JP2018536653A5 - - Google Patents
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- Publication number
- JP2018536653A5 JP2018536653A5 JP2018522540A JP2018522540A JP2018536653A5 JP 2018536653 A5 JP2018536653 A5 JP 2018536653A5 JP 2018522540 A JP2018522540 A JP 2018522540A JP 2018522540 A JP2018522540 A JP 2018522540A JP 2018536653 A5 JP2018536653 A5 JP 2018536653A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylate
- piperidin
- salt
- compound
- ethyl
- 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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- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 9
- -1 cyano, hydroxy Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- ZDAVQPOSWCQTLX-UHFFFAOYSA-N ethyl 2-ethylheptanoate Chemical compound CCCCCC(CC)C(=O)OCC ZDAVQPOSWCQTLX-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000002981 neuropathic effect Effects 0.000 claims 3
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- ULFNAOHBWGRYLW-UHFFFAOYSA-N 1-cyclononylazonane Chemical group C1CCCCCCCC1N1CCCCCCCC1 ULFNAOHBWGRYLW-UHFFFAOYSA-N 0.000 claims 1
- QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical compound C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 claims 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims 1
- PSNDWZOXFDKLLH-UHFFFAOYSA-N 2-azaspiro[3.4]octane Chemical compound C1NCC11CCCC1 PSNDWZOXFDKLLH-UHFFFAOYSA-N 0.000 claims 1
- NVZWMJWMTWOVNJ-UHFFFAOYSA-N 6-azaspiro[3.4]octane Chemical group C1CCC21CNCC2 NVZWMJWMTWOVNJ-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- JNMRXPADXOICLQ-UHFFFAOYSA-N ethyl 2-[4-(N-methoxy-C-propylcarbonimidoyl)piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound CON=C(CCC)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC JNMRXPADXOICLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 230000003551 muscarinic effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 0 CC1*N(C)*1 Chemical compound CC1*N(C)*1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1519352.7A GB201519352D0 (en) | 2015-11-02 | 2015-11-02 | Pharmaceutical compounds |
| GB1519352.7 | 2015-11-02 | ||
| PCT/GB2016/053396 WO2017077292A1 (en) | 2015-11-02 | 2016-11-02 | Oxime compounds as agonists of the muscarinic m1 and/or m4 receptor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018536653A JP2018536653A (ja) | 2018-12-13 |
| JP2018536653A5 true JP2018536653A5 (enExample) | 2019-09-05 |
| JP6799596B2 JP6799596B2 (ja) | 2020-12-23 |
Family
ID=55130557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018522540A Active JP6799596B2 (ja) | 2015-11-02 | 2016-11-02 | ムスカリンｍ１及び／またはｍ４受容体のアゴニストとしてのオキシム化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US11208396B2 (enExample) |
| EP (2) | EP3370828B1 (enExample) |
| JP (1) | JP6799596B2 (enExample) |
| CN (1) | CN108290055B (enExample) |
| AU (1) | AU2016348847B2 (enExample) |
| CA (1) | CA3003669C (enExample) |
| DK (1) | DK3370828T3 (enExample) |
| ES (1) | ES2804774T3 (enExample) |
| GB (1) | GB201519352D0 (enExample) |
| WO (1) | WO2017077292A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6083818B2 (ja) | 2011-11-18 | 2017-02-22 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ１受容体アゴニスト |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| ES2789756T3 (es) | 2015-12-23 | 2020-10-26 | Merck Sharp & Dohme | Moduladores alostéricos de 6,7-dihidro-5H-pirrolo[3,4-b]piridin-5-ona del receptor de acetilcolina muscarínico M4 |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| GB201709652D0 (en) | 2017-06-16 | 2017-08-02 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| JP7166331B2 (ja) * | 2017-08-01 | 2022-11-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 中間体化合物及び方法 |
| CA3079188A1 (en) * | 2017-10-17 | 2019-04-25 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| US11299481B2 (en) | 2017-10-20 | 2022-04-12 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| EP3703680B1 (en) * | 2017-10-31 | 2024-05-15 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| KR102798432B1 (ko) | 2019-10-09 | 2025-04-22 | 노파르티스 아게 | M4 작용제로서의 5-옥사-2-아자스피로[3.4]옥탄 유도체 |
| AU2020361735B2 (en) | 2019-10-09 | 2024-04-18 | Novartis Ag | 2-azaspiro(3.4)octane derivatives as M4 agonists |
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| JP6348492B2 (ja) | 2012-08-10 | 2018-06-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ブルトン型チロシンキナーゼ（ｂｔｋ）阻害剤としてのヘテロ芳香族化合物 |
| DK2897948T3 (en) | 2012-09-18 | 2016-12-05 | Heptares Therapeutics Ltd | BICYCLIC AZA RELATIONS AS MUSCARIN M1 RECEPTOR AGONISTS |
| ES2694299T3 (es) * | 2013-02-07 | 2018-12-19 | Heptares Therapeutics Limited | Carboxilatos de piperidin-1-ilo y azepin-1-ilo como agonistas del receptor muscarínico M4 |
| PL3102568T3 (pl) | 2014-02-06 | 2019-01-31 | Heptares Therapeutics Limited | Bicykliczne związki aza w postaci agonistów receptorów muskarynowych m1 |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| NZ734400A (en) | 2015-02-13 | 2018-03-23 | Suven Life Sciences Ltd | Amide compounds as 5-ht4 receptor agonists |
| GB201504675D0 (en) | 2015-03-19 | 2015-05-06 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513742D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201513740D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonist |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| US10259787B2 (en) | 2016-10-14 | 2019-04-16 | Heptares Therapeutics Limited | Substituted cyclohexanes as muscarinic M1 receptor and/or M4 receptor agonists |
| GB201709652D0 (en) | 2017-06-16 | 2017-08-02 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| US10501483B2 (en) | 2017-10-24 | 2019-12-10 | Allergan, Inc. | Enamines and diastereo-selective reduction of enamines |
| GB201810245D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB202103211D0 (en) | 2021-03-08 | 2021-04-21 | Heptares Therapeutics Ltd | Pharmaceutical compounds for use in therapy |
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2015
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2016
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- 2016-11-02 JP JP2018522540A patent/JP6799596B2/ja active Active
- 2016-11-02 WO PCT/GB2016/053396 patent/WO2017077292A1/en not_active Ceased
- 2016-11-02 AU AU2016348847A patent/AU2016348847B2/en active Active
- 2016-11-02 EP EP16793975.0A patent/EP3370828B1/en active Active
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2021
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