TW201920165A - 氮吲哚化合物作為組蛋白甲基轉移酶抑制劑 - Google Patents

Info

Publication number

TW201920165A

TW201920165A TW107119935A TW107119935A TW201920165A TW 201920165 A TW201920165 A TW 201920165A TW 107119935 A TW107119935 A TW 107119935A TW 107119935 A TW107119935 A TW 107119935A TW 201920165 A TW201920165 A TW 201920165A

Authority

TW

Taiwan

Prior art keywords

pharmaceutically acceptable

acceptable salt

group

compound

compound according

Prior art date

2017-06-09

Links

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• Global Dossier
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• 108010036115 Histone Methyltransferases Proteins 0.000 title abstract description 3
• 102000011787 Histone Methyltransferases Human genes 0.000 title abstract description 3
• 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title 1
• 239000003697 methyltransferase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 524
• 201000010099 disease Diseases 0.000 claims abstract description 80
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 80
• 238000000034 method Methods 0.000 claims abstract description 67
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 208000005980 beta thalassemia Diseases 0.000 claims abstract description 12
• 208000007056 sickle cell anemia Diseases 0.000 claims abstract description 11
• -1 NH 2 Chemical group 0.000 claims description 415
• 150000003839 salts Chemical class 0.000 claims description 371
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 120
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 92
• 125000000623 heterocyclic group Chemical group 0.000 claims description 91
• 229910052757 nitrogen Inorganic materials 0.000 claims description 70
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• 125000005843 halogen group Chemical group 0.000 claims description 64
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
• 125000003277 amino group Chemical group 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 56
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
• 150000003278 haem Chemical class 0.000 claims description 52
• 125000001188 haloalkyl group Chemical group 0.000 claims description 50
• 239000003814 drug Substances 0.000 claims description 46
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 125000002947 alkylene group Chemical group 0.000 claims description 32
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
• 230000002401 inhibitory effect Effects 0.000 claims description 30
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
• 238000004519 manufacturing process Methods 0.000 claims description 27
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
• 108091016366 Histone-lysine N-methyltransferase EHMT1 Proteins 0.000 claims description 25
• 229940079593 drug Drugs 0.000 claims description 24
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
• 150000002431 hydrogen Chemical class 0.000 claims description 21
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 230000000694 effects Effects 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 12
• 230000001605 fetal effect Effects 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• 230000001965 increasing effect Effects 0.000 claims description 12
• 102000006734 Beta-Globulins Human genes 0.000 claims description 11
• 108010087504 Beta-Globulins Proteins 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 230000001771 impaired effect Effects 0.000 claims description 11
• 108090000623 proteins and genes Proteins 0.000 claims description 11
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 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 claims description 8
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
• 125000005122 aminoalkylamino group Chemical group 0.000 claims description 7
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 7
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 7
• 238000006116 polymerization reaction Methods 0.000 claims description 7
• 102000004169 proteins and genes Human genes 0.000 claims description 7
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 6
• 108010044495 Fetal Hemoglobin Proteins 0.000 claims description 6
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 230000035772 mutation Effects 0.000 claims description 6
• 229910052698 phosphorus Inorganic materials 0.000 claims description 6
• 125000001116 prolino group Chemical group [H]OC(=O)C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 4
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 4
• 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 4
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 4
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 4
• 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 4
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 2
• 229910052770 Uranium Inorganic materials 0.000 claims description 2
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 22
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• 230000005764 inhibitory process Effects 0.000 abstract description 4
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• 208000034737 hemoglobinopathy Diseases 0.000 abstract 1
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 225
• 239000000203 mixture Substances 0.000 description 152
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
• 150000002500 ions Chemical class 0.000 description 87
• 230000002829 reductive effect Effects 0.000 description 84
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 80
• 235000019439 ethyl acetate Nutrition 0.000 description 76
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 62
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
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• 239000002904 solvent Substances 0.000 description 36
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
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• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 21
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• 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 18
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• 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 15
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• JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 13
• UUPCYQIIQHSPKR-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine;hydrochloride Chemical compound Cl.ClCCCN1CCCC1 UUPCYQIIQHSPKR-UHFFFAOYSA-N 0.000 description 13
• 229920000728 polyester Polymers 0.000 description 13
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