DE2221046A1 - Antibiotika und verfahren zu ihrer herstellung - Google Patents
Antibiotika und verfahren zu ihrer herstellungInfo
- Publication number
- DE2221046A1 DE2221046A1 DE19722221046 DE2221046A DE2221046A1 DE 2221046 A1 DE2221046 A1 DE 2221046A1 DE 19722221046 DE19722221046 DE 19722221046 DE 2221046 A DE2221046 A DE 2221046A DE 2221046 A1 DE2221046 A1 DE 2221046A1
- Authority
- DE
- Germany
- Prior art keywords
- product
- penicillin
- reaction zone
- fibers
- enzymatic
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 239000003242 anti bacterial agent Substances 0.000 title claims description 8
- 229940088710 antibiotic agent Drugs 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims description 53
- 230000002255 enzymatic effect Effects 0.000 claims description 45
- 229930182555 Penicillin Natural products 0.000 claims description 41
- 239000000835 fiber Substances 0.000 claims description 37
- 229940049954 penicillin Drugs 0.000 claims description 31
- 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 28
- 239000000243 solution Substances 0.000 claims description 28
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000002960 penicillins Chemical class 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000003786 synthesis reaction Methods 0.000 claims description 19
- 102000004190 Enzymes Human genes 0.000 claims description 17
- 108090000790 Enzymes Proteins 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- -1 penicillin compound Chemical class 0.000 claims description 13
- 230000003115 biocidal effect Effects 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 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 10
- 238000003776 cleavage reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000007017 scission Effects 0.000 claims description 10
- 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 9
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 241000588724 Escherichia coli Species 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 3
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical group C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 3
- 229960000723 ampicillin Drugs 0.000 claims description 3
- BQIMPGFMMOZASS-CLZZGJSISA-N (6r,7r)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(CO)=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 BQIMPGFMMOZASS-CLZZGJSISA-N 0.000 claims description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- BQIMPGFMMOZASS-UHFFFAOYSA-N beta-amino-3-hydroxymethyl-3-cefem-4-carboxylic acid Natural products S1CC(CO)=C(C(O)=O)N2C(=O)C(N)C21 BQIMPGFMMOZASS-UHFFFAOYSA-N 0.000 claims description 2
- 229940124587 cephalosporin Drugs 0.000 claims description 2
- 150000001780 cephalosporins Chemical class 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000012527 feed solution Substances 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 1
- 239000008366 buffered solution Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 241001446247 uncultured actinomycete Species 0.000 claims 1
- 125000002348 vinylic group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 229930195708 Penicillin V Natural products 0.000 description 2
- 241000228150 Penicillium chrysogenum Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229940056367 penicillin v Drugs 0.000 description 2
- 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 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000588813 Alcaligenes faecalis Species 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000194107 Bacillus megaterium Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940005347 alcaligenes faecalis Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000006862 enzymatic digestion Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- MAGPZHKLEZXLNU-UHFFFAOYSA-N mandelamide Chemical compound NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 108700004370 poly-gamma-methylglutamate Proteins 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/02—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by desacylation of the substituent in the 7 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
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/04—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by acylation of the substituent in the 7 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2377771 | 1971-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2221046A1 true DE2221046A1 (de) | 1973-11-15 |
Family
ID=11209882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221046 Pending DE2221046A1 (de) | 1971-04-28 | 1972-04-28 | Antibiotika und verfahren zu ihrer herstellung |
Country Status (21)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2409569A1 (de) * | 1974-02-28 | 1975-09-11 | Bayer Ag | Verfahren zur herstellung von 7-aminodelta hoch 3 -cephem-derivaten |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492937A (en) * | 1973-12-28 | 1977-11-23 | Beecham Group Ltd | Enzyme complexes and their use |
| US4113566A (en) * | 1976-11-26 | 1978-09-12 | Pfizer Inc. | Process for preparing 6-aminopenicillanic acid |
| US4596777A (en) * | 1983-08-10 | 1986-06-24 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[[2-(protected or unprotected amino)-4-thiazolyl]acetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
| DK0567323T3 (da) * | 1992-04-24 | 1999-12-13 | Lilly Co Eli | Forbedret fremgangsmåde til fremstilling af cephalosporiner |
| DE19646550A1 (de) * | 1996-10-31 | 1998-05-07 | Fzb Biotechnik Gmbh | Kombiniertes Verfahren zur lösungsmittelarmen Gewinnung von Produkten aus der biokatalytischen Spaltung von Penicillin- oder Cephalosporin G-Lösungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE727506A (enrdf_load_stackoverflow) * | 1968-02-15 | 1969-07-01 | ||
| ES365631A1 (es) * | 1968-04-05 | 1971-03-16 | Beecham Group Ltd | Un procedimiento para la preparacion de acido 6-aminopeni- cilanico. |
-
1972
- 1972-04-07 IL IL39158A patent/IL39158A/en unknown
- 1972-04-09 EG EG140/72A patent/EG10474A/xx active
- 1972-04-11 CS CS722414A patent/CS223812B2/cs unknown
- 1972-04-25 NL NL7205609A patent/NL7205609A/xx unknown
- 1972-04-26 BE BE782646A patent/BE782646A/xx not_active IP Right Cessation
- 1972-04-26 FR FR7214799A patent/FR2134530B1/fr not_active Expired
- 1972-04-26 PL PL1972154991A patent/PL98632B1/pl unknown
- 1972-04-26 DD DD162592A patent/DD100721A5/xx unknown
- 1972-04-26 JP JP4215072A patent/JPS5413514B1/ja active Pending
- 1972-04-26 AR AR241744A patent/AR192936A1/es active
- 1972-04-27 ES ES402865A patent/ES402865A1/es not_active Expired
- 1972-04-27 LU LU65258D patent/LU65258A1/xx unknown
- 1972-04-27 ZA ZA722837A patent/ZA722837B/xx unknown
- 1972-04-27 YU YU01125/72A patent/YU112572A/xx unknown
- 1972-04-27 HU HUSA2349A patent/HU168856B/hu unknown
- 1972-04-27 IE IE561/72A patent/IE36334B1/xx unknown
- 1972-04-27 GB GB1972672A patent/GB1348359A/en not_active Expired
- 1972-04-27 BR BR2723/72A patent/BR7202723D0/pt unknown
- 1972-04-28 CH CH643472A patent/CH550822A/fr not_active IP Right Cessation
- 1972-04-28 AT AT377372A patent/AT318805B/de not_active IP Right Cessation
- 1972-04-28 DE DE19722221046 patent/DE2221046A1/de active Pending
- 1972-04-28 CH CH440373A patent/CH565181A5/xx not_active IP Right Cessation
-
1979
- 1979-09-05 YU YU02166/79A patent/YU216679A/xx unknown
-
1980
- 1980-04-17 YU YU01061/80A patent/YU106180A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2409569A1 (de) * | 1974-02-28 | 1975-09-11 | Bayer Ag | Verfahren zur herstellung von 7-aminodelta hoch 3 -cephem-derivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5413514B1 (enrdf_load_stackoverflow) | 1979-05-31 |
| AR192936A1 (es) | 1973-03-21 |
| LU65258A1 (enrdf_load_stackoverflow) | 1972-07-14 |
| YU112572A (en) | 1982-02-28 |
| FR2134530B1 (enrdf_load_stackoverflow) | 1975-10-17 |
| BE782646A (fr) | 1972-08-16 |
| EG10474A (en) | 1976-04-30 |
| IL39158A (en) | 1977-08-31 |
| CH565181A5 (enrdf_load_stackoverflow) | 1975-08-15 |
| IE36334B1 (en) | 1976-10-13 |
| AT318805B (de) | 1974-11-25 |
| HU168856B (enrdf_load_stackoverflow) | 1976-07-28 |
| CS223812B2 (en) | 1983-11-25 |
| IL39158A0 (en) | 1972-06-28 |
| PL98632B1 (pl) | 1978-05-31 |
| FR2134530A1 (enrdf_load_stackoverflow) | 1972-12-08 |
| DD100721A5 (enrdf_load_stackoverflow) | 1973-10-05 |
| CH550822A (fr) | 1974-06-28 |
| GB1348359A (en) | 1974-03-13 |
| YU216679A (en) | 1982-05-31 |
| IE36334L (en) | 1972-10-28 |
| ES402865A1 (es) | 1976-02-01 |
| ZA722837B (en) | 1973-02-28 |
| YU106180A (en) | 1982-05-31 |
| NL7205609A (enrdf_load_stackoverflow) | 1972-10-31 |
| BR7202723D0 (pt) | 1974-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1932426C3 (de) | Geformte Enzymkörper und Verfahren zu ihrer Herstellung | |
| DE69029527T3 (de) | Verfahren zur Gewinnung von Klavulinsäure und deren pharmazeutisch annehmbare Salze aus Fermentationskulturen von Streptomyces sp. | |
| EP0562583B1 (de) | Neue Alkylendiammonium-diclavulanat-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung | |
| DE1939341C2 (de) | Cephalosporinderivate und Verfahren zur ihrer Herstellung | |
| DE2461642C2 (de) | Roter Farbstoff und Verfahren zu seiner Herstellung | |
| DE1545915C3 (de) | Verfahren zur Herstellung von 3-Hydroxymethylcephalosporinen | |
| DE1151803B (de) | Verfahren zur Herstellung von 6-Acylaminopenicillansaeuren | |
| DE2221046A1 (de) | Antibiotika und verfahren zu ihrer herstellung | |
| DE69628002T2 (de) | Herstellung von clavunalat-salzen | |
| DE69633330T2 (de) | Verfahren zur herstellung von pharmazeutisch verträglichen salzen der clavulansäure | |
| DE69826852T2 (de) | Verbessertes verfahren zur fermentativer herstellung von penizillin | |
| DE69615204T2 (de) | Verfahren zur herstellung von kaliumclavulanat | |
| DE69828940T2 (de) | Verbessertes verfahren zur fermentativen herstellung von cephalosporin | |
| DD209835A5 (de) | Verbessertes verfahren zur herstellung von penicillansaeureestern | |
| DE2621076B2 (de) | Verfahren zur Herstellung von D-Aminosäuren | |
| DE1945607B2 (de) | Verfahren zur Herstellung von p-Aminobenzylpenicillin | |
| DE3822595C2 (de) | Verfahren zur Herstellung von 6-[(1R)-Hydroxyethyl]-penemsäuren | |
| DE2409569C2 (de) | Verfahren zur Herstellung von 7-Amino- &Omega;3-cephem-Derivaten | |
| DE1255109B (de) | Verfahren zur Herstellung von 6-Aminopenicillansaeure | |
| DE2533820A1 (de) | Verfahren zur deacylierung von penicillintetrazolen | |
| DE2441637C2 (de) | Verfahren zur Herstellung von 6- Aminopenicillansäure-1-oxid | |
| DE2121517B2 (de) | Verfahren zur Gewinnung von Ampho tenzin B | |
| DE2058371A1 (de) | Verfahren zur Herstellung von 6-Aminopenicillansaeure | |
| DE2528622A1 (de) | Verfahren zur reinigung der bei der enzymatischen spaltung von beta-lactam- antibiotika anfallenden produkte | |
| DE2436772C2 (de) | Verfahren zur Extraktion von N-blockierten Cephalosporin- oder Penicillinverbindungen aus deren wäßrigen Lösungen |