JP2017508779A5

JP2017508779A5 -

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Publication number: JP2017508779A5
Authority: JP; Japan
Prior art keywords: alkyl; substituted; alkyloxy; hydrogen; cyano
Prior art date: 2015-03-26
Legal status : Granted

Application number

JP2016559326A

Other languages

English (en)

Japanese (ja)

Other versions

JP6522646B2 (ja

JP2017508779A (ja

Filing date

2015-03-26

Publication date

2019-02-28

2015-03-26 Application filed filed Critical

2015-03-26 Priority claimed from PCT/EP2015/056498 external-priority patent/WO2015144799A1/en

2017-03-30 Publication of JP2017508779A publication Critical patent/JP2017508779A/ja

2019-02-28 Publication of JP2017508779A5 publication Critical patent/JP2017508779A5/ja

2019-05-29 Application granted granted Critical

2019-05-29 Publication of JP6522646B2 publication Critical patent/JP6522646B2/ja

Status Active legal-status Critical Current

2035-03-26 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims description 543
150000001875 compounds Chemical class 0.000 claims description 304
229910052739 hydrogen Inorganic materials 0.000 claims description 257
239000001257 hydrogen Substances 0.000 claims description 256
125000003545 alkoxy group Chemical group 0.000 claims description 231
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 196
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 185
-1 —CH 2 OH Chemical group 0.000 claims description 142
125000004093 cyano group Chemical group *C#N 0.000 claims description 135
150000003839 salts Chemical class 0.000 claims description 126
125000001424 substituent group Chemical group 0.000 claims description 115
239000012453 solvate Substances 0.000 claims description 111
150000001204 N-oxides Chemical class 0.000 claims description 110
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
125000000623 heterocyclic group Chemical group 0.000 claims description 64
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
238000011282 treatment Methods 0.000 claims description 48
125000004429 atom Chemical group 0.000 claims description 45
229920006395 saturated elastomer Polymers 0.000 claims description 45
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 37
125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
201000010099 disease Diseases 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 24
125000002619 bicyclic group Chemical group 0.000 claims description 22
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 15
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 11
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
208000006990 cholangiocarcinoma Diseases 0.000 claims description 9
208000029742 colonic neoplasm Diseases 0.000 claims description 9
208000005017 glioblastoma Diseases 0.000 claims description 9
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
206010009944 Colon cancer Diseases 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
206010033128 Ovarian cancer Diseases 0.000 claims description 7
206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
201000003076 Angiosarcoma Diseases 0.000 claims description 6
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 6
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 6
208000001258 Hemangiosarcoma Diseases 0.000 claims description 6
201000003803 Inflammatory myofibroblastic tumor Diseases 0.000 claims description 6
206010067917 Inflammatory myofibroblastic tumour Diseases 0.000 claims description 6
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
201000006585 gastric adenocarcinoma Diseases 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
208000005726 Inflammatory Breast Neoplasms Diseases 0.000 claims description 5
206010021980 Inflammatory carcinoma of the breast Diseases 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
201000004653 inflammatory breast carcinoma Diseases 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
208000007207 Epithelioid hemangioendothelioma Diseases 0.000 claims description 4
201000010915 Glioblastoma multiforme Diseases 0.000 claims description 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
201000005202 lung cancer Diseases 0.000 claims description 3
208000020816 lung neoplasm Diseases 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims 16
125000004104 aryloxy group Chemical group 0.000 claims 2
239000000543 intermediate Substances 0.000 description 405
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 354
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
239000002904 solvent Substances 0.000 description 162
239000000203 mixture Substances 0.000 description 156
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 122
230000015572 biosynthetic process Effects 0.000 description 89
238000003786 synthesis reaction Methods 0.000 description 89
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 86
239000011541 reaction mixture Substances 0.000 description 81
238000006243 chemical reaction Methods 0.000 description 78
239000007787 solid Substances 0.000 description 78
235000019439 ethyl acetate Nutrition 0.000 description 75
239000000243 solution Substances 0.000 description 69
239000002585 base Substances 0.000 description 65
239000012071 phase Substances 0.000 description 65
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 61
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
229910020175 SiOH Inorganic materials 0.000 description 54
125000005843 halogen group Chemical group 0.000 description 49
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
239000012044 organic layer Substances 0.000 description 44
206010028980 Neoplasm Diseases 0.000 description 41
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
238000000034 method Methods 0.000 description 40
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 37
238000002360 preparation method Methods 0.000 description 36
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
239000002253 acid Substances 0.000 description 29
239000003921 oil Substances 0.000 description 29
235000019198 oils Nutrition 0.000 description 29
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 28
239000007864 aqueous solution Substances 0.000 description 25
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 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
101150003085 Pdcl gene Proteins 0.000 description 23
201000011510 cancer Diseases 0.000 description 23
239000003054 catalyst Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 19
239000012267 brine Substances 0.000 description 19
239000003814 drug Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
101150035397 Ros1 gene Proteins 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000000725 suspension Substances 0.000 description 18
229940125904 compound 1 Drugs 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
238000002844 melting Methods 0.000 description 17
101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 description 16
102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 description 16
239000003153 chemical reaction reagent Substances 0.000 description 16
239000012230 colorless oil Substances 0.000 description 16
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 15
210000004027 cell Anatomy 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000003112 inhibitor Substances 0.000 description 14
229910000104 sodium hydride Inorganic materials 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 13
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 13
239000002246 antineoplastic agent Substances 0.000 description 12
239000011521 glass Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
239000011877 solvent mixture Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
150000001721 carbon Chemical group 0.000 description 10
239000013058 crude material Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
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 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
239000003446 ligand Substances 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
230000001225 therapeutic effect Effects 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
108091000080 Phosphotransferase Proteins 0.000 description 7
230000012010 growth Effects 0.000 description 7
102000020233 phosphotransferase Human genes 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
229940124597 therapeutic agent Drugs 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 6
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 5
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 5
208000014767 Myeloproliferative disease Diseases 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
208000009956 adenocarcinoma Diseases 0.000 description 5
230000000259 anti-tumor effect Effects 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
229940126543 compound 14 Drugs 0.000 description 5
229940125782 compound 2 Drugs 0.000 description 5
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235000008504 concentrate Nutrition 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 5
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
230000001788 irregular Effects 0.000 description 5
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
239000012041 precatalyst Substances 0.000 description 5
238000010926 purge Methods 0.000 description 5
238000000746 purification Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002534 radiation-sensitizing agent Substances 0.000 description 5
238000004808 supercritical fluid chromatography Methods 0.000 description 5
GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 5
IOKGWQZQCNXXLD-UHFFFAOYSA-N tert-butyl n-(3-bromopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCBr IOKGWQZQCNXXLD-UHFFFAOYSA-N 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
229920000858 Cyclodextrin Polymers 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
230000006907 apoptotic process Effects 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
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229940127089 cytotoxic agent Drugs 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000008103 glucose Substances 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000003999 initiator Substances 0.000 description 4
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