CA2496386A1 - Sorbicillactone-a derivatives for the treatment of tumour and viral diseases - Google Patents
Sorbicillactone-a derivatives for the treatment of tumour and viral diseases Download PDFInfo
- Publication number
- CA2496386A1 CA2496386A1 CA002496386A CA2496386A CA2496386A1 CA 2496386 A1 CA2496386 A1 CA 2496386A1 CA 002496386 A CA002496386 A CA 002496386A CA 2496386 A CA2496386 A CA 2496386A CA 2496386 A1 CA2496386 A1 CA 2496386A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- treatment
- alkyl
- sorbicillacton
- pharmaceutical composition
- Prior art date
- 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
Links
- 238000011282 treatment Methods 0.000 title claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 23
- 201000010099 disease Diseases 0.000 title claims description 22
- 206010028980 Neoplasm Diseases 0.000 title claims description 18
- 230000003612 virological effect Effects 0.000 title claims description 15
- JACNBJFTXZEQNC-CVHNVBPNSA-N (e)-4-[[(3s,3ar,4z,7as)-5-hydroxy-4-[(2e,4e)-1-hydroxyhexa-2,4-dienylidene]-3,6,7a-trimethyl-2,7-dioxo-3ah-1-benzofuran-3-yl]amino]-4-oxobut-2-enoic acid Chemical class O=C1C(C)=C(O)C(=C(\O)/C=C/C=C/C)/[C@@H]2[C@](C)(NC(=O)\C=C\C(O)=O)C(=O)O[C@@]21C JACNBJFTXZEQNC-CVHNVBPNSA-N 0.000 title abstract 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- WVVJWXDENDJFEC-UHFFFAOYSA-N sorbicillactone A Natural products CC=CC=CC(=C1/C2C(C)(NC(=O)C=CC(=O)O)C(=O)OC2(C)C(=C(C)C1=O)O)O WVVJWXDENDJFEC-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 13
- 241000243142 Porifera Species 0.000 claims description 12
- 206010030113 Oedema Diseases 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 239000002243 precursor Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000002538 fungal effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- RKKPUBAAIGFXOG-YTXTXJHMSA-N Sorbicillin Chemical compound C\C=C\C=C\C(=O)C1=CC(C)=C(O)C(C)=C1O RKKPUBAAIGFXOG-YTXTXJHMSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- SJEYUYPBCPRFNM-UHFFFAOYSA-N sorbicillinol Natural products CC=CC=CC(=O)C1=CC(C)(O)C(=O)C(=C1O)C SJEYUYPBCPRFNM-UHFFFAOYSA-N 0.000 claims description 5
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims 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 claims description 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002028 Biomass Substances 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 230000003592 biomimetic effect Effects 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000008298 dragée Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000349 (Z)-3-carboxyprop-2-enoyl group Chemical group O=C([*])/C([H])=C([H])\C(O[H])=O 0.000 claims description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
- 241000228143 Penicillium Species 0.000 claims description 2
- 241000377427 Sarcotragus fasciculatus Species 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000001212 derivatisation Methods 0.000 claims description 2
- -1 droplets Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- QIQCZROILFZKAT-UHFFFAOYSA-N tetracarbon dioxide Chemical group O=C=C=C=C=O QIQCZROILFZKAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 1
- 241000228150 Penicillium chrysogenum Species 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 230000003450 growing effect Effects 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 6
- 230000000840 anti-viral effect Effects 0.000 abstract description 6
- 238000004113 cell culture Methods 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229930014626 natural product Natural products 0.000 description 11
- 230000000975 bioactive effect Effects 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000014509 gene expression Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 102100034343 Integrase Human genes 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 241000725303 Human immunodeficiency virus Species 0.000 description 5
- 241000700605 Viruses Species 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000013535 sea water Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- 150000002168 ethanoic acid esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 210000004698 lymphocyte Anatomy 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229930000044 secondary metabolite Natural products 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- JSPUCPNQXKTYRO-LWILDLIXSA-N 2-[[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]benzene-1,4-diol Chemical compound C([C@@]1(C)[C@H]2[C@](C(=CCC2)C)(C)CC[C@@H]1C)C1=CC(O)=CC=C1O JSPUCPNQXKTYRO-LWILDLIXSA-N 0.000 description 2
- VPRHEJGLNUDEEH-LWILDLIXSA-N 2-[[(1r,2s,4as,8as)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione Chemical compound C([C@@]1(C)[C@H]2[C@](C(=CCC2)C)(C)CC[C@@H]1C)C1=CC(=O)C=CC1=O VPRHEJGLNUDEEH-LWILDLIXSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HFRPPKGMFYMEJZ-UHFFFAOYSA-N Avarone Natural products CC1CCC2(C)C(=CCCC2(C)C1(C)CC3=CC(=O)C=CC3=O)C HFRPPKGMFYMEJZ-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 101710177291 Gag polyprotein Proteins 0.000 description 2
- 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 2
- 208000031886 HIV Infections Diseases 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 102100037611 Lysophospholipase Human genes 0.000 description 2
- 101710125418 Major capsid protein Proteins 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 108010058864 Phospholipases A2 Proteins 0.000 description 2
- 239000012979 RPMI medium Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241001185310 Symbiotes <prokaryote> Species 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 241000251555 Tunicata Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- TXJPJZWNYUQWCP-UHFFFAOYSA-N avarol Natural products CC1CCC2(C)C(=CCCC2(C)C1(C)Cc3cc(O)ccc3O)C TXJPJZWNYUQWCP-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000001142 circular dichroism spectrum Methods 0.000 description 2
- 238000005100 correlation spectroscopy Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000824 cytostatic agent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004362 fungal culture Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000036515 potency Effects 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 241000212977 Andira Species 0.000 description 1
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 108010062580 Concanavalin A Proteins 0.000 description 1
- 102100031673 Corneodesmosin Human genes 0.000 description 1
- 101710139375 Corneodesmosin Proteins 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 208000008771 Lymphadenopathy Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 229960005363 aluminium oxide Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 description 1
- 101150035354 araA gene Proteins 0.000 description 1
- 230000003816 axenic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011281 clinical therapy Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000010262 high-speed countercurrent chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 238000004460 liquid liquid chromatography Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 208000018555 lymphatic system disease Diseases 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JTJJJLSLKZFEPJ-ZAYCRUKZSA-N meleagrin Chemical compound C([C@]1(C2=CC=CC=C2N([C@@]21NC1=O)OC)C(C)(C)C=C)=C(O)C(=O)N2\C1=C\C1=CNC=N1 JTJJJLSLKZFEPJ-ZAYCRUKZSA-N 0.000 description 1
- JTJJJLSLKZFEPJ-GOTSBHOMSA-N meleagrin Natural products CON1c2ccccc2[C@@]3(C=C(O)C(=O)N4C(=Cc5c[nH]cn5)C(=O)N[C@@]134)C(C)(C)C=C JTJJJLSLKZFEPJ-GOTSBHOMSA-N 0.000 description 1
- 108010064507 meleagrin Proteins 0.000 description 1
- JTJJJLSLKZFEPJ-DHIUTWEWSA-N meleagrine Natural products CON1c2ccccc2[C@]3(C=C(O)C(=O)N4C(=Cc5c[nH]cn5)C(=O)N[C@]134)C(C)(C)C=C JTJJJLSLKZFEPJ-DHIUTWEWSA-N 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- SPWSUFUPTSJWNG-UHFFFAOYSA-N roquefortine C Natural products C=1C=CC=C2C=1NC1C2(C(C)(C=C)C)CC(C(N2)=O)N1C(=O)C2=CC1=CN=CN1 SPWSUFUPTSJWNG-UHFFFAOYSA-N 0.000 description 1
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 1
- 239000007289 sea water agar Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 230000031068 symbiosis, encompassing mutualism through parasitism Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10238257.3 | 2002-08-21 | ||
| DE10238257A DE10238257B4 (de) | 2002-08-21 | 2002-08-21 | Sorbicillacton A und Sorbicillacton-A-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| PCT/EP2003/007805 WO2004026854A1 (de) | 2002-08-21 | 2003-07-17 | Sorbicillacton-a-derivate zur behandlung von tumor- und viruserkrankungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2496386A1 true CA2496386A1 (en) | 2004-04-01 |
Family
ID=31501834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002496386A Abandoned CA2496386A1 (en) | 2002-08-21 | 2003-07-17 | Sorbicillactone-a derivatives for the treatment of tumour and viral diseases |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060111420A1 (enExample) |
| EP (1) | EP1532129B1 (enExample) |
| JP (1) | JP2006503049A (enExample) |
| AT (1) | ATE346057T1 (enExample) |
| AU (1) | AU2003250985A1 (enExample) |
| CA (1) | CA2496386A1 (enExample) |
| DE (2) | DE10238257B4 (enExample) |
| WO (1) | WO2004026854A1 (enExample) |
| ZA (1) | ZA200502226B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004004901B4 (de) * | 2004-01-30 | 2006-01-05 | Johannes-Gutenberg-Universität Mainz | Verfahren zur Herstellung von Sorbicillacton A |
| DE102004005106A1 (de) * | 2004-02-02 | 2005-08-18 | Johannes-Gutenberg-Universität Mainz | Sorbifuranone, Sorbivineton, Sorbivinetol und Derivate dieser Verbindungen, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung |
| KR102438137B1 (ko) | 2015-12-02 | 2022-08-30 | 에스케이이노베이션 주식회사 | 내열성 및 셧다운 특성이 우수한 이차전지용 분리막 |
| CN110037054B (zh) * | 2019-04-16 | 2021-04-20 | 云南大学 | 一种提高烟草抗病性的水溶性多肽诱导剂及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2252537A1 (en) * | 1996-05-20 | 1997-11-27 | Darwin Discovery Limited | Benzofuran carboxamides and their therapeutic use |
| WO2002026726A2 (en) * | 2000-09-26 | 2002-04-04 | The Johns Hopkins University | Antiviral compositions and methods of use |
-
2002
- 2002-08-21 DE DE10238257A patent/DE10238257B4/de not_active Expired - Fee Related
-
2003
- 2003-07-17 AU AU2003250985A patent/AU2003250985A1/en not_active Abandoned
- 2003-07-17 US US10/525,685 patent/US20060111420A1/en not_active Abandoned
- 2003-07-17 JP JP2004536901A patent/JP2006503049A/ja not_active Withdrawn
- 2003-07-17 AT AT03797201T patent/ATE346057T1/de not_active IP Right Cessation
- 2003-07-17 WO PCT/EP2003/007805 patent/WO2004026854A1/de not_active Ceased
- 2003-07-17 CA CA002496386A patent/CA2496386A1/en not_active Abandoned
- 2003-07-17 DE DE50305776T patent/DE50305776D1/de not_active Expired - Fee Related
- 2003-07-17 EP EP03797201A patent/EP1532129B1/de not_active Expired - Lifetime
-
2005
- 2005-03-16 ZA ZA200502226A patent/ZA200502226B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004026854A1 (de) | 2004-04-01 |
| DE10238257B4 (de) | 2007-04-19 |
| US20060111420A1 (en) | 2006-05-25 |
| ATE346057T1 (de) | 2006-12-15 |
| AU2003250985A1 (en) | 2004-04-08 |
| EP1532129B1 (de) | 2006-11-22 |
| ZA200502226B (en) | 2006-02-22 |
| DE10238257A1 (de) | 2004-03-11 |
| JP2006503049A (ja) | 2006-01-26 |
| EP1532129A1 (de) | 2005-05-25 |
| DE50305776D1 (de) | 2007-01-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Lin et al. | Polyketides from Penicillium sp. JP-1, an endophytic fungus associated with the mangrove plant Aegiceras corniculatum | |
| Schaffner-Sabba et al. | . beta.-Lapachone: synthesis of derivatives and activities in tumor models | |
| Kusano et al. | Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum | |
| CN113730391A (zh) | 桃金娘酮类化合物在制备抗新型冠状病毒SARS-CoV-2药物中的应用 | |
| Gupta et al. | Synthesis and Investigation of antidiabetic response of new coumarin derivatives against streptozotocin induced diabetes in experimental rats | |
| Qi et al. | Structurally various p-terphenyls with neuraminidase inhibitory from a sponge derived fungus Aspergillus sp. SCSIO41315 | |
| Uzor et al. | Anti-respiratory syncytial virus compounds from two endophytic fungi isolated from Nigerian medicinal plants | |
| Chen et al. | A new 9-nor-atractylodin from Atractylodes lancea and the antibacterial activity of the atractylodin derivatives | |
| CA2496386A1 (en) | Sorbicillactone-a derivatives for the treatment of tumour and viral diseases | |
| Lorenz et al. | An amide of l-threo-γ-hydroxyglutamic acid from Justicia ghiesbreghtiana | |
| CN114890882B (zh) | 柏木醇衍生物、其制备方法及其应用 | |
| CN100386316C (zh) | 来自牛樟芝菌丝体的化合物和混合物或组合物及其用途 | |
| CN113735814B (zh) | 桃金娘酮类化合物及其在制备抗流感病毒药物中的应用 | |
| CN113845559A (zh) | 一种雷公藤甲素衍生物及其制备方法和应用 | |
| TWI488969B (zh) | 牛蒡子苷進行生物轉化製備牛蒡子苷元二聚體的方法 | |
| JPH10504533A (ja) | バイオアクティブ アセトゲニン及び誘導体 | |
| US10639303B2 (en) | Alkaloids and their preparation and application as anti-HSV-1 agents | |
| CN102702221B (zh) | Xyloketal B 类似物及其制备方法和应用 | |
| US5091412A (en) | Novel antiviral terpene hydroquinones and methods of use | |
| US6872747B2 (en) | Decalactones, method for making, and pharmaceuticals there from | |
| US5204367A (en) | Novel antiviral and anti-leukemia terpene hydroquinones and methods of use | |
| CN111217824B (zh) | 4-o-芳氨丙基土甘草a衍生物及其制备及应用 | |
| CN116077508B (zh) | 齐墩果烷型三萜衍生物在制备心血管疾病药物中的应用 | |
| US5051519A (en) | Novel antiviral and antitumor terpene hydroquinones and methods of use | |
| JP2004534756A (ja) | 海綿共生カビ由来の新規デカラクトン類および医薬品としてのそれらの合成誘導体類 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |