SK6492002A3 - Oncolytic combinations for the treatment of cancer - Google Patents

Oncolytic combinations for the treatment of cancer Download PDF

Info

Publication number: SK6492002A3
Authority: SK; Slovakia
Prior art keywords: ethyl; phenoxy; propoxy; mmol; formula
Prior art date: 1999-11-11

Application number

SK649-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Jerome Herbert Fleisch

Roger Stuart Benjamin

Jason Scott Sawyer

Beverly Ann Teicher

Douglas Wade Beight

Edward C R Smith

William Thomas Mcmillen

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1999-11-11

Filing date

2000-11-09

Publication date

2003-09-11

2000-11-09 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2003-09-11 Publication of SK6492002A3 publication Critical patent/SK6492002A3/sk

Links

238000011282 treatment Methods 0.000 title description 34
206010028980 Neoplasm Diseases 0.000 title description 25
201000011510 cancer Diseases 0.000 title description 6
230000000174 oncolytic effect Effects 0.000 title 1
239000002246 antineoplastic agent Substances 0.000 claims abstract description 50
239000005557 antagonist Substances 0.000 claims abstract description 48
150000002617 leukotrienes Chemical class 0.000 claims abstract description 13
150000001875 compounds Chemical class 0.000 claims description 201
239000000203 mixture Substances 0.000 claims description 200
-1 4-amino-2-oxo-1 H -pyrimidin-1-yl Chemical group 0.000 claims description 100
125000001424 substituent group Chemical group 0.000 claims description 33
229940041181 antineoplastic drug Drugs 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 32
239000001257 hydrogen Substances 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 20
229960005144 gemcitabine hydrochloride Drugs 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
239000000651 prodrug Substances 0.000 claims description 19
229940002612 prodrug Drugs 0.000 claims description 19
239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
239000002777 nucleoside Substances 0.000 claims description 6
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000005647 linker group Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000002346 iodo group Chemical group I* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical group O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
229910052760 oxygen Chemical group 0.000 claims description 2
239000001301 oxygen Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims 1
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 204
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 158
239000000243 solution Substances 0.000 description 116
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
238000002360 preparation method Methods 0.000 description 79
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 77
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 56
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
239000000741 silica gel Substances 0.000 description 47
229910002027 silica gel Inorganic materials 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 42
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 42
229910052938 sodium sulfate Inorganic materials 0.000 description 42
235000011152 sodium sulphate Nutrition 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
238000004587 chromatography analysis Methods 0.000 description 39
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 38
239000003826 tablet Substances 0.000 description 36
238000000034 method Methods 0.000 description 35
239000012044 organic layer Substances 0.000 description 35
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 31
OKKDEIYWILRZIA-OSZBKLCCSA-N gemcitabine hydrochloride Chemical compound [H+].[Cl-].O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 OKKDEIYWILRZIA-OSZBKLCCSA-N 0.000 description 30
230000004614 tumor growth Effects 0.000 description 30
238000010183 spectrum analysis Methods 0.000 description 29
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
239000004480 active ingredient Substances 0.000 description 27
238000002531 positive electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 27
206010053759 Growth retardation Diseases 0.000 description 26
238000004458 analytical method Methods 0.000 description 26
231100000001 growth retardation Toxicity 0.000 description 26
239000007787 solid Substances 0.000 description 26
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 24
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 24
239000002464 receptor antagonist Substances 0.000 description 23
229940044551 receptor antagonist Drugs 0.000 description 23
229920002472 Starch Polymers 0.000 description 22
239000011734 sodium Substances 0.000 description 22
239000008107 starch Substances 0.000 description 22
235000019698 starch Nutrition 0.000 description 22
239000004615 ingredient Substances 0.000 description 21
238000004519 manufacturing process Methods 0.000 description 21
230000007062 hydrolysis Effects 0.000 description 20
238000006460 hydrolysis reaction Methods 0.000 description 20
235000019359 magnesium stearate Nutrition 0.000 description 20
239000000047 product Substances 0.000 description 20
229910052708 sodium Inorganic materials 0.000 description 19
239000012230 colorless oil Substances 0.000 description 18
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
239000002775 capsule Substances 0.000 description 17
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
239000002585 base Substances 0.000 description 16
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 15
239000005711 Benzoic acid Substances 0.000 description 15
101150003085 Pdcl gene Proteins 0.000 description 15
235000010233 benzoic acid Nutrition 0.000 description 15
238000006264 debenzylation reaction Methods 0.000 description 15
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
150000002431 hydrogen Chemical class 0.000 description 15
229910052763 palladium Inorganic materials 0.000 description 15
230000005588 protonation Effects 0.000 description 15
150000002148 esters Chemical class 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
235000019260 propionic acid Nutrition 0.000 description 14
238000009472 formulation Methods 0.000 description 13
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 13
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
238000010992 reflux Methods 0.000 description 13
229910015900 BF3 Inorganic materials 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
239000003085 diluting agent Substances 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
239000013543 active substance Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 10
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
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239000007864 aqueous solution Substances 0.000 description 9
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000007903 gelatin capsule Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
239000000829 suppository Substances 0.000 description 9
239000000454 talc Substances 0.000 description 9
235000012222 talc Nutrition 0.000 description 9
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
239000000969 carrier Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
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235000000346 sugar Nutrition 0.000 description 8
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230000001093 anti-cancer Effects 0.000 description 7
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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BPFQATAMBMJXBN-UHFFFAOYSA-N methyl 2-[3-[3-(4-bromo-2-ethyl-5-phenylmethoxyphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1Br)CC)=CC=1OCC1=CC=CC=C1 BPFQATAMBMJXBN-UHFFFAOYSA-N 0.000 description 6
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239000003981 vehicle Substances 0.000 description 6
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ZWGMJLNXIVRFRJ-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-2-yl]boronic acid Chemical compound CC(C)(C)OC(=O)N1C=CC=C1B(O)O ZWGMJLNXIVRFRJ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000004913 activation Effects 0.000 description 2
201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
206010003246 arthritis Diseases 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
229910000389 calcium phosphate Inorganic materials 0.000 description 2
235000011010 calcium phosphates Nutrition 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
238000011260 co-administration Methods 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
239000003086 colorant Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
235000019797 dipotassium phosphate Nutrition 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 2
CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 2
150000002240 furans Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000005456 glyceride group Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000008595 infiltration Effects 0.000 description 2
238000001764 infiltration Methods 0.000 description 2
230000004968 inflammatory condition Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
239000011344 liquid material Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
201000005202 lung cancer Diseases 0.000 description 2
208000020816 lung neoplasm Diseases 0.000 description 2
JJQQCKNUJPDQFB-UHFFFAOYSA-N methyl 2-(3-hydroxy-2-propylphenoxy)benzoate Chemical compound CCCC1=C(O)C=CC=C1OC1=CC=CC=C1C(=O)OC JJQQCKNUJPDQFB-UHFFFAOYSA-N 0.000 description 2
HCCCRBKNPSKUTL-UHFFFAOYSA-N methyl 2-[3-[3-(2-ethyl-4-ethynyl-5-phenylmethoxyphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C#C)CC)=CC=1OCC1=CC=CC=C1 HCCCRBKNPSKUTL-UHFFFAOYSA-N 0.000 description 2
GEWMTUVWZSKESO-UHFFFAOYSA-N methyl 2-[3-[3-(2-ethyl-5-hydroxy-4-pyrrol-1-ylphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1N1C=CC=C1 GEWMTUVWZSKESO-UHFFFAOYSA-N 0.000 description 2
ZPFVQUKDFURLHW-UHFFFAOYSA-N methyl 2-[3-[3-(2-ethyl-5-hydroxy-4-thiophen-2-ylphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=CS1 ZPFVQUKDFURLHW-UHFFFAOYSA-N 0.000 description 2
IHLVKMDVXVNXCN-UHFFFAOYSA-N methyl 2-[3-[3-(2-ethyl-5-phenylmethoxy-4-pyrrol-1-ylphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1N2C=CC=C2)CC)=CC=1OCC1=CC=CC=C1 IHLVKMDVXVNXCN-UHFFFAOYSA-N 0.000 description 2
CPAGKKYSJXMZGU-UHFFFAOYSA-N methyl 2-[3-[3-(4-bromo-2-ethyl-5-hydroxyphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC1=CC(O)=C(Br)C=C1CC CPAGKKYSJXMZGU-UHFFFAOYSA-N 0.000 description 2
QXJYOGHLVRSUPG-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(1,2-oxazol-5-yl)-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2ON=CC=2)CC)=CC=1OCC1=CC=CC=C1 QXJYOGHLVRSUPG-UHFFFAOYSA-N 0.000 description 2
HROJOCUSUFSMTH-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(1,3-oxazol-4-yl)-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2N=COC=2)CC)=CC=1OCC1=CC=CC=C1 HROJOCUSUFSMTH-UHFFFAOYSA-N 0.000 description 2
BKESRMXQNNIOGI-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(1-methylpyrazol-4-yl)-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C2=CN(C)N=C2)CC)=CC=1OCC1=CC=CC=C1 BKESRMXQNNIOGI-UHFFFAOYSA-N 0.000 description 2
DHKYFHDXWKZGEG-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(2-hydroxyacetyl)-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C(=O)CO)CC)=CC=1OCC1=CC=CC=C1 DHKYFHDXWKZGEG-UHFFFAOYSA-N 0.000 description 2
SHAJHZLCBBKZBJ-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(furan-2-yl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=CO1 SHAJHZLCBBKZBJ-UHFFFAOYSA-N 0.000 description 2
QIXVGLGBFGTJDN-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(furan-3-yl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C=1C=COC=1 QIXVGLGBFGTJDN-UHFFFAOYSA-N 0.000 description 2
GQBQNUNVWUJTBO-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-4-(furan-3-yl)-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C2=COC=C2)CC)=CC=1OCC1=CC=CC=C1 GQBQNUNVWUJTBO-UHFFFAOYSA-N 0.000 description 2
IGYHAQCEJNCMKW-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-5-hydroxy-4-(1,2-oxazol-5-yl)phenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=NO1 IGYHAQCEJNCMKW-UHFFFAOYSA-N 0.000 description 2
QESXVGZHGYYBOL-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-5-hydroxy-4-(1,3-oxazol-4-yl)phenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=COC=N1 QESXVGZHGYYBOL-UHFFFAOYSA-N 0.000 description 2
ULVDBQKNYVMTJG-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-5-hydroxy-4-(1,3-thiazol-4-yl)phenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CSC=N1 ULVDBQKNYVMTJG-UHFFFAOYSA-N 0.000 description 2
NSHBBTYKQRQJOJ-UHFFFAOYSA-N methyl 2-[3-[3-[2-ethyl-5-phenylmethoxy-4-(1,3-thiazol-4-yl)phenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2N=CSC=2)CC)=CC=1OCC1=CC=CC=C1 NSHBBTYKQRQJOJ-UHFFFAOYSA-N 0.000 description 2
UYEVNHUURVFIGL-UHFFFAOYSA-N methyl 2-[3-[3-[4-(2-benzylsulfanyl-1h-imidazol-5-yl)-2-ethyl-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2NC(SCC=3C=CC=CC=3)=NC=2)CC)=CC=1OCC1=CC=CC=C1 UYEVNHUURVFIGL-UHFFFAOYSA-N 0.000 description 2
OSWUSNOIJYZRGM-UHFFFAOYSA-N methyl 2-[3-[3-[4-(2-chloroacetyl)-2-ethyl-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C(=O)CCl)CC)=CC=1OCC1=CC=CC=C1 OSWUSNOIJYZRGM-UHFFFAOYSA-N 0.000 description 2
GETJYCPGHZBQLK-UHFFFAOYSA-N methyl 2-[3-[3-[4-(3-bromo-1,2,4-thiadiazol-5-yl)-2-ethyl-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2SN=C(Br)N=2)CC)=CC=1OCC1=CC=CC=C1 GETJYCPGHZBQLK-UHFFFAOYSA-N 0.000 description 2
WSTQVWNAIRONAV-UHFFFAOYSA-N methyl 2-[3-[3-[4-[3-(dimethylamino)prop-2-enoyl]-2-ethyl-5-phenylmethoxyphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C(=O)C=CN(C)C)CC)=CC=1OCC1=CC=CC=C1 WSTQVWNAIRONAV-UHFFFAOYSA-N 0.000 description 2
SNYDJDGUVUQXKJ-UHFFFAOYSA-N methyl 2-[3-[3-[4-bromo-5-[tert-butyl(dimethyl)silyl]oxy-2-ethylphenoxy]propoxy]-2-propylphenoxy]benzoate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC1=CC(O[Si](C)(C)C(C)(C)C)=C(Br)C=C1CC SNYDJDGUVUQXKJ-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
230000036457 multidrug resistance Effects 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
238000011580 nude mouse model Methods 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000123 paper Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
208000023958 prostate neoplasm Diseases 0.000 description 2
RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
235000003441 saturated fatty acids Nutrition 0.000 description 2
150000004671 saturated fatty acids Chemical class 0.000 description 2
230000035939 shock Effects 0.000 description 2
FDLSKWNNRUNGHG-UHFFFAOYSA-M sodium;2-[3-[3-(2-ethyl-5-hydroxy-4-thiophen-2-ylphenoxy)propoxy]-2-propylphenoxy]benzoate Chemical compound [Na+].C1=CC=C(OC=2C(=CC=CC=2)C([O-])=O)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=CS1 FDLSKWNNRUNGHG-UHFFFAOYSA-M 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
ASHFCEWWEACWRP-UHFFFAOYSA-N tert-butyl 2-[5-ethyl-2-hydroxy-4-[3-[3-(2-methoxycarbonylphenoxy)-2-propylphenoxy]propoxy]phenyl]pyrrolidine-1-carboxylate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1CCCN1C(=O)OC(C)(C)C ASHFCEWWEACWRP-UHFFFAOYSA-N 0.000 description 2
IINYSRKSVORNMC-UHFFFAOYSA-N tert-butyl 2-[5-ethyl-4-[3-[3-(2-methoxycarbonylphenoxy)-2-propylphenoxy]propoxy]-2-phenylmethoxyphenyl]pyrrole-1-carboxylate Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(=O)OC)C(CCC)=C1OCCCOC(C(=CC=1C=2N(C=CC=2)C(=O)OC(C)(C)C)CC)=CC=1OCC1=CC=CC=C1 IINYSRKSVORNMC-UHFFFAOYSA-N 0.000 description 2
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
150000003555 thioacetals Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
HOXWDFOEIDECNS-UHFFFAOYSA-N tributyl(ethyl)stannane Chemical compound CCCC[Sn](CC)(CCCC)CCCC HOXWDFOEIDECNS-UHFFFAOYSA-N 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
229940029284 trichlorofluoromethane Drugs 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
150000004684 trihydrates Chemical class 0.000 description 2
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
150000004670 unsaturated fatty acids Chemical class 0.000 description 2
235000021122 unsaturated fatty acids Nutrition 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
HMJKKUMPMAZJFK-UHFFFAOYSA-N 1-[4-(3-chloropropoxy)-5-ethyl-2-hydroxyphenyl]ethanone Chemical compound CCC1=CC(C(C)=O)=C(O)C=C1OCCCCl HMJKKUMPMAZJFK-UHFFFAOYSA-N 0.000 description 1
GUVPYRHDBBDFKQ-UHFFFAOYSA-N 2-(3-hydroxy-2-propylphenoxy)benzoic acid Chemical compound CCCC1=C(O)C=CC=C1OC1=CC=CC=C1C(O)=O GUVPYRHDBBDFKQ-UHFFFAOYSA-N 0.000 description 1
PAWXZXWYNRNGBQ-UHFFFAOYSA-N 2-(3-hydroxy-2-propylphenoxy)benzonitrile Chemical compound CCCC1=C(O)C=CC=C1OC1=CC=CC=C1C#N PAWXZXWYNRNGBQ-UHFFFAOYSA-N 0.000 description 1
BWSZHEONLXBVNB-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-ethyl-5-[6-methyl-6-(2h-tetrazol-5-yl)heptoxy]phenol Chemical class CCC1=CC(C=2C=CC(Cl)=CC=2)=C(O)C=C1OCCCCCC(C)(C)C=1N=NNN=1 BWSZHEONLXBVNB-UHFFFAOYSA-N 0.000 description 1
IIRMQXPORZFGKC-UHFFFAOYSA-N 2-[2-[3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenoxy]phenyl]acetic acid Chemical compound C1=CC=C(OC=2C(=CC=CC=2)CC(O)=O)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=C(F)C=C1 IIRMQXPORZFGKC-UHFFFAOYSA-N 0.000 description 1
LTTILCXEKABAIF-UHFFFAOYSA-N 2-[2-benzyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid Chemical compound CCC1=CC(C=2C=CC(F)=CC=2)=C(O)C=C1OCCCOC(C=1CC=2C=CC=CC=2)=CC=CC=1OC1=CC=CC=C1C(O)=O LTTILCXEKABAIF-UHFFFAOYSA-N 0.000 description 1
VZLISDKPNXNRGN-UHFFFAOYSA-N 2-[2-butyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(O)=O)C(CCCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=C(F)C=C1 VZLISDKPNXNRGN-UHFFFAOYSA-N 0.000 description 1
UDQJUNFZMYLZAE-UHFFFAOYSA-N 2-[3-(dimethylamino)phenyl]-4-ethyl-5-[6-methyl-6-(2H-tetrazol-5-yl)heptoxy]phenol Chemical compound CCC1=CC(C=2C=C(C=CC=2)N(C)C)=C(O)C=C1OCCCCCC(C)(C)C=1N=NNN=1 UDQJUNFZMYLZAE-UHFFFAOYSA-N 0.000 description 1
MAHXUFYQFCPCNJ-UHFFFAOYSA-N 2-[3-[3-(2-ethyl-5-hydroxy-4-phenylphenoxy)propoxy]-2-propylphenoxy]benzoic acid Chemical compound C1=CC=C(OC=2C(=CC=CC=2)C(O)=O)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=CC=C1 MAHXUFYQFCPCNJ-UHFFFAOYSA-N 0.000 description 1
ZIBIHRQXGKOFAR-UHFFFAOYSA-N 2-[3-[3-(2-ethyl-5-hydroxy-4-phenylphenoxy)propoxy]-2-propylphenoxy]propanoic acid Chemical compound C1=CC=C(OC(C)C(O)=O)C(CCC)=C1OCCCOC1=CC(O)=C(C=2C=CC=CC=2)C=C1CC ZIBIHRQXGKOFAR-UHFFFAOYSA-N 0.000 description 1
FTBUTMHYVSIDRY-UHFFFAOYSA-N 2-[3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylbenzoyl]benzoic acid Chemical compound C1=CC=C(C(=O)C=2C(=CC=CC=2)C(O)=O)C(CCC)=C1OCCCOC(C(=C1)CC)=CC(O)=C1C1=CC=C(F)C=C1 FTBUTMHYVSIDRY-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)

SK649-2002A 1999-11-11 2000-11-09 Oncolytic combinations for the treatment of cancer SK6492002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US16478699P	1999-11-11	1999-11-11
PCT/US2000/031039 WO2001034137A2 (en)	1999-11-11	2000-11-09	Oncolytic combinations for the treatment of cancer

Publications (1)

Publication Number	Publication Date
SK6492002A3 true SK6492002A3 (en)	2003-09-11

Family

ID=22596085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK649-2002A SK6492002A3 (en)	1999-11-11	2000-11-09	Oncolytic combinations for the treatment of cancer

Country Status (22)

Country	Link
EP (1)	EP1231938A2 (es)
JP (1)	JP2003513916A (es)
KR (1)	KR20020069512A (es)
CN (1)	CN1390139A (es)
AR (1)	AR032432A1 (es)
AU (1)	AU778829B2 (es)
BR (1)	BR0015490A (es)
CA (1)	CA2391416A1 (es)
CZ (1)	CZ20021551A3 (es)
EA (1)	EA200200545A1 (es)
HK (1)	HK1050132A1 (es)
HU (1)	HUP0204449A3 (es)
IL (1)	IL148579A0 (es)
MX (1)	MXPA02004733A (es)
NO (1)	NO20022245L (es)
NZ (1)	NZ517667A (es)
PE (1)	PE20010701A1 (es)
PL (1)	PL355172A1 (es)
SK (1)	SK6492002A3 (es)
TR (1)	TR200201245T2 (es)
WO (1)	WO2001034137A2 (es)
ZA (1)	ZA200202822B (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001034197A2 (en) *	1999-11-11	2001-05-17	Eli Lilly And Company	Oncolytic combinations for the treatment of cancer
US6797723B1 (en)	1999-11-11	2004-09-28	Eli Lilly And Company	Heterocycle substituted diphenyl leukotriene antagonists
WO2001034198A2 (en) *	1999-11-11	2001-05-17	Eli Lilly And Company	Oncolytic combinations for the treatment of cancer
JP2001247459A (ja)	2000-03-03	2001-09-11	Oakland Uniservices Ltd	癌の組み合わせ療法
WO2001085166A1 (en) *	2000-05-09	2001-11-15	Creighton University	Methods for inhibiting proliferation and inducing apoptosis in cancer cells
AU2001282717A1 (en)	2000-07-28	2002-02-13	Cancer Research Technology Limited	Cancer treatment by combination therapy
GB0121285D0 (en)	2001-09-03	2001-10-24	Cancer Res Ventures Ltd	Anti-cancer combinations
GB2386836B (en)	2002-03-22	2006-07-26	Cancer Res Ventures Ltd	Anti-cancer combinations
GB2394658A (en)	2002-11-01	2004-05-05	Cancer Rec Tech Ltd	Oral anti-cancer composition
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AU1599001A (en)	2001-06-06
CZ20021551A3 (cs)	2003-02-12
JP2003513916A (ja)	2003-04-15
NO20022245L (no)	2002-07-09
EA200200545A1 (ru)	2002-12-26
AR032432A1 (es)	2003-11-12
ZA200202822B (en)	2003-09-23
AU778829B2 (en)	2004-12-23
KR20020069512A (ko)	2002-09-04
NO20022245D0 (no)	2002-05-10
NZ517667A (en)	2004-05-28
WO2001034137A3 (en)	2002-02-14
HK1050132A1 (zh)	2003-06-13
TR200201245T2 (tr)	2004-08-23
MXPA02004733A (es)	2002-08-30
WO2001034137A2 (en)	2001-05-17
HUP0204449A2 (hu)	2003-04-28
CA2391416A1 (en)	2001-05-17
CN1390139A (zh)	2003-01-08
PL355172A1 (en)	2004-04-05
PE20010701A1 (es)	2001-07-07
BR0015490A (pt)	2002-07-09
EP1231938A2 (en)	2002-08-21
HUP0204449A3 (en)	2006-02-28
IL148579A0 (en)	2002-09-12

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