CA2582235A1 - Lactam compounds useful as protein kinase inhibitors - Google Patents

Info

Publication number

CA2582235A1

CA2582235A1 CA002582235A CA2582235A CA2582235A1 CA 2582235 A1 CA2582235 A1 CA 2582235A1 CA 002582235 A CA002582235 A CA 002582235A CA 2582235 A CA2582235 A CA 2582235A CA 2582235 A1 CA2582235 A1 CA 2582235A1

Authority

CA

Canada

Prior art keywords

pyrimido

dihydro

amino

benzazepin

oxo

Prior art date

2004-10-04

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Lactam compounds Chemical class 0.000 title claims description 161
• 239000003909 protein kinase inhibitor Substances 0.000 title description 12
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 7
• 238000000034 method Methods 0.000 claims abstract description 255
• 150000001875 compounds Chemical class 0.000 claims abstract description 178
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 125000001931 aliphatic group Chemical group 0.000 claims description 110
• 125000003118 aryl group Chemical group 0.000 claims description 81
• 229910052757 nitrogen Inorganic materials 0.000 claims description 79
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 66
• 239000001257 hydrogen Substances 0.000 claims description 62
• 206010028980 Neoplasm Diseases 0.000 claims description 56
• 229910052760 oxygen Inorganic materials 0.000 claims description 55
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 125000002947 alkylene group Chemical group 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 39
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
• 101150050673 CHK1 gene Proteins 0.000 claims description 24
• 230000000694 effects Effects 0.000 claims description 24
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
• 125000006413 ring segment Chemical group 0.000 claims description 23
• 239000005441 aurora Substances 0.000 claims description 22
• 201000011510 cancer Diseases 0.000 claims description 22
• 125000001475 halogen functional group Chemical group 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 108091000080 Phosphotransferase Proteins 0.000 claims description 14
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 14
• 102000020233 phosphotransferase Human genes 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 12
• 239000002246 antineoplastic agent Substances 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• 125000000532 dioxanyl group Chemical group 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 238000001959 radiotherapy Methods 0.000 claims description 5
• 125000000732 arylene group Chemical group 0.000 claims description 2
• 125000005549 heteroarylene group Chemical group 0.000 claims description 2
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
• 239000002254 cytotoxic agent Substances 0.000 claims 1
• 231100000599 cytotoxic agent Toxicity 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 72
• 102000001253 Protein Kinase Human genes 0.000 abstract description 32
• 108060006633 protein kinase Proteins 0.000 abstract description 32
• 239000003112 inhibitor Substances 0.000 abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 27
• 238000011282 treatment Methods 0.000 abstract description 16
• 201000010099 disease Diseases 0.000 abstract description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 320
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 199
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
• 239000000243 solution Substances 0.000 description 69
• 210000004027 cell Anatomy 0.000 description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
• NAMXZEZCNUIYCF-UHFFFAOYSA-N 8-chloro-4-(dimethylaminomethylidene)-1h-1-benzazepine-2,5-dione Chemical compound O=C1C(=CN(C)C)CC(=O)NC2=CC(Cl)=CC=C21 NAMXZEZCNUIYCF-UHFFFAOYSA-N 0.000 description 59
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
• 229910001868 water Inorganic materials 0.000 description 48
• 235000002639 sodium chloride Nutrition 0.000 description 46
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 44
• 239000011541 reaction mixture Substances 0.000 description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
• 125000000217 alkyl group Chemical group 0.000 description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 35
• 238000006243 chemical reaction Methods 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 27
• 238000003786 synthesis reaction Methods 0.000 description 27
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 239000003814 drug Substances 0.000 description 22
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• OCUSYBHPZIFMRI-UHFFFAOYSA-N 1-benzazepin-6-one Chemical compound N1=CC=CC=C2C(=O)C=CC=C21 OCUSYBHPZIFMRI-UHFFFAOYSA-N 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 238000000746 purification Methods 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• 238000004587 chromatography analysis Methods 0.000 description 19
• 230000005764 inhibitory process Effects 0.000 description 19
• SYEIAEYQBUCQFE-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-9-iodo-5,7-dihydropyrimido[5,4-d][1]benzazepin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(I)C=2)C3=N1 SYEIAEYQBUCQFE-UHFFFAOYSA-N 0.000 description 18
• 239000000725 suspension Substances 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 238000003556 assay Methods 0.000 description 16
• QAYPFHIZJSDUSF-UHFFFAOYSA-N azepin-3-one Chemical compound O=C1C=CC=CN=C1 QAYPFHIZJSDUSF-UHFFFAOYSA-N 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 208000035475 disorder Diseases 0.000 description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
• 239000011347 resin Substances 0.000 description 15
• 229920005989 resin Polymers 0.000 description 15
• 150000001721 carbon Chemical group 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 13
• 230000001404 mediated effect Effects 0.000 description 13
• 229910017604 nitric acid Inorganic materials 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
• RKRGZCAHMPOYJC-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepine-9-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(C=2)C(O)=O)C3=N1 RKRGZCAHMPOYJC-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 230000014509 gene expression Effects 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• WYWRZUGOOAILCD-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-10-iodo-5,7-dihydropyrimido[5,4-d][1]benzazepin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC(I)=CC=2)C3=N1 WYWRZUGOOAILCD-UHFFFAOYSA-N 0.000 description 11
• KJESCGNRQKHPDB-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepine-10-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC(=CC=2)C(O)=O)C3=N1 KJESCGNRQKHPDB-UHFFFAOYSA-N 0.000 description 11
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
• 108090000433 Aurora kinases Proteins 0.000 description 11
• 102000003989 Aurora kinases Human genes 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 229940079593 drug Drugs 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
• BUYMLVMIVKWJSQ-UHFFFAOYSA-N 8-chloro-3,4-dihydro-1h-1-benzazepine-2,5-dione Chemical compound N1C(=O)CCC(=O)C=2C1=CC(Cl)=CC=2 BUYMLVMIVKWJSQ-UHFFFAOYSA-N 0.000 description 10
• RQVFWSSKGKZGCU-UHFFFAOYSA-N 9-chloro-2-(4-iodoanilino)-5,7-dihydropyrimido[5,4-d][1]benzazepin-6-one Chemical compound C=1C(Cl)=CC=C(C2=N3)C=1NC(=O)CC2=CN=C3NC1=CC=C(I)C=C1 RQVFWSSKGKZGCU-UHFFFAOYSA-N 0.000 description 10
• 239000012623 DNA damaging agent Substances 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
• 150000002357 guanidines Chemical class 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• 239000000758 substrate Substances 0.000 description 10
• 229940124597 therapeutic agent Drugs 0.000 description 10
• SXTSBZBQQRIYCU-UHFFFAOYSA-N 4-guanidinobenzoic acid Chemical compound NC(=N)NC1=CC=C(C(O)=O)C=C1 SXTSBZBQQRIYCU-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 239000005711 Benzoic acid Substances 0.000 description 9
• 102000004190 Enzymes Human genes 0.000 description 9
• 108090000790 Enzymes Proteins 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 9
• 229960004365 benzoic acid Drugs 0.000 description 9
• 230000004663 cell proliferation Effects 0.000 description 9
• 238000006911 enzymatic reaction Methods 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 229960004198 guanidine Drugs 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 235000019198 oils Nutrition 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• AYQMNFRCBKOMIA-UHFFFAOYSA-N 1-benzazepin-2-one Chemical compound O=C1C=CC=C2C=CC=CC2=N1 AYQMNFRCBKOMIA-UHFFFAOYSA-N 0.000 description 8
• SFVCOZOGYYJPII-UHFFFAOYSA-N 7-bromo-4-(dimethylaminomethylidene)-1h-1-benzazepine-2,5-dione Chemical compound O=C1C(=CN(C)C)CC(=O)NC2=CC=C(Br)C=C21 SFVCOZOGYYJPII-UHFFFAOYSA-N 0.000 description 8
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• 229910052693 Europium Inorganic materials 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 238000007792 addition Methods 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 235000019439 ethyl acetate Nutrition 0.000 description 8
• OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 230000002062 proliferating effect Effects 0.000 description 8
• 108090000623 proteins and genes Proteins 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 235000017557 sodium bicarbonate Nutrition 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 238000006467 substitution reaction Methods 0.000 description 8
• KCEIBYAXTBNNRZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)guanidine Chemical compound COC1=CC=C(NC(N)=N)C=C1OC KCEIBYAXTBNNRZ-UHFFFAOYSA-N 0.000 description 7
• RCQMWDICUYFCQC-UHFFFAOYSA-N 2-acetamido-4-iodobenzoic acid Chemical compound CC(=O)NC1=CC(I)=CC=C1C(O)=O RCQMWDICUYFCQC-UHFFFAOYSA-N 0.000 description 7
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• 238000005859 coupling reaction Methods 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
• 125000000524 functional group Chemical group 0.000 description 7
• 230000012010 growth Effects 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• 125000004193 piperazinyl group Chemical group 0.000 description 7
• 125000003386 piperidinyl group Chemical group 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 102000004169 proteins and genes Human genes 0.000 description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 7
• 239000011780 sodium chloride Substances 0.000 description 7
• NTFZHFGLYBTEGG-UHFFFAOYSA-N tert-butyl n-[3-[2-(3,4-dimethoxyanilino)-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepin-9-yl]prop-2-ynyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(C=2)C#CCNC(=O)OC(C)(C)C)C3=N1 NTFZHFGLYBTEGG-UHFFFAOYSA-N 0.000 description 7
• 210000004881 tumor cell Anatomy 0.000 description 7
• LYZVMWUMQGNMPI-UHFFFAOYSA-N 2-amino-10-iodo-5,7-dihydropyrimido[5,4-d][1]benzazepin-6-one Chemical compound C1C(=O)NC2=CC=C(I)C=C2C2=NC(N)=NC=C21 LYZVMWUMQGNMPI-UHFFFAOYSA-N 0.000 description 6
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• QMADAJQMIDIYRU-UHFFFAOYSA-N 4-[(9-chloro-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(Cl)C=2)C3=N1 QMADAJQMIDIYRU-UHFFFAOYSA-N 0.000 description 6
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• 108020004414 DNA Proteins 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• 241000238631 Hexapoda Species 0.000 description 6
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• SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 125000004494 ethyl ester group Chemical group 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• 229940043355 kinase inhibitor Drugs 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 230000001105 regulatory effect Effects 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000012453 solvate Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
• XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
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