GB1341921A - Process for the preparation of semisynthetic penicillins - Google Patents
Process for the preparation of semisynthetic penicillinsInfo
- Publication number
- GB1341921A GB1341921A GB35371A GB1341921DA GB1341921A GB 1341921 A GB1341921 A GB 1341921A GB 35371 A GB35371 A GB 35371A GB 1341921D A GB1341921D A GB 1341921DA GB 1341921 A GB1341921 A GB 1341921A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- penicillins
- formula
- acid
- alkali metal
- 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 10
- 150000002960 penicillins Chemical class 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 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 5
- 229940049954 penicillin Drugs 0.000 abstract 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000012074 organic phase Substances 0.000 abstract 3
- 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 2
- 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 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 abstract 1
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000001694 spray drying Methods 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
- C07D499/04—Preparation
- C07D499/10—Modification of an amino radical directly attached in position 6
- C07D499/12—Acylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1341921 Preparation of penicillins FABRICA DE ANTIBIOTICE IASI 4 Jan 1971 353/71 Heading C2A A process for the preparation of semisynthetic penicillins of Formulµ I and II: wherein in Formula I R and R 1 are methoxy groups or hydrogen, and R 2 is a nitro group or hydrogen, and in Formula II R is an alkyl, aralkyl or aryl group, by acylating 6-aminopenicillanic acid with the appropriate acid chloride in the case of penicillins of Formula I or with the appropriate mixed anhydride of an N-protected alpha-aminoacid in the case of penicillins of Formula II, wherein the acylation is carried out in solution in an organic solvent using the 6-aminopenicillanic acid in the form of its triethylammonium salt and the triethylammonium salt of the resulting penicillin is extracted with water from the organic solvent. The aqueous extract containing the triethylammonium salt may be acidified with mineral acid in the presence of dichloromethane and the resulting organic phase containing the penicillin in its acid form is separated from the aqueous phase. The separated organic phase containing the penicillin in its acid form may be treated with an aqueous solution of an alkali metal hydroxide and the aqueous phase containing the penicillin in the form of its alkali metal salt is separated from the organic phase. The alkali metal salt of the penicillin may be recovered by spray drying the aqueous solution thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO6210770 | 1970-01-12 | ||
| GB35371 | 1971-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1341921A true GB1341921A (en) | 1973-12-25 |
Family
ID=26235872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35371A Expired GB1341921A (en) | 1970-01-12 | 1971-01-04 | Process for the preparation of semisynthetic penicillins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1341921A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126351A1 (en) * | 1983-05-19 | 1984-11-28 | Fried. Krupp Gesellschaft mit beschränkter Haftung | Process for the isolation and purification of antibiotics |
-
1971
- 1971-01-04 GB GB35371A patent/GB1341921A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0126351A1 (en) * | 1983-05-19 | 1984-11-28 | Fried. Krupp Gesellschaft mit beschränkter Haftung | Process for the isolation and purification of antibiotics |
| US4581166A (en) * | 1983-05-19 | 1986-04-08 | Fried. Krupp Gesellschaft Mit Beschrankter Haftung | Method for isolating and purifying antibiotics |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |