ZA200501853B - Imidazolopyridines and methods of making and usingthe same. - Google Patents
Imidazolopyridines and methods of making and usingthe same. Download PDFInfo
- Publication number
- ZA200501853B ZA200501853B ZA200501853A ZA200501853A ZA200501853B ZA 200501853 B ZA200501853 B ZA 200501853B ZA 200501853 A ZA200501853 A ZA 200501853A ZA 200501853 A ZA200501853 A ZA 200501853A ZA 200501853 B ZA200501853 B ZA 200501853B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridin
- methyl
- pyrimidin
- imidazo
- amino
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 48
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 66
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- -1 hydroxy, amino Chemical group 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 102000009618 Transforming Growth Factors Human genes 0.000 claims description 24
- 108010009583 Transforming Growth Factors Proteins 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 210000004027 cell Anatomy 0.000 claims description 16
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 230000003176 fibrotic effect Effects 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 10
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 210000002744 extracellular matrix Anatomy 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 9
- 230000019491 signal transduction Effects 0.000 claims description 9
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003435 aroyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 8
- 238000009825 accumulation Methods 0.000 claims description 7
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 6
- 230000004761 fibrosis Effects 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 230000002018 overexpression Effects 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims description 3
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 3
- QEQJSRLUCZMVDY-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=C(CO)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 QEQJSRLUCZMVDY-UHFFFAOYSA-N 0.000 claims description 3
- ANTKYHGNIZRNTI-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-7-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=CC(CO)=CC3=N2)C=2N=C(N)N=CC=2)=N1 ANTKYHGNIZRNTI-UHFFFAOYSA-N 0.000 claims description 3
- RQLBSRWECGGUKO-UHFFFAOYSA-N n-[(4-aminophenyl)methyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCC=3C=CC(N)=CC=3)N=CC=2)=N1 RQLBSRWECGGUKO-UHFFFAOYSA-N 0.000 claims description 3
- 201000002793 renal fibrosis Diseases 0.000 claims description 3
- GJXUUDPBMCBINS-UHFFFAOYSA-N tert-butyl n-[5-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]pentyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 GJXUUDPBMCBINS-UHFFFAOYSA-N 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000029663 wound healing Effects 0.000 claims description 3
- RMHURWLBIXLSDK-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(1h-pyrazol-5-yl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3NN=CC=3)N=CC=2)=N1 RMHURWLBIXLSDK-UHFFFAOYSA-N 0.000 claims description 2
- UMUBGGWVFYWKPC-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-2-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3N=CC=CC=3)N=CC=2)=N1 UMUBGGWVFYWKPC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 42
- 239000000126 substance Substances 0.000 claims 40
- 230000002401 inhibitory effect Effects 0.000 claims 16
- 230000037390 scarring Effects 0.000 claims 6
- 229940080818 propionamide Drugs 0.000 claims 5
- PREOONMJIVUPMI-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanamine Chemical compound NCC1COCCO1 PREOONMJIVUPMI-UHFFFAOYSA-N 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 206010069351 acute lung injury Diseases 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 230000009401 metastasis Effects 0.000 claims 4
- OYNAFVDEMSUPFN-UHFFFAOYSA-N n'-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]butane-1,4-diamine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCN)N=CC=2)=N1 OYNAFVDEMSUPFN-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 210000004881 tumor cell Anatomy 0.000 claims 4
- KLLKKKAXFTYAGU-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 KLLKKKAXFTYAGU-UHFFFAOYSA-N 0.000 claims 3
- VJJLFUGNAPGFAM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-N-hydroxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NO)C=2N=C(N)N=CC=2)=N1 VJJLFUGNAPGFAM-UHFFFAOYSA-N 0.000 claims 3
- WOBVNDLMPGASJH-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(2-methoxyethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WOBVNDLMPGASJH-UHFFFAOYSA-N 0.000 claims 3
- WNOGQPVYYPDYIN-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WNOGQPVYYPDYIN-UHFFFAOYSA-N 0.000 claims 3
- RIHSPLOZUDDXSE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 RIHSPLOZUDDXSE-UHFFFAOYSA-N 0.000 claims 3
- ITDLSWQHTALTPU-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCC2)=N1 ITDLSWQHTALTPU-UHFFFAOYSA-N 0.000 claims 3
- QVXCQUWCCGYXPM-UHFFFAOYSA-N 4-[7-(aminomethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(CN)=CC3=N2)C=2N=C(N)N=CC=2)=N1 QVXCQUWCCGYXPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims 3
- WSIRNNCRNKOMOB-UHFFFAOYSA-N methyl 3-[[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carbonyl]amino]propanoate Chemical compound N1=C2C=C(C(=O)NCCC(=O)OC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 WSIRNNCRNKOMOB-UHFFFAOYSA-N 0.000 claims 3
- WWSCCUJUUTZBPL-UHFFFAOYSA-N n-(2-methoxyethyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 WWSCCUJUUTZBPL-UHFFFAOYSA-N 0.000 claims 3
- IMZHFBNWTRKGPJ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3C=NC=C3)N=CC=2)=N1 IMZHFBNWTRKGPJ-UHFFFAOYSA-N 0.000 claims 3
- LNJWCRITIZFPCK-UHFFFAOYSA-N n-[2-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]ethyl]acetamide Chemical compound CC(=O)NCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LNJWCRITIZFPCK-UHFFFAOYSA-N 0.000 claims 3
- VXTGVZRNWICVJF-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound N1=C2N=C(NC(=O)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 VXTGVZRNWICVJF-UHFFFAOYSA-N 0.000 claims 3
- MCXIJRXEPGHSNX-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 MCXIJRXEPGHSNX-UHFFFAOYSA-N 0.000 claims 3
- BAFUGFTZYCDGRM-UHFFFAOYSA-N n-cyclopropyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC3CC3)N=CC=2)=N1 BAFUGFTZYCDGRM-UHFFFAOYSA-N 0.000 claims 3
- RRRGHOSHLCPQLU-UHFFFAOYSA-N n-methyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 RRRGHOSHLCPQLU-UHFFFAOYSA-N 0.000 claims 3
- WVAVXRCQIICYRN-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=CN=CC=2)=N1 WVAVXRCQIICYRN-UHFFFAOYSA-N 0.000 claims 2
- TVCVBBJSTVIFLY-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=CN=CC=2)=N1 TVCVBBJSTVIFLY-UHFFFAOYSA-N 0.000 claims 2
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 claims 2
- FEBFVHXQOMKXJX-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-thiophen-2-ylethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCC=2SC=CC=2)C=2N=C(N)N=CC=2)=N1 FEBFVHXQOMKXJX-UHFFFAOYSA-N 0.000 claims 2
- ZSGAZWNRAGROEO-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(piperidin-3-ylmethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC2CNCCC2)C=2N=C(N)N=CC=2)=N1 ZSGAZWNRAGROEO-UHFFFAOYSA-N 0.000 claims 2
- BAUQEWQBBHXUMG-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C#N)C=2N=C(N)N=CC=2)=N1 BAUQEWQBBHXUMG-UHFFFAOYSA-N 0.000 claims 2
- WBSWEUKONANKOY-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(N)=O)C=2N=C(N)N=CC=2)=N1 WBSWEUKONANKOY-UHFFFAOYSA-N 0.000 claims 2
- QAALUNOPVWULBE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 QAALUNOPVWULBE-UHFFFAOYSA-N 0.000 claims 2
- WMBVVXOGMONONM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCN(C)C)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WMBVVXOGMONONM-UHFFFAOYSA-N 0.000 claims 2
- DSZXRZARDVKLEJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCCN(C)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 DSZXRZARDVKLEJ-UHFFFAOYSA-N 0.000 claims 2
- HWDOSLVNGNQUSJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-cyclopropyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NC2CC2)C=2N=C(N)N=CC=2)=N1 HWDOSLVNGNQUSJ-UHFFFAOYSA-N 0.000 claims 2
- PTALXKKEJWSJGX-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 PTALXKKEJWSJGX-UHFFFAOYSA-N 0.000 claims 2
- AMODHECBNXJGPF-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NOC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 AMODHECBNXJGPF-UHFFFAOYSA-N 0.000 claims 2
- UDWZGKJGQUDLSG-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)-n-(pyridin-3-ylmethyl)pyrimidin-2-amine Chemical compound C=1C=CN=CC=1CNC(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC=N1 UDWZGKJGQUDLSG-UHFFFAOYSA-N 0.000 claims 2
- IUXZYJGBRTUWHZ-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)=N1 IUXZYJGBRTUWHZ-UHFFFAOYSA-N 0.000 claims 2
- YBHWFXBSFOTTDF-UHFFFAOYSA-N 4-[2-(6-chloropyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(Cl)C=CC=2)=N1 YBHWFXBSFOTTDF-UHFFFAOYSA-N 0.000 claims 2
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- PGEFNWQUJQHPLE-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-4-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=CN=CC=3)N=CC=2)=N1 PGEFNWQUJQHPLE-UHFFFAOYSA-N 0.000 claims 2
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- C07D471/00—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
- 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
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AR029803A1 (es) * | 2000-02-21 | 2003-07-16 | Smithkline Beecham Plc | Imidazoles sustituidos con piridilo y composiciones farmaceuticas que las comprenden |
JP4290858B2 (ja) * | 2000-06-12 | 2009-07-08 | 富士フイルム株式会社 | 有機電界発光素子 |
AU2002225730A1 (en) * | 2000-11-16 | 2002-05-27 | Smith Kline Beecham Corporation | Compounds |
GB0217783D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Compounds |
JP2005539000A (ja) * | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Alk5阻害剤としての2−フェニルピリジン−4−イル誘導体 |
PA8595001A1 (es) * | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
-
2003
- 2003-05-09 UA UAA200503149A patent/UA80296C2/uk unknown
- 2003-09-05 NZ NZ539068A patent/NZ539068A/en unknown
- 2003-09-05 AU AU2003270318A patent/AU2003270318B2/en not_active Ceased
- 2003-09-05 BR BR0314052-0A patent/BR0314052A/pt not_active IP Right Cessation
- 2003-09-05 GE GEAP20038732A patent/GEP20074165B/en unknown
- 2003-09-05 US US10/526,653 patent/US20060135517A1/en not_active Abandoned
- 2003-09-05 KR KR1020057003871A patent/KR20050035296A/ko not_active Application Discontinuation
- 2003-09-05 PL PL03375691A patent/PL375691A1/xx not_active Application Discontinuation
- 2003-09-05 RS YUP-2005/0199A patent/RS20050199A/sr unknown
- 2003-09-05 EA EA200500453A patent/EA010426B1/ru not_active IP Right Cessation
- 2003-09-05 JP JP2004534570A patent/JP2006502164A/ja active Pending
- 2003-09-05 CA CA002497968A patent/CA2497968A1/en not_active Abandoned
- 2003-09-05 CN CN038248662A patent/CN1694871B/zh not_active Expired - Fee Related
- 2003-09-05 WO PCT/US2003/027721 patent/WO2004021989A2/en active Application Filing
- 2003-09-05 MX MXPA05002442A patent/MXPA05002442A/es active IP Right Grant
- 2003-09-05 EP EP03752004A patent/EP1546112A4/en not_active Withdrawn
- 2003-09-08 MY MYPI20033385A patent/MY139566A/en unknown
- 2003-09-08 AR ARP030103249A patent/AR041206A1/es not_active Application Discontinuation
-
2005
- 2005-03-03 ZA ZA200501853A patent/ZA200501853B/en unknown
- 2005-03-21 NO NO20051493A patent/NO20051493D0/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
KR20050035296A (ko) | 2005-04-15 |
PL375691A1 (en) | 2005-12-12 |
AR041206A1 (es) | 2005-05-11 |
RS20050199A (en) | 2007-08-03 |
MY139566A (en) | 2009-10-30 |
EA010426B1 (ru) | 2008-08-29 |
AU2003270318A1 (en) | 2004-03-29 |
AU2003270318B2 (en) | 2010-01-14 |
GEP20074165B (en) | 2007-07-25 |
EA200500453A1 (ru) | 2005-10-27 |
NO20051493L (no) | 2005-03-21 |
NO20051493D0 (no) | 2005-03-21 |
CN1694871B (zh) | 2010-06-16 |
NZ539068A (en) | 2006-10-27 |
CA2497968A1 (en) | 2004-03-18 |
US20060135517A1 (en) | 2006-06-22 |
EP1546112A4 (en) | 2006-06-07 |
UA80296C2 (en) | 2007-09-10 |
WO2004021989A3 (en) | 2004-09-23 |
MXPA05002442A (es) | 2005-09-30 |
WO2004021989A2 (en) | 2004-03-18 |
JP2006502164A (ja) | 2006-01-19 |
EP1546112A2 (en) | 2005-06-29 |
BR0314052A (pt) | 2005-07-05 |
CN1694871A (zh) | 2005-11-09 |
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