CH397156A - Verfahren zur Herstellung von Penicillinen - Google Patents

Verfahren zur Herstellung von Penicillinen

Info

Publication number: CH397156A
Authority: CH; Switzerland
Prior art keywords: fermentation; acid; added; formula; precursor
Prior art date: 1959-11-24

Application number

CH1302160A

Other languages

German (de)

English (en)

Inventor

Ernst Dr Brandl

Richard Dr Brunner

Hans Dr Margreiter

Original Assignee

Beecham Group Ltd

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.)

1959-11-24

Filing date

1960-11-21

Publication date

1965-08-15

1959-11-24 Priority claimed from AT851759A external-priority patent/AT234270B/de

1960-11-21 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1965-08-15 Publication of CH397156A publication Critical patent/CH397156A/de

Links

229930182555 Penicillin Natural products 0.000 title claims description 62
238000000034 method Methods 0.000 title claims description 27
150000002960 penicillins Chemical class 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title claims description 5
238000000855 fermentation Methods 0.000 claims description 126
230000004151 fermentation Effects 0.000 claims description 126
239000002243 precursor Substances 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 25
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 16
150000004820 halides Chemical class 0.000 claims description 14
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
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 10
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 6
239000000872 buffer Substances 0.000 claims description 5
235000011054 acetic acid Nutrition 0.000 claims description 4
150000001243 acetic acids Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
229940072049 amyl acetate Drugs 0.000 claims description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
239000000243 solution Substances 0.000 description 52
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 47
229940049954 penicillin Drugs 0.000 description 46
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
235000015097 nutrients Nutrition 0.000 description 38
241000228150 Penicillium chrysogenum Species 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 22
239000002054 inoculum Substances 0.000 description 20
229910001220 stainless steel Inorganic materials 0.000 description 17
239000010935 stainless steel Substances 0.000 description 17
BDSSZTXPZHIYHM-UHFFFAOYSA-N 2-phenoxypropanoyl chloride Chemical compound ClC(=O)C(C)OC1=CC=CC=C1 BDSSZTXPZHIYHM-UHFFFAOYSA-N 0.000 description 14
240000004808 Saccharomyces cerevisiae Species 0.000 description 14
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
-1 araliphatic Chemical group 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
230000000694 effects Effects 0.000 description 5
229940056367 penicillin v Drugs 0.000 description 5
238000010998 test method Methods 0.000 description 5
229930195708 Penicillin V Natural products 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
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 4
235000011056 potassium acetate Nutrition 0.000 description 4
235000017060 Arachis glabrata Nutrition 0.000 description 3
244000105624 Arachis hypogaea Species 0.000 description 3
235000010777 Arachis hypogaea Nutrition 0.000 description 3
235000018262 Arachis monticola Nutrition 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
244000269722 Thea sinensis Species 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
235000020232 peanut Nutrition 0.000 description 3
229960004894 pheneticillin Drugs 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 2
OXMHWEVVXJXQGV-UHFFFAOYSA-N 2-phenyl-2-sulfanylacetyl chloride Chemical compound ClC(=O)C(S)C1=CC=CC=C1 OXMHWEVVXJXQGV-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000228143 Penicillium Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
WPTJBFNYRRZIDZ-UHFFFAOYSA-M sodium;2-phenoxyacetate Chemical compound [Na+].[O-]C(=O)COC1=CC=CC=C1 WPTJBFNYRRZIDZ-UHFFFAOYSA-M 0.000 description 2
229960005486 vaccine Drugs 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
CXIYBDIJKQJUMN-QMMMGPOBSA-N (2s)-2-anilino-3-hydroxypropanoic acid Chemical compound OC[C@@H](C(O)=O)NC1=CC=CC=C1 CXIYBDIJKQJUMN-QMMMGPOBSA-N 0.000 description 1
FBIGAJNVRFKBJL-UHFFFAOYSA-N (4-tert-Butyl-phenoxy)-acetic acid Chemical compound CC(C)(C)C1=CC=C(OCC(O)=O)C=C1 FBIGAJNVRFKBJL-UHFFFAOYSA-N 0.000 description 1
OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
OWEDBRWCJFWVFZ-UHFFFAOYSA-N 2-(2,4-dinitrophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O OWEDBRWCJFWVFZ-UHFFFAOYSA-N 0.000 description 1
JEJIBWJTYHKGFO-UHFFFAOYSA-N 2-(2-chloro-5-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C(OCC(O)=O)=C1 JEJIBWJTYHKGFO-UHFFFAOYSA-N 0.000 description 1
OPQYFNRLWBWCST-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC=C1Cl OPQYFNRLWBWCST-UHFFFAOYSA-N 0.000 description 1
IKODIMKOCSGKHQ-UHFFFAOYSA-N 2-(2-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1Cl IKODIMKOCSGKHQ-UHFFFAOYSA-N 0.000 description 1
IHONYPFTXGQWAX-UHFFFAOYSA-N 2-(2-methoxyphenoxy)acetic acid Chemical compound COC1=CC=CC=C1OCC(O)=O IHONYPFTXGQWAX-UHFFFAOYSA-N 0.000 description 1
VWVRTVRGLRSWEQ-UHFFFAOYSA-N 2-(2-methoxyphenoxy)acetyl chloride Chemical compound COC1=CC=CC=C1OCC(Cl)=O VWVRTVRGLRSWEQ-UHFFFAOYSA-N 0.000 description 1
AEWBGACGIKCIJH-UHFFFAOYSA-N 2-(2-nitrophenoxy)acetyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC(Cl)=O AEWBGACGIKCIJH-UHFFFAOYSA-N 0.000 description 1
GIEQJKZWTIFEJM-UHFFFAOYSA-N 2-(3,4-dimethylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C=C1C GIEQJKZWTIFEJM-UHFFFAOYSA-N 0.000 description 1
NIPZZANLNKBKIS-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)acetic acid Chemical compound CC1=CC(C)=CC(OCC(O)=O)=C1 NIPZZANLNKBKIS-UHFFFAOYSA-N 0.000 description 1
SJYYKYLTOMNRHA-UHFFFAOYSA-N 2-(3-chloro-4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C=C1Cl SJYYKYLTOMNRHA-UHFFFAOYSA-N 0.000 description 1
LYJCGBYEVXKOST-UHFFFAOYSA-N 2-(4-acetamidophenoxy)acetic acid Chemical compound CC(=O)NC1=CC=C(OCC(O)=O)C=C1 LYJCGBYEVXKOST-UHFFFAOYSA-N 0.000 description 1
IJOSXVVFEKXIGN-UHFFFAOYSA-N 2-(4-chloro-3,5-dimethylphenoxy)acetic acid Chemical compound CC1=CC(OCC(O)=O)=CC(C)=C1Cl IJOSXVVFEKXIGN-UHFFFAOYSA-N 0.000 description 1
FBGYNJKXMKWETB-UHFFFAOYSA-N 2-(4-chloro-3-methylphenoxy)acetic acid Chemical compound CC1=CC(OCC(O)=O)=CC=C1Cl FBGYNJKXMKWETB-UHFFFAOYSA-N 0.000 description 1
BJGOCBAHPWALBX-UHFFFAOYSA-N 2-(4-cyanophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C#N)C=C1 BJGOCBAHPWALBX-UHFFFAOYSA-N 0.000 description 1
WVELHLIHMYYZAT-UHFFFAOYSA-N 2-(4-ethylphenoxy)acetic acid Chemical compound CCC1=CC=C(OCC(O)=O)C=C1 WVELHLIHMYYZAT-UHFFFAOYSA-N 0.000 description 1
OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 1
LPYHDHGKBRMYBL-UHFFFAOYSA-N 2-(4-hexylphenoxy)acetic acid Chemical compound CCCCCCC1=CC=C(OCC(O)=O)C=C1 LPYHDHGKBRMYBL-UHFFFAOYSA-N 0.000 description 1
XCRDQVBOVYWDPH-UHFFFAOYSA-N 2-(4-methylphenyl)sulfanylacetic acid Chemical compound CC1=CC=C(SCC(O)=O)C=C1 XCRDQVBOVYWDPH-UHFFFAOYSA-N 0.000 description 1
LSYVSKGBAOTYNT-UHFFFAOYSA-N 2-(4-propylphenoxy)acetic acid Chemical compound CCCC1=CC=C(OCC(O)=O)C=C1 LSYVSKGBAOTYNT-UHFFFAOYSA-N 0.000 description 1
VDYXCTNJHWITDQ-UHFFFAOYSA-N 2-butoxyacetyl chloride Chemical compound CCCCOCC(Cl)=O VDYXCTNJHWITDQ-UHFFFAOYSA-N 0.000 description 1
VABYVFZVTIDNOA-UHFFFAOYSA-N 2-cyclohexylacetyl chloride Chemical compound ClC(=O)CC1CCCCC1 VABYVFZVTIDNOA-UHFFFAOYSA-N 0.000 description 1
YMAXCKYGIGCLPM-UHFFFAOYSA-N 2-heptoxyacetic acid Chemical compound CCCCCCCOCC(O)=O YMAXCKYGIGCLPM-UHFFFAOYSA-N 0.000 description 1
HJOGHUABHYACMH-UHFFFAOYSA-N 2-hexoxyacetic acid Chemical compound CCCCCCOCC(O)=O HJOGHUABHYACMH-UHFFFAOYSA-N 0.000 description 1
OARCPYUICLOWND-UHFFFAOYSA-N 2-oxo-2-(4-pentylphenoxy)acetic acid Chemical compound C(CCCC)C1=CC=C(OC(C(=O)O)=O)C=C1 OARCPYUICLOWND-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-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
NLVYFXLILFDECX-UHFFFAOYSA-N 2-pyridin-2-yloxyacetic acid Chemical compound OC(=O)COC1=CC=CC=N1 NLVYFXLILFDECX-UHFFFAOYSA-N 0.000 description 1
SNYRXHULAWEECU-UHFFFAOYSA-N 3,4-dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C(Cl)=C1 SNYRXHULAWEECU-UHFFFAOYSA-N 0.000 description 1
QATKOZUHTGAWMG-UHFFFAOYSA-N 4-fluoro-3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(O)=C1 QATKOZUHTGAWMG-UHFFFAOYSA-N 0.000 description 1
AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
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 1
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 1
239000005639 Lauric acid Substances 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
DZTHIGRZJZPRDV-LBPRGKRZSA-N N-acetyl-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-LBPRGKRZSA-N 0.000 description 1
DZTHIGRZJZPRDV-UHFFFAOYSA-N Nalpha-Acetyltryptophan Natural products C1=CC=C2C(CC(NC(=O)C)C(O)=O)=CNC2=C1 DZTHIGRZJZPRDV-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
125000004945 acylaminoalkyl group Chemical group 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000001851 biosynthetic effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
239000012531 culture fluid Substances 0.000 description 1
230000000254 damaging effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940116191 n-acetyltryptophan Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-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
- 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

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)

CH1302160A 1959-11-24 1960-11-21 Verfahren zur Herstellung von Penicillinen CH397156A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AT851759A AT234270B (de)	1959-11-24	1959-11-24	Verfahren zur Herstellung von α-Methylphenoxymethylpenicillin durch Fermentation
AT160360		1960-03-01
AT707160		1960-09-17

Publications (1)

Publication Number	Publication Date
CH397156A true CH397156A (de)	1965-08-15

Family

ID=27147696

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1302160A CH397156A (de)	1959-11-24	1960-11-21	Verfahren zur Herstellung von Penicillinen

Country Status (4)

Country	Link
BE (1)	BE597419A (fr)
CH (1)	CH397156A (fr)
DK (1)	DK119761B (fr)
GB (1)	GB958587A (fr)

1960
- 1960-11-21 CH CH1302160A patent/CH397156A/de unknown
- 1960-11-23 BE BE597419A patent/BE597419A/fr unknown
- 1960-11-23 DK DK466360A patent/DK119761B/da unknown
- 1960-11-24 GB GB4050560A patent/GB958587A/en not_active Expired

Also Published As

Publication number	Publication date
DK119761B (da)	1971-02-22
BE597419A (fr)	1961-03-15
GB958587A (en)	1964-05-21

Publication	Publication Date	Title
CH645891A5 (de)	1984-10-31	Verfahren zur herstellung von monacolin k.
CH513845A (de)	1971-10-15	Verfahren zur Herstellung neuer Halogenpregnadiene
DE2343587A1 (de)	1974-03-07	Verfahren zur herstellung von 2-ketol-gulonsaeure
EP0435152A2 (fr)	1991-07-03	Procédé de préparation énantiosélective de (oméga-1)-hydroxyalkyl-xanthines
DE2163791C2 (de)	1985-02-21	Verfahren zur Herstellung von 7-Amino-3-methyl-3-cephem-4-carbonsäure und ihrer Ester
DD156986A5 (de)	1982-10-06	Verfahren zur herstellung optisch aktiver phenylpropan-derivate
DE69628002T2 (de)	2004-03-04	Herstellung von clavunalat-salzen
CH647749A5 (de)	1985-02-15	Salze und ester von monacolin-k, verfahren zu ihrer herstellung und pharmazeutische praeparate.
DE3114242A1 (de)	1982-06-16	Carbonsaeurederivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel
CH646966A5 (de)	1984-12-28	Die cholesterinbiosynthese hemmende verbindungen, ihre herstellung und verwendung.
DE69908569T2 (de)	2004-05-13	Verfahren zur herstellung von fexofenadin
DE2153600A1 (fr)	1972-05-31
DE2819886C2 (fr)	1988-03-31
DE3618538C2 (de)	1996-02-29	queR
DE2327990A1 (de)	1973-12-20	Biologische ueberfuehrung von anhydrotetracyclinen in 6-desoxytetracycline
DE69904658T2 (de)	2003-11-06	Gegen Ralstonia Solanacearum aktive bakterizide Zusammensetzungen
DE60105016T3 (de)	2009-06-25	Verfahren zur reinigung eines salzes der clavulansäure
DE1118401B (de)	1961-11-30	Verfahren zur Herstellung von Penicillinen durch Fermentation
DE60204826T2 (de)	2006-04-27	Verfahren zur Herstellung von Natriumsalz der D-6-[(alpha-4-(Ethyl-2,3-dioxo-1-piperazinocarbonyl-amino)phenylacetamido]-penicillansäure
AT234270B (de)	1964-06-25	Verfahren zur Herstellung von α-Methylphenoxymethylpenicillin durch Fermentation
DE1620094A1 (de)	1970-02-12	Verfahren zur Herstellung von heterocyclischen Verbindungen
DE1967074B2 (de)	1978-03-09	Verfahren zur Herstellung von a-Aminobenzylpenicillin
US3093547A (en)	1963-06-11	Process of preparing penicillins
DE2302745A1 (de)	1973-07-26	Penicillinderivate
DE2949065C2 (fr)	1990-08-23