BE1009071A3 - Werkwijze voor de bereiding van een beta-lactam antibioticum. - Google Patents
Werkwijze voor de bereiding van een beta-lactam antibioticum. Download PDFInfo
- Publication number
- BE1009071A3 BE1009071A3 BE9500081A BE9500081A BE1009071A3 BE 1009071 A3 BE1009071 A3 BE 1009071A3 BE 9500081 A BE9500081 A BE 9500081A BE 9500081 A BE9500081 A BE 9500081A BE 1009071 A3 BE1009071 A3 BE 1009071A3
- Authority
- BE
- Belgium
- Prior art keywords
- lactam
- enzyme
- acylating agent
- beta
- core
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000003952 β-lactams Chemical class 0.000 title claims abstract description 21
- 239000003814 drug Substances 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 108090000790 Enzymes Proteins 0.000 claims abstract description 65
- 102000004190 Enzymes Human genes 0.000 claims abstract description 65
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims abstract description 18
- 239000002132 β-lactam antibiotic Substances 0.000 claims abstract description 18
- 229940124586 β-lactam antibiotics Drugs 0.000 claims abstract description 18
- 238000005917 acylation reaction Methods 0.000 claims abstract description 15
- 239000011541 reaction mixture Substances 0.000 claims abstract description 13
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000010933 acylation Effects 0.000 claims abstract description 6
- 150000001450 anions Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 15
- KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 6
- 108010093096 Immobilized Enzymes Proteins 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- -1 amino acid ester Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 29
- 230000003247 decreasing effect Effects 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 17
- 238000004448 titration Methods 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 238000004064 recycling Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 7
- NVIAYEIXYQCDAN-UHFFFAOYSA-N 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 3
- 108010073038 Penicillin Amidase Proteins 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 2
- 241000589220 Acetobacter Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 2
- 229940106164 cephalexin Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000003951 lactams Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GXBRYTMUEZNYJT-UHFFFAOYSA-N 2-anilinoacetamide Chemical compound NC(=O)CNC1=CC=CC=C1 GXBRYTMUEZNYJT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WNPVZANXRCPJPW-UHFFFAOYSA-N 5-[isocyano-(4-methylphenyl)sulfonylmethyl]-1,2,3-trimethoxybenzene Chemical class COC1=C(OC)C(OC)=CC(C([N+]#[C-])S(=O)(=O)C=2C=CC(C)=CC=2)=C1 WNPVZANXRCPJPW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 108700023418 Amidases Proteins 0.000 description 1
- 241000726092 Aphanocladium Species 0.000 description 1
- 241001619326 Cephalosporium Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000589565 Flavobacterium Species 0.000 description 1
- 241000721603 Mycoplana Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000586779 Protaminobacter Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 102000005922 amidase Human genes 0.000 description 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound 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 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 1
- 229960005361 cefaclor Drugs 0.000 description 1
- 229960004261 cefotaxime Drugs 0.000 description 1
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
- 229960002588 cefradine Drugs 0.000 description 1
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SZJUWKPNWWCOPG-UHFFFAOYSA-N methyl 2-anilinoacetate Chemical compound COC(=O)CNC1=CC=CC=C1 SZJUWKPNWWCOPG-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 150000005331 phenylglycines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
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)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9500081A BE1009071A3 (nl) | 1995-02-02 | 1995-02-02 | Werkwijze voor de bereiding van een beta-lactam antibioticum. |
| PL96321626A PL321626A1 (en) | 1995-02-02 | 1996-02-01 | Method of recovering ceophalexin |
| IN161MA1996 IN182469B (enrdf_load_stackoverflow) | 1995-02-02 | 1996-02-01 | |
| AU48461/96A AU4846196A (en) | 1995-02-02 | 1996-02-01 | Process for the recovery of cephalexin |
| KR1019970705249A KR100439322B1 (ko) | 1995-02-02 | 1996-02-01 | 세팔렉신의회수방법 |
| EP96904337A EP0815256A1 (en) | 1995-02-02 | 1996-02-01 | Process for the preparation of a beta-lactam antibiotic |
| CN96192915A CN1101395C (zh) | 1995-02-02 | 1996-02-01 | 头胞氨苄的回收方法 |
| AT96904336T ATE204580T1 (de) | 1995-02-02 | 1996-02-01 | Verfahren zur gewinnung von cephalexin |
| PCT/NL1996/000052 WO1996023897A1 (en) | 1995-02-02 | 1996-02-01 | PROCESS FOR THE PREPARATION OF A β-LACTAM ANTIBIOTIC |
| JP8523436A JPH11503408A (ja) | 1995-02-02 | 1996-02-01 | セファレキシンの回収方法 |
| PCT/NL1996/000051 WO1996023796A1 (en) | 1995-02-02 | 1996-02-01 | Process for the recovery of cephalexin |
| EP96904336A EP0869961B1 (en) | 1995-02-02 | 1996-02-01 | Process for the recovery of cephalexin |
| AU48462/96A AU4846296A (en) | 1995-02-02 | 1996-02-01 | Process for the preparation of a beta -lactam antibiotic |
| IN162MA1996 IN181940B (enrdf_load_stackoverflow) | 1995-02-02 | 1996-02-01 | |
| CZ972419A CZ241997A3 (cs) | 1995-02-02 | 1996-02-01 | Způsob oddělování cefalexinu |
| ES96904336T ES2163002T3 (es) | 1995-02-02 | 1996-02-01 | Procedimiento para la recuperacion de cefalexina. |
| DE69614711T DE69614711T2 (de) | 1995-02-02 | 1996-02-01 | Verfahren zur gewinnung von cephalexin |
| US08/903,879 US5874571A (en) | 1995-02-02 | 1997-07-31 | Process for the recovery of cephalexin |
| MX9705917A MX9705917A (es) | 1995-02-02 | 1997-08-01 | Procedimiento para la recuperacion de cefalexina. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9500081A BE1009071A3 (nl) | 1995-02-02 | 1995-02-02 | Werkwijze voor de bereiding van een beta-lactam antibioticum. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1009071A3 true BE1009071A3 (nl) | 1996-11-05 |
Family
ID=3888755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE9500081A BE1009071A3 (nl) | 1995-02-02 | 1995-02-02 | Werkwijze voor de bereiding van een beta-lactam antibioticum. |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0815256A1 (enrdf_load_stackoverflow) |
| AU (1) | AU4846296A (enrdf_load_stackoverflow) |
| BE (1) | BE1009071A3 (enrdf_load_stackoverflow) |
| IN (2) | IN182469B (enrdf_load_stackoverflow) |
| WO (1) | WO1996023897A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1007302C2 (nl) | 1997-10-17 | 1999-04-20 | Dsm Nv | Werkwijze voor de bereiding van een ß-lactam antibioticum. |
| DE19823332C2 (de) * | 1998-05-26 | 2000-09-07 | Unifar Kimya Sanayii Ve Ticare | Verfahren zur enzymatischen Herstellung von Betalactam-Antibiotika |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991009136A1 (es) * | 1989-12-12 | 1991-06-27 | Consejo Superior Investigaciones Cientificas | Procedimiento de sintesis de antibioticos semisinteticos en sistemas termodinamicamente controlados agua-cosolventes organicos miscibles apolares con el empleo de penicilina g acilasa |
| WO1992001061A1 (en) * | 1990-07-04 | 1992-01-23 | Novo Nordisk A/S | PROCESS FOR PREPARATION OF β-LACTAMS |
-
1995
- 1995-02-02 BE BE9500081A patent/BE1009071A3/nl not_active IP Right Cessation
-
1996
- 1996-02-01 AU AU48462/96A patent/AU4846296A/en not_active Abandoned
- 1996-02-01 EP EP96904337A patent/EP0815256A1/en not_active Ceased
- 1996-02-01 IN IN161MA1996 patent/IN182469B/en unknown
- 1996-02-01 IN IN162MA1996 patent/IN181940B/en unknown
- 1996-02-01 WO PCT/NL1996/000052 patent/WO1996023897A1/en not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991009136A1 (es) * | 1989-12-12 | 1991-06-27 | Consejo Superior Investigaciones Cientificas | Procedimiento de sintesis de antibioticos semisinteticos en sistemas termodinamicamente controlados agua-cosolventes organicos miscibles apolares con el empleo de penicilina g acilasa |
| WO1992001061A1 (en) * | 1990-07-04 | 1992-01-23 | Novo Nordisk A/S | PROCESS FOR PREPARATION OF β-LACTAMS |
Also Published As
| Publication number | Publication date |
|---|---|
| IN182469B (enrdf_load_stackoverflow) | 1999-04-17 |
| AU4846296A (en) | 1996-08-21 |
| IN181940B (enrdf_load_stackoverflow) | 1998-11-14 |
| EP0815256A1 (en) | 1998-01-07 |
| WO1996023897A1 (en) | 1996-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: DSM N.V. Effective date: 19970228 |