CA2792278C - 2,4-pyrimidinediamine compounds and prodrugs thereof and their uses - Google Patents
2,4-pyrimidinediamine compounds and prodrugs thereof and their uses Download PDFInfo
- Publication number
- CA2792278C CA2792278C CA2792278A CA2792278A CA2792278C CA 2792278 C CA2792278 C CA 2792278C CA 2792278 A CA2792278 A CA 2792278A CA 2792278 A CA2792278 A CA 2792278A CA 2792278 C CA2792278 C CA 2792278C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- fluoro
- oxo
- pyrimidinediamine
- dihydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229940002612 prodrug Drugs 0.000 title description 8
- 239000000651 prodrug Substances 0.000 title description 8
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 486
- 150000003839 salts Chemical class 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 61
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 133
- -1 -N(R7)2 Chemical group 0.000 claims description 108
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 201000010099 disease Diseases 0.000 claims description 81
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 230000019491 signal transduction Effects 0.000 claims description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 102000005962 receptors Human genes 0.000 claims description 43
- 108020003175 receptors Proteins 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical group 0.000 claims description 42
- 102000000551 Syk Kinase Human genes 0.000 claims description 40
- 108010016672 Syk Kinase Proteins 0.000 claims description 40
- 150000002431 hydrogen Chemical group 0.000 claims description 39
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 229910052805 deuterium Inorganic materials 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 32
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 30
- 230000000694 effects Effects 0.000 claims description 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 208000023275 Autoimmune disease Diseases 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 19
- 108010087819 Fc receptors Proteins 0.000 claims description 18
- 102000009109 Fc receptors Human genes 0.000 claims description 18
- 208000026935 allergic disease Diseases 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 230000037390 scarring Effects 0.000 claims description 17
- 230000001363 autoimmune Effects 0.000 claims description 16
- 125000005549 heteroarylene group Chemical group 0.000 claims description 16
- 208000027866 inflammatory disease Diseases 0.000 claims description 16
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 16
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 15
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 15
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 15
- 230000001419 dependent effect Effects 0.000 claims description 15
- 210000001519 tissue Anatomy 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 208000006673 asthma Diseases 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 238000000338 in vitro Methods 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
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- 206010061218 Inflammation Diseases 0.000 claims description 10
- 206010039710 Scleroderma Diseases 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 208000010125 myocardial infarction Diseases 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 230000006378 damage Effects 0.000 claims description 9
- 230000009885 systemic effect Effects 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 230000001684 chronic effect Effects 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 230000007613 environmental effect Effects 0.000 claims description 6
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
- 206010003011 Appendicitis Diseases 0.000 claims description 5
- 208000004300 Atrophic Gastritis Diseases 0.000 claims description 5
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims description 5
- 208000023328 Basedow disease Diseases 0.000 claims description 5
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 5
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 5
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 5
- 206010016654 Fibrosis Diseases 0.000 claims description 5
- 208000036495 Gastritis atrophic Diseases 0.000 claims description 5
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
- 208000024869 Goodpasture syndrome Diseases 0.000 claims description 5
- 208000015023 Graves' disease Diseases 0.000 claims description 5
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 5
- 208000002260 Keloid Diseases 0.000 claims description 5
- 206010024229 Leprosy Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 208000029082 Pelvic Inflammatory Disease Diseases 0.000 claims description 5
- 206010034277 Pemphigoid Diseases 0.000 claims description 5
- 208000031845 Pernicious anaemia Diseases 0.000 claims description 5
- 206010035664 Pneumonia Diseases 0.000 claims description 5
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
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- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
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- 201000010001 Silicosis Diseases 0.000 claims description 5
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 5
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims description 5
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 5
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 5
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 206010047163 Vasospasm Diseases 0.000 claims description 5
- 206010002022 amyloidosis Diseases 0.000 claims description 5
- 206010006451 bronchitis Diseases 0.000 claims description 5
- 208000000594 bullous pemphigoid Diseases 0.000 claims description 5
- 208000016644 chronic atrophic gastritis Diseases 0.000 claims description 5
- 208000007451 chronic bronchitis Diseases 0.000 claims description 5
- 201000001981 dermatomyositis Diseases 0.000 claims description 5
- 201000002491 encephalomyelitis Diseases 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 5
- 208000006454 hepatitis Diseases 0.000 claims description 5
- 231100000283 hepatitis Toxicity 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 210000001117 keloid Anatomy 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 201000008350 membranous glomerulonephritis Diseases 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 206010028417 myasthenia gravis Diseases 0.000 claims description 5
- 201000008383 nephritis Diseases 0.000 claims description 5
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 201000006292 polyarteritis nodosa Diseases 0.000 claims description 5
- 208000005987 polymyositis Diseases 0.000 claims description 5
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
- 125000005551 pyridylene group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 208000002574 reactive arthritis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 201000008827 tuberculosis Diseases 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 201000005737 orchitis Diseases 0.000 claims description 4
- 125000005961 oxazepanyl group Chemical group 0.000 claims description 4
- 201000000306 sarcoidosis Diseases 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 3
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 4
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 4
- 201000008482 osteoarthritis Diseases 0.000 claims 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 2
- KCWVVHMTNMXRBY-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCOCC1 KCWVVHMTNMXRBY-UHFFFAOYSA-N 0.000 claims 2
- HUSOKGLTYKFMAM-AWEZNQCLSA-N 6-[[5-fluoro-2-[4-[(3s)-3-methylmorpholin-4-yl]anilino]pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C[C@H]1COCCN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)C(C)(C)OC3=CC=2)=N1 HUSOKGLTYKFMAM-AWEZNQCLSA-N 0.000 claims 2
- QLBOHMYRHAJQGT-UHFFFAOYSA-N 1-[4-[[4-[(2,2-dimethyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)amino]-5-fluoropyrimidin-2-yl]amino]phenyl]piperidine-4-carbonitrile Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCC(C#N)CC1 QLBOHMYRHAJQGT-UHFFFAOYSA-N 0.000 claims 1
- BVYMWZUXNJVZML-UHFFFAOYSA-N 1-[4-[[4-[(2,2-dimethyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)amino]-5-fluoropyrimidin-2-yl]amino]phenyl]piperidine-4-carboxamide Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCC(C(N)=O)CC1 BVYMWZUXNJVZML-UHFFFAOYSA-N 0.000 claims 1
- QYGARPHDDICHDO-UHFFFAOYSA-N 6-[[2-(2,4,4a,5-tetrahydro-1h-[1,4]oxazino[3,4-c][1,4]benzoxazin-8-ylamino)-5-fluoropyrimidin-4-yl]amino]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(NC3=NC(NC=4C=C5OCC6COCCN6C5=CC=4)=NC=C3F)=CC=C21 QYGARPHDDICHDO-UHFFFAOYSA-N 0.000 claims 1
- LXOSBSPZUBSSOI-UHFFFAOYSA-N 6-[[2-[3-(difluoromethoxy)-4-morpholin-4-ylanilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1OC(F)F)=CC=C1N1CCOCC1 LXOSBSPZUBSSOI-UHFFFAOYSA-N 0.000 claims 1
- VKXHUFYDAOGVSM-UHFFFAOYSA-N 6-[[2-[4-(1,1-dioxo-1,4-thiazinan-4-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCS(=O)(=O)CC1 VKXHUFYDAOGVSM-UHFFFAOYSA-N 0.000 claims 1
- IRRGRXCCLNUWMT-UHFFFAOYSA-N 6-[[2-[4-(2,2-dimethylmorpholin-4-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1COC(C)(C)CN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)C(C)(C)OC3=CC=2)=N1 IRRGRXCCLNUWMT-UHFFFAOYSA-N 0.000 claims 1
- GURXUJOTOFVLIB-UHFFFAOYSA-N 6-[[2-[4-(2,2-dimethylmorpholin-4-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1COC(C)(C)CN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)COC3=CC=2)=N1 GURXUJOTOFVLIB-UHFFFAOYSA-N 0.000 claims 1
- NDWCIWDDBHXUSR-UHFFFAOYSA-N 6-[[2-[4-(4,4-difluoropiperidin-1-yl)-3-fluoroanilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1F)=CC=C1N1CCC(F)(F)CC1 NDWCIWDDBHXUSR-UHFFFAOYSA-N 0.000 claims 1
- XQBLWCWYVKEZRT-UHFFFAOYSA-N 6-[[2-[4-(4,4-difluoropiperidin-1-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCC(F)(F)CC1 XQBLWCWYVKEZRT-UHFFFAOYSA-N 0.000 claims 1
- HTEHNNMBXLAURT-UHFFFAOYSA-N 6-[[2-[4-(4-aminopiperidin-1-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCC(N)CC1 HTEHNNMBXLAURT-UHFFFAOYSA-N 0.000 claims 1
- QCIPVRLGKDDBTG-UHFFFAOYSA-N 6-[[2-[4-(4-ethoxypiperidin-1-yl)anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1CC(OCC)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)C(C)(C)OC3=CC=2)=N1 QCIPVRLGKDDBTG-UHFFFAOYSA-N 0.000 claims 1
- GIJZTBXEKBGSJX-GASCZTMLSA-N 6-[[2-[4-[(2r,6s)-2,6-dimethylmorpholin-4-yl]anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)C(C)(C)OC3=CC=2)=N1 GIJZTBXEKBGSJX-GASCZTMLSA-N 0.000 claims 1
- BMWJAVANSAMNTN-OKILXGFUSA-N 6-[[2-[4-[(2r,6s)-2,6-dimethylmorpholin-4-yl]anilino]-5-fluoropyrimidin-4-yl]amino]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)COC3=CC=2)=N1 BMWJAVANSAMNTN-OKILXGFUSA-N 0.000 claims 1
- IEDMYLDKMVJFHC-UHFFFAOYSA-N 6-[[2-[4-[4-(diethylamino)piperidin-1-yl]anilino]-5-fluoropyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound C1CC(N(CC)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2N=C3NC(=O)C(C)(C)OC3=CC=2)=N1 IEDMYLDKMVJFHC-UHFFFAOYSA-N 0.000 claims 1
- IOJKPXSZKXLGLN-UHFFFAOYSA-N 6-[[5-fluoro-2-(3-fluoro-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1F)=CC=C1N1CCOCC1 IOJKPXSZKXLGLN-UHFFFAOYSA-N 0.000 claims 1
- UFOAIOLBHOCGFB-UHFFFAOYSA-N 6-[[5-fluoro-2-(3-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound COC1=CC(NC=2N=C(NC=3N=C4NC(=O)C(C)(C)OC4=CC=3)C(F)=CN=2)=CC=C1N1CCOCC1 UFOAIOLBHOCGFB-UHFFFAOYSA-N 0.000 claims 1
- RAZASVVIJLHCCM-UHFFFAOYSA-N 6-[[5-fluoro-2-(3-methyl-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound CC1=CC(NC=2N=C(NC=3N=C4NC(=O)C(C)(C)OC4=CC=3)C(F)=CN=2)=CC=C1N1CCOCC1 RAZASVVIJLHCCM-UHFFFAOYSA-N 0.000 claims 1
- STTRPMKIYAHHRO-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-morpholin-4-yl-3-propan-2-yloxyanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound CC(C)OC1=CC(NC=2N=C(NC=3N=C4NC(=O)C(C)(C)OC4=CC=3)C(F)=CN=2)=CC=C1N1CCOCC1 STTRPMKIYAHHRO-UHFFFAOYSA-N 0.000 claims 1
- GIFJHZLZRZPIST-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C(NC=2N=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 GIFJHZLZRZPIST-UHFFFAOYSA-N 0.000 claims 1
- ZZJLCJZQXLUVMB-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-piperidin-1-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCCCC1 ZZJLCJZQXLUVMB-UHFFFAOYSA-N 0.000 claims 1
- YDIVRBPDEOJCCP-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-piperidin-1-ylanilino)pyrimidin-4-yl]amino]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C(NC=2N=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1N1CCCCC1 YDIVRBPDEOJCCP-UHFFFAOYSA-N 0.000 claims 1
- AXKXDYSEJYWLJX-UHFFFAOYSA-N 6-[[5-fluoro-2-(4-thiomorpholin-4-ylanilino)pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1N1CCSCC1 AXKXDYSEJYWLJX-UHFFFAOYSA-N 0.000 claims 1
- JZZFMAMDBUTHJO-UHFFFAOYSA-N 6-[[5-fluoro-2-[(2-pyridin-4-yl-3h-benzimidazol-5-yl)amino]pyrimidin-4-yl]amino]-2,2-dimethyl-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound N1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1N2)=CC=C1N=C2C1=CC=NC=C1 JZZFMAMDBUTHJO-UHFFFAOYSA-N 0.000 claims 1
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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| US32369910P | 2010-04-13 | 2010-04-13 | |
| US61/323,699 | 2010-04-13 | ||
| PCT/US2011/032291 WO2011130390A1 (en) | 2010-04-13 | 2011-04-13 | 2, 4-pyrimidinediamine compounds and prodrugs thereof and their uses |
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| CA2792278A1 CA2792278A1 (en) | 2011-10-20 |
| CA2792278C true CA2792278C (en) | 2019-05-14 |
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| ES (1) | ES2562419T3 (enExample) |
| WO (1) | WO2011130390A1 (enExample) |
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| ES2562419T3 (es) * | 2010-04-13 | 2016-03-04 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidinodiamina y sus profármacos y sus usos |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| HRP20190186T4 (hr) | 2011-07-28 | 2024-12-20 | Rigel Pharmaceuticals, Inc. | Nove formulacije (trimetoksifenilamino)pirimidinila |
| WO2013020132A1 (en) * | 2011-08-04 | 2013-02-07 | The Brigham And Women's Hospital, Inc. | Methods of treating cardiovascular and metabolic diseases |
| ES2984771T3 (es) | 2012-06-13 | 2024-10-31 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| WO2013189241A1 (zh) * | 2012-06-20 | 2013-12-27 | 上海恒瑞医药有限公司 | 嘧啶二胺类衍生物、其制备方法及其在医药上的应用 |
| CN102746337B (zh) * | 2012-06-21 | 2014-12-17 | 成都苑东药业有限公司 | 一种2，4-嘧啶二胺类化合物及其制备方法 |
| WO2014026125A1 (en) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Pyrazine derivatives as fgfr inhibitors |
| BR112015002493A8 (pt) * | 2012-08-30 | 2019-07-30 | Hoffmann La Roche | composto, composição farmacêutica, processo para a preparação de uma composição farmacêutica, kit e uso de um composto” |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| EP2970138B1 (en) | 2013-03-13 | 2019-01-16 | Canadian Blood Services | Pyrazole derivatives and their uses thereof |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| JP7118642B2 (ja) * | 2014-08-08 | 2022-08-16 | アリ リサーチ ソシエタ ア レスポンサビリタ リミタータ センプリフィカタ | 炎症性およびアレルギー性病変の治療に用いるための脂肪酸とパルミトイルエタノールアミドの混合物 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| EA038045B1 (ru) | 2015-02-20 | 2021-06-28 | Инсайт Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
| RS66310B1 (sr) | 2018-05-04 | 2025-01-31 | Incyte Corp | Čvrsti oblici inhibitora fgfr i procesi za njegovu pripremu |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| PH12022550892A1 (en) | 2019-10-14 | 2023-05-03 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| AU2020395185A1 (en) | 2019-12-04 | 2022-06-02 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CN116670127A (zh) * | 2021-03-30 | 2023-08-29 | 贝达药业股份有限公司 | Egfr抑制剂及其组合物和用途 |
| JP2024513575A (ja) | 2021-04-12 | 2024-03-26 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤及びネクチン－４標的化剤を含む併用療法 |
| WO2022236255A2 (en) * | 2021-05-03 | 2022-11-10 | Nuvation Bio Inc. | Heterocyclic compounds as kinase inhibitors |
| WO2022261160A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313610A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| EP4653444A1 (en) * | 2023-01-19 | 2025-11-26 | Hangzhou Innogate Pharma Co., Ltd. | Fused tricyclic compound as kinase inhibitor |
| CN119431398A (zh) * | 2023-07-31 | 2025-02-14 | 中国科学院上海有机化学研究所 | R406及其衍生物协同trail的抗肿瘤应用 |
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| US6573256B2 (en) | 1996-12-30 | 2003-06-03 | Bone Care International, Inc. | Method of inhibiting angiogenesis using active vitamin D analogues |
| FR2785284B1 (fr) | 1998-11-02 | 2000-12-01 | Galderma Res & Dev | Analogues de la vitamine d |
| US6358939B1 (en) | 1999-12-21 | 2002-03-19 | Northern Lights Pharmaceuticals, Llc | Use of biologically active vitamin D compounds for the prevention and treatment of inflammatory bowel disease |
| US6924400B2 (en) | 2001-12-10 | 2005-08-02 | Galderma Research & Development, Snc | Triaromatic vitamin D analogues |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| ATE451104T1 (de) | 2002-07-29 | 2009-12-15 | Rigel Pharmaceuticals Inc | Verfahren zur behandlung oder pruvention von autoimmunkrankheiten mit 2,4-pyrimidindiamin- verbindungen |
| US20060160834A1 (en) | 2003-06-06 | 2006-07-20 | Fong Tung M | Combination therapy for the treatment of hypertension |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| EP1663242B1 (en) | 2003-08-07 | 2011-04-27 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
| US20070092888A1 (en) | 2003-09-23 | 2007-04-26 | Cornelius Diamond | Diagnostic markers of hypertension and methods of use thereof |
| WO2006068770A1 (en) * | 2004-11-24 | 2006-06-29 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
| EP2161275A1 (en) | 2005-01-19 | 2010-03-10 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US8227455B2 (en) | 2005-04-18 | 2012-07-24 | Rigel Pharmaceuticals, Inc. | Methods of treating cell proliferative disorders |
| US7713987B2 (en) | 2005-12-06 | 2010-05-11 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2,4-diamines and their uses |
| US8163902B2 (en) | 2006-11-21 | 2012-04-24 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US7834024B2 (en) * | 2007-03-26 | 2010-11-16 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| US20090012045A1 (en) * | 2007-06-26 | 2009-01-08 | Rigel Pharmaceuticals, Inc. | Methods of Treating Cell Proliferative Disorders |
| TWI458721B (zh) * | 2008-06-27 | 2014-11-01 | Celgene Avilomics Res Inc | 雜芳基化合物及其用途 |
| CA2736258C (en) * | 2008-09-23 | 2016-11-29 | Rigel Pharmaceuticals, Inc. | Tricyclic carbamate jak inhibitors |
| WO2010078369A2 (en) * | 2008-12-30 | 2010-07-08 | Rigel Pharmaceuticals, Inc. | Pyrimidinediamine kinase inhibitors |
| WO2011063241A1 (en) * | 2009-11-20 | 2011-05-26 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and prodrugs thereof and their uses |
| ES2562419T3 (es) * | 2010-04-13 | 2016-03-04 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidinodiamina y sus profármacos y sus usos |
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- 2011-04-13 EP EP11730116.8A patent/EP2558474B1/en active Active
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Also Published As
| Publication number | Publication date |
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| CA2792278A1 (en) | 2011-10-20 |
| EP2558474B1 (en) | 2015-11-25 |
| US20110251177A1 (en) | 2011-10-13 |
| US8618095B2 (en) | 2013-12-31 |
| ES2562419T3 (es) | 2016-03-04 |
| WO2011130390A1 (en) | 2011-10-20 |
| JP6067550B2 (ja) | 2017-01-25 |
| EP2558474A1 (en) | 2013-02-20 |
| JP2016041700A (ja) | 2016-03-31 |
| JP2013523891A (ja) | 2013-06-17 |
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