JP2003528811A - アミノトリアゾロピリジン誘導体 - Google Patents

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Publication number

JP2003528811A

JP2003528811A JP2001522222A JP2001522222A JP2003528811A JP 2003528811 A JP2003528811 A JP 2003528811A JP 2001522222 A JP2001522222 A JP 2001522222A JP 2001522222 A JP2001522222 A JP 2001522222A JP 2003528811 A JP2003528811 A JP 2003528811A

Authority

JP

Japan

Prior art keywords

pyridin

phenyl

triazolo

ylamine

furan

Prior art date

1999-09-06

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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• KGUHUVQIJHGHLX-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridin-5-amine Chemical class NC1=CC=C2NN=NC2=N1 KGUHUVQIJHGHLX-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 193
• -1 — (CH 2 ) n -aryl Chemical group 0.000 claims abstract description 96
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 70
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 40
• 150000002367 halogens Chemical class 0.000 claims abstract description 40
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
• 239000001257 hydrogen Substances 0.000 claims abstract description 21
• 125000001424 substituent group Chemical group 0.000 claims abstract description 15
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
• 239000002253 acid Substances 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
• XGXOQBWTDDSGKT-UHFFFAOYSA-N 2-(1,4,5,6-tetrahydropyrimidin-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NCCCN1 XGXOQBWTDDSGKT-UHFFFAOYSA-N 0.000 claims abstract description 4
• DAFSXTNSQHDLLK-UHFFFAOYSA-N 2-(4,5,6,7-tetrahydro-1h-1,3-diazepin-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NCCCCN1 DAFSXTNSQHDLLK-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims abstract description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical class 0.000 claims abstract 7
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 42
• 238000000034 method Methods 0.000 claims description 38
• JFYJWEDLPLADGY-UHFFFAOYSA-N triazolo[1,5-a]pyridin-5-amine Chemical compound C1=C(N)C=CN2N=NC=C21 JFYJWEDLPLADGY-UHFFFAOYSA-N 0.000 claims description 29
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 21
• 229960005305 adenosine Drugs 0.000 claims description 21
• 102000005962 receptors Human genes 0.000 claims description 20
• 108020003175 receptors Proteins 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 11
• 102000009346 Adenosine receptors Human genes 0.000 claims description 10
• 108050000203 Adenosine receptors Proteins 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• RLCWLXLOTSWZPK-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound NC1=CC=CC2=NC=NN12 RLCWLXLOTSWZPK-UHFFFAOYSA-N 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• BFLQSIPICPESNY-UHFFFAOYSA-N 2,7-dipyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3N=CC=CC=3)=CC2=NC=1C1=CC=CC=N1 BFLQSIPICPESNY-UHFFFAOYSA-N 0.000 claims description 4
• ZZUBCMKZOLSNRX-UHFFFAOYSA-N 7-(2-fluoropyridin-4-yl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(F)N=CC=3)=CC2=NC=1C1=CC=CO1 ZZUBCMKZOLSNRX-UHFFFAOYSA-N 0.000 claims description 4
• LCQSFAQOIWWFOK-UHFFFAOYSA-N 7-(5-chloropyridin-2-yl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3N=CC(Cl)=CC=3)=CC2=NC=1C1=CC=CO1 LCQSFAQOIWWFOK-UHFFFAOYSA-N 0.000 claims description 4
• GLBOEFHZEAMDRF-UHFFFAOYSA-N 7-(5-chloropyridin-2-yl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3N=CC(Cl)=CC=3)=CC2=NC=1C1=CC=CC=N1 GLBOEFHZEAMDRF-UHFFFAOYSA-N 0.000 claims description 4
• UQPHSPQKGXGSSH-UHFFFAOYSA-N 7-(5-ethylpyridin-2-yl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N1=CC(CC)=CC=C1C1=CC2=NC(C=3N=CC=CC=3)=NN2C(N)=C1 UQPHSPQKGXGSSH-UHFFFAOYSA-N 0.000 claims description 4
• DKSIUIBDKDHOKG-UHFFFAOYSA-N 7-(6-chloropyridin-2-yl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3N=C(Cl)C=CC=3)=CC2=NC=1C1=CC=CC=N1 DKSIUIBDKDHOKG-UHFFFAOYSA-N 0.000 claims description 4
• RHGMJAZJTQZVAK-UHFFFAOYSA-N 2-(2-methylphenyl)-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)acetamide Chemical compound CC1=CC=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 RHGMJAZJTQZVAK-UHFFFAOYSA-N 0.000 claims description 3
• ITNCYLOZJAKKJU-UHFFFAOYSA-N 2-(furan-2-yl)-7-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(C)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 ITNCYLOZJAKKJU-UHFFFAOYSA-N 0.000 claims description 3
• QPSDCSNVLGCMRR-UHFFFAOYSA-N 2-(furan-2-yl)-7-(2-propan-2-ylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(C(C)C)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 QPSDCSNVLGCMRR-UHFFFAOYSA-N 0.000 claims description 3
• VVAGOZJUXFZWJK-UHFFFAOYSA-N 2-(furan-2-yl)-7-(2-propylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(CCC)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 VVAGOZJUXFZWJK-UHFFFAOYSA-N 0.000 claims description 3
• XYVRLCKVLAYFHQ-UHFFFAOYSA-N 2-(furan-2-yl)-7-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3N=CC=CC=3)=CC2=NC=1C1=CC=CO1 XYVRLCKVLAYFHQ-UHFFFAOYSA-N 0.000 claims description 3
• QMVJEOGXPUUNSI-UHFFFAOYSA-N 2-(furan-2-yl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=NC=CC=3)=CC2=NC=1C1=CC=CO1 QMVJEOGXPUUNSI-UHFFFAOYSA-N 0.000 claims description 3
• NAZMHULOIRNWSS-UHFFFAOYSA-N 2-(furan-2-yl)-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=CN=CC=3)=CC2=NC=1C1=CC=CO1 NAZMHULOIRNWSS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• UVKCEBORXTUBIG-UHFFFAOYSA-N 2-phenyl-7-pyridin-4-yl-n-[[4-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 UVKCEBORXTUBIG-UHFFFAOYSA-N 0.000 claims description 3
• VLLXVZVLUAQWTB-UHFFFAOYSA-N 2-phenyl-n-(3-phenylpropyl)-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C=1C=CC=CC=1CCCNC(N1N=2)=CC(C=3C=CN=CC=3)=CC1=NC=2C1=CC=CC=C1 VLLXVZVLUAQWTB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• WYJZKZDSBOVGJO-UHFFFAOYSA-N 3-phenyl-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)propanamide Chemical compound C=1C(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN2C=1NC(=O)CCC1=CC=CC=C1 WYJZKZDSBOVGJO-UHFFFAOYSA-N 0.000 claims description 3
• GNIHZZVASOQADT-UHFFFAOYSA-N 5-amino-2-(furan-2-yl)-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridine-6-carbonitrile Chemical compound N=1N2C(N)=C(C#N)C(C=3C=CN=CC=3)=CC2=NC=1C1=CC=CO1 GNIHZZVASOQADT-UHFFFAOYSA-N 0.000 claims description 3
• KOKWNHIJLWMWEQ-UHFFFAOYSA-N 7-(2-ethylpyridin-4-yl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(CC)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 KOKWNHIJLWMWEQ-UHFFFAOYSA-N 0.000 claims description 3
• MLQJNKJIFZLOCY-UHFFFAOYSA-N 7-(2-ethylpyridin-4-yl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(CC)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2N=CC=CC=2)=C1 MLQJNKJIFZLOCY-UHFFFAOYSA-N 0.000 claims description 3
• UCQLAKMCVDNCTN-UHFFFAOYSA-N 7-(2-methylpyridin-4-yl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=NC(C)=CC(C2=CC3=NC(=NN3C(N)=C2)C=2N=CC=CC=2)=C1 UCQLAKMCVDNCTN-UHFFFAOYSA-N 0.000 claims description 3
• XHONYMKHKBKRRP-UHFFFAOYSA-N 7-(4-chlorophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=CC(Cl)=CC=3)=CC2=NC=1C1=CC=CO1 XHONYMKHKBKRRP-UHFFFAOYSA-N 0.000 claims description 3
• DTMZPPANYZJBTP-UHFFFAOYSA-N 7-(4-fluorophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=CC(F)=CC=3)=CC2=NC=1C1=CC=CO1 DTMZPPANYZJBTP-UHFFFAOYSA-N 0.000 claims description 3
• XSKKNRMAYWKFBJ-UHFFFAOYSA-N 7-(5-butylpyridin-2-yl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N1=CC(CCCC)=CC=C1C1=CC2=NC(C=3OC=CC=3)=NN2C(N)=C1 XSKKNRMAYWKFBJ-UHFFFAOYSA-N 0.000 claims description 3
• IODOYXASJJPGLZ-UHFFFAOYSA-N 7-[3,5-bis(trifluoromethyl)phenyl]-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC2=NC=1C1=CC=CO1 IODOYXASJJPGLZ-UHFFFAOYSA-N 0.000 claims description 3
• QSEDUWGIVAJHLZ-UHFFFAOYSA-N ethyl n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)carbamate Chemical compound N=1N2C(NC(=O)OCC)=CC(C=3C=CN=CC=3)=CC2=NC=1C1=CC=CC=C1 QSEDUWGIVAJHLZ-UHFFFAOYSA-N 0.000 claims description 3
• PKSIGPVLQAFEKB-UHFFFAOYSA-N n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 PKSIGPVLQAFEKB-UHFFFAOYSA-N 0.000 claims description 3
• BJZDYLNZQLPWNC-UHFFFAOYSA-N n-ethyl-2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(NCC)=CC(C=3C=CN=CC=3)=CC2=NC=1C1=CC=CC=C1 BJZDYLNZQLPWNC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 3
• YKGCEYXKDQFHBV-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)acetamide Chemical compound ClC1=CC(Cl)=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 YKGCEYXKDQFHBV-UHFFFAOYSA-N 0.000 claims description 2
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• GHPAKNPNSNUUKK-UHFFFAOYSA-N 2-(2-iodophenyl)-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)acetamide Chemical compound IC1=CC=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 GHPAKNPNSNUUKK-UHFFFAOYSA-N 0.000 claims description 2
• HHCYLDWTHIPYMV-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NCCN1 HHCYLDWTHIPYMV-UHFFFAOYSA-N 0.000 claims description 2
• NBVQFHQOXHQRDG-UHFFFAOYSA-N 2-(furan-2-yl)-7-(1h-indol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C4C=CNC4=CC=3)=CC2=NC=1C1=CC=CO1 NBVQFHQOXHQRDG-UHFFFAOYSA-N 0.000 claims description 2
• SWHYOXSWTWFNIX-UHFFFAOYSA-N 2-(furan-2-yl)-7-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound COC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 SWHYOXSWTWFNIX-UHFFFAOYSA-N 0.000 claims description 2
• GNHOGDQVYNXNKY-UHFFFAOYSA-N 2-(furan-2-yl)-7-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1CN(C)CCN1C1=CC2=NC(C=3OC=CC=3)=NN2C(N)=C1 GNHOGDQVYNXNKY-UHFFFAOYSA-N 0.000 claims description 2
• USMVLDUMFVGYDM-UHFFFAOYSA-N 2-(furan-2-yl)-7-(4-methylsulfanylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(SC)=CC=C1C1=CC2=NC(C=3OC=CC=3)=NN2C(N)=C1 USMVLDUMFVGYDM-UHFFFAOYSA-N 0.000 claims description 2
• PKRCKISEAMHMSF-UHFFFAOYSA-N 2-(furan-2-yl)-7-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(C=CC=3)C(F)(F)F)=CC2=NC=1C1=CC=CO1 PKRCKISEAMHMSF-UHFFFAOYSA-N 0.000 claims description 2
• BOAFXBWWJXGJPS-UHFFFAOYSA-N 2-(furan-2-yl)-7-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(N3CCCC3)=CC2=NC=1C1=CC=CO1 BOAFXBWWJXGJPS-UHFFFAOYSA-N 0.000 claims description 2
• TYKHGZPMNRFENH-UHFFFAOYSA-N 2-(furan-2-yl)-7-thiophen-3-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C3=CSC=C3)=CC2=NC=1C1=CC=CO1 TYKHGZPMNRFENH-UHFFFAOYSA-N 0.000 claims description 2
• QDHMWSQHYFSXBH-UHFFFAOYSA-N 7-(3,4-dichlorophenyl)-2-(2,3-dihydrofuran-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(Cl)C(Cl)=CC=3)=CC2=NC=1C1=CCCO1 QDHMWSQHYFSXBH-UHFFFAOYSA-N 0.000 claims description 2
• NALRZNAKLBXNOQ-UHFFFAOYSA-N 7-(3,4-dichlorophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(Cl)C(Cl)=CC=3)=CC2=NC=1C1=CC=CO1 NALRZNAKLBXNOQ-UHFFFAOYSA-N 0.000 claims description 2
• QSNLVTFTCSASDA-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC(C=3OC(C)=CC=3)=NN2C(N)=C1 QSNLVTFTCSASDA-UHFFFAOYSA-N 0.000 claims description 2
• VOSVWWDLBZSWNU-UHFFFAOYSA-N 7-(3,4-dimethoxyphenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC2=NC(C=3OC=CC=3)=NN2C(N)=C1 VOSVWWDLBZSWNU-UHFFFAOYSA-N 0.000 claims description 2
• JSTWJAMAWLRVEM-UHFFFAOYSA-N 7-(3-aminophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound NC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 JSTWJAMAWLRVEM-UHFFFAOYSA-N 0.000 claims description 2
• KDLUZNAWKJPABH-UHFFFAOYSA-N 7-(3-aminophenyl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound NC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2N=CC=CC=2)=C1 KDLUZNAWKJPABH-UHFFFAOYSA-N 0.000 claims description 2
• MWEXBKORZZYJPO-UHFFFAOYSA-N 7-(3-fluorophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C=C(F)C=CC=3)=CC2=NC=1C1=CC=CO1 MWEXBKORZZYJPO-UHFFFAOYSA-N 0.000 claims description 2
• PWFNCZRLTONFFP-UHFFFAOYSA-N 7-(3-methoxyphenyl)-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound COC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC(C)=CC=2)=C1 PWFNCZRLTONFFP-UHFFFAOYSA-N 0.000 claims description 2
• LAWOYVQPLRNQAU-UHFFFAOYSA-N 7-(3-methoxyphenyl)-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound COC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2N=CC=CC=2)=C1 LAWOYVQPLRNQAU-UHFFFAOYSA-N 0.000 claims description 2
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