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)
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| EP99117578 | 1999-09-06 | ||
| EP99117578.7 | 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 (https=) | 2004-12-24 |
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| JP (1) | JP2003528811A (https=) |
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| AR (1) | AR037484A1 (https=) |
| AU (1) | AU7511000A (https=) |
| BR (1) | BR0013792A (https=) |
| CA (1) | CA2383998A1 (https=) |
| CZ (1) | CZ20021220A3 (https=) |
| HR (1) | HRP20020172A2 (https=) |
| HU (1) | HUP0203316A3 (https=) |
| IL (1) | IL148167A0 (https=) |
| MA (1) | MA26816A1 (https=) |
| MX (1) | MXPA02001748A (https=) |
| NO (1) | NO20021077L (https=) |
| PE (1) | PE20010629A1 (https=) |
| PL (1) | PL354240A1 (https=) |
| TR (1) | TR200200579T2 (https=) |
| WO (1) | WO2001017999A2 (https=) |
| YU (1) | YU13502A (https=) |
| ZA (1) | ZA200201055B (https=) |
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| AU2002347055B2 (en) * | 2001-10-08 | 2006-10-12 | F. Hoffmann-La Roche Ag | Substituted Triazolopyridine Compounds |
| US6693116B2 (en) | 2001-10-08 | 2004-02-17 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| ES2283625T3 (es) | 2001-11-30 | 2007-11-01 | Schering Corporation | Antagonistas del receptopr a2a de adenosina de (1,2,4)-triazol biciclicos. |
| 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 |
| CN101543497A (zh) | 2002-01-28 | 2009-09-30 | 协和发酵工业株式会社 | 治疗运动疾病患者的方法 |
| BR0312123A (pt) * | 2002-06-13 | 2005-03-29 | Pfizer | Agentes de gnrh não peptìdicos, composições farmacêuticas e métodos para o seu uso |
| US20080033006A1 (en) * | 2004-01-26 | 2008-02-07 | Altana Pharma Ag | 1,2,4-Triazolo[ 1,5-A] Pyridines as Gastric Acid Secretion Inhibitors |
| DE602005014891D1 (de) | 2004-12-21 | 2009-07-23 | Schering Corp | PYRAZOLOÄ1,5-AÜPYRIMIDINE ALS ANTAGONISTEN DES ADENOSIN-A2a-REZEPTORS |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| EP2081905B1 (en) * | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
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| EA201300152A1 (ru) * | 2006-11-27 | 2013-07-30 | Х. Лундбекк А/С | Гетероариламидные производные |
| JP2010511018A (ja) * | 2006-12-01 | 2010-04-08 | ガラパゴス・ナムローゼ・フェンノートシャップ | 変性疾患及び炎症性疾患の治療に有用なトリアゾロピリジン化合物 |
| BRPI0809567A2 (pt) * | 2007-04-10 | 2014-09-23 | Lundbeck & Co As H | Composto, composição farmacêutica, método para modular a atividade de um receptor de p2x7, para tratar uma condição responsiva à modulação do receptor de p2x7 em um paciente, para inibir a morte de células do gânglio retinal em um paciente, e para determinar a presença ou ausência do receptor de p2x7 em uma amostra, preparação farmacêutica acondiciaonada, e, uso de um composto |
| 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 |
| EP2418207A1 (en) * | 2008-05-13 | 2012-02-15 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the CB2 receptor |
| EP2288260A4 (en) * | 2008-06-20 | 2013-10-23 | Genentech Inc | TRIAZOLOPYRIDINE-JAK HEMMER COMPOUNDS AND METHOD |
| BRPI0909945A2 (pt) | 2008-06-20 | 2015-07-28 | Genentech Inc | "composto, composição farmacêutica, método para tratar ou atenuar a gravidade de uma doença ou condição responsiva à inibição da atividade jak2 quinase em um paciente, kit para o tratamento de uma doença ou distúrbio responsivo à inibição da jak quinase" |
| 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 |
| WO2010036630A2 (en) | 2008-09-25 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| 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 |
| CN102459258B (zh) | 2009-06-05 | 2015-11-25 | 赛福伦公司 | 1,2,4-三唑并[1,5a]吡啶衍生物的制备和用途 |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP5756800B2 (ja) | 2009-06-16 | 2015-07-29 | 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受容体を調節するアゼチジン２−カルボキサミド誘導体 |
| SI2455381T1 (sl) * | 2009-07-17 | 2014-08-29 | Japan Tobacco Inc. | Triazolopiridinova spojina in njeno delovanje kot zaviralec prolil-hidroksilaze in induktor produkcije eritropoietina |
| JP2013505295A (ja) * | 2009-09-22 | 2013-02-14 | 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受容体を選択的に調節する化合物 |
| US9315454B2 (en) | 2010-01-15 | 2016-04-19 | 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 |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | 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 |
| UA108711C2 (uk) * | 2011-09-19 | 2015-05-25 | Ф. Хоффманн-Ля Рош Аг | Сполуки триазолопіридину як інгібітори фосфодіестерази pde10a |
| US9193724B2 (en) * | 2011-09-22 | 2015-11-24 | Merck Sharp & Dohme Corp. | Triazolopyridyl compounds as aldosterone synthase inhibitors |
| WO2013043518A1 (en) | 2011-09-22 | 2013-03-28 | Merck Sharp & Dohme Corp. | Imidazopyridyl 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 |
| CN109963854B (zh) * | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| BR122023024273A2 (pt) | 2018-02-27 | 2024-02-20 | Incyte Corporation | Compostos imidazopirimidinas e triazolopirimidinas, seus usos, método para inibir uma atividade de um receptor de adenosina e composição farmacêutica dos mesmos |
| WO2019222677A1 (en) | 2018-05-18 | 2019-11-21 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| GEP20237548B (en) | 2018-07-05 | 2023-10-10 | Incyte Corp | Fused pyrazine derivatives as a2a /a2b inhibitors |
| JP7399589B2 (ja) * | 2018-09-12 | 2023-12-18 | 日本化薬株式会社 | 有害生物防除剤 |
| CA3124088A1 (en) | 2018-12-20 | 2020-06-25 | Incyte Corporation | Imidazopyridazine and imidazopyridine compounds as inhibitors of activin receptor-like kinase-2 |
| 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 |
| KR20230129291A (ko) * | 2021-01-09 | 2023-09-08 | 버그웍스 리서치 인코포레이션 | 아데노신 2A 수용체 및 아데노신 2B 수용체 길항제로서의 디아미노피라졸로[1,5-a]피리미딘-6-카르보니트릴 화합물 |
| CN116082335B (zh) * | 2023-01-16 | 2026-02-24 | 上海凌凯科技股份有限公司 | 一种二芳基醚化合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9226735D0 (en) | 1992-12-22 | 1993-02-17 | Ici Plc | Azole derivatives |
| WO1999043678A1 (en) | 1998-02-24 | 1999-09-02 | Kyowa Hakko Kogyo Co., Ltd. | Remedies/preventives for parkinson's disease |
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- 2000-08-28 HU HU0203316A patent/HUP0203316A3/hu unknown
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- 2000-08-28 YU YU13502A patent/YU13502A/sh unknown
- 2000-08-28 AU AU75110/00A patent/AU7511000A/en not_active Abandoned
- 2000-08-28 CA CA002383998A patent/CA2383998A1/en not_active Abandoned
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- 2000-08-28 MX MXPA02001748A patent/MXPA02001748A/es unknown
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- 2000-08-28 IL IL14816700A patent/IL148167A0/xx unknown
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- 2000-08-28 TR TR2002/00579T patent/TR200200579T2/xx unknown
- 2000-08-28 KR KR1020027002990A patent/KR20020027625A/ko not_active Ceased
- 2000-08-28 WO PCT/EP2000/008372 patent/WO2001017999A2/en not_active Ceased
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- 2002-03-06 MA MA26540A patent/MA26816A1/fr unknown
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