GB1467610A - 7-aminocephalosporanic acid and derivatives thereof - Google Patents
7-aminocephalosporanic acid and derivatives thereofInfo
- Publication number
- GB1467610A GB1467610A GB3039575A GB3039575A GB1467610A GB 1467610 A GB1467610 A GB 1467610A GB 3039575 A GB3039575 A GB 3039575A GB 3039575 A GB3039575 A GB 3039575A GB 1467610 A GB1467610 A GB 1467610A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- compounds
- ester
- acyl
- reacted
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- -1 imino halide Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Compounds of the formula: <IMAGE> in which X is hydrogen, azido or -YR1, Y is oxygen or sulphur and R1 is lower alkyl, acyl or a heterocyclic radical, and Z' is hydrogen or an ester radical, are prepared from corresponding compounds of the formula: <IMAGE> in which R is acyl and Z is hydrogen or the residue of a mixed anhydride or of an ester. To do this, the starting material is reacted with an agent which forms imino halide in the presence of an amine under anhydrous conditions, and the reaction product is reacted with an anhydrous alkanol; the resulting 1-deoxy-7-imino ether compound is then subjected to acid hydrolysis. The hydrolysis simultaneously unblocks the 4-carboxyl group when Z is a mixed anhydride or a readily hydrolysable ester. The compounds are intermediates for the preparation of antibiotics of the cephalosporin series.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49085509A JPS5826355B2 (en) | 1974-07-24 | 1974-07-24 | 7- Aminocephalosporan sanyuudoutaino Seizouhouhou |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1467610A true GB1467610A (en) | 1977-03-16 |
Family
ID=13860889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3039575A Expired GB1467610A (en) | 1974-07-24 | 1975-07-21 | 7-aminocephalosporanic acid and derivatives thereof |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5826355B2 (en) |
| CH (1) | CH612977A5 (en) |
| DE (1) | DE2532723A1 (en) |
| FR (1) | FR2279754A1 (en) |
| GB (1) | GB1467610A (en) |
| IE (1) | IE41837B1 (en) |
| NL (1) | NL7508837A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0137534A3 (en) * | 1983-10-07 | 1986-01-08 | Gist - Brocades N.V. | One-pot process for preparation of 7beta-amino- and 7beta-acylamino- 3-substituted methyl-3-cephem-4-carboxylic acid derivatives and process for deoxygenation of 7beta-acylamino-3-cephem-4-carboxylic acid 1-oxide derivatives |
| US10308666B2 (en) * | 2014-12-23 | 2019-06-04 | Merck Sharp & Dohme Corp. | 7-aminocephem derivative compounds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53144596A (en) * | 1977-05-20 | 1978-12-15 | Meiji Seika Kaisha Ltd | Cephalosporanic acid derivatives and process for their preparation |
| GR70261B (en) * | 1977-12-12 | 1982-09-02 | Takeda Chemical Industries Ltd | |
| JPS61116545U (en) * | 1985-01-08 | 1986-07-23 | ||
| IL86941A (en) * | 1987-07-10 | 1993-07-08 | Gist Brocades Nv | Process for the preparation of cephem compounds and some new cephalosporin derivatives prepared by this process |
| EP0300546B1 (en) * | 1987-07-10 | 1995-08-09 | Gist-Brocades N.V. | Process for the preparation of cephem compounds and cephalosporin derivatives |
-
1974
- 1974-07-24 JP JP49085509A patent/JPS5826355B2/en not_active Expired
-
1975
- 1975-07-18 IE IE160875A patent/IE41837B1/en unknown
- 1975-07-21 GB GB3039575A patent/GB1467610A/en not_active Expired
- 1975-07-22 DE DE19752532723 patent/DE2532723A1/en not_active Withdrawn
- 1975-07-23 CH CH963275A patent/CH612977A5/en not_active IP Right Cessation
- 1975-07-24 NL NL7508837A patent/NL7508837A/en not_active Application Discontinuation
- 1975-07-24 FR FR7523134A patent/FR2279754A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0137534A3 (en) * | 1983-10-07 | 1986-01-08 | Gist - Brocades N.V. | One-pot process for preparation of 7beta-amino- and 7beta-acylamino- 3-substituted methyl-3-cephem-4-carboxylic acid derivatives and process for deoxygenation of 7beta-acylamino-3-cephem-4-carboxylic acid 1-oxide derivatives |
| US10308666B2 (en) * | 2014-12-23 | 2019-06-04 | Merck Sharp & Dohme Corp. | 7-aminocephem derivative compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CH612977A5 (en) | 1979-08-31 |
| JPS5826355B2 (en) | 1983-06-02 |
| FR2279754A1 (en) | 1976-02-20 |
| IE41837B1 (en) | 1980-04-09 |
| JPS5113790A (en) | 1976-02-03 |
| IE41837L (en) | 1976-01-24 |
| DE2532723A1 (en) | 1976-02-12 |
| NL7508837A (en) | 1976-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |