PL94287B2 - - Google Patents

Info

Publication number

PL94287B2

PL94287B2 PL182512A PL18251275A PL94287B2 PL 94287 B2 PL94287 B2 PL 94287B2 PL 182512 A PL182512 A PL 182512A PL 18251275 A PL18251275 A PL 18251275A PL 94287 B2 PL94287 B2 PL 94287B2

Authority

PL

Poland

Prior art keywords

acid

zinc

water

reduction

adc

Prior art date

1975-08-02

Links

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• 238000000034 method Methods 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 26
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
• 229910052725 zinc Inorganic materials 0.000 claims description 14
• 239000011701 zinc Substances 0.000 claims description 14
• -1 2,2,2-trichlorethyl ester Chemical class 0.000 claims description 13
• PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
• 239000000203 mixture Substances 0.000 claims description 7
• 239000011541 reaction mixture Substances 0.000 claims description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 6
• 239000003960 organic solvent Substances 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 150000007524 organic acids Chemical class 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 3
• 150000002894 organic compounds Chemical class 0.000 claims description 3
• 125000002091 cationic group Chemical group 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 claims description 2
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
• 239000003795 chemical substances by application Substances 0.000 claims 2
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• 239000013522 chelant Substances 0.000 claims 1
• 229910052739 hydrogen Inorganic materials 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 claims 1
• 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
• 238000005342 ion exchange Methods 0.000 claims 1
• 239000011707 mineral Substances 0.000 claims 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000000243 solution Substances 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
• 238000001704 evaporation Methods 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000001556 precipitation Methods 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 229930186147 Cephalosporin Natural products 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 150000001768 cations Chemical class 0.000 description 3
• 229940124587 cephalosporin Drugs 0.000 description 3
• 150000002500 ions Chemical class 0.000 description 3
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
• VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 2
• 150000001780 cephalosporins Chemical class 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 230000008021 deposition Effects 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 229940049954 penicillin Drugs 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
• JTJMEBZVGQORDX-UHFFFAOYSA-N 2-aminobenzoic acid;zinc Chemical compound [Zn].NC1=CC=CC=C1C(O)=O JTJMEBZVGQORDX-UHFFFAOYSA-N 0.000 description 1
• 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 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 229960002588 cefradine Drugs 0.000 description 1
• ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
• 229940106164 cephalexin Drugs 0.000 description 1
• RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 238000006317 isomerization reaction Methods 0.000 description 1
• 150000002736 metal compounds Chemical class 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 238000011946 reduction process Methods 0.000 description 1
• 238000006722 reduction reaction Methods 0.000 description 1
• 231100000004 severe toxicity Toxicity 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1
• UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
• 229940007718 zinc hydroxide Drugs 0.000 description 1
• 229910021511 zinc hydroxide Inorganic materials 0.000 description 1