ES2310758T3 - Derivados de isoquinolina sustituidos y metodos de uso. - Google Patents

Info

Publication number

ES2310758T3

ES2310758T3 ES04782276T ES04782276T ES2310758T3 ES 2310758 T3 ES2310758 T3 ES 2310758T3 ES 04782276 T ES04782276 T ES 04782276T ES 04782276 T ES04782276 T ES 04782276T ES 2310758 T3 ES2310758 T3 ES 2310758T3

Authority

ES

Spain

Prior art keywords

optionally substituted

piperidin

substituted

heterocyclyl

members

Prior art date

2003-08-25

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.)

Expired - Lifetime

Links

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• 238000000034 method Methods 0.000 title abstract description 49
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 263
• 150000003839 salts Chemical class 0.000 claims abstract description 75
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
• 238000011282 treatment Methods 0.000 claims abstract description 38
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 37
• 230000033115 angiogenesis Effects 0.000 claims abstract description 15
• 201000011510 cancer Diseases 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• -1 -OR 3 Chemical group 0.000 claims description 1022
• 125000000623 heterocyclic group Chemical group 0.000 claims description 132
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 109
• 125000000217 alkyl group Chemical group 0.000 claims description 104
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 125000005843 halogen group Chemical group 0.000 claims description 50
• 239000000460 chlorine Substances 0.000 claims description 43
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 125000002757 morpholinyl group Chemical group 0.000 claims description 40
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 39
• 239000011737 fluorine Substances 0.000 claims description 39
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 38
• 229910052801 chlorine Inorganic materials 0.000 claims description 37
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 125000004043 oxo group Chemical group O=* 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 32
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 31
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 238000002360 preparation method Methods 0.000 claims description 29
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 26
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 23
• 229910052794 bromium Inorganic materials 0.000 claims description 23
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 22
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 16
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 16
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 14
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 14
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 14
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 11
• 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 11
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 11
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 230000035755 proliferation Effects 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002856 2-fluorophenylethyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 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 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 6
• 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• UBFZXVYANXWBCM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-8-(pyridin-4-ylmethylamino)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2CC1 UBFZXVYANXWBCM-UHFFFAOYSA-N 0.000 claims description 4
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
• SEXAJXZKQPYURX-UHFFFAOYSA-N CN(C)CC(=O)NBr Chemical compound CN(C)CC(=O)NBr SEXAJXZKQPYURX-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 239000002256 antimetabolite Substances 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 230000003115 biocidal effect Effects 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 3
• DURONAZNBKVEJO-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-8-(1h-pyrrolo[2,3-b]pyridin-3-ylmethylamino)phthalazin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C4=CC=CN=C4NC=3)C=CC=C2C=N1 DURONAZNBKVEJO-UHFFFAOYSA-N 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)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
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 230000017531 blood circulation Effects 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000003054 hormonal effect Effects 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 239000000677 immunologic agent Substances 0.000 claims description 2
• 229940124541 immunological agent Drugs 0.000 claims description 2
• 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
• 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 2
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 27
• 230000008569 process Effects 0.000 abstract description 21
• 239000000543 intermediate Substances 0.000 abstract description 5
• 230000001404 mediated effect Effects 0.000 abstract description 5
• 238000011321 prophylaxis Methods 0.000 abstract description 3
• 239000000651 prodrug Substances 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• 150000003254 radicals Chemical class 0.000 description 64
• 239000000203 mixture Substances 0.000 description 49
• 125000004432 carbon atom Chemical group C* 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 210000004027 cell Anatomy 0.000 description 31
• 239000002253 acid Substances 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 239000000243 solution Substances 0.000 description 22
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 21
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• 150000001299 aldehydes Chemical class 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 238000009472 formulation Methods 0.000 description 17
• 239000002246 antineoplastic agent Substances 0.000 description 16
• 125000004429 atom Chemical group 0.000 description 15
• 239000003981 vehicle Substances 0.000 description 15
• 229940034982 antineoplastic agent Drugs 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
• 241000700159 Rattus Species 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 230000014509 gene expression Effects 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• 210000004087 cornea Anatomy 0.000 description 10
• 230000012010 growth Effects 0.000 description 10
• 238000001819 mass spectrum Methods 0.000 description 10
• 229910052760 oxygen Inorganic materials 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000002671 adjuvant Substances 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 239000000377 silicon dioxide Substances 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• 239000013543 active substance Substances 0.000 description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 238000005984 hydrogenation reaction Methods 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
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• 239000003995 emulsifying agent Substances 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 239000002609 medium Substances 0.000 description 7
• 150000004702 methyl esters Chemical class 0.000 description 7
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
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• 125000004434 sulfur atom Chemical group 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 108010050904 Interferons Proteins 0.000 description 6
• 102000014150 Interferons Human genes 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 150000005840 aryl radicals Chemical class 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000006071 cream Substances 0.000 description 6
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• 229940079322 interferon Drugs 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 239000002953 phosphate buffered saline Substances 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 208000011580 syndromic disease Diseases 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 210000004881 tumor cell Anatomy 0.000 description 6
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 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 5
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