JP2018514560A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- 230000002124 endocrine Effects 0.000 claims 4
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 claims 4
- 210000003414 extremity Anatomy 0.000 claims 4
- 208000030533 eye disease Diseases 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 208000024908 graft versus host disease Diseases 0.000 claims 4
- 210000002216 heart Anatomy 0.000 claims 4
- 201000010884 herpes simplex virus keratitis Diseases 0.000 claims 4
- 210000003734 kidney Anatomy 0.000 claims 4
- 201000010982 kidney cancer Diseases 0.000 claims 4
- 208000032839 leukemia Diseases 0.000 claims 4
- 201000007270 liver cancer Diseases 0.000 claims 4
- 208000014018 liver neoplasm Diseases 0.000 claims 4
- 210000004072 lung Anatomy 0.000 claims 4
- 201000005202 lung cancer Diseases 0.000 claims 4
- 208000020816 lung neoplasm Diseases 0.000 claims 4
- 206010025135 lupus erythematosus Diseases 0.000 claims 4
- 208000024714 major depressive disease Diseases 0.000 claims 4
- 230000003211 malignant effect Effects 0.000 claims 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 4
- 201000006512 mast cell neoplasm Diseases 0.000 claims 4
- 208000008585 mastocytosis Diseases 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 201000008350 membranous glomerulonephritis Diseases 0.000 claims 4
- 208000021039 metastatic melanoma Diseases 0.000 claims 4
- 210000000214 mouth Anatomy 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- 210000003205 muscle Anatomy 0.000 claims 4
- 201000002077 muscle cancer Diseases 0.000 claims 4
- 206010028417 myasthenia gravis Diseases 0.000 claims 4
- 210000003098 myoblast Anatomy 0.000 claims 4
- 201000008383 nephritis Diseases 0.000 claims 4
- 210000005036 nerve Anatomy 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 230000000414 obstructive effect Effects 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 210000000496 pancreas Anatomy 0.000 claims 4
- 201000002528 pancreatic cancer Diseases 0.000 claims 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 4
- 208000015385 phacoanaphylactic uveitis Diseases 0.000 claims 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 4
- 201000007914 proliferative diabetic retinopathy Diseases 0.000 claims 4
- 230000001823 pruritic effect Effects 0.000 claims 4
- 230000002685 pulmonary effect Effects 0.000 claims 4
- 208000002574 reactive arthritis Diseases 0.000 claims 4
- 208000023504 respiratory system disease Diseases 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- 201000000306 sarcoidosis Diseases 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 230000036303 septic shock Effects 0.000 claims 4
- 210000003491 skin Anatomy 0.000 claims 4
- 201000000849 skin cancer Diseases 0.000 claims 4
- 210000000813 small intestine Anatomy 0.000 claims 4
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- 206010043778 thyroiditis Diseases 0.000 claims 4
- 210000003437 trachea Anatomy 0.000 claims 4
- 238000002054 transplantation Methods 0.000 claims 4
- 230000008733 trauma Effects 0.000 claims 4
- 230000009529 traumatic brain injury Effects 0.000 claims 4
- 231100000397 ulcer Toxicity 0.000 claims 4
- 201000005112 urinary bladder cancer Diseases 0.000 claims 4
- 201000005539 vernal conjunctivitis Diseases 0.000 claims 4
- 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
- XNDGDJJWBAMULC-SJLPKXTDSA-N 2-(1-prop-2-enoylpiperidin-4-yl)oxy-N-[(2R,3R)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]-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]([C@H](C(F)(F)F)O)C(C)C XNDGDJJWBAMULC-SJLPKXTDSA-N 0.000 claims 2
- XNDGDJJWBAMULC-WMZOPIPTSA-N 2-(1-prop-2-enoylpiperidin-4-yl)oxy-N-[(2S,3S)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]-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]([C@@H](C(F)(F)F)O)C(C)C XNDGDJJWBAMULC-WMZOPIPTSA-N 0.000 claims 2
- IDEMPLXABQXMOL-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(1-hydroxyhexan-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(CO)CCCC)(C)C IDEMPLXABQXMOL-UHFFFAOYSA-N 0.000 claims 2
- HCMAMXCGZPEZRT-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(1-methoxy-2-methylpropan-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)C HCMAMXCGZPEZRT-UHFFFAOYSA-N 0.000 claims 2
- 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
- JSLMYQWZTHUGJR-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(2,2,2-trifluoroethyl)-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)NCC(F)(F)F)(C)C JSLMYQWZTHUGJR-UHFFFAOYSA-N 0.000 claims 2
- QNXZLPZBFUMBFW-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(2,2-dimethylpropyl)-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)NCC(C)(C)C)(C)C QNXZLPZBFUMBFW-UHFFFAOYSA-N 0.000 claims 2
- RMARTEOQVCWZPA-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(4,4,4-trifluorobutyl)-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)NCCCC(F)(F)F)(C)C RMARTEOQVCWZPA-UHFFFAOYSA-N 0.000 claims 2
- XHLOTMPJEUNVPI-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(oxan-3-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)NC1COCCC1)(C)C XHLOTMPJEUNVPI-UHFFFAOYSA-N 0.000 claims 2
- MOBXTTXJDULMDB-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-(oxolan-3-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)NC1COCC1)(C)C MOBXTTXJDULMDB-UHFFFAOYSA-N 0.000 claims 2
- ODODTLPCAXQBMM-SFHVURJKSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(1R)-1-(4-fluorophenyl)-2-hydroxyethyl]-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](CO)C1=CC=C(C=C1)F)(C)C ODODTLPCAXQBMM-SFHVURJKSA-N 0.000 claims 2
- IPDPJOGABIYGON-CHWSQXEVSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(1R,2R)-2-(trifluoromethyl)cyclopropyl]-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]1[C@@H](C1)C(F)(F)F)(C)C IPDPJOGABIYGON-CHWSQXEVSA-N 0.000 claims 2
- DBAHQOBZZNBBAK-AOMKIAJQSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(1R,2S)-1-hydroxy-1-phenylpropan-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)N[C@H]([C@@H](C1=CC=CC=C1)O)C)(C)C DBAHQOBZZNBBAK-AOMKIAJQSA-N 0.000 claims 2
- UZDHWBCEZKWWHC-QFIPXVFZSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(1S)-2-hydroxy-2-methyl-1-phenylpropyl]-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](C(C)(C)O)C1=CC=CC=C1)(C)C UZDHWBCEZKWWHC-QFIPXVFZSA-N 0.000 claims 2
- WBNNHQGAQWXGJC-QGZVFWFLSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(2R)-1-phenoxypropan-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)N[C@@H](COC1=CC=CC=C1)C)(C)C WBNNHQGAQWXGJC-QGZVFWFLSA-N 0.000 claims 2
- ORIYOPJERRUZGB-GOSISDBHSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(2R)-1-phenylmethoxypropan-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)N[C@@H](COCC1=CC=CC=C1)C)(C)C ORIYOPJERRUZGB-GOSISDBHSA-N 0.000 claims 2
- UWSBABXVHBTWJQ-AWEZNQCLSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(2S)-1-hydroxypentan-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)N[C@H](CO)CCC)(C)C UWSBABXVHBTWJQ-AWEZNQCLSA-N 0.000 claims 2
- WBNNHQGAQWXGJC-KRWDZBQOSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(2S)-1-phenoxypropan-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)N[C@H](COC1=CC=CC=C1)C)(C)C WBNNHQGAQWXGJC-KRWDZBQOSA-N 0.000 claims 2
- ZRAWVMINQFKYOR-DZGCQCFKSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(2S,3R)-2-methyloxolan-3-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]1[C@H](C)OCC1)(C)C ZRAWVMINQFKYOR-DZGCQCFKSA-N 0.000 claims 2
- MOBXTTXJDULMDB-ZDUSSCGKSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(3S)-oxolan-3-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]1COCC1)(C)C MOBXTTXJDULMDB-ZDUSSCGKSA-N 0.000 claims 2
- JDWAVVSISKOYKH-SJORKVTESA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[(3S,4R)-4-(4-fluoropyrazol-1-yl)oxolan-3-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]1COC[C@@H]1N1N=CC(=C1)F)(C)C JDWAVVSISKOYKH-SJORKVTESA-N 0.000 claims 2
- XKAFXHBIHPMAAP-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[1-(2-fluorophenyl)-2-hydroxyethyl]-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(CO)C1=C(C=CC=C1)F)(C)C XKAFXHBIHPMAAP-UHFFFAOYSA-N 0.000 claims 2
- ODODTLPCAXQBMM-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[1-(4-fluorophenyl)-2-hydroxyethyl]-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(CO)C1=CC=C(C=C1)F)(C)C ODODTLPCAXQBMM-UHFFFAOYSA-N 0.000 claims 2
- NWOOCVOSDLNUBA-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-[3-(hydroxymethyl)pentan-3-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(CC)(CC)CO)(C)C NWOOCVOSDLNUBA-UHFFFAOYSA-N 0.000 claims 2
- IZZOHSQGSBUSSA-UHFFFAOYSA-N 2-(3,3-dimethyl-4-prop-2-enoylpiperazin-1-yl)-N-prop-2-ynyl-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)NCC#C)(C)C IZZOHSQGSBUSSA-UHFFFAOYSA-N 0.000 claims 2
- YQJJEQZFLVCYKY-UHFFFAOYSA-N 2-(4-prop-2-enoylpiperazin-1-yl)-N-(4,4,4-trifluoro-2-methylbutyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCN(CC1)C=1N=C2C(=NC=1)NC=C2C(=O)NCC(CC(F)(F)F)C YQJJEQZFLVCYKY-UHFFFAOYSA-N 0.000 claims 2
- VLPNSFVOEBGBBY-VXGBXAGGSA-N 2-(4-prop-2-enoylpiperazin-1-yl)-N-[(1R,2R)-2-(trifluoromethyl)cyclopropyl]-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]1[C@@H](C1)C(F)(F)F VLPNSFVOEBGBBY-VXGBXAGGSA-N 0.000 claims 2
- KWTANVQFBKTPIZ-UHFFFAOYSA-N 2-[(1-prop-2-enoylpiperidin-4-yl)amino]-N-[(4-pyrazol-1-ylphenyl)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=CC=C(C=C1)N1N=CC=C1 KWTANVQFBKTPIZ-UHFFFAOYSA-N 0.000 claims 2
- 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
- QLZKTRSBUVOWJI-UHFFFAOYSA-N 2-[(1-prop-2-enoylpiperidin-4-yl)amino]-N-propyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC QLZKTRSBUVOWJI-UHFFFAOYSA-N 0.000 claims 2
- UKDHINGMRKDDDZ-UHFFFAOYSA-N 2-[(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)N1C(CC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F)C UKDHINGMRKDDDZ-UHFFFAOYSA-N 0.000 claims 2
- YAOZEJNFMZGOOG-UHFFFAOYSA-N 2-[(2-methyl-1-prop-2-enoylpiperidin-4-yl)amino]-N-(4,4,4-trifluorobutyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCCC(F)(F)F)C YAOZEJNFMZGOOG-UHFFFAOYSA-N 0.000 claims 2
- KOCKRCVSFCMKLP-IYXRBSQSSA-N 2-[(2-methyl-1-prop-2-enoylpiperidin-4-yl)amino]-N-[(2R)-4,4,4-trifluoro-2-methylbutyl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NC[C@@H](CC(F)(F)F)C)C KOCKRCVSFCMKLP-IYXRBSQSSA-N 0.000 claims 2
- IUKYCBMTPZBLLP-NEPJUHHUSA-N 2-[(3S,5S)-1-prop-2-enoyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-3-yl]acetonitrile Chemical compound C(C=C)(=O)N1C[C@@H](C[C@@H](C1)NC=1C2=C(N=CN=1)NC=C2)CC#N IUKYCBMTPZBLLP-NEPJUHHUSA-N 0.000 claims 2
- OVCKWCILTYZTTA-UHFFFAOYSA-N 2-[(4-methyl-1-prop-2-enoylpiperidin-4-yl)amino]-N-(4,4,4-trifluoro-2-methylbutyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)(C)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC(CC(F)(F)F)C OVCKWCILTYZTTA-UHFFFAOYSA-N 0.000 claims 2
- 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
- BOQSAULJJRSAII-UHFFFAOYSA-N 2-[(5-prop-2-enoyl-5-azaspiro[2.4]heptan-7-yl)amino]-N-(3,3,3-trifluoropropyl)-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)NCCC(F)(F)F BOQSAULJJRSAII-UHFFFAOYSA-N 0.000 claims 2
- 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
- JOXAHTORCAPWOB-YXWRBFHGSA-N 2-[3-(methoxymethyl)-3-methyl-4-prop-2-enoylpiperazin-1-yl]-N-[(2S)-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)N[C@H](COC)C)(C)COC JOXAHTORCAPWOB-YXWRBFHGSA-N 0.000 claims 2
- LQQXGPGQRYJLBN-SECBINFHSA-N 2-[[(3R)-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-(2,2,2-trifluoroethyl)-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)NCC(F)(F)F LQQXGPGQRYJLBN-SECBINFHSA-N 0.000 claims 2
- 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
- CBKFLDREHRAFHW-GJZGRUSLSA-N 2-[[(3R,4R)-4-cyclopropyl-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@@H](C1)C1CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC CBKFLDREHRAFHW-GJZGRUSLSA-N 0.000 claims 2
- VTLZVUKUEQWJKV-KBPBESRZSA-N 2-[[(3R,4R)-4-cyclopropyl-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@@H](C1)C1CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC VTLZVUKUEQWJKV-KBPBESRZSA-N 0.000 claims 2
- XTYPDDNPTMLXEG-OCCSQVGLSA-N 2-[[(3R,4R)-4-ethyl-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@@H](C1)CC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC XTYPDDNPTMLXEG-OCCSQVGLSA-N 0.000 claims 2
- HLAHLYRLXZJPBM-UONOGXRCSA-N 2-[[(3R,4S)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-N-(4,4,4-trifluorobutyl)-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)NCCCC(F)(F)F)OC HLAHLYRLXZJPBM-UONOGXRCSA-N 0.000 claims 2
- YHRZRHXBCSDMBO-XJFOESAGSA-N 2-[[(3R,4S)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-N-[(1R,2R)-2-(trifluoromethyl)cyclopropyl]-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]1[C@@H](C1)C(F)(F)F)OC YHRZRHXBCSDMBO-XJFOESAGSA-N 0.000 claims 2
- AFSPOLHOYPOKRU-DJJJIMSYSA-N 2-[[(3R,4S)-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-DJJJIMSYSA-N 0.000 claims 2
- YFZKLGDAYASHCO-SGTLLEGYSA-N 2-[[(3R,4S)-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-SGTLLEGYSA-N 0.000 claims 2
- FTGLXLHGDCQUOM-KGLIPLIRSA-N 2-[[(3R,5S)-5-(ethoxymethyl)-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[C@H]1COCC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC FTGLXLHGDCQUOM-KGLIPLIRSA-N 0.000 claims 2
- FZSWGTCSFODRMB-OLZOCXBDSA-N 2-[[(3R,5S)-5-(ethoxymethyl)-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[C@H]1COCC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC FZSWGTCSFODRMB-OLZOCXBDSA-N 0.000 claims 2
- LQQXGPGQRYJLBN-VIFPVBQESA-N 2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-(2,2,2-trifluoroethyl)-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)NCC(F)(F)F LQQXGPGQRYJLBN-VIFPVBQESA-N 0.000 claims 2
- SKQOQYOYGIXPBS-JTQLQIEISA-N 2-[[(3S)-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-JTQLQIEISA-N 0.000 claims 2
- YBWSJJJUXBVBMJ-NSHDSACASA-N 2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]-N-(4,4,4-trifluorobutyl)-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)NCCCC(F)(F)F YBWSJJJUXBVBMJ-NSHDSACASA-N 0.000 claims 2
- RMQKVTJRRCLHJP-NEPJUHHUSA-N 2-[[(3S,4R)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-N-(2,2,2-trifluoroethyl)-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(F)(F)F)OC RMQKVTJRRCLHJP-NEPJUHHUSA-N 0.000 claims 2
- HBUOIOHAMSZQCZ-OLZOCXBDSA-N 2-[[(3S,4R)-3-methoxy-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)N1C[C@@H]([C@@H](CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F)OC HBUOIOHAMSZQCZ-OLZOCXBDSA-N 0.000 claims 2
- MKTFPVWULGNIAU-UCWKZMIHSA-N 2-[[(3S,4R)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-N-(4,4,4-trifluoro-2-methylbutyl)-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(CC(F)(F)F)C)OC MKTFPVWULGNIAU-UCWKZMIHSA-N 0.000 claims 2
- YHRZRHXBCSDMBO-SYQHCUMBSA-N 2-[[(3S,4R)-3-methoxy-1-prop-2-enoylpiperidin-4-yl]amino]-N-[(1R,2R)-2-(trifluoromethyl)cyclopropyl]-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]1[C@@H](C1)C(F)(F)F)OC YHRZRHXBCSDMBO-SYQHCUMBSA-N 0.000 claims 2
- CBKFLDREHRAFHW-HUUCEWRRSA-N 2-[[(3S,4S)-4-cyclopropyl-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@H](C1)C1CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC CBKFLDREHRAFHW-HUUCEWRRSA-N 0.000 claims 2
- VTLZVUKUEQWJKV-ZIAGYGMSSA-N 2-[[(3S,4S)-4-cyclopropyl-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@H](C1)C1CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC VTLZVUKUEQWJKV-ZIAGYGMSSA-N 0.000 claims 2
- PZWXDCGEVJHDIL-UHFFFAOYSA-N 2-[methyl-(1-prop-2-enoylpiperidin-4-yl)amino]-N-propan-2-yl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)N(C=1N=C2C(=NC=1)NC=C2C(=O)NC(C)C)C PZWXDCGEVJHDIL-UHFFFAOYSA-N 0.000 claims 2
- XBCPAFWIVOORMN-KGLIPLIRSA-N 3-[[(3R,5S)-1-prop-2-enoyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-3-yl]methoxy]propanenitrile Chemical compound C(C=C)(=O)N1C[C@@H](C[C@@H](C1)NC=1C2=C(N=CN=1)NC=C2)COCCC#N XBCPAFWIVOORMN-KGLIPLIRSA-N 0.000 claims 2
- XBCPAFWIVOORMN-UONOGXRCSA-N 3-[[(3S,5R)-1-prop-2-enoyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-3-yl]methoxy]propanenitrile Chemical compound C(C=C)(=O)N1C[C@H](C[C@H](C1)NC=1C2=C(N=CN=1)NC=C2)COCCC#N XBCPAFWIVOORMN-UONOGXRCSA-N 0.000 claims 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- GCXNBCPONFMEEV-DHXVBOOMSA-N 4-[[(3R,5S)-5-hydroxy-1-prop-2-enoylpiperidin-3-yl]amino]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile Chemical compound C=CC(=O)N1CCC(CC1)Oc1cnc2[nH]cc(C#N)c2n1.O[C@H]1C[C@H](CN(C1)C(=O)C=C)Nc1ncnc2[nH]cc(C#N)c12 GCXNBCPONFMEEV-DHXVBOOMSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- MCKBZAMFPSEVIC-UHFFFAOYSA-N 5-(1-prop-2-enoylpiperidin-4-yl)oxy-N-(3,3,3-trifluoropropyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1C=C2C(=NC=1)NC=C2C(=O)NCCC(F)(F)F MCKBZAMFPSEVIC-UHFFFAOYSA-N 0.000 claims 2
- NUSFSLJJSVANDU-UHFFFAOYSA-N C(C=C)(=O)N(C1CN(C1)C=1N=C2C(=NC=1)NC=C2C(=O)NCCOC)C Chemical compound C(C=C)(=O)N(C1CN(C1)C=1N=C2C(=NC=1)NC=C2C(=O)NCCOC)C NUSFSLJJSVANDU-UHFFFAOYSA-N 0.000 claims 2
- GLCZCSBYSFLTHE-NSHDSACASA-N C(C=C)(=O)N(C1CN(C1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C)C Chemical compound C(C=C)(=O)N(C1CN(C1)C=1N=C2C(=NC=1)NC=C2C(=O)N[C@H](COC)C)C GLCZCSBYSFLTHE-NSHDSACASA-N 0.000 claims 2
- RMTKHDHCRHINOI-CICJTZRQSA-N C(C=C)(=O)N1CC2(CC2)C(C1)NC=1N=C2C(=NC1)NC=C2C(=O)NCC.C(C=C)(=O)N2C[C@H](CC2)NC=2N=C1C(=NC2)NC=C1C(=O)NCC Chemical compound C(C=C)(=O)N1CC2(CC2)C(C1)NC=1N=C2C(=NC1)NC=C2C(=O)NCC.C(C=C)(=O)N2C[C@H](CC2)NC=2N=C1C(=NC2)NC=C1C(=O)NCC RMTKHDHCRHINOI-CICJTZRQSA-N 0.000 claims 2
- UYXTUSYLPCAZSD-UHFFFAOYSA-N C(C=C)(=O)N1CCC(CC1)N(C=1N=C2C(=NC1)NC=C2C(=O)NCC)C.C(C=C)(=O)N(C2CN(C2)C=2N=C1C(=NC2)NC=C1C(=O)NCC)C Chemical compound C(C=C)(=O)N1CCC(CC1)N(C=1N=C2C(=NC1)NC=C2C(=O)NCC)C.C(C=C)(=O)N(C2CN(C2)C=2N=C1C(=NC2)NC=C1C(=O)NCC)C UYXTUSYLPCAZSD-UHFFFAOYSA-N 0.000 claims 2
- MWTNPTQBLMKGRP-UHFFFAOYSA-N C(C=C)(=O)N1CCC(CC1)OC=1C=C2C(=NC1)NC=C2C(=O)NCCC.C(C=C)(=O)N2CCC(CC2)OC=2C=C1C(=NC2)NC=C1C(=O)NCC1=C(C=CC=C1)F Chemical compound C(C=C)(=O)N1CCC(CC1)OC=1C=C2C(=NC1)NC=C2C(=O)NCCC.C(C=C)(=O)N2CCC(CC2)OC=2C=C1C(=NC2)NC=C1C(=O)NCC1=C(C=CC=C1)F MWTNPTQBLMKGRP-UHFFFAOYSA-N 0.000 claims 2
- FNRKXFSZCPWLOD-SNVBAGLBSA-N C(C=C)(=O)N1C[C@@H](CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC Chemical compound C(C=C)(=O)N1C[C@@H](CC1)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC FNRKXFSZCPWLOD-SNVBAGLBSA-N 0.000 claims 2
- HPVGVDKZLBWXFE-PQEZBEDRSA-N C(C=C)(=O)N1[C@H](C[C@H](CC1)NC=1N=C2C(=NC1)NC=C2C(=O)NCC)C.C(C=C)(=O)N2CCC(CC2)OC=2C=C1C(=NC2)NC=C1C(=O)NCCCC Chemical compound C(C=C)(=O)N1[C@H](C[C@H](CC1)NC=1N=C2C(=NC1)NC=C2C(=O)NCC)C.C(C=C)(=O)N2CCC(CC2)OC=2C=C1C(=NC2)NC=C1C(=O)NCCCC HPVGVDKZLBWXFE-PQEZBEDRSA-N 0.000 claims 2
- DYDKKAOYCWUMRA-UHFFFAOYSA-N N-(1-bicyclo[1.1.1]pentanyl)-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)NC12CC(C1)C2 DYDKKAOYCWUMRA-UHFFFAOYSA-N 0.000 claims 2
- CQRGKSXGAHYRBL-UHFFFAOYSA-N N-(1-cyclopropylethyl)-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)NC(C)C1CC1 CQRGKSXGAHYRBL-UHFFFAOYSA-N 0.000 claims 2
- LZRWYOJPXMNLDP-UHFFFAOYSA-N N-(2,2-difluorocyclopentyl)-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)NC1C(CCC1)(F)F LZRWYOJPXMNLDP-UHFFFAOYSA-N 0.000 claims 2
- LOIBDFQPQNJWBM-UHFFFAOYSA-N N-(2,2-difluoropropyl)-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)NCC(C)(F)F LOIBDFQPQNJWBM-UHFFFAOYSA-N 0.000 claims 2
- WZLXTALANVIUKA-UHFFFAOYSA-N N-(2,2-difluoropropyl)-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)NCC(C)(F)F)(C)C WZLXTALANVIUKA-UHFFFAOYSA-N 0.000 claims 2
- IFHJYJZGQOWSPZ-UHFFFAOYSA-N N-(2,2-dimethylpropyl)-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound CC(C)(C)CNC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)nc12 IFHJYJZGQOWSPZ-UHFFFAOYSA-N 0.000 claims 2
- FOEQRVDBRWOKEG-UHFFFAOYSA-N N-(2,2-dimethylpropyl)-2-[(2-methyl-1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C(CC(CC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC(C)(C)C)C FOEQRVDBRWOKEG-UHFFFAOYSA-N 0.000 claims 2
- XJIUMGQIFSAVBD-UHFFFAOYSA-N N-(2-methoxyethyl)-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound COCCNC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)nc12 XJIUMGQIFSAVBD-UHFFFAOYSA-N 0.000 claims 2
- BBWFRRMLWDSTQD-UHFFFAOYSA-N N-(2-methoxyethyl)-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)NCCOC BBWFRRMLWDSTQD-UHFFFAOYSA-N 0.000 claims 2
- UCYZIIWTGLYXFY-CHWSQXEVSA-N N-(2-methoxyethyl)-2-[[(3R,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](C[C@@H]1COC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC UCYZIIWTGLYXFY-CHWSQXEVSA-N 0.000 claims 2
- UCYZIIWTGLYXFY-OLZOCXBDSA-N N-(2-methoxyethyl)-2-[[(3R,5S)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](C[C@H]1COC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCCOC UCYZIIWTGLYXFY-OLZOCXBDSA-N 0.000 claims 2
- OHHOHCIDZGXKRO-UHFFFAOYSA-N N-(2-methylbutan-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)NC(C)(CC)C OHHOHCIDZGXKRO-UHFFFAOYSA-N 0.000 claims 2
- QGAVYVAUSIPYBL-UHFFFAOYSA-N N-(2-methylpropyl)-2-(1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound CC(C)CNC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)nc12 QGAVYVAUSIPYBL-UHFFFAOYSA-N 0.000 claims 2
- WSVPJRFUBJTTLA-INIZCTEOSA-N N-(2-methylpropyl)-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)NCC(C)C)CC(C)C WSVPJRFUBJTTLA-INIZCTEOSA-N 0.000 claims 2
- UHYMEWNXEFWTDY-UHFFFAOYSA-N N-(2-methylpropyl)-2-[(5-prop-2-enoyl-5-azaspiro[2.4]heptan-7-yl)amino]-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(C)C UHYMEWNXEFWTDY-UHFFFAOYSA-N 0.000 claims 2
- MLBPSHQVAJUCGA-LBPRGKRZSA-N N-(2-methylpropyl)-2-[[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]-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)NCC(C)C MLBPSHQVAJUCGA-LBPRGKRZSA-N 0.000 claims 2
- DVGVCFAMUKFZPB-UHFFFAOYSA-N N-(3,3-difluorocyclobutyl)-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)NC1CC(C1)(F)F DVGVCFAMUKFZPB-UHFFFAOYSA-N 0.000 claims 2
- RVHORABJICBDFY-UHFFFAOYSA-N N-(3,3-difluorocyclobutyl)-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)NC1CC(C1)(F)F RVHORABJICBDFY-UHFFFAOYSA-N 0.000 claims 2
- YKPOGGNAVKBJOE-HNNXBMFYSA-N N-(3,3-difluorocyclobutyl)-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)NC1CC(C1)(F)F)CC(C)C YKPOGGNAVKBJOE-HNNXBMFYSA-N 0.000 claims 2
- NDSWZLWZPDIUPS-UONOGXRCSA-N N-(3,3-difluorocyclobutyl)-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)NC1CC(C1)(F)F)OC NDSWZLWZPDIUPS-UONOGXRCSA-N 0.000 claims 2
- PZUIMDYIXNUSML-UHFFFAOYSA-N N-(3,3-difluorocyclohexyl)-5-(1-prop-2-enoylpiperidin-4-yl)oxy-1H-pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound FC1(F)CCCC(C1)NC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)cc12 PZUIMDYIXNUSML-UHFFFAOYSA-N 0.000 claims 2
- 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
- MKIFSFNJROKCGS-UHFFFAOYSA-N N-[(3-fluorophenyl)methyl]-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)NCC1=CC(=CC=C1)F MKIFSFNJROKCGS-UHFFFAOYSA-N 0.000 claims 2
- VLDYODIGPJRGBU-QGZVFWFLSA-N N-[(3R)-3,4-dihydro-2H-chromen-3-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]1COC2=CC=CC=C2C1)(C)C VLDYODIGPJRGBU-QGZVFWFLSA-N 0.000 claims 2
- VLDYODIGPJRGBU-KRWDZBQOSA-N N-[(3S)-3,4-dihydro-2H-chromen-3-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]1COC2=CC=CC=C2C1)(C)C VLDYODIGPJRGBU-KRWDZBQOSA-N 0.000 claims 2
- VTYJSPQFLPNECM-UHFFFAOYSA-N N-[(4,4-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(CCC(CC1)(F)F)O VTYJSPQFLPNECM-UHFFFAOYSA-N 0.000 claims 2
- WRSPXKFLXIVLKM-UHFFFAOYSA-N N-[(4,4-difluoro-1-hydroxycyclohexyl)methyl]-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)NCC1(CCC(CC1)(F)F)O)(C)C WRSPXKFLXIVLKM-UHFFFAOYSA-N 0.000 claims 2
- IWVDUTQDZXCDGP-UHFFFAOYSA-N N-[(4-fluoro-3-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)F)OC IWVDUTQDZXCDGP-UHFFFAOYSA-N 0.000 claims 2
- RDEHCGLGBUTZDV-UHFFFAOYSA-N N-[(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 RDEHCGLGBUTZDV-UHFFFAOYSA-N 0.000 claims 2
- VNBIQOJEZSLZHB-UHFFFAOYSA-N N-[(5-chloropyridin-2-yl)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=NC=C(C=C1)Cl VNBIQOJEZSLZHB-UHFFFAOYSA-N 0.000 claims 2
- DBVAYJJNQCXQQO-UHFFFAOYSA-N N-[(5-cyclobutyl-2-methylpyrazol-3-yl)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(=NN1C)C1CCC1 DBVAYJJNQCXQQO-UHFFFAOYSA-N 0.000 claims 2
- CVFUGGVCMDYQGZ-UHFFFAOYSA-N N-[(5-ethyl-6-methylpyridin-2-yl)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=NC(=C(C=C1)CC)C CVFUGGVCMDYQGZ-UHFFFAOYSA-N 0.000 claims 2
- AYHIBHDVONMBKW-UHFFFAOYSA-N N-[(6-fluoro-1,3-benzoxazol-2-yl)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)NCC=1OC2=C(N=1)C=CC(=C2)F AYHIBHDVONMBKW-UHFFFAOYSA-N 0.000 claims 2
- MAHRGMZHCFHRCG-UHFFFAOYSA-N N-[1-(1-hydroxycyclobutyl)propyl]-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)NC(CC)C1(CCC1)O MAHRGMZHCFHRCG-UHFFFAOYSA-N 0.000 claims 2
- KSUDPOROWDLZEK-XESZBRCGSA-N N-[[(2R)-2-fluoro-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([C@@H](CCCC1)F)O KSUDPOROWDLZEK-XESZBRCGSA-N 0.000 claims 2
- KSUDPOROWDLZEK-CISYCMJJSA-N N-[[(2S)-2-fluoro-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([C@H](CCCC1)F)O KSUDPOROWDLZEK-CISYCMJJSA-N 0.000 claims 2
- VVJJREWVFZOZJG-STQMWFEESA-N N-[[(2S,5S)-1-prop-2-enoyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-2-yl]methyl]acetamide Chemical compound C(C=C)(=O)N1[C@@H](CC[C@@H](C1)NC=1C2=C(N=CN=1)NC=C2)CNC(C)=O VVJJREWVFZOZJG-STQMWFEESA-N 0.000 claims 2
- QKPQJLUXUWAMKR-HNNQXCQYSA-N N-[[(3R)-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(C[C@@H](CC1)C)O QKPQJLUXUWAMKR-HNNQXCQYSA-N 0.000 claims 2
- NPCRMXVQZOSKFF-UHFFFAOYSA-N N-[[1-(3-fluorophenyl)pyrazol-4-yl]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)NCC=1C=NN(C=1)C1=CC(=CC=C1)F NPCRMXVQZOSKFF-UHFFFAOYSA-N 0.000 claims 2
- MUMCQWUKEFRQSM-UHFFFAOYSA-N N-[[2-methyl-4-(trifluoromethyl)-1,3-thiazol-5-yl]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(N=C(S1)C)C(F)(F)F MUMCQWUKEFRQSM-UHFFFAOYSA-N 0.000 claims 2
- RFKSPRJFHUFDHP-UHFFFAOYSA-N N-[[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]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=NC(=CC(=N1)C)C(F)(F)F RFKSPRJFHUFDHP-UHFFFAOYSA-N 0.000 claims 2
- HQKDPAPKTVITQC-UHFFFAOYSA-N N-benzyl-5-(1-prop-2-enoylpiperidin-4-yl)oxy-1H-pyrrolo[2,3-b]pyridine-3-carboxamide N-(3,3-difluorocyclohexyl)-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)NCc3ccccc3)c2c1.FC1(F)CCCC(C1)NC(=O)c1c[nH]c2ncc(OC3CCN(CC3)C(=O)C=C)cc12 HQKDPAPKTVITQC-UHFFFAOYSA-N 0.000 claims 2
- DMJUIRDMRIHVAS-UHFFFAOYSA-N N-cyclobutyl-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)NC1CCC1)(C)C DMJUIRDMRIHVAS-UHFFFAOYSA-N 0.000 claims 2
- RFXGZDXYMLJJOX-UHFFFAOYSA-N N-ethyl-1-methyl-5-[(1-prop-2-enoylpiperidin-4-yl)amino]pyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)NC=1C=C2C(=NC=1)N(C=C2C(=O)NCC)C RFXGZDXYMLJJOX-UHFFFAOYSA-N 0.000 claims 2
- CKTXEMYCMDNPKA-UHFFFAOYSA-N N-ethyl-2-(4-methyl-1-prop-2-enoylpiperidin-4-yl)oxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)(C)OC=1N=C2C(=NC=1)NC=C2C(=O)NCC CKTXEMYCMDNPKA-UHFFFAOYSA-N 0.000 claims 2
- GPFQWSFBUIRREJ-RFVHGSKJSA-N N-ethyl-2-[(1-prop-2-enoylpiperidin-3-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide N-ethyl-2-[[(3R)-1-prop-2-enoylpiperidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound CCNC(=O)c1c[nH]c2ncc(NC3CCCN(C3)C(=O)C=C)nc12.CCNC(=O)c1c[nH]c2ncc(N[C@@H]3CCCN(C3)C(=O)C=C)nc12 GPFQWSFBUIRREJ-RFVHGSKJSA-N 0.000 claims 2
- JVYIHGXUMFZDGD-NEPJUHHUSA-N N-ethyl-2-[(2R,4S)-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-NEPJUHHUSA-N 0.000 claims 2
- AILGMNXUWVMNOR-UHFFFAOYSA-N N-ethyl-2-[(4-methyl-1-prop-2-enoylpiperidin-4-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CCC(CC1)(C)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC AILGMNXUWVMNOR-UHFFFAOYSA-N 0.000 claims 2
- DNSSBTCVQKCGPU-VXGBXAGGSA-N N-ethyl-2-[[(3R,4R)-3-hydroxy-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)O DNSSBTCVQKCGPU-VXGBXAGGSA-N 0.000 claims 2
- ZVCCICJBOYPQDJ-YPMHNXCESA-N N-ethyl-2-[[(3R,4R)-4-ethyl-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H]([C@@H](C1)CC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC ZVCCICJBOYPQDJ-YPMHNXCESA-N 0.000 claims 2
- IPVQSIWLNPQYAP-VXGBXAGGSA-N N-ethyl-2-[[(3R,5R)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](C[C@@H]1COC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC IPVQSIWLNPQYAP-VXGBXAGGSA-N 0.000 claims 2
- IPVQSIWLNPQYAP-NEPJUHHUSA-N N-ethyl-2-[[(3R,5S)-5-(methoxymethyl)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](C[C@H]1COC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC IPVQSIWLNPQYAP-NEPJUHHUSA-N 0.000 claims 2
- ULPRAWRMPMCTKU-NWDGAFQWSA-N N-ethyl-2-[[(3R,6S)-6-methyl-1-prop-2-enoylpiperidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC[C@@H]1C)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC ULPRAWRMPMCTKU-NWDGAFQWSA-N 0.000 claims 2
- AAKNFXWDGXDUGG-NSHDSACASA-N N-ethyl-2-[[(3S)-1-prop-2-enoylpiperidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CCC1)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC AAKNFXWDGXDUGG-NSHDSACASA-N 0.000 claims 2
- DNSSBTCVQKCGPU-RYUDHWBXSA-N N-ethyl-2-[[(3S,4S)-3-hydroxy-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)O DNSSBTCVQKCGPU-RYUDHWBXSA-N 0.000 claims 2
- ZVCCICJBOYPQDJ-WCQYABFASA-N N-ethyl-2-[[(3S,4S)-4-ethyl-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H]([C@H](C1)CC)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC ZVCCICJBOYPQDJ-WCQYABFASA-N 0.000 claims 2
- ULPRAWRMPMCTKU-NEPJUHHUSA-N N-ethyl-2-[[(3S,6R)-6-methyl-1-prop-2-enoylpiperidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC[C@H]1C)NC=1N=C2C(=NC=1)NC=C2C(=O)NCC ULPRAWRMPMCTKU-NEPJUHHUSA-N 0.000 claims 2
- KYGDINUZYIFFAT-UHFFFAOYSA-N N-ethyl-2-[methyl-(1-prop-2-enoylpyrrolidin-3-yl)amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)N(C=1N=C2C(=NC=1)NC=C2C(=O)NCC)C KYGDINUZYIFFAT-UHFFFAOYSA-N 0.000 claims 2
- KYGDINUZYIFFAT-LLVKDONJSA-N N-ethyl-2-[methyl-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@@H](CC1)N(C=1N=C2C(=NC=1)NC=C2C(=O)NCC)C KYGDINUZYIFFAT-LLVKDONJSA-N 0.000 claims 2
- KYGDINUZYIFFAT-NSHDSACASA-N N-ethyl-2-[methyl-[(3S)-1-prop-2-enoylpyrrolidin-3-yl]amino]-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide Chemical compound C(C=C)(=O)N1C[C@H](CC1)N(C=1N=C2C(=NC=1)NC=C2C(=O)NCC)C KYGDINUZYIFFAT-NSHDSACASA-N 0.000 claims 2
- LNSYWJJFDWERGU-CHWSQXEVSA-N N-ethyl-5-methyl-2-[[(2R,4R)-2-methyl-1-prop-2-enoylpiperidin-4-yl]amino]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)N(C=C2C(=O)NCC)C)C LNSYWJJFDWERGU-CHWSQXEVSA-N 0.000 claims 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- DJJKVDPNQIJDTR-GYBQEXSMSA-N formic acid 1-[(2R,5S)-2-[(1R)-1-hydroxyethyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl]prop-2-en-1-one Chemical compound OC=O.C[C@@H](O)[C@H]1CC[C@@H](CN1C(=O)C=C)Nc1ncnc2[nH]ccc12 DJJKVDPNQIJDTR-GYBQEXSMSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 229910052727 yttrium Inorganic materials 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- PLLJZTGSZXVTGP-UHFFFAOYSA-N N-(2-cyclopropylethyl)-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)NCCC1CC1 PLLJZTGSZXVTGP-UHFFFAOYSA-N 0.000 claims 1
- PJXVBNUKGVIHRY-AEGPPILISA-N N-[(2S)-1-methoxypropan-2-yl]-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)N[C@H](COC)C)OC PJXVBNUKGVIHRY-AEGPPILISA-N 0.000 claims 1
- PSVKVGPZESILJX-UHFFFAOYSA-N N-[(3-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(=CC=C1)F PSVKVGPZESILJX-UHFFFAOYSA-N 0.000 claims 1
- MKAUQAKDAAKSRU-UHFFFAOYSA-N N-benzyl-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=CC=C1 MKAUQAKDAAKSRU-UHFFFAOYSA-N 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562155824P | 2015-05-01 | 2015-05-01 | |
| US62/155,824 | 2015-05-01 | ||
| PCT/IB2016/052220 WO2016178110A1 (en) | 2015-05-01 | 2016-04-19 | Pyrrolo[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyrazinyl, pyrrolo[2,3-b]pyridinyl acrylamides and epoxides thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018514560A JP2018514560A (ja) | 2018-06-07 |
| JP2018514560A5 true JP2018514560A5 (https=) | 2019-05-23 |
| JP6761815B2 JP6761815B2 (ja) | 2020-09-30 |
Family
ID=55863136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556831A Active JP6761815B2 (ja) | 2015-05-01 | 2016-04-19 | ピロロ［２，３−ｄ］ピリミジニル、ピロロ［２，３−ｂ］ピラジニル、ピロロ［２，３−ｂ］ピリジニルアクリルアミド、およびそのエポキシド |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10703756B2 (https=) |
| EP (1) | EP3288943B1 (https=) |
| JP (1) | JP6761815B2 (https=) |
| AR (1) | AR104461A1 (https=) |
| CA (1) | CA2984183C (https=) |
| ES (1) | ES2928757T3 (https=) |
| TW (1) | TW201706274A (https=) |
| WO (1) | WO2016178110A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| US11957931B2 (en) * | 2017-04-26 | 2024-04-16 | Yale University | Compositions and methods for treating vitiligo |
| US11639346B2 (en) | 2017-05-25 | 2023-05-02 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant KRAS, HRAS or NRAS |
| MY200629A (en) | 2017-08-01 | 2024-01-06 | Theravance Biopharma R&D Ip Llc | Pyrazolo and triazolo bicyclic compounds as jak kinase inhibitors |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| MX2021000887A (es) | 2018-08-01 | 2021-03-31 | Araxes Pharma Llc | Compuestos espiroheterociclicos y metodos de uso de los mismos para el tratamiento de cancer. |
| WO2020033955A1 (en) | 2018-08-10 | 2020-02-13 | Aclaris Therapeutics, Inc. | Pyrrolopyrimidine itk 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 |
| 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 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9911365A (pt) | 1998-06-19 | 2001-03-13 | Pfizer Prod Inc | Compostos pirrolo[2,3-d]pirimidina |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| EP1382339B1 (en) | 1999-12-10 | 2007-12-05 | Pfizer Products Inc. | Compositions containing pyrrolo ¬2,3-d pyrimidine derivatives |
| IL152771A0 (en) | 2000-06-26 | 2003-06-24 | Pfizer Prod Inc | PYRROLO(2,3-d) PYRIMIDINE COMPOUNDS AS IMMUNOSUPPRESSIVE AGENTS |
| 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 |
| CN1863813B (zh) | 2003-08-27 | 2011-03-30 | 生物区科学管理控股有限公司 | 作为治疗剂的三环核苷或核苷酸 |
| BRPI0613876A2 (pt) | 2005-07-29 | 2011-02-15 | Pfizer Prod Inc | derivados de pirrolo [2,3-d] pirimidina; seus intermediários e sìntese |
| 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 |
| JP5368485B2 (ja) * | 2008-02-25 | 2013-12-18 | エフ．ホフマン−ラ ロシュ アーゲー | ピロロピラジンキナーゼインヒビター |
| ES2378513T3 (es) | 2008-08-06 | 2012-04-13 | Pfizer Inc. | Compuestos 2-heterociclilamino piracinas sustituidas en posición 6 como inhibidores de CHK-1 |
| PT2473049T (pt) | 2009-09-04 | 2019-03-04 | Sunesis Pharmaceuticals Inc | Inibidores de tirosina quinase de bruton |
| CA2799904A1 (en) * | 2010-05-20 | 2011-11-24 | F. Hoffmann-La Roche Ag | Pyrrolo [2, 3 - b] pyrazine - 7 - carboxamide derivatives and their use as jak and syk inhibitors |
| US9206188B2 (en) * | 2013-04-18 | 2015-12-08 | Arrien Pharmaceuticals Llc | Substituted pyrrolo[2,3-b]pyridines as ITK and JAK inhibitors |
| MX368464B (es) | 2013-12-05 | 2019-10-02 | Pfizer | Acrilamidas de pirrolo[2,3-d]pirimidinilo, pirrolo[2,3-b]pirazinil o y pirrolo[2,3-d]piridinilo. |
-
2016
- 2016-04-19 US US15/569,874 patent/US10703756B2/en active Active
- 2016-04-19 CA CA2984183A patent/CA2984183C/en active Active
- 2016-04-19 WO PCT/IB2016/052220 patent/WO2016178110A1/en not_active Ceased
- 2016-04-19 ES ES16719917T patent/ES2928757T3/es active Active
- 2016-04-19 JP JP2017556831A patent/JP6761815B2/ja active Active
- 2016-04-19 EP EP16719917.3A patent/EP3288943B1/en active Active
- 2016-04-27 TW TW105113139A patent/TW201706274A/zh unknown
- 2016-04-29 AR ARP160101237A patent/AR104461A1/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018514560A5 (https=) | ||
| JP6574039B2 (ja) | Ｐｉ３ｋ阻害剤としてのヘテロシクリルアミン | |
| JP6585158B2 (ja) | ヤヌスキナーゼの阻害に有用なピロロ［２，３−ｄ］ピリミジン誘導体 | |
| JP2017524007A5 (https=) | ||
| TWI494314B (zh) | ５,７－取代的－咪唑并［１,２－ｃ］嘧啶 | |
| CN105732636B (zh) | 杂芳化合物及其在药物中的应用 | |
| JP6229042B2 (ja) | ビヘテロアリール化合物及びその使用 | |
| TWI687220B (zh) | 吡唑并嘧啶衍生物治療PI3Kδ相關病症之用途 | |
| CN105164114B (zh) | C‑连接的杂环烷基取代的嘧啶类和它们的用途 | |
| ME02883B (me) | PIROLO[2,3-d]PIRIMIDINIL-, PIROLO[2,3-b]PIRAZINIL- I PIROLO[2,3-d] PIRIDINILAKRILAMIDI | |
| RU2450003C2 (ru) | Индазолы, бензотиазолы, бензоизотиазолы, бензоизоксазолы, пиразолопиридины, изотиазолопиридины, их получение и их применение | |
| JP2019523233A5 (https=) | ||
| EP3183247A1 (en) | Aminopyrimidinyl compounds as jak inhibitors | |
| JP2018532760A5 (https=) | ||
| CN105732637B (zh) | 杂芳化合物及其在药物中的应用 | |
| RU2016124178A (ru) | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет | |
| EA025520B1 (ru) | N-(ГЕТЕРО)АРИЛПИРРОЛИДИНОВЫЕ ПРОИЗВОДНЫЕ ПИРАЗОЛ-4-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ И ПИРРОЛ-3-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-КИНАЗЫ | |
| CA3107365A1 (en) | Pyrazine compounds and uses thereof | |
| TWI693227B (zh) | 新穎二環性或三環性雜環化合物 | |
| CN104271566A (zh) | 取代的联吡啶胺及其用途 | |
| JP2019522656A (ja) | ヘテロアリール置換のアミノピリジン化合物 | |
| JP2018514552A5 (https=) | ||
| JP2017518326A5 (https=) | ||
| JP2021504380A5 (https=) | ||
| JP2019537590A5 (https=) |