CS257292B2 - Production method of amikacine - Google Patents

Production method of amikacine Download PDF

Info

Publication number: CS257292B2
Authority: CS; Czechoslovakia
Prior art keywords: kanamycin; metal cation; formula; amikacin; complex
Prior art date: 1985-10-10

Application number

CS865913A

Other languages

Czech (cs)

English (en)

Inventor

Alberto Mangia

Vicenzo Giobbio

Giorgio Ornato

Original Assignee

Pierrel Spa

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.)

1985-10-10

Filing date

1986-08-07

Publication date

1988-04-15

1986-08-07 Application filed by Pierrel Spa filed Critical Pierrel Spa

1988-04-15 Publication of CS257292B2 publication Critical patent/CS257292B2/cs

Links

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 title claims abstract description 40
238000004519 manufacturing process Methods 0.000 title claims description 4
229960004821 amikacin Drugs 0.000 claims abstract description 39
229960000318 kanamycin Drugs 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 32
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 claims abstract description 31
229930182823 kanamycin A Natural products 0.000 claims abstract description 25
229910052751 metal Inorganic materials 0.000 claims abstract description 18
239000002184 metal Substances 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001768 cations Chemical class 0.000 claims abstract description 13
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 7
239000002904 solvent Substances 0.000 claims abstract description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052802 copper Inorganic materials 0.000 claims abstract description 5
239000010949 copper Substances 0.000 claims abstract description 5
229910052759 nickel Inorganic materials 0.000 claims abstract description 5
229910052725 zinc Inorganic materials 0.000 claims abstract description 5
239000011701 zinc Substances 0.000 claims abstract description 5
229910052793 cadmium Inorganic materials 0.000 claims abstract description 4
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 4
229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
239000010941 cobalt Substances 0.000 claims abstract description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052742 iron Inorganic materials 0.000 claims abstract description 4
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 4
239000006184 cosolvent Substances 0.000 claims abstract description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
-1 aliphatic alcohols Chemical class 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
229930027917 kanamycin Natural products 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
IVUOMFWNDGNLBJ-VKHMYHEASA-N (2s)-4-amino-2-hydroxybutanoic acid Chemical class NCC[C@H](O)C(O)=O IVUOMFWNDGNLBJ-VKHMYHEASA-N 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 4
230000009918 complex formation Effects 0.000 claims description 4
239000004246 zinc acetate Substances 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
239000000908 ammonium hydroxide Substances 0.000 claims description 2
IVUOMFWNDGNLBJ-UHFFFAOYSA-N 4-azaniumyl-2-hydroxybutanoate Chemical compound NCCC(O)C(O)=O IVUOMFWNDGNLBJ-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
229940006486 zinc cation Drugs 0.000 claims 1
230000010933 acylation Effects 0.000 abstract description 20
238000005917 acylation reaction Methods 0.000 abstract description 20
238000006243 chemical reaction Methods 0.000 abstract description 20
125000006239 protecting group Chemical group 0.000 abstract description 15
238000003786 synthesis reaction Methods 0.000 abstract description 10
230000015572 biosynthetic process Effects 0.000 abstract description 9
238000000746 purification Methods 0.000 abstract description 4
238000011065 in-situ storage Methods 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 17
125000003277 amino group Chemical group 0.000 description 15
239000000243 solution Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
239000000543 intermediate Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
238000007327 hydrogenolysis reaction Methods 0.000 description 5
SWOHHBNJQHDNFM-WYSMZKEGSA-N (2s)-4-amino-n-[(1s,2r,3r,4s,5r)-5-amino-4-[(2s,3r,4s,5s,6r)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2r,3r,4s,5s,6r)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide;sulfuric acid Chemical compound OS(O)(=O)=O.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](O)[C@H](O)[C@@H](CN)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O SWOHHBNJQHDNFM-WYSMZKEGSA-N 0.000 description 4
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 3
229960000314 zinc acetate Drugs 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
229940057499 anhydrous zinc acetate Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004255 ion exchange chromatography Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
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 2
230000002906 microbiologic effect Effects 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
238000005406 washing Methods 0.000 description 2
DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 2
HDXVFGYNQCBFKD-JGWLITMVSA-N (2r,3s,4r,5r)-6-amino-2,3,4,5-tetrahydroxyhexanal Chemical group NC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O HDXVFGYNQCBFKD-JGWLITMVSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
DTFAJAKTSMLKAT-JDCCYXBGSA-N 2-deoxystreptamine Chemical group N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O DTFAJAKTSMLKAT-JDCCYXBGSA-N 0.000 description 1
ULKOBRDRCYROKY-UHFFFAOYSA-N 2-hydroxy-4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound OC(=O)C(O)CCNC(=O)OCC1=CC=CC=C1 ULKOBRDRCYROKY-UHFFFAOYSA-N 0.000 description 1
YWMSSKBMOFPBDM-UHFFFAOYSA-N 4-carbamoylbenzenesulfonyl chloride Chemical compound NC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 YWMSSKBMOFPBDM-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
FOEXHEVNPRRHDY-SLPGGIOYSA-N aldehydo-D-kanosamine Chemical group O=C[C@H](O)[C@@H](N)[C@H](O)[C@H](O)CO FOEXHEVNPRRHDY-SLPGGIOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229960001656 amikacin sulfate Drugs 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
229940126574 aminoglycoside antibiotic Drugs 0.000 description 1
239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910001412 inorganic anion Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical compound OS(O)(=O)=O.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 OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
229960002064 kanamycin sulfate Drugs 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002891 organic anions Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Floor Finish (AREA)
Materials For Medical Uses (AREA)
Removal Of Specific Substances (AREA)
Peptides Or Proteins (AREA)
Quinoline Compounds (AREA)

CS865913A 1985-10-10 1986-08-07 Production method of amikacine CS257292B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT22425/85A IT1200774B (it)	1985-10-10	1985-10-10	Procedimento di sentisi dell'amikacina

Publications (1)

Publication Number	Publication Date
CS257292B2 true CS257292B2 (en)	1988-04-15

Family

ID=11196139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS865913A CS257292B2 (en)	1985-10-10	1986-08-07	Production method of amikacine

Country Status (21)

Country	Link
US (1)	US4902790A (fr)
EP (1)	EP0218292B1 (fr)
JP (1)	JPS6293297A (fr)
KR (1)	KR910005897B1 (fr)
AT (1)	ATE55391T1 (fr)
AU (1)	AU603998B2 (fr)
BG (1)	BG50164A3 (fr)
CA (1)	CA1296331C (fr)
CS (1)	CS257292B2 (fr)
DD (1)	DD258991A1 (fr)
DE (1)	DE3673305D1 (fr)
DK (1)	DK166829B1 (fr)
HU (1)	HU196421B (fr)
IT (1)	IT1200774B (fr)
NO (1)	NO165297C (fr)
NZ (1)	NZ217862A (fr)
PH (1)	PH22748A (fr)
PL (1)	PL147396B1 (fr)
RU (1)	RU1771477C (fr)
YU (1)	YU44579B (fr)
ZA (1)	ZA867440B (fr)

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IT1225484B (it) *	1987-11-27	1990-11-14	Pierrel Spa	Procedimento di sintesi dell'amikacina
IT1237490B (it) *	1989-09-22	1993-06-07	Chementecno S R L Monza Milano	Procedimento per la sintesi della 1 n (s delta ammino alfa idrossibutirril)kamanycin a basato sul trattamento della 1 n (s delta benzilossicarbonilammino alfa idrossibutirril) 3,6' di n benzilossicarbonilkanamycin a con acido formico
YU45590A (sh) *	1990-03-07	1992-07-20	PLIVA FARMACEVTSKA, KEMIJSKA, PREHRAMBENA I KOZMETIČKA INDUSTRIJA s.p.o.	Novi kompleksi odnosno helati antibiotika s dvovalentnim i/ili trovalentnim metalima i postupci za njihovo dobijanje
EP0446670B1 (fr) *	1990-03-08	1994-09-21	Biochimica Opos Spa	Procédé de préparation de précurseurs d'amikacine
US6653456B2 (en) *	2001-07-31	2003-11-25	Roche Diagnostics Corporation	Site-specific aminoglycoside derivatives and their use in immunodiagnostic assays
WO2003072735A2 (fr) *	2002-02-22	2003-09-04	New River Pharmaceuticals Inc.	Utilisation de la conjugaison peptide-medicament pour diminuer la variabilite entre sujets de niveaux de serum de medicament
US7794713B2 (en) *	2004-04-07	2010-09-14	Lpath, Inc.	Compositions and methods for the treatment and prevention of hyperproliferative diseases
US20090074720A1 (en) *	2005-10-28	2009-03-19	Sabbadini Roger A	Methods for decreasing immune response and treating immune conditions
US20080213274A1 (en) *	2005-10-28	2008-09-04	Sabbadini Roger A	Compositions and methods for the treatment and prevention of fibrotic, inflammatory, and neovascularization conditions of the eye
US7862812B2 (en) *	2006-05-31	2011-01-04	Lpath, Inc.	Methods for decreasing immune response and treating immune conditions
US8791245B2 (en) *	2008-10-03	2014-07-29	Glycan Bioscience LLC	Anionic conjugates of glycosylated bacterial metabolite
CN103113429B (zh) *	2013-03-05	2015-02-18	齐鲁天和惠世制药有限公司	一种由阿米卡星制备硫酸阿米卡星的方法
CN105440090B (zh) *	2014-08-27	2018-03-09	北大医药重庆大新药业股份有限公司	一种阿米卡星的合成方法
CN111138505B (zh) *	2020-02-17	2021-10-08	山东安信制药有限公司	一种阿米卡星的制备方法

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US4230847A (en) *	1976-06-17	1980-10-28	Schering Corporation	Aminoglycoside antibiotic compounds
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
IE48972B1 (en) *	1978-11-11	1985-06-26	Microbial Chem Res Found	The production of a selectively protected n-acylated derivative of an aminoglycosidic antibiotic
JPS5782399A (en) *	1980-09-22	1982-05-22	Lilly Co Eli	2-deoxystreptamine aminoglycoside derivative and manufacture
US4424344A (en) *	1980-09-22	1984-01-03	Eli Lilly And Company	2-N-Acylated and 2-N-alkylated derivatives of 4-O-substituted-2-deoxystreptamine aminoglycosides and process
US4468513A (en) *	1980-09-22	1984-08-28	Eli Lilly And Company	2'-N-Acylated and 2'-N-alkylated derivatives of 4-O-substituted-2-deoxystreptamine aminoglycosides

1985
- 1985-10-10 IT IT22425/85A patent/IT1200774B/it active
1986
- 1986-06-23 YU YU1086/86A patent/YU44579B/xx unknown
- 1986-06-30 HU HU862726A patent/HU196421B/hu not_active IP Right Cessation
- 1986-07-10 BG BG075682A patent/BG50164A3/xx unknown
- 1986-07-11 DD DD86292400A patent/DD258991A1/de not_active IP Right Cessation
- 1986-07-14 PL PL1986260615A patent/PL147396B1/pl unknown
- 1986-08-07 CS CS865913A patent/CS257292B2/cs unknown
- 1986-09-25 AT AT86201663T patent/ATE55391T1/de active
- 1986-09-25 DE DE8686201663T patent/DE3673305D1/de not_active Expired - Lifetime
- 1986-09-25 EP EP86201663A patent/EP0218292B1/fr not_active Expired - Lifetime
- 1986-09-30 ZA ZA867440A patent/ZA867440B/xx unknown
- 1986-10-02 US US06/914,451 patent/US4902790A/en not_active Expired - Fee Related
- 1986-10-03 DK DK475186A patent/DK166829B1/da not_active IP Right Cessation
- 1986-10-07 CA CA000520035A patent/CA1296331C/fr not_active Expired - Lifetime
- 1986-10-08 KR KR1019860008418A patent/KR910005897B1/ko not_active Expired
- 1986-10-08 PH PH34334A patent/PH22748A/en unknown
- 1986-10-08 NO NO864011A patent/NO165297C/no unknown
- 1986-10-09 AU AU63633/86A patent/AU603998B2/en not_active Ceased
- 1986-10-09 RU SU864028258A patent/RU1771477C/ru active
- 1986-10-09 JP JP61239398A patent/JPS6293297A/ja active Granted
- 1986-10-09 NZ NZ217862A patent/NZ217862A/xx unknown

Also Published As

Publication number	Publication date
PL147396B1 (en)	1989-05-31
ATE55391T1 (de)	1990-08-15
EP0218292B1 (fr)	1990-08-08
CA1296331C (fr)	1992-02-25
DE3673305D1 (de)	1990-09-13
RU1771477C (ru)	1992-10-23
YU108686A (en)	1987-12-31
HUT43084A (en)	1987-09-28
IT8522425A0 (it)	1985-10-10
JPS6293297A (ja)	1987-04-28
DD258991A1 (de)	1988-08-10
NO165297C (no)	1991-01-23
PL260615A1 (en)	1987-06-15
IT1200774B (it)	1989-01-27
BG50164A3 (en)	1992-05-15
PH22748A (en)	1988-11-28
KR910005897B1 (ko)	1991-08-06
NZ217862A (en)	1990-06-26
NO165297B (no)	1990-10-15
DK475186A (da)	1987-04-11
EP0218292A1 (fr)	1987-04-15
AU603998B2 (en)	1990-12-06
ZA867440B (en)	1987-06-24
JPH0212958B2 (fr)	1990-03-30
KR870004050A (ko)	1987-05-07
AU6363386A (en)	1987-04-16
DK475186D0 (da)	1986-10-03
NO864011D0 (no)	1986-10-08
YU44579B (en)	1990-10-31
US4902790A (en)	1990-02-20
HU196421B (en)	1988-11-28
NO864011L (no)	1987-04-13
DK166829B1 (da)	1993-07-19

Publication	Publication Date	Title
KR920002142B1 (ko)	1992-03-12	에리트로마이신 a 유도체의 선택적인 메틸화 방법
GB1575982A (en)	1980-10-01	Process of selectivity blocking amino groups
EP0218292B1 (fr)	1990-08-08	Procédé pour la synthèse de l'amikacine
CA1324375C (fr)	1993-11-16	Procede pour la synthese de l'amikacine
US4337335A (en)	1982-06-29	Transition metal salt complexes of polyamino organic compounds
JP2502412B2 (ja)	1996-05-29	アミカシン前駆体の製造方法
US4003922A (en)	1977-01-18	Synthesis of cis-1,4-cyclohexadiene dioxide
US5696244A (en)	1997-12-09	Method for preparing 1-N-ethylsisomicin
KR900001076B1 (ko)	1990-02-26	N-[4-(3-아미노프로필)아미노부틸]-2,2-디히드록시에탄아미드의 제조방법
US4812478A (en)	1989-03-14	Derivatives of L-amino acyl L-carnitine, process for their preparation and pharmaceutical compositions having hepatoprotecting activity containing same
JPS5811879B2 (ja)	1983-03-04	コウサイキンザイノセイホウ
GB1594786A (en)	1981-08-05	Fortimicin derivatives and method for production thereof
EP0048613B1 (fr)	1985-01-23	Dérivés de 2-désoxystreptamine-aminoglycosides-4-0-substitués, leur préparation et compositions les contenant
KR830002204B1 (ko)	1983-10-19	카나마이신 a 유도체의 제조 방법
KR790000960B1 (ko)	1979-08-14	3',4'-디데스옥시 가나마이신 b의 제조방법
JPH0130837B2 (fr)	1989-06-22
Tanaka et al.	1981	CHEMICAL MODIFICATION OF ANTHRACYCLINE ANTIBIOTICS. III 4
KR910003429B1 (ko)	1991-05-31	아미노글리코사이드계 항생물질 유도체의 제조방법
KR790001304B1 (ko)	1979-09-24	항생물질의 제조방법
KR20210077946A (ko)	2021-06-28	우리딘 5’-디인산(udp), 이의 염 또는 이의 수화물의 제조방법
JPS631317B2 (fr)	1988-01-12
JPS631950B2 (fr)	1988-01-14
JPH0134232B2 (fr)	1989-07-18
JPS6332799B2 (fr)	1988-07-01
JPS6310959B2 (fr)	1988-03-10