RU2012139830A - Производные пиразолопиперидина в качестве ингибиторов nadph - оксидазы - Google Patents
Производные пиразолопиперидина в качестве ингибиторов nadph - оксидазы Download PDFInfo
- Publication number
- RU2012139830A RU2012139830A RU2012139830/04A RU2012139830A RU2012139830A RU 2012139830 A RU2012139830 A RU 2012139830A RU 2012139830/04 A RU2012139830/04 A RU 2012139830/04A RU 2012139830 A RU2012139830 A RU 2012139830A RU 2012139830 A RU2012139830 A RU 2012139830A
- Authority
- RU
- Russia
- Prior art keywords
- pyridin
- pyrazolo
- hexahydro
- optionally substituted
- benzyl
- Prior art date
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- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 title claims 2
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 title 1
- 102000004316 Oxidoreductases Human genes 0.000 title 1
- 108090000854 Oxidoreductases Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 9
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 9
- 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 abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 36
- -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 230000033115 angiogenesis Effects 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 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
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 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 2
- 206010002199 Anaphylactic shock Diseases 0.000 claims 2
- 208000020084 Bone disease Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 2
- 102000004722 NADPH Oxidases Human genes 0.000 claims 2
- 108010002998 NADPH Oxidases Proteins 0.000 claims 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 208000003455 anaphylaxis Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 210000003027 ear inner Anatomy 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 230000002008 hemorrhagic effect Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000029515 lens disease Diseases 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000002314 neuroinflammatory effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000017443 reproductive system disease Diseases 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 230000000472 traumatic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PRRGIIYNKCYRFA-UHFFFAOYSA-N 2-(4-chlorophenyl)-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(C=2C=CC(Cl)=CC=2)C2=O)=C2CC1 PRRGIIYNKCYRFA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KYDYPXMCQMHKAB-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-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=2N=C3C=CC=CN3C=2)C2=O)=C2CC1 KYDYPXMCQMHKAB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- WRJVXSVTRPDXAT-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methyl]-6-[(4-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=CC(Cl)=CC=2)C2)=C2N1 WRJVXSVTRPDXAT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- WZLKKDLGUKEETK-UHFFFAOYSA-N 2-benzyl-6-[(2-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 WZLKKDLGUKEETK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CJLJFMUDVUVLMG-UHFFFAOYSA-N 2-benzyl-6-[(4-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 CJLJFMUDVUVLMG-UHFFFAOYSA-N 0.000 claims 1
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- LVSORTJQUKETFP-UHFFFAOYSA-N 6-[(3-chlorophenyl)methyl]-2-[4-(trifluoromethyl)phenyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 LVSORTJQUKETFP-UHFFFAOYSA-N 0.000 claims 1
- MKWXNSAPMBPEAT-UHFFFAOYSA-N 6-[(3-chlorophenyl)methyl]-2-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-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=4C=C(Cl)C=CC=4)CC=3N2)=O)N=C1 MKWXNSAPMBPEAT-UHFFFAOYSA-N 0.000 claims 1
- JGIPVGCPTHNTNR-UHFFFAOYSA-N 6-[(3-chlorophenyl)methyl]-2-[[2-(dimethylamino)phenyl]methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound CN(C)C1=CC=CC=C1CN1C(=O)C(CCN(CC=2C=C(Cl)C=CC=2)C2)=C2N1 JGIPVGCPTHNTNR-UHFFFAOYSA-N 0.000 claims 1
- HCABAMLLTUTIFP-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(1-methylpiperidin-4-yl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CN(C)CCC1N1C(=O)C(CCN(CC=2C=CC(Cl)=CC=2)C2)=C2N1 HCABAMLLTUTIFP-UHFFFAOYSA-N 0.000 claims 1
- JMBFFVLSJSAXCU-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(2-hydroxyethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCO)NC=2CN1CC1=CC=C(Cl)C=C1 JMBFFVLSJSAXCU-UHFFFAOYSA-N 0.000 claims 1
- AYWOKUZHPJXQFZ-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(2-methoxyethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(CCOC)NC=2CN1CC1=CC=C(Cl)C=C1 AYWOKUZHPJXQFZ-UHFFFAOYSA-N 0.000 claims 1
- VPTDZOPSRFGNTR-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(2-morpholin-4-ylethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(NN(CCN2CCOCC2)C2=O)=C2CC1 VPTDZOPSRFGNTR-UHFFFAOYSA-N 0.000 claims 1
- XKMDHLVRRLUEDF-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(2-piperidin-1-ylethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(NN(CCN2CCCCC2)C2=O)=C2CC1 XKMDHLVRRLUEDF-UHFFFAOYSA-N 0.000 claims 1
- FXDXTMLDAQNCSO-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-(3-methoxyphenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=4C=CC(Cl)=CC=4)CC=3N2)=O)=C1 FXDXTMLDAQNCSO-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
- ZIBJBUHUDUVDHW-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-2-[(3-methoxyphenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2C(C=3CCN(CC=4C=CC(Cl)=CC=4)CC=3N2)=O)=C1 ZIBJBUHUDUVDHW-UHFFFAOYSA-N 0.000 claims 1
- HMXJFXSFKVALHX-UHFFFAOYSA-N 6-[(6-chloropyridin-3-yl)methyl]-2-(2-methyl-1,3-benzothiazol-6-yl)-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=C(Cl)N=C1 HMXJFXSFKVALHX-UHFFFAOYSA-N 0.000 claims 1
- SHYOEQXYDOWQBI-UHFFFAOYSA-N 6-benzyl-2-(2-chloro-4-fluorophenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1N1C(=O)C(CCN(CC=2C=CC=CC=2)C2)=C2N1 SHYOEQXYDOWQBI-UHFFFAOYSA-N 0.000 claims 1
- WWGZXTLGLHHSEI-UHFFFAOYSA-N 6-benzyl-2-(2-methoxyphenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC=C1N1C(=O)C(CCN(CC=2C=CC=CC=2)C2)=C2N1 WWGZXTLGLHHSEI-UHFFFAOYSA-N 0.000 claims 1
- LUZBTOAWZPAURM-UHFFFAOYSA-N 6-benzyl-2-(3-chlorophenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound ClC1=CC=CC(N2C(C=3CCN(CC=4C=CC=CC=4)CC=3N2)=O)=C1 LUZBTOAWZPAURM-UHFFFAOYSA-N 0.000 claims 1
- HAQRZAVVVTWHIV-UHFFFAOYSA-N 6-benzyl-2-(3-methoxyphenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CCN(CC=4C=CC=CC=4)CC=3N2)=O)=C1 HAQRZAVVVTWHIV-UHFFFAOYSA-N 0.000 claims 1
- JLZJSYFDOQRARE-UHFFFAOYSA-N 6-benzyl-2-(3-phenylmethoxyphenyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C(=O)C=2CCN1CC1=CC=CC=C1 JLZJSYFDOQRARE-UHFFFAOYSA-N 0.000 claims 1
- ABRWPWBZYXPHPZ-UHFFFAOYSA-N 6-benzyl-2-[(4-chlorophenyl)methyl]-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C(CCN(CC=2C=CC=CC=2)C2)=C2N1 ABRWPWBZYXPHPZ-UHFFFAOYSA-N 0.000 claims 1
- LFJOTNIKJKMLNT-UHFFFAOYSA-N 6-benzyl-2-methyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1CC=2C(=O)N(C)NC=2CN1CC1=CC=CC=C1 LFJOTNIKJKMLNT-UHFFFAOYSA-N 0.000 claims 1
- OPLVIEAVHCSZEW-UHFFFAOYSA-N 6-benzyl-2-phenyl-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-3-one Chemical compound C1C=2NN(C=3C=CC=CC=3)C(=O)C=2CCN1CC1=CC=CC=C1 OPLVIEAVHCSZEW-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
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims 1
- 125000005002 aryl methyl group Chemical group 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000003795 chemical substances by application Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- NEBVBDJWYSPFQJ-UHFFFAOYSA-N n-[3-[3-oxo-6-(pyridin-3-ylmethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=3CCN(CC=4C=NC=CC=4)CC=3N2)=O)=C1 NEBVBDJWYSPFQJ-UHFFFAOYSA-N 0.000 claims 1
- WXNRXYJLYBLJOW-UHFFFAOYSA-N n-[3-[6-(4-methylphenyl)sulfonyl-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=3CCN(CC=3N2)S(=O)(=O)C=2C=CC(C)=CC=2)=O)=C1 WXNRXYJLYBLJOW-UHFFFAOYSA-N 0.000 claims 1
- RKWMMOHCISFEIH-UHFFFAOYSA-N n-[3-[6-[(3-chlorophenyl)methyl]-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=3CCN(CC=4C=C(Cl)C=CC=4)CC=3N2)=O)=C1 RKWMMOHCISFEIH-UHFFFAOYSA-N 0.000 claims 1
- RADCLNGGKIKVFZ-UHFFFAOYSA-N n-[3-[6-[(3-cyanophenyl)methyl]-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=3CCN(CC=4C=C(C=CC=4)C#N)CC=3N2)=O)=C1 RADCLNGGKIKVFZ-UHFFFAOYSA-N 0.000 claims 1
- DEYFXNLGLQGMFE-UHFFFAOYSA-N n-[4-[(2-benzyl-3-oxo-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(NN(CC=2C=CC=CC=2)C2=O)=C2CC1 DEYFXNLGLQGMFE-UHFFFAOYSA-N 0.000 claims 1
- 229950006238 nadide Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
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- Pain & Pain Management (AREA)
- Pulmonology (AREA)
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- Gastroenterology & Hepatology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10153929.4 | 2010-02-18 | ||
| EP10153929A EP2361912A1 (en) | 2010-02-18 | 2010-02-18 | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| PCT/IB2011/050668 WO2011101805A1 (en) | 2010-02-18 | 2011-02-17 | Pyrazolo piperidine derivatives as nadph oxidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012139830A true RU2012139830A (ru) | 2014-03-27 |
Family
ID=42635178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012139830/04A RU2012139830A (ru) | 2010-02-18 | 2011-02-17 | Производные пиразолопиперидина в качестве ингибиторов nadph - оксидазы |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8748456B2 (https=) |
| EP (2) | EP2361912A1 (https=) |
| JP (1) | JP2013520407A (https=) |
| KR (1) | KR20130002317A (https=) |
| CN (1) | CN102762562A (https=) |
| AU (1) | AU2011216894A1 (https=) |
| BR (1) | BR112012020742A2 (https=) |
| CA (1) | CA2789408A1 (https=) |
| IL (1) | IL221209A0 (https=) |
| RU (1) | RU2012139830A (https=) |
| WO (1) | WO2011101805A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2002835A1 (en) | 2007-06-04 | 2008-12-17 | GenKyo Tex | 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 |
| EP2166010A1 (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 |
| EP2166009A1 (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 |
| EP2911667B1 (en) | 2012-10-24 | 2017-02-22 | Glucox Biotech AB | Triazine derivatives for the treatment of conditions associated with nicotinamide adenine dinucleotide phosphate oxidase |
| 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 |
| US10173988B2 (en) | 2015-02-16 | 2019-01-08 | Glucox Biotech Ab | N2-(3,4-dimethylphenyl)-6-((4-(p-tolyl)piperazin-1-yl)methyl)-1,3,5-triazine-2,4-diamine |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| EA202193251A1 (ru) | 2019-06-05 | 2022-03-10 | Эмори Юниверсити | Пептидомиметики для лечения коронавирусной и пикорнавирусной инфекций |
| JP2023511302A (ja) * | 2020-01-13 | 2023-03-17 | アプタバイオ セラピューティクス インコーポレイテッド | 新規なピラゾール誘導体 |
| PH12022553516A1 (en) * | 2021-02-25 | 2024-06-03 | Aptabio Therapeutics Inc | Novel pyrazole derivatives |
| WO2025011546A1 (en) * | 2023-07-10 | 2025-01-16 | Acelon Therapeutics | Human caseinolytic protease p agonists and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW432073B (en) | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| EP1219609B1 (en) * | 1999-09-16 | 2007-04-04 | Tanabe Seiyaku Co., Ltd. | Aromatic nitrogenous six-membered ring 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 |
| US7947686B2 (en) * | 2005-12-12 | 2011-05-24 | Nerviano Medical Sciences S.R.L. | Substituted pyrazolo[4,3-c]pyridine derivatives active as kinase inhibitors |
| EP2002835A1 (en) * | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| TW200930713A (en) * | 2007-12-03 | 2009-07-16 | Takeda Pharmaceutical | Nitrogen-containing heterocyclic compound and use thereof |
| WO2010076525A1 (fr) * | 2008-12-29 | 2010-07-08 | Sanofi-Aventis | Dérivés de 2-pyridin-2-yl-pyrazol-3(2h)-one, leur préparation et leur application en thérapeutique |
| 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
- 2011-02-17 BR BR112012020742A patent/BR112012020742A2/pt not_active IP Right Cessation
- 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 EP EP11709483A patent/EP2536721A1/en not_active Withdrawn
- 2011-02-17 CA CA2789408A patent/CA2789408A1/en not_active Abandoned
- 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 AU AU2011216894A patent/AU2011216894A1/en not_active Abandoned
- 2011-02-17 WO PCT/IB2011/050668 patent/WO2011101805A1/en not_active Ceased
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2012
- 2012-07-31 IL IL221209A patent/IL221209A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL221209A0 (en) | 2012-10-31 |
| CA2789408A1 (en) | 2011-08-25 |
| KR20130002317A (ko) | 2013-01-07 |
| EP2361912A1 (en) | 2011-08-31 |
| US20120316380A1 (en) | 2012-12-13 |
| EP2536721A1 (en) | 2012-12-26 |
| US8748456B2 (en) | 2014-06-10 |
| AU2011216894A1 (en) | 2012-08-16 |
| BR112012020742A2 (pt) | 2016-04-26 |
| CN102762562A (zh) | 2012-10-31 |
| JP2013520407A (ja) | 2013-06-06 |
| WO2011101805A1 (en) | 2011-08-25 |
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| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20150507 |