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.)
- Pending
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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 (https=) | 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 (https=) |
| JP (2) | JP2019525900A (https=) |
| CN (1) | CN109311833B (https=) |
| WO (1) | WO2017215636A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017167180A1 (zh) * | 2016-03-29 | 2017-10-05 | 上海华汇拓医药科技有限公司 | 沃替西汀的帕莫酸盐及其晶型 |
| JP7389761B2 (ja) * | 2018-06-20 | 2023-11-30 | バイオ アーゲー ファーマシューティカルズ エス．エー． | ボルチオキセチンおよびボルチオキセチン中間体を調製するためのワンポット有機擬触媒ｃ－ｈ活性化手法 |
| WO2021115372A1 (zh) * | 2019-12-10 | 2021-06-17 | 江苏恩华药业股份有限公司 | 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 |
| CN120424027B (zh) * | 2024-02-05 | 2026-03-24 | 石药集团中奇制药技术（石家庄）有限公司 | 一种伏硫西汀半帕莫酸盐晶型 |
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 |
| WO2003053942A1 (en) | 2001-12-20 | 2003-07-03 | H. Lundbeck A/S | Aryloxyphenyl and arylsulfanylphenyl derivatives |
| EP2044043B2 (en) * | 2006-06-16 | 2021-03-03 | H. Lundbeck A/S | 1- ý[- (2, 4-dimethylphenylsulfanyl) -phenyl]piperazine hydrobromide 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 |
| NZ722096A (en) | 2011-12-15 | 2016-11-25 | Alkermes Pharma Ireland Ltd | Prodrugs of secondary amine compounds |
| WO2014191548A1 (en) | 2013-05-31 | 2014-12-04 | Lek Pharmaceuticals D.D. | New process for the synthesis of 1-(2-((2,4-dimethylphenyl)thio)phenyl)piperazine |
| 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 |
| CN106170480B (zh) | 2014-05-09 | 2019-09-20 | 上海科胜药物研发有限公司 | 新的沃替西汀中间体及其合成方法 |
| 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 |
| WO2017125504A1 (en) * | 2016-01-20 | 2017-07-27 | 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 |
| WO2017167180A1 (zh) * | 2016-03-29 | 2017-10-05 | 上海华汇拓医药科技有限公司 | 沃替西汀的帕莫酸盐及其晶型 |
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2017
- 2017-06-15 WO PCT/CN2017/088493 patent/WO2017215636A1/zh not_active Ceased
- 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 JP JP2018565312A patent/JP2019525900A/ja active Pending
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2021
- 2021-04-16 JP JP2021069689A patent/JP7123211B2/ja active Active