IE34699B1 - Method of cleaving the 7-carboxamido group of a cephalosporin compound - Google Patents

Method of cleaving the 7-carboxamido group of a cephalosporin compound

Info

Publication number
IE34699B1
IE34699B1 IE1411/70A IE141170A IE34699B1 IE 34699 B1 IE34699 B1 IE 34699B1 IE 1411/70 A IE1411/70 A IE 1411/70A IE 141170 A IE141170 A IE 141170A IE 34699 B1 IE34699 B1 IE 34699B1
Authority
IE
Ireland
Prior art keywords
group
formula
integer
hydroxy
blocked
Prior art date
Application number
IE1411/70A
Other versions
IE34699L (en
Original Assignee
Lilly Co Eli
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 Lilly Co Eli filed Critical Lilly Co Eli
Publication of IE34699L publication Critical patent/IE34699L/en
Publication of IE34699B1 publication Critical patent/IE34699B1/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
    • C07D501/14—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

1302015 Cephalosporins ELI LILLY & CO 5 Nov 1970 [13 Nov 1969] 52755/70 Heading C2A A method for the cleavage of the 7-carboxamido group of a cephalosporin of Formula I wherein R is aminoadipoyl, C 2 -C 8 alkanoyl, a group of Formula II, III or IV X is C 2 -C 6 alkanoyloxy, C 2 -C 6 thioalkanoyloxy, C 6 -C 12 thioaroyloxy, hydroxy, mercapto, hydrogen, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio, Y is O, S or a carbon-to-carbon bond; n is an integer of 0-3 and is at least 1 when Y is O or S; m is an integer of 1 to 3 and Q is amino or hydroxy; comprises blocking the carboxyl, amino, hydroxy and mercapto groups in the molecule, treating the blocked cephalosporin with a halogenating agent to convert the 7 -carboxamido group to an imino halide, treating the imino halide with an alkanol or benzyl alcohol to form an imino ether, and hydrolysing the imino ether to form a 7-amino group and blocking the carboxyl groups by converting them to a mixed anhydride derived from an acid having the formula R<SP>1</SP>-COOH, wherein R<SP>1</SP> is C 1 -C 8 alkyl, alkenyl or alkynyl or a group of Formula V or VI wherein Y is O, S or a carbon-to-carbon bond, n is an integer of 0 to 3 and is at least 1 when Y is O or S ; Z is O, S or and m is an integer of 1 to 3. The invention also comprises blocked cephalosporins of general formula VII whose carboxyl groups are blocked by converting them to a mixed anhydride derived from an acid which has the general formula R<SP>1</SP> being defined as above. [GB1302015A]
IE1411/70A 1969-11-13 1970-11-05 Method of cleaving the 7-carboxamido group of a cephalosporin compound IE34699B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
IE34699L IE34699L (en) 1971-05-13
IE34699B1 true IE34699B1 (en) 1975-07-23

Family

ID=25368102

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1411/70A IE34699B1 (en) 1969-11-13 1970-11-05 Method of cleaving the 7-carboxamido group of a cephalosporin compound

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
FR2067278B1 (en) 1973-02-02
RO58347A (en) 1975-09-15
NL7016199A (en) 1971-05-17
IL35522A0 (en) 1970-12-24
MY7500099A (en) 1975-12-31
CH550200A (en) 1974-06-14
FR2067278A1 (en) 1971-08-20
SU501676A3 (en) 1976-01-30
CS167298B2 (en) 1976-04-29
SE380808B (en) 1975-11-17
NO143318C (en) 1981-01-14
BE758800A (en) 1971-05-12
AT301027B (en) 1972-08-25
NL171899C (en) 1983-06-01
DE2056491A1 (en) 1971-08-26
JPS4940479B1 (en) 1974-11-02
CY798A (en) 1976-12-01
IL35522A (en) 1974-09-10
YU36183B (en) 1982-02-25
ZA707137B (en) 1972-05-31
YU276270A (en) 1981-06-30
NO143318B (en) 1980-10-06
NL171899B (en) 1983-01-03
ES385395A1 (en) 1973-04-16
BR6915070D0 (en) 1973-07-17
PL88926B1 (en) 1976-10-30
GB1302015A (en) 1973-01-04
HK17576A (en) 1976-04-02
CA977747A (en) 1975-11-11
IE34699L (en) 1971-05-13

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