GB1457421A - Cepham derivatives - Google Patents

Cepham derivatives

Info

Publication number
GB1457421A
GB1457421A GB61973A GB61973A GB1457421A GB 1457421 A GB1457421 A GB 1457421A GB 61973 A GB61973 A GB 61973A GB 61973 A GB61973 A GB 61973A GB 1457421 A GB1457421 A GB 1457421A
Authority
GB
United Kingdom
Prior art keywords
group
hydrogen atom
blocked
free
general 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
GB61973A
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 GB61973A priority Critical patent/GB1457421A/en
Priority to JP430174A priority patent/JPS49116092A/ja
Priority to BE139497A priority patent/BE809370A/en
Priority to DE19742400165 priority patent/DE2400165A1/en
Priority to FR7400163A priority patent/FR2224475B1/fr
Priority to NL7400058A priority patent/NL7400058A/xx
Priority to AT4274A priority patent/AT333950B/en
Priority to AT666275A priority patent/AT334535B/en
Publication of GB1457421A publication Critical patent/GB1457421A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3

Landscapes

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

Abstract

1457421 3 - Hydroxy- and 3 - oxo - 7 - amino- and blocked ammo-(6R, 7R)-cephams GLAXO LABORATORIES Ltd 2 Jan 1974 [4 Jan 1973] 619/73 Heading C2C 3 - Hydroxy- and 3 - oxo - 7 - amino- and blocked amino - (6R, 7R) - cephams of the general formula wherein R<SP>1</SP> is a free or blocked amino group; R<SP>a</SP>, R<SP>b</SP>, R<SP>e</SP> and R<SP>f</SP> are each a hydrogen atom or an alkyl, aralkyl, aryl, cyano or free or blocked carboxyl group; and either R<SP>c</SP> is a hydroxy group and R<SP>d</SP> is a hydrogen atom or R<SP>c</SP> and R<SP>d</SP> together form an oxygen atom, which are novel provided that at least one of R<SP>a</SP> and R<SP>b</SP> is other than a hydrogen atom when one of R<SP>e</SP> and R<SP>f</SP> is a blocked carboxyl group and the other of R<SP>e</SP> and R<SP>f</SP> is a hydrogen atom and that at least one of R<SP>a</SP> and R<SP>b</SP> is other than a hydrogen atom when R<SP>c</SP> is a hydroxy group and one of R<SP>e</SP> and R<SP>f</SP> is a free carboxyl group and the other of R<SP>e</SP> and R<SP>f</SP> is a hydrogen atom, are prepared (i) by cyclizing an azetidin-2-one of the general formula wherein either (a) R<SP>1</SP> is a free or blocked amino group; R<SP>2</SP> is a group, in which R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>8</SP> are each a hydrogen atom or an alkyl, aralkyl, aryl, cyano or free or blocked carboxyl group, and R<SP>9</SP> and R<SP>10</SP> together form an oxygen atom and R<SP>11</SP> is a hydrogen atom or R<SP>9</SP> is a hydrogen atom or a readily eliminable substituent and R<SP>10</SP> and R<SP>11</SP> together form an oxygen atom; and R<SP>4</SP> is a hydrogen atom; or (b) either R<SP>1</SP> is a free or blocked amino group and R<SP>2</SP> is an acyl (including sulphonyl, sulphinyl or phosphoryl) group, the residue -SR<SP>3</SP> of a thiophilic sulphur nucleophile R<SP>3</SP>SH, in which R<SP>3</SP> is an aliphatic, araliphatic or aromatic group, or a group of formula wherein R<SP>4a</SP> is a hydrogen atom or a group of Formula V, or R<SP>1</SP> and R<SP>2</SP>, together with the S atom to which R<SP>2</SP> is attached, form a group -N=C(R)-S- or -NH-CHR-S-, in which R is the residue of an acyl group RCO containing 1-20 carbon atoms; and R<SP>4</SP> is a group of Formula V; and (ii) when R<SP>c</SP> and R<SP>d</SP> together form an oxygen atom, by oxidation of the corresponding compound in which R<SP>c</SP> is a hydroxy group and R<SP>d</SP> is a hydrogen atom. Azetidin-2-ones of the second general formula above are prepared by reacting a compound of the general formula wherein R<SP>1</SP> and R<SP>2</SP> are as defined under (b) above, except that R<SP>4a</SP> is a hydrogen atom only, with a compound of the general formula R<SP>5</SP>R<SP>6</SP>R<SP>9</SP>-CR<SP>10</SP>R<SP>11</SP>-CR<SP>7</SP>R<SP>8</SP>X, wherein X is a readily eliminable substituent. Reference has been directed by the Comptroller to Specification 1,420,160.
GB61973A 1973-01-04 1973-01-04 Cepham derivatives Expired GB1457421A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB61973A GB1457421A (en) 1973-01-04 1973-01-04 Cepham derivatives
JP430174A JPS49116092A (en) 1973-01-04 1973-12-28
BE139497A BE809370A (en) 1973-01-04 1974-01-03 3-HYDROXY AND 3-OXO-7-AMINO
DE19742400165 DE2400165A1 (en) 1973-01-04 1974-01-03 ANTIBIOTICS
FR7400163A FR2224475B1 (en) 1973-01-04 1974-01-03
NL7400058A NL7400058A (en) 1973-01-04 1974-01-03
AT4274A AT333950B (en) 1973-01-04 1974-01-03 PROCESS FOR PRODUCING NEW CEPHAM CONNECTIONS
AT666275A AT334535B (en) 1973-01-04 1975-08-28 PROCESS FOR PRODUCING NEW CEPHAM CONNECTIONS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB61973A GB1457421A (en) 1973-01-04 1973-01-04 Cepham derivatives

Publications (1)

Publication Number Publication Date
GB1457421A true GB1457421A (en) 1976-12-01

Family

ID=9707545

Family Applications (1)

Application Number Title Priority Date Filing Date
GB61973A Expired GB1457421A (en) 1973-01-04 1973-01-04 Cepham derivatives

Country Status (7)

Country Link
JP (1) JPS49116092A (en)
AT (1) AT333950B (en)
BE (1) BE809370A (en)
DE (1) DE2400165A1 (en)
FR (1) FR2224475B1 (en)
GB (1) GB1457421A (en)
NL (1) NL7400058A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1136132A (en) * 1975-02-17 1982-11-23 Teruji Tsuji Cyclization to form cephem ring and intermediates therefor
US4024152A (en) * 1975-09-19 1977-05-17 Eli Lilly And Company 4-Dithio-3-imido-azetidin-2-ones
EP3610899B1 (en) * 2016-09-20 2023-11-01 Medela Holding AG Extraction and supply device with drive unit and connection piece

Also Published As

Publication number Publication date
BE809370A (en) 1974-07-03
NL7400058A (en) 1974-07-08
FR2224475B1 (en) 1979-02-23
AT333950B (en) 1976-12-27
FR2224475A1 (en) 1974-10-31
ATA4274A (en) 1976-04-15
DE2400165A1 (en) 1974-07-18
JPS49116092A (en) 1974-11-06

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Legal Events

Date Code Title Description
49R Reference inserted (sect. 9/1949)
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee