EA029789B1 - ПРОИЗВОДНЫЕ ИМИДАЗОПИРИДАЗИНА В КАЧЕСТВЕ ИНГИБИТОРОВ PI3Kβ - Google Patents

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Publication number

EA029789B1

EA029789B1 EA201791396A EA201791396A EA029789B1 EA 029789 B1 EA029789 B1 EA 029789B1 EA 201791396 A EA201791396 A EA 201791396A EA 201791396 A EA201791396 A EA 201791396A EA 029789 B1 EA029789 B1 EA 029789B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

substituents

substituted

mmol

formula

Prior art date

2014-12-19

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• 239000003112 inhibitor Substances 0.000 title abstract description 26
• 150000005233 imidazopyridazines Chemical class 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 320
• 239000003814 drug Substances 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 239000004480 active ingredient Substances 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 261
• 125000001424 substituent group Chemical group 0.000 claims description 151
• 150000003839 salts Chemical class 0.000 claims description 107
• 239000012453 solvate Substances 0.000 claims description 96
• 229910052799 carbon Inorganic materials 0.000 claims description 80
• 229910052739 hydrogen Inorganic materials 0.000 claims description 71
• 239000001257 hydrogen Substances 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 56
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 150000002367 halogens Chemical group 0.000 claims description 49
• 206010028980 Neoplasm Diseases 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 40
• 150000002431 hydrogen Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• 206010060862 Prostate cancer Diseases 0.000 claims description 8
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000003566 oxetanyl group Chemical group 0.000 claims description 6
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 210000001519 tissue Anatomy 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 206010020751 Hypersensitivity Diseases 0.000 claims description 4
• 208000034486 Multi-organ failure Diseases 0.000 claims description 4
• 208000010718 Multiple Organ Failure Diseases 0.000 claims description 4
• 206010033645 Pancreatitis Diseases 0.000 claims description 4
• 230000007815 allergy Effects 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 230000001771 impaired effect Effects 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 208000017169 kidney disease Diseases 0.000 claims description 4
• 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 4
• 230000004770 neurodegeneration Effects 0.000 claims description 4
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 230000019100 sperm motility Effects 0.000 claims description 4
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 4
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 231100000516 lung damage Toxicity 0.000 claims description 3
• 238000000034 method Methods 0.000 abstract description 112
• 230000008569 process Effects 0.000 abstract description 3
• 239000000543 intermediate Substances 0.000 description 714
• 239000002904 solvent Substances 0.000 description 229
• -1 hydrocarbyl radical Chemical class 0.000 description 226
• 239000000203 mixture Substances 0.000 description 212
• 238000002360 preparation method Methods 0.000 description 196
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 174
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
• 239000011541 reaction mixture Substances 0.000 description 127
• 239000002585 base Chemical class 0.000 description 107
• 239000000243 solution Substances 0.000 description 104
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
• 230000015572 biosynthetic process Effects 0.000 description 90
• 239000003054 catalyst Substances 0.000 description 88
• 239000007858 starting material Substances 0.000 description 86
• 238000006243 chemical reaction Methods 0.000 description 85
• 238000003786 synthesis reaction Methods 0.000 description 84
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 81
• 239000012044 organic layer Substances 0.000 description 78
• 239000000047 product Substances 0.000 description 74
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
• 239000000741 silica gel Substances 0.000 description 71
• 229910002027 silica gel Inorganic materials 0.000 description 71
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 68
• 238000004587 chromatography analysis Methods 0.000 description 68
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 50
• 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 50
• 230000001788 irregular Effects 0.000 description 44
• 239000003446 ligand Substances 0.000 description 43
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 42
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
• 239000002253 acid Substances 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 36
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 36
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 34
• 239000007864 aqueous solution Substances 0.000 description 31
• MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• 229910052757 nitrogen Inorganic materials 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 239000003795 chemical substances by application Substances 0.000 description 28
• 239000012071 phase Substances 0.000 description 28
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
• 150000001721 carbon Chemical group 0.000 description 26
• 229910000027 potassium carbonate Inorganic materials 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 23
• 235000011181 potassium carbonates Nutrition 0.000 description 22
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 22
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 21
• 239000002244 precipitate Substances 0.000 description 21
• 239000012267 brine Substances 0.000 description 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 20
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 19
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 18
• UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 18
• 230000001965 increasing effect Effects 0.000 description 18
• 229910052763 palladium Inorganic materials 0.000 description 18
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 239000012299 nitrogen atmosphere Substances 0.000 description 16
• USVZFSNDGFNNJT-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yl(diphenyl)phosphane (2,3-dichlorocyclopenta-1,4-dien-1-yl)-diphenylphosphane iron(2+) Chemical compound [Fe++].c1cc[c-](c1)P(c1ccccc1)c1ccccc1.Clc1c(cc[c-]1Cl)P(c1ccccc1)c1ccccc1 USVZFSNDGFNNJT-UHFFFAOYSA-N 0.000 description 15
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
• 229940043279 diisopropylamine Drugs 0.000 description 14
• 239000010410 layer Substances 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 13
• 229910052740 iodine Inorganic materials 0.000 description 13
• 239000003208 petroleum Substances 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000002246 antineoplastic agent Substances 0.000 description 12
• 229910000024 caesium carbonate Inorganic materials 0.000 description 12
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 12
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
• 239000011592 zinc chloride Substances 0.000 description 12
• 235000005074 zinc chloride Nutrition 0.000 description 12
• 108091000080 Phosphotransferase Proteins 0.000 description 11
• 102000020233 phosphotransferase Human genes 0.000 description 11
• 229910000160 potassium phosphate Inorganic materials 0.000 description 11
• 235000011009 potassium phosphates Nutrition 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 238000012545 processing Methods 0.000 description 11
• 229960002429 proline Drugs 0.000 description 11
• 238000000746 purification Methods 0.000 description 10
• 230000001225 therapeutic effect Effects 0.000 description 10
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
• 239000000654 additive Substances 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• QLRSIDWDWVMAIR-UHFFFAOYSA-N 1-(chloromethyl)-2-methyl-3-(trifluoromethyl)benzene Chemical compound CC1=C(CCl)C=CC=C1C(F)(F)F QLRSIDWDWVMAIR-UHFFFAOYSA-N 0.000 description 8
• 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 8
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 8
• 229930182821 L-proline Natural products 0.000 description 8
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
• 239000011630 iodine Substances 0.000 description 8
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 8
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 8
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• 229940124597 therapeutic agent Drugs 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 7
• SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 230000002950 deficient Effects 0.000 description 7
• 229940043355 kinase inhibitor Drugs 0.000 description 7
• 229940102396 methyl bromide Drugs 0.000 description 7
• 230000035772 mutation Effects 0.000 description 7
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 230000000996 additive effect Effects 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• WOHIRSIRDGJACD-UHFFFAOYSA-N 2-(bromomethyl)-1-nitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(F)F)=C1CBr WOHIRSIRDGJACD-UHFFFAOYSA-N 0.000 description 5
• 206010006187 Breast cancer Diseases 0.000 description 5
• 208000026310 Breast neoplasm Diseases 0.000 description 5
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
• 229920000858 Cyclodextrin Polymers 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
• 241000282414 Homo sapiens Species 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 230000003213 activating effect Effects 0.000 description 5
• 230000000259 anti-tumor effect Effects 0.000 description 5
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• 239000002552 dosage form Substances 0.000 description 5
• 239000003480 eluent Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 5
• 229910052697 platinum Inorganic materials 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 239000011269 tar Substances 0.000 description 5
• NFRBUOMQJKUACC-UHFFFAOYSA-N triethyl(pentyl)azanium Chemical compound CCCCC[N+](CC)(CC)CC NFRBUOMQJKUACC-UHFFFAOYSA-N 0.000 description 5
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 4
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