BE519389A - - Google Patents
Info
- Publication number
- BE519389A BE519389A BE519389DA BE519389A BE 519389 A BE519389 A BE 519389A BE 519389D A BE519389D A BE 519389DA BE 519389 A BE519389 A BE 519389A
- Authority
- BE
- Belgium
- Prior art keywords
- acids
- penicillins
- salts
- penicillin
- extraction
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 72
- 150000007513 acids Chemical class 0.000 claims description 51
- 150000002960 penicillins Chemical class 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 32
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000012045 crude solution Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 102000014961 Protein Precursors Human genes 0.000 claims description 6
- 108010078762 Protein Precursors Proteins 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- -1 alkali metal salts Chemical class 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 235000011056 potassium acetate Nutrition 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 230000001476 alcoholic Effects 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L Barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims 1
- 241000243251 Hydra Species 0.000 claims 1
- 229910001626 barium chloride Inorganic materials 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 36
- 229940049954 Penicillin Drugs 0.000 description 32
- 229960000626 benzylpenicillin Drugs 0.000 description 32
- 238000000855 fermentation Methods 0.000 description 21
- 230000004151 fermentation Effects 0.000 description 21
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 12
- 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 9
- 239000012071 phase Substances 0.000 description 9
- 229960004331 phenoxymethylpenicillin Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- QCDWFXQBSFUVSP-UHFFFAOYSA-N Phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940056360 Penicillin G Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 210000002784 Stomach Anatomy 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 159000000009 barium salts Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000001131 transforming Effects 0.000 description 2
- 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
- MDQGTDMBVJCTBN-JCGDXUMPSA-N 6-formamidopenicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC=O)C(=O)N21 MDQGTDMBVJCTBN-JCGDXUMPSA-N 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N Amyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 230000037408 Distribution ratio Effects 0.000 description 1
- 230000036499 Half live Effects 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229960005323 Phenoxyethanol Drugs 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229940076185 Staphylococcus aureus Drugs 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 101700061366 acl-2 Proteins 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000010564 aerobic fermentation Methods 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000037348 biosynthesis Effects 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 235000021403 cultural food Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N 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
- 239000008101 lactose Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE519389A true BE519389A (de) |
Family
ID=155626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE519389D BE519389A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE519389A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820789A (en) * | 1954-06-21 | 1958-01-21 | American Home Prod | Dibenzylethylenediamine-penicillin v |
-
0
- BE BE519389D patent/BE519389A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820789A (en) * | 1954-06-21 | 1958-01-21 | American Home Prod | Dibenzylethylenediamine-penicillin v |
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