NL8103639A - Nieuwe 1-n-(alfa-hydroxy-omega-aminoalkanoyl)-derivaten van 5,3',4'-trideoxy-,5,3',4'-trideoxy-6'-methyl-of 5,3',4',6"-tetradeoxykanamycine-b, en werkwijze voor het bereiden daarvan. - Google Patents

Nieuwe 1-n-(alfa-hydroxy-omega-aminoalkanoyl)-derivaten van 5,3',4'-trideoxy-,5,3',4'-trideoxy-6'-methyl-of 5,3',4',6"-tetradeoxykanamycine-b, en werkwijze voor het bereiden daarvan. Download PDF

Info

Publication number: NL8103639A
Authority: NL; Netherlands
Prior art keywords: formula; amino; group; compound; trideoxy
Prior art date: 1980-08-12

Application number

NL8103639A

Other languages

English (en)

Dutch (nl)

Original Assignee

Microbial Chem Res Found

Priority date (The priority date 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 date listed.)

1980-08-12

Filing date

1981-07-31

Publication date

1982-03-01

1980-08-12 Priority claimed from JP55109854A external-priority patent/JPS5753496A/ja

1981-04-20 Priority claimed from JP56058389A external-priority patent/JPS57175198A/ja

1981-07-31 Application filed by Microbial Chem Res Found filed Critical Microbial Chem Res Found

1982-03-01 Publication of NL8103639A publication Critical patent/NL8103639A/nl

Links

238000000034 method Methods 0.000 title claims description 38
150000001875 compounds Chemical class 0.000 claims description 114
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
125000006239 protecting group Chemical group 0.000 claims description 51
-1 (S) -4-amino-2-hydroxybutyryl Chemical group 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 45
229960001192 bekanamycin Drugs 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 21
241000894006 Bacteria Species 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 13
230000001580 bacterial effect Effects 0.000 claims description 10
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 67
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
239000000047 product Substances 0.000 description 38
239000007858 starting material Substances 0.000 description 29
239000000843 powder Substances 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
229910021529 ammonia Inorganic materials 0.000 description 22
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
235000011114 ammonium hydroxide Nutrition 0.000 description 21
230000008569 process Effects 0.000 description 20
238000002360 preparation method Methods 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000003277 amino group Chemical group 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
238000005917 acylation reaction Methods 0.000 description 17
229960003807 dibekacin Drugs 0.000 description 16
239000000126 substance Substances 0.000 description 15
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229960001760 dimethyl sulfoxide Drugs 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
230000010933 acylation Effects 0.000 description 10
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 10
150000002148 esters Chemical class 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 8
229920001429 chelating resin Polymers 0.000 description 8
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 8
229930182824 kanamycin B Natural products 0.000 description 8
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 8
230000003287 optical effect Effects 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
UTUVRPOLEMRKQC-XDJMXTNXSA-N arbekacin sulfate Chemical compound OS(O)(=O)=O.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)CC[C@H]1N UTUVRPOLEMRKQC-XDJMXTNXSA-N 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
229940058499 habekacin Drugs 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 6
150000004682 monohydrates Chemical class 0.000 description 6
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229940125898 compound 5 Drugs 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
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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 4
150000007522 mineralic acids Chemical class 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000001629 suppression Effects 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
239000004246 zinc acetate Substances 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 3
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
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229930027917 kanamycin Natural products 0.000 description 3
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229910052987 metal hydride Inorganic materials 0.000 description 3
150000004681 metal hydrides Chemical class 0.000 description 3
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238000003756 stirring Methods 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
IWBTVBUNSFJIIE-UHFFFAOYSA-N 5-amino-2-hydroxypentanoic acid Chemical compound NCCCC(O)C(O)=O IWBTVBUNSFJIIE-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010033109 Ototoxicity Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
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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 2
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RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
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QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
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238000010253 intravenous injection Methods 0.000 description 2
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XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
IVUOMFWNDGNLBJ-UHFFFAOYSA-N 4-azaniumyl-2-hydroxybutanoate Chemical compound NCCC(O)C(O)=O IVUOMFWNDGNLBJ-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
101100337994 Arabidopsis thaliana GSO2 gene Proteins 0.000 description 1
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 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
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000231739 Rutilus rutilus Species 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
PAAZCQANMCYGAW-UHFFFAOYSA-N acetic acid;2,2,2-trifluoroacetic acid Chemical compound CC(O)=O.OC(=O)C(F)(F)F PAAZCQANMCYGAW-UHFFFAOYSA-N 0.000 description 1
AOZUYISQWWJMJC-UHFFFAOYSA-N acetic acid;methanol;hydrate Chemical compound O.OC.CC(O)=O AOZUYISQWWJMJC-UHFFFAOYSA-N 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
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229940126574 aminoglycoside antibiotic Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
230000000474 nursing effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910003445 palladium oxide Inorganic materials 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
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 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
- 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

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

NL8103639A 1980-08-12 1981-07-31 Nieuwe 1-n-(alfa-hydroxy-omega-aminoalkanoyl)-derivaten van 5,3',4'-trideoxy-,5,3',4'-trideoxy-6'-methyl-of 5,3',4',6"-tetradeoxykanamycine-b, en werkwijze voor het bereiden daarvan. NL8103639A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP55109854A JPS5753496A (en)	1980-08-12	1980-08-12	1-n-acyl derivative of 5,3',4'-trideoxykanamycin b or 5,3',4',6'- tetradeoxykanamycin b, and their preparation
JP10985480		1980-08-12
JP56058389A JPS57175198A (en)	1981-04-20	1981-04-20	1-n-acyl derivative of 5,3,4-trideoxy-6-n-methylkanamycin b and their preparation
JP5838981		1981-04-20

Publications (1)

Publication Number	Publication Date
NL8103639A true NL8103639A (nl)	1982-03-01

Family

ID=26399440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8103639A NL8103639A (nl)	1980-08-12	1981-07-31	Nieuwe 1-n-(alfa-hydroxy-omega-aminoalkanoyl)-derivaten van 5,3',4'-trideoxy-,5,3',4'-trideoxy-6'-methyl-of 5,3',4',6"-tetradeoxykanamycine-b, en werkwijze voor het bereiden daarvan.

Country Status (9)

Country	Link
KR (1)	KR850000979B1 (2)
CA (1)	CA1175816A (2)
CH (1)	CH648564A5 (2)
DE (1)	DE3131731C2 (2)
ES (4)	ES504697A0 (2)
FR (1)	FR2491073A1 (2)
GB (1)	GB2082575B (2)
IT (1)	IT1167959B (2)
NL (1)	NL8103639A (2)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS554118B2 (2) *	1973-08-29	1980-01-29

1981
- 1981-07-31 KR KR1019810002784A patent/KR850000979B1/ko not_active Expired
- 1981-07-31 NL NL8103639A patent/NL8103639A/nl active Search and Examination
- 1981-08-07 IT IT09493/81A patent/IT1167959B/it active
- 1981-08-10 CH CH5133/81A patent/CH648564A5/de not_active IP Right Cessation
- 1981-08-10 FR FR8115781A patent/FR2491073A1/fr active Granted
- 1981-08-11 GB GB8124490A patent/GB2082575B/en not_active Expired
- 1981-08-11 DE DE3131731A patent/DE3131731C2/de not_active Expired
- 1981-08-11 ES ES504697A patent/ES504697A0/es active Granted
- 1981-08-12 CA CA000383690A patent/CA1175816A/en not_active Expired
1982
- 1982-07-31 ES ES514621A patent/ES514621A0/es active Granted
- 1982-07-31 ES ES514620A patent/ES514620A0/es active Granted
- 1982-07-31 ES ES514622A patent/ES514622A0/es active Granted

Also Published As

Publication number	Publication date
ES8401093A1 (es)	1983-12-16
ES8308334A1 (es)	1983-08-16
ES514622A0 (es)	1983-08-16
ES8301486A1 (es)	1982-12-01
ES8401092A1 (es)	1983-12-16
FR2491073A1 (fr)	1982-04-02
DE3131731C2 (de)	1984-02-16
IT8109493A0 (it)	1981-08-07
ES514621A0 (es)	1983-12-16
FR2491073B1 (2)	1984-08-03
ES514620A0 (es)	1983-12-16
GB2082575A (en)	1982-03-10
ES504697A0 (es)	1982-12-01
KR850000979B1 (ko)	1985-07-05
KR830006325A (ko)	1983-09-24
GB2082575B (en)	1984-04-18
CA1175816A (en)	1984-10-09
CH648564A5 (de)	1985-03-29
DE3131731A1 (de)	1982-03-11
IT1167959B (it)	1987-05-20

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1987-10-01	BA	A request for search or an international-type search has been filed
1988-01-04	BB	A search report has been drawn up
1988-02-01	BC	A request for examination has been filed
1999-03-01	BN	A decision not to publish the application has become irrevocable

Publication	Publication Date	Title
US6835807B1 (en)	2004-12-28	Drug complex and drug delivery system
DE69919695T2 (de)	2005-09-15	Texaphyrin-konjugate und ihre anwendiung
AU2021203691B2 (en)	2023-02-23	Aminoglycoside derivatives and uses thereof in treating genetic disorders
JPS6368546A (ja)	1988-03-28	シス−白金錯化合物およびその製法
JPH07504922A (ja)	1995-06-01	１６員環マクロライド系抗生物質の誘導体
CZ285703B6 (cs)	1999-10-13	Amidové deriváty antibiotika A 40926
US4169141A (en)	1979-09-25	1-Peptidyl derivatives of di-O-aminoglycosyl-1,3-diaminocyclitol antibacterial agents
NL7906756A (nl)	1980-03-18	Aminoglycosiden en werkwijzen voor het bereiden van deze glycosiden en van genmeesmiddelen die ze bevatten.
NL8103639A (nl)	1982-03-01	Nieuwe 1-n-(alfa-hydroxy-omega-aminoalkanoyl)-derivaten van 5,3',4'-trideoxy-,5,3',4'-trideoxy-6'-methyl-of 5,3',4',6"-tetradeoxykanamycine-b, en werkwijze voor het bereiden daarvan.
EP3400232A1 (en)	2018-11-14	Aminoglycoside derivatives and uses thereof in treating genetic disorders
US20130203693A1 (en)	2013-08-08	4,6-substituted 2,5-dideoxystreptamine aminoglycoside antibiotics
DK149775B (da)	1986-09-29	Analogifremgangsmaade til fremstilling af 6'-n-methylkanamycin a- og b-derivater
KR840001622B1 (ko)	1984-10-12	3-0-데메틸 이스타마이신 b의 제조방법
Cassinelli et al.	1979	Synthesis and antitumor activity of 4'-O-methyldaunorubicin, 4'-O-methyladriamycin, and their 4'-epi analogs
US4472388A (en)	1984-09-18	N-Methanesulfonic acid derivatives of 3-O-demethylistamycin B and production thereof
CA1175818A (en)	1984-10-09	Derivatives of istamycins a and b and their preparation
GB2098219A (en)	1982-11-17	Daunorubicin-protein conjugates
US4547492A (en)	1985-10-15	1-N-(ω-Amino-α-hydroxyalkanoyl-2',3'-dideoxykanamycin A and pharmaceutical composition containing same
US4302449A (en)	1981-11-24	Carminomycin analogue
CA1050536A (en)	1979-03-13	3'-deoxybutirosin a
NL8402477A (nl)	1985-03-01	4'-halogeenantracyclineglycosiden.
CN101152195A (zh)	2008-04-02	一种氨基糖苷类抗生素在制备治疗耐药菌感染的药用组合物中的应用
US4140849A (en)	1979-02-20	Kanamycin C derivatives
GB1594780A (en)	1981-08-05	1-n-(aminoalkenesulfonyl)derivative of aminoglycosidic antibiotic and process for preparation thereof
AU656137B2 (en)	1995-01-27	Mitomycin derivatives having reduced bone marrow toxicity, processes for their preparation, and the uses thereof