JP2003528811A5 - - Google Patents
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- JP2003528811A5 JP2003528811A5 JP2001522222A JP2001522222A JP2003528811A5 JP 2003528811 A5 JP2003528811 A5 JP 2003528811A5 JP 2001522222 A JP2001522222 A JP 2001522222A JP 2001522222 A JP2001522222 A JP 2001522222A JP 2003528811 A5 JP2003528811 A5 JP 2003528811A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- phenyl
- triazolo
- ylamine
- furan
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- -1 1,3,4,9-tetrahydro-β-carbolin-2-yl Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 102000009346 Adenosine receptors Human genes 0.000 claims 2
- 108050000203 Adenosine receptors Proteins 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 2
- CRCOKEDXDNFVGG-UHFFFAOYSA-N 1-[3-[5-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 CRCOKEDXDNFVGG-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 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 1
- 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 1
- WVVDXRUQPCPOJZ-UHFFFAOYSA-N 2-(2,3-dihydrofuran-5-yl)-7-(3-fluorophenyl)-[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=CCCO1 WVVDXRUQPCPOJZ-UHFFFAOYSA-N 0.000 claims 1
- BVEFAFGNISJMPR-UHFFFAOYSA-N 2-(2,3-dihydrofuran-5-yl)-7-(3-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound CC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OCCC=2)=C1 BVEFAFGNISJMPR-UHFFFAOYSA-N 0.000 claims 1
- TVSLJOVWKFPMKB-UHFFFAOYSA-N 2-(2,3-dihydrofuran-5-yl)-7-(4-fluorophenyl)-[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=CCCO1 TVSLJOVWKFPMKB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IMUFWXZIIDOQAQ-UHFFFAOYSA-N 2-(2-bromophenyl)-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)acetamide Chemical compound BrC1=CC=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 IMUFWXZIIDOQAQ-UHFFFAOYSA-N 0.000 claims 1
- MWSYEAKDIDVAAZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)acetamide Chemical compound ClC1=CC=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 MWSYEAKDIDVAAZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- KJLALFLXCGEMNI-UHFFFAOYSA-N 2-(furan-2-yl)-7-(3-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound CC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 KJLALFLXCGEMNI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- DVQLSDFSJSMFNH-UHFFFAOYSA-N 2-pyrazol-1-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=1N1C=CC=N1 DVQLSDFSJSMFNH-UHFFFAOYSA-N 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- MHXFXAGDVVLZFO-UHFFFAOYSA-N 7-(2-fluorophenyl)-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound N=1N2C(N)=CC(C=3C(=CC=CC=3)F)=CC2=NC=1C1=CC=CO1 MHXFXAGDVVLZFO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZQWDKRYETWFRHF-UHFFFAOYSA-N 7-(3,5-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=C(Cl)C=3)=CC2=NC=1C1=CC=CO1 ZQWDKRYETWFRHF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LLPKFHYIIJFUIT-UHFFFAOYSA-N 7-(4-chlorophenyl)-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine Chemical compound O1C(C)=CC=C1C1=NN2C(N)=CC(C=3C=CC(Cl)=CC=3)=CC2=N1 LLPKFHYIIJFUIT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- VIEQYENWRGCUQK-UHFFFAOYSA-N 7-(4-fluorophenyl)-2-pyridin-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=CC=N1 VIEQYENWRGCUQK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- 229930192627 Naphthoquinone Natural products 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SLIBDLGBBDOHKB-UHFFFAOYSA-N n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-[2-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 SLIBDLGBBDOHKB-UHFFFAOYSA-N 0.000 claims 1
- YCLOADXWKJBGLT-UHFFFAOYSA-N n-(2-phenyl-7-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(=O)NC1=CC(C=2C=CN=CC=2)=CC2=NC(C=3C=CC=CC=3)=NN12 YCLOADXWKJBGLT-UHFFFAOYSA-N 0.000 claims 1
- NDKWJTYXGSHIPY-UHFFFAOYSA-N n-[3-[5-amino-2-(5-methylfuran-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC(C)=CC=2)=C1 NDKWJTYXGSHIPY-UHFFFAOYSA-N 0.000 claims 1
- FAWMVHVNJSSLMA-UHFFFAOYSA-N n-[3-[5-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C2=CC3=NC(=NN3C(N)=C2)C=2OC=CC=2)=C1 FAWMVHVNJSSLMA-UHFFFAOYSA-N 0.000 claims 1
- JYIYWVDZWJAXEG-UHFFFAOYSA-N n-[4-[5-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-2-methylphenyl]acetamide Chemical compound C1=C(C)C(NC(=O)C)=CC=C1C1=CC2=NC(C=3OC=CC=3)=NN2C(N)=C1 JYIYWVDZWJAXEG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000002791 naphthoquinones Chemical class 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 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 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP99117578.7 | 1999-09-06 | ||
| EP99117578 | 1999-09-06 | ||
| PCT/EP2000/008372 WO2001017999A2 (en) | 1999-09-06 | 2000-08-28 | Amino-triazolopyridine derivatives |
Publications (2)
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| JP2003528811A JP2003528811A (ja) | 2003-09-30 |
| JP2003528811A5 true JP2003528811A5 (cg-RX-API-DMAC7.html) | 2004-12-24 |
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| JP2001522222A Pending JP2003528811A (ja) | 1999-09-06 | 2000-08-28 | アミノトリアゾロピリジン誘導体 |
Country Status (22)
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| US6506772B1 (en) * | 2000-12-15 | 2003-01-14 | Hoffmann-La Roche Inc. | Substituted [1,2,4]triazolo[1,5a]pyridine derivatives with activity as adenosine receptor ligands |
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| US6693116B2 (en) * | 2001-10-08 | 2004-02-17 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| MXPA04003277A (es) * | 2001-10-08 | 2004-07-23 | Hoffmann La Roche | Amida del acido 8-amino-?1,2,4?triazolo?1,5-a?piridina-6-carboxilico. |
| ATE358130T1 (de) | 2001-11-30 | 2007-04-15 | Schering Corp | Bicyclische (1,2,4ö-triazol adenosin a2a rezeptor antagonisten |
| HUP0105407A3 (en) * | 2001-12-21 | 2004-04-28 | Sanofi Aventis | Triazolo[1,5-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| KR101166000B1 (ko) | 2002-01-28 | 2012-07-16 | 교와 핫꼬 기린 가부시키가이샤 | 운동성 질환에 걸린 환자의 치료 방법 |
| WO2003106446A1 (en) * | 2002-06-13 | 2003-12-24 | Pfizer Inc. | Non-peptide gnrh agents, pharmaceutical compositions and methods for their use |
| US20080033006A1 (en) * | 2004-01-26 | 2008-02-07 | Altana Pharma Ag | 1,2,4-Triazolo[ 1,5-A] Pyridines as Gastric Acid Secretion Inhibitors |
| MX2007007604A (es) * | 2004-12-21 | 2007-08-02 | Schering Corp | Antagonistas del receptor de pirazolo[1,5-a]pirimidina adenosina a2a. |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| US7935715B2 (en) * | 2006-07-28 | 2011-05-03 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| JP5030114B2 (ja) * | 2006-09-25 | 2012-09-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体をモジュレートする化合物 |
| EA018036B1 (ru) * | 2006-11-27 | 2013-05-30 | Х. Лундбекк А/С | Гетероариламидные производные |
| US7977352B2 (en) | 2006-12-01 | 2011-07-12 | Galapagos Nv | Triazolopyridine compounds useful for the treatment of degenerative and inflammatory diseases |
| EA200970931A1 (ru) * | 2007-04-10 | 2010-04-30 | Х. Лундбекк А/С | Аналоги гетероариламидов |
| WO2009017954A1 (en) * | 2007-08-01 | 2009-02-05 | Phenomix Corporation | Inhibitors of jak2 kinase |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| JP5492092B2 (ja) * | 2007-11-07 | 2014-05-14 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ２受容体を調節する化合物 |
| EP2283001A2 (en) * | 2008-05-13 | 2011-02-16 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| CN102131390A (zh) * | 2008-06-20 | 2011-07-20 | 健泰科生物技术公司 | 三唑并吡啶jak抑制剂化合物和方法 |
| JP5512665B2 (ja) | 2008-06-20 | 2014-06-04 | ジェネンテック， インコーポレイテッド | トリアゾロピリジンｊａｋ阻害剤化合物と方法 |
| EP2326629B1 (en) * | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| TWI453207B (zh) * | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| BRPI0919172A2 (pt) * | 2008-09-25 | 2015-12-15 | Boehringer Ingelheim Int | compostos os quais modulam seletivamente o receptor de cb2 |
| MY153913A (en) * | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| NZ597140A (en) | 2009-06-05 | 2014-01-31 | Cephalon Inc | Preparation and uses of 1,2,4-triazolo [1,5a] pyridine derivatives |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| WO2010147791A1 (en) | 2009-06-16 | 2010-12-23 | Boehringer Ingelheim International Gmbh | Azetidine 2 -carboxamide derivatives which modulate the cb2 receptor |
| PE20120629A1 (es) * | 2009-07-17 | 2012-05-30 | Japan Tobacco Inc | Compuesto triazolopiridina y su accion como inhibidor de prolil hidroxilasa e inductor de la produccion de eritropoyetina |
| EP2480544A1 (en) * | 2009-09-22 | 2012-08-01 | Boehringer Ingelheim International GmbH | Compounds which selectively modulate the cb2 receptor |
| WO2011088015A1 (en) | 2010-01-15 | 2011-07-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2542539B1 (en) | 2010-03-05 | 2014-02-26 | Boehringer Ingelheim International GmbH | Tetrazole compounds which selectively modulate the cb2 receptor |
| WO2012012307A1 (en) | 2010-07-22 | 2012-01-26 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the cb2 rece |
| AU2012311713A1 (en) * | 2011-09-19 | 2014-03-13 | F. Hoffmann-La Roche Ag | Triazolopyridine compounds as PDE10A inhibitors |
| EP2757882B1 (en) | 2011-09-22 | 2020-11-04 | Merck Sharp & Dohme Corp. | Imidazopyridyl compounds as aldosterone synthase inhibitors |
| EP2757883B1 (en) * | 2011-09-22 | 2021-01-13 | Merck Sharp & Dohme Corp. | Triazolopyridyl compounds as aldosterone synthase inhibitors |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| CN109071444A (zh) | 2016-03-16 | 2018-12-21 | 拜耳作物科学股份公司 | 作为农药和植物保护剂的n-(氰苄基)-6-(环丙基-羰基氨基)-4-(苯基)-吡啶-2-羧酰胺衍生物及相关化合物 |
| CN106543175B (zh) * | 2016-10-28 | 2018-06-01 | 上海大学 | 三芳基[1,2,4]三氮唑[1,5-a]吡啶衍生物及其制备方法 |
| JP7111733B2 (ja) * | 2017-03-16 | 2022-08-02 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ヘテロアリール［４，３－ｃ］ピリミジン－５－アミン誘導体、その製造方法、およびその医薬の使用 |
| CR20230030A (es) | 2018-02-27 | 2023-03-10 | Incyte Corp | Imidazopirimidinas y triazolopirimidinas como inhibidores de a2a / a2b (divisional 2020-0441) |
| MA52940A (fr) | 2018-05-18 | 2021-04-28 | Incyte Corp | Dérivés de pyrimidine fusionnés utilisés en tant qu'inhibiteurs de a2a/a2b |
| CN117304191A (zh) * | 2018-07-05 | 2023-12-29 | 因赛特公司 | 作为a2a/a2b抑制剂的稠合吡嗪衍生物 |
| WO2020054712A1 (ja) * | 2018-09-12 | 2020-03-19 | 日本化薬株式会社 | 有害生物防除剤 |
| IL318278A (en) | 2018-12-20 | 2025-03-01 | Incyte Corp | Imidazopyridazine and imidazopyridine compounds and their use |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| CA3172939A1 (en) * | 2021-01-09 | 2022-07-14 | Bugworks Research, Inc. | Diaminopyrazolo[1,5-a]pyrimidine-6-carbonitrile compounds as adenosine 2a receptor and adenosine 2b receptor antagonist |
| CN116082335A (zh) * | 2023-01-16 | 2023-05-09 | 上海凌凯医药科技有限公司 | 一种二芳基醚化合物的制备方法 |
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| GB9226735D0 (en) | 1992-12-22 | 1993-02-17 | Ici Plc | Azole derivatives |
| AU2639299A (en) | 1998-02-24 | 1999-09-15 | Kyowa Hakko Kogyo Co. Ltd. | Remedies/preventives for parkinson's disease |
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- 2000-08-28 PL PL00354240A patent/PL354240A1/xx not_active Application Discontinuation
- 2000-08-28 BR BR0013792-8A patent/BR0013792A/pt not_active IP Right Cessation
- 2000-08-28 HR HR20020172A patent/HRP20020172A2/hr not_active Application Discontinuation
- 2000-08-28 JP JP2001522222A patent/JP2003528811A/ja active Pending
- 2000-08-28 CZ CZ20021220A patent/CZ20021220A3/cs unknown
- 2000-08-28 HU HU0203316A patent/HUP0203316A3/hu unknown
- 2000-08-28 EP EP00964043A patent/EP1214322A2/en not_active Withdrawn
- 2000-08-28 YU YU13502A patent/YU13502A/sh unknown
- 2000-08-28 CA CA002383998A patent/CA2383998A1/en not_active Abandoned
- 2000-08-28 CN CN00812501A patent/CN1379777A/zh active Pending
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- 2000-08-28 TR TR2002/00579T patent/TR200200579T2/xx unknown
- 2000-08-28 AU AU75110/00A patent/AU7511000A/en not_active Abandoned
- 2000-08-28 KR KR1020027002990A patent/KR20020027625A/ko not_active Ceased
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2002
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- 2002-03-06 MA MA26540A patent/MA26816A1/fr unknown
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