AU2008225833A1 - Amide compounds and their use as antitumor agents - Google Patents
Amide compounds and their use as antitumor agents Download PDFInfo
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- AU2008225833A1 AU2008225833A1 AU2008225833A AU2008225833A AU2008225833A1 AU 2008225833 A1 AU2008225833 A1 AU 2008225833A1 AU 2008225833 A AU2008225833 A AU 2008225833A AU 2008225833 A AU2008225833 A AU 2008225833A AU 2008225833 A1 AU2008225833 A1 AU 2008225833A1
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- -1 Amide compounds Chemical class 0.000 title description 23
- 239000002246 antineoplastic agent Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 21
- 210000004027 cell Anatomy 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 210000004881 tumor cell Anatomy 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 102000003964 Histone deacetylase Human genes 0.000 claims description 9
- 108090000353 Histone deacetylase Proteins 0.000 claims description 9
- 230000004069 differentiation Effects 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000011712 cell development Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- 230000035755 proliferation Effects 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 210000005170 neoplastic cell Anatomy 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 208000011571 secondary malignant neoplasm Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 216
- 238000000034 method Methods 0.000 description 209
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 177
- 238000005160 1H NMR spectroscopy Methods 0.000 description 119
- 235000019439 ethyl acetate Nutrition 0.000 description 108
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- 239000000543 intermediate Substances 0.000 description 76
- 239000000203 mixture Substances 0.000 description 71
- 239000000243 solution Substances 0.000 description 70
- 238000003818 flash chromatography Methods 0.000 description 69
- 239000002253 acid Substances 0.000 description 66
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000003921 oil Substances 0.000 description 58
- 235000019198 oils Nutrition 0.000 description 58
- 239000012230 colorless oil Substances 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 150000004702 methyl esters Chemical class 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000004128 high performance liquid chromatography Methods 0.000 description 42
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 36
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 150000002678 macrocyclic compounds Chemical class 0.000 description 25
- 150000001336 alkenes Chemical group 0.000 description 23
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 150000003931 anilides Chemical class 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 19
- 239000012300 argon atmosphere Substances 0.000 description 18
- 238000011097 chromatography purification Methods 0.000 description 18
- 238000010511 deprotection reaction Methods 0.000 description 18
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 18
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 17
- 230000009467 reduction Effects 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 229910052786 argon Inorganic materials 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 13
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000005937 allylation reaction Methods 0.000 description 10
- 150000001540 azides Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 9
- 150000001993 dienes Chemical group 0.000 description 9
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 8
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 8
- 238000006798 ring closing metathesis reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- XNCNNDVCAUWAIT-UHFFFAOYSA-N Methyl heptanoate Chemical compound CCCCCCC(=O)OC XNCNNDVCAUWAIT-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000005686 cross metathesis reaction Methods 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- SDTORDSXCYSNTD-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methoxymethyl]benzene Chemical compound C1=CC(OC)=CC=C1COCC1=CC=C(OC)C=C1 SDTORDSXCYSNTD-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FSNCEEGOMTYXKY-JTQLQIEISA-N Lycoperodine 1 Natural products N1C2=CC=CC=C2C2=C1CN[C@H](C(=O)O)C2 FSNCEEGOMTYXKY-JTQLQIEISA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 238000006640 acetylation reaction Methods 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 5
- 239000008241 heterogeneous mixture Substances 0.000 description 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 5
- 229960000237 vorinostat Drugs 0.000 description 5
- FIOJWGRGPONADF-UHFFFAOYSA-N (sulfinylamino)benzene Chemical class O=S=NC1=CC=CC=C1 FIOJWGRGPONADF-UHFFFAOYSA-N 0.000 description 4
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 238000010934 O-alkylation reaction Methods 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- PNPBGYBHLCEVMK-UHFFFAOYSA-L benzylidene(dichloro)ruthenium;tricyclohexylphosphane Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-L 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- VVDIWAYJRNKZLB-UHFFFAOYSA-N methyl 8-anilino-7-[(3-methoxyphenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=CC(OC)=C1 VVDIWAYJRNKZLB-UHFFFAOYSA-N 0.000 description 4
- QXMVBURPOIZXPZ-UHFFFAOYSA-N methyl 8-anilino-7-[(4-bromophenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=C(Br)C=C1 QXMVBURPOIZXPZ-UHFFFAOYSA-N 0.000 description 4
- KUVIRDUPAGKTER-UHFFFAOYSA-N n-phenylmethoxyaniline Chemical compound C=1C=CC=CC=1CONC1=CC=CC=C1 KUVIRDUPAGKTER-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JUQLUIFNNFIIKC-UHFFFAOYSA-N 2-aminopimelic acid Chemical compound OC(=O)C(N)CCCCC(O)=O JUQLUIFNNFIIKC-UHFFFAOYSA-N 0.000 description 3
- WJXSWCUQABXPFS-UHFFFAOYSA-N 3-hydroxyanthranilic acid Chemical compound NC1=C(O)C=CC=C1C(O)=O WJXSWCUQABXPFS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
- 239000000411 inducer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- KNONKIHTJXXNFJ-NRFANRHFSA-N methyl (6s)-7-[tert-butyl(diphenyl)silyl]oxy-6-methoxyheptanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OC[C@H](CCCCC(=O)OC)OC)C1=CC=CC=C1 KNONKIHTJXXNFJ-NRFANRHFSA-N 0.000 description 1
- BZRBQTSDUWHKRH-ZDUSSCGKSA-N methyl (6s)-7-anilino-6-methoxy-7-oxoheptanoate Chemical compound COC(=O)CCCC[C@H](OC)C(=O)NC1=CC=CC=C1 BZRBQTSDUWHKRH-ZDUSSCGKSA-N 0.000 description 1
- GBFYGZNWRPUWJL-OAQYLSRUSA-N methyl (7r)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyoctanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OC[C@H](O)CCCCCC(=O)OC)C1=CC=CC=C1 GBFYGZNWRPUWJL-OAQYLSRUSA-N 0.000 description 1
- RNFUZEBPZQPFHS-OAQYLSRUSA-N methyl (7r)-8-anilino-7-[(4-methoxyphenyl)methoxy]-8-oxooctanoate Chemical compound O([C@H](CCCCCC(=O)OC)C(=O)NC=1C=CC=CC=1)CC1=CC=C(OC)C=C1 RNFUZEBPZQPFHS-OAQYLSRUSA-N 0.000 description 1
- SONJSYVLGLPOAA-CYBMUJFWSA-N methyl (7r)-8-anilino-7-hydroxy-8-oxooctanoate Chemical compound COC(=O)CCCCC[C@@H](O)C(=O)NC1=CC=CC=C1 SONJSYVLGLPOAA-CYBMUJFWSA-N 0.000 description 1
- KKNRJMMREMVRJK-DEOSSOPVSA-N methyl (7s)-8-[tert-butyl(diphenyl)silyl]oxy-7-[(2-methylpropan-2-yl)oxycarbonylamino]octanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OC[C@H](CCCCCC(=O)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 KKNRJMMREMVRJK-DEOSSOPVSA-N 0.000 description 1
- GBFYGZNWRPUWJL-NRFANRHFSA-N methyl (7s)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyoctanoate Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OC[C@@H](O)CCCCCC(=O)OC)C1=CC=CC=C1 GBFYGZNWRPUWJL-NRFANRHFSA-N 0.000 description 1
- RNFUZEBPZQPFHS-NRFANRHFSA-N methyl (7s)-8-anilino-7-[(4-methoxyphenyl)methoxy]-8-oxooctanoate Chemical compound O([C@@H](CCCCCC(=O)OC)C(=O)NC=1C=CC=CC=1)CC1=CC=C(OC)C=C1 RNFUZEBPZQPFHS-NRFANRHFSA-N 0.000 description 1
- SONJSYVLGLPOAA-ZDUSSCGKSA-N methyl (7s)-8-anilino-7-hydroxy-8-oxooctanoate Chemical compound COC(=O)CCCCC[C@H](O)C(=O)NC1=CC=CC=C1 SONJSYVLGLPOAA-ZDUSSCGKSA-N 0.000 description 1
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 1
- DRAVDPWPYMLGBK-UHFFFAOYSA-N methyl 6-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)hexanoate Chemical compound COC(=O)CCCCCC1OC(C)(C)OC1=O DRAVDPWPYMLGBK-UHFFFAOYSA-N 0.000 description 1
- FPOLLXCIQCNBGZ-UHFFFAOYSA-N methyl 6-(3-oxo-5,10-dioxa-2-azabicyclo[9.4.0]pentadeca-1(15),11,13-trien-4-yl)hexanoate Chemical compound N1C(=O)C(CCCCCC(=O)OC)OCCCCOC2=CC=CC=C21 FPOLLXCIQCNBGZ-UHFFFAOYSA-N 0.000 description 1
- FDJMUUIOYWMJRA-UHFFFAOYSA-N methyl 6-(3-oxo-5,11-dioxa-2-azabicyclo[10.4.0]hexadeca-1(16),12,14-trien-4-yl)hexanoate Chemical compound N1C(=O)C(CCCCCC(=O)OC)OCCCCCOC2=CC=CC=C21 FDJMUUIOYWMJRA-UHFFFAOYSA-N 0.000 description 1
- OBPHODDDZTUOMY-UHFFFAOYSA-N methyl 7-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)hept-2-enoate Chemical compound COC(=O)C=CCCCCC1OC(C)(C)OC1=O OBPHODDDZTUOMY-UHFFFAOYSA-N 0.000 description 1
- KXHYWVQDVCJJJZ-UHFFFAOYSA-N methyl 7-anilino-6-[(4-methoxyphenyl)methoxy]-7-oxoheptanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCC(=O)OC)OCC1=CC=C(OC)C=C1 KXHYWVQDVCJJJZ-UHFFFAOYSA-N 0.000 description 1
- NMAXFHMZUMCBBK-UHFFFAOYSA-N methyl 7-anilino-6-hydroxy-7-oxoheptanoate Chemical compound COC(=O)CCCCC(O)C(=O)NC1=CC=CC=C1 NMAXFHMZUMCBBK-UHFFFAOYSA-N 0.000 description 1
- BZRBQTSDUWHKRH-UHFFFAOYSA-N methyl 7-anilino-6-methoxy-7-oxoheptanoate Chemical compound COC(=O)CCCCC(OC)C(=O)NC1=CC=CC=C1 BZRBQTSDUWHKRH-UHFFFAOYSA-N 0.000 description 1
- XMJFRJQQPLMBOA-UHFFFAOYSA-N methyl 7-anilino-7-oxo-6-phenylmethoxyheptanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCC(=O)OC)OCC1=CC=CC=C1 XMJFRJQQPLMBOA-UHFFFAOYSA-N 0.000 description 1
- FEUMTTDUYSKWED-UHFFFAOYSA-N methyl 7-anilino-7-oxo-6-propoxyheptanoate Chemical compound COC(=O)CCCCC(OCCC)C(=O)NC1=CC=CC=C1 FEUMTTDUYSKWED-UHFFFAOYSA-N 0.000 description 1
- XKDCMMMIFVPWKI-UHFFFAOYSA-N methyl 7-hydroxy-8-(4-methoxyanilino)-8-oxooctanoate Chemical compound COC(=O)CCCCCC(O)C(=O)NC1=CC=C(OC)C=C1 XKDCMMMIFVPWKI-UHFFFAOYSA-N 0.000 description 1
- BBUPVWSIFYJSMX-UHFFFAOYSA-N methyl 8-(4-methoxyanilino)-7-[(4-methoxyphenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=C(OC)C=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=C(OC)C=C1 BBUPVWSIFYJSMX-UHFFFAOYSA-N 0.000 description 1
- PPZBUJURNSUKGW-UHFFFAOYSA-N methyl 8-(4-methoxyanilino)-8-oxo-7-phenylmethoxyoctanoate Chemical compound C=1C=C(OC)C=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=CC=C1 PPZBUJURNSUKGW-UHFFFAOYSA-N 0.000 description 1
- IGGJCZWCOLENGD-UHFFFAOYSA-N methyl 8-anilino-7-[(3,5-dimethoxyphenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC(OC)=CC(OC)=C1 IGGJCZWCOLENGD-UHFFFAOYSA-N 0.000 description 1
- RNFUZEBPZQPFHS-UHFFFAOYSA-N methyl 8-anilino-7-[(4-methoxyphenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=C(OC)C=C1 RNFUZEBPZQPFHS-UHFFFAOYSA-N 0.000 description 1
- XODNCVDPRFJDLW-UHFFFAOYSA-N methyl 8-anilino-7-[(4-methylphenyl)methoxy]-8-oxooctanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC1=CC=C(C)C=C1 XODNCVDPRFJDLW-UHFFFAOYSA-N 0.000 description 1
- SONJSYVLGLPOAA-UHFFFAOYSA-N methyl 8-anilino-7-hydroxy-8-oxooctanoate Chemical compound COC(=O)CCCCCC(O)C(=O)NC1=CC=CC=C1 SONJSYVLGLPOAA-UHFFFAOYSA-N 0.000 description 1
- LQWSTMAAIQMLGH-UHFFFAOYSA-N methyl 8-anilino-7-methoxy-8-oxooctanoate Chemical compound COC(=O)CCCCCC(OC)C(=O)NC1=CC=CC=C1 LQWSTMAAIQMLGH-UHFFFAOYSA-N 0.000 description 1
- YWHCKJVIMMXZAJ-UHFFFAOYSA-N methyl 8-anilino-8-oxo-7-[(3-phenoxyphenyl)methoxy]octanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCC(=O)OC)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 YWHCKJVIMMXZAJ-UHFFFAOYSA-N 0.000 description 1
- LVKZFFZWSSWNMK-UHFFFAOYSA-N methyl 9-anilino-8-[(4-methoxyphenyl)methoxy]-9-oxononanoate Chemical compound C=1C=CC=CC=1NC(=O)C(CCCCCCC(=O)OC)OCC1=CC=C(OC)C=C1 LVKZFFZWSSWNMK-UHFFFAOYSA-N 0.000 description 1
- AQPZNQPTSMSNOL-UHFFFAOYSA-N methyl 9-anilino-8-hydroxy-9-oxononanoate Chemical compound COC(=O)CCCCCCC(O)C(=O)NC1=CC=CC=C1 AQPZNQPTSMSNOL-UHFFFAOYSA-N 0.000 description 1
- CPDQGHVRVJFVQA-UHFFFAOYSA-N methyl 9-anilino-8-methoxy-9-oxononanoate Chemical compound COC(=O)CCCCCCC(OC)C(=O)NC1=CC=CC=C1 CPDQGHVRVJFVQA-UHFFFAOYSA-N 0.000 description 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- ARHBOFOEZHVZGQ-UHFFFAOYSA-N n-(1h-indol-3-ylmethoxy)aniline Chemical class C=1NC2=CC=CC=C2C=1CONC1=CC=CC=C1 ARHBOFOEZHVZGQ-UHFFFAOYSA-N 0.000 description 1
- OYKBQNOPCSXWBL-SNAWJCMRSA-N n-hydroxy-3-[(e)-3-(hydroxyamino)-3-oxoprop-1-enyl]benzamide Chemical compound ONC(=O)\C=C\C1=CC=CC(C(=O)NO)=C1 OYKBQNOPCSXWBL-SNAWJCMRSA-N 0.000 description 1
- BYDKWDBDTCCLPK-UHFFFAOYSA-N n-hydroxy-6-[10-(4-methoxyphenyl)-3-oxo-5,11-dioxa-2-azabicyclo[10.4.0]hexadeca-1(16),12,14-trien-4-yl]hexanamide Chemical compound C1=CC(OC)=CC=C1C1OC2=CC=CC=C2NC(=O)C(CCCCCC(=O)NO)OCCCC1 BYDKWDBDTCCLPK-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000010309 neoplastic transformation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004999 nitroaryl group Chemical group 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- 208000000649 small cell carcinoma Diseases 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- HQDRMGGGWLMUBF-NRFANRHFSA-N tert-butyl (4s)-4-(6-methoxy-6-oxohexyl)-3-oxo-12-oxa-2,5-diazabicyclo[11.4.0]heptadeca-1(17),13,15-triene-5-carboxylate Chemical compound N1C(=O)[C@H](CCCCCC(=O)OC)N(C(=O)OC(C)(C)C)CCCCCCOC2=CC=CC=C21 HQDRMGGGWLMUBF-NRFANRHFSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 108010072897 transcription factor Brn-2 Proteins 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 108010060597 trapoxin A Proteins 0.000 description 1
- RTKIYFITIVXBLE-QEQCGCAPSA-N trichostatin A Chemical compound ONC(=O)/C=C/C(/C)=C/[C@@H](C)C(=O)C1=CC=C(N(C)C)C=C1 RTKIYFITIVXBLE-QEQCGCAPSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000000717 tumor promoter Substances 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07104071 | 2007-03-13 | ||
| EP07104071.1 | 2007-03-13 | ||
| PCT/EP2008/052965 WO2008110583A1 (en) | 2007-03-13 | 2008-03-12 | Amide compounds and their use as antitumor agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008225833A1 true AU2008225833A1 (en) | 2008-09-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008225833A Abandoned AU2008225833A1 (en) | 2007-03-13 | 2008-03-12 | Amide compounds and their use as antitumor agents |
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| Country | Link |
|---|---|
| US (1) | US20100113504A1 (enExample) |
| EP (1) | EP2137169A1 (enExample) |
| JP (1) | JP2010520915A (enExample) |
| KR (1) | KR20100014974A (enExample) |
| CN (1) | CN101641341A (enExample) |
| AU (1) | AU2008225833A1 (enExample) |
| BR (1) | BRPI0809000A2 (enExample) |
| CA (1) | CA2677874A1 (enExample) |
| EA (1) | EA200970848A1 (enExample) |
| IL (1) | IL200188A0 (enExample) |
| MX (1) | MX2009009374A (enExample) |
| WO (1) | WO2008110583A1 (enExample) |
| ZA (1) | ZA200907077B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2230227A1 (en) * | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
| JP2013508323A (ja) * | 2009-10-21 | 2013-03-07 | シグマ−タウ・インドゥストリエ・ファルマチェウチケ・リウニテ・ソシエタ・ペル・アチオニ | 合成大環状アミドｈｄａｃ６阻害剤化合物およびそれらの治療剤としての用途 |
| CN109516926B (zh) * | 2018-07-27 | 2021-09-17 | 四川大学 | 一种荜茇明碱衍生物制备及用途 |
| EP3941457A4 (en) * | 2019-03-21 | 2023-04-26 | Merck Sharp & Dohme LLC | HISTONE-DEACETYLASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF HIV INFECTION |
| CN120924186B (zh) * | 2025-10-14 | 2025-12-23 | 长沙市芯星新能源科技有限公司 | 负极粘结剂、锂离子电池负极及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0014254A (pt) * | 1999-09-08 | 2002-08-27 | Sloan Kettering Inst Cancer | Nova classe de agentes de citodiferenciação e inibidores de desacetilase de histona, e métodos de uso dos mesmos |
| US20060264415A1 (en) * | 2005-04-01 | 2006-11-23 | Methylgene Inc. | Inhibitors of histone deacetylase |
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2008
- 2008-03-12 JP JP2009553140A patent/JP2010520915A/ja not_active Withdrawn
- 2008-03-12 AU AU2008225833A patent/AU2008225833A1/en not_active Abandoned
- 2008-03-12 CA CA002677874A patent/CA2677874A1/en not_active Abandoned
- 2008-03-12 US US12/528,912 patent/US20100113504A1/en not_active Abandoned
- 2008-03-12 BR BRPI0809000-9A2A patent/BRPI0809000A2/pt not_active IP Right Cessation
- 2008-03-12 WO PCT/EP2008/052965 patent/WO2008110583A1/en not_active Ceased
- 2008-03-12 CN CN200880008093A patent/CN101641341A/zh active Pending
- 2008-03-12 KR KR1020097018936A patent/KR20100014974A/ko not_active Withdrawn
- 2008-03-12 MX MX2009009374A patent/MX2009009374A/es not_active Application Discontinuation
- 2008-03-12 EA EA200970848A patent/EA200970848A1/ru unknown
- 2008-03-12 EP EP08717710A patent/EP2137169A1/en not_active Withdrawn
-
2009
- 2009-07-30 IL IL200188A patent/IL200188A0/en unknown
- 2009-10-12 ZA ZA200907077A patent/ZA200907077B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200907077B (en) | 2010-07-28 |
| EA200970848A1 (ru) | 2010-02-26 |
| US20100113504A1 (en) | 2010-05-06 |
| EP2137169A1 (en) | 2009-12-30 |
| KR20100014974A (ko) | 2010-02-11 |
| WO2008110583A1 (en) | 2008-09-18 |
| IL200188A0 (en) | 2010-04-15 |
| BRPI0809000A2 (pt) | 2014-11-11 |
| CA2677874A1 (en) | 2008-09-18 |
| MX2009009374A (es) | 2009-09-21 |
| JP2010520915A (ja) | 2010-06-17 |
| CN101641341A (zh) | 2010-02-03 |
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| Date | Code | Title | Description |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |