GB1208014A - Cephalosporins - Google Patents
CephalosporinsInfo
- Publication number
- GB1208014A GB1208014A GB03867/67A GB1386767A GB1208014A GB 1208014 A GB1208014 A GB 1208014A GB 03867/67 A GB03867/67 A GB 03867/67A GB 1386767 A GB1386767 A GB 1386767A GB 1208014 A GB1208014 A GB 1208014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- chloro
- chloride
- prepared
- cephalosporanic
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 150000001780 cephalosporins Chemical class 0.000 title abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- IWLHOUBDKCKJJQ-UHFFFAOYSA-N 1-(3-iodophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(I)=C1 IWLHOUBDKCKJJQ-UHFFFAOYSA-N 0.000 abstract 2
- ARKIFHPFTHVKDT-UHFFFAOYSA-N 1-(3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC([N+]([O-])=O)=C1 ARKIFHPFTHVKDT-UHFFFAOYSA-N 0.000 abstract 2
- RYMLPVGCISRSRQ-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 RYMLPVGCISRSRQ-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000006193 diazotization reaction Methods 0.000 abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 230000020477 pH reduction Effects 0.000 abstract 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- SDGMUBWPXBSKCT-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Cl)C(C)=C1 SDGMUBWPXBSKCT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- -1 2 - phenanthryl Chemical group 0.000 abstract 1
- BCGITRTXBFIXCC-UHFFFAOYSA-N 2-(2-bromophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1Br BCGITRTXBFIXCC-UHFFFAOYSA-N 0.000 abstract 1
- LSETZDOAPDISOL-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 LSETZDOAPDISOL-UHFFFAOYSA-N 0.000 abstract 1
- VRHXMFFTZGFEPY-UHFFFAOYSA-N 2-(4-formamidophenyl)-2-oxoacetic acid Chemical compound C(=O)NC1=CC=C(C=C1)C(C(=O)O)=O VRHXMFFTZGFEPY-UHFFFAOYSA-N 0.000 abstract 1
- QPDHXOFINFQQBM-UHFFFAOYSA-N 2-(5-chloro-2-methoxy-4-methylphenyl)-2-oxoacetic acid Chemical compound COC1=CC(C)=C(Cl)C=C1C(=O)C(O)=O QPDHXOFINFQQBM-UHFFFAOYSA-N 0.000 abstract 1
- MQMWPBBDMIYYMI-UHFFFAOYSA-N 2-aminophenylglyoxylic acid Chemical compound NC1=CC=CC=C1C(=O)C(O)=O MQMWPBBDMIYYMI-UHFFFAOYSA-N 0.000 abstract 1
- ISFFCSPHFNWPST-UHFFFAOYSA-N 2-methoxyimino-2-phenylacetic acid Chemical compound CON=C(C(O)=O)C1=CC=CC=C1 ISFFCSPHFNWPST-UHFFFAOYSA-N 0.000 abstract 1
- UIBNKYDBTMDABC-UHFFFAOYSA-N 2-methoxyimino-2-phenylacetyl chloride Chemical compound CON=C(C(Cl)=O)C1=CC=CC=C1 UIBNKYDBTMDABC-UHFFFAOYSA-N 0.000 abstract 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 abstract 1
- YNNOFVDQHAHVFG-UHFFFAOYSA-N 3-phenylmethoxycyclobutane-1-carboxylic acid Chemical compound C1C(C(=O)O)CC1OCC1=CC=CC=C1 YNNOFVDQHAHVFG-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- HETBKLHJEWXWBM-UHFFFAOYSA-N 4-chloro-3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(C=O)=CC=C1Cl HETBKLHJEWXWBM-UHFFFAOYSA-N 0.000 abstract 1
- RREPYIWLDJQENS-UHFFFAOYSA-N 4-nitrophenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 RREPYIWLDJQENS-UHFFFAOYSA-N 0.000 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- SXJSICIFYMGOFE-UHFFFAOYSA-N IC=1C=C(C=CC1)C(C(=O)O)=O Chemical compound IC=1C=C(C=CC1)C(C(=O)O)=O SXJSICIFYMGOFE-UHFFFAOYSA-N 0.000 abstract 1
- 229920002125 Sokalan® Polymers 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000011790 ferrous sulphate Substances 0.000 abstract 1
- 235000003891 ferrous sulphate Nutrition 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- QOWOXBFFQOXPHM-UHFFFAOYSA-O oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]pyridin-4-ylidene]methyl]azanium;chloride Chemical compound [Cl-].C1=CC(=C[NH+]=O)C=CN1CN1C=CC(=C[NH+]=O)C=C1 QOWOXBFFQOXPHM-UHFFFAOYSA-O 0.000 abstract 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005546 pivalic acid group Chemical group 0.000 abstract 1
- 239000004584 polyacrylic acid Substances 0.000 abstract 1
- 229920005990 polystyrene resin Polymers 0.000 abstract 1
- 235000011056 potassium acetate Nutrition 0.000 abstract 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 abstract 1
- 229960004919 procaine Drugs 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000007659 semicarbazones Chemical class 0.000 abstract 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 abstract 1
- 235000010262 sodium metabisulphite Nutrition 0.000 abstract 1
- 239000004296 sodium metabisulphite Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/32—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an araliphatic carboxylic acid, which is substituted on the aliphatic radical by hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB03867/67A GB1208014A (en) | 1967-03-23 | 1967-03-23 | Cephalosporins |
| CH411968A CH507984A (de) | 1967-03-23 | 1968-03-20 | Verfahren zur Herstellung von 7-Acylaminocephalosporansäuren |
| FR144493A FR7572M (enrdf_load_stackoverflow) | 1967-03-23 | 1968-03-20 | |
| FR1556822D FR1556822A (enrdf_load_stackoverflow) | 1967-03-23 | 1968-03-20 | |
| NL6804139A NL156702B (nl) | 1967-03-23 | 1968-03-22 | Werkwijze voor de bereiding van een cefalosporinederivaat, alsmede gevormd preparaat met anti-bacteriele werking dat zo'n cefalosporinederivaat bevat. |
| DK124068A DK124265B (da) | 1967-03-23 | 1968-03-22 | Analogifremgangsmåde til fremstilling af cephalosporanderivater eller α-karbonylderivater eller salte deraf eller af α-karbonylderivaterne. |
| DE19681770031 DE1770031A1 (de) | 1967-03-23 | 1968-03-22 | Neue Derivate von Cephalosporin C und Verfahren zu ihrer Herstellung(1) |
| SE388168A SE364284B (enrdf_load_stackoverflow) | 1967-03-23 | 1968-03-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB03867/67A GB1208014A (en) | 1967-03-23 | 1967-03-23 | Cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1208014A true GB1208014A (en) | 1970-10-07 |
Family
ID=10030837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB03867/67A Expired GB1208014A (en) | 1967-03-23 | 1967-03-23 | Cephalosporins |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH507984A (enrdf_load_stackoverflow) |
| DE (1) | DE1770031A1 (enrdf_load_stackoverflow) |
| DK (1) | DK124265B (enrdf_load_stackoverflow) |
| FR (2) | FR7572M (enrdf_load_stackoverflow) |
| GB (1) | GB1208014A (enrdf_load_stackoverflow) |
| NL (1) | NL156702B (enrdf_load_stackoverflow) |
| SE (1) | SE364284B (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2223375A1 (de) * | 1971-05-14 | 1972-11-23 | Glaxo Lab Ltd | Antibiotika und Verfahren zu ihrer Herstellung |
| JPS52108997A (en) * | 1976-03-09 | 1977-09-12 | Fujisawa Pharmaceut Co Ltd | 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and their salts and their preparation |
| JPS5248996B1 (enrdf_load_stackoverflow) * | 1971-01-29 | 1977-12-14 | Glaxo Lab Ltd | |
| US4201779A (en) | 1977-03-12 | 1980-05-06 | Hoechst Aktiengesellschaft | 7[(2-Amino-thiazol-4-yl)glyoxylamido]-cephem derivatives and processes for their preparation |
| US8993574B2 (en) | 2008-04-24 | 2015-03-31 | F2G Ltd | Pyrrole antifungal agents |
| US10201524B2 (en) | 2014-11-21 | 2019-02-12 | F2G Limited | Antifungal agents |
| US10973821B2 (en) | 2016-05-25 | 2021-04-13 | F2G Limited | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1389194A (en) * | 1971-01-29 | 1975-04-03 | Glaxo Lab Ltd | Antibiotics |
| IE36041B1 (en) * | 1971-01-29 | 1976-08-04 | Glaxo Lab Ltd | Improvements in or relating to antibiotics |
| DE2818263A1 (de) * | 1978-04-26 | 1979-11-08 | Bayer Ag | Beta-lactamantibiotika |
| IT1211080B (it) * | 1981-07-21 | 1989-09-29 | Craf Sud | Idrazonocefem derivati biologicamente attivi. |
| GB8810393D0 (en) * | 1988-05-03 | 1988-06-08 | Glaxo Group Ltd | Chemical process |
-
1967
- 1967-03-23 GB GB03867/67A patent/GB1208014A/en not_active Expired
-
1968
- 1968-03-20 CH CH411968A patent/CH507984A/de not_active IP Right Cessation
- 1968-03-20 FR FR144493A patent/FR7572M/fr not_active Expired
- 1968-03-20 FR FR1556822D patent/FR1556822A/fr not_active Expired
- 1968-03-22 DK DK124068A patent/DK124265B/da unknown
- 1968-03-22 NL NL6804139A patent/NL156702B/xx unknown
- 1968-03-22 DE DE19681770031 patent/DE1770031A1/de not_active Ceased
- 1968-03-22 SE SE388168A patent/SE364284B/xx unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248996B1 (enrdf_load_stackoverflow) * | 1971-01-29 | 1977-12-14 | Glaxo Lab Ltd | |
| DE2223375A1 (de) * | 1971-05-14 | 1972-11-23 | Glaxo Lab Ltd | Antibiotika und Verfahren zu ihrer Herstellung |
| DE2265234A1 (de) * | 1971-05-14 | 1976-12-30 | Glaxo Lab Ltd | Zwischenprodukte fuer antibiotika und verfahren zu ihrer herstellung |
| JPS531280B1 (enrdf_load_stackoverflow) * | 1971-05-14 | 1978-01-17 | ||
| JPS52108997A (en) * | 1976-03-09 | 1977-09-12 | Fujisawa Pharmaceut Co Ltd | 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and their salts and their preparation |
| US4201779A (en) | 1977-03-12 | 1980-05-06 | Hoechst Aktiengesellschaft | 7[(2-Amino-thiazol-4-yl)glyoxylamido]-cephem derivatives and processes for their preparation |
| US8993574B2 (en) | 2008-04-24 | 2015-03-31 | F2G Ltd | Pyrrole antifungal agents |
| US9452168B2 (en) | 2008-04-24 | 2016-09-27 | F2G Ltd | Pyrrole antifungal agents |
| US10201524B2 (en) | 2014-11-21 | 2019-02-12 | F2G Limited | Antifungal agents |
| US10596150B2 (en) | 2014-11-21 | 2020-03-24 | F2G Limited | Antifungal agents |
| US11065228B2 (en) | 2014-11-21 | 2021-07-20 | F2G Limited | Antifungal agents |
| US10973821B2 (en) | 2016-05-25 | 2021-04-13 | F2G Limited | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1556822A (enrdf_load_stackoverflow) | 1969-02-07 |
| NL6804139A (enrdf_load_stackoverflow) | 1968-09-24 |
| NL156702B (nl) | 1978-05-16 |
| DK124265B (da) | 1972-10-02 |
| CH507984A (de) | 1971-05-31 |
| DE1770031A1 (de) | 1971-09-16 |
| FR7572M (enrdf_load_stackoverflow) | 1970-01-05 |
| SE364284B (enrdf_load_stackoverflow) | 1974-02-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |