JP2017527631A5 - - Google Patents
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- Publication number
- JP2017527631A5 JP2017527631A5 JP2017534017A JP2017534017A JP2017527631A5 JP 2017527631 A5 JP2017527631 A5 JP 2017527631A5 JP 2017534017 A JP2017534017 A JP 2017534017A JP 2017534017 A JP2017534017 A JP 2017534017A JP 2017527631 A5 JP2017527631 A5 JP 2017527631A5
- Authority
- JP
- Japan
- Prior art keywords
- diazaspiro
- fluorophenoxy
- oxa
- undecane
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- -1 ethylenedioxy group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- CLTNRKNBPJLOCT-UHFFFAOYSA-N C1(CC1)C1=NC(=NC(=C1)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 Chemical compound C1(CC1)C1=NC(=NC(=C1)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 CLTNRKNBPJLOCT-UHFFFAOYSA-N 0.000 claims 2
- OSYDLANVDZCPRE-UHFFFAOYSA-N CC1=CC(=NC(=N1)N1CCC2(CNCCO2)CC1)OC=1C=C(C#N)C=CC=1 Chemical compound CC1=CC(=NC(=N1)N1CCC2(CNCCO2)CC1)OC=1C=C(C#N)C=CC=1 OSYDLANVDZCPRE-UHFFFAOYSA-N 0.000 claims 2
- GCNZXETZIBQOCG-UHFFFAOYSA-N CC1=NC(=NC(=C1)OC1=CC(=CC=C1)C)N1CCC2(CNCCO2)CC1 Chemical compound CC1=NC(=NC(=C1)OC1=CC(=CC=C1)C)N1CCC2(CNCCO2)CC1 GCNZXETZIBQOCG-UHFFFAOYSA-N 0.000 claims 2
- NLLQBYDAGGXFCP-UHFFFAOYSA-N CC1=NC(=NC(=C1)OC1=CC=CC=C1)N1CCC2(CNCCO2)CC1 Chemical compound CC1=NC(=NC(=C1)OC1=CC=CC=C1)N1CCC2(CNCCO2)CC1 NLLQBYDAGGXFCP-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- FLDAMRNIVUVJRK-UHFFFAOYSA-N FC1=C(C(=CC=C1OC1=CC(=CC=C1)F)F)N1CCC2(CNCCO2)CC1 Chemical compound FC1=C(C(=CC=C1OC1=CC(=CC=C1)F)F)N1CCC2(CNCCO2)CC1 FLDAMRNIVUVJRK-UHFFFAOYSA-N 0.000 claims 2
- NDUZYNZHAAONON-UHFFFAOYSA-N FC1=C(C=C(C=C1F)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 Chemical compound FC1=C(C=C(C=C1F)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 NDUZYNZHAAONON-UHFFFAOYSA-N 0.000 claims 2
- UPTRBXKTOJZNAB-UHFFFAOYSA-N FC1=C(C=C(C=C1OC1=CC(=CC=C1)F)F)N1CCC2(CNCCO2)CC1 Chemical compound FC1=C(C=C(C=C1OC1=CC(=CC=C1)F)F)N1CCC2(CNCCO2)CC1 UPTRBXKTOJZNAB-UHFFFAOYSA-N 0.000 claims 2
- IFKASTTVCISIPF-UHFFFAOYSA-N FC1=C(C=CC=C1OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 Chemical compound FC1=C(C=CC=C1OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 IFKASTTVCISIPF-UHFFFAOYSA-N 0.000 claims 2
- UQJOXFKJBZTQRN-UHFFFAOYSA-N FC1=C(C=CC=C1OC1=CC=CC=C1)N1CCC2(CNCCO2)CC1 Chemical compound FC1=C(C=CC=C1OC1=CC=CC=C1)N1CCC2(CNCCO2)CC1 UQJOXFKJBZTQRN-UHFFFAOYSA-N 0.000 claims 2
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- TVKDOMFQEAUPSL-UHFFFAOYSA-N FC1=CC(=C(C=C1F)N1CCC2(CC1)CCNCC2)OC1=CC(=CC=C1)F Chemical compound FC1=CC(=C(C=C1F)N1CCC2(CC1)CCNCC2)OC1=CC(=CC=C1)F TVKDOMFQEAUPSL-UHFFFAOYSA-N 0.000 claims 2
- BRHOSLMTYNSPCU-UHFFFAOYSA-N FC1=CC(=C(C=C1F)N1CCC2(CCCNC2)CC1)OC1=CC(=CC=C1)F Chemical compound FC1=CC(=C(C=C1F)N1CCC2(CCCNC2)CC1)OC1=CC(=CC=C1)F BRHOSLMTYNSPCU-UHFFFAOYSA-N 0.000 claims 2
- XZGDMJHTSNODSG-UHFFFAOYSA-N FC1=CC(=C(C=C1F)N1CCC2(CCNC2)CC1)OC1=CC(=CC=C1)F Chemical compound FC1=CC(=C(C=C1F)N1CCC2(CCNC2)CC1)OC1=CC(=CC=C1)F XZGDMJHTSNODSG-UHFFFAOYSA-N 0.000 claims 2
- GQORDSCTOHJVGL-UHFFFAOYSA-N FC1=CC(=C(C=C1F)N1CCC2(CNCCO2)CC1)OC1=CC(=CC=C1)F Chemical compound FC1=CC(=C(C=C1F)N1CCC2(CNCCO2)CC1)OC1=CC(=CC=C1)F GQORDSCTOHJVGL-UHFFFAOYSA-N 0.000 claims 2
- MHZZVGCHJXSMAS-UHFFFAOYSA-N FC=1C=C(C=C(C=1)OC1=CC(=CC=C1)F)N1CCC2(CCNC2)CC1 Chemical compound FC=1C=C(C=C(C=1)OC1=CC(=CC=C1)F)N1CCC2(CCNC2)CC1 MHZZVGCHJXSMAS-UHFFFAOYSA-N 0.000 claims 2
- OZUKNWTZRJTZAM-UHFFFAOYSA-N FC=1C=C(C=C(C=1)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 Chemical compound FC=1C=C(C=C(C=1)OC1=CC(=CC=C1)F)N1CCC2(CNCCO2)CC1 OZUKNWTZRJTZAM-UHFFFAOYSA-N 0.000 claims 2
- AQKXRQBPFRGBIM-UHFFFAOYSA-N FC=1C=C(OC2=CC(=CC(=N2)N2CCC3(CNCCO3)CC2)C(F)(F)F)C=CC=1 Chemical compound FC=1C=C(OC2=CC(=CC(=N2)N2CCC3(CNCCO3)CC2)C(F)(F)F)C=CC=1 AQKXRQBPFRGBIM-UHFFFAOYSA-N 0.000 claims 2
- FRYWDPTWXKMFIV-UHFFFAOYSA-N FC=1C=C(OC2=CC(=NC(=N2)N2CCC3(CNCCO3)CC2)C#N)C=CC=1 Chemical compound FC=1C=C(OC2=CC(=NC(=N2)N2CCC3(CNCCO3)CC2)C#N)C=CC=1 FRYWDPTWXKMFIV-UHFFFAOYSA-N 0.000 claims 2
- ZESZUQXZFYWEDZ-UHFFFAOYSA-N FC=1C=C(OC2=NC(=CC(=C2)C#N)N2CCC3(CNCCO3)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=CC(=C2)C#N)N2CCC3(CNCCO3)CC2)C=CC=1 ZESZUQXZFYWEDZ-UHFFFAOYSA-N 0.000 claims 2
- SVGZGCKBHLFPIC-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(C2)OCCNC3)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(C2)OCCNC3)C=CC=1 SVGZGCKBHLFPIC-UHFFFAOYSA-N 0.000 claims 2
- GEVZPLPEKJKIBV-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(CC2)C(CNCC3)O)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(CC2)C(CNCC3)O)C=CC=1 GEVZPLPEKJKIBV-UHFFFAOYSA-N 0.000 claims 2
- ZIYHUPRJRJTSIY-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(CC2)CNCCC3=O)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CC3(CC2)CNCCC3=O)C=CC=1 ZIYHUPRJRJTSIY-UHFFFAOYSA-N 0.000 claims 2
- MYDYISTUWKZONW-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CC2)N(CCCNC3)C)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CC2)N(CCCNC3)C)C=CC=1 MYDYISTUWKZONW-UHFFFAOYSA-N 0.000 claims 2
- BVCHXSYBWUKBPX-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CC2)N(CCCNC3=O)C)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CC2)N(CCCNC3=O)C)C=CC=1 BVCHXSYBWUKBPX-UHFFFAOYSA-N 0.000 claims 2
- JZANIIBHVHLPQJ-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNC(CO3)=O)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNC(CO3)=O)CC2)C=CC=1 JZANIIBHVHLPQJ-UHFFFAOYSA-N 0.000 claims 2
- MUMVFZQOXPRNRA-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNC(O3)=O)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNC(O3)=O)CC2)C=CC=1 MUMVFZQOXPRNRA-UHFFFAOYSA-N 0.000 claims 2
- XNETVVQWLBRUNT-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCN3)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCN3)CC2)C=CC=1 XNETVVQWLBRUNT-UHFFFAOYSA-N 0.000 claims 2
- WOQJOOVJNSJTHF-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCN3C)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCN3C)CC2)C=CC=1 WOQJOOVJNSJTHF-UHFFFAOYSA-N 0.000 claims 2
- PGRBNOKBXBCQOX-UHFFFAOYSA-N FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCO3)CC2)C=CC=1 Chemical compound FC=1C=C(OC2=NC(=NC(=C2)C(F)(F)F)N2CCC3(CNCCO3)CC2)C=CC=1 PGRBNOKBXBCQOX-UHFFFAOYSA-N 0.000 claims 2
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- VOGWKIDOYQXACT-UHFFFAOYSA-N FC=1C=C(OC=2C(=C(C#N)C=C(C=2)N2CCC3(CNCCO3)CC2)C)C=CC=1 Chemical compound FC=1C=C(OC=2C(=C(C#N)C=C(C=2)N2CCC3(CNCCO3)CC2)C)C=CC=1 VOGWKIDOYQXACT-UHFFFAOYSA-N 0.000 claims 2
- WGUWYPRRZSZZLF-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=NC(=NC(=C1)C(F)(F)F)N1CCC2(CNCCO2)CC1 Chemical compound O(C1=CC=CC=C1)C1=NC(=NC(=C1)C(F)(F)F)N1CCC2(CNCCO2)CC1 WGUWYPRRZSZZLF-UHFFFAOYSA-N 0.000 claims 2
- XCMMHZAUCGKKPD-UHFFFAOYSA-N O1CCNCC11CCN(CC1)C1=C(C#N)C=CC(=C1)OC1=CC=CC=C1 Chemical compound O1CCNCC11CCN(CC1)C1=C(C#N)C=CC(=C1)OC1=CC=CC=C1 XCMMHZAUCGKKPD-UHFFFAOYSA-N 0.000 claims 2
- LVTITHFSOZBRMM-UHFFFAOYSA-N O1CCNCC11CCN(CC1)C1=NC(=CC(=N1)OC=1C=C(C#N)C=CC=1)C(F)(F)F Chemical compound O1CCNCC11CCN(CC1)C1=NC(=CC(=N1)OC=1C=C(C#N)C=CC=1)C(F)(F)F LVTITHFSOZBRMM-UHFFFAOYSA-N 0.000 claims 2
- NNDGBQCSFXUKBN-UHFFFAOYSA-N O1CCNCC11CCN(CC1)C=1C=C(C#N)C=C(C=1)OC1=CC=CC=C1 Chemical compound O1CCNCC11CCN(CC1)C=1C=C(C#N)C=C(C=1)OC1=CC=CC=C1 NNDGBQCSFXUKBN-UHFFFAOYSA-N 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
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- 208000019901 Anxiety disease Diseases 0.000 claims 1
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- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- MONPFLRTHMVDCM-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=NC(=NC(=C1)OC)N1CCC2(CNCCO2)CC1 Chemical compound C(C1=CC=CC=C1)C1=NC(=NC(=C1)OC)N1CCC2(CNCCO2)CC1 MONPFLRTHMVDCM-UHFFFAOYSA-N 0.000 claims 1
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- VACUEQHHEBYVMP-UHFFFAOYSA-N COC1=C(OC2=NC(=NC(=C2)C)N2CCC3(CNCCO3)CC2)C=CC=C1 Chemical compound COC1=C(OC2=NC(=NC(=C2)C)N2CCC3(CNCCO3)CC2)C=CC=C1 VACUEQHHEBYVMP-UHFFFAOYSA-N 0.000 claims 1
- WIPVJHVRGPHILG-UHFFFAOYSA-N COC=1C=C(OC2=NC(=NC(=C2)C)N2CCC3(CNCCO3)CC2)C=CC=1 Chemical compound COC=1C=C(OC2=NC(=NC(=C2)C)N2CCC3(CNCCO3)CC2)C=CC=1 WIPVJHVRGPHILG-UHFFFAOYSA-N 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims 1
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 claims 1
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000027534 Emotional disease Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
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| CN106831818A (zh) * | 2017-02-07 | 2017-06-13 | 上海合全药业股份有限公司 | 一种2‑叔丁基‑7‑甲基‑5‑氧杂‑2,8‑二氮杂螺烷‑[3,5]壬烷‑2,7‑二羧酸的制备方法 |
| ES2988457T3 (es) | 2017-03-24 | 2024-11-20 | Wakunaga Pharma Co Ltd | Derivado novedoso del ácido piridona carboxílico o sal del mismo |
| CN108164542A (zh) * | 2018-01-05 | 2018-06-15 | 天津药明康德新药开发有限公司 | 外消旋-9-氨基-6-氧杂-2-氮杂螺[4.5]癸烷-2-羧酸叔丁基酯的合成方法 |
| WO2020048827A1 (en) | 2018-09-03 | 2020-03-12 | Bayer Aktiengesellschaft | 1, 3, 9-triazaspiro[5.5] undecan-2-one compounds |
| CN112679405B (zh) * | 2019-10-17 | 2023-12-15 | 南京富润凯德生物医药有限公司 | 一种(s)-7-氧杂-2-氮杂螺[4.5]癸烷衍生物的制备方法 |
| MX2022007652A (es) | 2019-12-19 | 2022-09-23 | Janssen Pharmaceutica Nv | Derivados espiráncos sustituidos de cadena lineal. |
| CN113200997B (zh) * | 2021-05-07 | 2023-10-03 | 上海合全医药有限公司 | 2,5-二氧杂-8-氮杂螺[3.5]壬烷及其盐的合成方法 |
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| CN115894489A (zh) * | 2021-09-22 | 2023-04-04 | 中国药科大学 | 一种受体相互作用蛋白激酶1的抑制剂及其制备方法、应用 |
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| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| FR2734265B1 (fr) | 1995-05-17 | 1997-06-13 | Adir | Nouveaux composes spiro heterocycliques, leur procede de preparation et les compositions pharmaceutiques les contenant |
| US6835371B1 (en) | 1997-09-12 | 2004-12-28 | David R. Elmaleh | Diagnostic and therapeutic piperazine and piperidine compounds and process |
| AU2152001A (en) | 1999-12-30 | 2001-07-16 | H. Lundbeck A/S | Phenylpiperazinyl derivatives |
| SI1315750T1 (sl) | 2000-08-30 | 2007-06-30 | Hoffmann La Roche | Cikliäśni peptidi kot agonisti za receptorje melanokortina-4 |
| AU2003245753B2 (en) * | 2002-07-05 | 2009-12-24 | Targacept, Inc. | N-aryl diazaspiracyclic compounds and methods of preparation and use thereof |
| WO2005047286A1 (ja) * | 2003-11-13 | 2005-05-26 | Ono Pharmaceutical Co., Ltd. | スピロ複素環化合物 |
| CN101022801A (zh) * | 2004-08-20 | 2007-08-22 | 塔加西普特公司 | N－芳基二氮杂螺环化合物在成瘾治疗中的用途 |
| EP1940406A4 (en) * | 2005-10-21 | 2009-11-18 | Merck & Co Inc | POTASSIUM CHANNEL INHIBITORS |
| GB0707934D0 (en) * | 2007-04-24 | 2007-05-30 | Glaxo Group Ltd | Chemical compounds |
| WO2012024397A2 (en) * | 2010-08-17 | 2012-02-23 | Albany Molecular Research, Inc. | 2,5-methano-and 2,5-ethano-tetrahydrobenzazepine derivatives and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US20130116241A1 (en) * | 2011-11-09 | 2013-05-09 | Abbvie Inc. | Novel inhibitor compounds of phosphodiesterase type 10a |
| US9884865B2 (en) | 2013-08-26 | 2018-02-06 | Purdue Pharma L.P. | Azaspiro[4.5] decane derivatives and use thereof |
| RS57129B1 (sr) * | 2014-03-17 | 2018-07-31 | Remynd Nv | Jedinjenja 2,7-diazaspiro[3.5]nonana |
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- 2015-09-14 CN CN201580059377.7A patent/CN107108625A/zh active Pending
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