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
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
Abstract
1,208,014. Cephalosporins. GLAXO LABORATORIES Ltd. 12 March, 1968 [23 March, 1967], No. 13867/67. Headings C2A and C2C. [Also in Division A5] The invention comprises 7 - arylglyoxamido cephalosporanic acids of Formula I wherein Ar is an aromatic group (including a heterocyclic aromatic group e.g. pyridyl or thienyl) having an atomic weight of at least 78; a salt thereof and an α - carbonyl derivative thereof e.g. oxime, methoxime, hydrazone, semicarbazone, thiosemicarbazone and isonicotinoylhydrazone. Ar may be the group where R is NH 2 , substituted NH 2 , halo, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonyl, NO 2 or CN, n is 1 to 4, the groups R when n is greater than 1 being the same or different. Ar may be 1 - naphthyl or 2 - phenanthryl. Typical compounds are 7 - (p - dimethylaminophenylglyoxamido) cephalosporanic acid and 7 - (p - chlorophenylglyoxamido) cephalosporanic acid. The compounds are produced by acylating 7 - amino cephalosporanic acid with an aromatic glyoxylic acid Ar.CO.CO.COOH wherein Ar has the above meaning, or a reactive derivative thereof e.g. acid halide, reactive azide, anhydride or mixed acid anhydride with e.g. butyric, valeric, isovaleric, trifluoroacetic or pivalic acids. Salts are formed with the alkali and alkaline earth metals, organic bases e.g. procaine, acids (where Ar contains a basic group) and resins e.g. a polystyrene resin containing amino, quarternary amino or sulphonic acid groups or a resin containing carboxyl groups e.g. a polyacrylic acid resin. 5 - chloro - 2 - methoxy - 4 - methylphenylglyoxylic acid is prepared by reacting 2 - chloro - 5 - methoxy toluene with ethyl oxalyl chloride in the presence of aluminium chloride, followed by treatment with hydrochloric acid and hydrolysis with NaOH to remove the ester group. m - iodophenylglyoxylic acid is prepared by nitrating acetophenone to produce m - nitroacetophenone, subjecting m - nitroacetophenone to reduction, diazotization and treatment with potassium iodide to give m - iodoacetophenone, and treating m - iodoacetophenone with KMnO 4 and KOH, followed by acidification with hydrochloric acid. 4 - chloro - 3 - nitrophenyl glyoxylic acid is produced by reacting 4 - chloro - 3 - nitrobenzaldehyde with sodium metabisulphite and sodium cyanide to give 4 - chloro - 3 - nitromandelic acid, esterifying the 4 - chloro - 3 - nitromandelic acid with CH 3 OH and H 2 SO 4 and treating the resultant methyl ester with lead tetra acetate and then with NaOH followed by acidification. o - Bromophenylglyoxylic acid is produced by the diazotization of isatin and the addition of the resultant diazonium salt to a boiling mixture of CuSO 4 , copper, NaBr, H 2 SO 4 and water. p - Formamidophenylglyoxylic acid is prepared by reducing p - nitrophenylglyoxylic acid with ferrous sulphate in aqueous NH 4 OH to give p aminophenylglyoxylic acid, which is then treated with dry formic acid and acetic anhydride. α - methoximinophenylacetyl chloride is prepared by reacting phenylglyoxylic acid with methoxyammonium chloride previously treated with potassium acetate in methanol to form α - methoximinophenylacetic acid which is then treated with thionyl chloride. The cephalosporins are active antibiotics which may be administered orally (see Division A5). Specification 1,104,937 is referred to.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB03867/67A GB1208014A (en) | 1967-03-23 | 1967-03-23 | Cephalosporins |
CH411968A CH507984A (en) | 1967-03-23 | 1968-03-20 | Process for the preparation of 7-acylaminocephalosporanic acids |
FR144493A FR7572M (en) | 1967-03-23 | 1968-03-20 | |
FR1556822D FR1556822A (en) | 1967-03-23 | 1968-03-20 | |
DE19681770031 DE1770031A1 (en) | 1967-03-23 | 1968-03-22 | New derivatives of cephalosporin C and process for their preparation (1) |
SE388168A SE364284B (en) | 1967-03-23 | 1968-03-22 | |
NL6804139A NL156702B (en) | 1967-03-23 | 1968-03-22 | PROCESS FOR THE PREPARATION OF A CEPHALOSPORIN DERIVATIVE AND FORMED PREPARATION WITH ANTI-BACTERIAL ACTION CONTAINING SUCH CEPHALOSPORIN DERIVATIVE. |
DK124068A DK124265B (en) | 1967-03-23 | 1968-03-22 | Analogous process for the preparation of cephalosporan derivatives or α-carbonyl derivatives or salts thereof or of the α-carbonyl derivatives. |
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 (en) |
DE (1) | DE1770031A1 (en) |
DK (1) | DK124265B (en) |
FR (2) | FR1556822A (en) |
GB (1) | GB1208014A (en) |
NL (1) | NL156702B (en) |
SE (1) | SE364284B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2223375A1 (en) * | 1971-05-14 | 1972-11-23 | Glaxo Lab Ltd | Antibiotics and their method of manufacture |
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 (en) * | 1971-01-29 | 1977-12-14 | Glaxo Lab Ltd | |
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 (en) * | 1978-04-26 | 1979-11-08 | Bayer Ag | BETA LACTAMANTIBIOTICS |
IT1211080B (en) * | 1981-07-21 | 1989-09-29 | Craf Sud | BIOLOGICALLY ACTIVE HYDRAZONOCEFEM. |
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/en not_active IP Right Cessation
- 1968-03-20 FR FR1556822D patent/FR1556822A/fr not_active Expired
- 1968-03-20 FR FR144493A patent/FR7572M/fr not_active Expired
- 1968-03-22 DE DE19681770031 patent/DE1770031A1/en not_active Ceased
- 1968-03-22 SE SE388168A patent/SE364284B/xx unknown
- 1968-03-22 NL NL6804139A patent/NL156702B/en unknown
- 1968-03-22 DK DK124068A patent/DK124265B/en unknown
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5248996B1 (en) * | 1971-01-29 | 1977-12-14 | Glaxo Lab Ltd | |
DE2223375A1 (en) * | 1971-05-14 | 1972-11-23 | Glaxo Lab Ltd | Antibiotics and their method of manufacture |
DE2265234A1 (en) * | 1971-05-14 | 1976-12-30 | Glaxo Lab Ltd | INTERMEDIATE PRODUCTS FOR ANTIBIOTICS AND PROCESS FOR THEIR MANUFACTURING |
JPS531280B1 (en) * | 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 |
JPS633867B2 (en) * | 1976-03-09 | 1988-01-26 | Fujisawa Pharmaceutical Co | |
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 |
---|---|
FR7572M (en) | 1970-01-05 |
DK124265B (en) | 1972-10-02 |
CH507984A (en) | 1971-05-31 |
SE364284B (en) | 1974-02-18 |
NL156702B (en) | 1978-05-16 |
NL6804139A (en) | 1968-09-24 |
DE1770031A1 (en) | 1971-09-16 |
FR1556822A (en) | 1969-02-07 |
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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 |