JPH0733393B2 - 新規ｂｂｍ―１６７５ｃ抗腫瘍性抗生物質 - Google Patents
新規ｂｂｍ―１６７５ｃ抗腫瘍性抗生物質Info
- Publication number
- JPH0733393B2 JPH0733393B2 JP61201199A JP20119986A JPH0733393B2 JP H0733393 B2 JPH0733393 B2 JP H0733393B2 JP 61201199 A JP61201199 A JP 61201199A JP 20119986 A JP20119986 A JP 20119986A JP H0733393 B2 JPH0733393 B2 JP H0733393B2
- Authority
- JP
- Japan
- Prior art keywords
- bbm
- antibiotic
- antitumor
- cdcl
- magnetic resonance
- 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.)
- Expired - Lifetime
Links
- 239000003972 antineoplastic antibiotic Substances 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 239000003242 anti bacterial agent Substances 0.000 claims description 25
- 229940088710 antibiotic agent Drugs 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 230000003115 biocidal effect Effects 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 230000000259 anti-tumor effect Effects 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 238000001228 spectrum Methods 0.000 claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000000862 absorption spectrum Methods 0.000 claims description 9
- 238000004809 thin layer chromatography Methods 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims 2
- 239000012429 reaction media Substances 0.000 claims 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims 2
- 150000001793 charged compounds Chemical class 0.000 claims 1
- 238000002000 high resolution fast-atom bombardment mass spectrometry Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 19
- 238000006460 hydrolysis reaction Methods 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- 230000007062 hydrolysis Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 230000000975 bioactive effect Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- 239000012634 fragment Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 241000201778 Actinomadura verrucosospora Species 0.000 description 5
- 230000007073 chemical hydrolysis Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010265 fast atom bombardment Methods 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 241000187362 Actinomadura Species 0.000 description 4
- 208000001382 Experimental Melanoma Diseases 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PTUJLUSPXWWJSQ-KAOVMFEUSA-N esperamycin a1 Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1O[C@@H](C1\C=C/C#C[C@@]2(O)C3=C1)C3=C(NC(=O)OC)C(=O)[C@@H]2OC1OC(C)C(O)C(OC(=O)C=2C(=CC(OC)=C(OC)C=2)NC(=O)C(=C)OC)C1 PTUJLUSPXWWJSQ-KAOVMFEUSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000012790 confirmation Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- -1 methyl glycoside Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- 241000187361 Actinomadura sp. Species 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 101150034980 BRDT gene Proteins 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 229930189413 Esperamicin Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- PEIYAHAOJOISPN-WCXFNBEESA-N [(2s,3s,4s,6s)-4-hydroxy-6-[[(5z,13e)-9-hydroxy-2-[(2s,3s,4r,5r,6s)-4-hydroxy-5-[[(2r,4r,5r,6s)-4-hydroxy-6-methyl-5-methylsulfanyloxan-2-yl]oxyamino]-3-[(2s,4s,5s)-4-methoxy-5-(propan-2-ylamino)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-12-(methoxycarbonylamino Chemical compound O1C[C@H](NC(C)C)[C@@H](OC)C[C@@H]1O[C@H]1[C@H](O)[C@@H](NO[C@H]2O[C@@H](C)[C@H](SC)[C@H](O)C2)[C@H](C)O[C@@H]1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(O[C@@H]3O[C@@H](C)[C@@H](OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)[C@@H](O)C3)C2(O)C#C\C=C/C#C1 PEIYAHAOJOISPN-WCXFNBEESA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LJQQFQHBKUKHIS-WJHRIEJJSA-N esperamicin Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(OC3OC(C)C(O)C(OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)C3)C2(O)C#C\C=C/C#C1 LJQQFQHBKUKHIS-WJHRIEJJSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 102220201851 rs143406017 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002100 tumorsuppressive effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
- 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/06—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using actinomycetales
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/03—Actinomadura
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77033585A | 1985-08-27 | 1985-08-27 | |
| US770335 | 1985-08-27 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6195156A Division JPH07233186A (ja) | 1985-08-27 | 1994-08-19 | 新規ｂｂｍ−１６７５ｄ抗腫瘍性抗生物質 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62116589A JPS62116589A (ja) | 1987-05-28 |
| JPH0733393B2 true JPH0733393B2 (ja) | 1995-04-12 |
Family
ID=25088206
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61201199A Expired - Lifetime JPH0733393B2 (ja) | 1985-08-27 | 1986-08-27 | 新規ｂｂｍ―１６７５ｃ抗腫瘍性抗生物質 |
| JP6195156A Pending JPH07233186A (ja) | 1985-08-27 | 1994-08-19 | 新規ｂｂｍ−１６７５ｄ抗腫瘍性抗生物質 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6195156A Pending JPH07233186A (ja) | 1985-08-27 | 1994-08-19 | 新規ｂｂｍ−１６７５ｄ抗腫瘍性抗生物質 |
Country Status (26)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1215212A3 (en) * | 1987-01-30 | 2003-05-21 | Wyeth Holdings Corporation | Dihydro derivatives of LL-E33288 antibiotics |
| US4916065A (en) * | 1988-06-10 | 1990-04-10 | Bristol-Myers Company | BU-3420T Antitumor antibiotic |
| US5028536A (en) * | 1989-03-15 | 1991-07-02 | Bristol-Myers Squibb Company | Antitumor antibiotic BMY-41339 |
| US5086045A (en) * | 1989-03-15 | 1992-02-04 | Bristol-Myers Squibb Company | Antitumor antibiotic |
| CA2027601A1 (en) * | 1989-11-06 | 1991-05-07 | Koko Sugawara | Antitumor antibiotic bu-3983t |
| CA2039789A1 (en) * | 1990-04-27 | 1991-10-28 | Samuel J. Danishefsky | Calicheamicinone, derivatives and analogs thereof and methods of making the same |
| US5116845A (en) * | 1990-05-04 | 1992-05-26 | Bristol-Myers Company | BU-3420T antitumor antibiotic |
| US5264586A (en) * | 1991-07-17 | 1993-11-23 | The Scripps Research Institute | Analogs of calicheamicin gamma1I, method of making and using the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3148023A1 (de) * | 1981-12-04 | 1983-06-09 | Rudolf Dipl.-Ing. 8901 Oberottmarshausen Fischer | Heizungskessel fuer heisse rauchgase |
| US4578271A (en) * | 1982-05-24 | 1986-03-25 | Fujisawa Pharmaceutical Co., Ltd. | Biologically active WS 6049 substances, a process for the production thereof and their pharmaceutical compositions |
| NZ208013A (en) * | 1983-05-16 | 1987-07-31 | Bristol Myers Co | Antitumour antibiotic bbm-1675 and production by cultivating actinomadura verrucosospora |
| JPS606194A (ja) * | 1983-06-23 | 1985-01-12 | Meiji Seika Kaisha Ltd | 新規抗生物質ｓｆ−２２８８及びその製造法 |
| US4530835A (en) * | 1983-07-08 | 1985-07-23 | Warner-Lambert Company | CL-1577 Antibiotic compounds and their production |
-
1986
- 1986-07-25 IL IL79519A patent/IL79519A0/xx not_active IP Right Cessation
- 1986-08-01 ZA ZA865796A patent/ZA865796B/xx unknown
- 1986-08-15 CA CA000516111A patent/CA1307256C/en not_active Expired - Fee Related
- 1986-08-19 GB GB08620118A patent/GB2179649A/en active Granted
- 1986-08-20 GR GR862160A patent/GR862160B/el unknown
- 1986-08-22 FI FI863405A patent/FI83422C/fi not_active IP Right Cessation
- 1986-08-22 AU AU61751/86A patent/AU604464B2/en not_active Ceased
- 1986-08-26 CH CH3417/86A patent/CH668598A5/de not_active IP Right Cessation
- 1986-08-26 IT IT8621527A patent/IT1229176B/it active
- 1986-08-26 LU LU86562A patent/LU86562A1/fr unknown
- 1986-08-26 FR FR868612085A patent/FR2586686B1/fr not_active Expired - Fee Related
- 1986-08-26 DK DK406086A patent/DK170671B1/da not_active IP Right Cessation
- 1986-08-26 ES ES8601355A patent/ES2002728A6/es not_active Expired
- 1986-08-26 NL NL8602165A patent/NL8602165A/nl not_active Application Discontinuation
- 1986-08-26 BE BE0/217084A patent/BE905332A/fr not_active IP Right Cessation
- 1986-08-26 KR KR1019860007092A patent/KR920010226B1/ko not_active Expired
- 1986-08-26 IE IE228086A patent/IE59204B1/en not_active IP Right Cessation
- 1986-08-26 SE SE8603597A patent/SE469632B/sv not_active IP Right Cessation
- 1986-08-27 AT AT2317/86A patent/AT392971B/de not_active IP Right Cessation
- 1986-08-27 HU HU863709A patent/HU197915B/hu not_active IP Right Cessation
- 1986-08-27 DE DE3629052A patent/DE3629052C2/de not_active Expired - Fee Related
- 1986-08-27 JP JP61201199A patent/JPH0733393B2/ja not_active Expired - Lifetime
- 1986-08-27 PT PT83261A patent/PT83261B/pt unknown
-
1992
- 1992-02-13 SE SE9200428A patent/SE9200428L/xx not_active Application Discontinuation
- 1992-10-16 SG SG1096/92A patent/SG109692G/en unknown
-
1993
- 1993-01-07 HK HK7/93A patent/HK793A/xx not_active IP Right Cessation
- 1993-10-10 CY CY1676A patent/CY1676A/en unknown
-
1994
- 1994-08-19 JP JP6195156A patent/JPH07233186A/ja active Pending
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