KR20130010109A - Ｎａｄｐｈ 옥시다아제 억제제인 피라졸로 피페리딘 유도체 - Google Patents
Ｎａｄｐｈ 옥시다아제 억제제인 피라졸로 피페리딘 유도체 Download PDFInfo
- Publication number
- KR20130010109A KR20130010109A KR1020127021407A KR20127021407A KR20130010109A KR 20130010109 A KR20130010109 A KR 20130010109A KR 1020127021407 A KR1020127021407 A KR 1020127021407A KR 20127021407 A KR20127021407 A KR 20127021407A KR 20130010109 A KR20130010109 A KR 20130010109A
- Authority
- KR
- South Korea
- Prior art keywords
- pyrazolo
- hexahydro
- pyridin
- optionally substituted
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 108010002998 NADPH Oxidases Proteins 0.000 title claims abstract description 37
- 102000004722 NADPH Oxidases Human genes 0.000 title claims abstract description 37
- RTTBBADOMOOPTQ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-b]pyridine Chemical class C1CCNC2=C1NN=C2 RTTBBADOMOOPTQ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000003112 inhibitor Substances 0.000 title description 2
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 claims abstract description 7
- 101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 claims abstract description 7
- 102100021217 Dual oxidase 2 Human genes 0.000 claims abstract description 4
- -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 132
- 150000001875 compounds Chemical class 0.000 claims description 105
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 91
- 201000010099 disease Diseases 0.000 claims description 87
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 87
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 72
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 69
- 125000003107 substituted aryl group Chemical group 0.000 claims description 59
- 206010028980 Neoplasm Diseases 0.000 claims description 53
- 230000033115 angiogenesis Effects 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 43
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 39
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 37
- 208000024891 symptom Diseases 0.000 claims description 36
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 35
- 201000011510 cancer Diseases 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 30
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 30
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 208000014674 injury Diseases 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 208000023504 respiratory system disease Diseases 0.000 claims description 17
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 15
- 208000020084 Bone disease Diseases 0.000 claims description 14
- 208000022555 Genital disease Diseases 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 230000004770 neurodegeneration Effects 0.000 claims description 14
- 208000017169 kidney disease Diseases 0.000 claims description 13
- 208000017520 skin disease Diseases 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 12
- 208000026935 allergic disease Diseases 0.000 claims description 12
- 230000036407 pain Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 210000003027 ear inner Anatomy 0.000 claims description 11
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 230000002008 hemorrhagic effect Effects 0.000 claims description 11
- 208000019423 liver disease Diseases 0.000 claims description 11
- 208000030159 metabolic disease Diseases 0.000 claims description 11
- 230000035939 shock Effects 0.000 claims description 11
- 230000008736 traumatic injury Effects 0.000 claims description 11
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 230000001419 dependent effect Effects 0.000 claims description 10
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 9
- 208000016097 disease of metabolism Diseases 0.000 claims description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 230000002314 neuroinflammatory effect Effects 0.000 claims description 8
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 230000002491 angiogenic effect Effects 0.000 claims description 6
- 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 description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000001959 radiotherapy Methods 0.000 claims description 5
- 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 description 4
- PKZMKBGLUCUHJV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-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(C=2C=C3OCOC3=CC=2)N2)=C2CC1 PKZMKBGLUCUHJV-UHFFFAOYSA-N 0.000 claims description 4
- TZNRCUWFPYPPMY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-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(C=2C=C3OCOC3=CC=2)N2)=C2CC1 TZNRCUWFPYPPMY-UHFFFAOYSA-N 0.000 claims description 4
- RYZISLNAQUCHEB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[(4-methylsulfonylphenyl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(C(=O)N(C=2C=C3OCOC3=CC=2)N2)=C2CC1 RYZISLNAQUCHEB-UHFFFAOYSA-N 0.000 claims description 4
- UAMOIDZFJAUOJA-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-5-[[3-(trifluoromethyl)phenyl]methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound FC(F)(F)C1=CC=CC(CN2CC=3C(=O)N(C=4C=C5OCOC5=CC=4)NC=3CC2)=C1 UAMOIDZFJAUOJA-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- WCZQRJQFJUFSBM-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[(6-chloropyridin-3-yl)methyl]-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(CN(CC=2C=NC(Cl)=CC=2)CC2)=C2N1 WCZQRJQFJUFSBM-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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- 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 description 4
- ZVWRZVMOGXVZOW-UHFFFAOYSA-N 3-[5-[(6-chloropyridin-3-yl)methyl]-3-oxo-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-yl]benzonitrile Chemical compound C1=NC(Cl)=CC=C1CN1CC(C(=O)N(C=2C=C(C=CC=2)C#N)N2)=C2CC1 ZVWRZVMOGXVZOW-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
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Classifications
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Landscapes
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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 |
|---|---|
| KR20130010109A true KR20130010109A (ko) | 2013-01-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127021407A Withdrawn KR20130010109A (ko) | 2010-02-18 | 2011-02-17 | Ｎａｄｐｈ 옥시다아제 억제제인 피라졸로 피페리딘 유도체 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020247665A1 (en) | 2019-06-05 | 2020-12-10 | Emory University | Peptidomimetics for the treatment of coronavirus and picornavirus infections |
Families Citing this family (16)
| 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 |
| 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 |
| 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 |
| 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 |
| AU2013358892B2 (en) * | 2012-12-13 | 2018-06-21 | 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 |
| 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 |
| WO2016207785A1 (en) * | 2015-06-22 | 2016-12-29 | Actelion Pharmaceuticals Ltd | Nadph oxidase 4 inhibitors |
| EP3479843A1 (en) | 2017-11-01 | 2019-05-08 | GenKyoTex Suisse SA | Use of nox inhibitors for treatment of cancer |
| BR112022013849A2 (pt) * | 2020-01-13 | 2022-09-13 | Aptabio Therapeutics Inc | Novo derivado de pirazol |
| MX2023000926A (es) * | 2021-02-25 | 2023-02-22 | Aptabio Therapeutics Inc | Nuevo derivado de pirazol. |
| WO2025011546A1 (en) * | 2023-07-10 | 2025-01-16 | Acelon Therapeutics | Human caseinolytic protease p agonists and uses thereof |
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| TW432073B (en) * | 1995-12-28 | 2001-05-01 | Pfizer | Pyrazolopyridine compounds |
| HU225917B1 (en) * | 1999-09-16 | 2007-12-28 | Tanabe Seiyaku Co | Pyrimidine and pyrazine derivatives, pharmaceutical compositions containing them and their use |
| 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 |
| 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 |
| MX2011007061A (es) * | 2008-12-29 | 2011-12-16 | Sanofi Sa | Derivados de 2 piridin- 2-il-pirazol-3 (2h)-ona, su preparacion y aplicacion terapeutica. |
| 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 |
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2010
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2011
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- 2011-02-17 EP EP11709807.9A patent/EP2536723B1/en active Active
- 2011-02-17 US US13/579,290 patent/US8865758B2/en not_active Expired - Fee Related
- 2011-02-17 CA CA2789406A patent/CA2789406A1/en not_active Abandoned
- 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 BR BR112012020736A patent/BR112012020736A2/pt not_active IP Right Cessation
-
2012
- 2012-07-31 IL IL221207A patent/IL221207A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020247665A1 (en) | 2019-06-05 | 2020-12-10 | Emory University | Peptidomimetics for the treatment of coronavirus and picornavirus infections |
Also Published As
| Publication number | Publication date |
|---|---|
| US20120316163A1 (en) | 2012-12-13 |
| CN102762563A (zh) | 2012-10-31 |
| BR112012020736A2 (pt) | 2016-04-26 |
| ES2446727T3 (es) | 2014-03-10 |
| JP2013519724A (ja) | 2013-05-30 |
| EP2536723A1 (en) | 2012-12-26 |
| IL221207A0 (en) | 2012-10-31 |
| WO2011101804A1 (en) | 2011-08-25 |
| IL221207A (en) | 2015-01-29 |
| AU2011216893A1 (en) | 2012-08-16 |
| RU2012139828A (ru) | 2014-03-27 |
| CA2789406A1 (en) | 2011-08-25 |
| US8865758B2 (en) | 2014-10-21 |
| EP2361911A1 (en) | 2011-08-31 |
| EP2536723B1 (en) | 2013-12-11 |
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Legal Events
| Date | Code | Title | Description |
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| PA0105 | International application |
Patent event date: 20120814 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |