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
- Authority
- RU
- Russia
- Prior art keywords
- pyridin
- pyrazolo
- hexahydro
- methyl
- optionally substituted
- Prior art date
Links
- 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
- PTIWONVVKXTEBX-UHFFFAOYSA-N 5-[(3-chloro-4-fluorophenyl)methyl]-2-(4-chlorophenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(C(=O)N(C=2C=CC(Cl)=CC=2)N2)=C2CC1 PTIWONVVKXTEBX-UHFFFAOYSA-N 0.000 claims 3
- KOIRZCHDSGZXNA-UHFFFAOYSA-N 5-[(3-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=C(Cl)C=CC=4)CCC=3N2)=O)=C1 KOIRZCHDSGZXNA-UHFFFAOYSA-N 0.000 claims 3
- OBOIQEPEXXCBLD-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-2-methyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(C)NC=2CCN1CC1=CC=CC(Cl)=C1 OBOIQEPEXXCBLD-UHFFFAOYSA-N 0.000 claims 3
- HEAUNENNFPCHJV-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(1-methylpiperidin-4-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CN(C)CCC1N1C(=O)C(CN(CC=2C=CC(Cl)=CC=2)CC2)=C2N1 HEAUNENNFPCHJV-UHFFFAOYSA-N 0.000 claims 3
- NNPSYURULNVWIA-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-hydroxyethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(CCO)NC=2CCN1CC1=CC=C(Cl)C=C1 NNPSYURULNVWIA-UHFFFAOYSA-N 0.000 claims 3
- KBSUQMSGGKUBFX-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-methoxyethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(CCOC)NC=2CCN1CC1=CC=C(Cl)C=C1 KBSUQMSGGKUBFX-UHFFFAOYSA-N 0.000 claims 3
- VVDRVIGOBFJPMU-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(2-morpholin-4-ylethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(CCN2CCOCC2)N2)=C2CC1 VVDRVIGOBFJPMU-UHFFFAOYSA-N 0.000 claims 3
- RADAISFGUZBEMD-UHFFFAOYSA-N 5-[(4-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(Cl)=CC=4)CCC=3N2)=O)=C1 RADAISFGUZBEMD-UHFFFAOYSA-N 0.000 claims 3
- JKKLSWJKXOGWQW-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-(4-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(CN(CC=2C=CC(Cl)=CC=2)CC2)=C2N1 JKKLSWJKXOGWQW-UHFFFAOYSA-N 0.000 claims 3
- FBQNLYWYSIYSBL-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-[(2-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC=C1CN1C(=O)C(CN(CC=2C=CC(Cl)=CC=2)CC2)=C2N1 FBQNLYWYSIYSBL-UHFFFAOYSA-N 0.000 claims 3
- UQDACGXPVIJDRO-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-methyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(C)NC=2CCN1CC1=CC=C(Cl)C=C1 UQDACGXPVIJDRO-UHFFFAOYSA-N 0.000 claims 3
- NAROMPHLBKOKAK-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=CC=CC=2)N2)=C2CC1 NAROMPHLBKOKAK-UHFFFAOYSA-N 0.000 claims 3
- BVZBJRSSDNRJKI-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-(1-methylpiperidin-4-yl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(C2CCN(C)CC2)N2)=C2CC1 BVZBJRSSDNRJKI-UHFFFAOYSA-N 0.000 claims 3
- ZIJSZDWCOCDEKK-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-(2-morpholin-4-ylethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(CCN2CCOCC2)N2)=C2CC1 ZIJSZDWCOCDEKK-UHFFFAOYSA-N 0.000 claims 3
- FMLKDGIEWJOHQR-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-2-methyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(OC)=CC=C1CN1CC(C(=O)N(C)N2)=C2CC1 FMLKDGIEWJOHQR-UHFFFAOYSA-N 0.000 claims 3
- IILBFTYPDQHQCU-UHFFFAOYSA-N 5-benzyl-2-(2-chloro-4-fluorophenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1N1C(=O)C(CN(CC=2C=CC=CC=2)CC2)=C2N1 IILBFTYPDQHQCU-UHFFFAOYSA-N 0.000 claims 3
- LGXAAGRYHFGQKL-UHFFFAOYSA-N 5-benzyl-2-(2-methoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC=C1N1C(=O)C(CN(CC=2C=CC=CC=2)CC2)=C2N1 LGXAAGRYHFGQKL-UHFFFAOYSA-N 0.000 claims 3
- HAMGHRIGEAPRPL-UHFFFAOYSA-N 5-benzyl-2-(3-chlorophenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC=CC(N2C(C=3CN(CC=4C=CC=CC=4)CCC=3N2)=O)=C1 HAMGHRIGEAPRPL-UHFFFAOYSA-N 0.000 claims 3
- LPBRLXZOOFQRIU-UHFFFAOYSA-N 5-benzyl-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)CCC=3N2)=O)=C1 LPBRLXZOOFQRIU-UHFFFAOYSA-N 0.000 claims 3
- NQMWROZHRTYZSD-UHFFFAOYSA-N 5-benzyl-2-(3-phenylmethoxyphenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1CC=2NN(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C(=O)C=2CN1CC1=CC=CC=C1 NQMWROZHRTYZSD-UHFFFAOYSA-N 0.000 claims 3
- NPOAPKLRCNEVKL-UHFFFAOYSA-N 5-benzyl-2-[(4-chlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C(CN(CC=2C=CC=CC=2)CC2)=C2N1 NPOAPKLRCNEVKL-UHFFFAOYSA-N 0.000 claims 3
- RUSLEORXLZGVHZ-UHFFFAOYSA-N 5-benzyl-2-[2-(4-chlorophenoxy)ethyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1OCCN1C(=O)C(CN(CC=2C=CC=CC=2)CC2)=C2N1 RUSLEORXLZGVHZ-UHFFFAOYSA-N 0.000 claims 3
- APOLWDJJWGJUCD-UHFFFAOYSA-N 5-benzyl-2-methyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1C=2C(=O)N(C)NC=2CCN1CC1=CC=CC=C1 APOLWDJJWGJUCD-UHFFFAOYSA-N 0.000 claims 3
- FPIPOTOBYXNMOK-UHFFFAOYSA-N 5-benzyl-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=2CN1CC1=CC=CC=C1 FPIPOTOBYXNMOK-UHFFFAOYSA-N 0.000 claims 3
- LEMRYHURXLEJJZ-UHFFFAOYSA-N 5-methylsulfonyl-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(S(=O)(=O)C)CCC=2NN1C1=CC=CC=C1 LEMRYHURXLEJJZ-UHFFFAOYSA-N 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- BNTZTHNDTQGMBU-UHFFFAOYSA-N n-[3-[3-oxo-5-(pyridin-3-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2C(C=3CN(CC=4C=NC=CC=4)CCC=3N2)=O)=C1 BNTZTHNDTQGMBU-UHFFFAOYSA-N 0.000 claims 3
- MTWMVHPHRCVMMV-UHFFFAOYSA-N n-[4-[(3-oxo-2-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(C(=O)N(C=2C=CC=CC=2)N2)=C2CC1 MTWMVHPHRCVMMV-UHFFFAOYSA-N 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- CJLBRUMVRUVXJC-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(F)=CC=C1N1C(=O)C(CNCC2)=C2N1 CJLBRUMVRUVXJC-UHFFFAOYSA-N 0.000 claims 2
- ZISOBPVMGZLFBU-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-(pyridin-2-ylmethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(N2C(C=3CN(CC=4N=CC=CC=4)CCC=3N2)=O)=C1 ZISOBPVMGZLFBU-UHFFFAOYSA-N 0.000 claims 2
- PRRHYVHHAPBLLV-UHFFFAOYSA-N 2-benzyl-4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CNCCC=2NN1CC1=CC=CC=C1 PRRHYVHHAPBLLV-UHFFFAOYSA-N 0.000 claims 2
- UDUWUZWRUZZOBQ-UHFFFAOYSA-N 2-benzyl-5-[(3,5-dichlorophenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound ClC1=CC(Cl)=CC(CN2CC=3C(=O)N(CC=4C=CC=CC=4)NC=3CC2)=C1 UDUWUZWRUZZOBQ-UHFFFAOYSA-N 0.000 claims 2
- UYDCAQTZYYBNMQ-UHFFFAOYSA-N 2-benzyl-5-methylsulfonyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound O=C1C=2CN(S(=O)(=O)C)CCC=2NN1CC1=CC=CC=C1 UYDCAQTZYYBNMQ-UHFFFAOYSA-N 0.000 claims 2
- ANMMZJDZZMDJNA-UHFFFAOYSA-N 3-[5-[(3-chloro-4-fluorophenyl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1=C(Cl)C(F)=CC=C1CN1CC(C(=O)N(C=2C=C(C=CC=2)C#N)N2)=C2CC1 ANMMZJDZZMDJNA-UHFFFAOYSA-N 0.000 claims 2
- 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
- ZLFBGKHABGPHJG-UHFFFAOYSA-N 5-[(3-chloro-4-fluorophenyl)methyl]-2-(2-methyl-1,3-benzothiazol-6-yl)-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(F)C(Cl)=C1 ZLFBGKHABGPHJG-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
- 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
- 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
- 208000019423 liver disease Diseases 0.000 claims 2
- 230000004060 metabolic process Effects 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
- 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
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 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
- AMDHKJNCXJUHHU-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-[(3-methoxyphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound COC1=CC=CC(CN2C(C=3CN(CC=4C=CC(Cl)=CC=4)CCC=3N2)=O)=C1 AMDHKJNCXJUHHU-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 208000029515 lens disease Diseases 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 229950006238 nadide Drugs 0.000 claims 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 238000001959 radiotherapy Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/41—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10153927.8 | 2010-02-18 | ||
| EP10153927A EP2361911A1 (en) | 2010-02-18 | 2010-02-18 | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| 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 (OSRAM) |
| EP (2) | EP2361911A1 (OSRAM) |
| JP (1) | JP2013519724A (OSRAM) |
| KR (1) | KR20130010109A (OSRAM) |
| CN (1) | CN102762563A (OSRAM) |
| AU (1) | AU2011216893A1 (OSRAM) |
| BR (1) | BR112012020736A2 (OSRAM) |
| CA (1) | CA2789406A1 (OSRAM) |
| ES (1) | ES2446727T3 (OSRAM) |
| IL (1) | IL221207A (OSRAM) |
| RU (1) | RU2012139828A (OSRAM) |
| WO (1) | WO2011101804A1 (OSRAM) |
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 |
| EP2166009A1 (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 |
| EP2166010A1 (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 |
| 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 |
| US9687490B2 (en) | 2012-10-24 | 2017-06-27 | Glucox Biotech Ab | Triazine derivatives for the treatment of conditions associated with nicotinamide adenine dinucleotide phosphate oxidase |
| BR112015013440B1 (pt) * | 2012-12-13 | 2020-12-08 | Aduro Biotech, Inc | composições compreendendo dinucleotídeos de purina cíclicos com estereoquímicas |
| 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 |
| JP2018505226A (ja) | 2015-02-16 | 2018-02-22 | グルコックス・バイオテック・アーベー | Ｎ２−（３，４−ジメチルフェニル）−６−（（４−（ｐ−トリル）ピペラジン−１−イル）メチル）−１，３，５−トリアジン−２，４−ジアミン |
| ES2824450T3 (es) * | 2015-06-22 | 2021-05-12 | Actelion Pharmaceuticals Ltd | Compuestos de benzoxazol y de benzotiazol 2,5-disustituidos como inhibidores de la NADPH oxidasa 4 |
| 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 |
| BR112022013849A2 (pt) * | 2020-01-13 | 2022-09-13 | Aptabio Therapeutics Inc | Novo derivado de pirazol |
| AU2022224918B2 (en) | 2021-02-25 | 2023-04-13 | 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 (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| EP2166010A1 (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 |
| EP2166009A1 (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 |
| DK2382215T3 (da) * | 2008-12-29 | 2014-10-27 | Sanofi Sa | Derivater af 2-pyridin-2-yl-pyrazol-3(2h)-on, fremstilling og terapeutisk anvendelse heraf |
| 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 AU AU2011216893A patent/AU2011216893A1/en not_active Abandoned
- 2011-02-17 WO PCT/IB2011/050667 patent/WO2011101804A1/en not_active Ceased
- 2011-02-17 RU RU2012139828/04A patent/RU2012139828A/ru not_active Application Discontinuation
- 2011-02-17 EP EP11709807.9A patent/EP2536723B1/en active Active
- 2011-02-17 JP JP2012553434A patent/JP2013519724A/ja active Pending
- 2011-02-17 US US13/579,290 patent/US8865758B2/en not_active Expired - Fee Related
- 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 ES ES11709807.9T patent/ES2446727T3/es active Active
- 2011-02-17 CN CN2011800096795A patent/CN102762563A/zh active Pending
- 2011-02-17 KR KR1020127021407A patent/KR20130010109A/ko not_active Withdrawn
-
2012
- 2012-07-31 IL IL221207A patent/IL221207A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US8865758B2 (en) | 2014-10-21 |
| CN102762563A (zh) | 2012-10-31 |
| EP2536723A1 (en) | 2012-12-26 |
| ES2446727T3 (es) | 2014-03-10 |
| WO2011101804A1 (en) | 2011-08-25 |
| KR20130010109A (ko) | 2013-01-25 |
| US20120316163A1 (en) | 2012-12-13 |
| BR112012020736A2 (pt) | 2016-04-26 |
| EP2361911A1 (en) | 2011-08-31 |
| IL221207A0 (en) | 2012-10-31 |
| AU2011216893A1 (en) | 2012-08-16 |
| EP2536723B1 (en) | 2013-12-11 |
| JP2013519724A (ja) | 2013-05-30 |
| IL221207A (en) | 2015-01-29 |
| CA2789406A1 (en) | 2011-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2012139828A (ru) | Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы | |
| JP2013519724A5 (OSRAM) | ||
| RU2485114C2 (ru) | Карбоксамидные соединения и их применение в качестве ингибиторов кальпаинов | |
| RU2012139830A (ru) | Производные пиразолопиперидина в качестве ингибиторов nadph - оксидазы | |
| RU2011116232A (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| TWI579284B (zh) | 咪唑并吡咯啶酮化合物 | |
| RU2436780C2 (ru) | Производные 5-фенилтиазола и их применение в качестве ингибиторов рi3 киназы | |
| RU2011116230A (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| RU2492167C2 (ru) | Производные аминотриазола в качестве агонистов alх | |
| RU2379292C2 (ru) | Производные пиразола в качестве ингибиторов фосфодиэстеразы 4 | |
| JP2008523041A5 (OSRAM) | ||
| RU2011116226A (ru) | Пиразолопиридиновые производные как ингибиторы надфн-оксидазы | |
| JP2013520407A5 (OSRAM) | ||
| RU2010128240A (ru) | Производные аминопиразола | |
| JP2008513499A5 (OSRAM) | ||
| RU2009123525A (ru) | ПРОИЗВОДНЫЕ 5-СУЛЬФАНИЛМЕТИЛ[1,2,4}ТРИАЗОЛ[1,5-а]ПИРИМИДИН-7-ОЛА В КАЧЕСТВЕ АНТАГОНИСТОВ CXCR2 | |
| JP2020531498A5 (OSRAM) | ||
| RU2017121044A (ru) | Производные амидотиадиазола в качестве ингибиторов надфн-оксидазы | |
| JP2015503507A5 (OSRAM) | ||
| RU2017138549A (ru) | Ингибиторы репликации вируса иммунодефицита человека | |
| JP2005536475A5 (OSRAM) | ||
| JP2013544893A5 (OSRAM) | ||
| RU2009136299A (ru) | Новые производные 3-({1,2,4}триазоло{4,3-а}пиридин-7-ил)бензамида | |
| JP2003511384A5 (OSRAM) | ||
| JP2010533160A5 (OSRAM) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20150427 |