JP5914667B2 - ピロロピリミジンおよびプリン誘導体 - Google Patents

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Publication number

JP5914667B2

JP5914667B2 JP2014531341A JP2014531341A JP5914667B2 JP 5914667 B2 JP5914667 B2 JP 5914667B2 JP 2014531341 A JP2014531341 A JP 2014531341A JP 2014531341 A JP2014531341 A JP 2014531341A JP 5914667 B2 JP5914667 B2 JP 5914667B2

Authority

JP

Japan

Prior art keywords

methyl

pharmaceutically acceptable

formula

acceptable salt

alkyl

Prior art date

2011-09-22

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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• KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title description 2
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 2
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 510
• 150000003839 salts Chemical class 0.000 claims description 369
• -1 cyano, difluoromethyl Chemical group 0.000 claims description 206
• 229910052736 halogen Inorganic materials 0.000 claims description 86
• 150000002367 halogens Chemical class 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• 239000001257 hydrogen Substances 0.000 claims description 80
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 67
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 55
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
• 239000000460 chlorine Substances 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 230000002159 abnormal effect Effects 0.000 claims description 39
• 230000010261 cell growth Effects 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 241000124008 Mammalia Species 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 5
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• FESKVIPHVGGMNZ-MFKMUULPSA-N 1-[(3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxymethyl]-4-fluoropyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC(OC[C@@H]2[C@H](CN(C2)C(=O)C=C)F)=C(C(Cl)=CN2)C2=N1 FESKVIPHVGGMNZ-MFKMUULPSA-N 0.000 claims description 3
• ODMXWZROLKITMS-RISCZKNCSA-N 1-[(3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxymethyl]-4-methoxypyrrolidin-1-yl]prop-2-en-1-one Chemical compound CO[C@H]1CN(C(=O)C=C)C[C@@H]1COC1=NC(NC2=CN(C)N=C2)=NC2=C1C(Cl)=CN2 ODMXWZROLKITMS-RISCZKNCSA-N 0.000 claims description 3
• SXHNYSZARHNXML-JQWIXIFHSA-N 1-[(3r,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-4-(trifluoromethyl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC(N[C@@H]2[C@H](CN(C2)C(=O)C=C)C(F)(F)F)=C(C(Cl)=CN2)C2=N1 SXHNYSZARHNXML-JQWIXIFHSA-N 0.000 claims description 3
• MKJVMRBTYPHRMX-UONOGXRCSA-N 1-[(3s,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-4-(triazol-1-yl)pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC(N[C@@H]2[C@@H](CN(C2)C(=O)C=C)N2N=NC=C2)=C(C(Cl)=CN2)C2=N1 MKJVMRBTYPHRMX-UONOGXRCSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• LKVQXJRVWLXFLH-WKILWMFISA-N C1[C@@H](N(C)C(=O)C=C)C[C@@H]1OC1=NC(NC=2C(=NN(C)C=2)C)=NC2=C1C(C=1N=CC=CC=1)=CN2 Chemical compound C1[C@@H](N(C)C(=O)C=C)C[C@@H]1OC1=NC(NC=2C(=NN(C)C=2)C)=NC2=C1C(C=1N=CC=CC=1)=CN2 LKVQXJRVWLXFLH-WKILWMFISA-N 0.000 claims description 3
• IKXHZNFGPFFALI-UHFFFAOYSA-N n-[3-[[5-(1-methylpyrazol-4-yl)-2-[(1-methylpyrazol-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide Chemical compound C1=NN(C)C=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(C(=CN2)C3=CN(C)N=C3)C2=N1 IKXHZNFGPFFALI-UHFFFAOYSA-N 0.000 claims description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 351
• 235000019439 ethyl acetate Nutrition 0.000 description 162
• 238000002360 preparation method Methods 0.000 description 148
• 239000000203 mixture Substances 0.000 description 128
• 239000000243 solution Substances 0.000 description 118
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
• 238000006243 chemical reaction Methods 0.000 description 115
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 115
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 109
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 90
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 86
• 238000005481 NMR spectroscopy Methods 0.000 description 79
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 74
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
• 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 68
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
• 239000007787 solid Substances 0.000 description 62
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 57
• 239000003921 oil Substances 0.000 description 56
• 235000019198 oils Nutrition 0.000 description 56
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
• 239000011734 sodium Substances 0.000 description 53
• 239000011541 reaction mixture Substances 0.000 description 51
• 238000000034 method Methods 0.000 description 48
• 239000012044 organic layer Substances 0.000 description 47
• 239000012267 brine Substances 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
• 206010028980 Neoplasm Diseases 0.000 description 38
• 238000003818 flash chromatography Methods 0.000 description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 37
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 36
• 239000000047 product Substances 0.000 description 35
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• 239000003112 inhibitor Substances 0.000 description 30
• 229920006395 saturated elastomer Polymers 0.000 description 30
• 239000003208 petroleum Substances 0.000 description 29
• 238000003756 stirring Methods 0.000 description 29
• 239000002585 base Substances 0.000 description 28
• 239000000706 filtrate Substances 0.000 description 28
• 229910052731 fluorine Inorganic materials 0.000 description 28
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 28
• 239000011737 fluorine Substances 0.000 description 27
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 26
• 150000001412 amines Chemical class 0.000 description 26
• 238000004809 thin layer chromatography Methods 0.000 description 26
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 23
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• 235000019441 ethanol Nutrition 0.000 description 22
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 21
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
• 239000003039 volatile agent Substances 0.000 description 20
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 19
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 239000012230 colorless oil Substances 0.000 description 18
• 239000010410 layer Substances 0.000 description 18
• 201000011510 cancer Diseases 0.000 description 17
• BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
• HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
• 238000004440 column chromatography Methods 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 239000012453 solvate Substances 0.000 description 12
• LBGSWBJURUFGLR-UHFFFAOYSA-N 1-methylpyrazol-4-amine Chemical compound CN1C=C(N)C=N1 LBGSWBJURUFGLR-UHFFFAOYSA-N 0.000 description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 10
• 230000000340 anti-metabolite Effects 0.000 description 10
• 229940100197 antimetabolite Drugs 0.000 description 10
• 239000002256 antimetabolite Substances 0.000 description 10
• 239000002246 antineoplastic agent Substances 0.000 description 10
• 239000013058 crude material Substances 0.000 description 10
• 238000001914 filtration Methods 0.000 description 10
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 10
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 10
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 229910004298 SiO 2 Inorganic materials 0.000 description 9
• 208000002495 Uterine Neoplasms Diseases 0.000 description 9
• 150000004703 alkoxides Chemical class 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 9
• 238000004808 supercritical fluid chromatography Methods 0.000 description 9
• 206010046766 uterine cancer Diseases 0.000 description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 8
• 230000010933 acylation Effects 0.000 description 8
• 238000005917 acylation reaction Methods 0.000 description 8
• 229940100198 alkylating agent Drugs 0.000 description 8
• 239000002168 alkylating agent Substances 0.000 description 8
• 238000005576 amination reaction Methods 0.000 description 8
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 201000005202 lung cancer Diseases 0.000 description 8
• 208000020816 lung neoplasm Diseases 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• 210000003169 central nervous system Anatomy 0.000 description 7
• 238000005859 coupling reaction Methods 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 201000001441 melanoma Diseases 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
• 229940123587 Cell cycle inhibitor Drugs 0.000 description 6
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
• 102000001301 EGF receptor Human genes 0.000 description 6
• 108060006698 EGF receptor Proteins 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• 102000014150 Interferons Human genes 0.000 description 6
• 108010050904 Interferons Proteins 0.000 description 6
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 239000000051 antiandrogen Substances 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 229940088598 enzyme Drugs 0.000 description 6
• 239000003102 growth factor Substances 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
• 239000011591 potassium Substances 0.000 description 6
• 229910052700 potassium Inorganic materials 0.000 description 6
• ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• 125000001424 substituent group Chemical group 0.000 description 6
• BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 5
• HSSJZWWCSQLAQN-UHFFFAOYSA-N 2-[(2,4-dichloropyrrolo[2,3-d]pyrimidin-7-yl)methoxy]ethyl-trimethylsilane Chemical compound N1=C(Cl)N=C2N(COCC[Si](C)(C)C)C=CC2=C1Cl HSSJZWWCSQLAQN-UHFFFAOYSA-N 0.000 description 5
• 206010005003 Bladder cancer Diseases 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 5
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 5
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