GB1342241A - Cephalosporin compounds - Google Patents

Cephalosporin compounds

Info

Publication number
GB1342241A
GB1342241A GB346470A GB1342241DA GB1342241A GB 1342241 A GB1342241 A GB 1342241A GB 346470 A GB346470 A GB 346470A GB 1342241D A GB1342241D A GB 1342241DA GB 1342241 A GB1342241 A GB 1342241A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
amino
group
naphthyl
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
Application number
GB346470A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Publication of GB1342241A publication Critical patent/GB1342241A/en
Expired legal-status Critical Current

Links

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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1342241 Cephalosporins GLAXO LABORATORIES Ltd 12 Jan 1971 [23 Jan 1970 6 May 1970 10 June 1970] 3464/70 21907/70 and 28194/70 Headings C2A and C2C [Also in Divisions A5 and A6] Novel cephalosporins of Formula (I) wherein R<SP>1</SP> is a carboxylic acyl group; and R<SP>3</SP> and R<SP>4</SP> may be the same or different and are each H, or a substituted or unsubstituted aliphatic, cycloaliphatic, aromatic or araliphatic group; or R<SP>3</SP> is hydrogen and R<SP>4</SP> is C 1 -C 6 alkoxycarbonyl, carboxy or cyano; and salts and esters thereof, and aldehyde or ketone condensation products of compounds (I) in which the 7-side chain R<SP>1</SP> has an α-amino group of an α-acylamino group, are prepared by (a) acylating a compound of formula wherein R<SP>6</SP> is H or a carboxyl-blocking group, Z is -S- or and R<SP>3</SP> and R<SP>4</SP> are as previously defined, which compounds themselves form part of the invention, with an acylating agent corresponding to the acid R<SP>1</SP>OH; or (b) reacting a compound of formula wherein R is an alkyl, aralkyl or aryl group; which may be substituted by one or more of halogen, nitro, cyano, amino, acyl or acylamino, and R<SP>1</SP>, R<SP>9</SP> and Z are as previously defined, with a carbonyl compound of formula in which R<SP>3</SP> and R<SP>4</SP> have the aforesaid meaning; or (c) reacting a compound of formula wherein R<SP>1</SP>, Z and R<SP>6</SP> are as previously defined, with a phosphorane ylid of formula in which R, R<SP>3</SP> and R<SP>4</SP> have the aforesaid meanings; and if necessary, subsequently carrying out any of the following reactions : (i) conversion of a #<SP>2</SP> isomer into the desired #<SP>3</SP> isomer, (ii) removal of any groups protecting any amino or carboxyl groups, (iii) reduction of a compound in which Z is to form the desired compound wherein Z is -S-. DL - 2 - Amino - 2 - (2 - naphthyl)acetic acid is prepared by hydrolysing 5-(2-naphthyl)hydantoin with 10% NaOH. The amino acid is subsequently N-protected by reaction with t-butylp-nitrophenylcarbonate to give DL-2-t-butoxycarbonylamino-2-(2-naphthyl)acetic acid.
GB346470A 1970-01-23 1970-01-23 Cephalosporin compounds Expired GB1342241A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB346470 1970-01-23

Publications (1)

Publication Number Publication Date
GB1342241A true GB1342241A (en) 1974-01-03

Family

ID=9758822

Family Applications (1)

Application Number Title Priority Date Filing Date
GB346470A Expired GB1342241A (en) 1970-01-23 1970-01-23 Cephalosporin compounds

Country Status (3)

Country Link
AT (2) AT318812B (en)
GB (1) GB1342241A (en)
ZA (1) ZA71429B (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012382A (en) * 1974-06-05 1977-03-15 Daniel Bouzard α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives
EP0030630A2 (en) * 1979-11-19 1981-06-24 Fujisawa Pharmaceutical Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
DE3402642A1 (en) * 1983-01-28 1984-08-02 Bristol-Myers Co., New York, N.Y. SUBSTITUTED VINYLCEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
DE3404615A1 (en) * 1983-02-10 1984-08-16 Bristol-Myers Co., New York, N.Y. CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
GB2137993A (en) * 1983-04-12 1984-10-17 Lilly Co Eli Improvements in or relating to naphthylglycyl cephalosporin derivatives
DE3512225A1 (en) * 1984-04-09 1985-10-17 Bristol-Myers Co., New York, N.Y. CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS
US4591641A (en) * 1983-01-28 1986-05-27 Bristol-Myers Company Substituted vinyl cephalosporins
DE3613365A1 (en) * 1985-04-22 1987-01-02 Bristol Myers Co 7-AMINO-3-PROPENYLCEPHALOSPORANIC ACID AND ITS ESTERS AND METHOD FOR PRODUCING THESE COMPOUNDS
US4666899A (en) * 1984-05-10 1987-05-19 Glaxo Group Limited 3-(Optionally substituted-but-1-en-3-ynyl) cephalosporins
US4699979A (en) * 1985-04-22 1987-10-13 Bristol-Meyers Company 7-amino-3-propenylcephalosporanic acid and esters thereof
WO2000053609A1 (en) * 1999-03-09 2000-09-14 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime
US6235896B1 (en) 1998-03-30 2001-05-22 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT390439B (en) * 1983-01-28 1990-05-10 Bristol Myers Squibb Co Process for the preparation of the novel benzhydryl 7 beta-(D-2-(t-butoxycarbonylamino)-2-(4- hydroxyphenyl)acetamido)-3-(triphenylphosphonio)methyl-3- cephem-4-carboxylate iodide

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012382A (en) * 1974-06-05 1977-03-15 Daniel Bouzard α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives
EP0030630A2 (en) * 1979-11-19 1981-06-24 Fujisawa Pharmaceutical Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
EP0030630A3 (en) * 1979-11-19 1981-09-09 Fujisawa Pharmaceutical Co., Ltd. 7-acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
EP0123024A2 (en) * 1979-11-19 1984-10-31 Fujisawa Pharmaceutical Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
EP0123024A3 (en) * 1979-11-19 1985-03-13 Fujisawa Pharmaceutical Co., Ltd. 7-acylamino-3-vinylcephalosporanic acid derivatives, processes for their preparation, pharmaceutical compositions containing them; their starting compounds and their preparation
US4520022A (en) * 1983-01-28 1985-05-28 Bristol-Myers Company Substituted vinyl cephalosporins
DE3402642A1 (en) * 1983-01-28 1984-08-02 Bristol-Myers Co., New York, N.Y. SUBSTITUTED VINYLCEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
GB2135305A (en) * 1983-01-28 1984-08-30 Bristol Myers Co Substituted vinyl cephalosporins
US4591641A (en) * 1983-01-28 1986-05-27 Bristol-Myers Company Substituted vinyl cephalosporins
DE3404615A1 (en) * 1983-02-10 1984-08-16 Bristol-Myers Co., New York, N.Y. CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME
GB2137993A (en) * 1983-04-12 1984-10-17 Lilly Co Eli Improvements in or relating to naphthylglycyl cephalosporin derivatives
DE3512225A1 (en) * 1984-04-09 1985-10-17 Bristol-Myers Co., New York, N.Y. CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS
US4666899A (en) * 1984-05-10 1987-05-19 Glaxo Group Limited 3-(Optionally substituted-but-1-en-3-ynyl) cephalosporins
DE3613365A1 (en) * 1985-04-22 1987-01-02 Bristol Myers Co 7-AMINO-3-PROPENYLCEPHALOSPORANIC ACID AND ITS ESTERS AND METHOD FOR PRODUCING THESE COMPOUNDS
US4699979A (en) * 1985-04-22 1987-10-13 Bristol-Meyers Company 7-amino-3-propenylcephalosporanic acid and esters thereof
US6235896B1 (en) 1998-03-30 2001-05-22 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime
WO2000053609A1 (en) * 1999-03-09 2000-09-14 Ranbaxy Laboratories Limited Process for the preparation of cefuroxime

Also Published As

Publication number Publication date
ZA71429B (en) 1972-09-27
AT318812B (en) 1974-11-25
AT318811B (en) 1974-11-25

Similar Documents

Publication Publication Date Title
GB1342241A (en) Cephalosporin compounds
GB1432576A (en) Substituted phenylacetic acids
GB1448810A (en) Fungicidal n-substituted furoic amide derivatives
GB1495676A (en) Cephalosporins having an alpha-acylamino-acetic acid side chain
GB1377762A (en) 8-oxo-5-thia-1-azabicyclo-4,2,0 oct- 2-ene-compounds process for their manufacture and compositions containing them
GB1262965A (en) Butyrophenones
GB1362918A (en) Thioesters of guanidinoorganic acids and production thereof
GB1336318A (en) Derivatives of 7-aminocephalosporanic acid
GB1460916A (en) Preparation of 3-thiolated-7-acylamido-cephalosporanic acid derivatives
GB1463282A (en) Sugar ureide and thiooureide derivatives
GB1497039A (en) Penicillins and cephalosporins
GB1363833A (en) 3-heterocyclic thiomethylcephalosporins
GB1339053A (en) Method for the preparation of aromatic a-amino acids and intermediates therefor
GB1368074A (en) Substituted beta-lactams and their preparation
ES252422A1 (en) Improvements in or relating to penicillin derivatives
GB1351932A (en) Chromone-3-carboxylic acids
GB1334382A (en) Antibiotics
GB1313429A (en) Penicillins
GB1210472A (en) Penicillins
GB1363692A (en) Benzothiazolyl acetic acid derivatives
GB1392554A (en) Cephalosporins
GB1374281A (en) Thiazolino-pyrimidin-5-one derivatives process for their pre paration and applications thereof
GB1333524A (en) Penicilloic acid derivatives
GB1377692A (en) Antibacterial agents and a process for the preparation thereof
ES401264A1 (en) Penicillins

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee