JP2020524687A5 - - Google Patents
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- JP2020524687A5 JP2020524687A5 JP2019570547A JP2019570547A JP2020524687A5 JP 2020524687 A5 JP2020524687 A5 JP 2020524687A5 JP 2019570547 A JP2019570547 A JP 2019570547A JP 2019570547 A JP2019570547 A JP 2019570547A JP 2020524687 A5 JP2020524687 A5 JP 2020524687A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- pyridin
- dihydro
- dimethyl
- optionally substituted
- 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 Chemical group 0.000 claims 58
- 150000001204 N-oxides Chemical class 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 37
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 29
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 206010002022 amyloidosis Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- QFQAXYYKZBIRPP-HOTGVXAUSA-N 5,6,7-trimethyl-2-[2-[(1S,2R)-2-pyridin-3-ylcyclopropyl]acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound CN1C(C2=C(C(=C1C)C)CN(C2)C(C[C@H]1[C@@H](C1)C=1C=NC=CC=1)=O)=O QFQAXYYKZBIRPP-HOTGVXAUSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- SDZQJMCXLDSQML-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(1H-pyrazol-4-yl)propan-1-one Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CCC=1C=NNC=1)=O)C SDZQJMCXLDSQML-UHFFFAOYSA-N 0.000 claims 1
- YHVZLWRQGISNQE-UHFFFAOYSA-N 1-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-(4-methoxyphenyl)propan-1-one Chemical compound C1=C(C=CC(=C1)CCC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)OC YHVZLWRQGISNQE-UHFFFAOYSA-N 0.000 claims 1
- MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- YPHCYHOTYHNIMX-UHFFFAOYSA-N 4-[3-[2-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-2-oxoethyl]azetidin-1-yl]pyridine-2-carbonitrile Chemical compound CC1=C(C2=C(C(=N1)NC)CN(C2)C(CC1CN(C1)C1=CC(=NC=C1)C#N)=O)C YPHCYHOTYHNIMX-UHFFFAOYSA-N 0.000 claims 1
- NACFKBRRTJAIRY-UHFFFAOYSA-N 4-[3-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-3-oxopropyl]benzonitrile Chemical compound C1=C(C=CC(=C1)CCC(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1)C#N NACFKBRRTJAIRY-UHFFFAOYSA-N 0.000 claims 1
- YRZUDHYYIUIDIZ-UHFFFAOYSA-N 5,6,7-trimethyl-2-[2-(1-pyridin-3-ylazetidin-3-yl)acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CN=CC=C2)CC(CC(=O)N2CC3=C(C(=O)N(C(=C3C)C)C)C2)C1 YRZUDHYYIUIDIZ-UHFFFAOYSA-N 0.000 claims 1
- MASQMSKSYJLVPR-UHFFFAOYSA-N 5,6,7-trimethyl-2-[2-[1-[2-(trifluoromethyl)pyridin-4-yl]azetidin-3-yl]acetyl]-1,3-dihydropyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CC(C(F)(F)F)=NC=C2)CC(CC(=O)N2CC3=C(C(=O)N(C(=C3C)C)C)C2)C1 MASQMSKSYJLVPR-UHFFFAOYSA-N 0.000 claims 1
- LYYCRODRVBDGRZ-UHFFFAOYSA-N 6,7-dimethyl-2-[2-(1-pyridin-3-ylazetidin-3-yl)acetyl]-3,5-dihydro-1H-pyrrolo[3,4-c]pyridin-4-one Chemical compound N1(C2=CN=CC=C2)CC(CC(=O)N2CC3=C(C(=O)NC(C)=C3C)C2)C1 LYYCRODRVBDGRZ-UHFFFAOYSA-N 0.000 claims 1
- 208000024667 ABeta amyloidosis, Dutch type Diseases 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 102000029797 Prion Human genes 0.000 claims 1
- 108091000054 Prion Proteins 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- MXKFZWRULHJPIV-LLVKDONJSA-N [6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]-[(3R)-oxolan-3-yl]methanone Chemical compound O1CC[C@H](C1)C(=O)N1CC2=C(C(=NC(=C2C)C)NC)C1 MXKFZWRULHJPIV-LLVKDONJSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- FQCIVZDKIPZMHS-UHFFFAOYSA-N cyclopropyl-[6,7-dimethyl-4-(methylamino)-1,3-dihydropyrrolo[3,4-c]pyridin-2-yl]methanone Chemical compound C1(C(=O)N2CC3=C(C(=NC(=C3C2)NC)C)C)CC1 FQCIVZDKIPZMHS-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 125000005879 dioxolanyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013781 dry mouth Diseases 0.000 claims 1
- 208000036536 dutch type ABeta amyloidosis Diseases 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 229960004502 levodopa Drugs 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762523306P | 2017-06-22 | 2017-06-22 | |
| US62/523,306 | 2017-06-22 | ||
| PCT/IB2018/054390 WO2018234953A1 (en) | 2017-06-22 | 2018-06-14 | Dihydro-pyrrolo-pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020524687A JP2020524687A (ja) | 2020-08-20 |
| JP2020524687A5 true JP2020524687A5 (enExample) | 2021-07-26 |
| JP7263266B2 JP7263266B2 (ja) | 2023-04-24 |
Family
ID=62981279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019570547A Active JP7263266B2 (ja) | 2017-06-22 | 2018-06-14 | ジヒドロ－ピロロ－ピリジン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US11198692B2 (enExample) |
| EP (1) | EP3642202B1 (enExample) |
| JP (1) | JP7263266B2 (enExample) |
| KR (1) | KR20200013783A (enExample) |
| CN (1) | CN110944998B (enExample) |
| AU (1) | AU2018287787A1 (enExample) |
| BR (1) | BR112019026955A2 (enExample) |
| CA (1) | CA3066986A1 (enExample) |
| DK (1) | DK3642202T3 (enExample) |
| ES (1) | ES2937236T3 (enExample) |
| FI (1) | FI3642202T3 (enExample) |
| HU (1) | HUE060914T2 (enExample) |
| IL (1) | IL271290B2 (enExample) |
| MX (1) | MX2019015371A (enExample) |
| PL (1) | PL3642202T3 (enExample) |
| PT (1) | PT3642202T (enExample) |
| SG (1) | SG11201913014YA (enExample) |
| TW (1) | TWI680128B (enExample) |
| WO (1) | WO2018234953A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114728964A (zh) * | 2019-11-22 | 2022-07-08 | 豪夫迈·罗氏有限公司 | 吡咯烷衍生物 |
| CN112174869B (zh) * | 2020-10-12 | 2023-04-25 | 蔡霈 | N-苯乙酰基-2-羟甲基吡咯烷-2-甲酰胺的制备方法及其药用用途 |
| CN117946112A (zh) * | 2022-10-28 | 2024-04-30 | 纽欧申医药(上海)有限公司 | 一种含氮杂环化合物、其药学上可接受的盐及其制备方法与应用 |
| KR20250133677A (ko) * | 2022-12-16 | 2025-09-08 | 카루나 세러퓨틱스 인코포레이티드 | 치환된 디하이드로피롤로[3,4-d]피리미딘 화합물 및 의학적 병태 치료에서의 이의 용도 |
| KR20250121123A (ko) | 2022-12-16 | 2025-08-11 | 카루나 세러퓨틱스 인코포레이티드 | 치환된 테트라히드로피롤로-피리디논 화합물 및 의학적 병태를 치료하는 데 있어서의 이의 용도 |
| CN120641421A (zh) * | 2022-12-16 | 2025-09-12 | 卡鲁娜治疗学有限公司 | 经取代的二氢吡咯并[3,4-d]嘧啶化合物及其在治疗医学病状中的用途 |
| CN120641414A (zh) * | 2022-12-16 | 2025-09-12 | 卡鲁娜治疗学有限公司 | 经取代的四氢吡咯并-吡啶酮化合物及其在治疗医学病状中的用途 |
| EP4634183A1 (en) * | 2022-12-16 | 2025-10-22 | Karuna Therapeutics, Inc. | Substituted tetrahydropyrrolo-pyridinone compounds and their use in treating medical conditions |
| WO2024260386A1 (zh) * | 2023-06-20 | 2024-12-26 | 西藏海思科制药有限公司 | 毒蕈碱m4受体激动剂及其用途 |
| WO2025055970A1 (zh) * | 2023-09-15 | 2025-03-20 | 江苏恩华药业股份有限公司 | 氮杂环丁烷衍生物、其制备方法及其医药用途 |
| WO2025083630A1 (en) | 2023-10-19 | 2025-04-24 | Suven Life Sciences Limited | Heteroaromatic compounds as muscarinic m4 receptor positive allosteric modulators (m4 pams) |
| WO2025099660A1 (en) | 2023-11-10 | 2025-05-15 | Suven Life Sciences Limited | Piperidine substituted compounds as muscarinic m4 receptor positive allosteric modulators (m4 pams) |
| WO2025103475A1 (zh) * | 2023-11-17 | 2025-05-22 | 上海翰森生物医药科技有限公司 | 杂环羰基类衍生物调节剂、其制备方法和应用 |
| WO2025122809A1 (en) * | 2023-12-07 | 2025-06-12 | Acadia Pharmaceuticals Inc. | M4 positive allosteric modulators |
| WO2025131049A1 (en) * | 2023-12-21 | 2025-06-26 | Ignis Therapeutics (Suzhou) Limited | Dihydro-pyrrolo-pyridine derivatives and uses thereof |
| WO2025134078A1 (en) | 2023-12-22 | 2025-06-26 | Suven Life Sciences Limited | Organic compounds as muscarinic m4 receptor positive allosteric modulators (m4 pams) |
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-
2018
- 2018-06-14 KR KR1020207001865A patent/KR20200013783A/ko not_active Withdrawn
- 2018-06-14 AU AU2018287787A patent/AU2018287787A1/en not_active Abandoned
- 2018-06-14 MX MX2019015371A patent/MX2019015371A/es unknown
- 2018-06-14 IL IL271290A patent/IL271290B2/en unknown
- 2018-06-14 EP EP18743584.7A patent/EP3642202B1/en active Active
- 2018-06-14 CN CN201880049365.XA patent/CN110944998B/zh active Active
- 2018-06-14 DK DK18743584.7T patent/DK3642202T3/da active
- 2018-06-14 HU HUE18743584A patent/HUE060914T2/hu unknown
- 2018-06-14 SG SG11201913014YA patent/SG11201913014YA/en unknown
- 2018-06-14 CA CA3066986A patent/CA3066986A1/en active Pending
- 2018-06-14 US US16/625,202 patent/US11198692B2/en active Active
- 2018-06-14 PL PL18743584.7T patent/PL3642202T3/pl unknown
- 2018-06-14 BR BR112019026955-0A patent/BR112019026955A2/pt not_active Application Discontinuation
- 2018-06-14 FI FIEP18743584.7T patent/FI3642202T3/fi active
- 2018-06-14 JP JP2019570547A patent/JP7263266B2/ja active Active
- 2018-06-14 ES ES18743584T patent/ES2937236T3/es active Active
- 2018-06-14 WO PCT/IB2018/054390 patent/WO2018234953A1/en not_active Ceased
- 2018-06-14 PT PT187435847T patent/PT3642202T/pt unknown
- 2018-06-19 TW TW107120944A patent/TWI680128B/zh active
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