JPWO2020051153A5 - - Google Patents
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- Publication number
- JPWO2020051153A5 JPWO2020051153A5 JP2021536673A JP2021536673A JPWO2020051153A5 JP WO2020051153 A5 JPWO2020051153 A5 JP WO2020051153A5 JP 2021536673 A JP2021536673 A JP 2021536673A JP 2021536673 A JP2021536673 A JP 2021536673A JP WO2020051153 A5 JPWO2020051153 A5 JP WO2020051153A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- compound
- solvate
- acceptable salt
- alkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 35
- 150000003839 salts Chemical class 0.000 claims 31
- 239000012453 solvate Substances 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 208000016192 Demyelinating disease Diseases 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 5
- 229910052805 deuterium Inorganic materials 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229960000556 fingolimod Drugs 0.000 claims 4
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000002981 neuropathic effect Effects 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- YLOCGHYTXIINAI-XKUOMLDTSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 YLOCGHYTXIINAI-XKUOMLDTSA-N 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 claims 2
- 102100024217 CAMPATH-1 antigen Human genes 0.000 claims 2
- 108010065524 CD52 Antigen Proteins 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 108010072051 Glatiramer Acetate Proteins 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 claims 2
- 101001002508 Homo sapiens Immunoglobulin-binding protein 1 Proteins 0.000 claims 2
- 101001057504 Homo sapiens Interferon-stimulated gene 20 kDa protein Proteins 0.000 claims 2
- 101001055144 Homo sapiens Interleukin-2 receptor subunit alpha Proteins 0.000 claims 2
- 102100021042 Immunoglobulin-binding protein 1 Human genes 0.000 claims 2
- 108010038453 Interleukin-2 Receptors Proteins 0.000 claims 2
- 102000010789 Interleukin-2 Receptors Human genes 0.000 claims 2
- 102100026878 Interleukin-2 receptor subunit alpha Human genes 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- 102000018154 Muscarinic acetylcholine receptor M1 Human genes 0.000 claims 2
- 108050007299 Muscarinic acetylcholine receptor M1 Proteins 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229960000548 alemtuzumab Drugs 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical compound C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- 229960001334 corticosteroids Drugs 0.000 claims 2
- 229960002806 daclizumab Drugs 0.000 claims 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims 2
- 229960004419 dimethyl fumarate Drugs 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 229940042385 glatiramer Drugs 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- 230000002519 immonomodulatory effect Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 102000006495 integrins Human genes 0.000 claims 2
- 108010044426 integrins Proteins 0.000 claims 2
- 235000018977 lysine Nutrition 0.000 claims 2
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 2
- 229960001156 mitoxantrone Drugs 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 229960005027 natalizumab Drugs 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 210000001428 peripheral nervous system Anatomy 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 229960000331 teriflunomide Drugs 0.000 claims 2
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 235000002374 tyrosine Nutrition 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862726915P | 2018-09-04 | 2018-09-04 | |
| US62/726,915 | 2018-09-04 | ||
| PCT/US2019/049374 WO2020051153A1 (en) | 2018-09-04 | 2019-09-03 | Muscarinic acetylcholine m1 receptor antagonists |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021536505A JP2021536505A (ja) | 2021-12-27 |
| JPWO2020051153A5 true JPWO2020051153A5 (https=) | 2022-09-01 |
| JP2021536505A5 JP2021536505A5 (https=) | 2022-09-01 |
| JP7460264B2 JP7460264B2 (ja) | 2024-04-02 |
Family
ID=69721873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021536673A Active JP7460264B2 (ja) | 2018-09-04 | 2019-09-03 | ムスカリン性アセチルコリンｍ１受容体アンタゴニスト |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US12054487B2 (https=) |
| EP (1) | EP3846806A4 (https=) |
| JP (1) | JP7460264B2 (https=) |
| CN (2) | CN112638381B (https=) |
| AU (1) | AU2019336671B2 (https=) |
| CA (1) | CA3108076A1 (https=) |
| WO (1) | WO2020051153A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019241131A1 (en) | 2018-06-11 | 2019-12-19 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine m1 receptor antagonists |
| US12054487B2 (en) | 2018-09-04 | 2024-08-06 | Contineum Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
| IL326597A (en) * | 2019-10-07 | 2026-04-01 | Contineum Therapeutics Inc | Muscarinic M1 acetylcholine receptor antagonists |
| US11752149B2 (en) | 2019-12-02 | 2023-09-12 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
| CN117279917A (zh) * | 2021-05-21 | 2023-12-22 | 成都百裕制药股份有限公司 | 哌嗪衍生物及其在医药上的应用 |
| EP4359401A1 (en) * | 2021-06-23 | 2024-05-01 | Blueprint Medicines Corporation | Process for preparing egfr inhibitors |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4803203A (en) | 1986-11-05 | 1989-02-07 | Warner-Lambert Company | Phenyl and heterocyclic piperazinyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| US4873331A (en) | 1988-12-09 | 1989-10-10 | American Home Products Corporation | Noradamantyl-carboxylic acid piperazinoalkyl esters |
| US5089497A (en) | 1990-09-20 | 1992-02-18 | Warner-Lambert Company | Substituted piperazines as central nervous system agents |
| CN1061350C (zh) * | 1995-12-21 | 2001-01-31 | 美国辉瑞有限公司 | 2,7－取代的八氢－吡咯并[1,2－a]吡嗪衍生物 |
| WO2003066595A2 (en) | 2002-02-01 | 2003-08-14 | Euro-Celtique S.A. | 2 - piperazine - pyridines useful for treating pain |
| EP1596867A4 (en) | 2003-02-19 | 2006-03-22 | Merck & Co Inc | TREATMENT OF PSYCHOSIS WITH A MUSCARIN M1 RECEPTOR ECTOPIC ACTIVATOR |
| CA2570903C (en) | 2004-07-26 | 2013-09-17 | Applied Research Systems Ars Holding N.V. | N-hydroxyamide derivatives and use thereof |
| WO2007064732A1 (en) | 2005-12-01 | 2007-06-07 | Schering Corporation | Compounds for the treatment of inflammatory disorders and microbial diseases |
| US20090156465A1 (en) | 2005-12-30 | 2009-06-18 | Sattigeri Jitendra A | Derivatives of beta-amino acid as dipeptidyl peptidase-iv inhibitors |
| WO2012020567A1 (en) | 2010-08-09 | 2012-02-16 | Raqualia Pharma Inc. | Acyl piperazine derivatives as ttx-s blockers |
| WO2013049174A1 (en) | 2011-09-29 | 2013-04-04 | Abbvie Inc. | Substituted octahydropyrrolo[1,2-a]pyrazine sulfonamides as calcium channel blockers |
| EP3153167B1 (en) | 2011-10-28 | 2019-10-02 | Vanderbilt University | Substituted 2-(4-heterocyclylbenzyl)isoindolin-1-one analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
| US8697888B2 (en) | 2012-01-06 | 2014-04-15 | Vanderbilt University | Substituted (1-(methylsulfonyl)azetidin-3-yl)(heterocycloalkyl)methanone analogs as antagonists of muscarinic acetylcholine M1 receptors |
| US20130289019A1 (en) | 2012-04-26 | 2013-10-31 | Amazing Grace, Inc. | Methods of treating behaviorial and/or mental disorders |
| BR112015006029B1 (pt) | 2012-09-18 | 2022-01-25 | Heptares Therapeutics Limited | Compostos aza bicíclicos como agonistas de receptor m1 muscarínicos, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou distúrbio psicótico ou para tratar ou reduzir a gravidade de dores agudas, crônicas, neuropáticas ou inflamatórias |
| EP3371164B1 (en) * | 2015-11-06 | 2022-03-16 | Neurocrine Biosciences, Inc. | N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(pyrazin-2-yl)-piperazine-1-carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
| WO2018085803A1 (en) * | 2016-11-07 | 2018-05-11 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| WO2018089433A1 (en) | 2016-11-08 | 2018-05-17 | Navitor Pharmaceuticals, Inc. | PHENYL mTORC INHIBITORS AND USES THEREOF |
| JP7291711B2 (ja) | 2018-02-15 | 2023-06-15 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｔｒｐｃ６阻害剤 |
| EP3788040B1 (en) | 2018-04-30 | 2023-04-12 | Ribon Therapeutics Inc. | Pyridazinones as parp7 inhibitors |
| WO2019241131A1 (en) | 2018-06-11 | 2019-12-19 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine m1 receptor antagonists |
| US12054487B2 (en) | 2018-09-04 | 2024-08-06 | Contineum Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
| IL326597A (en) | 2019-10-07 | 2026-04-01 | Contineum Therapeutics Inc | Muscarinic M1 acetylcholine receptor antagonists |
| US11752149B2 (en) | 2019-12-02 | 2023-09-12 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
-
2019
- 2019-09-03 US US17/267,677 patent/US12054487B2/en active Active
- 2019-09-03 AU AU2019336671A patent/AU2019336671B2/en active Active
- 2019-09-03 EP EP19857624.1A patent/EP3846806A4/en active Pending
- 2019-09-03 WO PCT/US2019/049374 patent/WO2020051153A1/en not_active Ceased
- 2019-09-03 JP JP2021536673A patent/JP7460264B2/ja active Active
- 2019-09-03 CA CA3108076A patent/CA3108076A1/en active Pending
- 2019-09-03 CN CN201980057628.6A patent/CN112638381B/zh active Active
- 2019-09-03 CN CN202411263115.XA patent/CN119112895A/zh active Pending
-
2024
- 2024-06-18 US US18/747,272 patent/US20250026758A1/en active Pending
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