NO115254B - - Google Patents
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- Publication number
- NO115254B NO115254B NO138179A NO13817960A NO115254B NO 115254 B NO115254 B NO 115254B NO 138179 A NO138179 A NO 138179A NO 13817960 A NO13817960 A NO 13817960A NO 115254 B NO115254 B NO 115254B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- penicillin
- aminopenicillanic
- acids
- solution
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 claims description 43
- 150000002960 penicillins Chemical class 0.000 claims description 25
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 24
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 19
- -1 mercapto compounds Chemical class 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 12
- 102000004190 Enzymes Human genes 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 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 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229940049954 penicillin Drugs 0.000 description 29
- 230000000694 effects Effects 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 20
- 230000001580 bacterial effect Effects 0.000 description 19
- 229940056360 penicillin g Drugs 0.000 description 19
- 239000000725 suspension Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 238000006911 enzymatic reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- 239000008055 phosphate buffer solution Substances 0.000 description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- IKODIMKOCSGKHQ-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1Cl IKODIMKOCSGKHQ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- WMQCHKLNXUXWQJ-UHFFFAOYSA-N 4-(2-chlorophenoxy)-2-hydroxy-3-oxobutanoic acid Chemical compound OC(C(O)=O)C(=O)COC1=C(Cl)C=CC=C1 WMQCHKLNXUXWQJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZANZGGBOONMBTC-UHFFFAOYSA-N CC(C(C(C(O)=O)S)=O)OC1=CC=CC=C1 Chemical compound CC(C(C(C(O)=O)S)=O)OC1=CC=CC=C1 ZANZGGBOONMBTC-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010087702 Penicillinase Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229950009506 penicillinase Drugs 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BDSSZTXPZHIYHM-UHFFFAOYSA-N 2-phenoxypropanoyl chloride Chemical compound ClC(=O)C(C)OC1=CC=CC=C1 BDSSZTXPZHIYHM-UHFFFAOYSA-N 0.000 description 2
- JMDHAJAGWXYICI-UHFFFAOYSA-N 4-(2-chlorophenoxy)-3-oxo-2-sulfanylbutanoic acid Chemical compound ClC1=C(OCC(=O)C(C(=O)O)S)C=CC=C1 JMDHAJAGWXYICI-UHFFFAOYSA-N 0.000 description 2
- AHCPXFAEPQNEJM-UHFFFAOYSA-N 4-(4-methoxyphenoxy)-3-oxo-2-sulfanylbutanoic acid Chemical compound COC1=CC=C(OCC(=O)C(C(=O)O)S)C=C1 AHCPXFAEPQNEJM-UHFFFAOYSA-N 0.000 description 2
- OBWCTIYGJXKKCZ-UHFFFAOYSA-N 4-(4-nitrophenoxy)-3-oxo-2-sulfanylbutanoic acid Chemical compound [N+](=O)([O-])C1=CC=C(OCC(=O)C(C(=O)O)S)C=C1 OBWCTIYGJXKKCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WDTIEXOUEVMYAD-UHFFFAOYSA-N OC(C(C(COC(C(Cl)=CC=C1)=C1Cl)=O)S)=O Chemical compound OC(C(C(COC(C(Cl)=CC=C1)=C1Cl)=O)S)=O WDTIEXOUEVMYAD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- JUUYZCCKKAMCFI-UHFFFAOYSA-N phenyl 2-(2-chlorophenoxy)acetate Chemical compound ClC1=CC=CC=C1OCC(=O)OC1=CC=CC=C1 JUUYZCCKKAMCFI-UHFFFAOYSA-N 0.000 description 2
- JFOZPCWVLIBFCH-UHFFFAOYSA-M potassium;2-phenylacetate Chemical compound [K+].[O-]C(=O)CC1=CC=CC=C1 JFOZPCWVLIBFCH-UHFFFAOYSA-M 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- BWRPEDIXOHZKFD-UHFFFAOYSA-N 2,2-diphenoxyacetic acid Chemical compound C=1C=CC=CC=1OC(C(=O)O)OC1=CC=CC=C1 BWRPEDIXOHZKFD-UHFFFAOYSA-N 0.000 description 1
- RPNBBIYJWHBRED-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=C(Cl)C=CC=C1Cl RPNBBIYJWHBRED-UHFFFAOYSA-N 0.000 description 1
- JVXJGLIGBHCEDP-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetyl chloride Chemical compound COC1=CC=C(OCC(Cl)=O)C=C1 JVXJGLIGBHCEDP-UHFFFAOYSA-N 0.000 description 1
- FLUYDOVOMDZUEV-UHFFFAOYSA-N 2-(4-nitrophenoxy)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(OCC(Cl)=O)C=C1 FLUYDOVOMDZUEV-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical compound CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 description 1
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- WYPCNYPOTCATPW-UHFFFAOYSA-N 3-oxo-5-phenoxy-2-sulfanylpentanoic acid Chemical compound O(C1=CC=CC=C1)CCC(=O)C(C(=O)O)S WYPCNYPOTCATPW-UHFFFAOYSA-N 0.000 description 1
- XBZQFHGGHQSHOQ-UHFFFAOYSA-N 4-(2-chlorophenoxy)-3-oxo-2-sulfanylbutanamide Chemical compound ClC1=C(OCC(=O)C(C(=O)N)S)C=CC=C1 XBZQFHGGHQSHOQ-UHFFFAOYSA-N 0.000 description 1
- 241000186063 Arthrobacter Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 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 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- PTSRBZOZSRJCKX-JTQLQIEISA-N N-Phenylacetylglutamic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)CC1=CC=CC=C1 PTSRBZOZSRJCKX-JTQLQIEISA-N 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- BZCKRPHEZOHHBK-UHFFFAOYSA-N methyl 2-phenoxyacetate Chemical compound COC(=O)COC1=CC=CC=C1 BZCKRPHEZOHHBK-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WINGEFIITRDOLJ-UHFFFAOYSA-N tert-butyl 2-hydroxyacetate Chemical compound CC(C)(C)OC(=O)CO WINGEFIITRDOLJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
- C12P37/04—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by acylation of the substituent in the 6 position
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/848—Escherichia
- Y10S435/849—Escherichia coli
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30003A DE1151803B (de) | 1959-12-04 | 1959-12-04 | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115254B true NO115254B (sv) | 1968-09-09 |
Family
ID=7093558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO138179A NO115254B (sv) | 1959-12-04 | 1960-11-30 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3079306A (sv) |
| BE (1) | BE597759A (sv) |
| BR (1) | BR6024673D0 (sv) |
| DE (1) | DE1151803B (sv) |
| DK (1) | DK127254B (sv) |
| GB (1) | GB904576A (sv) |
| NO (1) | NO115254B (sv) |
| SE (1) | SE304269B (sv) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB878233A (en) * | 1959-01-22 | 1961-09-27 | Beecham Res Lab | Improvements in or relating to penicillins |
| CH410961A (de) * | 1961-02-22 | 1966-04-15 | Yoshitomi Pharmaceutical | Verfahren zur Herstellung N-substituierter Piperazinderivate |
| US3297692A (en) * | 1961-04-03 | 1967-01-10 | Lilly Co Eli | 7-alkylmercaptoacetamidocephalosporanic acid |
| US3178466A (en) * | 1962-07-17 | 1965-04-13 | Olin Mathieson | 2-(2, 6-dimethoxybenzoylthio) acetic acid |
| US3152050A (en) * | 1962-12-27 | 1964-10-06 | American Home Prod | Enzymatic process for preparing penicillins |
| US3248387A (en) * | 1963-02-07 | 1966-04-26 | American Home Prod | Amino-acylamino-penicillanic acids |
| BE650488A (sv) * | 1963-07-13 | |||
| US3301849A (en) * | 1963-09-04 | 1967-01-31 | Bristol Myers Co | 6-(alpha-phenoxyalkanoylamino) thiopenicillanic acid |
| DE1745619B1 (de) * | 1963-09-14 | 1969-09-11 | Bayer Ag | Verfahren zur Herstellung von halbsynthetischen 6-Acylaminopenicillansaeuren |
| US3445463A (en) * | 1965-06-17 | 1969-05-20 | Lilly Co Eli | 3-(cyclic acyl)oxymethyl cephalosporins |
| US3324118A (en) * | 1965-12-27 | 1967-06-06 | Lilly Co Eli | Phenalkylmercaptomethyl cephalosporins |
| US3335136A (en) * | 1965-12-27 | 1967-08-08 | Lilly Co Eli | Halophenylmercaptomethyl cephalosporins |
| US8360298B2 (en) | 2008-09-23 | 2013-01-29 | Covidien Lp | Surgical instrument and loading unit for use therewith |
| US7988028B2 (en) * | 2008-09-23 | 2011-08-02 | Tyco Healthcare Group Lp | Surgical instrument having an asymmetric dynamic clamping member |
| US8225979B2 (en) | 2009-10-30 | 2012-07-24 | Tyco Healthcare Group Lp | Locking shipping wedge |
| US10092290B2 (en) | 2015-03-17 | 2018-10-09 | Covidien Lp | Surgical instrument, loading unit for use therewith and related methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2475920A (en) * | 1944-07-11 | 1949-07-12 | Therapeutic Res Corp Of Great | Manufacture of penicillin |
| US2422777A (en) * | 1944-12-06 | 1947-06-24 | Baker Chem Co J T | Method for producing penicillin by mold culture |
| US2934540A (en) * | 1957-05-15 | 1960-04-26 | Research Corp | Thiazolidine intermediates for penicillin |
| US2941995A (en) * | 1957-08-02 | 1960-06-21 | Beecham Res Lab | Recovery of solid 6-aminopenicillanic acid |
-
1959
- 1959-12-04 DE DEF30003A patent/DE1151803B/de active Pending
-
1960
- 1960-11-24 GB GB40489/60A patent/GB904576A/en not_active Expired
- 1960-11-29 US US72311A patent/US3079306A/en not_active Expired - Lifetime
- 1960-11-30 NO NO138179A patent/NO115254B/no unknown
- 1960-12-02 DK DK481460AA patent/DK127254B/da unknown
- 1960-12-02 BR BR124673/60A patent/BR6024673D0/pt unknown
- 1960-12-02 BE BE597759A patent/BE597759A/fr unknown
- 1960-12-05 SE SE11767/60A patent/SE304269B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK127254B (da) | 1973-10-08 |
| US3079306A (en) | 1963-02-26 |
| SE304269B (sv) | 1968-09-23 |
| GB904576A (en) | 1962-08-29 |
| DE1151803B (de) | 1963-07-25 |
| BR6024673D0 (pt) | 1973-06-12 |
| BE597759A (fr) | 1961-06-02 |
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