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GB1498025A - 3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation - Google Patents

3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation

Info

Publication number
GB1498025A
GB1498025A GB4942374A GB4942374A GB1498025A GB 1498025 A GB1498025 A GB 1498025A GB 4942374 A GB4942374 A GB 4942374A GB 4942374 A GB4942374 A GB 4942374A GB 1498025 A GB1498025 A GB 1498025A
Authority
GB
United Kingdom
Prior art keywords
compound
reacting
prepared
group
derivative
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
GB4942374A
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB4942374A priority Critical patent/GB1498025A/en
Priority to FR7533385A priority patent/FR2290904A1/en
Priority to BE161574A priority patent/BE835238A/en
Priority to DE19752550151 priority patent/DE2550151A1/en
Priority to JP13559375A priority patent/JPS5170791A/en
Priority to NL7513327A priority patent/NL7513327A/en
Publication of GB1498025A publication Critical patent/GB1498025A/en
Priority to US05/930,217 priority patent/US4198503A/en
Expired legal-status Critical Current

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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1498025 3 - Carbamoyloxymethyl - 7 - substituted acetamido-cephalosporins BEECHAM GROUP Ltd 1 Oct 1975 [15 Nov 1974] 49423/74 Heading C2C Novel compounds (II) and salts and esters thereof in which Y is O or S R<SP>1</SP> is an organic radical of up to 20 C atoms R<SP>2</SP> is C 1-3 alkyl or benzyl R<SP>1</SP> or and R<SP>2</SP> together with C and N atoms to which they are attached form a 5 to 7 membered ring R<SP>3</SP> is phenyl (optionally substituted by OH, halogen, NO 2 , C 1-3 alkoxy and/or NH 2 ), thienyl, C 3-7 cycloalkyl, C 3-7 cycloalkenyl, or C 1-4 alkyl are prepared by (1) reacting a compound III or a salt, ester or silyl derivative thereof wherein the dotted line represents a bond in the 2- or 3- position and n is 0 or 1 with an N-acylating derivative of an acid (in which any reactive group is blocked) or (2) reacting a compound V with a compound R<SP>1</SP>-C(=Y)-N(R<SP>2</SP>)-COCl or (3) reacting a compound VII with an isocyanate R<SP>5</SP>-NCO where R<SP>5</SP> is Me 3 Si-, CCl 3 CH 2 or ClSO 2 - under mild conditions and if desired carrying out one or more of the following steps (i) converting a #<SP>2</SP> into a #<SP>3</SP> isomer, (ii) removing any silyl groups by alcoholysis or hydrolysis, (iii) reducing a sulphoxide group (n=1) to a sulphide (n=0), (iv) removing any blocking group in the acyl side chain or (v) converting an ester to a free acid or salt thereof. Compounds I prepared are those in which R 3 is Ph, Y is O, R<SP>2</SP> is H and R<SP>3</SP> is Ph, 2-phenylethenyl, 2 - phenylethyl or 1 - methyl - prop- 2-ethyl or R<SP>1</SP>-C(= Y)-N-(-R<SP>2</SP>)- represents imidazolidin-2-on-1-yl. Compounds VII are prepared by hydrolysis of the corresponding 3-acetoxymethyl derivative using citrus acetyl-esterase enzyme solution.
GB4942374A 1974-11-05 1975-10-01 3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation Expired GB1498025A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB4942374A GB1498025A (en) 1975-10-01 1975-10-01 3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation
FR7533385A FR2290904A1 (en) 1975-10-01 1975-10-31 CEPHALOSPORINS
BE161574A BE835238A (en) 1975-10-01 1975-11-04 CEPHALOSPORINS
DE19752550151 DE2550151A1 (en) 1975-10-01 1975-11-07 NEW CEPHALOSPORINE, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
JP13559375A JPS5170791A (en) 1975-10-01 1975-11-11 SEFUAROSUHORINNOSEIHO
NL7513327A NL7513327A (en) 1975-10-01 1975-11-13 PROCEDURE FOR PREPARING NEW CEFALOSPORINS.
US05/930,217 US4198503A (en) 1974-11-05 1978-08-02 3-Carbamoyl substituted-7-ureido substituted cephalosporins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4942374A GB1498025A (en) 1975-10-01 1975-10-01 3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation

Publications (1)

Publication Number Publication Date
GB1498025A true GB1498025A (en) 1978-01-18

Family

ID=10452295

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4942374A Expired GB1498025A (en) 1974-11-05 1975-10-01 3-carbamoyloxymethyl-7-8-(substituted acetamido)-3-cephem-4-carboxylic acid derivatives and methods for their preparation

Country Status (6)

Country Link
JP (1) JPS5170791A (en)
BE (1) BE835238A (en)
DE (1) DE2550151A1 (en)
FR (1) FR2290904A1 (en)
GB (1) GB1498025A (en)
NL (1) NL7513327A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298605A (en) 1978-06-22 1981-11-03 Chugai Seiyaku Kabushiki Kaisha Cephalosporin derivatives

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH634848A5 (en) * 1976-08-17 1983-02-28 Fujisawa Pharmaceutical Co METHOD FOR PRODUCING NEW 7- (N-SUBSTITUTED 2-PHENYLGLYCINAMIDO) -3-SUBSTITUTED-3-CEPHEM-4-CARBONIC ACIDS.
GB8320520D0 (en) * 1983-07-29 1983-09-01 Glaxo Group Ltd Chemical process
CN100372489C (en) * 2003-06-23 2008-03-05 乐金电子(天津)电器有限公司 Vacuum cleaner

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3687949A (en) * 1969-01-21 1972-08-29 Bristol Myers Co Synthetic cephalosporins

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298605A (en) 1978-06-22 1981-11-03 Chugai Seiyaku Kabushiki Kaisha Cephalosporin derivatives
US4301161A (en) 1978-06-22 1981-11-17 Chugai Seiyaku Kabushiki Kaisha Cephalosporin derivatives
US4328224A (en) 1978-06-22 1982-05-04 Chugai Seiyaku Kabushiki Kaisha Cephalosporin derivatives
US4341776A (en) 1978-06-22 1982-07-27 Chugai Seiyaku Kabushiki Kaisha Cephalosporin derivatives

Also Published As

Publication number Publication date
NL7513327A (en) 1976-05-18
FR2290904B1 (en) 1979-09-14
BE835238A (en) 1976-05-04
FR2290904A1 (en) 1976-06-11
DE2550151A1 (en) 1976-05-26
JPS5170791A (en) 1976-06-18

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Legal Events

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