ZA200501853B - Imidazolopyridines and methods of making and usingthe same. - Google Patents

Imidazolopyridines and methods of making and usingthe same. Download PDF

Info

Publication number: ZA200501853B
Authority: ZA; South Africa
Prior art keywords: pyridin; methyl; pyrimidin; imidazo; amino
Prior art date: 2002-09-06

Application number

ZA200501853A

Other languages

English (en)

Inventor

Wen-Cherng Lee

Mary Beth Carter

Lihong Sun

Claudio Chuaqui

Juswinder Singh

Paula Boriack-Sjodin

Michael J Choi

Original Assignee

Biogen Idec Inc

Priority date (The priority date 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 date listed.)

2002-09-06

Filing date

2005-03-03

Publication date

2005-11-30

2005-03-03 Application filed by Biogen Idec Inc filed Critical Biogen Idec Inc

2005-11-30 Publication of ZA200501853B publication Critical patent/ZA200501853B/en

Links

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
WSEICPQOLNGCPR-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(OCC=4C=CC=CC=4)C3=N2)C=2N=C(N)N=CC=2)=N1 WSEICPQOLNGCPR-UHFFFAOYSA-N 0.000 claims 2
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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AGSSPIXIGIFOKP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(F)(F)F)C=2N=C(N)N=CC=2)=N1 AGSSPIXIGIFOKP-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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ZA200501853A 2002-09-06 2005-03-03 Imidazolopyridines and methods of making and usingthe same. ZA200501853B (en)

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CO5271680A1 (es) *	2000-02-21	2003-04-30	Smithkline Beecham Corp	Compuestos
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
EP1539748A1 (en) *	2002-07-31	2005-06-15	Smithkline Beecham Corporation	2-phenylpyridin-4-yl derivatives as alk5 inhibitors
GB0217783D0 (en) *	2002-07-31	2002-09-11	Glaxo Group Ltd	Compounds
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 WO PCT/US2003/027721 patent/WO2004021989A2/en not_active Ceased
- 2003-09-05 GE GEAP20038732A patent/GEP20074165B/en unknown
- 2003-09-05 EA EA200500453A patent/EA010426B1/ru not_active IP Right Cessation
- 2003-09-05 CA CA002497968A patent/CA2497968A1/en not_active Abandoned
- 2003-09-05 BR BR0314052-0A patent/BR0314052A/pt not_active IP Right Cessation
- 2003-09-05 MX MXPA05002442A patent/MXPA05002442A/es active IP Right Grant
- 2003-09-05 NZ NZ539068A patent/NZ539068A/en unknown
- 2003-09-05 PL PL03375691A patent/PL375691A1/xx not_active Application Discontinuation
- 2003-09-05 EP EP03752004A patent/EP1546112A4/en not_active Withdrawn
- 2003-09-05 RS YUP-2005/0199A patent/RS20050199A/sr unknown
- 2003-09-05 JP JP2004534570A patent/JP2006502164A/ja active Pending
- 2003-09-05 AU AU2003270318A patent/AU2003270318B2/en not_active Ceased
- 2003-09-05 US US10/526,653 patent/US20060135517A1/en not_active Abandoned
- 2003-09-05 CN CN038248662A patent/CN1694871B/zh not_active Expired - Fee Related
- 2003-09-05 KR KR1020057003871A patent/KR20050035296A/ko not_active Withdrawn
- 2003-09-08 AR ARP030103249A patent/AR041206A1/es not_active Application Discontinuation
- 2003-09-08 MY MYPI20033385A patent/MY139566A/en unknown
2005
- 2005-03-03 ZA ZA200501853A patent/ZA200501853B/en unknown
- 2005-03-21 NO NO20051493A patent/NO20051493L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP1546112A4 (en)	2006-06-07
AU2003270318B2 (en)	2010-01-14
JP2006502164A (ja)	2006-01-19
RS20050199A (sr)	2007-08-03
US20060135517A1 (en)	2006-06-22
EP1546112A2 (en)	2005-06-29
UA80296C2 (en)	2007-09-10
NZ539068A (en)	2006-10-27
EA010426B1 (ru)	2008-08-29
BR0314052A (pt)	2005-07-05
CA2497968A1 (en)	2004-03-18
GEP20074165B (en)	2007-07-25
AR041206A1 (es)	2005-05-11
NO20051493D0 (no)	2005-03-21
WO2004021989A2 (en)	2004-03-18
NO20051493L (no)	2005-03-21
AU2003270318A1 (en)	2004-03-29
PL375691A1 (en)	2005-12-12
EA200500453A1 (ru)	2005-10-27
MY139566A (en)	2009-10-30
KR20050035296A (ko)	2005-04-15
MXPA05002442A (es)	2005-09-30
CN1694871B (zh)	2010-06-16
WO2004021989A3 (en)	2004-09-23
CN1694871A (zh)	2005-11-09

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