JPS631319B2 - - Google Patents
Info
- Publication number
- JPS631319B2 JPS631319B2 JP53138402A JP13840278A JPS631319B2 JP S631319 B2 JPS631319 B2 JP S631319B2 JP 53138402 A JP53138402 A JP 53138402A JP 13840278 A JP13840278 A JP 13840278A JP S631319 B2 JPS631319 B2 JP S631319B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- zinc
- water
- kanamycin
- mmol
- 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
- 125000003277 amino group Chemical group 0.000 claims description 59
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 55
- 239000011701 zinc Substances 0.000 claims description 55
- 229910052725 zinc Inorganic materials 0.000 claims description 55
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 35
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229940006486 zinc cation Drugs 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 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 6
- 230000009471 action Effects 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- 229960000318 kanamycin Drugs 0.000 description 58
- 229930182823 kanamycin A Natural products 0.000 description 58
- 239000000126 substance Substances 0.000 description 57
- 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 51
- 239000007787 solid Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- -1 cadmium cations Chemical class 0.000 description 36
- 239000012458 free base Substances 0.000 description 31
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
- 238000005917 acylation reaction Methods 0.000 description 26
- 239000003960 organic solvent Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 150000003751 zinc Chemical class 0.000 description 20
- MJSHDCCLFGOEIK-UHFFFAOYSA-N benzyl (2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)OCC1=CC=CC=C1 MJSHDCCLFGOEIK-UHFFFAOYSA-N 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 150000001768 cations Chemical class 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 239000012456 homogeneous solution Substances 0.000 description 13
- 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 description 13
- 150000003839 salts Chemical class 0.000 description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 229960001192 bekanamycin Drugs 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 229930182824 kanamycin B Natural products 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000003282 alkyl amino group Chemical group 0.000 description 11
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 239000013076 target substance Substances 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000010933 acylation Effects 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 229960003807 dibekacin Drugs 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 239000003957 anion exchange resin Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003729 cation exchange resin Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229930027917 kanamycin Natural products 0.000 description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229920001661 Chitosan Polymers 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 229930182825 Kanamycin C Natural products 0.000 description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000013522 chelant Chemical group 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
- 230000009918 complex formation Effects 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- JJCQSGDBDPYCEO-XVZSLQNASA-N dibekacin Chemical compound O1[C@H](CN)CC[C@@H](N)[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 JJCQSGDBDPYCEO-XVZSLQNASA-N 0.000 description 6
- WZDRWYJKESFZMB-FQSMHNGLSA-N kanamycin C Chemical compound O([C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)N)N)[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O WZDRWYJKESFZMB-FQSMHNGLSA-N 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000004246 zinc acetate Substances 0.000 description 6
- 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 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052793 cadmium Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 229930192786 Sisomicin Natural products 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000005083 Zinc sulfide Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229960005456 sisomicin Drugs 0.000 description 4
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 229910052984 zinc sulfide Inorganic materials 0.000 description 4
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- SOHCYNFHNYKSTM-UHFFFAOYSA-N methylsulfinylmethane;oxolane Chemical compound CS(C)=O.C1CCOC1 SOHCYNFHNYKSTM-UHFFFAOYSA-N 0.000 description 3
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229930182566 Gentamicin Natural products 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QHZNYGVZDCMWKX-UHFFFAOYSA-N benzyl (1,3-dioxoisoindol-2-yl) carbonate Chemical compound O=C1C2=CC=CC=C2C(=O)N1OC(=O)OCC1=CC=CC=C1 QHZNYGVZDCMWKX-UHFFFAOYSA-N 0.000 description 2
- 238000005976 benzyloxycarbonylation reaction Methods 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000002021 butanolic extract Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- LKKVGKXCMYHKSL-LLZRLKDCSA-N gentamycin A Chemical compound O[C@H]1[C@H](NC)[C@@H](O)CO[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](N)C[C@H]1N LKKVGKXCMYHKSL-LLZRLKDCSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[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 NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
- 229940007718 zinc hydroxide Drugs 0.000 description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 2
- ULKOBRDRCYROKY-JTQLQIEISA-N (2s)-2-hydroxy-4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound OC(=O)[C@@H](O)CCNC(=O)OCC1=CC=CC=C1 ULKOBRDRCYROKY-JTQLQIEISA-N 0.000 description 1
- NZKFUBQRAWPZJP-BXKLGIMVSA-N (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.N[C@@H]1C[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.N[C@@H]1C[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 NZKFUBQRAWPZJP-BXKLGIMVSA-N 0.000 description 1
- IDSYVBBNVYBBAF-PBSUHMDJSA-N (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r,5s,6r)-3-amino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol Chemical compound N[C@@H]1C[C@H](O)[C@@H](CO)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 IDSYVBBNVYBBAF-PBSUHMDJSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- RDEIXVOBVLKYNT-UHFFFAOYSA-N 2-[4,6-diamino-3-[3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;2-[4,6-diamino-3-[3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;2-[4,6-diamino-3-[ Chemical compound OS(O)(=O)=O.O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CCC(CN)O2)N)C(N)CC1N.O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CCC(O2)C(C)N)N)C(N)CC1N.O1C(C(C)NC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N RDEIXVOBVLKYNT-UHFFFAOYSA-N 0.000 description 1
- GMWQKAHYINBSDJ-UHFFFAOYSA-N 2-hydroxy-3-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC(=O)C(O)CNC(=O)OCC1=CC=CC=C1 GMWQKAHYINBSDJ-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KSPIHGBHKVISFI-UHFFFAOYSA-N Diphenylcarbazide Chemical compound C=1C=CC=CC=1NNC(=O)NNC1=CC=CC=C1 KSPIHGBHKVISFI-UHFFFAOYSA-N 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- ANTGQBPGYZDWAW-UHFFFAOYSA-N azane;1,4-dioxane Chemical compound N.C1COCCO1 ANTGQBPGYZDWAW-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 description 1
- 150000004652 butanoic acids Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- JRZBPELLUMBLQU-UHFFFAOYSA-N carbonazidic acid Chemical class OC(=O)N=[N+]=[N-] JRZBPELLUMBLQU-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- CEAZRRDELHUEMR-UHFFFAOYSA-N gentamicin Chemical class O1C(C(C)NC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N CEAZRRDELHUEMR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
- PGXWDLGWMQIXDT-UHFFFAOYSA-N methylsulfinylmethane;hydrate Chemical compound O.CS(C)=O PGXWDLGWMQIXDT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
- OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000006289 propionylation Effects 0.000 description 1
- 238000010515 propionylation reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005583 trifluoroacetylation reaction Methods 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- 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
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)
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13840278A JPS5564598A (en) | 1978-11-11 | 1978-11-11 | Preparation of aminoglycoside antibiotic having selectively protected amino group |
| IE2026/79A IE48972B1 (en) | 1978-11-11 | 1979-10-23 | The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic |
| IE1521/83A IE48973B1 (en) | 1978-11-11 | 1979-10-23 | The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic |
| ZA00795691A ZA795691B (en) | 1978-11-11 | 1979-10-24 | The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic |
| IN1104/CAL/79A IN151454B (fr) | 1978-11-11 | 1979-10-24 | |
| SE7908850A SE446632B (sv) | 1978-11-11 | 1979-10-25 | Sett att framstella ett selektivt skyddat n-acylerat derivat av ett aminoglykosidantibiotikum |
| NL7907892A NL7907892A (nl) | 1978-11-11 | 1979-10-26 | Werkwijze voor de bereiding van een selectief beschermd n-geacyleerd derivaat van een aminoglycosidisch antibioticum. |
| CH9682/79A CH650004A5 (de) | 1978-11-11 | 1979-10-29 | Verfahren zur herstellung eines selektiv geschuetzten n-acylierten aminoglycosid-antibiotikums. |
| CH184/84A CH650005A5 (de) | 1978-11-11 | 1979-10-29 | Verfahren zur herstellung eines selektiv geschuetzten n-acylierten aminoglycosid-antibiotikums. |
| AT0707979A AT367066B (de) | 1978-11-11 | 1979-11-02 | Verfahren zur herstellung eines selektiv geschuetzten n-acylierten derivates eines aminoglycosid-antibiotikums |
| US06/090,591 US4297485A (en) | 1978-11-11 | 1979-11-02 | Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic |
| DE2953878A DE2953878C2 (de) | 1978-11-11 | 1979-11-08 | Verfahren zur Herstellung von durch Schutzgruppen N-acylierten Aminoglycosiden |
| YU2743/79A YU44185B (en) | 1978-11-11 | 1979-11-08 | Process of a selective acylated n-protected derivatives of an amino-glycoside antibiotic |
| FR7928015A FR2441631A1 (fr) | 1978-11-11 | 1979-11-08 | Procede de preparation d'un derive n-acyle selectivement protege d'un antibiotique aminoglycosidique |
| MX798478U MX6181E (es) | 1978-11-11 | 1979-11-08 | Procedimiento para la preparacion de derivados n-protegidos de antibioticos aminoglucosidicos |
| PH23263A PH16263A (en) | 1978-11-11 | 1979-11-08 | The production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic |
| DE2945010A DE2945010C2 (de) | 1978-11-11 | 1979-11-08 | Verfahren zur Herstellung von durch Schutzgruppen N-acylierten Aminoglycosiden |
| ES485830A ES485830A1 (es) | 1978-11-11 | 1979-11-08 | Proceso para la produccion de un derivado selectivamente a- cilado n-protegido, de un antibiotico aminoglicoidico. |
| AU52622/79A AU529682B2 (en) | 1978-11-11 | 1979-11-08 | N-acylated derivatives of aminoglyosidic antibiotics |
| DK476679A DK476679A (da) | 1978-11-11 | 1979-11-09 | Fremgangsmaade til fremstilling af et selektivt beskyttet n-acyleret derivat af et aminoglycosidantibioticum |
| BE2/58198A BE879925A (fr) | 1978-11-11 | 1979-11-09 | Procede nouveau de preparation d'un derive n-acyle selectivement protege d'un antibiotique amino-glycosidique |
| GB8103076A GB2065123B (en) | 1978-11-11 | 1979-11-09 | Production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic |
| HU79ZA414A HU183050B (en) | 1978-11-11 | 1979-11-09 | Process for producing n-acyl-derivatives of aminoglycoside antibiotics |
| CA000339531A CA1118416A (fr) | 1978-11-11 | 1979-11-09 | Preparation d'un derive n-acyle protege selectivement, a partir d'un antibiotique aminoglycosidique |
| GB7938894A GB2036020B (en) | 1978-11-11 | 1979-11-09 | Production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic |
| LU81881A LU81881A1 (fr) | 1978-11-11 | 1979-11-09 | Procede de preparation d'un derive n-acyle selectivement protege d'un antibiotique aminoglycosidique |
| AR79278828A AR241915A1 (es) | 1978-11-11 | 1979-11-09 | Procedimiento para preparar derivados 1-n- no protegidos y n-peracilados de antibioticos aminoglicocidos. |
| IT09592/79A IT1166021B (it) | 1978-11-11 | 1979-11-12 | Procedimento per la produzione di un derivato n acilato selettivamente protetto di un antibiotico amino glicasidico |
| CS797711A CS261853B2 (en) | 1978-11-11 | 1979-11-12 | Method of aminoglycoside antibiotic's selectively acylated n-protected derivative production |
| ES492479A ES492479A0 (es) | 1978-11-11 | 1980-06-16 | Proceso para la produccion de un derivado n-acilado, selec- tivamente protegido, de un antibiotico aminoglicosidico |
| PH25015A PH15906A (en) | 1978-11-11 | 1980-12-22 | The production of a selectively protected n-acylated derivatives of an aminoglycosidic antibiotic |
| FR8110968A FR2482109A1 (fr) | 1978-11-11 | 1981-06-03 | Procede de preparation d'un derive n-acyle selectivement protege d'un antibiotique aminoglycosidique |
| CA386,540A CA1131628A (fr) | 1978-11-11 | 1981-09-23 | Obtention d'un derive n-acyle protege selectivement, a partir d'un antibiotique aminoglycosidique |
| CS829399A CS261859B2 (cs) | 1978-11-11 | 1982-12-20 | Způsob přípravy selektivně chráněného N-acylovaného derivátu aminoglykosidového antibiotika |
| SE8406344A SE463264B (sv) | 1978-11-11 | 1984-12-13 | Saett att framstaella 1-n-oskyddat men i oevrigt n-acylerat derivat av ett aminoglykosidantibiotikum |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13840278A JPS5564598A (en) | 1978-11-11 | 1978-11-11 | Preparation of aminoglycoside antibiotic having selectively protected amino group |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5564598A JPS5564598A (en) | 1980-05-15 |
| JPS631319B2 true JPS631319B2 (fr) | 1988-01-12 |
Family
ID=15221109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13840278A Granted JPS5564598A (en) | 1978-11-11 | 1978-11-11 | Preparation of aminoglycoside antibiotic having selectively protected amino group |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5564598A (fr) |
| BE (1) | BE879925A (fr) |
| CS (1) | CS261853B2 (fr) |
| HU (1) | HU183050B (fr) |
| ZA (1) | ZA795691B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136254A (en) * | 1976-06-17 | 1979-01-23 | Schering Corporation | Process of selectively blocking amino functions in aminoglycosides using transition metal salts and intermediates used thereby |
| EP0446670B1 (fr) * | 1990-03-08 | 1994-09-21 | Biochimica Opos Spa | Procédé de préparation de précurseurs d'amikacine |
| KR100450607B1 (ko) * | 2002-07-11 | 2004-09-30 | 경동제약 주식회사 | 가라민 유도체의 제조방법 |
-
1978
- 1978-11-11 JP JP13840278A patent/JPS5564598A/ja active Granted
-
1979
- 1979-10-24 ZA ZA00795691A patent/ZA795691B/xx unknown
- 1979-11-09 BE BE2/58198A patent/BE879925A/fr not_active IP Right Cessation
- 1979-11-09 HU HU79ZA414A patent/HU183050B/hu unknown
- 1979-11-12 CS CS797711A patent/CS261853B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU183050B (en) | 1984-04-28 |
| CS261853B2 (en) | 1989-02-10 |
| ZA795691B (en) | 1980-11-26 |
| BE879925A (fr) | 1980-03-03 |
| CS771179A2 (en) | 1988-06-15 |
| JPS5564598A (en) | 1980-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4297485A (en) | Production of a selectively protected N-acylated derivative of an aminoglycosidic antibiotic | |
| JPS6127997A (ja) | ３，２′，６′−トリ−ｎ−アシル−３′，４′−ジデオキシカナマイシンｂ | |
| EP0218292B1 (fr) | Procédé pour la synthèse de l'amikacine | |
| JPS631319B2 (fr) | ||
| US4547492A (en) | 1-N-(ω-Amino-α-hydroxyalkanoyl-2',3'-dideoxykanamycin A and pharmaceutical composition containing same | |
| KR840001622B1 (ko) | 3-0-데메틸 이스타마이신 b의 제조방법 | |
| JPS631954B2 (fr) | ||
| KR830001613B1 (ko) | 아미노기를 선택적으로 보호한 아미노글리코사이드 항생물질의 제조방법 | |
| US4140849A (en) | Kanamycin C derivatives | |
| GB1589936A (en) | Processes for the production of 3',4'-dideoxykanamycin b | |
| JPS6332799B2 (fr) | ||
| JPS633874B2 (fr) | ||
| CA1131628A (fr) | Obtention d'un derive n-acyle protege selectivement, a partir d'un antibiotique aminoglycosidique | |
| JPH0134231B2 (fr) | ||
| JPS6312079B2 (fr) | ||
| EP0104125B1 (fr) | 5,2',3',4',4",6"-Hexadeoxykanamicine et son dérivé 1-N-acylé | |
| CA1152063A (fr) | 3',4'-DIDESOXYKANAMYCINE A ET SES DERIVES 1-N-((S-.alpha.-HYDROXY-.omega.-AMINOALCANOYL) | |
| JPS6310959B2 (fr) | ||
| JPS631951B2 (fr) | ||
| JPS6043356B2 (ja) | 耐性菌に有効なカナマイシンｃ誘導体およびそれらの製造法 | |
| JPH0631295B2 (ja) | 低毒性の２′−デアミノ−２′−ヒドロキシイスタマイシンＢｏ誘導体 | |
| JPH0134232B2 (fr) | ||
| IE48973B1 (en) | The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic | |
| JPS631317B2 (fr) | ||
| JPH0631296B2 (ja) | ２′，３′−ジデオキシ−２′−フルオロカナマイシンａ誘導体、およびその製造法 |