GB1510795A - 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates - Google Patents

2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates

Info

Publication number
GB1510795A
GB1510795A GB4121577A GB4121577A GB1510795A GB 1510795 A GB1510795 A GB 1510795A GB 4121577 A GB4121577 A GB 4121577A GB 4121577 A GB4121577 A GB 4121577A GB 1510795 A GB1510795 A GB 1510795A
Authority
GB
United Kingdom
Prior art keywords
methyl
azetidinyl
oxo
chloro
alkyl
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
GB4121577A
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.)
Queens University at Kingston
Original Assignee
Queens University at Kingston
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 GB34614/74A external-priority patent/GB1510794A/en
Application filed by Queens University at Kingston filed Critical Queens University at Kingston
Priority to GB4121577A priority Critical patent/GB1510795A/en
Priority to SE7508824A priority patent/SE7508824L/en
Publication of GB1510795A publication Critical patent/GB1510795A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • 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
    • 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
    • C07D205/085—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 nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1510795 2(2 - Chloro - 4 - oxo)azetidinyl- 3-methyl-3-butenoates QUEEN'S UNIVERSITY AT KINGSTON 30 June 1975 [6 Aug 1974] 41215/77 Divided out of 1510794 Heading C2C Novel 2 - (2 - chloro - 4 - oxo)azetidinyl- 3-methyl-3-butenoates of general formula wherein R<SP>8</SP> is H or RCO- or R<SP>8</SP>NH- forms a phthalimido group; R is C 1-5 alkyl, Ar-X-C(R<SP>5</SP>)(R<SP>6</SP>)-, Z<SP>1</SP>Z<SP>2</SP>Z<SP>3</SP>C- or R<SP>12</SP>-O-, Ar is a radical in which R, R 2 and R 3 , same or different, are H, Cl, Br, I, CF 3 , phenyl, C 1-5 alkyl or C 1-5 alkoxy, but only one may be phenyl; R<SP>4</SP> is H, -NH 2 , C 6 H 5 OCONH-, phenyl, F, Cl, Br, I, -COOH, -SO 3 H,-N 3 , -OH C 1-5 alkanoyloxy or C 1-5 alkoxy; X is -O- or -S-; R<SP>5</SP> and R<SP>6</SP> are each H, phenyl, benzyl, phenethyl or C 1-5 alkyl; Z<SP>1</SP>, Z<SP>2</SP> and Z<SP>3</SP> are each C 1-5 alkyl or on Ar group; R<SP>12</SP> is CCl 3 CH 2 - or benzyl; R<SP>1</SP> is H, alkyl, benzyl, benzhydryl, alkoxyalkyl, alkoxybenzyl, phenacyl, (CH 3 ) 3 Si-, CClCH 3 or pivaloyl groups, are prepared by debromination of a compound with 2-4 molar equivalents of Zn in an alkanoio acid. Alternatively a mixture of the 4-bromo- 3-methyl- and 3-bromomethylazetidinyl-but- 2-enoic acid derivatives may be debrominated with Zn in glacial acetic acid. The compounds 2-(2<SP>1</SP>R or 2<SP>2</SP>S-chloro-3<SP>1</SP>5-phthalimido-4<SP>1</SP>-oxo)- azetidinyl - 3 - methyl - 3 - butenoate and methyl or benzhydryl 2-(2<SP>1</SP>R-chloro-3<SP>1</SP>S-trichloroethoxycarbonylamino - 4<SP>1</SP>- oxo) azetidinyl-3-methyl-3-butenoate are described. 3-Methyl or 3-hydroxy-1-oxacephems of general formula are obtained from the compounds of the invention. Reference has been directed by the Comptroller to Specification 1,346,744.
GB4121577A 1974-08-06 1975-06-30 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates Expired GB1510795A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB4121577A GB1510795A (en) 1974-08-06 1975-06-30 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates
SE7508824A SE7508824L (en) 1974-08-06 1975-08-05 WAY TO PRODUCE L-OXACEFEMER AND INTERMEDIATE ASSOCIATIONS THEREOF.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB34614/74A GB1510794A (en) 1974-08-06 1974-08-06 1-oxacephems and intermediates therefor
GB4121577A GB1510795A (en) 1974-08-06 1975-06-30 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates

Publications (1)

Publication Number Publication Date
GB1510795A true GB1510795A (en) 1978-05-17

Family

ID=26262362

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4121577A Expired GB1510795A (en) 1974-08-06 1975-06-30 2-(2'-chloro-3'-substituted-4-oxo)azetidinyl-3-methyl-3-butenoates

Country Status (2)

Country Link
GB (1) GB1510795A (en)
SE (1) SE7508824L (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0864570A1 (en) * 1997-03-13 1998-09-16 PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo Epoxy-azetidinones, preparation and use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0864570A1 (en) * 1997-03-13 1998-09-16 PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo Epoxy-azetidinones, preparation and use thereof

Also Published As

Publication number Publication date
SE7508824L (en) 1976-02-09

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee