JP2002537300A5 - - Google Patents

Info

Publication number

JP2002537300A5

JP2002537300A5 JP2000599757A JP2000599757A JP2002537300A5 JP 2002537300 A5 JP2002537300 A5 JP 2002537300A5 JP 2000599757 A JP2000599757 A JP 2000599757A JP 2000599757 A JP2000599757 A JP 2000599757A JP 2002537300 A5 JP2002537300 A5 JP 2002537300A5

Authority

JP

Japan

Prior art keywords

amino

phenyl

radical

ethyl

substituted

Prior art date

2000-02-16

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 heterocyclic radical Chemical class 0.000 description 782
• 125000000217 alkyl group Chemical group 0.000 description 156
• 150000003254 radicals Chemical class 0.000 description 148
• 150000001875 compounds Chemical class 0.000 description 132
• 125000004432 carbon atom Chemical group C* 0.000 description 119
• 229910052736 halogen Inorganic materials 0.000 description 111
• 125000003282 alkyl amino group Chemical group 0.000 description 107
• 239000001257 hydrogen Substances 0.000 description 100
• 229910052739 hydrogen Inorganic materials 0.000 description 100
• 125000003545 alkoxy group Chemical group 0.000 description 97
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
• 150000002367 halogens Chemical class 0.000 description 65
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 56
• 150000003839 salts Chemical class 0.000 description 56
• 239000000126 substance Substances 0.000 description 56
• 235000002639 sodium chloride Nutrition 0.000 description 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 53
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 46
• 239000002253 acid Substances 0.000 description 45
• 150000002431 hydrogen Chemical class 0.000 description 43
• 229910052760 oxygen Inorganic materials 0.000 description 43
• 239000001301 oxygen Substances 0.000 description 43
• YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• 229910052757 nitrogen Inorganic materials 0.000 description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 41
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 39
• 229910052717 sulfur Inorganic materials 0.000 description 38
• 125000001424 substituent group Chemical group 0.000 description 37
• 125000000623 heterocyclic group Chemical group 0.000 description 36
• 125000001931 aliphatic group Chemical group 0.000 description 35
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 34
• 125000005115 alkyl carbamoyl group Chemical group 0.000 description 34
• 239000011593 sulfur Substances 0.000 description 34
• 125000003118 aryl group Chemical group 0.000 description 33
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 32
• 125000002837 carbocyclic group Chemical group 0.000 description 32
• 125000000304 alkynyl group Chemical group 0.000 description 30
• 238000000034 method Methods 0.000 description 30
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 27
• 125000006239 protecting group Chemical group 0.000 description 27
• 125000000524 functional group Chemical group 0.000 description 26
• 125000002947 alkylene group Chemical group 0.000 description 25
• 239000000243 solution Substances 0.000 description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• 239000000203 mixture Substances 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• 238000006243 chemical reaction Methods 0.000 description 21
• 239000000460 chlorine Substances 0.000 description 19
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
• 238000001914 filtration Methods 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 150000005840 aryl radicals Chemical class 0.000 description 18
• 229910052801 chlorine Inorganic materials 0.000 description 16
• 125000003342 alkenyl group Chemical group 0.000 description 15
• 125000004450 alkenylene group Chemical group 0.000 description 15
• 125000003277 amino group Chemical group 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 15
• 125000002757 morpholinyl group Chemical group 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 241001465754 Metazoa Species 0.000 description 14
• 206010028980 Neoplasm Diseases 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• 125000004076 pyridyl group Chemical group 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 125000002252 acyl group Chemical group 0.000 description 13
• 125000001072 heteroaryl group Chemical group 0.000 description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 description 13
• 125000003386 piperidinyl group Chemical group 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
• 238000004587 chromatography analysis Methods 0.000 description 12
• 125000004104 aryloxy group Chemical group 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 125000002883 imidazolyl group Chemical group 0.000 description 11
• KDDZQNZNSORQST-UHFFFAOYSA-N 4-[[6-(3-aminoanilino)-9-ethylpurin-2-yl]amino]cyclohexan-1-ol Chemical compound N1=C(NC2CCC(O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(N)=C1 KDDZQNZNSORQST-UHFFFAOYSA-N 0.000 description 10
• 125000005133 alkynyloxy group Chemical group 0.000 description 10
• 125000005015 aryl alkynyl group Chemical group 0.000 description 10
• 125000005312 heteroarylalkynyl group Chemical group 0.000 description 10
• 125000001183 hydrocarbyl group Chemical group 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• 125000004193 piperazinyl group Chemical group 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 description 10
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 239000013078 crystal Substances 0.000 description 9
• 235000019439 ethyl acetate Nutrition 0.000 description 9
• 125000001624 naphthyl group Chemical group 0.000 description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
• 239000008194 pharmaceutical composition Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• 239000004215 Carbon black (E152) Substances 0.000 description 8
• 150000001412 amines Chemical class 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
• 229930195733 hydrocarbon Natural products 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 125000005415 substituted alkoxy group Chemical group 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 239000000052 vinegar Substances 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• 125000002541 furyl group Chemical group 0.000 description 7
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 125000002950 monocyclic group Chemical group 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 125000003396 thiol group Chemical group [H]S* 0.000 description 7
• RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 6
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
• POYRXPOVIRHBRO-UHFFFAOYSA-N 4-[[6-(3-aminoanilino)-9-propan-2-ylpurin-2-yl]amino]cyclohexan-1-ol Chemical compound N1=C(NC2CCC(O)CC2)N=C2N(C(C)C)C=NC2=C1NC1=CC=CC(N)=C1 POYRXPOVIRHBRO-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 102000016736 Cyclin Human genes 0.000 description 6
• 108050006400 Cyclin Proteins 0.000 description 6
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
• DLTUNRUSGNUVJF-CTYIDZIISA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(C(O)=O)=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC(C(O)=O)=C1 DLTUNRUSGNUVJF-CTYIDZIISA-N 0.000 description 6
• 208000001132 Osteoporosis Diseases 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 125000004043 oxo group Chemical group O=* 0.000 description 6
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 5
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 5
• AWRCGEJILTVONY-UHFFFAOYSA-N 6-n-phenyl-7h-purine-2,6-diamine Chemical compound C=12NC=NC2=NC(N)=NC=1NC1=CC=CC=C1 AWRCGEJILTVONY-UHFFFAOYSA-N 0.000 description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 5
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
• PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 5
• 125000002015 acyclic group Chemical group 0.000 description 5
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 5
• 125000004414 alkyl thio group Chemical group 0.000 description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 238000001514 detection method Methods 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 125000001041 indolyl group Chemical group 0.000 description 5
• 230000002401 inhibitory effect Effects 0.000 description 5
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 5
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 125000002971 oxazolyl group Chemical group 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 5
• 125000005493 quinolyl group Chemical group 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
• 125000000335 thiazolyl group Chemical group 0.000 description 5
• 125000001544 thienyl group Chemical group 0.000 description 5
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
• AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
• LKALYIOCUAEKHT-NNUKFRKNSA-N N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC([N+]([O-])=O)=C1 Chemical compound N1=C(N[C@@H]2CC[C@@H](O)CC2)N=C2N(CC)C=NC2=C1NC1=CC=CC([N+]([O-])=O)=C1 LKALYIOCUAEKHT-NNUKFRKNSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 125000004442 acylamino group Chemical group 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 239000003610 charcoal Substances 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 125000001309 chloro group Chemical group Cl* 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 239000003925 fat Substances 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
• 150000002430 hydrocarbons Chemical class 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 125000001841 imino group Chemical group [H]N=* 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 238000003797 solvolysis reaction Methods 0.000 description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
• 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 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 239000005711 Benzoic acid Substances 0.000 description 3
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
• 102000004190 Enzymes Human genes 0.000 description 3
• 108090000790 Enzymes Proteins 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 241001024304 Mino Species 0.000 description 3
• 108091000080 Phosphotransferase Proteins 0.000 description 3
• 102000001332 SRC Human genes 0.000 description 3
• 108060006706 SRC Proteins 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 238000006136 alcoholysis reaction Methods 0.000 description 3
• 125000005236 alkanoylamino group Chemical group 0.000 description 3
• 125000000033 alkoxyamino group Chemical group 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 3
• 235000001014 amino acid Nutrition 0.000 description 3
• 229940024606 amino acid Drugs 0.000 description 3
• 150000001413 amino acids Chemical class 0.000 description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 150000001540 azides Chemical class 0.000 description 3
• 235000010233 benzoic acid Nutrition 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000004305 biphenyl Substances 0.000 description 3
• 210000000988 bone and bone Anatomy 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
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