GB820535A - A new salt of phenoxymethyl-penicillin and its use for the isolation of said penicillin - Google Patents
A new salt of phenoxymethyl-penicillin and its use for the isolation of said penicillinInfo
- Publication number
- GB820535A GB820535A GB27447/57A GB2744757A GB820535A GB 820535 A GB820535 A GB 820535A GB 27447/57 A GB27447/57 A GB 27447/57A GB 2744757 A GB2744757 A GB 2744757A GB 820535 A GB820535 A GB 820535A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- salt
- beta
- phenoxymethylpenicillin
- organic solvent
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title abstract 7
- 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 title abstract 5
- 229930195708 Penicillin V Natural products 0.000 title abstract 5
- 229940056367 penicillin v Drugs 0.000 title abstract 5
- 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 title abstract 5
- 229930182555 Penicillin Natural products 0.000 title abstract 3
- 229940049954 penicillin Drugs 0.000 title abstract 3
- 238000002955 isolation Methods 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 5
- 239000003960 organic solvent Substances 0.000 abstract 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000000284 extract Substances 0.000 abstract 3
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 235000010633 broth Nutrition 0.000 abstract 2
- 230000004151 fermentation Effects 0.000 abstract 2
- 238000000855 fermentation Methods 0.000 abstract 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 abstract 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 2
- LFXFALZEDWJECS-UHFFFAOYSA-N 2-hydroxy-3-phenoxypropanoic acid Chemical compound OC(=O)C(O)COC1=CC=CC=C1 LFXFALZEDWJECS-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000012062 aqueous buffer Substances 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract 1
- 229940056360 penicillin g Drugs 0.000 abstract 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 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 229910000162 sodium phosphate Inorganic materials 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to the phenoxymethylpenicillinate of N,N-di-isopropyl-beta-hydroxy-ethylamine. The salt is prepared by reacting the free base with the free acid in an organic solvent, or by reacting a salt of the base, e.g. the acetate, with a salt of the penicillin, e.g. potassium phenoxymethylpenicillin. The salt is sparingly soluble in organic solvents such as n-butyl acetate, n-amyl acetate, ethyl acetate, acetone, methyl ethyl ketone and ether. It is used in recovering phenoxymethylpenicillin from fermentation broths, the penicillin so recovered being substantially free from phenoxyacetic acid or beta-phenoxylactic acid (precursors used in the fermentation) and from benzyl penicillin. The broth is acidified to solubilize the phenoxymethyl penicillin, e.g. by the addition of phosphoric acid to pH 2.0, extracted with n-butyl acetate or other organic solvent sparingly soluble in water, N,N-diisopropyl - beta - hydroxyethylamine added to the extract and the phenoxymethylpenicillinate of N,N - diisopropyl - beta - hydroxy - ethylamine crystals filtered off, washed with acetone and dried. Alternatively, the organic solvent extract is treated with an aqueous buffer, e.g. aqueous sodium phosphate of pH 6.5, and the aqueous extract so obtained is then extracted with the organic solvent and the base added to that extract. The salt may be converted to other salts of phenoxymethylpenicillin; or may be converted to the free phenoxymethylpenicillin by treatment with strong acid in aqueous solution or suspension.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK820535X | 1956-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB820535A true GB820535A (en) | 1959-09-23 |
Family
ID=8153046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27447/57A Expired GB820535A (en) | 1956-09-04 | 1957-08-30 | A new salt of phenoxymethyl-penicillin and its use for the isolation of said penicillin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB820535A (en) |
-
1957
- 1957-08-30 GB GB27447/57A patent/GB820535A/en not_active Expired
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