JP2013502429A5 - - Google Patents
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- JP2013502429A5 JP2013502429A5 JP2012525664A JP2012525664A JP2013502429A5 JP 2013502429 A5 JP2013502429 A5 JP 2013502429A5 JP 2012525664 A JP2012525664 A JP 2012525664A JP 2012525664 A JP2012525664 A JP 2012525664A JP 2013502429 A5 JP2013502429 A5 JP 2013502429A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- isoxazol
- acetamide
- amino
- tert
- 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.)
- Pending
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- -1 cyano, amino, hydroxy Chemical group 0.000 claims description 221
- 238000000034 method Methods 0.000 claims description 53
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 29
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- FPDVVQNKNNSRLM-UHFFFAOYSA-N [3-chloro-5-[4-[2-[[3-(3-methyloxetan-3-yl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=C(Cl)C([NH3+])=NC=2)ON=C1C1(C)COC1 FPDVVQNKNNSRLM-UHFFFAOYSA-N 0.000 claims description 3
- AGEUMEIHAWSGRB-UHFFFAOYSA-N [3-fluoro-5-[4-[2-[[3-(3-methyloxetan-3-yl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=C(F)C([NH3+])=NC=2)ON=C1C1(C)COC1 AGEUMEIHAWSGRB-UHFFFAOYSA-N 0.000 claims description 3
- IKDRSFWPIPAGNT-UHFFFAOYSA-N [5-[4-[2-[[3-(1-fluorocyclobutyl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium;acetate Chemical compound CC([O-])=O.C1=NC([NH3+])=CC=C1C(C=C1)=CC=C1CC(=O)NC1=CC(C2(F)CCC2)=NO1 IKDRSFWPIPAGNT-UHFFFAOYSA-N 0.000 claims description 3
- RKKQZFBAJHFZGY-UHFFFAOYSA-N [5-[4-[2-[[3-(2,2-difluoro-1-methylcyclopropyl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium;acetate Chemical compound CC([O-])=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)CC1(F)F RKKQZFBAJHFZGY-UHFFFAOYSA-N 0.000 claims description 3
- PRTSTZPQCQSCBN-UHFFFAOYSA-N [5-[4-[[3-(2,2-difluoro-1-methylcyclopropyl)-1,2-oxazol-5-yl]carbamoylamino]phenyl]pyridin-2-yl]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)NC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)CC1(F)F PRTSTZPQCQSCBN-UHFFFAOYSA-N 0.000 claims description 3
- SFJLVUJTINFARG-UHFFFAOYSA-N methanesulfonate;[3-methyl-5-[4-[2-[[3-(3-methyloxetan-3-yl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.N1=C([NH3+])C(C)=CC(C=2C=CC(CC(=O)NC=3ON=C(C=3)C3(C)COC3)=CC=2)=C1 SFJLVUJTINFARG-UHFFFAOYSA-N 0.000 claims description 3
- UNTLQTVIPKUNEY-UHFFFAOYSA-N methanesulfonate;[5-[4-[2-[[3-(1-methylcyclobutyl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)CCC1 UNTLQTVIPKUNEY-UHFFFAOYSA-N 0.000 claims description 3
- GVGQXQNYLMDSJE-UHFFFAOYSA-N methanesulfonate;[5-[4-[2-[[3-(1-methylcyclopropyl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)CC1 GVGQXQNYLMDSJE-UHFFFAOYSA-N 0.000 claims description 3
- QVHUNFOFBXHTMW-UHFFFAOYSA-N methanesulfonate;[5-[4-[[3-(1-methylcyclopropyl)-1,2-oxazol-5-yl]carbamoylamino]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)NC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)CC1 QVHUNFOFBXHTMW-UHFFFAOYSA-N 0.000 claims description 3
- DCSZHAYOJIRJLI-UHFFFAOYSA-N methanesulfonate;[5-[4-[[3-[1-(trifluoromethyl)cyclobutyl]-1,2-oxazol-5-yl]carbamoylamino]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=NC([NH3+])=CC=C1C(C=C1)=CC=C1NC(=O)NC1=CC(C2(CCC2)C(F)(F)F)=NO1 DCSZHAYOJIRJLI-UHFFFAOYSA-N 0.000 claims description 3
- OCIHCSSBEQZYCO-UHFFFAOYSA-N [3-fluoro-5-[4-[2-[[3-(1-methylcyclopropyl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=C(F)C([NH3+])=NC=2)ON=C1C1(C)CC1 OCIHCSSBEQZYCO-UHFFFAOYSA-N 0.000 claims description 2
- LLERAPLNDGIZHE-UHFFFAOYSA-N methanesulfonate;[5-[4-[2-[[3-(3-methyloxetan-3-yl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]-3-(trifluoromethyl)pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=C(C([NH3+])=NC=2)C(F)(F)F)ON=C1C1(C)COC1 LLERAPLNDGIZHE-UHFFFAOYSA-N 0.000 claims description 2
- SUHXGCFMRUZQGI-UHFFFAOYSA-N methanesulfonate;[5-[4-[2-[[3-(3-methyloxetan-3-yl)-1,2-oxazol-5-yl]amino]-2-oxoethyl]phenyl]pyridin-2-yl]azanium Chemical compound CS([O-])(=O)=O.C1=C(NC(=O)CC=2C=CC(=CC=2)C=2C=NC([NH3+])=CC=2)ON=C1C1(C)COC1 SUHXGCFMRUZQGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 89
- 125000005843 halogen group Chemical group 0.000 claims 56
- 125000000753 cycloalkyl group Chemical group 0.000 claims 47
- 125000001188 haloalkyl group Chemical group 0.000 claims 42
- 125000003342 alkenyl group Chemical group 0.000 claims 40
- 125000000304 alkynyl group Chemical group 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 39
- 239000001257 hydrogen Substances 0.000 claims 39
- 125000003545 alkoxy group Chemical group 0.000 claims 38
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 36
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 claims 3
- 101710150918 Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000004968 inflammatory condition Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- RGTIEGZKUCTIQI-UHFFFAOYSA-N 1-[4-(6-aminopyridin-3-yl)-2-fluorophenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=NC(N)=CC=2)F)=N1 RGTIEGZKUCTIQI-UHFFFAOYSA-N 0.000 claims 2
- UATVAZZIRWDZJW-UHFFFAOYSA-N 2-[4-(6-amino-2-fluoropyridin-3-yl)phenyl]-n-[5-(1-methylcyclopropyl)-1,2-oxazol-3-yl]acetamide Chemical compound C=1C(NC(=O)CC=2C=CC(=CC=2)C=2C(=NC(N)=CC=2)F)=NOC=1C1(C)CC1 UATVAZZIRWDZJW-UHFFFAOYSA-N 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- XMOCKPBLBBBAJX-UHFFFAOYSA-N [5-[4-[[3-(2-fluoropropan-2-yl)-1,2-oxazol-5-yl]carbamoylamino]phenyl]pyridin-2-yl]azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.O1N=C(C(C)(F)C)C=C1NC(=O)NC1=CC=C(C=2C=NC([NH3+])=CC=2)C=C1 XMOCKPBLBBBAJX-UHFFFAOYSA-N 0.000 claims 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
- KTAQMNBLMYYEAS-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)-3-[4-[2-(2-morpholin-4-ylethylamino)pyrimidin-5-yl]phenyl]urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCN3CCOCC3)=NC=2)=C1 KTAQMNBLMYYEAS-UHFFFAOYSA-N 0.000 claims 1
- LEZCBVQHLRKTMJ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-fluoro-4-[6-(2-piperidin-1-ylethylamino)pyridin-3-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C(=CC(=CC=2)C=2C=NC(NCCN3CCCCC3)=CC=2)F)=N1 LEZCBVQHLRKTMJ-UHFFFAOYSA-N 0.000 claims 1
- NGNLGAMSLBPUIA-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-7-yl)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3COCCNC3=NC=2)=N1 NGNLGAMSLBPUIA-UHFFFAOYSA-N 0.000 claims 1
- NRRJVZAUAVEQBB-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(3,4-dihydro-2h-pyrido[3,2-b][1,4]oxazin-7-yl)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3OCCNC3=NC=2)=N1 NRRJVZAUAVEQBB-UHFFFAOYSA-N 0.000 claims 1
- MSRGLTKWJUZZNV-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3OCC(=O)NC3=NC=2)=N1 MSRGLTKWJUZZNV-UHFFFAOYSA-N 0.000 claims 1
- KBYOYINAQFXNAF-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C3CCCNC3=NC=2)=N1 KBYOYINAQFXNAF-UHFFFAOYSA-N 0.000 claims 1
- GAZUXIRBXBWACN-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(2-methoxyethylamino)pyrimidin-5-yl]phenyl]urea Chemical compound C1=NC(NCCOC)=NC=C1C(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 GAZUXIRBXBWACN-UHFFFAOYSA-N 0.000 claims 1
- KNIVYSHNIIOYFC-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(2-morpholin-4-ylethoxy)pyrimidin-5-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(OCCN3CCOCC3)=NC=2)=N1 KNIVYSHNIIOYFC-UHFFFAOYSA-N 0.000 claims 1
- XOMFKSVMGOXAIE-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(2-morpholin-4-ylethylamino)pyrimidin-5-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCN3CCOCC3)=NC=2)=N1 XOMFKSVMGOXAIE-UHFFFAOYSA-N 0.000 claims 1
- DYZYDDOUBUBTQK-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(2-piperidin-1-ylethylamino)pyrimidin-5-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCN3CCCCC3)=NC=2)=N1 DYZYDDOUBUBTQK-UHFFFAOYSA-N 0.000 claims 1
- LTZXBGLHIROMLC-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(3-morpholin-4-ylpropyl)pyrimidin-5-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(CCCN3CCOCC3)=NC=2)=N1 LTZXBGLHIROMLC-UHFFFAOYSA-N 0.000 claims 1
- AAGGNJKQIKQHRZ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-(morpholin-4-ylmethyl)pyrimidin-5-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(CN3CCOCC3)=NC=2)=N1 AAGGNJKQIKQHRZ-UHFFFAOYSA-N 0.000 claims 1
- UPATUIXPVLRHJN-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[2-[2-(dimethylamino)ethylamino]pyrimidin-5-yl]phenyl]urea Chemical compound C1=NC(NCCN(C)C)=NC=C1C(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 UPATUIXPVLRHJN-UHFFFAOYSA-N 0.000 claims 1
- KNQQFXNBIFIPKB-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[5-cyano-6-(2-morpholin-4-ylethylamino)pyridin-3-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=C(C(NCCN3CCOCC3)=NC=2)C#N)=N1 KNQQFXNBIFIPKB-UHFFFAOYSA-N 0.000 claims 1
- WWIKKSQAXGYMGO-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-(2-morpholin-4-ylethylamino)pyridin-3-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCN3CCOCC3)=CC=2)=N1 WWIKKSQAXGYMGO-UHFFFAOYSA-N 0.000 claims 1
- VGULJDCUEBSQME-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-(3-morpholin-4-ylpropylamino)pyridin-3-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCCN3CCOCC3)=CC=2)=N1 VGULJDCUEBSQME-UHFFFAOYSA-N 0.000 claims 1
- OFXMAYYQCCXYAL-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-[2-(1-methylpyrrolidin-2-yl)ethylamino]pyridin-3-yl]phenyl]urea Chemical compound CN1CCCC1CCNC1=CC=C(C=2C=CC(NC(=O)NC3=NOC(=C3)C(C)(C)C)=CC=2)C=N1 OFXMAYYQCCXYAL-UHFFFAOYSA-N 0.000 claims 1
- CSFBAOXZJQXBBJ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-[2-(4,4-difluoropiperidin-1-yl)ethylamino]pyridin-3-yl]phenyl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(NCCN3CCC(F)(F)CC3)=CC=2)=N1 CSFBAOXZJQXBBJ-UHFFFAOYSA-N 0.000 claims 1
- DMPWOQSOJPXOBG-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-(2-morpholin-4-ylethylamino)pyrimidin-5-yl]pyridin-2-yl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2N=CC(=CC=2)C=2C=NC(NCCN3CCOCC3)=NC=2)=N1 DMPWOQSOJPXOBG-UHFFFAOYSA-N 0.000 claims 1
- IEQWBUTYOGLBGK-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-(cyclopropylamino)pyrimidin-5-yl]pyridin-2-yl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2N=CC(=CC=2)C=2C=NC(NC3CC3)=NC=2)=N1 IEQWBUTYOGLBGK-UHFFFAOYSA-N 0.000 claims 1
- QGPYNUUKSPTOFE-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-(oxan-4-ylamino)pyrimidin-5-yl]pyridin-2-yl]urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2N=CC(=CC=2)C=2C=NC(NC3CCOCC3)=NC=2)=N1 QGPYNUUKSPTOFE-UHFFFAOYSA-N 0.000 claims 1
- BCTJHMLFSBSISN-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-(propan-2-ylamino)pyrimidin-5-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(C)C)=NC=C1C(C=N1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 BCTJHMLFSBSISN-UHFFFAOYSA-N 0.000 claims 1
- YHFGRESZZUIFBR-UHFFFAOYSA-N 1-[3-(2-fluoropropan-2-yl)-1,2-oxazol-5-yl]-3-[4-[6-(2-morpholin-4-ylethylamino)pyridin-3-yl]phenyl]urea Chemical compound O1N=C(C(C)(F)C)C=C1NC(=O)NC1=CC=C(C=2C=NC(NCCN3CCOCC3)=CC=2)C=C1 YHFGRESZZUIFBR-UHFFFAOYSA-N 0.000 claims 1
- PNLBQQOEXGSXCW-UHFFFAOYSA-N 1-[4-(2-amino-4-methoxypyrimidin-5-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound COC1=NC(N)=NC=C1C(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 PNLBQQOEXGSXCW-UHFFFAOYSA-N 0.000 claims 1
- DJKOWYRZGPYGFB-UHFFFAOYSA-N 1-[4-(2-amino-4-methylpyrimidin-5-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound CC1=NC(N)=NC=C1C(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 DJKOWYRZGPYGFB-UHFFFAOYSA-N 0.000 claims 1
- WBSARNYAQLZHGW-UHFFFAOYSA-N 1-[4-(2-aminopyrimidin-5-yl)-2-methoxyphenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound COC1=CC(C=2C=NC(N)=NC=2)=CC=C1NC(=O)NC=1C=C(C(C)(C)C)ON=1 WBSARNYAQLZHGW-UHFFFAOYSA-N 0.000 claims 1
- JSVVHGVXWNWTHD-UHFFFAOYSA-N 1-[4-(2-aminopyrimidin-5-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O1C(C(C)(C)C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2C=NC(N)=NC=2)=N1 JSVVHGVXWNWTHD-UHFFFAOYSA-N 0.000 claims 1
- DPKSRMNYQJZOIX-UHFFFAOYSA-N 1-[4-(6-amino-2-methylpyridin-3-yl)phenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound CC1=NC(N)=CC=C1C(C=C1)=CC=C1NC(=O)NC1=NOC(C(C)(C)C)=C1 DPKSRMNYQJZOIX-UHFFFAOYSA-N 0.000 claims 1
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- ZVXAFVCHEIPHDR-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)C(F)(F)F ZVXAFVCHEIPHDR-UHFFFAOYSA-N 0.000 description 1
- IFFNDNZRDKTJEH-UHFFFAOYSA-N methyl 3-fluoro-2-(fluoromethyl)-2-methylpropanoate Chemical compound COC(=O)C(C)(CF)CF IFFNDNZRDKTJEH-UHFFFAOYSA-N 0.000 description 1
- KJRFTNVYOAGTHK-UHFFFAOYSA-N methyl 3-hydroxy-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CO KJRFTNVYOAGTHK-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KDJWLVDAZBRXOD-UHFFFAOYSA-N phenyl n-[5-(1,1,1-trifluoro-2-methylpropan-2-yl)-1,2-oxazol-3-yl]carbamate Chemical compound O1C(C(C)(C)C(F)(F)F)=CC(NC(=O)OC=2C=CC=CC=2)=N1 KDJWLVDAZBRXOD-UHFFFAOYSA-N 0.000 description 1
- JDQCLNBTRQPLGY-UHFFFAOYSA-N phenyl n-[5-(1,3-difluoro-2-methylpropan-2-yl)-1,2-oxazol-3-yl]carbamate Chemical compound O1C(C(CF)(CF)C)=CC(NC(=O)OC=2C=CC=CC=2)=N1 JDQCLNBTRQPLGY-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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| US23531609P | 2009-08-19 | 2009-08-19 | |
| US61/235,316 | 2009-08-19 | ||
| PCT/US2010/045876 WO2011022473A1 (en) | 2009-08-19 | 2010-08-18 | Biaryl compounds and methods of use thereof |
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| EP (1) | EP2467137A1 (https=) |
| JP (1) | JP2013502429A (https=) |
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| CN (1) | CN102470127A (https=) |
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| MX (1) | MX2012001974A (https=) |
| WO (1) | WO2011022473A1 (https=) |
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| JP6097998B2 (ja) * | 2010-12-16 | 2017-03-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成のビアリールアミドインヒビター |
| CA2835835C (en) | 2011-05-13 | 2019-04-02 | Array Biopharma Inc. | Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as trka kinase inhibitors |
| US8877763B2 (en) * | 2012-03-22 | 2014-11-04 | Genosco | Substituted pyridopyrimidine compounds and their use as FLT3 inhibitors |
| KR101529496B1 (ko) * | 2012-12-27 | 2015-06-22 | 한국과학기술원 | 낮은 열팽창 계수를 갖는 신규한 폴리아미드이미드 |
| SMT201700152T1 (it) | 2013-03-15 | 2017-05-08 | Glaxosmithkline Ip Dev Ltd | Derivati piridinici come inibitori della chinasi riarrangiata durante la trasfezione (ret) |
| AR095308A1 (es) | 2013-03-15 | 2015-10-07 | Glaxosmithkline Ip Dev Ltd | Compuesto de 2-piridona, composición farmacéutica que lo comprende y su uso para preparar un medicamento |
| KR20160055170A (ko) * | 2013-08-30 | 2016-05-17 | 암비트 바이오사이언시즈 코포레이션 | 바이아릴 아세트아미드 화합물 및 이의 사용 방법 |
| CN104513259B (zh) * | 2013-09-26 | 2017-06-16 | 广东东阳光药业有限公司 | 取代脲衍生物及其在药物中的应用 |
| CN104513253A (zh) | 2013-10-01 | 2015-04-15 | 南京波尔泰药业科技有限公司 | 用于治疗增殖性疾病的大环化合物 |
| LT3466955T (lt) | 2014-01-13 | 2021-02-25 | Aurigene Discovery Technologies Limited | Oksazol[4,5-b]piridino ir tiazol[4,5-b]piridino darinių, kaip irak4 inhibitorių, skirtų vėžio gydymui, gamybos būdas |
| WO2016038519A1 (en) * | 2014-09-08 | 2016-03-17 | Glaxosmithkline Intellectual Property Development Limited | Crystalline forms of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-n-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide |
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| WO2016037578A1 (en) | 2014-09-10 | 2016-03-17 | Glaxosmithkline Intellectual Property Development Limited | Novel compounds as rearranged during transfection (ret) inhibitors |
| CN105461709B (zh) * | 2014-09-26 | 2020-01-21 | 广东东阳光药业有限公司 | 取代脲衍生物及其在药物中的应用 |
| CN104387331A (zh) * | 2014-10-27 | 2015-03-04 | 湖南华腾制药有限公司 | 一种吡嗪衍生物的制备方法 |
| CN105001172B (zh) * | 2015-06-30 | 2018-02-09 | 浙江大学 | 5,6‑二取代氮杂嘧啶酮类化合物及制备方法 |
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| US20240116962A1 (en) * | 2020-12-31 | 2024-04-11 | Tsinghua University | Pyridine-2-amine derivative and pharmaceutical composition and use thereof |
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- 2010-08-18 KR KR1020127007076A patent/KR20120059558A/ko not_active Withdrawn
- 2010-08-18 EP EP10745711A patent/EP2467137A1/en not_active Withdrawn
- 2010-08-18 JP JP2012525664A patent/JP2013502429A/ja active Pending
- 2010-08-18 WO PCT/US2010/045876 patent/WO2011022473A1/en not_active Ceased
- 2010-08-18 CN CN2010800366234A patent/CN102470127A/zh active Pending
- 2010-08-18 BR BR112012003661A patent/BR112012003661A2/pt not_active IP Right Cessation
- 2010-08-18 CA CA2770454A patent/CA2770454A1/en not_active Abandoned
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