GB1433141A - Antibiotics - Google Patents
AntibioticsInfo
- Publication number
- GB1433141A GB1433141A GB3200472A GB3200472A GB1433141A GB 1433141 A GB1433141 A GB 1433141A GB 3200472 A GB3200472 A GB 3200472A GB 3200472 A GB3200472 A GB 3200472A GB 1433141 A GB1433141 A GB 1433141A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- prepared
- thien
- compound
- hydroxyimino
- 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
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- -1 2-hydroxyimino-2- (thien - 3 - yl)acetamido Chemical group 0.000 abstract 18
- 150000001875 compounds Chemical class 0.000 abstract 14
- 239000002253 acid Substances 0.000 abstract 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 239000002243 precursor Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- RNNIWANKYVVTII-UHFFFAOYSA-N 2-(furan-2-yl)-2-hydroxyiminoacetic acid Chemical class ON=C(C(O)=O)C1=CC=CO1 RNNIWANKYVVTII-UHFFFAOYSA-N 0.000 abstract 2
- SOJMCLNKLZLQLH-UHFFFAOYSA-N 2-hydroxyimino-2-thiophen-3-ylacetic acid Chemical compound ON=C(C(O)=O)C=1C=CSC=1 SOJMCLNKLZLQLH-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 125000006267 biphenyl group Chemical group 0.000 abstract 2
- 230000000903 blocking effect Effects 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 239000012038 nucleophile Substances 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 abstract 2
- 229940086542 triethylamine Drugs 0.000 abstract 2
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 abstract 1
- DGOUJJSVYKEJKS-TVKKRMFBSA-N (6r)-8-oxo-4-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C([C@H]1S2)C(=O)N1C(C(=O)O)=CC2NC(=O)CC1=CC=CS1 DGOUJJSVYKEJKS-TVKKRMFBSA-N 0.000 abstract 1
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 abstract 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 abstract 1
- FOHWXVBZGSVUGO-UHFFFAOYSA-N 5-phenyl-3h-1,3,4-oxadiazole-2-thione Chemical compound O1C(S)=NN=C1C1=CC=CC=C1 FOHWXVBZGSVUGO-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- OKOSMFFGEKAORW-UHFFFAOYSA-N [(2-chloro-2-oxo-1-thiophen-2-ylethylidene)amino] 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)ON=C(C(Cl)=O)C1=CC=CS1 OKOSMFFGEKAORW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 abstract 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 abstract 1
- SGCFFCMXADEZEU-UHFFFAOYSA-N ethyl 2-oxo-2-thiophen-3-ylacetate Chemical compound CCOC(=O)C(=O)C=1C=CSC=1 SGCFFCMXADEZEU-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 235000010262 sodium metabisulphite Nutrition 0.000 abstract 1
- 239000004296 sodium metabisulphite Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Landscapes
- Cephalosporin Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3200472A GB1433141A (en) | 1972-07-07 | 1972-07-07 | Antibiotics |
| PH13759A PH11435A (en) | 1972-07-07 | 1972-07-28 | 7 b-acylamidoceph-3em-4-carboxylic acid derivatives and pharmaceutical compositions containing same |
| AU57851/73A AU490918B2 (en) | 1972-07-07 | 1973-07-06 | Improvements in or relating to antibiotics |
| FR7324943A FR2191883B2 (enrdf_load_stackoverflow) | 1972-07-07 | 1973-07-06 | |
| IE114573A IE39743B1 (en) | 1972-07-07 | 1973-07-06 | Improvements in or relating to cephalsoporing an penicillin derivatives |
| BE133186A BE801997R (fr) | 1972-07-07 | 1973-07-06 | Perfectionnements aux antibiotiques de la serie des cephalosporines et des penicillines |
| ES416646A ES416646A2 (es) | 1972-07-07 | 1973-07-06 | Un procedimiento para la preparacion de compuustos de cefa- losporina. |
| LU67955D LU67955A1 (enrdf_load_stackoverflow) | 1972-07-07 | 1973-07-06 | |
| ZA734593A ZA734593B (en) | 1972-07-07 | 1973-07-06 | Improvements in or relating to antibiotics |
| US466780A US3926957A (en) | 1971-01-29 | 1974-05-03 | Penicillin antibiotics |
| US05/554,014 US4024134A (en) | 1971-01-29 | 1975-02-28 | Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7 |
| US05/612,262 US3991046A (en) | 1972-07-07 | 1975-09-11 | Penicillin antibiotics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3200472A GB1433141A (en) | 1972-07-07 | 1972-07-07 | Antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1433141A true GB1433141A (en) | 1976-04-22 |
Family
ID=10331586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3200472A Expired GB1433141A (en) | 1971-01-29 | 1972-07-07 | Antibiotics |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE801997R (enrdf_load_stackoverflow) |
| ES (1) | ES416646A2 (enrdf_load_stackoverflow) |
| FR (1) | FR2191883B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1433141A (enrdf_load_stackoverflow) |
| IE (1) | IE39743B1 (enrdf_load_stackoverflow) |
| LU (1) | LU67955A1 (enrdf_load_stackoverflow) |
| PH (1) | PH11435A (enrdf_load_stackoverflow) |
| ZA (1) | ZA734593B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1472534A (en) * | 1973-07-06 | 1977-05-04 | Glaxo Lab Ltd | 7beta-hydroxyiminoacylamido-cephalosporins |
| GB9104238D0 (en) * | 1990-03-16 | 1991-04-17 | Ici Pharma | 3-tetrazolylthiomethyl cephalosporin antibiotics |
-
1972
- 1972-07-07 GB GB3200472A patent/GB1433141A/en not_active Expired
- 1972-07-28 PH PH13759A patent/PH11435A/en unknown
-
1973
- 1973-07-06 ES ES416646A patent/ES416646A2/es not_active Expired
- 1973-07-06 BE BE133186A patent/BE801997R/xx not_active IP Right Cessation
- 1973-07-06 ZA ZA734593A patent/ZA734593B/xx unknown
- 1973-07-06 IE IE114573A patent/IE39743B1/xx unknown
- 1973-07-06 LU LU67955D patent/LU67955A1/xx unknown
- 1973-07-06 FR FR7324943A patent/FR2191883B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2191883A2 (enrdf_load_stackoverflow) | 1974-02-08 |
| AU5785173A (en) | 1975-01-09 |
| BE801997R (fr) | 1974-01-07 |
| FR2191883B2 (enrdf_load_stackoverflow) | 1976-12-17 |
| IE39743L (en) | 1974-01-07 |
| PH11435A (en) | 1978-02-01 |
| LU67955A1 (enrdf_load_stackoverflow) | 1973-09-11 |
| IE39743B1 (en) | 1978-12-20 |
| ES416646A2 (es) | 1977-05-16 |
| ZA734593B (en) | 1974-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |