CA2273436A1 - Basiliskamides antifongiques et antimycobacteriens - Google Patents

Basiliskamides antifongiques et antimycobacteriens Download PDF

Info

Publication number: CA2273436A1
Authority: CA; Canada
Prior art keywords: compound; branched; optionally substituted; saturated; linear
Prior art date: 1999-06-01
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

CA 2273436

Other languages

English (en)

Inventor

Michael Thomas Kelly

Raymond J. Andersen

Todd A. Barsby

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.)

University of British Columbia

Ocean Pharmaceuticals Inc

Original Assignee

Individual

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.)

1999-06-01

Filing date

1999-06-01

Publication date

2000-12-01

1999-06-01 Application filed by Individual filed Critical Individual

1999-06-01 Priority to CA 2273436 priority Critical patent/CA2273436A1/fr

2000-12-01 Publication of CA2273436A1 publication Critical patent/CA2273436A1/fr

Status Abandoned legal-status Critical Current

Links

229940121375 antifungal agent Drugs 0.000 title claims description 8
239000003926 antimycobacterial agent Substances 0.000 title claims description 5
229930194896 basiliskamide Natural products 0.000 title description 26
230000000843 anti-fungal effect Effects 0.000 title description 11
230000001355 anti-mycobacterial effect Effects 0.000 title description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 19
229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
229910052799 carbon Inorganic materials 0.000 claims abstract description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004122 cyclic group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 8
239000012634 fragment Substances 0.000 claims abstract description 7
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
239000005864 Sulphur Substances 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
125000002619 bicyclic group Chemical group 0.000 claims abstract description 5
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
125000002950 monocyclic group Chemical group 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
150000002118 epoxides Chemical class 0.000 claims abstract description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
229910006069 SO3H Inorganic materials 0.000 claims abstract 6
150000001875 compounds Chemical class 0.000 claims description 56
QAHZDGAHECEVRM-HXKCHMFGSA-N [(3r,4s,5r,6r,8e,10z)-12-amino-6-hydroxy-3,5-dimethyl-12-oxododeca-8,10-dien-4-yl] (e)-3-phenylprop-2-enoate Chemical compound NC(=O)\C=C/C=C/C[C@@H](O)[C@@H](C)[C@H]([C@H](C)CC)OC(=O)\C=C\C1=CC=CC=C1 QAHZDGAHECEVRM-HXKCHMFGSA-N 0.000 claims description 45
QAHZDGAHECEVRM-UHFFFAOYSA-N basiliskamide A Natural products NC(=O)C=CC=CCC(O)C(C)C(C(C)CC)OC(=O)C=CC1=CC=CC=C1 QAHZDGAHECEVRM-UHFFFAOYSA-N 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 22
HCZNVGHFFHRIFM-HXKCHMFGSA-N [(3r,4s,5s,6r,8e,10z)-12-amino-4-hydroxy-3,5-dimethyl-12-oxododeca-8,10-dien-6-yl] (e)-3-phenylprop-2-enoate Chemical compound NC(=O)\C=C/C=C/C[C@H]([C@@H](C)[C@@H](O)[C@H](C)CC)OC(=O)\C=C\C1=CC=CC=C1 HCZNVGHFFHRIFM-HXKCHMFGSA-N 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
HCZNVGHFFHRIFM-UHFFFAOYSA-N basiliskamide B Natural products NC(=O)C=CC=CCC(C(C)C(O)C(C)CC)OC(=O)C=CC1=CC=CC=C1 HCZNVGHFFHRIFM-UHFFFAOYSA-N 0.000 claims description 17
239000008194 pharmaceutical composition Substances 0.000 claims description 8
230000001413 cellular effect Effects 0.000 claims description 7
239000000356 contaminant Substances 0.000 claims description 6
239000003429 antifungal agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
229940034014 antimycobacterial agent Drugs 0.000 claims description 2
-1 polyketide compounds Chemical class 0.000 abstract description 12
230000003115 biocidal effect Effects 0.000 abstract description 7
229930001119 polyketide Natural products 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 9
230000000694 effects Effects 0.000 description 9
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
241000222122 Candida albicans Species 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
229940095731 candida albicans Drugs 0.000 description 8
APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 7
APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 7
229960003942 amphotericin b Drugs 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000003919 heteronuclear multiple bond coherence Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
241001225321 Aspergillus fumigatus Species 0.000 description 5
240000004808 Saccharomyces cerevisiae Species 0.000 description 5
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 5
238000002000 high resolution fast-atom bombardment mass spectrometry Methods 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229960000549 4-dimethylaminophenol Drugs 0.000 description 4
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
229940091771 aspergillus fumigatus Drugs 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
238000005100 correlation spectroscopy Methods 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000006257 total synthesis reaction Methods 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241001529734 Ocimum Species 0.000 description 3
235000010676 Ocimum basilicum Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241000223229 Trichophyton rubrum Species 0.000 description 3
239000008272 agar Substances 0.000 description 3
238000002814 agar dilution Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
210000002950 fibroblast Anatomy 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
150000003140 primary amides Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000004007 reversed phase HPLC Methods 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
201000008827 tuberculosis Diseases 0.000 description 3
241000556533 uncultured marine bacterium Species 0.000 description 3
JJYKJUXBWFATTE-SECBINFHSA-N (2r)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid Chemical compound CO[C@](C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-SECBINFHSA-N 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
241000193830 Bacillus <bacterium> Species 0.000 description 2
241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 2
241000222120 Candida <Saccharomycetales> Species 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 description 2
206010062207 Mycobacterial infection Diseases 0.000 description 2
241000187479 Mycobacterium tuberculosis Species 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002815 broth microdilution Methods 0.000 description 2
231100000135 cytotoxicity Toxicity 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000006196 drop Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000401 methanolic extract Substances 0.000 description 2
208000027531 mycobacterial infectious disease Diseases 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
244000052769 pathogen Species 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
239000003643 water by type Substances 0.000 description 2
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
244000189799 Asimina triloba Species 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
241000545499 Mycobacterium avium-intracellulare Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000237908 Riftia pachyptila Species 0.000 description 1
241000235070 Saccharomyces Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
YSZMNDWBGVOMRK-UHFFFAOYSA-N [C+3]C.CC([CH2-])=O.CC([CH2-])=O.CC([CH2-])=O Chemical compound [C+3]C.CC([CH2-])=O.CC([CH2-])=O.CC([CH2-])=O YSZMNDWBGVOMRK-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
238000002827 antifungal susceptibility testing Methods 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
238000010260 bioassay-guided fractionation Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000006143 cell culture medium Substances 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000000287 crude extract Substances 0.000 description 1
230000000120 cytopathologic effect Effects 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
244000052637 human pathogen Species 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
231100001083 no cytotoxicity Toxicity 0.000 description 1
238000012587 nuclear overhauser effect experiment Methods 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000007430 reference method Methods 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002356 single layer Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000004793 spatially offset Raman spectroscopy Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000006150 trypticase soy agar Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA 2273436 1999-06-01 1999-06-01 Basiliskamides antifongiques et antimycobacteriens Abandoned CA2273436A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2273436 CA2273436A1 (fr)	1999-06-01	1999-06-01	Basiliskamides antifongiques et antimycobacteriens

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2273436 CA2273436A1 (fr)	1999-06-01	1999-06-01	Basiliskamides antifongiques et antimycobacteriens

Publications (1)

Publication Number	Publication Date
CA2273436A1 true CA2273436A1 (fr)	2000-12-01

Family

ID=30774248

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2273436 Abandoned CA2273436A1 (fr)	1999-06-01	1999-06-01	Basiliskamides antifongiques et antimycobacteriens

Country Status (1)

Country	Link
CA (1)	CA2273436A1 (fr)

1999
- 1999-06-01 CA CA 2273436 patent/CA2273436A1/fr not_active Abandoned

Publication	Publication Date	Title
EP0749432B1 (fr)	2001-05-09	Composes du 9-desoxotaxane
US5589470A (en)	1996-12-31	Reducing tetracycline resistance in living cells
US7732429B2 (en)	2010-06-08	Reducing tetracycline resistance in living cells
EP1471052B1 (fr)	2011-08-10	Composes de geranyle
IE46883B1 (en)	1983-10-19	Cyclosporin derivatives
CH624124A5 (fr)	1981-07-15
Naglah et al.	2017	Synthesis, characterization and in vitro antimicrobial investigation of novel amino acids and dipeptides based on dibenzofuran-2-sulfonyl-chloride
EP0870761B1 (fr)	2004-02-25	Dérivés de thiocolchicine ayant une activité antiinfammatoire et relaxante des muscles
CN113024404B (zh)	2024-05-24	季胺盐型和厚朴酚/厚朴酚类衍生物及其制备方法和应用
JP2010505777A (ja)	2010-02-25	アクチノマデュラ・ナミビエンシス由来の抗菌性・抗ウイルス性ペプチド
FR2475040A1 (fr)	1981-08-07
CA2273436A1 (fr)	2000-12-01	Basiliskamides antifongiques et antimycobacteriens
EP0687673A1 (fr)	1995-12-20	Dérivés d'oxazole comme agents anti-tumoraux
JPH0631301B2 (ja)	1994-04-27	抗細菌性９−デオキソ―９ａ―アリルおよびプロパルギル―９ａ―アザ―９ａ―ホモエリスロマイシンＡ誘導体
FR2523583A1 (fr)	1983-09-23	Procede de production de 6'-alkylspectinomycines et de leurs analogues et nouveaux composes intermediaires utilises dans ce procede
FR2605321A1 (fr)	1988-04-22	Anthracycline glycosides a activite antitumorale, leur preparation, les composes intermediaires de cette preparation et compositions et utilisation de ces substances.
US20050277779A1 (en)	2005-12-15	Antifungal and antimycobacterial basiliskamides
EP1353926B1 (fr)	2006-03-08	Derives de mikanolide, leur preparation et leurs applications therapeutiques
US5925369A (en)	1999-07-20	Bis alkanoyl esters of carnitine having bactericidal, fungicidal and antiprotozoal activity
FR2646081A1 (fr)	1990-10-26
EP0315519B1 (fr)	1993-03-24	Nouveaux dérivés de l'acide aminopimélique, leur procédé de préparation et leur application comme médicaments
FR2465746A1 (fr)	1981-03-27	1-epi-2-desoxyfortimicine b et ses derives utiles notamment comme antibiotiques
NZ211376A (en)	1991-05-28	Compounds, methods and compositions for the treating of protozoal infections wherein the compounds are produced from actinomadura madurae subspecies simaoensis or mutant thereof
US20240317800A1 (en)	2024-09-26	Novel compounds and antibacterial composition comprising the same
FR2468582A1 (fr)	1981-05-08	Antibiotiques de type macrolide, leur procede de preparation et compositions therapeutiques les contenant

Legal Events

Date	Code	Title	Description
2004-05-31	EEER	Examination request
2007-06-01	FZDE	Dead