DE2710694C2 - Aminocyclitol-glycoside, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Präparate - Google Patents
Aminocyclitol-glycoside, Verfahren zu deren Herstellung und diese Verbindungen enthaltende PräparateInfo
- Publication number
- DE2710694C2 DE2710694C2 DE2710694A DE2710694A DE2710694C2 DE 2710694 C2 DE2710694 C2 DE 2710694C2 DE 2710694 A DE2710694 A DE 2710694A DE 2710694 A DE2710694 A DE 2710694A DE 2710694 C2 DE2710694 C2 DE 2710694C2
- Authority
- DE
- Germany
- Prior art keywords
- antibiotics
- neomycin
- antibiotic
- aminocyclitol
- paromomycin
- 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
Links
- 238000000034 method Methods 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 13
- 229930182470 glycoside Natural products 0.000 title claims description 6
- 150000002338 glycosides Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 32
- 229940088710 antibiotic agent Drugs 0.000 claims description 25
- 230000003115 biocidal effect Effects 0.000 claims description 21
- 229930193140 Neomycin Natural products 0.000 claims description 17
- 229960004927 neomycin Drugs 0.000 claims description 16
- 239000002609 medium Substances 0.000 claims description 15
- 241000187419 Streptomyces rimosus Species 0.000 claims description 13
- 241000187438 Streptomyces fradiae Species 0.000 claims description 12
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 claims description 11
- UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 claims description 10
- 229960001914 paromomycin Drugs 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- PGBHMTALBVVCIT-VZXHOKRSSA-N neomycin C Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VZXHOKRSSA-N 0.000 claims description 9
- 235000015097 nutrients Nutrition 0.000 claims description 8
- AQAVLWBEEHYBHV-UHFFFAOYSA-N 6-Deoxyparomomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2)OC2C(C(O)C(O)C(CO)O2)N)OC1CO AQAVLWBEEHYBHV-UHFFFAOYSA-N 0.000 claims description 7
- 241000187132 Streptomyces kanamyceticus Species 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229960003704 framycetin Drugs 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002474 experimental method Methods 0.000 claims description 5
- 239000001963 growth medium Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 241000588770 Proteus mirabilis Species 0.000 claims description 3
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- DTFAJAKTSMLKAT-JDCCYXBGSA-N 2-deoxystreptamine Chemical compound N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O DTFAJAKTSMLKAT-JDCCYXBGSA-N 0.000 claims description 2
- UOZODPSAJZTQNH-VZXHOKRSSA-N Paromomycin II Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-VZXHOKRSSA-N 0.000 claims description 2
- 241000607760 Shigella sonnei Species 0.000 claims description 2
- ANLMVXSIPASBFL-UHFFFAOYSA-N Streptamin D Natural products NC1C(O)C(N)C(O)C(O)C1O ANLMVXSIPASBFL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 235000021321 essential mineral Nutrition 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229940115939 shigella sonnei Drugs 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 244000052616 bacterial pathogen Species 0.000 claims 2
- 230000002779 inactivation Effects 0.000 claims 2
- 241000588724 Escherichia coli Species 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- 241000191938 Micrococcus luteus Species 0.000 claims 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- 230000001156 adenylylating effect Effects 0.000 claims 1
- 230000004075 alteration Effects 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000000865 phosphorylative effect Effects 0.000 claims 1
- ANLMVXSIPASBFL-FAEUDGQSSA-N streptamine Chemical compound N[C@H]1[C@H](O)[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O ANLMVXSIPASBFL-FAEUDGQSSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 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
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- SYJXFKPQNSDJLI-HKEUSBCWSA-N neamine Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](N)C[C@@H]1N SYJXFKPQNSDJLI-HKEUSBCWSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 235000019764 Soybean Meal Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004816 paper chromatography Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004455 soybean meal Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241001302584 Escherichia coli str. K-12 substr. W3110 Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- JGSMDVGTXBPWIM-UHFFFAOYSA-N Paromamine Natural products OC1C(O)C(N)CC(N)C1OC1C(N)C(O)C(O)C(CO)O1 JGSMDVGTXBPWIM-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- JGSMDVGTXBPWIM-HKEUSBCWSA-N paromamine Chemical compound O[C@@H]1[C@@H](O)[C@H](N)C[C@H](N)[C@H]1O[C@@H]1[C@H](N)[C@@H](O)[C@H](O)[C@@H](CO)O1 JGSMDVGTXBPWIM-HKEUSBCWSA-N 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- QRJMLIPXTTYRMQ-SYJWXDLUSA-N Actinamine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](NC)[C@H]1O QRJMLIPXTTYRMQ-SYJWXDLUSA-N 0.000 description 1
- -1 CaCO Chemical compound 0.000 description 1
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UVMKZRHHUOWSAC-UHFFFAOYSA-N Hyosamine Natural products CNC1CC(N)C(O)C(O)C1O UVMKZRHHUOWSAC-UHFFFAOYSA-N 0.000 description 1
- 241000511989 Neomys Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000405383 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Species 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930183544 Streptamin Natural products 0.000 description 1
- RQLDKUSQKQMFCN-DOOXDOMHSA-N [(1s,2s,3s,4s,5r,6r)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl] carbamate Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@H]1[C@@H](N=C(N)N)[C@H](O)[C@H](OC(N)=O)[C@H](O)[C@H]1O RQLDKUSQKQMFCN-DOOXDOMHSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229950004374 bluensomycin Drugs 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- MSXMXWJPFIDEMT-FAEUDGQSSA-N streptidine Chemical compound NC(=N)N[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@@H]1O MSXMXWJPFIDEMT-FAEUDGQSSA-N 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000012138 yeast extract Substances 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
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
-
- 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
- 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
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/228—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings
- C07H15/232—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to adjacent ring-carbon atoms of the cyclohexane rings with at least three saccharide radicals in the molecule, e.g. lividomycin, neomycin, paromomycin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9859/76A GB1549320A (en) | 1976-03-11 | 1976-03-11 | Aminoglycoside antibiotic compounds and process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2710694A1 DE2710694A1 (de) | 1977-09-15 |
| DE2710694C2 true DE2710694C2 (de) | 1985-08-01 |
Family
ID=9880112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2710694A Expired DE2710694C2 (de) | 1976-03-11 | 1977-03-11 | Aminocyclitol-glycoside, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Präparate |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5937077B2 (enExample) |
| BE (1) | BE852142A (enExample) |
| CA (1) | CA1068226A (enExample) |
| CH (1) | CH620944A5 (enExample) |
| DD (1) | DD130047A5 (enExample) |
| DE (1) | DE2710694C2 (enExample) |
| ES (1) | ES456743A1 (enExample) |
| FR (1) | FR2343751A1 (enExample) |
| GB (1) | GB1549320A (enExample) |
| HU (1) | HU178039B (enExample) |
| IT (1) | IT1114756B (enExample) |
| NL (1) | NL7702341A (enExample) |
| NO (1) | NO148558C (enExample) |
| PL (1) | PL104557B1 (enExample) |
| SE (1) | SE433091B (enExample) |
| SU (1) | SU952109A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109111376B (zh) * | 2018-09-18 | 2021-09-14 | 四川医立特生物医药有限公司 | 一种2,5-双脱氧链霉胺衍生物及其应用 |
-
1976
- 1976-03-11 GB GB9859/76A patent/GB1549320A/en not_active Expired
-
1977
- 1977-03-03 FR FR7706178A patent/FR2343751A1/fr active Granted
- 1977-03-04 NL NL7702341A patent/NL7702341A/xx not_active Application Discontinuation
- 1977-03-07 BE BE175514A patent/BE852142A/xx not_active IP Right Cessation
- 1977-03-08 IT IT21025/77A patent/IT1114756B/it active
- 1977-03-10 SE SE7702721A patent/SE433091B/xx unknown
- 1977-03-10 CA CA273,830A patent/CA1068226A/en not_active Expired
- 1977-03-10 CH CH305177A patent/CH620944A5/fr not_active IP Right Cessation
- 1977-03-10 NO NO770852A patent/NO148558C/no unknown
- 1977-03-11 JP JP52027528A patent/JPS5937077B2/ja not_active Expired
- 1977-03-11 DE DE2710694A patent/DE2710694C2/de not_active Expired
- 1977-03-11 DD DD7700197807A patent/DD130047A5/xx unknown
- 1977-03-11 SU SU772458602A patent/SU952109A3/ru active
- 1977-03-11 HU HU77LA910A patent/HU178039B/hu unknown
- 1977-03-11 PL PL1977196605A patent/PL104557B1/pl unknown
- 1977-03-11 ES ES456743A patent/ES456743A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7702721L (sv) | 1977-09-12 |
| HU178039B (en) | 1982-02-28 |
| FR2343751B1 (enExample) | 1981-10-16 |
| GB1549320A (en) | 1979-08-01 |
| SE433091B (sv) | 1984-05-07 |
| NL7702341A (nl) | 1977-09-13 |
| JPS5937077B2 (ja) | 1984-09-07 |
| BE852142A (fr) | 1977-09-07 |
| PL104557B1 (pl) | 1979-08-31 |
| NO148558C (no) | 1983-11-02 |
| DE2710694A1 (de) | 1977-09-15 |
| CA1068226A (en) | 1979-12-18 |
| IT1114756B (it) | 1986-01-27 |
| SU952109A3 (ru) | 1982-08-15 |
| DD130047A5 (de) | 1978-03-01 |
| NO770852L (no) | 1977-09-13 |
| CH620944A5 (en) | 1980-12-31 |
| FR2343751A1 (fr) | 1977-10-07 |
| NO148558B (no) | 1983-07-25 |
| PL196605A1 (pl) | 1978-02-13 |
| JPS52142044A (en) | 1977-11-26 |
| ES456743A1 (es) | 1978-06-01 |
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