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
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- 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 |
|---|---|---|---|
| GB1402013.5 | 2014-02-06 | ||
| GBGB1402013.5A GB201402013D0 (en) | 2014-02-06 | 2014-02-06 | Pharmaceutical compounds |
| GB1416622.7 | 2014-09-19 | ||
| GBGB1416622.7A GB201416622D0 (en) | 2014-09-19 | 2014-09-19 | Pharmaceutical compounds |
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 (cg-RX-API-DMAC10.html) | 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)
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| IN2014KN01075A (cg-RX-API-DMAC10.html) | 2011-11-18 | 2015-10-09 | Heptares Therapeutics Ltd | |
| BR112015022340A2 (pt) | 2013-03-15 | 2017-07-18 | Verseon Corp | método para tratamento ou prevenção de uma doença ou distúrbio relacionado à calicreína em um sujeito, composto, e, composição farmacêutica |
| RS57843B1 (sr) * | 2014-02-06 | 2018-12-31 | Heptares Therapeutics Ltd | Biciklična aza jedinjenja kao agonisti muskarinskog receptora m1 |
| 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 |
| 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 |
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| 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 |
| WO2017112719A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 6,7-dihydro-5h-pyrrolo[3,4-b]pyridin-5-one allosteric modulators of the m4 muscarinic acetylcholine receptor |
| SG11201811712QA (en) * | 2016-07-01 | 2019-01-30 | Pfizer | 5,7-dihydro-pyrrolo-pyridine derivatives for treating neurological and neurodegenerative diseases |
| 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 |
| GB201709652D0 (en) * | 2017-06-16 | 2017-08-02 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| TW201906838A (zh) | 2017-06-21 | 2019-02-16 | 日商第一三共股份有限公司 | Ｅｐ３００／ｃｒｅｂｂｐ抑制劑 |
| 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 |
| 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 |
| WO2019000238A1 (en) | 2017-06-27 | 2019-01-03 | Merck Sharp & Dohme Corp. | 5- (PYRIDIN-3-YL) OXAZOLE ALLOSTERIC MODULATORS OF M4 ACETYLCHOLINE MUSCARINIC RECEPTOR |
| US20200369611A1 (en) * | 2017-08-01 | 2020-11-26 | Boehringer Ingelheim International Gmbh | Intermediate compounds and methods |
| TW201922758A (zh) | 2017-10-24 | 2019-06-16 | 美商歐樂根公司 | 烯胺及烯胺的非鏡像選擇性還原 |
| US11325896B2 (en) | 2017-12-20 | 2022-05-10 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| CA3094366A1 (en) * | 2018-03-23 | 2019-09-26 | Pfizer Inc. | Piperazine azaspiro derivatives |
| 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 |
| PE20221453A1 (es) | 2019-10-09 | 2022-09-21 | Novartis Ag | Derivados de 2-azaspiro[3,4]octano como agonistas de m4 |
| AU2020364186B2 (en) * | 2019-10-09 | 2023-11-30 | Novartis Ag | 5-oxa-2-azaspiro(3.4)octane derivatives as M4 agonists |
| EP4069367B1 (en) | 2019-12-06 | 2024-05-15 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| EP4100410A1 (en) * | 2020-02-05 | 2022-12-14 | Neurocrine Biosciences, Inc. | Muscarinic receptor 4 antagonists and methods of use |
| US11912705B2 (en) * | 2020-08-20 | 2024-02-27 | The Corporation Of Mercer University | Cathinone derivatives, pharmaceutical formulations, and methods |
| EP4447953A1 (en) | 2021-12-13 | 2024-10-23 | Sage Therapeutics, Inc. | Combination of muscarinic receptor positive modulators and nmda positive allosteric modulators |
| AR130114A1 (es) | 2022-08-04 | 2024-11-06 | Heptares Therapeutics Ltd | Agonistas de receptores muscarínicos |
| WO2024059249A1 (en) * | 2022-09-16 | 2024-03-21 | Cerevel Therapeutics, Llc | M4 activators/modulators and uses thereof |
| EP4649077A1 (en) * | 2023-01-12 | 2025-11-19 | Cerevel Therapeutics, LLC | Spiro derivatives as m4 activators/modulators and uses thereof |
| CN120569376A (zh) * | 2023-01-24 | 2025-08-29 | 纽罗克里生物科学有限公司 | 氘代化合物 |
| CN116496195A (zh) * | 2023-05-10 | 2023-07-28 | 南京优氟医药科技有限公司 | 一种（r）-4,4-二氟代吡咯烷-2-羧酸的制备方法 |
| WO2025030095A1 (en) | 2023-08-03 | 2025-02-06 | Neurocrine Biosciences, Inc. | Methods of synthesis |
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2015
- 2015-02-06 RS RS20181127A patent/RS57843B1/sr unknown
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