JPS5772986A - Production of cephalosporin derviative - Google Patents
Production of cephalosporin derviativeInfo
- Publication number
- JPS5772986A JPS5772986A JP55149112A JP14911280A JPS5772986A JP S5772986 A JPS5772986 A JP S5772986A JP 55149112 A JP55149112 A JP 55149112A JP 14911280 A JP14911280 A JP 14911280A JP S5772986 A JPS5772986 A JP S5772986A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formulai
- lower alkyl
- acid
- acyl
- 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.)
- Granted
Links
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- -1 1H-tetrazol-5-yl Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical group S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000007858 starting material Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
PURPOSE: Various kinds of conditions such as the kind of ester, solvent or acid acceptor, are selected to effect the direct acyl interchange reaction of the starting compound to produce the titled compound used as an antibiotic with industrial advantage.
CONSTITUTION: A compound of formulaI[R1 is acylamide; R2 is lower alkyl; R3 is heteroring (1H-tetrazol-5-yl group)] is made to react with both a compound of formula II (R4 is lower alkyl) and the third compound of R5-X(R5 is acyl X is halogen) in a halogenated hydrocarbon solvent containing more than 1 equivalent amount of water based on the compound of formulaI. The reaction product is treated with an acid such as hydrochloric acid to eliminate ester to give the objective compound of formula III. This process enables the continuous interchange of groups in the 3 and 7 positions of cephamycin obtained by the cultivation of a microorganism and is very useful in industry.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55149112A JPS5772986A (en) | 1980-10-24 | 1980-10-24 | Production of cephalosporin derviative |
| IT68386/81A IT1144849B (en) | 1980-10-24 | 1981-10-23 | METHOD FOR THE PREPARATION OF Cephalosporin derivatives |
| ES506532A ES506532A0 (en) | 1980-10-24 | 1981-10-23 | A PROCEDURE FOR THE PREPARATION OF A CEFA-LOSPORINA DERIVATIVE |
| CA000388592A CA1155835A (en) | 1980-10-24 | 1981-10-23 | Process for preparing cephalosporin derivatives |
| FI813320A FI72122C (en) | 1980-10-24 | 1981-10-23 | Process for the preparation of derivatives of cephalosporin. |
| CH6792/81A CH649088A5 (en) | 1980-10-24 | 1981-10-23 | Process for the preparation of cephalosporin derivatives |
| NL8104831A NL8104831A (en) | 1980-10-24 | 1981-10-26 | PROCESS FOR THE PREPARATION OF CEPHALOSPORINE DERIVATIVES. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55149112A JPS5772986A (en) | 1980-10-24 | 1980-10-24 | Production of cephalosporin derviative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5772986A true JPS5772986A (en) | 1982-05-07 |
| JPH0157116B2 JPH0157116B2 (en) | 1989-12-04 |
Family
ID=15467965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55149112A Granted JPS5772986A (en) | 1980-10-24 | 1980-10-24 | Production of cephalosporin derviative |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5772986A (en) |
| CA (1) | CA1155835A (en) |
| CH (1) | CH649088A5 (en) |
| ES (1) | ES506532A0 (en) |
| FI (1) | FI72122C (en) |
| IT (1) | IT1144849B (en) |
| NL (1) | NL8104831A (en) |
-
1980
- 1980-10-24 JP JP55149112A patent/JPS5772986A/en active Granted
-
1981
- 1981-10-23 CA CA000388592A patent/CA1155835A/en not_active Expired
- 1981-10-23 ES ES506532A patent/ES506532A0/en active Granted
- 1981-10-23 FI FI813320A patent/FI72122C/en not_active IP Right Cessation
- 1981-10-23 IT IT68386/81A patent/IT1144849B/en active
- 1981-10-23 CH CH6792/81A patent/CH649088A5/en not_active IP Right Cessation
- 1981-10-26 NL NL8104831A patent/NL8104831A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0157116B2 (en) | 1989-12-04 |
| CH649088A5 (en) | 1985-04-30 |
| FI813320L (en) | 1982-04-25 |
| FI72122B (en) | 1986-12-31 |
| CA1155835A (en) | 1983-10-25 |
| NL8104831A (en) | 1982-05-17 |
| IT1144849B (en) | 1986-10-29 |
| IT8168386A0 (en) | 1981-10-23 |
| ES8303430A1 (en) | 1983-02-01 |
| FI72122C (en) | 1987-04-13 |
| ES506532A0 (en) | 1983-02-01 |
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