JP2016534054A5 - - Google Patents
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- Publication number
- JP2016534054A5 JP2016534054A5 JP2016525001A JP2016525001A JP2016534054A5 JP 2016534054 A5 JP2016534054 A5 JP 2016534054A5 JP 2016525001 A JP2016525001 A JP 2016525001A JP 2016525001 A JP2016525001 A JP 2016525001A JP 2016534054 A5 JP2016534054 A5 JP 2016534054A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ylamino
- indol
- pyrazol
- hydroxyisoxazolidin
- 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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- 150000001875 compounds Chemical class 0.000 claims 31
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- -1 amino, hydroxy Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 3
- 230000000172 allergic effect Effects 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 208000010668 atopic eczema Diseases 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000001448 anilines Chemical class 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000003325 follicular Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- NYENOWAOSWSSCL-KRWDZBQOSA-N (4S)-2-[[1-[2-[(3-chloro-1,2-dimethylindol-5-yl)amino]pyrimidin-4-yl]-3-methylpyrazol-4-yl]methyl]-1,2-oxazolidin-4-ol Chemical compound Cc1nn(cc1CN1C[C@H](O)CO1)-c1ccnc(Nc2ccc3n(C)c(C)c(Cl)c3c2)n1 NYENOWAOSWSSCL-KRWDZBQOSA-N 0.000 claims 1
- XHZBYLHQKQHUCB-INIZCTEOSA-N (4S)-2-[[3-methyl-1-[2-[(1-methyl-3-methylsulfonylindazol-5-yl)amino]pyrimidin-4-yl]pyrazol-4-yl]methyl]-1,2-oxazolidin-4-ol Chemical compound Cc1nn(cc1CN1C[C@H](O)CO1)-c1ccnc(Nc2ccc3n(C)nc(c3c2)S(C)(=O)=O)n1 XHZBYLHQKQHUCB-INIZCTEOSA-N 0.000 claims 1
- BLFQYOOGPVKCNI-IBGZPJMESA-N 1-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]-2-methylpropan-1-one Chemical compound O[C@H]1CN(OC1)CC=1C(=NN(C1)C1=NC(=NC=C1)NC=1C=C2C(=CN(C2=CC1)C)C(C(C)C)=O)C BLFQYOOGPVKCNI-IBGZPJMESA-N 0.000 claims 1
- UTFPDGMYJZGSMM-SFHVURJKSA-N 1-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]ethanone Chemical compound O[C@H]1CN(OC1)CC=1C(=NN(C1)C1=NC(=NC=C1)NC=1C=C2C(=CN(C2=CC1)C)C(C)=O)C UTFPDGMYJZGSMM-SFHVURJKSA-N 0.000 claims 1
- DPOHUTMUGRCITM-HNNXBMFYSA-N 1-[5-[[5-chloro-4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]-2,2,2-trifluoroethanone Chemical compound ClC=1C(=NC(=NC1)NC=1C=C2C(=CN(C2=CC1)C)C(C(F)(F)F)=O)N1N=C(C(=C1)CN1OC[C@H](C1)O)C DPOHUTMUGRCITM-HNNXBMFYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- BIYFOBJTTQVRAK-MRXNPFEDSA-N 2,2-difluoro-1-[5-[[4-[4-[[(4R)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]ethanone Chemical compound FC(C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@@H](C1)O)C)C)F BIYFOBJTTQVRAK-MRXNPFEDSA-N 0.000 claims 1
- BIYFOBJTTQVRAK-INIZCTEOSA-N 2,2-difluoro-1-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]ethanone Chemical compound FC(C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)C)F BIYFOBJTTQVRAK-INIZCTEOSA-N 0.000 claims 1
- QBMTYWVIJIBXCG-UHFFFAOYSA-N 2-(1H-pyrazol-4-ylmethyl)-1,2-oxazolidin-4-ol Chemical compound OC1CON(Cc2cn[nH]c2)C1 QBMTYWVIJIBXCG-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000010000 Agranulocytosis Diseases 0.000 claims 1
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 206010006555 Bullous conditions Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010048768 Dermatosis Diseases 0.000 claims 1
- 208000004332 Evans syndrome Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 206010018687 Granulocytopenia Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 1
- 206010052178 Lymphocytic lymphoma Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000035268 Mast Cell Activation disease Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010049088 Osteopenia Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 241000721454 Pemphigus Species 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 230000036783 anaphylactic response Effects 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- IYIKRZHAOWGOJG-SFHVURJKSA-N cyclopropyl-[1-(2,2-difluoroethyl)-5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]pyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=CC(=C1)CN1OC[C@H](C1)O)CC(F)F IYIKRZHAOWGOJG-SFHVURJKSA-N 0.000 claims 1
- SBYVJMFCOAMQIQ-AIBWNMTMSA-N cyclopropyl-[1-(2-fluoroethyl)-5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-2,3-dihydroindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)CCF SBYVJMFCOAMQIQ-AIBWNMTMSA-N 0.000 claims 1
- LDLAKDPWNYHTNA-IBGZPJMESA-N cyclopropyl-[1-(2-fluoroethyl)-5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]pyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=CC(=C1)CN1OC[C@H](C1)O)CCF LDLAKDPWNYHTNA-IBGZPJMESA-N 0.000 claims 1
- FUBSRPKXGDKVIE-NRFANRHFSA-N cyclopropyl-[1-ethyl-5-[[4-[3-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1C=C(C(=C1)C)CN1OC[C@H](C1)O)CC FUBSRPKXGDKVIE-NRFANRHFSA-N 0.000 claims 1
- IJTHACUZXNAFPR-UHFFFAOYSA-N cyclopropyl-[1-ethyl-5-[[4-[4-[(4-hydroxy-4-methyl-1,2-oxazolidin-2-yl)methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound CCn1cc(C(=O)C2CC2)c2cc(Nc3nccc(n3)-n3cc(CN4CC(C)(O)CO4)c(C)n3)ccc12 IJTHACUZXNAFPR-UHFFFAOYSA-N 0.000 claims 1
- PWEKRGOZHHLNMO-HXUWFJFHSA-N cyclopropyl-[1-ethyl-5-[[4-[4-[[(4R)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@@H](C1)O)C)CC PWEKRGOZHHLNMO-HXUWFJFHSA-N 0.000 claims 1
- PWEKRGOZHHLNMO-FQEVSTJZSA-N cyclopropyl-[1-ethyl-5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)CC PWEKRGOZHHLNMO-FQEVSTJZSA-N 0.000 claims 1
- LHLCSKXMDFMMSX-FQEVSTJZSA-N cyclopropyl-[1-ethyl-5-[[5-fluoro-4-[3-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=C(C(=N1)N1C=C(C(=C1)C)CN1OC[C@H](C1)O)F)CC LHLCSKXMDFMMSX-FQEVSTJZSA-N 0.000 claims 1
- KCQSZKBRMVTRRJ-IBGZPJMESA-N cyclopropyl-[1-ethyl-5-[[5-fluoro-4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=C(C(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)F)CC KCQSZKBRMVTRRJ-IBGZPJMESA-N 0.000 claims 1
- LIDCFKBKXOTSEC-NRFANRHFSA-N cyclopropyl-[5-[[4-[3-cyclopropyl-4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]pyrazol-1-yl]pyrimidin-2-yl]amino]-1-ethylindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C1CC1)CC LIDCFKBKXOTSEC-NRFANRHFSA-N 0.000 claims 1
- IBTPVKVXHQWXCK-UHFFFAOYSA-N cyclopropyl-[5-[[4-[4-[(4-hydroxy-4-methyl-1,2-oxazolidin-2-yl)methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-(2,2,2-trifluoroethyl)indol-3-yl]methanone Chemical compound Cc1nn(cc1CN1CC(C)(O)CO1)-c1ccnc(Nc2ccc3n(CC(F)(F)F)cc(C(=O)C4CC4)c3c2)n1 IBTPVKVXHQWXCK-UHFFFAOYSA-N 0.000 claims 1
- QLSIKNVCSGLJIF-UHFFFAOYSA-N cyclopropyl-[5-[[4-[4-[(4-hydroxy-4-methyl-1,2-oxazolidin-2-yl)methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone Chemical compound Cc1nn(cc1CN1CC(C)(O)CO1)-c1ccnc(Nc2ccc3n(C)cc(C(=O)C4CC4)c3c2)n1 QLSIKNVCSGLJIF-UHFFFAOYSA-N 0.000 claims 1
- UILWLKMAKNGENX-FQEVSTJZSA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]-5-methylpyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=C(C(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)C)C UILWLKMAKNGENX-FQEVSTJZSA-N 0.000 claims 1
- LVECTQJBPIVAIR-IBGZPJMESA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-(2,2,2-trifluoroethyl)indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)CC(F)(F)F LVECTQJBPIVAIR-IBGZPJMESA-N 0.000 claims 1
- HOFPWOAFILPHER-IBGZPJMESA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylsulfonylindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)S(=O)(=O)C HOFPWOAFILPHER-IBGZPJMESA-N 0.000 claims 1
- QFFPVRRLEUQNPK-NRFANRHFSA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-propan-2-ylindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C)C(C)C QFFPVRRLEUQNPK-NRFANRHFSA-N 0.000 claims 1
- RNHQHTDFADEGJD-SFHVURJKSA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1H-indol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CNC2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=C(C(=C1)CN1OC[C@H](C1)O)C RNHQHTDFADEGJD-SFHVURJKSA-N 0.000 claims 1
- LGAANFVKOYQKJI-SFHVURJKSA-N cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]pyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone Chemical compound C1(CC1)C(=O)C1=CN(C2=CC=C(C=C12)NC1=NC=CC(=N1)N1N=CC(=C1)CN1OC[C@H](C1)O)C LGAANFVKOYQKJI-SFHVURJKSA-N 0.000 claims 1
- YCZUBLQESBVOSH-IBGZPJMESA-N cyclopropyl-[5-[[4-[4-[[(4s)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone Chemical compound CC1=NN(C=2N=C(NC=3C=C4C(C(=O)C5CC5)=CN(C)C4=CC=3)N=CC=2)C=C1CN1C[C@H](O)CO1 YCZUBLQESBVOSH-IBGZPJMESA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 150000003278 haem Chemical class 0.000 claims 1
- 208000007475 hemolytic anemia Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 230000036210 malignancy Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000004235 neutropenia Diseases 0.000 claims 1
- 230000000010 osteolytic effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000002269 spontaneous effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 206010043207 temporal arteritis Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361893866P | 2013-10-21 | 2013-10-21 | |
| US61/893,866 | 2013-10-21 | ||
| PCT/US2014/061649 WO2015061369A1 (en) | 2013-10-21 | 2014-10-21 | Substituted pyrimidine compounds and their use as syk inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
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| EP3942045A1 (en) | 2019-03-21 | 2022-01-26 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| EP4054579A1 (en) | 2019-11-08 | 2022-09-14 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN113248472B (zh) * | 2020-02-12 | 2022-06-28 | 中国药科大学 | 抗骨质疏松化合物及其衍生物，药物组合物、制备方法和应用 |
| KR20210152312A (ko) * | 2020-06-08 | 2021-12-15 | 주식회사 종근당 | 카나비노이드 수용체 (cb1 수용체) 길항제로서의 4-(4,5-디하이드로-1h-피라졸-1-닐)피리미딘 화합물 및 이를 포함하는 약제학적 조성물 |
| CN116323595B (zh) * | 2020-09-23 | 2025-08-19 | 内尔维亚诺医疗科学公司 | 作为激酶抑制剂的吡唑基-嘧啶衍生物 |
| KR20260039645A (ko) * | 2023-04-24 | 2026-03-20 | 셴젠 이오노바 라이프 사이언스 시오., 엘티디. | Cdk2 억제제 및 이의 사용 방법 |
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| US20030158195A1 (en) | 2001-12-21 | 2003-08-21 | Cywin Charles L. | 1,6 naphthyridines useful as inhibitors of SYK kinase |
| WO2004035604A2 (en) | 2002-10-16 | 2004-04-29 | Millennium Pharmaceuticals, Inc. | Spleen tyrosine kinase catalytic domain:crystal structure and binding pockets thereof |
| SE0300119D0 (sv) * | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| SE0300120D0 (sv) * | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| WO2004065395A1 (en) * | 2003-01-17 | 2004-08-05 | Astrazeneca Ab | Thienopyridazinones and their use in modulation of autoimmune disease |
| US20080004295A1 (en) * | 2005-10-13 | 2008-01-03 | Gore Paul M | Novel compounds |
| WO2009032703A1 (en) * | 2007-08-28 | 2009-03-12 | Irm Llc | 2- (het) arylamino-6-aminopyridine derivatives and fused forms thereof as anaplastic lymphoma kinase inhibitors |
| EP2313406B1 (de) | 2008-08-05 | 2015-02-25 | Boehringer Ingelheim International GmbH | 4-dimethylaminophenyl-substituierte napththyridine und ihre verwendung als arzneimittel |
| WO2010015520A1 (de) | 2008-08-05 | 2010-02-11 | Boehringer Ingelheim International Gmbh | Substituierte naphthyridine und ihre verwendung als arzneimittel |
| US8629132B2 (en) * | 2009-11-13 | 2014-01-14 | Genosco | Kinase inhibitors |
| CN102822172A (zh) | 2010-01-29 | 2012-12-12 | 贝林格尔.英格海姆国际有限公司 | 取代的二氮杂萘及其作为syk 激酶抑制剂的用途 |
| GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
| BR112012029437A2 (pt) | 2010-05-20 | 2017-03-07 | F Hoffmann - La Roche Ag | derivados de pirrolo[2,3-b]pirazina-7-carboxamida e seu uso como inibidores de jak e syk |
| WO2011156698A2 (en) * | 2010-06-11 | 2011-12-15 | Abbott Laboratories | NOVEL PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS |
| UY34484A (es) * | 2011-12-15 | 2013-07-31 | Bayer Ip Gmbh | Benzotienilo-pirrolotriazinas disustituidas y sus usos |
| CA2863517C (en) * | 2012-01-20 | 2019-11-05 | Genosco | Substituted pyrimidine compounds and their use as syk inhibitors |
| EA031267B1 (ru) * | 2012-03-22 | 2018-12-28 | Оскотек, Инк. | Замещенные пиридопиримидиновые соединения и их применение в качестве flt3 ингибиторов |
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