JPWO2021191838A5 - - Google Patents
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- Publication number
- JPWO2021191838A5 JPWO2021191838A5 JP2022557102A JP2022557102A JPWO2021191838A5 JP WO2021191838 A5 JPWO2021191838 A5 JP WO2021191838A5 JP 2022557102 A JP2022557102 A JP 2022557102A JP 2022557102 A JP2022557102 A JP 2022557102A JP WO2021191838 A5 JPWO2021191838 A5 JP WO2021191838A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- group
- methoxy
- tetrahydro
- methylpyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 5
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 208000029560 autism spectrum disease Diseases 0.000 claims 4
- 206010027175 memory impairment Diseases 0.000 claims 4
- 239000002207 metabolite Substances 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- -1 2,2,2-trifluoro-1-[6-({5-methyl-3-[6-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl}methoxy)- 1,2,3,4-tetrahydro-2,7-naphthyridin-2-yl]ethane-1-one Chemical compound 0.000 claims 2
- 208000009575 Angelman syndrome Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims 2
- 208000027626 Neurocognitive disease Diseases 0.000 claims 2
- 208000029726 Neurodevelopmental disease Diseases 0.000 claims 2
- 201000010769 Prader-Willi syndrome Diseases 0.000 claims 2
- 208000006289 Rett Syndrome Diseases 0.000 claims 2
- 208000027520 Somatoform disease Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000007278 cognition impairment Effects 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- 230000006806 disease prevention Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 208000027753 pain disease Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- HYQHYVSPOHMFAL-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C Chemical compound C(C1=CC=CC=C1)(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C HYQHYVSPOHMFAL-UHFFFAOYSA-N 0.000 claims 1
- YNUSMBWLLBZKFW-UHFFFAOYSA-N C1(CC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C Chemical compound C1(CC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C YNUSMBWLLBZKFW-UHFFFAOYSA-N 0.000 claims 1
- ZFUMTAHHKXOOAE-UHFFFAOYSA-N C1(CC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC=1C(=NOC=1C)C=1C=NC(=CC=1)C Chemical compound C1(CC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC=1C(=NOC=1C)C=1C=NC(=CC=1)C ZFUMTAHHKXOOAE-UHFFFAOYSA-N 0.000 claims 1
- LVJBBXYWAWPZCO-UHFFFAOYSA-N C1(CC1)C(=O)N1CC=2N=NC(=CC=2CC1)OCC=1C(=NOC=1C)C=1C=CC(=NC=1)C Chemical compound C1(CC1)C(=O)N1CC=2N=NC(=CC=2CC1)OCC=1C(=NOC=1C)C=1C=CC(=NC=1)C LVJBBXYWAWPZCO-UHFFFAOYSA-N 0.000 claims 1
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- ZIFLIKRPKKAEMG-UHFFFAOYSA-N C1(CCC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C Chemical compound C1(CCC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C ZIFLIKRPKKAEMG-UHFFFAOYSA-N 0.000 claims 1
- QXEDALDPHGEJDY-UHFFFAOYSA-N C1(CCC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC=1C(=NOC=1C)C=1C=NC(=CC=1)C Chemical compound C1(CCC1)C(=O)N1CC2=CN=C(C=C2CC1)OCC=1C(=NOC=1C)C=1C=NC(=CC=1)C QXEDALDPHGEJDY-UHFFFAOYSA-N 0.000 claims 1
- IQMXWPWBRBJEBB-UHFFFAOYSA-N C1=C(N=CC(=C1)C=1C(=C(ON=1)C)COC1=NC=C2C(=C1)CCN(C(=O)C1CCC(=O)N(C1)C)C2)C Chemical compound C1=C(N=CC(=C1)C=1C(=C(ON=1)C)COC1=NC=C2C(=C1)CCN(C(=O)C1CCC(=O)N(C1)C)C2)C IQMXWPWBRBJEBB-UHFFFAOYSA-N 0.000 claims 1
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- QTANMKKDFSOQHK-UHFFFAOYSA-N CC(C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C)(C)C Chemical compound CC(C(=O)N1CC2=CN=C(C=C2CC1)OCC1=C(N=NN1C=1C=NC(=CC=1)C)C)(C)C QTANMKKDFSOQHK-UHFFFAOYSA-N 0.000 claims 1
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| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
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| HU230518B1 (hu) | 2005-12-20 | 2016-10-28 | Richter Gedeon Nyrt. | Bradykinin B1 receptor szelektív antagonista hatással rendelkező új fenatridin származékok, eljárás előállításukra, és az ezeket tartalmazó gyógyszerkészítmények |
| HUP0600810A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New sulfonamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| HUP0600808A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New benzamide derivatives as bradykinin antagonists, process for their preparation and pharmaceutical compositions containing them |
| HUP0600809A3 (en) | 2006-10-27 | 2008-09-29 | Richter Gedeon Nyrt | New phenylsulfamoyl-benzamide derivatives as bradykinin antagonists, process and intermediates for their preparation and pharmaceutical compositions containing them |
| US7943619B2 (en) | 2007-12-04 | 2011-05-17 | Hoffmann-La Roche Inc. | Isoxazolo-pyridazine derivatives |
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| CA2828578A1 (en) * | 2011-03-04 | 2012-09-13 | Lexicon Pharmaceuticals, Inc. | Mst1 kinase inhibitors and methods of their use |
| DK2937349T3 (en) | 2011-03-23 | 2017-02-20 | Amgen Inc | CONDENSED TRICYCLIC DUAL INHIBITORS OF CDK 4/6 AND FLT3 |
| US9206160B2 (en) * | 2012-06-26 | 2015-12-08 | Saniona Aps | Phenyl triazole derivative and its use for modulating the GABAA receptor complex |
| CA2876780A1 (en) | 2012-06-26 | 2014-01-03 | Saniona Aps | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
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| WO2014001278A1 (en) | 2012-06-26 | 2014-01-03 | Aniona Aps | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| CN102924452B (zh) * | 2012-11-16 | 2015-01-21 | 苏州施亚生物科技有限公司 | 5,6,7,8-四氢-2H-吡啶并[3,4-c]哒嗪-3-酮的合成方法 |
| HUP1300139A2 (en) | 2013-03-06 | 2014-09-29 | Richter Gedeon Nyrt | Phenoxypiperidine h3 antagonists |
| JP6883988B2 (ja) | 2013-12-20 | 2021-06-09 | エージンバイオ， インコーポレイテッド | ベンゾジアゼピン誘導体、組成物、および認知障害を処置するための方法 |
| US9296747B1 (en) * | 2014-10-10 | 2016-03-29 | Allergan, Inc. | Piperidylpyrimidine derivatives as modulators of protein kinase inhibitors and of vascular endothelial growth factor receptor 2 |
| KR20180030545A (ko) * | 2015-06-22 | 2018-03-23 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 바이사이클릭 헤테로사이클릭 아미드 유도체 |
| MX2018002446A (es) | 2015-08-28 | 2019-01-10 | Abbvie Inc | Compuestos heterociclicos fusionados como moduladores s1p. |
| EP4129297A1 (en) | 2016-03-18 | 2023-02-08 | UWM Research Foundation, Inc. | Treatment of cognitive and mood symptoms in neurodegenerative and neuropsychiatric disorders with alpha5-containing gabaa receptor agonists |
| CR20190268A (es) * | 2016-12-08 | 2019-07-11 | Hoffmann La Roche | Nuevos deribados de isoxazolil éter como pam de gaba a alfa5 |
| US20200268728A1 (en) * | 2016-12-20 | 2020-08-27 | Sumitomo Dainippon Pharma Co., Ltd. | Drug targeting cancer stem cell |
| HU231058B1 (hu) | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt. | Gyógyászatilag hatékony aliciklusos-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| HU231057B1 (hu) | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt | Gyógyászatilag hatékony aril-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| CA3120971A1 (en) | 2017-11-27 | 2019-05-31 | Dart Neuroscience, Llc | Substituted furanopyrimidine compounds as pde1 inhibitors |
| TW201938171A (zh) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | 作為血管升壓素Ｖ１ａ受體拮抗劑之三環化合物 |
| HU231206B1 (hu) | 2017-12-15 | 2021-10-28 | Richter Gedeon Nyrt. | Triazolobenzazepinek |
| SG11202012200QA (en) | 2018-06-13 | 2021-01-28 | Hoffmann La Roche | New isoxazolyl ether derivatives as gaba a alpha5 pam |
| HU231414B1 (hu) | 2018-07-13 | 2023-08-28 | Richter Gedeon Nyrt. | Tiadiazin származékok |
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| HU231478B1 (hu) | 2018-07-13 | 2024-02-28 | Richter Gedeon Nyrt. | Szubsztituált (aza)indol származékok |
| BR102019014802A2 (pt) * | 2018-07-20 | 2020-02-04 | Boehringer Ingelheim Int | difluorometil-fenil triazóis |
| HU231223B1 (hu) * | 2018-09-28 | 2022-01-28 | Richter Gedeon Nyrt. | GABAA A5 receptor modulátor hatású biciklusos vegyületek |
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