GB1364088A - 3-substituted-thio-methyl-3-cephem-4-carboxylic acid derivatives and preparation thereof - Google Patents
3-substituted-thio-methyl-3-cephem-4-carboxylic acid derivatives and preparation thereofInfo
- Publication number
- GB1364088A GB1364088A GB6058871A GB6058871A GB1364088A GB 1364088 A GB1364088 A GB 1364088A GB 6058871 A GB6058871 A GB 6058871A GB 6058871 A GB6058871 A GB 6058871A GB 1364088 A GB1364088 A GB 1364088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cephem
- thio
- substituted
- methyl
- preparation
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Starting from novel cephalosporin derivatives of the formula <IMAGE> in which R represents a heterocyclic radical optionally carrying several substituents and A represents one of the groups <IMAGE> in which groups R1 and R2 represent hydrogen or lower alkyl or aryl radicals which can have one or more substituents, X represents oxygen or sulphur and R3 represents a lower alkyl radical, corresponding 7-aminocephemcarboxylic acids can be prepared in high yield by reacting a compound of the formula I with a silylating agent and then treating the reaction product first with an iminohalide-forming agent and then with an iminoether-forming reagent, after which the reaction mixture is subjected to a hydrolysis. The N-unsubstituted 7-aminocephemcarboxylic acid compounds thus obtained carrying the radical R-S-CH2- in position 3 are important intermediates in the synthesis of cephalosporin antibiotics.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12946770A JPS505719B1 (en) | 1970-12-30 | 1970-12-30 | |
| JP4408871A JPS5439392B1 (en) | 1971-06-19 | 1971-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364088A true GB1364088A (en) | 1974-08-21 |
Family
ID=26383937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6058871A Expired GB1364088A (en) | 1970-12-30 | 1971-12-29 | 3-substituted-thio-methyl-3-cephem-4-carboxylic acid derivatives and preparation thereof |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH611301A5 (en) |
| DE (1) | DE2164561A1 (en) |
| FR (1) | FR2120121B1 (en) |
| GB (1) | GB1364088A (en) |
| NL (1) | NL7117960A (en) |
| SE (1) | SE415180B (en) |
-
1971
- 1971-12-23 CH CH1887271A patent/CH611301A5/en not_active IP Right Cessation
- 1971-12-24 DE DE19712164561 patent/DE2164561A1/en not_active Ceased
- 1971-12-28 SE SE1676371A patent/SE415180B/en unknown
- 1971-12-28 NL NL7117960A patent/NL7117960A/xx not_active Application Discontinuation
- 1971-12-29 GB GB6058871A patent/GB1364088A/en not_active Expired
- 1971-12-29 FR FR7147357A patent/FR2120121B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2120121B1 (en) | 1975-08-01 |
| FR2120121A1 (en) | 1972-08-11 |
| NL7117960A (en) | 1972-07-04 |
| DE2164561A1 (en) | 1972-07-27 |
| SE415180B (en) | 1980-09-15 |
| CH611301A5 (en) | 1979-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |