US2017240556A1PendingUtilityA1
Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders
Est. expiryJun 27, 2032(~6 yrs left)· nominal 20-yr term from priority
A61P 35/00A61P 37/02A61P 43/00A61P 25/20A61P 29/00A61P 25/00C07D 491/056C07D 491/02C07D 491/048C07D 519/00C07D 417/12A61K 31/4188C07D 403/12
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Claims
Abstract
The invention relates to a compound of the general formula (I) or a physiologically functional derivative, solvate or salt thereof, wherein A is a bond, alkyl or alkoxy optionally substituted with one or more R″ as defined herein, *—N(R′″)CO—, *—CON(R′″)—, *—N(R′″)CON(R′″)—, —S—, —SO—, *—N(R′″)—, *—N(R′″)CO—, *—CON(R′″)—, —CO—, *—COO—, *—OOC—, *—SO 2 N(R′″)—, —SO 2 , or *—N(R′″)—SO 2 —, wherein R′″ is as defined herein and * specifies the point of attachment to X; X is aryl, cycloalkyl, aralkyl, heterocyclyl or heteroaryl, which may be substituted with one or more R X further described herein; L is a bond or *—N(R N )CO—, *—CON(R N )—, *—N(R N )—, *—C═N(R N )—, *—N(R N )-alkyl-, *-alkyl-N(R N )—, *—N(R N )CON(R N )—, *—CO—, *—CO 2 —, alkyl, *-alkyl-O-alkyl-, *—NCO—CH═CH—, *—CH═CH—CONH—, *—SO 2 N(R N )—, *—N(R N )SO 2 —, or heterocyclyl, wherein * specifies the point of attachment to X; Y is H, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl or heteroaryl, which may be substituted with one or more R Y further described herein; and R and R N are further described herein; as well as their use as a medicament, a pharmaceutical composition comprising them, a method of treatment or prevention of a medical condition entailing the administration thereof, and the use thereof in the manufacture of a medicament for the treatment or prevention of a medical condition, particularly autoimmune inflammatory disorders, CNS disorders, sleeping disorders, or proliferative diseases including cancer. The invention further relates to a specific process for the preparation of said compounds.
Claims
exact text as granted — not AI-modified1 . A compound of the general formula (I) or a physiologically functional derivative, solvate or salt thereof,
wherein
R is independently selected from the group comprising H, halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, —S—R′″, —SO—R′″, nitro, —N(R′″) 2 , —NH(R′″), —NHCO(R′″), —CONH 2 , —CONH(R′″), —CO(R′″), —COH, —COO(R′″), —COOH, —SO 2 NH 2 , —SO 2 NH(R′″), —SO 2 (R′″), and —NH—SO 2 (R′″),
wherein in the cases where said group R is C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, or C 1-6 -alkoxy, said group R may be substituted with one or more substituents R″ independently selected from the group comprising H, halogen, OH, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —CO(C 1-6 -alkyl), —COH, —COO(C 1-6 -alkyl), —COOH, and —CN,
and wherein R′″ is independently selected from the group comprising H, C 1-6 -alkyl, C 1-6 -haloalkyl, aryl, heteroaryl, cycloalkyl and heterocyclyl;
R N is independently selected from the group comprising H, alkyl, haloalkyl, OH, aryl, heteroaryl, cycloalkyl, heterocyclyl, —SO—R′″, —NH 2 , —N(R′″) 2 , —NH(R′″), —NHCO(R′″), —CONH 2 , —CONH(R′″), —CO(R′″), —COH, —COO(R′″), —COOH, —SO 2 NH 2 , —SO 2 NH(R′″), —SO 2 (R′″), and —NH—SO 2 (R′″), wherein R′″ is as defined above,
wherein in the cases where said group R N is alkyl, haloalkyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl, said group R N may be substituted with one or more substituents R′″ as defined above;
A is independently selected from *—N(R a )CO—, *—CON(R a )—, *—SO 2 N(R a )—, and *—N(R a )—SO 2 —,
wherein R a is selected from H and C 1-4 -alkyl,
and wherein * specifies the point of attachment to X;
X is independently selected from the group comprising aryl, cycloalkyl, aralkyl, heterocyclyl and heteroaryl, wherein said group X may be substituted with one or more R X independently selected from the group comprising halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, aryl, heteroaryl, cycloalkyl, heterocyclyl, —S—C 1-6 -alkyl, —S—C 1-6 -haloalkyl, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —CO(C 1-6 -alkyl), —COH, —COO(C 1-6 -alkyl), —COOH, —SO 2 NH 2 , —SO 2 NH(C 1-6 -alkyl), —SO 2 (C 1-6 -alkyl), —NH—SO 2 (C 1-6 -alkyl), C 3-6 -cycloalkyl, and —CN;
L is independently a bond or a linker group selected from the group comprising *—NHCO—, *—CONH—, *—NH—, *—N(C 1-4 -alkyl)-, *—C═N(C 1-4 -alkyl)-, *—NH—C 1-4 -alkyl-, *—C 1-4 -alkyl-NH—, *—NHCONH—, *—CO—, *−SO 2 —, C 1-4 -alkyl, *—C 1-2 -alkyl-O—C 1-2 -alkyl-, *—NHCO—CH═CH—, *—CH═CH—CONH—, *—SO 2 NH—, *—NHSO 2 —, and pyridinyl, wherein * specifies the point of attachment to X; and
Y is independently selected from the group comprising H, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl and heteroaryl, wherein said group Y may optionally be substituted with one or more R Y independently selected from the group comprising halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, aryl, heteroaryl, cycloalkyl, heterocyclyl, —S—C 1-6 -alkyl, —S—C 1-6 -haloalkyl, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —CO(C 1-6 -alkyl), —COH, —COO(C 1-6 -alkyl), —COOH, —SO 2 NH 2 , —SO 2 NH(C 1-6 -alkyl), —SO 2 (C 1-6 -alkyl), —NH—SO 2 (C 1-6 -alkyl), C 1-6 -alkyl-heterocyclyl, cycloalkyl and —CN.
2 . A compound according to claim 1 , which is a compound of the general formula (Ia) or a physiologically functional derivative, solvate or salt thereof,
wherein
X is independently selected from the group comprising aryl, cycloalkyl, aralkyl, heterocyclyl and heteroaryl, wherein said group X may be substituted with one or more R X independently selected from the group comprising halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, aryl, heteroaryl, cycloalkyl, heterocyclyl, —S—C 1-6 -alkyl, —S—C 1-6 -haloalkyl, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —CO(C 1-6 -alkyl), —COH, —COO(C 1-6 -alkyl), —COOH, —SO 2 NH 2 , —SO 2 NH(C 1-6 -alkyl), —SO 2 (C 1-6 -alkyl), —NH—SO 2 (C 1-6 -alkyl), C 3-6 -cycloalkyl, and —CN;
L is independently a bond or a linker group selected from the group comprising *—NHCO—, *—CONH—, *—NH—, *—N(C 1-4 -alkyl)-, *—C═N(C 1-4 -alkyl)-, *—NH—C 1-4 -alkyl-, *—C 1-4 -alkyl-NH—, *—NHCONH—, *—CO—, *—SO 2 —, C 1-4 -alkyl, *—C 1-2 -alkyl-O—C 1-2 -alkyl-, *—NHCO—CH═CH—, *—CH═CH—CONH—, *—SO 2 NH—, *—NHSO 2 —, and pyridinyl, wherein * specifies the point of attachment to X; and
Y is independently selected from the group comprising H, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl and heteroaryl, wherein said group Y may optionally be substituted with one or more R Y independently selected from the group comprising halogen, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, aryl, heteroaryl, cycloalkyl, heterocyclyl, —S—C 1-6 -alkyl, —S—C 1-6 -haloalkyl, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —CO(C 1-6 -alkyl), —COH, —COO(C 1-6 -alkyl), —COOH, —SO 2 NH 2 , —SO 2 NH(C 1-6 -alkyl), —SO 2 (C 1-6 -alkyl), —NH—SO 2 (C 1-6 -alkyl), C 1-6 -alkyl-heterocyclyl, cycloalkyl and —CN.
3 . The compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof, wherein
X is independently selected from the group comprising aryl, aralkyl, cycloalkyl, heterocyclyl and heteroaryl, wherein said group X may be substituted with one or more R X independently selected from the group comprising F, Cl, Br, I, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, OH, C 1-6 -alkoxy, nitro, —NH 2 , —N(C 1-6 -alkyl) 2 , —NH(C 1-6 -alkyl), —NHCO(C 1-6 -alkyl), —CONH 2 , —CONH(C 1-6 -alkyl), —SO 2 NH 2 , —SO 2 NH(C 1-6 -alkyl), —SO 2 (C 1-6 -alkyl), C 3-6 -cycloalkyl, —NH—SO 2 (C 1-6 -alkyl), —COOH, —COO—C 1-6 -alkyl, and —CN;
L is independently a bond or a linker group selected from the group comprising *—NHCO—, *—NH—, *—NHCH 2 —, *—NHCONH—, *—NHCO—CH═CH—, *—NHSO 2 —, *—SO 2 —, and pyridinyl, wherein * specifies the point of attachment to X; and
Y is independently selected from the group comprising H, aryl, cycloalkyl, heterocyclyl and heteroaryl, wherein said group Y may optionally be substituted with one or more R Y independently selected from the group comprising F, Cl, Br, C 1-6 -alkyl, C 1-6 -haloalkyl, C 1-6 -haloalkoxy, C 1-6 -alkoxy, C 1-6 -alkyl-morpholinyl, and nitro.
4 . The compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof, wherein
X is independently selected from the group comprising 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1H-1,2,3-triazolyl, 1H-1,2,4-triazolyl, 1H-pyrazolyl, 1H-pyrrolyl, phenyl, benzo[b]thiophenyl, cyclohexyl, furyl, isoxazolyl, oxazolyl, imidazolyl, 1H-pyrazolyl, pyrazinyl, pyridyl, quinolinyl, 1-(naphthalen-2-yl)ethyl, thiazolyl, benzyl and thiophenyl, wherein said group X may be substituted with one or more R X independently selected from the group comprising F, Cl, Br, methyl, tert-butyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, OH, acetyl, methylcarbamoyl, methoxy, nitro, —NH 2 , —NEt 2 , —NMe 2 , —NHEt, —NHCOCH 3 , —CONH 2 , —SO 2 NH 2 , —SO 2 Me, —NH—SO 2 Me, —COOH, and —CN;
L is independently a bond or a linker group selected from the group comprising comprising *—NHCO—, *—NH—, *—NHCH 2 —, *—NHCONH—, *—NHCO—CH═CH—, *-pyridinyl-, —SO 2 —, and *—NHSO 2 —, wherein * specifies the point of attachment to X; and
Y is independently selected from the group comprising H, phenyl, furyl, thiophenyl, pyridyl, pyrimidyl, 2,3-dihydrobenzo[b][1,4]dioxinyl, 2,3-dihydrobenzofuranyl, benzo[d][1,3]dioxolyl, thieno[3,2-d]pyrimidinyl, 2-oxo-2,3-dihydrobenzoimidazolyl, pyrrolidinyl, tetrazolyl, piperidinyl, pyrazolyl, 1,2,4-oxadiazolyl, 1,2,3-thiadiazolyl, pyrrolyl, imidazolyl, isoxazolyl, thiazolyl, thiomorpholinyl, and morpholinyl, wherein said group Y may be substituted with one or two R Y independently selected from the group comprising F, Cl, methyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethoxy, methoxy, methylcarbamoyl, cyclopropyl, 2-morpholinoethyl, and nitro.
5 . The compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof, wherein
X is independently selected from the group comprising
wherein * specifies the point of attachment to the central moiety, # specifies the point of attachment to L and wherein the group X may be substituted with one or more R X ;
L is independently a bond or a linker group selected from the group comprising *—NHCO—, *—NH—, *—NHCH 2 —, *—NHCONH—, *—NHCO—CH═CH—, *-pyridinyl-, —SO 2 —, and *—NHSO 2 —, wherein * specifies the point of attachment to X;
Y is independently H or selected from the group comprising
wherein * specifies the point of attachment to L and wherein the group Y may be substituted with one or more R Y ; or
wherein X is selected from the group comprising
wherein * specifies the point of attachment to the central moiety, wherein L is a bond, Y is H, and wherein the group X may be substituted with one or more R X ;
wherein each R Y is independently selected from the group comprising F, Cl, methyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethoxy, methoxy, methylcarbamoyl, cyclopropyl, 2-morpholinoethyl, and nitro; and
wherein each R X is independently selected from the group comprising F, Cl, Br, methyl, tert-butyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, OH, acetyl, methylcarbamoyl, methoxy, nitro, —NH 2 , —NEt 2 , —NMe 2 , —NHEt, —NHCOCH 3 , —CONH 2 , —SO 2 NH 2 , —SO 2 Me, —NH—SO 2 Me, —COOH and —CN.
6 . The compound according to claim 1 , wherein said compound is selected from one of the following:
or a physiologically functional derivative, solvate or salt thereof.
7 . The compound according to claim 1 , wherein said compound is selected from one of the following:
No.
Structure
1
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-2-(2-(trifluoromethoxy)benzamido)thiazole-4-carboxamide
2
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-1-(4-fluorophenyl)-5-methyl-1H-
pyrazole-4-carboxamide
3
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(2,3-dihydrobenzofuran-5-
yl)thiazole-4-carboxamide
11
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-2-
(furan-2-carboxamido)thiazole-4-carboxamide
17
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-5-(2-(trifluoromethoxy)benzamido)-
1,2,4-thiadiazole-3-carboxamide
18
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)isonicotinamide
19
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(2,5-
dimethoxyphenylsulfonamido)thiazole-4-carboxamide
20
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)thiophene-3-carboxamide
21
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(isonicotinamido)thiazole-4-
carboxamide
26
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(3-(2-
(trifluoromethoxy)phenyl)ureido)thiazole-4-carboxamide
29
5-bromo-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)thiophene-3-carboxamide
30
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-5-nitrothiophene-3-carboxamide
31
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)benzo[b]thiophene-3-carboxamide
33
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-2-methylfuran-
3-carboxamide
37
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-morpholinothiazole-4-carboxamide
38
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-5-(2,3-dihydrobenzofuran-5-
yl)thiophene-3-carboxamide
41
3-chloro-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)benzamide
48
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(2-
(trifluoromethoxy)benzamido)oxazole-5-carboxamide
49
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)benzamide
51
3-(2,4-dichlorobenzamido)-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-1H-
1,2,4-triazole-5-carboxamide
52
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-(2-(trifluoromethoxy)benzamido)-
1H-1,2,4-triazole-5-carboxamide
56
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-methoxybenzamide
57
5-(3-chlorobenzamido)-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-1,2,4-thiadiazole-3-
carboxamide
60
4-amino-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)benzamide
62
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-4-sulfamoylbenzamide
65
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-nitrobenzamide
66
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-(trifluoromethyl)benzamide
69
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol- 6-yl)-2-(4-methoxybenzamido)thiazole-4-carboxamide
70
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-fluorobenzamide
75
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-4-(dimethylamino)benzamide
76
4-(benzylamino)-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)benzamide
77
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-4-(ethylamino)benzamide
78
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)nicotinamide
80
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)cyclohexanecarboxamide
81
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-2-(thiophen-3-yl)thiazole-4-
carboxamide
82
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-
yl)thiazole-4-carboxamide
83
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-5-sulfamoylthiophene-3-
carboxamide
87
88
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-4-nitro-1H-
pyrrole-2-carboxamide
91
5-(4-chlorobenzamido)-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-
1,2,4-thiadiazole-3-carboxamide
92
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-5-(4-fluorobenzamido)-1,2,4-
thiadiazole-3-carboxamide
94
N 1 -(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-fluoroterephthalamide
100
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-
sulfamoylbenzamide
101
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)-4-sulfamoyl-1H-pyrrole-2-carboxamide
102
N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-
(dimethylamino)benzamide
104
4-acetyl-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-
1H-pyrrole-2-carboxamide
105
methyl 3-((2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)carbamoyl)benzoate
108
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-
(methylsulfonamido)benzamide
111
N 1 -(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)terephthalamide
112
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-
6-sulfamoylnicotinamide
113
N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-3-hydroxybenzamide
114
3-acetyl-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)
benzamide
116
3-cyano-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)
benzamide
117
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-4-(morpholinosulfonyl)benzamide
118
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-(1H-tetrazol-5-yl)benzamide
121
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)-3-(difluoromethoxy)benzamide
122
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-(pyrrolidin-1-
yl)benzamide
123
N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-5-
methoxynicotinamide
124
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-2-
methoxyisonicotinamide
125
N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-2-
(dimethylamino)isonicotinamide
126
4-amino-N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-
(trifluoromethyl)benzamide
128
N-(2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-3-
(piperidin-1-yl)benzamide
130
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-(3,5-
dimethyl-1H-pyrazol-1-yl)benzamide
131
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-3-(5-isopropyl-1,2,4-
oxadiazol-3-yl)benzamide
132
3-(5-(tert-butyl)-1,2,4-oxadiazol-3-yl)-N-(2,2-
difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)benzamide
133
(S)-N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-2-(6-methoxynaphthalen-2-
yl)propanamide
134
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-2-(4-methyl-1,2,3-
thiadiazol-5-yl)thiazole-4-carboxamide
135
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-[2,4′-bithiazole]-
4-carboxamide
136
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-2-(thiophen-2-
yl)oxazole-4-carboxamide
137
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo
[1,2-d]imidazol-6-yl)-3-(5-methyl-1,2,4-
oxadiazol-3-yl)benzamide
138
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-5-(thiophen-2-
yl)isoxazole-3-carboxamide
139
ethyl 1-(3-((2,2-difluoro-5H-[1,3]dioxolo
[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)carbamoyl)
phenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate
140
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-(1H-
imidazol-2-yl)benzamide
141
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-2-(5-
methylisoxazol-3-yl)thiazole-4-carboxamide
142
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-4-(1H-pyrazol-1-yl)benzamide
144
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-5-(1,3-dimethyl-1H-pyrazol-4-
yl)isoxazole-3-carboxamide
147
3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-N-(2,2-
difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)benzamide
148
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-(5-methyl-1H-
tetrazol-1-yl)benzamide
149
N-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]
benzo[1,2-d]imidazol-6-yl)-3-(1H-tetrazol-1-
yl)benzamide
1B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)-3,5-dimethoxybenzamide
2B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-3-(thiazol-2-yl)benzamide
3B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-2-(3-methoxyphenyl)acetamide
4B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-5-(furan-2-yl)nicotinamide
5B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-3-(1H-pyrazol-3-yl)benzamide
6B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-2-(furan-2-yl)thiazole-4-carboxamide
7B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-5-(dimethylamino)nicotinamide
8B
2-(3-chlorophenyl)-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)acetamide
9B
4-amino-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)-3-methoxybenzamide
10B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-yl)-5-
(thiophene-3-carboxamido)-1,2,4-thiadiazole-3-carboxamide
11B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)-2-(thiophen-2-yl)thiazole-4-carboxamide
12B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-
yl)-2-(3-fluorophenyl)thiazole-4-carboxamide
13B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-1-methyl-1H-pyrazole-4-carboxamide
14B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-2-thiomorpholinoisonicotinamide
15B
4-amino-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-1H-pyrrole-2-carboxamide
16B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-2-(furan-3-yl)thiazole-4-carboxamide
17B
2-(3-chlorophenyl)-N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-
d]imidazol-6-yl)thiazole-4-carboxamide
22B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-4-(1H-tetrazol-1-yl)benzamide
23B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-5-(thiophen-2-yl)nicotinamide
25B
N-(2,2-difluoro-5H-
[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-
6-yl)-5-morpholinonicotinamide
or a physiologically functional derivative, solvate or salt thereof.
8 . The compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof for use as a medicament.
9 . The compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof for use in the treatment or prevention of a medical condition selected from the group comprising autoimmune inflammatory disorders, CNS disorders, sleeping disorders, and proliferative diseases including cancer.
10 . A pharmaceutical composition comprising a compound according to claim 1 or a physiologically functional derivative, solvate or salt thereof and one or more pharmaceutically acceptable excipients.
11 . A method of treatment or prevention of a medical condition selected from the group comprising autoimmune inflammatory disorders, CNS disorders, sleeping disorders, and proliferative diseases including cancer, which comprises the administration of an effective amount of a compound according to claim 1 , or a physiologically functional derivative, solvate or salt thereof to a subject in need thereof.
12 . Use of a compound according to claim 1 , or a physiologically functional derivative, solvate or salt thereof in the manufacture of a medicament for the treatment or prevention of a medical condition selected from the group comprising autoimmune inflammatory disorders, CNS disorders, sleeping disorders, and proliferative diseases including cancer.
13 . Process for the preparation of a compound according to claim 1 , wherein A is an —CONH— or —NHCO—, the process comprising the step of coupling a compound of below Formula IV with a compound of below formula II;
wherein Y, L and X are as defined above, and
wherein either R 1 is NH 2 and R 2 is COOH or COOCl, or wherein R 2 is NH 2 and R 1 is COOH or COOCl.Cited by (0)
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