JP2019530725A5 - - Google Patents
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- Publication number
- JP2019530725A5 JP2019530725A5 JP2019520420A JP2019520420A JP2019530725A5 JP 2019530725 A5 JP2019530725 A5 JP 2019530725A5 JP 2019520420 A JP2019520420 A JP 2019520420A JP 2019520420 A JP2019520420 A JP 2019520420A JP 2019530725 A5 JP2019530725 A5 JP 2019530725A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- cyclohexane
- cyano
- diazepan
- dihydrospiro
- 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
- -1 cyano, hydroxy, amino Chemical group 0.000 claims 50
- 150000003839 salts Chemical class 0.000 claims 39
- 150000001875 compounds Chemical class 0.000 claims 38
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 27
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- LLHRWZOIAVWPKH-UHFFFAOYSA-N spiro[1h-indole-3,1'-cyclohexane]-2-one Chemical compound O=C1NC2=CC=CC=C2C11CCCCC1 LLHRWZOIAVWPKH-UHFFFAOYSA-N 0.000 claims 3
- WVAVALYHMUJZPG-UHFFFAOYSA-N spiro[cyclohexane-1,3'-indole] Chemical compound C1CCCCC21C1=CC=CC=C1N=C2 WVAVALYHMUJZPG-UHFFFAOYSA-N 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 230000001272 neurogenic effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical class C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- ARCSBFATIFHVTF-UHFFFAOYSA-N 3-ethyl-1,2,4-oxadiazole Chemical compound CCC=1N=CON=1 ARCSBFATIFHVTF-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- ZTMLEOCMWMGOHV-ZLSHJHNNSA-N 4'-[[(1R,3S)-3-[3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl]cyclopentyl]amino]spiro[1H-indole-3,1'-cyclohexane]-2-one Chemical compound FC(C1=NOC(=N1)[C@@H]1C[C@@H](CC1)NC1CCC2(C(NC3=CC=CC=C23)=O)CC1)(F)F ZTMLEOCMWMGOHV-ZLSHJHNNSA-N 0.000 claims 1
- RZXRTMBVAYMUON-RPTYLJJZSA-N 4-[[(1R,3S)-3-(3-methyl-1,2,4-oxadiazol-5-yl)cyclopentyl]amino]-1-pyridin-2-ylcyclohexane-1-carbonitrile Chemical compound CC1=NOC(=N1)[C@@H]1C[C@@H](CC1)NC1CCC(CC1)(C#N)C1=NC=CC=C1 RZXRTMBVAYMUON-RPTYLJJZSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 230000007278 cognition impairment 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 230000003551 muscarinic effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662408468P | 2016-10-14 | 2016-10-14 | |
| GB1617454.2 | 2016-10-14 | ||
| US62/408,468 | 2016-10-14 | ||
| GBGB1617454.2A GB201617454D0 (en) | 2016-10-14 | 2016-10-14 | Pharmaceutical compounds |
| PCT/GB2017/053115 WO2018069732A1 (en) | 2016-10-14 | 2017-10-16 | Heterocyclic compounds having activity as modulators of muscarinic m1 and/or m4 receptors in the treatment of cns diseases and pains. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019530725A JP2019530725A (ja) | 2019-10-24 |
| JP2019530725A5 true JP2019530725A5 (cg-RX-API-DMAC7.html) | 2020-11-26 |
| JP7100634B2 JP7100634B2 (ja) | 2022-07-13 |
Family
ID=57680777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019520420A Active JP7100634B2 (ja) | 2016-10-14 | 2017-10-16 | Ｃｎｓ疾患及び疼痛の治療におけるムスカリンｍ１及び／又はｍ４受容体の調節因子として活性を有する複素環式化合物。 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11834407B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3526207B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP7100634B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN109996792B (cg-RX-API-DMAC7.html) |
| DK (1) | DK3526207T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2898206T3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB201617454D0 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018069732A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2780015B1 (en) | 2011-11-18 | 2017-01-04 | Heptares Therapeutics Limited | Muscarinic m1 receptor agonists |
| 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 |
| 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 |
| 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 |
| CN119390705A (zh) | 2019-10-09 | 2025-02-07 | 诺华股份有限公司 | 作为m4激动剂的5-氧杂-2-氮杂螺[3.4]辛烷衍生物 |
| AU2020361735B2 (en) | 2019-10-09 | 2024-04-18 | Novartis Ag | 2-azaspiro(3.4)octane derivatives as M4 agonists |
| CN114728964A (zh) * | 2019-11-22 | 2022-07-08 | 豪夫迈·罗氏有限公司 | 吡咯烷衍生物 |
| BR112023015210A2 (pt) | 2021-01-29 | 2023-11-07 | Cedilla Therapeutics Inc | Inibidores de cdk2 e métodos de uso dos mesmos |
| CN117561058A (zh) | 2021-06-26 | 2024-02-13 | 塞迪拉治疗股份有限公司 | Cdk2抑制剂及其使用方法 |
| WO2025076632A1 (en) * | 2023-10-13 | 2025-04-17 | Fibrocor Therapeutics Inc. | Compounds and uses thereof |
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2016
- 2016-10-14 GB GBGB1617454.2A patent/GB201617454D0/en not_active Ceased
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2017
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- 2017-10-16 DK DK17787581.2T patent/DK3526207T3/da active
- 2017-10-16 CN CN201780073082.4A patent/CN109996792B/zh active Active
- 2017-10-16 EP EP17787581.2A patent/EP3526207B1/en active Active
- 2017-10-16 ES ES17787581T patent/ES2898206T3/es active Active
- 2017-10-16 WO PCT/GB2017/053115 patent/WO2018069732A1/en not_active Ceased
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2021
- 2021-05-03 US US17/306,390 patent/US11834407B2/en active Active
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