FR2335212A2 - Antibacterial azetidinones with a carboxyalk(en)yl side chain - prepd. e.g. by acylation and cyclisation of imines - Google Patents

Antibacterial azetidinones with a carboxyalk(en)yl side chain - prepd. e.g. by acylation and cyclisation of imines

Info

Publication number
FR2335212A2
FR2335212A2 FR7637763A FR7637763A FR2335212A2 FR 2335212 A2 FR2335212 A2 FR 2335212A2 FR 7637763 A FR7637763 A FR 7637763A FR 7637763 A FR7637763 A FR 7637763A FR 2335212 A2 FR2335212 A2 FR 2335212A2
Authority
FR
France
Prior art keywords
substd
opt
haloalkyl
arylthio
heterocyclyl
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.)
Pending
Application number
FR7637763A
Other languages
French (fr)
Inventor
Takashi Kamiya
Yoshihisa Saito
Masashi Hashimoto
Tsutomu Teraji
Takao Takaya
Tadaaki Komori
Osamu Nakagui
Teruo Oku
Youichi Shiokawa
Keiji Hemmi
Hisashi Takasugi
Yoshiharu Nakai
Hidekazu Takeno
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.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical 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
Priority claimed from JP49077091A external-priority patent/JPS51125061A/en
Priority claimed from JP49085526A external-priority patent/JPS51125062A/en
Priority claimed from JP49088452A external-priority patent/JPS51125064A/en
Priority claimed from JP50002650A external-priority patent/JPS5175056A/en
Priority claimed from JP50150909A external-priority patent/JPS5273854A/en
Priority claimed from JP50150910A external-priority patent/JPS5273855A/en
Priority claimed from JP50150912A external-priority patent/JPS5273857A/en
Priority claimed from JP50150911A external-priority patent/JPS5273856A/en
Priority claimed from JP15851175A external-priority patent/JPS5283451A/en
Priority claimed from JP51000190A external-priority patent/JPS6042237B2/en
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of FR2335212A2 publication Critical patent/FR2335212A2/en
Priority to JP15027577A priority Critical patent/JPS5395957A/en
Pending 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
    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Azetidinones of formula (I) are new (R1 is opt. substd. amino, substd. OH, N3 or halo. R3 is H, hydroxymethyl, arylalkoxylminomethyl, aryl, aralkenyl, formyl, carboxy or a nucleophile residue. R3 is CHR4R5 or -CR5=CR6R7. R4 = aryl, aralkyl, arylthioalkyl or heterocyclyl, R5 = COOH or one of its derivs. R6 = alkyl, haloalkyl, heterocyclythioalkyl, or arylthio. R7 = H, haloalkyl or heterocyclylthioalkyl; provided that (A) when R1 = NH2 or acylamino derived from carboxylic or sulphonic acid, and R2 = H, then R3 is CHR4R5, CR5=CR6R7 or CR5=CHR8, with R4 = phenyl substd. by opt. N-substd. alkanesulphonamido or aroylalkoxy, naphthyl, aralkyl, arylthioalkyl or heterocyclyl. R6 = alkyl, haloalkyl or heterocyclyl thioalkyl. R7 = haloalkyl or heterocyclythioalkyl. R8 = arylthio. (B) when R1 is opt. substd. amino or N3, and R2 = aryl, halo or residue of an S-contg. nucleophile, then R6 = alkyl or heterocyclylic thioalkyl; R7 is heterocyclic thioalkyl; R8 is arylthio. Alkane, arene and heterocyclic gps. are opt. substd.). (I) are antibacterials useful for treating Gram positive and negative inections in animal including humans. The usual dose is 1-2g/day. A typical cpd., 0.2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(2-thienyl)acetate, was prepd. from 2-phthalimidoacetyl chloride and 1,3,5-tris D-1-(2-thienyl)-1-methoxycarbonylmethyl perhydro-1,3,5- -triazine.
FR7637763A 1974-07-04 1976-12-15 Antibacterial azetidinones with a carboxyalk(en)yl side chain - prepd. e.g. by acylation and cyclisation of imines Pending FR2335212A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15027577A JPS5395957A (en) 1976-12-13 1977-12-13 Novel azetidinone derivatives

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
JP49077091A JPS51125061A (en) 1974-07-04 1974-07-04 A process for 3-acylaminoazetidinone derivatives
JP49085526A JPS51125062A (en) 1974-07-24 1974-07-24 A process for preparing 3-aminoazetidinone
JP49088452A JPS51125064A (en) 1974-07-31 1974-07-31 A process for preparing 1-substituted-3- acylaminoazetidinone derivati ves
JP50002650A JPS5175056A (en) 1974-12-23 1974-12-23 33 chikanazejinonjudotaino seizoho
JP50150909A JPS5273854A (en) 1975-12-16 1975-12-16 Preparation of 3-iminoaralkylamino substituted acylamino-2-azetidinone derivatives
JP50150910A JPS5273855A (en) 1975-12-16 1975-12-16 Preparation of 1-substituted-3-acylamino-2-azetidinones having acyloxy groups
JP50150912A JPS5273857A (en) 1975-12-16 1975-12-16 Preparation of 1,3-disubstituted-2-azetidinones having acyloxy goup
JP50150911A JPS5273856A (en) 1975-12-16 1975-12-16 Synthesis of 3-acylamino-2-azetidinone derivatives having substituted amino groups
JP15851175A JPS5283451A (en) 1975-12-30 1975-12-30 Preparation of 3-imino-substituted acylamino-2-azetidinone derivative
JP51000190A JPS6042237B2 (en) 1976-01-01 1976-01-01 Azetidinone derivatives
GB2150776 1976-05-25

Publications (1)

Publication Number Publication Date
FR2335212A2 true FR2335212A2 (en) 1977-07-15

Family

ID=27581644

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7637763A Pending FR2335212A2 (en) 1974-07-04 1976-12-15 Antibacterial azetidinones with a carboxyalk(en)yl side chain - prepd. e.g. by acylation and cyclisation of imines

Country Status (2)

Country Link
DE (1) DE2657079A1 (en)
FR (1) FR2335212A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2396751A1 (en) * 1977-07-05 1979-02-02 Farmaceutici Italia NEW PROCESS FOR MANUFACTURING AZETIDINONES OF THE NOCARDINIC FAMILY

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005507A1 (en) * 1978-05-18 1979-11-28 Ciba-Geigy Ag Process for the fragmentation of 3-(2-hydroxyimino-acetylamino)-2-oxo azetidin compounds and compounds obtained thereby

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2396751A1 (en) * 1977-07-05 1979-02-02 Farmaceutici Italia NEW PROCESS FOR MANUFACTURING AZETIDINONES OF THE NOCARDINIC FAMILY

Also Published As

Publication number Publication date
DE2657079A1 (en) 1977-07-07

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