EA010426B1 - Имидазопиридины и способы их получения и применения - Google Patents

Info

Publication number

EA010426B1

EA010426B1 EA200500453A EA200500453A EA010426B1 EA 010426 B1 EA010426 B1 EA 010426B1 EA 200500453 A EA200500453 A EA 200500453A EA 200500453 A EA200500453 A EA 200500453A EA 010426 B1 EA010426 B1 EA 010426B1

Authority

EA

Eurasian Patent Office

Prior art keywords

imidazo

methylpyridin

pyridin

pyrimidin

aminopyrimidin

Prior art date

2002-09-06

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 35
• TUWAZKGQESCABO-UHFFFAOYSA-N 3h-pyrazolo[4,3-f]quinoline Chemical class C1=CC=C2C3=CNN=C3C=CC2=N1 TUWAZKGQESCABO-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 143
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 201000010099 disease Diseases 0.000 claims abstract description 19
• 230000003176 fibrotic effect Effects 0.000 claims abstract description 14
• -1 guanidino, amidino, carboxy, sulfo, mercapto Chemical class 0.000 claims description 513
• 125000000217 alkyl group Chemical group 0.000 claims description 178
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 99
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 73
• 125000001072 heteroaryl group Chemical group 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 56
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 42
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 40
• DRUPRNRFTAHFGT-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 DRUPRNRFTAHFGT-UHFFFAOYSA-N 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 32
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 31
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
• 210000004027 cell Anatomy 0.000 claims description 29
• 125000004414 alkyl thio group Chemical group 0.000 claims description 28
• 125000002252 acyl group Chemical group 0.000 claims description 27
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
• 206010016654 Fibrosis Diseases 0.000 claims description 24
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 20
• 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 20
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 20
• 230000004761 fibrosis Effects 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 19
• 125000004104 aryloxy group Chemical group 0.000 claims description 19
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 19
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 19
• 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 description 18
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 18
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 17
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 16
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 16
• 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 description 15
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000003435 aroyl group Chemical group 0.000 claims description 14
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 12
• 239000004202 carbamide Substances 0.000 claims description 12
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 12
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 11
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 11
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
• 210000002744 extracellular matrix Anatomy 0.000 claims description 11
• 230000019491 signal transduction Effects 0.000 claims description 11
• VYFQAELHCIQANB-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 VYFQAELHCIQANB-UHFFFAOYSA-N 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 9
• WHIRSMPBKKWVNL-UHFFFAOYSA-N 6-[8-bromo-6-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound N12C=C(C)C=C(Br)C2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(O)=N1 WHIRSMPBKKWVNL-UHFFFAOYSA-N 0.000 claims description 8
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 210000004185 liver Anatomy 0.000 claims description 8
• NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 claims description 7
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 7
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 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 description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 235000019260 propionic acid Nutrition 0.000 claims description 7
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• FLMHPOCIZIPARJ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 FLMHPOCIZIPARJ-UHFFFAOYSA-N 0.000 claims description 6
• 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 description 6
• UDPIROHVSULNKG-UHFFFAOYSA-N 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(N)N=CC=2)=N1 UDPIROHVSULNKG-UHFFFAOYSA-N 0.000 claims description 6
• AMZCVYMZEGXAJP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-2-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C#N)=N1 AMZCVYMZEGXAJP-UHFFFAOYSA-N 0.000 claims description 6
• XBQDWPKMVWEZHR-UHFFFAOYSA-N 4-[6-chloro-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=C(Cl)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 XBQDWPKMVWEZHR-UHFFFAOYSA-N 0.000 claims description 6
• BVOUXZMZTDMVGT-UHFFFAOYSA-N 4-[7-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N1=C2C=C(C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 BVOUXZMZTDMVGT-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 230000003902 lesion Effects 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
• PGCUQJWVGDBCCN-UHFFFAOYSA-N methyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(S(C)(=O)=O)=N1 PGCUQJWVGDBCCN-UHFFFAOYSA-N 0.000 claims description 6
• LHBQJBASKOAGGW-UHFFFAOYSA-N n,n-dimethyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LHBQJBASKOAGGW-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 230000002018 overexpression Effects 0.000 claims description 6
• XPYZSOJKFJRHIS-UHFFFAOYSA-N tert-butyl n-[3-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]propyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 XPYZSOJKFJRHIS-UHFFFAOYSA-N 0.000 claims description 6
• 210000004881 tumor cell Anatomy 0.000 claims description 6
• QBVDQHQMPZYGCP-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCCC2)=N1 QBVDQHQMPZYGCP-UHFFFAOYSA-N 0.000 claims description 5
• CRXCBJUEAVHWOS-UHFFFAOYSA-N 3-[2-(2-methylaziridin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1CN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 CRXCBJUEAVHWOS-UHFFFAOYSA-N 0.000 claims description 5
• NKZVQBJACLKGJT-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 NKZVQBJACLKGJT-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• ATHLSRWZRBEENC-UHFFFAOYSA-N 4-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]morpholine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCOCC2)=N1 ATHLSRWZRBEENC-UHFFFAOYSA-N 0.000 claims description 5
• BPNIKRRCKQDOMY-UHFFFAOYSA-N 4-[8-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(C)C3=N2)C=2N=C(N)N=CC=2)=N1 BPNIKRRCKQDOMY-UHFFFAOYSA-N 0.000 claims description 5
• VTCFAEGIUJRJNF-UHFFFAOYSA-N 8-methyl-2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(C)C3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 VTCFAEGIUJRJNF-UHFFFAOYSA-N 0.000 claims description 5
• 238000009825 accumulation Methods 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 239000003513 alkali Substances 0.000 claims description 5
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
• XCFCMXMGTBEOGF-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]pyridine-3-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)C=4C=NC=CC=4)=NC3=N2)C=2N=C(N)N=CC=2)=N1 XCFCMXMGTBEOGF-UHFFFAOYSA-N 0.000 claims description 5
• XNAAOIBANVQHDR-UHFFFAOYSA-N n-cyclopentyl-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(NC3CCCC3)N=CC=2)=N1 XNAAOIBANVQHDR-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• ZXZQBJLOMCZQHF-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-pyrrolidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCC2)=N1 ZXZQBJLOMCZQHF-UHFFFAOYSA-N 0.000 claims description 4
• IYTJQGUUWQZKMH-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(2h-tetrazol-5-yl)pyrimidin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C=2NN=NN=2)=N1 IYTJQGUUWQZKMH-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• CLIRYVSLRLIRFS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-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(N)=O)C=2N=C(N)N=CC=2)=N1 CLIRYVSLRLIRFS-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• JJRWXPAUYRHWSS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=C(N)N=CC=2)=N1 JJRWXPAUYRHWSS-UHFFFAOYSA-N 0.000 claims description 4
• GNCJJLAGVLNJOB-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-2-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=CC=N1 GNCJJLAGVLNJOB-UHFFFAOYSA-N 0.000 claims description 4
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