JP2009523845A - たんぱく質キナーゼの活性を阻害するイミダゾピリジン誘導体、これの製造方法およびこれを含む薬学組成物 - Google Patents
たんぱく質キナーゼの活性を阻害するイミダゾピリジン誘導体、これの製造方法およびこれを含む薬学組成物 Download PDFInfo
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- JP2009523845A JP2009523845A JP2008552225A JP2008552225A JP2009523845A JP 2009523845 A JP2009523845 A JP 2009523845A JP 2008552225 A JP2008552225 A JP 2008552225A JP 2008552225 A JP2008552225 A JP 2008552225A JP 2009523845 A JP2009523845 A JP 2009523845A
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- JP
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- Prior art keywords
- imidazo
- pyridine
- carboxylic acid
- amide
- phenyl
- Prior art date
- 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.)
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- 238000000034 method Methods 0.000 title claims description 31
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- 239000000126 substance Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000012453 solvate Substances 0.000 claims abstract description 11
- -1 acetylamino, carboxyl Chemical group 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- 150000001408 amides Chemical class 0.000 claims description 39
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- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 31
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 24
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- 238000010992 reflux Methods 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 22
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- DIEZPEIBLRSBCS-UHFFFAOYSA-N 2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(F)C=C1 DIEZPEIBLRSBCS-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 10
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- FEQIQCKIKLJLFO-UHFFFAOYSA-N 2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=CSC=1 FEQIQCKIKLJLFO-UHFFFAOYSA-N 0.000 claims description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- RPHWPBRVXJHHLL-UHFFFAOYSA-N 2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=COC=1 RPHWPBRVXJHHLL-UHFFFAOYSA-N 0.000 claims description 7
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- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- ZXISZMDLMKPPRD-UHFFFAOYSA-N 2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC=C1 ZXISZMDLMKPPRD-UHFFFAOYSA-N 0.000 claims description 6
- FXLXAUUIWODDSG-UHFFFAOYSA-N 2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CS1 FXLXAUUIWODDSG-UHFFFAOYSA-N 0.000 claims description 6
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims description 6
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- 239000007822 coupling agent Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- CHXNAASGPJTHBO-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(Cl)C=C1 CHXNAASGPJTHBO-UHFFFAOYSA-N 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000003226 mitogen Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- RTGHKIIZLAVHKB-UHFFFAOYSA-N 2-cyclopropyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=NC=2N=C1C1CC1 RTGHKIIZLAVHKB-UHFFFAOYSA-N 0.000 claims description 3
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 3
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- ASIPQJZKVFOMPJ-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 ASIPQJZKVFOMPJ-UHFFFAOYSA-N 0.000 claims description 3
- QLXAAIYGPASHLZ-UHFFFAOYSA-N n-[2-(4-acetamidophenyl)ethyl]-2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 QLXAAIYGPASHLZ-UHFFFAOYSA-N 0.000 claims description 3
- CGHKOVFXIOIALW-JEDNCBNOSA-N (2S)-2,6-diaminohexanoic acid 1,3-thiazole Chemical compound S1C=NC=C1.N[C@@H](CCCCN)C(=O)O CGHKOVFXIOIALW-JEDNCBNOSA-N 0.000 claims description 2
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- HJDNYULQEGIHAU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-n-[2-[4-(methanesulfonamido)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(F)=CC=1)F)N2 HJDNYULQEGIHAU-UHFFFAOYSA-N 0.000 claims description 2
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- QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 claims description 2
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- YTHVZLQCXJKFCN-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 YTHVZLQCXJKFCN-UHFFFAOYSA-N 0.000 claims 6
- ODJBWKPAXQTWRT-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 ODJBWKPAXQTWRT-UHFFFAOYSA-N 0.000 claims 5
- MADDGOYCVBBCPW-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCOCC1 MADDGOYCVBBCPW-UHFFFAOYSA-N 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
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- VDNHHYXGZIFLMB-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCCC1 VDNHHYXGZIFLMB-UHFFFAOYSA-N 0.000 claims 1
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- UZWOFJUJQLOLCY-UHFFFAOYSA-N n-(4-chloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)Cl)C=CN=C2N1 UZWOFJUJQLOLCY-UHFFFAOYSA-N 0.000 claims 1
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- VILVOBGLGPSMAH-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)-2-[4-(2-morpholin-4-ylethylamino)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CC(O)CCC1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(NCCN3CCOCC3)=CC=1)N2 VILVOBGLGPSMAH-UHFFFAOYSA-N 0.000 claims 1
- QLQGELDYENXNOJ-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCOCC1)N2 QLQGELDYENXNOJ-UHFFFAOYSA-N 0.000 claims 1
- SFZKLLFYZVCCKG-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 SFZKLLFYZVCCKG-UHFFFAOYSA-N 0.000 claims 1
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- RZINWQFCBHNFHO-UHFFFAOYSA-N n-(4-methylpyridin-3-yl)-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CN=CC=1)N2 RZINWQFCBHNFHO-UHFFFAOYSA-N 0.000 claims 1
- CHKSEMFNPTXEIK-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1N=C(C)C=C1NC(=O)C1=CC=NC2=C1N=C(C1=CSC=C1)N2 CHKSEMFNPTXEIK-UHFFFAOYSA-N 0.000 claims 1
- HBZKSGZWXGZKGL-UHFFFAOYSA-N n-(6-acetamidopyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(NC(=O)C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 HBZKSGZWXGZKGL-UHFFFAOYSA-N 0.000 claims 1
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- QVJINTSNTMHOCE-UHFFFAOYSA-N n-(6-chloro-5-methylpyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N1=C(Cl)C(C)=CC(NC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(F)=CC=2)=C1 QVJINTSNTMHOCE-UHFFFAOYSA-N 0.000 claims 1
- MUEZNHNQLOPZND-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(Cl)=CC=3)C=CN=C2N1 MUEZNHNQLOPZND-UHFFFAOYSA-N 0.000 claims 1
- DXGDWEHQDPWOEH-UHFFFAOYSA-N n-(6-chloropyridin-3-yl)-2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(Cl)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=NC=CC=1)N2 DXGDWEHQDPWOEH-UHFFFAOYSA-N 0.000 claims 1
- IVIFFFJHOAWHTN-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-(4-piperidin-1-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(OC)=CC(C)=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)N1CCCCC1)N2 IVIFFFJHOAWHTN-UHFFFAOYSA-N 0.000 claims 1
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- ZROJYFAEJLPIAW-UHFFFAOYSA-N n-[2-[2-(aminomethyl)pyridin-4-yl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(CN)=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2SC=CC=2)=C1 ZROJYFAEJLPIAW-UHFFFAOYSA-N 0.000 claims 1
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
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- Hematology (AREA)
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- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20060006834 | 2006-01-23 | ||
| US84641106P | 2006-09-21 | 2006-09-21 | |
| PCT/KR2007/000393 WO2007083978A1 (en) | 2006-01-23 | 2007-01-23 | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009523845A true JP2009523845A (ja) | 2009-06-25 |
| JP2009523845A5 JP2009523845A5 (https=) | 2012-02-16 |
Family
ID=38287858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008552225A Pending JP2009523845A (ja) | 2006-01-23 | 2007-01-23 | たんぱく質キナーゼの活性を阻害するイミダゾピリジン誘導体、これの製造方法およびこれを含む薬学組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090170847A1 (https=) |
| EP (1) | EP1984370A4 (https=) |
| JP (1) | JP2009523845A (https=) |
| KR (1) | KR20070077468A (https=) |
| CA (1) | CA2637392A1 (https=) |
| WO (1) | WO2007083978A1 (https=) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013517225A (ja) * | 2010-01-15 | 2013-05-16 | 山東軒竹医薬科技有限公司 | 縮環ピリジン誘導体 |
| JP2015503552A (ja) * | 2011-12-28 | 2015-02-02 | ハンミ ファーム． シーオー．， エルティーディー． | チロシンキナーゼ阻害剤としての新規イミダゾピリジン誘導体 |
| JP2015527406A (ja) * | 2012-09-11 | 2015-09-17 | ジェンザイム・コーポレーション | グルコシルセラミド合成酵素阻害剤 |
| JP2019535790A (ja) * | 2016-11-28 | 2019-12-12 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｇｓｋ−３阻害剤 |
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| JP2013517225A (ja) * | 2010-01-15 | 2013-05-16 | 山東軒竹医薬科技有限公司 | 縮環ピリジン誘導体 |
| JP2015503552A (ja) * | 2011-12-28 | 2015-02-02 | ハンミ ファーム． シーオー．， エルティーディー． | チロシンキナーゼ阻害剤としての新規イミダゾピリジン誘導体 |
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| JP2019535790A (ja) * | 2016-11-28 | 2019-12-12 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｇｓｋ−３阻害剤 |
| JP2021525752A (ja) * | 2018-05-31 | 2021-09-27 | シー・アンド・シー・リサーチ・ラボラトリーズＣ＆Ｃ Ｒｅｓｅａｒｃｈ Ｌａｂｏｒａｔｏｒｉｅｓ | 複素環誘導体及びその使用 |
| JP7558066B2 (ja) | 2018-05-31 | 2024-09-30 | シー・アンド・シー・リサーチ・ラボラトリーズ | 複素環誘導体及びその使用 |
| US12404249B2 (en) | 2018-05-31 | 2025-09-02 | C&C Research Laboratories | Heterocyclic derivatives and use thereof |
| JP2023529294A (ja) * | 2020-05-19 | 2023-07-10 | バイエル、アクチエンゲゼルシャフト、（ディビジョン、クロップサイエンス） | 殺真菌性化合物としてのアザ二環式（チオ）アミド |
| JP7854398B2 (ja) | 2020-05-19 | 2026-05-01 | バイエル、アクチエンゲゼルシャフト、（ディビジョン、クロップサイエンス） | 殺真菌性化合物としてのアザ二環式（チオ）アミド |
| JP2024508761A (ja) * | 2020-12-18 | 2024-02-28 | ザ スクリプス リサーチ インスティテュート | 神経変性、変性及び代謝性障害の処置のための化合物並びにその使用 |
| WO2024071439A1 (ja) * | 2022-09-30 | 2024-04-04 | 科研製薬株式会社 | 縮環化合物及びそれを含有する医薬 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070077468A (ko) | 2007-07-26 |
| EP1984370A1 (en) | 2008-10-29 |
| US20090170847A1 (en) | 2009-07-02 |
| CA2637392A1 (en) | 2007-07-26 |
| EP1984370A4 (en) | 2010-03-31 |
| WO2007083978A1 (en) | 2007-07-26 |
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