JP2013035842A5 - - Google Patents
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- Publication number
- JP2013035842A5 JP2013035842A5 JP2012186110A JP2012186110A JP2013035842A5 JP 2013035842 A5 JP2013035842 A5 JP 2013035842A5 JP 2012186110 A JP2012186110 A JP 2012186110A JP 2012186110 A JP2012186110 A JP 2012186110A JP 2013035842 A5 JP2013035842 A5 JP 2013035842A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- hexane
- alkyl
- formula
- alkoxy
- 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 C 1 -C 3 alkyl Chemical group 0.000 claims description 48
- CCLICHYMXOOKTC-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC=C2C(C)=CC=C(C34C(C3)CNC4)C2=C1 CCLICHYMXOOKTC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims 78
- 238000000034 method Methods 0.000 claims 78
- 150000003839 salts Chemical class 0.000 claims 53
- 125000001475 halogen functional group Chemical group 0.000 claims 40
- 125000003545 alkoxy group Chemical group 0.000 claims 38
- 125000001624 naphthyl group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 20
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 20
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 20
- 125000003282 alkyl amino group Chemical group 0.000 claims 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 18
- 125000001589 carboacyl group Chemical group 0.000 claims 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- BRLQWZUYTZBJKN-VKHMYHEASA-N (-)-Epichlorohydrin Chemical compound ClC[C@H]1CO1 BRLQWZUYTZBJKN-VKHMYHEASA-N 0.000 claims 3
- KFAICONQWSILFT-XRZFDKQNSA-N (1R,5S)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane hydrochloride Chemical group Cl.C1=CC=C2C([C@@]34CNC[C@H]4C3)=CC=CC2=C1 KFAICONQWSILFT-XRZFDKQNSA-N 0.000 claims 3
- KFAICONQWSILFT-NXCSSKFKSA-N (1S,5R)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane hydrochloride Chemical group Cl.C1=CC=C2C([C@]34CNC[C@@H]4C3)=CC=CC2=C1 KFAICONQWSILFT-NXCSSKFKSA-N 0.000 claims 3
- JXCCCXJMHZUFOM-IUODEOHRSA-N (1r,5s)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=C2C([C@@]34CNC[C@H]4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-IUODEOHRSA-N 0.000 claims 3
- HKHCSWPSUSWGLI-CABCVRRESA-N (1r,5s)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=CC2=CC([C@@]34CNC[C@H]4C3)=CC=C21 HKHCSWPSUSWGLI-CABCVRRESA-N 0.000 claims 3
- ACVMJAJGCQUPKX-LIOBNPLQSA-N (1r,5s)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical group Cl.C1=CC=CC2=CC([C@@]34CNC[C@H]4C3)=CC=C21 ACVMJAJGCQUPKX-LIOBNPLQSA-N 0.000 claims 3
- JXCCCXJMHZUFOM-WFASDCNBSA-N (1s,5r)-1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=C2C([C@]34CNC[C@@H]4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-WFASDCNBSA-N 0.000 claims 3
- HKHCSWPSUSWGLI-LSDHHAIUSA-N (1s,5r)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=CC2=CC([C@]34CNC[C@@H]4C3)=CC=C21 HKHCSWPSUSWGLI-LSDHHAIUSA-N 0.000 claims 3
- ACVMJAJGCQUPKX-LDXVYITESA-N (1s,5r)-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical group Cl.C1=CC=CC2=CC([C@]34CNC[C@@H]4C3)=CC=C21 ACVMJAJGCQUPKX-LDXVYITESA-N 0.000 claims 3
- JBEISIMRAMNVTP-UHFFFAOYSA-N 1-(4-methylnaphthalen-1-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=C2C(C)=CC=C(C34C(C3)CNC4)C2=C1 JBEISIMRAMNVTP-UHFFFAOYSA-N 0.000 claims 3
- PZSAUCRKLIVWSM-UHFFFAOYSA-N 1-(6-ethoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C1(CNC2)C2C1 PZSAUCRKLIVWSM-UHFFFAOYSA-N 0.000 claims 3
- REMNBRUUVNHKLO-UHFFFAOYSA-N 1-(6-ethoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC2=CC(OCC)=CC=C2C=C1C1(CNC2)C2C1 REMNBRUUVNHKLO-UHFFFAOYSA-N 0.000 claims 3
- XEECWPXYCFHQRV-UHFFFAOYSA-N 1-(6-ethoxynaphthalen-2-yl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C1(CN(C)C2)C2C1 XEECWPXYCFHQRV-UHFFFAOYSA-N 0.000 claims 3
- QGLYIJQWOLIXCL-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane Chemical group C1=CC2=CC(OC)=CC=C2C=C1C1(CNC2)C2C1 QGLYIJQWOLIXCL-UHFFFAOYSA-N 0.000 claims 3
- VLKZPBIIKBIPCD-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC2=CC(OC)=CC=C2C=C1C1(CNC2)C2C1 VLKZPBIIKBIPCD-UHFFFAOYSA-N 0.000 claims 3
- ZQDUBTPWXSFQGA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-3-methyl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C1(CN(C)C2)C2C1 ZQDUBTPWXSFQGA-UHFFFAOYSA-N 0.000 claims 3
- JXCCCXJMHZUFOM-UHFFFAOYSA-N 1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=C2C(C34CNCC4C3)=CC=CC2=C1 JXCCCXJMHZUFOM-UHFFFAOYSA-N 0.000 claims 3
- KFAICONQWSILFT-UHFFFAOYSA-N 1-naphthalen-1-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical group Cl.C1=CC=C2C(C34CNCC4C3)=CC=CC2=C1 KFAICONQWSILFT-UHFFFAOYSA-N 0.000 claims 3
- HKHCSWPSUSWGLI-UHFFFAOYSA-N 1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical group C1=CC=CC2=CC(C34CNCC4C3)=CC=C21 HKHCSWPSUSWGLI-UHFFFAOYSA-N 0.000 claims 3
- ACVMJAJGCQUPKX-UHFFFAOYSA-N 1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical group Cl.C1=CC=CC2=CC(C34CNCC4C3)=CC=C21 ACVMJAJGCQUPKX-UHFFFAOYSA-N 0.000 claims 3
- RBSUWUVPTHHLHV-UHFFFAOYSA-N 1-naphthalen-2-yl-3-propan-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CC3CN(C4)C(C)C)=CC=C21 RBSUWUVPTHHLHV-UHFFFAOYSA-N 0.000 claims 3
- MHTNGUFDGSMXPO-UHFFFAOYSA-N 1-naphthalen-2-yl-3-propan-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C34CC3CN(C4)C(C)C)=CC=C21 MHTNGUFDGSMXPO-UHFFFAOYSA-N 0.000 claims 3
- CIRWXGMYHWXKHE-UHFFFAOYSA-N 3-ethyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane Chemical compound C1=CC=CC2=CC(C34CC3CN(C4)CC)=CC=C21 CIRWXGMYHWXKHE-UHFFFAOYSA-N 0.000 claims 3
- JWONXBLAMGLBFI-UHFFFAOYSA-N 3-ethyl-1-naphthalen-2-yl-3-azabicyclo[3.1.0]hexane;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C34CC3CN(C4)CC)=CC=C21 JWONXBLAMGLBFI-UHFFFAOYSA-N 0.000 claims 3
- MCQMSXKZCZQBBW-UHFFFAOYSA-N CCOC1=CC2=C(C=C1)C=C(C=C2)C34CC3CN(C4)C.Cl Chemical compound CCOC1=CC2=C(C=C1)C=C(C=C2)C34CC3CN(C4)C.Cl MCQMSXKZCZQBBW-UHFFFAOYSA-N 0.000 claims 3
- XLUJMZVGWFEJTJ-UHFFFAOYSA-N CN1CC2CC2(C1)C3=CC4=C(C=C3)C=C(C=C4)OC.Cl Chemical compound CN1CC2CC2(C1)C3=CC4=C(C=C3)C=C(C=C4)OC.Cl XLUJMZVGWFEJTJ-UHFFFAOYSA-N 0.000 claims 3
- HJLHTTJLVALHOP-UHFFFAOYSA-N hexane;hydron;chloride Chemical compound Cl.CCCCCC HJLHTTJLVALHOP-UHFFFAOYSA-N 0.000 claims 3
- 230000002152 alkylating effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UNEURVGVRYJOMG-UHFFFAOYSA-N (4-methoxynaphthalen-1-yl)boronic acid Chemical compound C1=CC=C2C(OC)=CC=C(B(O)O)C2=C1 UNEURVGVRYJOMG-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- QJYHLROZBKJKDS-UHFFFAOYSA-N O=C(C1C2)NCC12[AlH2] Chemical compound O=C(C1C2)NCC12[AlH2] QJYHLROZBKJKDS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70336405P | 2005-07-27 | 2005-07-27 | |
| US60/703,364 | 2005-07-27 | ||
| US11/493,431 US20070082940A1 (en) | 2005-07-27 | 2006-07-25 | Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders |
| US11/493,431 | 2006-07-25 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008524100A Division JP5184354B2 (ja) | 2005-07-27 | 2006-07-25 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015030541A Division JP2015134786A (ja) | 2005-07-27 | 2015-02-19 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013035842A JP2013035842A (ja) | 2013-02-21 |
| JP2013035842A5 true JP2013035842A5 (enExample) | 2014-08-07 |
| JP5767178B2 JP5767178B2 (ja) | 2015-08-19 |
Family
ID=37709141
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008524100A Active JP5184354B2 (ja) | 2005-07-27 | 2006-07-25 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
| JP2012186110A Expired - Fee Related JP5767178B2 (ja) | 2005-07-27 | 2012-08-27 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
| JP2015030541A Pending JP2015134786A (ja) | 2005-07-27 | 2015-02-19 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008524100A Active JP5184354B2 (ja) | 2005-07-27 | 2006-07-25 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015030541A Pending JP2015134786A (ja) | 2005-07-27 | 2015-02-19 | 新規１−アリール−３−アザビシクロ［３．１．０］ヘキサン：調製および神経精神障害の処理への使用 |
Country Status (16)
| Country | Link |
|---|---|
| US (9) | US20070082940A1 (enExample) |
| EP (2) | EP1915146A4 (enExample) |
| JP (3) | JP5184354B2 (enExample) |
| KR (3) | KR101733180B1 (enExample) |
| CN (2) | CN101272781A (enExample) |
| AU (1) | AU2006275870B2 (enExample) |
| BR (1) | BRPI0613943B1 (enExample) |
| CA (1) | CA2659215C (enExample) |
| CY (1) | CY1122238T1 (enExample) |
| IL (2) | IL189008A (enExample) |
| NO (1) | NO343037B1 (enExample) |
| NZ (1) | NZ592836A (enExample) |
| PL (1) | PL2719384T3 (enExample) |
| RU (1) | RU2008107336A (enExample) |
| WO (1) | WO2007016155A2 (enExample) |
| ZA (1) | ZA200801825B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070043100A1 (en) | 2005-08-16 | 2007-02-22 | Hagen Eric J | Novel polymorphs of azabicyclohexane |
| CN101272781A (zh) | 2005-07-27 | 2008-09-24 | 多夫药品公司 | 新的1-芳基-3-氮杂二环[3.1.0]己烷：其制备方法和用于治疗神经精神障碍的用途 |
| EP2016053B1 (en) * | 2006-04-28 | 2010-11-10 | Merck Sharp & Dohme Corp. | Process for the synthesis of (+) and (-)-1-aryl-3-azabicyclo[3.1.0]hexanes |
| US20080045725A1 (en) * | 2006-04-28 | 2008-02-21 | Murry Jerry A | Process For The Synthesis of (+) And (-)-1-(3,4-Dichlorophenyl)-3-Azabicyclo[3.1.0]Hexane |
| US8138377B2 (en) | 2006-11-07 | 2012-03-20 | Dov Pharmaceutical, Inc. | Arylbicyclo[3.1.0]hexylamines and methods and compositions for their preparation and use |
| US9133159B2 (en) | 2007-06-06 | 2015-09-15 | Neurovance, Inc. | 1-heteroaryl-3-azabicyclo[3.1.0]hexanes, methods for their preparation and their use as medicaments |
| GB0716632D0 (en) * | 2007-08-24 | 2007-10-03 | Glaxo Group Ltd | Compounds |
| GB0716633D0 (en) * | 2007-08-24 | 2007-10-03 | Glaxo Group Ltd | Compounds |
| GB0804326D0 (en) * | 2008-03-07 | 2008-04-16 | Glaxo Group Ltd | Novel compounds |
| WO2010075064A1 (en) * | 2008-12-16 | 2010-07-01 | Sepracor Inc. | Triple reuptake inhibitors and methods of their use |
| CN102803224A (zh) | 2009-06-26 | 2012-11-28 | 万能药生物有限公司 | 新的氮杂双环己烷类化合物 |
| WO2012033956A1 (en) | 2010-09-08 | 2012-03-15 | Mithridion, Inc. | Cognition enhancing compounds and compositions, methods of making, and methods of treating |
| WO2012042539A2 (en) | 2010-09-28 | 2012-04-05 | Panacea Biotec Ltd | Novel bicyclic compounds |
| US20140206740A1 (en) | 2011-07-30 | 2014-07-24 | Neurovance, Inc. | Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters |
| HRP20200424T1 (hr) * | 2011-07-30 | 2020-09-04 | Otsuka America Pharmaceutical, Inc. | Uporaba (1r,5s)-(+)-1-(naftalen-2-il)-3-azabiciklo(3.1.0)heksana u liječenju uvjeta koji su pod utjecajem monoaminskih neurotransmitera |
| JP6284140B2 (ja) * | 2013-06-17 | 2018-02-28 | 株式会社タムラ製作所 | Ｇａ２Ｏ３系半導体素子 |
| US20160303077A1 (en) * | 2013-12-09 | 2016-10-20 | Neurovance, Inc. | Novel compositions |
| CN107921021A (zh) | 2015-06-17 | 2018-04-17 | 大塚制药美国公司 | 结晶化合物 |
| WO2018119291A1 (en) * | 2016-12-21 | 2018-06-28 | Otsuka America Pharmaceutical, Inc. | Synthetic methods |
| US12054448B2 (en) | 2018-04-26 | 2024-08-06 | Api Corporation | Method for manufacturing aromatic nitrile compound |
| CN113661166A (zh) * | 2019-01-09 | 2021-11-16 | 卫材R&D管理有限公司 | 用于合成二氮杂二环[6.2.0]癸烷相关化合物的方法 |
| WO2021075494A1 (ja) | 2019-10-16 | 2021-04-22 | 大塚製薬株式会社 | センタナファジンの製造方法 |
| WO2021085468A1 (ja) | 2019-10-29 | 2021-05-06 | 株式会社エーピーアイ コーポレーション | 高純度２－ナフチルアセトニトリル及びその製造方法 |
| JP7787190B2 (ja) | 2021-02-23 | 2025-12-16 | 大塚製薬株式会社 | センタナファジン製剤ならびにその製造および使用方法 |
| WO2022256215A1 (en) | 2021-05-31 | 2022-12-08 | Teva Pharmaceuticals International Gmbh | Solid state form of centanafadine hcl and process for preparation thereof |
| EP4357335A4 (en) * | 2021-06-15 | 2025-11-26 | Otsuka Pharma Co Ltd | AZABICYCLO[3.1.0]HEXANE COMPOUND |
| CA3264158A1 (en) | 2022-09-02 | 2024-03-07 | Otsuka Pharmaceutical Co., Ltd. | 1-(NAPHTALENE-2-YL)-3-AZABICYCLO[3.1.0]HEXANE FOR THE TREATMENT OF MAJOR DEPRESSIVE DISORDER |
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| JPS535994B2 (enExample) * | 1974-09-26 | 1978-03-03 | ||
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