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1. WO1992007866 - ANTHRACYCLINE ANALOGUES BEARING LATENT ALKYLATING SUBSTITUENTS

Publication Number WO/1992/007866
Publication Date 14.05.1992
International Application No. PCT/US1991/007687
International Filing Date 16.10.1991
Chapter 2 Demand Filed 23.04.1992
IPC
C07H 15/252 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
15Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
20Carbocyclic rings
24Condensed ring systems having three or more rings
252Naphthacene radicals, e.g. daunomycins, adriamycins
CPC
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
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
C07H 15/252
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
15Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
20Carbocyclic rings
24Condensed ring systems having three or more rings
252Naphthacene radicals, e.g. daunomycins, adriamycins
Applicants
  • BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM [US]/[US]
Inventors
  • FARQUHAR, David
  • CHARIF, Abdallah
Agents
  • HODGINS, Daniel, S.
  • ALLARD, Susan, Joyce
Priority Data
608,14901.11.1990US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) ANTHRACYCLINE ANALOGUES BEARING LATENT ALKYLATING SUBSTITUENTS
(FR) ANALOGUES DE L'ANTHRACYCLINE PORTANT DES SUBSTITUANTS ALKYLANTS LATENTS
Abstract
(EN)
The present invention is a compound having structure (I) where: anthracycline is doxorubicin, daunorubicin or a derivative thereof; N is the 3' nitrogen of daunosamine; Ra is H or alkyl; X is O, S, CRc2 or NRc where Rc is H or alkyl; Rb is alkyl or aryl; n is 1 to 6; and m is 0 to 6. Ra and Rc are preferably H, methyl, ethyl, propyl or butyl, although other alkyl substituents are usable. Rb is alkyl or aryl. The compound of the present invention as described above is activatable $i(in vivo) by esterases and spontaneous dehydration to form an aldehyde. The aldehyde may couple to nucleophiles of intracellular macromolecules. The compounds of the present invention are cytotoxically effective in the inhibition of human myeloma cells.
(FR)
La présente invention concerne un composé présentant la structure (I) dans laquelle l'anthracycline est de la doxorubicine, de la daunorubicine ou un dérivé de ces substances, n représente l'azote 3' de la daunosamine; Ra représente H ou alkyle; X représente O, S, CRc2 ou NRc, Rc représentant ici H ou alkyle; Rb représente alkyle ou aryle; n vaut 1 à 6; et m vaut 0 à 6. Ra et Rc sont de préférence H, méthyle, éthyle, propyle ou butyle, bien que d'autres substituants alkyle puissent être utilisés. Rb représente alkyle ou aryle. Le composé selon la présente invention peut être activé $i(in vivo) par des estérases et une déshydratation spontanée pour former un aldéhyde. L'aldéhyde peut s'accoupler avec des nucléophiles de macromolécules intracellulaires. Les composés selon la présente invention présentent une efficacité cytotoxique dans l'inhibition de cellules de myélome humaines.
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