JP2018522032A5 - - Google Patents
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- Publication number
- JP2018522032A5 JP2018522032A5 JP2018504985A JP2018504985A JP2018522032A5 JP 2018522032 A5 JP2018522032 A5 JP 2018522032A5 JP 2018504985 A JP2018504985 A JP 2018504985A JP 2018504985 A JP2018504985 A JP 2018504985A JP 2018522032 A5 JP2018522032 A5 JP 2018522032A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- azaspiro
- octane
- piperidin
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 25
- 125000005842 heteroatom Chemical group 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 22
- 229910052717 sulfur Inorganic materials 0.000 claims 22
- 229910052760 oxygen Inorganic materials 0.000 claims 21
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 15
- 150000002430 hydrocarbons Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- -1 cyano, hydroxy, amino Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 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 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 208000000094 Chronic Pain Diseases 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 208000005298 acute pain Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 230000002981 neuropathic effect Effects 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000006001 difluoroethyl group Chemical group 0.000 claims 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000005976 1-phenylethyloxy group Chemical group 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 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
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- AJIPGNUNWQKPLB-UHFFFAOYSA-N ethyl 2-[4-[acetyl(1,3-oxazol-2-ylmethyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC=1OC=CN=1 AJIPGNUNWQKPLB-UHFFFAOYSA-N 0.000 claims 1
- IIKLTKOTICGSHO-UHFFFAOYSA-N ethyl 2-[4-[acetyl(2-methylpropyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC(C)C IIKLTKOTICGSHO-UHFFFAOYSA-N 0.000 claims 1
- SVLHLBHIUNWCMN-UHFFFAOYSA-N ethyl 2-[4-[acetyl(cyclopropylmethyl)amino]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CC1CC1 SVLHLBHIUNWCMN-UHFFFAOYSA-N 0.000 claims 1
- GWYMXLWBAKWFDE-UHFFFAOYSA-N ethyl 6-[4-[acetyl(cyclopropyl)amino]piperidin-1-yl]-2-azaspiro[3.4]octane-2-carboxylate Chemical compound C(C)(=O)N(C1CCN(CC1)C1CC2(CN(C2)C(=O)OCC)CC1)C1CC1 GWYMXLWBAKWFDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 230000003551 muscarinic effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CCC1C(C)(*)C[C@@]1CN(C)C1*(C)CC(*)C(CC2)(CN2C(O)OC*)C1 Chemical compound CCC1C(C)(*)C[C@@]1CN(C)C1*(C)CC(*)C(CC2)(CN2C(O)OC*)C1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1513742.5A GB201513742D0 (en) | 2015-08-03 | 2015-08-03 | Muscarinic agonists |
| GB1513742.5 | 2015-08-03 | ||
| PCT/GB2016/052386 WO2017021730A1 (en) | 2015-08-03 | 2016-08-03 | Muscarinic agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018522032A JP2018522032A (ja) | 2018-08-09 |
| JP2018522032A5 true JP2018522032A5 (https=) | 2019-08-29 |
| JP6876675B2 JP6876675B2 (ja) | 2021-05-26 |
Family
ID=54063148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018504985A Active JP6876675B2 (ja) | 2015-08-03 | 2016-08-03 | ムスカリンアゴニスト |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US9758506B2 (https=) |
| EP (2) | EP3331869B1 (https=) |
| JP (1) | JP6876675B2 (https=) |
| KR (1) | KR102664558B1 (https=) |
| CN (1) | CN107949558B (https=) |
| AR (1) | AR105593A1 (https=) |
| AU (1) | AU2016302048B2 (https=) |
| BR (1) | BR112018002279B1 (https=) |
| CA (1) | CA2993484C (https=) |
| CL (1) | CL2018000292A1 (https=) |
| CO (1) | CO2018002060A2 (https=) |
| DK (1) | DK3331869T3 (https=) |
| ES (2) | ES2850298T3 (https=) |
| GB (1) | GB201513742D0 (https=) |
| IL (1) | IL257064A (https=) |
| MX (1) | MX379530B (https=) |
| MY (1) | MY195244A (https=) |
| PH (1) | PH12018500259A1 (https=) |
| RU (1) | RU2737158C2 (https=) |
| TW (1) | TWI723037B (https=) |
| UA (1) | UA123315C2 (https=) |
| WO (1) | WO2017021730A1 (https=) |
| ZA (1) | ZA201800715B (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012338581B2 (en) | 2011-11-18 | 2016-12-08 | Nxera Pharma Uk Limited | Muscarinic M1 receptor agonists |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| PE20181366A1 (es) | 2015-08-03 | 2018-08-27 | Bristol Myers Squibb Co | Compuestos heterociclicos utiles como moduladores de factor de necrosis tumoral (tnf) alfa |
| CN108026050B (zh) | 2015-08-03 | 2021-04-30 | 格兰马克药品股份有限公司 | 作为RORγ调节剂的新型化合物 |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201513742D0 (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 |
| 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 |
| US10329289B2 (en) | 2015-12-23 | 2019-06-25 | Merck Sharp & Dohme Corp. | 6,7-dihydro-5H-pyrrolo[3,4-B]pyridin-5-one allosteric modulators of the M4 muscarinic acetylcholine receptor |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| 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 |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2019000237A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000238A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | 5- (PYRIDIN-3-YL) OXAZOLE ALLOSTERIC MODULATORS OF M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| WO2019000236A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | ALLOSTERIC MODULATORS OF 3- (1H-PYRAZOL-4-YL) PYRIDINE FROM THE M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| US12600726B2 (en) | 2017-07-12 | 2026-04-14 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| 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 |
| WO2019079410A1 (en) | 2017-10-17 | 2019-04-25 | Vanderbilt University | ANTAGONISTS OF THE MUSCARINIC RECEPTOR OF ACETYLCHOLINE M4 |
| IL310346A (en) | 2017-10-20 | 2024-03-01 | Univ Vanderbilt | Muscarinic acetylcholine M4 receptor antagonists |
| EP3732163A4 (en) * | 2017-12-20 | 2021-07-14 | Vanderbilt University | MUSCARIN M4 ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| EP4219464A1 (en) | 2018-03-23 | 2023-08-02 | Pfizer Inc. | Piperazine azaspiro derivaves |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201810245D0 (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 |
| KR20220079921A (ko) * | 2019-10-09 | 2022-06-14 | 노파르티스 아게 | M4 작용제로서의 2-아자스피로[3.4]옥탄 유도체 |
| PE20221454A1 (es) | 2019-10-09 | 2022-09-21 | Novartis Ag | Derivados de 2-azaespiro[3.4]octano como agonistas de m4 |
| WO2023114224A1 (en) | 2021-12-13 | 2023-06-22 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ570497A (en) * | 2006-02-22 | 2011-09-30 | Vertex Pharma | Spiro condensed 4,4'-quinilino-piperidines derivatives as modulators of muscarinic receptors |
| UY31672A1 (es) * | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| US20130197027A1 (en) * | 2010-03-10 | 2013-08-01 | Craig Lindsley | Heterocyclyl-azabicyclo[3.2.1]octane analogs as selective m1 agonists and methods of making and using same |
| AU2012338581B2 (en) * | 2011-11-18 | 2016-12-08 | Nxera Pharma Uk Limited | Muscarinic M1 receptor agonists |
| BR112015006029B1 (pt) * | 2012-09-18 | 2022-01-25 | Heptares Therapeutics Limited | Compostos aza bicíclicos como agonistas de receptor m1 muscarínicos, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou distúrbio psicótico ou para tratar ou reduzir a gravidade de dores agudas, crônicas, neuropáticas ou inflamatórias |
| KR102352388B1 (ko) | 2014-02-06 | 2022-01-17 | 헵테얼즈 테라퓨틱스 리미티드 | 무스카린성 m1 수용체 및/또는 m4 수용체 작용제로서 바이사이클릭 아자 화합물 |
| PE20181366A1 (es) | 2015-08-03 | 2018-08-27 | Bristol Myers Squibb Co | Compuestos heterociclicos utiles como moduladores de factor de necrosis tumoral (tnf) alfa |
| CN108026050B (zh) | 2015-08-03 | 2021-04-30 | 格兰马克药品股份有限公司 | 作为RORγ调节剂的新型化合物 |
| GB201513742D0 (en) * | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| AR105556A1 (es) | 2015-08-03 | 2017-10-18 | Hoffmann La Roche | Derivados de etinilo |
-
2015
- 2015-08-03 GB GBGB1513742.5A patent/GB201513742D0/en not_active Ceased
-
2016
- 2016-08-03 MX MX2018001564A patent/MX379530B/es unknown
- 2016-08-03 TW TW105124670A patent/TWI723037B/zh active
- 2016-08-03 JP JP2018504985A patent/JP6876675B2/ja active Active
- 2016-08-03 CA CA2993484A patent/CA2993484C/en active Active
- 2016-08-03 US US15/227,325 patent/US9758506B2/en active Active
- 2016-08-03 ES ES16750223T patent/ES2850298T3/es active Active
- 2016-08-03 BR BR112018002279-9A patent/BR112018002279B1/pt active IP Right Grant
- 2016-08-03 RU RU2018105020A patent/RU2737158C2/ru active
- 2016-08-03 AR ARP160102378A patent/AR105593A1/es unknown
- 2016-08-03 KR KR1020187006156A patent/KR102664558B1/ko active Active
- 2016-08-03 MY MYPI2018000148A patent/MY195244A/en unknown
- 2016-08-03 UA UAA201801267A patent/UA123315C2/uk unknown
- 2016-08-03 DK DK16750223.6T patent/DK3331869T3/da active
- 2016-08-03 CN CN201680043661.XA patent/CN107949558B/zh active Active
- 2016-08-03 EP EP16750223.6A patent/EP3331869B1/en active Active
- 2016-08-03 AU AU2016302048A patent/AU2016302048B2/en active Active
- 2016-08-03 ES ES20213929T patent/ES2980578T3/es active Active
- 2016-08-03 EP EP20213929.1A patent/EP3822262B1/en active Active
- 2016-08-03 WO PCT/GB2016/052386 patent/WO2017021730A1/en not_active Ceased
-
2017
- 2017-09-08 US US15/699,674 patent/US10351545B2/en active Active
-
2018
- 2018-01-21 IL IL257064A patent/IL257064A/en unknown
- 2018-02-01 US US15/886,057 patent/US10167272B2/en active Active
- 2018-02-01 CL CL2018000292A patent/CL2018000292A1/es unknown
- 2018-02-02 ZA ZA2018/00715A patent/ZA201800715B/en unknown
- 2018-02-02 PH PH12018500259A patent/PH12018500259A1/en unknown
- 2018-02-26 CO CONC2018/0002060A patent/CO2018002060A2/es unknown
-
2019
- 2019-05-21 US US16/418,354 patent/US11091456B2/en active Active
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