HRP20100378T1 - Spojevi triazolopirazina učinkoviti za tretman degenerativnih i upalnih bolesti - Google Patents
Spojevi triazolopirazina učinkoviti za tretman degenerativnih i upalnih bolesti Download PDFInfo
- Publication number
- HRP20100378T1 HRP20100378T1 HR20100378T HRP20100378T HRP20100378T1 HR P20100378 T1 HRP20100378 T1 HR P20100378T1 HR 20100378 T HR20100378 T HR 20100378T HR P20100378 T HRP20100378 T HR P20100378T HR P20100378 T1 HRP20100378 T1 HR P20100378T1
- Authority
- HR
- Croatia
- Prior art keywords
- triazolo
- pyrazin
- pyrazol
- piperazin
- ylamino
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract 4
- 208000027866 inflammatory disease Diseases 0.000 title claims 2
- CJGGKSPGRJHZNP-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyrazine Chemical class C1=CN=C2NN=NC2=N1 CJGGKSPGRJHZNP-UHFFFAOYSA-N 0.000 title 1
- 230000003412 degenerative effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 51
- -1 Amide 4-{8-[4-(4-methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophen-2- carboxylic acids Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 150000001408 amides Chemical class 0.000 claims 6
- 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
- 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
- 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 2
- 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
- 229940079593 drug Drugs 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 230000000155 isotopic effect Effects 0.000 claims 2
- 238000011321 prophylaxis Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- XTOZATPZCUYVPR-UHFFFAOYSA-N (4-piperidin-1-ylpiperidin-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)CCC1N1CCCCC1 XTOZATPZCUYVPR-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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- 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
- JYBCHEQZETVKRB-UHFFFAOYSA-N 3-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1-benzothiophene-7-carboxamide Chemical compound C=1SC=2C(C(=O)N)=CC=CC=2C=1C(N1N=CN=C11)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 JYBCHEQZETVKRB-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
- 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
- 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
- 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
- AHMHYVIPXVLMLM-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-carboxylic acid Chemical compound S1C(C(=O)O)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)C3CCN(CC(F)(F)F)CC3)=NC=2)=C1 AHMHYVIPXVLMLM-UHFFFAOYSA-N 0.000 claims 1
- VLHDUMDOLLDKJW-UHFFFAOYSA-N 4-[8-[[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]amino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-2,3-dihydroisoindol-1-one Chemical compound C1CN(C(C)C)CCN1C(N=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=CC2=C1CNC2=O VLHDUMDOLLDKJW-UHFFFAOYSA-N 0.000 claims 1
- NNAAHUUFMAXYRO-UHFFFAOYSA-N 4-[8-[[6-[(2-phenylacetyl)amino]pyridin-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)CC=4C=CC=CC=4)=CC=3)=NC=2)=C1 NNAAHUUFMAXYRO-UHFFFAOYSA-N 0.000 claims 1
- BROKFMHCLYAGQE-UHFFFAOYSA-N 4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]-N-(2-pyridin-4-ylethyl)benzamide Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)NCCC1=CC=NC=C1 BROKFMHCLYAGQE-UHFFFAOYSA-N 0.000 claims 1
- LCRWIORMRJTMFA-UHFFFAOYSA-N 4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]-N-(pyridin-3-ylmethyl)benzamide Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)NCC1=CC=CN=C1 LCRWIORMRJTMFA-UHFFFAOYSA-N 0.000 claims 1
- QTKFTAILYNCRCP-UHFFFAOYSA-N 4-[[5-(2-oxo-1h-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]-n-(pyridin-3-ylmethyl)benzamide Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CC(=O)NC=C3)=CN=2)C=CC=1C(=O)NCC1=CC=CN=C1 QTKFTAILYNCRCP-UHFFFAOYSA-N 0.000 claims 1
- DEFMVBAGGURMRQ-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-n-(4-morpholin-4-ylphenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=C(N=CS2)C2=C1 DEFMVBAGGURMRQ-UHFFFAOYSA-N 0.000 claims 1
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- KEJPHZROOKODRB-UHFFFAOYSA-N N-[4-(4-methylpiperazin-1-yl)phenyl]-5-(5-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=C(C)NN=C1 KEJPHZROOKODRB-UHFFFAOYSA-N 0.000 claims 1
- MGRBMXPGSUXSTD-UHFFFAOYSA-N N-[4-(4-propan-2-ylpiperazin-1-yl)phenyl]-5-(1H-pyrazol-4-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=CNN=C1 MGRBMXPGSUXSTD-UHFFFAOYSA-N 0.000 claims 1
- SJFCALIVDFEXCP-UHFFFAOYSA-N N-[4-[4-(cyclopropylmethyl)piperazin-1-yl]phenyl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C=2C=CC(NC=3C4=NC=NN4C(C4=CNN=C4)=CN=3)=CC=2)CCN1CC1CC1 SJFCALIVDFEXCP-UHFFFAOYSA-N 0.000 claims 1
- SRKUNLZTJIAOGZ-UHFFFAOYSA-N N-[5-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]pyridin-2-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(N=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C=1C=NNC=1 SRKUNLZTJIAOGZ-UHFFFAOYSA-N 0.000 claims 1
- KERZSNOOXAGUFL-UHFFFAOYSA-N N-[6-(4-cyclopropylpiperazin-1-yl)pyridin-3-yl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CC1N1CCN(C=2N=CC(NC=3C4=NC=NN4C(C4=CNN=C4)=CN=3)=CC=2)CC1 KERZSNOOXAGUFL-UHFFFAOYSA-N 0.000 claims 1
- JINMLVRMKSGVRV-UHFFFAOYSA-N N-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C(C)C)CCN1C(N=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 JINMLVRMKSGVRV-UHFFFAOYSA-N 0.000 claims 1
- FCYIPZNUCTWQFY-UHFFFAOYSA-N N-[6-[4-(cyclopropylmethyl)piperazin-1-yl]pyridin-3-yl]-5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1CN(C=2N=CC(NC=3C4=NC=NN4C(C4=CNN=C4)=CN=3)=CC=2)CCN1CC1CC1 FCYIPZNUCTWQFY-UHFFFAOYSA-N 0.000 claims 1
- DGACUWHSLZOGAZ-SFHVURJKSA-N N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 DGACUWHSLZOGAZ-SFHVURJKSA-N 0.000 claims 1
- MIRIRWWYQHEKPE-UHFFFAOYSA-N N-benzyl-2-methoxy-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=CC=CC=2)C(OC)=CC=1NC(C1=NC=NN11)=NC=C1C=1C=NNC=1 MIRIRWWYQHEKPE-UHFFFAOYSA-N 0.000 claims 1
- GBIAFQRZAYQVBC-UHFFFAOYSA-N N-benzyl-3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound C=1C=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=CC=1C(=O)NCC1=CC=CC=C1 GBIAFQRZAYQVBC-UHFFFAOYSA-N 0.000 claims 1
- IKEUUXDJMMATCV-UHFFFAOYSA-N N-benzyl-N-methyl-3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound C=1C=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=CC=1C(=O)N(C)CC1=CC=CC=C1 IKEUUXDJMMATCV-UHFFFAOYSA-N 0.000 claims 1
- RPBFPZSBRGQZAF-UHFFFAOYSA-N N-ethyl-3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound CCNC(=O)C1=CC=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=C1 RPBFPZSBRGQZAF-UHFFFAOYSA-N 0.000 claims 1
- MRMRRGWJZIPTEQ-UHFFFAOYSA-N N-ethyl-N-(2-methoxyethyl)-4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzamide Chemical compound C1=CC(C(=O)N(CCOC)CC)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 MRMRRGWJZIPTEQ-UHFFFAOYSA-N 0.000 claims 1
- FGJJUTFVNJSGHQ-UHFFFAOYSA-N N-methyl-1-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzoyl]piperidine-4-carboxamide Chemical class C1CC(C(=O)NC)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 FGJJUTFVNJSGHQ-UHFFFAOYSA-N 0.000 claims 1
- NYBGGMPLCJTBCY-UHFFFAOYSA-N N-methyl-N-[1-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzoyl]pyrrolidin-3-yl]acetamide Chemical compound C1C(N(C)C(C)=O)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 NYBGGMPLCJTBCY-UHFFFAOYSA-N 0.000 claims 1
- AVAQBDJGLMVHMR-UHFFFAOYSA-N N-propan-2-yl-2-[4-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]benzoyl]piperazin-1-yl]acetamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 AVAQBDJGLMVHMR-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 1
- JFDPEWDADGRRQZ-UHFFFAOYSA-N [2-morpholin-4-yl-5-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanol Chemical compound C=1C=C(N2CCOCC2)C(CO)=CC=1NC(C1=NC=NN11)=NC=C1C=1C=NNC=1 JFDPEWDADGRRQZ-UHFFFAOYSA-N 0.000 claims 1
- SSPDVDXYRRZJBK-UHFFFAOYSA-N [3-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=CC(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)=CC=1C(=O)N1CCCC1 SSPDVDXYRRZJBK-UHFFFAOYSA-N 0.000 claims 1
- IFMOEGNAPRSVHB-UHFFFAOYSA-N [4-(2-ethoxyethyl)piperazin-1-yl]-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CN(CCOCC)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 IFMOEGNAPRSVHB-UHFFFAOYSA-N 0.000 claims 1
- RZKJJLFMOSCVCC-UHFFFAOYSA-N [4-(2-methoxyethyl)piperazin-1-yl]-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1CN(CCOC)CCN1C(=O)C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 RZKJJLFMOSCVCC-UHFFFAOYSA-N 0.000 claims 1
- XXXRYBDZRYYDSC-UHFFFAOYSA-N [4-[(4-fluorophenyl)methyl]piperazin-1-yl]-[4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]methanone Chemical compound C1=CC(F)=CC=C1CN1CCN(C(=O)C=2C=CC(NC=3C4=NC=NN4C(C4=CNN=C4)=CN=3)=CC=2)CC1 XXXRYBDZRYYDSC-UHFFFAOYSA-N 0.000 claims 1
- NFPDZRYLXOILPI-UHFFFAOYSA-N [4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-1H-pyrazol-5-yl]methanol Chemical compound N1N=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1CO NFPDZRYLXOILPI-UHFFFAOYSA-N 0.000 claims 1
- CPICEHFVWBSXJW-UHFFFAOYSA-N [4-[8-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]pyridin-2-yl]methanol Chemical compound C1=NC(CO)=CC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 CPICEHFVWBSXJW-UHFFFAOYSA-N 0.000 claims 1
- XMGJRIGZLBBPSS-UHFFFAOYSA-N [4-[8-[4-(4-propan-2-ylpiperazin-1-yl)anilino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]pyridin-2-yl]methanol Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=NC(CO)=C1 XMGJRIGZLBBPSS-UHFFFAOYSA-N 0.000 claims 1
- WIWYXIDDANSIFL-UHFFFAOYSA-N [4-[8-[[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]amino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]pyridin-2-yl]methanol Chemical compound C1CN(C(C)C)CCN1C(N=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=NC(CO)=C1 WIWYXIDDANSIFL-UHFFFAOYSA-N 0.000 claims 1
- CVSBUKOCITYUCO-UHFFFAOYSA-N [4-[[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]amino]phenyl]-(4-pyridin-2-ylpiperazin-1-yl)methanone Chemical compound C=1C=C(NC=2C3=NC=NN3C(C3=CNN=C3)=CN=2)C=CC=1C(=O)N(CC1)CCN1C1=CC=CC=N1 CVSBUKOCITYUCO-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- WSPYBPVYCFYIRM-UHFFFAOYSA-N chembl1956687 Chemical compound C1COCCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CNN=C1 WSPYBPVYCFYIRM-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004474 heteroalkylene group Chemical group 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- VSHZLKVKHKMKFB-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-5-(1h-pyrazol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC(C1=NC=NN11)=NC=C1C1=CC=NN1 VSHZLKVKHKMKFB-UHFFFAOYSA-N 0.000 claims 1
- 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
- BDKKNNARTAMORY-UHFFFAOYSA-N n-methyl-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)NC)=NC(C=2N3N=CN=C3C(NC=3C=CC(=CC=3)N3CCOCC3)=NC=2)=C1 BDKKNNARTAMORY-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 150000003217 pyrazoles Chemical class 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- YAFOJTVLHTUFQV-UHFFFAOYSA-N triazolo[1,5-a]pyrazine Chemical class C1=CN=CC2=CN=NN21 YAFOJTVLHTUFQV-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- Cardiology (AREA)
- Urology & Nephrology (AREA)
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Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
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| US80355206P | 2006-05-31 | 2006-05-31 | |
| US93176407P | 2007-05-25 | 2007-05-25 | |
| US93176307P | 2007-05-25 | 2007-05-25 | |
| US93184407P | 2007-05-25 | 2007-05-25 | |
| US93210007P | 2007-05-29 | 2007-05-29 | |
| PCT/EP2007/055246 WO2007138072A2 (en) | 2006-05-31 | 2007-05-30 | Triazolopyrazine compounds useful for the treatment of degenerative & inflammatory diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100378T1 true HRP20100378T1 (hr) | 2010-08-31 |
Family
ID=38618932
Family Applications (1)
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|---|---|---|---|
| HR20100378T HRP20100378T1 (hr) | 2006-05-31 | 2010-07-06 | Spojevi triazolopirazina učinkoviti za tretman degenerativnih i upalnih bolesti |
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| JP (1) | JP2009538877A (da) |
| KR (1) | KR20090026288A (da) |
| AT (1) | ATE465164T1 (da) |
| AU (1) | AU2007267121A1 (da) |
| BR (1) | BRPI0712531A2 (da) |
| CA (1) | CA2653506A1 (da) |
| CR (1) | CR10458A (da) |
| DE (1) | DE602007006010D1 (da) |
| DK (1) | DK2029602T3 (da) |
| EA (1) | EA200870592A1 (da) |
| EC (1) | ECSP088923A (da) |
| HR (1) | HRP20100378T1 (da) |
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| MX (1) | MX2008015057A (da) |
| NI (1) | NI200800299A (da) |
| NO (1) | NO20084703L (da) |
| NZ (1) | NZ573015A (da) |
| PT (1) | PT2029602E (da) |
| WO (1) | WO2007138072A2 (da) |
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| NZ573015A (en) * | 2006-05-31 | 2010-11-26 | Galapagos Nv | Triazolopyrazine compounds useful for the treatment of degenerative & inflammatory diseases |
| WO2008065198A1 (en) | 2006-12-01 | 2008-06-05 | Galapagos N.V. | Triazolopyridine compounds useful for the treatment of degenerative & inflammatory diseases |
| WO2008138842A1 (en) * | 2007-05-10 | 2008-11-20 | Galapagos N.V. | Imidazopyrazines and triazolopyrazine for the treatment of joint degenerative and inflammatory diseases |
| US8133895B2 (en) * | 2007-05-10 | 2012-03-13 | Janssen Pharmaceutica N.V. | Fused pyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| DE102007060172A1 (de) | 2007-12-13 | 2009-06-25 | Bayer Healthcare Ag | Triazolotriazine und Triazolopyrazine und ihre Verwendung |
| DE102008035209A1 (de) | 2008-07-29 | 2010-02-04 | Bayer Schering Pharma Aktiengesellschaft | Triazolotriazine und Triazolopyrazine und ihre Verwendung |
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2007
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- 2007-05-30 DE DE602007006010T patent/DE602007006010D1/de active Active
- 2007-05-30 DK DK07729660.6T patent/DK2029602T3/da active
- 2007-05-30 BR BRPI0712531-3A patent/BRPI0712531A2/pt not_active IP Right Cessation
- 2007-05-30 EA EA200870592A patent/EA200870592A1/ru unknown
- 2007-05-30 AT AT07729660T patent/ATE465164T1/de active
- 2007-05-30 US US11/809,294 patent/US7501411B2/en not_active Expired - Fee Related
- 2007-05-30 PT PT07729660T patent/PT2029602E/pt unknown
- 2007-05-30 MX MX2008015057A patent/MX2008015057A/es active IP Right Grant
- 2007-05-30 WO PCT/EP2007/055246 patent/WO2007138072A2/en active Application Filing
- 2007-05-30 JP JP2009512585A patent/JP2009538877A/ja not_active Abandoned
- 2007-05-30 CA CA002653506A patent/CA2653506A1/en not_active Abandoned
- 2007-05-30 AU AU2007267121A patent/AU2007267121A1/en not_active Abandoned
- 2007-05-30 KR KR1020087030751A patent/KR20090026288A/ko not_active Application Discontinuation
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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
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2010
- 2010-07-06 HR HR20100378T patent/HRP20100378T1/hr unknown
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2011
- 2011-01-09 US US12/987,129 patent/US20110178067A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL195033A0 (en) | 2009-08-03 |
| US7915256B2 (en) | 2011-03-29 |
| ATE465164T1 (de) | 2010-05-15 |
| US20080090818A1 (en) | 2008-04-17 |
| NO20084703L (no) | 2009-02-19 |
| ECSP088923A (es) | 2009-01-30 |
| PT2029602E (pt) | 2010-07-08 |
| CR10458A (es) | 2009-02-26 |
| NI200800299A (es) | 2010-05-25 |
| EA200870592A1 (ru) | 2009-08-28 |
| DE602007006010D1 (de) | 2010-06-02 |
| CA2653506A1 (en) | 2007-12-06 |
| WO2007138072A2 (en) | 2007-12-06 |
| KR20090026288A (ko) | 2009-03-12 |
| JP2009538877A (ja) | 2009-11-12 |
| US7501411B2 (en) | 2009-03-10 |
| BRPI0712531A2 (pt) | 2012-12-25 |
| NZ573015A (en) | 2010-11-26 |
| WO2007138072A3 (en) | 2008-02-14 |
| US20110178067A1 (en) | 2011-07-21 |
| MX2008015057A (es) | 2008-12-10 |
| AU2007267121A1 (en) | 2007-12-06 |
| DK2029602T3 (da) | 2010-08-09 |
| US20100298300A1 (en) | 2010-11-25 |
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