TWI619704B - 羧酸化合物 - Google Patents

Info

Publication number

TWI619704B

TWI619704B TW102117615A TW102117615A TWI619704B TW I619704 B TWI619704 B TW I619704B TW 102117615 A TW102117615 A TW 102117615A TW 102117615 A TW102117615 A TW 102117615A TW I619704 B TWI619704 B TW I619704B

Authority

TW

Taiwan

Prior art keywords

compound

amino

pharmaceutically acceptable

cancer

methyl

Prior art date

2012-05-18

Links

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• Global Dossier
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• -1 Carboxylic acid compounds Chemical class 0.000 title claims description 148
• 150000001875 compounds Chemical class 0.000 claims abstract description 447
• 150000003839 salts Chemical class 0.000 claims abstract description 138
• 238000000034 method Methods 0.000 claims abstract description 85
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 82
• 201000011510 cancer Diseases 0.000 claims abstract description 65
• 238000011282 treatment Methods 0.000 claims abstract description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 239000003814 drug Substances 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 102
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 125000006239 protecting group Chemical group 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 28
• 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 208000006673 asthma Diseases 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
• 206010038389 Renal cancer Diseases 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
• 206010009944 Colon cancer Diseases 0.000 claims description 11
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
• 230000001404 mediated effect Effects 0.000 claims description 11
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 10
• 208000029742 colonic neoplasm Diseases 0.000 claims description 10
• 201000010982 kidney cancer Diseases 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• NZMIALRJUDGDME-SFHVURJKSA-N 2-[[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-(2,2-difluoroethyl)amino]acetic acid Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(F)F)CC(O)=O)C=C1OC NZMIALRJUDGDME-SFHVURJKSA-N 0.000 claims description 8
• 208000035143 Bacterial infection Diseases 0.000 claims description 8
• 206010005003 Bladder cancer Diseases 0.000 claims description 8
• 206010006187 Breast cancer Diseases 0.000 claims description 8
• 208000026310 Breast neoplasm Diseases 0.000 claims description 8
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
• 206010033128 Ovarian cancer Diseases 0.000 claims description 8
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 8
• 206010060862 Prostate cancer Diseases 0.000 claims description 8
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 8
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 8
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 8
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 8
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 206010017758 gastric cancer Diseases 0.000 claims description 8
• 201000010536 head and neck cancer Diseases 0.000 claims description 8
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 8
• 201000007270 liver cancer Diseases 0.000 claims description 8
• 208000014018 liver neoplasm Diseases 0.000 claims description 8
• 201000005202 lung cancer Diseases 0.000 claims description 8
• 208000020816 lung neoplasm Diseases 0.000 claims description 8
• 230000003211 malignant effect Effects 0.000 claims description 8
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 8
• 201000002528 pancreatic cancer Diseases 0.000 claims description 8
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 201000000849 skin cancer Diseases 0.000 claims description 8
• 201000011549 stomach cancer Diseases 0.000 claims description 8
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 8
• 206010046766 uterine cancer Diseases 0.000 claims description 8
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 7
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
• 208000005176 Hepatitis C Diseases 0.000 claims description 7
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
• 201000010105 allergic rhinitis Diseases 0.000 claims description 7
• 201000008937 atopic dermatitis Diseases 0.000 claims description 7
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 208000002672 hepatitis B Diseases 0.000 claims description 7
• 210000003563 lymphoid tissue Anatomy 0.000 claims description 7
• 201000000050 myeloid neoplasm Diseases 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 6
• XWGKZKKNJOQUSG-SFHVURJKSA-N 2-[[4-[[2-amino-4-[[(3s)-1-hydroxyhexan-3-yl]amino]-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-(2,2,2-trifluoroethyl)amino]acetic acid Chemical compound CCC[C@@H](CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(O)=O)CC(F)(F)F)C=C1OC XWGKZKKNJOQUSG-SFHVURJKSA-N 0.000 claims description 6
• 208000015898 Bacterial Skin disease Diseases 0.000 claims description 6
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 6
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 6
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 5
• ZXPNPUZYBKVZFN-UHFFFAOYSA-N 2-[[4-[[2-amino-4-(butylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]acetic acid Chemical compound CCCCNC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CC(O)=O)C=C1OC ZXPNPUZYBKVZFN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 235000019260 propionic acid Nutrition 0.000 claims description 3
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• FIMNMHMOKYVGGK-UHFFFAOYSA-N 2-[acetyl-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl]amino]acetic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC(O)=O)C(C)=O)C=C1OC FIMNMHMOKYVGGK-UHFFFAOYSA-N 0.000 claims description 2
• WKSQSVJHSIYNRQ-UHFFFAOYSA-N 3-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]propanoic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CCC(O)=O)C=C1OC WKSQSVJHSIYNRQ-UHFFFAOYSA-N 0.000 claims description 2
• XWGKZKKNJOQUSG-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(O)=O)CC(F)(F)F)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(CN(CC(O)=O)CC(F)(F)F)cc1OC XWGKZKKNJOQUSG-UHFFFAOYSA-N 0.000 claims description 2
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
• ANCBWBFMSIQTEX-UHFFFAOYSA-N 2-[[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenyl]methyl-ethylamino]acetic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(CN(CC)CC(O)=O)C=C1OC ANCBWBFMSIQTEX-UHFFFAOYSA-N 0.000 claims 1
• VLBOFYFPALJWKB-UHFFFAOYSA-N 3-[3-[4-[[2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl]methyl]-3-methoxyphenoxy]propyl-ethylamino]propanoic acid Chemical compound CCCC(CCO)NC1=NC(N)=NC(C)=C1CC1=CC=C(OCCCN(CC)CCC(O)=O)C=C1OC VLBOFYFPALJWKB-UHFFFAOYSA-N 0.000 claims 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
• QZFXSCDMRRGGHK-UHFFFAOYSA-N CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN(CC)CC(O)=O)cc1OC Chemical compound CCCC(CCO)Nc1nc(N)nc(C)c1Cc1ccc(OCCCN(CC)CC(O)=O)cc1OC QZFXSCDMRRGGHK-UHFFFAOYSA-N 0.000 claims 1
• 208000022361 Human papillomavirus infectious disease Diseases 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 13
• 239000000543 intermediate Substances 0.000 abstract description 8
• 230000003612 virological effect Effects 0.000 abstract description 5
• 206010020751 Hypersensitivity Diseases 0.000 abstract description 4
• 208000023275 Autoimmune disease Diseases 0.000 abstract description 3
• 230000007815 allergy Effects 0.000 abstract description 3
• 208000015891 sexual disease Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
• 239000000203 mixture Substances 0.000 description 101
• 239000000047 product Substances 0.000 description 69
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
• 238000005481 NMR spectroscopy Methods 0.000 description 64
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
• 235000019439 ethyl acetate Nutrition 0.000 description 47
• 239000000243 solution Substances 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 40
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 40
• 238000000634 powder X-ray diffraction Methods 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• 239000007787 solid Substances 0.000 description 38
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 33
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 210000004027 cell Anatomy 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 239000012044 organic layer Substances 0.000 description 26
• 230000002829 reductive effect Effects 0.000 description 25
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 239000002246 antineoplastic agent Substances 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
• 238000003818 flash chromatography Methods 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• 239000003112 inhibitor Substances 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 241001465754 Metazoa Species 0.000 description 17
• 239000002585 base Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• 239000000741 silica gel Substances 0.000 description 17
• 229910002027 silica gel Inorganic materials 0.000 description 17
• 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000003795 chemical substances by application Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 241000699670 Mus sp. Species 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000012230 colorless oil Substances 0.000 description 14
• 230000000694 effects Effects 0.000 description 14
• 238000004458 analytical method Methods 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 239000000651 prodrug Substances 0.000 description 13
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• 102000002689 Toll-like receptor Human genes 0.000 description 12
• 108020000411 Toll-like receptor Proteins 0.000 description 12
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
• YZOKDOZIDBMHOK-LURJTMIESA-N (3s)-3-aminohexan-1-ol Chemical compound CCC[C@H](N)CCO YZOKDOZIDBMHOK-LURJTMIESA-N 0.000 description 11
• 239000012043 crude product Substances 0.000 description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 239000002552 dosage form Substances 0.000 description 10
• 238000005259 measurement Methods 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 230000002265 prevention Effects 0.000 description 10
• 238000001959 radiotherapy Methods 0.000 description 10
• 230000004614 tumor growth Effects 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• 102000004127 Cytokines Human genes 0.000 description 8
• 108090000695 Cytokines Proteins 0.000 description 8
• 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 8
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• 238000002474 experimental method Methods 0.000 description 8
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• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 235000015497 potassium bicarbonate Nutrition 0.000 description 8
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 8
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• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 8
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
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• 239000007864 aqueous solution Substances 0.000 description 7
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• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 7
• 210000004072 lung Anatomy 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• YCQYVAHQMLJURF-UHFFFAOYSA-N 3-[(2-amino-6-methylpyrimidin-4-yl)amino]hexan-1-ol Chemical compound NC1=NC(=CC(=N1)NC(CCO)CCC)C YCQYVAHQMLJURF-UHFFFAOYSA-N 0.000 description 6
• 206010004593 Bile duct cancer Diseases 0.000 description 6
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• 241001529936 Murinae Species 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 208000024770 Thyroid neoplasm Diseases 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
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• 201000002510 thyroid cancer Diseases 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• 241000699666 Mus <mouse, genus> Species 0.000 description 5
• 230000001154 acute effect Effects 0.000 description 5
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