GB1350772A - Antibiotics and processes for their production - Google Patents

Antibiotics and processes for their production

Info

Publication number
GB1350772A
GB1350772A GB329571A GB329571A GB1350772A GB 1350772 A GB1350772 A GB 1350772A GB 329571 A GB329571 A GB 329571A GB 329571 A GB329571 A GB 329571A GB 1350772 A GB1350772 A GB 1350772A
Authority
GB
United Kingdom
Prior art keywords
acid
group
benzyl
compounds
chloride
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
GB329571A
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.)
Merck and Co Inc
Original Assignee
Merck and 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 and Co Inc filed Critical Merck and Co Inc
Priority to GB329571A priority Critical patent/GB1350772A/en
Priority to AR24020972A priority patent/AR204899A1/en
Priority to NL7200469A priority patent/NL7200469A/en
Priority to SU1739052A priority patent/SU457224A3/en
Priority to CA132,726A priority patent/CA1003404A/en
Priority to HUME001460 priority patent/HU165403B/hu
Priority to PL15300672A priority patent/PL83113B1/pl
Priority to IE8972A priority patent/IE36192B1/en
Priority to IL3862072A priority patent/IL38620A/en
Priority to AT58072A priority patent/AT320847B/en
Priority to BE778508A priority patent/BE778508A/en
Priority to CH112472A priority patent/CH569021A5/xx
Priority to ZA720519A priority patent/ZA72519B/en
Priority to DE19722264651 priority patent/DE2264651C2/en
Priority to DE19722203653 priority patent/DE2203653C3/en
Priority to PH13234A priority patent/PH10742A/en
Priority to ES399220A priority patent/ES399220A1/en
Priority to AU38356/72A priority patent/AU468248B2/en
Priority to CS51472A priority patent/CS192455B2/en
Priority to JP1018372A priority patent/JPS5418274B1/ja
Priority to FR7202751A priority patent/FR2161866B1/fr
Publication of GB1350772A publication Critical patent/GB1350772A/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
    • C07D501/02—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.
GB329571A 1971-01-27 1971-01-27 Antibiotics and processes for their production Expired GB1350772A (en)

Priority Applications (21)

Application Number Priority Date Filing Date Title
GB329571A GB1350772A (en) 1971-01-27 1971-01-27 Antibiotics and processes for their production
AR24020972A AR204899A1 (en) 1971-01-27 1972-01-01 PROCEDURE FOR THE PREPARATION OF 3-CARBAMOYLOXIMETHYLCHALOSPORINS
NL7200469A NL7200469A (en) 1971-01-27 1972-01-12 Carbamate prodn from alcohols - esp from 3-hydroxymethyl- cephem cpds by reaction with halosulphonyl isocyanates
SU1739052A SU457224A3 (en) 1971-01-27 1972-01-18 The method of obtaining -substituted carbamoyloxymethyl cephalus
CA132,726A CA1003404A (en) 1971-01-27 1972-01-18 Cephalosporin carbamates and processes
HUME001460 HU165403B (en) 1971-01-27 1972-01-18
PL15300672A PL83113B1 (en) 1971-01-27 1972-01-20
IE8972A IE36192B1 (en) 1971-01-27 1972-01-24 Antibiotics and processes for their production
IL3862072A IL38620A (en) 1971-01-27 1972-01-24 Cephalosporin carbamates and their preparation
AT58072A AT320847B (en) 1971-01-27 1972-01-25 Process for the preparation of new 3-carbamoyloxymethylcephalosporin derivatives
BE778508A BE778508A (en) 1971-01-27 1972-01-26 CEPHALOSPORIN CARBAMATES AND THEIR OBTAINING
CH112472A CH569021A5 (en) 1971-01-27 1972-01-26
ZA720519A ZA72519B (en) 1971-01-27 1972-01-26 Cephalosporin carbamates and processes
DE19722264651 DE2264651C2 (en) 1971-01-27 1972-01-26 Process for the preparation of 3-carbamoyloxy-methyl-7-methoxy-7- (2-thienylacetamido) -3-ce-phem-4-carboxylic acid
DE19722203653 DE2203653C3 (en) 1971-01-27 1972-01-26 3-Carbamoyloxymethyl-7- (2-thienylacetamido) -3-cephem-4-carboxylic acid and its salts, processes for the preparation of these compounds and medicaments containing such compounds
PH13234A PH10742A (en) 1971-01-27 1972-01-26 3-carbamoyloxymethyl cephalosporins and process for the preparation thereof
ES399220A ES399220A1 (en) 1971-01-27 1972-01-26 A procedure for the obtaining of alcohol carbamates. (Machine-translation by Google Translate, not legally binding)
AU38356/72A AU468248B2 (en) 1971-01-27 1972-01-26 Chemical processes and products
CS51472A CS192455B2 (en) 1971-01-27 1972-01-27 Process for preparing 3-carbamoyloxymethylcephalosporines
JP1018372A JPS5418274B1 (en) 1971-01-27 1972-01-27
FR7202751A FR2161866B1 (en) 1971-01-27 1972-01-27

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 (1)

Publication Number Publication Date
GB1350772A true GB1350772A (en) 1974-04-24

Family

ID=27447180

Family Applications (1)

Application Number Title Priority Date Filing Date
GB329571A Expired GB1350772A (en) 1971-01-27 1971-01-27 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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004083217A1 (en) * 2003-03-20 2004-09-30 Orchid Chemicals & Pharmaceuticals Ltd An improved process for the preparation of cefoxitin
CN101830913A (en) * 2010-04-09 2010-09-15 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
CN103848851A (en) * 2012-11-29 2014-06-11 上海交通大学 Synthetic method of cefcapene pivoxil hydrochloride

Families Citing this family (4)

* 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
CA2109084C (en) * 1991-05-03 2004-02-24 John William Fisher Costerton Biofilm reduction method
BR112021013710A2 (en) 2019-01-29 2021-09-21 Nipro Corporation 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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004083217A1 (en) * 2003-03-20 2004-09-30 Orchid Chemicals & Pharmaceuticals Ltd An improved process for the preparation of cefoxitin
CN101830913A (en) * 2010-04-09 2010-09-15 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
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
CN103848851A (en) * 2012-11-29 2014-06-11 上海交通大学 Synthetic method of cefcapene pivoxil hydrochloride
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

Also Published As

Publication number Publication date
FR2161866B1 (en) 1975-08-01
CA1003404A (en) 1977-01-11
DE2203653C3 (en) 1975-07-31
DE2203653A1 (en) 1972-08-10
AU3835672A (en) 1973-08-02
IE36192B1 (en) 1976-09-15
IE36192L (en) 1972-07-27
AR204899A1 (en) 1976-03-19
AU468248B2 (en) 1976-01-08
CH569021A5 (en) 1975-11-14
JPS5418274B1 (en) 1979-07-06
DE2203653B2 (en) 1974-12-19
FR2161866A1 (en) 1973-07-13
BE778508A (en) 1972-07-26

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Legal Events

Date Code Title Description
414F Notice of opposition given (sect. 14/1949)
414A Case decided by the comptroller ** specification amended (sect. 14/1949)
SPA Amended specification published
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee