FR2375240A1 - 1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity - Google Patents

1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity

Info

Publication number
FR2375240A1
FR2375240A1 FR7739065A FR7739065A FR2375240A1 FR 2375240 A1 FR2375240 A1 FR 2375240A1 FR 7739065 A FR7739065 A FR 7739065A FR 7739065 A FR7739065 A FR 7739065A FR 2375240 A1 FR2375240 A1 FR 2375240A1
Authority
FR
France
Prior art keywords
substd
opt
alkyl
thiazolidine
het
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.)
Withdrawn
Application number
FR7739065A
Other languages
French (fr)
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of FR2375240A1 publication Critical patent/FR2375240A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

New beta-lactam antibiotics of formula (I) (including the R-and S-isomers as well as diastereomer mixtures) and their non-toxic pharmaceutically tolerable salts. In (I) A is H, opt. substd. alkyl, aryl or a gp. -X'-R1 in which X' is CO or SO2 and R1 is H, opt. substd. alkyl, aryl, thienyl, furyl, amino, mono- or dialkylamino, pyrrolidyl, piperidyl or (when X' is CO) alkoxy, R is CO) alkoxy, R is H or OCH3, B is phenyl, tolyl, chlorophenyl, hydroxyphenyl, furyl or 1,4-cyclohexadien-1-yl, X is S, O, SO, SO2 or CH2, and Y is a gp. (Ia) or (Ib): in which T is H, alkyl-CO-O-, pyridinium, aminopyridinium, carbamoyloxy, azido, CN, OH, opt. substd. phenylthio, or a gp. -S-Het in which Het is an opt. substd. 5- or 6-membrane heterocyclic ring. The asterisk indicates chiral centre. (I) are useful as antibacterials and as agents for promoting growth and improving feed utilisation in animals. The spectrum of antibacterial activity of (I) is broader than that of known beta-lactam anti-biotics in particular, (I) are active against several gram-negative bacteria. Specific cpds. (I) include 6- Front brace D-alpha- (2-methyl-1, 1-dioxido-1,2,5-thiazolidin-5-yl)carbonylamino phenylacetamido Rear brace penicillanic acid. In an example, this was prepd. in 60% yield by reacting ampicillin trihydrate in aqs. tetrahydrofuran with 2-methyl-5-chlorocarbonyl-1,2,5-thiazolidine 1,1,-dioxide in the presence of NaOH. The product was isolated in the form of its Na salt.
FR7739065A 1976-12-24 1977-12-23 1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity Withdrawn FR2375240A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762658906 DE2658906A1 (en) 1976-12-24 1976-12-24 BETA-LACTAM ANTIBIOTICS, THE METHOD OF MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT

Publications (1)

Publication Number Publication Date
FR2375240A1 true FR2375240A1 (en) 1978-07-21

Family

ID=5996677

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7739065A Withdrawn FR2375240A1 (en) 1976-12-24 1977-12-23 1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity

Country Status (3)

Country Link
JP (1) JPS5379894A (en)
DE (1) DE2658906A1 (en)
FR (1) FR2375240A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY174415A (en) * 2015-10-26 2020-04-17 Jiangsu Kanion Parmaceutical Co Ltd Salt form, crystal form and intermediate of 1,2,5-thiadiazolidine-1,1-dioxide and preparation method thereof
WO2021098840A1 (en) * 2019-11-22 2021-05-27 南京明德新药研发有限公司 SULFONYLUREA RING SUBSTITUTED MONOCYCLIC β-LACTAM ANTIBIOTICS

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE767647A (en) * 1970-05-25 1971-11-25 Bayer Ag
FR2261010A1 (en) * 1974-02-18 1975-09-12 Bayer Ag

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE767647A (en) * 1970-05-25 1971-11-25 Bayer Ag
FR2261010A1 (en) * 1974-02-18 1975-09-12 Bayer Ag

Also Published As

Publication number Publication date
DE2658906A1 (en) 1978-07-06
JPS5379894A (en) 1978-07-14

Similar Documents

Publication Publication Date Title
GB1526978A (en) 3-thiosubstituted cephalosporin antibiotics
US4609652A (en) Methods of using β-lactam antibacterial agents
GB1282743A (en) Antibacterial penicillin derivatives
DE2304226A1 (en) NEW PENICILLIN AND CEPHALOSPORIN COMPOUNDS
KR840004118A (en) Method for preparing cephalosporin derivative
FR2375240A1 (en) 1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity
IE781111L (en) Oxo-nicotinyl penicillin and cephalosporin derivatives.
IE33535B1 (en) New penicillins
US3647781A (en) Imines of nitroheterocyclic aldehydes and compounds of the penicllanic acid or cepham series
GB1164457A (en) Activated Esters of 6-Aminopenicillanic Acid
GB1429539A (en) Derivatives of penam-3-carboxylic acid and cephem-4-carboxylic acid and processes for their manufacture
US3406185A (en) Antibiotics
GB1425827A (en) Penicillins and cephalosporins
US3492297A (en) Guanidino cephalosporins
GB1250611A (en)
US3946003A (en) Hydroxy substituted phenylglycylamido-3-heterocyclic thiomethyl cephalosporins
GB1293590A (en) New penicillanic acid derivatives
US3846417A (en) 1,4-cyclohexadienyl imidazolidinyl cephalosporanic acids and derivatives thereof
AU616453B2 (en) Beta-lactam antibiotics, processes for their preparation and their use as and in medicaments
FR2219775A1 (en) Isoxazolylacetamido penicillanic and cephalosporanic acids - partic. active against Gram-positive bacteria
FR2442240A1 (en) 2-Thiazolyl-2-hydroxy-imino-acetamido cephalosporin derivs. - useful as antibacterials (BE 5.6.79)
IE39373L (en) 3-(substituted-ethyl)-cephalosporin derivatives
GB1261780A (en) Orally active sulfur-containing cephalosporin antibiotics
US3904607A (en) 2,3-lower alkylenepenam-3-carboxylic acid derivatives and processes for the preparation thereof
FR2372630A1 (en) Antibacterial cephalosporin type cpds - eg 7-beta-(substd-acetamido)-3-(3-heterocyclyl prop-1-enyl)-ceph-3-em-4-carboxylic acids

Legal Events

Date Code Title Description
ST Notification of lapse