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 192
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 132
- 125000000217 alkyl group Chemical group 0.000 claims 90
- 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 62
- 125000003118 aryl group Chemical group 0.000 claims 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 32
- 208000035475 disorder Diseases 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 230000001363 autoimmune Effects 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 19
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 15
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 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
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 12
- 206010013774 Dry eye Diseases 0.000 claims 12
- 206010023332 keratitis Diseases 0.000 claims 12
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 12
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 9
- 201000004384 Alopecia Diseases 0.000 claims 8
- 208000024827 Alzheimer disease Diseases 0.000 claims 8
- 208000003174 Brain Neoplasms Diseases 0.000 claims 8
- 206010006187 Breast cancer Diseases 0.000 claims 8
- 208000026310 Breast neoplasm Diseases 0.000 claims 8
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 8
- 201000004624 Dermatitis Diseases 0.000 claims 8
- 206010028980 Neoplasm 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
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 8
- 206010046851 Uveitis Diseases 0.000 claims 8
- 230000001154 acute effect Effects 0.000 claims 8
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 8
- 231100000360 alopecia Toxicity 0.000 claims 8
- 230000001684 chronic effect Effects 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 210000004185 liver Anatomy 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 208000022873 Ocular disease Diseases 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 206010061218 Inflammation Diseases 0.000 claims 5
- 230000004054 inflammatory process Effects 0.000 claims 5
- 208000014674 injury Diseases 0.000 claims 5
- 210000000056 organ Anatomy 0.000 claims 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- UKDHINGMRKDDDZ-VXGBXAGGSA-N 2-[[(2R,4R)-2-methyl-1-prop-2-enoylpiperidin-4-yl]amino]-N-(3,3,3-trifluoropropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 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
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
- 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims 4
- 208000016683 Adult T-cell leukemia/lymphoma Diseases 0.000 claims 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 4
- 208000023328 Basedow disease Diseases 0.000 claims 4
- 208000009137 Behcet syndrome Diseases 0.000 claims 4
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 4
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 4
- 208000020925 Bipolar disease Diseases 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 4
- 206010005949 Bone cancer Diseases 0.000 claims 4
- 208000018084 Bone neoplasm Diseases 0.000 claims 4
- 201000006474 Brain Ischemia Diseases 0.000 claims 4
- 208000014644 Brain disease Diseases 0.000 claims 4
- 206010006895 Cachexia Diseases 0.000 claims 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 4
- 208000015943 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
- 208000006069 Corneal Opacity Diseases 0.000 claims 4
- 208000011231 Crohn disease Diseases 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 208000032274 Encephalopathy Diseases 0.000 claims 4
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 4
- 206010018338 Glioma Diseases 0.000 claims 4
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 4
- 208000015023 Graves' disease Diseases 0.000 claims 4
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 4
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 4
- 208000005100 Herpetic Keratitis Diseases 0.000 claims 4
- 208000023105 Huntington disease Diseases 0.000 claims 4
- 206010020751 Hypersensitivity Diseases 0.000 claims 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 4
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 4
- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 claims 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 4
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 4
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims 4
- 241001502129 Mullus Species 0.000 claims 4
- 208000034578 Multiple myelomas Diseases 0.000 claims 4
- 208000002231 Muscle Neoplasms Diseases 0.000 claims 4
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 4
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 4
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 4
- 201000002481 Myositis Diseases 0.000 claims 4
- SNIRVBFENQVIFM-RDBSUJKOSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(2S,4S)-2-methyl-1-prop-2-enoylpiperidin-4-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1[C@H](C[C@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C)C SNIRVBFENQVIFM-RDBSUJKOSA-N 0.000 claims 4
- JVYIHGXUMFZDGD-NWDGAFQWSA-N N-ethyl-2-[(2S,4R)-2-methyl-1-prop-2-enoylpiperidin-4-yl]oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 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
- MBKMZPKDZJQSMY-UHFFFAOYSA-N N-ethyl-2-[(4-methyl-1-prop-2-enoylpyrrolidin-3-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(C(C1)C)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC MBKMZPKDZJQSMY-UHFFFAOYSA-N 0.000 claims 4
- RCRWUKIWWBKMBH-CHWSQXEVSA-N N-ethyl-2-[[(3R,4R)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide 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
- 206010029113 Neovascularisation Diseases 0.000 claims 4
- 201000010133 Oligodendroglioma Diseases 0.000 claims 4
- 206010073938 Ophthalmic herpes simplex Diseases 0.000 claims 4
- 206010033128 Ovarian cancer Diseases 0.000 claims 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 206010034277 Pemphigoid Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 4
- 206010036774 Proctitis Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 208000003251 Pruritus Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- 208000033464 Reiter syndrome Diseases 0.000 claims 4
- 206010038389 Renal cancer Diseases 0.000 claims 4
- 206010039705 Scleritis Diseases 0.000 claims 4
- 206010040070 Septic Shock Diseases 0.000 claims 4
- 208000000453 Skin Neoplasms Diseases 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 4
- 206010042953 Systemic sclerosis Diseases 0.000 claims 4
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 4
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 4
- 208000024799 Thyroid disease Diseases 0.000 claims 4
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 4
- 208000025865 Ulcer Diseases 0.000 claims 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 4
- 208000001445 Uveomeningoencephalitic Syndrome Diseases 0.000 claims 4
- 206010047115 Vasculitis Diseases 0.000 claims 4
- 206010047642 Vitiligo Diseases 0.000 claims 4
- 208000034705 Vogt-Koyanagi-Harada syndrome Diseases 0.000 claims 4
- 201000006966 adult T-cell leukemia Diseases 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 208000026935 allergic disease Diseases 0.000 claims 4
- 230000007815 allergy Effects 0.000 claims 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
- 208000007502 anemia Diseases 0.000 claims 4
- 230000036506 anxiety Effects 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 210000001130 astrocyte Anatomy 0.000 claims 4
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 4
- 208000010668 atopic eczema Diseases 0.000 claims 4
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 210000001185 bone marrow Anatomy 0.000 claims 4
- 208000000594 bullous pemphigoid Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 230000002612 cardiopulmonary effect Effects 0.000 claims 4
- 210000000845 cartilage Anatomy 0.000 claims 4
- 210000004027 cell Anatomy 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- 206010008118 cerebral infarction Diseases 0.000 claims 4
- 230000006720 chronic neuroinflammation Effects 0.000 claims 4
- 210000004240 ciliary body Anatomy 0.000 claims 4
- 208000029742 colonic neoplasm Diseases 0.000 claims 4
- 210000004087 cornea Anatomy 0.000 claims 4
- 231100000269 corneal opacity Toxicity 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 201000001981 dermatomyositis Diseases 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 4
- 230000004064 dysfunction Effects 0.000 claims 4
- 206010014599 encephalitis Diseases 0.000 claims 4
- 201000002491 encephalomyelitis Diseases 0.000 claims 4
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- 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims 4
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- 201000008350 membranous glomerulonephritis Diseases 0.000 claims 4
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- 210000003098 myoblast Anatomy 0.000 claims 4
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- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 210000000496 pancreas Anatomy 0.000 claims 4
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- 208000015385 phacoanaphylactic uveitis Diseases 0.000 claims 4
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- 201000007914 proliferative diabetic retinopathy Diseases 0.000 claims 4
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- 210000003437 trachea Anatomy 0.000 claims 4
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- 208000004300 Atrophic Gastritis Diseases 0.000 claims 3
- 206010012289 Dementia Diseases 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- 208000036495 Gastritis atrophic Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- SZFMAOFYBMXHKS-GFCCVEGCSA-N N-[(2R)-1-methoxypropan-2-yl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C SZFMAOFYBMXHKS-GFCCVEGCSA-N 0.000 claims 3
- SZFMAOFYBMXHKS-LBPRGKRZSA-N N-[(2S)-1-methoxypropan-2-yl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C SZFMAOFYBMXHKS-LBPRGKRZSA-N 0.000 claims 3
- 206010058461 Orchitis noninfective Diseases 0.000 claims 3
- 229920001774 Perfluoroether Polymers 0.000 claims 3
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 3
- 208000016644 chronic atrophic gastritis Diseases 0.000 claims 3
- 230000001079 digestive effect Effects 0.000 claims 3
- 150000002118 epoxides Chemical class 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000020431 spinal cord injury Diseases 0.000 claims 3
- MPHBTNFPFIVIIC-PMPSAXMXSA-N (3S)-1-[[(3S,5S)-1-prop-2-enoyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-3-yl]methyl]pyrrolidine-3-carbonitrile Chemical compound N1=CN=C(C2=C1NC=C2)N[C@H]1C[C@H](CN(C1)C(C=C)=O)CN1C[C@H](CC1)C#N MPHBTNFPFIVIIC-PMPSAXMXSA-N 0.000 claims 2
- IMAPOKUACNUJLR-CMFFWLDZSA-N 1-[(2R,5R)-2-(methoxymethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one 1-[(2S,5S)-2-(methoxymethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one Chemical compound COC[C@H]1CC[C@H](CN1C(=O)C=C)Nc1ncnc2[nH]ccc12.COC[C@@H]1CC[C@@H](CN1C(=O)C=C)Nc1ncnc2[nH]ccc12 IMAPOKUACNUJLR-CMFFWLDZSA-N 0.000 claims 2
- UPNRCANLPOQMIO-QWRGUYRKSA-N 1-[(3R,5S)-3-(fluoromethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one Chemical compound FC[C@H]1CN(C[C@H](C1)NC=1C2=C(N=CN=1)NC=C2)C(C=C)=O UPNRCANLPOQMIO-QWRGUYRKSA-N 0.000 claims 2
- RXCPWGAEEBSNNX-MNOVXSKESA-N 1-[(3R,5S)-3-(hydroxymethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one Chemical compound OC[C@H]1CN(C[C@H](C1)NC=1C2=C(N=CN=1)NC=C2)C(C=C)=O RXCPWGAEEBSNNX-MNOVXSKESA-N 0.000 claims 2
- UPNRCANLPOQMIO-GHMZBOCLSA-N 1-[(3S,5R)-3-(fluoromethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one Chemical compound FC[C@@H]1CN(C[C@@H](C1)NC=1C2=C(N=CN=1)NC=C2)C(C=C)=O UPNRCANLPOQMIO-GHMZBOCLSA-N 0.000 claims 2
- UAKYVZGGOULDQS-UHFFFAOYSA-N 1-[4-[[7-(1,3,4-oxadiazol-2-yl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound O1C(=NN=C1)C1=CNC2=NC=C(N=C21)OC1CCN(CC1)C(C=C)=O UAKYVZGGOULDQS-UHFFFAOYSA-N 0.000 claims 2
- OVJKIMJZWIZPOM-UHFFFAOYSA-N 1-[4-[[7-(5-methyl-1H-1,2,4-triazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=NC(=NN1)C1=CNC2=NC=C(N=C21)OC1CCN(CC1)C(C=C)=O OVJKIMJZWIZPOM-UHFFFAOYSA-N 0.000 claims 2
- YRYGPGVQNYOPOT-UHFFFAOYSA-N 1-[4-[[7-(5-propan-2-yl-1H-1,2,4-triazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound CC(C)C1=NC(=NN1)C1=CNC2=NC=C(N=C21)OC1CCN(CC1)C(C=C)=O YRYGPGVQNYOPOT-UHFFFAOYSA-N 0.000 claims 2
- ITFBVGBELFLENH-UHFFFAOYSA-N 1-[4-[[7-(azetidine-1-carbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-methylamino]piperidin-1-yl]prop-2-en-1-one Chemical compound N1(CCC1)C(=O)C1=CNC2=NC=C(N=C21)N(C1CCN(CC1)C(C=C)=O)C ITFBVGBELFLENH-UHFFFAOYSA-N 0.000 claims 2
- LWFUVHFJKXHKHX-UHFFFAOYSA-N 2-(1-prop-2-enoylpiperidin-4-yl)oxy-N-(3,3,3-trifluoropropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F LWFUVHFJKXHKHX-UHFFFAOYSA-N 0.000 claims 2
- BDMXXLAUOATSMD-CHWSQXEVSA-N 2-(1-prop-2-enoylpiperidin-4-yl)oxy-N-[(1R,2R)-2-(trifluoromethyl)cyclopropyl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H]1[C@@H](C1)C(F)(F)F BDMXXLAUOATSMD-CHWSQXEVSA-N 0.000 claims 2
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- HHCYPBMCLPJCHC-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(1-methoxypropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)NC(COC)C)(C)C HHCYPBMCLPJCHC-UHFFFAOYSA-N 0.000 claims 2
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- IHEBHRUKGJGTBR-UHFFFAOYSA-N 2-[(1-prop-2-enoylpiperidin-4-yl)amino]-N-[[4-(trifluoromethyl)-1,3-thiazol-5-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1=C(N=CS1)C(F)(F)F IHEBHRUKGJGTBR-UHFFFAOYSA-N 0.000 claims 2
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- NTMYSKNQTNJIJT-UHFFFAOYSA-N 2-[(5-prop-2-enoyl-5-azaspiro[2.4]heptan-7-yl)amino]-N-(2,2,2-trifluoroethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC2(CC2)C(C1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC(F)(F)F NTMYSKNQTNJIJT-UHFFFAOYSA-N 0.000 claims 2
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- MRZPXISDUBZUQI-UHFFFAOYSA-N 2-[(5-prop-2-enoyl-5-azaspiro[2.4]heptan-7-yl)amino]-N-(4,4,4-trifluorobutyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC2(CC2)C(C1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCCC(F)(F)F MRZPXISDUBZUQI-UHFFFAOYSA-N 0.000 claims 2
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- SKQOQYOYGIXPBS-SNVBAGLBSA-N 2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-(3,3,3-trifluoropropyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F SKQOQYOYGIXPBS-SNVBAGLBSA-N 0.000 claims 2
- AFSPOLHOYPOKRU-ORAYPTAESA-N 2-[[(3R,4R)-4-cyano-4-methyl-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-(2-methoxyethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H]([C@](C1)(C)C#N)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC AFSPOLHOYPOKRU-ORAYPTAESA-N 0.000 claims 2
- YFZKLGDAYASHCO-KPZWWZAWSA-N 2-[[(3R,4R)-4-cyano-4-methyl-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-ethyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H]([C@](C1)(C)C#N)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC YFZKLGDAYASHCO-KPZWWZAWSA-N 0.000 claims 2
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- WHJDBARGHLTGBR-UHFFFAOYSA-N N-(3-cyanopropyl)-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCCCC#N WHJDBARGHLTGBR-UHFFFAOYSA-N 0.000 claims 2
- ACIRDZIHARPJMZ-UHFFFAOYSA-N N-(cyclobutylmethyl)-2-[(1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1CCC1 ACIRDZIHARPJMZ-UHFFFAOYSA-N 0.000 claims 2
- ZZBBZKMIDVMLEW-UHFFFAOYSA-N N-(cyclobutylmethyl)-5-(1-prop-2-enoylpiperidin-4-yl)oxy-1H-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C=CC(=O)N1CCC(CC1)Oc1cnc2[nH]cc(C(=O)NCC3CCC3)c2c1 ZZBBZKMIDVMLEW-UHFFFAOYSA-N 0.000 claims 2
- FRMPOHJQSMECGT-UHFFFAOYSA-N N-(cyclopentylmethyl)-2-(4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)NCC1CCCC1 FRMPOHJQSMECGT-UHFFFAOYSA-N 0.000 claims 2
- KKJKNUMDTWCWAH-DLBZAZTESA-N N-(cyclopentylmethyl)-2-[[(3R,4S)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H]([C@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1CCCC1)OC KKJKNUMDTWCWAH-DLBZAZTESA-N 0.000 claims 2
- XAHPTKWNUGEFCW-UHFFFAOYSA-N N-(cyclopropylmethyl)-2-[(1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1CC1 XAHPTKWNUGEFCW-UHFFFAOYSA-N 0.000 claims 2
- KVJKPFOQINZAKO-UHFFFAOYSA-N N-(cyclopropylmethyl)-5-(1-prop-2-enoylpiperidin-4-yl)oxy-1H-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1C=C2C(=NC=1)NC=C2C(=O)NCC1CC1 KVJKPFOQINZAKO-UHFFFAOYSA-N 0.000 claims 2
- QKPQJLUXUWAMKR-UHFFFAOYSA-N N-[(1-hydroxy-3-methylcyclopentyl)methyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC1(CC(CC1)C)O QKPQJLUXUWAMKR-UHFFFAOYSA-N 0.000 claims 2
- LLXYDEHYYRBOAM-UHFFFAOYSA-N N-[(1-hydroxycyclobutyl)methyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC1(CCC1)O LLXYDEHYYRBOAM-UHFFFAOYSA-N 0.000 claims 2
- UEYBAGIDTNOHPH-UHFFFAOYSA-N N-[(1-hydroxycyclopentyl)methyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC1(CCCC1)O UEYBAGIDTNOHPH-UHFFFAOYSA-N 0.000 claims 2
- STFDTGAGIRHBTI-HUUCEWRRSA-N N-[(1R,2R)-2-fluorocyclopentyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H]1[C@@H](CCC1)F STFDTGAGIRHBTI-HUUCEWRRSA-N 0.000 claims 2
- STFDTGAGIRHBTI-LSDHHAIUSA-N N-[(1R,2S)-2-fluorocyclopentyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H]1[C@H](CCC1)F STFDTGAGIRHBTI-LSDHHAIUSA-N 0.000 claims 2
- UIYJTQKBSYPJBR-QWHCGFSZSA-N N-[(1R,3S)-3-fluorocyclopentyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H]1C[C@H](CC1)F UIYJTQKBSYPJBR-QWHCGFSZSA-N 0.000 claims 2
- UIYJTQKBSYPJBR-OLZOCXBDSA-N N-[(1S,3R)-3-fluorocyclopentyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H]1C[C@@H](CC1)F UIYJTQKBSYPJBR-OLZOCXBDSA-N 0.000 claims 2
- COUBAMSIYIHZMU-KGLIPLIRSA-N N-[(1S,3R)-3-fluorocyclopentyl]-5-(1-prop-2-enoylpiperidin-4-yl)oxy-1H-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1C=C2C(=NC=1)NC=C2C(=O)N[C@@H]1C[C@@H](CC1)F COUBAMSIYIHZMU-KGLIPLIRSA-N 0.000 claims 2
- UIYJTQKBSYPJBR-STQMWFEESA-N N-[(1S,3S)-3-fluorocyclopentyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H]1C[C@H](CC1)F UIYJTQKBSYPJBR-STQMWFEESA-N 0.000 claims 2
- BWAZNSJLEDTLMJ-UHFFFAOYSA-N N-[(2-fluorophenyl)methyl]-2-[(1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1=C(C=CC=C1)F BWAZNSJLEDTLMJ-UHFFFAOYSA-N 0.000 claims 2
- DKTGMJXTLSFBGB-LJQANCHMSA-N N-[(2R)-1-(3-cyanophenyl)-3-hydroxypropan-2-yl]-2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](CC1=CC(=CC=C1)C#N)CO)(C)C DKTGMJXTLSFBGB-LJQANCHMSA-N 0.000 claims 2
- LRGVKLZBLIFELO-CQSZACIVSA-N N-[(2R)-1-cyanobutan-2-yl]-2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](CC#N)CC)(C)C LRGVKLZBLIFELO-CQSZACIVSA-N 0.000 claims 2
- AEFQCMHCBVNHGM-CYBMUJFWSA-N N-[(2R)-1-cyanobutan-2-yl]-2-(4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](CC#N)CC AEFQCMHCBVNHGM-CYBMUJFWSA-N 0.000 claims 2
- RWGWCOBUWGMSGH-CYBMUJFWSA-N N-[(2R)-1-cyanopropan-2-yl]-2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](CC#N)C)(C)C RWGWCOBUWGMSGH-CYBMUJFWSA-N 0.000 claims 2
- JGLTVVFEADXYFK-PZORYLMUSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[(1-prop-2-enoylpyrrolidin-3-yl)methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C JGLTVVFEADXYFK-PZORYLMUSA-N 0.000 claims 2
- RIBMLGOGCQASQY-PZORYLMUSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[(1-prop-2-enoylpyrrolidin-3-yl)methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C RIBMLGOGCQASQY-PZORYLMUSA-N 0.000 claims 2
- JGLTVVFEADXYFK-CHWSQXEVSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C JGLTVVFEADXYFK-CHWSQXEVSA-N 0.000 claims 2
- RIBMLGOGCQASQY-CHWSQXEVSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C RIBMLGOGCQASQY-CHWSQXEVSA-N 0.000 claims 2
- VBMLOUXBTJEXQV-YUELXQCFSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(3R,4S)-4-methoxy-1-prop-2-enoylpiperidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H]([C@H](CC1)OC)NC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C VBMLOUXBTJEXQV-YUELXQCFSA-N 0.000 claims 2
- JGLTVVFEADXYFK-OLZOCXBDSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C JGLTVVFEADXYFK-OLZOCXBDSA-N 0.000 claims 2
- RIBMLGOGCQASQY-OLZOCXBDSA-N N-[(2R)-1-methoxypropan-2-yl]-2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@@H](COC)C RIBMLGOGCQASQY-OLZOCXBDSA-N 0.000 claims 2
- UGUOYVUAYBBPFP-GFCCVEGCSA-N N-[(2R)-butan-2-yl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound CC[C@@H](C)NC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)nc12 UGUOYVUAYBBPFP-GFCCVEGCSA-N 0.000 claims 2
- JLSRDLJGNSNJIM-UEWDXFNNSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[(1-prop-2-enoylpyrrolidin-2-yl)methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CCC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JLSRDLJGNSNJIM-UEWDXFNNSA-N 0.000 claims 2
- JGLTVVFEADXYFK-UEWDXFNNSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[(1-prop-2-enoylpyrrolidin-3-yl)methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JGLTVVFEADXYFK-UEWDXFNNSA-N 0.000 claims 2
- RIBMLGOGCQASQY-UEWDXFNNSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[(1-prop-2-enoylpyrrolidin-3-yl)methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C RIBMLGOGCQASQY-UEWDXFNNSA-N 0.000 claims 2
- JLSRDLJGNSNJIM-QWHCGFSZSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(2R)-1-prop-2-enoylpyrrolidin-2-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1[C@H](CCC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JLSRDLJGNSNJIM-QWHCGFSZSA-N 0.000 claims 2
- JLSRDLJGNSNJIM-STQMWFEESA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(2S)-1-prop-2-enoylpyrrolidin-2-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1[C@@H](CCC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JLSRDLJGNSNJIM-STQMWFEESA-N 0.000 claims 2
- SNIRVBFENQVIFM-IHRRRGAJSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(2S,4S)-2-methyl-1-prop-2-enoylpiperidin-4-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1[C@H](C[C@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C)C SNIRVBFENQVIFM-IHRRRGAJSA-N 0.000 claims 2
- JGLTVVFEADXYFK-QWHCGFSZSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JGLTVVFEADXYFK-QWHCGFSZSA-N 0.000 claims 2
- RIBMLGOGCQASQY-QWHCGFSZSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C RIBMLGOGCQASQY-QWHCGFSZSA-N 0.000 claims 2
- JGLTVVFEADXYFK-STQMWFEESA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]methoxy]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)COC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C JGLTVVFEADXYFK-STQMWFEESA-N 0.000 claims 2
- RIBMLGOGCQASQY-STQMWFEESA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]methylamino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)CNC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C RIBMLGOGCQASQY-STQMWFEESA-N 0.000 claims 2
- PJXVBNUKGVIHRY-CFVMTHIKSA-N N-[(2S)-1-methoxypropan-2-yl]-2-[[(3S,4R)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H]([C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C)OC PJXVBNUKGVIHRY-CFVMTHIKSA-N 0.000 claims 2
- UGUOYVUAYBBPFP-LBPRGKRZSA-N N-[(2S)-butan-2-yl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound CC[C@H](C)NC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)nc12 UGUOYVUAYBBPFP-LBPRGKRZSA-N 0.000 claims 2
- LZDWYCNFYNRXOJ-UHFFFAOYSA-N N-[(3,3-difluoro-1-hydroxycyclohexyl)methyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC1(CC(CCC1)(F)F)O LZDWYCNFYNRXOJ-UHFFFAOYSA-N 0.000 claims 2
- UNPFLMSOTTWTTD-UHFFFAOYSA-N N-[(3,3-difluorocyclobutyl)methyl]-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC1CC(C1)(F)F UNPFLMSOTTWTTD-UHFFFAOYSA-N 0.000 claims 2
- GQIMLDLQYHXMML-UHFFFAOYSA-N N-[(3,3-difluorocyclobutyl)methyl]-2-(4-prop-2-enoylpiperazin-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)NCC1CC(C1)(F)F GQIMLDLQYHXMML-UHFFFAOYSA-N 0.000 claims 2
- VPOGSQNZJKOZPD-INIZCTEOSA-N N-[(3,3-difluorocyclobutyl)methyl]-2-[(3S)-3-(2-methylpropyl)-4-prop-2-enoylpiperazin-1-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1[C@H](CN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)NCC1CC(C1)(F)F)CC(C)C VPOGSQNZJKOZPD-INIZCTEOSA-N 0.000 claims 2
- ZBVMXEIIKKKYDI-UHFFFAOYSA-N N-[(3-cyano-4-fluorophenyl)methyl]-2-[(1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1=CC(=C(C=C1)F)C#N ZBVMXEIIKKKYDI-UHFFFAOYSA-N 0.000 claims 2
- KMEVSPGGUIHLCC-UHFFFAOYSA-N N-[(3-fluoro-4-methoxyphenyl)methyl]-2-[(1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC1=CC(=C(C=C1)OC)F KMEVSPGGUIHLCC-UHFFFAOYSA-N 0.000 claims 2
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| WO2018140600A1 (en) * | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Fused hetero-hetero bicyclic compounds and methods of use thereof |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | 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 |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| US10392368B2 (en) | 2017-08-01 | 2019-08-27 | Theravance Biopharma R&D Ip, Llc | Pyrazolo and triazolo bicyclic compounds as JAK kinase inhibitors |
| TWI903299B (zh) | 2018-03-08 | 2025-11-01 | 美商英塞特公司 | 作為PI3K-γ抑制劑之胺基吡嗪二醇化合物 |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CA3107168A1 (en) | 2018-08-01 | 2020-02-06 | Araxes Pharma Llc | Heterocyclic spiro compounds and methods of use thereof for the treatment of cancer |
| CN112823005B (zh) | 2018-08-10 | 2024-08-20 | 阿克拉瑞斯治疗股份有限公司 | 吡咯并嘧啶itk抑制剂 |
| 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 |
| CN119060058A (zh) * | 2024-08-21 | 2024-12-03 | 武汉九州钰民医药科技有限公司 | 一种甲苯磺酸利特昔替尼的合成方法 |
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|---|---|---|---|---|
| TW505646B (en) | 1998-06-19 | 2002-10-11 | Pfizer Prod Inc | Pyrrolo [2,3-d] pyrimidine compounds |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| PT1382339E (pt) | 1999-12-10 | 2008-02-06 | Pfizer Prod Inc | Composições que contêm derivados de pirrolo[2,3-d]- pirimidina |
| PL359563A1 (pl) | 2000-06-26 | 2004-08-23 | Pfizer Products Inc. | Związki pirolo [2,3-d] pirymidynowe jako środki immunosupresyjne |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| KR100678800B1 (ko) | 2002-11-21 | 2007-02-05 | 화이자 프로덕츠 인코포레이티드 | 3-아미노-피페리딘 유도체 및 그의 제조 방법 |
| 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 |
| CA2614907C (en) | 2005-07-29 | 2012-02-28 | Pfizer Products Inc. | Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis |
| 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 |
| MX2010008198A (es) | 2008-02-25 | 2010-08-23 | Hoffmann La Roche | Inhibidores de cinasa de pirrolopirazina. |
| ES2378513T3 (es) | 2008-08-06 | 2012-04-13 | Pfizer Inc. | Compuestos 2-heterociclilamino piracinas sustituidas en posición 6 como inhibidores de CHK-1 |
| CA2771822C (en) | 2009-09-04 | 2020-08-11 | Daniel A. Erlanson | Bruton's tyrosine kinase inhibitors |
| KR20130083386A (ko) | 2010-05-20 | 2013-07-22 | 에프. 호프만-라 로슈 아게 | 피롤로[2,3-ｂ]피라진-7-카복스아마이드 유도체 및 ＪＡＫ 및 ＳＹＫ 억제제로서의 그의 용도 |
| US9206188B2 (en) * | 2013-04-18 | 2015-12-08 | Arrien Pharmaceuticals Llc | Substituted pyrrolo[2,3-b]pyridines as ITK and JAK inhibitors |
| WO2015083028A1 (en) | 2013-12-05 | 2015-06-11 | Pfizer Inc. | Pyrrolo[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyrazinyl and pyrrolo[2,3-d]pyridinyl acrylamides |
-
2016
- 2016-04-19 ES ES16719917T patent/ES2928757T3/es active Active
- 2016-04-19 JP JP2017556831A patent/JP6761815B2/ja active Active
- 2016-04-19 CA CA2984183A patent/CA2984183C/en active Active
- 2016-04-19 EP EP16719917.3A patent/EP3288943B1/en active Active
- 2016-04-19 WO PCT/IB2016/052220 patent/WO2016178110A1/en not_active Ceased
- 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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