IE55996B1 - Beta-lactams - Google Patents

Beta-lactams

Info

Publication number
IE55996B1
IE55996B1 IE1931/83A IE193183A IE55996B1 IE 55996 B1 IE55996 B1 IE 55996B1 IE 1931/83 A IE1931/83 A IE 1931/83A IE 193183 A IE193183 A IE 193183A IE 55996 B1 IE55996 B1 IE 55996B1
Authority
IE
Ireland
Prior art keywords
signifies
group
alkenyl
general formula
amino
Prior art date
Application number
IE1931/83A
Other versions
IE831931L (en
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of IE831931L publication Critical patent/IE831931L/en
Publication of IE55996B1 publication Critical patent/IE55996B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/14—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 three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE. Optically uniform beta-lactams of the general formula see diagramm : EP0101598,P12,F5 wherein R**1 signifies lower 2- or 1-alkenyl or a group of the formula -CH2 -CH(OR**4 )2 -CH2 -CHO -CO-CH(OH)2 see diagramm : EP0101598,P13,F1 R**4 signifies lower alkyl, n signifies the number 0 or 1, R**2 signifies amino, azido, phthalimido. ROCO-CH=C(CH3 )-NH- or Z-NH- ; R signifies lower alkyl, Z signifies a readily cleavable acyl group and R**6 and R**7 each signify a lower hydrocarbon residue which optionally contains oxygen and which is attached via a carbon atom, said residues being optionally joined with one another, whereby R**1 signifies lower 2- or 1-alkenyl or one of the groups (a), (c) and (d) when R**2 signifies amino and the residues denotes as lower contain up ot 8 carbon atoms, and the corresponding optical antipodes thereof. 1. Claims for the Contracting State AT A process for the manufacture of optically uniform beta-lactams of the general formula see diagramm : EP0101598,P14,F6 wherein R**1 signifies lower 2- or 1-alkenyl or a group of the formula -CH2 -CH(OR**4 )2 -CH2 -CHO -CO-CH(OH)2 see diagramm : EP0101598,P14,F2 R**4 signifies lower alkyl, n signifies the number 0 or 1, R**2 signifies amino, azido, phthalimido, ROCO-CH=C(CH3 )-NH- or Z-NH- ; R signifies lower alkyl, Z signifies a readily cleavable acyl group and R**6 and R**7 each signify a lower hydrocarbon residue which optionally contains oxygen and which is attached via a carbon atom, said residues being optionally joined with one another, whereby R**1 signifies lower 2- or 1-alkenyl or one of the groups (a), (c) and (d) when R**2 signifies amino and the residues denoted as lower contain up to 8 carbon atoms, and of the corresponding optical antipodes thereof, characterized by reacting a reactive derivative of a carboxylic acid of the general formula R**20 -CH2 -COOH wherein R**20 signifies azido, phthalimido or the group ROCO-CH=C(CH3 )-NH- and R signifies lower alkyl, in the presence of a base with a compound or the general formula see diagramm : EP0101598,P14,F3 wherein R**11 signifies lower 2-alkenyl or one of the groups (a) and (d) defined above and R**6 and R**7 have the above significance, or the corresponding optical antipode thereof to give a compound of the general formula see diagramm : EP0101598,P14,F5 wherein R**11 , R**20 , R**6 and R**7 have the above significance, or the corresponding optical antipode thereof and, if desired, converting a lower 2-alkenyl group present as R**11 into the corresponding 1-alkenyl group or converting a group (a) present as R**11 into the group (b) or (c) or converting a group (d) present as R**11 into the vinyl group, whereby previously or subsequently the group R**20 is converted, if desired, into the amino group and, if desired, this is acylated with a readily cleavable acyl group. [EP0101598A1]
IE1931/83A 1982-08-19 1983-08-18 Beta-lactams IE55996B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH496182 1982-08-19
CH364383 1983-07-01

Publications (2)

Publication Number Publication Date
IE831931L IE831931L (en) 1984-02-19
IE55996B1 true IE55996B1 (en) 1991-03-13

Family

ID=25693512

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1931/83A IE55996B1 (en) 1982-08-19 1983-08-18 Beta-lactams

Country Status (10)

Country Link
EP (1) EP0101598B1 (en)
JP (1) JPS5953465A (en)
AU (1) AU564378B2 (en)
CA (1) CA1204746A (en)
DE (1) DE3376319D1 (en)
DK (1) DK378683A (en)
IE (1) IE55996B1 (en)
IL (1) IL69486A (en)
NZ (1) NZ205246A (en)
PH (1) PH22479A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1251454A (en) * 1983-01-20 1989-03-21 Gerard Schmid PROCESS FOR THE MANUFACTURE OF .beta.-LACTAMES
DK36784A (en) * 1983-02-25 1984-08-26 Hoffmann La Roche PROCEDURE FOR PREPARING CHIRAL ALDEHYDES
US4576749A (en) * 1983-10-03 1986-03-18 E. R. Squibb & Sons, Inc. 3-Acylamino-1-carboxymethylaminocarbonyl-2-azetidinones
JPH0649710B2 (en) * 1984-08-06 1994-06-29 藤沢薬品工業株式会社 Azetidinone derivative and method for producing the same
WO1987004429A1 (en) * 1986-01-23 1987-07-30 The Upjohn Company Antimicrobial n-acyl-2-azetidinones
IT1282956B1 (en) * 1996-05-06 1998-04-02 Opos Biochimica Srl PROCEDURE FOR THE PREPARATION OF AN AZETIDINONE

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012383A (en) * 1975-01-02 1977-03-15 Bristol-Myers Company Δ2,3 -1,4-morpholine-2-carboxylic acids and derivatives thereof useful in preparation of antibacteria agents
AU516665B2 (en) * 1975-10-06 1981-06-18 Fujisawa Pharmaceutical Co., Ltd 2-azetidone compounds
JPS56125361A (en) * 1980-03-07 1981-10-01 Sagami Chem Res Center Azetidinone compound
CA1262128A (en) * 1981-08-27 1989-10-03 Christian N. Hubschwerlen .beta.-lactams

Also Published As

Publication number Publication date
EP0101598A1 (en) 1984-02-29
PH22479A (en) 1988-09-12
AU564378B2 (en) 1987-08-13
CA1204746A (en) 1986-05-20
JPH0587515B2 (en) 1993-12-16
IL69486A (en) 1987-07-31
JPS5953465A (en) 1984-03-28
IE831931L (en) 1984-02-19
NZ205246A (en) 1986-12-05
DK378683D0 (en) 1983-08-18
IL69486A0 (en) 1983-11-30
EP0101598B1 (en) 1988-04-20
AU1797983A (en) 1984-02-23
DE3376319D1 (en) 1988-05-26
DK378683A (en) 1984-02-20

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