IE35418L - Substituted azetidinones - Google Patents

Substituted azetidinones

Info

Publication number
IE35418L
IE35418L IE710843A IE84371A IE35418L IE 35418 L IE35418 L IE 35418L IE 710843 A IE710843 A IE 710843A IE 84371 A IE84371 A IE 84371A IE 35418 L IE35418 L IE 35418L
Authority
IE
Ireland
Prior art keywords
sch
och
prepared
reacting
cooch
Prior art date
Application number
IE710843A
Other versions
IE35418B1 (en
Original Assignee
Yeda Res & Dev
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 Yeda Res & Dev filed Critical Yeda Res & Dev
Publication of IE35418L publication Critical patent/IE35418L/en
Publication of IE35418B1 publication Critical patent/IE35418B1/en

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
    • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1315995 Azetidinone derivatives YEDA RESEARCH & DEVELOPMENT CO Ltd 22 June 1971 [31 July 1970] 37057/70 Heading C2C Azetidin-2-ones having a thioether substituent in the 4-position and a halogen, azido or dicarboxylic acid imido group in the 3-position, and especially novel compounds of formula where X is halogen, azido or dicarboxylic acid imido, R is optionally substituted alkyl or aralkyl, R<SP>1</SP> is optionally substituted alkoxy or aralkoxy, R<SP>2</SP> and R<SP>3</SP> are H or optionally substituted alkyl, aralkoxy or alkylthioalkyl, and Y and Z are each H or together represent a bond joining the carbons to which they are attached, are prepared by reacting a thioimidate derivative of an α-amino acid with XCHCOHal under anhydrous conditions in the presence of a tertiary base. X=Cl may subsequently be converted to X=azido by means of NaN 3 . Compounds of formula where R<SP>4</SP> is -CH(CH 3 ) 2 , -CH 2 OCH 2 C 6 H 5 , -CH 2 CH 2 SCH 3 and -C(CH 3 ) 2 SCH 3 are prepared by reacting appropriate amino acid esters with HCSOC 2 H 5 . is obtained from HC(NH)OC 2 H 5 and the corresponding amino acid ester. Starting materials of formula where: R<SP>5</SP>=CH 3 , R<SP>4</SP>=-CH(CH 3 ) 2 ; R<SP>5</SP>= C 6 H 5 CH 2 -, R<SP>4</SP> =-CH(CH 3 ) 2 ; R<SP>5</SP> = CH 3 , R<SP>4</SP>=-CH 2 OCH 2 C 6 H 5 ; R<SP>5</SP> = CH 3 , R<SP>4</SP>= -CH 2 CH 2 SCH 3 ; R<SP>5</SP>=4-NO 2 -C 6 H 4 CH 2 -, R<SP>4</SP>=-CH 2 CH 2 SCH 3 ; and R<SP>5</SP>=CH 3 , R<SP>4</SP> = -C(CH 3 ) 2 SCH 3 are prepared by reacting R<SP>5</SP>Hal with HC(S)NHCHR<SP>4</SP>COOCH 3 ; where R<SP>5</SP>= CH 3 OOCCH 2 CH 2 - and R<SP>4</SP>=-CH(CH 3 ) 2 and -CH 2 OCH 2 C 6 H 5 by reacting with the compounds in which R<SP>5</SP> = CH 3 or with C 2 H 5 OCH = NCH(COOCH 3 )CH(CH 3 ) 2 . CH 3 SCH = NC(COOCH 3 ) = C(CH 3 ) 2 is prepared from and CH 3 I in the presence of NaH. Phthaloylglycylvaline methyl ester is obtained as a by-product of the reaction between phthaloylglycylchloride and when R<SP>5</SP> is CH 3 - or C 6 H 5 CH 2 -. [GB1315995A]
IE843/71A 1970-07-31 1971-07-01 Substituted azetidinones IE35418B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3705770 1970-07-31

Publications (2)

Publication Number Publication Date
IE35418L true IE35418L (en) 1972-01-31
IE35418B1 IE35418B1 (en) 1976-02-04

Family

ID=10393398

Family Applications (1)

Application Number Title Priority Date Filing Date
IE843/71A IE35418B1 (en) 1970-07-31 1971-07-01 Substituted azetidinones

Country Status (13)

Country Link
AT (1) AT311374B (en)
AU (1) AU461641B2 (en)
BE (1) BE770796A (en)
CA (1) CA960677A (en)
CH (1) CH570979A5 (en)
DE (1) DE2138333A1 (en)
ES (1) ES393757A1 (en)
FR (1) FR2103772A5 (en)
GB (1) GB1315995A (en)
IE (1) IE35418B1 (en)
IL (1) IL37118A (en)
NL (1) NL7109058A (en)
ZA (1) ZA715081B (en)

Also Published As

Publication number Publication date
AU3187271A (en) 1973-02-01
ES393757A1 (en) 1975-09-16
IL37118A0 (en) 1971-08-25
GB1315995A (en) 1973-05-09
IL37118A (en) 1974-11-29
NL7109058A (en) 1972-02-02
CA960677A (en) 1975-01-07
ZA715081B (en) 1972-04-26
FR2103772A5 (en) 1972-04-14
BE770796A (en) 1972-01-31
IE35418B1 (en) 1976-02-04
CH570979A5 (en) 1975-12-31
AU461641B2 (en) 1975-06-05
AT311374B (en) 1973-11-12
DE2138333A1 (en) 1972-02-10

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