CH669379A5 - - Google Patents
Download PDFInfo
- Publication number
- CH669379A5 CH669379A5 CH3957/84A CH395784A CH669379A5 CH 669379 A5 CH669379 A5 CH 669379A5 CH 3957/84 A CH3957/84 A CH 3957/84A CH 395784 A CH395784 A CH 395784A CH 669379 A5 CH669379 A5 CH 669379A5
- Authority
- CH
- Switzerland
- Prior art keywords
- fredericamycin
- max
- connection
- nmr
- formula
- Prior art date
Links
- NJLAGDPRCAPJIF-MHSJTTIKSA-N (8S)-1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone Chemical class COc1cc(=O)c2c(c1=O)c(=O)c1=C(O)[C@]3(CCc4cc5cc(\C=C\C=C\C)[nH]c(=O)c5c(O)c34)C(O)=c1c2=O NJLAGDPRCAPJIF-MHSJTTIKSA-N 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- BZONSJUONOFNNP-UHFFFAOYSA-N ent-fredericamycin A Natural products C1=C(C=CC=CC)NC(=O)C(C(O)=C23)=C1C=C3CCC21C(=O)C(C(O)=C2C(=O)C=C(C(C2=C2O)=O)OC)=C2C1=O BZONSJUONOFNNP-UHFFFAOYSA-N 0.000 description 28
- 239000013078 crystal Substances 0.000 description 25
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 101150041968 CDC13 gene Proteins 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 244000005700 microbiome Species 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NJLAGDPRCAPJIF-VNKDHWASSA-N 1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone Chemical class COc1cc(=O)c2c(c1=O)c(=O)c1=C(O)C3(CCc4cc5cc(\C=C\C=C\C)[nH]c(=O)c5c(O)c34)C(O)=c1c2=O NJLAGDPRCAPJIF-VNKDHWASSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 201000009030 Carcinoma Diseases 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229930188640 fredericamycin Natural products 0.000 description 4
- 238000009630 liquid culture Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000008342 Leukemia P388 Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000191938 Micrococcus luteus Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- XIRRDAWDNHRRLB-UHFFFAOYSA-N 2,6-dibromoaniline Chemical compound NC1=C(Br)C=CC=C1Br XIRRDAWDNHRRLB-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 241000235035 Debaryomyces Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000221778 Fusarium fujikuroi 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
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- 241000893976 Nannizzia gypsea Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- -1 Rr COOH Chemical class 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 240000000452 Sesamum alatum Species 0.000 description 1
- 235000009367 Sesamum alatum Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 241000624602 Shigella flexneri 2b Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000751182 Staphylococcus epidermidis ATCC 12228 Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000187392 Streptomyces griseus Species 0.000 description 1
- 241000187180 Streptomyces sp. Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003972 antineoplastic antibiotic Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229960001170 rokitamycin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15052283A JPS6042368A (ja) | 1983-08-18 | 1983-08-18 | フレデリカマイシンａ−ジアシル誘導体 |
| JP16548983A JPS6056960A (ja) | 1983-09-08 | 1983-09-08 | ロイコテトラアシルテトラハイドロフレデリカマイシンａ |
| JP16608283A JPS6058964A (ja) | 1983-09-09 | 1983-09-09 | 新規なフレデリカマイシンａ誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH669379A5 true CH669379A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-03-15 |
Family
ID=27319939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3957/84A CH669379A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-08-18 | 1984-08-17 |
Country Status (7)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4673678A (en) * | 1986-07-25 | 1987-06-16 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble derivatives of fredericamycin A |
| US5166208A (en) * | 1991-10-09 | 1992-11-24 | Boston College | Fredericamycin A derivatives |
| US6462173B1 (en) * | 1997-09-08 | 2002-10-08 | Max-Planck-Gesellschaft Zur Forderung Der | Inhibitors of phosphoserine and phosphothreonine-proline-specific isomerases |
| US6495376B1 (en) * | 1999-02-18 | 2002-12-17 | Beth Israel Deaconess Medical Center | Methods and compositions for regulating protein-protein interactions |
| EP1363620A2 (en) * | 2000-12-22 | 2003-11-26 | Pintex Pharmaceuticals, Inc. | Use of fredericamycin and its derivatives in the treatment of pin1-associated states |
| DE10248451A1 (de) | 2002-03-26 | 2003-10-09 | Bioleads Gmbh | Fredericamycin-Derivate |
| US8247424B2 (en) * | 2002-03-26 | 2012-08-21 | Zentopharm Gmbh | Fredericamycin derivatives |
| DE10217046A1 (de) * | 2002-04-17 | 2003-11-06 | Bioleads Gmbh | Fredericamycin-Derivate |
| AU2003258982A1 (en) * | 2002-06-28 | 2004-01-19 | Pintex Pharmaceuticals, Inc. | Methods of inhibiting pin1-associated states using a fredericamycin a compound |
| DE10230917A1 (de) * | 2002-07-09 | 2004-02-05 | Bioleads Gmbh | Fredericamycin-Derivate |
| US20040176277A1 (en) * | 2003-03-03 | 2004-09-09 | Pintex Pharmaceuticals, Inc. | Methods of treating Pin1 associated disorders |
| EP2338056B1 (en) | 2008-10-10 | 2018-01-03 | Dana Farber Cancer Institute | Chemical modulators of pro-apoptotic bax and bcl-2 polypeptides |
| WO2010068684A2 (en) | 2008-12-09 | 2010-06-17 | Dana Farber Cancer Institute, Inc. | Methods and compositions for specific modulation of mcl-1 |
-
1984
- 1984-08-09 GB GB08420246A patent/GB2145084B/en not_active Expired
- 1984-08-09 US US06/639,113 patent/US4584377A/en not_active Expired - Fee Related
- 1984-08-13 CA CA000460842A patent/CA1267147A/en not_active Expired
- 1984-08-14 IT IT48730/84A patent/IT1177967B/it active
- 1984-08-17 FR FR8412905A patent/FR2550791B1/fr not_active Expired
- 1984-08-17 CH CH3957/84A patent/CH669379A5/de not_active IP Right Cessation
- 1984-08-17 DE DE19843430365 patent/DE3430365A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IT8448730A1 (it) | 1986-02-14 |
| FR2550791A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-22 |
| GB2145084B (en) | 1987-01-28 |
| IT8448730A0 (it) | 1984-08-14 |
| IT1177967B (it) | 1987-09-03 |
| US4584377A (en) | 1986-04-22 |
| FR2550791B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-10-14 |
| DE3430365A1 (de) | 1985-03-07 |
| GB2145084A (en) | 1985-03-20 |
| CA1267147A (en) | 1990-03-27 |
| GB8420246D0 (en) | 1984-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH648037A5 (de) | Imidazo-rifamycin-derivate mit antibakterieller wirksamkeit. | |
| CH669379A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2743654C3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE69127691T2 (de) | Be-13793c-derivat mit antitumorwirkung | |
| DE3881576T2 (de) | Anthracyclinderivate und ihre Verwendung. | |
| DD211565A5 (de) | Verfahren zur herstellung von 4"-epi-erythromycin a und derivaten hiervon als brauchbare antibakterielle mittel | |
| DE2132445C2 (de) | Ester der Antibiotika B5050 und Tetrahydro-B-5050 und Verfahren zu ihrer Herstellung | |
| DE2953969C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2164564C2 (de) | Antibiotikum A-201A und Verfahren zu seiner Herstellung | |
| DE2715255A1 (de) | Anthracyclinglykoside | |
| DE3044970C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3788389T2 (de) | Cervinomycinabkömmlinge als antibiotika und deren herstellungsverfahren. | |
| DE2607459A1 (de) | Neue antibiotische verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE69816621T2 (de) | Macrolide mit antitumoraktivität | |
| DE69400352T2 (de) | 3- oder 4-Glykosyloxybenzopyranderivat und dieses enthaltende antiallergisches Mittel | |
| EP0660825B1 (de) | Entzündungshemmende makrolactame (cyclamenol) | |
| DE2804507A1 (de) | Halbsynthetische 4"-erythromycin-a-derivate und verfahren zu ihrer herstellung | |
| DE3149608C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3425357A1 (de) | 1-hydroxy-cytorhodine, ein mikrobiologisches verfahren zu ihrer herstellung und ihre verwendung als cytostatika | |
| DE3248280A1 (de) | Salbomycin und verfahren zu seiner herstellung | |
| DE2213674C3 (de) | Gemisch aus Pepstatin B und Pepstatin C, Verfahren zu dessen Herstellung und dieses Gemisch enthaltende Arzneimittel | |
| DE2261832C3 (de) | 5-Dihydrocoriolin C und Verfahren zu seiner Gewinnung | |
| DE1617585C3 (de) | Leucomycin-Antibiotica A3 bis A9 | |
| CH629226A5 (de) | Verfahren zur herstellung von neuen d-homosteroiden. | |
| DE1939045C (de) | Verfahren zur Herstellung des Antibiotikums 289-F |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |