Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-12-15
1997-06-24
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544142, 544373, 546187, 548433, A61K 31495, C07D48704
Patent
active
056417802
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/00779 Apr. 20, 1995.
TECHNICAL FIELD
The present invention relates to DC-89 derivatives. The compounds of the present invention exhibit excellent anti-tumor activity and are useful as anti-tumor agents.
BACKGROUND ART
As compounds related to DC-89 derivatives of the present invention, DC-89A1, DC-89A2, DC-89B1 and DC-89B2 represented by the following structural formula are known, and these compounds exhibit antibacterial activity against various bacteria and also antitumor activity against melanoma B-16, etc. ##STR3##
DC-89A1 :X.sup.0 =--CH.sub.2 --, Y.sup.0 =Cl
DC-89A2:X.sup.0 =single bond, Y.sup.0 =CH.sub.2 Cl
DC-89B1 :X.sup.0 =--CH.sub.2 --, Y.sup.0 =Br
DC-89B2:X.sup.0 =single bond, Y.sup.0 =CH.sub.2 Br
DC-89A1 is disclosed in WO87/06265, and DC-89A2, DC-89B1 and DC-89B2 are disclosed in JP,A,2-119787. SF2582A and SF2582B, which are the same compounds as DC-89A2 and DC-89A1, are disclosed in JP,A,1-139590. DC-88A and DC113 are disclosed in WO87/06265 and JP,A,2-177890, respectively. These compounds exhibit not only antibacterial activity against various bacteria but also anti-tumor activity against melanoma B-16, etc.
DC-88A derivatives and DC-89 derivatives are disclosed in JP,A,2-288879, JP,A,3-7287, JP,A,3-128379 and JP,A,5-178858.
JP,A,3-128379 discloses Compounds (A) and (C) represented by the following formulae, and JP,A,5-178858 discloses Compounds (B) and (D) represented by the following formulae. ##STR4##
Further, CC-1065 and its derivatives are disclosed in JP,A,54-64695, JP,A,60-193989, WO88/04659, EP-359454 and JP,A,3-14581. Related derivatives are disclosed in JP,A,6-116269.
It is an object of the present invention to provide DC-89 derivatives which exhibit excellent anti-tumor activity.
DISCLOSURE OF THE INVENTION
The present invention provides DC-89 derivatives represented by formula (I) ##STR5## wherein X represents Cl or Br; R represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aralkyl, COR.sup.1 {in which R.sup.1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, OR.sup.2 (in which R.sup.2 represents substituted or unsubstituted lower alkyl or aryl), SR.sup.2 (in which R.sup.2 is the same meaning as defined above), NR.sup.3 R.sup.4 (in which R.sup.3 and R.sup.4 independently represent hydrogen, substituted lower alkyl, amino, or mono- or di(lower alkyl)amino, provided that R.sup.3 and R.sup.4 are not hydrogen at the same time), ##STR6## in which R.sup.5 represents NR.sup.7 (in which R.sup.7 represents hydrogen or substituted or unsubstituted lower alkyl) or oxygen, and R.sup.6 is the same meaning as R.sup.7 defined above or ##STR7## (in which R.sup.6 is the same meaning as defined above)} or SO.sub.2 R.sup.8 (in which R.sup.8 represents substituted or unsubstituted lower alkyl or substituted or unsubstituted aryl); and Y represents ##STR8## and pharmaceutically acceptable salts thereof.
The compounds represented by formula (I) are hereinafter referred to as Compounds (I). Similarly, the compounds represented by formulae (I) to (IX) are referred to as Compounds (I) to (IX). Compounds (I)a, (I)b, etc. are intended to be included in Compounds (I), and Compounds (I)b-1, (I)b-2, etc. are intended to be included in Compounds (I)b.
In the definition of the above-mentioned formula (I), lower alkyl and the alkyl moiety of mono- or di(lower alkyl)amino include linear or branched alkyl groups having 1 to 8 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl, heptyl, octyl and iso-octyl. Examples of aryl include phenyl and naphthyl. Examples of aralkyl include groups having 7 to 20 carbon atoms such as benzyl, phenetyl, styryl, benzhydryl and trityl. Examples of the heterocyclic group include pyridyl, pyrazinyl and pyrimidinyl. The substituted lower alkyl has 1 to 3 independently-selected substituents such as lower alkoxy, alkylthio optionally substit
REFERENCES:
patent: 5070092 (1991-12-01), Kanda et al.
patent: 5258383 (1993-11-01), Nagamura et al.
Amishiro Nobuyoshi
Gomi Katsushige
Kobayashi Eiji
Nagamura Satoru
Okamoto Akihiko
Kyowa Hakko Kogyo Co. Ltd.
Shah Mukund J.
Sripada Pavanaram K.
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