BE569728A - - Google Patents
Info
- Publication number
- BE569728A BE569728A BE569728DA BE569728A BE 569728 A BE569728 A BE 569728A BE 569728D A BE569728D A BE 569728DA BE 569728 A BE569728 A BE 569728A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- acid
- chloride
- liquor
- fermentation liquor
- Prior art date
Links
- 238000000855 fermentation Methods 0.000 claims description 63
- 230000004151 fermentation Effects 0.000 claims description 63
- 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 55
- 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 55
- 238000000034 method Methods 0.000 claims description 51
- 229930182555 Penicillin Natural products 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 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 claims description 27
- 239000002253 acid Substances 0.000 claims description 22
- 229940049954 penicillin Drugs 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 18
- 150000002960 penicillins Chemical class 0.000 claims description 17
- 238000012360 testing method Methods 0.000 claims description 16
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 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 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 229930195708 Penicillin V Natural products 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 235000015097 nutrients Nutrition 0.000 claims description 6
- 229940056360 penicillin g Drugs 0.000 claims description 6
- 229940056367 penicillin v Drugs 0.000 claims description 6
- 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 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 235000019371 penicillin G benzathine Nutrition 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- FGEAOSXMQZWHIQ-UHFFFAOYSA-N 2-chloro-2-phenylacetyl chloride Chemical compound ClC(=O)C(Cl)C1=CC=CC=C1 FGEAOSXMQZWHIQ-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims description 2
- 230000036961 partial effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- ODIDKWCPMQVCRG-UHFFFAOYSA-N 6-[(2-chloro-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(Cl)C1=CC=CC=C1 ODIDKWCPMQVCRG-UHFFFAOYSA-N 0.000 claims 1
- NGWKGSCSHDHHAJ-YPFQVHCOSA-N Liquoric acid Chemical compound C1C[C@H](O)C(C)(C)C2CC[C@@]3(C)[C@]4(C)C[C@H]5O[C@@H]([C@](C6)(C)C(O)=O)C[C@@]5(C)[C@@H]6C4=CC(=O)C3[C@]21C NGWKGSCSHDHHAJ-YPFQVHCOSA-N 0.000 claims 1
- NGWKGSCSHDHHAJ-UHFFFAOYSA-N Liquoric acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CC5OC(C(C6)(C)C(O)=O)CC5(C)C6C4=CC(=O)C3C21C NGWKGSCSHDHHAJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 159000000000 sodium salts Chemical class 0.000 description 41
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 230000003115 biocidal effect Effects 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002609 medium Substances 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- -1 chlorocarbonic acid ester Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000001963 growth medium Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000017060 Arachis glabrata Nutrition 0.000 description 5
- 241001553178 Arachis glabrata Species 0.000 description 5
- 235000010777 Arachis hypogaea Nutrition 0.000 description 5
- 235000018262 Arachis monticola Nutrition 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 235000020232 peanut Nutrition 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 241000228143 Penicillium Species 0.000 description 4
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 238000004816 paper chromatography Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 3
- DSVAZLXLRDXHKO-UHFFFAOYSA-N 2-naphthalen-1-ylacetyl chloride Chemical compound C1=CC=C2C(CC(=O)Cl)=CC=CC2=C1 DSVAZLXLRDXHKO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010087702 Penicillinase Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 235000010216 calcium carbonate Nutrition 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229950009506 penicillinase Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRHCKIKUFJDDPK-UHFFFAOYSA-N 3-carbonochloridoylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C(Cl)=O)=C1 WRHCKIKUFJDDPK-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-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
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- ZOORULWLQVVPOJ-UHFFFAOYSA-N 2-naphthalen-1-yloxyacetyl chloride Chemical compound C1=CC=C2C(OCC(=O)Cl)=CC=CC2=C1 ZOORULWLQVVPOJ-UHFFFAOYSA-N 0.000 description 1
- UJXIOVIFPTXDHU-UHFFFAOYSA-N 2-phenylethanethioyl chloride Chemical compound ClC(=S)CC1=CC=CC=C1 UJXIOVIFPTXDHU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- YQHZEPRHQQLJQE-UHFFFAOYSA-N ethoxycarbonyl 2-(phenylmethoxycarbonylamino)acetate Chemical compound C(C)OC(=O)OC(CNC(=O)OCC1=CC=CC=C1)=O YQHZEPRHQQLJQE-UHFFFAOYSA-N 0.000 description 1
- QTLGLRZMNGPJCD-UHFFFAOYSA-N ethoxycarbonyl 2-aminoacetate Chemical compound CCOC(=O)OC(=O)CN QTLGLRZMNGPJCD-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002207 metabolite 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
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/42—Compounds with a free primary amino radical attached in position 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569728A true BE569728A (https=) |
Family
ID=188570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569728D BE569728A (https=) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569728A (https=) |
Cited By (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2951839A (en) * | 1959-07-15 | 1960-09-06 | Doyle Frank Peter | Synthetic penicillins |
| US3007920A (en) * | 1960-10-28 | 1961-11-07 | Rech Et Ind Therapeutiques En | New 6-aminopenicillanic acid derivatives |
| US3008956A (en) * | 1959-08-03 | 1961-11-14 | Beecham Res Lab | Process for the recovery of 6-aminopenicillanic acid |
| US3008955A (en) * | 1959-08-03 | 1961-11-14 | Beecham Res Lab | Process for the recovery of 6-aminopenicillanic acid |
| US3025290A (en) * | 1959-06-09 | 1962-03-13 | Doyle Frank Peter | Synthetic penicillin and salts thereof |
| DE1126878B (de) * | 1960-11-02 | 1962-04-05 | Hoechst Ag | Verfahren zur Herstellung von 6-Sulfenamidopenicillansaeuren |
| US3040032A (en) * | 1959-07-02 | 1962-06-19 | Doyle Frank Peter | Synthetic penicillins and salts thereof |
| US3041333A (en) * | 1960-05-11 | 1962-06-26 | Smith Kline French Lab | Substituted cyclopropylcarboxyamido derivatives of penicillanic acid |
| US3041332A (en) * | 1960-05-11 | 1962-06-26 | Smith Kline French Lab | Phenylcyclopropylcarboxyamido derivatives of penicillanic acid |
| US3053831A (en) * | 1961-05-05 | 1962-09-11 | American Home Prod | Dialkoxynaphthyl penicillins |
| DE1141640B (de) * | 1960-03-19 | 1962-12-27 | Hoechst Ag | Verfahren zur Herstellung von Acylderivaten von 6-Ureido-penicillansaeuren |
| US3071576A (en) * | 1959-11-13 | 1963-01-01 | Beecham Res Lab | Synthetic penicillins |
| US3071575A (en) * | 1959-07-15 | 1963-01-01 | Beecham Res Lab | Synthetic penicillins and salts thereof |
| DE1142170B (de) * | 1959-03-31 | 1963-01-10 | Rech S Et D Applic Et Medicale | Verfahren zur Herstellung einer neuen Verbindung des Phenoxymethylpenicillins |
| US3078268A (en) * | 1959-10-05 | 1963-02-19 | Doyle Frank Peter | Process for the preparation of penicillins |
| US3078269A (en) * | 1961-01-10 | 1963-02-19 | Pfizer & Co C | Derivatives of 6-amino penicillanic acid |
| DE1143817B (de) * | 1959-05-25 | 1963-02-21 | Beecham Res Lab | Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben |
| US3082204A (en) * | 1959-11-04 | 1963-03-19 | Perron Yvon Gaston | Alpha-alkoxy, alpha, alpha-dialkylmethyl penicillins |
| US3088880A (en) * | 1961-04-10 | 1963-05-07 | Pfizer & Co C | 6-aminopenicillanic acid amide production |
| US3092620A (en) * | 1960-10-05 | 1963-06-04 | Pfizer & Co C | Derivatives of penicillanic acid |
| DE1149717B (de) * | 1960-03-31 | 1963-06-06 | Beecham Res Lab | Verfahren zur Herstellung neuer Penicilline |
| US3093633A (en) * | 1960-06-29 | 1963-06-11 | Pfizer & Co C | Novel penicillin compounds |
| US3107250A (en) * | 1960-02-04 | 1963-10-15 | Smith Kline French Lab | Process for the preparation of 6-aminopenicillanic acid and novel intermediates useful therein |
| DE1156078B (de) * | 1960-08-25 | 1963-10-24 | Beecham Res Lab | Verfahren zur Herstellung von D(-)-ª‡-Aminobenzylpenicillin und von L(+)-ª‡-Aminobenzylpenicillin |
| DE1159449B (de) * | 1961-03-22 | 1963-12-19 | Gruenenthal Chemie | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren und deren Salzen |
| DE1159448B (de) * | 1959-11-13 | 1963-12-19 | Beecham Res Lab | Verfahren zur Herstellung neuer Penicilline |
| US3116285A (en) * | 1960-05-25 | 1963-12-31 | Pfizer & Co C | Novel penicillin compounds |
| US3118878A (en) * | 1959-06-09 | 1964-01-21 | Beecham Res Lab | Substituted phosphoramidopenicillanic acids |
| US3120512A (en) * | 1960-03-19 | 1964-02-04 | Hoechst Ag | Acyl derivatives of 4-ureido-penicillanic acids and process of preparing them |
| DE1162373B (de) * | 1959-01-22 | 1964-02-06 | Beecham Res Lab | Verfahren zur Herstellung von Penicillinen |
| DE1162374B (de) * | 1959-11-04 | 1964-02-06 | Beecham Res Lab | Verfahren zur Herstellung von Penicillinen und deren nichttoxischen Salzen |
| DE1163329B (de) * | 1961-01-18 | 1964-02-20 | Rhone Poulenc Sa | Verfahren zur Extraktion von 6-Aminopenicillansaeure |
| US3129217A (en) * | 1959-08-19 | 1964-04-14 | Beecham Group Ltd | Derivatives of 6-(9-anthramido) penicillanic acid |
| US3142673A (en) * | 1961-03-31 | 1964-07-28 | Pfizer & Co C | Derivatives of 6-aminopenicillanic acid |
| DE1174784B (de) * | 1960-10-28 | 1964-07-30 | Rech Et Ind Therapeutique R I | Verfahren zur Herstellung von ª‡-Methoxybenzyl-penicillinderivaten |
| US3144444A (en) * | 1960-09-27 | 1964-08-11 | Pfizer & Co C | Novel derivatives of 6-aminopenicillanic acid |
| DE1179207B (de) * | 1961-09-26 | 1964-10-08 | Lepetit Spa | Verfahren zur Herstellung von Penicillinen |
| US3157639A (en) * | 1959-08-19 | 1964-11-17 | Beecham Group Ltd | Synthetic penicillins |
| DE1185190B (de) * | 1960-10-13 | 1965-01-14 | Smith Kline French Lab | Verfahren zur Herstellung von Penicillinen |
| US3174964A (en) * | 1959-12-10 | 1965-03-23 | Pfizer & Co C | Derivatives of 6-aminopenicillanic acid |
| DE1191819B (de) * | 1959-11-16 | 1965-04-29 | Beecham Group Ltd | Verfahren zur Herstellung von Phenylmercaptoalkylpenicillinen |
| DE1191822B (de) * | 1961-05-03 | 1965-04-29 | Smith Kline French Lab | Verfahren zur Herstellung von 7-Acylaminocephalosporansaeurederivaten |
| DE1203274B (de) * | 1962-08-31 | 1965-10-21 | Roussel Uclaf | Verfahren zur Herstellung des Propionylerythro-mycinsalzes der N-Hexahydroben-zyloxycarbonyl-6-aminopenicillansaeure |
| DE1212089B (de) * | 1961-05-03 | 1966-03-10 | Smith Kline French Lab | Verfahren zur Herstellung heterocyclischer 6-Acylaminopenicillansaeuren |
| US3248386A (en) * | 1960-12-30 | 1966-04-26 | American Home Prod | 6-(tetrahydro-1'-naphthoylamino)-penicillanic acid derivatives |
| DE1225342B (de) * | 1961-08-03 | 1966-09-22 | Merck & Co Inc | Verfahren zur Gewinnung von 6-Aminopenicillansaeure aus Gaerloesungen |
-
0
- BE BE569728D patent/BE569728A/fr unknown
Cited By (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1162373B (de) * | 1959-01-22 | 1964-02-06 | Beecham Res Lab | Verfahren zur Herstellung von Penicillinen |
| DE1142170B (de) * | 1959-03-31 | 1963-01-10 | Rech S Et D Applic Et Medicale | Verfahren zur Herstellung einer neuen Verbindung des Phenoxymethylpenicillins |
| DE1143817B (de) * | 1959-05-25 | 1963-02-21 | Beecham Res Lab | Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben |
| DE1143817C2 (de) * | 1959-05-25 | 1973-03-29 | Beecham Res Lab | Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben |
| US3025290A (en) * | 1959-06-09 | 1962-03-13 | Doyle Frank Peter | Synthetic penicillin and salts thereof |
| DE1294383B (de) * | 1959-06-09 | 1969-05-08 | Beecham Group Ltd | Penicilline und deren Salze sowie Verfahren zu ihrer Herstellung |
| US3118878A (en) * | 1959-06-09 | 1964-01-21 | Beecham Res Lab | Substituted phosphoramidopenicillanic acids |
| US3040032A (en) * | 1959-07-02 | 1962-06-19 | Doyle Frank Peter | Synthetic penicillins and salts thereof |
| US2951839A (en) * | 1959-07-15 | 1960-09-06 | Doyle Frank Peter | Synthetic penicillins |
| US3071575A (en) * | 1959-07-15 | 1963-01-01 | Beecham Res Lab | Synthetic penicillins and salts thereof |
| US3008955A (en) * | 1959-08-03 | 1961-11-14 | Beecham Res Lab | Process for the recovery of 6-aminopenicillanic acid |
| US3008956A (en) * | 1959-08-03 | 1961-11-14 | Beecham Res Lab | Process for the recovery of 6-aminopenicillanic acid |
| DE1146060B (de) * | 1959-08-03 | 1963-03-28 | Beecham Res Lab | Verfahren zur Gewinnung von 6-Aminopenicillansaeure aus ihren waessrigen Loesungen |
| DE1146059B (de) * | 1959-08-03 | 1963-03-28 | Beecham Res Lab | Verfahren zur Anreicherung oder Isolierung von 6-Aminopenicillansaeure aus ihren waesserigen Loesungen |
| US3129217A (en) * | 1959-08-19 | 1964-04-14 | Beecham Group Ltd | Derivatives of 6-(9-anthramido) penicillanic acid |
| US3157639A (en) * | 1959-08-19 | 1964-11-17 | Beecham Group Ltd | Synthetic penicillins |
| US3078268A (en) * | 1959-10-05 | 1963-02-19 | Doyle Frank Peter | Process for the preparation of penicillins |
| US3082204A (en) * | 1959-11-04 | 1963-03-19 | Perron Yvon Gaston | Alpha-alkoxy, alpha, alpha-dialkylmethyl penicillins |
| DE1162374B (de) * | 1959-11-04 | 1964-02-06 | Beecham Res Lab | Verfahren zur Herstellung von Penicillinen und deren nichttoxischen Salzen |
| DE1159448B (de) * | 1959-11-13 | 1963-12-19 | Beecham Res Lab | Verfahren zur Herstellung neuer Penicilline |
| US3071576A (en) * | 1959-11-13 | 1963-01-01 | Beecham Res Lab | Synthetic penicillins |
| DE1191819B (de) * | 1959-11-16 | 1965-04-29 | Beecham Group Ltd | Verfahren zur Herstellung von Phenylmercaptoalkylpenicillinen |
| US3174964A (en) * | 1959-12-10 | 1965-03-23 | Pfizer & Co C | Derivatives of 6-aminopenicillanic acid |
| US3107250A (en) * | 1960-02-04 | 1963-10-15 | Smith Kline French Lab | Process for the preparation of 6-aminopenicillanic acid and novel intermediates useful therein |
| DE1141640B (de) * | 1960-03-19 | 1962-12-27 | Hoechst Ag | Verfahren zur Herstellung von Acylderivaten von 6-Ureido-penicillansaeuren |
| US3120512A (en) * | 1960-03-19 | 1964-02-04 | Hoechst Ag | Acyl derivatives of 4-ureido-penicillanic acids and process of preparing them |
| DE1149717B (de) * | 1960-03-31 | 1963-06-06 | Beecham Res Lab | Verfahren zur Herstellung neuer Penicilline |
| US3041332A (en) * | 1960-05-11 | 1962-06-26 | Smith Kline French Lab | Phenylcyclopropylcarboxyamido derivatives of penicillanic acid |
| US3041333A (en) * | 1960-05-11 | 1962-06-26 | Smith Kline French Lab | Substituted cyclopropylcarboxyamido derivatives of penicillanic acid |
| US3116285A (en) * | 1960-05-25 | 1963-12-31 | Pfizer & Co C | Novel penicillin compounds |
| US3093633A (en) * | 1960-06-29 | 1963-06-11 | Pfizer & Co C | Novel penicillin compounds |
| DE1156078B (de) * | 1960-08-25 | 1963-10-24 | Beecham Res Lab | Verfahren zur Herstellung von D(-)-ª‡-Aminobenzylpenicillin und von L(+)-ª‡-Aminobenzylpenicillin |
| DE1156078C2 (de) * | 1960-08-25 | 1973-10-25 | Beecham Res Lab | Verfahren zur Herstellung von D(-)-ª‡-Aminobenzylpenicillin und von L(+)-ª‡-Aminobenzylpenicillin |
| US3144444A (en) * | 1960-09-27 | 1964-08-11 | Pfizer & Co C | Novel derivatives of 6-aminopenicillanic acid |
| US3092620A (en) * | 1960-10-05 | 1963-06-04 | Pfizer & Co C | Derivatives of penicillanic acid |
| DE1185190B (de) * | 1960-10-13 | 1965-01-14 | Smith Kline French Lab | Verfahren zur Herstellung von Penicillinen |
| US3007920A (en) * | 1960-10-28 | 1961-11-07 | Rech Et Ind Therapeutiques En | New 6-aminopenicillanic acid derivatives |
| DE1174784B (de) * | 1960-10-28 | 1964-07-30 | Rech Et Ind Therapeutique R I | Verfahren zur Herstellung von ª‡-Methoxybenzyl-penicillinderivaten |
| DE1126878B (de) * | 1960-11-02 | 1962-04-05 | Hoechst Ag | Verfahren zur Herstellung von 6-Sulfenamidopenicillansaeuren |
| US3248386A (en) * | 1960-12-30 | 1966-04-26 | American Home Prod | 6-(tetrahydro-1'-naphthoylamino)-penicillanic acid derivatives |
| US3078269A (en) * | 1961-01-10 | 1963-02-19 | Pfizer & Co C | Derivatives of 6-amino penicillanic acid |
| DE1163329B (de) * | 1961-01-18 | 1964-02-20 | Rhone Poulenc Sa | Verfahren zur Extraktion von 6-Aminopenicillansaeure |
| DE1159449B (de) * | 1961-03-22 | 1963-12-19 | Gruenenthal Chemie | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren und deren Salzen |
| US3142673A (en) * | 1961-03-31 | 1964-07-28 | Pfizer & Co C | Derivatives of 6-aminopenicillanic acid |
| US3088880A (en) * | 1961-04-10 | 1963-05-07 | Pfizer & Co C | 6-aminopenicillanic acid amide production |
| DE1191822B (de) * | 1961-05-03 | 1965-04-29 | Smith Kline French Lab | Verfahren zur Herstellung von 7-Acylaminocephalosporansaeurederivaten |
| DE1212089B (de) * | 1961-05-03 | 1966-03-10 | Smith Kline French Lab | Verfahren zur Herstellung heterocyclischer 6-Acylaminopenicillansaeuren |
| US3053831A (en) * | 1961-05-05 | 1962-09-11 | American Home Prod | Dialkoxynaphthyl penicillins |
| DE1225342B (de) * | 1961-08-03 | 1966-09-22 | Merck & Co Inc | Verfahren zur Gewinnung von 6-Aminopenicillansaeure aus Gaerloesungen |
| DE1179207B (de) * | 1961-09-26 | 1964-10-08 | Lepetit Spa | Verfahren zur Herstellung von Penicillinen |
| DE1203274B (de) * | 1962-08-31 | 1965-10-21 | Roussel Uclaf | Verfahren zur Herstellung des Propionylerythro-mycinsalzes der N-Hexahydroben-zyloxycarbonyl-6-aminopenicillansaeure |
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