IE36192B1 - Antibiotics and processes for their production - Google Patents

Antibiotics and processes for their production

Info

Publication number
IE36192B1
IE36192B1 IE8972A IE8972A IE36192B1 IE 36192 B1 IE36192 B1 IE 36192B1 IE 8972 A IE8972 A IE 8972A IE 8972 A IE8972 A IE 8972A IE 36192 B1 IE36192 B1 IE 36192B1
Authority
IE
Ireland
Prior art keywords
acid
group
benzyl
compounds
chloride
Prior art date
Application number
IE8972A
Other versions
IE36192L (en
Original Assignee
Merck & Co Inc
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 Merck & Co Inc filed Critical Merck & Co Inc
Publication of IE36192L publication Critical patent/IE36192L/en
Publication of IE36192B1 publication Critical patent/IE36192B1/en

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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • 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
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • 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
    • C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1350772 Cephalosporin compounds MERCK & CO Inc 14 Jan 1972 [27 Jan 1971 17 June 1971 24 Aug 1971 29 Nov 1971] 3295/71 28522/71 39654/71 and 1829/72 Divided out of 1350772 Headings C2A and C2C 3 - Carbamoyloxymethyl - cephalosporin compounds having the general Formula (I) and the corresponding #<SP>2</SP> compounds, and salts and esters thereof, wherein R<SP>1</SP> is hydrogen or an acyl group and R 1 is hydrogen or methoxy, the said compounds being novel when R 1 is hydrogen, are prepared by reacting a corresponding 3- hydroxymethyl - cephalosporin compound, in which if necessary any isocyanate-reactive group other than the 3-hydroxymethyl group is suitably blocked, the bromo- or chloro-sulphonyl isocyanate and hydrolysing the product and if necessary removing any blocking group. The reaction is preferably effected in a polar organic solvent and the hydrolysis is carried out by treatment with aqueous acid. Monobenzhydryl phenylmalonyl chloride is prepared by treating phenylmalonic acid with diphenyldiazomethane followed by alkaline hydrolysis to give monobenzhydryl phenylmalonate which is converted to the acid chloride with oxalyl chloride. Benzyl alcohol is esterified with D-α-aminoadipic acid in the presence of c.H 2 SO 4 to give benzyl - D - 5 - amino - 5 - carboxypentanoate, which is then N-protected by reacting with tbutyloxycarbonyl azide in the presence of MgO giving benzyl - D - 5 - t - butyloxycarbonylamino - 5 - carboxypentanoate. The carboxyl group is protected by reacting the latter with 2,2,2 - trichloroethanol in pyridine, and the resulting benzyl D - 5 - t - butoxycarbonylamino - 5 - (2,2,2 - trichloroethoxy)carbonylpentanoate is catalytically hydrogenated to remove the benzyl ester group. The product, D- 5 - t - butoxy - carbonylamino - 5 - (2,2,2 - trichloroethoxy)carbonylpentanoic acid is reacted with oxalyl chloride to give the corresponding acid chloride. The cephalosporin compounds of Formula I and their #<SP>2</SP> isomers, salts and esters, wherein R<SP>1</SP> is an acyl group, have antibacterial activity and may be used with a suitable carrier, diluent or coating to provide pharmaceutical and disinfectant compositions. [GB1350772A]
IE8972A 1971-01-27 1972-01-24 Antibiotics and processes for their production IE36192B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB329571A GB1350772A (en) 1971-01-27 1971-01-27 Antibiotics and processes for their production
GB2852271 1971-06-17
GB3965471 1971-08-24
GB182972 1972-01-14

Publications (2)

Publication Number Publication Date
IE36192L IE36192L (en) 1972-07-27
IE36192B1 true IE36192B1 (en) 1976-09-15

Family

ID=27447180

Family Applications (1)

Application Number Title Priority Date Filing Date
IE8972A IE36192B1 (en) 1971-01-27 1972-01-24 Antibiotics and processes for their production

Country Status (10)

Country Link
JP (1) JPS5418274B1 (en)
AR (1) AR204899A1 (en)
AU (1) AU468248B2 (en)
BE (1) BE778508A (en)
CA (1) CA1003404A (en)
CH (1) CH569021A5 (en)
DE (1) DE2203653C3 (en)
FR (1) FR2161866B1 (en)
GB (1) GB1350772A (en)
IE (1) IE36192B1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3905963A (en) * 1972-01-25 1975-09-16 Lilly Co Eli Process for preparing primary 3-carbamoyloxymethyl cephalosporins
US3994875A (en) * 1974-06-24 1976-11-30 Yeda Research & Development Co. Ltd. Antibiotics
AU1672492A (en) * 1991-05-03 1992-12-21 University Technologies International Inc. Biofilm reduction method
WO2004083217A1 (en) * 2003-03-20 2004-09-30 Orchid Chemicals & Pharmaceuticals Ltd An improved process for the preparation of cefoxitin
CN101830913B (en) * 2010-04-09 2012-10-31 烟台宝华生物技术有限公司 Cephalosporins parent nucleus derived compound, cephem onium salt compound prepared by same and method for preparing cephalosporins pyrazol sulfate by adopting same
CN103848851B (en) * 2012-11-29 2016-03-02 上海交通大学 A kind of synthetic method of Method of cefcapene pivoxil hydrochloride
WO2020158777A1 (en) 2019-01-29 2020-08-06 ニプロ株式会社 Artificial lung device

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1445633A1 (en) 1963-10-07 1968-12-05 Ciba Geigy Process for the preparation of new amides
CH480365A (en) * 1965-01-18 1969-10-31 Ciba Geigy Process for the preparation of new derivatives of 7-aminocephalosporanic acid

Also Published As

Publication number Publication date
DE2203653B2 (en) 1974-12-19
AU3835672A (en) 1973-08-02
CH569021A5 (en) 1975-11-14
AR204899A1 (en) 1976-03-19
IE36192L (en) 1972-07-27
DE2203653A1 (en) 1972-08-10
DE2203653C3 (en) 1975-07-31
FR2161866B1 (en) 1975-08-01
CA1003404A (en) 1977-01-11
JPS5418274B1 (en) 1979-07-06
AU468248B2 (en) 1976-01-08
GB1350772A (en) 1974-04-24
BE778508A (en) 1972-07-26
FR2161866A1 (en) 1973-07-13

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