JP2016506959A5 - - Google Patents
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- JP2016506959A5 JP2016506959A5 JP2015556099A JP2015556099A JP2016506959A5 JP 2016506959 A5 JP2016506959 A5 JP 2016506959A5 JP 2015556099 A JP2015556099 A JP 2015556099A JP 2015556099 A JP2015556099 A JP 2015556099A JP 2016506959 A5 JP2016506959 A5 JP 2016506959A5
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- Prior art keywords
- alkyl
- group
- compound according
- phenyl
- optionally
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- -1 9-fluorenylmethyloxycarbonyl Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 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 1
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241001553014 Myrsine salicina Species 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361757920P | 2013-01-29 | 2013-01-29 | |
| US61/757,920 | 2013-01-29 | ||
| PCT/US2014/013621 WO2014120784A1 (en) | 2013-01-29 | 2014-01-29 | Spiro-lactam nmda receptor modulators and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016506959A JP2016506959A (ja) | 2016-03-07 |
| JP2016506959A5 true JP2016506959A5 (enExample) | 2019-03-28 |
| JP6531042B2 JP6531042B2 (ja) | 2019-06-12 |
Family
ID=50069346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015556099A Active JP6531042B2 (ja) | 2013-01-29 | 2014-01-29 | スピロラクタム系ｎｍｄａ受容体モジュレーターおよびその使用 |
Country Status (16)
| Country | Link |
|---|---|
| US (5) | US9828384B2 (enExample) |
| EP (1) | EP2951182B1 (enExample) |
| JP (1) | JP6531042B2 (enExample) |
| KR (1) | KR102410989B1 (enExample) |
| CN (1) | CN105408336B (enExample) |
| AU (1) | AU2014212485C1 (enExample) |
| BR (1) | BR112015018089B1 (enExample) |
| CA (1) | CA2898774C (enExample) |
| CL (1) | CL2015002122A1 (enExample) |
| EA (1) | EA032153B1 (enExample) |
| IL (1) | IL240162B (enExample) |
| MX (1) | MX375286B (enExample) |
| PE (1) | PE20151427A1 (enExample) |
| PH (1) | PH12015501596B1 (enExample) |
| SG (1) | SG11201505942YA (enExample) |
| WO (1) | WO2014120784A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101769999B1 (ko) | 2008-09-18 | 2017-08-21 | 노오쓰웨스턴 유니버시티 | Ｎｍｄａ 수용체 조절제 및 그의 용도 |
| MX2015009773A (es) | 2013-01-29 | 2016-08-05 | Aptinyx Inc | Moduladores de receptores nmda de espiro-lactama y sus usos. |
| BR112015018087B1 (pt) | 2013-01-29 | 2022-09-20 | Aptinyx Inc | Compostos moduladores de receptor n-metil-d-aspartato (nmda) de espiro-lactama, composição farmacêutica e uso dos mesmos |
| CA2899010A1 (en) | 2013-01-29 | 2014-08-07 | Naurex, Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| PE20151436A1 (es) | 2013-01-29 | 2015-10-10 | Naurex Inc | Moduladores de receptores nmda de espiro-lactama y sus usos |
| JP6531042B2 (ja) * | 2013-01-29 | 2019-06-12 | アプティニックス インコーポレイテッド | スピロラクタム系ｎｍｄａ受容体モジュレーターおよびその使用 |
| PE20190174A1 (es) * | 2016-05-19 | 2019-02-01 | Aptinyx Inc | Moduladores del receptor espiro-lactama n-metil-d-aspartato y usos de los mismos |
| WO2017201285A1 (en) | 2016-05-19 | 2017-11-23 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| BR112019001921A2 (pt) | 2016-08-01 | 2019-05-14 | Aptinyx Inc. | moduladores do receptor nmda de espiro-lactama e seus usos |
| US10918637B2 (en) | 2016-08-01 | 2021-02-16 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
| AU2017306152A1 (en) * | 2016-08-01 | 2019-01-31 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
| SG11201900554YA (en) | 2016-08-01 | 2019-02-27 | Aptinyx Inc | Spiro-lactam nmda modulators and methods of using same |
| CN109661398B (zh) | 2016-08-01 | 2022-07-05 | 阿普廷伊克斯股份有限公司 | 螺-内酰胺和二-螺-内酰胺nmda受体调节剂及其用途 |
| WO2019152685A1 (en) * | 2018-01-31 | 2019-08-08 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and methods of using same |
| WO2019152681A1 (en) * | 2018-01-31 | 2019-08-08 | Aptinyx Inc. | Spiro-lactam and bis-spiro-lactam nmda receptor modulators and uses thereof |
| CA3089559A1 (en) * | 2018-01-31 | 2019-08-08 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| WO2019152696A1 (en) * | 2018-01-31 | 2019-08-08 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| WO2019152688A1 (en) * | 2018-01-31 | 2019-08-08 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| US11578072B2 (en) * | 2018-01-31 | 2023-02-14 | Aptinyx Inc. | Spiro-lactam NMDA receptor modulators and uses thereof |
| US12215114B2 (en) * | 2019-06-24 | 2025-02-04 | Naurex Inc. | Processes and intermediates for producing diazaspiro lactam compounds |
| US12012413B2 (en) | 2019-11-11 | 2024-06-18 | Tenacia Biotechnology (Hong Kong) Co., Limited | Methods of treating painful diabetic peripheral neuropathy |
| WO2021228123A1 (zh) * | 2020-05-12 | 2021-11-18 | 北京广为医药科技有限公司 | 调节nmda受体活性的化合物、其药物组合物及用途 |
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| DE102009001460B4 (de) | 2009-03-11 | 2010-12-02 | Zf Friedrichshafen Ag | Ölbehälter |
| WO2011003064A2 (en) | 2009-07-02 | 2011-01-06 | Naurex, Inc. | Methods of treating neuropathic pain |
| US8951968B2 (en) | 2009-10-05 | 2015-02-10 | Northwestern University | Methods of treating depression and other related diseases |
| PL2485751T3 (pl) | 2009-10-05 | 2014-10-31 | Univ Northwestern | GLYX-13 do stosowania w sposobie leczenia depresji opornej na leczenie |
| KR101692275B1 (ko) | 2010-02-11 | 2017-01-04 | 노오쓰웨스턴 유니버시티 | ２차 구조 안정화된 ｎｍｄａ 수용체 조절제 및 그의 용도 |
| CA2789331C (en) | 2010-02-11 | 2017-11-07 | Northwestern University | Secondary structure stabilized nmda receptor modulators and uses thereof |
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| PE20151436A1 (es) | 2013-01-29 | 2015-10-10 | Naurex Inc | Moduladores de receptores nmda de espiro-lactama y sus usos |
| CA2899010A1 (en) | 2013-01-29 | 2014-08-07 | Naurex, Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| BR112015018087B1 (pt) | 2013-01-29 | 2022-09-20 | Aptinyx Inc | Compostos moduladores de receptor n-metil-d-aspartato (nmda) de espiro-lactama, composição farmacêutica e uso dos mesmos |
| JP6531042B2 (ja) | 2013-01-29 | 2019-06-12 | アプティニックス インコーポレイテッド | スピロラクタム系ｎｍｄａ受容体モジュレーターおよびその使用 |
-
2014
- 2014-01-29 JP JP2015556099A patent/JP6531042B2/ja active Active
- 2014-01-29 SG SG11201505942YA patent/SG11201505942YA/en unknown
- 2014-01-29 EA EA201591402A patent/EA032153B1/ru unknown
- 2014-01-29 KR KR1020157023289A patent/KR102410989B1/ko active Active
- 2014-01-29 EP EP14703247.8A patent/EP2951182B1/en active Active
- 2014-01-29 CN CN201480018643.7A patent/CN105408336B/zh active Active
- 2014-01-29 MX MX2015009772A patent/MX375286B/es active IP Right Grant
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- 2014-01-29 PE PE2015001568A patent/PE20151427A1/es unknown
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- 2014-01-29 BR BR112015018089-2A patent/BR112015018089B1/pt not_active IP Right Cessation
- 2014-01-29 US US14/764,402 patent/US9828384B2/en active Active
- 2014-01-29 WO PCT/US2014/013621 patent/WO2014120784A1/en not_active Ceased
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2017
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2018
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2020
- 2020-07-02 US US16/919,438 patent/US20210155632A1/en not_active Abandoned
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