CA2771432A1 - Heterocyclic oxime compounds - Google Patents

Info

Publication number

CA2771432A1

CA2771432A1 CA2771432A CA2771432A CA2771432A1 CA 2771432 A1 CA2771432 A1 CA 2771432A1 CA 2771432 A CA2771432 A CA 2771432A CA 2771432 A CA2771432 A CA 2771432A CA 2771432 A1 CA2771432 A1 CA 2771432A1

Authority

CA

Canada

Prior art keywords

mmol

cndot

alkyl

methyl

compound

Prior art date

2009-08-20

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Heterocyclic oxime compounds Chemical class 0.000 title claims description 170
• 150000001875 compounds Chemical class 0.000 claims abstract description 499
• 238000000034 method Methods 0.000 claims abstract description 267
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
• 150000003839 salts Chemical class 0.000 claims abstract description 74
• 201000010099 disease Diseases 0.000 claims abstract description 53
• 238000011282 treatment Methods 0.000 claims abstract description 51
• 239000003814 drug Substances 0.000 claims abstract description 41
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 12
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• 125000005843 halogen group Chemical group 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 56
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• 229910052805 deuterium Inorganic materials 0.000 claims description 29
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 229940124597 therapeutic agent Drugs 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000013543 active substance Substances 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 230000002062 proliferating effect Effects 0.000 claims description 11
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
• 230000004968 inflammatory condition Effects 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 150000002431 hydrogen Chemical group 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• IVGLGVJCVDBHBJ-UHFFFAOYSA-N CC=NOCCO Chemical compound CC=NOCCO IVGLGVJCVDBHBJ-UHFFFAOYSA-N 0.000 claims description 3
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 3
• 125000003566 oxetanyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 241001465754 Metazoa Species 0.000 abstract description 9
• 230000008569 process Effects 0.000 abstract description 9
• 238000002360 preparation method Methods 0.000 abstract description 7
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 294
• 239000000243 solution Substances 0.000 description 205
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 184
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 172
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 154
• 238000005160 1H NMR spectroscopy Methods 0.000 description 141
• 239000000543 intermediate Substances 0.000 description 120
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 117
• 239000000203 mixture Substances 0.000 description 107
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 102
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 94
• 235000019439 ethyl acetate Nutrition 0.000 description 91
• 239000007787 solid Substances 0.000 description 82
• 229910001868 water Inorganic materials 0.000 description 80
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
• 239000002904 solvent Substances 0.000 description 78
• 239000007832 Na2SO4 Substances 0.000 description 67
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 67
• 229910052938 sodium sulfate Inorganic materials 0.000 description 67
• 235000011152 sodium sulphate Nutrition 0.000 description 67
• 230000000694 effects Effects 0.000 description 64
• 230000015572 biosynthetic process Effects 0.000 description 62
• 238000003786 synthesis reaction Methods 0.000 description 62
• 239000012044 organic layer Substances 0.000 description 58
• 101150041968 CDC13 gene Proteins 0.000 description 57
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
• 239000011541 reaction mixture Substances 0.000 description 54
• 230000002829 reductive effect Effects 0.000 description 50
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• 239000000741 silica gel Substances 0.000 description 34
• 229910002027 silica gel Inorganic materials 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 206010028980 Neoplasm Diseases 0.000 description 32
• 239000012267 brine Substances 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 32
• 238000004440 column chromatography Methods 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• 239000012043 crude product Substances 0.000 description 30
• 238000003818 flash chromatography Methods 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 26
• IIOMIXQUKPORSZ-UHFFFAOYSA-N 6-[(6-bromoimidazo[1,2-a]pyrimidin-3-yl)methyl]quinoline Chemical compound N1=CC=CC2=CC(CC3=CN=C4N=CC(=CN43)Br)=CC=C21 IIOMIXQUKPORSZ-UHFFFAOYSA-N 0.000 description 25
• 208000035475 disorder Diseases 0.000 description 25
• 239000003112 inhibitor Substances 0.000 description 25
• 230000002401 inhibitory effect Effects 0.000 description 24
• 238000003756 stirring Methods 0.000 description 23
• 230000007423 decrease Effects 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 230000003247 decreasing effect Effects 0.000 description 20
• 238000010992 reflux Methods 0.000 description 20
• 230000008685 targeting Effects 0.000 description 20
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 19
• 239000000460 chlorine Chemical group 0.000 description 19
• HGXJOXHYPGNVNK-UHFFFAOYSA-N butane;ethenoxyethane;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C)OCC HGXJOXHYPGNVNK-UHFFFAOYSA-N 0.000 description 18
• 238000001816 cooling Methods 0.000 description 18
• 235000017557 sodium bicarbonate Nutrition 0.000 description 18
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
• 239000004480 active ingredient Substances 0.000 description 17
• 229940079593 drug Drugs 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• 239000000725 suspension Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 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 16
• 201000011510 cancer Diseases 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 14
• 229910052740 iodine Inorganic materials 0.000 description 14
• 108090000623 proteins and genes Proteins 0.000 description 14
• 238000000746 purification Methods 0.000 description 14
• 230000001225 therapeutic effect Effects 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• MQWFFAABAAZNMB-UHFFFAOYSA-N 1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethanone Chemical compound N1=CC=CC2=CC(CN3N=NC4=NC=C(N=C43)C(=O)C)=CC=C21 MQWFFAABAAZNMB-UHFFFAOYSA-N 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• 102000004169 proteins and genes Human genes 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000003545 alkoxy group Chemical group 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 12
• 125000004429 atom Chemical group 0.000 description 12
• 150000002923 oximes Chemical class 0.000 description 12
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
• QEWBLEMJAWTJOO-UHFFFAOYSA-N 1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethanone Chemical compound N1=CC=CC2=CC(CC3=NN=C4C=CC(=NN43)C(=O)C)=CC=C21 QEWBLEMJAWTJOO-UHFFFAOYSA-N 0.000 description 11
• MVAXDJWUDYBAAH-UHFFFAOYSA-N 2-aminooxyethanol;hydrochloride Chemical compound Cl.NOCCO MVAXDJWUDYBAAH-UHFFFAOYSA-N 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
• 239000005557 antagonist Substances 0.000 description 11
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 238000010348 incorporation Methods 0.000 description 10
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• FKDCFTCWGQQZSP-WYMPLXKRSA-N 2-[(e)-1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanamine Chemical compound N1=CC=CC2=CC(CN3N=NC4=NC=C(N=C43)C(=N/OCCN)/C)=CC=C21 FKDCFTCWGQQZSP-WYMPLXKRSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• 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 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 239000002246 antineoplastic agent Substances 0.000 description 9
• 229910052801 chlorine Chemical group 0.000 description 9
• 239000013078 crystal Substances 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 108091000080 Phosphotransferase Proteins 0.000 description 8
• 230000001028 anti-proliverative effect Effects 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 229940088679 drug related substance Drugs 0.000 description 8
• VSHRKGLXEAWCKI-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-2-quinolin-6-ylacetohydrazide Chemical compound N1=NC(Cl)=CC=C1NNC(=O)CC1=CC=C(N=CC=C2)C2=C1 VSHRKGLXEAWCKI-UHFFFAOYSA-N 0.000 description 8
• 102000020233 phosphotransferase Human genes 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• QCNYMKCQVLOAOU-UHFFFAOYSA-N 1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethanone Chemical compound C1=CN=C2C=C(F)C(CN3N=NC4=NC=C(N=C43)C(=O)C)=CC2=C1 QCNYMKCQVLOAOU-UHFFFAOYSA-N 0.000 description 7
• ASKREEJRSDOYKI-KKMKTNMSSA-N 2-[(e)-1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound N1=CC=CC2=C(F)C(C(C=3N4N=C(C=CC4=NN=3)C(\C)=N\OCCO)C)=C(F)C=C21 ASKREEJRSDOYKI-KKMKTNMSSA-N 0.000 description 7
• 229910004373 HOAc Inorganic materials 0.000 description 7
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 125000000623 heterocyclic group Chemical group 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 150000002632 lipids Chemical class 0.000 description 7
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 7
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 7
• 238000000926 separation method Methods 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
• 238000002560 therapeutic procedure Methods 0.000 description 7
• 229940086542 triethylamine Drugs 0.000 description 7
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
• YFCXQUJKPIVRBF-STBIYBPSSA-N 2-[(e)-1-[3-[[3-(4-methylpiperazin-1-yl)quinolin-6-yl]methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]oxyethanol Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(CC=2N3N=C(C=CC3=NN=2)C(\C)=N\OCCO)=C2)C2=C1 YFCXQUJKPIVRBF-STBIYBPSSA-N 0.000 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 6
• 206010027476 Metastases Diseases 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 208000006265 Renal cell carcinoma Diseases 0.000 description 6
• 235000011114 ammonium hydroxide Nutrition 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 6
• FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 235000019198 oils Nutrition 0.000 description 6
• 230000003287 optical effect Effects 0.000 description 6
• 201000010279 papillary renal cell carcinoma Diseases 0.000 description 6
• 238000002953 preparative HPLC Methods 0.000 description 6
• 239000003755 preservative agent Substances 0.000 description 6
• 235000010288 sodium nitrite Nutrition 0.000 description 6
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