BE494818A - - Google Patents

Info

Publication number

BE494818A

BE494818A BE494818DA BE494818A BE 494818 A BE494818 A BE 494818A BE 494818D A BE494818D A BE 494818DA BE 494818 A BE494818 A BE 494818A

Authority

BE

Belgium

Prior art keywords

streptomycin

dihydrostreptomycin

process according

catalyst

hydrogenation

Prior art date

Links

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• Global Dossier
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• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 41
• 229960005322 streptomycin Drugs 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 16
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
• ASXBYYWOLISCLQ-HZYVHMACSA-N dihydrostreptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O ASXBYYWOLISCLQ-HZYVHMACSA-N 0.000 claims description 13
• 229960002222 dihydrostreptomycin Drugs 0.000 claims description 12
• ASXBYYWOLISCLQ-UHFFFAOYSA-N Dihydrostreptomycin Natural products O1C(CO)C(O)C(O)C(NC)C1OC1C(CO)(O)C(C)OC1OC1C(N=C(N)N)C(O)C(N=C(N)N)C(O)C1O ASXBYYWOLISCLQ-UHFFFAOYSA-N 0.000 claims description 11
• 239000003054 catalyst Substances 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• 239000000243 solution Substances 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
• 239000007868 Raney catalyst Substances 0.000 claims description 3
• 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
• 239000007864 aqueous solution Substances 0.000 claims description 2
• 239000007858 starting material Substances 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• 238000005984 hydrogenation reaction Methods 0.000 description 13
• 238000006243 chemical reaction Methods 0.000 description 6
• 230000001066 destructive effect Effects 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 229910052759 nickel Inorganic materials 0.000 description 3
• XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• 239000010953 base metal Substances 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 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 1
• WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
• XGAKTAXPHNYSTK-RMIBZTJPSA-N 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;hydrochloride Chemical compound Cl.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O XGAKTAXPHNYSTK-RMIBZTJPSA-N 0.000 description 1
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 239000001110 calcium chloride Substances 0.000 description 1
• 229910001628 calcium chloride Inorganic materials 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 239000003729 cation exchange resin Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 230000008014 freezing Effects 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 229940043353 maltol Drugs 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 150000002739 metals Chemical class 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 229910000510 noble metal Inorganic materials 0.000 description 1
• 229910052763 palladium 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
• 229910052697 platinum Inorganic materials 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 239000012266 salt solution Substances 0.000 description 1
• 238000007086 side reaction Methods 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000010935 stainless steel Substances 0.000 description 1
• 229910001220 stainless steel Inorganic materials 0.000 description 1
• 229960002385 streptomycin sulfate Drugs 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1