DD287509A5 - Verfahren zur herstellung antibiotischer verbindungen - Google Patents
Verfahren zur herstellung antibiotischer verbindungen Download PDFInfo
- Publication number
- DD287509A5 DD287509A5 DD89330937A DD33093789A DD287509A5 DD 287509 A5 DD287509 A5 DD 287509A5 DD 89330937 A DD89330937 A DD 89330937A DD 33093789 A DD33093789 A DD 33093789A DD 287509 A5 DD287509 A5 DD 287509A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- group
- following formula
- pharmaceutically acceptable
- hydrogen atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002466 imines Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000000988 D-alanyl group Chemical group N[C@@H](C(=O)*)C 0.000 claims description 2
- 125000001980 alanyl group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000003404 beta-D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 abstract description 4
- 239000003429 antifungal agent Substances 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003242 anti bacterial agent Substances 0.000 description 10
- 229940088710 antibiotic agent Drugs 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 8
- 230000004151 fermentation Effects 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 239000002953 phosphate buffered saline Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 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 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 241000972646 Actinomadura hibisca Species 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 229940041514 candida albicans extract Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012138 yeast extract Substances 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000013587 production medium Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000011218 seed culture Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000000214 D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 150000003141 primary amines Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000776296 Cryptococcus neoformans var. grubii Species 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 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
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/244—Anthraquinone radicals, e.g. sennosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/221,144 US4960755A (en) | 1988-07-19 | 1988-07-19 | BU-3608 derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD287509A5 true DD287509A5 (de) | 1991-02-28 |
Family
ID=22826542
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89330937A DD287509A5 (de) | 1988-07-19 | 1989-07-18 | Verfahren zur herstellung antibiotischer verbindungen |
| DD89338278A DD296081A5 (de) | 1988-07-19 | 1989-07-18 | Verfahren zur herstellung antibiotischer verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89338278A DD296081A5 (de) | 1988-07-19 | 1989-07-18 | Verfahren zur herstellung antibiotischer verbindungen |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4960755A (cs) |
| EP (1) | EP0351799B1 (cs) |
| JP (1) | JP2772549B2 (cs) |
| KR (1) | KR970003127B1 (cs) |
| AT (1) | ATE100459T1 (cs) |
| AU (1) | AU622197B2 (cs) |
| CA (1) | CA1337907C (cs) |
| CS (1) | CS274700B2 (cs) |
| DD (2) | DD287509A5 (cs) |
| DE (1) | DE68912438T2 (cs) |
| DK (1) | DK170778B1 (cs) |
| ES (1) | ES2048793T3 (cs) |
| FI (1) | FI92206C (cs) |
| HU (2) | HU203112B (cs) |
| IE (1) | IE62586B1 (cs) |
| IL (1) | IL91001A (cs) |
| MY (1) | MY105128A (cs) |
| NO (1) | NO170544C (cs) |
| NZ (1) | NZ229964A (cs) |
| PT (1) | PT91203B (cs) |
| RU (2) | RU2032693C1 (cs) |
| YU (1) | YU138289A (cs) |
| ZA (1) | ZA895455B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5183808A (en) * | 1988-11-10 | 1993-02-02 | Bristol-Myers Squibb Company | Method for treating fungal infections with serine analogs of BU-3608 antibiotics |
| US5114857A (en) * | 1988-11-10 | 1992-05-19 | Bristol-Myers Company | Actinomadura hibisca microorganism useful for preparing serine analogs of BU-3608 antibiotics |
| JP2643404B2 (ja) * | 1989-01-13 | 1997-08-20 | 財団法人微生物化学研究会 | 新抗生物質ｎ―アセチルベナノマイシンｂならびにその製造法 |
| EP0407939A1 (en) * | 1989-07-10 | 1991-01-16 | Bristol-Myers Squibb Company | Antiviral antibiotic BU-3889V |
| US5098708A (en) * | 1990-06-14 | 1992-03-24 | Bristol-Myers Squibb Company | Antiviral antibiotic BU-3889V |
| FI92207C (fi) * | 1989-11-14 | 1994-10-10 | Squibb Bristol Myers Co | Menetelmä terapeuttisesti käyttökelpoisten pradimisiinijohdannaisten valmistamiseksi |
| US5227370A (en) * | 1989-11-14 | 1993-07-13 | Bristol-Myers Squibb Company | Pradimicin derivatives |
| CA2030166C (en) * | 1989-11-22 | 1997-10-07 | Shimpei Aburaki | Pradimicin derivatives |
| US5843908A (en) * | 1990-09-28 | 1998-12-01 | Bristol-Myers Squibb Company | Pradimicins l and fl, and derivatives thereof |
| US5696096A (en) * | 1990-09-28 | 1997-12-09 | Bristol-Myers Squibb Company | Pradimicin derivatives |
| US5326867A (en) * | 1992-07-16 | 1994-07-05 | Bristol-Myers Squibb Company | Pradimic acids, amides, and pradimicin derivatives |
| US5338728A (en) * | 1992-08-14 | 1994-08-16 | Bristol-Myers Squibb | Pradimicin compounds |
| RU2220706C2 (ru) * | 2001-11-15 | 2004-01-10 | Научный Центр Здоровья детей РАМН | Лекарственное противогрибковое средство |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4591637A (en) * | 1985-01-17 | 1986-05-27 | Sri International | Open chain-morpholino adriamycins |
| US4870165A (en) * | 1987-02-02 | 1989-09-26 | Bristol-Myers Company | Antifungal antibiotics |
| JP2512050B2 (ja) * | 1987-12-25 | 1996-07-03 | 財団法人微生物化学研究会 | 新規抗かび性抗生物質デキシロシルベナノマイシンｂならびにその製造法 |
| US5055453A (en) * | 1987-11-02 | 1991-10-08 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Benanomicins a and antibiotic compositions |
| US5696096A (en) * | 1990-09-28 | 1997-12-09 | Bristol-Myers Squibb Company | Pradimicin derivatives |
-
1988
- 1988-07-19 US US07/221,144 patent/US4960755A/en not_active Expired - Lifetime
-
1989
- 1989-07-07 CA CA000605139A patent/CA1337907C/en not_active Expired - Fee Related
- 1989-07-11 YU YU01382/89A patent/YU138289A/xx unknown
- 1989-07-14 FI FI893426A patent/FI92206C/fi not_active IP Right Cessation
- 1989-07-17 IL IL9100189A patent/IL91001A/en not_active IP Right Cessation
- 1989-07-17 NZ NZ229964A patent/NZ229964A/en unknown
- 1989-07-18 PT PT91203A patent/PT91203B/pt active IP Right Grant
- 1989-07-18 EP EP89113184A patent/EP0351799B1/en not_active Expired - Lifetime
- 1989-07-18 DE DE68912438T patent/DE68912438T2/de not_active Expired - Fee Related
- 1989-07-18 NO NO892939A patent/NO170544C/no not_active IP Right Cessation
- 1989-07-18 AT AT89113184T patent/ATE100459T1/de not_active IP Right Cessation
- 1989-07-18 ZA ZA895455A patent/ZA895455B/xx unknown
- 1989-07-18 ES ES89113184T patent/ES2048793T3/es not_active Expired - Lifetime
- 1989-07-18 IE IE232589A patent/IE62586B1/en not_active IP Right Cessation
- 1989-07-18 DD DD89330937A patent/DD287509A5/de not_active IP Right Cessation
- 1989-07-18 RU SU894614706A patent/RU2032693C1/ru active
- 1989-07-18 DD DD89338278A patent/DD296081A5/de unknown
- 1989-07-18 DK DK354689A patent/DK170778B1/da not_active IP Right Cessation
- 1989-07-18 KR KR1019890010190A patent/KR970003127B1/ko not_active Expired - Fee Related
- 1989-07-19 HU HU893664A patent/HU203112B/hu not_active IP Right Cessation
- 1989-07-19 MY MYPI89000980A patent/MY105128A/en unknown
- 1989-07-19 AU AU38274/89A patent/AU622197B2/en not_active Ceased
- 1989-07-19 HU HU908256A patent/HU205131B/hu not_active IP Right Cessation
- 1989-07-19 CS CS440889A patent/CS274700B2/cs unknown
- 1989-07-19 JP JP1184858A patent/JP2772549B2/ja not_active Expired - Lifetime
-
1990
- 1990-09-10 RU SU904830946A patent/RU2026302C1/ru active
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