WO2004046153A1 - Esters de promedicament de ceftriaxone - Google Patents

Esters de promedicament de ceftriaxone Download PDF

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Publication number
WO2004046153A1
WO2004046153A1 PCT/IB2003/005327 IB0305327W WO2004046153A1 WO 2004046153 A1 WO2004046153 A1 WO 2004046153A1 IB 0305327 W IB0305327 W IB 0305327W WO 2004046153 A1 WO2004046153 A1 WO 2004046153A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
pharmaceutically acceptable
ethyl
acceptable salt
Prior art date
Application number
PCT/IB2003/005327
Other languages
English (en)
Inventor
Vandana RAINA
Yatendra Kumar
Ram Chander Aryan
Original Assignee
Ranbaxy Laboratories Limited
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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Priority to AU2003302109A priority Critical patent/AU2003302109A1/en
Publication of WO2004046153A1 publication Critical patent/WO2004046153A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • 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

Definitions

  • the field of the invention relates to prodrug esters of ceftriaxone.
  • the invention also relates to processes for preparing prodrug esters of ceftriaxone, pharmaceutical compositions that include the prodrug esters and to methods for using the prodrug esters.
  • cephalosporin antibiotics focusing on the structural modification to circumvent mechanisms of resistance as well as to enhance oral bioavailability and bio-disposition profiles.
  • these goals have been realized with some success by modification of the substi uents at positions 2, 3, 4 and 7 of the cephalosporin rings.
  • Perhaps the most significant modifications have involved incorporation of an aminothiazole ring and an alkoxyimino group at the 7-position.
  • These substituents present in the third generation cephalosporins improve antibacterial spectrum by enhancing affinity for target transpeptidase enzyme and by imparting resistance to mactivation by a variety of beta lactamases.
  • cephalosporins also contain chemically and metabolically stable substituents at the 3-position of the ⁇ -lactam ring, allowing for oral activity.
  • the 4-carboxyl group has been converted to a lipophilic ester prodrug moiety. This modification enhances oral absorption.
  • the present invention provides certain prodrug esters of ceftriaxone and are useful as antimicrobial agents.
  • the prodrug esters have good solubility in water, easily absorbable from digestive tract and are suitable for oral administration.
  • R] is an alkyl, 1-alkanoyloxyalkyl, 1-alkoxycarbonyloxyalkyl, cycloalkyl, cycloalkyloxy or alkoxy having from one to ten carbon atoms.
  • esterified carboxyl group refers to compounds of Formula I, wherein
  • the alkanoyloxy has from two to ten carbon atoms. In particular, the alkanoyloxy has from two to seven carbon atoms and the alkyl moiety has from one to six carbon atoms.
  • Examples include acetoxymethyl, propionyloxymethyl n-butyryloxymethyl, iso- valeryloxymethyl, pivaloxylmethyl, 1-acetoxyethyl, n-valeroxymethyl, 2- methylbutyryloxy- methyl, isovaleroxymethyl, n-hexanoyloxymethyl, 3- methylvaleroxymethyl, neohexanoyloxy-methyl, 2-methylhexanoyloxymethyl, 2,2- dimethylbutyryloxymethyl, 2,2-dimethylpropionyloxy-methyl, diethylacetoxymethyl, dipropylacetoxymethyl, 1-propionyloxyethyl, 1-isobutyryloxyethyl, 1-n-valoryloxyethyl, 1-pivaloxyloxy
  • carboxyl protecting groups include 1-cyclohexyloxycarbonyloxyethyl (cilexetil), 2,2,-dimethylpropionyloxymethyl (pivoxil), and 1- methylethoxycarbonyloxyethyl (proxetil) .
  • the base includes any compound having at least one nitrogen as a heteroatom, including, for example, diisopropylethylamine, diphenylamine, N-tert- butylcyclohexylamine, hexamethyldisilazide, l,5-diazabicyclo[4.3.0]non-5-ene, 1,8- diazabicyclo[5.4.0]undec-7-ene, and mixtures thereof.
  • the reaction is carried out at a temperature ranging from about 40°C to about - 20°C.
  • compositions include dosage forms suitable for oral and parenteral (including subcutaneous, intramuscular, and ophthalmic) administration.
  • the oral dosage forms may include solid dosage forms, like powder, tablets, capsules, as well as liquid suspensions.
  • Parenteral dosage forms may include intravenous infusions, sterile solutions for intramuscular, subcutaneous or intravenous administration, dry powders to be reconstituted with sterile water for parenteral administration, and the like.

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

L'invention concerne des esters de promédicament de ceftriaxone. L'invention concerne également des procédés permettant de préparer des esters de promédicament de ceftriaxone, des compositions pharmaceutiques comprenant lesdits esters de promédicament et des procédés permettant d'utiliser ces esters de promédicaments. On utilise les esters de promédicament de ceftriaxone comme agents antimicrobiens, ces esters étant appropriés pour être administrés oralement.
PCT/IB2003/005327 2002-11-21 2003-11-21 Esters de promedicament de ceftriaxone WO2004046153A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003302109A AU2003302109A1 (en) 2002-11-21 2003-11-21 Prodrug esters of ceftriaxone

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1175/DEL/2002 2002-11-21
IN1175DE2002 2002-11-21

Publications (1)

Publication Number Publication Date
WO2004046153A1 true WO2004046153A1 (fr) 2004-06-03

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2003/005327 WO2004046153A1 (fr) 2002-11-21 2003-11-21 Esters de promedicament de ceftriaxone

Country Status (2)

Country Link
AU (1) AU2003302109A1 (fr)
WO (1) WO2004046153A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013501733A (ja) * 2009-08-10 2013-01-17 ビーエイチアイ リミテッド パートナーシップ １，３−プロパンジスルホン酸を送達するための方法、化合物、および組成物
US9238616B2 (en) 2001-06-11 2016-01-19 Xenoport, Inc. Prodrugs of gaba analogs, compositions and uses thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0188781A1 (fr) * 1984-12-28 1986-07-30 Merck & Co. Inc. Dérivés de 1-oxa-1-déthia-céphalosporine et médicament antibactérien les contenant
EP0791597A1 (fr) * 1996-02-21 1997-08-27 Lupin Laboratories Limited Procédé pour la préparation de céphalosporines et d'intermédiaires
EP0842937A2 (fr) * 1996-11-19 1998-05-20 Hichem Pharma S.p.A. Procédé pour la préparation de cefotaxime et ceftriaxone, des dérivés de la cephalosporine
US20020128469A1 (en) * 1999-04-15 2002-09-12 Benjamin Gerlach Beta-lactam production

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0188781A1 (fr) * 1984-12-28 1986-07-30 Merck & Co. Inc. Dérivés de 1-oxa-1-déthia-céphalosporine et médicament antibactérien les contenant
EP0791597A1 (fr) * 1996-02-21 1997-08-27 Lupin Laboratories Limited Procédé pour la préparation de céphalosporines et d'intermédiaires
EP0842937A2 (fr) * 1996-11-19 1998-05-20 Hichem Pharma S.p.A. Procédé pour la préparation de cefotaxime et ceftriaxone, des dérivés de la cephalosporine
US20020128469A1 (en) * 1999-04-15 2002-09-12 Benjamin Gerlach Beta-lactam production

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
P. ZUCK ET. AL.: "Efficacy and tolerance of cefpodoxime proxetil compared with ceftriaxonen in vulnerable patients with bronchopneumonia", JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, vol. 26, 1990, pages 71 - 7, XP009026667 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9238616B2 (en) 2001-06-11 2016-01-19 Xenoport, Inc. Prodrugs of gaba analogs, compositions and uses thereof
JP2013501733A (ja) * 2009-08-10 2013-01-17 ビーエイチアイ リミテッド パートナーシップ １，３−プロパンジスルホン酸を送達するための方法、化合物、および組成物
JP2016034960A (ja) * 2009-08-10 2016-03-17 ビーエイチアイ リミテッド パートナーシップ １，３−プロパンジスルホン酸を送達するための方法、化合物、および組成物

Also Published As

Publication number Publication date
AU2003302109A1 (en) 2004-06-15

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