GB1409801A - Azetidinones - Google Patents

Azetidinones

Info

Publication number
GB1409801A
GB1409801A GB14272*[A GB14272A GB1409801A GB 1409801 A GB1409801 A GB 1409801A GB 14272 A GB14272 A GB 14272A GB 1409801 A GB1409801 A GB 1409801A
Authority
GB
United Kingdom
Prior art keywords
ynylthio
group
formula
substituted
compound
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
GB14272*[A
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 to BE791159D priority Critical patent/BE791159A/en
Priority to BE791160D priority patent/BE791160A/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Priority to GB14272*[A priority patent/GB1409801A/en
Priority to AU48563/72A priority patent/AU4856372A/en
Priority to AU48562/72A priority patent/AU4856272A/en
Priority to FR7239483A priority patent/FR2166355B1/fr
Priority to DE2254632A priority patent/DE2254632A1/en
Priority to AT948672A priority patent/AT329579B/en
Priority to FR7239482A priority patent/FR2166354B1/fr
Priority to DE2254631A priority patent/DE2254631A1/en
Priority to CH1644972A priority patent/CH577518A5/xx
Priority to ZA727960A priority patent/ZA727960B/en
Priority to IL40799A priority patent/IL40799A/en
Priority to NL7215297A priority patent/NL7215297A/xx
Priority to ZA727961A priority patent/ZA727961B/en
Priority to ZA727962A priority patent/ZA727962B/en
Priority to IL40801A priority patent/IL40801A0/en
Priority to US05/493,453 priority patent/US3939157A/en
Priority to US05/501,846 priority patent/US3975383A/en
Priority to US05/501,961 priority patent/US3959267A/en
Publication of GB1409801A publication Critical patent/GB1409801A/en
Priority to JP57206826A priority patent/JPS6040234B2/en
Priority to JP58156217A priority patent/JPS6040235B2/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/568—Four-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1409801 Substituted ceph-3-ems and sulphoxides BEECHAM GROUP Ltd 8 Nov 1972 [3 Jan 1972 21 April 1972 5 Sept 1972] 142/72 18693/72 and 41091/72 Headings C2C and C2P Substituted ceph-3-ems and their sulphoxides, having the Formula (VIII) wherein n is 0 or 1, X is a substituted amino group, R<SP>3</SP> is an esterified carboxylic group and R is H or an organic radical, can be obtained by heating a compound of the Formula (IA) or (IB) where R a , R b and R c are substituted or unsubstituted alkyl, aryl or aralkyl groups, R a <SP>1</SP> and R b <SP>1</SP> are substituted or unsubstituted alkoxy or aralkoxy groups, at a temperature of from 30‹ to 150‹ C. in an inert organic solvent. Examples of the group X are triphenylmethylamino, t - butoxycarbonylamino, trichloroethoxycarbonylamino, phenoxyacetylamino, α - (t - butoxycarbonylamino), phenylacetylamino or 2-thienylacetylamino. Intermediates of Formulae IA and IB may be obtained by reacting a compound of Formula (IX) where Z is a halogen atom or an organic sulphonyloxy group (i) with a phosphine of Formula (IIIC) and if necessary eliminating HZ to form IA or (ii) with a compound (IIID) where R a <SP>1</SP>, R b <SP>1</SP> and R c <SP>1</SP> are substituted or unsubstituted alkoxy or aralkoxy groups, to yield IB. Alternatively, a compound of Formula (X) is reacted with a phosphine of Formula (IIIC) or (IIID), if necessary with elimination of HZ, to form a compound of Formula (XI) or (XIA) which is (i) treated with a primary or secondary amine, and, if the enamine formed does not hydrolyse spontaneously, the enamine is subjected to acid hydrolysis, or (ii) treated with water in the presence of a source of mercuric ions, or (iii) treated with a C 1-3 alkanol in the presence of a source of mercuric ions and an acid. The preparation of the following additional intermediates is also described:- 1-(1-benzyloxycarbonyl - 2 - methylpropenyl) - 3 - (triphenylmethylamino) - 4 - allenylthio - azetidin - 2 - one and corresponding 4 - (3 - phenylprop - 2- ynylthio)- and 4 - propargylthio - azetidin - 2- ones; 3 - triphenylmethylamino - 4 - propargylthio- (or 4 - (3 - phenylprop - 2 - ynylthio)- azetidin - 2 - ones and their 1 - (1 - hydroxy - 1 - methoxycarbonylmethyl)- and 1 - (1 - chloro- 1 - methoxycarbonylmethyl)- derivatives; 1 - (1 - methoxycarbonyl - 1 - triphenylphosphoranylidenemethyl) - 3 - triphenylmethylamino - 4 - propargylthio- (or 4 - (3 - phenylprop - 2 - ynylthio) - azetidin - 2 - ones; also disclosed are similar compounds containing a 4-(3-p-fluorophenylprop-2-ynylthio)- group or 4-(but-2-ynylthio) group or 4-[4-(2-tetrahydropyranyloxy) - but - 2 - ynylthio] group 4[3 - (2 - tetrahydropyranyl) - prop - 2 - ynylthio] or 4-(4-phenylbut-2-ynylthio) group and sulphoxides of some of these compounds.
GB14272*[A 1972-01-03 1972-01-03 Azetidinones Expired GB1409801A (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
BE791159D BE791159A (en) 1972-01-03 PROCESS FOR THE PREPARATION OF CEPHEMES
BE791160D BE791160A (en) 1972-01-03 NEW SUBSTITUTE CEPHEMES
GB14272*[A GB1409801A (en) 1972-01-03 1972-01-03 Azetidinones
AU48563/72A AU4856372A (en) 1972-01-03 1972-11-06 Cephalosporins
AU48562/72A AU4856272A (en) 1972-01-03 1972-11-06 Cephalosporins
FR7239483A FR2166355B1 (en) 1972-01-03 1972-11-08
DE2254632A DE2254632A1 (en) 1972-01-03 1972-11-08 SUBSTITUTED CEPH-3-EME AND CEPH3-EM-SULFOXIDE AND THE METHOD OF MANUFACTURING THEM
AT948672A AT329579B (en) 1972-01-03 1972-11-08 PROCESS FOR PRODUCING NEW SUBSTITUTED CEPH-3-EMEN AND CEPH-3-EM-SULFOXYDEN
FR7239482A FR2166354B1 (en) 1972-01-03 1972-11-08
DE2254631A DE2254631A1 (en) 1972-01-03 1972-11-08 SUBSTITUTED CEPH-3-EME
ZA727960A ZA727960B (en) 1972-01-03 1972-11-10 Azetidinones
CH1644972A CH577518A5 (en) 1972-01-03 1972-11-10
IL40799A IL40799A (en) 1972-01-03 1972-11-10 Preparation of ceph-3-ems and ceph-3-em sulphoxides
NL7215297A NL7215297A (en) 1972-01-03 1972-11-10
ZA727961A ZA727961B (en) 1972-01-03 1972-11-10 Azetidinones
ZA727962A ZA727962B (en) 1972-01-03 1972-11-10 Azetidinones
IL40801A IL40801A0 (en) 1972-01-03 1972-11-10 Novel substituted ceph-3-ems
US05/493,453 US3939157A (en) 1972-01-03 1974-07-31 3-Benzyl-7-substituted acetamido-3-cephem-4-carboxylic acids and halogenated benzyl derivatives
US05/501,846 US3975383A (en) 1972-01-03 1974-08-29 3-Benzyl-7-triphenylmethylamino-3-cephem-4-carboxylic acid and salts and esters thereof
US05/501,961 US3959267A (en) 1972-01-03 1974-08-30 3-(2'-Tetrahydropyranylmethyl)-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid and non-toxic salts thereof
JP57206826A JPS6040234B2 (en) 1972-01-03 1982-11-25 video signal processing equipment
JP58156217A JPS6040235B2 (en) 1972-01-03 1983-08-26 video signal processing equipment

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB14272*[A GB1409801A (en) 1972-01-03 1972-01-03 Azetidinones
GB1869372 1972-04-21
GB4109172 1972-09-05

Publications (1)

Publication Number Publication Date
GB1409801A true GB1409801A (en) 1975-10-15

Family

ID=27253669

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14272*[A Expired GB1409801A (en) 1972-01-03 1972-01-03 Azetidinones

Country Status (8)

Country Link
AU (1) AU4856372A (en)
BE (1) BE791159A (en)
CH (1) CH577518A5 (en)
DE (1) DE2254632A1 (en)
FR (1) FR2166354B1 (en)
GB (1) GB1409801A (en)
IL (1) IL40799A (en)
NL (1) NL7215297A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1426072A (en) * 1973-01-18 1976-02-25 Beecham Group Ltd Cephalosporins
FR2625798B1 (en) * 1988-01-08 1990-07-06 Perez Benoit BALLOON FOR PRODUCING HOT WATER AND METHOD FOR HEATING SAID BALLOON

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE759440A (en) * 1969-11-27 1971-05-26 Ciba Geigy Ag NEW THIADIAZABICYCLO-ALCENE
BE759439A (en) * 1969-11-27 1971-05-26 Ciba Geigy Ag

Also Published As

Publication number Publication date
FR2166354B1 (en) 1977-12-23
CH577518A5 (en) 1976-07-15
NL7215297A (en) 1973-07-05
DE2254632A1 (en) 1973-07-19
IL40799A0 (en) 1973-01-30
AU4856372A (en) 1974-05-09
BE791159A (en) 1973-05-09
FR2166354A1 (en) 1973-08-17
IL40799A (en) 1975-10-15

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees