JP2017500334A5 - - Google Patents
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- JP2017500334A5 JP2017500334A5 JP2016541280A JP2016541280A JP2017500334A5 JP 2017500334 A5 JP2017500334 A5 JP 2017500334A5 JP 2016541280 A JP2016541280 A JP 2016541280A JP 2016541280 A JP2016541280 A JP 2016541280A JP 2017500334 A5 JP2017500334 A5 JP 2017500334A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aliphatic
- independently
- aryl
- compound
- 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.)
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 163
- 150000001875 compounds Chemical class 0.000 claims description 146
- 125000001931 aliphatic group Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 44
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000012453 solvate Substances 0.000 claims description 36
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 208000010877 cognitive disease Diseases 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 208000015114 central nervous system disease Diseases 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 229940124597 therapeutic agent Drugs 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 8
- -1 —C (O) OEt Chemical group 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 6
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 4
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 4
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims description 4
- 229960004640 memantine Drugs 0.000 claims description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 4
- 208000028698 Cognitive impairment Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims description 2
- 206010003805 Autism Diseases 0.000 claims description 2
- 208000020706 Autistic disease Diseases 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims description 2
- 208000036626 Mental retardation Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 230000000561 anti-psychotic effect Effects 0.000 claims description 2
- 239000000164 antipsychotic agent Substances 0.000 claims description 2
- 229960004372 aripiprazole Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229960003530 donepezil Drugs 0.000 claims description 2
- 229960003980 galantamine Drugs 0.000 claims description 2
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 2
- 229960005017 olanzapine Drugs 0.000 claims description 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229960004136 rivastigmine Drugs 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 229960000607 ziprasidone Drugs 0.000 claims description 2
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 description 15
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- 0 Cc1nnc(*)[n]1C Chemical compound Cc1nnc(*)[n]1C 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 230000037410 cognitive enhancement Effects 0.000 description 1
- 231100000867 compulsive behavior Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HICZHPFZMDTJBP-UHFFFAOYSA-N methyl 3,5-diphenylpyridazine-4-carboxylate Chemical compound COC(=O)C1=C(C=2C=CC=CC=2)C=NN=C1C1=CC=CC=C1 HICZHPFZMDTJBP-UHFFFAOYSA-N 0.000 description 1
- 230000000897 modulatory effect Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361919390P | 2013-12-20 | 2013-12-20 | |
| US201361919394P | 2013-12-20 | 2013-12-20 | |
| US61/919,390 | 2013-12-20 | ||
| US61/919,394 | 2013-12-20 | ||
| US201462075743P | 2014-11-05 | 2014-11-05 | |
| US62/075,743 | 2014-11-05 | ||
| PCT/US2014/071644 WO2015095783A1 (en) | 2013-12-20 | 2014-12-19 | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019193538A Division JP2020011998A (ja) | 2013-12-20 | 2019-10-24 | 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 |
| JP2021031721A Division JP2021080287A (ja) | 2013-12-20 | 2021-03-01 | 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017500334A JP2017500334A (ja) | 2017-01-05 |
| JP2017500334A5 true JP2017500334A5 (enExample) | 2018-02-01 |
| JP6883988B2 JP6883988B2 (ja) | 2021-06-09 |
Family
ID=53403769
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016541280A Active JP6883988B2 (ja) | 2013-12-20 | 2014-12-19 | 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 |
| JP2019193538A Pending JP2020011998A (ja) | 2013-12-20 | 2019-10-24 | 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 |
| JP2021031721A Withdrawn JP2021080287A (ja) | 2013-12-20 | 2021-03-01 | 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 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019193538A Pending JP2020011998A (ja) | 2013-12-20 | 2019-10-24 | 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 |
| JP2021031721A Withdrawn JP2021080287A (ja) | 2013-12-20 | 2021-03-01 | 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 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10329301B2 (enExample) |
| EP (2) | EP4032889A1 (enExample) |
| JP (3) | JP6883988B2 (enExample) |
| CN (2) | CN106068256B (enExample) |
| AU (1) | AU2014368961B2 (enExample) |
| CA (2) | CA3123897C (enExample) |
| IL (1) | IL246261B (enExample) |
| MX (2) | MX381561B (enExample) |
| NZ (2) | NZ722077A (enExample) |
| WO (1) | WO2015095783A1 (enExample) |
| ZA (1) | ZA201605027B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO3034079T3 (enExample) | 2010-11-15 | 2018-06-09 | ||
| US10329301B2 (en) | 2013-12-20 | 2019-06-25 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| CA2990004C (en) * | 2015-06-19 | 2024-04-23 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US10449181B2 (en) | 2016-08-25 | 2019-10-22 | Sarah E. Labance | Treatment of autism and autism spectrum disorders (ASD) |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| BR112020026062B1 (pt) * | 2018-06-19 | 2023-04-04 | Agenebio, Inc | Compostos derivados de benzodiazepina ou um sal farmaceuticamente aceitavel, isômero ou combinação dos mesmos, composição farmacêutica compreendendo os mesmos e usos dos mesmos para o tratamento de comprometimento cognitivo, câncer cerebral e psicose da doença de parkinson |
| WO2020165802A1 (en) * | 2019-02-13 | 2020-08-20 | Centre For Addiction And Mental Health | Compositions and methods relating to use of agonists of alpha5-containing gabaa receptors |
| KR20220016918A (ko) | 2019-06-04 | 2022-02-10 | 하거 바이오사이언시즈, 엘엘씨 | 오렉신 길항제로서의 이미다졸로 유도체, 조성물 및 방법 |
| MX2022007725A (es) * | 2019-12-19 | 2022-07-19 | Agenebio Inc | Derivados de benzodiazepinas, composiciones y metodos para tratar deterioro cognitivo. |
| IL296716A (en) | 2020-03-26 | 2022-11-01 | Richter Gedeon Nyrt | History of naphthyridine and pyrido[4,3-c]pyridazine as gabaa alpha 5 receptor modulators |
| IL299754A (en) * | 2020-07-10 | 2023-03-01 | Agenebio Inc | Combinations of gaba alpha 5 agonists and sv2a inhibitors and methods of using in the treatment of cognitive impairment |
| IL299761A (en) * | 2020-07-10 | 2023-03-01 | Agenebio Inc | GABAA alpha 5 agonist polymorphs and methods of use for the treatment of cognitive impairment |
| CN113284553B (zh) * | 2021-05-28 | 2023-01-10 | 南昌大学 | 一种用于治疗药物成瘾的药物靶点结合能力测试方法 |
| HU231691B1 (hu) | 2021-09-29 | 2025-10-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
| EP4572852A1 (en) | 2022-08-19 | 2025-06-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
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2014
- 2014-12-19 US US15/104,494 patent/US10329301B2/en active Active
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- 2014-12-19 WO PCT/US2014/071644 patent/WO2015095783A1/en not_active Ceased
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