JP2013520407A5 - - Google Patents
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- JP2013520407A5 JP2013520407A5 JP2012553435A JP2012553435A JP2013520407A5 JP 2013520407 A5 JP2013520407 A5 JP 2013520407A5 JP 2012553435 A JP2012553435 A JP 2012553435A JP 2012553435 A JP2012553435 A JP 2012553435A JP 2013520407 A5 JP2013520407 A5 JP 2013520407A5
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- JP
- Japan
- Prior art keywords
- pyrazolo
- hexahydro
- pyridin
- benzyl
- chlorobenzyl
- 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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- -1 substituted Chemical class 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- RTTBBADOMOOPTQ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-b]pyridine Chemical class C1CCNC2=C1NN=C2 RTTBBADOMOOPTQ-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 4
- XDDWGECWOBJRNT-UHFFFAOYSA-N 6-benzyl-2,4,5,7-tetrahydro-1h-pyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)NNC=2CN1CC1=CC=CC=C1 XDDWGECWOBJRNT-UHFFFAOYSA-N 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- CFRBCNVIUKICRC-UHFFFAOYSA-N 2,6-dibenzyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CC=C1 CFRBCNVIUKICRC-UHFFFAOYSA-N 0.000 claims 2
- QNQQRYAZASXZDH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C=3C=C4OCOC4=CC=3)C(=O)C=2CCN1CC1=CC=CN=C1 QNQQRYAZASXZDH-UHFFFAOYSA-N 0.000 claims 2
- SASSMIWJRUDEKS-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(CN2CC3=C(C(N(C=4C=C5OCOC5=CC=4)N3)=O)CC2)=C1 SASSMIWJRUDEKS-UHFFFAOYSA-N 0.000 claims 2
- WFBHNVIEROQRPO-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-[(4-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(NN(C=2C=C3OCOC3=CC=2)C2=O)=C2CC1 WFBHNVIEROQRPO-UHFFFAOYSA-N 0.000 claims 2
- GOHBSBGXDWUZNP-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-[(6-chloropyridin-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=NC(Cl)=CC=C1CN1CC(NN(C=2C=C3OCOC3=CC=2)C2=O)=C2CC1 GOHBSBGXDWUZNP-UHFFFAOYSA-N 0.000 claims 2
- NMFWYSNVLVTFHM-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C2CCN(CC=3C=CC=CC=3)CC2)C2=O)=C2CC1 NMFWYSNVLVTFHM-UHFFFAOYSA-N 0.000 claims 2
- COKSBKLBYZEIAK-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(CN2CC3=C(C(N(C4CCN(CC=5C=CC=CC=5)CC4)N3)=O)CC2)=C1 COKSBKLBYZEIAK-UHFFFAOYSA-N 0.000 claims 2
- NQTFOHGPHACNIH-UHFFFAOYSA-N 2-(1-phenylethyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound N1C=2CN(CC=3C=NC=CC=3)CCC=2C(=O)N1C(C)C1=CC=CC=C1 NQTFOHGPHACNIH-UHFFFAOYSA-N 0.000 claims 2
- FLTMNZQDFLXCLI-UHFFFAOYSA-N 2-(2-benzyl-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl)-n-methylacetamide Chemical compound C1N(CC(=O)NC)CCC(C2=O)=C1NN2CC1=CC=CC=C1 FLTMNZQDFLXCLI-UHFFFAOYSA-N 0.000 claims 2
- KRCPDJLMALLDNE-UHFFFAOYSA-N 2-(2-methoxyethyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCOC)NC=2CN1CC1=CC=CN=C1 KRCPDJLMALLDNE-UHFFFAOYSA-N 0.000 claims 2
- CORSDXIQXLUJNY-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-(pyridin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CC=N1 CORSDXIQXLUJNY-UHFFFAOYSA-N 0.000 claims 2
- IZGGRIQXARYORT-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CN=C1 IZGGRIQXARYORT-UHFFFAOYSA-N 0.000 claims 2
- KMBHUBYAENPCRU-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1CC2)=O)NC=1CN2CC1=CC=CC(C(F)(F)F)=C1 KMBHUBYAENPCRU-UHFFFAOYSA-N 0.000 claims 2
- MFYMJQPWMKYMHF-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2CC3=C(C(N(CCN4CCOCC4)N3)=O)CC2)=C1 MFYMJQPWMKYMHF-UHFFFAOYSA-N 0.000 claims 2
- MKRSLCOCHLJMCP-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-(1-phenylethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=3N2)C(C)C=2C=CC=CC=2)=O)=C1 MKRSLCOCHLJMCP-UHFFFAOYSA-N 0.000 claims 2
- LNPVHEDDQJQZOO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-[(2-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=4C(=CC=CC=4)OC)CC=3N2)=O)=C1 LNPVHEDDQJQZOO-UHFFFAOYSA-N 0.000 claims 2
- JIXVKEKCFRBLNB-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 JIXVKEKCFRBLNB-UHFFFAOYSA-N 0.000 claims 2
- LPWPONPWEWKKIG-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(C=2C=CC(Cl)=CC=2)C2=O)=C2CC1 LPWPONPWEWKKIG-UHFFFAOYSA-N 0.000 claims 2
- IJMSEUZVPUIVCO-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(pyridin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2N=CC=CC=2)C2)=C2N1 IJMSEUZVPUIVCO-UHFFFAOYSA-N 0.000 claims 2
- XBTPTSLULYFGBV-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 XBTPTSLULYFGBV-UHFFFAOYSA-N 0.000 claims 2
- NOBYTVHFKBSJNT-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 NOBYTVHFKBSJNT-UHFFFAOYSA-N 0.000 claims 2
- GXAIIDAYJXNZKJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[(6-chloropyridin-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CCN(CC=2C=NC(Cl)=CC=2)C2)=C2N1 GXAIIDAYJXNZKJ-UHFFFAOYSA-N 0.000 claims 2
- FUINMUKVMGTPBS-UHFFFAOYSA-N 2-(4-methoxyphenyl)-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 FUINMUKVMGTPBS-UHFFFAOYSA-N 0.000 claims 2
- STDCAOJSYGMDLF-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-6-(4-phenylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3N=C4C=CC=CN4C=3)C(=O)C=2CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 STDCAOJSYGMDLF-UHFFFAOYSA-N 0.000 claims 2
- HKAGVFGNBIZIRP-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-6-[3-(trifluoromethyl)phenyl]sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4N=C5C=CC=CN5C=4)N3)=O)CC2)=C1 HKAGVFGNBIZIRP-UHFFFAOYSA-N 0.000 claims 2
- RYOIADQIOPOORM-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=NC=CC=2)C2)=C2N1 RYOIADQIOPOORM-UHFFFAOYSA-N 0.000 claims 2
- KUOIWOBYKKKFIB-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 KUOIWOBYKKKFIB-UHFFFAOYSA-N 0.000 claims 2
- KTOKHUFMULXOFS-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[(6-chloropyridin-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=NC(Cl)=CC=2)C2)=C2N1 KTOKHUFMULXOFS-UHFFFAOYSA-N 0.000 claims 2
- DKEFMFMCUOVDHE-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[[3-(trifluoromethyl)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1CN1C(=O)C(CCN(CC=2C=C(C=CC=2)C(F)(F)F)C2)=C2N1 DKEFMFMCUOVDHE-UHFFFAOYSA-N 0.000 claims 2
- HOKRJJOKSYHKMT-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1OCCN1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 HOKRJJOKSYHKMT-UHFFFAOYSA-N 0.000 claims 2
- AKZCHNGFMGAGCJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCN(C)C)NC=2CN1S(=O)(=O)C1=CC=C(C)C=C1 AKZCHNGFMGAGCJ-UHFFFAOYSA-N 0.000 claims 2
- BDMVKYCKECTDIN-UHFFFAOYSA-N 2-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-6-methylsulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(N2C(C=3CCN(CC=3N2)S(C)(=O)=O)=O)N=C1 BDMVKYCKECTDIN-UHFFFAOYSA-N 0.000 claims 2
- VEQHWEUDVUEBLO-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methyl]-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound CN(C)C1=CC=CC=C1CN1C(=O)C(CCN(C2)S(=O)(=O)C=3C=CC(C)=CC=3)=C2N1 VEQHWEUDVUEBLO-UHFFFAOYSA-N 0.000 claims 2
- YLUVRZAURDXDJR-UHFFFAOYSA-N 2-benzhydryl-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CN=C1 YLUVRZAURDXDJR-UHFFFAOYSA-N 0.000 claims 2
- HHHKFTOWZDMTFS-UHFFFAOYSA-N 2-benzyl-6-(3-chlorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 HHHKFTOWZDMTFS-UHFFFAOYSA-N 0.000 claims 2
- UTVHZEPXLBLCGT-UHFFFAOYSA-N 2-benzyl-6-(3-fluorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound FC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 UTVHZEPXLBLCGT-UHFFFAOYSA-N 0.000 claims 2
- QYQLPRRJCSWQTR-UHFFFAOYSA-N 2-benzyl-6-(3-methoxyphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(S(=O)(=O)N2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 QYQLPRRJCSWQTR-UHFFFAOYSA-N 0.000 claims 2
- AISWSLGKTPVRKF-UHFFFAOYSA-N 2-benzyl-6-(4-chlorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 AISWSLGKTPVRKF-UHFFFAOYSA-N 0.000 claims 2
- IMCUFDDOLALXDR-UHFFFAOYSA-N 2-benzyl-6-(4-fluorophenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 IMCUFDDOLALXDR-UHFFFAOYSA-N 0.000 claims 2
- JFNCVRPTLRXDPR-UHFFFAOYSA-N 2-benzyl-6-(4-methoxyphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 JFNCVRPTLRXDPR-UHFFFAOYSA-N 0.000 claims 2
- OTRHSAWGPJYRPT-UHFFFAOYSA-N 2-benzyl-6-(4-methylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 OTRHSAWGPJYRPT-UHFFFAOYSA-N 0.000 claims 2
- WYADQLRLTGTKIG-UHFFFAOYSA-N 2-benzyl-6-(4-tert-butylphenyl)sulfonyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 WYADQLRLTGTKIG-UHFFFAOYSA-N 0.000 claims 2
- OGMYOQWQJYGGIM-UHFFFAOYSA-N 2-benzyl-6-(pyridin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CC=N1 OGMYOQWQJYGGIM-UHFFFAOYSA-N 0.000 claims 2
- LXBNUKJKFDPTQI-UHFFFAOYSA-N 2-benzyl-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(CC=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CN=C1 LXBNUKJKFDPTQI-UHFFFAOYSA-N 0.000 claims 2
- UCUDAXQFEYSRNB-UHFFFAOYSA-N 2-benzyl-6-(quinolin-2-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound O=C1C=2CCN(CC=3N=C4C=CC=CC4=CC=3)CC=2NN1CC1=CC=CC=C1 UCUDAXQFEYSRNB-UHFFFAOYSA-N 0.000 claims 2
- KKSINXZFANJVIS-UHFFFAOYSA-N 2-benzyl-6-[(1-methylpyrazol-3-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound CN1C=CC(CN2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=N1 KKSINXZFANJVIS-UHFFFAOYSA-N 0.000 claims 2
- SGRQMFVGLKFALW-UHFFFAOYSA-N 2-benzyl-6-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound S1C(C)=NC(CN2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 SGRQMFVGLKFALW-UHFFFAOYSA-N 0.000 claims 2
- AYBZGFCLEOFYFG-UHFFFAOYSA-N 2-benzyl-6-[(3-chloro-4-fluorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 AYBZGFCLEOFYFG-UHFFFAOYSA-N 0.000 claims 2
- XCIJNDIJNKQGKW-UHFFFAOYSA-N 2-benzyl-6-[(3-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(CN2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 XCIJNDIJNKQGKW-UHFFFAOYSA-N 0.000 claims 2
- UJILPGOOXVCFOK-UHFFFAOYSA-N 2-benzyl-6-[(3-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2CC3=C(C(N(CC=4C=CC=CC=4)N3)=O)CC2)=C1 UJILPGOOXVCFOK-UHFFFAOYSA-N 0.000 claims 2
- LZGPIURGCINMEL-UHFFFAOYSA-N 2-benzyl-6-[(4-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 LZGPIURGCINMEL-UHFFFAOYSA-N 0.000 claims 2
- QDNUBODMKIVTEN-UHFFFAOYSA-N 2-benzyl-6-[(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)sulfonyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C2N(C)CCOC2=CC=C1S(=O)(=O)N(C1)CCC(C2=O)=C1NN2CC1=CC=CC=C1 QDNUBODMKIVTEN-UHFFFAOYSA-N 0.000 claims 2
- NTASKDYFPWCFQH-UHFFFAOYSA-N 2-benzyl-6-[(4-methylsulfonylphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 NTASKDYFPWCFQH-UHFFFAOYSA-N 0.000 claims 2
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- TTWUPKTUCLUHSM-UHFFFAOYSA-N 6-[(3-chloro-4-fluorophenyl)methyl]-2-(4-chlorophenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(NN(C=2C=CC(Cl)=CC=2)C2=O)=C2CC1 TTWUPKTUCLUHSM-UHFFFAOYSA-N 0.000 claims 1
- HWTDMWIIJTWPBQ-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-[(2-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC=C1CN1C(=O)C(CCN(CC=2C=CC(Cl)=CC=2)C2)=C2N1 HWTDMWIIJTWPBQ-UHFFFAOYSA-N 0.000 claims 1
- ADAIEKAITRRAEN-UHFFFAOYSA-N 6-benzyl-3a,4,5,7-tetrahydro-2h-pyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC2C(=O)NN=C2CN1CC1=CC=CC=C1 ADAIEKAITRRAEN-UHFFFAOYSA-N 0.000 claims 1
- VXBVYYQZHZRYQU-UHFFFAOYSA-N 6-methyl-2-phenyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1N(C)CCC(C2=O)=C1NN2C1=CC=CC=C1 VXBVYYQZHZRYQU-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 206010002199 Anaphylactic shock Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003027 ear inner Anatomy 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000003959 neuroinflammation Effects 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10153929A EP2361912A1 (en) | 2010-02-18 | 2010-02-18 | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP10153929.4 | 2010-02-18 | ||
| PCT/IB2011/050668 WO2011101805A1 (en) | 2010-02-18 | 2011-02-17 | Pyrazolo piperidine derivatives as nadph oxidase inhibitors |
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| Publication Number | Publication Date |
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| JP2013520407A JP2013520407A (ja) | 2013-06-06 |
| JP2013520407A5 true JP2013520407A5 (enExample) | 2014-04-03 |
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Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8748456B2 (enExample) |
| EP (2) | EP2361912A1 (enExample) |
| JP (1) | JP2013520407A (enExample) |
| KR (1) | KR20130002317A (enExample) |
| CN (1) | CN102762562A (enExample) |
| AU (1) | AU2011216894A1 (enExample) |
| BR (1) | BR112012020742A2 (enExample) |
| CA (1) | CA2789408A1 (enExample) |
| IL (1) | IL221209A0 (enExample) |
| RU (1) | RU2012139830A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2002835A1 (en) | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166010A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166009A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
| EP2165707A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166008A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| GB2494679A (en) | 2011-09-15 | 2013-03-20 | Univ Jw Goethe Frankfurt Main | Treatment of neuropathic pain and nerve injury by Nox4 inhibition |
| JP2015535225A (ja) | 2012-10-24 | 2015-12-10 | グルソックス・バイオテック・アーベー | ニコチンアミドアデニンジヌクレオチドリン酸オキシダーゼに関連する状態を処置するためのトリアジン誘導体 |
| WO2014186704A2 (en) * | 2013-05-17 | 2014-11-20 | N30 Pharmaceuticals, Inc. | Novel compounds for the treatment of cystic fibrosis |
| CN105315275B (zh) * | 2014-07-14 | 2019-10-01 | 中国科学院上海药物研究所 | 一类吡唑酮化合物及其用途 |
| CN107427519A (zh) | 2015-02-16 | 2017-12-01 | 格卢科克斯生物科技有限公司 | N2‑(3,4‑二甲基苯基)‑6‑((4‑(对甲苯基)哌嗪‑1‑基)甲基)‑1,3,5‑三嗪‑2,4‑二胺 |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| KR20220026538A (ko) | 2019-06-05 | 2022-03-04 | 에모리 유니버시티 | 코로나바이러스 및 피코르나바이러스 감염 치료용 펩티도모방체 |
| BR112022013849A2 (pt) * | 2020-01-13 | 2022-09-13 | Aptabio Therapeutics Inc | Novo derivado de pirazol |
| CA3189497A1 (en) * | 2021-02-25 | 2022-09-01 | Aptabio Therapeutics Inc. | 4, 5, 6, 7-tetrahydro-2h-indazol-3-ol derivatives and oxidative stress inhibitory activity thereof |
| WO2025011546A1 (en) * | 2023-07-10 | 2025-01-16 | Acelon Therapeutics | Human caseinolytic protease p agonists and uses thereof |
Family Cites Families (10)
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| TW432073B (en) | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| IL148291A0 (en) * | 1999-09-16 | 2002-09-12 | Tanabe Seiyaku Co | Aromatic nitrogen-containing 6-membered cyclic compounds |
| IL144468A0 (en) * | 2000-07-27 | 2002-05-23 | Pfizer Prod Inc | Use of growth hormone secretagogues for improvement of functional health status |
| JP2004217654A (ja) * | 2002-12-27 | 2004-08-05 | Japan Tobacco Inc | 縮合ｎ含有へテロ環化合物及びその医薬用途 |
| US7759337B2 (en) * | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| JP5219150B2 (ja) * | 2005-12-12 | 2013-06-26 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | キナーゼ阻害薬として活性な置換ピラゾロ［４，３−ｃ］ピリジン誘導体 |
| EP2002835A1 (en) * | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| PE20091093A1 (es) * | 2007-12-03 | 2009-08-25 | Takeda Pharmaceutical | Compuesto heterociclico que contiene nitrogeno y su uso |
| AU2009334570B2 (en) * | 2008-12-29 | 2016-06-09 | Sanofi | Derivatives of 2-pyridin-2-yl-pyrazol-3(2h)-one, preparation and therapeutic use thereof |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
-
2010
- 2010-02-18 EP EP10153929A patent/EP2361912A1/en not_active Withdrawn
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2011
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- 2011-02-17 EP EP11709483A patent/EP2536721A1/en not_active Withdrawn
- 2011-02-17 CA CA2789408A patent/CA2789408A1/en not_active Abandoned
- 2011-02-17 BR BR112012020742A patent/BR112012020742A2/pt not_active IP Right Cessation
- 2011-02-17 KR KR1020127021663A patent/KR20130002317A/ko not_active Withdrawn
- 2011-02-17 RU RU2012139830/04A patent/RU2012139830A/ru not_active Application Discontinuation
- 2011-02-17 JP JP2012553435A patent/JP2013520407A/ja active Pending
- 2011-02-17 US US13/579,293 patent/US8748456B2/en not_active Expired - Fee Related
- 2011-02-17 CN CN2011800096780A patent/CN102762562A/zh active Pending
- 2011-02-17 AU AU2011216894A patent/AU2011216894A1/en not_active Abandoned
-
2012
- 2012-07-31 IL IL221209A patent/IL221209A0/en unknown
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