JP2018514560A5 - - Google Patents
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- Publication number
- JP2018514560A5 JP2018514560A5 JP2017556831A JP2017556831A JP2018514560A5 JP 2018514560 A5 JP2018514560 A5 JP 2018514560A5 JP 2017556831 A JP2017556831 A JP 2017556831A JP 2017556831 A JP2017556831 A JP 2017556831A JP 2018514560 A5 JP2018514560 A5 JP 2018514560A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- carboxamide
- pyrazine
- acryloyl
- amino
- 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
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- -1 Cyano, hydroxyl Chemical group 0.000 claims 463
- 125000003277 amino group Chemical compound 0.000 claims 145
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 111
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 98
- 125000000217 alkyl group Chemical group 0.000 claims 90
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 60
- 201000010099 disease Diseases 0.000 claims 43
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000004200 2-methoxyethyl group Chemical compound [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 22
- 230000001363 autoimmune Effects 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 20
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 19
- 125000004194 piperazin-1-yl group Chemical compound [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 18
- LVOICKNPHXSSQM-UHFFFAOYSA-N prop-2-en-1-one Chemical compound C=C[C]=O LVOICKNPHXSSQM-UHFFFAOYSA-N 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 15
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (E)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 claims 14
- LYVWJKRCILVKOI-UHFFFAOYSA-N 1,1,1-trifluorobutane Chemical compound [CH2]CCC(F)(F)F LYVWJKRCILVKOI-UHFFFAOYSA-N 0.000 claims 14
- GTIIVHODSNYECK-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical group [CH2]CC(F)(F)F GTIIVHODSNYECK-UHFFFAOYSA-N 0.000 claims 14
- 125000004575 3-pyrrolidinyl group Chemical compound [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000001559 cyclopropyl group Chemical compound [H]C1([H])C([H])([H])C1([H])* 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 239000011780 sodium chloride Substances 0.000 claims 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 13
- 229910052805 deuterium Inorganic materials 0.000 claims 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 13
- GJWHXWMUGWZNTO-UHFFFAOYSA-N 2,2-dimethylpropane Chemical compound [CH2]C(C)(C)C GJWHXWMUGWZNTO-UHFFFAOYSA-N 0.000 claims 12
- 206010013774 Dry eye Diseases 0.000 claims 12
- 206010023332 Keratitis Diseases 0.000 claims 12
- 206010046851 Uveitis Diseases 0.000 claims 12
- 230000001684 chronic Effects 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- VZIHTQKMHLOIII-UHFFFAOYSA-N 3,5-dihydro-2H-furan Chemical group [CH]1CCOC1 VZIHTQKMHLOIII-UHFFFAOYSA-N 0.000 claims 8
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- 206010006187 Breast cancer Diseases 0.000 claims 8
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- 206010012601 Diabetes mellitus Diseases 0.000 claims 8
- 241000721454 Pemphigus Species 0.000 claims 8
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims 8
- 206010052779 Transplant rejections Diseases 0.000 claims 8
- 230000001154 acute Effects 0.000 claims 8
- 201000004384 alopecia Diseases 0.000 claims 8
- 231100000360 alopecia Toxicity 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 201000004624 dermatitis Diseases 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 8
- 125000004184 methoxymethyl group Chemical compound [H]C([H])([H])OC([H])([H])* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 210000004185 Liver Anatomy 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004851 cyclopentylmethyl group Chemical compound C1(CCCC1)C* 0.000 claims 6
- 210000001508 Eye Anatomy 0.000 claims 5
- 206010061218 Inflammation Diseases 0.000 claims 5
- 206010022114 Injury Diseases 0.000 claims 5
- 230000002496 gastric Effects 0.000 claims 5
- 230000004054 inflammatory process Effects 0.000 claims 5
- 210000000056 organs Anatomy 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 206010000880 Acute myeloid leukaemia Diseases 0.000 claims 4
- 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims 4
- 208000002205 Allergic Conjunctivitis Diseases 0.000 claims 4
- 206010002026 Amyotrophic lateral sclerosis Diseases 0.000 claims 4
- 208000007502 Anemia Diseases 0.000 claims 4
- 208000009094 Anemia, Hemolytic, Autoimmune Diseases 0.000 claims 4
- 206010002556 Ankylosing spondylitis Diseases 0.000 claims 4
- 206010002855 Anxiety Diseases 0.000 claims 4
- 206010057666 Anxiety disease Diseases 0.000 claims 4
- 208000006673 Asthma Diseases 0.000 claims 4
- 210000001130 Astrocytes Anatomy 0.000 claims 4
- 208000005783 Autoimmune Thyroiditis Diseases 0.000 claims 4
- 206010003816 Autoimmune disease Diseases 0.000 claims 4
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 4
- 206010004161 Basedow's disease Diseases 0.000 claims 4
- 208000009137 Behcet Syndrome Diseases 0.000 claims 4
- 201000008335 Behcet's disease Diseases 0.000 claims 4
- 206010004661 Biliary cirrhosis primary Diseases 0.000 claims 4
- 206010004938 Bipolar disease Diseases 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 4
- 210000001185 Bone Marrow Anatomy 0.000 claims 4
- 206010005949 Bone cancer Diseases 0.000 claims 4
- 208000008581 Brain Disease Diseases 0.000 claims 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims 4
- 208000000594 Bullous Pemphigoid Diseases 0.000 claims 4
- RCRWUKIWWBKMBH-CHWSQXEVSA-N C(C=C)(=O)N1C[C@H]([C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC)OC Chemical compound C(C=C)(=O)N1C[C@H]([C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC)OC RCRWUKIWWBKMBH-CHWSQXEVSA-N 0.000 claims 4
- UKDHINGMRKDDDZ-VXGBXAGGSA-N C(C=C)(=O)N1[C@@H](C[C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F)C Chemical compound C(C=C)(=O)N1[C@@H](C[C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F)C UKDHINGMRKDDDZ-VXGBXAGGSA-N 0.000 claims 4
- JVYIHGXUMFZDGD-NWDGAFQWSA-N C(C=C)(=O)N1[C@H](C[C@@H](CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC)C Chemical compound C(C=C)(=O)N1[C@H](C[C@@H](CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC)C JVYIHGXUMFZDGD-NWDGAFQWSA-N 0.000 claims 4
- JDAIJCHVJIBIDH-RYUDHWBXSA-N COC[C@H]1N(C[C@H](CC1)NC=1C2=C(N=CN=1)NC=C2)C(C=C)=O Chemical compound COC[C@H]1N(C[C@H](CC1)NC=1C2=C(N=CN=1)NC=C2)C(C=C)=O JDAIJCHVJIBIDH-RYUDHWBXSA-N 0.000 claims 4
- 206010006895 Cachexia Diseases 0.000 claims 4
- 210000000845 Cartilage Anatomy 0.000 claims 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 4
- 210000004240 Ciliary Body Anatomy 0.000 claims 4
- 206010009839 Coeliac disease Diseases 0.000 claims 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims 4
- 206010009944 Colon cancer Diseases 0.000 claims 4
- 206010010904 Convulsion Diseases 0.000 claims 4
- 210000004087 Cornea Anatomy 0.000 claims 4
- 208000006069 Corneal Opacity Diseases 0.000 claims 4
- 206010070976 Craniocerebral injury Diseases 0.000 claims 4
- 206010011401 Crohn's disease Diseases 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 206010012818 Diffuse large B-cell lymphoma Diseases 0.000 claims 4
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 4
- 208000005679 Eczema Diseases 0.000 claims 4
- 210000002351 Embryonic Muscle Cell Anatomy 0.000 claims 4
- 206010014599 Encephalitis Diseases 0.000 claims 4
- 206010014623 Encephalopathy Diseases 0.000 claims 4
- 206010014625 Encephalopathy Diseases 0.000 claims 4
- 210000003414 Extremities Anatomy 0.000 claims 4
- 208000009745 Eye Disease Diseases 0.000 claims 4
- 208000005017 Glioblastoma Diseases 0.000 claims 4
- 206010018338 Glioma Diseases 0.000 claims 4
- 208000003807 Graves Disease Diseases 0.000 claims 4
- 201000004779 Graves' disease Diseases 0.000 claims 4
- 210000002216 Heart Anatomy 0.000 claims 4
- 208000005100 Herpetic Keratitis Diseases 0.000 claims 4
- 201000001971 Huntington's disease Diseases 0.000 claims 4
- 206010020751 Hypersensitivity Diseases 0.000 claims 4
- 206010021972 Inflammatory bowel disease Diseases 0.000 claims 4
- 210000000554 Iris Anatomy 0.000 claims 4
- 208000007766 Kaposi Sarcoma Diseases 0.000 claims 4
- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 claims 4
- 210000003734 Kidney Anatomy 0.000 claims 4
- 206010024324 Leukaemias Diseases 0.000 claims 4
- 208000007046 Leukemia, Myeloid, Acute Diseases 0.000 claims 4
- 210000004072 Lung Anatomy 0.000 claims 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 4
- 206010025135 Lupus erythematosus Diseases 0.000 claims 4
- 206010057840 Major depression Diseases 0.000 claims 4
- 208000008585 Mastocytosis Diseases 0.000 claims 4
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims 4
- 210000000214 Mouth Anatomy 0.000 claims 4
- 241001502129 Mullus Species 0.000 claims 4
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- 206010028417 Myasthenia gravis Diseases 0.000 claims 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
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- 125000005745 ethoxymethyl group Chemical compound [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 4
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- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 3
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
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- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
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| CN110382482A (zh) * | 2017-01-26 | 2019-10-25 | 亚瑞克西斯制药公司 | 稠合的杂-杂二环化合物及其使用方法 |
| US11358959B2 (en) | 2017-01-26 | 2022-06-14 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| WO2018200786A1 (en) * | 2017-04-26 | 2018-11-01 | Yale University | Compositions and methods for treating vitiligo |
| EP3630747A1 (en) | 2017-05-25 | 2020-04-08 | Araxes Pharma LLC | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| UA125318C2 (uk) * | 2017-08-01 | 2022-02-16 | Тереванс Байофарма Ар Енд Ді Айпі, Елелсі | Піразоло- і триазолобіциклічні сполуки як інгібітори jak-кінази |
| HRP20220331T1 (hr) | 2018-03-08 | 2022-05-13 | Incyte Corporation | Spojevi aminopirazin diola kao inhibitori pi3k-y |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| EP3833350A4 (en) | 2018-08-10 | 2022-05-18 | Aclaris Therapeutics, Inc. | PYRROLOPYRIMIDINE TKI INHIBITORS |
| CA3125039A1 (en) | 2019-01-23 | 2020-07-30 | Theravance Biopharma R&D Ip, Llc | Imidazo[1,5-a]pyridine, 1,2,4-triazolo[4,3-a]pyridine and imidazo[1,5-a]pyrazine as jak inhibitors |
| CN112430235B (zh) * | 2019-08-26 | 2024-04-05 | 东莞市东阳光仿制药研发有限公司 | 一种pf-06651600中间体的制备方法 |
| KR102228668B1 (ko) * | 2019-10-08 | 2021-03-17 | (주)부흥산업사 | 메틸피퍼리딘 아미노피롤로 피리미딘의 제조방법 |
| CN111407767B (zh) * | 2020-03-28 | 2021-05-25 | 中山大学 | 一种磺胺间甲氧嘧啶衍生物在制备抗肿瘤药物中的应用 |
| WO2023151069A1 (zh) * | 2022-02-14 | 2023-08-17 | 湖南南新制药股份有限公司 | 吡咯并[2,3-d]六元杂芳环衍生物、其制备方法和药物用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RS50087B (sr) | 1998-06-19 | 2009-01-22 | Pfizer Products Inc., | Pirolo (2,3-d) pirimidin jedinjenja |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| EA006227B1 (ru) | 1999-12-10 | 2005-10-27 | Пфайзер Продактс Инк. | СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА |
| CA2412560C (en) | 2000-06-26 | 2008-12-30 | Pfizer Products Inc. | Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| CN1726192A (zh) | 2002-11-21 | 2006-01-25 | 辉瑞产品公司 | 3－氨基－哌啶衍生物及其制备方法 |
| US7491827B2 (en) | 2002-12-23 | 2009-02-17 | Millennium Pharmaceuticals, Inc. | Aryl sulfonamides useful as inhibitors of chemokine receptor activity |
| WO2005021568A2 (en) | 2003-08-27 | 2005-03-10 | Biota, Inc. | Novel tricyclic nucleosides or nucleotides as therapeutic agents |
| SI1913000T1 (sl) | 2005-07-29 | 2012-02-29 | Pfizer Prod Inc | Derivati pirolo(2,3-d)pirimidina; njihovi intermediati in sinteza |
| JP5098843B2 (ja) | 2007-06-29 | 2012-12-12 | Ｊｆｅスチール株式会社 | 金属試料中の着目元素の固溶含有率を求める方法 |
| WO2009106442A1 (en) | 2008-02-25 | 2009-09-03 | F. Hoffmann-La Roche Ag | Pyrrolopyrazine kinase inhibitors |
| ES2378513T3 (es) | 2008-08-06 | 2012-04-13 | Pfizer Inc. | Compuestos 2-heterociclilamino piracinas sustituidas en posición 6 como inhibidores de CHK-1 |
| TWI711610B (zh) | 2009-09-04 | 2020-12-01 | 美商百健Ｍａ公司 | 布魯頓氏酪胺酸激酶抑制劑 |
| BR112012029437A2 (pt) | 2010-05-20 | 2017-03-07 | F Hoffmann - La Roche Ag | derivados de pirrolo[2,3-b]pirazina-7-carboxamida e seu uso como inibidores de jak e syk |
| US9206188B2 (en) | 2013-04-18 | 2015-12-08 | Arrien Pharmaceuticals Llc | Substituted pyrrolo[2,3-b]pyridines as ITK and JAK inhibitors |
| TN2016000227A1 (fr) | 2013-12-05 | 2017-10-06 | Pfizer | Pyrrolo[2,3-d]pyrimidinyle, pyrrolo[2,3-b]pyrazinyle et pyrollo[2,3-d]pyridinyle acrylamides. |
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- 2016-04-19 CA CA2984183A patent/CA2984183C/en active Active
- 2016-04-19 ES ES16719917T patent/ES2928757T3/es active Active
- 2016-04-19 WO PCT/IB2016/052220 patent/WO2016178110A1/en active Application Filing
- 2016-04-19 EP EP16719917.3A patent/EP3288943B1/en active Active
- 2016-04-19 JP JP2017556831A patent/JP6761815B2/ja active Active
- 2016-04-19 US US15/569,874 patent/US10703756B2/en active Active
- 2016-04-27 TW TW105113139A patent/TW201706274A/zh unknown
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