KR20110015699A - 디아자카르바졸 및 사용 방법 - Google Patents

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Publication number

KR20110015699A

KR20110015699A KR1020117000608A KR20117000608A KR20110015699A KR 20110015699 A KR20110015699 A KR 20110015699A KR 1020117000608 A KR1020117000608 A KR 1020117000608A KR 20117000608 A KR20117000608 A KR 20117000608A KR 20110015699 A KR20110015699 A KR 20110015699A

Authority

KR

South Korea

Prior art keywords

alkyl

groups

compound

heterocyclyl

heteroaryl

Prior art date

2008-06-11

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.)

Withdrawn

Links

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• BZHCVCNZIJZMRN-UHFFFAOYSA-N 9h-pyridazino[3,4-b]indole Chemical compound N1=CC=C2C3=CC=CC=C3NC2=N1 BZHCVCNZIJZMRN-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 242
• -1 diazacarbazole compound Chemical class 0.000 claims abstract description 107
• 238000000034 method Methods 0.000 claims abstract description 81
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 201000011510 cancer Diseases 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 117
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 96
• 125000000623 heterocyclic group Chemical group 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 65
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
• 125000005843 halogen group Chemical group 0.000 claims description 55
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000005842 heteroatom Chemical group 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 241000124008 Mammalia Species 0.000 claims description 27
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical group [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 20
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 18
• 229940127089 cytotoxic agent Drugs 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 239000012453 solvate Substances 0.000 claims description 18
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 230000002159 abnormal effect Effects 0.000 claims description 11
• 230000010261 cell growth Effects 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000006413 ring segment Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
• 206010039491 Sarcoma Diseases 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 201000000050 myeloid neoplasm Diseases 0.000 claims description 6
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
• 239000012623 DNA damaging agent Substances 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 239000000203 mixture Substances 0.000 abstract description 57
• 239000003112 inhibitor Substances 0.000 abstract description 18
• 101150050673 CHK1 gene Proteins 0.000 abstract description 16
• 238000011282 treatment Methods 0.000 abstract description 12
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• 238000011065 in-situ storage Methods 0.000 abstract description 4
• 229940043355 kinase inhibitor Drugs 0.000 abstract description 4
• 210000004962 mammalian cell Anatomy 0.000 abstract description 4
• 230000001575 pathological effect Effects 0.000 abstract description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 abstract description 4
• 102000006459 Checkpoint Kinase 1 Human genes 0.000 abstract description 3
• 108010019244 Checkpoint Kinase 1 Proteins 0.000 abstract description 3
• 239000012830 cancer therapeutic Substances 0.000 abstract description 2
• 229940124597 therapeutic agent Drugs 0.000 abstract description 2
• 239000002904 solvent Substances 0.000 description 104
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• 239000002585 base Substances 0.000 description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• 210000004027 cell Anatomy 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 239000007787 solid Substances 0.000 description 27
• 239000003054 catalyst Substances 0.000 description 25
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
• 238000010992 reflux Methods 0.000 description 22
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• 229940002612 prodrug Drugs 0.000 description 17
• 239000000651 prodrug Substances 0.000 description 17
• 229960004132 diethyl ether Drugs 0.000 description 15
• 238000003556 assay Methods 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 14
• 150000004677 hydrates Chemical class 0.000 description 14
• 239000000543 intermediate Substances 0.000 description 14
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
• 238000001914 filtration Methods 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 239000003814 drug Substances 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 229910000029 sodium carbonate Inorganic materials 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• 239000000758 substrate Substances 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 10
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 230000009467 reduction Effects 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 9
• 239000001257 hydrogen Substances 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 101100220616 Caenorhabditis elegans chk-2 gene Proteins 0.000 description 8
• 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 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000010168 coupling process Methods 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 108090000765 processed proteins & peptides Proteins 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
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• 239000000126 substance Substances 0.000 description 7
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 238000005516 engineering process Methods 0.000 description 6
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
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• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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• 125000003386 piperidinyl group Chemical group 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000018102 proteins Nutrition 0.000 description 5
• 102000004169 proteins and genes Human genes 0.000 description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
• 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 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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