JPS5772987A - Production of cephalosporanic acid derivative - Google Patents
Production of cephalosporanic acid derivativeInfo
- Publication number
- JPS5772987A JPS5772987A JP14685980A JP14685980A JPS5772987A JP S5772987 A JPS5772987 A JP S5772987A JP 14685980 A JP14685980 A JP 14685980A JP 14685980 A JP14685980 A JP 14685980A JP S5772987 A JPS5772987 A JP S5772987A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- acid derivative
- compound
- acylations
- 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.)
- Pending
Links
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 230000003115 biocidal effect Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000007970 thio esters Chemical class 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
- KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 150000001540 azides Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000009257 reactivity Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Landscapes
- Cephalosporin Compounds (AREA)
Abstract
PURPOSE: To reaction between 7-aminocephalosporanic acid derivative and a novel active thioester affords a cephalosporanic acid derivative used as an antibiotic with a very wide range of antibiotic spectrum with high safety in high yield.
CONSTITUTION: The reaction of 7-aminocephalosporanic acid derivative of formula I(R1 is halogen, azide, acetoxy) or its salt with with a 1-methyl-tetrazol-5-ylthiol ester of formula II (R2 is trifuoromethylthioacetic acid) gives the objective compound of formula III. A new compound of thioester of formula II has a almost the same level of reactivity as an acid chloride or mixed acid anyhdride, which are said to be highest reactive in acylations and effects acylations not only in the 7-position but also in the 3-position. The compound of formula II is obtained from a compound of formula IV and 2-trifluoromethylacetic acid in high yield.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14685980A JPS5772987A (en) | 1980-10-22 | 1980-10-22 | Production of cephalosporanic acid derivative |
| AT84109690T ATE31416T1 (en) | 1980-09-02 | 1981-09-01 | PROCESS FOR THE PRODUCTION OF CEPHALOSPORIN DERIVATIVES USING NEW THIOESTERS. |
| DE8181106833T DE3173499D1 (en) | 1980-09-02 | 1981-09-01 | Novel thioesters and process for the preparation of the same |
| EP81106833A EP0047014B1 (en) | 1980-09-02 | 1981-09-01 | Novel thioesters and process for the preparation of the same |
| EP84109690A EP0137227B1 (en) | 1980-09-02 | 1981-09-01 | Process for the preparation of cephalosporin derivatives using novel thioesters |
| DE8484109690T DE3176575D1 (en) | 1980-09-02 | 1981-09-01 | Process for the preparation of cephalosporin derivatives using novel thioesters |
| US06/298,884 US4463179A (en) | 1980-09-02 | 1981-09-02 | 1H-1,2,3-triazol-5-ylthio ester of N-carbobenzyloxy-p-hydroxyphenylglycine |
| US06/414,946 US4456754A (en) | 1980-09-02 | 1982-09-03 | Process for the preparation of cephalosporin derivatives using thioesters |
| US06/545,202 US4454323A (en) | 1980-09-02 | 1983-10-25 | 1-Methyltetrazol-5-ylthio ester of cyanomethylthioacetic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14685980A JPS5772987A (en) | 1980-10-22 | 1980-10-22 | Production of cephalosporanic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5772987A true JPS5772987A (en) | 1982-05-07 |
Family
ID=15417169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14685980A Pending JPS5772987A (en) | 1980-09-02 | 1980-10-22 | Production of cephalosporanic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5772987A (en) |
-
1980
- 1980-10-22 JP JP14685980A patent/JPS5772987A/en active Pending
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