JP2020531505A5 - - Google Patents
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- JP2020531505A5 JP2020531505A5 JP2020510595A JP2020510595A JP2020531505A5 JP 2020531505 A5 JP2020531505 A5 JP 2020531505A5 JP 2020510595 A JP2020510595 A JP 2020510595A JP 2020510595 A JP2020510595 A JP 2020510595A JP 2020531505 A5 JP2020531505 A5 JP 2020531505A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- urea
- methylpiperidin
- difluorophenyl
- phenyl
- 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
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- -1 polymorph Substances 0.000 claims 102
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 84
- 229910052739 hydrogen Inorganic materials 0.000 claims 49
- 239000001257 hydrogen Substances 0.000 claims 49
- 150000001875 compounds Chemical class 0.000 claims 47
- 150000003839 salts Chemical class 0.000 claims 41
- 229940002612 prodrug Drugs 0.000 claims 40
- 239000000651 prodrug Substances 0.000 claims 40
- 239000012453 solvate Substances 0.000 claims 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 35
- 150000002431 hydrogen Chemical class 0.000 claims 32
- 206010012289 Dementia Diseases 0.000 claims 29
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 26
- 239000004202 carbamide Substances 0.000 claims 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 201000010099 disease Diseases 0.000 claims 16
- 208000035475 disorder Diseases 0.000 claims 16
- 150000004677 hydrates Chemical class 0.000 claims 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 15
- 208000018737 Parkinson disease Diseases 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 201000000980 schizophrenia Diseases 0.000 claims 11
- 208000030990 Impulse-control disease Diseases 0.000 claims 10
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 10
- 206010022437 insomnia Diseases 0.000 claims 10
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 208000020016 psychiatric disease Diseases 0.000 claims 9
- 208000024827 Alzheimer disease Diseases 0.000 claims 8
- 101710088194 Dehydrogenase Proteins 0.000 claims 8
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims 8
- 125000005336 allyloxy group Chemical group 0.000 claims 8
- 208000010877 cognitive disease Diseases 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 102000029797 Prion Human genes 0.000 claims 5
- 108091000054 Prion Proteins 0.000 claims 5
- 201000006061 fatal familial insomnia Diseases 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 4
- 102100034452 Alternative prion protein Human genes 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- 208000027534 Emotional disease Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 208000028017 Psychotic disease Diseases 0.000 claims 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims 4
- 230000003247 decreasing effect Effects 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 230000033001 locomotion Effects 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims 4
- 230000001568 sexual effect Effects 0.000 claims 4
- 208000019116 sleep disease Diseases 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 206010003805 Autism Diseases 0.000 claims 3
- 208000020706 Autistic disease Diseases 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 206010012239 Delusion Diseases 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 230000003542 behavioural effect Effects 0.000 claims 3
- 229960003920 cocaine Drugs 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 231100000868 delusion Toxicity 0.000 claims 3
- 206010013663 drug dependence Diseases 0.000 claims 3
- 231100000518 lethal Toxicity 0.000 claims 3
- 230000001665 lethal effect Effects 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 2
- JKLZKCLYQHDHBP-UHFFFAOYSA-N 1-[(2,4-dichlorophenyl)methyl]-3-[[4-(2-methylpropoxy)phenyl]methyl]-1-piperidin-4-ylurea Chemical compound ClC1=C(C=CC(=C1)Cl)CN(C(=O)NCC1=CC=C(C=C1)OCC(C)C)C1CCNCC1 JKLZKCLYQHDHBP-UHFFFAOYSA-N 0.000 claims 2
- IAGYJTOHBSNGQQ-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[(4-propoxyphenyl)methyl]urea Chemical compound FC1=C(C=CC(=C1)F)CN(C(=O)NCC1=CC=C(C=C1)OCCC)C1CCN(CC1)C IAGYJTOHBSNGQQ-UHFFFAOYSA-N 0.000 claims 2
- IDEIRLOMDSGIKX-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea Chemical compound FC1=C(C=CC(=C1)F)CN(C(=O)NCC1=CC=C(C=C1)OCC(C)C)C1CCN(CC1)C IDEIRLOMDSGIKX-UHFFFAOYSA-N 0.000 claims 2
- JPHOIRGTTXUHIO-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-[(2-methylpropan-2-yl)oxy]phenyl]methyl]urea Chemical compound C(C)(C)(C)OC1=CC=C(CNC(N(C2CCN(CC2)C)CC2=C(C=C(C=C2)F)F)=O)C=C1 JPHOIRGTTXUHIO-UHFFFAOYSA-N 0.000 claims 2
- GVAXOXIYNWHNSO-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(CN(C(=O)NCC=2C=CC3=C(CCO3)C=2)C2CCN(CC2)C)C=CC(=C1)F GVAXOXIYNWHNSO-UHFFFAOYSA-N 0.000 claims 2
- CHWXBPOMLXDJHC-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[(2-fluoro-4-nitrophenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(C=CC(=C1)F)CN(C(=O)NCC1=C(C=C(C=C1)[N+](=O)[O-])F)C1CCN(CC1)C CHWXBPOMLXDJHC-UHFFFAOYSA-N 0.000 claims 2
- YJJQCKSUDJPKER-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[(4-ethoxyphenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(CN(C(=O)NCC2=CC=C(C=C2)OCC)C2CCN(CC2)C)C=CC(=C1)F YJJQCKSUDJPKER-UHFFFAOYSA-N 0.000 claims 2
- NOARZTCBKQBTRU-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[(4-methoxyphenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(C=CC(=C1)F)CN(C(NCC1=CC=C(C=C1)OC)=O)C1CCN(CC1)C NOARZTCBKQBTRU-UHFFFAOYSA-N 0.000 claims 2
- VTKHDTYAIGKYTC-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[(4-methoxyphenyl)methyl]-1-piperidin-4-ylurea Chemical compound COC1=CC=C(CNC(=O)N(CC2=C(F)C=C(F)C=C2)C2CCNCC2)C=C1 VTKHDTYAIGKYTC-UHFFFAOYSA-N 0.000 claims 2
- ONQUFYALJGNEOY-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[[4-(2-fluoroethoxy)phenyl]methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(CN(C(=O)NCC2=CC=C(C=C2)OCCF)C2CCN(CC2)C)C=CC(=C1)F ONQUFYALJGNEOY-UHFFFAOYSA-N 0.000 claims 2
- RCHZCSVXKPFLCG-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[[4-(3-fluoropropoxy)phenyl]methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC1=C(C=CC(=C1)F)CN(C(NCC1=CC=C(C=C1)OCCCF)=O)C1CCN(CC1)C RCHZCSVXKPFLCG-UHFFFAOYSA-N 0.000 claims 2
- ZBEZKVHVIGFETB-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-[[4-[(2-methylpropan-2-yl)oxy]phenyl]methyl]-1-piperidin-4-ylurea Chemical compound C(C)(C)(C)OC1=CC=C(C=C1)CNC(N(C1CCNCC1)CC1=C(C=C(C=C1)F)F)=O ZBEZKVHVIGFETB-UHFFFAOYSA-N 0.000 claims 2
- BXKKNKJISFFWTC-UHFFFAOYSA-N 1-[(4-chloro-2-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[(4-propan-2-yloxyphenyl)methyl]urea Chemical compound ClC1=CC(=C(C=C1)CN(C(=O)NCC1=CC=C(C=C1)OC(C)C)C1CCN(CC1)C)F BXKKNKJISFFWTC-UHFFFAOYSA-N 0.000 claims 2
- MSOBYGSZDWDNHW-UHFFFAOYSA-N 1-[[4-chloro-2-(trifluoromethyl)phenyl]methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea Chemical compound ClC1=CC(=C(C=C1)CN(C(=O)NCC1=CC=C(C=C1)OCC(C)C)C1CCN(CC1)C)C(F)(F)F MSOBYGSZDWDNHW-UHFFFAOYSA-N 0.000 claims 2
- RLWOTCQGTFOYQE-UHFFFAOYSA-N 3-(1-benzofuran-5-ylmethyl)-1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound O1C=CC2=C1C=CC(=C2)CNC(N(C1CCN(CC1)C)CC1=C(C=C(C=C1)F)F)=O RLWOTCQGTFOYQE-UHFFFAOYSA-N 0.000 claims 2
- UYRCLXJMWZFKDG-UHFFFAOYSA-N 3-[(4-cyclopropyloxyphenyl)methyl]-1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound C1(CC1)OC1=CC=C(CNC(N(C2CCN(CC2)C)CC2=C(C=C(C=C2)F)F)=O)C=C1 UYRCLXJMWZFKDG-UHFFFAOYSA-N 0.000 claims 2
- YIRMADSVSJJJLF-UHFFFAOYSA-N 3-[[4-(2,2-difluoroethoxy)phenyl]methyl]-1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound FC(COC1=CC=C(C=C1)CNC(N(C1CCN(CC1)C)CC1=C(C=C(C=C1)F)F)=O)F YIRMADSVSJJJLF-UHFFFAOYSA-N 0.000 claims 2
- FKZGIGYVYMLAJU-UHFFFAOYSA-N 3-[[4-(cyclopropylmethoxy)phenyl]methyl]-1-[(2,4-difluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)urea Chemical compound C1(CC1)COC1=CC=C(C=C1)CNC(N(C1CCN(CC1)C)CC1=C(C=C(C=C1)F)F)=O FKZGIGYVYMLAJU-UHFFFAOYSA-N 0.000 claims 2
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| WO2019040104A2 (en) | 2017-08-21 | 2019-02-28 | Acadia Pharmaceuticals Inc. | COMPOUNDS, RELATED SALTS AND METHODS OF TREATING DISEASES |
| ES2906868T3 (es) * | 2019-05-22 | 2022-04-20 | Zakl Farmaceutyczne Polpharma S A | Intermedio farmacéutico para preparar pimavanserina |
| CA3130821A1 (en) | 2019-06-12 | 2020-12-17 | East China University Of Science And Technology | Antihypertensive polyol compound and derivative thereof |
| CN113214289B (zh) * | 2020-01-21 | 2022-10-28 | 瀚远医药有限公司 | 5-ht2a受体拮抗剂及其治疗中枢神经系统疾病的应用 |
| CN113214231B (zh) * | 2020-01-21 | 2022-04-08 | 瀚远医药有限公司 | 5ht2a受体拮抗剂及其医疗应用 |
| WO2021147818A1 (zh) * | 2020-01-21 | 2021-07-29 | 瀚远医药有限公司 | 5-ht2a受体拮抗剂及其治疗中枢神经系统疾病的应用 |
| CN113214141B (zh) * | 2020-01-21 | 2022-04-08 | 瀚远医药有限公司 | 5ht2a受体拮抗剂及其制备和应用 |
| CN115605202B (zh) | 2020-03-26 | 2025-10-28 | 盐野义制药株式会社 | 具有血清素受体结合活性的芳香族杂环衍生物 |
| CN111548257B (zh) * | 2020-05-28 | 2022-11-15 | 安道麦马克西姆有限公司 | 一种（4-异丙氧基-2-甲基）苯基异丙基酮的制备方法 |
| WO2022017440A1 (zh) * | 2020-07-22 | 2022-01-27 | 山东绿叶制药有限公司 | 5-ht 2a受体抑制剂或反向激动剂及其制备方法和应用 |
| US20240083872A1 (en) * | 2020-12-28 | 2024-03-14 | Shionogi & Co., Ltd. | Cyclic amine derivatives having serotonin receptor binding activity |
| CN113292484B (zh) * | 2021-06-04 | 2022-11-15 | 沈阳药科大学 | 3-(4-甲基哌啶-1-基)-3-苄基脲类化合物及其类似物、制备方法及应用 |
| AU2022326885A1 (en) * | 2021-08-11 | 2024-02-15 | Curadev Pharma Pvt. Ltd. | Small molecule urea derivatives as sting antagonists |
| AU2023319750A1 (en) * | 2022-08-03 | 2025-02-13 | Luye Innomind Pharma Shijiazhuang Co., Ltd. | 5-ht2a receptor inverse agonist, and preparation method therefor and use thereof |
| WO2024067304A1 (zh) * | 2022-09-28 | 2024-04-04 | 瀚远医药有限公司 | 一种具有Sigma2和5HT2A抑制活性的化合物及用途 |
| WO2024105007A1 (en) * | 2022-11-15 | 2024-05-23 | Samsara Therapeutics Inc. | Autophagy inducing compounds and uses thereof |
| KR20260048603A (ko) | 2023-08-02 | 2026-04-10 | 아카디아 파마슈티칼스 인코포레이티드 | 세로토닌-수용체 5-ht와 관련된 질환의 치료에서 사용하기 위한 3-(4-사이클로-프로폭시벤질)-1-(2,4-다이플루오로벤질)-1-(1-메틸피페리딘-4-일)유레아 |
| WO2025162237A1 (zh) * | 2024-02-02 | 2025-08-07 | 绿叶嘉奥制药石家庄有限公司 | 一种5-ht2a受体反向激动剂的盐型、晶型及其制备方法和应用 |
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| ATE450262T1 (de) * | 2005-11-25 | 2009-12-15 | Galapagos Sas | Harnstoff-derivate als calcium-rezeptor- modulatoren |
| TW200831517A (en) | 2006-12-15 | 2008-08-01 | Astrazeneca Ab | Chemical compounds |
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| JP2010540454A (ja) | 2007-09-21 | 2010-12-24 | アカディア ファーマシューティカルズ，インコーポレーテッド | ピマバンセリンと他の薬剤との併用投与 |
| WO2009039461A2 (en) * | 2007-09-21 | 2009-03-26 | Acadia Pharmaceuticals, Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
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| EP3082805B1 (en) | 2013-12-20 | 2020-02-05 | Institute for Drug Discovery, LLC | Substituted amino triazoles, and methods using same |
| CN104844502B (zh) | 2015-06-05 | 2018-07-31 | 齐鲁师范学院 | 一种匹莫范色林的制备方法 |
| PL3325444T3 (pl) | 2015-07-20 | 2021-12-06 | Acadia Pharmaceuticals Inc. | Sposoby wytwarzania N-(4-fluorobenzylo)-N-(1-metylopiperydyn-4-ylo)-N'-(4-(2-metylopropyloksy)fenylometylo)karbamidu oraz jego soli winianowej i postaci polimorficznej C |
| CN105481757A (zh) | 2015-12-25 | 2016-04-13 | 北京康立生医药技术开发有限公司 | 一种哌马色林的制备方法 |
| WO2019040104A2 (en) | 2017-08-21 | 2019-02-28 | Acadia Pharmaceuticals Inc. | COMPOUNDS, RELATED SALTS AND METHODS OF TREATING DISEASES |
| SG11202001062XA (en) | 2017-08-21 | 2020-03-30 | Acadia Pharm Inc | Compounds, salts thereof and methods for treatment of diseases |
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