JP2004524349A5

JP2004524349A5 -

Info

Publication number: JP2004524349A5
Application number: JP2002576233A
Authority: JP
Filing date: 2002-03-22
Publication date: 2005-12-22

Claims

The following general formula:
Nitrogen-containing aromatic ring —NR ₃ —partitioning group—NR ′ ₃ —aromatic ring {wherein
・ The nitrogen-containing aromatic ring is
The group N (Ra) (Rb) wherein Ra and Rb are the same or different and are hydrogen or a C1-C4 alkyl group, and one or more bonded to the carbon or nitrogen atom of the quinoline or isoquinoline ring A quinoline or isoquinoline optionally substituted with at least one group selected from a short chain C1-C4 alkoxy or alkyl group, or a quinoline or isoquinoline having a quaternary form of a nitrogen atom, or a benzamidine, or pyridine,
・ Aromatic rings are
The group N (Ra) (Rb) wherein Ra and Rb are the same or different and are hydrogen or a C1-C4 alkyl group, and one or more bonded to the carbon or nitrogen atom of the quinoline or isoquinoline ring A quinoline or isoquinoline optionally substituted with at least one group selected from a short chain C1-C4 alkoxy or alkyl group, or a quinoline or isoquinoline having a quaternary form of a nitrogen atom, or a benzamidine, or a pyridine, or a halogen group A C1-C4 alkoxy group; a cyano group; a carbonylamino group optionally substituted with one or more C1-C4 alkyl groups; a guanyl group; a C1-C4 alkylthio group; an amino group, a C1-C4 alkylamino group; Each alkyl group is a C1-C4 dialkylamino group (al Le moieties together may form a C3~C8 ring), a nitro group; a phenyl ring optionally substituted with C2~C4 alkenylene amino group; C1 -C4 alkylene amino group;
Monocyclic or bicyclic or tricyclic heterocycle having 0 to 2 heteroatoms per ring, provided that at least one heteroatom is one or more C1-C4 alkyl groups, or Present in at least one ring optionally substituted with a C1-C4 alkylene or C2-C4 alkenylene group)
And
R ₃ and R ′ ₃ are the same or different and, independently of one another, hydrogen or C1-C
4 alkyl groups,
・ Distributing group is
An aromatic ring as defined above, or a group XR1 (R2), wherein X is a nitrogen atom N forming NR1R2, a linear or branched C1-C6 alkyl group forming alkR1R2, O
A triazine group optionally substituted with an oxygen atom O forming R 1 or a sulfur atom S forming SR 1;
Wherein R1 and R2 are the same or different and are hydrogen atoms; C1-C8 alkyl groups optionally substituted with one or more identical or different groups; optionally substituted as defined above Quinuclidine group; itself a pyrrolidinyl group optionally substituted with an alkyl or phenylalkyl group (alkyl is C1-C4); itself optionally substituted with an alkyl, cycloalkyl or phenylalkyl group A modified piperazinyl or homopiperazinyl group; a morpholinyl group; a pyridyl or piperidinyl group or piperidyl group optionally substituted with one or more alkyl or phenylalkyl groups (alkyl is C1-C4); an indazolyl group; a naphthyl group; A benzotriazole group; A azoimidazolyl group; a pyrimidinyl group optionally substituted with one or more alkyls (alkyl is C1-C4); an acenaphthene group; itself selected from alkyl, phenylalkyl, alkylaminoalkyl and dialkylaminoalkyl Selected from one or two identical or different amino groups optionally substituted with different groups;
When XR1R2 is NR1R2, when R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is hydrogen and the other is unsubstituted C1-C4 alkyl not,
Alternatively, when X is N or alkyl, R1 and R2 together with X to which they are attached are one or two identical selected from N, O or S, or Forming a saturated or unsaturated 3-6 membered monocyclic group or 8-10 membered bicyclic group optionally having different heteroatoms, which group is optionally substituted;
-Is a diazine group optionally substituted with the same groups as triazine}
A compound which binds the G-quadruplex structure of DNA or RNA, or one of its salts (these compounds are all possible isomeric forms, racemates, enantiomers and diastereoisomers) Is also present).

A compound which binds the G-quadruplex structure of telomeres, which corresponds to the general formula according to claim 1.

When one or both of R1 and R2 are C1-C8 alkyl groups optionally substituted with one or more groups that are the same or different, these groups are the following groups: Optionally in one or two identical or different groups selected from hydroxyalkyl, alkoxyalkyl, alkylphenylalkyl, phenylalkyl, carboxyalkyl, hydroxycarboxyalkyl, acyl, naphthyl, phenyl and alkylphenyl groups Substituted amino group; trialkylammonium group; hydroxyl group; C1-C4 alkoxy group; thioalkoxy group; trifluoromethyl group; acyl group; free, salt-forming, esterified or amidated carboxyl group; ; C1-C4 alkyl in place Pyrrolidinyl group substituted by: piperidyl and piperazinyl group optionally substituted with alkyl or phenylalkyl (alkyl is C1-C4); morpholinyl group; pyridyl group; itself a C1-C4 alkoxy group, halogen, or the above 1 selected from optionally substituted amino groups as defined in
3. A compound according to claim 1 or 2, characterized in that it is selected from naphthyl or phenyl groups optionally substituted with one or more groups.

The partitioning group is:
-An aromatic ring as defined above or a group XR1 (R2) [X is a nitrogen atom N forming NR1R2, a linear or branched C1-C6 alkyl group forming alkR1R2, OR1 forming An oxygen atom O, or a sulfur atom S that forms SR1] optionally substituted triazine group,
In which R1 and R2 are the same or different and are hydrogen atoms; groups amino, alkylamino, dialkylamino, alkoxyalkylamino, dialkoxyalkylamino, hydroxyalkylamino, dihydroxyalkylamino, hydroxycarboxyalkylamino, trialkyl Ammonium, naphthylamino, phenylamino, acylamino, (alkyl) (phenylalkyl) amino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, hydroxyl, C1-C4 alkoxy, C1-C4 thioalkoxy, tri Fluoromethyl, acyl, free, salt-forming, esterified or amidated carboxyl, imidazolyl, C1-C4 alkyl optionally substituted pyrrolidinyl, piperidyl, al One selected from piperazinyl and homopiperazinyl, morpholinyl, pyridyl, or a group C1-C4 alkoxy, halogen, amino, alkylamino and dialkylamino, optionally substituted with thio or phenylalkyl (alkyl is C1-C4) A C1-C8 alkyl optionally substituted with one or more groups, selected from naphthyl or phenyl optionally substituted with further groups; an aromatic ring as defined above; a quinuclidine group; A pyrrolidinyl group optionally substituted with an alkyl or phenylalkyl group (alkyl is C1-C4); a piperazinyl group optionally substituted itself with an alkyl, cycloalkyl or phenylalkyl group; a morpholinyl group; one or more A pyridyl or piperidyl group optionally substituted with an alkyl or phenylalkyl group above (wherein alkyl is C1-C4); an indazolyl group; a naphthyl group, a benzotriazole group; one or more alkyls (alkyl is C1 -C4) optionally substituted pyrimidinyl group; selected from acenaphthene group;
Here, when XR1R2 is NR1R2, when R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is hydrogen and the other is unsubstituted C1 Not ~ C4 alkyl,
Alternatively, when X is N or alkyl, R1 and R2 together with the X to which they are attached are optionally substituted with the following groups: one or more identical or different groups Substituted piperazinyl or homopiperazinyl; C1-C4 alkyl or alkoxy, hydroxyl, acylamino, pyrrolidinylalkyl, pyridinyl and pyridinyl optionally substituted with pyrrolidinyl; 1,2,3,4-tetrahydroquinolinyl and 1,2 1,3,4-tetrahydroisoquinolinyl; diazepine optionally substituted with alkyl or pyrrolidinylalkyl; 1 selected from alkyl, alkoxy, alkoxyalkyl, pyrrolylalkyl, piperidinyl, piperidyl, hydroxyl and cycloalkylalkyl Pieces or it Optionally piperidyl substituted or piperidinyl above groups; morpholinyl; thiomorpholinyl; form a group selected from imidazolinyl optionally substituted with alkyl, or
A diazine group optionally substituted with the same groups as triazine,
3. A compound according to claim 1 or 2, or one of its salts, characterized in that these compounds are also present in all possible isomeric forms, racemates, enantiomers and diastereomers.

The compound according to claim 1, wherein the diazine group is pyrimidine and quinazoline.

When X of XR1 (R2) is N, either one of R1 and R2 is a hydrogen atom or a C1-C4 alkyl group optionally substituted with amino, alkylamino, dialkylamino or phenyl, and R1 And the other of R2 is selected from those defined for R1 and R2 in any one of claims 1-5, or R1 and R2, together with the nitrogen atom to which they are attached, Cyclic groups selected from groups: alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, phenylalkyl, alkoxyalkyl, hydroxyalkyl, dihydroxyalkyl, hydroxyalkoxyalkyl (with alkoxy), imidazolylaminoalkyl, imidazolylalkylamino Alkyl, imida Rylhydroxyalkylaminoalkyl, pyridylalkyl, pyridinylalkyl, imidazopyridinylalkyl, pyrrolidinylalkyl, imidazolylalkyl, morpholinylalkyl, alkyl optionally substituted with one or more alkyl or phenyl groups Or one or more groups selected from benzoimidazole alkyl, C3-C8 cycloalkyl, pyrazinyl, pyrimidinyl, pyridyl, piperidyl, furylcarbonyl, furfurylcarbonyl, quinolyl or isoquinolyl optionally substituted with hydroxyalkyl Optionally substituted piperazinyl or homopiperazinyl groups; C1-C4 alkyl or alkoxy, hydroxyl, acylamino, pyrrolidinylalkyl, pyridinyl and Pyrrolidinyl group optionally substituted with lysyl; 1,2,3,4-tetrahydroquinolinyl group or 1,2,3,4-tetrahydroisoquinolinyl group; optionally substituted with alkyl or pyrrolidinylalkyl A diazepine group; a piperidyl group optionally substituted with one or more groups selected from alkyl, alkoxy, alkoxyalkyl, pyrrolylalkyl, piperidinyl, hydroxyl, cycloalkylalkyl and piperidyl groups; optionally substituted with piperidinyl 6. A compound according to any one of claims 1 to 5, characterized in that it forms an imidazolinyl group optionally substituted with alkyl; a piperidinyl group; a morpholinyl or thiomorpholinyl group;

The following general formula:
Nitrogen-containing aromatic ring —NR ₃ —partition group —NR ′ ₃ —aromatic ring {wherein the nitrogen-containing aromatic ring, aromatic ring, and R ₃ and R ′ ₃ are any one of claims 1 to 6 Has the meaning indicated in the section,
And the partitioning group
The group XR1 (R2) [X forms a nitrogen atom N forming NR1R2, a linear or branched C1-C6 alkyl group forming alkR1R2, an oxygen atom O forming OR1, or SR1 Optionally substituted triazine group (wherein R1 and R2 are the same or different and have the meanings given in any one of claims 1-6).
-Is a diazine group optionally substituted with the same groups as triazine}
3. A compound according to claim 1 or 2 or a salt thereof (these compounds also exist in all possible isomeric forms, racemates, enantiomers and diastereomers, characterized in that ).

The partition group is
A triazine optionally substituted with a group XR1 (R2), wherein X is a nitrogen atom N for forming NR1R2, an oxygen atom O for forming OR1, or a sulfur atom S for forming SR1 Group,
Wherein R1 and R2 are the same or different and are a hydrogen atom; group amino, alkylamino, dialkylamino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, C1-C4 alkoxy, acyl group A C1-C8 alkyl optionally substituted with an imidazolyl group, a pyrrolidinyl group, a pyridyl or phenyl group; an aromatic ring as defined in claim 1; a quinuclidine group, a pyrrolidinyl group optionally substituted with a C1-C4 alkyl, or Selected from piperidyl groups;
When R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is not hydrogen and the other is not unsubstituted C1-C4 alkyl,
Or in addition, when X is N, R1 and R2 together with X to which they are attached are piperazinyl, homopiperazinyl, piperidyl, pyrrolidinyl, optionally substituted with one or more groups, Form a morpholinyl or thiomorpholinyl group, or
A diazine group optionally substituted with the same groups as triazine,
3. A compound according to claim 1 or 2, or one of its salts, characterized in that these compounds are also present in all possible isomeric forms, racemates, enantiomers and diastereomers .

Formula (I) below:

{Where,
A is a group XR1 (R2), where X is the group:
NR1R2 [R1 and R2 are the same or different and a hydrogen atom; a C1-C8 alkyl group optionally substituted with one or more identical or different groups; an aromatic as defined in claim 1 A quinuclidine group; a pyrrolidinyl group optionally substituted with alkyl or phenylalkyl itself (alkyl is C1-C4); a piperazinyl or homopiperazinyl itself optionally substituted with an alkyl, cycloalkyl or phenylalkyl group A morpholinyl group; a pyridyl or piperidinyl group or piperidyl group optionally substituted with one or more alkyl or phenylalkyl groups (alkyl is C1-C4); an indazolyl group; a naphthyl group; a benzotriazole group; Imidazo A pyrimidinyl group optionally substituted with one or more alkyl (alkyl is C1-C4); an acenaphthene group; itself selected from alkyl, phenylalkyl, alkylaminoalkyl and dialkylaminoalkyl Selected from one or two identical or different amino groups optionally substituted with different groups],
Here, when XR1R2 is NR1R2, when R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is hydrogen and the other is unsubstituted C1 Not ~ C4 alkyl,
Alternatively, when X is N or alkyl, R1 and R2 together with X to which they are attached are one or two identical selected from N, O or S, or Forming a saturated or unsaturated 3-6 membered monocyclic group or 8-10 membered bicyclic group optionally having different heteroatoms;
A group OR1 or SR1 (R1 has the same meaning as above, but R1 is not hydrogen or unsubstituted C1-C4 alkyl) or 1-6 carbon atoms substituted by R1, R2 as defined above An alkyl group having
A nitrogen, oxygen or sulfur atom, or a C1-C6 alkyl group to form one of
R ₃ and R ′ ₃ are the same or different and, independently of one another, hydrogen or C1-C
4 alkyl groups,
-Ar ₁ and Ar ₂ are the same or different;
* When Ar ₁ and Ar ₂ are the same,
The radicals N (Ra) (Rb) [wherein Ra and Rb are identical or different, hydrogen or C
Optionally substituted with at least one group selected from one or more short-chain C1-C4 alkoxy or alkyl groups attached to the carbon or nitrogen atom of the quinoline or isoquinoline ring. An quinoline or isoquinoline motif, or a quinoline or isoquinoline having a quaternary form of a nitrogen atom, or Pyridine fused with a heteroaryl group,
* When Ar ₁ and Ar ₂ are different,
Ar ₁ and Ar ₂ are both one of the possibilities described above for Ar ₁ and Ar ₂ , or Ar ₁ is _one of the above possibilities, and Ar ₂ is
* Halogen group, C1-C4 alkoxy group, cyano group, carbonylamino group, guanyl group, C1-C4 alkylthio group, amino group, C1-C4 alkyl optionally substituted with one or more C1-C4 alkyl groups An amino group, a phenyl ring optionally substituted with a C1-C4 dialkylamino group, a nitro group, a C1-C4 alkyleneamino group, or (or) a C2-C4 alkenyleneamino group, or a C1-C4 alkyl group. An optionally substituted piperazinyl group,
* Monocyclic or bicyclic or tricyclic heterocycle having 0 to 2 heteroatoms per ring, provided that at least one heteroatom is one or more C1-C4 alkyl groups, Or present in at least one ring optionally substituted with a C1-C4 alkylene or C2-C4 alkenylene group)
Is}
Or a salt thereof (these compounds of the formula (I) are all possible isomeric forms, racemates, enantiomers and diastereomers), characterized in that Even stereomers).

When one or both of R1 and R2 are C1-C8 alkyl groups optionally substituted with one or more groups that are the same or different, these groups are themselves alkyl, hydroxyalkyl An amino group optionally substituted with one or two identical or different groups selected from alkoxyalkyl, phenylalkyl, carboxyalkyl, hydroxycarboxyalkyl, acyl, naphthyl, phenyl and alkylphenyl groups; Hydroxyl group; alkoxy group; thioalkoxy group; trifluoromethyl group; acyl group; free, salt-forming, esterified or amidated carboxyl group; imidazolyl group; optionally substituted with C1-C4 alkyl Pyrrolidinyl group; alkyl or Piperidyl and piperazinyl groups optionally substituted with phenylalkyl (alkyl is C1-C4); morpholinyl groups; pyridyl groups; themselves are C1-C4 alkoxy groups, halogen, or optionally substituted as defined above 10. A compound according to claim 9, characterized in that it is selected from naphthyl or phenyl groups optionally substituted with one or more groups selected from amino groups.

When X of XR1 (R2) is N, one of R1 and R2 is a hydrogen atom, and the other of R1 and R2 is defined for R1 and R2 in any one of claims 1-10. R1 and R2 together with the nitrogen atom to which they are attached are piperazinyl, homopiperazinyl, pyrrolidinyl, piperidyl, pyridinyl, morpholinyl, thiomorpholinyl, imidazolinyl, diazepine, 1,2 Forming a 1,2,4-tetrahydroquinoline or 1,2,3,4-tetrahydroisoquinoline group, all these groups being one or more groups as defined in any one of claims 1-10. 11. A compound according to any one of claims 1 to 10, characterized in that it is substituted by

A is an aromatic ring as defined in claim 1 or a group XR1 (R2), wherein X is a nitrogen atom N forming NR1R2, a linear or branched C1-C6 alkyl group forming alkR1R2, An oxygen atom O that forms OR1, or a sulfur atom S that forms SR1].
In which R1 and R2 are the same or different and are hydrogen atoms; groups amino, alkylamino, dialkylamino, dialkoxyalkylamino, dihydroxyalkylamino, alkoxyalkylamino, hydroxyalkylamino, hydroxycarboxyalkylamino, trialkyl Ammonium, naphthylamino, phenylamino, acylamino, (alkyl) (phenylalkyl) amino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, hydroxyl, C1-C4 alkoxy, C1-C4 thioalkoxy, tri Fluoromethyl, acyl, free, salt-forming, esterified or amidated carboxyl, imidazolyl, pyrrolidinyl optionally substituted with C1-C4 alkyl, alkyl or One or more selected from piperidyl and piperazinyl, morpholinyl, pyridyl, or a group C1-C4 alkoxy optionally substituted with an phenylalkyl (alkyl is C1-C4), halogen, amino, alkylamino and dialkylamino A C1-C8 alkyl optionally substituted with one or more groups selected from naphthyl or phenyl optionally substituted with a group of: an aromatic ring as defined above; a quinuclidine group; A pyrrolidinyl group optionally substituted with phenylalkyl (alkyl is C1-C4); a piperazinyl group optionally substituted itself with an alkyl, cycloalkyl or phenylalkyl group; a morpholinyl group; one or more alkyls Mock A pyridyl or piperidyl group optionally substituted with a phenylalkyl group (alkyl is C1-C4); an indazolyl group; a naphthyl group, a benzotriazole group; one or more alkyls (alkyl is C1-C4) A pyrimidinyl group optionally substituted with: an acenaphthene group;
Here, when XR1R2 is NR1R2, when R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is hydrogen and the other is unsubstituted C1 Not ~ C4 alkyl,
Alternatively, when X is N or alkyl, R1 and R2 together with the X to which they are attached are optionally substituted with the following groups: one or more identical or different groups Substituted piperazinyl or homopiperazinyl; pyrrolidinyl optionally substituted with C1-C4 alkyl or alkoxy, hydroxyl, acylamino, pyrrolidinylalkyl, pyridinyl or pyridyl; 1,2,3,4-tetrahydroquinolinyl and 1,2 1,3,4-tetrahydroisoquinolinyl; diazepine optionally substituted with alkyl or pyrrolidinylalkyl; 1 selected from alkyl, alkoxy, alkoxyalkyl, pyrrolylalkyl, piperidinyl, piperidyl, hydroxyl and cycloalkylalkyl Pieces or it Is piperidyl or piperidinyl optionally substituted with the above groups; morpholinyl; thiomorpholinyl; alkyl and forming a group selected from imidazolinyl, optionally substituted with A compound according to claim 9.

When X of XR1 (R2) is N, one of R1 and R2 is a hydrogen atom or a C1-C4 alkyl group optionally substituted with an amino, alkylamino, dialkylamino or phenyl group, and The other of R1 and R2 is selected from those defined for R1 and R2 in any one of claims 1-8, or R1 and R2 together with the nitrogen atom to which they are attached. Alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, phenylalkyl, alkoxyalkyl, hydroxyalkyl, dihydroxyalkyl, hydroxyalkoxyalkyl (alkoxy is C1-C6), imidazolylaminoalkyl, imidazolylalkylaminoalkyl, imidazolyl Droxyalkylaminoalkyl, pyridylalkyl, pyridinylalkyl, imidazopyridinylalkyl, pyrrolidinylalkyl, imidazolylalkyl, morpholinylalkyl, alkyl optionally substituted with one or more alkyl or phenyl groups Or one or more groups selected from benzoimidazole alkyl, C3-C8 cycloalkyl, pyrazinyl, pyrimidinyl, pyridyl, piperidyl, furylcarbonyl, furfurylcarbonyl, quinolyl or isoquinolyl optionally substituted with hydroxyalkyl Optionally substituted piperazinyl or homopiperazinyl groups; C1-C4 alkyl or alkoxy, hydroxyl, acylamino, pyrrolidinylalkyl, pyridinyl and pyridyl Pyrrolidinyl group optionally substituted with 1, 2,3,4-tetrahydroquinolinyl group or 1,2,3,4-tetrahydroisoquinolinyl group; optionally substituted with alkyl or pyrrolidinylalkyl Diazepine group; piperidyl group optionally substituted with one or more groups selected from alkyl, alkoxy, alkoxyalkyl, pyrrolylalkyl, piperidinyl, hydroxyl, cycloalkylalkyl and piperidyl groups; optionally substituted with piperidinyl 10. A compound according to claim 9, characterized in that it forms a piperidinyl group; a morpholinyl or thiomorpholinyl group; an imidazolinyl group optionally substituted with alkyl.

Formula (I) below:

{Where,
A is a group XR1 (R2), where X is the following group:
NR1R2 [R1 and R2 are the same or different, hydrogen atom; group amino, alkylamino, dialkylamino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, C1-C4 alkoxy, C1- C1-C8 alkyl optionally substituted with C4 thioalkoxy, trifluoromethyl, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, pyridyl or phenyl; an aromatic ring as defined in claim 1; a quinuclidine group, a group pyrrolidinyl, piperazinyl, morpholinyl, Selected from pyridyl, or piperidyl groups optionally substituted with C1-C4 alkyl],
Where R1 and R2 are both not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is not hydrogen and the other is not unsubstituted C1-C4 alkyl,
Alternatively, when X is N or alkyl, R1 and R2 together with X to which they are attached are one or two identical selected from N, O or S, or Forming a saturated or unsaturated 3-6 membered monocyclic group or 8-10 membered bicyclic group optionally having different heteroatoms;
A group OR1 or SR1 (R1 has the same meaning as above, but R1 is not hydrogen or unsubstituted C1-C4 alkyl), or 1-6 carbons substituted by R1, R2 as defined above A nitrogen, oxygen or sulfur atom or a C1-C6 alkyl group to form one of the alkyl groups having an atom;
R ₃ and R ′ ₃ are the same or different and, independently of one another, hydrogen or C1-C
4 alkyl groups,
-Ar ₁ and Ar ₂ are the same or different;
* When Ar ₁ and Ar ₂ are the same:
At least one group N (Ra) (Rb) [Ra and Rb are the same or different and are hydrogen or a C1-C4 alkyl group], or (or) a short chain having 1 to 4 carbon atoms A quinoline motif optionally substituted with an alkoxy or alkyl group, or a quinoline having a quaternary form of a nitrogen atom, or a benzamidine, or attached at the 4-position, or optionally substituted with a C1-C4 alkyl group Pyridine fused with an aryl or heteroaryl group formed,
* When Ar ₁ and Ar ₂ are different:
Ar ₁ and Ar ₂ are both one of the possibilities described above for Ar ₁ and Ar ₂ , or Ar ₁ is _one of the above possibilities, and Ar ₂ is
* Halogen group, C1-C4 alkoxy group, cyano group, carbonylamino group, guanyl group, C1-C4 alkylthio group, amino group, C1-C4 alkyl optionally substituted with one or more C1-C4 alkyl groups An amino group, a phenyl ring optionally substituted with a C1-C4 dialkylamino group, a nitro group, a C1-C4 alkyleneamino group, (or) a C2-C4 alkenyleneamino group, or a C1-C4 alkyl group An optionally substituted piperazinyl group,
* A monocyclic or bicyclic or tricyclic heterocycle having 0 to 2 heteroatoms per ring, provided that at least one heteroatom is one or more C1-C4 alkyl groups, Or present in at least one ring optionally substituted with a C1-C4 alkylene or C2-C4 alkenylene group)
Is}
10. The compound according to claim 9, or one of its salts (these compounds of formula (I) are characterized by the fact that all the possible isomeric forms, racemates, enantiomers and diastereomers But it exists).

Formula (I) below:

{Where,
A is a group XR1 (R2), where X is the following group:
NR1R2 [R1 and R2 are the same or different, hydrogen atom; group amino, alkylamino, dialkylamino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, C1-C4 alkoxy, C1- C1-C8 alkyl optionally substituted with C4 thioalkoxy, trifluoromethyl, pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, pyridyl or phenyl; an aromatic ring as defined in claim 1; a quinuclidine group, a group pyrrolidinyl, piperazinyl, morpholinyl, Selected from pyridyl, or piperidyl groups optionally substituted with C1-C4 alkyl],
Where R1 and R2 are the same, both are not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is not hydrogen and the other is not unsubstituted C1-C4 alkyl,
Alternatively, when X is N or alkyl, R1 and R2 together with X to which they are attached are one or two identical selected from N, O or S, or Forming a saturated or unsaturated 3-6 membered monocyclic group or 8-10 membered bicyclic group optionally having different heteroatoms;
A group OR1 or SR1 (R1 has the same meaning as above, but R1 is not hydrogen or unsubstituted C1-C4 alkyl), or 1-6 carbons substituted by R1, R2 as defined above An alkyl group having an atom,
A nitrogen, oxygen or sulfur atom or a C1-C6 alkyl group to form one of
R ₃ and R ′ ₃ are the same or different and, independently of one another, hydrogen or C1-C
4 alkyl groups,
-Ar ₁ and Ar ₂ are the same or different;
* When Ar ₁ and Ar ₂ are the same:
At least one group N (Ra) (Rb) [Ra and Rb are the same or different and are hydrogen or a C1-C4 alkyl group], or (or) a short chain having 1 to 4 carbon atoms A quinoline motif optionally substituted with an alkoxy or alkyl group, or a quinoline having a quaternary form of a nitrogen atom, or a benzamidine, or attached at the 4-position, or optionally substituted with a C1-C4 alkyl group Pyridine fused with an aryl or heteroaryl group formed,
* When Ar ₁ and Ar ₂ are different:
Ar ₁ and Ar ₂ are both one of the possibilities described above for Ar ₁ and Ar ₂ , or Ar ₁ is _one of the above possibilities, and Ar ₂ is
* Halogen group, C1-C4 alkoxy group, cyano group, carbonylamino group, guanyl group, C1-C4 alkylthio group, amino group, C1-C4 alkyl optionally substituted with one or more C1-C4 alkyl groups An amino group, a phenyl ring optionally substituted with a C1-C4 dialkylamino group, a nitro group, a C1-C4 alkyleneamino group, (or) a C2-C4 alkenyleneamino group, or a C1-C4 alkyl group An optionally substituted piperazinyl group,
* A monocyclic or bicyclic or tricyclic heterocycle having 0 to 2 heteroatoms per ring, provided that at least one heteroatom is one or more C1-C4 alkyl groups, Or present in at least one ring optionally substituted with a C1-C4 alkylene or C2-C4 alkenylene group)
Is}
10. The compound according to claim 9, or one of its salts (these compounds of formula (I) are characterized by the fact that all the possible isomeric forms, racemates, enantiomers and diastereomers But it exists).

A is a group XR1 (R2), where X is:
NR1R2 wherein R1 and R2 are the same or different and are hydrogen atoms; groups amino, alkylamino, dialkylamino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, C1-C4 alkoxy A C1-C8 alkyl optionally substituted with the groups imidazolyl, pyrrolidinyl, pyridyl, or with a phenyl group; an aromatic ring as defined in claim 1; optionally substituted with a quinuclidine group, a pyrrolidinyl group or a C1-C4 alkyl Selected from piperidyl groups;
Where R1 and R2 are both not hydrogen or unsubstituted C1-C4 alkyl, and when R1 and R2 are different, one is not hydrogen and the other is not unsubstituted C1-C4 alkyl,
Alternatively, when X is N, R1 and R2 together with the X to which they are attached form a piperazinyl, piperidyl, pyrrolidinyl, morpholinyl or thiomorpholinyl group], or a group OR1 or SR1 (R1 has the same meaning as above, but R1 is not hydrogen or unsubstituted C1-C4 alkyl)
A nitrogen atom N for forming NR1R2 as defined above, an oxygen atom O for forming OR1, or a sulfur atom S for forming SR1, respectively. Or a salt thereof (these compounds also exist in all possible isomeric forms, racemates, enantiomers and diastereomers).

When A is NR1R2, one of R1 and R2 is a hydrogen atom, and the other of R1 and R2 is selected from those defined for R1 and R2, or the nitrogen atom to which they are attached 16. A compound according to any one of claims 9-15, characterized in that together with it forms a piperazinyl, pyrrolidinyl, piperidyl or morpholinyl group optionally substituted with alkyl or piperidyl.

Ar ₁ and Ar ₂ are the following groups: 4-amino- or 4-methylamino- or 4-dimethylaminoquinolyl, -isoquinolyl, -quinolinium or -isoquinolinium (quinolyl, isoquinolyl, quinolinium or isoquinolinium ring Or a group selected from phenyl optionally substituted with one or more methyl groups bonded to a carbon or nitrogen atom of; or; optionally substituted with one or more halogen atoms. 18. A compound according to any one of claims 1 to 17, characterized.

Group A is
The following groups: 4-amino- or 4-methylamino- or 4-dimethylaminoquinolyl, -isoquinolyl, -quinolinium or -isoquinolinium (quinolyl, isoquinolyl, quinolinium or isoquinolinium rings are attached to the carbon or nitrogen atom of this ring Optionally substituted with one or more methyl groups); pyridyl; phenyl optionally substituted with one or more halogen atoms or with the group piperazinyl or alkylpiperazinyl; groups amino, alkyl Amino or dialkylamino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, C2-C4 alkoxy, alkylpiperazinylcarbonyl, imidazolyl or pyrrolidinyl groups, or phenyl groups (these In which the alkyl group has 1 to 4 carbon atoms) substituted C1-C4 alkyl; pyrrolidinyl group; piperidyl group optionally substituted with C1-C4 alkyl group; or substituted with a group selected from quinuclidine group An amino group,
Or a pyrrolidinyl group, a morpholino group, or a piperazinyl group optionally substituted with a C1-C4 alkyl or piperidyl group,
Or according to any one of claims 9 to 18, characterized in that it is one of the groups O-phenyl, O-pyridyl or O-alkyl substituted with an amino, alkylamino or dialkylamino group. Compound.

When Ar ₁ and Ar ₂ are the same,
Ar ₁ and Ar ₂ are 4-amino- or 4-methylamino- or 4-dimethylaminoquinolyl, -isoquinolyl, -quinolinium or -isoquinolinium (quinolyl, isoquinolyl, quinolinium or isoquinolinium ring is carbon or nitrogen of this ring 20. A compound according to any one of claims 1 to 19, characterized in that it is optionally substituted with one or more methyl groups bonded to the atom.

When Ar ₁ and Ar ₂ are different,
Ar ₁ is at least one group N (Ra) (Rb) wherein Ra and Rb are the same or different;
A hydrogen or C1-C4 alkyl group], or a quinoline or isoquinoline motif substituted with a short-chain alkoxy or alkyl group having 1 to 4 carbon atoms, or a quinoline or isoquinoline having a quaternary form of a nitrogen atom, Or benzamidine (unless A is diethylamine, hydrogen or an amine group), or pyridine bonded in the 4-position or condensed with an aryl or heteroaryl group,
Ar ₂ is
* Ring defined above (but different), or
* A phenyl ring optionally substituted with a halogen, methoxy, cyano, carbonylamino, guanyl, methylthio, amino, methylamino, dimethylamino, morpholine, C1-C4 alkyleneamino or C2-C4 alkenyleneamino group,
* Quinoline or isoquinoline, benzimidazole, indole, benzothiophene, benzofuran, benzothiazole, benzoxazole optionally substituted with one or more C1-C4 alkyl groups or with C1-C4 alkylene or C2-C4 alkenylene groups 21. A compound according to any one of claims 1 to 19, characterized in that it is a carbazole, quinazoline or quinoxaline ring.

A is the following group: 4-amino- or 4-methylamino- or 4-dimethylaminoquinolinyl or -quinolinium group (the quinolinium ring is optionally substituted with a methyl group); amino, alkylamino, dialkyl An amino group substituted with a group selected from amino, (phenyl) (alkyl) amino, (alkylphenyl) (alkyl) amino, a C1-C4 alkyl group substituted with a pyrrolidinyl or pyridyl group; or a quinuclidine group 22. A compound according to any one of claims 9 to 21, characterized in that

A is an amino group substituted with one or more groups as defined in any one of claims 9 to 21, or one or as defined in any one of claims 9 to 21. 22. A compound according to any one of claims 9 to 21, characterized in that it is a piperazinyl, homopiperazinyl, piperidinyl or pyrrolidinyl group optionally substituted with further groups.

22. A according to any one of claims 9 to 21, characterized in that A is a group O (or S) -aromatic ring or a group O (or S) -alkyl, wherein alkyl is optionally substituted. Compound described in 1.

A is a group O-phenyl, O-pyridyl, O-pyrimidinyl or O-alkyl substituted by an amino, alkylamino or dialkylamino group, or else the group S-phenyl, S-pyridyl, S-pyrimidyl or S- 22. A compound according to any one of claims 9 to 21, characterized in that it is quinolinyl.

The following products:
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6,
(3-Dimethylaminopropyl) amino- [1,3,5] triazine (Example 1),
2,4,6-tris (4-amino-2-methylquinolin-6-yl) amino- [1,3,5] triazine (Example 2),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (4-dimethylamino-2-methylquinolin-6-yl) amino- [1,3,5] triazine Example 11),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (quinuclidin-3-yl) amino- [1,3,5] triazine (Example 17),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylpiperidin-4-yl)-[1,3,5] triazine (Example 19),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylpiperazin-4-yl)-[1,3,5] triazine (Example 20),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
Pyridin-4-yl) methylamino- [1,3,5] triazine (Example 27),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6-phenoxy- [1,3,5] triazine (Example 29),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (3-dimethylaminopropyl) oxy- [1,3,5] triazine (Example 31),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (pyridin-4-yl) oxy- [1,3,5] triazine (Example 32),
2,4-Bis (4-amino-2-methylquinolin-6-yl) amino-6- (phenylmethyl) oxy- [1,3,5] triazine (Example 33)
The compound according to claim 1 or 2, corresponding to:

The following products:
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
3-dimethylaminopropyl) amino- [1,3,5] triazine (Example 1),
2,4,6-tris (4-amino-2-methylquinolin-6-yl) amino- [1,3,5] triazine (Example 2),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (4-dimethylamino-2-methylquinolin-6-yl) amino- [1,3,5] triazine Example 11),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylpiperazin-4-yl)-[1,3,5] triazine (Example 20),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
Pyridin-4-yl) oxy- [1,3,5] triazine (Example 115),
2,4-bis (4-amino-2-methylquinolin-6-yl) amino-6- (quinolin-2-yl) thio- [1,3,5] triazine (Example 128),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6-phenyl- [1,3,5] triazine (Example 134),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
1- (2-dipropylaminoethyl) piperazin-4-yl]-[1,3,5] triazine (Example 137),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- {
[1-2- (2-hydroxyethyl) oxyethyl] piperazin-4-yl}-[1,3,5] triazine (Example 141),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
2 (S)-(Pyrrolidin-1-yl) methylpyrrolidin-1-yl]-[1,3,5] triazine (Example 149),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
Quinolin-2-yl) thio- [1,3,5] triazine (Example 133),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylhomopiperazin-4-yl)-[1,3,5] triazine (Example 135),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
1- (3-dimethylaminopropyl) piperazin-4-yl]-[1,3,5] triazine (Example 136),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
N- (1-methylpiperidin-4-yl) -N-methylamino]-[1,3,5] triazine (Example 138),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- {
1- [3- (pyrrolidin-1-yl) propylhomopiperazin-4-yl)-[1,3,5] triazine (Example 139),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
1- (Pyridin-4-yl) piperazin-4-yl]-[1,3,5] triazine (Example 144)
The compound according to claim 1 or 2, corresponding to:

The following products:
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylpiperazin-4-yl)-[1,3,5] triazine (Example 20),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
Quinolin-2-yl) thio- [1,3,5] triazine (Example 133),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- (
1-methylhomopiperazin-4-yl)-[1,3,5] triazine (Example 135),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
1- (3-dimethylaminopropyl) piperazin-4-yl]-[1,3,5] triazine (Example 136),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
N- (1-methylpiperidin-4-yl) -N-methylamino]-[1,3,5] triazine (Example 138),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- {
1- [3- (pyrrolidin-1-yl) propylhomopiperazin-4-yl)-[1,3,5] triazine (Example 139),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
1- (pyridin-4-yl) piperazin-4-yl]-[1,3,5] triazine (Example 144),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
4- (piperidin-4-yl) piperazin-1-yl]-[1,3,5] triazine (Example 199),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
4- (piperidin-1-yl) butyl] amino- [1,3,5] triazine (Example 200),
2,4-bis (4-dimethylamino-2-methylquinolin-6-yl) amino-6- [
(Imidazole-1-yl) methyl] amino [1,3,5] triazine (Example 202)
The compound according to claim 1, which corresponds to

A pharmaceutical composition comprising the product according to claim 1 or 2 as an active ingredient.

30. A pharmaceutical composition comprising the product of claim 26, 27 or 28 as an active ingredient.

The compound according to claim 1 or 2, which has telomerase inhibitory activity.

The compound according to any one of claims 1 to 31, which has anticancer activity.

Use of a compound according to claim 32 as a medicament for use in humans.

A therapeutic combination comprising the compound of claim 1 or 2 and another anticancer compound.

Anticancer compounds include alkylating agents, platinum derivatives, antibiotics, anti-microtubule agents, anthracyclines, topoisomerases type I and II, fluoropyrimidines, cytidine analogs, adenosine analogs, L-asparaginase, hydroxyurea , Trans-retinoic acid, suramin, irinotecan, topotecan, dextrazoxane, amifostine, herceptin, and various enzymes and compounds such as estrus and androgen, and antivascular agents 34. The combination according to 34.

A therapeutic combination comprising a compound according to claim 1 or 2 and radiation.

37. A combination according to any one of claims 34 to 36, characterized in that each of the compounds or treatments is administered simultaneously, separately or sequentially.