RU2012139828A - Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы - Google Patents
Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы Download PDFInfo
- Publication number
- RU2012139828A RU2012139828A RU2012139828/04A RU2012139828A RU2012139828A RU 2012139828 A RU2012139828 A RU 2012139828A RU 2012139828/04 A RU2012139828/04 A RU 2012139828/04A RU 2012139828 A RU2012139828 A RU 2012139828A RU 2012139828 A RU2012139828 A RU 2012139828A
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- RU
- Russia
- Prior art keywords
- pyridin
- pyrazolo
- hexahydro
- methyl
- optionally substituted
- Prior art date
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- 102000004722 NADPH Oxidases Human genes 0.000 title claims 3
- 108010002998 NADPH Oxidases Proteins 0.000 title claims 3
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 12
- 125000001072 heteroaryl 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 6
- 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
- -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims 46
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 28
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 11
- 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 230000033115 angiogenesis Effects 0.000 claims 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 3
- KMPMTELUDJZGLM-UHFFFAOYSA-N 2,5-dibenzyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CC=C1 KMPMTELUDJZGLM-UHFFFAOYSA-N 0.000 claims 3
- BAXUJWIIOPNZMJ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(4-methylsulfonylphenyl)methyl]-3,4,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Chemical compound O1COC2=C1C=CC(=C2)N1NC2=C(CN(CC2)CC2=CC=C(C=C2)S(=O)(=O)C)C1 BAXUJWIIOPNZMJ-UHFFFAOYSA-N 0.000 claims 3
- CROUGORCXRDWOE-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[[3-(trifluoromethyl)phenyl]methyl]-3,4,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Chemical compound O1COC2=C1C=CC(=C2)N1NC2=C(CN(CC2)CC2=CC(=CC=C2)C(F)(F)F)C1 CROUGORCXRDWOE-UHFFFAOYSA-N 0.000 claims 3
- NLIIFVXJSJMVAM-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound FC1=CC=CC=C1N1C(=O)C(CN(CC=2C=NC=CC=2)CC2)=C2N1 NLIIFVXJSJMVAM-UHFFFAOYSA-N 0.000 claims 3
- KFOSIZPIWHVOKY-UHFFFAOYSA-N 2-(2-hydroxyethyl)-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CCO)N2)=C2CC1 KFOSIZPIWHVOKY-UHFFFAOYSA-N 0.000 claims 3
- NSZAEAYIHSNZLK-UHFFFAOYSA-N 2-(2-methoxyethyl)-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(CCOC)NC=2CCN1CC1=CC=C(OC)C=C1 NSZAEAYIHSNZLK-UHFFFAOYSA-N 0.000 claims 3
- FAZQTVRCISFNSB-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=CC=N1 FAZQTVRCISFNSB-UHFFFAOYSA-N 0.000 claims 3
- ZGUZDIDQNIPNSF-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=CN=C1 ZGUZDIDQNIPNSF-UHFFFAOYSA-N 0.000 claims 3
- NNJNFAWSUKXJIO-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-[(4-methylsulfonylphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=C(S(C)(=O)=O)C=C1 NNJNFAWSUKXJIO-UHFFFAOYSA-N 0.000 claims 3
- QHMKECIARRUGGA-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=CC(C(F)(F)F)=C1 QHMKECIARRUGGA-UHFFFAOYSA-N 0.000 claims 3
- DYLYFEADADAEKQ-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-[(4-phenylmethoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=CC(OCC=5C=CC=CC=5)=CC=4)CCC=3N2)=O)=C1 DYLYFEADADAEKQ-UHFFFAOYSA-N 0.000 claims 3
- UEACRNOYALDGCN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CN(CC=2C=NC=CC=2)CC2)=C2N1 UEACRNOYALDGCN-UHFFFAOYSA-N 0.000 claims 3
- DMUJTXHJTLRTFT-UHFFFAOYSA-N 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-5-(4-methylphenyl)sulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(C(=O)N(CC=2N=C3C=CC=CN3C=2)N2)=C2CC1 DMUJTXHJTLRTFT-UHFFFAOYSA-N 0.000 claims 3
- HRNRSZZIOPOOHA-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC=C1CN1C(=O)C(CN(CC=2C=NC=CC=2)CC2)=C2N1 HRNRSZZIOPOOHA-UHFFFAOYSA-N 0.000 claims 3
- UMQOBSSEPIBXJA-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl]-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CC=2C(=CC=CC=2)OC)N2)=C2CC1 UMQOBSSEPIBXJA-UHFFFAOYSA-N 0.000 claims 3
- AOEPYPXMYVFQGI-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2C(C=3CN(CC=4C=NC=CC=4)CCC=3N2)=O)=C1 AOEPYPXMYVFQGI-UHFFFAOYSA-N 0.000 claims 3
- HYPRWZQSFIMVOE-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CC=2C=C(OC)C=CC=2)N2)=C2CC1 HYPRWZQSFIMVOE-UHFFFAOYSA-N 0.000 claims 3
- HZUUJMNCGZMIMV-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-5-[(4-methoxyphenyl)methyl]-1,3a,4,6,7,7a-hexahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC2C(=O)N(CCOC=3C=CC(Cl)=CC=3)NC2CC1 HZUUJMNCGZMIMV-UHFFFAOYSA-N 0.000 claims 3
- HYCGNGLYTNISJG-UHFFFAOYSA-N 2-benzyl-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CC=N1 HYCGNGLYTNISJG-UHFFFAOYSA-N 0.000 claims 3
- PZMBBXPKGHCAJG-UHFFFAOYSA-N 2-benzyl-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CN=C1 PZMBBXPKGHCAJG-UHFFFAOYSA-N 0.000 claims 3
- BMRMPINGYPPQEA-UHFFFAOYSA-N 2-benzyl-5-[(2,4-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 BMRMPINGYPPQEA-UHFFFAOYSA-N 0.000 claims 3
- XDYTVJRRXCISHF-UHFFFAOYSA-N 2-benzyl-5-[(3,4-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 XDYTVJRRXCISHF-UHFFFAOYSA-N 0.000 claims 3
- DVHJCTHTLRUBPC-UHFFFAOYSA-N 2-benzyl-5-[(3,5-dimethoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC(OC)=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 DVHJCTHTLRUBPC-UHFFFAOYSA-N 0.000 claims 3
- VDEYOADUTDTYKW-UHFFFAOYSA-N 2-benzyl-5-[(3-chloro-4-fluorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 VDEYOADUTDTYKW-UHFFFAOYSA-N 0.000 claims 3
- SYENWDPXFSLRND-UHFFFAOYSA-N 2-benzyl-5-[(3-chlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 SYENWDPXFSLRND-UHFFFAOYSA-N 0.000 claims 3
- XGELNRUSJOBKMV-UHFFFAOYSA-N 2-benzyl-5-[(3-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 XGELNRUSJOBKMV-UHFFFAOYSA-N 0.000 claims 3
- MGEBTRCHBGFTBE-UHFFFAOYSA-N 2-benzyl-5-[(4-chlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 MGEBTRCHBGFTBE-UHFFFAOYSA-N 0.000 claims 3
- WKNWGQVNORKXCO-UHFFFAOYSA-N 2-benzyl-5-[(4-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 WKNWGQVNORKXCO-UHFFFAOYSA-N 0.000 claims 3
- TXTPFFPIHIHGGZ-UHFFFAOYSA-N 2-benzyl-5-[(6-chloropyridin-3-yl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=NC(Cl)=CC=C1CN1CC(C(=O)N(CC=2C=CC=CC=2)N2)=C2CC1 TXTPFFPIHIHGGZ-UHFFFAOYSA-N 0.000 claims 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- JXPHMWUWWPQRIJ-UHFFFAOYSA-N 2-phenyl-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(C=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CN=C1 JXPHMWUWWPQRIJ-UHFFFAOYSA-N 0.000 claims 3
- GXQGTFOSFHZWCX-UHFFFAOYSA-N 3-[(2-benzyl-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methyl]benzonitrile Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=CC(C#N)=C1 GXQGTFOSFHZWCX-UHFFFAOYSA-N 0.000 claims 3
- JLWSIOHQGBPHMA-UHFFFAOYSA-N 3-[3-oxo-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1CC=2NN(C=3C=C(C=CC=3)C#N)C(=O)C=2CN1CC1=CC=CN=C1 JLWSIOHQGBPHMA-UHFFFAOYSA-N 0.000 claims 3
- NVJHAYQWBUUOHP-UHFFFAOYSA-N 3-[3-oxo-5-[[3-(trifluoromethyl)phenyl]methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(CN2CC=3C(=O)N(C=4C=C(C=CC=4)C#N)NC=3CC2)=C1 NVJHAYQWBUUOHP-UHFFFAOYSA-N 0.000 claims 3
- JMQKBJPRXWKQPV-UHFFFAOYSA-N 3-[5-[(4-chlorophenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=C(C=CC=2)C#N)N2)=C2CC1 JMQKBJPRXWKQPV-UHFFFAOYSA-N 0.000 claims 3
- CSHZQYUUJUNVQV-UHFFFAOYSA-N 3-fluoro-4-[[2-(2-methyl-1,3-benzothiazol-6-yl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=C2SC(C)=NC2=CC=C1N(C(C=1C2)=O)NC=1CCN2CC1=CC=C(C#N)C=C1F CSHZQYUUJUNVQV-UHFFFAOYSA-N 0.000 claims 3
- XABOZUZUESTPPY-UHFFFAOYSA-N 3a-benzyl-5-[(4-chlorophenyl)methyl]-2-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-3-one Chemical compound C1C2(CC=3C=CC=CC=3)C(=O)N(C)N=C2CCN1CC1=CC=C(Cl)C=C1 XABOZUZUESTPPY-UHFFFAOYSA-N 0.000 claims 3
- HSWCBWVBJFLVMT-UHFFFAOYSA-N 4-[(2-benzyl-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methyl]benzonitrile Chemical compound C1CC=2NN(CC=3C=CC=CC=3)C(=O)C=2CN1CC1=CC=C(C#N)C=C1 HSWCBWVBJFLVMT-UHFFFAOYSA-N 0.000 claims 3
- FNJFPVVOXMEHRH-UHFFFAOYSA-N 4-[5-[(4-chlorophenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=CC(=CC=2)C#N)N2)=C2CC1 FNJFPVVOXMEHRH-UHFFFAOYSA-N 0.000 claims 3
- NZMCPKDOUPMLRX-UHFFFAOYSA-N 4-[[2-(2-fluorophenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound FC1=CC=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 NZMCPKDOUPMLRX-UHFFFAOYSA-N 0.000 claims 3
- BNQSWOGSBZOBLN-UHFFFAOYSA-N 4-[[2-(2-hydroxyethyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1C=2C(=O)N(CCO)NC=2CCN1CC1=CC=C(C#N)C=C1 BNQSWOGSBZOBLN-UHFFFAOYSA-N 0.000 claims 3
- KBIQWEDKTDFZEM-UHFFFAOYSA-N 4-[[2-(3-methoxyphenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C=CC(=CC=4)C#N)CCC=3N2)=O)=C1 KBIQWEDKTDFZEM-UHFFFAOYSA-N 0.000 claims 3
- FJIHSDZFHIEHSX-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 FJIHSDZFHIEHSX-UHFFFAOYSA-N 0.000 claims 3
- WQZAKMZSGPBIPB-UHFFFAOYSA-N 4-[[2-(4-methoxyphenyl)-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 WQZAKMZSGPBIPB-UHFFFAOYSA-N 0.000 claims 3
- BQGAGLRRHJUASH-UHFFFAOYSA-N 4-[[2-[(2-methoxyphenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC=C1CN1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 BQGAGLRRHJUASH-UHFFFAOYSA-N 0.000 claims 3
- QKXSHACDEDMFNR-UHFFFAOYSA-N 4-[[2-[(3-methoxyphenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound COC1=CC=CC(CN2C(C=3CN(CC=4C=CC(=CC=4)C#N)CCC=3N2)=O)=C1 QKXSHACDEDMFNR-UHFFFAOYSA-N 0.000 claims 3
- BMWOMNBUOAVJQI-UHFFFAOYSA-N 4-[[2-[(4-methoxyphenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(CN(CC=2C=CC(=CC=2)C#N)CC2)=C2N1 BMWOMNBUOAVJQI-UHFFFAOYSA-N 0.000 claims 3
- HCYCSPMSWMDIJU-UHFFFAOYSA-N 4-[[3-oxo-2-(2-piperidin-1-ylethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]methyl]benzonitrile Chemical compound C1CC=2NN(CCN3CCCCC3)C(=O)C=2CN1CC1=CC=C(C#N)C=C1 HCYCSPMSWMDIJU-UHFFFAOYSA-N 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- LKIXTJRUUVYWJM-UHFFFAOYSA-N 5-(2-phenoxyethyl)-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(C=3C=CC=CC=3)C(=O)C=2CN1CCOC1=CC=CC=C1 LKIXTJRUUVYWJM-UHFFFAOYSA-N 0.000 claims 3
- CQTTYEHPKJSPLG-UHFFFAOYSA-N 5-(4-methylphenyl)sulfonyl-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CC(C(=O)N(C=2C=CC=CC=2)N2)=C2CC1 CQTTYEHPKJSPLG-UHFFFAOYSA-N 0.000 claims 3
- LTVZALXAPQDEHS-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-2-(3-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C(=CC(Cl)=CC=4)Cl)CCC=3N2)=O)=C1 LTVZALXAPQDEHS-UHFFFAOYSA-N 0.000 claims 3
- NICZTBWNLVKZSO-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-2-(3-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4C(=CC=CC=4)Cl)CCC=3N2)=O)=C1 NICZTBWNLVKZSO-UHFFFAOYSA-N 0.000 claims 3
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- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
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- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
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- WPDSDEXJLCZUDR-UHFFFAOYSA-N 2-phenyl-5-propyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CCC)CCC=2NN1C1=CC=CC=C1 WPDSDEXJLCZUDR-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- UEFJJIWOSRKCBI-UHFFFAOYSA-N 5-(3-methylbutyl)-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CCC(C)C)CCC=2NN1C1=CC=CC=C1 UEFJJIWOSRKCBI-UHFFFAOYSA-N 0.000 claims 1
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- JLSFFUFNROMPPO-UHFFFAOYSA-N 5-benzyl-2,4,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)NNC=2CCN1CC1=CC=CC=C1 JLSFFUFNROMPPO-UHFFFAOYSA-N 0.000 claims 1
- ZGCAQZOMVOVRSM-UHFFFAOYSA-N 5-butyl-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CCCC)CCC=2NN1C1=CC=CC=C1 ZGCAQZOMVOVRSM-UHFFFAOYSA-N 0.000 claims 1
- MLXGANPROYXHAU-UHFFFAOYSA-N 5-ethyl-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(CC)CCC=2NN1C1=CC=CC=C1 MLXGANPROYXHAU-UHFFFAOYSA-N 0.000 claims 1
- QKOKQHCOJNMPBE-UHFFFAOYSA-N 5-methyl-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(C)CCC=2NN1C1=CC=CC=C1 QKOKQHCOJNMPBE-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
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- 208000029515 lens disease Diseases 0.000 claims 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- 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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
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- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10153927A EP2361911A1 (en) | 2010-02-18 | 2010-02-18 | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP10153927.8 | 2010-02-18 | ||
| PCT/IB2011/050667 WO2011101804A1 (en) | 2010-02-18 | 2011-02-17 | Pyrazolo piperidine derivatives as nadph oxidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012139828A true RU2012139828A (ru) | 2014-03-27 |
Family
ID=42617431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012139828/04A RU2012139828A (ru) | 2010-02-18 | 2011-02-17 | Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8865758B2 (enExample) |
| EP (2) | EP2361911A1 (enExample) |
| JP (1) | JP2013519724A (enExample) |
| KR (1) | KR20130010109A (enExample) |
| CN (1) | CN102762563A (enExample) |
| AU (1) | AU2011216893A1 (enExample) |
| BR (1) | BR112012020736A2 (enExample) |
| CA (1) | CA2789406A1 (enExample) |
| ES (1) | ES2446727T3 (enExample) |
| IL (1) | IL221207A (enExample) |
| RU (1) | RU2012139828A (enExample) |
| WO (1) | WO2011101804A1 (enExample) |
Families Citing this family (18)
| 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 |
| 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 |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| IN2015DN03761A (enExample) | 2012-10-24 | 2015-10-02 | Glucox Biotech Ab | |
| SG11201502796RA (en) * | 2012-12-13 | 2015-05-28 | Aduro Biotech Inc | Compositions comprising cyclic purine dinucleotides having defined stereochemistries and methods for their preparation and use |
| 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 |
| EP3258937A4 (en) | 2015-02-16 | 2018-10-31 | Glucox Biotech AB | N2-(3,4-dimethylphenyl)-6-((4-(p-tolyl)piperazin-1-yl)methyl)-1,3,5-triazine-2,4-diamine |
| CN107743483B (zh) * | 2015-06-22 | 2022-01-28 | 埃科特莱茵药品有限公司 | Nadph氧化酶4抑制剂 |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| AU2020289560A1 (en) | 2019-06-05 | 2021-12-23 | Emory University | Peptidomimetics for the treatment of coronavirus and picornavirus infections |
| WO2021145655A1 (ko) * | 2020-01-13 | 2021-07-22 | 압타바이오 주식회사 | 신규한 피라졸 유도체 |
| CN115916766A (zh) * | 2021-02-25 | 2023-04-04 | 阿普塔生物治疗公司 | 新型吡唑衍生物 |
| CN121816351A (zh) * | 2023-07-10 | 2026-04-07 | 苏州安赛隆医药科技有限公司 | 人源酪蛋白水解蛋白酶p激动剂及其用途 |
| CN122342831A (zh) * | 2025-01-06 | 2026-07-07 | 苏州安赛隆医药科技有限公司 | 抗体-ClpP激动剂的偶连物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW432073B (en) * | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| CA2383466C (en) * | 1999-09-16 | 2009-08-25 | Tanabe Seiyaku Co., Ltd. | Aromatic nitrogen-containing 6-membered cyclic compounds |
| 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 |
| EP1968976A1 (en) * | 2005-12-12 | 2008-09-17 | 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 |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole 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 |
| MY155244A (en) * | 2008-12-29 | 2015-09-30 | Sanofi Sa | Derivatives of 2-pyridin-2-yl-pyrazol-3(2h)-one, preparation and therapeutic use thereof |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
-
2010
- 2010-02-18 EP EP10153927A patent/EP2361911A1/en not_active Withdrawn
-
2011
- 2011-02-17 RU RU2012139828/04A patent/RU2012139828A/ru not_active Application Discontinuation
- 2011-02-17 AU AU2011216893A patent/AU2011216893A1/en not_active Abandoned
- 2011-02-17 KR KR1020127021407A patent/KR20130010109A/ko not_active Withdrawn
- 2011-02-17 US US13/579,290 patent/US8865758B2/en not_active Expired - Fee Related
- 2011-02-17 ES ES11709807.9T patent/ES2446727T3/es active Active
- 2011-02-17 CN CN2011800096795A patent/CN102762563A/zh active Pending
- 2011-02-17 EP EP11709807.9A patent/EP2536723B1/en active Active
- 2011-02-17 JP JP2012553434A patent/JP2013519724A/ja active Pending
- 2011-02-17 BR BR112012020736A patent/BR112012020736A2/pt not_active IP Right Cessation
- 2011-02-17 CA CA2789406A patent/CA2789406A1/en not_active Abandoned
- 2011-02-17 WO PCT/IB2011/050667 patent/WO2011101804A1/en not_active Ceased
-
2012
- 2012-07-31 IL IL221207A patent/IL221207A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2536723B1 (en) | 2013-12-11 |
| CN102762563A (zh) | 2012-10-31 |
| IL221207A0 (en) | 2012-10-31 |
| IL221207A (en) | 2015-01-29 |
| WO2011101804A1 (en) | 2011-08-25 |
| ES2446727T3 (es) | 2014-03-10 |
| BR112012020736A2 (pt) | 2016-04-26 |
| EP2361911A1 (en) | 2011-08-31 |
| US20120316163A1 (en) | 2012-12-13 |
| CA2789406A1 (en) | 2011-08-25 |
| US8865758B2 (en) | 2014-10-21 |
| KR20130010109A (ko) | 2013-01-25 |
| AU2011216893A1 (en) | 2012-08-16 |
| JP2013519724A (ja) | 2013-05-30 |
| EP2536723A1 (en) | 2012-12-26 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20150427 |