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1. WO2010027280 - NITROBENZINDOLES AND THEIR USE IN CANCER THERAPY

Publication Number WO/2010/027280
Publication Date 11.03.2010
International Application No. PCT/NZ2009/000184
International Filing Date 03.09.2009
IPC
C07D 209/60 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
209Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
56Ring systems containing three or more rings
58- or -condensed
60Naphtho pyrroles; Hydrogenated naphtho pyrroles
A61K 31/496 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
495having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
A61K 31/5377 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
535having six-membered rings with at least one nitrogen and at least one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
53751,4-Oxazines, e.g. morpholine
5377not condensed and containing further heterocyclic rings, e.g. timolol
A61K 35/00 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
35Medicinal preparations containing materials or reaction products thereof with undetermined constitution
CPC
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
C07D 209/60
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
209Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
56Ring systems containing three or more rings
58[b]- or [c]-condensed
60Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
C07F 9/5728
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
9Compounds containing elements of Groups 5 or 15 of the Periodic System
02Phosphorus compounds
547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
553having one nitrogen atom as the only ring hetero atom
572Five-membered rings
5728condensed with carbocyclic rings or carbocyclic ring systems
C07F 9/65583
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
9Compounds containing elements of Groups 5 or 15 of the Periodic System
02Phosphorus compounds
547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
6558containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
65583each of the hetero rings containing nitrogen as ring hetero atom
Applicants
  • AUCKLAND UNISERVICES LIMITED (AllExceptUS)
  • TERCEL, Moana [NZ]/[NZ] (UsOnly)
  • PRUIJN, Frederik, Bastiaan [NL]/[NZ] (UsOnly)
  • STEVENSON, Ralph, James [NZ]/[NZ] (UsOnly)
  • YANG, Shangjin [NZ]/[NZ] (UsOnly)
  • LEE, Ho Huat [NZ]/[NZ] (UsOnly)
  • TENDOUNG, Jean-Jacques Youte [FR]/[NZ] (UsOnly)
Inventors
  • TERCEL, Moana
  • PRUIJN, Frederik, Bastiaan
  • STEVENSON, Ralph, James
  • YANG, Shangjin
  • LEE, Ho Huat
  • TENDOUNG, Jean-Jacques Youte
Agents
  • ADAMS, Matthew, D
Priority Data
57102803.09.2008NZ
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) NITROBENZINDOLES AND THEIR USE IN CANCER THERAPY
(FR) NITROBENZINDOLES ET LEUR UTILISATION EN THÉRAPIE ANTICANCÉREUSE
Abstract
(EN) The invention provides novel nitro-l,2-dihydro-3.H-benzo[e]indole compounds and related analogues that are useful in cancer treatment, pharmaceutical compositions containing such compounds and methods of treating cancer comprising administering the compounds. The compounds of the invention include compounds of the Formula (I), wherein Y is selected from Cl or Br, and wherein X is selected from SO2NR1 2 or CONR12, where X is located at either position 7 or 8, and where each R1 independently represents H or a C1-4alkyl, optionally substituted with one or more hydroxyl groups, and wherein Z is a side chain selected from either structure (Ia) or (Ib), wherein R2 represents a lower C2-4 alkyl bearing a morpholine (Ic) or N-methylpiperazine (Id) substituent, and R3 represents H, C1-4 alkyl, C1-4alkoxy, C1-4alkynyl or C1-4alkynyloxy and pharmaceutically acceptable salts thereof. Also provided are compounds of Formula (II), where the nitro group of Formula (I) is replaced with an amino group, and compounds of Formula (III), where a free hydroxyl group of a compound of Formula (I) or (II) is functionalised with a phosphate, amino acid, short polypeptide chain or monosaccharide, or a free hydroxyl or secondary or tertiary amine group of a compound of Formula (I) or (II) is functionalised with a phosphonooxymethyl substituent.
(FR) L'invention porte sur de nouveaux composés nitro-1,2-dihydro-3H-benzo[e]indoles et sur des analogues associés qui sont utiles dans le traitement du cancer, sur des compositions pharmaceutiques contenant de tels composés et sur des procédés de traitement du cancer comportant l'administration des composés. Les composés de l'invention comprennent les composés représentés par la formule (I), dans laquelle Y est choisi parmi Cl ou Br et dans laquelle X est choisi parmi SO2NR12 ou CONR12, X étant situé soit en position 7, soit en position 8, et chaque R1 représentant indépendamment H ou un alkyle en C1-4, facultativement substitué par un ou plusieurs groupes hydroxyles, et dans laquelle Z est une chaîne latérale choisie parmi la structure soit (Ia) soit (Ib), dans laquelle R2 représente un alkyle inférieur en C2-4 portant un substituant morpholine (Ic) ou N-méthylpipérazine (Id) et R3 représente H, alkyle en C1-4, alcoxy en C1-4, alcynyle en C1-4 ou alcynyloxy en C1-4, et les sels de qualité pharmaceutique de ceux-ci. L'invention porte également sur des composés de la formule (II), dans laquelle le groupe nitro de la formule (I) est remplacé par un groupe amino, et sur des composés de la formule (III), dans laquelle un groupe hydroxyle libre d'un composé de la  formule (I) ou (II) est fonctionnalisé par un phosphate, un acide aminé, une chaîne polypeptidique courte ou un monosaccharide, ou bien un hydroxyle libre ou un groupe amine secondaire ou tertiaire d'un composé de la formule (I) ou (II) est fonctionnalisé par un substituant phosphono-oxyméthyle.
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