DC-89 derivatives

Details DC-89 derivatives DC-89 derivatives

1995-11-28

1997-09-23

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Silicon containing doai

514252, 514253, 514410, 514322, 514411, 544315, 544316, 544360, 544364, 544238, 544373, 546 14, 546 19, 548406, 548421, 548433, A61K 3140, A61K 31495, A61K 31405, C07D48704

Patent

active

056704925

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/JP95/00626, filed Mar. 31, 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 DC-89 derivatives, 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.o =Cl
DC-89A2: X.sup.0 =single bond, Y.sup.o =CH.sub.2 Cl
DC-89B1: X.sup.0 =--CH.sub.2 --, Y.sup.o =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. In relation to the compounds of the present invention, DC-88A and DC113 having the following structural formulae 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. ##STR4##
DC-88A derivatives and DC-89 derivatives are disclosed in JP,A,2-288879, JP,A,3-7287, JP,A,3-128379, JP,A,4-226988, JP,A,4-356485, JP,A,5-51384 and JP,A,5-178858 .
Derivatives of SF2582C are disclosed in JP,A,1-278881. CC-1065 and derivatives thereof 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.
JP,A,5-178858 discloses Compounds (A) , (B) and (C) represented by the following formulae. However, Compounds (B) and (C) lack satisfactory water-solubility when these compounds are used as injections. ##STR5##
It is an object of this invention to provide DC-89 derivatives which have excellent anti-tumor activity and excellent water-solubility.


Disclosure of the Invention

The present invention provides DC-89 derivatives represented by formula (I): ##STR6## in which X represents Cl or Br, R represents hydrogen or COR.sup.1 in which R.sup.1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, NR.sup.2 R.sup.3 (in which R.sup.2 and R.sup.3 independently represent hydrogen or substituted or unsubstituted lower alkyl, amino, or mono- or di(lower alkyl)amino), ##STR7## in which R.sup.4 represents oxygen, N--R.sup.5 (in which R.sup.5 represents hydrogen or lower alkyl), CH.sub.2 or ##STR8## (in which R.sup.4 and R.sup.5 are the same meanings as defined above), or OR.sup.6 (in which R.sup.6 represents substituted or unsubstituted lower alkyl, or substituted or unsubstituted aryl); and ##STR9## in which Y.sup.1, Y.sup.2 and Y.sup.3 independently represent CH or N, Q.sup.1 and Q.sup.2 independently represent hydrogen, OR.sup.7 (in which R.sup.7 represents hydrogen or substituted or unsubstituted lower alkyl), NR.sup.2a R.sup.3a (in which R.sup.2a and R.sup.3a are the same meanings as R.sup.2 and R.sup.3 defined above), NHCO.sub.2 R.sup.6a (in which R.sup.6a is the same meaning as R.sup.6 defined above), or O(CH.sub.2).sub.n R.sup.8 in which n represents an integer of 1 to 4, and R.sup.8 represents CO.sub.2 R.sup.7a (in which R.sup.7a is the same meaning as R.sup.7 defined above), N.sub.3, or NR.sup.2b R.sup.3b (in which R.sup.2b and R.sup.3b are the same meanings as R.sup.2 and R.sup.3 defined above), provided that when Q.sup.1 is OCH.sub.3 and Y.sup.1, Y.sup.2 and Y.sup.3 are CH, Q.sup.2 is a group other than hydrogen, or ##STR10## (in which Y.sup.4 represents oxygen, sulfur or NH, and R.sup.7b is the same meaning as R.sup.7 defined above), and pharmaceutically acceptable salts thereof.
The compounds represented by formula (I) are hereinafter referred to as Compounds (I). Similarly, the compounds represented by formula (I) to (IV) are referred to as Compounds (I) to (IV). Compounds (I)a, (I)b and the like are intended to

REFERENCES:
patent: 4912227 (1990-03-01), Kelly et al.
patent: 5070092 (1991-12-01), Kanda et al.
patent: 5258383 (1993-11-01), Nagamura et al.
patent: 5332837 (1994-07-01), Kelly et al.

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