AU2001270183A1 - Novel compounds possessing antibacterial, antifungal or antitumor activity - Google Patents

Novel compounds possessing antibacterial, antifungal or antitumor activity

Info

Publication number: AU2001270183A1
Authority: AU; Australia
Prior art keywords: alkyl; hydrogen; compound; substituted; indole
Prior art date: 2000-06-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

AU2001270183A

Other languages

English (en)

Inventor

Janos Botyanszki

Natalia B. Dyatkina

Alexander Khorlin

Sebastian Johannes R. Liehr

Joseph Martin Muchowski

Peter Harold Nelson

Christopher Don Roberts

Dong-Fang Shi

Mark Douglas Velligan

Wentao Zhang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Genelabs Technologies Inc

Original Assignee

Genelabs Technologies Inc

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.)

2000-06-27

Filing date

2001-06-26

Publication date

2002-01-08

2001-06-26 Application filed by Genelabs Technologies Inc filed Critical Genelabs Technologies Inc

2002-01-08 Publication of AU2001270183A1 publication Critical patent/AU2001270183A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 350
230000000843 anti-fungal effect Effects 0.000 title description 12
230000000844 anti-bacterial effect Effects 0.000 title description 11
230000000259 anti-tumor effect Effects 0.000 title description 8
229940121375 antifungal agent Drugs 0.000 title description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 132
239000001257 hydrogen Substances 0.000 claims description 128
125000000217 alkyl group Chemical group 0.000 claims description 107
238000000034 method Methods 0.000 claims description 90
125000001072 heteroaryl group Chemical group 0.000 claims description 85
150000002431 hydrogen Chemical group 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
125000000547 substituted alkyl group Chemical group 0.000 claims description 44
125000000623 heterocyclic group Chemical group 0.000 claims description 43
125000003107 substituted aryl group Chemical group 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
125000004429 atom Chemical group 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000002252 acyl group Chemical group 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 14
230000002401 inhibitory effect Effects 0.000 claims description 10
101710183280 Topoisomerase Proteins 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
230000001580 bacterial effect Effects 0.000 claims description 8
208000035143 Bacterial infection Diseases 0.000 claims description 5
206010017533 Fungal infection Diseases 0.000 claims description 5
208000031888 Mycoses Diseases 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
208000022362 bacterial infectious disease Diseases 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
230000002538 fungal effect Effects 0.000 claims description 4
241000222122 Candida albicans Species 0.000 claims description 3
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000003275 alpha amino acid group Chemical group 0.000 claims 3
241000758250 Aspergillus fumigatus A1163 Species 0.000 claims 1
240000001817 Cereus hexagonus Species 0.000 claims 1
241000606768 Haemophilus influenzae Species 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 222
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 206
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 189
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 157
230000015572 biosynthetic process Effects 0.000 description 154
238000003786 synthesis reaction Methods 0.000 description 150
239000000243 solution Substances 0.000 description 120
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
-1 cyclobutanyl Chemical group 0.000 description 104
239000000203 mixture Substances 0.000 description 98
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 95
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 79
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 79
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 72
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
239000011347 resin Substances 0.000 description 60
229920005989 resin Polymers 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
238000006243 chemical reaction Methods 0.000 description 58
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 57
229910000041 hydrogen chloride Inorganic materials 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
239000000047 product Substances 0.000 description 51
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
238000005481 NMR spectroscopy Methods 0.000 description 40
239000000725 suspension Substances 0.000 description 40
150000001412 amines Chemical class 0.000 description 38
238000004128 high performance liquid chromatography Methods 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 33
108020004414 DNA Proteins 0.000 description 31
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 29
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 29
239000002244 precipitate Substances 0.000 description 28
239000007787 solid Substances 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 25
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 25
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 24
239000000706 filtrate Substances 0.000 description 24
230000002829 reductive effect Effects 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
229960004132 diethyl ether Drugs 0.000 description 21
238000005984 hydrogenation reaction Methods 0.000 description 21
230000027455 binding Effects 0.000 description 20
239000012043 crude product Substances 0.000 description 20
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 20
238000005160 1H NMR spectroscopy Methods 0.000 description 19
MUABQYJAPOQWCH-UHFFFAOYSA-N 1h-indole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2NC(C(=O)O)=CC2=C1 MUABQYJAPOQWCH-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
235000019439 ethyl acetate Nutrition 0.000 description 18
238000000746 purification Methods 0.000 description 18
125000003710 aryl alkyl group Chemical group 0.000 description 17
201000010099 disease Diseases 0.000 description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
239000007789 gas Substances 0.000 description 15
239000000546 pharmaceutical excipient Substances 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 15
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
125000006239 protecting group Chemical group 0.000 description 13
238000005406 washing Methods 0.000 description 13
AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
125000004475 heteroaralkyl group Chemical group 0.000 description 12
IDBIFFKSXLYUOT-UHFFFAOYSA-N netropsin Chemical compound C1=C(C(=O)NCCC(N)=N)N(C)C=C1NC(=O)C1=CC(NC(=O)CN=C(N)N)=CN1C IDBIFFKSXLYUOT-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
BNUJDWUUWSJSLZ-UHFFFAOYSA-N Cl.CC(C)CCN1C=C([N+]([O-])=O)C=C1C(=O)NCCCC(N)=N Chemical compound Cl.CC(C)CCN1C=C([N+]([O-])=O)C=C1C(=O)NCCCC(N)=N BNUJDWUUWSJSLZ-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
229940093499 ethyl acetate Drugs 0.000 description 11
239000008194 pharmaceutical composition Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
239000013078 crystal Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 10
150000003840 hydrochlorides Chemical class 0.000 description 10
239000000463 material Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
102000053602 DNA Human genes 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 9
229960001701 chloroform Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000003446 ligand Substances 0.000 description 9
125000005647 linker group Chemical group 0.000 description 9
JLUIOEOHOOLSJC-UHFFFAOYSA-N pyrrole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N1 JLUIOEOHOOLSJC-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
SBEWTFPSDHKYRA-UHFFFAOYSA-N 4-amino-n-(4-amino-4-iminobutyl)-1-(3-methylbutyl)pyrrole-2-carboxamide Chemical compound CC(C)CCN1C=C(N)C=C1C(=O)NCCCC(N)=N SBEWTFPSDHKYRA-UHFFFAOYSA-N 0.000 description 8
125000004442 acylamino group Chemical group 0.000 description 8
YPPKTPHBWNZWML-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) 1h-pyrrole-2,5-dicarboxylate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)C1=CC=C(C(=O)OC=2C(=C(F)C(F)=C(F)C=2F)F)N1 YPPKTPHBWNZWML-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
230000012010 growth Effects 0.000 description 8
239000004615 ingredient Substances 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
DQQPXUZTRJJRCT-UHFFFAOYSA-N 4-amino-n-(6-amino-6-iminohexyl)-1-(3-methylbutyl)pyrrole-2-carboxamide Chemical compound CC(C)CCN1C=C(N)C=C1C(=O)NCCCCCC(N)=N DQQPXUZTRJJRCT-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 7
150000001409 amidines Chemical class 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 7
238000003556 assay Methods 0.000 description 7
125000001188 haloalkyl group Chemical group 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
239000007788 liquid Substances 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
MUEOQEUSJMFYHV-UHFFFAOYSA-N 4-amino-1-methylpyrrole-2-carboxylic acid Chemical group CN1C=C(N)C=C1C(O)=O MUEOQEUSJMFYHV-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
108010016626 Dipeptides Proteins 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
QIALEJYXTQNNIV-UHFFFAOYSA-N NCCCCCC(N)=N.Cl Chemical compound NCCCCCC(N)=N.Cl QIALEJYXTQNNIV-UHFFFAOYSA-N 0.000 description 6
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240000004808 Saccharomyces cerevisiae Species 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
DVFJMQCNICEPAI-UHFFFAOYSA-N ethyl 5-nitro-1h-indole-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2NC(C(=O)OCC)=CC2=C1 DVFJMQCNICEPAI-UHFFFAOYSA-N 0.000 description 6
239000002054 inoculum Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
230000004048 modification Effects 0.000 description 6
238000012986 modification Methods 0.000 description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
125000006413 ring segment Chemical group 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
125000006296 sulfonyl amino group Chemical class [H]N(*)S(*)(=O)=O 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002178 crystalline material Substances 0.000 description 5
125000005343 heterocyclic alkyl group Chemical group 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
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239000012044 organic layer Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
230000001376 precipitating effect Effects 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
125000005017 substituted alkenyl group Chemical group 0.000 description 5
125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 5
YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 description 5
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
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LHFOJSCXLFKDIR-UHFFFAOYSA-N 5-nitro-1h-indole-2-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2NC(C(=O)O)=CC2=C1 LHFOJSCXLFKDIR-UHFFFAOYSA-N 0.000 description 4
OKSGPUBQGGPKNH-UHFFFAOYSA-N 5-nitro-n-[2-(propylamino)ethyl]-1h-indole-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=C2NC(C(=O)NCCNCCC)=CC2=C1 OKSGPUBQGGPKNH-UHFFFAOYSA-N 0.000 description 4
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 description 4
241000894006 Bacteria Species 0.000 description 4
230000004568 DNA-binding Effects 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
108010042309 Netropsin Proteins 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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229940107700 pyruvic acid Drugs 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002824 redox indicator Substances 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
235000020183 skimmed milk Nutrition 0.000 description 1
239000007974 sodium acetate buffer Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

AU2001270183A 2000-06-27 2001-06-26 Novel compounds possessing antibacterial, antifungal or antitumor activity Abandoned AU2001270183A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US21447800P	2000-06-27	2000-06-27
US60/214,478		2000-06-27
PCT/US2001/020334 WO2002000650A2 (fr)	2000-06-27	2001-06-26	Nouveaux composes possedant une activite anti-bacterienne, antifongique et anti-tumeur

Publications (1)

Publication Number	Publication Date
AU2001270183A1 true AU2001270183A1 (en)	2002-01-08

Family

ID=22799223

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001270183A Abandoned AU2001270183A1 (en)	2000-06-27	2001-06-26	Novel compounds possessing antibacterial, antifungal or antitumor activity

Country Status (15)

Country	Link
US (2)	US6849713B2 (fr)
EP (1)	EP1294713A2 (fr)
JP (1)	JP2004501915A (fr)
KR (1)	KR20030011371A (fr)
CN (1)	CN1439006A (fr)
AU (1)	AU2001270183A1 (fr)
BR (1)	BR0112030A (fr)
CA (1)	CA2414512A1 (fr)
IL (1)	IL153119A0 (fr)
MX (1)	MXPA02012271A (fr)
NO (1)	NO20025720L (fr)
NZ (1)	NZ522839A (fr)
RU (1)	RU2003101969A (fr)
WO (1)	WO2002000650A2 (fr)
ZA (1)	ZA200209774B (fr)

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2001
- 2001-06-26 EP EP01948740A patent/EP1294713A2/fr not_active Withdrawn
- 2001-06-26 IL IL15311901A patent/IL153119A0/xx unknown
- 2001-06-26 WO PCT/US2001/020334 patent/WO2002000650A2/fr not_active Ceased
- 2001-06-26 CN CN01811885A patent/CN1439006A/zh active Pending
- 2001-06-26 MX MXPA02012271A patent/MXPA02012271A/es unknown
- 2001-06-26 RU RU2003101969/04A patent/RU2003101969A/ru not_active Application Discontinuation
- 2001-06-26 CA CA002414512A patent/CA2414512A1/fr not_active Abandoned
- 2001-06-26 NZ NZ522839A patent/NZ522839A/en unknown
- 2001-06-26 JP JP2002505774A patent/JP2004501915A/ja not_active Withdrawn
- 2001-06-26 AU AU2001270183A patent/AU2001270183A1/en not_active Abandoned
- 2001-06-26 US US09/892,327 patent/US6849713B2/en not_active Expired - Fee Related
- 2001-06-26 BR BR0112030-1A patent/BR0112030A/pt not_active IP Right Cessation
- 2001-06-26 KR KR1020027017685A patent/KR20030011371A/ko not_active Withdrawn
2002
- 2002-10-23 US US10/277,666 patent/US6906103B2/en not_active Expired - Fee Related
- 2002-11-28 NO NO20025720A patent/NO20025720L/no not_active Application Discontinuation
- 2002-12-02 ZA ZA200209774A patent/ZA200209774B/en unknown

Also Published As

Publication number	Publication date
NO20025720L (no)	2003-02-26
BR0112030A (pt)	2003-04-29
ZA200209774B (en)	2004-03-02
WO2002000650A2 (fr)	2002-01-03
RU2003101969A (ru)	2004-07-10
US20020037856A1 (en)	2002-03-28
WO2002000650A9 (fr)	2003-03-06
CA2414512A1 (fr)	2002-01-03
NO20025720D0 (no)	2002-11-28
CN1439006A (zh)	2003-08-27
US20030119749A1 (en)	2003-06-26
KR20030011371A (ko)	2003-02-07
WO2002000650A3 (fr)	2002-10-24
JP2004501915A (ja)	2004-01-22
NZ522839A (en)	2004-11-26
EP1294713A2 (fr)	2003-03-26
MXPA02012271A (es)	2004-09-06
US6906103B2 (en)	2005-06-14
IL153119A0 (en)	2003-06-24
US6849713B2 (en)	2005-02-01

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