ES385395A1 - An improved method for the split of the 7-carboxamido group of a cephalosporine. (Machine-translation by Google Translate, not legally binding) - Google Patents

An improved method for the split of the 7-carboxamido group of a cephalosporine. (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES385395A1
ES385395A1 ES385395A ES385395A ES385395A1 ES 385395 A1 ES385395 A1 ES 385395A1 ES 385395 A ES385395 A ES 385395A ES 385395 A ES385395 A ES 385395A ES 385395 A1 ES385395 A1 ES 385395A1
Authority
ES
Spain
Prior art keywords
sulfur
oxygen
integer
formula
see 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
ES385395A
Other languages
Spanish (es)
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 ES385395A1 publication Critical patent/ES385395A1/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
    • 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
    • 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

Landscapes

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

Abstract

An improved method for cleavage of the 7-carboxamide group from a cephalosporin of formula: **(See formula)** where R is aminoadipoyl, C2-C3 alkanoyl, or **(See formula)** X is C2-C6 alkanoyloxy, C2-C6 thioalkanoyloxy, C6-C12 thioaroyloxy, hydroxy, percapto, hyurogen, C1-C6 alkoxy, C1-C6 alkylthio, Y is oxygen, sulfur, or a carbon-carbon bond; n is an integer from 0 to 3 and is worth at least 1 when Y is oxygen or sulfur; m is an integer from 1 to 3; and Q is amino or hydroxy; by the steps of blocking the carboxyl, amino, hydroxy, and mercapto groups of the molecule, treating the blocked cephalosporin with a halogenating agent to convert the 7-carboxamide group to an iminohalide, treating the iminohalide with a lower alkanol or benzyl alcohol to form a iminoether and hydrolyze the iminoether to form a 7-amino group, in which method the improvement is characterized by blocking the carboxyl groups converting them into a mixed anhydride derived from an acid of formula R'-CO2H where R'is alkyl, alkenyl or C1-C8 alkynyl; haloalkyl, haloalkenyl, or C1-C8 haloalkynyl; **(See formula)** Y is oxygen, sulfur, or a carbon-carbon bond; n is an integer from 0 to 3 and is worth at least 1 when Y is oxygen or sulfur; Z is oxygen, sulfur, or (see formula) and m is an integer from 1 to 3. (Machine-translation by Google Translate, not legally binding)
ES385395A 1969-11-13 1970-11-10 An improved method for the split of the 7-carboxamido group of a cephalosporine. (Machine-translation by Google Translate, not legally binding) Expired ES385395A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US87659769A 1969-11-13 1969-11-13

Publications (1)

Publication Number Publication Date
ES385395A1 true ES385395A1 (en) 1973-04-16

Family

ID=25368102

Family Applications (1)

Application Number Title Priority Date Filing Date
ES385395A Expired ES385395A1 (en) 1969-11-13 1970-11-10 An improved method for the split of the 7-carboxamido group of a cephalosporine. (Machine-translation by Google Translate, not legally binding)

Country Status (24)

Country Link
JP (1) JPS4940479B1 (en)
AT (1) AT301027B (en)
BE (1) BE758800A (en)
BR (1) BR6915070D0 (en)
CA (1) CA977747A (en)
CH (1) CH550200A (en)
CS (1) CS167298B2 (en)
CY (1) CY798A (en)
DE (1) DE2056491A1 (en)
ES (1) ES385395A1 (en)
FR (1) FR2067278B1 (en)
GB (1) GB1302015A (en)
HK (1) HK17576A (en)
IE (1) IE34699B1 (en)
IL (1) IL35522A (en)
MY (1) MY7500099A (en)
NL (1) NL171899C (en)
NO (1) NO143318C (en)
PL (1) PL88926B1 (en)
RO (1) RO58347A (en)
SE (1) SE380808B (en)
SU (1) SU501676A3 (en)
YU (1) YU36183B (en)
ZA (1) ZA707137B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5248993B1 (en) * 1971-07-29 1977-12-14
US4008231A (en) * 1975-09-15 1977-02-15 Eli Lilly And Company Preparation of 3-methoxymethylcephalosporins
GR70261B (en) * 1977-12-12 1982-09-02 Takeda Chemical Industries Ltd

Also Published As

Publication number Publication date
ZA707137B (en) 1972-05-31
YU276270A (en) 1981-06-30
MY7500099A (en) 1975-12-31
IL35522A (en) 1974-09-10
SU501676A3 (en) 1976-01-30
JPS4940479B1 (en) 1974-11-02
FR2067278A1 (en) 1971-08-20
CY798A (en) 1976-12-01
NO143318B (en) 1980-10-06
IE34699B1 (en) 1975-07-23
GB1302015A (en) 1973-01-04
IE34699L (en) 1971-05-13
AT301027B (en) 1972-08-25
HK17576A (en) 1976-04-02
PL88926B1 (en) 1976-10-30
RO58347A (en) 1975-09-15
YU36183B (en) 1982-02-25
CS167298B2 (en) 1976-04-29
IL35522A0 (en) 1970-12-24
SE380808B (en) 1975-11-17
NL7016199A (en) 1971-05-17
NL171899C (en) 1983-06-01
CA977747A (en) 1975-11-11
CH550200A (en) 1974-06-14
DE2056491A1 (en) 1971-08-26
BE758800A (en) 1971-05-12
BR6915070D0 (en) 1973-07-17
NO143318C (en) 1981-01-14
FR2067278B1 (en) 1973-02-02
NL171899B (en) 1983-01-03

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19930209