TW201602113A - 作為ｐｉ３ｋ抑制劑之嘧啶酮 - Google Patents

Info

Publication number

TW201602113A

TW201602113A TW104110745A TW104110745A TW201602113A TW 201602113 A TW201602113 A TW 201602113A TW 104110745 A TW104110745 A TW 104110745A TW 104110745 A TW104110745 A TW 104110745A TW 201602113 A TW201602113 A TW 201602113A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

heteroaryl

mmol

independently selected

Prior art date

2009-06-29

Links

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• Global Dossier
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• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title abstract description 3
• 239000012828 PI3K inhibitor Substances 0.000 title description 4
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 268
• 125000000217 alkyl group Chemical group 0.000 claims description 214
• 125000001072 heteroaryl group Chemical group 0.000 claims description 128
• 125000005843 halogen group Chemical group 0.000 claims description 121
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 120
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 118
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 115
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 111
• 125000001424 substituent group Chemical group 0.000 claims description 109
• 125000003118 aryl group Chemical group 0.000 claims description 103
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 96
• -1 halothio Chemical group 0.000 claims description 82
• 229910052799 carbon Inorganic materials 0.000 claims description 57
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 54
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 49
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
• 150000001336 alkenes Chemical class 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 150000001924 cycloalkanes Chemical class 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
• 108091007960 PI3Ks Proteins 0.000 abstract description 85
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract description 82
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 56
• 201000010099 disease Diseases 0.000 abstract description 49
• 230000000694 effects Effects 0.000 abstract description 23
• 206010028980 Neoplasm Diseases 0.000 abstract description 10
• 201000011510 cancer Diseases 0.000 abstract description 9
• 208000035475 disorder Diseases 0.000 abstract description 7
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract description 4
• 208000027866 inflammatory disease Diseases 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 311
• 239000000203 mixture Substances 0.000 description 284
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 181
• 235000019439 ethyl acetate Nutrition 0.000 description 135
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 115
• 239000000243 solution Substances 0.000 description 109
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 99
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
• 239000002253 acid Substances 0.000 description 91
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 86
• 102000038030 PI3Ks Human genes 0.000 description 82
• 238000005481 NMR spectroscopy Methods 0.000 description 81
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 80
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 79
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
• 238000000034 method Methods 0.000 description 71
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 68
• 239000000047 product Substances 0.000 description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 54
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 52
• 229910052763 palladium Inorganic materials 0.000 description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
• 239000007787 solid Substances 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 42
• 239000012267 brine Substances 0.000 description 38
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
• YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 36
• 229910000029 sodium carbonate Inorganic materials 0.000 description 34
• 238000001816 cooling Methods 0.000 description 30
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 29
• ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 29
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 239000000706 filtrate Substances 0.000 description 26
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 24
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 24
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
• 238000004128 high performance liquid chromatography Methods 0.000 description 23
• 108091000080 Phosphotransferase Proteins 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 22
• 102000020233 phosphotransferase Human genes 0.000 description 22
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 238000002360 preparation method Methods 0.000 description 21
• DKLLTWYYZDFILI-UHFFFAOYSA-N 7-(1-azidoethyl)-6-bromo-3-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C(Br)=C(C(N=[N+]=[N-])C)N=C2SC=C(C)N21 DKLLTWYYZDFILI-UHFFFAOYSA-N 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 20
• 239000011734 sodium Substances 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 125000003963 dichloro group Chemical group Cl* 0.000 description 17
• 239000000284 extract Substances 0.000 description 16
• 238000004007 reversed phase HPLC Methods 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• RYCNUAWREJKWPR-UHFFFAOYSA-N 6-bromo-1H-indol-2-amine Chemical compound Nc1cc2ccc(Br)cc2[nH]1 RYCNUAWREJKWPR-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
• 239000007858 starting material Substances 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 13
• 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 13
• 239000002585 base Substances 0.000 description 12
• 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 12
• 238000009472 formulation Methods 0.000 description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• UEZROEGYRDHMRV-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C=CN=C2SC=CN12 UEZROEGYRDHMRV-UHFFFAOYSA-N 0.000 description 10
• 125000004429 atom Chemical group 0.000 description 10
• 239000012458 free base Substances 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 239000000546 pharmaceutical excipient Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 9
• 239000013058 crude material Substances 0.000 description 9
• 239000002552 dosage form Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 8
• QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 241000699670 Mus sp. Species 0.000 description 8
• 230000035772 mutation Effects 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000000926 separation method Methods 0.000 description 8
• 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 8
• VFDBWGUPPLPDBN-UHFFFAOYSA-N 1h-pyrimidin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1C=CN=CN1 VFDBWGUPPLPDBN-UHFFFAOYSA-N 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 229940043355 kinase inhibitor Drugs 0.000 description 7
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 7
• 229920000137 polyphosphoric acid Polymers 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 238000006467 substitution reaction Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 6
• KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 229910052736 halogen Inorganic materials 0.000 description 6
• 230000004054 inflammatory process Effects 0.000 description 6
• 230000014759 maintenance of location Effects 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 description 6
• 208000034578 Multiple myelomas Diseases 0.000 description 5
• 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 description 5
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• 102000001708 Protein Isoforms Human genes 0.000 description 5
• 108010029485 Protein Isoforms Proteins 0.000 description 5
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• 239000002246 antineoplastic agent Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 229940127089 cytotoxic agent Drugs 0.000 description 5
• 229960003957 dexamethasone Drugs 0.000 description 5
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
• 150000002367 halogens Chemical class 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 239000007937 lozenge Substances 0.000 description 5
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 5
• 229960001924 melphalan Drugs 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 230000007170 pathology Effects 0.000 description 5
• 239000002002 slurry Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• 108010072897 transcription factor Brn-2 Proteins 0.000 description 5
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
• YOKHBHBBIFOQIS-UHFFFAOYSA-N 2-(1-azidoethyl)-3-iodo-6-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=C(C)N2C(=O)C(I)=C(C(N=[N+]=[N-])C)N=C21 YOKHBHBBIFOQIS-UHFFFAOYSA-N 0.000 description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
• WLOKHPAZKILPQD-UHFFFAOYSA-N 6-bromo-7-(1-bromoethyl)-3-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C(Br)=C(C(Br)C)N=C2SC=C(C)N21 WLOKHPAZKILPQD-UHFFFAOYSA-N 0.000 description 4
• CTGFGRDVWBZYNB-UHFFFAOYSA-N 6-bromo-7h-purine Chemical compound BrC1=NC=NC2=C1NC=N2 CTGFGRDVWBZYNB-UHFFFAOYSA-N 0.000 description 4
• QXKNXDWUQIEHSW-UHFFFAOYSA-N 7-(1-azidoethyl)-6-bromo-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C(Br)=C(C(N=[N+]=[N-])C)N=C2SC=CN21 QXKNXDWUQIEHSW-UHFFFAOYSA-N 0.000 description 4
• XOHWDJGQJHNKLV-UHFFFAOYSA-N 7-(1-bromoethyl)-3-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound CC(Br)C1=CC(=O)N2C(C)=CSC2=N1 XOHWDJGQJHNKLV-UHFFFAOYSA-N 0.000 description 4
• AJOXLQVOCJSNFN-VIFPVBQESA-N 7-[(1s)-1-aminoethyl]-6-(3-fluorophenyl)-3-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C[C@H](N)C=1N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 AJOXLQVOCJSNFN-VIFPVBQESA-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
• 201000001320 Atherosclerosis Diseases 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• 102000001253 Protein Kinase Human genes 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
• 125000003342 alkenyl group Chemical group 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 208000006673 asthma Diseases 0.000 description 4
• 150000001540 azides Chemical class 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
• 230000014509 gene expression Effects 0.000 description 4
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
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