DK3186259T3 - TETRAHYDRONAPHTHALENE DERIVATIVES INHIBITING MCL-1 PROTEIN - Google Patents

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Publication number

DK3186259T3

DK3186259T3 DK15772048.3T DK15772048T DK3186259T3 DK 3186259 T3 DK3186259 T3 DK 3186259T3 DK 15772048 T DK15772048 T DK 15772048T DK 3186259 T3 DK3186259 T3 DK 3186259T3

Authority

DK

Denmark

Prior art keywords

compound

mmol

chloro

naphthalene

spiro

Prior art date

2014-08-29

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• 101001056180 Homo sapiens Induced myeloid leukemia cell differentiation protein Mcl-1 Proteins 0.000 title claims description 37
• 102100026539 Induced myeloid leukemia cell differentiation protein Mcl-1 Human genes 0.000 title claims description 37
• 230000002401 inhibitory effect Effects 0.000 title claims description 6
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 310
• 238000000034 method Methods 0.000 claims description 106
• 150000003839 salts Chemical class 0.000 claims description 51
• 206010028980 Neoplasm Diseases 0.000 claims description 33
• 210000004027 cell Anatomy 0.000 claims description 32
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 26
• 201000011510 cancer Diseases 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 239000000126 substance Substances 0.000 claims description 14
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 208000034578 Multiple myelomas Diseases 0.000 claims description 8
• 239000007924 injection Substances 0.000 claims description 8
• 238000002347 injection Methods 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 201000000050 myeloid neoplasm Diseases 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• 201000000849 skin cancer Diseases 0.000 claims description 3
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
• BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims description 2
• 229960002438 carfilzomib Drugs 0.000 claims description 2
• 108010021331 carfilzomib Proteins 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• 206010066476 Haematological malignancy Diseases 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 278
• 239000000203 mixture Substances 0.000 description 271
• 239000000243 solution Substances 0.000 description 189
• 241000534944 Thia Species 0.000 description 169
• MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 164
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
• 235000019439 ethyl acetate Nutrition 0.000 description 139
• FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 127
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
• 239000000543 intermediate Substances 0.000 description 121
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 98
• 238000006243 chemical reaction Methods 0.000 description 91
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 78
• 150000002500 ions Chemical class 0.000 description 69
• 238000005160 1H NMR spectroscopy Methods 0.000 description 64
• 239000007787 solid Substances 0.000 description 63
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 62
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 62
• 239000011541 reaction mixture Substances 0.000 description 61
• -1 diastereomers Chemical class 0.000 description 57
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
• 229910052681 coesite Inorganic materials 0.000 description 51
• 229910052906 cristobalite Inorganic materials 0.000 description 51
• 229910052682 stishovite Inorganic materials 0.000 description 51
• 229910052905 tridymite Inorganic materials 0.000 description 51
• 239000012044 organic layer Substances 0.000 description 50
• 239000012267 brine Substances 0.000 description 48
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
• 239000013058 crude material Substances 0.000 description 47
• 125000005605 benzo group Chemical group 0.000 description 46
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 46
• 239000002904 solvent Substances 0.000 description 46
• 235000002639 sodium chloride Nutrition 0.000 description 45
• 230000002829 reductive effect Effects 0.000 description 40
• 239000000499 gel Substances 0.000 description 39
• 239000007832 Na2SO4 Substances 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
• 235000012239 silicon dioxide Nutrition 0.000 description 38
• 229910052938 sodium sulfate Inorganic materials 0.000 description 38
• 235000011152 sodium sulphate Nutrition 0.000 description 38
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 36
• 229910052737 gold Inorganic materials 0.000 description 36
• 239000010931 gold Substances 0.000 description 36
• 239000003921 oil Substances 0.000 description 36
• 239000000377 silicon dioxide Substances 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 235000019198 oils Nutrition 0.000 description 35
• VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 34
• 229960001124 trientine Drugs 0.000 description 34
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 33
• 239000010410 layer Substances 0.000 description 32
• 229910052786 argon Inorganic materials 0.000 description 31
• 239000003795 chemical substances by application Substances 0.000 description 29
• 238000000746 purification Methods 0.000 description 29
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
• 238000004587 chromatography analysis Methods 0.000 description 25
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 239000012043 crude product Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 238000004007 reversed phase HPLC Methods 0.000 description 21
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 17
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 17
• 239000002002 slurry Substances 0.000 description 17
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 16
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
• 238000010828 elution Methods 0.000 description 16
• 238000009472 formulation Methods 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• 235000019341 magnesium sulphate Nutrition 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000000463 material Substances 0.000 description 15
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 15
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
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• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000002390 rotary evaporation Methods 0.000 description 12
• 239000000725 suspension Substances 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
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• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• ZRPFJAPZDXQHSM-UHFFFAOYSA-L 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole;dichloro-[(2-propan-2-yloxyphenyl)methylidene]ruthenium Chemical compound CC(C)OC1=CC=CC=C1C=[Ru](Cl)(Cl)=C1N(C=2C(=CC(C)=CC=2C)C)CCN1C1=C(C)C=C(C)C=C1C ZRPFJAPZDXQHSM-UHFFFAOYSA-L 0.000 description 10
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• 238000002360 preparation method Methods 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 230000014759 maintenance of location Effects 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
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• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 238000003556 assay Methods 0.000 description 8
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 8
• 239000006196 drop Substances 0.000 description 8
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• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• 238000010966 qNMR Methods 0.000 description 8
• OCSITWXGPHLSLB-NKWVEPMBSA-N (2R,3S)-3-methylhex-5-ene-2-sulfonamide Chemical compound C[C@H]([C@@H](C)S(=O)(=O)N)CC=C OCSITWXGPHLSLB-NKWVEPMBSA-N 0.000 description 7
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
• 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 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 238000010521 absorption reaction Methods 0.000 description 7
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• 239000000872 buffer Substances 0.000 description 7
• 239000000969 carrier Substances 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
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• 239000002552 dosage form Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
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• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 6
• UFRVZURFOQRSHF-KSAVMPJKSA-N ClC=1C=C2CCC[C@]3(C2=CC=1)CN(C1=C(OC3)C=CC(=C1)C(=O)O)C[C@H]1[C@@H](CC1)[C@H](\C=C\CCC)O Chemical compound ClC=1C=C2CCC[C@]3(C2=CC=1)CN(C1=C(OC3)C=CC(=C1)C(=O)O)C[C@H]1[C@@H](CC1)[C@H](\C=C\CCC)O UFRVZURFOQRSHF-KSAVMPJKSA-N 0.000 description 6
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• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 6
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• 239000012488 sample solution Substances 0.000 description 6
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
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• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• 241000416162 Astragalus gummifer Species 0.000 description 5
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• IBYWSCDAGMKKIC-GOSISDBHSA-N COC1=CC=C(CN(S(=O)(=O)C[C@@H](CC=C)C)CC2=CC=C(C=C2)OC)C=C1 Chemical compound COC1=CC=C(CN(S(=O)(=O)C[C@@H](CC=C)C)CC2=CC=C(C=C2)OC)C=C1 IBYWSCDAGMKKIC-GOSISDBHSA-N 0.000 description 5
• IBYWSCDAGMKKIC-SFHVURJKSA-N COC1=CC=C(CN(S(=O)(=O)C[C@H](CC=C)C)CC2=CC=C(C=C2)OC)C=C1 Chemical compound COC1=CC=C(CN(S(=O)(=O)C[C@H](CC=C)C)CC2=CC=C(C=C2)OC)C=C1 IBYWSCDAGMKKIC-SFHVURJKSA-N 0.000 description 5
• 238000010268 HPLC based assay Methods 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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