JPWO2020016129A5 - - Google Patents
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- Publication number
- JPWO2020016129A5 JPWO2020016129A5 JP2021501323A JP2021501323A JPWO2020016129A5 JP WO2020016129 A5 JPWO2020016129 A5 JP WO2020016129A5 JP 2021501323 A JP2021501323 A JP 2021501323A JP 2021501323 A JP2021501323 A JP 2021501323A JP WO2020016129 A5 JPWO2020016129 A5 JP WO2020016129A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- pyrrolo
- oxy
- phenyl
- 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.)
- Pending
Links
- -1 heterocyclic radical Chemical class 0.000 claims 49
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- PKZDPOGLGBWEGP-UHFFFAOYSA-N 3-methyl-1H-pyrrolo[2,3-b]pyridine Chemical compound C1=CC=C2C(C)=CNC2=N1 PKZDPOGLGBWEGP-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000002815 Pulmonary Hypertension Diseases 0.000 claims 2
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 2
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims 2
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims 2
- 102100009445 TPH1 Human genes 0.000 claims 2
- 101700050772 TPH1 Proteins 0.000 claims 2
- 125000005418 aryl aryl group Chemical group 0.000 claims 2
- 125000004429 atoms Chemical class 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N cAMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims 2
- 201000009794 idiopathic pulmonary fibrosis Diseases 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000007921 spray Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
- FOQWCSIQBWFFOM-UHFFFAOYSA-N 5-methyl-7H-pyrrolo[2,3-d]pyrimidine Chemical compound C1=NC=C2C(C)=CNC2=N1 FOQWCSIQBWFFOM-UHFFFAOYSA-N 0.000 claims 1
- 102100000003 ACVR1B Human genes 0.000 claims 1
- 101710026724 ACVR1B Proteins 0.000 claims 1
- 229940116904 ANTIINFLAMMATORY THERAPEUTIC RADIOPHARMACEUTICALS Drugs 0.000 claims 1
- 229940064005 Antibiotic throat preparations Drugs 0.000 claims 1
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims 1
- 229940042052 Antibiotics for systemic use Drugs 0.000 claims 1
- 229940042786 Antitubercular Antibiotics Drugs 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 102000016911 Deoxyribonucleases Human genes 0.000 claims 1
- 108010053770 Deoxyribonucleases Proteins 0.000 claims 1
- 229940112141 Dry Powder Inhaler Drugs 0.000 claims 1
- 101000457332 ELANE Proteins 0.000 claims 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N Epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 claims 1
- 102000009079 Epoprostenol Receptors Human genes 0.000 claims 1
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims 1
- NYHBQMYGNKIUIF-PXMDKTAGSA-N Guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1O[C@@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-PXMDKTAGSA-N 0.000 claims 1
- 229940029575 Guanosine Drugs 0.000 claims 1
- 229940093922 Gynecological Antibiotics Drugs 0.000 claims 1
- 208000009856 Lung Disease Diseases 0.000 claims 1
- 229940071648 Metered Dose Inhaler Drugs 0.000 claims 1
- HGYLVHDQAMEBCR-QHCPKHFHSA-N N[C@H](C(=O)N1CCC(CC1)S(=O)(=O)C1=CC=CC=C1)CC1=CC(=C(C(=C1)F)OC1=C2C(=NC=C1)NC=C2C)F Chemical compound N[C@H](C(=O)N1CCC(CC1)S(=O)(=O)C1=CC=CC=C1)CC1=CC(=C(C(=C1)F)OC1=C2C(=NC=C1)NC=C2C)F HGYLVHDQAMEBCR-QHCPKHFHSA-N 0.000 claims 1
- MGZVUECTJUZKTM-QFIPXVFZSA-N N[C@H](C(=O)N1CCC(CC1)S(=O)(=O)C1=CC=CC=C1)CC1=CC(=C(C(=C1)F)OC=1C2=C(N=CN=1)NC=C2C)F Chemical compound N[C@H](C(=O)N1CCC(CC1)S(=O)(=O)C1=CC=CC=C1)CC1=CC(=C(C(=C1)F)OC=1C2=C(N=CN=1)NC=C2C)F MGZVUECTJUZKTM-QFIPXVFZSA-N 0.000 claims 1
- XSIVHNLABTXKBH-ZDUSSCGKSA-N N[C@H](C(=O)NC)CC1=CC(=C(C=C1)OC1=C2C(=NC=C1)NC=C2C)F Chemical compound N[C@H](C(=O)NC)CC1=CC(=C(C=C1)OC1=C2C(=NC=C1)NC=C2C)F XSIVHNLABTXKBH-ZDUSSCGKSA-N 0.000 claims 1
- 229940074726 OPHTHALMOLOGIC ANTIINFLAMMATORY AGENTS Drugs 0.000 claims 1
- 108091006303 Prostaglandin I receptors Proteins 0.000 claims 1
- 102100017669 SMAD2 Human genes 0.000 claims 1
- 102100017668 SMAD3 Human genes 0.000 claims 1
- 108010007585 Smad2 Protein Proteins 0.000 claims 1
- 108010042057 Smad3 Protein Proteins 0.000 claims 1
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 230000000954 anitussive Effects 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 239000003434 antitussive agent Substances 0.000 claims 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 230000003115 biocidal Effects 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000002559 chemokine receptor antagonist Substances 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 102000027751 corticosteroid receptors Human genes 0.000 claims 1
- 108091008045 corticosteroid receptors Proteins 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000004059 degradation Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 239000002713 epithelial sodium channel blocking agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 102000032800 human ELANE protein Human genes 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229940079866 intestinal antibiotics Drugs 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000003591 leukocyte elastase inhibitor Substances 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 239000003595 mist Substances 0.000 claims 1
- 150000004712 monophosphates Chemical class 0.000 claims 1
- 239000006199 nebulizer Substances 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 239000002840 nitric oxide donor Substances 0.000 claims 1
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 claims 1
- 239000002357 osmotic agent Substances 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 101710027185 pgiA1 Proteins 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 238000006366 phosphorylation reaction Methods 0.000 claims 1
- 230000000865 phosphorylative Effects 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003815 prostacyclins Chemical class 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18183733.7 | 2018-07-16 | ||
| EP18183733 | 2018-07-16 | ||
| PCT/EP2019/068832 WO2020016129A1 (en) | 2018-07-16 | 2019-07-12 | Tyrosine amide derivatives as rho- kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021529819A JP2021529819A (ja) | 2021-11-04 |
| JPWO2020016129A5 true JPWO2020016129A5 (sl) | 2022-07-12 |
Family
ID=62975943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021501323A Pending JP2021529819A (ja) | 2018-07-16 | 2019-07-12 | Ｒｈｏキナーゼ阻害剤としてのチロシンアミド誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20210284639A1 (sl) |
| EP (1) | EP3823969A1 (sl) |
| JP (1) | JP2021529819A (sl) |
| KR (1) | KR20210032977A (sl) |
| CN (1) | CN112752757B (sl) |
| AR (1) | AR115766A1 (sl) |
| AU (1) | AU2019304472A1 (sl) |
| BR (1) | BR112021000101A2 (sl) |
| CA (1) | CA3104955A1 (sl) |
| MA (1) | MA53164A (sl) |
| MX (1) | MX2021000270A (sl) |
| TW (1) | TW202019923A (sl) |
| WO (1) | WO2020016129A1 (sl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2021403631A1 (en) | 2020-12-15 | 2023-07-27 | Chiesi Farmaceutici S.P.A. | Dihydrofuropyridine derivatives as rho- kinase inhibitors |
| CN116600810A (zh) | 2020-12-15 | 2023-08-15 | 奇斯药制品公司 | 作为rho-激酶抑制剂的二氢呋喃并吡啶衍生物 |
| CN116600811A (zh) | 2020-12-15 | 2023-08-15 | 奇斯药制品公司 | 作为rho-激酶抑制剂的二氢呋喃并吡啶衍生物 |
| WO2023110700A1 (en) | 2021-12-13 | 2023-06-22 | Chiesi Farmaceutici S.P.A. | Dihydrofuropyridine derivatives as rho-kinase inhibitors |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2503646C (en) | 2002-10-28 | 2011-09-27 | Bayer Healthcare Ag | Heteroaryloxy-substituted phenylaminopyrimidines as rho-kinase inhibitors |
| US7521465B2 (en) * | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| DE102004017438A1 (de) * | 2004-04-08 | 2005-11-03 | Bayer Healthcare Ag | Hetaryloxy-substituierte Phenylaminopyrimidine |
| US20080125427A1 (en) | 2004-06-17 | 2008-05-29 | Smithkline Beecham Corporation | Novel Inhibitors of Rho-Kinases |
| KR20080040027A (ko) * | 2005-09-02 | 2008-05-07 | 아스테라스 세이야쿠 가부시키가이샤 | Ｒｏｃｋ 억제제로서 아미드 유도체 |
| JP2011507848A (ja) | 2007-12-21 | 2011-03-10 | ザ スクリプス リサーチ インスティチュート | Ｒｈｏキナーゼインヒビターとしてのベンゾピランおよびアナログ |
| EP2100598A1 (en) * | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| US20110166161A1 (en) | 2008-09-18 | 2011-07-07 | Astellas Pharma Inc. | Heterocyclic carboxamide compounds |
| PT2593452T (pt) | 2010-07-14 | 2017-04-24 | Novartis Ag | Compostos heterocíclicos agonistas do receptor ip |
| KR101906630B1 (ko) * | 2011-06-10 | 2018-10-10 | 키에시 파르마슈티시 엣스. 피. 에이. | 무스카린 수용체 길항제 및 베타2 아드레날린 수용체 작용제 효능을 갖는 화합물 |
| LT2951172T (lt) | 2013-01-29 | 2017-07-25 | Redx Pharma Plc | Piridino dariniai, kaip lengvai suyrantys rock inhibitoriai |
| AR110401A1 (es) | 2016-12-21 | 2019-03-27 | Chiesi Farm Spa | Derivados dihidropirimidina bicíclica-carboxamida como inhibidores de rho-quinasa |
| PL3573987T3 (pl) * | 2017-01-30 | 2021-08-30 | Chiesi Farmaceutici S.P.A. | Pochodne amidu tyrozynowego jako inhibitory kinazy Rho |
-
2019
- 2019-06-24 TW TW108121992A patent/TW202019923A/zh unknown
- 2019-07-11 AR ARP190101969A patent/AR115766A1/es unknown
- 2019-07-12 MA MA053164A patent/MA53164A/fr unknown
- 2019-07-12 CA CA3104955A patent/CA3104955A1/en active Pending
- 2019-07-12 JP JP2021501323A patent/JP2021529819A/ja active Pending
- 2019-07-12 US US17/260,631 patent/US20210284639A1/en active Pending
- 2019-07-12 BR BR112021000101-8A patent/BR112021000101A2/pt unknown
- 2019-07-12 AU AU2019304472A patent/AU2019304472A1/en active Pending
- 2019-07-12 CN CN201980047406.6A patent/CN112752757B/zh active Active
- 2019-07-12 MX MX2021000270A patent/MX2021000270A/es unknown
- 2019-07-12 EP EP19744641.2A patent/EP3823969A1/en active Pending
- 2019-07-12 WO PCT/EP2019/068832 patent/WO2020016129A1/en unknown
- 2019-07-12 KR KR1020217003030A patent/KR20210032977A/ko not_active Application Discontinuation
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