JP2020502063A5 - - Google Patents
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- Publication number
- JP2020502063A5 JP2020502063A5 JP2019526621A JP2019526621A JP2020502063A5 JP 2020502063 A5 JP2020502063 A5 JP 2020502063A5 JP 2019526621 A JP2019526621 A JP 2019526621A JP 2019526621 A JP2019526621 A JP 2019526621A JP 2020502063 A5 JP2020502063 A5 JP 2020502063A5
- Authority
- JP
- Japan
- Prior art keywords
- benzopyran
- dihydro
- alkyl
- compound
- trans
- 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, hydroxyl Chemical group 0.000 claims 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 24
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 229920006395 saturated elastomer Polymers 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 11
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 11
- 239000000556 agonist Substances 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 claims 5
- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 claims 5
- 150000000660 7-membered heterocyclic compounds Chemical class 0.000 claims 5
- 150000000643 6-membered carbocyclic compounds Chemical class 0.000 claims 4
- 150000000659 7-membered carbocyclic compounds Chemical class 0.000 claims 4
- 208000007848 Alcoholism Diseases 0.000 claims 4
- 206010011878 Deafness Diseases 0.000 claims 4
- 206010057852 Nicotine dependence Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 208000009205 Tinnitus Diseases 0.000 claims 4
- 208000025569 Tobacco Use disease Diseases 0.000 claims 4
- 208000029560 autism spectrum disease Diseases 0.000 claims 4
- 206010013663 drug dependence Diseases 0.000 claims 4
- 230000010370 hearing loss Effects 0.000 claims 4
- 231100000888 hearing loss Toxicity 0.000 claims 4
- 208000016354 hearing loss disease Diseases 0.000 claims 4
- 230000003957 neurotransmitter release Effects 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 208000011117 substance-related disease Diseases 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 150000000537 4-membered heterocyclic compounds Chemical class 0.000 claims 3
- 150000000564 5-membered carbocyclic compounds Chemical class 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000000502 3-membered carbocyclic compounds Chemical class 0.000 claims 2
- 150000000536 4-membered carbocyclic compounds Chemical class 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010003805 Autism Diseases 0.000 claims 2
- 208000020706 Autistic disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 230000009530 GABAergic signaling pathway Effects 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 claims 2
- 102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 claims 2
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims 2
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims 2
- 208000012471 X-linked intellectual disability Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 230000003281 allosteric effect Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 claims 2
- 230000009206 glutamatergic signaling Effects 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 201000010901 lateral sclerosis Diseases 0.000 claims 2
- 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 claims 2
- 108010038448 metabotropic glutamate receptor 8 Proteins 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 210000003205 muscle Anatomy 0.000 claims 2
- 239000002858 neurotransmitter agent Substances 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 208000031906 susceptibility to X-linked 2 autism Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- QWQSNYIPDQFUAK-BVYCBKJFSA-N (1S)-2-(3-fluoropropyl)-N-[(3R,4R)-4-methoxy-3,4-dihydro-2H-chromen-3-yl]-3-oxo-1,4-dihydroisoquinoline-1-carboxamide Chemical compound FCCCN1[C@@H](C2=CC=CC=C2CC1=O)C(=O)N[C@@H]1COC2=C([C@H]1OC)C=CC=C2 QWQSNYIPDQFUAK-BVYCBKJFSA-N 0.000 claims 1
- HQTSLTMZHSQONT-SFVWDYPZSA-N (2S)-N-(4-oxo-2,3-dihydrochromen-3-yl)-2-phenylpropanamide Chemical compound O=C1C(COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O HQTSLTMZHSQONT-SFVWDYPZSA-N 0.000 claims 1
- FLTBOZYGVSRIHV-XGWLTEMNSA-N (2S)-N-[(3R,4R)-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound O[C@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O FLTBOZYGVSRIHV-XGWLTEMNSA-N 0.000 claims 1
- FYJVPDIPCFSONK-FDQGKXFDSA-N (2S)-N-[(3R,4R)-4-methoxy-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound CO[C@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O FYJVPDIPCFSONK-FDQGKXFDSA-N 0.000 claims 1
- CDQZZCHPOLEVMS-FDQGKXFDSA-N (2S)-N-[(3R,4R)-4-methylsulfonyl-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound CS(=O)(=O)[C@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O CDQZZCHPOLEVMS-FDQGKXFDSA-N 0.000 claims 1
- FLTBOZYGVSRIHV-MJEQTWJJSA-N (2S)-N-[(3R,4S)-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound O[C@@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O FLTBOZYGVSRIHV-MJEQTWJJSA-N 0.000 claims 1
- BQSCKAGEIGVVHB-CXMBCZLWSA-N (2S)-N-[(3R,4S)-6-fluoro-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound FC=1C=CC2=C([C@@H]([C@@H](CO2)NC([C@@H](C)C2=CC=CC=C2)=O)O)C=1 BQSCKAGEIGVVHB-CXMBCZLWSA-N 0.000 claims 1
- DWHRIEUCCQEPTN-FDQGKXFDSA-N (2S)-N-[(3S,4R)-4-(methylamino)-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound CN[C@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O DWHRIEUCCQEPTN-FDQGKXFDSA-N 0.000 claims 1
- DWHRIEUCCQEPTN-XCRHUMRWSA-N (2S)-N-[(3S,4S)-4-(methylamino)-3,4-dihydro-2H-chromen-3-yl]-2-phenylpropanamide Chemical compound CN[C@@H]1[C@@H](COC2=C1C=CC=C2)NC([C@@H](C)C1=CC=CC=C1)=O DWHRIEUCCQEPTN-XCRHUMRWSA-N 0.000 claims 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- DNDJRJRRHJPBOU-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-dicarboxamide Chemical compound C1(C(C=CC=C1)C(=O)N)(C)C(=O)N DNDJRJRRHJPBOU-UHFFFAOYSA-N 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
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- GBXQDCYLIGEJOA-TYIXABJVSA-N N-[(3R,4R)-4-methoxy-3,4-dihydro-2H-chromen-3-yl]-2-(oxan-4-ylmethyl)-3-oxo-1,4-dihydroisoquinoline-1-carboxamide Chemical compound CO[C@H]1[C@@H](COC2=C1C=CC=C2)NC(=O)C1N(C(CC2=CC=CC=C12)=O)CC1CCOCC1 GBXQDCYLIGEJOA-TYIXABJVSA-N 0.000 claims 1
- UBKWBSQNCGCPDH-TYIXABJVSA-N N-[(3R,4R)-4-methoxy-3,4-dihydro-2H-chromen-3-yl]-3-oxo-2-(pyridin-2-ylmethyl)-1,4-dihydroisoquinoline-1-carboxamide Chemical compound CO[C@H]1[C@@H](COC2=C1C=CC=C2)NC(=O)C1N(C(CC2=CC=CC=C12)=O)CC1=NC=CC=C1 UBKWBSQNCGCPDH-TYIXABJVSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1619514.1 | 2016-11-18 | ||
| GBGB1619514.1A GB201619514D0 (en) | 2016-11-18 | 2016-11-18 | Novel compounds |
| US201762566832P | 2017-10-02 | 2017-10-02 | |
| US62/566,832 | 2017-10-02 | ||
| PCT/JP2017/042308 WO2018092921A1 (en) | 2016-11-18 | 2017-11-17 | Mglur7 agonist compounds for treating mglur7- regulated diseases, disorders, or conditions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020502063A JP2020502063A (ja) | 2020-01-23 |
| JP2020502063A5 true JP2020502063A5 (enExample) | 2020-12-24 |
| JP7048601B2 JP7048601B2 (ja) | 2022-04-05 |
Family
ID=57993991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019526621A Active JP7048601B2 (ja) | 2016-11-18 | 2017-11-17 | ｍＧｌｕＲ７調節疾患、障害、または病状を処置するためのｍＧｌｕＲ７アゴニスト化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11465994B2 (enExample) |
| EP (1) | EP3541812B1 (enExample) |
| JP (1) | JP7048601B2 (enExample) |
| GB (1) | GB201619514D0 (enExample) |
| WO (1) | WO2018092921A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2020270992B2 (en) | 2019-04-12 | 2025-10-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | D3 receptor agonist compounds; methods of preparation; intermediates thereof; and methods of use thereof |
| CN111004198B (zh) * | 2019-12-24 | 2023-03-28 | 瑞安宝源化工有限公司 | 一种苯并吡喃衍生物的合成方法 |
| WO2024040266A2 (en) * | 2022-08-19 | 2024-02-22 | Mitokinin, Inc. | Disubstituted benzoimidazole and indole analogs as modulators of pink1 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3708962B2 (ja) | 1994-08-24 | 2005-10-19 | アストラゼネカ・アクチエボラーグ | 治療に有用なスピロ−アザ二環式化合物 |
| JPH11503116A (ja) * | 1995-03-27 | 1999-03-23 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 二環式アミン誘導体および抗精神病薬としてのそれらの使用 |
| SE9504661D0 (sv) | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| AR013184A1 (es) | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9702799D0 (sv) | 1997-07-25 | 1997-07-25 | Astra Ab | New compounds |
| SE9900100D0 (sv) | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| SE9903760D0 (sv) | 1999-10-18 | 1999-10-18 | Astra Ab | New compounds |
| SE9904176D0 (sv) | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
| SE0000540D0 (sv) | 2000-02-18 | 2000-02-18 | Astrazeneca Ab | New compounds |
| SE0002729D0 (sv) | 2000-07-20 | 2000-07-20 | Astrazeneca Ab | Novel compound form |
| WO2002094794A1 (en) | 2001-05-18 | 2002-11-28 | Astrazeneca Ab | 4 (phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain anxiety or gastrointestinal disorders |
| ES2280538T3 (es) | 2001-06-01 | 2007-09-16 | Astrazeneca Ab | Nuevo ligando para receptores nicotinicos de acetilcolina utiles en terapia. |
| BR0309342A (pt) | 2002-04-18 | 2005-02-15 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, método de tratamento ou profilaxia de doenças ou condições humanas |
| MXPA04010190A (es) | 2002-04-18 | 2005-02-03 | Astrazeneca Ab | Compuestos heterociclicos. |
| DE60334536D1 (de) | 2002-04-18 | 2010-11-25 | Astrazeneca Ab | Furylverbindungen |
| SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| SE0202465D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| SE0202598D0 (sv) | 2002-09-02 | 2002-09-02 | Astrazeneca Ab | Alpha-7 Nicotinic receptor agonists and statins in combination |
| GB0517740D0 (en) | 2005-08-31 | 2005-10-12 | Novartis Ag | Organic compounds |
| CN107207476B (zh) | 2014-12-15 | 2021-03-19 | 默克专利有限公司 | 吲哚和氮杂吲哚衍生物及其用于神经退化性疾病中的用途 |
-
2016
- 2016-11-18 GB GBGB1619514.1A patent/GB201619514D0/en not_active Ceased
-
2017
- 2017-11-17 WO PCT/JP2017/042308 patent/WO2018092921A1/en not_active Ceased
- 2017-11-17 EP EP17817201.1A patent/EP3541812B1/en active Active
- 2017-11-17 US US16/461,427 patent/US11465994B2/en active Active
- 2017-11-17 JP JP2019526621A patent/JP7048601B2/ja active Active
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