GB1008170A - Improvements in or relating to the preparation of semisynthetic penicillins - Google Patents
Improvements in or relating to the preparation of semisynthetic penicillinsInfo
- Publication number
- GB1008170A GB1008170A GB32221/63A GB3222163A GB1008170A GB 1008170 A GB1008170 A GB 1008170A GB 32221/63 A GB32221/63 A GB 32221/63A GB 3222163 A GB3222163 A GB 3222163A GB 1008170 A GB1008170 A GB 1008170A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- acid
- amino
- group
- reacting
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Penicillins of formula <FORM:1008170/C2/1> where R is (a) <FORM:1008170/C2/2> wherein X is an aryl, heterocyclic or alicyclic group, Y is hydrogen or a residue of an acid serving to protect the amino group, e.g. carbobenzoxy; or (b) an aryl, aralkyl, aryloxyalkyl, arylmercaptoalkyl or heterocyclic group which may be substituted and Z is hydrogen or the cation of an inorganic or organic nitrogen base, are prepared by reacting 6-amino penicillanic acid with an acid of formula R.COOH, where R has the above meaning, which acid has been activated by reaction with N,N-dimethylchloroformiminium chloride, the acylation taking place in an anhydrous or aqueous medium at - 20 DEG to 0 DEG C. in the presence of inorganic or organic basically reacting agents and, where required, removing the amino protecting group. The acylation may be carried out with (a) aqueous acetone and sodium bicarbonate, (b) anhydrous acetone and an aliphatic or hetero cyclic amine. Examples relate to the preparation of (a) a -aminobenzyl penicillin, (b) a -amino a -phenylacetyl penicillin, (c) phenoxymethyl penicillin, (d) bis-phenoxymethyl penicillin, (e) a -phenylbutyryl penicillin and (f) 2,5,7,8-tetramethyl - 6 - acetoxy chroman - 2 - (p - propionyl) penicillin. N,N-dimethylchloroforminium chloride [(CH3)2N = CHCl)Cl is produced by reacting phosgene with dimethyl formamide in a solvent. Specification 873,049 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS478662 | 1962-08-15 | ||
| CS478562 | 1962-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008170A true GB1008170A (en) | 1965-10-27 |
Family
ID=25746058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32221/63A Expired GB1008170A (en) | 1962-08-15 | 1963-08-15 | Improvements in or relating to the preparation of semisynthetic penicillins |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT245168B (en) |
| CH (1) | CH473834A (en) |
| GB (1) | GB1008170A (en) |
-
1963
- 1963-08-13 CH CH1000163A patent/CH473834A/en not_active IP Right Cessation
- 1963-08-15 GB GB32221/63A patent/GB1008170A/en not_active Expired
- 1963-08-16 AT AT657963A patent/AT245168B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT245168B (en) | 1966-02-10 |
| CH473834A (en) | 1969-06-15 |
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