PL83206B1 - 3,-4,-dideoxykanamycin b active against resistant bacteria and its synthesis[gb1349302a] - Google Patents
3,-4,-dideoxykanamycin b active against resistant bacteria and its synthesis[gb1349302a] Download PDFInfo
- Publication number
- PL83206B1 PL83206B1 PL1971149704A PL14970471A PL83206B1 PL 83206 B1 PL83206 B1 PL 83206B1 PL 1971149704 A PL1971149704 A PL 1971149704A PL 14970471 A PL14970471 A PL 14970471A PL 83206 B1 PL83206 B1 PL 83206B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- chr
- formula
- nhcor
- kanamycin
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- 229960003807 dibekacin Drugs 0.000 title abstract 4
- 241000894006 Bacteria Species 0.000 title description 9
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B 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@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 229960001192 bekanamycin Drugs 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000006239 protecting group Chemical group 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- -1 alMlsulfonyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229930182824 kanamycin B Natural products 0.000 abstract description 13
- 230000001603 reducing effect Effects 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 21
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[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@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229930027917 kanamycin Natural products 0.000 description 4
- 229960000318 kanamycin Drugs 0.000 description 4
- 229930182823 kanamycin A Natural products 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- FLJPGEWQYJVDPF-UHFFFAOYSA-L caesium sulfate Chemical compound [Cs+].[Cs+].[O-]S([O-])(=O)=O FLJPGEWQYJVDPF-UHFFFAOYSA-L 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- XPIJMQVLTXAGME-UHFFFAOYSA-N 1,1-dimethoxycyclohexane Chemical compound COC1(OC)CCCCC1 XPIJMQVLTXAGME-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- HYGYSIDIKIGPJA-UHFFFAOYSA-N chloroform;ethyl acetate;methanol Chemical compound OC.ClC(Cl)Cl.CCOC(C)=O HYGYSIDIKIGPJA-UHFFFAOYSA-N 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 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
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45065760A JPS507595B1 (en, 2012) | 1970-07-29 | 1970-07-29 | |
| JP46030871A JPS5146110B1 (en, 2012) | 1971-05-11 | 1971-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83206B1 true PL83206B1 (en) | 1975-12-31 |
Family
ID=26369303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971149704A PL83206B1 (en) | 1970-07-29 | 1971-07-28 | 3,-4,-dideoxykanamycin b active against resistant bacteria and its synthesis[gb1349302a] |
Country Status (23)
| Country | Link |
|---|---|
| AT (1) | AT320846B (en, 2012) |
| BE (1) | BE770692A (en, 2012) |
| BG (1) | BG19188A3 (en, 2012) |
| CA (1) | CA953294A (en, 2012) |
| CH (1) | CH552586A (en, 2012) |
| DK (1) | DK127778B (en, 2012) |
| ES (1) | ES392570A1 (en, 2012) |
| FI (1) | FI57596C (en, 2012) |
| FR (1) | FR2103935A5 (en, 2012) |
| GB (1) | GB1349302A (en, 2012) |
| HK (1) | HK57477A (en, 2012) |
| HU (1) | HU162704B (en, 2012) |
| IE (1) | IE35480B1 (en, 2012) |
| IL (1) | IL36973A (en, 2012) |
| LU (1) | LU63625A1 (en, 2012) |
| MY (1) | MY7800147A (en, 2012) |
| NL (1) | NL163219C (en, 2012) |
| NO (1) | NO134117C (en, 2012) |
| PL (1) | PL83206B1 (en, 2012) |
| RO (1) | RO63815A (en, 2012) |
| SE (1) | SE398753B (en, 2012) |
| SU (1) | SU511007A3 (en, 2012) |
| YU (1) | YU35895B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1537905A (en) * | 1975-12-09 | 1979-01-10 | Microbial Chem Res Found | Processes for the preparation of 3',4'-dideoxykanamycin b |
| JPS6029720B2 (ja) * | 1975-12-11 | 1985-07-12 | 財団法人微生物化学研究会 | ３′，４′‐ジデオキシカナマイシンｂの新規な製造法 |
| JPS52153942A (en) * | 1976-06-16 | 1977-12-21 | Microbial Chem Res Found | Preparation of kanamicin c deoxy derivatives and kanamicine c or its deoxy derivatives |
| HU177398B (en) * | 1976-12-16 | 1981-12-28 | Microbial Chem Res Found | New process for producing 3:4'-dideoxi-kanamycin b |
| CA2654561A1 (en) * | 2006-06-02 | 2007-12-13 | Meiji Seika Kaisha, Ltd. | Novel aminoglycoside antibiotics |
-
1971
- 1971-06-01 GB GB1831771A patent/GB1349302A/en not_active Expired
- 1971-06-02 IL IL36973A patent/IL36973A/xx unknown
- 1971-06-18 FI FI1744/71A patent/FI57596C/fi active
- 1971-06-23 ES ES392570A patent/ES392570A1/es not_active Expired
- 1971-06-25 CH CH937771A patent/CH552586A/xx not_active IP Right Cessation
- 1971-06-29 NL NL7109001.A patent/NL163219C/xx not_active IP Right Cessation
- 1971-07-19 HU HUZA335A patent/HU162704B/hu unknown
- 1971-07-23 SU SU1685994A patent/SU511007A3/ru active
- 1971-07-26 RO RO7100067797A patent/RO63815A/ro unknown
- 1971-07-27 YU YU1963/71A patent/YU35895B/xx unknown
- 1971-07-28 DK DK371271AA patent/DK127778B/da unknown
- 1971-07-28 CA CA119,288A patent/CA953294A/en not_active Expired
- 1971-07-28 LU LU63625D patent/LU63625A1/xx unknown
- 1971-07-28 AT AT657571A patent/AT320846B/de not_active IP Right Cessation
- 1971-07-28 FR FR7128504A patent/FR2103935A5/fr not_active Expired
- 1971-07-28 PL PL1971149704A patent/PL83206B1/pl unknown
- 1971-07-28 NO NO2852/71A patent/NO134117C/no unknown
- 1971-07-28 IE IE964/71A patent/IE35480B1/xx unknown
- 1971-07-29 BE BE770692A patent/BE770692A/xx unknown
- 1971-07-29 SE SE7109756A patent/SE398753B/xx unknown
- 1971-07-29 BG BG018187A patent/BG19188A3/xx unknown
-
1977
- 1977-11-17 HK HK574/77A patent/HK57477A/xx unknown
-
1978
- 1978-12-30 MY MY147/78A patent/MY7800147A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134117B (en, 2012) | 1976-05-10 |
| MY7800147A (en) | 1978-12-31 |
| CH552586A (de) | 1974-08-15 |
| FI57596B (fi) | 1980-05-30 |
| NO134117C (en, 2012) | 1976-08-18 |
| FR2103935A5 (en, 2012) | 1972-04-14 |
| NL7109001A (en, 2012) | 1972-02-01 |
| IL36973A (en) | 1974-06-30 |
| GB1349302A (en) | 1974-04-03 |
| SE398753B (sv) | 1978-01-16 |
| YU196371A (en) | 1981-02-28 |
| CA953294A (en) | 1974-08-20 |
| ES392570A1 (es) | 1974-06-16 |
| DE2135191B2 (de) | 1976-09-02 |
| RO63815A (fr) | 1979-01-15 |
| BE770692A (fr) | 1971-12-01 |
| FI57596C (fi) | 1980-09-10 |
| NL163219C (nl) | 1980-08-15 |
| IE35480B1 (en) | 1976-03-03 |
| NL163219B (nl) | 1980-03-17 |
| HU162704B (en, 2012) | 1973-03-28 |
| DK127778B (da) | 1974-01-07 |
| YU35895B (en) | 1981-08-31 |
| DE2135191A1 (en, 2012) | 1972-02-03 |
| AT320846B (de) | 1975-02-25 |
| BG19188A3 (bg) | 1975-04-30 |
| HK57477A (en) | 1977-11-25 |
| LU63625A1 (en, 2012) | 1971-11-26 |
| IE35480L (en) | 1972-01-29 |
| SU511007A3 (ru) | 1976-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3753973A (en) | The preparation of 3'-4'-dideoxykanamycin b active against resistant bacteria | |
| EP0638584B1 (en) | 5-o-desosaminylerythronolide a derivative | |
| US4518590A (en) | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method | |
| JPS582960B2 (ja) | 新規なプソイドサッカライド類の製造方法 | |
| US4454123A (en) | O-xylopyranoside series compounds and methods of use | |
| US3956274A (en) | New compound 6'-deoxy-'-substituted or unsubstituted amino-lividomycins and the production thereof | |
| HU206221B (en) | Process for producing acylated derivatives of etoposide and pharmaceutical compositions comprising such compounds as active ingredient | |
| PL83206B1 (en) | 3,-4,-dideoxykanamycin b active against resistant bacteria and its synthesis[gb1349302a] | |
| US3953422A (en) | Deoxyglucose derivatives | |
| USRE28647E (en) | Preparation of 3-4 dideoxykanamycin B active against resistant bacteria | |
| CH639972A5 (de) | 4-deoxy-4-acylamido-derivate von oleandomycin und erythromycin. | |
| US4282152A (en) | Intermediates for preparing spectinomycin and analogs thereof | |
| JPH08217788A (ja) | １−ｎ−エチルシソマイシンの製造方法 | |
| US4367226A (en) | N-Sugar compounds, compositions and uses thereof | |
| US3935184A (en) | Synthetic polyoxin type nucleosides | |
| JPWO2004067544A1 (ja) | 新規化合物カプラゼンとカプラゼン誘導体、ならびに新規化合物カプラゾールとカプラゾール誘導体 | |
| US2659733A (en) | Process of producing butyrolactones | |
| US3751408A (en) | Imidazole-ribosyl cyclophosphate compounds and therapeutic compositions | |
| US4166901A (en) | 4"-Deoxy-4"-arylglyoxamido- and aroylthioformamido derivatives of oleandomycin and its esters | |
| EP0075449A1 (en) | Penicillin derivatives | |
| US4208407A (en) | 5-Deoxyfortimicin A, 2,5-dideoxyfortimicin A and the corresponding 4-N-acyl and alkyl fortimicin B derivatives thereof and intermediates therefor | |
| US4345086A (en) | Intermediate compounds in the preparation of spectinomycin | |
| US4129719A (en) | 5,6-Epineamine and process for preparing the same | |
| US4232147A (en) | 4-N-Acylfortimicin B-1,5-carbamates | |
| JPS61200998A (ja) | エリスロマイシンエステル誘導体 |