US 10,501,473 B2 · Fused heterocyclic ring compounds and method of treating retinal disease using same

Abstract

The present invention relates to a novel indene derivative, a preparation method for the same, and a pharmaceutical composition for treating retinal disease comprising the same as an active ingredient. The novel indene derivative of the present invention, the optional isomer of the same, or the pharmaceutically acceptable salts of the same have excellent inhibitory efficiency of receptor-interacting serine-threonine-protein kinase 1 (RIPK1). Therefore, the composition containing the same as an active ingredient can be effectively used as a pharmaceutical composition for treating retinal disease.

A compound, an optical isomer, or a pharmaceutically acceptable salt of the same, wherein the compound is selected from the group consisting of:

(1) (4-bromo-7-chlorothieno[2,3-c]pyridine-2-yl)(morpholino)methanone;
(2) (4-(4-fluorophenyl)thieno[2,3-c]pyridine-2-yl)(morpholino)methanone;
(3) (4-bromothieno[2,3-c]pyridine-2-yl)(morpholino)methanone;
(4) (4-(4-fluorophenyl)thieno[2,3-b]pyridine-2-yl)(morpholino)methanone;
(5) (7-chloro-4-(4-fluorophenyl)thieno[2,3-c]pyridine-2-yl)(morpholino)methanone;
(7) 4-((4-(4-fluorophenyl)benzo[b]thiophene-2-yl)methyl)morpholine;
(8) 4-(4-(4-fluorophenyl)benzo[b]thiophene-2-carbonyl)morpholine-3-carboxylic acid;
(9) (4-(1H-indole-5-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(10) N-(4-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)phenyl)acetamide;
(14) (5-bromo-1H-benzo[d]imidazole-2-yl)(morpholino)methanone;
(17) (4,6-dimethylbenzo[b]thiophene-2-yl)(morpholino)methanone;
(18) (6,7-dimethylbenzo[b]thiophene-2-yl)(morpholino)methanone;
(19) (6-methoxybenzo[b]thiophene-2-yl)(morpholino)methanone;
(20) N,N-diethyl-2-(morpholine-4-carbonyl)benzo[b]thiophene-4-carboxamide;
(24) (5-methoxy-1H-benzo[d]imidazole-2-yl)(morpholino)methanone;
(27) (6-methylbenzofuran-2-yl)(morpholino)methanone;
(29) (7-bromobenzo[b]thiophene-2-yl)(morpholino)methanone;
(30) (4-(2-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(31) (4-(biphenyl-4-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(32) morpholino(4-p-tolylbenzo[b]thiophene-2-yl)methanone;
(33) 4-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)benzoic acid;
(34) (4-(4-methoxyphenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(35) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(pyrrolidine-1-yl)methanone;
(36) (4-(3-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(37) (4-aminopiperidine-1-yl)(4-(4-fluorophenyl)benzo[b]thiophene-2-yl)methanone hydrochloride;
(38) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(piperazine-1-yl)methanone hydrochloride;
(39) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(40) (5-(4-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(41) (4-(biphenyl-3-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(42) (4-(3-aminophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(43) 4-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)benzamide;
(44) (4-(4-hydroxyphenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(45) morpholino(4-(4-(trifluoromethoxy)phenyl)benzo[b]thiophene-2-yl)methanone;
(46) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(oxazolidine-3-yl)ethanone;
(47) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(piperidine-1-yl)methanone;
(48) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(4-hydroxypiperidine-1-yl)methanone;
(49) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(4-methylpiperazine-1-yl)methanone hydrochloride;
(50) (4-(4-(methylthio)phenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(51) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(thiomorpholino)methanone;
(52) (4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(1,4-oxazepane-4-yl)ethanone;
(53) (7-chloro-4-(4-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(54) (4-(4-bromophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(55) (4-(6-methoxypyridine-3-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(56) (4-(3-fluorobenzyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(57) (4-(2,4-difluorobenzyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(58) (4-(2,4-difluorophenylamino)benzo[b]thiophene-2-yl)(morpholino)methanone;
(59) (4-(4-fluorophenoxy)benzo[b]thiophene-2-yl)(morpholino)methanone;
(60) (4-(4-fluorophenethyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(61) (4-(4-fluorobenzyloxy)benzo[b]thiophene-2-yl)(morpholino)methanone;
(62) (4-(4-fluorobenzylsulfonyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(63) (4-(2,4-difluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(64) methyl 4-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)benzene sulfiante;
(65) (7-(4-fluorophenyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(66) (4-(6-fluoropyridine-3-yl)benzo[b]thiophene-2-yl)(morpholino)methanone hydrochloride;
(67) (4-(4-fluorobenzyl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(68) (4-(4-fluorophenylamino)benzo[b]thiophene-2-yl)(morpholino)methanone;
(69) (4-((4-fluorophenyl)(methyl)amino)benzo[b]thiophene-2-yl)(morpholino)methanone;
(70) 4-fluoro-N-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)benzenesulfonamide;
(71) (4-(4-fluorobenzylthio)benzo[b]thiophene-2-yl)(morpholino)methanone;
(72) 1-methyl-5-(2-(morpholine-4-carbonyl)benzo[b]thiophene-4-yl)-1H-pyrrole-2-carbonitrile;
(73) (4-(1-methyl-1H-pyrazol-4-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
(74) morpholino(4-(thiophene-2-yl)benzo[b]thiophene-2-yl)methanone;
(75) (4-(furan-3-yl)benzo[b]thiophene-2-yl)(morpholino)methanone;
and
(76) morpholino(4-(thiophene-3-yl)benzo[b]thiophene-2-yl)methanone.

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Fused heterocyclic ring compounds and method of treating retinal disease using same

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Fused heterocyclic ring compounds and method of treating retinal disease using same

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Abstract

Claims7