 8G : [1] a hydroxycarbonyl group, [2] a hydroxy group, or [3] a (C 1-8 alkyl) m8l3 -amino group,
m8l3: 0˜2,
(21) a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyloxy group which may be substituted by C 1-8 alkyl group(s),
(22) a C 2-8 alkenyloxy group, and
(23) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s);
R 9 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 9A ,
R 9A : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9A1 , [3] a hydroxy group, [4] a C 1-8 alkoxy group, or [5] a hydroxycarbonyl group,
R 9A1 : [1] a C 1-8 alkyl group, [2] a C 3-8 cycloalkyl group, or [3] a 4- to 10-membered heterocycloalkyl group,
(3) a C 2-8 alkenyl group which may be substituted by one or more R 9B ,
R 9B : [1] a (C 1-8 alkyl) m9a -amino group, [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more group R 9B1 ,
R 9B1 : [1] a C 3-8 cycloalkyl group, or [2] a 4- to 10-membered heterocycloalkyl group,
m9a: 0˜2,
(4) a C 2-8 alkynyl group which may be substituted by one or more R 9C ,
R 9C : [1] a C 1-8 alkoxy group, [2] a (C 1-8 alkyl) m9b -amino group which may be substituted by C 6-10 aryl group(s), [3] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9C1 , [4] a C 3-8 cycloalkyl group, [5] a hydroxy group, [6] a hydroxycarbonyl group, or [7] a C 1-8 alkyloxycarbonyl group,
m9b: 0˜2,
R 9C1 : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group, or [3] an oxo group,
(5) a C 3-8 cycloalkyl group,
(6) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9D ,
R 9D : [1] a C 1-8 alkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s), [2] a C 3-8 cycloalkyl group, [3] a 4- to 10-membered heterocycloalkyl group, or [4] a C 1-6 alkylsulfonyl group, or [5] a C 1-8 alkoxycarbonyl group,
(7) a C 6-10 aryl group which may be substituted by one or more R 9E ,
R 9E : [1] a halogen atom, [2] a hydroxy group, [3] a hydroxycarbonyl group, or [4] a C 1-8 alkyl group which may be substituted by hydroxy group(s), or [5] a C 1-8 alkoxy group,
(8) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s),
(9) a cyano group,
(10) a C 1-8 alkanoyl group,
(11) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by C 1-8 alkyl group(s),
(12) a halogen atom,
(13) a (C 1-8 alkyl) m9c -amino group which may be substituted by one or more R 9F ,
m9c: 0˜2,
(14) a C 1-8 alkylcarbonyl(C 0-8 alkyl)amino group which may be substituted by (C 1-8 alkyl) m9d -amino group(s),
m9d: 0˜2,
(15) a C 1-8 alkylsulfonyl(C 0-8 alkyl)amino group,
(16) a (C 1-8 alkyl) m9e -aminosulfonyl(C 0-8 alkyl)amino group,
m9e: 0˜2,
(17) a nitro group,
(18) a hydroxy group,
(19) a C 1-8 alkoxy group which may be substituted by one or more R 9G ,
R 9G : [1] a hydroxy group, [2] a hydroxycarbonyl group, [3] a C 6-10 aryl group which may be substituted by C 1-8 alkoxy group(s), [4] a (C 1-8 alkyl) m9g1 -amino group, [5] a C 1-8 alkoxy group which may be substituted by one or more R 9G1 , [6] a 5- to 14-membered heteroaryl group, or [7] a 4- to 10-membered heterocycloalkyloxy group which may be substituted by C 1-8 alkyl group(s),
m9g1: 0˜2,
R 9G1 : [1] a C 1-8 alkoxy group, or [2] a hydroxycarbonyl group,
(20) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by [1] 4-to 10-membered heterocycloalkyl group(s), or [2] C 1-8 alkoxycarbonyl group(s),
(21) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s),
(22) a C 1-8 alkylthio group which may be substituted by (C 1-8 alkyl) m9f -amino group(s),
m9f: 0˜2,
(23) a C 1-8 alkylsulfonyl group which may be substituted by (C 1-8 alkyl) m9g -amino group(s),
m9g: 0˜2,
(24) a (C 1-8 alkyl) m9h -aminosulfonyl group,
m9h: 0˜2,
(25) a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s), and
(26) a hydroxycarbonyl group.
18 . The compound according to claim 17 , or a salt or solvate thereof, wherein R 3 is a cyano group or a halogen atom.
19 . The compound according to claim 17 , or a salt or solvate thereof, wherein A 5 is NR 5 and R 5 is a hydrogen atom.
20 . The compound according to claim 17 , or a salt or solvate thereof, wherein all of the A 1 , A 2 , A 3 , A 4 , A 7 , A 8 , A 9 and A 10 are a carbon atom.
21 . The compound according to claim 17 , or a salt or solvate thereof, wherein: A 1 , A 2 , A 3 , A 4 , A 7 , A 8 , A 9 and A 10 all represent C, or any one of A 2 , A 3 , A 4 , A 7 , A 8 and A 9 represents N (with the proviso that, when it represents N, no substituent group exists therefor) and remaining ones represent C;
A 5 is selected from NR 5 , O and S; R 1 represents [1] a hydrogen atom, [2] a cyano group, or [3] a halogen atom; R 2 is selected from the group consisting of: (1) a hydrogen atom, (2) a C 1-8 alkyl group, (3) a cyano group, (4) a halogen atom, and (5) a (C 1-8 alkyl) m2 -amino group which may be substituted by C 1-8 alkylsulfonyl group(s), m2: 0˜2; R 3 is selected from the group consisting of: (1) a hydrogen atom, (2) a C 1-8 alkyl group which may be substituted by halogen atom(s), (3) a cyano group, (4) a (C 1-8 alkyl) m3a -aminocarbonyl group which may be substituted by one or more R 3A , R 3A : [1] a C 6-10 aryl group, [2] a C 1-8 alkoxy group, [3] a 5- to 14-membered heteroaryl group, or [4] a C 6-10 aryl sulfonyl group, m3a: 0˜2, (5) a hydroxycarbonyl group, (6) a C 1-8 alkoxycarbonyl group which may be substituted by hydroxy group(s), (7) a halogen atom, (8) a (C 1-8 alkyl) m3b -amino group which may be substituted by C 6-10 aryl group(s), m3b: 0˜2, (9) a C 1-8 alkylcarbonyl (C 0-8 alkyl) amino group which may be substituted by [1] C 6-10 aryl group(s) or [2] C 6-10 aryloxy group(s), (10) a C 6-10 arylcarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s), (11) a nitro group, (12) a hydroxy group, (13) a C 1-8 alkoxy group which may be substituted by one or more R 3B , R 3B : [1] a hydroxy group, [2] a C 1-8 alkoxy group, [3] a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl group, [4] a (C 1-8 alkyl) m3d -amino group, or [5] a halogen atom, m3d: 0˜2, (14) a 4- to 10-membered heterocycloalkyloxy group, (15) a 5- to 14-membered heteroaryloxy group, (16) a (C 1-8 alkyl) m3e -aminocarbonyloxy group which may be substituted by C 6-10 aryl group(s), m3e: 0˜2, (17) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group, (18) a C 1-8 alkylthio group, (19) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by C 1-8 alkoxy group(s), (20) a C 1-8 alkoxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkoxy group(s), (21) a C 6-10 aryloxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s), (22) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkoxy group(s), (23) a C 3-8 cycloalkyl (C 0-8 alkyl) aminocarbonyloxy group, and (24) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyloxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkyl group and [2] a C 1-8 alkoxy group; R 4 is selected from the group consisting of: (1) a hydrogen atom, (2) a C 1-8 alkyl group which may be substituted by halogen atom(s), (3) a C 3-8 cycloalkyl group, (4) a cyano group, (5) an aminocarbonyl group, (6) a hydroxycarbonyl group, (7) a halogen atom, (8) a (C 1-8 alkyl) m4b -amino group, m4b: 0˜2, (9) a hydroxy group, and (10) a C 1-8 alkoxy group which may be substituted by hydroxy group(s); R 5 is selected from the group consisting of: (1) a hydrogen atom, (2) a C 1-8 alkyl group which may be substituted by one or more R 5A , R 5A : [1] a hydroxycarbonyl group, [2] a C 1-8 alkoxycarbonyl group, [3] a hydroxy group, [4] a C 1-8 alkoxy group, [5] a (C 1-8 alkyl)m5-amino group, or [6] a C 1-8 alkylthio group, m5: 0˜2, and (3) a C 1-8 alkylsulfonyl group; R 6 and R 6′ are each independently: (1) a C 1-8 alkyl group, or R 6 and R 6′ are taken together with the carbon atoms to which they are bound to form, (2) a C 3-8 cycloalkyl group, or (3) a 4- to 10-membered heterocycloalkyl group; R 7 is selected from the group consisting of: (1) a hydrogen atom, (2) a halogen atom, and (3) a C 1-8 alkoxy group which may be substituted by one or more R 7A , R 7A : [1] a (C 1-8 alkyl) m7a -amino group, or [2] a hydroxy group, m7a: 0˜2; R 8 is selected from the group consisting of: (1) a hydrogen atom, (2) a C 1-8 alkyl group which may be substituted by one or more R 8A , R 8A : [1] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8A1 , [2] a (C 1-8 alkyl) m8a -amino group which may be substituted by a halogen atom, or [3] a hydroxy group, m8a: 0˜2, R 8A1 : [1] a C 1-8 alkyl group, [2] a C 1-8 alkylsulfonyl group, [3] a (C 1-8 alkyl)m8b-aminosulfonyl group, or [4] an oxo group, m8b: 0˜2, (3) a C 2-8 alkenyl group, (4) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B , R 8B :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8B1 ,
<2> a C 2-8 alkynyl group,
<3> a C 3-8 cycloalkyl group which may be substituted by [1] cyano group(s) or [2] C 1-8 alkyl group(s),
<4> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B2 ,
<5> a C 1-8 alkoxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkoxy group and [2] a C 3-8 cycloalkyl group,
<6> a C 1-8 alkylsulfonyl group,
<7> an oxo group,
<8> a cyano group,
<9> a C 1-8 alkanoyl group which may be substituted by one or more R 8B3 ,
<10> a C 3-8 cycloalkylcarbonyl group,
<11> a (C 1-8 alkyl) m8c -aminosulfonyl group,
<12> a C 1-8 alkylsulfonyl (C 0-8 alkyl) amino group,
<13> a (C 1-8 alkyl) m8d -amino group which may be substituted by one or more R 8B4 ,
<14> a hydroxy group, or
<15> a (C 1-8 alkyl) m8e -aminocarbonyl group,
m8c: 0˜2,
m8d: 0˜2,
m8e: 0˜2,
R 8B1 : [1] a C 3-8 cycloalkyl group, [2] a hydroxy group, or [3] C 1-8 alkoxy group which may be substituted by C 1-8 alkoxy group(s),
R 8B2 : [1] a halogen atom, [2] a C 1-8 alkyl group, [3] an oxo group, or [4] a hydroxy group,
R 8B3 : a (C 1-8 alkyl) m8f -amino group,
m8f: 0˜2,
R 8B4 : [1] a C 3-8 cycloalkyl group, or [2] a hydroxy group,
(5) a 5- to 14-membered heteroaryl group which may be substituted by a C 1-8 alkyl group,
(6) a (C 1-8 alkyl) m8g -aminocarbonyl group which may be substituted by one or more R 8C ,
m8g: 0˜2,
R 8C :[1] a hydroxy group, [2] a (C 1-8 alkyl) m8h -amino group which may be substituted by substituent(s) selected from the group consisting of <1> a (C 1-8 alkyl) m8i -aminosulfonyl group and <2> a C 1-8 alkylsulfonyl group, or [3] a C 1-8 alkylsulfonyl group,
m8h: 0˜2,
m8i: 0˜2,
(7) a 4- to 10-membered heterocycloalkyl (C 0-8 alkyl) aminocarbonyl group which may be substituted by oxo group(s),
(8) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8D ,
R 8D : [1] a C 1-8 alkyl group which may be substituted by one or more R 8D1 , [2] a hydroxy group, or [3] a C 1-8 alkylsulfonyl group,
R 8D1 : [1] a hydroxy group, or [2] a C 1-8 alkoxy group,
(9) a hydroxycarbonyl group,
(10) a C 0-8 alkoxy (C 0-8 alkyl) aminocarbonyl group which may be substituted by hydroxy group(s),
(11) a halogen atom,
(12) a (C 1-8 alkyl) m8j -amino group which may be substituted by 4- to 10-membered heterocycloalkyl group(s),
m8j: 0˜2,
(13) a hydroxyl group,
(14) a C 1-8 alkoxy group which may be substituted by one or more R 8E ,
R 8E :
<1> a hydroxy group,
<2> a C 1-8 alkoxycarbonyl group,
<3> a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8E1 ,
<4> a (C 1-8 alkyl) m8k1 -amino group which may be substituted by one or more R 8E2 ,
m8k1: 0˜2,
<5> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8E3 ,
<6> a 5- to 14-membered heteroaryl group,
<7> a (C 1-8 alkyl) m8k2 -aminocarbonyl group which may be substituted by one or more R 8E6 ,
m8k2: 0˜2,
<8> a C 1-8 alkoxy group which may be substituted by one or more R 8E7 ,
<9> a C 1-8 alkylthio group,
<10> a C 1-8 alkylsulfinyl group, or
<11> a C 1-8 alkylsulfonyl group,
R 8E1 :
<1> a C 1-8 alkoxycarbonyl group,
<2> a C 1-8 alkanoyl group,
<3> a C 1-8 alkylsulfonyl group,
<4> a (C 1-8 alkyl) m8k3 -aminosulfonyl group
m8k3: 0˜2, or
<5> a 4- to 10-membered heterocycloalkyl group,
R 8E2 :
<1> a hydroxy group,
<2> a C 1-8 alkoxycarbonyl group,
<3> a C 3-8 cycloalkyl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by hydroxy group(s),
<4> a C 1-8 alkanoyl group which may be substituted by substituent(s) selected from the group consisting of [1] a (C 1-8 alkyl) m8k4 -amino group and [2] a halogen atom,
m8k4: 0˜2,
<5> a (C 1-8 alkyl) m8k5 -aminocarbonyl group,
m8k5: 0˜2,
<6> a C 1-8 alkylsulfonyl group,
<7> a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s),
<8> a (C 1-8 alkyl) m8k6 -aminosulfonyl group,
m8k6: 0˜2, or
R 8E3 :
<1> a C 1-8 alkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a hydroxy group and [2] a C 1-8 alkylcarbonyloxy group,
<2> a hydroxy group,
<3> a C 3-8 cycloalkyl group,
<4> a C 1-8 alkylsulfonyl group,
<5> a (C 1-8 alkyl) m8k8 -aminocarbonyl group,
m8k8: 0˜2,
<6> a C 1-8 alkanoyl group which may be substituted by hydroxy group(s),
<7> an oxo group, or
<8> a 4- to 10-membered heterocycloalkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkanoyl group, and [2] a C 1-8 alkylsulfonyl group,
R 8E6 :
<1> a C 2-8 alkenylcarbonyloxy group,
<2> a hydroxy group,
<3> a cyano group,
<4> a (C 1-8 alkyl) m8k9 -amino group which may be substituted by hydroxy group(s),
m8k9: 0˜2,
<5> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
<6> a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl group(s), or
<7> a 5- to 14-membered heteroaryl group,
R 8E7 :
<1> a hydroxy group, or
<2> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
(15) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by one or more R 8F :
R 8F :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8F1 ,
<2> a C 3-8 cycloalkyl group,
<3> a C 1-8 alkanoyl group which may be substituted by halogen atom(s),
<4> a C 1-8 alkoxycarbonyl group,
<5> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8F2 ,
<6> a C 1-8 alkyl sulfonyl group, or
<7> a hydroxy group,
R 8F1 : [1] a hydroxy group, [2] a C 1-8 alkoxy group, or [3] a halogen atom,
R 8F2 : [1] a 4- to 10-membered heterocycloalkyl group, [2] a C 1-8 alkoxycarbonyl group, or [3] a C 1-8 alkylsulfonyl group,
(16) a 5- to 14-membered heteroaryloxy group,
(17) a (C 1-8 alkyl) m8l1 -aminosulfonyloxy group,
m8l1: 0˜2,
(18) a C 1-8 alkylthio group which may be substituted by (C 1-8 alkyl) m8l2 -amino group(s),
m8l2: 0˜2,
(19) a C 1-8 alkylsulfonyl group which may be substituted by one or more R 8G ,
R 8G : [1] a hydroxycarbonyl group, [2] a hydroxy group, or [3] a (C 1-8 alkyl) m8l3 -amino group,
m8l3: 0˜2,
(20) a C 2-8 alkenyloxy group, and
(21) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s);
R 9 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 9A ,
R 9A : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9A1 , [3] a hydroxy group, or [4] a C 1-8 alkoxy group,
R 9A1 : [1] a C 1-8 alkyl group, [2] a C 3-8 cycloalkyl group, or [3] a 4- to 10-membered heterocycloalkyl group,
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group which may be substituted by one or more R 9C ,
R 9C : [1] a C 1-8 alkoxy group, [2] a (C 1-8 alkyl) m9b -amino group which may be substituted by C 6-10 aryl group(s), [3] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9C1 , [4] a C 3-8 cycloalkyl group, [5] a hydroxy group, or [6] a hydroxycarbonyl group,
m9b: 0˜2,
R 9C1 : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group, or [3] an oxo group,
(5) a C 3-8 cycloalkyl group,
(6) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9D ,
R 9D : [1] a C 1-8 alkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s), [2] a C 3-8 cycloalkyl group, [3] a 4- to 10-membered heterocycloalkyl group, or [4] a C 1-6 alkylsulfonyl group,
(7) a C 6-10 aryl group which may be substituted by one or more R 9E ,
R 9E : [1] a halogen atom, [2] a hydroxy group, [3] a hydroxycarbonyl group, or [4] a C 1-8 alkyl group which may be substituted by hydroxy group(s),
(8) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s),
(9) a cyano group,
(10) a C 1-8 alkanoyl group,
(11) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by C 1-8 alkyl group(s),
(12) a halogen atom,
(13) a (C 1-8 alkyl) m9c -amino group,
m9c: 0˜2,
(14) a C 1-8 alkylcarbonyl(C 0-8 alkyl)amino group which may be substituted by (C 1-8 alkyl) m9d -amino group(s),
m9d: 0˜2,
(15) a C 1-8 alkylsulfonyl(C 0-8 alkyl)amino group,
(16) a (C 1-8 alkyl) m9e -aminosulfonyl(C 0-8 alkyl)amino group,
m9e: 0˜2,
(17) a nitro group,
(18) a hydroxy group,
(19) a C 1-8 alkoxy group which may be substituted by one or more R 9G ,
R 9G : [1] a hydroxy group, [2] a hydroxycarbonyl group, [3] a C 6-10 aryl group which may be substituted by C 1-8 alkoxy group(s), [4] a (C 1-8 alkyl) m9g1 -amino group, [5] a C 1-8 alkoxy group which may be substituted by one or more R 9G1 , or [6] a 5- to 14-membered heteroaryl group,
m9g1: 0˜2,
R 9G1 : [1] a C 1-8 alkoxy group, or [2] a hydroxycarbonyl group,
(20) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by 4- to 10-membered heterocycloalkyl group(s),
(21) a C 1-8 alkylthio group which may be substituted by (C 1-8 alkyl) m9f -amino group(s),
m9f: 0˜2,
(22) a C 1-8 alkylsulfonyl group which may be substituted by (C 1-8 alkyl) m9g -amino group(s),
m9g: 0˜2,
(23) a (C 1-8 alkyl) m9h -aminosulfonyl group,
m9h: 0˜2, and
(24) a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s);
R 10 represents [1] a hydrogen atom, or [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s)].
22 . A compound or salt or solvate thereof, which said compound is selected from the group consisting of:
9-(4-isopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-9-prop-1-ynyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-cyclopropylethynyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-8-(4-cyclopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-chloro-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-prop-1-ynyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6,9-trimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-6,6-dimethyl-11-oxo-8-(4-pyrrolidin-1-yl-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-11-oxo-8-(4-pyrrolidin-1-yl-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-ethynyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-propyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(1-isopropyl-piperidin-4-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-isopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-cyclopropyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(2-tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-8-(4-methanesulfonyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-9-propyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; and 9-ethynyl-6,6-dimethyl-8-morpholin-4-yl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile.
23 . A medicament comprising as an active ingredient the compound according to claim 17 , or a salt or solvate thereof.
24 . An ALK inhibitor comprising as an active ingredient the compound according to claim 17 , or a salt or solvate thereof.
25 . A pharmaceutical for the prophylaxis or treatment of cancer, cancer metastasis, depression or cognitive function disorder, comprising as an active ingredient the compound according to claim 17 , or a salt or solvate thereof.
26 . A pharmaceutical composition comprising the compound according to claim 17 , or a salt or solvate thereof and a pharmaceutically acceptable carrier(s).
27 . An intermediate of Formula IIe:
wherein, A 7 to A 10 , R 6 and R 6′ are as defined in claim 17 ; PR 7 to PR 10 are the same as R 7 to R 10 that are defined in claim 1 or represent a group which can be converted to R 7 to R 10 .
28 . An intermediate of Formula IIIb:
wherein, A 1 to A 4 , A 7 to A 10 , R 6 and R 6′ are as defined in claim 17 ; PR 1 to PR 4 and PR 7 to PR 10 are the same as R 1 to R 4 and R 7 to R 10 that are defined in claim 1 or represent a group which can be converted to R 1 to R 4 and R 7 to R 10 ; PG represents a protecting group.
29 . A method of treating or preventing cancer, cancer metastasis, depression or cognitive function disorder in a subject in need thereof comprising administering an effective amount of a pharmaceutical for the treatment of cancer, cancer metastasis, depression or cognitive function disorder, comprising as an active ingredient a compound represented by Formula (I):
wherein,
A 5 is selected from NR 5 , O and S;
A 4 , A 7 , and A 9 represent CR 4 , CR 7 , and CR 9 respectively, or wherein A 4 is N and A 7 and A 9 represent CR 7 and CR 9 respectively;
R 1 and R 10 each independently represent [1] a hydrogen atom, [2] a cyano group, [3] a halogen atom or [4] a 4- to 10-membered heterocycloalkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s);
R 2 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group,
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a cyano group,
(6) a halogen atom,
(7) a (C 1-8 alkyl) m2 -amino group which may be substituted by C 1-8 alkylsulfonyl group(s),
m2: 0˜2, and
(8) a nitro group;
R 3 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by [1] halogen atom(s), [2] hydroxy group(s) or [3] C 1-8 alkoxy group(s),
(3) a C 6-10 aryl group,
(4) a cyano group,
(5) a C 1-8 alkanoyl group which may be substituted by C 6-10 aryl group(s),
(6) a (C 1-8 alkyl) m3a -aminocarbonyl group which may be substituted by one or more R 3A ,
R 3A : [1] a C 6-10 aryl group, [2] a C 1-8 alkoxy group, [3] a 5- to 14-membered heteroaryl group, or [4] a C 6-10 arylsulfonyl group,
m3a: 0˜2,
(7) a hydroxycarbonyl group,
(8) a C 1-8 alkoxycarbonyl group which may be substituted by [1] hydroxy group(s) or [2]C 1-8 alkoxy group(s),
(9) a halogen atom,
(10) a (C 1-8 alkyl) m3b -amino group which may be substituted by C 6-10 aryl group(s),
m3b: 0˜2,
(11) a C 1-8 alkylcarbonyl (C 0-8 alkyl) amino group which may be substituted by [1] C 6-10 aryl group(s) or [2] C 6-10 aryloxy group(s),
(12) a C 6-10 arylcarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s),
(13) a (C 1-8 alkyl) m3c -aminocarbonyl (C 0-8 alkyl) amino group which may be substituted by C 6-10 aryl group(s),
m3c: 0˜2,
(14) a nitro group,
(15) a hydroxy group,
(16) a C 1-8 alkoxy group which may be substituted by one or more R 3B ,
R 3B : [1] a hydroxy group, [2] a C 1-8 alkoxy group, [3] a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl group, [4] a (C 1-8 alkyl) m3d -amino group, or [5] a halogen atom,
m3d: 0˜2,
(17) a 4- to 10-membered heterocycloalkyloxy group,
(18) a 5- to 14-membered heteroaryloxy group,
(19) a (C 1-8 alkyl) m3e -aminocarbonyloxy group which may be substituted by C 6-10 aryl group(s)
m3e: 0˜2,
(20) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group,
(21) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s),
(22) a C 1-8 alkylthio group,
(23) a C 1-8 alkylsulfonyl group which may be substituted by C 6-10 aryl group(s),
(24) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by C 1-8 alkoxy group(s),
(25) a C 1-8 alkoxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkoxy group(s),
(26) a C 6-10 aryloxycarbonyl (C 0-8 alkyl) amino group which may be substituted by C 1-8 alkyl group(s) which may be substituted by halogen atom(s),
(27) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyl (C 0-8 alkyl) amino group which may be substituted by one or more R 3C ,
R 3C : [1] a C 1-8 alkyl group which may be substituted by halogen atom(s), or [2] a C 1-8 alkoxy group,
(28) a C 3-8 cycloalkyl (C 0-8 alkyl) aminocarbonyloxy group, and
(29) a C 6-10 aryl (C 0-8 alkyl) aminocarbonyloxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkyl group and [2] a C 1-8 alkoxy group;
R 4 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by halogen atom(s),
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a C 3-8 cycloalkyl group,
(6) a cyano group,
(7) an aminocarbonyl group,
(8) a (C 1-8 alkyl) m4a -aminocarbonyl group,
m4a: 1˜2,
(9) a hydroxycarbonyl group,
(10) a C 1-8 alkoxycarbonyl group,
(11) a halogen atom,
(12) a (C 1-8 alkyl) m4b -amino group,
m4b: 0˜2,
(13) a hydroxy group, and
(14) a C 1-8 alkoxy group which may be substituted by hydroxy group(s);
R 5 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 5A ,
R 5A : [1] a hydroxycarbonyl group, [2] a C 1-8 alkoxycarbonyl group, [3] a hydroxy group, [4] a C 1-8 alkoxy group, [5] a (C 1-8 alkyl) m5 -amino group, [6] a C 6-10 aryl group, or [7] a C 1-8 alkylthio group,
m5: 0˜2,
(3) a C 2-8 alkenyl group,
(4) a C 2-8 alkynyl group,
(5) a C 3-8 cycloalkyl group, and
(6) a C 1-8 alkylsulfonyl group;
R 6 and R 6′ are each independently selected from the group consisting of:
(1) a C 1-8 alkyl group which may be substituted by halogen atom(s),
(2) a C 2-8 alkenyl group, and
(3) a C 2-8 alkynyl group; or
R 6 and R 6′ are taken together with the carbon atoms to which they are bound to form:
(4) a C 3-8 cycloalkyl group, or
(5) a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl C 6-10 aryl sulfonyl group(s) which may be substituted by C 1-8 alkyl group(s);
R 7 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a halogen atom,
(3) a C 1-8 alkoxy group which may be substituted by one or more R 7A ,
R 7A : [1] a (C 1-8 alkyl)m7a-amino group, [2] a hydroxy, [3] a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl group(s),
m7a: 0˜2,
(4) a C 1-8 alkylsulfonyl group,
(5) a nitro group, and
(6) a hydroxyl group;
R 8 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 8A ,
R 8A : [1] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R8A 1 , [2] a (C 1-8 alkyl) m8a -amino group which may be substituted by a halogen atom, or [3] a hydroxy group,
m8a: 0˜2,
R 8A1 : [1] a C 1-8 alkyl group, [2] a C 1-8 alkylsulfonyl group, [3] a (C 1-8 alkyl) m8b -aminosulfonyl group, [4] an oxo group, [5] a C 1-8 alkoxycarbonyl, or [6] a C 1-8 alkoxycarbonyl (C 0-8 alkyl) aminosulfonyl,
m8b: 0˜2,
(3) a C 2-8 alkenyl group,
(4) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B ,
R 8B :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8B1 ,
<2> a C 2-8 alkynyl group,
<3> a C 2-8 alkynyl group,
<4> a C 3-8 cycloalkyl group which may be substituted by [1] cyano group(s) or [2] C 1-8 alkyl group(s),
<5> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8B2 ,
<6> a C 1-8 alkoxy group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkoxy group and [2] a C 3-8 cycloalkyl group,
<7> a C 1-8 alkoxycarbonyl group,
<8> a C 1-8 alkylsulfonyl group,
<9> a 5- to 14-membered heteroarylsulfonyl group,
<10> an oxo group,
<11> a cyano group,
<12> a C 1-8 alkanoyl group which may be substituted by one or more R 8B3 ,
<13> a C 3-8 cycloalkylcarbonyl group,
<14> a (C 1-8 alkyl) m8c -aminosulfonyl group,
<15> a C 1-8 alkylsulfonyl (C 0-8 alkyl) amino group,
<16> a (C 1-8 alkyl) m8d -amino group which may be substituted by one or more R 8B4 ,
<17> a hydroxy group,
<18> a (C 1-8 alkyl) m8e -aminocarbonyl group, or
<19> a C 1-8 alkoxycarbonyl (C 0-8 alkyl) amino group
m8c: 0˜2
m8d: 0˜2
m8e: 0˜2
R 8B1 : [1] a C 3-8 cycloalkyl group, [2] a hydroxy group, or [3] a C 1-8 alkoxy group(s),
R 8B2 : [1] a halogen atom, [2] a C 1-8 alkyl group, [3] an oxo group, [4] a hydroxy group, or [5] a deuterium atom,
R 8B3 : a (C 1-8 alkyl) m8f -amino group,
m8f: 0˜2,
R 8B4 : [1] a C 3-8 cycloalkyl group, or [2] a hydroxy group,
(5) a 5- to 14-membered heteroaryl group which may be substituted by a C 1-8 alkyl group,
(6) a (C 1-8 alkyl) m8g -aminocarbonyl group which may be substituted by one or more R 8C ,
m8g: 0˜2,
R 8C : [1] a hydroxy group, [2] a (C 1-8 alkyl) m8h -amino group which may be substituted by substituent(s) selected from the group consisting of <1> a (C 1-8 alkyl) m8i -aminosulfonyl group,
<2> a C 1-8 alkylsulfonyl group, <3> a C 1-8 alkoxycarbonyl group and <4> a C 1-8 alkoxycarbonyl(C 0-8 alkyl) aminosulfonyl group, [3] a C 1-8 alkylsulfonyl group, or [4] a C 1-8 alkoxy group which may be substituted by a hydroxy group,
m8h: 0˜2,
m8i: 0˜2,
(7) a 4- to 10-membered heterocycloalkyl (C 0-8 alkyl) aminocarbonyl group which may be substituted by oxo group(s),
(8) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8D ,
R 8D : [1] a C 1-8 alkyl group which may be substituted by one or more R 8D1 , [2] a hydroxy group, [3] a C 1-8 alkylsulfonyl group, or [4] a C 1-8 alkoxycarbonyl group,
R 8D1 : [1] a hydroxy group, or [2] a C 1-8 alkoxy group,
(9) a hydroxycarbonyl group,
(10) a C 0-8 alkoxy (C 0-8 alkyl) aminocarbonyl group which may be substituted by hydroxy group(s),
(11) a halogen atom,
(12) a (C 1-8 alkyl) m8j -amino group which may be substituted by one or more R 8H ,
m8j: 0˜2,
R 8H : [1] a hydroxy group, or [2] a 4- to 10-membered heterocycloalkyl group,
(13) a hydroxyl group,
(14) a C 1-8 alkoxy group which may be substituted by one or more R 8E ,
R 8E :
<1> a hydroxy group,
<2> halogen atom,
<3> a hydroxycarbonyl group,
<4> a C 1-8 alkoxycarbonyl group,
<5> a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by one or more R 8E1 ,
<6> a (C 1-8 alkyl) m8k1 -amino group which may be substituted by one or more R 8E2 ,
m8k1: 0˜2,
<7> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8E3 ,
<8> a 5- to 14-membered heteroaryl group,
<9> a (C 1-8 alkyl) m8k2 -aminocarbonyl group which may be substituted by one or more R 8E6 ,
m8k2: 0˜2,
<10> a C 1-8 alkoxy group which may be substituted by one or more R 8E7 ,
<11> a C 1-8 alkylthio group,
<12> a C 1-8 alkylsulfinyl group,
<13> a C 1-8 alkylsulfonyl group,
R 8E1 :
<1> a C 1-8 alkoxycarbonyl group,
<2> a C 1-8 alkanoyl group,
<3> a C 1-8 alkylsulfonyl group,
<4> a (C 1-8 alkyl) m8k3 -aminosulfonyl group,
m8k3: 0˜2, or
<5> a 4- to 10-membered heterocycloalkyl group,
R 8E2 :
<1> a hydroxy group,
<2> a C 1-8 alkoxycarbonyl group which may be substituted by halogen atom(s),
<3> a C 3-8 cycloalkyl group which may be substituted by C 1-8 alkyl group(s) which may be substituted by hydroxy group(s),
<4> a C 1-8 alkanoyl group which may be substituted by substituent(s) selected from the group consisting of [1] a (C 1-8 alkyl) m8k4 -amino group and [2] a halogen atom(s),
m8k4: 0˜2,
<5> a (C 1-8 alkyl) m8k5 -aminocarbonyl group,
m8k5: 0˜2,
<6> a C 1-8 alkylsulfonyl group,
<7> a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s),
<8> a (C 1-8 alkyl) m8k6 -aminosulfonyl group which may be substituted by C 1-8 alkoxycarbonyl group(s),
m8k6: 0˜2, or
R 8E3 :
<1> a C 1-8 alkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a hydroxy group and [2] a C 1-8 alkylcarbonyloxy group,
<2> a C 1-8 alkylcarbonyloxy group,
<3> a hydroxy group,
<4> a C 3-8 cycloalkyl group,
<5> a C 1-8 alkoxy group,
<6> a C 1-8 alkoxycarbonyl group,
<7> a C 1-8 alkylsulfonyl group,
<8> a (C 1-8 alkyl) m8k8 -aminocarbonyl group
m8k8: 0˜2,
<9> a C 1-8 alkanoyl group which may be substituted by hydroxy group(s),
<10> an oxo group, or
<11> a 4- to 10-membered heterocycloalkyl group which may be substituted by substituent(s) selected from the group consisting of [1] a C 1-8 alkanoyl group, [2] a C 1-8 alkoxycarbonyl group and [3] a C 1-8 alkylsulfonyl group,
R 8E6 :
<1> a C 2-8 alkenylcarbonyloxy group,
<2> a hydroxy group,
<3> a cyano group,
<4> a (C 1-8 alkyl) m8k9 -amino group which may be substituted by hydroxy group(s)
m8k9: 0˜2,
<5> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
<6> a C 1-8 alkylcarbonyloxy group,
<7> a 4- to 10-membered heterocycloalkyl group which may be substituted by C 1-8 alkyl group(s), or
<8> a 5- to 14-membered heteroaryl group,
R 8E7 :
<1> a hydroxy group, or
<2> a C 1-8 alkoxy group which may be substituted by hydroxy group(s),
(15) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by one or more R 8F ,
R 8F :
<1> a C 1-8 alkyl group which may be substituted by one or more R 8F1 ,
<2> a C 3-8 cycloalkyl group,
<3> a C 1-8 alkanoyl group which may be substituted by halogen atom(s),
<4> a C 1-8 alkylcarbonyloxy group,
<5> a C 1-8 alkoxycarbonyl group,
<6> a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 8F2 ,
<7> a C 1-8 alkyl sulfonyl group,
<8> a hydroxy group, or
[9] a C 6-10 aryl group,
R 8F1 : [1] a hydroxy group, [2] a C 1-8 alkoxy group, or [3] a halogen atom,
R 8F2 : [1] a 4- to 10-membered heterocycloalkyl group, [2] a C 1-8 alkoxycarbonyl group, or [3] a C 1-8 alkylsulfonyl group,
(16) a 5- to 14-membered heteroaryloxy group,
(17) a 4- to 10-membered heterocycloalkylcarbonyloxy group,
(18) a (C 1-8 alkyl) m8l1 -aminosulfonyloxy group,
m8l1: 0˜2,
(19) a C 1-8 alkyl thio group which may be substituted by [1] (C 1-8 alkyl) m8l2 -amino group(s), [2] hydroxy group(s) or [3] hydroxycarbonyl group(s),
m8l2: 0˜2,
(20) a C 1-8 alkylsulfonyl group which may be substituted by one or more R 8G ,
R 8G : [1] a hydroxycarbonyl group, [2] a hydroxy group, or [3] a (C 1-8 alkyl) m8l3 -amino group,
m8l3: 0˜2,
(21) a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyloxy group which may be substituted by C 1-8 alkyl group(s),
(22) a C 2-8 alkenyloxy group, and
(23) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s);
R 9 is selected from the group consisting of:
(1) a hydrogen atom,
(2) a C 1-8 alkyl group which may be substituted by one or more R 9A ,
R 9A : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9A1 , [3] a hydroxy group, [4] a C 1-8 alkoxy group, or [5] a hydroxycarbonyl group,
R 9A1 : [1] a C 1-8 alkyl group, [2] a C 3-8 cycloalkyl group, or [3] a 4- to 10-membered heterocycloalkyl group,
(3) a C 2-8 alkenyl group which may be substituted by one or more R 9B ,
R 9B : [1] a (C 1-8 alkyl) m9a -amino group, [2] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more group R 9B1 ,
R 9B1 : [1] a C 3-8 cycloalkyl group, or [2] a 4- to 10-membered heterocycloalkyl group,
m9a: 0˜2,
(4) a C 2-8 alkynyl group which may be substituted by one or more R 9C ,
R 9C : [1] a C 1-8 alkoxy group, [2] a (C 1-8 alkyl) m9b -amino group which may be substituted by C 6-10 aryl group(s), [3] a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9C1 , [4] a C 3-8 cycloalkyl group, [5] a hydroxy group, [6] a hydroxycarbonyl group, or [7] a C 1-8 alkyloxycarbonyl group,
m9b: 0˜2,
R 9C1 : [1] a C 3-8 cycloalkyl group, [2] a 4- to 10-membered heterocycloalkyl group, or [3] an oxo group,
(5) a C 3-8 cycloalkyl group,
(6) a 4- to 10-membered heterocycloalkyl group which may be substituted by one or more R 9D ,
R 9D : [1] a C 1-8 alkyl group which may be substituted by 4- to 10-membered heterocycloalkyl group(s), [2] a C 3-8 cycloalkyl group, [3] a 4- to 10-membered heterocycloalkyl group, or [4] a C 1-6 alkylsulfonyl group, or [5] a C 1-8 alkoxycarbonyl group,
(7) a C 6-10 aryl group which may be substituted by one or more R 9E ,
R 9E : [1] a halogen atom, [2] a hydroxy group, [3] a hydroxycarbonyl group, or [4] a C 1-8 alkyl group which may be substituted by hydroxy group(s), or [5] a C 1-8 alkoxy group,
(8) a 5- to 14-membered heteroaryl group which may be substituted by C 1-8 alkyl group(s),
(9) a cyano group,
(10) a C 1-8 alkanoyl group,
(11) a 4- to 10-membered nitrogen-containing heterocycloalkylcarbonyl group which may be substituted by C 1-8 alkyl group(s),
(12) a halogen atom,
(13) a (C 1-8 alkyl) m9c -amino group which may be substituted by one or more R 9F ,
m9c: 0˜2,
R 9F : [9F-1] a C 1-3 alkylsulfonyl group, [9F-2] a (C 1-3 alkyl) m9f1 -aminosulfonyl group (m9f1: 0˜2), or [9F-3] a C 1-3 alkanoyl group which may be substituted by (C 1-3 alkyl) m9f2 -amino group(s) (m9f2: 0˜2),
(14) a C 1-8 alkylcarbonyl(C 0-8 alkyl)amino group which may be substituted by (C 1-8 alkyl) m9d -amino group(s),
m9d: 0˜2,
(15) a C 1-8 alkylsulfonyl(C 0-8 alkyl)amino group,
(16) a (C 1-8 alkyl) m9e -aminosulfonyl(C 0-8 alkyl)amino group,
m9e: 0˜2,
(17) a nitro group,
(18) a hydroxy group,
(19) a C 1-8 alkoxy group which may be substituted by one or more R 9G ,
R 9G : [1] a hydroxy group, [2] a hydroxycarbonyl group, [3] a C 6-10 aryl group which may be substituted by C 1-8 alkoxy group(s), [4] a (C 1-8 alkyl) m9g1 -amino group, [5] a C 1-8 alkoxy group which may be substituted by one or more R 9G1 , [6] a 5- to 14-membered heteroaryl group, or [7] a 4- to 10-membered heterocycloalkyloxy group which may be substituted by C 1-8 alkyl group(s),
m9g1: 0˜2,
R 9G1 : [1] a C 1-8 alkoxy group, or [2] a hydroxycarbonyl group,
(20) a 4- to 10-membered heterocycloalkyloxy group which may be substituted by [1] 4-to 10-membered heterocycloalkyl group(s), or [2] C 1-8 alkoxycarbonyl group(s),
(21) a C 1-8 alkylsulfonyloxy group which may be substituted by halogen atom(s),
(22) a C 1-8 alkylthio group which may be substituted by (C 1-8 alkyl) m9f -amino group(s),
m9f: 0˜2,
(23) a C 1-8 alkylsulfonyl group which may be substituted by (C 1-8 alkyl) m9g -amino group(s),
m9g: 0˜2,
(24) a (C 1-8 alkyl) m9h -aminosulfonyl group,
m9h: 0˜2,
(25) a 4- to 10-membered nitrogen-containing heterocycloalkylsulfonyl group which may be substituted by C 1-8 alkyl group(s), and
(26) a hydroxycarbonyl group,
or a salt or solvate thereof.
30 . The method of claim 29 , wherein the method comprises treating cancer or cancer metastasis in the subject in need thereof.
31 . The method of claim 30 , wherein the cancer is selected from the group consisting of lung cancer, anaplastic large cell lymphoma, inflammatory myofibroblastic tumor, esophageal cancer, and neuroblastoma.
32 . The method of claim 29 , wherein the method comprises treating depression or cognitive function disorder in the subject in need thereof.
33 . The method of claim 29 , wherein the pharmaceutical comprises as an active ingredient a compound selected from the group consisting of 9-(4-isopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-9-prop-1-ynyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-cyclopropylethynyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-8-(4-cyclopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-chloro-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-prop-1-ynyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6,9-trimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-ethyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-6,6-dimethyl-11-oxo-8-(4-pyrrolidin-1-yl-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-11-oxo-8-(4-pyrrolidin-1-yl-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-ethynyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-9-propyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(1-isopropyl-piperidin-4-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-isopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(4-cyclobutyl-piperazin-1-yl)-9-cyclopropyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 8-(2-tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-ethynyl-8-(4-methanesulfonyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 9-bromo-8-(4-cyclobutyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; 6,6-dimethyl-8-(4-oxetan-3-yl-piperazin-1-yl)-11-oxo-9-propyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile; and 9-ethynyl-6,6-dimethyl-8-morpholin-4-yl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile, or a salt or solvate thereof.
34 . The method of claim 29 , wherein the pharmaceutical comprises as an active ingredient 9-ethyl-6,6-dimethyl-8-(4-morpholin-4-yl-piperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile or a salt thereof.
35 . The method of claim 29 , which is a method of treating cancer or cancer metastasis, wherein the effective amount is an effective amount for the treatment of cancer or cancer metastasis.
36 . The method of claim 29 , which is a method of treating cancer, wherein the effective amount is an effective amount for the treatment of cancer.
37 . The method of claim 29 , which is a method of treating cancer metastasis, wherein the effective amount is an effective amount for the treatment of cancer metastasis.
38 . The method of claim 29 , which is a method of treating cancer metastasis, wherein the cancer metastasis is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
39 . The method of claim 29 , which is a method of treating depression, wherein the effective amount is an effective amount for the treatment of depression.
40 . The method of claim 29 , which is a method of treating depression, wherein the depression is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
41 . The method of claim 29 , which is a method of treating a cognitive function disorder, wherein the effective amount is an effective amount for the treatment of a cognitive function disorder.
42 . The method of claim 29 , which is a method of treating a cognitive function disorder, wherein the cognitive function disorder is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
43 . The method of claim 29 , which is a method of preventing cancer, wherein the cancer is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
44 . The method of claim 29 , which is a method of preventing cancer metastasis, wherein the cancer metastasis is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
45 . The method of claim 29 , which is a method of preventing depression, wherein the depression is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
46 . The method of claim 29 , which is a method of preventing a cognitive function disorder, wherein the cognitive function disorder is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
47 . The method of claim 34 , which is a method of treating cancer or cancer metastasis, wherein the effective amount is an effective amount for the treatment of cancer or cancer metastasis.
48 . The method of claim 34 , which is a method of treating cancer, wherein the effective amount is an effective amount for the treatment of cancer.
49 . The method of claim 34 , which is a method of treating cancer metastasis, wherein the effective amount is an effective amount for the treatment of cancer metastasis.
50 . The method of claim 34 , which is a method of treating cancer metastasis, wherein the cancer metastasis is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
51 . The method of claim 34 , which is a method of treating depression, wherein the effective amount is an effective amount for the treatment of depression.
52 . The method of claim 34 , which is a method of treating depression, wherein the depression is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
53 . The method of claim 34 , which is a method of treating a cognitive function disorder, wherein the effective amount is an effective amount for the treatment of a cognitive function disorder.
54 . The method of claim 34 , which is a method of treating a cognitive function disorder, wherein the cognitive function disorder is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
55 . The method of claim 34 , which is a method of preventing cancer, wherein the cancer is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
56 . The method of claim 34 , which is a method of preventing cancer metastasis, wherein the cancer metastasis is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
57 . The method of claim 34 , which is a method of preventing depression, wherein the depression is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.
58 . The method of claim 34 , which is a method of preventing a cognitive function disorder, wherein the cognitive function disorder is accompanied by abnormality in ALK and the effective amount is an effective amount for inhibiting activity of the ALK.Join the waitlist — get patent alerts
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