JP2019525900A5 - - Google Patents
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- JP2019525900A5 JP2019525900A5 JP2018565312A JP2018565312A JP2019525900A5 JP 2019525900 A5 JP2019525900 A5 JP 2019525900A5 JP 2018565312 A JP2018565312 A JP 2018565312A JP 2018565312 A JP2018565312 A JP 2018565312A JP 2019525900 A5 JP2019525900 A5 JP 2019525900A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- heterocyclyl
- heteroaryl
- independently
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 9
- -1 amino, hydroxy Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- 208000020401 Depressive disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 0 Cc1cc(*)ccc1Sc(cccc1)c1N1CCNCC1 Chemical compound Cc1cc(*)ccc1Sc(cccc1)c1N1CCNCC1 0.000 description 6
- YQNWZWMKLDQSAC-UHFFFAOYSA-N Cc(cc1)cc(C)c1Sc(cccc1)c1N1CCNCC1 Chemical compound Cc(cc1)cc(C)c1Sc(cccc1)c1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 description 2
- SBSRWSXAHJUMBW-UHFFFAOYSA-N CC(O1)=C(COC(N(CC2)CCN2c(cccc2)c2Sc2c(C)cc(C)cc2)=O)OC1=O Chemical compound CC(O1)=C(COC(N(CC2)CCN2c(cccc2)c2Sc2c(C)cc(C)cc2)=O)OC1=O SBSRWSXAHJUMBW-UHFFFAOYSA-N 0.000 description 1
- MBEUMBAASFQBDP-UHFFFAOYSA-N CC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O Chemical compound CC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O MBEUMBAASFQBDP-UHFFFAOYSA-N 0.000 description 1
- GFKLIWAYGVTZGH-UHFFFAOYSA-N CCCC(O)OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O Chemical compound CCCC(O)OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O GFKLIWAYGVTZGH-UHFFFAOYSA-N 0.000 description 1
- RBIXAJVDPNWHSU-UHFFFAOYSA-N CCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1c(C)cc(C)cc1)=O)=O Chemical compound CCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1c(C)cc(C)cc1)=O)=O RBIXAJVDPNWHSU-UHFFFAOYSA-N 0.000 description 1
- IWXOWEMAKZPDBE-UHFFFAOYSA-N CCCCCCCC(OCOC(N(CC1)CCN1c1ccccc1Sc1c(C)cc(C)cc1)=O)=O Chemical compound CCCCCCCC(OCOC(N(CC1)CCN1c1ccccc1Sc1c(C)cc(C)cc1)=O)=O IWXOWEMAKZPDBE-UHFFFAOYSA-N 0.000 description 1
- JHJYJMFQVKJPMH-UHFFFAOYSA-N CCCCCCCCCCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O Chemical compound CCCCCCCCCCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O JHJYJMFQVKJPMH-UHFFFAOYSA-N 0.000 description 1
- OKKCVWQHDFXFOL-UHFFFAOYSA-O CCCCCCCCCCCCCCC(CCC(O)=O)c(cc1)cc(N2CC[NH2+]CC2)c1Sc1c(C)cc(C)cc1 Chemical compound CCCCCCCCCCCCCCC(CCC(O)=O)c(cc1)cc(N2CC[NH2+]CC2)c1Sc1c(C)cc(C)cc1 OKKCVWQHDFXFOL-UHFFFAOYSA-O 0.000 description 1
- JCESALWPDRHVCW-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O Chemical compound CCCCCCCCCCCCCCCCCC(OCOC(N(CC1)CCN1c(cccc1)c1Sc1ccc(C)cc1C)=O)=O JCESALWPDRHVCW-UHFFFAOYSA-N 0.000 description 1
- FOECFFUHJXHBDV-UHFFFAOYSA-N CCOC(N(CC1)CCN1c(cccc1)c1Sc1c(C)cc(C)cc1)=O Chemical compound CCOC(N(CC1)CCN1c(cccc1)c1Sc1c(C)cc(C)cc1)=O FOECFFUHJXHBDV-UHFFFAOYSA-N 0.000 description 1
- MGFQAQLBDLHSJE-UHFFFAOYSA-N Cc(cc1)cc(C)c1Sc(cccc1)c1N(CC1)CCN1C(OCOC(c1ccccc1)=O)=O Chemical compound Cc(cc1)cc(C)c1Sc(cccc1)c1N(CC1)CCN1C(OCOC(c1ccccc1)=O)=O MGFQAQLBDLHSJE-UHFFFAOYSA-N 0.000 description 1
- YQNWZWMKLDQSAC-UHFFFAOYSA-O Cc(cc1C)ccc1Sc(cccc1)c1N1CC[NH2+]CC1 Chemical compound Cc(cc1C)ccc1Sc(cccc1)c1N1CC[NH2+]CC1 YQNWZWMKLDQSAC-UHFFFAOYSA-O 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021069689A JP7123211B2 (ja) | 2016-06-16 | 2021-04-16 | ジアリールチオエーテルピペラジン化合物、その調製方法及び使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610446737.5 | 2016-06-16 | ||
| CN201610446737 | 2016-06-16 | ||
| PCT/CN2017/088493 WO2017215636A1 (zh) | 2016-06-16 | 2017-06-15 | 二芳基硫醚哌嗪类化合物及其制备方法和用途 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021069689A Division JP7123211B2 (ja) | 2016-06-16 | 2021-04-16 | ジアリールチオエーテルピペラジン化合物、その調製方法及び使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019525900A JP2019525900A (ja) | 2019-09-12 |
| JP2019525900A5 true JP2019525900A5 (enExample) | 2020-05-28 |
Family
ID=60662997
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018565312A Pending JP2019525900A (ja) | 2016-06-16 | 2017-06-15 | ジアリールチオエーテルピペラジン化合物、その調製方法及び使用 |
| JP2021069689A Active JP7123211B2 (ja) | 2016-06-16 | 2021-04-16 | ジアリールチオエーテルピペラジン化合物、その調製方法及び使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021069689A Active JP7123211B2 (ja) | 2016-06-16 | 2021-04-16 | ジアリールチオエーテルピペラジン化合物、その調製方法及び使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10927089B2 (enExample) |
| JP (2) | JP2019525900A (enExample) |
| CN (1) | CN109311833B (enExample) |
| WO (1) | WO2017215636A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2017242867B9 (en) * | 2016-03-29 | 2019-07-04 | Shanghai Synergy Pharmaceutical Sciences Co., Ltd | Vortioxetine pamoic acid salt and crystal form thereof |
| US11198671B2 (en) * | 2018-06-20 | 2021-12-14 | Vio Ag Pharmaceuticals S.A. | One-pot organo-pseudocatalytic C—H activation approach for the preparation of vortioxetine and vortioxetine intermediate |
| CN114728920B (zh) * | 2019-12-10 | 2023-07-21 | 苏州恩华生物医药科技有限公司 | 一种沃替西汀前药及其应用 |
| CN115448895B (zh) * | 2021-06-09 | 2025-07-11 | 苏州恩华生物医药科技有限公司 | 一种沃替西汀前药的晶型、其制备方法和应用 |
| EP4382096A4 (en) * | 2021-08-05 | 2025-06-18 | Zhejiang Huahai Pharmaceutical Co., Ltd. | Lyophilized vortioxetine pamoate powder for injection and manufacturing process therefor |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB507565A (en) * | 1937-12-10 | 1939-06-12 | May & Baker Ltd | Process for the preparation of amidine derivatives |
| IL161966A0 (en) | 2001-12-20 | 2005-11-20 | Lundbeck & Co As H | Aryloxyphenyl and arylsulfanylphenyl |
| US8722684B2 (en) * | 2006-06-16 | 2014-05-13 | H. Lundbeck A/S | 1-[2-(2,4-dimethylphenylsulfanyl)-phenyl] piperazine as a compound with combined serotonin reuptake, 5-HT3 and 5-HT1A activity for the treatment of cognitive impairment |
| TW200848411A (en) | 2007-03-20 | 2008-12-16 | Lundbeck & Co As H | Novel therapeutic uses of 1-[2-(2, 4-dimethylphenylsulfanyl)phenyl]-piperazine |
| CN103087060B (zh) * | 2011-10-28 | 2016-08-03 | 华东理工大学 | 高活性哌虫啶异构体及其制备方法 |
| JP5952912B2 (ja) | 2011-12-15 | 2016-07-13 | アルカーメス ファーマ アイルランド リミテッド | 二級アミン化合物のプロドラッグ |
| CN105339361A (zh) | 2013-05-31 | 2016-02-17 | 斯洛文尼亚莱柯制药股份有限公司 | 用于合成1-(2-((2，4-二甲基苯基)硫代)苯基)哌嗪的新方法 |
| CN104829558B (zh) | 2014-02-10 | 2020-03-03 | 江苏豪森药业集团有限公司 | 二芳基硫醚胺类化合物的制备方法 |
| ES2913282T3 (es) | 2014-05-09 | 2022-06-01 | Shanghai Syncores Tech Inc Ltd | Producto intermedio de vortioxetina y procedimiento de síntesis del mismo |
| CZ2014471A3 (cs) * | 2014-07-08 | 2016-01-20 | Zentiva, K.S. | Způsob přípravy vortioxetinu |
| WO2016079751A2 (en) * | 2014-11-17 | 2016-05-26 | Megafine Pharma (P) Ltd. | A process for preparation of vortioxetine and polymorphs thereof |
| EP3023417B1 (en) * | 2014-11-21 | 2017-06-28 | Dipharma Francis S.r.l. | Process for the preparation of an antidepressant and the intermediates thereof |
| CN105461656A (zh) | 2015-11-11 | 2016-04-06 | 北京万全德众医药生物技术有限公司 | 一种制备沃替西汀的新工艺 |
| US20190194154A1 (en) * | 2016-01-20 | 2019-06-27 | Amneal Pharmaceuticals Company Gmbh | Polymorphic Forms Of Vortioxetine Hydrobromide Tert-Butanolate |
| WO2017162536A1 (en) | 2016-03-21 | 2017-09-28 | H. Lundbeck A/S | Vortioxetine prodrugs |
| AU2017242867B9 (en) * | 2016-03-29 | 2019-07-04 | Shanghai Synergy Pharmaceutical Sciences Co., Ltd | Vortioxetine pamoic acid salt and crystal form thereof |
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2017
- 2017-06-15 CN CN201780032963.1A patent/CN109311833B/zh active Active
- 2017-06-15 US US16/308,462 patent/US10927089B2/en active Active
- 2017-06-15 WO PCT/CN2017/088493 patent/WO2017215636A1/zh not_active Ceased
- 2017-06-15 JP JP2018565312A patent/JP2019525900A/ja active Pending
-
2021
- 2021-04-16 JP JP2021069689A patent/JP7123211B2/ja active Active