JP2018522034A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018522034A5 JP2018522034A5 JP2018504993A JP2018504993A JP2018522034A5 JP 2018522034 A5 JP2018522034 A5 JP 2018522034A5 JP 2018504993 A JP2018504993 A JP 2018504993A JP 2018504993 A JP2018504993 A JP 2018504993A JP 2018522034 A5 JP2018522034 A5 JP 2018522034A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- azaspiro
- piperidin
- compound
- hydrogen
- 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 24
- 150000003839 salts Chemical class 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 12
- -1 cyano, hydroxy, methoxy Chemical group 0.000 claims 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 239000011737 fluorine Substances 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- AQTFKGDWFRRIHR-UHFFFAOYSA-L 3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoate;cobalt(2+);hydron Chemical compound [Co+2].[N-]1C(C=C2C(=C(C)C(C=C3C(=C(C)C(=C4)[N-]3)C=C)=N2)C=C)=C(C)C(CCC(O)=O)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 AQTFKGDWFRRIHR-UHFFFAOYSA-L 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- GKODYOLWAJKWOR-OAHLLOKOSA-N ethyl 6-[4-[(2R)-2-ethyl-5-oxopyrrolidin-1-yl]piperidin-1-yl]-2-azaspiro[3.3]heptane-2-carboxylate Chemical compound C(C)[C@H]1N(C(CC1)=O)C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)C1 GKODYOLWAJKWOR-OAHLLOKOSA-N 0.000 claims 1
- PIAGNFVSQQDWNF-MRXNPFEDSA-N ethyl 6-[4-[(2R)-4,4-difluoro-2-(hydroxymethyl)pyrrolidin-1-yl]piperidin-1-yl]-2-azaspiro[3.3]heptane-2-carboxylate Chemical compound FC1(C[C@@H](N(C1)C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)C1)CO)F PIAGNFVSQQDWNF-MRXNPFEDSA-N 0.000 claims 1
- ZVYGUQXJVNRSMW-ATNAJCNCSA-N ethyl 6-[4-[(2S)-2-ethyl-5-oxopyrrolidin-1-yl]piperidin-1-yl]-2-azaspiro[3.4]octane-2-carboxylate Chemical compound C(C)[C@@H]1N(C(CC1)=O)C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)CC1 ZVYGUQXJVNRSMW-ATNAJCNCSA-N 0.000 claims 1
- FNPNRGQANRLYMU-MYJWUSKBSA-N ethyl 6-[4-[(2S)-2-methyl-5-oxopyrrolidin-1-yl]piperidin-1-yl]-2-azaspiro[3.4]octane-2-carboxylate Chemical compound C[C@@H]1N(C(CC1)=O)C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)CC1 FNPNRGQANRLYMU-MYJWUSKBSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- DVZYRUCGRJANBZ-QRWMCTBCSA-N methyl 6-[4-[(2R)-2-(1,3-oxazol-5-yl)pyrrolidin-1-yl]piperidin-1-yl]-2-azaspiro[3.4]octane-2-carboxylate Chemical compound O1C=NC=C1[C@@H]1N(CCC1)C1CCN(CC1)C1CC2(CN(C2)C(=O)OC)CC1 DVZYRUCGRJANBZ-QRWMCTBCSA-N 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 230000003551 muscarinic effect Effects 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1513740.9A GB201513740D0 (en) | 2015-08-03 | 2015-08-03 | Muscarinic agonist |
| GB1513740.9 | 2015-08-03 | ||
| PCT/GB2016/052384 WO2017021728A1 (en) | 2015-08-03 | 2016-08-03 | Muscarinic agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522034A JP2018522034A (ja) | 2018-08-09 |
| JP2018522034A5 true JP2018522034A5 (enExample) | 2019-09-12 |
| JP6847093B2 JP6847093B2 (ja) | 2021-03-24 |
Family
ID=54063147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018504993A Active JP6847093B2 (ja) | 2015-08-03 | 2016-08-03 | ムスカリン様アゴニスト |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10548884B2 (enExample) |
| EP (1) | EP3331528B1 (enExample) |
| JP (1) | JP6847093B2 (enExample) |
| CN (1) | CN107949384B (enExample) |
| AU (1) | AU2016302047B2 (enExample) |
| CA (1) | CA2994143C (enExample) |
| DK (1) | DK3331528T3 (enExample) |
| ES (1) | ES2894855T3 (enExample) |
| GB (1) | GB201513740D0 (enExample) |
| WO (1) | WO2017021728A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2780015B1 (en) | 2011-11-18 | 2017-01-04 | Heptares Therapeutics Limited | Muscarinic m1 receptor agonists |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201513740D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonist |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| TW201726675A (zh) | 2015-12-23 | 2017-08-01 | 默沙東藥廠 | M4毒蕈鹼乙醯膽鹼受體之異位調節劑6,7-二氫-5h-吡咯并[3,4-b]吡啶-5-酮 |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| AU2018300980A1 (en) | 2017-07-12 | 2020-01-02 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| IL273924B2 (en) | 2017-10-20 | 2024-07-01 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| WO2019126559A1 (en) | 2017-12-20 | 2019-06-27 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| PT3768669T (pt) * | 2018-03-23 | 2023-04-24 | Pfizer | Derivados de piperazina azaspiro |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| MX2022002881A (es) * | 2019-09-25 | 2022-06-08 | Oncoarendi Therapeutics Sa | Proceso para la produccion de 5-(4-((2s,5s)-5-(4-clorobencil)-2-me tilmorfolino)piperidin-1-il)-1h-1,2,4-triazol-3-amina. |
| WO2021070090A1 (en) * | 2019-10-09 | 2021-04-15 | Novartis Ag | 2-azaspiro[3.4]octane derivatives as m4 agonists |
| CN119390705A (zh) * | 2019-10-09 | 2025-02-07 | 诺华股份有限公司 | 作为m4激动剂的5-氧杂-2-氮杂螺[3.4]辛烷衍生物 |
| US12486250B2 (en) | 2019-12-06 | 2025-12-02 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| JP7707176B2 (ja) * | 2020-02-05 | 2025-07-14 | ニューロクライン バイオサイエンシーズ，インコーポレイテッド | ムスカリン性受容体４アンタゴニストおよび使用方法 |
| WO2023114224A1 (en) | 2021-12-13 | 2023-06-22 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
| WO2025030095A1 (en) * | 2023-08-03 | 2025-02-06 | Neurocrine Biosciences, Inc. | Methods of synthesis |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080098070A (ko) * | 2006-02-22 | 2008-11-06 | 버텍스 파마슈티칼스 인코포레이티드 | 무스카린성 수용체의 조절제로서의 스피로 축합된 피페리딘 |
| AU2007221214A1 (en) | 2006-02-22 | 2007-09-07 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| MX2011004340A (es) | 2008-10-29 | 2011-05-23 | Gruenenthal Gmbh | Espiroaminas sustituidas. |
| FR2945531A1 (fr) | 2009-05-12 | 2010-11-19 | Sanofi Aventis | Derives de 7-aza-spiro°3,5!nonane-7-carboxylates, leur preparation et leur application en therapeutique |
| EP2780015B1 (en) * | 2011-11-18 | 2017-01-04 | Heptares Therapeutics Limited | Muscarinic m1 receptor agonists |
| CN107098899B (zh) * | 2012-09-18 | 2019-09-06 | 赫普泰雅治疗有限公司 | 作为毒蕈碱的m1受体激动剂的二环氮杂化合物 |
| JP6478923B2 (ja) * | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| SG11201606269WA (en) * | 2014-02-06 | 2016-09-29 | Heptares Therapeutics Ltd | Bicyclic aza compounds as muscarinic m1 receptor and/or m4 receptor agonists |
| GB201504675D0 (en) * | 2015-03-19 | 2015-05-06 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513740D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonist |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
-
2015
- 2015-08-03 GB GBGB1513740.9A patent/GB201513740D0/en not_active Ceased
-
2016
- 2016-08-03 ES ES16750221T patent/ES2894855T3/es active Active
- 2016-08-03 AU AU2016302047A patent/AU2016302047B2/en active Active
- 2016-08-03 WO PCT/GB2016/052384 patent/WO2017021728A1/en not_active Ceased
- 2016-08-03 DK DK16750221.0T patent/DK3331528T3/da active
- 2016-08-03 CA CA2994143A patent/CA2994143C/en active Active
- 2016-08-03 EP EP16750221.0A patent/EP3331528B1/en active Active
- 2016-08-03 JP JP2018504993A patent/JP6847093B2/ja active Active
- 2016-08-03 CN CN201680045225.6A patent/CN107949384B/zh active Active
- 2016-08-03 US US15/749,743 patent/US10548884B2/en active Active
-
2019
- 2019-12-27 US US16/728,762 patent/US11324738B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018522034A5 (enExample) | ||
| ES2688548T3 (es) | Compuestos aza bicíclicos como agonistas del receptor muscarínico M1 | |
| KR102722493B1 (ko) | Mdm2-p53 억제제로서의 스피로[3h-인돌-3,2'-피롤리딘]-2(1h)-온 화합물 및 유도체 | |
| US9828379B2 (en) | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof | |
| JP6847093B2 (ja) | ムスカリン様アゴニスト | |
| JP2018522033A5 (enExample) | ||
| JP2021528446A5 (enExample) | ||
| RU2007120454A (ru) | Производные хинуклидина и их применение в качестве антагонистов мускариновых рецепторов м3 | |
| TN2018000130A1 (en) | 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 | |
| RU2016138788A (ru) | Агонисты мускариновых рецепторов | |
| CN114786673A (zh) | Cdk抑制剂及其作为药物的用途 | |
| RU2019143759A (ru) | Новое соединение бифенила или его соль | |
| RU2017115305A (ru) | Ингибиторы биосинтеза гепарансульфата для лечения заболеваний | |
| JP2015501799A5 (enExample) | ||
| RU2018114518A (ru) | Новые бициклические соединения в качестве двойных ингибиторов аутотаксина (atx)/карбоангидразы (ca) | |
| JP2013508382A5 (enExample) | ||
| JP2016513681A5 (enExample) | ||
| MX344109B (es) | Formulaciones de sal de meglumina del ácido 1-(5,6-dicloro-1h-benz o[d]imidazol-2-il)-1h-pirazol-4-carboxílico. | |
| JP2016517409A5 (enExample) | ||
| RU2015143676A (ru) | Модулятолры ship1 и относящиеся к ним способы | |
| JP2018522929A5 (enExample) | ||
| NZ629453A (en) | Thiazole derivatives as alpha 7 nachr modulators | |
| WO2017157792A1 (en) | Combinations of copanlisib | |
| CA2619897A1 (fr) | Nouveaux derives tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| JPWO2013002365A1 (ja) | 止痒剤 |