TW202332436A - 治療用化合物 - Google Patents

Info

Publication number

TW202332436A

TW202332436A TW111146299A TW111146299A TW202332436A TW 202332436 A TW202332436 A TW 202332436A TW 111146299 A TW111146299 A TW 111146299A TW 111146299 A TW111146299 A TW 111146299A TW 202332436 A TW202332436 A TW 202332436A

Authority

TW

Taiwan

Prior art keywords

methyl

pyrazol

pyridin

benzyl

dihydro

Prior art date

2017-04-18

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 244
• 230000001225 therapeutic effect Effects 0.000 title abstract description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 59
• 125000000217 alkyl group Chemical group 0.000 claims description 66
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims 5
• 239000000203 mixture Substances 0.000 abstract description 113
• 238000000034 method Methods 0.000 abstract description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 33
• 102000001805 Bromodomains Human genes 0.000 abstract description 32
• 108050009021 Bromodomains Proteins 0.000 abstract description 31
• 206010028980 Neoplasm Diseases 0.000 abstract description 28
• 201000010099 disease Diseases 0.000 abstract description 27
• 108090000623 proteins and genes Proteins 0.000 abstract description 24
• 201000011510 cancer Diseases 0.000 abstract description 20
• 102000004169 proteins and genes Human genes 0.000 abstract description 20
• 230000002401 inhibitory effect Effects 0.000 abstract description 14
• 230000005764 inhibitory process Effects 0.000 abstract description 11
• 230000001404 mediated effect Effects 0.000 abstract description 11
• 108010033040 Histones Proteins 0.000 abstract description 10
• 238000011282 treatment Methods 0.000 abstract description 10
• 208000027866 inflammatory disease Diseases 0.000 abstract description 9
• 102000006947 Histones Human genes 0.000 abstract description 8
• 230000001613 neoplastic effect Effects 0.000 abstract description 5
• 230000005754 cellular signaling Effects 0.000 abstract description 3
• DTERQYGMUDWYAZ-ZETCQYMHSA-N N(6)-acetyl-L-lysine Chemical group CC(=O)NCCCC[C@H]([NH3+])C([O-])=O DTERQYGMUDWYAZ-ZETCQYMHSA-N 0.000 abstract description 2
• 230000001594 aberrant effect Effects 0.000 abstract description 2
• 108091005625 BRD4 Proteins 0.000 abstract 1
• 102100029895 Bromodomain-containing protein 4 Human genes 0.000 abstract 1
• 230000006718 epigenetic regulation Effects 0.000 abstract 1
• -1 1-propyl (n-propyl) Chemical group 0.000 description 715
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 396
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 115
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 79
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
• 238000005481 NMR spectroscopy Methods 0.000 description 76
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 75
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 72
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• 239000007787 solid Substances 0.000 description 61
• 230000002829 reductive effect Effects 0.000 description 57
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 54
• 229910052938 sodium sulfate Inorganic materials 0.000 description 54
• 235000011152 sodium sulphate Nutrition 0.000 description 54
• 239000012044 organic layer Substances 0.000 description 51
• 239000000243 solution Substances 0.000 description 50
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 45
• 235000019439 ethyl acetate Nutrition 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 43
• 239000007832 Na2SO4 Substances 0.000 description 42
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
• 238000004440 column chromatography Methods 0.000 description 35
• 201000006417 multiple sclerosis Diseases 0.000 description 33
• 239000000377 silicon dioxide Substances 0.000 description 29
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 26
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 26
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 25
• 238000002953 preparative HPLC Methods 0.000 description 25
• MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical compound C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 description 24
• 239000012267 brine Substances 0.000 description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 24
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
• 239000000126 substance Substances 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 21
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 19
• 235000018102 proteins Nutrition 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
• 239000011734 sodium Substances 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• 125000001424 substituent group Chemical group 0.000 description 17
• 125000004452 carbocyclyl group Chemical group 0.000 description 15
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 15
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 14
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
• GHEVWWOXJKDQHV-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-1-methylpyridin-2-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C=CC(N(C=1)C)=O GHEVWWOXJKDQHV-UHFFFAOYSA-N 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 239000000651 prodrug Substances 0.000 description 12
• 229940002612 prodrug Drugs 0.000 description 12
• 125000004122 cyclic group Chemical group 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• FPAVPKYINGLQCE-UHFFFAOYSA-N 5-bromo-4-chloro-1-methylpyridin-2-one Chemical compound CN1C=C(Br)C(Cl)=CC1=O FPAVPKYINGLQCE-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 125000000304 alkynyl group Chemical group 0.000 description 10
• 229910052799 carbon Inorganic materials 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 210000000068 Th17 cell Anatomy 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 150000001412 amines Chemical group 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 150000004820 halides Chemical class 0.000 description 9
• 238000012746 preparative thin layer chromatography Methods 0.000 description 9
• 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 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• 238000010828 elution Methods 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• 150000002430 hydrocarbons Chemical group 0.000 description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 8
• 210000003289 regulatory T cell Anatomy 0.000 description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 229960004365 benzoic acid Drugs 0.000 description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 239000000546 pharmaceutical excipient Substances 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 125000003226 pyrazolyl group Chemical group 0.000 description 7
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• CBUYISHIFQEYJS-UHFFFAOYSA-N 4-chloro-1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound ClC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)=O CBUYISHIFQEYJS-UHFFFAOYSA-N 0.000 description 6
• TWXIMNCZAUVQPV-UHFFFAOYSA-N 4-ethoxy-1-methyl-5-[1-[1-[4-(1-methylpyrazol-4-yl)phenyl]ethyl]pyrazol-4-yl]pyridin-2-one Chemical compound C(C)OC1=CC(N(C=C1C=1C=NN(C=1)C(C)C1=CC=C(C=C1)C=1C=NN(C=1)C)C)=O TWXIMNCZAUVQPV-UHFFFAOYSA-N 0.000 description 6
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• 230000008901 benefit Effects 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 229910052805 deuterium Inorganic materials 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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• FVYKDNOAEDISTK-UHFFFAOYSA-N 1-methyl-4-phenyl-5-(5-phenyl-1,3-oxazol-2-yl)pyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1OC(=CN=1)C1=CC=CC=C1)C1=CC=CC=C1)=O FVYKDNOAEDISTK-UHFFFAOYSA-N 0.000 description 5
• VLBHAFKKGCSTGF-UHFFFAOYSA-N 1-methyl-5-[1-(1-phenylethyl)pyrazol-4-yl]-4-pyrrolidin-1-ylpyridin-2-one Chemical compound CN1C(C=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)N1CCCC1)=O VLBHAFKKGCSTGF-UHFFFAOYSA-N 0.000 description 5
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• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
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• XGDGIPOBQPRVHE-UHFFFAOYSA-N 4-ethoxy-1-methyl-5-(1H-pyrazol-4-yl)pyridin-2-one Chemical compound C(C)OC1=CC(N(C=C1C=1C=NNC=1)C)=O XGDGIPOBQPRVHE-UHFFFAOYSA-N 0.000 description 5
• YXAIAZBATBMHAC-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-1,6-dimethylpyridin-2-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C=CC(N(C=1C)C)=O YXAIAZBATBMHAC-UHFFFAOYSA-N 0.000 description 5
• NTKHBSWZEOEHGO-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-1-methyl-4-(1,2-oxazol-3-yl)pyridin-2-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=NOC=C1 NTKHBSWZEOEHGO-UHFFFAOYSA-N 0.000 description 5
• ZNVUXNJXHZSJRK-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-1-methyl-4-(2-methylphenyl)pyridin-2-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=C(C=CC=C1)C ZNVUXNJXHZSJRK-UHFFFAOYSA-N 0.000 description 5
• GJHVMZMWHMYURT-UHFFFAOYSA-N 5-(1-benzylpyrazol-4-yl)-1-methyl-4-(5-methyl-1H-pyrazol-3-yl)pyridin-2-one Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)C1=CC(=NN1)C GJHVMZMWHMYURT-UHFFFAOYSA-N 0.000 description 5
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• CRIRTIVBYPDNBK-UHFFFAOYSA-N 5-[1-(2-chlorophenyl)pyrazol-4-yl]-1-methyl-4-[(1-methylpyrazol-4-yl)methoxy]pyridin-2-one Chemical compound ClC1=C(C=CC=C1)N1N=CC(=C1)C=1C(=CC(N(C=1)C)=O)OCC=1C=NN(C=1)C CRIRTIVBYPDNBK-UHFFFAOYSA-N 0.000 description 5
• YBSDCTRRMZDSCT-UHFFFAOYSA-N 5-[1-[cyclopropyl(phenyl)methyl]pyrazol-4-yl]-1,3-dimethylpyridin-2-one Chemical compound C1(CC1)C(N1N=CC(=C1)C=1C=C(C(N(C=1)C)=O)C)C1=CC=CC=C1 YBSDCTRRMZDSCT-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
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• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
• 239000004472 Lysine Substances 0.000 description 5
• OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 5
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• 150000001642 boronic acid derivatives Chemical class 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 230000004069 differentiation Effects 0.000 description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
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• 125000003709 fluoroalkyl group Chemical group 0.000 description 5
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• 239000012299 nitrogen atmosphere Substances 0.000 description 5
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• 239000001301 oxygen Chemical group 0.000 description 5
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• 108090000765 processed proteins & peptides Proteins 0.000 description 5
• 238000003860 storage Methods 0.000 description 5
• CJBIOEKIFDRINV-UHFFFAOYSA-N 1,3,4-trimethyl-5-[1-(1-phenylethyl)pyrazol-4-yl]pyridin-2-one Chemical compound CN1C(C(=C(C(=C1)C=1C=NN(C=1)C(C)C1=CC=CC=C1)C)C)=O CJBIOEKIFDRINV-UHFFFAOYSA-N 0.000 description 4
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