GB1212551A - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- GB1212551A GB1212551A GB01530/68A GB1153068A GB1212551A GB 1212551 A GB1212551 A GB 1212551A GB 01530/68 A GB01530/68 A GB 01530/68A GB 1153068 A GB1153068 A GB 1153068A GB 1212551 A GB1212551 A GB 1212551A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- apa
- solvent
- micro
- hydrolysis
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 8
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- 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 abstract 10
- 229940049954 penicillin Drugs 0.000 abstract 6
- 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 abstract 5
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 244000005700 microbiome Species 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 2
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract 2
- 229940056360 penicillin g Drugs 0.000 abstract 2
- 229960003424 phenylacetic acid Drugs 0.000 abstract 2
- 239000003279 phenylacetic acid Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 241000588724 Escherichia coli Species 0.000 abstract 1
- 108010073038 Penicillin Amidase Proteins 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 229920001429 chelating resin Polymers 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000007071 enzymatic hydrolysis Effects 0.000 abstract 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 abstract 1
- 239000000284 extract Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 239000011780 sodium chloride Substances 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/014—Ion-exchange processes in general; Apparatus therefor in which the adsorbent properties of the ion-exchanger are involved, e.g. recovery of proteins or other high-molecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
1,212,551. Penicillins. ANKERFARM S.p.A. 8 March, 1968 [8 March, 1967], No. 11530/68. Heading C2A. A semi-synthetic penicillin is produced by the acylatiqn of 6 - aminopenicillanic acid adsorbed on an anion exchange resin e.g. Amberlite (Registered Trade Mark) IRA-401. The 6-APA is obtained by the enzymatic hydrolysis of a penicillin such as benzyl penicillin. Preferably the penicillin acylase is derived from a micro-organism resistant to high concentrations of the acyl moiety of the starting penicillin, e.g. phenylacetic acid or phenoxyacetic acid. Thus, in the case of benzylpenicillin, the micro-organism may be a mutant of E. coli Ankerfarm Sp. 27/14 (CBS 128À67) cultured serially on media containing increasing concentrations of phenylacetic acid or phenoxyacetic acid. The hydrolysis of the penicillin may be carried out with cultures or enzyme extracts of the micro-organisms. After hydrolysis, impurities may be removed by extraction with a water-immiscible solvent, e.g. ether, and the aqueous phase containing the 6- APA treated with the resin at pH 6À0. The 6-APA resinate is separated from the solvent, washed to remove impurities and then suspended in water of pH 7 to 9 containing sodium chloride. The acylating agent is used as the chloride or anhydride, which is dissolved in a watermiscible solvent such as acetone and added to the aqueous suspension of 6-APA resinate at e.g. 0‹ C. After acidifying to e.g. pH 2À0, the result ant penicillin may be extracted with a waterimmiscible solvent e.g. ethyl acetate. The penicillin may be recovered as a salt by extracting the organic solution thereof with an aqueous solution of a base, e.g. sodium bicarbonate solution.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1345267 | 1967-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1212551A true GB1212551A (en) | 1970-11-18 |
Family
ID=11144455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB01530/68A Expired GB1212551A (en) | 1967-03-08 | 1968-03-08 | Penicillins |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT284336B (en) |
| CH (1) | CH529787A (en) |
| DE (1) | DE1670024A1 (en) |
| ES (1) | ES340130A1 (en) |
| GB (1) | GB1212551A (en) |
| NL (1) | NL6705787A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113941A (en) | 1975-06-26 | 1978-09-12 | Bayer Aktiengesellschaft | Process for purifying products obtained from enzymatic cleavage of beta-lactam antibiotics |
| EP0012395A1 (en) * | 1978-12-07 | 1980-06-25 | Mitsubishi Kasei Corporation | Method for synthesis of penicillin |
| WO1997035029A1 (en) * | 1996-03-15 | 1997-09-25 | Antibioticos, S.A. | Alternative process for producing 6-amino-penicillanic acid (6-apa) |
| ES2105988A1 (en) * | 1996-03-15 | 1997-10-16 | Antibioticos Sa | Process for purifying 7-substituted-amino-desacetoxy-cephalosporines through the use of filtration membranes |
-
1967
- 1967-04-25 NL NL6705787A patent/NL6705787A/xx unknown
- 1967-05-03 ES ES340130A patent/ES340130A1/en not_active Expired
-
1968
- 1968-01-12 CH CH46268A patent/CH529787A/en not_active IP Right Cessation
- 1968-02-08 DE DE19681670024 patent/DE1670024A1/en active Pending
- 1968-02-28 AT AT193568A patent/AT284336B/en not_active IP Right Cessation
- 1968-03-08 GB GB01530/68A patent/GB1212551A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113941A (en) | 1975-06-26 | 1978-09-12 | Bayer Aktiengesellschaft | Process for purifying products obtained from enzymatic cleavage of beta-lactam antibiotics |
| EP0012395A1 (en) * | 1978-12-07 | 1980-06-25 | Mitsubishi Kasei Corporation | Method for synthesis of penicillin |
| WO1997035029A1 (en) * | 1996-03-15 | 1997-09-25 | Antibioticos, S.A. | Alternative process for producing 6-amino-penicillanic acid (6-apa) |
| ES2105988A1 (en) * | 1996-03-15 | 1997-10-16 | Antibioticos Sa | Process for purifying 7-substituted-amino-desacetoxy-cephalosporines through the use of filtration membranes |
| US6110699A (en) * | 1996-03-15 | 2000-08-29 | Antibioticos, S.A. | Process for producing 6-amino-penicillanic acid and phenylacetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1670024A1 (en) | 1971-02-25 |
| AT284336B (en) | 1970-09-10 |
| ES340130A1 (en) | 1968-08-16 |
| NL6705787A (en) | 1968-09-09 |
| CH529787A (en) | 1972-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |