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1. WO2004052904 - NOVEL SEMISYNTHETIC MACROLIDE ANTIBIOTICS OF THE AZALIDE SERIES

Publication Number WO/2004/052904
Publication Date 24.06.2004
International Application No. PCT/HR2003/000062
International Filing Date 10.12.2003
IPC
A61K 31/70 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
70Carbohydrates; Sugars; Derivatives thereof
A61P 31/04 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
04Antibacterial agents
C07H 17/00 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
17Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
CPC
A61K 31/70
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
70Carbohydrates; Sugars; Derivatives thereof
A61P 31/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
A61P 31/04
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
04Antibacterial agents
C07H 17/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
17Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
C07H 17/08
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
17Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
04Heterocyclic radicals containing only oxygen as ring hetero atoms
08Hetero rings containing eight or more ring members, e.g. erythromycins
Applicants
  • PLIVA - ISTRAZIVACKI INSTITUT D.O.O. [HR]/[HR] (AllExceptUS)
  • KUJUNDZIC, Nedjeljko [HR]/[HR] (UsOnly)
  • BUKVIC KRAJACIC, Mirjana [HR]/[HR] (UsOnly)
  • BRAJSA, Karmen [HR]/[HR] (UsOnly)
Inventors
  • KUJUNDZIC, Nedjeljko
  • BUKVIC KRAJACIC, Mirjana
  • BRAJSA, Karmen
Priority Data
P20020991A12.12.2002HR
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) NOVEL SEMISYNTHETIC MACROLIDE ANTIBIOTICS OF THE AZALIDE SERIES
(FR) DERIVES 9A-N-(N'-CARBAMOYL-$G(G)-AMINOPROPYLE), 9A-N-(N'- -THIOCARBAMOYL-$G(G)-AMINOPROPYLE), 9A-N-[N'-(($G(B)-CYANOETHYL)-N'-CARBAMOYL-$G(G)-AMINOPROPYLE] ET 9A-N-[N'-($G(B)-CYANOETHYL)-N'-THIOCARBAMOYL-$G(G)-AMINOPROPYLE] N'-SUBSTITUES DE 9-DEOXO-9-DIHYDRO-9A-AZA-9A-HOMOERYTHROMYCINE A ET 5-O-DESOSAMINYL-9-DEOXO-9- DIHYDR
Abstract
(EN) The invention relates to N'-substituted 9a-N-(N'-carbamoyl-ϝ-aminopropyl), 9a--N-(N'-thiocarbamoyl-ϝ-aminopropyl), 9a-N-[N'-((&bgr;-cyanoethyl)-N'-carbamoyl-ϝ -aminopropyl] and 9a-N-[N'-((&bgr;-cyanoethyl)-N'-thiocarbamoyl-ϝ-aminopropyl] derivatives of 9-deoxo-9-dihydro-9a-aza-9a-homoerithromycin A and 5-0-desosaminyl-9-deoxo-9-dihydro-9a-aza-9a-homoerithronolide A, novel semisynthetic macrolide antibiotics of the azalide series, of the general formula 1, wherein R represents H or cladinosyl moiety, R1 represents H or (&bgr;-cyanoethyl moiety, R2 represents isopropyl, 1-naphtyl, 2-naphtyl, benzyl, 2-(trifluoromethyl)phenyl, 3-phenylpropyl, &bgr;-phenylethyl, ethoxycarbonylmethyl, 1-(1-naphtyl)ethyl, 3,4,5-trimethoxyphenyl and 2,4-dichlorophenyl group, and X represents 0 and S, and their acceptable addition salts thereof with inorganic or organic acids, to the process for preparation of their pharmaceutical compositions as well as the use their compositions in the treatment of bacterial infections.
(FR) L'invention concerne des dérivés 9a-N-(N'-carbamoyl-$g(g)-aminopropyle), 9a-N-(N'- -thiocarbamoyl-$g(g)-aminopropyle), 9a-N-[N'-(($g(b)-cyanoéthyl)-N'-carbamoyl-$g(g)-aminopropyle] et 9a-N-[N'-($g(b)-cyanoéthyl)-N'-thiocarbamoyl-$g(g)-aminopropyle] N'-substitués de 9-déoxo-9-dihydro-9a-aza-9a-homoérythromycine A, qui constituent de nouveaux antibiotiques semi-synthétiques de la série des azalides, de formule générale (1), dans laquelle R représente H ou une fraction cladinosyle, R1 représente H ou une fraction $g(b)-cyanoéthyle, R2 représente un groupe isopropyle, 1-naphtyle, 2-naphtyle, benzyle, 2-(trifluorométhyl)phényle, 3-phénylpropyle, $g(b)-phényléthyle, éthoxycarbonylméthyle, 1-(1-naphtyl)éthyle, 3,4,5-triméthoxyphényle et 2,4-dichlorophényle, et X représente O et S. L'invention concerne également les sels d'addition avec des acides inorganiques ou organiques, pharmaceutiquement acceptables, desdits dérivés. L'invention concerne en outre un procédé de préparation de compositions pharmaceutiques ainsi que l'utilisation de ces dernières pour le traitement d'infections bactériennes.
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