TWI492946B - 吡咯并嘧啶及嘌呤衍生物 - Google Patents

Info

Publication number

TWI492946B

TWI492946B TW101134547A TW101134547A TWI492946B TW I492946 B TWI492946 B TW I492946B TW 101134547 A TW101134547 A TW 101134547A TW 101134547 A TW101134547 A TW 101134547A TW I492946 B TWI492946 B TW I492946B

Authority

TW

Taiwan

Prior art keywords

pharmaceutically acceptable

compound

acceptable salt

methyl

group

Prior art date

2011-09-22

Links

• Espacenet
• Global Dossier
• Discuss

• KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title description 2
• 150000001454 anthracenes Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 535
• 150000003839 salts Chemical class 0.000 claims description 389
• -1 cyano, difluoromethyl Chemical group 0.000 claims description 223
• 238000002360 preparation method Methods 0.000 claims description 153
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 134
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 104
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 93
• 229910052739 hydrogen Inorganic materials 0.000 claims description 89
• 239000001257 hydrogen Substances 0.000 claims description 89
• 229910052736 halogen Inorganic materials 0.000 claims description 76
• 150000002367 halogens Chemical class 0.000 claims description 76
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 65
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 56
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 239000000460 chlorine Substances 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
• 230000002159 abnormal effect Effects 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 230000010261 cell growth Effects 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 150000002431 hydrogen Chemical class 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 26
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000006413 ring segment Chemical group 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 229910052720 vanadium Inorganic materials 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 5
• 230000000670 limiting effect Effects 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 125000006168 tricyclic group Chemical group 0.000 claims description 3
• FXDRONVVHLDETA-JCNLHEQBSA-N CNCC=C[C@@H]1C[C@H](C1)OC=1C2=C(N=C(N1)NC=1C=NN(C1)C)NC=C2C2=NC=CC=C2 Chemical compound CNCC=C[C@@H]1C[C@H](C1)OC=1C2=C(N=C(N1)NC=1C=NN(C1)C)NC=C2C2=NC=CC=C2 FXDRONVVHLDETA-JCNLHEQBSA-N 0.000 claims description 2
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 claims description 2
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
• 125000000172 C5-C10 aryl group Chemical group 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 402
• 235000019439 ethyl acetate Nutrition 0.000 description 192
• 239000000203 mixture Substances 0.000 description 133
• 239000000243 solution Substances 0.000 description 120
• 238000006243 chemical reaction Methods 0.000 description 117
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 103
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 89
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 75
• 238000005481 NMR spectroscopy Methods 0.000 description 73
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
• 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
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 52
• 239000011734 sodium Substances 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 48
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 46
• 239000012044 organic layer Substances 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• 206010028980 Neoplasm Diseases 0.000 description 42
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 39
• 238000000034 method Methods 0.000 description 38
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 37
• 239000002585 base Substances 0.000 description 35
• 239000003921 oil Substances 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 31
• 239000003112 inhibitor Substances 0.000 description 30
• 150000001412 amines Chemical class 0.000 description 29
• 239000007787 solid Substances 0.000 description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• 229920006395 saturated elastomer Polymers 0.000 description 27
• 241000124008 Mammalia Species 0.000 description 26
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
• 239000002253 acid Substances 0.000 description 25
• 239000002904 solvent Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• 239000000706 filtrate Substances 0.000 description 20
• 125000001153 fluoro group Chemical group F* 0.000 description 20
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 19
• 201000011510 cancer Diseases 0.000 description 19
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 19
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 18
• 125000000217 alkyl group Chemical group 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
• 239000010410 layer Substances 0.000 description 18
• 239000003208 petroleum Substances 0.000 description 18
• 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 18
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• 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 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000002246 antineoplastic agent Substances 0.000 description 12
• 238000003818 flash chromatography Methods 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
• 230000000340 anti-metabolite Effects 0.000 description 11
• 229940100197 antimetabolite Drugs 0.000 description 11
• 239000002256 antimetabolite Substances 0.000 description 11
• 239000012043 crude product Substances 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 239000012453 solvate Substances 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• 239000003039 volatile agent Substances 0.000 description 11
• 102000014150 Interferons Human genes 0.000 description 10
• 108010050904 Interferons Proteins 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
• 239000000126 substance Substances 0.000 description 10
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 9
• 239000011591 potassium Substances 0.000 description 9
• 229910052700 potassium Inorganic materials 0.000 description 9
• 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 9
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 9
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 8
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
• 208000002495 Uterine Neoplasms Diseases 0.000 description 8
• 229940100198 alkylating agent Drugs 0.000 description 8
• 239000002168 alkylating agent Substances 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 239000013058 crude material Substances 0.000 description 8
• 201000005202 lung cancer Diseases 0.000 description 8
• 208000020816 lung neoplasm Diseases 0.000 description 8
• LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 8
• 206010046766 uterine cancer Diseases 0.000 description 8
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 230000002280 anti-androgenic effect Effects 0.000 description 7
• 239000000051 antiandrogen Substances 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 230000008878 coupling Effects 0.000 description 7
• 238000010168 coupling process Methods 0.000 description 7
• 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
• 201000001441 melanoma Diseases 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
• SWDHPDPYROTODE-UHFFFAOYSA-N NN.C=CC.Cl Chemical compound NN.C=CC.Cl SWDHPDPYROTODE-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 238000005576 amination reaction Methods 0.000 description 6
• 239000003242 anti bacterial agent Substances 0.000 description 6
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 6
• 229940088710 antibiotic agent Drugs 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 229940088598 enzyme Drugs 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 239000003102 growth factor Substances 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 238000004808 supercritical fluid chromatography Methods 0.000 description 6
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 5
• VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
• 206010005003 Bladder cancer Diseases 0.000 description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 5
• 230000003388 anti-hormonal effect Effects 0.000 description 5
• 230000000259 anti-tumor effect Effects 0.000 description 5
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 5
• 229960004316 cisplatin Drugs 0.000 description 5
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 231100000599 cytotoxic agent Toxicity 0.000 description 5
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 5
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
• 239000000367 immunologic factor Substances 0.000 description 5
• 229940079322 interferon Drugs 0.000 description 5
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