JP2009538877A5 - - Google Patents
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- JP2009538877A5 JP2009538877A5 JP2009512585A JP2009512585A JP2009538877A5 JP 2009538877 A5 JP2009538877 A5 JP 2009538877A5 JP 2009512585 A JP2009512585 A JP 2009512585A JP 2009512585 A JP2009512585 A JP 2009512585A JP 2009538877 A5 JP2009538877 A5 JP 2009538877A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyrazin
- pyrazol
- piperazin
- ylamino
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- -1 2-morpholin-4-yl-ethoxy Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- CHQJJYPKXYBSSN-UHFFFAOYSA-N N-[4-(4-tert-butylpiperazin-1-yl)phenyl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C(C)(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 CHQJJYPKXYBSSN-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 230000000155 isotopic effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003230 pyrimidines Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- DXISVZIQEPORSC-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 DXISVZIQEPORSC-UHFFFAOYSA-N 0.000 claims 1
- VBVSWIUDHKAUIO-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 VBVSWIUDHKAUIO-UHFFFAOYSA-N 0.000 claims 1
- AGRRXZLTXIRFHF-UHFFFAOYSA-N (4-phenylpiperazin-1-yl)-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC=C1 AGRRXZLTXIRFHF-UHFFFAOYSA-N 0.000 claims 1
- XSDUUIHPTXGMTN-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=C1 XSDUUIHPTXGMTN-UHFFFAOYSA-N 0.000 claims 1
- FFFUXLUPRZEMIL-UHFFFAOYSA-N 1-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]piperazin-2-one Chemical compound O=C1CNCCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 FFFUXLUPRZEMIL-UHFFFAOYSA-N 0.000 claims 1
- QDKZNYZQKYAEMW-UHFFFAOYSA-N 1-[5-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C(N1N=CN=C11)=CN=C1NC1=CC=C(N2CCOCC2)C=C1 QDKZNYZQKYAEMW-UHFFFAOYSA-N 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- YBUAZHKDDGUHHM-UHFFFAOYSA-N 2,5-dihydropyrrol-1-yl-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)N1CC=CC1 YBUAZHKDDGUHHM-UHFFFAOYSA-N 0.000 claims 1
- HRPXCAHEPGIUMW-UHFFFAOYSA-N 2,6-difluoro-4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=C(F)C=C1C(N1N=CN=C11)=CN=C1NC1=CC=C(N2CCOCC2)C=C1 HRPXCAHEPGIUMW-UHFFFAOYSA-N 0.000 claims 1
- YLMHOHHWOPOHBH-UHFFFAOYSA-N 2,6-difluoro-4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC(F)=C(C(N)=O)C(F)=C1 YLMHOHHWOPOHBH-UHFFFAOYSA-N 0.000 claims 1
- BFSRNZLXCZKVNW-UHFFFAOYSA-N 2-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-4,5-dihydrothieno[2,3-c]pyrrol-6-one Chemical compound S1C=2C(=O)NCC=2C=C1C(N1N=CN=C11)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 BFSRNZLXCZKVNW-UHFFFAOYSA-N 0.000 claims 1
- CGZZIEITQLQBOG-UHFFFAOYSA-N 2-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-5,6-dihydrofuro[2,3-c]pyrrol-4-one Chemical compound C=1C=2C(=O)NCC=2OC=1C(N1N=CN=C11)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 CGZZIEITQLQBOG-UHFFFAOYSA-N 0.000 claims 1
- VKUVJWJZEWKBRP-UHFFFAOYSA-N 2-fluoro-4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=CC=C1C(N1N=CN=C11)=CN=C1NC1=CC=C(N2CCOCC2)C=C1 VKUVJWJZEWKBRP-UHFFFAOYSA-N 0.000 claims 1
- BNNUKUVBEFWNMO-UHFFFAOYSA-N 2-fluoro-4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=C(C(N)=O)C(F)=C1 BNNUKUVBEFWNMO-UHFFFAOYSA-N 0.000 claims 1
- VBVIHCRFIFYNSO-UHFFFAOYSA-N 2-methoxy-N-[(6-methylpyridin-3-yl)methyl]-4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound C=1C=C(C(=O)NCC=2C=NC(C)=CC=2)C(OC)=CC=1NC(C1=NC=NN11)=NC=C1C=1C=NNC=1 VBVIHCRFIFYNSO-UHFFFAOYSA-N 0.000 claims 1
- GIAQJIIDNXNNSY-UHFFFAOYSA-N 3,3-dimethyl-5-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-2h-isoindol-1-one Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=C(C(=O)NC2(C)C)C2=C1 GIAQJIIDNXNNSY-UHFFFAOYSA-N 0.000 claims 1
- QVDSFKDOVDIPSJ-UHFFFAOYSA-N 3,6-dihydro-2H-pyridin-1-yl-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)N1CCC=CC1 QVDSFKDOVDIPSJ-UHFFFAOYSA-N 0.000 claims 1
- ZIJWGGAFCXAOPN-UHFFFAOYSA-N 3-[4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound N1C(=O)CCC(C=2C=CC(=CC=2)C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=N1 ZIJWGGAFCXAOPN-UHFFFAOYSA-N 0.000 claims 1
- MMPDHCPOSYHTSV-UHFFFAOYSA-N 3-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1-benzothiophene-7-carboxylic acid Chemical compound C=1SC=2C(C(=O)O)=CC=CC=2C=1C(N1N=CN=C11)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 MMPDHCPOSYHTSV-UHFFFAOYSA-N 0.000 claims 1
- UXDBSBVOMPXFBF-UHFFFAOYSA-N 3-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1-benzothiophene-7-carboxamide Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC2=C(C(N)=O)C=CC=C12 UXDBSBVOMPXFBF-UHFFFAOYSA-N 0.000 claims 1
- JHOJVWLTDDKOKE-UHFFFAOYSA-N 3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]-N-(pyridin-2-ylmethyl)benzamide Chemical compound C=1C=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=CC=1C(=O)NCC1=CC=CC=N1 JHOJVWLTDDKOKE-UHFFFAOYSA-N 0.000 claims 1
- GZYQVOQCWOVTBW-UHFFFAOYSA-N 3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound NC(=O)C1=CC=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=C1 GZYQVOQCWOVTBW-UHFFFAOYSA-N 0.000 claims 1
- ZSUFWZOCGCTTBU-UHFFFAOYSA-N 3-fluoro-4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound FC1=CC(C(=O)N)=CC=C1C(N1N=CN=C11)=CN=C1NC1=CC=C(N2CCOCC2)C=C1 ZSUFWZOCGCTTBU-UHFFFAOYSA-N 0.000 claims 1
- ZKIPRFSOFNNCMK-UHFFFAOYSA-N 3-fluoro-4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=C(C(N)=O)C=C1F ZKIPRFSOFNNCMK-UHFFFAOYSA-N 0.000 claims 1
- BUYLMIPFLKSPIS-UHFFFAOYSA-N 4-[4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]phenyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC(=CC=2)C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 BUYLMIPFLKSPIS-UHFFFAOYSA-N 0.000 claims 1
- QSPAEZUXLKWALT-UHFFFAOYSA-N 4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1,3-thiazole-2-carboxamide Chemical compound S1C(C(=O)N)=NC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 QSPAEZUXLKWALT-UHFFFAOYSA-N 0.000 claims 1
- IUSQIOFMDVXKRJ-UHFFFAOYSA-N 4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(N1N=CN=C11)=CN=C1NC1=CC=C(N2CCOCC2)C=C1 IUSQIOFMDVXKRJ-UHFFFAOYSA-N 0.000 claims 1
- FYSTUPGUTFXHBJ-UHFFFAOYSA-N 4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 FYSTUPGUTFXHBJ-UHFFFAOYSA-N 0.000 claims 1
- SFEDCFUOTZYOEK-UHFFFAOYSA-N 4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 SFEDCFUOTZYOEK-UHFFFAOYSA-N 0.000 claims 1
- WNDKNBCWYSXUPN-UHFFFAOYSA-N 4-[8-(4-piperazin-1-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCNCC3)=NC=2)=C1 WNDKNBCWYSXUPN-UHFFFAOYSA-N 0.000 claims 1
- JPRCFWLPRKUDRL-UHFFFAOYSA-N 4-[8-[(6-benzamidopyridin-3-yl)amino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=NC(NC(=O)C=4C=CC=CC=4)=CC=3)=NC=2)=C1 JPRCFWLPRKUDRL-UHFFFAOYSA-N 0.000 claims 1
- ZWOSSIVBFAYQDW-UHFFFAOYSA-N 4-[8-[(6-morpholin-4-ylpyridin-3-yl)amino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=NC(=CC=3)N3CCOCC3)=NC=2)=C1 ZWOSSIVBFAYQDW-UHFFFAOYSA-N 0.000 claims 1
- MDGOPRLPIZCNLF-UHFFFAOYSA-N 4-[8-[(6-morpholin-4-ylpyridin-3-yl)amino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=NC(=CC=3)N3CCOCC3)=NC=2)=C1 MDGOPRLPIZCNLF-UHFFFAOYSA-N 0.000 claims 1
- IMPPWUFSZPGBCS-UHFFFAOYSA-N 4-[8-[3-methoxy-4-[(6-methylpyridin-3-yl)methylcarbamoyl]anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC=2C=NC(C)=CC=2)C(OC)=CC=1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=C1 IMPPWUFSZPGBCS-UHFFFAOYSA-N 0.000 claims 1
- CBDPFOMIDRBHPG-UHFFFAOYSA-N 4-[8-[4-(2-morpholin-4-ylethoxy)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical class S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(OCCN4CCOCC4)=CC=3)=NC=2)=C1 CBDPFOMIDRBHPG-UHFFFAOYSA-N 0.000 claims 1
- ULADOTYNHIXXPX-UHFFFAOYSA-N 4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1h-pyridin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC(=O)NC=C1 ULADOTYNHIXXPX-UHFFFAOYSA-N 0.000 claims 1
- RPTBHZFWKPSPBV-UHFFFAOYSA-N 4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=C(C(N)=O)C=C1 RPTBHZFWKPSPBV-UHFFFAOYSA-N 0.000 claims 1
- JGGDMMYPOPZHLL-UHFFFAOYSA-N 4-[8-[4-(4-methylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical class C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=C1 JGGDMMYPOPZHLL-UHFFFAOYSA-N 0.000 claims 1
- JQWATXZJZVGVRZ-UHFFFAOYSA-N 4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1,3-thiazole-2-carboxamide Chemical class C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=N1 JQWATXZJZVGVRZ-UHFFFAOYSA-N 0.000 claims 1
- ZYVZHYOXPSBOIR-UHFFFAOYSA-N 4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=CC2=C1CNC2=O ZYVZHYOXPSBOIR-UHFFFAOYSA-N 0.000 claims 1
- COGVMNOHISNIOE-UHFFFAOYSA-N 4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]furan-2-carboxamide Chemical class C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=COC(C(N)=O)=C1 COGVMNOHISNIOE-UHFFFAOYSA-N 0.000 claims 1
- WZVOWQNLPSCZPI-UHFFFAOYSA-N 4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical class C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=C1 WZVOWQNLPSCZPI-UHFFFAOYSA-N 0.000 claims 1
- HIXXPXGQJXLBEW-UHFFFAOYSA-N 4-[8-[4-(benzylcarbamoyl)-3-methoxyanilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound C=1C=C(C(=O)NCC=2C=CC=CC=2)C(OC)=CC=1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=C1 HIXXPXGQJXLBEW-UHFFFAOYSA-N 0.000 claims 1
- IAPMHNPGQOHSOR-OKILXGFUSA-N 4-[8-[4-[(2s,6r)-2,6-dimethylmorpholin-4-yl]anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC(C(N)=O)=C1 IAPMHNPGQOHSOR-OKILXGFUSA-N 0.000 claims 1
- IIBPKZRWJHPSBG-UHFFFAOYSA-N 4-[8-[4-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)C3CCN(CC(F)(F)F)CC3)=NC=2)=C1 IIBPKZRWJHPSBG-UHFFFAOYSA-N 0.000 claims 1
- SFFPRZBXKZPBER-UHFFFAOYSA-N 4-[8-[4-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCN(CC(F)(F)F)CC3)=NC=2)=C1 SFFPRZBXKZPBER-UHFFFAOYSA-N 0.000 claims 1
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- PBERAIPVANFQPF-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-5-thiophen-3-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC=C1 PBERAIPVANFQPF-UHFFFAOYSA-N 0.000 claims 1
- ZJKDVULACFEGOT-UHFFFAOYSA-N n-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-5-thiophen-3-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CSC=C1 ZJKDVULACFEGOT-UHFFFAOYSA-N 0.000 claims 1
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- UPWIOQFFWNNUKK-UHFFFAOYSA-N n-methyl-4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1,3-thiazole-2-carboxamide Chemical compound S1C(C(=O)NC)=NC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCN(CC3)C(C)C)=NC=2)=C1 UPWIOQFFWNNUKK-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
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| WO2008065198A1 (en) | 2006-12-01 | 2008-06-05 | Galapagos N.V. | Triazolopyridine compounds useful for the treatment of degenerative & inflammatory diseases |
| WO2008138843A1 (en) * | 2007-05-10 | 2008-11-20 | Galapagos N.V. | Imidazopyridines and triazolopyrimidines useful for the treatment of joint degenerative & inflammatory diseases |
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- 2007-05-30 HR HR20100378T patent/HRP20100378T1/hr unknown
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- 2007-05-30 AU AU2007267121A patent/AU2007267121A1/en not_active Abandoned
- 2007-05-30 JP JP2009512585A patent/JP2009538877A/ja not_active Abandoned
- 2007-05-30 WO PCT/EP2007/055246 patent/WO2007138072A2/en not_active Ceased
- 2007-05-30 US US11/809,294 patent/US7501411B2/en not_active Expired - Fee Related
- 2007-05-30 DE DE602007006010T patent/DE602007006010D1/de active Active
- 2007-05-30 EA EA200870592A patent/EA200870592A1/ru unknown
- 2007-05-30 BR BRPI0712531-3A patent/BRPI0712531A2/pt not_active IP Right Cessation
- 2007-05-30 NZ NZ573015A patent/NZ573015A/en not_active IP Right Cessation
- 2007-05-30 KR KR1020087030751A patent/KR20090026288A/ko not_active Withdrawn
- 2007-05-30 DK DK07729660.6T patent/DK2029602T3/da active
- 2007-05-30 CA CA002653506A patent/CA2653506A1/en not_active Abandoned
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2008
- 2008-10-30 IL IL195033A patent/IL195033A0/en unknown
- 2008-11-10 NO NO20084703A patent/NO20084703L/no not_active Application Discontinuation
- 2008-11-20 NI NI200800299A patent/NI200800299A/es unknown
- 2008-11-25 CR CR10458A patent/CR10458A/es unknown
- 2008-11-28 EC EC2008008923A patent/ECSP088923A/es unknown
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2009
- 2009-03-08 US US12/399,979 patent/US7915256B2/en not_active Expired - Fee Related
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2011
- 2011-01-09 US US12/987,129 patent/US20110178067A1/en not_active Abandoned
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