MXPA06002014A

MXPA06002014A - Derivados de quinolinona sustituida y metodos de uso.

Derivados de quinolinona sustituida y metodos de uso.

Info

Publication number: MXPA06002014A
Authority: MX; Mexico
Prior art keywords: optionally substituted; carbon atoms; piperidin; substituted; boc
Prior art date: 2003-08-25

Application number

MXPA06002014A

Other languages

English (en)

Spanish (es)

Inventor

Christopher Tegley

Original Assignee

Amgen Inc

Priority date

2003-08-25

Filing date

2004-08-25

Publication date

2006-05-17

2004-08-25 Application filed by Amgen Inc filed Critical Amgen Inc

2006-05-17 Publication of MXPA06002014A publication Critical patent/MXPA06002014A/es

Links

238000000034 method Methods 0.000 title abstract description 54
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 268
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
238000011282 treatment Methods 0.000 claims abstract description 39
206010028980 Neoplasm Diseases 0.000 claims abstract description 35
230000033115 angiogenesis Effects 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
201000011510 cancer Diseases 0.000 claims abstract description 8
-1 -0R3 Chemical group 0.000 claims description 967
125000004432 carbon atom Chemical group C* 0.000 claims description 273
125000000623 heterocyclic group Chemical group 0.000 claims description 147
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 110
125000000217 alkyl group Chemical group 0.000 claims description 106
239000001257 hydrogen Substances 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 76
125000001424 substituent group Chemical group 0.000 claims description 64
150000002431 hydrogen Chemical group 0.000 claims description 60
125000005843 halogen group Chemical group 0.000 claims description 51
125000002757 morpholinyl group Chemical group 0.000 claims description 42
125000003282 alkyl amino group Chemical group 0.000 claims description 40
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 38
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 38
125000004043 oxo group Chemical group O=* 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 34
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 24
125000001153 fluoro group Chemical group F* 0.000 claims description 23
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 19
125000004663 dialkyl amino group Chemical group 0.000 claims description 19
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 17
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 17
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 17
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
239000000460 chlorine Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 15
208000035475 disorder Diseases 0.000 claims description 15
125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
125000001072 heteroaryl group Chemical group 0.000 claims description 15
125000000547 substituted alkyl group Chemical group 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
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
125000003118 aryl group Chemical group 0.000 claims description 13
125000002883 imidazolyl group Chemical group 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 12
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 11
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 11
229910052799 carbon Inorganic materials 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
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
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 8
125000004438 haloalkoxy group Chemical group 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 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
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 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
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
125000001786 isothiazolyl group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
125000004940 pyridazin-4-yl group Chemical group N1=NC=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
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 5
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 5
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 5
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 5
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
125000003806 alkyl carbonyl amino group Chemical group 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
239000011737 fluorine Substances 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
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 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
125000000335 thiazolyl group Chemical group 0.000 claims description 4
101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
239000002256 antimetabolite Substances 0.000 claims description 3
150000001721 carbon Chemical class 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
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
229940125697 hormonal agent Drugs 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
229910052701 rubidium Inorganic materials 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
APDAFIKLBAXHBX-UHFFFAOYSA-N 1h-pyrrole-2,4-diol Chemical compound OC1=CNC(O)=C1 APDAFIKLBAXHBX-UHFFFAOYSA-N 0.000 claims description 2
UKZRSGZEHCFYIH-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-8-(pyridin-4-ylmethylamino)phthalazin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C=N1 UKZRSGZEHCFYIH-UHFFFAOYSA-N 0.000 claims description 2
125000005466 alkylenyl group Chemical group 0.000 claims description 2
230000017531 blood circulation Effects 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
239000000677 immunologic agent Substances 0.000 claims description 2
229940124541 immunological agent Drugs 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 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
125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims 1
125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 36
201000010099 disease Diseases 0.000 abstract description 26
230000008569 process Effects 0.000 abstract description 26
230000001404 mediated effect Effects 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 3
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 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
238000006243 chemical reaction Methods 0.000 description 51
239000000203 mixture Substances 0.000 description 45
235000002639 sodium chloride Nutrition 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
210000004027 cell Anatomy 0.000 description 33
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 23
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 22
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 22
235000019439 ethyl acetate Nutrition 0.000 description 19
150000001299 aldehydes Chemical class 0.000 description 18
239000002253 acid Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
238000009472 formulation Methods 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
229940034982 antineoplastic agent Drugs 0.000 description 15
239000002246 antineoplastic agent Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
125000006239 protecting group Chemical group 0.000 description 13
239000004480 active ingredient Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
241000700159 Rattus Species 0.000 description 11
239000002671 adjuvant Substances 0.000 description 11
125000004433 nitrogen atom Chemical group N* 0.000 description 11
238000000746 purification Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
238000001819 mass spectrum Methods 0.000 description 10
239000000463 material Substances 0.000 description 10
125000004430 oxygen atom Chemical group O* 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000003981 vehicle Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
206010003246 arthritis Diseases 0.000 description 9
230000012010 growth Effects 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000004434 sulfur atom Chemical group 0.000 description 8
230000002792 vascular Effects 0.000 description 8
206010030113 Oedema Diseases 0.000 description 7
150000005840 aryl radicals Chemical class 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
125000003277 amino group Chemical group 0.000 description 6
239000012267 brine Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
210000004087 cornea Anatomy 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000002609 medium Substances 0.000 description 6
125000002911 monocyclic heterocycle group Chemical group 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
230000001225 therapeutic effect Effects 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
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
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 5
108010047761 Interferon-alpha Proteins 0.000 description 5
102000006992 Interferon-alpha Human genes 0.000 description 5
102000014150 Interferons Human genes 0.000 description 5
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