2,4Dioxo-5-arylidenimino-1,3-pyrimidines

Details 2,4Dioxo-5-arylidenimino-1,3-pyrimidines 2,4Dioxo-5-arylidenimino-1,3-pyrimidines

2001-07-02

2004-05-04

Ford, John M. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

active

06730787

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to medicine, and more specifically to pharmacology, and in particular to synthetic biologically active derivatives of pyrimidine.
The claimed compounds possess pronounced antiviral, immune-stimulating (interferon-inducing), antichiamydial, antituberculous, psychodepressant, analgesic, and hepatoprotective activities.
Compounds are mainly intended for use in medicine practice for treating viral infections, the infections caused by chlamydia, the diseases followed by immune-deficiency, in particular, malignant neoplasms, and also tuberculosis. Besides that, the given compounds can be used in veterinary for the same purposes.
TECHNICAL LEVEL
It is known that microbial and viral diseases are one of the most significant problems of modern medicine. Most of them hardly respond to treatment. It is connected with lack of efficiency of current drugs as well as high rate of variability of microorganisms that leads to origination of resistant forms [1, 2, 8].
Viral diseases often take a course on the background of lowering activity of the immune system, and they are followed by secondary infections; the same is also true for oncologic diseases. Therefore the problem of the development of effective antiviral or antitumoral drugs is closely related with the searching for remedies intended for treating the immune-deficient states of various origination.
Existing antiviral drugs may be conventionally divided into two groups according to types of mechanisms of their action. An action of the drugs of the first group involves suppression of virus reproduction in a body [1]. Antiviral drugs of the second group produce their effect though stimulating the body's immune protection and increase of producing endogenic interferons [2] to a greater extent rather than affecting the viruses in themselves. Interferons and their inducers are also used for treatment of a various tumoral diseases [3].
The given invention falls into the second group.
R-aminouracils of the following general formula:
where R=phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-bromophenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2-chlorophenyl, 2-chlorophenyl, 3-chlorophenyl, 1-naphthyl, 2-naphthyl, cyclohexyl, may be chemical analogs of the claimed compounds. These analogs are described, for example, in [9].
The closest, by its chemical nature, to the claimed compounds is 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-amino]-1,3-dimethyluracil, which was taken by us as the prototype.
6-[[3-[4-(2-methoxyphenyl)- 1-piperazinyl]propyl]-amino]-1,3-dimethyluracil produces an hypotensive action. Its major application is to decrease the arterial pressure under hypertensive crisis. It is described in details in [10].
Unfortunately, range of its biological activity is comparatively narrow.
OBJECTIVE OF THE INVENTION
An objective of the invention is obtaining new chemical compounds possessing a wider range of biological activity, including antiviral activity (with respect to Herpes Simplex virus), immune-stimulating activity (at the expense of induction of producing endogenic interferons in a body), and antimicrobial activity. In other words, the objective of the invention is to provide chemical synthesis of biologically active compounds that outperform the prototype in their biological activity, and also in the range of action.
SUBJECT OF THE INVENTION
The proposed objective is achieved by synthesis of new chemical compounds, that are 2,4-dioxo-5-arylidenimino-1,3-pyrimidines of the general formula (1)
where R is taken from the group of H, OH, alkoxyl, dialkylamino, benzo, dibenzo, or 3,4-dioxolano
A list of all 25 synthesized and identified compounds is presented in Table 1.
TABLE 1
List of the synthesized compounds that are claimed.
Empirical
Number and name of the compound
R
formula
I-
2,4-dioxo-5-benzylidenimino-1,3-pyrimidine
H
C
11
H
9
N
3
O
2
II-
2,4-dioxo-5-(4-chlorobenzylidene) imino-1,3-
4-Cl
C
11
H
8
N
3
O
2
Cl
pyrimidine
III-
2,4-dioxo-5-(3-chlorobenzylidene) imino-1,3-
3-Cl
C
11
H
8
N
3
O
2
Cl
pyrimidine
IV-
2,4-dioxo-5-(2-chlorobenzylidene) imino-1,3-
2-Cl
C
11
H
8
N
3
O
2
Cl
pyrimidine
V-
2,4-dioxo-5-(4-bromobenzylidene) imino-1,3-
4-Br
C
11
H
8
N
3
O
2
Br
pyrimidine
VI-
2,4-dioxo-5-(4-hydroxybenzylidene) imino-
4-OH
C
11
H
9
N
3
O
3
1,3-pyrimidine
VII-
2,4-dioxo-5-(2,4-dihydroxybenzylidene)
2,4-(OH)
2
C
11
H
9
N
3
O
3
imino-1,3-pyrimidine
VIII-
2,4-dioxo-5-(2-hydroxy-5-
2-OH-5-Br
C
11
H
8
N
3
O
3
Br
bromobenzylidene) imino-1,3-pyrimidine
IX-
2,4-dioxo-5-(2-hydroxy-5-
2-OH-5-Cl
C
11
H
8
N
3
O
3
Cl
chlorobenzylidene) imino-1,3-pyrimidine
X-
2,4-dioxo-5-(4-fluorobenzylidene) imino-1,3-
4-F
C
11
H
8
FN
3
O
2
pyrimidine
XI-
2,4-dioxo-5-(2,4-dichlorobenzylidene) imino-
2,4-Cl
2
C
11
H
7
N
3
O
2
Cl
2
1,3-pyrimidine
XII-
2,4-dioxo-5-(2-hydroxy-3,5-
2-OH-3,5-Cl
2
C
11
H
7
N
3
O
3
Cl
2
dichlorobenzylidene) imino-1,3-pyrimidine
XIII-
2,4-dioxo-5-(2-hydroxy-3,5-
2-OH-3,5-Br
2
C
11
H
7
N
3
O
3
Br
2
dibromobenzylidene) imino-1,3-pyrimidine
XIV-
2,4-dioxo-5-(4-methoxybenzylidene) imino-
4-OCH
3
C
12
H
11
N
3
O
3
1,3-pyrimidine
XV-
2,4-dioxo-5-(4-hydroxy-3-
4-OH-3-OCH
3
C
12
H
11
N
3
O
4
methoxybenzylidene) imino-1,3-pyrimidine
XVI-
2,4-dioxo-5-(4-nitrobenzylidene) imino-1,3-
4-NO
2
C
11
H
8
N
4
O
4
pyrimidine
XVII-
2,4-dioxo-5-(3-nitrobenzylidene) imino-
3-NO
2
C
11
H
8
N
4
O
4
1,3-pyrimidine
XVIII-
2,4-dioxo-5-(2-nitrobenzylidene) imino-
2-NO
2
C
11
H
8
N
4
O
4
1,3-pyrimidine
XIX-
2,4-dioxo-5-(2-hydroxy-5-
2-OH-5-NO
2
C
11
H
8
N
4
O
5
nitrobenzylidene) imino-1,3-pyrimidine
XX-
2,4-dioxo-5-(2-hydroxy-5,6-
2-OH-5,6-benzo
C
15
H
11
N
3
O
3
benzobenzylidene) imino-1,3-pyrimidine
XXI-
2,4-dioxo-5-(3,4-dioxolano-benzylidene)
dioxolan-3,4-
C
12
H
9
N
3
O
4
imino-1,3-pyrimidine
diyl
XXII-
2,4-dioxo-5-(2-nitro-5,6-dioxolano-
2-NO
2
-dioxolan-
C
12
H
8
N
4
O
6
benzylidene) imino-1,3-pyrimidine
4,5-diyl
XXIII-
2,4-dioxo-5-(2,3,5,6-dibenzobenzylidene)
2,3,5,6-dibenzo
C
19
H
13
N
3
O
2
imino-1,3-pyrimidine
XXIV-
2,4-dioxo-5-(2-hydroxy-3,5-
2-OH-3,5-I
2
C
11
H
7
I
2
N
3
O
3
diiodobenzylidene) imino-1,3-pyrimidine
XXV-
2,4-dioxo-5-(4-dimethylamino-
4-N(CH
3
)
2
C
13
H
14
N
4
O
2
benzylidene) imino-1,3-pyrimidine
The compounds claimed are new because they are not known from available information sources.
The presence of effective biological activity of wide range that the claimed compounds possess does not obviously stem from preceded level of technique, i.e. the presence of the indicated activities is not obvious for a specialist.


REFERENCES:
Chemical Abstracts vol. 79: 532 55 (1973) Chakraber.*
Chemical Abstracts, vol. 124: 145 723 (1996) Kuzmenko et al.*
Chemical Abstracts, vol. 114:164148 (1991) Hurst et al.*
Chemical Abstracts, vol. 114:74161 (1991) Cherayath et al.*
Chemical Abstracts, vol. 127:293188 (1997) Seitembov.*
Chemical Abstracts, vol. 86:89762 (1977) Yoheda et al.

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