JP2017519754A5 - - Google Patents
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- JP2017519754A5 JP2017519754A5 JP2016572754A JP2016572754A JP2017519754A5 JP 2017519754 A5 JP2017519754 A5 JP 2017519754A5 JP 2016572754 A JP2016572754 A JP 2016572754A JP 2016572754 A JP2016572754 A JP 2016572754A JP 2017519754 A5 JP2017519754 A5 JP 2017519754A5
- Authority
- JP
- Japan
- Prior art keywords
- disease
- alkyl
- compound according
- lymphoma
- cycloalkyl
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 206010025323 Lymphomas Diseases 0.000 claims 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 13
- 201000010099 disease Diseases 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 10
- 208000032839 leukemia Diseases 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 208000003950 B-cell lymphoma Diseases 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 208000023275 Autoimmune disease Diseases 0.000 claims 6
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 6
- 208000026278 immune system disease Diseases 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 210000003719 b-lymphocyte Anatomy 0.000 claims 5
- 125000002837 carbocyclic group Chemical group 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 206010025135 lupus erythematosus Diseases 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 206010005949 Bone cancer Diseases 0.000 claims 4
- 208000018084 Bone neoplasm Diseases 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 208000011231 Crohn disease Diseases 0.000 claims 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 4
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- 208000034578 Multiple myelomas Diseases 0.000 claims 4
- -1 NR b R c Chemical group 0.000 claims 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 4
- 201000000023 Osteosclerosis Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims 4
- 206010003246 arthritis Diseases 0.000 claims 4
- 210000000988 bone and bone Anatomy 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 230000009401 metastasis Effects 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 210000002768 hair cell Anatomy 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 3
- 210000003734 kidney Anatomy 0.000 claims 3
- 238000002054 transplantation Methods 0.000 claims 3
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 2
- 230000036210 malignancy Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 1
- 208000016025 Waldenstroem macroglobulinemia Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 239000013066 combination product Substances 0.000 claims 1
- 229940127555 combination product Drugs 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 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
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002831 pharmacologic agent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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| EA201890730A1 (ru) * | 2015-09-16 | 2018-10-31 | Локсо Онколоджи, Инк. | Производные пиразолопиримидина в качестве ингибиторов btk для лечения злокачественного новообразования |
| WO2017103611A1 (en) | 2015-12-16 | 2017-06-22 | Redx Pharma Plc | Compounds useful as kinase inhibitors |
| US9630968B1 (en) | 2015-12-23 | 2017-04-25 | Arqule, Inc. | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
| WO2017111787A1 (en) * | 2015-12-23 | 2017-06-29 | Arqule, Inc. | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
| US10662187B2 (en) * | 2016-01-21 | 2020-05-26 | Zibo Biopolar Changsheng Pharmaceutical Co. Ltd. | Bruton's tyrosine kinase inhibitors |
| CN109153680B (zh) * | 2016-07-07 | 2021-04-23 | 株式会社大熊制药 | 4-氨基吡唑并[3,4-d]嘧啶基氮杂双环衍生物及含其的药物组合物 |
| TW201811795A (zh) | 2016-08-24 | 2018-04-01 | 美商亞闊股份有限公司 | 胺基－吡咯并嘧啶酮化合物及其用途 |
| WO2019130229A1 (en) * | 2017-12-28 | 2019-07-04 | Mylan Laboratories Ltd | Methods and intermediates for preparing rucaparib |
| US20220362357A1 (en) | 2018-08-31 | 2022-11-17 | Stichting Radboud Universitair Medisch Centrum | Synergistic Combinations of Amino Acid Depletion Agent Sensitizers (AADAS) and Amino Acid Depletion Agents (AADA), and Therapeutic Methods of Use Thereof |
| KR102801205B1 (ko) | 2019-12-04 | 2025-04-29 | 허난 즈웨이 바이오메디슨 씨오., 엘티디. | 브루톤 티로신 키나제 억제제인 이미다졸 카복사마이드 유도체 |
| JP7011638B2 (ja) * | 2019-12-16 | 2022-02-10 | アークル インコーポレイテッド | テトラヒドロピラニルアミノ－ピロロピリミジノンおよびその使用の方法 |
| CN113214265B (zh) * | 2020-01-21 | 2023-07-07 | 江苏先声药业有限公司 | 嘧啶并五元环类化合物 |
| RU2747991C1 (ru) * | 2020-02-18 | 2021-05-18 | Аркьюл, Инк. | Тетрагидропиранил амино-пирролопиримидинон и способы его применения |
| WO2021180107A1 (en) * | 2020-03-12 | 2021-09-16 | Fochon Pharmaceuticals, Ltd. | Compounds useful as kinase inhibitors |
| CN114075190A (zh) * | 2020-08-20 | 2022-02-22 | 北京诺诚健华医药科技有限公司 | 杂环类btk抑制剂 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2385747A1 (en) | 1999-09-17 | 2001-03-22 | Gavin C. Hirst | Pyrazolopyrimidines as therapeutic agents |
| US6921763B2 (en) | 1999-09-17 | 2005-07-26 | Abbott Laboratories | Pyrazolopyrimidines as therapeutic agents |
| US20030225098A1 (en) | 2002-03-21 | 2003-12-04 | Hirst Gavin C. | Kinase inhibitors |
| BRPI0622054B8 (pt) | 2006-09-22 | 2021-05-25 | Oxford Amherst Llc | composto e composição farmacêutica |
| CA2668286C (en) | 2006-11-03 | 2014-09-16 | Pharmacyclics, Inc. | Bruton's tyrosine kinase activity probe and method of using |
| IL295053A (en) * | 2007-03-28 | 2022-09-01 | Pharmacyclics Llc | Broton tyrosine kinase inhibitors |
| US8338439B2 (en) | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| TWI546290B (zh) | 2008-06-27 | 2016-08-21 | 賽基艾維洛米斯研究股份有限公司 | 雜芳基化合物及其用途 |
| ES2660418T3 (es) * | 2008-07-16 | 2018-03-22 | Pharmacyclics Llc | Inhibidores de la tirosina quinasa de Bruton para el tratamiento de tumores sólidos |
| SI2324008T1 (sl) | 2008-07-24 | 2012-08-31 | Nerviano Medical Sciences Srl | 3,4-diarilpirazoli kot protein-kinazni inhibitorji |
| US8426428B2 (en) | 2008-12-05 | 2013-04-23 | Principia Biopharma, Inc. | EGFR kinase knockdown via electrophilically enhanced inhibitors |
| US7718662B1 (en) | 2009-10-12 | 2010-05-18 | Pharmacyclics, Inc. | Pyrazolo-pyrimidine inhibitors of bruton's tyrosine kinase |
| CN107898791A (zh) | 2010-06-03 | 2018-04-13 | 药品循环有限责任公司 | 布鲁顿酪氨酸激酶(btk)抑制剂的应用 |
| CA2836449C (en) | 2011-05-17 | 2021-04-27 | The Regents Of The University Of California | Kinase inhibitors |
| EA025496B1 (ru) | 2011-05-17 | 2016-12-30 | Принсипиа Биофарма Инк. | Ингибиторы тирозинкиназы |
| US9138436B2 (en) * | 2011-07-13 | 2015-09-22 | Pharmacyclics Llc | Inhibitors of Bruton's tyrosine kinase |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| US8377946B1 (en) * | 2011-12-30 | 2013-02-19 | Pharmacyclics, Inc. | Pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine compounds as kinase inhibitors |
| CN104487441B (zh) | 2012-06-18 | 2018-06-01 | 普林斯匹亚生物制药公司 | 有用于治疗癌症和自身免疫性疾病的可逆的共价吡咯并嘧啶或吡唑并嘧啶 |
| WO2014022569A1 (en) | 2012-08-03 | 2014-02-06 | Principia Biopharma Inc. | Treatment of dry eye |
| JP6178861B2 (ja) | 2012-11-02 | 2017-08-09 | ファイザー・インク | ブルトン型チロシンキナーゼ阻害剤 |
| CN103848810A (zh) | 2012-11-30 | 2014-06-11 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
| US8957080B2 (en) * | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| GB201309085D0 (en) * | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| JP6615752B2 (ja) | 2013-09-30 | 2019-12-04 | グアンジョウ・イノケア・ファーマ・テク・カンパニー・リミテッド | Ｂｔｋの置換ニコチンイミド阻害剤およびそれらの調製、ならびにがん、炎症および自己免疫疾患の治療における使用 |
| US9637486B2 (en) | 2013-12-20 | 2017-05-02 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| PT3107544T (pt) | 2014-02-21 | 2021-01-05 | Principia Biopharma Inc | Sais e forma sólida de um inibidor de btk |
| GB201404987D0 (en) | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| CN105085474B (zh) | 2014-05-07 | 2018-05-18 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
| GB201410430D0 (en) | 2014-06-11 | 2014-07-23 | Redx Pharma Ltd | Compounds |
| EA201890730A1 (ru) | 2015-09-16 | 2018-10-31 | Локсо Онколоджи, Инк. | Производные пиразолопиримидина в качестве ингибиторов btk для лечения злокачественного новообразования |
| WO2017103611A1 (en) | 2015-12-16 | 2017-06-22 | Redx Pharma Plc | Compounds useful as kinase inhibitors |
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