US2015051208A1PendingUtilityA1
Pyridinones
Est. expiryAug 14, 2033(~7.1 yrs left)· nominal 20-yr term from priority
A61P 35/00A61P 35/02A61P 43/00C07D 401/14C07D 403/14C07D 405/14C07D 403/04C07D 401/04C07D 471/04C07D 413/14C07D 473/32
49
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Claims
Abstract
The present invention encompasses compounds of general formula (I) wherein the groups R 1 to R 3 and X 1 through X 6 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.
Claims
exact text as granted — not AI-modified1 . A compound of the formula (I)
wherein,
R 1 is selected from —H or —C 1-3 alkyl and R 2 is —C 1-3 alkyl; or
R 1 is —C 1-3 alkyl and R 2 is selected from —H, —C 1-3 alkyl, —C 1-3 haloalkyl, —NH 2 , —NH—C 1-3 alkyl, halogen;
R 3 is —C 1-4 alkyl substituted with one or more groups independently selected from halogen, —C 1-2 haloalkyl, —O—C 1-3 alkyl, —O—C 1-3 haloalkyl, 4-7 membered heterocycloalkyl, —C 3-7 cycloalkyl, phenyl and 5-6 membered heteroaryl, wherein the phenyl and the 5-6 membered heteroaryl groups can be optionally substituted with one or more groups independently selected from halogen and —C 1-2 alkyl;
X 1 is —CH═ or —N═
X 2 is —CR 7 ═ or —N═,
wherein X 1 is —CH═ and X 2 is —N═, or X 1 is —N═ and X 2 is —CH═, or X 1 is —CH═ and X 2 is —CR 7 ═
X 3 is —CR 8 ═ or —N═;
X 4 is —CR 4 ═ or —N═;
X 5 is —CR 5 ═ or —N═;
X 6 is —CH═ or —N═;
with the proviso that none or only one or two among X 3 , X 4 , X 5 and X 6 are —N═;
R 4 is selected from —H, halogen, —CN, —NH 2 , —O—R 6 , —N(C 1-3 alkyl) 2 , —C(O)N(C 1-3 alkyl) 2 and —C 1-5 alkyl, wherein the —C 1-5 alkyl group can be optionally and independently substituted with one or more groups independently selected from halogen or —CN, or
R 4 is selected from 5-6 membered heteroaryl and 4-7 membered heterocycloalkyl, wherein the heteroaryl groups can be optionally and independently substituted with one or more groups independently selected from —C 1-3 alkyl, and the heterocycloalkyl group can be optionally and independently substituted with one or more groups independently selected from —C 1-3 alkyl or ═O, or
R 4 is a —C 3-6 cycloalkyl wherein the cycloalkyl group can be optionally and independently substituted with one or more groups independently selected from C 1-3 alkyl, —C 1-3 haloalkyl and halogen;
R 5 is selected from —H, halogen, —NH 2 , —C 1-3 alkyl, —SO 2 N(C 1-3 alkyl) 2 and 5-6 membered heterocycloalkyl, which heterocycloalkyl can be optionally substituted with one or more groups independently selected from ═O, —C 1-3 alkyl, and —C 1-5 haloalkyl;
R 6 is selected from 4-7 membered heterocycloalkyl, —C 3-7 cycloalkyl and —C 1-5 alkyl, wherein the —C 1-5 alkyl group can be optionally substituted with —C 3-7 cycloalkyl,
R 7 is selected from —H, —C 1-5 alkyl and —O—C 1-5 alkyl;
R 8 is —H or —C 1-3 alkyl;
or a pharmaceutically acceptable salt thereof.
2 . A compound according to claim 1 , having a formula selected from the group consisting of
wherein R 1 to R 5 , X 1 and X 2 are defined as in claim 1 .
3 . A compound according to claim 2 , having a formula selected from the group consisting of
wherein R 1 to R 5 are defined as in claim 1 .
4 . A compound according to claim 1 , having the formula
wherein R 1 to R 3 and X 3 to X 6 are defined as in claim 1 .
5 . A compound according to claim 4 , having the formula
wherein R 1 to R 5 are defined as in claim 1 .
6 . A compound according to claim 1 , wherein R 1 is —C 1-3 alkyl.
7 . A compound according to claim 6 , wherein R 1 is —CH 3 .
8 . A compound according to claim 1 , wherein R 2 is —H, —NH 2 , —NH—C 1-3 alkyl or —C 1-3 alkyl.
9 . A compound according to claim 8 , wherein R 2 is —H, —NH 2 , —NHCH 3 or —CH 3 .
10 . A compound according to claim 1 , wherein R 1 is —C 1-3 alkyl.
11 . A compound according to claim 10 , wherein R 2 is —CH 3 .
12 . A compound according to claim 1 , wherein R 3 is —CH(CH 3 )—CH 2 —O—CH 3 , —CH(CH 3 )—CH 2 -cyclopropyl, —CH 2 -phenyl, —CH 2 -pyridyl, —CH(CH 3 )phenyl, or —CH(CH 3 )-pyridyl, wherein the phenyl and pyridyl groups are optionally and independently substituted with —Cl or with one or two —F.
13 . A compound according to claim 12 , wherein R 3 is —CH 2 -phenyl, —CH 2 -pyridyl, —CH(CH 3 )phenyl or —CH(CH 3 )-pyridyl.
14 . A compound according to claim 13 , wherein R 3 is —CH 2 -phenyl
or —CH(CH 3 )phenyl.
15 . A compound according to claim 1 , wherein R 4 is —H,
halogen, —CN, —NH 2 , —C 1-5 alkyl, —N(C 1-3 alkyl) 2 , —C(O)N(C 1-3 alkyl) 2 , —O—C 1-5 alkyl, —O—CH 2 -cyclopropyl, —O-(6 membered heterocycloalkyl), —O-cyclopropyl, 5-6 membered heteroaryl or 4-7 membered heterocycloalkyl, wherein the heterocycloalkyl is optionally substituted with one or more groups independently selected from —C 1-3 alkyl.
16 . A compound according to claim 15 , wherein R 4 is selected from —H, —F, —Cl, —CN, isopropyl, —NH 2 , —N(CH 3 ) 2 , —C(O)N(CH 3 ) 2 , —O—CH 3 , —O—CH(CH 3 ), —O—(CH 2 ) 2 CH 3 , —O-tetrahydrofuran, —O-piperidine, —O-cyclopropyl, —O—CH 2 -cyclopropyl, imidazole, tetrahydropyran, cyclopropyl substituted with —CF 3 , piperazine substituted with —CH 3 or ═O, and morpholine optionally substituted with —CH 3 or
17 . A compound according to claim 15 , wherein R 4 is selected from —C 1-5 alkyl or 4-7 membered heterocycloalkyl, which heterocycloalkyl can be optionally substituted with one or more groups independently selected from —C 1-3 alkyl.
18 . A compound according to claim 17 , wherein R 4 is selected from isopropyl, tetrahydropyran, piperazine substituted with —CH 3 and morpholine optionally substituted with —CH 3 .
19 . A compound according to claim 1 , wherein R 5 is selected from —H, —Cl, —NH 2 , —SO 2 N(CH 3 ), piperazine optionally substituted with —CH 3 , tetrahydropyran
20 . A compound according to claim 1 selected from the group consisting of
EX#
Structure
I-1
I-2
I-3
I-4
I-5
I-6
I-7
I-8
I-9
I-10
I-11
I-12
I-13
I-14
I-15
I-16
I-17
I-18
I-19
I-20
I-21
I-22
I-23
I-24
I-25
I-26
I-27
I-28
I-29
I-30
I-31
I-32
I-33
I-34
I-35
I-36
I-37
I-38
I-39
II-1
II-2
II-3
II-4
II-5
II-6
II-7
II-8
II-9
II-10
II-11
II-12
II-13
II-14
II-15
II-16
II-17
II-18
II-19
II-20
II-21
II-22
II-23
II-24
II-25
II-26
II-27
II-28
II-29
II-30
II-31
II-32
II-33
II-34
II-35
II-36
II-37
II-38
II-39
II-40
II-41
II-42
II-43
II-44
II-45
III-1
III-2
III-3
III-4
III-5
III-6
III-7
III-8
III-9
IV-1
IV-2
IV-3
IV-4
IV-5
IV-6
IV-7
IV-8
IV-9
IV-10
IV-11
IV-12
IV-13
IV-14
IV-15
V-1
V-2
V-3
V-4
and
VI-1
or a pharmaceutically acceptable salt thereof.
21 . A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.Cited by (0)
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