JPWO2020132661A5 - - Google Patents
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- JPWO2020132661A5 JPWO2020132661A5 JP2021535552A JP2021535552A JPWO2020132661A5 JP WO2020132661 A5 JPWO2020132661 A5 JP WO2020132661A5 JP 2021535552 A JP2021535552 A JP 2021535552A JP 2021535552 A JP2021535552 A JP 2021535552A JP WO2020132661 A5 JPWO2020132661 A5 JP WO2020132661A5
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- Prior art keywords
- compound
- pharmaceutically acceptable
- acceptable salt
- alkyl
- composition
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 55
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 15
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- -1 -NR15R16 Chemical group 0.000 claims description 11
- 210000004027 cell Anatomy 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 210000002950 fibroblast Anatomy 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 6
- 102000003973 Fibroblast growth factor 21 Human genes 0.000 claims description 6
- 108090000376 Fibroblast growth factor 21 Proteins 0.000 claims description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002207 metabolite Substances 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 5
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- 102000023984 PPAR alpha Human genes 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000000411 inducer Substances 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 3
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 3
- 102000004877 Insulin Human genes 0.000 claims description 3
- 108090001061 Insulin Proteins 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 230000006020 chronic inflammation Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 229940125396 insulin Drugs 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000007838 tissue remodeling Effects 0.000 claims description 3
- 206010052747 Adenocarcinoma pancreas Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 102000005593 Endopeptidases Human genes 0.000 claims description 2
- 108010059378 Endopeptidases Proteins 0.000 claims description 2
- 102000018389 Exopeptidases Human genes 0.000 claims description 2
- 108010091443 Exopeptidases Proteins 0.000 claims description 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 2
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims description 2
- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims description 2
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 230000003143 atherosclerotic effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 230000008355 cartilage degradation Effects 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 229960002297 fenofibrate Drugs 0.000 claims description 2
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 230000003176 fibrotic effect Effects 0.000 claims description 2
- 230000028993 immune response Effects 0.000 claims description 2
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims description 2
- 208000011379 keloid formation Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 230000001394 metastastic effect Effects 0.000 claims description 2
- 206010061289 metastatic neoplasm Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 210000004872 soft tissue Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 22
- 239000000126 substance Substances 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 6
- 208000008999 Giant Cell Carcinoma Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000032383 Soft tissue cancer Diseases 0.000 description 1
- 201000000014 lung giant cell carcinoma Diseases 0.000 description 1
- 208000015347 renal cell adenocarcinoma Diseases 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862784291P | 2018-12-21 | 2018-12-21 | |
| US62/784,291 | 2018-12-21 | ||
| US201962863853P | 2019-06-19 | 2019-06-19 | |
| US62/863,853 | 2019-06-19 | ||
| PCT/US2019/068189 WO2020132661A2 (en) | 2018-12-21 | 2019-12-21 | Inhibitors of fibroblast activation protein |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022514352A JP2022514352A (ja) | 2022-02-10 |
| JPWO2020132661A5 true JPWO2020132661A5 (https=) | 2022-12-28 |
| JP2022514352A5 JP2022514352A5 (https=) | 2022-12-28 |
Family
ID=71101996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021535552A Pending JP2022514352A (ja) | 2018-12-21 | 2019-12-21 | 線維芽細胞活性化タンパク質の阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US11504364B2 (https=) |
| EP (1) | EP3898654A4 (https=) |
| JP (1) | JP2022514352A (https=) |
| CN (1) | CN113811529A (https=) |
| WO (1) | WO2020132661A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021506972A (ja) | 2017-12-15 | 2021-02-22 | プラクシス バイオテック エルエルシー | 線維芽細胞活性化タンパク質の阻害剤 |
| BR112021011861A2 (pt) * | 2019-01-04 | 2021-09-08 | Praxis Biotech LLC | Inibidores da proteína de ativação de fibroblastos |
| WO2021155292A1 (en) * | 2020-01-31 | 2021-08-05 | Philip Stewart Low | Fibroblast activation protein (fap) - targeted antifibrotic therapy |
| CA3176497A1 (en) | 2020-05-07 | 2021-11-11 | Fatima MECHTA-GRIGORIOU | Antxr1 as a biomarker of immunosuppressive fibroblast populations and its use for predicting response to immunotherapy |
| CN114380795A (zh) * | 2020-10-22 | 2022-04-22 | 四川大学华西医院 | 氘代fap抑制剂及其应用 |
| CN114621155A (zh) * | 2020-12-14 | 2022-06-14 | 四川科伦药物研究院有限公司 | 一种制备卡马替尼的方法 |
| CN116745291A (zh) * | 2020-12-17 | 2023-09-12 | 阿斯利康(瑞典)有限公司 | N-(2-(4-氰基噻唑烷-3-基)-2-氧代乙基)-喹啉-4-甲酰胺 |
| EP4122499A1 (en) * | 2021-07-23 | 2023-01-25 | 3B Pharmaceuticals GmbH | Fibroblast activation protein inhibitors and use thereof |
| EP4531932A1 (en) | 2022-06-03 | 2025-04-09 | Universiteit Antwerpen | Inhibitors of fibroblast activation protein |
| JP2025525344A (ja) * | 2022-06-21 | 2025-08-05 | アストラゼネカ・アクチエボラーグ | Ｎ－（２－（４－シアノチアゾリジン－３－イル）－２－オキソエチル）－キノリン－４－カルボキサミド |
| WO2023247488A1 (en) * | 2022-06-21 | 2023-12-28 | Astrazeneca Ab | N-(2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)- quinoline-4-carboxamides |
| CA3260370A1 (en) * | 2022-06-21 | 2023-12-28 | Astrazeneca Ab | SOLID FORMS OF N-(2-(4-CYANOTHIAZOLIDIN-3-YL)-2-OXOEETHYL)-6-MORPHOLINOQUINOLEIN-4-CARBOXAMIDE |
| WO2025037000A1 (en) | 2023-08-17 | 2025-02-20 | Universiteit Antwerpen | Novel fibroblast activation protein inhibitors and medical uses thereof |
| CN121752300A (zh) | 2023-08-31 | 2026-03-27 | 荷兰拉德堡德大学学术医学中心 | 子宫内膜异位症示踪剂 |
| WO2025106939A1 (en) * | 2023-11-16 | 2025-05-22 | Praxis Biotech LLC | Conjugates targeting fibroblast activation protein and uses thereof |
| WO2025106926A1 (en) * | 2023-11-16 | 2025-05-22 | Praxis Biotech LLC | Conjugates targeting fibroblast activation protein and uses thereof |
| CN120400145A (zh) * | 2025-04-03 | 2025-08-01 | 江南大学 | 基因fap在制备非酒精性脂肪型肝炎的药物中的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60221983T2 (de) | 2001-06-27 | 2008-05-15 | Smithkline Beecham Corp. | Fluorpyrrolidine als dipeptidyl-peptidase inhibitoren |
| WO2004071454A2 (en) * | 2003-02-13 | 2004-08-26 | Guilford Pharmaceuticals Inc. | Substituted azetidine compounds as inhibitors of dipeptidyl peptidase iv |
| EP1943257A2 (en) | 2005-05-19 | 2008-07-16 | Genentech, Inc. | Fibroblast activation protein inhibitor compounds and methods |
| AU2006278039B2 (en) | 2005-08-11 | 2010-10-21 | F. Hoffmann-La Roche Ag | Pharmaceutical composition comprising a DPP-lV inhibitor |
| EP1760076A1 (en) | 2005-09-02 | 2007-03-07 | Ferring B.V. | FAP Inhibitors |
| CN101230058A (zh) | 2007-01-23 | 2008-07-30 | 上海恒瑞医药有限公司 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| US8338450B2 (en) | 2007-09-21 | 2012-12-25 | Lupin Limited | Compounds as dipeptidyl peptidase IV (DPP IV) inhibitors |
| MX2010007593A (es) | 2008-01-10 | 2010-10-13 | Sun Pharma Advanced Res Co Ltd | Derivados novedosos de acil cianopirrolidinas. |
| WO2010083570A1 (en) | 2009-01-23 | 2010-07-29 | The University Of Sydney | Novel metabolic disease therapy |
| WO2013107820A1 (en) * | 2012-01-17 | 2013-07-25 | Universiteit Antwerpen | Novel fap inhibitors |
| EP2730571A1 (en) | 2012-11-12 | 2014-05-14 | Universitat De Barcelona | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
| CN116059219A (zh) | 2015-07-16 | 2023-05-05 | 比奥克斯塞尔医疗股份有限公司 | 一种使用免疫调节治疗癌症的新颖方法 |
| WO2017189569A1 (en) | 2016-04-25 | 2017-11-02 | Trustees Of Tufts College | Multimediator dpp4 and fap inhibitors, and uses related thereto |
| IL267093B (en) | 2016-12-14 | 2022-08-01 | Medimmune Llc | Embedded multiple-part sensor within a plunger rod to capture and transmit injection information |
| CN116474108A (zh) * | 2016-12-14 | 2023-07-25 | 普渡研究基金会 | 成纤维细胞活化蛋白(fap)-靶向成像和治疗 |
| EA202090776A1 (ru) | 2017-10-23 | 2020-07-27 | Дзе Джонс Хопкинс Юниверсити | Визуализирующие и радиотерапевтические агенты, нацеленные на фибробласт-активирующий белок-альфа (fapalpha) |
| JP2021506972A (ja) * | 2017-12-15 | 2021-02-22 | プラクシス バイオテック エルエルシー | 線維芽細胞活性化タンパク質の阻害剤 |
| SG11202007180QA (en) | 2018-02-06 | 2020-08-28 | Univ Heidelberg | Fap inhibitor |
| BR112021011861A2 (pt) | 2019-01-04 | 2021-09-08 | Praxis Biotech LLC | Inibidores da proteína de ativação de fibroblastos |
-
2019
- 2019-12-21 CN CN201980092135.6A patent/CN113811529A/zh active Pending
- 2019-12-21 EP EP19901288.1A patent/EP3898654A4/en not_active Withdrawn
- 2019-12-21 WO PCT/US2019/068189 patent/WO2020132661A2/en not_active Ceased
- 2019-12-21 US US16/724,198 patent/US11504364B2/en active Active
- 2019-12-21 JP JP2021535552A patent/JP2022514352A/ja active Pending
-
2022
- 2022-09-14 US US17/944,963 patent/US20230144841A1/en not_active Abandoned
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