GB1341827A - Derivatives of cephalosporanic acid - Google Patents

Derivatives of cephalosporanic acid

Info

Publication number
GB1341827A
GB1341827A GB6184269A GB1341827DA GB1341827A GB 1341827 A GB1341827 A GB 1341827A GB 6184269 A GB6184269 A GB 6184269A GB 1341827D A GB1341827D A GB 1341827DA GB 1341827 A GB1341827 A GB 1341827A
Authority
GB
United Kingdom
Prior art keywords
group
phenyl
alkyl
formula
acid
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
GB6184269A
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.)
DSM Delft BV
Original Assignee
Koninklijke Nederlandsche Gist en Spiritusfabriek BV
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 Koninklijke Nederlandsche Gist en Spiritusfabriek BV filed Critical Koninklijke Nederlandsche Gist en Spiritusfabriek BV
Publication of GB1341827A publication Critical patent/GB1341827A/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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1341827 Silyl derivatives of 7-isocyanatocephalosporanic acid KONINKLIJKE NEDERLANDSCHE GIST-EN SPIRITUSFABRIEK NV 18 Dec 1970 [18 Dec 1969] 61842/69 Heading C3S [Also in Division C2] The invention comprises 7-isocyanatocephalosporanic acid derivatives of the formula wherein R represents a hydrogen atom, a protected hydroxy group or an acyloxy group, and E represents a carboxylic protecting group such as a silyl group of general formula (R 1 ) 3 Siin which R 1 represents C 1 -C 6 alkyl, phenyl or phenyl (C 1 -C 6 ) alkyl. In particular E may represent the trimethylsilyl group. The above compounds also include those in which R is a protected hydroxy group of formula -OSi(R 1 ) 3 in which R 1 is C 1 -C 6 alkyl, phenyl or phenyl (C 1 -C 6 ) alkyl. Examples of such compounds are trimethylsilyl esters of 7-isocyanato-cephalosporanic and 7-isocyanatodesacetoxycephalosporanic acid. The 7-isocyanate cephalosporanic acid derivatives are prepared by reacting phosgene with a cephalosporanic acid derivative of formula wherein W represents a hydrogen atom or a group (R 1 ) 3 Siin which R 1 represents a C 1 -C 6 alkyl group, phenyl group or phenyl (C 1 -C 6 ) alkyl group in an inert organic solvent, to convert the grouping W-NH- into the isocyanate group without affecting the rest of the molecule. Reference has been directed by the Comptroller to Specification 1,174,335.
GB6184269A 1969-12-18 1970-12-18 Derivatives of cephalosporanic acid Expired GB1341827A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6184269 1969-12-18

Publications (1)

Publication Number Publication Date
GB1341827A true GB1341827A (en) 1973-12-25

Family

ID=10487533

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6184269A Expired GB1341827A (en) 1969-12-18 1970-12-18 Derivatives of cephalosporanic acid

Country Status (10)

Country Link
CA (1) CA985670A (en)
CS (1) CS165353B2 (en)
DE (1) DE2062296C3 (en)
ES (1) ES386599A1 (en)
FR (1) FR2081379B1 (en)
GB (1) GB1341827A (en)
HU (1) HU162432B (en)
NL (1) NL148321B (en)
SU (1) SU416948A3 (en)
ZA (1) ZA708521B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1193478B (en) * 1979-06-14 1988-07-08 Ausonia Farma Srl PROCEDURE FOR THE PREPARATION OF 7- (L-AMINO-L-PHENYLACETAMIDE) -3-METHYL-3-CEFEM-4-PIVALOYLOXYSIMETYL CARBOXYLATE

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1432507A (en) * 1959-08-04 1966-03-25 Nat Res Dev Cephalosporin derivatives c.
US3173916A (en) * 1960-06-28 1965-03-16 Pfizer & Co C Derivatives of 7-aminocephalosporanic acid
SE311519B (en) * 1962-12-14 1969-06-16 Astra Ab
CH480365A (en) * 1965-01-18 1969-10-31 Ciba Geigy Process for the preparation of new derivatives of 7-aminocephalosporanic acid
NL155260B (en) * 1968-06-19 1977-12-15 Koninklijke Gist Spiritus PROCESS FOR THE PREPARATION OF DERIVATIVES OF 6-AMINOPENICILLAAN ACID.

Also Published As

Publication number Publication date
ZA708521B (en) 1971-09-29
FR2081379A1 (en) 1971-12-03
DE2062296B2 (en) 1974-08-15
DE2065462B2 (en) 1976-01-15
HU162432B (en) 1973-02-28
SU416948A3 (en) 1974-02-25
DE2065462A1 (en) 1973-10-18
DE2062296C3 (en) 1975-04-17
ES386599A1 (en) 1973-11-16
CA985670A (en) 1976-03-16
NL7018387A (en) 1971-06-22
DE2062296A1 (en) 1971-07-01
FR2081379B1 (en) 1974-08-30
CS165353B2 (en) 1975-12-22
NL148321B (en) 1976-01-15

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees