JPS5569591A - Azetidinone derivative and its preparation - Google Patents
Azetidinone derivative and its preparationInfo
- Publication number
- JPS5569591A JPS5569591A JP14269278A JP14269278A JPS5569591A JP S5569591 A JPS5569591 A JP S5569591A JP 14269278 A JP14269278 A JP 14269278A JP 14269278 A JP14269278 A JP 14269278A JP S5569591 A JPS5569591 A JP S5569591A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- protecting group
- eliminated
- 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
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 2
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract 1
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction 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
- 239000002132 β-lactam antibiotic Substances 0.000 abstract 1
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:An azetidinone derivative of formula I: (R1 is H or acyl group; R2 is H, alkyl, halogenoalkyl group, etc.; n is an integer 2-5), and a 2-ketopenicillin ester derivative of formula II: (R3 is R2 except H).
EXAMPLE: 5R-3-(2'-Hydroxy)ethoxy-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2- carboxylic acid.
USE: Antibacterials, β-lactamase inhibitors, and intermediates for their synthesis, effective against β-lactam antibiotic-resistant bacteria.
PROCESS: The compound of formula II, obtained from a compound of formula III: (X is halogen), is reacted with a compound of formula IV (R4 is OH-protecting group), and the protecting group is eliminated to give a compound of formula V. The group R1 is changed into an acyl group, or the carboxyl-protecting group is eliminated to form the compound of formula I.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14269278A JPS5569591A (en) | 1978-11-17 | 1978-11-17 | Azetidinone derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14269278A JPS5569591A (en) | 1978-11-17 | 1978-11-17 | Azetidinone derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5569591A true JPS5569591A (en) | 1980-05-26 |
Family
ID=15321302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14269278A Pending JPS5569591A (en) | 1978-11-17 | 1978-11-17 | Azetidinone derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5569591A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
-
1978
- 1978-11-17 JP JP14269278A patent/JPS5569591A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
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