GB1315995A - Substituted azetidinones - Google Patents

Substituted azetidinones

Info

Publication number
GB1315995A
GB1315995A GB3705770A GB1315995DA GB1315995A GB 1315995 A GB1315995 A GB 1315995A GB 3705770 A GB3705770 A GB 3705770A GB 1315995D A GB1315995D A GB 1315995DA GB 1315995 A GB1315995 A GB 1315995A
Authority
GB
United Kingdom
Prior art keywords
sch
och
prepared
reacting
cooch
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
GB3705770A
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.)
Yeda Research and Development Co Ltd
Original Assignee
Yeda Research and Development Co 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 Yeda Research and Development Co Ltd filed Critical Yeda Research and Development Co Ltd
Publication of GB1315995A publication Critical patent/GB1315995A/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
    • 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 -.
GB3705770A 1970-07-31 1970-07-31 Substituted azetidinones Expired GB1315995A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
GB1315995A true GB1315995A (en) 1973-05-09

Family

ID=10393398

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3705770A Expired GB1315995A (en) 1970-07-31 1970-07-31 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
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
IE35418L (en) 1972-01-31
AU461641B2 (en) 1975-06-05
AT311374B (en) 1973-11-12
DE2138333A1 (en) 1972-02-10

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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