TWI557127B - 布魯頓氏酪胺酸激酶抑制劑 - Google Patents

Info

Publication number

TWI557127B

TWI557127B TW099129993A TW99129993A TWI557127B TW I557127 B TWI557127 B TW I557127B TW 099129993 A TW099129993 A TW 099129993A TW 99129993 A TW99129993 A TW 99129993A TW I557127 B TWI557127 B TW I557127B

Authority

TW

Taiwan

Prior art keywords

compound

ring

group

aliphatic

substituted

Prior art date

2009-09-04

Links

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• 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 title claims 8
• 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 title claims 8
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 497
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 180
• 238000006243 chemical reaction Methods 0.000 claims description 168
• 229920006395 saturated elastomer Polymers 0.000 claims description 161
• -1 hydroxyethyl group Chemical group 0.000 claims description 157
• 229910052757 nitrogen Inorganic materials 0.000 claims description 129
• 125000005842 heteroatom Chemical group 0.000 claims description 107
• 229910052760 oxygen Inorganic materials 0.000 claims description 107
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 105
• 229910052717 sulfur Chemical group 0.000 claims description 105
• 239000011593 sulfur Chemical group 0.000 claims description 105
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 103
• 239000001301 oxygen Substances 0.000 claims description 103
• 125000001931 aliphatic group Chemical group 0.000 claims description 85
• 239000001257 hydrogen Substances 0.000 claims description 80
• 229910052739 hydrogen Inorganic materials 0.000 claims description 80
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 77
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 67
• 125000001424 substituent group Chemical group 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 48
• 125000002950 monocyclic group Chemical group 0.000 claims description 46
• 239000000126 substance Substances 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
• 125000002619 bicyclic group Chemical group 0.000 claims description 39
• 125000004429 atom Chemical group 0.000 claims description 37
• 229910052799 carbon Inorganic materials 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
• 230000000694 effects Effects 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 238000006467 substitution reaction Methods 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 19
• 102000004190 Enzymes Human genes 0.000 claims description 18
• 108090000790 Enzymes Proteins 0.000 claims description 18
• 125000002837 carbocyclic group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 208000035475 disorder Diseases 0.000 claims description 17
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 125000005549 heteroarylene group Chemical group 0.000 claims description 11
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 206010025323 Lymphomas Diseases 0.000 claims description 4
• 108091000080 Phosphotransferase Proteins 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 102000020233 phosphotransferase Human genes 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 150000003233 pyrroles Chemical class 0.000 claims description 3
• 230000004044 response Effects 0.000 claims description 3
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
• 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 324
• 238000005481 NMR spectroscopy Methods 0.000 description 198
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 156
• 238000004458 analytical method Methods 0.000 description 142
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 140
• 230000002829 reductive effect Effects 0.000 description 137
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 133
• 235000019439 ethyl acetate Nutrition 0.000 description 122
• 230000015572 biosynthetic process Effects 0.000 description 121
• 238000003786 synthesis reaction Methods 0.000 description 120
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 111
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 104
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
• 239000000243 solution Substances 0.000 description 96
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 90
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 89
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 73
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 66
• 238000004440 column chromatography Methods 0.000 description 59
• 239000012044 organic layer Substances 0.000 description 59
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 48
• 229910052938 sodium sulfate Inorganic materials 0.000 description 48
• 235000011152 sodium sulphate Nutrition 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 46
• 239000000203 mixture Substances 0.000 description 42
• 239000000047 product Substances 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
• 238000010189 synthetic method Methods 0.000 description 38
• 239000002904 solvent Substances 0.000 description 37
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
• 239000012267 brine Substances 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• 238000000746 purification Methods 0.000 description 33
• 239000004202 carbamide Substances 0.000 description 31
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 31
• 238000001308 synthesis method Methods 0.000 description 31
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
• 125000006239 protecting group Chemical group 0.000 description 29
• 238000003756 stirring Methods 0.000 description 29
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
• 150000002430 hydrocarbons Chemical group 0.000 description 24
• 239000012071 phase Substances 0.000 description 23
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• 229940124291 BTK inhibitor Drugs 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 18
• 239000007864 aqueous solution Substances 0.000 description 17
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 17
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 17
• 239000003112 inhibitor Substances 0.000 description 16
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 230000002194 synthesizing effect Effects 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 14
• 150000001721 carbon Chemical group 0.000 description 14
• DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 13
• 230000002441 reversible effect Effects 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
• 201000010099 disease Diseases 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 230000002401 inhibitory effect Effects 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 235000019198 oils Nutrition 0.000 description 10
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
• 125000002947 alkylene group Chemical group 0.000 description 9
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• 125000003277 amino group Chemical group 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• FEIFDRDCVMVUJA-UHFFFAOYSA-N 6-chloro-5-fluoropyrimidin-4-amine Chemical compound NC1=NC=NC(Cl)=C1F FEIFDRDCVMVUJA-UHFFFAOYSA-N 0.000 description 7
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 7
• XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 239000012265 solid product Substances 0.000 description 7
• 229960003732 tyramine Drugs 0.000 description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 238000001035 drying Methods 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 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 6
• LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
• 238000010898 silica gel chromatography Methods 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
• 238000005160 1H NMR spectroscopy Methods 0.000 description 5
• 229940126062 Compound A Drugs 0.000 description 5
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 125000000753 cycloalkyl group Chemical group 0.000 description 5
• 239000003937 drug carrier Substances 0.000 description 5
• 235000019441 ethanol Nutrition 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
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