GB994402A - Process for the separation of 6-aminopenicillanic acid and ampicillin - Google Patents
Process for the separation of 6-aminopenicillanic acid and ampicillinInfo
- Publication number
- GB994402A GB994402A GB3404063A GB3404063A GB994402A GB 994402 A GB994402 A GB 994402A GB 3404063 A GB3404063 A GB 3404063A GB 3404063 A GB3404063 A GB 3404063A GB 994402 A GB994402 A GB 994402A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trialkylamine
- aminopenicillanic acid
- mixture
- aminobenzyl penicillin
- ampicillin
- 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
- 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 title abstract 4
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 title abstract 4
- 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 title abstract 2
- 229960000723 ampicillin Drugs 0.000 title abstract 2
- 238000000926 separation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- -1 demethyl sulphoxide Chemical compound 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008247 solid mixture Substances 0.000 abstract 1
- 239000000725 suspension Substances 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 separation of 6-aminopenicillanic acid and a -aminobenzyl penicillin from mixtures containing same, is obtained by suspending a solid mixture of 6-aminopenicillanic acid and a -aminobenzyl penicillin in an inert organic solvent capable of dissolving trialkylamine salts of a -aminobenzyl penicillin, cooling the resulting suspension to approximately 0 DEG C., adding thereto one mol. of a trialkylamine per mol. of a -aminobenzylpenicillin contained in the origina-mixture at 0 DEG C. to effect dissolution of the a -aminobenzyl penicillin and filtering the mixture to remove the undissolved 6-aminopenicillanic acid therefrom and recovering from the residual filtrate the ampicillin as its trialkylamine salt. Specified organic solvents are methylene chloride, chloroform, methanol, dimethylformamide, formamide, acetone, acetonitrile, ethanol, demethyl sulphoxide and glycol monomethyl ether. The trialkylamine may be trimethylamine, triethylamine, methyldiethylamine or tripolyamine. Reference has been directed by the Comptroller to Specification 870,396.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF37739A DE1178434B (en) | 1962-09-04 | 1962-09-04 | Process for the separation of 6-aminopenicillanic acid and ª ‡ -aminobenzylpenicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994402A true GB994402A (en) | 1965-06-10 |
Family
ID=7097031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3404063A Expired GB994402A (en) | 1962-09-04 | 1963-08-28 | Process for the separation of 6-aminopenicillanic acid and ampicillin |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1178434B (en) |
| GB (1) | GB994402A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996030376A1 (en) * | 1995-03-31 | 1996-10-03 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| US5916762A (en) * | 1995-03-31 | 1999-06-29 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| EP0997199A1 (en) * | 1998-10-26 | 2000-05-03 | Dsm N.V. | Method for separation of solid compounds in suspension |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES270202A1 (en) * | 1960-09-06 | 1962-02-01 | Pfizer & Co C | A procedure for the recovery of amphalt amino acids (Machine-translation by Google Translate, not legally binding) |
-
1962
- 1962-09-04 DE DEF37739A patent/DE1178434B/en active Pending
-
1963
- 1963-08-28 GB GB3404063A patent/GB994402A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996030376A1 (en) * | 1995-03-31 | 1996-10-03 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| BE1009264A3 (en) * | 1995-03-31 | 1997-01-07 | Dsm Nv | Process for the extraction of ampicillin. |
| US5916762A (en) * | 1995-03-31 | 1999-06-29 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| EP0997199A1 (en) * | 1998-10-26 | 2000-05-03 | Dsm N.V. | Method for separation of solid compounds in suspension |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1178434B (en) | 1964-09-24 |
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