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 (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2727179C2 (ru) | 2015-11-06 | 2020-07-21 | Ф. Хоффманн-Ля Рош Аг | Производные индолин-2-она |
| MY194461A (en) * | 2015-11-06 | 2022-11-30 | Neurocrine Biosciences Inc | N-[2-(1-benzylpiperidin-4-yl)4-(pyrazin-2-yl)-piperazine-1-carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
| AU2018300980A1 (en) | 2017-07-12 | 2020-01-02 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| CA3072081A1 (en) | 2017-08-08 | 2019-02-14 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| EP3697781B1 (en) | 2017-10-17 | 2023-06-07 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| ES3064093T3 (en) | 2017-10-20 | 2026-04-22 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| AU2018360581A1 (en) | 2017-10-31 | 2020-06-11 | 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 |
| US11414406B2 (en) | 2018-02-02 | 2022-08-16 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| MD3762368T2 (ro) | 2018-03-08 | 2022-07-31 | Incyte Corp | Compuși diol aminopirazină ca inhibitori ai PI3K-Y |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| WO2020048827A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 1, 3, 9-triazaspiro[5.5] undecan-2-one compounds |
| WO2020048826A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 5-substituted 1-oxa-3,9-diazaspiro[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 |
| US12054487B2 (en) | 2018-09-04 | 2024-08-06 | Contineum 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 |
| EP4031540A1 (en) * | 2019-09-17 | 2022-07-27 | Bial-R&D Investments, S.A. | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
| 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 |
| TW202134231A (zh) | 2019-12-06 | 2021-09-16 | 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 |
| 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 |
| 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 |
| WO2022156708A1 (en) * | 2021-01-20 | 2022-07-28 | Jacobio Pharmaceuticals Co., Ltd. | Parp7 enzyme inhibitor |
| EP4352058A4 (en) * | 2021-06-11 | 2025-09-24 | Neuronascent Inc | METHODS AND COMPOSITIONS FOR LIPID FORMULATION OF SMALL MOLECULE THERAPIES WITH LIPOPHILIC HETEROCYCLIC TYPES |
| CN118076585A (zh) * | 2021-07-23 | 2024-05-24 | 国家医疗保健研究所 | 革兰氏阴性菌外排泵抑制剂 |
| AU2022319930A1 (en) * | 2021-07-30 | 2024-03-07 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| JP2025539787A (ja) * | 2022-11-16 | 2025-12-09 | ヴァーンウィ セラピューティクス，インコーポレイテッド | Ｔｙｋ２阻害剤 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0619814A1 (en) * | 1991-12-31 | 1994-10-19 | 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 |
| PL192083B1 (pl) * | 1997-11-18 | 2006-08-31 | Dupont Pharmaceuticals Res Lab | Pochodne amin cyklicznych i ich zastosowanie |
| ES2250132T3 (es) * | 1999-05-18 | 2006-04-16 | Teijin Limited | Remedios preventivos para enfermedades asociadas a quimioquinas. |
| CN1167682C (zh) * | 1999-09-22 | 2004-09-22 | 先灵公司 | 毒蕈碱拮抗剂 |
| ATE346042T1 (de) * | 1999-12-08 | 2006-12-15 | Teijin Ltd | Zyklische aminverbindungen als ccr5-rezeptor antagonisten |
| US6362177B1 (en) * | 2000-05-16 | 2002-03-26 | Teijin Limited | Cyclic amine derivatives and their use as drugs |
| WO2003062234A1 (en) | 2002-01-23 | 2003-07-31 | Yamanouchi Pharmaceutical Co., Ltd. | Quinoxaline compounds |
| US8673924B2 (en) * | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
| RU2005118407A (ru) * | 2002-12-13 | 2006-03-10 | СмитКлайн Бичем Корпорейшн (US) | Производные пиперидина в качестве антагонистов ccr5 |
| TW200536830A (en) | 2004-02-06 | 2005-11-16 | Chugai Pharmaceutical Co Ltd | 1-(2H)-isoquinolone derivative |
| WO2007007282A2 (en) * | 2005-07-11 | 2007-01-18 | Ranbaxy Laboratories Limited | Azabicyclo derivatives as muscarinic receptor antagonists |
| EP1976848A2 (en) * | 2005-12-21 | 2008-10-08 | Schering Corporation | Phenoxypiperidines and analogs thereof useful as histamine h3 antagonists |
| 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 |
| AU2012342562B2 (en) | 2011-11-25 | 2017-02-23 | Nerviano Medical Sciences S.R.L. | 3-phenyl-isoquinolin-1(2H)-one derivatives as PARP-1 inhibitors |
| US20150259649A1 (en) | 2012-11-08 | 2015-09-17 | Emory University | Cellular compositions used to restore stem cell or progenitor cell function and methods related thereto |
| EP2922540A1 (en) | 2012-11-20 | 2015-09-30 | F. Hoffmann-La Roche AG | Substituted 1,6-naphthyridines |
| CA2902734A1 (en) | 2013-03-18 | 2014-09-25 | Genoscience Pharma | Quinolines derivatives as novel anticancer agents |
| US9598398B2 (en) * | 2013-04-04 | 2017-03-21 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP3044221B1 (en) * | 2013-09-11 | 2018-02-21 | Institute of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| PE20170127A1 (es) * | 2014-03-20 | 2017-03-30 | Samumed Llc | Indazol-3-carboxamidas 5-sustituidas y preparacion y uso de las mismas |
| MY194461A (en) * | 2015-11-06 | 2022-11-30 | Neurocrine Biosciences Inc | N-[2-(1-benzylpiperidin-4-yl)4-(pyrazin-2-yl)-piperazine-1-carboxamide derivatives and related compounds as muscarinic receptor 4 (m4) antagonists for treating neurological diseases |
-
2016
- 2016-11-04 MY MYPI2018000570A patent/MY194461A/en unknown
- 2016-11-04 CA CA3001873A patent/CA3001873A1/en not_active Abandoned
- 2016-11-04 KR KR1020187015620A patent/KR20180073685A/ko not_active Ceased
- 2016-11-04 SG SG11201803757UA patent/SG11201803757UA/en unknown
- 2016-11-04 JP JP2018522553A patent/JP6917989B2/ja active Active
- 2016-11-04 WO PCT/US2016/060659 patent/WO2017079641A1/en not_active Ceased
- 2016-11-04 US US15/773,915 patent/US11033539B2/en active Active
- 2016-11-04 TN TNP/2018/000130A patent/TN2018000130A1/en unknown
- 2016-11-04 EP EP16798333.7A patent/EP3371164B1/en active Active
- 2016-11-04 CN CN201680064834.6A patent/CN108349936B/zh active Active
- 2016-11-04 AU AU2016348524A patent/AU2016348524B2/en not_active Ceased
- 2016-11-04 MX MX2018005215A patent/MX386148B/es unknown
- 2016-11-04 HK HK18112407.2A patent/HK1253029A1/zh unknown
- 2016-11-04 BR BR112018008630A patent/BR112018008630A2/pt not_active IP Right Cessation
- 2016-11-04 PE PE2018000730A patent/PE20181010A1/es unknown
- 2016-11-04 ES ES16798333T patent/ES2915266T3/es active Active
- 2016-11-04 MA MA043168A patent/MA43168A/fr unknown
-
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 CO CONC2018/0004800A patent/CO2018004800A2/es unknown
- 2018-05-04 CL CL2018001217A patent/CL2018001217A1/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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