GB1480027A - Cephalosporin derivatives - Google Patents

Cephalosporin derivatives

Info

Publication number
GB1480027A
GB1480027A GB21509/75A GB2150975A GB1480027A GB 1480027 A GB1480027 A GB 1480027A GB 21509/75 A GB21509/75 A GB 21509/75A GB 2150975 A GB2150975 A GB 2150975A GB 1480027 A GB1480027 A GB 1480027A
Authority
GB
United Kingdom
Prior art keywords
prepared
reaction
pyridazine
hydroxy
tetrazolo
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
GB21509/75A
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.)
Bristol Myers Co
Original Assignee
Bristol Myers 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
Priority claimed from US05/473,040 external-priority patent/US3985738A/en
Priority claimed from US473021A external-priority patent/US3910900A/en
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1480027A publication Critical patent/GB1480027A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1480027 Cephalosporin derivatives BRISTOLMYERS CO 20 May 1975 [24 May 1974 (2)] 21509/75 Heading C2C Novel compounds I having the D configuration in the 7-side chain (X is 3-hydroxy-pyridazin-6-yl or tetrazolo- [4,5 - b]pyridazin - 6 - yl; R=2- or 3-thienyl or phenyl optionally substituted by Cl, Br, F, CF 3 , NH 2 , NO 2 , OH, 1-4 C alkyl or 1-4 C alkoxy) and salts and easily hydrolysed esters thereof are prepared by reaction of the corresponding 7-amino derivatives with an acylating agent RCH(OH)COOH or a reactive derivative thereof in which the hydroxy group may be protected or by reaction of the corresponding 3 - acetoxymethyl derivatives with 6 - mercapto - 3 - hydroxy - pyridazine or 6 - mercapto-tetrazolo-[4,5-b]pyridazine. The 7-amino derivatives are prepared by conventional methods. Other intermediates isolated are 3-chloro-6- hydroxy - pyridazine (A), prepared by hydrolysis of the 3,6-dichloro derivative; 3-hydroxy-6- mercapto - pyridarine (B), prepared by reaction of (A) with KSH or of 3,6-dihydroxypyridazine with P 2 S 5 ; 3,6-dihydroxy-pyridazine (C), prepared by reaction of maleic anhydride with hydrazine; 3,6-dichloro-pyridazine (D), prepared by reaction of (C) with POCl 3 ; 3 - chloro - 6 - hydrazinopryidazine (E), prepared by reaction of (D) with hydrazine hydrate; 6 - chloro - tetrazolo[4,5 - b]pyridazine (F), prepared by reaction of (E) with NaNO 2 ; 6 - mercapto - tetrazolo[4,5 - b]pyridazine (G), prepared by reaction of (F) with KSH; and D - mandelic acid carboxy anhydride (H), prepared by reaction of phosgene with D(-)- mandelic acid. Pharmaceutical compositions having antibacterial activity comprise a compound I together with a suitable diluent and/or carrier.
GB21509/75A 1974-05-24 1975-05-20 Cephalosporin derivatives Expired GB1480027A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/473,040 US3985738A (en) 1974-05-24 1974-05-24 7-(D-.alpha.-Hydroxy-2-arylacetamido)-3-(tetrazolo-[4,5-b]pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US473021A US3910900A (en) 1974-05-24 1974-05-24 7-(D-a-hydroxy-2-arylacetamido)-3-(3-hydroxypyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acids

Publications (1)

Publication Number Publication Date
GB1480027A true GB1480027A (en) 1977-07-20

Family

ID=27044006

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21509/75A Expired GB1480027A (en) 1974-05-24 1975-05-20 Cephalosporin derivatives

Country Status (9)

Country Link
JP (1) JPS50160292A (en)
CA (1) CA1052770A (en)
DE (1) DE2522997A1 (en)
DK (1) DK223775A (en)
FR (2) FR2271828B1 (en)
GB (1) GB1480027A (en)
NL (1) NL7505960A (en)
SE (1) SE421702B (en)
YU (1) YU37479B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859123A (en) * 1987-04-25 1989-08-22 Mitsubishi Kinzoku Kabushiki Kaisha Insert boring tool

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI771866A (en) * 1976-06-28 1977-12-29 Fujisawa Pharmaceutical Co
JPS53153692U (en) * 1977-05-11 1978-12-02

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4859123A (en) * 1987-04-25 1989-08-22 Mitsubishi Kinzoku Kabushiki Kaisha Insert boring tool

Also Published As

Publication number Publication date
SE7505808L (en) 1975-11-25
SE421702B (en) 1982-01-25
DK223775A (en) 1975-11-25
DE2522997A1 (en) 1975-12-04
FR2271828B1 (en) 1980-02-08
YU37479B (en) 1984-08-31
NL7505960A (en) 1975-11-26
AU8112775A (en) 1976-11-18
YU131675A (en) 1983-04-27
FR2400900A1 (en) 1979-03-23
CA1052770A (en) 1979-04-17
FR2400900B1 (en) 1982-09-03
JPS50160292A (en) 1975-12-25
FR2271828A1 (en) 1975-12-19

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee