GB1508978A - Esters of clavulanic acid - Google Patents
Esters of clavulanic acidInfo
- Publication number
- GB1508978A GB1508978A GB3656377A GB3656377A GB1508978A GB 1508978 A GB1508978 A GB 1508978A GB 3656377 A GB3656377 A GB 3656377A GB 3656377 A GB3656377 A GB 3656377A GB 1508978 A GB1508978 A GB 1508978A
- Authority
- GB
- United Kingdom
- Prior art keywords
- clavulanic acid
- penicillin
- april
- ester
- esters
- 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.)
- Expired
Links
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title abstract 3
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title abstract 2
- 229960003324 clavulanic acid Drugs 0.000 title abstract 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 2
- UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 229930195708 Penicillin V Natural products 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229960003022 amoxicillin Drugs 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
- 229960000723 ampicillin 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
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 229960003669 carbenicillin Drugs 0.000 abstract 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229960003972 cefacetrile Drugs 0.000 abstract 1
- RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 abstract 1
- 229950004030 cefaloglycin Drugs 0.000 abstract 1
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 abstract 1
- 229960003866 cefaloridine Drugs 0.000 abstract 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 abstract 1
- 229960000603 cefalotin Drugs 0.000 abstract 1
- 229960003012 cefamandole Drugs 0.000 abstract 1
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 abstract 1
- 229960004350 cefapirin Drugs 0.000 abstract 1
- 229960001139 cefazolin Drugs 0.000 abstract 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 abstract 1
- 229960002588 cefradine Drugs 0.000 abstract 1
- 229940106164 cephalexin Drugs 0.000 abstract 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 abstract 1
- RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- -1 cyolacillin Chemical compound 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229960002457 epicillin Drugs 0.000 abstract 1
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 238000001802 infusion Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229960003085 meticillin Drugs 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
- 229940049954 penicillin Drugs 0.000 abstract 1
- 235000019371 penicillin G benzathine Nutrition 0.000 abstract 1
- 229940056360 penicillin g Drugs 0.000 abstract 1
- 229940056367 penicillin v Drugs 0.000 abstract 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 229960003672 propicillin Drugs 0.000 abstract 1
- HOCWPKXKMNXINF-XQERAMJGSA-N propicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(CC)OC1=CC=CC=C1 HOCWPKXKMNXINF-XQERAMJGSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 229960004659 ticarcillin Drugs 0.000 abstract 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1508978 Antibiotic compositions containing clavulanic acid esters BEECHAM GROUP Ltd 11 April 1975 [20 April 1974 21 June 1974 9 Oct 1974 11 Dec 1974] 36563/77 36564/77 36565/77 and 36566/77 Divided out of 1508977 Heading A5B [Also in Division C2] Pharmceutical compositions having antibacterial and #-lactamase inhibitory properties comprise, as active ingredient, an ester (formed at the carboxyl group) of clavulanic acid of the formula together with a pharmaceutically acceptable carrier and optionally therapeutic agents such as a penicillin or cephalosporin, e.g. benzylpenicillin, phenoxymethyl - penicillin, carbenicillin, methicillin, propicillin, ampicillin, amoxycillin, epicillin, ticarcillin, cyolacillin, cephaloridine, cephalothin, cefazolin, cephalexin, cephacetrile, cephamandole, cephapirin, cephradine, cephaloglycine or a salt or in vivo hydrolysable ester thereof or an aldehyde or ketone adduct of such a compound having a 6- or 7 - α - amino - acylamido side chain. They may be administered, orally, topically or parenterally, e.g. as tablets, capsules, creams, syrups, suspensions, solutions, reconstitutable powders and sterile forms suitable for injection or infusion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3656377A GB1508978A (en) | 1975-04-11 | 1975-04-11 | Esters of clavulanic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3656377A GB1508978A (en) | 1975-04-11 | 1975-04-11 | Esters of clavulanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1508978A true GB1508978A (en) | 1978-04-26 |
Family
ID=10389283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3656377A Expired GB1508978A (en) | 1975-04-11 | 1975-04-11 | Esters of clavulanic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1508978A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0672670A1 (en) | 1992-06-11 | 1995-09-20 | Smithkline Beecham Plc | Process for the preparation of clavulanic acid |
| WO1997010247A1 (en) * | 1995-09-15 | 1997-03-20 | Smithkline Beecham P.L.C. | Clavulanic acid derivatives for treating atherosclerosis |
| US5859238A (en) * | 1992-03-26 | 1999-01-12 | Lek, Tovarna Farmacevtskih | Alkylenediammonium diclavulanate derivatives, a process for the preparation thereof as well as the use thereof |
-
1975
- 1975-04-11 GB GB3656377A patent/GB1508978A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5859238A (en) * | 1992-03-26 | 1999-01-12 | Lek, Tovarna Farmacevtskih | Alkylenediammonium diclavulanate derivatives, a process for the preparation thereof as well as the use thereof |
| EP0672670A1 (en) | 1992-06-11 | 1995-09-20 | Smithkline Beecham Plc | Process for the preparation of clavulanic acid |
| WO1997010247A1 (en) * | 1995-09-15 | 1997-03-20 | Smithkline Beecham P.L.C. | Clavulanic acid derivatives for treating atherosclerosis |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19950410 |