JPS5573681A - 2-thio substituted-1-carbapenam-3-carboxylic acid derivative and its preparation - Google Patents
2-thio substituted-1-carbapenam-3-carboxylic acid derivative and its preparationInfo
- Publication number
- JPS5573681A JPS5573681A JP14846178A JP14846178A JPS5573681A JP S5573681 A JPS5573681 A JP S5573681A JP 14846178 A JP14846178 A JP 14846178A JP 14846178 A JP14846178 A JP 14846178A JP S5573681 A JPS5573681 A JP S5573681A
- Authority
- JP
- Japan
- Prior art keywords
- compound shown
- formula
- carbapenam
- alkyl
- carboxylic acid
- 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
- 150000001875 compounds Chemical class 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- -1 e.g. Substances 0.000 abstract 2
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 abstract 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:A compound shown by the formula I (R1 is H, 1W6C alkyl, OH, acyloxy, etc.; R2 is 1W6C alkyl, aryl, aralkyl, etc.; R3 is H, ester residue, salt- forming group together with carboxyl).
EXAMPLE: 2-(2'-Aminoethyl)mercarto-1-carbapenam-3-carboxylic acid.
USE: Antibiotics and a synthetic intermediate of thienamycin dirivative useful as antibacterial agents.
PROCESS: 1-Carba-2-penam compound shown by the formula II is reacted with a compound shown by the formula R2-S-R4 (R4 is H or alkali metal) in an inert solvent, e.g., THF at -78W30°C to give a compound shown by the fomula I. The addition of a base, e.g., triethylamine, shortens the reaction time extremely. The compound shown by the formula II usable as a starting material is obtained by reacting a compound shown by the formula III (R9 is alkyl, etc.) with a compound shown by the formula IV (X is halogen, etc.).
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14846178A JPS5573681A (en) | 1978-11-30 | 1978-11-30 | 2-thio substituted-1-carbapenam-3-carboxylic acid derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14846178A JPS5573681A (en) | 1978-11-30 | 1978-11-30 | 2-thio substituted-1-carbapenam-3-carboxylic acid derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5573681A true JPS5573681A (en) | 1980-06-03 |
Family
ID=15453265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14846178A Pending JPS5573681A (en) | 1978-11-30 | 1978-11-30 | 2-thio substituted-1-carbapenam-3-carboxylic acid derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5573681A (en) |
-
1978
- 1978-11-30 JP JP14846178A patent/JPS5573681A/en active Pending
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