Pyrroloimidazole derivatives and their use as medicaments

Details Pyrroloimidazole derivatives and their use as medicaments Pyrroloimidazole derivatives and their use as medicaments

2002-04-04

2004-03-02

Dentz, Bernard (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S397000, C546S201000, C548S312100

Reexamination Certificate

active

06699883

ABSTRACT:

The present invention relates to new 3-pyrroloimidazole derivatives, to pharmaceutical compositions comprising them, to the preparation and use thereof, especially as tumour- and cancer-lysing and more especially as antibiotic, very especially antibacterial, medicaments.
Cancer and tumour diseases are among civilisation's problematic clinical entities. In many cases, the tumour tissue has to be surgically removed and/or treated by chemotherapy. Long-term patient survival is, however, very uncertain. Moreover, chemotherapy and surgical treatment frequently involve pain and other problems for the cancer patient. The provision of new, complementary medicaments for the treatment of tumour and cancer diseases is, therefore, of great interest. Also, it can be assumed, in the light of the general increase in the formation of resistance in micro-organisms and bacteria, that there exists a need for new and similarly active, or even more active, antibiotics.
The problem of the present invention was accordingly to provide new active ingredients having improved and/or complementary action in the prophylaxis and/or therapy of cancer and tumours and/or especially strong antibiotic, more especially antibacterial, activity in the prophylaxis and/or combating/therapy of infections by micro-organisms.
The problems are solved by provision of 3-pyrroloimidazole derivatives of the general formula (I):
wherein
the imidazole radical is an optionally substituted imidazole ring, which may also be present in salt form,
X, Y, A and B are, each independently of the others, carbon or nitrogen atoms, X, Y, A and B preferably being carbon atoms,
the radicals Z can denote, each independently of the others, a hydrogen atom, a halogen atom, a pseudohalogen, an optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, aralkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, cycloaralkyl, cycloaralkenyl, cycloaralkynyl, aryl or alkoxy radical and/or an optionally substituted ring, to which one or two further, optionally substituted rings may be fused, and/or at least two of the radicals Z may be part of an optionally substituted ring, to which one or two further, optionally substituted rings may be fused. The radicals Z preferably are, each independently of the others, a hydrogen atom, a halogen atom or a pseudohalogen, more preferably a hydrogen atom, fluorine, chlorine, bromine or iodine, most preferably a hydrogen atom.
Preferably, the radicals Z—A═B—Z together have the formula
wherein R
1
is a substituent, preferably a group of formula —G— substituted C
1
-C
6
alkyl, such as —G—C
1
-C
6
alkyl-aryl, especially —G-benzyl; —G-aryl; —G—C
1
-C
6
alkyl; —G-cycloalkyl; —G-heterocycloalkyl; —G—C
1
-C
6
alkyl-heteroaryl, wherein G is CH
2
, O, N or S, preferably O, or R
1
is an aryl, heteroaryl, cycloalkyl, heterocycloalkyl or cycloalkenyl, and wherein the radicals Z bonded to N and Y are, each independently of the other, C
1
-C
6
alkyl radicals, such as methyl radicals, cycloalkyl radicals or H atoms, preferably H atoms.
Throughout the description and the claims, the expression “alkyl” can denote, for example, a C
1-50
alkyl group, preferably a C
1-12
alkyl, especially a C
1-6
alkyl group; for example, an alkyl group may be a methyl, ethyl, propyl, isopropyl or butyl group;
the expression “alk”, for example in the expression “alkoxy”, is defined as for “alkyl”;
“aromatic compounds” or “aryls” or corresponding radicals are, for example, substituted or optionally unsubstituted phenyl, benzyl, naphthyl, biphenyl or anthracene groups or aromatic heterocycles having 5 or 6 ring atoms;
the expression “ar”, for example in the expressions “aralkyl”, “aralkenyl”, “aralkynyl”etc. and “cycloaralkyl”, “cycloaralkenyl”, “cycloaralkynyl” etc., is defined as for “aryl”;
the expression “alkenyl” can denote, for example, a C
2-10
alkenyl group, preferably a C
2-6
alkenyl group, which has the double bond(s) at any desired location and may be unsubstituted or substituted; for example, an ethenyl, propenyl, isopropenyl or butenyl group;
the expression “alkynyl” can denote, for example, a C
2-10
alkynyl group, preferably a C
2-6
alkynyl group, which has the triple bond(s) at any desired location and may be unsubstituted or substituted; for example, an ethynyl, propynyl, isopropynyl or butynyl group;
the expression “cycloalkyl” can denote, for example, an optionally substituted carbocycle having from 3 to 20 C atoms, preferably having from 5 to 15 C atoms and especially having 5 or 6 C atoms, which has no multiple bond in the carbocycle;
the expression “cycloalkenyl” can denote, for example, an optionally substituted carbocycle having from 3 to 20 C atoms, preferably having from 5 to 15 C atoms and especially having 5 or 6 C atoms, which has at least one double bond in the carbocycle;
the expression “cycloalkynyl” can denote, for example, an optionally substituted carbocycle having from 3 to 20 C atoms, preferably having from 5 to 15 C atoms and especially having 9 or 10 C atoms, which has at least one triple bond in the carbocycle;
the expression “alkoxy” can denote, for example, a group of formula —O-alkyl, —O-alkenyl, —O-alkynyl, —O-cycloalkyl, —O-cycloalkenyl, —O-cycloalkynyl or —O-aryl,
the expression “heteroaroyl” can denote, for example, 5-6-membered heterocyclic aromatic heterocycles having 1, 2 or 3 hetero atoms, for example substituted (as defined hereinbelow) pyrrole, furan, thiophene pyrazole, isoxazole, isothiazole, imidazole, oxazole, thiazole 1,2,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,5-oxadiazole, 1,2,5-thiadiazole, tetrazole, pyridine, pyrylium, thiapyrylium, pyridazine, pyrimidine, pyrazine, 1,2,3-triazine, 1,2,4-triazine, 1,3,5-triazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, 1,2,4,5-tetrazine, indole, coumarone, thio-naphthene, carbazole, bibenzofuran, dibenzothiophene, 1H-indazole, indoxazole, benzo[d]isothiazole, anthranile, benzimidazole, benzoxazole, benzothiazole, benzotriazole, quinoline, isoquinoline, benzopyrylium, thiabenzopyrylium, acridine, benzo[g]quinoline, benzo[g]isoquinoline, benzo[c]quinoline, cinnoline, phthalazine, quinazoline, quinoxaline, phenazine, benzo[g]cinnoline, benzo[g]quin-azoline, benzo[g]quinoxaline, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, 1,8-naphthyridine, 2,6-naphthyridine, 2,7-naphthyridine, 1,7-phenanthroline, 1,8-phenanthroline, 1,9-phenanthroline,1,10-phenanthroline, indolizine, 4H-quinolizine, carboline, ergoline, purine, pteridine, alloxazine or flavin;
the expression “substituted” or substituent can be defined as follows: —H, —OH, —R
a
, —O-alkyl, —O-aryl, —O-heteroaroyl, —O-heterocycle, —NH
2
, —NO
2
, —CN, —N
3
, —CNR
a
NR
b
R
c
, —NR
a
R
b
, NR
a
R
b
R
c
+
, fluorine, chlorine, bromine, a-, b-, to w-amino acid esters, —NR
a
COR
b
, —NR
a
COXR
b
(X=—O, —NR, —PO
0,2,3,4
R, —SO
0,1,2,4,
R or —NR
a
NR
b
R
c
), —COR
a
, —COOR
a
, —OCOOR
a
, —CONR
a
R
b
, —OCONR
a
R
b
, —NR
c
CONR
a
R
b
, —R
a
—O—R
b
, —R
c
—NR
a
R
b
, —R
a
—S—R
b
, —R
a
—SO—R
b
, —R
a
—S(O)
2
—R
b
—OR
a
—O—R
b
, —NR
a
R
b
—O—R
c
, —SO
2
R
a
, —SO
1,2,3,4
R
a
—O—R
b
, —COR
a
—OR
b
, —COOR
a
—O—R
b
, —OCOR
a
, —O—R
b
, —OCOOR
a
—O—R
b
, —NR
b
COR
a
—O—R
b
, —CONR
a
R
b
—O—R
c
, —OCONR
a
R
b
—O—R
c
, —NR
c
CONR
a
R
b
—O—R
d
, —NR
a
COR
b
—O—R
c
, —OR
a
—S—R
b
, —NR
a
R
b
—S—R
c
, —SO
1,2,3,4
R
a
—S—R
b
, —COR
a
—S—R
b
, —OCOR
a
—S—R
b
, —OCOR
a
—S—R
b
, —NR
a
COR
b
—S—R
c
, —CONR
a
R
b
—S—R
c
, —NR
a
CONR
b
R
c
—S—R
d
, —OR
a
—NR
b
R
c
, —NR
a
R
b
—NR
c
R
d
, —SO
1,2,3,4
R
b
—NR
b
R
c
, —COR
a
—NR
b
R
c
, —COOR
a
—NR
b
R
c
, —OCOR
a
—NR
b
R
c
, —OCOOR
a
—NR
b
R
c
, —NR
a
CONR
b
R
c
—NR
d
Re, —NR
a
COOR
b
—NR
c
R
d
, —OCONR
a
R
b
—NR
c
R
d
, —NR
a
—CONR
b
R
c
—NHR
d
, —NR
a
COOR
b
—NR
c
—R
d
, —POOR
a
OR
b
, —NR
c
POOR
a
OR
b
, —SO
2
NR
a
R
b
, —SONR
a
NR
b
R
c
, —SNR
a
R
b
NR
c
R
d
, —NR
a
SO
2
R
b
, —NR
a
SONR
b
R
c
, —NR
a
SNR
b
NR
c
R
d
, —NR
a
SO
2
NR
b
Re, —NR
a
SONR
b
NR
c
Rd or —NR
a
SNR
b
NR
c
NR
d
Re, it being possible for the substituents to be, for example, bonded by way of a

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