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 (https=) | 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 (https=) |
| EP (1) | EP3371164B1 (https=) |
| JP (2) | JP6917989B2 (https=) |
| KR (1) | KR20180073685A (https=) |
| CN (1) | CN108349936B (https=) |
| AU (1) | AU2016348524B2 (https=) |
| BR (1) | BR112018008630A2 (https=) |
| CA (1) | CA3001873A1 (https=) |
| CL (1) | CL2018001217A1 (https=) |
| CO (1) | CO2018004800A2 (https=) |
| ES (1) | ES2915266T3 (https=) |
| HK (1) | HK1253029A1 (https=) |
| IL (1) | IL258862B (https=) |
| MA (1) | MA43168A (https=) |
| MX (1) | MX386148B (https=) |
| MY (1) | MY194461A (https=) |
| PE (1) | PE20181010A1 (https=) |
| PH (1) | PH12018500940A1 (https=) |
| SA (1) | SA518391518B1 (https=) |
| SG (1) | SG11201803757UA (https=) |
| TN (1) | TN2018000130A1 (https=) |
| WO (1) | WO2017079641A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ES2808920T3 (es) | 2015-11-06 | 2021-03-02 | Hoffmann La Roche | Derivados de indolin-2-ona |
| US12600726B2 (en) | 2017-07-12 | 2026-04-14 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| AU2018313802A1 (en) | 2017-08-08 | 2020-02-20 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2019079410A1 (en) | 2017-10-17 | 2019-04-25 | Vanderbilt University | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
| IL310346A (en) | 2017-10-20 | 2024-03-01 | Univ Vanderbilt | Muscarinic acetylcholine M4 receptor antagonists |
| AU2018360581A1 (en) | 2017-10-31 | 2020-06-11 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| EP3732163A4 (en) | 2017-12-20 | 2021-07-14 | Vanderbilt University | MUSCARIN M4 ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| CN111788182B (zh) * | 2018-02-02 | 2023-09-26 | 范德堡大学 | 毒蕈碱性乙酰胆碱受体m4的拮抗剂 |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| 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 |
| US12054487B2 (en) | 2018-09-04 | 2024-08-06 | Contineum Therapeutics, Inc. | Muscarinic acetylcholine M1 receptor antagonists |
| IL325201A (en) * | 2019-06-17 | 2026-02-01 | Deciphera Pharmaceuticals Llc | Aminopyrimidine amide autophagy inhibitors and methods of using them |
| KR20220100860A (ko) * | 2019-09-17 | 2022-07-18 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 질병의 치료에 사용하기 위한 치환된, 포화 및 불포화 n-헤테로시클릭 카르복사미드 및 관련 화합물 |
| 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 |
| 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 |
| EP4100410B1 (en) * | 2020-02-05 | 2026-04-22 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| 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 |
| 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 |
| WO2023010078A1 (en) * | 2021-07-30 | 2023-02-02 | 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 |
| IL135488A0 (en) * | 1997-11-18 | 2001-05-20 | Teijin Ltd | Cyclic amine derivatives |
| DE60023878T2 (de) * | 1999-05-18 | 2006-07-20 | Teijin Ltd. | Heilmittel und vorbeugung für mit chemokinen verbundenen erkrankungen |
| HK1043590A1 (zh) * | 1999-09-22 | 2002-09-20 | Schering Corporation | 毒蕈碱性拮抗物 |
| US20070010509A1 (en) * | 1999-12-08 | 2007-01-11 | Tatsuki Shiota | Cycloamine ccr5 receptor antagonists |
| US6410566B1 (en) * | 2000-05-16 | 2002-06-25 | 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 |
| BR0317230A (pt) | 2002-12-13 | 2005-10-25 | Smithkline Beecham Corp | Composto, composição, métodos de antagonizar uma atividade do receptor de quimiocina ccr-5, e de tratar uma infecção viral em um paciente, e, uso de um composto |
| 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 |
| 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 |
| IN2014CN04671A (https=) | 2011-11-25 | 2015-09-18 | Nerviano Medical Sciences Srl | |
| 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 |
| CN104812387A (zh) * | 2012-11-20 | 2015-07-29 | 霍夫曼-拉罗奇有限公司 | 取代的1,6-萘啶 |
| AU2014233757B2 (en) | 2013-03-18 | 2017-12-21 | Genoscience Pharma | Quinolines derivatives as novel anticancer agents |
| JP6272832B2 (ja) | 2013-04-04 | 2018-01-31 | 武田薬品工業株式会社 | 複素環化合物 |
| US9611223B2 (en) * | 2013-09-11 | 2017-04-04 | Institute Of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| MX2016012208A (es) * | 2014-03-20 | 2017-01-26 | Samumed Llc | Indazol-3-carboxamidas 5-substituidas y preparacion y uso de las mismas. |
| 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 |
-
2016
- 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 JP JP2018522553A patent/JP6917989B2/ja active Active
- 2016-11-04 TN TNP/2018/000130A patent/TN2018000130A1/en unknown
- 2016-11-04 KR KR1020187015620A patent/KR20180073685A/ko not_active Ceased
- 2016-11-04 SG SG11201803757UA patent/SG11201803757UA/en unknown
- 2016-11-04 MA MA043168A patent/MA43168A/fr unknown
- 2016-11-04 AU AU2016348524A patent/AU2016348524B2/en not_active Ceased
- 2016-11-04 CA CA3001873A patent/CA3001873A1/en not_active Abandoned
- 2016-11-04 US US15/773,915 patent/US11033539B2/en active Active
- 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 MX MX2018005215A patent/MX386148B/es unknown
- 2016-11-04 ES ES16798333T patent/ES2915266T3/es active Active
- 2016-11-04 MY MYPI2018000570A patent/MY194461A/en unknown
- 2016-11-04 WO PCT/US2016/060659 patent/WO2017079641A1/en not_active Ceased
- 2016-11-04 PE PE2018000730A patent/PE20181010A1/es 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 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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