JP2010521458A5 - - Google Patents

Info

Publication number

JP2010521458A5

JP2010521458A5 JP2009553600A JP2009553600A JP2010521458A5 JP 2010521458 A5 JP2010521458 A5 JP 2010521458A5 JP 2009553600 A JP2009553600 A JP 2009553600A JP 2009553600 A JP2009553600 A JP 2009553600A JP 2010521458 A5 JP2010521458 A5 JP 2010521458A5

Authority

JP

Japan

Prior art keywords

group

trifluoromethyl

ylamino

pyridin

compound

Prior art date

2008-03-10

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

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims description 251
• 238000000034 method Methods 0.000 claims description 210
• -1 cyano, thio, nitro Chemical group 0.000 claims description 200
• 239000000203 mixture Substances 0.000 claims description 97
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 91
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 102000001253 Protein Kinase Human genes 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 108060006633 protein kinase Proteins 0.000 claims description 21
• 125000002950 monocyclic group Chemical group 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 229910052763 palladium Inorganic materials 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 17
• 108091000080 Phosphotransferase Proteins 0.000 claims description 17
• 102000020233 phosphotransferase Human genes 0.000 claims description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
• 201000011510 cancer Diseases 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 238000011282 treatment Methods 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 210000001650 focal adhesion Anatomy 0.000 claims description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 230000000694 effects Effects 0.000 claims description 11
• 230000003211 malignant effect Effects 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 238000001914 filtration Methods 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 239000003446 ligand Substances 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 230000002159 abnormal effect Effects 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 6
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
• 230000009286 beneficial effect Effects 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 229910052723 transition metal Inorganic materials 0.000 claims description 6
• 150000003624 transition metals Chemical class 0.000 claims description 6
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 238000000338 in vitro Methods 0.000 claims description 5
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 5
• 150000003852 triazoles Chemical class 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 claims description 2
• 102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 230000036210 malignancy Effects 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 125
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 110
• 238000005481 NMR spectroscopy Methods 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
• 239000007787 solid Substances 0.000 description 71
• 238000005160 1H NMR spectroscopy Methods 0.000 description 61
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 239000002904 solvent Substances 0.000 description 37
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 36
• 239000012043 crude product Substances 0.000 description 35
• 239000000243 solution Substances 0.000 description 35
• 235000019439 ethyl acetate Nutrition 0.000 description 34
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 33
• 229910000024 caesium carbonate Inorganic materials 0.000 description 33
• 238000010898 silica gel chromatography Methods 0.000 description 32
• 239000000047 product Substances 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 30
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 29
• 102100037813 Focal adhesion kinase 1 Human genes 0.000 description 28
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• YNNUSGIPVFPVBX-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC(C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-UHFFFAOYSA-N 0.000 description 22
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 22
• 229910052786 argon Inorganic materials 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 21
• 150000003840 hydrochlorides Chemical class 0.000 description 16
• 238000002953 preparative HPLC Methods 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 13
• BLDAPDVJFOJWMZ-UHFFFAOYSA-N 2-[[2-chloro-5-(trifluoromethyl)pyridin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=CC(Cl)=NC=C1C(F)(F)F BLDAPDVJFOJWMZ-UHFFFAOYSA-N 0.000 description 12
• 238000003556 assay Methods 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• XEEQBBXEZSNIQV-UHFFFAOYSA-N 2-chloro-4-iodo-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C=C1I XEEQBBXEZSNIQV-UHFFFAOYSA-N 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 239000000872 buffer Substances 0.000 description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 239000007924 injection Substances 0.000 description 9
• 238000002347 injection Methods 0.000 description 9
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 9
• 239000003039 volatile agent Substances 0.000 description 9
• 239000003085 diluting agent Substances 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 7
• BQTMHUUWYHEPNQ-UHFFFAOYSA-N 2-methoxy-4-morpholin-4-ylaniline Chemical compound C1=C(N)C(OC)=CC(N2CCOCC2)=C1 BQTMHUUWYHEPNQ-UHFFFAOYSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 235000014113 dietary fatty acids Nutrition 0.000 description 7
• 239000000194 fatty acid Substances 0.000 description 7
• 229930195729 fatty acid Natural products 0.000 description 7
• 239000003999 initiator Substances 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 125000004149 thio group Chemical group *S* 0.000 description 7
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 150000001502 aryl halides Chemical class 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 description 6
• 125000001041 indolyl group Chemical group 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 208000024891 symptom Diseases 0.000 description 6
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• 0 **Nc1cc(N*)ncc1* Chemical compound **Nc1cc(N*)ncc1* 0.000 description 5
• FBBFBZJZXFGFCK-UHFFFAOYSA-N 2-[[2-chloro-5-(trifluoromethyl)pyridin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=CC(Cl)=NC=C1C(F)(F)F FBBFBZJZXFGFCK-UHFFFAOYSA-N 0.000 description 5
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 150000001721 carbon Chemical class 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• 238000001727 in vivo Methods 0.000 description 5
• 102000006495 integrins Human genes 0.000 description 5
• 108010044426 integrins Proteins 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 230000001394 metastastic effect Effects 0.000 description 5
• 206010061289 metastatic neoplasm Diseases 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 230000002829 reductive effect Effects 0.000 description 5
• 239000011593 sulfur Substances 0.000 description 5
• 125000000335 thiazolyl group Chemical group 0.000 description 5
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
• HMYXHQDSYJOVBG-UHFFFAOYSA-N 2-chloro-n-(2-pyrimidin-2-ylphenyl)-5-(trifluoromethyl)pyridin-4-amine Chemical compound FC(F)(F)C1=CN=C(Cl)C=C1NC1=CC=CC=C1C1=NC=CC=N1 HMYXHQDSYJOVBG-UHFFFAOYSA-N 0.000 description 4
• CCFGTKQIRWHYTB-UHFFFAOYSA-N 2-methyl-3-nitropyridine Chemical compound CC1=NC=CC=C1[N+]([O-])=O CCFGTKQIRWHYTB-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 4
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 4
• 229940124783 FAK inhibitor Drugs 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
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• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
• 230000002255 enzymatic effect Effects 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 125000005241 heteroarylamino group Chemical group 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• IQEKCKQBCMCLQF-UHFFFAOYSA-N n,n-dimethyl-2-(5-nitro-1h-indol-3-yl)-2-oxoacetamide Chemical compound C1=C([N+]([O-])=O)C=C2C(C(=O)C(=O)N(C)C)=CNC2=C1 IQEKCKQBCMCLQF-UHFFFAOYSA-N 0.000 description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 125000002971 oxazolyl group Chemical group 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 125000003367 polycyclic group Chemical group 0.000 description 4
• 125000003226 pyrazolyl group Chemical group 0.000 description 4
• 125000004076 pyridyl group Chemical group 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 125000003107 substituted aryl group Chemical group 0.000 description 4
• 125000001425 triazolyl group Chemical group 0.000 description 4
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
• WQYDASORCSDVNY-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-4-morpholin-4-ylanilino)pyridin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=CC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1Br WQYDASORCSDVNY-UHFFFAOYSA-N 0.000 description 3
• SVIILPGBQTUQPJ-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyridin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=CC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1Cl SVIILPGBQTUQPJ-UHFFFAOYSA-N 0.000 description 3
• JMHVADDHAXZSPT-UHFFFAOYSA-N 2-[[5-cyano-2-(2-methoxy-4-morpholin-4-ylanilino)pyridin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=CC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1C#N JMHVADDHAXZSPT-UHFFFAOYSA-N 0.000 description 3
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