GB1171603A - Improvements in or relating to cephalosporins - Google Patents

Improvements in or relating to cephalosporins

Info

Publication number
GB1171603A
GB1171603A GB1571966A GB1571966A GB1171603A GB 1171603 A GB1171603 A GB 1171603A GB 1571966 A GB1571966 A GB 1571966A GB 1571966 A GB1571966 A GB 1571966A GB 1171603 A GB1171603 A GB 1171603A
Authority
GB
United Kingdom
Prior art keywords
salt
acid
acid addition
addition salt
pyridinium
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
GB1571966A
Inventor
Harold Alfred Crisp
John Francis Oughton
Chrisopher John Sharp
Peter Alfred Wilkinson
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
Priority to GB1571966A priority Critical patent/GB1171603A/en
Priority to GR670135150A priority patent/GR35150B/en
Priority to CH494767A priority patent/CH504472A/en
Priority to BE696775D priority patent/BE696775A/xx
Priority to FR101871A priority patent/FR1518199A/en
Priority to DE1967G0049776 priority patent/DE1695015C3/en
Priority to SE489467A priority patent/SE370080B/xx
Priority to AT333467A priority patent/AT287189B/en
Priority to ES339028A priority patent/ES339028A1/en
Priority to DK195867A priority patent/DK136609C/en
Priority to NL6704945A priority patent/NL6704945A/xx
Priority to CH1898269A priority patent/CH533135A/en
Publication of GB1171603A publication Critical patent/GB1171603A/en
Priority to US220537A priority patent/US3887551A/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
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

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

Abstract

1,171,603. Cephalosporin C A compounds. GLAXO LABORATORIES Ltd. 22 March, 1967 [7 April, 1966], No. 15719/66. Heading C2A. An N - (7 - acylamido - ceph - 3 - em - 3 - ylmethyl) - pyridinium - 4 - carboxylate is produced by (A) reacting a 7-acylamidocephalosporanic acid or a salt thereof with pyridine or a substituted pyridine in solution in a reaction medium in the presence of at least an equivalent equimolar proportion, calculated on the 7-acylamido cephalosporanic acid, of thiocyanate or iodide ions and recovering the resultant N-(7- acylamidoceph - 3 - em - 3 - yl - methyl)- pyridinium-4-carboxylate as its crude hydrothiocyanate or hydroidide acid addition salt; (B) converting the crude hydrothiocyanate or hydroiodide acid addition salt from (A) to the betaine form by reacting said salt with a base, the betaine being recovered in an aqueous phase; (C) if desired, passing the aqueous phase from (B) through one or more ion-exchangers and, if desired, decolouring absorbent, to remove further impurities, e.g. acidic and basic impurities as well as colourants; (D) reacting the aqueous phase from (B) or (C) with an acid to form an insoluble acid addition salt; (E) separating the acid addition salt from (D) from the mother liquor and converting the salt to the betaine form by reaction with a base. The examples relate to the preparation of N-(7-2<SP>1</SP>- thienylacetamidoceph - 3 - em - 3 - ylmethyl)- pyridinium - 4 - carboxylate - (cephaloridine). The pyridine may be substituted by one or more alkyl, carboxy or carbamoyl groups. Specifications 912,541, 966,221, 1,028,563, 1,101,561, 1,101,562 and 1,132,621 are referred to.
GB1571966A 1964-11-04 1966-04-07 Improvements in or relating to cephalosporins Expired GB1171603A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB1571966A GB1171603A (en) 1966-04-07 1966-04-07 Improvements in or relating to cephalosporins
GR670135150A GR35150B (en) 1966-04-07 1967-04-04 PERFECTIONS IN OR IN RELATION TO THE METHOD OF ANTIBIOTICS.
AT333467A AT287189B (en) 1966-04-07 1967-04-07 Process for the preparation of N- (7-acylamidoceph-3-em-3-ylmethyl) -pyridinium-4-carboxylates
BE696775D BE696775A (en) 1966-04-07 1967-04-07
FR101871A FR1518199A (en) 1966-04-07 1967-04-07 Method for the preparation of cephalosporin-type antibiotics
DE1967G0049776 DE1695015C3 (en) 1966-04-07 1967-04-07 Process for the recovery of highly purified N- (7-2'-thienylacetamidoceph-3-em-3-y! -Methyl) -pyridinium-4carboxylate
SE489467A SE370080B (en) 1966-04-07 1967-04-07
CH494767A CH504472A (en) 1966-04-07 1967-04-07 N-(7-acylamidoceph-3-em-3-ylmethyl)-pyridinium-4-carboxylate, antibiot
ES339028A ES339028A1 (en) 1966-04-07 1967-04-07 Improvements in or relating to cephalosporins
DK195867A DK136609C (en) 1966-04-07 1967-04-07 PROCEDURE FOR PREPARATION AND PURIFICATION OF CEPHALORIDINE
NL6704945A NL6704945A (en) 1966-04-07 1967-04-07
CH1898269A CH533135A (en) 1966-04-07 1967-04-07 N-(7-acylamidoceph-3-em-3-ylmethyl)-pyridinium-4-carboxylate, antibiot
US220537A US3887551A (en) 1964-11-04 1972-01-24 Crystalline forms of cephaloridine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1571966A GB1171603A (en) 1966-04-07 1966-04-07 Improvements in or relating to cephalosporins

Publications (1)

Publication Number Publication Date
GB1171603A true GB1171603A (en) 1969-11-26

Family

ID=10064258

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1571966A Expired GB1171603A (en) 1964-11-04 1966-04-07 Improvements in or relating to cephalosporins

Country Status (10)

Country Link
AT (1) AT287189B (en)
BE (1) BE696775A (en)
CH (1) CH504472A (en)
DE (1) DE1695015C3 (en)
DK (1) DK136609C (en)
ES (1) ES339028A1 (en)
GB (1) GB1171603A (en)
GR (1) GR35150B (en)
NL (1) NL6704945A (en)
SE (1) SE370080B (en)

Also Published As

Publication number Publication date
CH504472A (en) 1971-03-15
ES339028A1 (en) 1968-07-01
DK136609B (en) 1977-10-31
SE370080B (en) 1974-09-30
DE1695015B2 (en) 1977-09-22
GR35150B (en) 1968-08-21
DK136609C (en) 1978-04-10
BE696775A (en) 1967-10-09
NL6704945A (en) 1967-10-09
DE1695015C3 (en) 1978-05-03
DE1695015A1 (en) 1972-03-09
AT287189B (en) 1971-01-11

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