JP2019077725A5 - - Google Patents
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- Publication number
- JP2019077725A5 JP2019077725A5 JP2019017086A JP2019017086A JP2019077725A5 JP 2019077725 A5 JP2019077725 A5 JP 2019077725A5 JP 2019017086 A JP2019017086 A JP 2019017086A JP 2019017086 A JP2019017086 A JP 2019017086A JP 2019077725 A5 JP2019077725 A5 JP 2019077725A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- ethyl
- azaspiro
- 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 21
- 150000003839 salts Chemical class 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- HZMNRFTWMDFPNO-UHFFFAOYSA-N ethyl 2-(4-pyrazol-1-ylpiperidin-1-yl)-6-azaspiro[3.4]octane-6-carboxylate Chemical compound N1(N=CC=C1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC HZMNRFTWMDFPNO-UHFFFAOYSA-N 0.000 claims 1
- HEJAEKBVOZHTRA-UHFFFAOYSA-N ethyl 2-[4-(2-methylpyrazol-3-yl)piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound CN1N=CC=C1C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC HEJAEKBVOZHTRA-UHFFFAOYSA-N 0.000 claims 1
- QZVYLGBTRSXKIE-UHFFFAOYSA-N ethyl 2-[4-(2-oxopyrrolidin-1-yl)piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound O=C1N(CCC1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC QZVYLGBTRSXKIE-UHFFFAOYSA-N 0.000 claims 1
- QKTXQEYKBXLLNQ-TVRKMHQQSA-N ethyl 2-[4-[(2R)-4,4-difluoro-2-(hydroxymethyl)pyrrolidin-1-yl]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound FC1(C[C@@H](N(C1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CO)F QKTXQEYKBXLLNQ-TVRKMHQQSA-N 0.000 claims 1
- BOEACPBYTRPLBC-UORCXSCMSA-N ethyl 2-[4-[(2R,4R)-4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound F[C@@H]1C[C@@H](N(C1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CO BOEACPBYTRPLBC-UORCXSCMSA-N 0.000 claims 1
- BOEACPBYTRPLBC-JQZVFVSYSA-N ethyl 2-[4-[(2R,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidin-1-yl]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound F[C@H]1C[C@@H](N(C1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)CO BOEACPBYTRPLBC-JQZVFVSYSA-N 0.000 claims 1
- XBYWKKNGSJNKJG-JJXOGSGTSA-N ethyl 2-[4-[(2R,4S)-4-fluoro-2-methoxycarbonylpyrrolidin-1-yl]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound F[C@H]1C[C@@H](N(C1)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC)C(=O)OC XBYWKKNGSJNKJG-JJXOGSGTSA-N 0.000 claims 1
- IKKKUWUFDRRBSC-AFJQURTJSA-N ethyl 2-[4-[(2S)-2-ethyl-5-oxopyrrolidin-1-yl]piperidin-1-yl]-6-azaspiro[3.4]octane-6-carboxylate Chemical compound C(C)[C@@H]1N(C(CC1)=O)C1CCN(CC1)C1CC2(C1)CN(CC2)C(=O)OCC IKKKUWUFDRRBSC-AFJQURTJSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- -1 hydroxy, methoxy, methyl Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000002981 neuropathic effect Effects 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 0 C*(C)C(CCC1)N1C(C(F)(F)F)=O Chemical compound C*(C)C(CCC1)N1C(C(F)(F)F)=O 0.000 description 17
- ZAVNAIXXOHWBDG-UHFFFAOYSA-N CC(CCC1)N1C(CC(F)(F)F)=O Chemical compound CC(CCC1)N1C(CC(F)(F)F)=O ZAVNAIXXOHWBDG-UHFFFAOYSA-N 0.000 description 1
- YQSRKFAOUYPUAC-UHFFFAOYSA-N CC(CCC1)N1C(CCN)=O Chemical compound CC(CCC1)N1C(CCN)=O YQSRKFAOUYPUAC-UHFFFAOYSA-N 0.000 description 1
- FMOMSFCVAGTHGO-UHFFFAOYSA-N CC(CCC1)N1C(COC)=O Chemical compound CC(CCC1)N1C(COC)=O FMOMSFCVAGTHGO-UHFFFAOYSA-N 0.000 description 1
- VXQOOMPIHVLABQ-UHFFFAOYSA-N CC(CCC1)N1C(NC1CCC1)=O Chemical compound CC(CCC1)N1C(NC1CCC1)=O VXQOOMPIHVLABQ-UHFFFAOYSA-N 0.000 description 1
- PJVFUINVNVDZBV-UHFFFAOYSA-N CC(CCC1)N1C(OC1CCC1)=O Chemical compound CC(CCC1)N1C(OC1CCC1)=O PJVFUINVNVDZBV-UHFFFAOYSA-N 0.000 description 1
- GBKJBXGCDXMHPY-UHFFFAOYSA-N CC1N(COCCN(C)C)CCC1 Chemical compound CC1N(COCCN(C)C)CCC1 GBKJBXGCDXMHPY-UHFFFAOYSA-N 0.000 description 1
- LCXFKHBYVGVYGH-UHFFFAOYSA-N CCC(CCC1)N1C(C1CC1)=O Chemical compound CCC(CCC1)N1C(C1CC1)=O LCXFKHBYVGVYGH-UHFFFAOYSA-N 0.000 description 1
- UZOZSUUBKDDEPD-MLWJPKLSSA-N CCC(N(C1)C(C)C[C@@H]1F)=O Chemical compound CCC(N(C1)C(C)C[C@@H]1F)=O UZOZSUUBKDDEPD-MLWJPKLSSA-N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1402013.5A GB201402013D0 (en) | 2014-02-06 | 2014-02-06 | Pharmaceutical compounds |
| GB1402013.5 | 2014-02-06 | ||
| GBGB1416622.7A GB201416622D0 (en) | 2014-09-19 | 2014-09-19 | Pharmaceutical compounds |
| GB1416622.7 | 2014-09-19 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016550483A Division JP6479029B2 (ja) | 2014-02-06 | 2015-02-06 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020168341A Division JP2021006571A (ja) | 2014-02-06 | 2020-10-05 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019077725A JP2019077725A (ja) | 2019-05-23 |
| JP2019077725A5 true JP2019077725A5 (https=) | 2019-09-26 |
| JP6774513B2 JP6774513B2 (ja) | 2020-10-28 |
Family
ID=52465550
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016550483A Active JP6479029B2 (ja) | 2014-02-06 | 2015-02-06 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2019017086A Active JP6774513B2 (ja) | 2014-02-06 | 2019-02-01 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2020168341A Withdrawn JP2021006571A (ja) | 2014-02-06 | 2020-10-05 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023060030A Active JP7652829B2 (ja) | 2014-02-06 | 2023-04-03 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023076024A Active JP7652832B2 (ja) | 2014-02-06 | 2023-05-02 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023076025A Active JP7652833B2 (ja) | 2014-02-06 | 2023-05-02 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2025041135A Pending JP2025085736A (ja) | 2014-02-06 | 2025-03-14 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016550483A Active JP6479029B2 (ja) | 2014-02-06 | 2015-02-06 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020168341A Withdrawn JP2021006571A (ja) | 2014-02-06 | 2020-10-05 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023060030A Active JP7652829B2 (ja) | 2014-02-06 | 2023-04-03 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023076024A Active JP7652832B2 (ja) | 2014-02-06 | 2023-05-02 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2023076025A Active JP7652833B2 (ja) | 2014-02-06 | 2023-05-02 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
| JP2025041135A Pending JP2025085736A (ja) | 2014-02-06 | 2025-03-14 | ムスカリンｍ１受容体アゴニストとしての二環式アザ化合物 |
Country Status (30)
| Country | Link |
|---|---|
| US (6) | US9670183B2 (https=) |
| EP (4) | EP3102568B1 (https=) |
| JP (7) | JP6479029B2 (https=) |
| KR (1) | KR102352388B1 (https=) |
| CN (2) | CN109851610B (https=) |
| AU (3) | AU2015213900B2 (https=) |
| BR (1) | BR112016017979B1 (https=) |
| CA (1) | CA2938169C (https=) |
| CL (1) | CL2016001983A1 (https=) |
| CY (1) | CY1120834T1 (https=) |
| DK (2) | DK3102568T3 (https=) |
| ES (2) | ES2986327T3 (https=) |
| FI (1) | FI3406609T3 (https=) |
| HR (2) | HRP20241145T1 (https=) |
| HU (1) | HUE068301T2 (https=) |
| IL (1) | IL247117B (https=) |
| LT (2) | LT3102568T (https=) |
| MX (2) | MX371529B (https=) |
| NZ (1) | NZ723103A (https=) |
| PH (1) | PH12016501570A1 (https=) |
| PL (2) | PL3102568T3 (https=) |
| PT (2) | PT3102568T (https=) |
| RS (2) | RS57843B1 (https=) |
| RU (1) | RU2685230C2 (https=) |
| SA (1) | SA516371614B1 (https=) |
| SG (1) | SG11201606269WA (https=) |
| SI (2) | SI3406609T1 (https=) |
| SM (1) | SMT202400446T1 (https=) |
| UA (1) | UA122121C2 (https=) |
| WO (1) | WO2015118342A1 (https=) |
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| EP2780015B1 (en) | 2011-11-18 | 2017-01-04 | Heptares Therapeutics Limited | Muscarinic m1 receptor agonists |
| LT2968297T (lt) | 2013-03-15 | 2019-01-10 | Verseon Corporation | Multipakeistieji aromatiniai junginiai kaip serino proteazės inhibitoriai |
| SG11201606269WA (en) | 2014-02-06 | 2016-09-29 | Heptares Therapeutics Ltd | Bicyclic aza compounds as muscarinic m1 receptor and/or m4 receptor agonists |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| CN106687445A (zh) | 2014-09-17 | 2017-05-17 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的吡唑基取代的吡啶酮化合物 |
| RU2017131562A (ru) | 2015-02-27 | 2019-03-27 | Версеон Корпорейшн | Замещенные пиразольные соединения как ингибиторы сериновых протеаз |
| GB201504675D0 (en) | 2015-03-19 | 2015-05-06 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| 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 |
| 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 |
| TW201726675A (zh) | 2015-12-23 | 2017-08-01 | 默沙東藥廠 | M4毒蕈鹼乙醯膽鹼受體之異位調節劑6,7-二氫-5h-吡咯并[3,4-b]吡啶-5-酮 |
| 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 |
| PT3478679T (pt) | 2016-07-01 | 2021-06-30 | Pfizer | Derivados de 5,7-dihidro-pirrolo-piridina para o tratamento de doenças neurológicas e neurodegenerativas |
| 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 |
| US11274100B2 (en) | 2017-06-21 | 2022-03-15 | Daiichi Sankyo Company, Limited | EP300/CREBBP inhibitor |
| 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 |
| 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 |
| AU2018300980A1 (en) | 2017-07-12 | 2020-01-02 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| WO2019027860A1 (en) * | 2017-08-01 | 2019-02-07 | Boehringer Ingelheim International Gmbh | INTERMEDIATE COMPOUNDS AND METHODS |
| IL273924B2 (en) | 2017-10-20 | 2024-07-01 | Univ Vanderbilt | Antagonists of the muscarinic acetylcholine receptor m4 |
| US10501483B2 (en) | 2017-10-24 | 2019-12-10 | Allergan, Inc. | Enamines and diastereo-selective reduction of enamines |
| WO2019126559A1 (en) | 2017-12-20 | 2019-06-27 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| PT3768669T (pt) * | 2018-03-23 | 2023-04-24 | Pfizer | Derivados de piperazina azaspiro |
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| US11912705B2 (en) * | 2020-08-20 | 2024-02-27 | The Corporation Of Mercer University | Cathinone derivatives, pharmaceutical formulations, and methods |
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| WO2026050231A1 (en) | 2024-08-27 | 2026-03-05 | Neurocrine Biosciences, Inc. | Method of treating a bipolar disorder |
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| AU2007226715A1 (en) * | 2006-03-03 | 2007-09-20 | Novartis Ag | N-formyl hydroxylamine compounds |
| GB0706188D0 (en) * | 2007-03-29 | 2007-05-09 | Glaxo Group Ltd | Compounds |
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| MX2011004340A (es) | 2008-10-29 | 2011-05-23 | Gruenenthal Gmbh | Espiroaminas sustituidas. |
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| PE20170937A1 (es) | 2014-09-19 | 2017-07-13 | Glaxosmithkline Ip Dev Ltd | Nuevos activadores de la guanilato ciclasa soluble y su uso |
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