GB1266252A - - Google Patents

Info

Publication number
GB1266252A
GB1266252A GB1266252DA GB1266252A GB 1266252 A GB1266252 A GB 1266252A GB 1266252D A GB1266252D A GB 1266252DA GB 1266252 A GB1266252 A GB 1266252A
Authority
GB
United Kingdom
Prior art keywords
acid
methyl
hydrogen
solvent
formula
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
Inventor
B G Jackson
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1266252A publication Critical patent/GB1266252A/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
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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

Abstract

1,266,252. Preparing 3-methyl-7-aminocephalosporins. ELI LILLY & CO. 10 March, 1970 [10 March, 1969], No. 11343/70. Heading C2A. 3 - Methyl - 7 - amino - cephalosporins of formula wherein R<SP>1</SP> is hydrogen or an easily removable carboxyl-protecting group, are prepared by treating a corresponding 3-methyl-7-acylamino cephalosporin with at least 1 molar proportion of a solvent of formula R<SP>11</SP>-OH at 0-125‹ C. in the presence of at least 0À25 equivalent of an acid having a pKa below 3, R<SP>11</SP> being hydrogen, methyl, ethyl or propyl and the acylating group in the starting cephalosporin having the formula or in which Q is hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyano, nitro, hydroxy, chloro, bromo or fluoro; Y is hydrogen or hydroxy; X is oxygen or sulphur; m is 0, 1 or 2; and n is 1, 2 or 3. The carboxyl-protecting group may be an easily removable esterifying group; preferred starting materials are those wherein the acylating group is benzyl or phenoxymethyl. When the solvent R<SP>11</SP>-OH is water, an inert watermiscible organic co-solvent is preferably added to maintain the reactants and products in solution. Suitable acids are p-toluenesulphonic acid, methanesulphonic acid, trifluoroacetic acid, hydrochloric acid, phosphoric acid and sulphuric acid. The product may be obtained in the form of the salt of the acid used, e.g. pnitrobenzyl - 3 - methyl - 7 - amino - A<SP>3</SP> - cephem- 4 - carboxylate p - toluenesulphonic acid salt monohydrate.
GB1266252D 1969-03-10 1970-03-10 Expired GB1266252A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US80582369A 1969-03-10 1969-03-10

Publications (1)

Publication Number Publication Date
GB1266252A true GB1266252A (en) 1972-03-08

Family

ID=25192601

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1266252D Expired GB1266252A (en) 1969-03-10 1970-03-10

Country Status (13)

Country Link
JP (1) JPS4931999B1 (en)
AT (1) AT293620B (en)
BE (1) BE746860A (en)
CA (1) CA974516A (en)
CH (1) CH529788A (en)
DE (1) DE2010757A1 (en)
ES (1) ES377228A1 (en)
FR (1) FR2037887A5 (en)
GB (1) GB1266252A (en)
IE (1) IE33722B1 (en)
IL (1) IL33889A (en)
NL (1) NL7003048A (en)
SE (1) SE374374B (en)

Also Published As

Publication number Publication date
NL7003048A (en) 1970-09-14
BE746860A (en) 1970-09-07
AT293620B (en) 1971-10-25
CH529788A (en) 1972-10-31
IE33722B1 (en) 1974-10-02
CA974516A (en) 1975-09-16
FR2037887A5 (en) 1970-12-31
JPS4931999B1 (en) 1974-08-27
IL33889A0 (en) 1970-04-20
IE33722L (en) 1970-09-10
DE2010757A1 (en) 1970-09-17
IL33889A (en) 1973-04-30
SE374374B (en) 1975-03-03
ES377228A1 (en) 1972-06-01

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
PS Patent sealed [section 19, patents act 1949]
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee