IE791283L - Penicillin derivatives - Google Patents
Penicillin derivativesInfo
- Publication number
- IE791283L IE791283L IE791283A IE128379A IE791283L IE 791283 L IE791283 L IE 791283L IE 791283 A IE791283 A IE 791283A IE 128379 A IE128379 A IE 128379A IE 791283 L IE791283 L IE 791283L
- Authority
- IE
- Ireland
- Prior art keywords
- acid chloride
- penicillin derivatives
- anhydrous
- acid
- trimethylsilyloxycarbonylaminopenicillanic
- Prior art date
Links
- 150000002960 penicillins Chemical class 0.000 title 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 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 abstract 1
- 229960003022 amoxicillin Drugs 0.000 abstract 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 abstract 1
- 229960000723 ampicillin Drugs 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- -1 e.g. Natural products 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Trimethylsilyl or another easily hydrolyzed ester of 6- trimethylsilyloxycarbonylaminopenicillanic acid was prepared by bubbling dry carbon dioxide into an anhydrous solution of the corresponding 6- trimethylsilylaminopenicillanate and found to be a useful intermediate in the production of penicillins, e.g., amoxicillin and ampicillin, by its acylation in anhydrous media with the appropriate acid chloride or acid chloride hydrochloride.
[GB2037275A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97070478A | 1978-12-18 | 1978-12-18 | |
| US478079A | 1979-01-19 | 1979-01-19 | |
| US06/021,852 US4240960A (en) | 1979-03-19 | 1979-03-19 | Trimethylsilyl substituted penicillins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791283L true IE791283L (en) | 1980-06-18 |
| IE48521B1 IE48521B1 (en) | 1985-02-20 |
Family
ID=27357705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1283/79A IE48521B1 (en) | 1978-12-18 | 1979-08-08 | 6-trimethylsilyloxycarbonyl penicillanic acid esters and the production of penicillins therefrom |
Country Status (20)
| Country | Link |
|---|---|
| AR (1) | AR225898A1 (en) |
| AT (1) | AT364849B (en) |
| AU (1) | AU531779B2 (en) |
| CA (1) | CA1141752A (en) |
| CH (1) | CH642972A5 (en) |
| DK (2) | DK160613C (en) |
| ES (2) | ES482986A1 (en) |
| FI (1) | FI69846C (en) |
| FR (1) | FR2444683A1 (en) |
| GB (1) | GB2037275B (en) |
| GR (1) | GR73899B (en) |
| IE (1) | IE48521B1 (en) |
| IL (1) | IL57909A (en) |
| IT (1) | IT1117760B (en) |
| LU (1) | LU81432A1 (en) |
| NL (1) | NL171271C (en) |
| NO (1) | NO158541C (en) |
| PH (1) | PH16327A (en) |
| SE (2) | SE436281B (en) |
| YU (1) | YU221082A (en) |
-
1979
- 1979-05-22 SE SE7904483A patent/SE436281B/en not_active IP Right Cessation
- 1979-05-23 DK DK213779A patent/DK160613C/en not_active IP Right Cessation
- 1979-05-29 GR GR59209A patent/GR73899B/el unknown
- 1979-05-29 CA CA000328553A patent/CA1141752A/en not_active Expired
- 1979-05-30 FI FI791732A patent/FI69846C/en not_active IP Right Cessation
- 1979-05-31 NO NO791823A patent/NO158541C/en unknown
- 1979-06-01 GB GB7919231A patent/GB2037275B/en not_active Expired
- 1979-06-05 AU AU47774/79A patent/AU531779B2/en not_active Ceased
- 1979-06-12 FR FR7915037A patent/FR2444683A1/en active Granted
- 1979-06-13 CH CH554179A patent/CH642972A5/en not_active IP Right Cessation
- 1979-06-13 AT AT0421579A patent/AT364849B/en not_active IP Right Cessation
- 1979-06-19 NL NLAANVRAGE7904805,A patent/NL171271C/en not_active IP Right Cessation
- 1979-06-27 LU LU81432A patent/LU81432A1/en unknown
- 1979-07-16 PH PH22784A patent/PH16327A/en unknown
- 1979-07-26 AR AR277486A patent/AR225898A1/en active
- 1979-07-27 IL IL57909A patent/IL57909A/en not_active IP Right Cessation
- 1979-07-30 ES ES482986A patent/ES482986A1/en not_active Expired
- 1979-08-01 IT IT49919/79A patent/IT1117760B/en active
- 1979-08-08 IE IE1283/79A patent/IE48521B1/en not_active IP Right Cessation
-
1980
- 1980-04-16 ES ES490644A patent/ES8104301A1/en not_active Expired
-
1982
- 1982-10-01 YU YU02210/82A patent/YU221082A/en unknown
-
1984
- 1984-03-02 SE SE8401182A patent/SE448630B/en not_active IP Right Cessation
-
1990
- 1990-06-13 DK DK143990A patent/DK162055C/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |