JPS5536404A - New penicillanic acid derivative, its optically active isomer, its salt, and its preparation - Google Patents
New penicillanic acid derivative, its optically active isomer, its salt, and its preparationInfo
- Publication number
- JPS5536404A JPS5536404A JP9735778A JP9735778A JPS5536404A JP S5536404 A JPS5536404 A JP S5536404A JP 9735778 A JP9735778 A JP 9735778A JP 9735778 A JP9735778 A JP 9735778A JP S5536404 A JPS5536404 A JP S5536404A
- Authority
- JP
- Japan
- Prior art keywords
- protecting group
- salt
- acid derivative
- formula
- optically active
- 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
- 150000003839 salts Chemical class 0.000 title abstract 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 4
- -1 ammouium Chemical group 0.000 abstract 3
- 125000006241 alcohol protecting group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940080818 propionamide Drugs 0.000 abstract 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 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: A penicillanic acid derivative of formula I (R1=phenyl, heterocyclic, pyridylthio; R2=H, alkali metal, ammouium, organic base cation, carboxyl protecting group), its optically active isomer, or its salt.
EXAMPLE: Sodium 6-[3'-hydroxy-2'-(1H-tetrazol-1-yl)propionamide] penicillanate.
USE: Anti-microbial agents, effective against gram negative (positive) bacteria.
PROCESS: 6-Aminopenicillanic acid of formula II or its derivative is made to react with 3-hydroxy-2-substituted propionic acid derivative of formula III (R3=H, alcohol protecting group) or its reactive derivative. Then, when R3 is an alcohol protecting group, the protecting group is removed, and when R2 is a carboxyl protecting group, the protecting group is removed if necessary. And if desired, the mixture is then subjected to the optical resolution and/or converted to the salt to give the compound of formula I, its stereoisomer and its salt.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9735778A JPS5536404A (en) | 1978-08-11 | 1978-08-11 | New penicillanic acid derivative, its optically active isomer, its salt, and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9735778A JPS5536404A (en) | 1978-08-11 | 1978-08-11 | New penicillanic acid derivative, its optically active isomer, its salt, and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5536404A true JPS5536404A (en) | 1980-03-14 |
Family
ID=14190235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9735778A Pending JPS5536404A (en) | 1978-08-11 | 1978-08-11 | New penicillanic acid derivative, its optically active isomer, its salt, and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5536404A (en) |
-
1978
- 1978-08-11 JP JP9735778A patent/JPS5536404A/en active Pending
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