JP2018531981A5 - - Google Patents
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- Publication number
- JP2018531981A5 JP2018531981A5 JP2018522553A JP2018522553A JP2018531981A5 JP 2018531981 A5 JP2018531981 A5 JP 2018531981A5 JP 2018522553 A JP2018522553 A JP 2018522553A JP 2018522553 A JP2018522553 A JP 2018522553A JP 2018531981 A5 JP2018531981 A5 JP 2018531981A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- alkyl
- acceptable salt
- solvate
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 178
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 57
- 239000012453 solvate Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 208000012902 Nervous system disease Diseases 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- -1 -C (= O) NH 2 Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 12
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 12
- 208000025966 Neurological disease Diseases 0.000 claims description 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 11
- 210000004027 cell Anatomy 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 208000012661 Dyskinesia Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 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 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010008748 Chorea Diseases 0.000 claims description 3
- 208000014094 Dystonic disease Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 3
- 201000002832 Lewy body dementia Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010034010 Parkinsonism Diseases 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- 206010008129 cerebral palsy Diseases 0.000 claims description 3
- 208000012601 choreatic disease Diseases 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 208000010118 dystonia Diseases 0.000 claims description 3
- 229960004502 levodopa Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims 11
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CMGDKBYBRVTZIC-LJQANCHMSA-N (2R)-N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-methyl-4-[5-(trifluoromethyl)pyrimidin-2-yl]piperazine-1-carboxamide Chemical group C(C1=CC=CC=C1)N1CCC(CC1)CCNC(=O)N1[C@@H](CN(CC1)C1=NC=C(C=N1)C(F)(F)F)C CMGDKBYBRVTZIC-LJQANCHMSA-N 0.000 claims 1
- WYRMWVLWIJOYMF-OAQYLSRUSA-N (2R)-N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(3-cyano-5-fluorophenyl)-2-methylpiperazine-1-carboxamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)CCNC(=O)N1[C@@H](CN(CC1)C1=CC(=CC(=C1)F)C#N)C WYRMWVLWIJOYMF-OAQYLSRUSA-N 0.000 claims 1
- SFCDZMQWBYMULT-NHCUHLMSSA-N (2R,6R)-N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(5-cyanopyrimidin-2-yl)-2,6-dimethylpiperazine-1-carboxamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)CCNC(=O)N1[C@@H](CN(C[C@H]1C)C1=NC=C(C=N1)C#N)C SFCDZMQWBYMULT-NHCUHLMSSA-N 0.000 claims 1
- SFCDZMQWBYMULT-OYRHEFFESA-N (2R,6S)-N-[2-(1-benzylpiperidin-4-yl)ethyl]-4-(5-cyanopyrimidin-2-yl)-2,6-dimethylpiperazine-1-carboxamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)CCNC(=O)N1[C@H](CN(C[C@H]1C)C1=NC=C(C=N1)C#N)C SFCDZMQWBYMULT-OYRHEFFESA-N 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 210000003370 receptor cell Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 8
- 229940002612 prodrug Drugs 0.000 description 8
- 239000000651 prodrug Substances 0.000 description 8
- 0 C1=CSC2=CC=*=CC=C12 Chemical compound C1=CSC2=CC=*=CC=C12 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004474 heteroalkylene group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562252179P | 2015-11-06 | 2015-11-06 | |
| US62/252,179 | 2015-11-06 | ||
| US201662275708P | 2016-01-06 | 2016-01-06 | |
| US62/275,708 | 2016-01-06 | ||
| PCT/US2016/060659 WO2017079641A1 (en) | 2015-11-06 | 2016-11-04 | 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021000354A Division JP2021050243A (ja) | 2015-11-06 | 2021-01-05 | 神経学的疾患を処置するためのムスカリン受容体４（ｍ４）アンタゴニストとしての、ｎ−［２−（１−ベンジルピペリジン−４−イル）エチル］−４−（ピラジン−２−イル）−ピペラジン−１−カルボキサミド誘導体および関連化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018531981A JP2018531981A (ja) | 2018-11-01 |
| JP2018531981A5 true JP2018531981A5 (enExample) | 2019-12-19 |
| JP6917989B2 JP6917989B2 (ja) | 2021-08-11 |
Family
ID=57349137
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018522553A Active JP6917989B2 (ja) | 2015-11-06 | 2016-11-04 | 神経学的疾患を処置するためのムスカリン受容体４（ｍ４）アンタゴニストとしての、ｎ−［２−（１−ベンジルピペリジン−４−イル）エチル］−４−（ピラジン−２−イル）−ピペラジン−１−カルボキサミド誘導体および関連化合物 |
| JP2021000354A Withdrawn JP2021050243A (ja) | 2015-11-06 | 2021-01-05 | 神経学的疾患を処置するためのムスカリン受容体４（ｍ４）アンタゴニストとしての、ｎ−［２−（１−ベンジルピペリジン−４−イル）エチル］−４−（ピラジン−２−イル）−ピペラジン−１−カルボキサミド誘導体および関連化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021000354A Withdrawn JP2021050243A (ja) | 2015-11-06 | 2021-01-05 | 神経学的疾患を処置するためのムスカリン受容体４（ｍ４）アンタゴニストとしての、ｎ−［２−（１−ベンジルピペリジン−４−イル）エチル］−４−（ピラジン−２−イル）−ピペラジン−１−カルボキサミド誘導体および関連化合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US11033539B2 (enExample) |
| EP (1) | EP3371164B1 (enExample) |
| JP (2) | JP6917989B2 (enExample) |
| KR (1) | KR20180073685A (enExample) |
| CN (1) | CN108349936B (enExample) |
| AU (1) | AU2016348524B2 (enExample) |
| BR (1) | BR112018008630A2 (enExample) |
| CA (1) | CA3001873A1 (enExample) |
| CL (1) | CL2018001217A1 (enExample) |
| CO (1) | CO2018004800A2 (enExample) |
| ES (1) | ES2915266T3 (enExample) |
| HK (1) | HK1253029A1 (enExample) |
| IL (1) | IL258862B (enExample) |
| MA (1) | MA43168A (enExample) |
| MX (1) | MX386148B (enExample) |
| MY (1) | MY194461A (enExample) |
| PE (1) | PE20181010A1 (enExample) |
| PH (1) | PH12018500940A1 (enExample) |
| SA (1) | SA518391518B1 (enExample) |
| SG (1) | SG11201803757UA (enExample) |
| TN (1) | TN2018000130A1 (enExample) |
| WO (1) | WO2017079641A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108349944B (zh) | 2015-11-06 | 2021-03-30 | 豪夫迈·罗氏有限公司 | 二氢吲哚-2-酮衍生物 |
| HK1253029A1 (zh) * | 2015-11-06 | 2019-06-06 | Neurocrine Biosciences, Inc. | 作为毒蕈碱性受体4(m4)拮抗剂用於治疗神经系统疾病的n-[2-(1-苄基哌啶-4-基)乙基]-4-(吡嗪-2-基)-哌嗪-1-甲酰胺衍生物及相关化合物 |
| JP2020530451A (ja) | 2017-08-08 | 2020-10-22 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
| JP2020537667A (ja) | 2017-10-17 | 2020-12-24 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
| CN111491920B (zh) | 2017-10-20 | 2024-01-30 | 范德比尔特大学 | 毒蕈碱性乙酰胆碱受体m4的拮抗剂 |
| US11352344B2 (en) | 2017-10-31 | 2022-06-07 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2019126559A1 (en) | 2017-12-20 | 2019-06-27 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| CA3090130A1 (en) | 2018-02-02 | 2019-08-08 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| IL277071B2 (en) | 2018-03-08 | 2024-07-01 | Incyte Corp | AMINOPYRAZINE DIOL COMPOUNDS AS PI3K-y INHIBITORS |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| WO2020048826A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 5-substituted 1-oxa-3,9-diazaspiro[5.5]undecan-2-one compounds |
| WO2020048827A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 1, 3, 9-triazaspiro[5.5] undecan-2-one compounds |
| WO2020048828A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Pharma Aktiengesellschaft | 5-heteroaryl-3,9-diazaspiro[5.5]undecane compounds |
| EP3846806A4 (en) * | 2018-09-04 | 2022-06-08 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine m1 receptor antagonists |
| JP7626722B2 (ja) * | 2019-06-17 | 2025-02-04 | デシフェラ・ファーマシューティカルズ，エルエルシー | アミノピリミジンアミドオートファジー阻害剤およびその使用方法 |
| CA3150906A1 (en) * | 2019-09-17 | 2021-03-25 | Renato T. Skerlj | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
| US11752149B2 (en) | 2019-12-02 | 2023-09-12 | Pipeline Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
| EP4069367B1 (en) | 2019-12-06 | 2024-05-15 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| CN111072551A (zh) * | 2019-12-30 | 2020-04-28 | 上海睿瓦科技有限公司 | 催化氢化一步法制取哌啶胺的方法 |
| TWI889751B (zh) * | 2020-02-05 | 2025-07-11 | 美商紐羅克里生物科學有限公司 | 蕈毒受體4拮抗劑及使用方法 |
| WO2022156708A1 (en) * | 2021-01-20 | 2022-07-28 | Jacobio Pharmaceuticals Co., Ltd. | Parp7 enzyme inhibitor |
| AU2022289728A1 (en) * | 2021-06-11 | 2023-11-16 | Neuronascent, Inc. | Methods and compositions for lipid formulation of lipophilic small molecule therapies of the heterocyclic type |
| TW202321222A (zh) * | 2021-07-30 | 2023-06-01 | 美商紐羅克里生物科學有限公司 | 蕈毒鹼受體4拮抗劑及使用方法 |
| AU2023382489A1 (en) * | 2022-11-16 | 2025-06-05 | Vyrnwy Therapeutics, Inc. | Inhibitors of tyk2 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013083A1 (en) * | 1991-12-31 | 1993-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity |
| GB9313201D0 (en) * | 1993-06-25 | 1993-08-11 | Fujisawa Pharmaceutical Co | New heterocyclic compounds |
| US5700801A (en) | 1994-12-23 | 1997-12-23 | Karl Thomae, Gmbh | Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
| AU744685B2 (en) * | 1997-11-18 | 2002-02-28 | Teijin Pharma Limited | Cyclic amine derivatives and their use as drugs |
| DE60023878T2 (de) * | 1999-05-18 | 2006-07-20 | Teijin Ltd. | Heilmittel und vorbeugung für mit chemokinen verbundenen erkrankungen |
| ES2215055T3 (es) | 1999-09-22 | 2004-10-01 | Schering Corporation | Antagonistas muscarinicos. |
| AU778173B2 (en) * | 1999-12-08 | 2004-11-18 | Teijin Limited | Cycloamine CCR5 receptor antagonists |
| US6362177B1 (en) * | 2000-05-16 | 2002-03-26 | Teijin Limited | Cyclic amine derivatives and their use as drugs |
| JPWO2003062234A1 (ja) * | 2002-01-23 | 2005-05-19 | 山之内製薬株式会社 | キノキサリン化合物 |
| US8673924B2 (en) | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
| EP1569646A2 (en) * | 2002-12-13 | 2005-09-07 | Smithkline Beecham Corporation | Piperidine derivatives as ccr5 antagonists |
| TW200536830A (en) | 2004-02-06 | 2005-11-16 | Chugai Pharmaceutical Co Ltd | 1-(2H)-isoquinolone derivative |
| EP1904446A2 (en) * | 2005-07-11 | 2008-04-02 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| JP2009521448A (ja) * | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用なフェノキシピペリジンおよびそのアナログ |
| WO2007130383A2 (en) | 2006-04-28 | 2007-11-15 | Northwestern University | Compositions and treatments using pyridazine compounds and secretases |
| EP1997805A1 (en) * | 2007-06-01 | 2008-12-03 | Commissariat à l'Energie Atomique | Compounds with antiparasitic activity, applications thereof to the treatment of infectious diseases caused by apicomplexans |
| JP2013028538A (ja) | 2009-11-13 | 2013-02-07 | Dainippon Sumitomo Pharma Co Ltd | 新規アミド誘導体 |
| WO2013076090A1 (en) | 2011-11-25 | 2013-05-30 | Nerviano Medical Sciences S.R.L. | 3-phenyl-isoquinolin-1(2h)-one derivatives as parp-1 inhibitors |
| WO2014074517A1 (en) * | 2012-11-08 | 2014-05-15 | Emory University | Cellular compositions used to restore stem cell or progenitor cell function and methods related thereto |
| WO2014079787A1 (en) * | 2012-11-20 | 2014-05-30 | F. Hoffmann-La Roche Ag | Substituted 1,6-naphthyridines |
| MX2015013396A (es) * | 2013-03-18 | 2016-07-08 | Genoscience Pharma | Derivados de quinolinas como nuevos agentes contra el cancer. |
| EP2982666B1 (en) * | 2013-04-04 | 2019-08-07 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN105722835B (zh) * | 2013-09-11 | 2018-07-31 | 癌症研究协会:皇家癌症医院 | 3-芳基-5-取代的-异喹啉-1-酮化合物及它们的疗法应用 |
| MA39763A (fr) * | 2014-03-20 | 2017-01-25 | Samumed Llc | Indazole-3-carboxamides 5-substitués, et préparation et utilisation de ceux-ci |
| HK1253029A1 (zh) * | 2015-11-06 | 2019-06-06 | Neurocrine Biosciences, Inc. | 作为毒蕈碱性受体4(m4)拮抗剂用於治疗神经系统疾病的n-[2-(1-苄基哌啶-4-基)乙基]-4-(吡嗪-2-基)-哌嗪-1-甲酰胺衍生物及相关化合物 |
-
2016
- 2016-11-04 HK HK18112407.2A patent/HK1253029A1/zh unknown
- 2016-11-04 AU AU2016348524A patent/AU2016348524B2/en not_active Ceased
- 2016-11-04 MX MX2018005215A patent/MX386148B/es unknown
- 2016-11-04 CN CN201680064834.6A patent/CN108349936B/zh active Active
- 2016-11-04 KR KR1020187015620A patent/KR20180073685A/ko not_active Ceased
- 2016-11-04 MA MA043168A patent/MA43168A/fr unknown
- 2016-11-04 MY MYPI2018000570A patent/MY194461A/en unknown
- 2016-11-04 TN TNP/2018/000130A patent/TN2018000130A1/en unknown
- 2016-11-04 BR BR112018008630A patent/BR112018008630A2/pt not_active IP Right Cessation
- 2016-11-04 EP EP16798333.7A patent/EP3371164B1/en active Active
- 2016-11-04 CA CA3001873A patent/CA3001873A1/en not_active Abandoned
- 2016-11-04 WO PCT/US2016/060659 patent/WO2017079641A1/en not_active Ceased
- 2016-11-04 SG SG11201803757UA patent/SG11201803757UA/en unknown
- 2016-11-04 ES ES16798333T patent/ES2915266T3/es active Active
- 2016-11-04 PE PE2018000730A patent/PE20181010A1/es unknown
- 2016-11-04 JP JP2018522553A patent/JP6917989B2/ja active Active
- 2016-11-04 US US15/773,915 patent/US11033539B2/en active Active
-
2018
- 2018-04-23 IL IL258862A patent/IL258862B/en active IP Right Grant
- 2018-05-02 PH PH12018500940A patent/PH12018500940A1/en unknown
- 2018-05-04 CL CL2018001217A patent/CL2018001217A1/es unknown
- 2018-05-04 CO CONC2018/0004800A patent/CO2018004800A2/es unknown
- 2018-05-05 SA SA518391518A patent/SA518391518B1/ar unknown
-
2021
- 2021-01-05 JP JP2021000354A patent/JP2021050243A/ja not_active Withdrawn
- 2021-04-26 US US17/239,726 patent/US20210338653A1/en not_active Abandoned
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