JP7225125B2 - ヒストンメチルトランスフェラーゼ阻害剤としてのアザインドール化合物 - Google Patents
ヒストンメチルトランスフェラーゼ阻害剤としてのアザインドール化合物 Download PDFInfo
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- JP7225125B2 JP7225125B2 JP2019567574A JP2019567574A JP7225125B2 JP 7225125 B2 JP7225125 B2 JP 7225125B2 JP 2019567574 A JP2019567574 A JP 2019567574A JP 2019567574 A JP2019567574 A JP 2019567574A JP 7225125 B2 JP7225125 B2 JP 7225125B2
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- Prior art keywords
- mmol
- methoxy
- pharmaceutically acceptable
- acceptable salt
- pyrido
- Prior art date
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- 102000011787 Histone Methyltransferases Human genes 0.000 title description 2
- 108010036115 Histone Methyltransferases Proteins 0.000 title description 2
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title description 2
- 239000003697 methyltransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 452
- 150000003839 salts Chemical class 0.000 claims description 260
- -1 NH 2 Chemical group 0.000 claims description 200
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 100
- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000004476 heterocycloamino group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 239000003814 drug Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 208000034737 hemoglobinopathy Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 208000005980 beta thalassemia Diseases 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000007056 sickle cell anemia Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 6
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 208000018337 inherited hemoglobinopathy Diseases 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 322
- 239000000203 mixture Substances 0.000 description 230
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 218
- 150000002500 ions Chemical class 0.000 description 147
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 139
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 132
- 238000000034 method Methods 0.000 description 122
- 235000019439 ethyl acetate Nutrition 0.000 description 117
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 103
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 101
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 100
- 230000002829 reductive effect Effects 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
- 239000011541 reaction mixture Substances 0.000 description 78
- 230000008569 process Effects 0.000 description 76
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 74
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 72
- 239000000243 solution Substances 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
- 239000007787 solid Substances 0.000 description 68
- 239000000741 silica gel Substances 0.000 description 67
- 229910002027 silica gel Inorganic materials 0.000 description 67
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 63
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 60
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 55
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 49
- 239000002904 solvent Substances 0.000 description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 46
- 201000010099 disease Diseases 0.000 description 45
- 238000002953 preparative HPLC Methods 0.000 description 45
- 125000005843 halogen group Chemical group 0.000 description 41
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 40
- 229910000027 potassium carbonate Inorganic materials 0.000 description 37
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 235000019341 magnesium sulphate Nutrition 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 238000010828 elution Methods 0.000 description 33
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
- 238000001914 filtration Methods 0.000 description 27
- 238000000746 purification Methods 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 23
- UUPCYQIIQHSPKR-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine;hydrochloride Chemical compound Cl.ClCCCN1CCCC1 UUPCYQIIQHSPKR-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 229940079593 drug Drugs 0.000 description 20
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 20
- 102100035043 Histone-lysine N-methyltransferase EHMT1 Human genes 0.000 description 19
- 108091016366 Histone-lysine N-methyltransferase EHMT1 Proteins 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- UQJGZCRZQZFSMV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C(=CC=2C3=C(N(C=2C=1)C(=O)OC(C)(C)C)C=CN=C3Cl)OC Chemical compound C(C1=CC=CC=C1)OC=1C(=CC=2C3=C(N(C=2C=1)C(=O)OC(C)(C)C)C=CN=C3Cl)OC UQJGZCRZQZFSMV-UHFFFAOYSA-N 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 17
- DRYBMFJLYYEOBZ-UHFFFAOYSA-N methyl 1h-indole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC=CC2=C1 DRYBMFJLYYEOBZ-UHFFFAOYSA-N 0.000 description 17
- 108010016797 Sickle Hemoglobin Proteins 0.000 description 16
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 16
- 125000001153 fluoro group Chemical group F* 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
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- 239000012298 atmosphere Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 239000003643 water by type Substances 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 14
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- JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 230000002401 inhibitory effect Effects 0.000 description 13
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- 229920000728 polyester Polymers 0.000 description 13
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 125000006413 ring segment Chemical group 0.000 description 11
- JNIKZZXESUBNKP-UHFFFAOYSA-N 1-bromo-5-methoxy-2-nitro-4-phenylmethoxybenzene Chemical compound COC1=CC(Br)=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 JNIKZZXESUBNKP-UHFFFAOYSA-N 0.000 description 10
- 108010044495 Fetal Hemoglobin Proteins 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 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 9
- 238000003818 flash chromatography Methods 0.000 description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 9
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- ORGROBFCUNGUFR-UHFFFAOYSA-N C1(CC1)C1=NC=CC=2N(C=3C=C(C(=CC=3C=21)OC)O)C(=O)OC(C)(C)C Chemical compound C1(CC1)C1=NC=CC=2N(C=3C=C(C(=CC=3C=21)OC)O)C(=O)OC(C)(C)C ORGROBFCUNGUFR-UHFFFAOYSA-N 0.000 description 7
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
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- WDVGNXKCFBOKDF-UHFFFAOYSA-N dicyclohexyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane Chemical compound COC1=CC=C(OC)C(C=2C(=CC(=CC=2C(C)C)C(C)C)C(C)C)=C1P(C1CCCCC1)C1CCCCC1 WDVGNXKCFBOKDF-UHFFFAOYSA-N 0.000 description 7
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- RSINODOECJDHGY-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C(=CC=2C3=C(N(C=2C=1)C(=O)OC(C)(C)C)C=CN=C3C1CC1)OC Chemical compound C(C1=CC=CC=C1)OC=1C(=CC=2C3=C(N(C=2C=1)C(=O)OC(C)(C)C)C=CN=C3C1CC1)OC RSINODOECJDHGY-UHFFFAOYSA-N 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
- 102100021519 Hemoglobin subunit beta Human genes 0.000 description 6
- 108091005904 Hemoglobin subunit beta Proteins 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
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- 239000010931 gold Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US201762517410P | 2017-06-09 | 2017-06-09 | |
| US62/517,410 | 2017-06-09 | ||
| PCT/US2018/036521 WO2018226998A1 (en) | 2017-06-09 | 2018-06-07 | Azaindole compounds as histone methyltransferase inhibitors |
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| JP2020523315A JP2020523315A (ja) | 2020-08-06 |
| JP2020523315A5 JP2020523315A5 (enExample) | 2021-07-26 |
| JP7225125B2 true JP7225125B2 (ja) | 2023-02-20 |
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| JP (1) | JP7225125B2 (enExample) |
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| BR (1) | BR112019025770A2 (enExample) |
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| TW (1) | TW201920165A (enExample) |
| WO (1) | WO2018226998A1 (enExample) |
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| MX2019014759A (es) * | 2017-06-09 | 2020-02-12 | Global Blood Therapeutics Inc | Compuestos de azaindol como inhibidores de metiltransferasa de histona. |
| JP7749679B2 (ja) * | 2021-02-05 | 2025-10-06 | シンノハブ ファーマシューティカル カンパニー，リミティド | プラスミン阻害剤、その製造方法およびその適用 |
| CN114394971B (zh) * | 2022-01-24 | 2023-01-31 | 云南大学 | 一种吲哚咔唑类化合物的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003527394A (ja) | 2000-03-15 | 2003-09-16 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換ベーターカルボリン |
| WO2008055233A1 (en) | 2006-10-31 | 2008-05-08 | Supergen, Inc. | Protein kinase inhibitors |
| JP2013533239A (ja) | 2010-06-25 | 2013-08-22 | ファキュルテ ユニヴェルシテール ノートル−ダム ド ラ ペ | 増殖性疾患の治療に有用なβカルボリン誘導体 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| RU2532135C2 (ru) | 2007-02-22 | 2014-10-27 | Зингента Партисипейшнс Аг | Производные иминопиридина и их применение в качестве микробиоцидов |
| AU2008343932B2 (en) * | 2007-12-19 | 2013-08-15 | Amgen Inc. | Fused pyridine, pyrimidine and triazine compounds as cell cycle inhibitors |
| US8932557B2 (en) * | 2008-02-14 | 2015-01-13 | Eli Lilly And Company | Imaging agents for detecting neurological dysfunction |
| GB2465405A (en) | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| PL2364983T3 (pl) | 2008-11-11 | 2014-04-30 | Jeil Pharmaceutical Co Ltd | Nowa pochodna tricykliczna lub jej farmaceutycznie dopuszczalne sole, sposób jej wytwarzania, oraz zawierająca ją kompozycja farmaceutyczna |
| PL2485731T4 (pl) * | 2009-10-06 | 2017-07-31 | Millennium Pharmaceuticals, Inc. | Związki heterocykliczne użyteczne jako inhibitory PDK1 |
| WO2011133795A2 (en) * | 2010-04-22 | 2011-10-27 | The Brigham And Women's Hospital, Inc. | Beta-carbolines as inhibitors of haspin and dyrk kinases |
| TW201236880A (en) | 2011-03-11 | 2012-09-16 | Primax Electronics Ltd | Sheet feeding apparatus |
| KR101606250B1 (ko) | 2011-03-23 | 2016-03-24 | 암젠 인크 | Cdk 4/6 및 flt3의 융합된 트리사이클릭 이중 저해제 |
| US10662193B2 (en) * | 2014-01-21 | 2020-05-26 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins |
| US9284272B2 (en) | 2014-03-28 | 2016-03-15 | Abbvie Inc. | Inhibitors of histone methyltransferase G9a |
| DK3154957T3 (da) | 2014-06-16 | 2020-02-17 | Fundacion Para La Investig Medica Aplicada | Hidtil ukendte forbindelser som dobbelte inhibitorer af histonmethyltransferaser og dna-methyltransferaser |
| US10407423B2 (en) | 2015-11-16 | 2019-09-10 | Fundación Para La Investigación Médica Aplicada | Compounds as inhibitors of DNA methyltransferases |
| MX2019014759A (es) * | 2017-06-09 | 2020-02-12 | Global Blood Therapeutics Inc | Compuestos de azaindol como inhibidores de metiltransferasa de histona. |
-
2018
- 2018-06-07 MX MX2019014759A patent/MX2019014759A/es unknown
- 2018-06-07 WO PCT/US2018/036521 patent/WO2018226998A1/en not_active Ceased
- 2018-06-07 JP JP2019567574A patent/JP7225125B2/ja active Active
- 2018-06-07 BR BR112019025770-5A patent/BR112019025770A2/pt not_active Application Discontinuation
- 2018-06-07 EP EP18735073.1A patent/EP3634962B1/en active Active
- 2018-06-07 ES ES18735073T patent/ES2949402T3/es active Active
- 2018-06-07 US US16/002,408 patent/US11111243B2/en active Active
- 2018-06-07 CN CN201880050882.9A patent/CN110997671A/zh active Pending
- 2018-06-08 AR ARP180101557 patent/AR112192A1/es unknown
- 2018-06-08 TW TW107119935A patent/TW201920165A/zh unknown
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2019
- 2019-12-01 IL IL271066A patent/IL271066A/en unknown
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2021
- 2021-08-06 US US17/396,312 patent/US20210371417A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003527394A (ja) | 2000-03-15 | 2003-09-16 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換ベーターカルボリン |
| WO2008055233A1 (en) | 2006-10-31 | 2008-05-08 | Supergen, Inc. | Protein kinase inhibitors |
| JP2013533239A (ja) | 2010-06-25 | 2013-08-22 | ファキュルテ ユニヴェルシテール ノートル−ダム ド ラ ペ | 増殖性疾患の治療に有用なβカルボリン誘導体 |
Non-Patent Citations (3)
| Title |
|---|
| ACS Chem. Biol.，2013年，8，543-548 |
| ACS Med. Chem. Lett.，2014年，5，205-209 |
| J. Med. Chem.，2013年，56，8931-8942 |
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| Publication number | Publication date |
|---|---|
| AR112192A1 (es) | 2019-10-02 |
| JP2020523315A (ja) | 2020-08-06 |
| IL271066A (en) | 2020-01-30 |
| CN110997671A (zh) | 2020-04-10 |
| EP3634962A1 (en) | 2020-04-15 |
| EP3634962B1 (en) | 2023-05-24 |
| TW201920165A (zh) | 2019-06-01 |
| WO2018226998A1 (en) | 2018-12-13 |
| US20180354947A1 (en) | 2018-12-13 |
| ES2949402T3 (es) | 2023-09-28 |
| US20210371417A1 (en) | 2021-12-02 |
| MX2019014759A (es) | 2020-02-12 |
| US11111243B2 (en) | 2021-09-07 |
| BR112019025770A2 (pt) | 2020-06-23 |
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