KR20090024295A - 글리코겐 신타제 키나제 (ｇｓｋ3) 관련 질환의 치료를 위한 이미다졸-피리미딘 유도체 - Google Patents

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Publication number

KR20090024295A

KR20090024295A KR1020097001643A KR20097001643A KR20090024295A KR 20090024295 A KR20090024295 A KR 20090024295A KR 1020097001643 A KR1020097001643 A KR 1020097001643A KR 20097001643 A KR20097001643 A KR 20097001643A KR 20090024295 A KR20090024295 A KR 20090024295A

Authority

KR

South Korea

Prior art keywords

alkyl

methyl

heterocyclyl

pyran

tetrahydro

Prior art date

2006-06-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 201000010099 disease Diseases 0.000 title claims description 13
• 108091007911 GSKs Proteins 0.000 title description 2
• KNDAOVHRTCJABP-UHFFFAOYSA-N 1h-imidazole;pyrimidine Chemical class C1=CNC=N1.C1=CN=CN=C1 KNDAOVHRTCJABP-UHFFFAOYSA-N 0.000 title 1
• 102000004103 Glycogen Synthase Kinases Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 207
• 238000000034 method Methods 0.000 claims abstract description 56
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• -1 nitro, cyano, hydroxy, amino, sulfamoyl Chemical group 0.000 claims description 188
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• 125000004452 carbocyclyl group Chemical group 0.000 claims description 98
• 125000005843 halogen group Chemical group 0.000 claims description 70
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 46
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 43
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 241000124008 Mammalia Species 0.000 claims description 37
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
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• 150000002431 hydrogen Chemical class 0.000 claims description 24
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• 125000003545 alkoxy group Chemical group 0.000 claims description 20
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
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• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 9
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
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• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
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• 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
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• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
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• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
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• 125000004423 acyloxy group Chemical group 0.000 claims description 6
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• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
• 230000002123 temporal effect Effects 0.000 claims description 6
• JAJMSUGMMRKEJS-UHFFFAOYSA-N tert-butyl 4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]piperidine-1-carboxylate Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1CCN(C(=O)OC(C)(C)C)CC1 JAJMSUGMMRKEJS-UHFFFAOYSA-N 0.000 claims description 6
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• BDSBULQPKFMZDX-UHFFFAOYSA-N 2-bromo-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidine Chemical compound C1COCCC1N1C(C)=NC=C1C1=NC(Br)=NC=C1F BDSBULQPKFMZDX-UHFFFAOYSA-N 0.000 claims description 5
• SKAQUBBZLUGQFR-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridine-2-carbaldehyde Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C=O)N=C1 SKAQUBBZLUGQFR-UHFFFAOYSA-N 0.000 claims description 5
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• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
• VTCQOLUUQCFBAL-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[6-(1,4-oxazepan-4-ylmethyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1CN1CCCOCC1 VTCQOLUUQCFBAL-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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