SU865128A3 - Способ получени 2-дезоксистрептаминаминогликозидов или их солей - Google Patents
Способ получени 2-дезоксистрептаминаминогликозидов или их солей Download PDFInfo
- Publication number
- SU865128A3 SU865128A3 SU772494017A SU2494017A SU865128A3 SU 865128 A3 SU865128 A3 SU 865128A3 SU 772494017 A SU772494017 A SU 772494017A SU 2494017 A SU2494017 A SU 2494017A SU 865128 A3 SU865128 A3 SU 865128A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- kanamycin
- alkyl
- solution
- group
- methanol
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical class 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 abstract description 20
- 229960000707 tobramycin Drugs 0.000 abstract description 7
- 229940126575 aminoglycoside Drugs 0.000 abstract description 5
- 229930027917 kanamycin Natural products 0.000 abstract description 5
- 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 abstract description 5
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 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 abstract 2
- 229930182566 Gentamicin Natural products 0.000 abstract 1
- 229930193140 Neomycin Natural products 0.000 abstract 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 abstract 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 abstract 1
- 229930190553 ribostamycin Natural products 0.000 abstract 1
- 229960003485 ribostamycin Drugs 0.000 abstract 1
- NSKGQURZWSPSBC-NLZFXWNVSA-N ribostamycin 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]2[C@@H]([C@@H](O)[C@H](CO)O2)O)[C@H](O)[C@@H](N)C[C@H]1N NSKGQURZWSPSBC-NLZFXWNVSA-N 0.000 abstract 1
- NSKGQURZWSPSBC-UHFFFAOYSA-N ribostamycin A Natural products NC1C(O)C(O)C(CN)OC1OC1C(OC2C(C(O)C(CO)O2)O)C(O)C(N)CC1N NSKGQURZWSPSBC-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 45
- 229960000318 kanamycin Drugs 0.000 description 29
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 23
- 239000000908 ammonium hydroxide Substances 0.000 description 23
- 229930182823 kanamycin A Natural products 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 229960001192 bekanamycin Drugs 0.000 description 18
- 229930182824 kanamycin B Natural products 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 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 11
- 239000002904 solvent 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
- 239000011780 sodium chloride Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- 229920001429 chelating resin Polymers 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 6
- -1 oxyl groups Chemical group 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
- 229920005654 Sephadex Polymers 0.000 description 5
- 239000012507 Sephadex™ Substances 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 2
- 206010056474 Erythrosis Diseases 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Inorganic materials [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GZMYLSJUNSCMTD-MOPGFXCFSA-N OC[C@@H](C)NC1=NC(=CC(=C1)C=1C=C(C=CC=1C)NC(=O)N1C[C@@H](CC1)CC(F)(F)F)N1CCOCC1 Chemical compound OC[C@@H](C)NC1=NC(=CC(=C1)C=1C=C(C=CC=1C)NC(=O)N1C[C@@H](CC1)CC(F)(F)F)N1CCOCC1 GZMYLSJUNSCMTD-MOPGFXCFSA-N 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PYMYPHUHKUWMLA-MROZADKFSA-N aldehydo-L-ribose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-MROZADKFSA-N 0.000 description 1
- PYMYPHUHKUWMLA-WISUUJSJSA-N aldehydo-L-xylose Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WISUUJSJSA-N 0.000 description 1
- 229930195726 aldehydo-L-xylose Natural products 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000027096 gram-negative bacterial infections Diseases 0.000 description 1
- 208000027136 gram-positive bacterial infections Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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
- C07H15/22—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
-
- 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
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)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24989/76A GB1530202A (en) | 1976-06-16 | 1976-06-16 | Aminoglycosides |
| GB4014576 | 1976-09-28 | ||
| GB5129476 | 1976-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU865128A3 true SU865128A3 (ru) | 1981-09-15 |
Family
ID=27258386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772494017A SU865128A3 (ru) | 1976-06-16 | 1977-06-15 | Способ получени 2-дезоксистрептаминаминогликозидов или их солей |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4214074A (enExample) |
| JP (1) | JPS52153943A (enExample) |
| AR (1) | AR222781A1 (enExample) |
| AT (1) | AT350722B (enExample) |
| BG (1) | BG28071A3 (enExample) |
| CA (1) | CA1075235A (enExample) |
| CH (1) | CH606079A5 (enExample) |
| CS (1) | CS203157B2 (enExample) |
| DD (1) | DD131019A5 (enExample) |
| DE (1) | DE2726839C3 (enExample) |
| DK (1) | DK147942C (enExample) |
| EG (1) | EG12742A (enExample) |
| ES (1) | ES459832A1 (enExample) |
| FI (1) | FI771873A7 (enExample) |
| FR (1) | FR2355029A1 (enExample) |
| GR (1) | GR66411B (enExample) |
| HU (1) | HU179054B (enExample) |
| IE (1) | IE45389B1 (enExample) |
| IL (1) | IL52181A (enExample) |
| LU (1) | LU77557A1 (enExample) |
| MX (1) | MX4323E (enExample) |
| NL (1) | NL170736C (enExample) |
| NO (1) | NO144851C (enExample) |
| NZ (1) | NZ184213A (enExample) |
| PH (1) | PH14663A (enExample) |
| PL (1) | PL108094B1 (enExample) |
| PT (1) | PT66669B (enExample) |
| RO (1) | RO73516A (enExample) |
| SE (1) | SE7706944L (enExample) |
| SU (1) | SU865128A3 (enExample) |
| YU (1) | YU132577A (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK308878A (da) * | 1977-08-18 | 1979-02-19 | Pfizer | Aminoglyosidderivater og fremgangsmaader til deres fremstilling |
| DE2832268A1 (de) | 1978-07-22 | 1980-01-31 | Bayer Ag | Pseudotrisaccharide |
| DE2928183A1 (de) * | 1979-07-12 | 1981-01-29 | Bayer Ag | 1-n-alkylsisomicin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| JPS5931266A (ja) * | 1982-08-11 | 1984-02-20 | 株式会社日立製作所 | エレベ−タ−の制御装置 |
| KR100450607B1 (ko) * | 2002-07-11 | 2004-09-30 | 경동제약 주식회사 | 가라민 유도체의 제조방법 |
| US7794713B2 (en) | 2004-04-07 | 2010-09-14 | Lpath, Inc. | Compositions and methods for the treatment and prevention of hyperproliferative diseases |
| US7862812B2 (en) | 2006-05-31 | 2011-01-04 | Lpath, Inc. | Methods for decreasing immune response and treating immune conditions |
| HRP20170154T1 (hr) | 2007-11-21 | 2017-03-24 | Achaogen, Inc. | Analozi antibakterijskog aminoglikozida |
| CA2761756A1 (en) * | 2009-05-14 | 2010-11-18 | Achaogen, Inc. | Treatment of urinary tract infections with antibacterial aminoglycoside compounds |
| WO2010132760A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of tobramycin |
| WO2010132768A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of sisomicin |
| WO2010132757A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132765A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132759A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of dibekacin |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1033394A (en) * | 1962-04-03 | 1966-06-22 | Rit Rech Ind Therapeut | New therapeutic agents |
| US4002742A (en) * | 1974-03-19 | 1977-01-11 | Schering Corporation | 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods for their manufacture, methods for their use as antibacterial agents, and compositions useful therefor |
| US4000261A (en) * | 1974-11-29 | 1976-12-28 | Schering Corporation | 5-epi-4,6-di-o-(aminoglycosyl)-2-deoxystreptamines, methods for their manufacture and intermediates useful therein, methods for their use as antibacterial agents and compositions useful therefor |
| US4000262A (en) * | 1974-11-29 | 1976-12-28 | Schering Corporation | 5-epi-amino and 5-epi-azido-4,6-di-o-(aminoglycosyl)-2,5-dideoxystreptamines 1-n-alkyl-5-epi-amino and 1-n-alkyl-5-epi-azido-4,6-di-o-(aminoglycosyl)-2,5-dideoxystreptamines |
| US4062947A (en) * | 1975-11-04 | 1977-12-13 | Schering Corporation | Di-N-alkylaminoglycosides, methods for their manufacture and novel intermediates useful therein, method for their use as antibacterial agents and pharmaceutical compositions useful therefor |
| US4085208A (en) * | 1976-06-21 | 1978-04-18 | Schering Corporation | Process for preparing 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols and novel 1-epimers and 1-N-alkyl derivatives produced thereby; methods for the use of the 1-epimer derivatives as antibacterial agents and compositions useful therefor |
-
1977
- 1977-05-26 NZ NZ184213A patent/NZ184213A/xx unknown
- 1977-05-27 YU YU01325/77A patent/YU132577A/xx unknown
- 1977-05-27 IL IL52181A patent/IL52181A/xx unknown
- 1977-05-30 EG EG329/77A patent/EG12742A/xx active
- 1977-05-31 PH PH19833A patent/PH14663A/en unknown
- 1977-06-02 MX MX775775U patent/MX4323E/es unknown
- 1977-06-03 CA CA279,773A patent/CA1075235A/en not_active Expired
- 1977-06-03 AR AR267934A patent/AR222781A1/es active
- 1977-06-08 CS CS773790A patent/CS203157B2/cs unknown
- 1977-06-13 AT AT414277A patent/AT350722B/de not_active IP Right Cessation
- 1977-06-13 BG BG036611A patent/BG28071A3/xx unknown
- 1977-06-14 NL NLAANVRAGE7706514,A patent/NL170736C/xx not_active IP Right Cessation
- 1977-06-14 GR GR53699A patent/GR66411B/el unknown
- 1977-06-14 PT PT66669A patent/PT66669B/pt unknown
- 1977-06-14 DE DE2726839A patent/DE2726839C3/de not_active Expired
- 1977-06-14 NO NO772089A patent/NO144851C/no unknown
- 1977-06-14 FI FI771873A patent/FI771873A7/fi not_active Application Discontinuation
- 1977-06-15 SU SU772494017A patent/SU865128A3/ru active
- 1977-06-15 JP JP7094477A patent/JPS52153943A/ja active Granted
- 1977-06-15 CH CH737577A patent/CH606079A5/xx not_active IP Right Cessation
- 1977-06-15 FR FR7718367A patent/FR2355029A1/fr active Granted
- 1977-06-15 IE IE1222/77A patent/IE45389B1/en unknown
- 1977-06-15 PL PL1977198872A patent/PL108094B1/pl not_active IP Right Cessation
- 1977-06-15 SE SE7706944A patent/SE7706944L/xx not_active Application Discontinuation
- 1977-06-15 HU HU77PI580A patent/HU179054B/hu unknown
- 1977-06-15 DD DD7700199503A patent/DD131019A5/xx unknown
- 1977-06-15 DK DK265577A patent/DK147942C/da not_active IP Right Cessation
- 1977-06-15 RO RO7790693A patent/RO73516A/ro unknown
- 1977-06-16 ES ES459832A patent/ES459832A1/es not_active Expired
- 1977-06-16 LU LU77557A patent/LU77557A1/xx unknown
-
1978
- 1978-11-07 US US05/958,409 patent/US4214074A/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU865128A3 (ru) | Способ получени 2-дезоксистрептаминаминогликозидов или их солей | |
| US3753973A (en) | The preparation of 3'-4'-dideoxykanamycin b active against resistant bacteria | |
| US4001208A (en) | 1-N-[(S)-α-hydroxy-ω-aminoacyl] | |
| US4107424A (en) | 1-N-[(S)-α-hydroxy-ω-aminoacyl] derivatives of 3',4'-dideoxykanamycin B and 3'-deoxykanamycin B antibiotics | |
| US4170642A (en) | Derivatives of kanamycin A | |
| US4120955A (en) | Method for production of kanamycin C and its derivatives | |
| Yasuzawa et al. | CV-1, a new antibiotic produced by a strain of Streptomyces sp. II. structure determination | |
| US4145253A (en) | Process for producing fortimicin factors | |
| US4296106A (en) | Istamycins and production thereof | |
| Umezawa et al. | Synthesis of paromamine | |
| HU177271B (en) | Process for preparing neamine-6-0- and -3-0-d-glycosyl analogues | |
| US4008362A (en) | 1-N-((S)-α-substituted-ω-aminoacyl)-neamine or -ribostamycin and the production thereof | |
| US4140849A (en) | Kanamycin C derivatives | |
| US4330673A (en) | Process for producing 3-O-demethylaminoglycoside and novel 3-O-demethylfortimicin derivatives | |
| Nishimura et al. | Studies on Aminosugars. XXVII. Synthesis of Several Glycosides Containing (6-Amino-6-deoxy-D-glucopyranosyl)-2-deoxystreptamine | |
| US4332794A (en) | 6"-Deoxydibekacin, 4",6"-dideoxydibekacin and 1-N-aminoacyl derivatives thereof, and the production of these new compounds | |
| US4008218A (en) | 1-N-((S)-α-substituted-ω-aminoacyl)-neamine or -ribostamycin and the production thereof | |
| US4214077A (en) | 1-N-Substituted derivatives of seldomycin factor 5 | |
| TSUNAKAWA et al. | Inosamycin, a Complex of new Aminoglycoside Antibiotics II. Structure Determination | |
| EP0546179B1 (en) | 4-o-(aminoglycosyl)- or 4,6-di-o-(aminoglycosyl)-2,5-dideoxy-5,5-difluorostreptamine derivative and production thereof | |
| US4634688A (en) | 3'-fluoro-3'-deoxykanamycin A | |
| Nishimura et al. | A synthesis of 3', 4'-dideoxykanamycin B. | |
| Suami et al. | Chemical modification of fortimicin A | |
| US4213974A (en) | 4-N,2'-N and 4,2'-Di-N-fortimicin AO derivatives | |
| KR820000753B1 (ko) | 2-데옥시스트렙타민 아미노글리코사이드류의 제조방법 |