JP2016504292A - Heteroquinoline-3-carboxamide as a KCNQ2 / 3 modulator - Google Patents

Abstract

The present invention relates to substituted heteroquinoline-3-carboxamides, pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and / or prevention of pain and further diseases and / or disorders.

Description

  The present invention relates to substituted heteroquinoline-3-carboxamides, pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and / or prevention of pain and further diseases and / or disorders.

  The treatment of pain, especially neuropathic pain, is extremely important in medicine. There is a need for effective pain treatment worldwide. What is understood as a successful and satisfactory treatment for pain is also applicable where there is an urgent need for treatment directed to chronic and non-chronic pain targets appropriate to the patient. It has been described in a number of recently published scientific studies in the field of analgesics and basic research on nociception.

The pathophysiological feature of chronic pain is neuronal overexcitability. Neuronal excitability is critically affected by the activity of the K ⁺ channel, since they clearly determine the resting membrane potential of the cell and hence the excitability threshold. Heteromeric K ⁺ channels of molecular subtype KCNQ2 / 3 (Kv7.2 / 7.3) are expressed in neurons in various regions of the central nervous system (hippocampus, amygdala) and peripheral nervous system (dorsal root ganglia); Adjust its excitability. Activation of the KCNQ2 / 3K ⁺ channel leads to hyperpolarization of the cell membrane and concomitant reduction of the electrical excitability of these neurons. KCNQ2 / 3-expressing neurons in the dorsal root ganglia are involved in the transmission of nociceptive stimuli from the periphery to the spinal cord (Passmore et al., J. Neurosci. 2003, 23 (18): 7227-36. (Non-Patent Document 1)).

  As a result, it was possible to detect analgesia in the preclinical neuropathy and inflammatory pain model for the KCNQ2 / 3 agonist retigabine (Blackburn-Munro and Jensen, Eur J Pharmacol. 2003; 460 (2- 3), pages 109 to 16 (Non-Patent Document 2); Dost et al., Naunyn Schmiedebergs Arch Pharmacol 2004, 369 (4), 382-390 (Non-Patent Document 3)).

Thus, the KCNQ2 / 3 K ⁺ channel is a pain selected from the group consisting of pain, particularly chronic pain, acute pain, neuropathic pain, inflammatory pain, visceral pain and muscle pain (Nielsen et al., Eur J Pharmacol., 2004, 487 (1-3), 93-103 (Non-Patent Document 4)), in particular, is a suitable starting point for the treatment of neuropathic and inflammatory pain.

Furthermore, the KCNQ2 / 3 K ⁺ channel is associated with a number of additional diseases, such as migraine (US2002 / 0128277), cognitive disorders (Gribkoff, Expert Opin Ther Targets 2003, 7 (6): 737. 748 (Non-patent Document 5)), anxiety (Korsgaard et al., J Pharmacol Exp Ther. 2005, 14 (1), 282-92 (Non-patent Document 6)), epilepsy (Wickenden et al., Expert) Opin Ther Pat 2004, 14 (4), 457-469 (Non-Patent Document 7); Gribkoff, Expert Opin The Targets 2008, 12 (5), 565-81 (Non-Patent Document 8) Micheli et al., Curr O pin Pharmacol 2008, 8 (1), 65-74 (Non-Patent Document 9)), urinary incontinence (Streng et al., J Urol 2004, 172, 2054-2058 (Non-Patent Document 10)), Addiction (Hansen et al., Eur J Pharmacol 2007, 570 (1-3), 77-88 (Non-Patent Document 11)), Gonorrhea / bipolar disorder (Dencker et al., Epilepsy Behav 2008, 12 (1) ), 49-53 (Non-patent Document 12)) and dystonia-related dyskinesia (Richter et al., Br J Pharmacol 2006, 149 (6), 747-53 (Non-patent Document 13)). A suitable target.

Substituted compounds having affinity for the KCNQ2 / 3 K ⁺ channel are known from, for example, the prior art (WO2008 / 046582 (Patent Document 2), WO2010 / 046108 (Patent Document 3)). In particular, specific quinoline-3-carboxamides have been described for KCNQ regulation (WO2010 / 102811 (Patent Document 4), WO2012 / 025236 (Patent Document 5), WO2012 / 025237 (Patent Document 6), WO2012 / 025238 ( Patent Document 7)).

There is a need for additional compounds that have comparable or better properties (efficacy, efficacy), not only with respect to affinity for the KCNQ2 / 3 K ⁺ channel itself.

  Thus, it may be advantageous to improve metabolic stability, solubility in aqueous media or compound permeability. These factors can have a beneficial effect on oral bioavailability or can alter the PK / PD (pharmacokinetic / pharmacodynamic) profile, which, for example, has a more beneficial efficacy Can lead to a period. The absence of weak interactions or interactions with transporter molecules involved in oral intake and excretion of the pharmaceutical composition should also be considered an indicator of improved bioavailability and, at best, low interaction of the pharmaceutical composition It is. Furthermore, the interaction with the enzymes involved in the degradation and excretion of the pharmaceutical composition should also be as low as possible, since this is also the case when the results of such tests also show the lowest interaction or interaction of the pharmaceutical composition. This is because it suggests that there is no effect at all.

  Furthermore, it may be advantageous if the compound shows a high selectivity (specificity) for other receptors of the KCNQ family, for example for KCNQ1, KCNQ3 / 5 or KCNQ4. High selectivity can have a positive effect on the side effect profile, for example, compounds that have (and also have) an affinity for KCNQ1 may have potential for cardiac side effects. know. Thus, high selectivity for KCNQ1 may be desirable. However, it may also be advantageous for a compound to exhibit high selectivity for other receptors. For example, it may be advantageous for compounds to show low affinity for hERG ion channels or L-type calcium ion channels (phenylalkylamine-, benzothiazepine-, dihydropyridine-binding sites), which This is because it is known that the receptor has a high potential for cardiac side effects. Furthermore, improved selectivity for binding with other endogenous proteins (ie, receptors or enzymes) can result in a better side effect profile and consequently improved tolerance.

US2002 / 0128277 WO2008 / 046582 WO2010 / 046108 WO2010 / 102811 WO2012 / 025236 WO2012 / 025237 WO2012 / 025238

Passmore et al., J. MoI. Neurosci. 2003, 23 (18): 7227-36 Blackburn-Munro and Jensen, Eur J Pharmacol. 2003; 460 (2-3), 109-16 Dost et al., Naunyn Schmiedebergs Arch Pharmacol 2004, 369 (4), 382-390 Nielsen et al., Eur J Pharmacol. 2004, 487 (1-3), 93-103 Griboff, Expert Opin The Targets 2003, 7 (6): 737-748 Korsgaard et al., J Pharmacol Exp Ther. 2005, 14 (1), 282-92 Wickenden et al., Expert Opin Ther Pat 2004, 14 (4), 457-469. Griboff, Expert Opin The Targets 2008, 12 (5), 565-81 Micheli et al., Curr Opin Pharmacol 2008, 8 (1), 65-74. Strength et al., J Urol 2004, 172, 2054-2058. Hansen et al., Eur J Pharmacol 2007, 570 (1-3), 77-88. Dencker et al., Epilepsy Behav 2008, 12 (1), 49-53. Richter et al., Br J Pharmacol 2006, 149 (6), 747-53, 363, 330-336.

The object of the present invention was therefore to provide novel compounds which have advantages over prior art compounds. These compounds are particularly useful in pharmaceutical compositions, preferably in pharmaceutical compositions for the treatment and / or prevention of disorders and / or diseases mediated at least in part by the KCNQ2 / 3 K ⁺ channel. Must be suitable as an effective active ingredient.

  That object is achieved by the claimed subject matter.

Surprisingly, it has been found that the substituted compounds of general formula (I) shown below are suitable for the treatment of pain. Also, surprisingly, substituted compounds of general formula (I) shown below can also have excellent affinity for KCNQ2 / 3 ^{K +} channels, thus, the KCNQ2 / 3 ^{K +} channel, the at least one It has also been found suitable for the prevention and / or treatment of part-mediated disorders and / or diseases. Thereby, the substituted compound acts as a modulator of the KCNQ2 / 3 K ⁺ channel, ie an agonist or antagonist.

  Accordingly, in a first aspect, the present invention provides a compound of the general formula (I)

［式中、
Ａ^１、Ａ^２およびＡ^３は、互いに独立に、ＣＲ^４、Ｎ、Ｏ、ＳまたはＮ（ＣＨ_３）を表し、
Ａ^４は、ＣＲ^４またはＮを表し、
ｎは、０または１を示し、
ただし、
Ａ^１、Ａ^２、Ａ^３およびＡ^４のうち少なくとも１種は、ＣＲ^４を表さず、
ただし、
ｎが０を示す場合には、正確にＡ^１、Ａ^２およびＡ^３のうち１種がＯ、ＳもしくはＮ（ＣＨ_３）を表すか、または
ｎが１を示す場合には、Ａ^１、Ａ^２およびＡ^３が互いに独立に、ＣＲ^４もしくはＮを表し、
Ｒ^１は、非置換であるかまたは一置換もしくは多置換されたＣ_１〜１０−脂肪族残基あるいは各場合において非置換を表すか、
一置換もしくは多置換された、および各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結したＣ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を表すか、
各場合において非置換であるか、または一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結したアリールまたはヘテロアリールを表し、
Ｒ^２は、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＣＮ、ＣＦ_３、Ｃ（＝Ｏ）Ｈ、ＮＯ_２、ＯＣＦ_３、ＳＣＦ_３、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−ＮＨ−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｎ（Ｃ_１〜４−脂肪族残基）_２、Ｏ−Ｃ_１〜４−脂肪族残基、Ｏ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｓ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｏ−Ｃ_１〜４−脂肪族残基を表し、
ここで、Ｃ_１〜４−脂肪族残基は、各場合において、非置換であり得るかまたは一置換もしくは多置換され得、
Ｒ^２は、各場合において非置換であるか、または一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜４−脂肪族基を介して連結した、Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基を表し、
Ｒ^３は、
非置換であるかまたは一置換もしくは多置換されたＣ_２〜１０−脂肪族残基を表し、あるいは
各場合において非置換であるか、または一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結したＣ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を表すか、あるいは、
Ｓ−Ｒ^５、Ｏ−Ｒ^６またはＮ（Ｒ^７Ｒ^８）を示し、
ここで、
Ｒ^５およびＲ^６は、各場合において、
非置換であるかまたは一置換もしくは多置換されたＣ_１〜１０−脂肪族残基、
各場合において非置換であるか、または一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結した、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を表し、
ただし、Ｒ^５またはＲ^６が、３〜１０員のヘテロ脂環式残基を示す場合には、３〜１０員のヘテロ脂環式残基は、炭素原子を介して連結し、
Ｒ^７は、
非置換であるかまたは一置換もしくは多置換されたＣ_１〜１０−脂肪族残基、
各場合において非置換であるか、または一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたは一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結した、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を表し、
ただし、Ｒ^７が、３〜１０員のヘテロ脂環式残基を示す場合には、３〜１０員のヘテロ脂環式残基は、炭素原子を介して連結し、
Ｒ^８は、非置換であるかまたは一置換もしくは多置換された、Ｃ_１〜１０−脂肪族残基を示すか、
あるいは、
Ｒ^７およびＲ^８は、それらを接続している窒素原子と一緒になって、非置換であるかまたは一置換もしくは多置換された、３〜１０員のヘテロ脂環式残基を形成し、
各Ｒ^４は独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＣＮ、ＣＦ_３、ＣＨＦ_２、ＣＨ_２Ｆ、ＯＣＦ_３、ＯＣＨＦ_２、ＯＣＨ_２Ｆ、ＳＣＦ_３、Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_１〜４−脂肪族残基またはＳ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基を表し、
ここで、「脂肪族基」および「脂肪族残基」は、各場合において、分岐または非分岐であり得、飽和または不飽和であり得、
「脂環式残基」および「ヘテロ脂環式残基」は、各場合において、飽和または不飽和であり得、
「脂肪族基」、「脂肪族残基」、「脂環式残基」および「ヘテロ脂環式残基」に関して「一置換または多置換された」は、対応する残基または基に関して、各々互いに独立に、１個または複数の水素原子の、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＮＨ−Ｃ（＝Ｏ）−Ｃ_１〜４脂肪族残基、Ｎ（Ｃ_１〜４脂肪族残基）−Ｃ（＝Ｏ）−Ｃ_１〜４脂肪族残基、ＮＨ−Ｓ（＝Ｏ）_２−Ｃ_１〜４脂肪族残基、Ｎ（Ｃ_１〜４脂肪族残基）−Ｓ（＝Ｏ）_２−Ｃ_１〜４脂肪族残基、＝Ｏ、ＯＨ、ＯＣＦ_３、Ｏ−Ｃ_１〜４−脂肪族残基、Ｏ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２ＯＨ、Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｏ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｓ（＝Ｏ）_２−Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＣＮ、ＣＦ_３、ＣＨＯ、ＣＯＯＨ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、Ｃ（＝Ｏ）ＮＨ_２、Ｃ（＝Ｏ）−ＮＨ（Ｃ_１〜４−脂肪族残基）およびＣ（＝Ｏ）−Ｎ（Ｃ_１〜４−脂肪族残基）_２からなる群から選択される少なくとも１つの置換基による置換に関し、
「アリール」および「ヘテロアリール」に関して「一置換または多置換された」は、対応する残基に関して、各々互いに独立に、１個または複数の水素原子の、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、

[Where:
A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
However,
when n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N;
R ¹ is unsubstituted or represents a mono- or polysubstituted C _{1-10 -aliphatic} residue or in each case unsubstituted,
C _3-10- mono- or poly-substituted and optionally in each case can be likewise unsubstituted or linked via a C _{1-8 -aliphatic} radical which can be mono- or polysubstituted Represents an alicyclic residue or a 3-10 membered heteroalicyclic residue,
Via a C _{1-8 -aliphatic} group which in each case is unsubstituted or mono- or polysubstituted and optionally in each case can likewise be unsubstituted or mono- or polysubstituted Represents aryl or heteroaryl linked together,
R ² is F, Cl, Br, I, CN, CF ₃ , C (═O) H, NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, C (═O) —C _{1-4 -aliphatic} residue, C (= O) -O-C _1-4 -aliphatic residue, C (= O) -NH-C _1-4 -aliphatic residue, C (= O) -N (C _1-4 -aliphatic residue) ₂ , O-C _{1-4 -aliphatic} residue, OC (= O) -C _{1-4 -aliphatic} residue, S-C _{1- 4} -aliphatic residue, S (═O) ₂ -C _{1-4 -aliphatic} residue, S (═O) ₂ -O—C _1-4 -aliphatic residue,
Here, the C _{1-4 -aliphatic} residue can in each case be unsubstituted or mono- or polysubstituted,
R ² is unsubstituted or mono- or polysubstituted in each case, and in each case is optionally C _1-4 -fatty acid that can likewise be unsubstituted or mono- or polysubstituted Represents a C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue linked via a group,
R ³ is
Represents an unsubstituted or mono- or polysubstituted C _{2-10 -aliphatic} residue, or in each case unsubstituted or mono- or polysubstituted, optionally in each case, Similarly, a C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic residue linked via a C _{1-8 -aliphatic} group which may be unsubstituted or mono- or polysubstituted Represents a group, or
S—R ⁵ , O—R ⁶ or N (R ⁷ R ⁸ )
here,
R ⁵ and R ⁶ are in each case
An unsubstituted or mono- or polysubstituted C _{1-10 -aliphatic} residue,
Via a C _{1-8 -aliphatic} group which in each case is unsubstituted or mono- or polysubstituted and optionally in each case can likewise be unsubstituted or mono- or polysubstituted Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue,
Provided that when R ⁵ or R ⁶ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁷ is
An unsubstituted or mono- or polysubstituted C _{1-10 -aliphatic} residue,
Via a C _{1-8 -aliphatic} group which in each case is unsubstituted or mono- or polysubstituted and optionally in each case can likewise be unsubstituted or mono- or polysubstituted Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue,
However, when R ⁷ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ represents a C _{1-10 -aliphatic} residue which is unsubstituted or mono- or polysubstituted,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them form an unsubstituted or mono- or polysubstituted 3- to 10-membered heteroalicyclic residue;
Each R ⁴ is independently H, F, Cl, Br, I, CN, CF ₃ , CHF ₂ , CH ₂ F, OCF ₃ , OCHF ₂ , OCH ₂ F, SCF ₃ , O—C _1-4 -Fat. Represents a group residue, a C _1-4 -aliphatic residue or S (= O) ₂ -C _1-4 -aliphatic residue,
Here, the “aliphatic group” and “aliphatic residue” may in each case be branched or unbranched, saturated or unsaturated,
“Cycloaliphatic residue” and “heteroalicyclic residue” can in each case be saturated or unsaturated,
“Mono-substituted or poly-substituted” with respect to “aliphatic group”, “aliphatic residue”, “alicyclic residue” and “heteroalicyclic residue” respectively refers to the corresponding residue or group respectively. Independently of each other, F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) of one or more hydrogen atoms Group) ₂ , NH—C (═O) —C _1-4 aliphatic residue, N (C _1-4 aliphatic residue) —C (═O) —C _1-4 aliphatic residue, NH— S (= O) _{2- C1-4} aliphatic residue, N ( _C1-4 aliphatic residue) -S (= O) _{2- C1-4} aliphatic residue, = O, OH, OCF ₃ , O-C _{1-4 -aliphatic} residue, O-C (= O) -C _1-4 -aliphatic residue, SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, S _{(= O) 2 OH, S} (= O) 2 -C 1 ₄ - aliphatic _{residue, S (= O) 2 -O} -C 1~4 - aliphatic _{residue, S (= O) 2 -NH} (C 1~4 - aliphatic residues), S (= O ) _2- N (C _1-4 -aliphatic residue) ₂ , CN, CF ₃ , CHO, COOH, C _1-4 -aliphatic residue, C (= O) -C _{1-4 -aliphatic} residue Group, C (═O) —O—C _{1-4 -aliphatic} residue, C _{3-6 -alicyclic} residue, 3-7 membered heteroalicyclic residue, C (═O) NH ₂ , C (═O) —NH (C _1-4 -aliphatic residue) and C (═O) —N (C _{1-4 -aliphatic} residue) _2. Regarding substitution with groups,
“Monosubstituted or polysubstituted” with respect to “aryl” and “heteroaryl”, independently of each other with respect to the corresponding residues, are F, Cl, Br, I, NO _{2 of} one or more hydrogen atoms. , NH ₂ ,

ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＮＨ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｎ（Ｃ_１〜４脂肪族残基）−Ｃ（＝Ｏ）−Ｃ_１〜４脂肪族残基、ＮＨ−Ｓ（＝Ｏ）_２−Ｃ_１〜４脂肪族残基、Ｎ（Ｃ_１〜４脂肪族残基）−Ｓ（＝Ｏ）_２−Ｃ_１〜４脂肪族残基、ＯＨ、ＯＣＦ_３、Ｏ−Ｃ_１〜４−脂肪族残基、Ｏ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２ＯＨ、Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｏ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｓ（＝Ｏ）_２−Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＣＮ、ＣＦ_３、Ｃ（＝Ｏ）Ｈ、Ｃ（＝Ｏ）ＯＨ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、ベンジル、アリール、ヘテロアリール、Ｃ（＝Ｏ）ＮＨ_２、Ｃ（＝Ｏ）−ＮＨ（Ｃ_１〜４−脂肪族残基）およびＣ（＝Ｏ）−Ｎ（Ｃ_１〜４−脂肪族残基）_２からなる群から選択される少なくとも１つの置換基による置換に関する］
の、
個々の単一の立体異性体または任意の混合比の立体異性体の混合物の形態、ならびに／または遊離化合物、溶媒和物およびおよび／もしくは生理学的に許容される塩の形態の化合物
に関する。

NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , NH—C (═O) —C _{1-4 -aliphatic} residue, N (C _{1-1 4} aliphatic residue) -C (= O) _-C1-4 aliphatic residue, NH-S (= O) _{2- C1-4} aliphatic residue, N ( _C1-4 aliphatic residue) _{) -S (= O) 2 -C} 1~4 aliphatic _{residue, OH, OCF 3, O-} C 1~4 - aliphatic _{residues, O-C (= O)} -C 1~4 - aliphatic Residue, SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, S (═O) ₂ OH, S (═O) ₂ -C _{1-4 -aliphatic} residue, S (═O) _2- O-C _1-4 -aliphatic residue, S (= O) ₂ -NH (C _1-4 -aliphatic residue), S (= O) ₂ -N (C _{1-4 -aliphatic residues) 2, CN, CF 3,} C (= O) H, C (= O) OH, C 1~4 - aliphatic residue, C ( _{O) -C 1 to 4} - aliphatic _{residue, C (= O) -O-} C 1~4 - aliphatic _{residue, C 3 to 6} - cycloaliphatic residue, 3-7 membered heteroalicyclic Formula residues, benzyl, aryl, heteroaryl, C (═O) NH ₂ , C (═O) —NH (C _1-4 -aliphatic residue) and C (═O) —N (C _1-4 -Aliphatic residue) regarding substitution with at least one substituent selected from the group consisting of ₂ ]
of,
It relates to compounds in the form of individual single stereoisomers or mixtures of stereoisomers of any mixing ratio and / or in the form of free compounds, solvates and / or physiologically acceptable salts.

Within the scope of the present invention, the term “aliphatic residue” or “aliphatic group” means 1-10 or 1-8 or 1-6 or 1-4 or 1-2 or 2-6. Acyclic saturated or unsaturated aliphatic hydrocarbon radicals having ₁ carbon atom, which may be branched or unbranched and may be unsubstituted or mono- or polysubstituted, ie C _1-10 -alkanyl, C _{2 -10} -alkenyl and _C2-10 -alkynyl or _C1-8 -alkanyl, _C2-8 -alkenyl and _C2-8 -alkynyl or _C1-6 -alkanyl, _C2-6 -alkenyl and _{C2- 6} - alkynyl or _{C 1 to 4} - _{alkanyl, C 2 to 4} - alkenyl, and _{C 2 to 4} - alkynyl or _{C 1 to 2} - alkanyl, _{C 2} - alkenyl and _{C 2} - alkynyl Other _{C 2 to 6} - includes alkynyl - _{alkanyl, C 2 to 6} - alkenyl, and _{C 2 to 6.} Alkenyl contains at least one C—C double bond and alkynyl contains at least one C—C triple bond. Alkyl is preferably methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n- Includes octyl, n-nonyl, n-decyl, ethenyl (vinyl), ethynyl, propenyl, propynyl, butenyl, butynyl, pentenyl, pentynyl, hexenyl and hexynyl, heptenyl, heptynyl, octenyl, octynyl, nonenyl, nonenyl, decenyl and decynyl Selected from the group.

For the purposes of the present invention, the terms “alicyclic residue” or “C _{3-10 -alicyclic} residue” and “C _{3-6 -alicyclic} residue” are 3, 4, 5, 6 , 7, 8, 9 or 10 carbon atoms or cycloaliphatic hydrocarbons having 3, 4, 5 or 6 carbon atoms, wherein the hydrocarbon is saturated or unsaturated ( Provided that it is not aromatic), unsubstituted, mono- or polysubstituted. The attachment of the alicyclic residue to the higher order general structure can occur through any desired and possible ring member of the cycloalkyl group. Cycloaliphatic residues can also be further saturated, (partially) unsaturated, (hetero) cycloaliphatic, aromatic or heteroaromatic ring systems, ie per se, unsubstituted or mono- or polysubstituted. It can be fused with an alicyclic residue, heteroalicyclic residue, aryl or heteroaryl, which can be substituted. The alicyclic residue group can be further crosslinked one or more times, as in, for example, adamantyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl. Cycloalkyl is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenylcyclononyl, cyclodecyl, adamantyl and

を含む群から選択される。好ましいＣ_３〜６−脂環式残基は、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロペンテニルおよびシクロヘキセニルからなる群から選択される。

Selected from the group comprising Preferred C _{3-6 -alicyclic} residues are selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl and cyclohexenyl.

The term “3-10 membered heteroalicyclic residue” or “3-7 membered heteroalicyclic residue” or “heteroalicyclic residue” preferably has at least one carbon atom, Also optionally, 2 or 3 carbon atoms in each case O, S, S (═O), S (═O) ₂ , N, NH and the ring members may be unsubstituted or N (C _1-8 -alkyl), which may be substituted or polysubstituted, preferably 3-10, substituted by a heteroatom or heteroatom group independently selected from the group consisting of N (CH ₃ ) That is, aliphatic saturated or unsaturated having 3, 4, 5, 6, 7, 8, 9 or 10 ring members, or 3-7, ie 3, 4, 5, 6 or 7 ring members ( However, it includes heteroalicyclic residues that are not aromatic. The binding of the heteroalicyclic residue to the higher order general structure can occur through any desired and possible ring member of the heteroalicyclic residue. Heteroalicyclic residues may also be further saturated, (partially) unsaturated (hetero) alicyclic or aromatic or heteroaromatic ring systems, which may themselves be unsubstituted or mono- or polysubstituted Ie, fused to an alicyclic residue, heteroalicyclic residue, aryl or heteroaryl. Heteroalicyclic residues are preferably azetidinyl, aziridinyl, azepanyl, azocanyl, diazepanyl, dithiolanyl, dihydroquinolinyl, dihydropyrrolyl, dioxanyl, dioxolanyl, dihydroindenyl, dihydropyridinyl, dihydrofuranyl, dihydroiso Quinolinyl, dihydroindolinyl, dihydroisoindolyl, imidazolidinyl, isoxazolidinyl, morpholinyl, oxiranyl, oxetanyl, pyrrolidinyl, piperazinyl, piperidinyl, pyrazolidinyl, pyranyl, tetrahydropyrrolyl, tetrahydropyranyl, tetrahydroquinolinyl, Tetrahydroisoquinolinyl, tetrahydroindolinyl, tetrahydrofuranyl, tetrahydropyridinyl, tetrahydrothiophenyl, tetrahydropyridinyl Indolyl, tetrahydronaphthyl, tetrahydrocarboline Li sulfonyl, tetrahydroisoquinoline oxazolone pyridinylcarbonyl, is selected from the group comprising thiazolidinyl and thiomorpholinyl.

  Within the scope of the present invention, the term “aryl” denotes aromatic hydrocarbons having a maximum of 14 ring members, in particular phenyl and naphthyl. Each aryl group can be unsubstituted or mono- or polysubstituted, and the aryl substituents can be the same or different and can be in any desired position of the aryl. The aryl can be linked to a higher order general structure via any desired and possible ring member of the aryl group. Aryl groups can also be unsubstituted, mono- or polysubstituted, and can be further saturated, (partially) unsaturated, (hetero) alicyclic, aromatic or heteroaromatic ring systems, ie , Alicyclic residues, heteroalicyclic residues, aryl or heteroaryl. Examples of aryl groups that are fused include benzodioxolanyl and benzodioxanyl. Aryl is preferably selected from the group containing phenyl, 1-naphthyl and 2-naphthyl, each of which can be unsubstituted or mono- or polysubstituted. Particularly preferred aryls are unsubstituted or mono- or polysubstituted phenyl.

  The term “heteroaryl” refers to a 5- or 6-membered cyclic aromatic group containing at least one heteroatom and optionally 2, 3, 4 or 5 heteroatoms, where the heteroatom Are in each case independently selected from the groups S, N and O, the heteroaryl group can be unsubstituted or mono- or polysubstituted, and in the case of substitution on the heteroaryl, The groups can be the same or different and can be in any desired possible position of the heteroaryl. The bond to the higher order general structure can occur through any desired and possible ring member of the heteroaryl group. A heteroaryl can also be part of a bicyclic or polycyclic system having up to 14 ring members, where the ring system can itself be unsubstituted or mono- or polysubstituted. Can be formed with further saturated, (partially) unsaturated, (hetero) alicyclic residues or aromatic or heteroaromatic rings, ie with alicyclic residues, heteroalicyclic residues, aryl or heteroaryl . For heteroaryl groups, benzofuranyl, benzimidazolyl, benzothienyl, benzothiadiazolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, benzooxadiazolyl, quinazolinyl, quinoxalinyl, carbazolyl, quinolinyl, dibenzofuranyl, dibenzothienyl, furyl (Furanyl), imidazolyl, imidazolothiazolyl, indazolyl, indolizinyl, indolyl, isoquinolinyl, isoxazolyl, isothiazolyl, indolyl, naphthyridinyl, oxazolyl, oxadiazolyl, phenazinyl, phenothiazinyl, phthalazinyl, pyrazolyl, pyridyl (2-pyridyl, 3-pyridyl, 4-pyridyl), pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, purinyl, phenazinyl, Enyl (thiophenyl), triazolyl, tetrazolyl, thiazolyl, be selected from the group comprising thiadiazolyl, and triazinyl preferred. Furyl, pyridyl and thienyl are particularly preferred.

Within the scope of the present invention, in connection with an aryl, heteroaryl, heteroalicyclic residue or alicyclic residue, the expression “linked via a C _1-4 aliphatic group” or “C _1-8 “Linked via an aliphatic group” means that the C _{1-8 -aliphatic} group or C _{1-4 -aliphatic} group and the aryl or heteroaryl or heteroalicyclic residue or alicyclic residue is as defined above. Having the meaning as defined, wherein the aryl or heteroaryl or heteroalicyclic residue or alicyclic residue is via a C _{1-4 -aliphatic} group or via a C _{1-8 -aliphatic} group It is understood that it is combined with higher general structures. Aliphatic groups in all cases can be saturated or unsaturated, can be branched or unbranched, can be unsubstituted, or can be mono- or polysubstituted. The C _{1-4 -aliphatic} group is preferably a C _1-4 -alkyl group, preferably —CH ₂ —, —CH ₂ CH ₂ —, —CH (CH ₃ ) —, —CH ₂ CH _{2. CH 2 -, - CH (CH} 3) CH 2 -, - CH (CH 2 CH 3) -, - CH 2 (CH 2) 2 CH 2 -, - CH (CH 3) CH 2 CH 2 -, - CH ₂ CH (CH ₃ ) CH ₂ —, —CH (CH ₃ CH (CH ₃ ) —, —CH (CH ₂ CH ₃ ) CH ₂ —, —C (CH ₃ ) ₂ CH ₂ —, —CH (CH _{2 CH 2 CH 3) -, -} C (CH 3) (CH 2 CH 3) -, - CH = CH -, - CH = CHCH 2 -, - C (CH 3) = CH 2 -, - CH = CHCH 2 _{CH 2 -, - CH 2 CH} = CHCH 2 -, - CH = CHCH = CH -, - C (CH 3 _{= CHCH 2 -, - CH =} C (CH 3) CH 2 -, - C (CH 3) = C (CH 3) -, - C (CH 2 CH 3) = CH -, - C≡C -, - Selected from the group comprising C≡CCH ₂ —, —C≡CCH ₂ CH ₂ —, —C≡CCH (CH ₃ ) —, —CH ₂ C≡CCH ₂ —, and —C≡CC (CH ₃ ) ₂ —. The

In connection with “aliphatic residue”, “aliphatic group”, “heteroalicyclic residue” and “alicyclic residue”, the expression “monosubstituted or polysubstituted” is within the scope of the present invention. In each case, independently of each other, F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue, N (C _{1-4 -aliphatic} residue) ₂ , NH-C (= O) _-C1-4 aliphatic residue, N ( _C1-4 -aliphatic residue) -C (= O) _-C1-4 aliphatic residue, NH-S (= O) ₂ -C _{1-4 -aliphatic} residue, N (C _1-4 -aliphatic residue) -S (= O) ₂ -C _1-4 -aliphatic residue, = O, OH, OCF ₃ , O—C _1-4 aliphatic residue, O—C (═O) —C _1-4 -aliphatic residue, SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, S ( _{= O) 2 OH, S (} = O) 2 -C 1~4 - aliphatic residue _{S (= O) 2 -O-} C 1~4 - aliphatic _{residue, S (= O) 2 -NH} (C 1~4 - aliphatic _{residues), S (= O) 2} -N (C 1 _˜4 -aliphatic residue) ₂ , CN, CF ₃ , CHO, COOH, C _1-4 -aliphatic residue, C (═O) —C _{1-4 -aliphatic} residue, C (═O) -O-C _{1-4 -aliphatic} residue, C _{3-6 -alicyclic} residue, 3-7 membered heteroalicyclic residue, benzyl, aryl, heteroaryl, C (= O) NH ₂ By a substituent selected from the group comprising C (═O) —NH (C _1-4 -aliphatic residue) and C (═O) —N (C _{1-4 -aliphatic} residue) ₂ , It is understood to mean one or more substitutions of one or more hydrogen atoms, for example 2, 3 or 4 times, wherein the polysubstituent is a number either on different atoms or on the same atom. Times, example If, three or four times, for example, 3 times on the same carbon atom in the case of CF ₃ or _CH 2 CF _3, or at different planes as in the case of CH (OH) -CH = CH- CHCI 2 It should be understood that a substituent is itself a substituent, which may optionally be mono- or polysubstituted, which may be substituted with the same substituent or with different substituents. Can occur with.

Preferred substituents for “aliphatic residue”, “aliphatic group”, “heteroalicyclic residue” or “alicyclic residue” are F, CI, Br, NH ₂ , NH (C _1-4 -Aliphatic residue), N (C _{1-4 -aliphatic} residue) ₂ , NH-C (= O) -C _1-4 aliphatic residue, NH-S (= O) ₂ -C _{1- 4} -aliphatic residue, ═O, OH, OCF ₃ , O—C _1-4 -aliphatic residue, O—C (═O) —C _{1-4 -aliphatic} residue, S (═O) _{2- C1-4} -aliphatic residue, S (= O) _2- NH ( _C1-4 -aliphatic residue), S (= O) _2- N ( _C1-4 -aliphatic residue) ) ₂ , CN, CF ₃ , COOH, C _1-4 -aliphatic residue, C (═O) -C _{1-4 -aliphatic} residue, C _3-6 -alicyclic residue, 3-7 heterocycloaliphatic residues _{membered, C (= O) NH 2} , C (= O) -NH (C 1~ - aliphatic residue) and _{C (= O) -N (C} 1~4 - is selected from the group comprising aliphatic _{residues) 2.}

In the context of “aryl” and “heteroaryl”, the term “monosubstituted or polysubstituted” means that within the scope of the present invention, a substituent may itself optionally be monosubstituted or polysubstituted. F, Cl, Br, I, NO ₂ , NH ₂ , on one atom or optionally on different atoms

、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＮＨ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｎ（Ｃ_１〜４−脂肪族残基）−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、ＮＨ−Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、Ｎ（Ｃ_１〜４−脂肪族残基）−Ｓ（＝Ｏ）_２−Ｃ_１〜４脂肪族残基、ＯＨ、ＯＣＦ_３、Ｏ−Ｃ_１〜４−脂肪族残基、Ｏ−Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２ＯＨ、Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｏ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｓ（＝Ｏ）_２−Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＣＮ、ＣＦ_３、Ｃ（＝Ｏ）Ｈ、Ｃ（＝Ｏ）ＯＨ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、ベンジル、アリール、ヘテロアリール、Ｃ（＝Ｏ）ＮＨ_２、Ｃ（＝Ｏ）−ＮＨ（Ｃ_１〜４−脂肪族残基）およびＣ（＝Ｏ）−Ｎ（Ｃ_１〜４−脂肪族残基）_２を含む群から選択される置換基による、各場合において互いに独立に、環系の１個または複数の水素原子の１回または複数回、例えば、２、３または４回の置換を意味すると理解される。多置換は、同一の置換基を用いて、または異なる置換基を用いて実施される。

, NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , NH—C (═O) —C _{1-4 -aliphatic} residue, N (C _{1 to 4} - aliphatic _{residue) -C (= O) -C 1~4} - aliphatic _{residue, NH-S (= O)} 2 -C 1~4 - aliphatic residue, _{N (C 1 to 4} - aliphatic _{residue) -S (= O) 2 -C} 1~4 aliphatic _{residue, OH, OCF 3, O-} C 1~4 - aliphatic residues, O-C (= O) -C 1 _˜4 -aliphatic residue, SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, S (═O) ₂ OH, S (═O) ₂ -C _{1-4 -aliphatic} residue, S (═O) ₂ —O—C _1-4 -aliphatic residue, S (═O) ₂ —NH (C _1-4 -aliphatic residue), S (═O) ₂ —N (C _{1 ˜4} -aliphatic residue) ₂ , CN, CF ₃ , C (═O) H, C (═O) OH, C _1-4 -fatty Group residue, C (═O) —C _1-4 -aliphatic residue, C (═O) —O—C _1-4 -aliphatic residue, C _3-6 -alicyclic residue, 3 heterocycloaliphatic residues to 7-membered, benzyl, aryl, _{heteroaryl, C (= O) NH 2} , C (= O) -NH (C 1~4 - aliphatic residues) and C (= O) One or more times of one or more hydrogen atoms of the ring system, in each case, independently of one another, by a substituent selected from the group comprising -N (C _1-4 -aliphatic residue) ₂ , for example It is understood to mean 2, 3 or 4 substitutions. Multi-substitution is performed with the same substituent or with different substituents.

Preferred “aryl” and “heteroaryl” substituents are F, Cl, Br, CF ₃ , CN, C _{1-4 -aliphatic} residues, phenyl, naphthyl, pyridyl, thienyl, furyl, C _3-6 -aliphatic. Cyclic residue, 3-7 membered heteroalicyclic residue, C (═O) —C _{1-4 -aliphatic} residue, CO ₂ H, C (═O) —O—C _1-4 — Aliphatic residue, CONH ₂ , C (═O) —NH (C _1-4 -aliphatic residue), C (═O) —N (C _{1-4 -aliphatic} residue) ₂ , OH, O -C _{1 to 4} - aliphatic _{residue, OCF 3, O-C (} = O) -C 1~4 - aliphatic _{residues, NH 2, NH (C 1~4} - aliphatic residues), N ( C _{1-4 -aliphatic} residue) ₂ , N (H) C (═O) —C _{1-4 -aliphatic} residue, S—C _1-8 -alkyl, SCF ₃ , S (═O) ₂ C _{1 to 4} - aliphatic residue _{, S (= O) 2 -N} (H) C 1~4 - aliphatic residue.

The compounds of the present invention are defined by substituents, for example, themselves optionally substituted (second generation substituents) R ^A , R ^B and R ^c (first generation substituents). . Depending on the definition, the substituents of these substituents can likewise be substituted themselves (third generation substituents). For example, when R ^A = aryl (first generation substituent), the aryl can itself be substituted, eg, by a C _{1-4 -aliphatic} residue (second generation substituent). This results in a functional group aryl-C _{1-4 -aliphatic} residue. Similarly, C _{1-4 -aliphatic} residues can themselves be substituted, for example, by Cl (third generation substituent). Overall, this results in the functional group aryl-C _1-4 -aliphatic residue —Cl.

  However, in a preferred embodiment, the third generation substituents cannot themselves be substituted, ie there are no fourth generation substituents.

In another preferred embodiment, the second generation substituent cannot itself be substituted, i.e., there is no even any third generation substituent. In other words, in this embodiment, for example, in the case of general formula (I), the functional groups of R ^{1 to} R ¹⁴ can be optionally substituted in each case, but the substituents in each case are It cannot be replaced by itself.

In some cases, the compounds of the present invention in each case are unsubstituted, mono- or poly-substituted, or carbon atom (s) connecting them as ring member (s). ) Or an aryl or heteroaryl group that, together with the heteroatom (s), forms a ring, eg, in each case unsubstituted or mono- or polysubstituted aryl or heteroaryl; Or defined by the substituents that hold it. Both these aryl or heteroaryl groups and the aromatic ring systems so formed are optionally C _{3-10 -alicyclic} residues or heteroalicyclic rings, which in each case are saturated or unsaturated. and formula radical, i.e., C _{3 to 10,} such as cyclopentyl _- cycloaliphatic residue or heteroalicyclic residues fused to give a morpholinyl,, C _{3 to 10} fused Thus _- alicyclic The residue or heteroalicyclic residue group can be unsubstituted or mono- or polysubstituted.

In some cases, the compounds of the present invention are in each case unsubstituted, mono- or poly-substituted, or carbon atom (s) connecting them as ring member (s) Or a C _3-10 -heteroalicyclic residue or heteroalicyclic residue that forms or forms a ring with the heteroatom (s), or a substituent that carries them, eg, each In some cases, it is defined by unsubstituted or _mono- or polysubstituted C _{3-10 -alicyclic} or heteroalicyclic residues. Both these C _{3-10 -alicyclic} or heteroalicyclic residues and the aliphatic ring system formed are optionally aryl and heteroaryl, ie aryl such as phenyl, or pyridyl, etc. The aryl or heteroaryl group so fused can be unsubstituted or mono- or polysubstituted.

  Symbols used in formulas within the scope of the present invention

は、対応する基の高次の一般構造との連結を示す。

Shows the connection with the higher order general structure of the corresponding group.

  The expression “salt formed with a physiologically acceptable acid” means the active ingredient in question with a physiologically acceptable inorganic or organic acid, especially when used in humans and / or mammals. Are understood within the scope of the present invention. Hydrochloride is particularly preferred.

  Physiologically acceptable salts with cations or bases, especially when used in humans and / or mammals, of physiologically acceptable anions with at least one, preferably inorganic cation, are used. In the form of a salt of the compound in question.

In one embodiment of the invention, the compound of general formula (I) is
A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
However,
when n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N;
R ¹ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} C _{1-10 -aliphatic} residues mono- or polysubstituted with at least one substituent selected from the group consisting of residues and C (═O) OH,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Alternatively, R ¹ is unsubstituted in each case or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4 -fatty Group residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4 -aliphatic residue, CF ₃ , CN, C _{1 With} at least one substituent selected from the group consisting of _˜4 -aliphatic residue, C (═O) OH, C _{3-6 -alicyclic} residue and 3-7 membered heteroalicyclic residue Represents a mono- or polysubstituted C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substitution selected from C (═O) OH _Can be linked via a C _{1-8 -aliphatic} group, which can be mono- or polysubstituted by groups,
Alternatively, R ¹ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue). Group) ₂ , OH, O—C—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4- Aliphatic residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ , C (═O) OC ₂ H ₅ , C _{3 -6} -alicyclic residue, 3-7 membered heteroalicyclic residue,

、ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、アリールまたはヘテロアリールを示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＯＣＨ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
アリールまたはヘテロアリール残基は、各場合において、任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮおよびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結し得、
Ｒ^２が、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＣＮ、ＣＦ_３、ＮＯ_２、ＯＣＦ_３、ＳＣＦ_３、Ｃ_１〜４−脂肪族残基、Ｓ−Ｃ_１〜４−脂肪族残基、Ｏ−Ｃ_１〜４−脂肪族残基を表し、
ここで、Ｃ_１〜４−脂肪族残基が、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
Ｒ^２が、各場合において非置換であり得るかまたは一置換もしくは多置換され、各場合において任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮおよびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜４−脂肪族基を介して連結した、Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基を表し、
Ｒ^３は、非置換であるかまたは、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_２〜１０−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
Ｒ^３は、各場合において非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基は、各場合において、任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結し得るか、
あるいは、
Ｒ^３は、Ｓ−Ｒ^５、Ｏ−Ｒ^６またはＮ（Ｒ^７Ｒ^８）を示し、
ここで、
Ｒ^５およびＲ^６は、非置換であるかまたは、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜１０−脂肪族残基を各場合において表し、
ここで、各場合におけるＣ_１〜４脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、各場合において非置換であるか、または、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−ＯＨ、Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を各場合において表し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基は、各場合において、任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結し得、
ただし、Ｒ^５またはＲ^６が、３〜１０員のヘテロ脂環式残基を示す場合には、３〜１０員のヘテロ脂環式残基は、炭素原子を介して連結し、
Ｒ^７は、非置換であるかまたは、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜１０−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３および非置換Ｏ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、Ｒ^７は、各場合において非置換であるか、または、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を示し、
ここで、Ｃ_１〜４−脂肪族残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）−ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基は、各場合において、任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜８−脂肪族基を介して連結し得、
ただし、Ｒ^７が、３〜１０員のヘテロ脂環式残基を示す場合には、３〜１０員のヘテロ脂環式残基は、炭素原子を介して連結し、
Ｒ^８は、非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜１０−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
Ｒ^７およびＲ^８は、それらを接続している窒素原子と一緒になって、非置換であるかまたは、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）−ＯＨ、Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された３〜１０員のヘテロ脂環式残基を形成し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｒ^７およびＲ^８によって、それらを接続している窒素原子と一緒になって形成される３〜１０員のヘテロ脂環式残基は、任意選択で、アリールまたはヘテロアリールと縮合し得、このように縮合するアリールまたはヘテロアリール残基は、その部分について、それぞれ、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、

Aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ can be mono- or polysubstituted with at least one substituent selected from the group consisting of C (═O) OCH ₃ and C (═O) OC ₂ H ₅ ,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
An aryl or heteroaryl residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue ), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} Linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from the group consisting of residues, CF ₃ , CN and C (═O) OH;
R ² is F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S—C _{1-4 -aliphatic} residue, O— _{Represents a} C _{1-4 -aliphatic} residue,
Here, the C _{1-4 -aliphatic} residue can in each case be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic.} Can be mono- or polysubstituted with at least one substituent selected from the group consisting of residues;
Or
R ² can be unsubstituted or mono- or polysubstituted in each case and optionally in each case can also be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF _{3, S-C 1~4} - aliphatic residue, _CF 3, CN and _C (= O) C 1~4 which may be mono- or polysubstituted with at least one substituent selected from the group consisting of OH _{-Represents a C3-6} -alicyclic residue or a 3-7 membered heteroalicyclic residue linked via an aliphatic group,
R ³ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4 -fatty Zokuzanmoto and C (= O) in one least one substituent selected from the group consisting of OH substituted or polysubstituted C _{2 to 10 -} represents an aliphatic residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Or
R ³ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) Group) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4 A C _3-10 alicyclic residue or a 3-10 membered heterolipid mono- or polysubstituted with at least one substituent selected from the group consisting of an aliphatic residue and C (═O) OH Indicates a cyclic residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH _Can be linked via a C _{1-8 -aliphatic} group which can be mono- or polysubstituted by substituents,
Or
R ³ represents S—R ⁵ , O—R ⁶ or N (R ⁷ R ⁸ );
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} ) Residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1- A C _{1-10 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues and C (═O) OH in each case;
Here, the C _1-4 aliphatic residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Monosubstituted or polysubstituted with at least one substituent selected from the group consisting of:
Alternatively, in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) Group) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4 -At least one substituent selected from the group consisting of aliphatic residues, C (= O) -OH, _C3-6 -alicyclic residues and 3-7 membered heteroalicyclic residues A substituted or polysubstituted C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue in each case;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH Can be linked via a C _{1-8 -aliphatic} group which can be mono- or polysubstituted with substituents;
Provided that when R ⁵ or R ⁶ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁷ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4 -fatty _{Zokuzanmoto, C (= O) -O-} C 1~4 - aliphatic residues and _C (= O) C ₁ which is mono- or polysubstituted with at least one substituent selected from the group consisting of OH _-10- represents an aliphatic residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Alternatively, R ⁷ is unsubstituted in each case, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4 - aliphatic _{residue) 2, OH, = O,} O-C 1~4 - aliphatic _{residue, OCF 3, SH, SCF 3} , S-C 1~4 - aliphatic _residue, CF _{3, CN,} C _{1-4 -aliphatic} residues, C (═O) OH, C (═O) —O—C _{1-4 -aliphatic} residues, C _{3-6 -alicyclic} residues and 3-7 members A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue that is mono- or polysubstituted with at least one substituent selected from the group consisting of: Indicate
Here, C _{1-4 -aliphatic} residues can in each case be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic.} May be mono- or polysubstituted with at least one substituent selected from the group consisting of residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) —OH Or can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _{1-4 -aliphatic} residue, C (═O) —O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue Linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from the group consisting of a group and C (═O) OH;
However, when R ⁷ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} A C _{1-10 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of a residue and C (═O) OH;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _1-4 -fatty Group residue), N (C _1-4 -aliphatic residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _1-4 - aliphatic _{residue, CF 3, CN, C 1~4} - aliphatic _{residue, C (= O) -OH,} C 3~6 - cycloaliphatic residues and 3-7 membered heteroalicyclic residue Forming a 3-10 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of groups;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
A 3 to 10 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them may optionally be fused with an aryl or heteroaryl, aryl or heteroaryl residues fused, as, for that portion, respectively, possible or F _{unsubstituted, Cl, Br, I, NO} 2, NH 2, NH (C 1~4 - aliphatic residues ), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C ( _{= O) OC 2 H 5,} C 3~6 - cycloaliphatic residue, 3-7 membered heteroalicyclic residues,

、ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＯＣＨ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各Ｒ^４が独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＣＮ、ＣＦ_３、ＣＨＦ_２、ＣＨ_２Ｆ、ＯＣＦ_３、ＯＣＨＦ_２、ＯＣＨ_２Ｆ、ＳＣＦ_３、Ｏ−Ｃ_１〜４−脂肪族残基、Ｃ_１〜４−脂肪族残基またはＳ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基を表す
ことを特徴とする。

, Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can be mono- or polysubstituted with at least one substituent selected from the group consisting of
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ can be mono- or polysubstituted with at least one substituent selected from the group consisting of C (═O) OCH ₃ and C (═O) OC ₂ H ₅ ,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
Each R ⁴ is independently H, F, Cl, Br, I, CN, CF ₃ , CHF ₂ , CH ₂ F, OCF ₃ , OCHF ₂ , OCH ₂ F, SCF ₃ , OC ₄ -Fat. It represents a group residue, a C _1-4 -aliphatic residue or S (═O) ₂ -C _1-4 -aliphatic residue.

  Within the scope of the present invention, the general formula (I)

の中心構造要素は、二環式［５，６］（ｎ＝０について）または二環式［６，６］（ｎ＝１について）ヘテロアリール残基を表す。ヘテロアリール残基は、破線の結合提示によって表されるような芳香族である。

The central structural element of represents a bicyclic [5,6] (for n = 0) or bicyclic [6,6] (for n = 1) heteroaryl residue. A heteroaryl residue is aromatic as represented by the dashed bond presentation.

  When n represents 1, the central structural element in the general formula (I) represents a bicyclic [6,6] heteroaryl residue (I-1).

  When n represents 0, the partial structure in the general formula (I) is a bicyclic [5,6] heteroaryl residue (I-2) or (I-3) or (I-4). Represent.

In order to preserve the aromaticity of the 5-membered heterocycle, within the scope of the present invention,
When n represents 0 and A ³ represents O or S or NR ⁸ , the compound of general formula (I) is represented by formula (I-2)
When n represents 0 and A ¹ represents O or S or NR ⁸ , the compound of general formula (I) is represented by formula (I-3)
It is understood that when n represents 0 and A ² represents O or S or NR ⁸ , the compound of general formula (I) is represented by formula (I-4).

In another embodiment of the invention the compound of general formula (I) is
n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents CR ⁴ , and A ⁴ represents CR ⁴ (formula (I-1a))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＮを表し、Ａ^３がＣＲ^４を表し、Ａ^４がＣＲ^４を表すか（式（Ｉ−１ｂ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents CR ⁴ , and A ⁴ represents CR ⁴ (formula (I-1b))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＣＲ^４を表し、Ａ^３がＣＲ^４を表し、Ａ^４がＣＲ^４を表すか（式（Ｉ−１ｃ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents CR ⁴ , and A ⁴ represents CR ⁴ (formula (I-1c))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＣＲ^４を表し、Ａ^３がＣＲ^４を表し、Ａ^４がＮを表すか（式（Ｉ−１ｄ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents CR ⁴ , and A ⁴ represents N (formula (I-1d))

または
ｎが１を示し、Ａ^１がＮを表し、Ａ^２がＮを表し、Ａ^３がＣＲ^４を表し、Ａ^３がＣＲ^４を表すか（式（Ｉ−１ｅ））

Or n represents ¹ , A ¹ represents N, A ² represents N, A ³ represents CR ⁴ and A ³ represents CR ⁴ (formula (I-1e))

または
ｎが１を示し、Ａ^１がＮを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＮを表し、Ａ^３がＣＲ^４を表すか（式（Ｉ−１ｆ））

Or n represents ¹ ; A ¹ represents N; A ² represents CR ⁴ ; A ³ represents N; and A ³ represents CR ⁴ (formula (I-1f))

または
ｎが１を示し、Ａ^１がＮを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＣＲ^４を表し、Ａ^４がＮを表すか（式（Ｉ−１ｇ））

Or n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents CR ⁴ , and A ⁴ represents N (formula (I-1g))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＮを表し、Ａ^３がＣＲ^４を表し、Ａ^４がＮを表すか（式（Ｉ−１ｈ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents CR ⁴ , and A ⁴ represents N (formula (I-1h))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＮを表し、Ａ^３がＮを表し、Ａ^４がＣＲ^４を表すか（式（Ｉ−１ｉ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents N, and A ⁴ represents CR ⁴ (formula (I-1i))

または
ｎが１を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＣＲ^４を表し、Ａ^３がＮを表し、Ａ^３がＮを表すか（式（Ｉ−１ｊ））

Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents N, and A ³ represents N (formula (I-1j))

または
ｎが０を示し、Ａ^１がＳを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＣＲ^４を表すか（式（Ｉ−３ａ））

Or n represents 0, A ¹ represents S, A ² represents CR ⁴ and A ³ represents CR ⁴ (formula (I-3a))

または
ｎが０を示し、Ａ^１がＳを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＮを表すか（式（Ｉ−３ｂ））

Or n represents 0, A ¹ represents S, A ² represents CR ⁴ and A ³ represents N (formula (I-3b))

または
ｎが０を示し、Ａ^１がＯを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＣＲ^４を表すか（式（Ｉ−３ｃ））

Or n represents 0, A ¹ represents O, A ² represents CR ⁴ and A ³ represents CR ⁴ (formula (I-3c))

または
ｎが０を示し、Ａ^１がＯを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＮを表すか（式（Ｉ−３ｄ））

Or n represents 0, A ¹ represents O, A ² represents CR ⁴ and A ³ represents N (formula (I-3d))

または
ｎが０を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＣＲ^４を表し、Ａ^３がＳを表すか（式（Ｉ−２ａ））

Or n represents 0, A ¹ represents CR ⁴ , A ² represents CR ⁴ and A ³ represents S (formula (I-2a))

または
ｎが０を示し、Ａ^１がＮを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＳを表すか（式（Ｉ−２ｂ））

Or n represents 0, A ¹ represents N, A ² represents CR ⁴ and A ³ represents S (formula (I-2b))

または
ｎが０を示し、Ａ^１がＣＲ^４を表し、Ａ^２がＣＲ^４を表し、Ａ^３がＯを表すか（式（Ｉ−２ｃ））

Or n represents 0, A ¹ represents CR ⁴ , A ² represents CR ⁴ and A ³ represents O (formula (I-2c))

または
ｎが０を示し、Ａ^１がＮを表し、Ａ^２がＣＲ^４を表し、Ａ^３がＯを表す（式（Ｉ−２ｄ））

Or n represents 0, A ¹ represents N, A ² represents CR ⁴ and A ³ represents O (formula (I-2d))

ことを特徴とする。

It is characterized by that.

In a preferred embodiment of the invention, the compound of general formula (I) is
n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents CR ⁴ , A ⁴ represents CR ⁴ (I-1a) or n represents 1, ¹ represents CR ⁴ ; A ² represents N; A ³ represents CR ⁴ ; A ⁴ represents CR ⁴ (I-1b) or n represents ¹ ; A ¹ represents CR ⁴ ; A ² represents CR ⁴ , A ³ represents N, A ⁴ represents CR ⁴ (I-1c) or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents CR ⁴ and A ⁴ represents N (I-1d) or n represents 0, A ¹ represents CR ⁴ , A ² represents CR ⁴ and A ³ represents S (I-2a) or n represents 0, A ¹ represents S, A ² represents CR ⁴ and A ³ represents CR ⁴ (I-3a)
It is characterized by that.

In a preferred embodiment of the invention, the compound of general formula (I) is
R ¹ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, S (= O) ₂ -C _1-4- aliphatic _{residue, CF 3, CN, C 1~4} - monosubstituted or polysubstituted by at least one substituent selected from the group consisting of aliphatic residues and _{C (= O) -OH, C} 1 _{-10 -aliphatic} residues, preferably C _{1-8 -aliphatic} residues,
Preferably, it is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue A C _{1-10 -aliphatic} residue, more preferably C _{1-8 -aliphatic} , mono- or polysubstituted with at least one substituent selected from the group consisting of a group and C (═O) OH Indicate residues,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Alternatively, R ¹ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4- Aliphatic residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _At least one substitution selected from the group consisting of _{1-4 -aliphatic} residues, C (= O) -OH, C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with a radical,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Mono- or poly-substituted with at least one substituent selected from the group consisting of group residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH _Can be linked via a _C1-4 aliphatic group, preferably a _C1-4 aliphatic group, which can be mono- or polysubstituted by substituents,
Alternatively, R ¹ is unsubstituted in each case, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4 - aliphatic _{residue) 2, OH, O-C} 1~4 - aliphatic _{residue, OCF 3, SH, SCF 3} , S-C 1~4 - aliphatic _residue, CF _{3, CN, C 1~ 4} -aliphatic residues, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ , C (═O) OC ₂ H ₅ , C _{3-6 -alicyclic} residue, 3-7 membered heteroalicyclic residue,

、ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、アリールまたはヘテロアリールを示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３および非置換Ｏ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４脂肪族残基、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＯＣＨ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
アリールまたはヘテロアリール残基は、各場合において、任意選択で、同様に非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮおよびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るＣ_１〜４−脂肪族基を介して連結し得る
ことを特徴とする。

Aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Mono- or poly-substituted with at least one substituent selected from the group consisting of group residues;
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S -C _{1 to 4} - aliphatic _{residue, CF 3, CN, C 1~4} - aliphatic _{residue, C (= O) OH,} C (= O) CH 3, C (= O) C 2 H 5 , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ may be mono- or polysubstituted with at least one substituent selected from the group consisting of:
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
An aryl or heteroaryl residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue ), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} It can be linked via a C _{1-4 -aliphatic} group that can be mono- or poly-substituted with at least one substituent selected from the group consisting of residues, CF ₃ , CN and C (═O) OH. Features.

In a further embodiment of the invention, the compound of general formula (I), the residue R ¹ has the partial structure (T1)

［式中、
ｍは、０、１、２、３または４を示し、好ましくは、０、１、２または３を示し、より好ましくは、０、１または２を示し、
Ｒ^１ａおよびＲ^１ｂは、各々互いに独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基またはＣ（＝Ｏ）−ＯＨ表すか、または一緒になって、＝Ｏを示し、
好ましくは、各々互いに独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基またはＣ_１〜４−脂肪族残基を表すか、または一緒になって、＝Ｏを示し、
より好ましくは、各々互いに独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基またはＣ_１〜４−脂肪族残基を表すか、または一緒になって、＝Ｏを示し、
さらにより好ましくは、各々互いに独立に、Ｈ、Ｆ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基またはＣ_１〜４−脂肪族残基を表すか、または一緒になって、＝Ｏを示し、
Ｒ^１ｃは、非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、Ｓ（＝Ｏ）_２−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）−ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜４−脂肪族残基を示し、
好ましくは、非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜４−脂肪族残基を示すか、
あるいは、好ましくは、ｍ≠０である場合には、各場合において非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（_〜Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３および非置換Ｏ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）−ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
あるいは、
Ｒ^１ｃは、好ましくは、ｍが０または２である場合、より好ましくは、ｍが０である場合は、各場合において非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５、Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基、

[Where:
m represents 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, more preferably 0, 1 or 2;
R ^1a and R ^1b are each independently H, F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _1-4 aliphatic residue), N (C _{1-4 -aliphatic} residue) Group) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4 aliphatic residue, CF ₃ , CN, C _{1-4 -aliphatic} residue A group or C (═O) —OH, or taken together to denote ═O,
Preferably, independently of each other, H, F, Cl, Br, I, NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, Represents an O—C _{1-4 -aliphatic} residue or a C _{1-4 -aliphatic} residue, or taken together to represent ═O,
More preferably, each independently represents H, F, Cl, Br, I, OH, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue or together. Indicates = O,
Even more preferably, each independently of each other represents H, F, OH, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue, or together, ═O Show
R ^1c is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, S (= O) ₂ -C _1-4- aliphatic _{residue, CF 3, CN, C 1~4} - aliphatic residues and C (= O) monosubstituted at least one substituent selected from the group consisting of -OH or polysubstituted _{C. 1 to 4} - represents an aliphatic residue,
Preferably, it is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue A C _{1-4 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of the group and C (= O) OH,
Alternatively, preferably if m ≠ 0, in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N _{(~ C} 1~4 - aliphatic _{residues) 2, OH, = O,} O-C 1~4 - aliphatic _{residue, OCF 3, SH, SCF 3} , S-C 1~4 - aliphatic residue From the group consisting of a group, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C _{3-6 -alicyclic} residue and 3-7 membered heteroalicyclic residue Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with at least one selected substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) —OH Or can be polysubstituted,
Or
R ^1c is preferably unsubstituted or F, Cl, Br, I, NO ₂ , NH _{2 in} each case when m is 0 or 2, more preferably when m is 0. , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H _{5, C (= O) OCH} 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue or 3-7 membered heteroalicyclic residues,

、ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたアリールまたはヘテロアリールを示し、
好ましくは、ｍが０である場合には、
各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３および非置換Ｏ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得る］
を表す。

, Aryl, or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl,
Preferably, when m is 0,
The C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue , CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ , C (═O) can be mono- or polysubstituted with at least one substituent selected from the group consisting of OC ₂ H ₅ ;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted]
Represents.

Preferably,
R ¹ represents a partial structure (T1)
[Where:
m represents 0, 1 or 2;
R ^1a and R ^1b each independently represent H, F, Cl, Br, I, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue,
R ^1c is at least selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{1-4 -aliphatic} residue which is mono- or polysubstituted by one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
R ^1c is at least selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ^1c is unsubstituted or in each case F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic residues, C (= O) CH 3} , C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue, Represents aryl or heteroaryl mono- or poly-substituted with at least one substituent selected from the group consisting of 3-7 membered heteroalicyclic residues, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH obtain]
Represents.

In a further preferred embodiment of the compound of general formula (I), the residue R ¹ has the partial structure (T1)
[Where:
m is 0, 1 or 2, preferably 0 or 2, more preferably 2,
R ^1a and R ^1b are each independently of each other H, F, OH, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue, preferably H, F, OH, CH ₃ or OCH ₃
R ^1c is unsubstituted or F, Cl, Br, I, CN, OH, unsubstituted O—C _{1-4 -aliphatic} residue, CF ₃ and unsubstituted C _{1-4 -aliphatic} residue A C _{1-4 -aliphatic} residue that is mono- or polysubstituted with at least one substituent selected from the group consisting of: preferably unsubstituted or F, Cl, Br, I, non-substituted substituted _{O-C 1 to 4} - aliphatic residue, CF ₃ and unsubstituted _{C 1 to 4} - _{C. 1 to} monosubstituted or polysubstituted by at least one substituent selected from the group consisting of aliphatic residues _4- indicates an aliphatic residue,
Alternatively, the group which is unsubstituted or in each case consists of F, Cl, Br, I, unsubstituted O—C _{1-4 -aliphatic} residue, CF ₃ and unsubstituted C _{1-4 -aliphatic} residue Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue that is mono- or polysubstituted with at least one substituent selected from
Or
Where
m is 0 or 2, more preferably 0;
R ^1a and R ^1b are each independently of each other H, F, OH, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue, preferably H, F, OH, CH ₃ or OCH ₃
R ^1c is in each case unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCF ₂ H, SCF ₃ , NO ₂ , N ( A C _{1-4 -aliphatic} residue) ₂ ,

、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５およびフェニルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、アリールまたはヘテロアリールを示し、
好ましくは、各場合において非置換であるかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５およびフェニルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたアリールまたはヘテロアリールを示し、
ここで、フェニルは、非置換であり得るかまたは一置換もしくは多置換され得る、好ましくは、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で、好ましくは、Ｆ、Ｃｌ、ＣＨ_３、ＯＣＨ_３、ＣＦ_３およびＯＣＦ_３からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得る］
を表す。

, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ , C (═O) OC ₂ H Aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of ₅ and phenyl;
Preferably, in each case unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue At least one substitution selected from the group consisting of the group C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ , C (═O) OC ₂ H ₅ and phenyl. Represents aryl or heteroaryl mono- or polysubstituted by a radical,
Here, phenyl can be unsubstituted or mono- or polysubstituted, preferably unsubstituted or F, Cl, Br, I, OH, O—C _{1-4 -aliphatic residues, OCF 3, CF 3, CN} , C 1~4 - aliphatic _{residue, C (= O) CH 3} , C (= O) C 2 H 5, C (= O) OCH 3 and C (= O) at least one substituent selected from the group consisting of OC ₂ H ₅ , preferably at least one substituent selected from the group consisting of F, Cl, CH ₃ , OCH ₃ , CF ₃ and OCF ₃ Can be mono- or poly-substituted]
Represents.

Preferably,
R ¹ represents a partial structure (T1)
[Where:
m represents 1 or 2,
R ^1a and R ^1b represent H,
R ^1c is at least selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{1-4 -aliphatic} residue which is mono- or polysubstituted by one substituent,
Or
At least one selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residues, CF ₃ and C _{1-4 -aliphatic} residues in each case Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with one substituent,
Or
m represents 0,
R ^1c is unsubstituted or in each case F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic residues, C (= O) CH 3} , C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue, Represents aryl or heteroaryl mono- or poly-substituted with at least one substituent selected from the group consisting of 3-7 membered heteroalicyclic residues, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH obtain]
Represents.

In another embodiment of the invention the compound of general formula (I) is
R ² is H, F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue, Represents an O-C _{1-4 -aliphatic} residue;
Here, the C _1-4 aliphatic residue can in each case be unsubstituted or mono- or polysubstituted,
Via a C _1-4 aliphatic group which in each case is unsubstituted or mono- or poly-substituted, optionally in each case can likewise be unsubstituted or mono- or poly-substituted It represents a linked C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue.

Preferably,
R ² is H, F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue, Represents an O-C _{1-4 -aliphatic} residue;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, ═O, OH and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
In each case, it is unsubstituted or selected from the group consisting of F, Cl, Br, I, ═O, OH, C _{1-4 -aliphatic} residues and O—C _{1-4 -aliphatic} residues. Represents a C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue which is mono- or polysubstituted with at least one substituent.
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, ═O, OH and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue can in each case be optionally unsubstituted as well, or F, Cl, Br, I, = C that may be mono- or polysubstituted with at least one substituent selected from the group consisting of O, OH, unsubstituted C _{1-4 -aliphatic} residue and unsubstituted O-C _{1-4 -aliphatic} residue _It may be linked via a _1-4 aliphatic group.

More preferably,
R ² is H, F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue, Represents an O-C _{1-4 -aliphatic} residue;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, ═O, OH and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
In each case, it is unsubstituted or consists of F, Cl, Br, I, ═O, OH, an unsubstituted C _{1-4 -aliphatic} residue and an unsubstituted O—C _{1-4 -aliphatic} residue. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperazinyl, 4-methylpiperazinyl, morpholinyl or piperidinyl, preferably cyclopropyl, cyclobutyl, mono- or polysubstituted with at least one substituent selected from the group Represents cyclopentyl or cyclohexyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, pyrrolidinyl, piperazinyl, 4-methylpiperazinyl, morpholinyl or piperidinyl in each case may optionally be likewise unsubstituted or F, Cl, OH, unsubstituted C _{1 to 4 -} aliphatic residues and unsubstituted _O-C 1~4 _- C 1~4 which may be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues _- aliphatic It can be linked via a group.

Even more preferably,
R ² is
H, F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , CH ₃ , CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) ₂ , CH ₂ (CH _{2) 2 CH 3, CH 2} CH (CH 3) 2, CH (CH 3) CH 2 CH 3, C (CH 3) 3, OCH 3, OCH 2 CH 3, O- (CH 2) 2 -OCH 3 , O— (CH ₂ ) ₂ OH; SCH ₃ , SCH ₂ CH ₃ , cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Even more preferably,
R ² is
H, F, Cl, CN, CF ₃ , OCF ₃ , SCF ₃ , CH ₃ , CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) ₂ , C (CH ₃ ) ₃ , cyclopropyl; OCH ₃ and OCH ₂ CH ₃
Selected from the group consisting of

In particular,
R ² is selected from the group consisting of H, F, Cl, CF ₃ , CF ₃ , CH ₃ , CH ₂ CH ₃ , CH (CH ₃ ) ₂ , cyclopropyl and OCH ₃ .

In another embodiment of the invention the compound of general formula (I) is
R ² represents a C _{1-4 -aliphatic} residue, preferably CH ₃ .

In another particularly preferred embodiment of the invention, the compound of general formula (I) is
R ² is not H.

In another embodiment of the invention the compound of general formula (I) is
R ³ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} A _C2-10 -aliphatic residue mono- or polysubstituted with at least one substituent selected from the group consisting of a residue and C (= O) OH;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Or
R ³ can be unsubstituted or in each case F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4 -fatty Group residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4 -aliphatic residue, CF ₃ , CN, C _{1 to 4 -} aliphatic residue and C (= O) may be mono- or polysubstituted with at least one substituent selected from the group consisting of OH, C _{3 to 6 -} cycloaliphatic residues and 3-7 membered A heteroalicyclic residue of
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Mono- or poly-substituted with at least one substituent selected from the group consisting of group residues;
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH _Can be linked via a C _1-4 -aliphatic group which can be mono- or polysubstituted by substituents,
Or
R ³ represents S—R ⁵ , O—R ⁶ or N (R ⁷ R ⁸ );
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} ) Residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1- A C _{1-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues and C (═O) OH in each case;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Alternatively, R ⁵ and R ⁶ are unsubstituted in each case, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4 - aliphatic _{residue) 2, OH, = O,} O-C 1~4 - aliphatic _{residue, OCF 3, SH, SCF 3} , S-C 1~4 - aliphatic residue, CF ₃ CN, C _{1-4 -aliphatic} residue, C (═O) OH, C _{3-6 -alicyclic} residue and at least selected from the group consisting of 3-7 membered heteroalicyclic residues Represents in each case a C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue, mono- or polysubstituted by one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Mono- or poly-substituted with at least one substituent selected from the group consisting of group residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH Can be linked via a C _1-4 -aliphatic group which can be mono- or polysubstituted with substituents;
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁷ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} C _1- or poly-substituted with at least one substituent selected from the group consisting of a residue, C (═O) —O—C _1-4 -aliphatic residue and C (═O) OH _6- represents an aliphatic residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Alternatively, R ⁷ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1- 4} -aliphatic residue) ₂ , OH, ═O, O—C _1-4, aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4, aliphatic residue, CF ₃ , CN , C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) —O—C _{1-4 -aliphatic} residue, C _3-6 -alicyclic residue and 3-7 A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of member heteroalicyclic residues Group,
Here, the C _{1-4 -aliphatic} residues can in each case be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4- May be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) —OH Or can be polysubstituted,
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _{1-4 -aliphatic} residue, C (═O) —O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue Linked via a C _{1-4 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from the group consisting of a group and C (═O) OH;
However, when R ¹¹ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4- A C _{1-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of an aliphatic residue and C (═O) OH;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _1-4 -fatty Group residue), N (C _1-4 -aliphatic residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _1-4 - aliphatic _{residue, CF 3, CN, C 1~4} - aliphatic _{residue, C (= O) -OH,} C 3~6 - cycloaliphatic residues and 3-7 membered heteroalicyclic residue Forming a 3-10 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of groups;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Mono- or poly-substituted with at least one substituent selected from the group consisting of group residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
A 3 to 10 membered heteroalicyclic residue formed by R ¹¹ and R ¹² together with the nitrogen atom connecting them may optionally be fused with an aryl or heteroaryl, aryl or heteroaryl residues fused, as, for that portion, respectively, possible or F _{unsubstituted, Cl, Br, I, NO} 2, NH 2, NH (C 1~4 - aliphatic residues ), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) —OH, C (═O) —CH ₃ , C (═O) —C ₂ H ₅ , C (═O) —OCH ₃ and _{C (= O) -OC 2 H} 5, C 3~6 - cycloaliphatic residue, 3-7 membered heteroalicyclic residue Group,

、ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、ＯＣＦ_３、ＣＦ_３および非置換Ｏ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニル、ピリジル、フリル、チアゾリルおよびオキサゾリルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＯＣＨ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＮＯ_２、ＮＨ_２、ＮＨ（Ｃ_１〜４−脂肪族残基）、Ｎ（Ｃ_１〜４−脂肪族残基）_２、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＨ、ＳＣＦ_３、Ｓ−Ｃ_１〜４−脂肪族残基、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得る
ことを特徴とする。

, Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can be mono- or polysubstituted with at least one substituent selected from the group consisting of
The C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ can be mono- or polysubstituted with at least one substituent selected from the group consisting of C (═O) OCH ₃ and C (═O) OC ₂ H ₅ ,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or It can be polysubstituted.

Preferably,
R ³ is unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4- A C _{2-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of an aliphatic residue, CF ₃ , CN and C _{1-4 -aliphatic} residue Show
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Alternatively, R ³ is unsubstituted in each case, or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , C _{3 -monosubstituted} or polysubstituted with at least one substituent selected from the group consisting of S—C _{1-4 -aliphatic} residues, CF ₃ , CN and C _{1-4 -aliphatic} residues Represents a ₆ -alicyclic residue or a 3-7 membered heteroalicyclic residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, OH, ═O, O—C _1-4 - aliphatic _{residue, OCF 3, SCF 3, CF} 3 CN , and _{C 1 to 4} - or may be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues,
Or
R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{From 1-4} aliphatic groups, NH (C _{1-4 -aliphatic} residues), N (C _{1-4 -aliphatic} residues) ₂ , CF ₃ , and C _{1-4 -aliphatic} residues Each case represents a C _{1-8 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or consist of F, Cl, Br, I, OH, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or polysubstituted with at least one substituent selected from the group;
Alternatively, R ⁵ and R ⁶ are unsubstituted in each case, or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{3-6 -alicyclic} residue or 3-7 membered heteroalicyclic, mono- or polysubstituted with at least one substituent selected from the group consisting of C _1-4 -aliphatic residues The residues are shown in each case;
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue and the 3-7 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, OH, ═O, C which may be mono- or polysubstituted with at least one substituent selected from the group consisting of O-C _1-4 -aliphatic residues, OCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residues _Can be linked via a _1-4 aliphatic group, preferably a C _1-4 aliphatic group,
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1-4 -fatty. A C _{1-6 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Alternatively, R ⁷ is unsubstituted in each case, or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue, which may be mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues Show
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or from F, Cl, OH, OCF ₃ , CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of:
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue may in each case be likewise unsubstituted or F, Cl, OH, ═O, O—C _{1 to 4} - aliphatic _{residue, OCF 3, SCF 3, CF} 3, CN and _{C 1 to 4} - _{C 1,} which may be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues _~ Can be linked via an aliphatic group, preferably linked,
However, when R ⁷ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN and C _1-4 -fatty. C _{1-6 -aliphatic} residues mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are in each case unsubstituted or F, Cl, OH, ═O, O—C _{1-4 -aliphatic} residues _3- to 10-membered heteroalicyclic mono- or poly-substituted with at least one substituent selected from the group consisting of, OCF ₃ , SCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residues Forming a heteroalicyclic residue selected from the group consisting of a residue, preferably 3-7 members, more preferably morpholinyl, piperidinyl, pyrrolidinyl, azetidinyl and piperazinyl;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group consisting of:
The 3 to 10 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them is optionally aryl or heteroaryl, preferably phenyl Or can be condensed with pyridyl,
The aryl or heteroaryl residues thus fused may be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , respectively, for that moiety. CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) —OH, C _3-6 alicyclic residue, 3-7 membered heteroalicyclic residue,

、ベンジル、フェニル、チエニルおよびピリジルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニル、チエニルおよびピリジルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＯＣＨ_３、ＳＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得る。

Monosubstituted or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl and pyridyl;
The C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Benzyl, phenyl, thienyl and pyridyl may in each case be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , mono- or poly-substituted with at least one substituent selected from the group consisting of SCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue and C (═O) OH;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, OH, ═O, O—C _1-4 - aliphatic _{residue, OCF 3, CF 3, CN} , C 1~4 - may be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH .

More preferably,
R ³ is unsubstituted or from the group consisting of F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ and C _1-4 -aliphatic residue. _Represents a _C2-6 -aliphatic residue mono- or polysubstituted with at least one selected substituent,
Where the C _{1-4 -aliphatic} residue in each case is unsubstituted or
Or R ³ is unsubstituted or in each case F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues, mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Where the C _{1-4 -aliphatic} residue in each case can be unsubstituted or mono- or polysubstituted with OH or unsubstituted O—C _{1-4 -aliphatic} residue,
The C _{3-6 -alicyclic} residue and the 3-7 membered heteroalicyclic residue may in each case optionally be linked via an unsubstituted C _{1-4 -aliphatic} group,
Or
R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. Mono- or polysubstituted with at least one substituent selected from the group consisting of:
A C _{1-6 -aliphatic} residue is indicated in each case;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or from the group consisting of F, Cl, OH, CF ₃ and unsubstituted O-C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one selected substituent;
Alternatively, R ⁵ and R ⁶ are unsubstituted in each case, or F, Cl, OH, ═O, O—C _1-4 aliphatic residue, OCF ₃ , CF ₃ and C _1-4. Each C _{3-6 -alicyclic} residue or 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues Show in case
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or from F, Cl, OH, OCF ₃ , CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of:
Can the C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic residue in each case be linked, preferably via an unsubstituted C _{1-4 -aliphatic} group? ,
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or from the group consisting of F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ and C _1-4 -aliphatic residue. Mono- or polysubstituted with at least one selected substituent,
C _1-6- represents an aliphatic residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or from the group consisting of F, Cl, OH, CF ₃ and unsubstituted O-C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one selected substituent;
Or
R ⁷ is unsubstituted or in each case F, Cl, OH, ═O, O—C _1-4 aliphatic residue, OCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue A C _{3-7 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or from F, Cl, OH, OCF ₃ , CF ₃ and unsubstituted O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of:
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may be linked via an unsubstituted C _{1-4 -aliphatic} residue;
However, when R ⁵ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is preferably selected from the group consisting of methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, s-butyl and t-butyl, more preferably the group consisting of methyl and ethyl Selected from the
_Represents an unsubstituted C _{1-4 -aliphatic} residue;
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , 3-7 membered, preferably morpholinyl, piperidinyl, pyrrolidinyl, mono- or polysubstituted with at least one substituent selected from the group consisting of ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residues Forming a heteroalicyclic residue selected from the group consisting of and azetidinyl,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or from the group consisting of F, Cl, OH, CF ₃ and unsubstituted O-C _{1-4 -aliphatic} residues. May be mono- or polysubstituted with at least one selected substituent;
The 3-7 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them can optionally be fused with phenyl or pyridyl, such as The phenyl or pyridyl residue fused to can be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, respectively, for that moiety. May be mono- or polysubstituted with at least one substituent selected from the group consisting of C _{1-4 -aliphatic} residues, benzyl, phenyl and pyridyl;
The C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least one selected from the group consisting of F, Cl, OH and unsubstituted O-C _{1-4 -aliphatic} residues Can be mono- or polysubstituted with substituents;
Benzyl, phenyl and pyridyl in each case may be unsubstituted or at least one selected from the group consisting of F, Cl, OCH ₃ , OCF ₃ , CF ₃ and C _1-4 -aliphatic residues It can be mono- or polysubstituted with substituents.

Even more preferably,
R ³ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. _Represents a C _2-6 -aliphatic residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of:
Or
In each case it is unsubstituted or consists of F, Cl, OH, ═O, O—C _1-4 -aliphatic residues, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residues A _C3-6 -alicyclic residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group;
Where the C _{1-4 -aliphatic} residue in each case can be unsubstituted or mono- or polysubstituted with OH or O—C _{1-4 -aliphatic} residues;
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue may in each case optionally be linked via a C _{1-4 -aliphatic} group,
Or
R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic.} C _{1-6 -aliphatic} residues mono- or polysubstituted with at least one substituent selected from the group consisting of residues are shown in each case;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues In each case,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or 3-7 membered heteroalicyclic residue in each case may be linked via an unsubstituted C _{1-4 -aliphatic} group,
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom. As a condition,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{1-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or R ⁷ is in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1-4- A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues;
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue is in each case linked via an unsubstituted C _{1-4 -aliphatic} group;
Provided that when R ⁷ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ represents in each case an unsubstituted C _{1-4 -aliphatic} residue, or R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or At least one selected from the group consisting of F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residue Forming a 3-7 membered heteroalicyclic residue mono- or poly-substituted with one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
The 3-7 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them can optionally be condensed with phenyl or pyridyl and thus condensed The phenyl or pyridyl residue can be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN, C, respectively, for that moiety. _May be mono- or polysubstituted with at least one substituent selected from the group consisting of _{1-4 -aliphatic} residues, C (= O) OH, benzyl, phenyl and pyridyl;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least one selected from the group consisting of F, Cl, OH and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Benzyl, phenyl and pyridyl can in each case be unsubstituted or F, Cl, OCH ₃ , OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ CH ₂ OCH ₃ , SCF ₃ , CF ₃ and C _1- It can be mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues.

More preferably,
R ³ is in each case unsubstituted or selected from the group consisting of F, Cl, OH, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue. Mono- or polysubstituted with at least one substituent
Preferably, in each case, it is unsubstituted or at least one substituent selected from the group consisting of F, Cl and O—C _{1-4 -aliphatic} residues, preferably monosubstituted with OCH ₃ or Polysubstituted,
More preferably, in each case, unsubstituted.
CH ₂ CH ₃ , CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) ₂ , CH ₂ (CH ₂ ) ₂ CH ₃ , CH ₂ CH (CH ₃ ) ₂ , CH (CH ₃ ) CH ₂ CH ₃ , C ( _{CH 3) 3, CH 2 (} CH 2) 3 CH 3, CH 2 CH 2 CH (CH 3) 2, CH 2 C (CH 3) 3, CH 2 (CH 2) 4 CH 3, CH = CH 2 or CH ₂ CH═CH ₂
Indicate
Where the C _{1-4 -aliphatic} residue in each case is unsubstituted or
Alternatively, in each case at least selected from the group consisting of unsubstituted or F, Cl, OH, O—C _{1-4 -aliphatic} residues, CF ₃ and C _{1-4 -aliphatic} residues Mono- or poly-substituted with one substituent,
Preferably, in each case, it is unsubstituted or monosubstituted with at least one substituent selected from the group consisting of F, Cl and O—C _1-4 -aliphatic residues, preferably OCH ₃ or Polysubstituted,
More preferably, in each case, unsubstituted.
Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, oxetanyl, piperidinyl, tetrahydrofuranyl or tetrahydropyranyl,
Preferably, cyclopropyl or tetrahydropyranyl,
More preferably, it represents cyclopropyl,
Here, the C _{1-4 -aliphatic} residue in each case is unsubstituted,
Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, oxetanyl, piperidinyl, tetrahydrofuranyl and tetrahydropyranyl, in each case optionally unsubstituted C _{1 to 4 -} through an aliphatic group, preferably, unsubstituted C _{1 Can} be cross-linked via an aliphatic group
Or R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are in each case when R ⁵ or R ⁶ represents piperidinyl, oxetanyl, tetrahydrofuranyl or tetrahydropyranyl, each of these residues is said to be linked via a carbon atom. Condition
In each case, unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F, Cl, OH and O—C _{1-4 -aliphatic} residues,
_{CH 3, CH 2 CH 3,} CH 2 CH 2 CH 3, CH (CH 3) 2, CH 2 (CH 2) 2 CH 3, CH 2 CH (CH 3) 2, CH (CH 3) CH 2 CH 3 , C (CH ₃ ) ₃ , CH ₂ (CH ₂ ) ₃ CH ₃ , CH ₂ CH ₂ CH (CH ₃ ) ₂ , CH ₂ C (CH ₃ ) ₃ , CH ₂ (CH ₂ ) ₄ CH ₃ , CH = CH ₂ or CH ₂ CH═CH ₂
Indicate
Where the C _{1-4 -aliphatic} residue in each case is unsubstituted or
Alternatively, in each case at least selected from the group consisting of unsubstituted or F, Cl, OH, O—C _{1-4 -aliphatic} residues, CF ₃ and C _{1-4 -aliphatic} residues Mono- or poly-substituted with one substituent,
Preferably, in each case, it is unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F, Cl and O—C _{1-4 -aliphatic} residues, Preferably, in each case, unsubstituted, cyclopropyl, cyclobutyl, cyclopentyl cyclohexyl, oxetanyl, piperidinyl, tetrahydrofuranyl or tetrahydropyranyl, preferably cyclopropyl or oxetanyl is indicated in each case,
Here, the C _{1-4 -aliphatic} residue in each case is unsubstituted,
Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, oxetanyl, piperidinyl, tetrahydrofuranyl and tetrahydropyranyl may in each case optionally be linked via an unsubstituted C _{1-4 -aliphatic} group,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F, Cl, ═O, OH and OCH ₃ ,
Preferably, it is unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F, Cl and OCH ₃ .
More preferably, it represents a C _{1-6 -aliphatic} residue which is unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F and OCH ₃ ;
Preferably, an unsubstituted C _{1-6 -aliphatic} residue,
More preferably,
_{CH 3, CH 2 CH 3,} CH 2 CH 2 CH 3, CH (CH 3) 2, CH 2 (CH 2) 2 CH 3, CH 2 CH (CH 3) 2, CH (CH 3) CH 2 CH 3 , C (CH ₃ ) ₃ , CH ₂ (CH ₂ ) ₃ CH ₃ , CH ₂ CH ₂ CH (CH ₃ ) ₂ , CH ₂ C (CH ₃ ) ₃ and CH ₂ (CH ₂ ) ₄ CH ₃
Is selected from the group consisting of
R ⁸ is
_{CH 3, CH 2 CH 3,} CH 2 CH 2 CH 3, CH (CH 3) 2, CH 2 (CH 2) 2 CH 3, CH 2 CH (CH 3) 2, CH (CH 3) CH 2 CH 3 Or C (CH ₃ ) ₃ ,
More preferably CH ₃ or CH ₂ CH ₃
Or
Or
R ⁷ and R ⁸ , together with the nitrogen atom connecting them, in each case are unsubstituted or F, Cl, OH, O—C _{1-4 -aliphatic} residues and C _1- Mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues,
More preferably, morpholinyl, piperidinyl, which is unsubstituted or mono- or polysubstituted with at least one substituent selected from the group consisting of F, Cl and O—C _{1-4 -aliphatic} residues, Form pyrrolidinyl or azetidinyl, or
Preferably, together with the nitrogen atoms connecting them form in each case unsubstituted morpholinyl, piperidinyl, pyrrolidinyl or azetidinyl.

In certain preferred embodiments of the invention the compound of general formula (I) is
R ³ is
In each case, C ₂ H ₅ , CH ₂ CH ₂ CH ₃ , CH (CH ₃ ) ₂ , CH ₂ CH ₂ CH that are unsubstituted or mono- or polysubstituted by F, OH and / or OCH _{3 2 CH 3, CH 2 CH (} CH 3) 2, CH (CH 3) CH 2 CH 3, C (CH 3) 3, CH 2 - _{cyclopropyl, OCH 3, OC 2 H 5} , OCH 2 CH 2 CH 3 , OCH (CH ₃ ) ₂ , O-cyclopropyl, SCH ₃ , SC ₂ H ₅ , SCH ₂ CH ₂ CH ₃ , SCH (CH ₃ ) ₂ , S-cyclopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, N _{(CH 3) 2, N (} CH 3) C 2 H 5, N (CH 3) CH 2 CH 2 CH 3, N (CH 3) CH (CH 3) 2, N (CH 3 - _{cyclopropyl, N (C 2 H 5)} 2, N (C 2 H 5) CH 2 CH 2 CH 3, N (C 2 H 5) CH (CH 3) 2, N (C 2 H 5) - cyclo It is selected from the group consisting of propyl, N-aziridinyl, N-azetidinyl, N-pyrrolidinyl, N-piperidinyl or N-morpholinyl.

In another embodiment of the invention the compound of general formula (I) is
Each R ⁴ is
Independently, H, F, Cl, Br, I, CN, CF ₃ , CHF ₂ , CH ₂ F, OCF ₃ , OCHF ₂ , OCH ₂ F, SCF ₃ , O—C _{1-4 -aliphatic} residue, It represents a C _{1-4 -aliphatic} residue or S (═O) ₂ -C _{1-4 -aliphatic} residue.

Preferably,
Each R ⁴ independently represents H, F, Cl, Br, CN, CF ₃ , OCF ₃ , CH ₃ , OCH ₃ or S (═O) ₂ CH ₃ .

More preferably,
Each R ⁴ independently represents H or CF ₃ .

In one preferred embodiment of the invention, each R ⁴ represents H.

In another preferred embodiment of the invention, at least one R ⁴ does not represent H.

In another preferred embodiment of the invention, at least one R ⁴ represents CF ₃ .

In a particularly preferred embodiment of the invention, the compound of general formula (I) is
A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
However,
when n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N;
R ¹ represents a partial structure (T1)

［式中、
ｍは、０、１または２を示し、
Ｒ^１ａおよびＲ^１ｂは、各々互いに独立に、Ｈ、Ｆ、Ｃｌ、Ｏ−Ｃ_１〜４−脂肪族残基またはＣ_１〜４−脂肪族残基を表し、
Ｒ^１ｃは、非置換であるかまたはＦ、Ｃｌ、Ｏ−Ｃ_１〜４−脂肪族残基、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_１〜４−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
各場合において非置換であるかまたはＦ、Ｃｌ、Ｏ−Ｃ_１〜４−脂肪族残基、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
Ｒ^１ｃは、各場合において非置換であるかまたはＦ、Ｃｌ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、ベンジル、フェニル、チエニルまたはピリジルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、アリールまたはヘテロアリールを示し、
ここで、ベンジル、フェニル、チエニルおよびピリジルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｒ^２が、Ｆ、Ｃｌ、Ｂｒ、Ｉ、ＣＮ、ＣＦ_３、ＮＯ_２、ＯＣＦ_３、ＳＣＦ_３、Ｃ_１〜４−脂肪族残基、Ｓ−Ｃ_１〜４−脂肪族残基またはＯ−Ｃ_１〜４−脂肪族残基を表し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、＝Ｏ、ＯＨおよびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｒ^３が、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_２〜６−脂肪族残基を示すか、
あるいは、
各場合において、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るか、またはＯＨもしくはＯ−Ｃ_１〜４−脂肪族残基で一置換もしくは多置換され得、
Ｃ_３〜１０−脂環式残基または３〜１０員のヘテロ脂環式残基は、各場合において、任意選択で、Ｃ_１〜４−脂肪族基を介して連結し得るか、
あるいは、
Ｒ^３が、Ｓ−Ｒ^５またはＯ−Ｒ^６を示し、
ここで、
Ｒ^５およびＲ^６は、Ｒ^５またはＲ^６が、３〜７員のヘテロ脂環式残基を示す場合には、３〜７員のヘテロ脂環式残基は、炭素原子を介して連結するという条件で、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜８−脂肪族残基を各場合において示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
Ｒ^５およびＲ^６は、各場合において、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された、Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基を各場合において示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各場合におけるＣ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基は、非置換Ｃ_１〜４−脂肪族基を介して連結し得るか、
あるいは、
Ｒ^３が、Ｎ（Ｒ^７Ｒ^８）を示し、
ここで、
Ｒ^７は、Ｒ^７が、３〜７員のヘテロ脂環式残基を示す場合には、３〜７員のヘテロ脂環式残基は、炭素原子を介して連結するという条件で、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜８−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得るか、
あるいは、
Ｒ^７は、各場合において、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、Ｃ（＝Ｏ）−Ｏ−Ｃ_１〜４−脂肪族残基、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＯＣＦ_３、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基または３〜７員のヘテロ脂環式残基は、各場合において、非置換Ｃ_１〜４−脂肪族基を介して連結し、
Ｒ^８は、非置換Ｃ_１〜４−脂肪族残基を示すか、
あるいは、
Ｒ^７およびＲ^８は、それらを接続する窒素原子と一緒になって、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３、ＣＮおよびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換された３〜７員のヘテロ脂環式残基を形成し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
それらを接続する窒素原子と一緒になってＲ^７およびＲ^８によって形成される３〜７員のヘテロ脂環式残基は、任意選択で、フェニルまたはピリジルと縮合し得、このように縮合するフェニルまたはピリジル残基は、その部分について、それぞれ、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＯＨ、ベンジル、フェニルおよびピリジルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨおよびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
ベンジル、フェニルおよびピリジルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、ＯＣＨ_３、ＯＣＦ_３、ＯＣＨ_２ＣＨ_２ＯＨ、ＯＣＨ_２ＣＨ_２ＯＣＨ_３、ＳＨ、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各Ｒ^４が独立に、Ｈ、Ｆ、Ｃｌ、Ｂｒ、ＣＮ、ＣＦ_３、ＯＣＦ_３、ＣＨ_３、ＯＣＨ_３またはＳ（＝Ｏ）_２ＣＨ_３を表す
ことを特徴とする。

[Where:
m represents 0, 1 or 2;
R ^1a and R ^1b each independently represent H, F, Cl, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue,
R ^1c is unsubstituted or at least one substituent selected from the group consisting of F, Cl, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue A C _{1-4 -aliphatic} residue which is _mono- or polysubstituted with
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
In each case unsubstituted or with at least one substituent selected from the group consisting of F, Cl, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue Represents a mono- or polysubstituted C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
R ^1c is unsubstituted or in each case F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue, C _{(= O) CH 3, C} (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue, 3-7 membered An aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of a heteroalicyclic residue of benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH Get
R ² is F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue or O- _{Represents a} C _{1-4 -aliphatic} residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, ═O, OH and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
R ³ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{2-6 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of:
Or
In each case, it is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with at least one substituent selected from the group consisting of:
Where the C _{1-4 -aliphatic} residue in each case can be unsubstituted or mono- or polysubstituted with OH or O—C _{1-4 -aliphatic} residues;
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case optionally be linked via a C _{1-4 -aliphatic} group,
Or
R ³ represents S—R ⁵ or O—R ⁶ ;
here,
R ⁵ and R ⁶ , when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom. Or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue, provided that A C _{1-8 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues In each case,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or 3-7 membered heteroalicyclic residue in each case may be linked via an unsubstituted C _{1-4 -aliphatic} group,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is a non-reactive compound, provided that when R ⁷ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom. Is substituted or selected from the group consisting of F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue A C _{1-8 -aliphatic} residue which is mono- or polysubstituted with at least one substituent
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁷ is in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , C (═O) —O—C _{1-4 -} aliphatic residue, CF ₃ and C _{1-4 -} at least one substituent selected from the group consisting of aliphatic residues mono- or polysubstituted C _{3 to 6 -} cycloaliphatic residue A group or a 3-7 membered heteroalicyclic residue,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue is in each case linked via an unsubstituted C _{1-4 -aliphatic} group;
R ⁸ represents an unsubstituted C _{1-4 -aliphatic} residue,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF Forming a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₃ , CF ₃ , CN and C _1-4 -aliphatic residues ,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
The 3-7 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them can optionally be condensed with phenyl or pyridyl and thus condensed The phenyl or pyridyl residue can be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN, C, respectively, for that moiety. _May be mono- or polysubstituted with at least one substituent selected from the group consisting of _{1-4 -aliphatic} residues, C (= O) OH, benzyl, phenyl and pyridyl;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least one selected from the group consisting of F, Cl, OH and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Benzyl, phenyl and pyridyl may in each case be unsubstituted or F, Cl, OCH ₃ , OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ CH ₂ OCH ₃ , SH, SCF ₃ , CF ₃ and C _May be mono- or polysubstituted with at least one substituent selected from the group consisting of _1-4 aliphatic groups;
Each R ⁴ independently represents H, F, Cl, Br, CN, CF ₃ , OCF ₃ , CH ₃ , OCH ₃ or S (═O) ₂ CH ₃ .

In a more particularly preferred embodiment of the invention the compound of general formula (I) is
A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
However,
when n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N;
R ¹ represents a partial structure (T1)

［式中、
ｍは、０を示し、
Ｒ^１ｃは、非置換であるかまたはＦ、Ｃｌ、ＯＨ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３、Ｃ（＝Ｏ）ＯＣ_２Ｈ_５、Ｃ_３〜６−脂環式残基、３〜７員のヘテロ脂環式残基、ベンジル、フェニル、チエニルまたはピリジルからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたアリールまたはヘテロアリールを示し、
ここで、ベンジル、フェニル、チエニルおよびピリジルは、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３、ＣＮ、Ｃ_１〜４−脂肪族残基、Ｃ（＝Ｏ）ＣＨ_３、Ｃ（＝Ｏ）Ｃ_２Ｈ_５、Ｃ（＝Ｏ）ＯＣＨ_３およびＣ（＝Ｏ）ＯＣ_２Ｈ_５からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
Ｃ_３〜６−脂環式残基および３〜７員のヘテロ脂環式残基は、各場合において、非置換であり得るかまたはＦ、Ｃｌ、Ｂｒ、Ｉ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＣＦ_３ Ｃ_１〜４−脂肪族残基およびＣ（＝Ｏ）ＯＨからなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得る］
を表し、
Ｒ^２は、Ｆ、Ｃｌ、ＣＮ、ＣＦ_３、ＯＣＦ_３、ＣＨ_３またはＯＣＨ_３を表し、
Ｒ^３は、Ｓ−Ｒ^５またはＯ−Ｒ^６を示し、
ここで、
Ｒ^５およびＲ^６は、各場合において、非置換であるかまたはＦ、Ｃｌ、ＯＨ、＝Ｏ、Ｏ−Ｃ_１〜４−脂肪族残基、ＯＣＦ_３、ＳＣＦ_３、ＣＦ_３およびＣ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換されたＣ_１〜８−脂肪族残基を示し、
ここで、各場合におけるＣ_１〜４−脂肪族残基は、非置換であり得るかまたはＦ、Ｃｌ、ＯＨ、ＣＦ_３およびＯ−Ｃ_１〜４−脂肪族残基からなる群から選択される少なくとも１つの置換基で一置換もしくは多置換され得、
各Ｒ^４は独立に、Ｈ、Ｆ、ＣｌまたはＣＦ_３を表す
ことを特徴とする。

[Where:
m represents 0,
R ^1c is unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O _{) CH 3, C (= O} ) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue, 3-7 membered heteroalicyclic Represents aryl or heteroaryl mono- or poly-substituted with at least one substituent selected from the group consisting of a cyclic residue, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl may in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H Mono- or poly-substituted with at least one substituent selected from the group consisting of ₅ ;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH obtain]
Represents
R ² represents F, Cl, CN, CF ₃ , OCF ₃ , CH ₃ or OCH ₃ ,
R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1- A C _{1-8 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Each R ⁴ independently represents H, F, Cl or CF ₃ .

Each as a racemate, as an individual enantiomer, as an individual diastereomer, as a mixture of enantiomers of any mixing ratio, or as a mixture of diastereomers of any mixing ratio, free compounds, solvates In the form of products and / or physiologically acceptable salts,
1 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,5] naphthyridine-3-carboxylic acid amide;
2 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,5] naphthyridine-3-carboxylic acid amide;
3 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide;
4 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide;
5 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide;
6 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide;
7 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,8] naphthyridine-3-carboxylic acid amide;
8 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,8] naphthyridine-3-carboxylic acid amide;
9 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,8] naphthyridine-3-carboxylic acid amide;
10 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,8] naphthyridine-3-carboxylic acid amide;
11 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,6] naphthyridine-3-carboxylic acid amide;
12 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,6] naphthyridine-3-carboxylic acid amide;
13 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide;
14 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide;
15 5-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -7-methyl-thieno [3,2-b] pyridine-6-carboxylic acid amide;
16 6-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-thieno [2,3-b] pyridine-5-carboxylic acid amide;
17 5-ethoxy-N-[(3-fluorophenyl) -methyl] -7-methyl-2- (trifluoromethyl) -thieno [3,2-b] pyridine-6-carboxylic acid amide;
18 selected from the group comprising 6-ethoxy-N-[(3-fluorophenyl) -methyl] -4-methyl-2- (trifluoromethyl) -thieno [2,3-b] pyridine-5-carboxylic acid amide Especially preferred are the compounds of the general formula (I)

  The compounds of the general formula (I) and the corresponding stereoisomers as well as the respective corresponding salts and solvates are toxicologically safe and are therefore suitable as pharmaceutically active ingredients in pharmaceutical compositions.

  Thus, in another aspect, the invention further comprises in each case where appropriate the pure stereoisomer, in particular one of the enantiomers or diastereomers, in the form of its racemates, or In any desired mixing ratio, in the form of stereoisomers, in particular in the form of mixtures of enantiomers and / or diastereomers, or in the form of physiologically acceptable salts, or in the corresponding solvates, respectively. It relates to a pharmaceutical composition containing at least one compound of general formula (I) in the form of a substance and also, where appropriate, one or more pharmaceutically acceptable auxiliaries.

These pharmaceutical compositions of the invention are particularly suitable for the modulation of KCNQ2 / 3 K ⁺ channels, preferably for KCNQ2 / 3 K ⁺ channel inhibition and / or KCNQ2 / 3 K ⁺ channel stimulation, ie Exerts an agonistic or antagonistic effect.

Similarly, the pharmaceutical composition of the present invention is preferably suitable for the prevention and / or treatment of disorders and / or diseases mediated at least in part by the KCNQ2 / 3 K ⁺ channel. The pharmaceutical compositions of the present invention are suitable for administration to adults and children, including infants and infants.

  The pharmaceutical composition of the present invention is, for example, an injection solution, droplet, juice, syrup, spray, suspension, tablet, patch, capsule, plaster, suppository, ointment, cream, lotion, gel, emulsion, In the form of an aerosol or multiparticulate, for example, if appropriate, compressed into tablets, decanted into capsules or suspended in liquid, and just administered in pellets or granules It can be prepared as a liquid, semi-solid or solid pharmaceutical form.

  Where appropriate, its pure stereoisomers, especially one of its enantiomers or diastereomers, its racemic form, or any desired mixing ratio of stereoisomers, especially its enantiomers. At least one substitution of the general formula (I) in the form of a mixture of isomers and / or diastereomers or, where appropriate, in the form of the corresponding salts or in the form of the corresponding solvates, respectively. In addition to the compounds, the pharmaceutical compositions of the present invention are conventionally used in, for example, excipients, bulking agents, solvents, diluents, surfactants, dyes, preservatives, blasting agents, slip additives. Further physiologically acceptable pharmaceutical auxiliaries which can be selected from the group consisting of lubricants, fragrances and binders.

  The choice of physiologically acceptable adjuvants and also the amount used is determined so that the pharmaceutical composition is orally, subcutaneously, parenterally, intravenously, against skin, mucosal and ocular infections. Depending on whether applied intraperitoneally, intradermally, intramuscularly, intranasally, buccal, rectally or topically. Preparations in the form of tablets, dragees, capsules, granules, pellets, droplets, juices and syrups are preferably suitable for oral application; solutions, suspensions, easily reconstituted dry preparations And also preferably the spray is suitable for parenteral, topical and inhalation applications. The replacement compounds of the present invention used in the pharmaceutical composition of the present invention in the dissolved form of the repository or in the plaster and the additional agents that promote skin penetration added where appropriate are suitable It is a preparation for skin application. Preparation forms which can be applied orally or transdermally can also release the respective substituted compounds of the invention in a delayed manner.

  The pharmaceutical composition of the present invention is disclosed in, for example, “Remington's Pharmaceutical Sciences”, A.I. R. Conventional means and devices known in the art, such as those described in Gennaro (ed.), 17th edition, Mack Publishing Company, Easton, Pa, 1985, in particular, Part 8, Chapters 76-93. Can be prepared using methods and processes. The corresponding description is hereby incorporated by reference and forms part of the present disclosure. The amount administered to the patient of each of the substituted compounds of the invention of general formula (I) shown above can vary, for example depending on the weight or age of the patient and the type of application, indications and disorders It depends on the severity. Conventionally, 0.001 to 100 mg / kg, preferably 0.05 to 75 mg / kg, particularly preferably 0.05 to 50 mg of at least one compound of the invention is applied per kg of patient body weight. .

The pharmaceutical composition of the invention is preferably suitable for the prevention and / or treatment of disorders and / or diseases mediated at least in part by the KCNQ2 / 3 K ⁺ channel. The pharmaceutical composition of the present invention is pain, in particular acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and pain selected from the group consisting of inflammatory pain, epilepsy, urinary incontinence, anxiety, dependence More preferably, it is suitable for the treatment and / or prevention of one or more diseases and / or disorders selected from the group consisting of symptom, mania, bipolar disorder, migraine, cognitive disease and dystonia-related dyskinesia.

  It is particularly preferred that the pharmaceutical composition of the present invention is suitable for the treatment of pain, more particularly suitable for the treatment of acute pain, chronic pain, neuropathic pain, visceral pain, inflammatory pain and muscle pain. Preferably, it is most particularly preferred that it is suitable for the treatment of neuropathic pain.

  The pharmaceutical composition of the present invention is also preferably suitable for the treatment and / or prevention of epilepsy.

Accordingly, in a further aspect of the invention, the invention provides at least one of the general formula (I) for the prevention and / or treatment of disorders and / or diseases mediated at least in part by KCNQ2 / 3 K ⁺ channels. And, where appropriate, one or more pharmaceutically acceptable adjuvants.

  Pain, especially acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and inflammatory pain, epilepsy, urinary incontinence, anxiety, addiction, mania, bipolar disorder, At least one compound of general formula (I) and optionally one or more for the prevention and / or treatment of disorders and / or diseases selected from the group consisting of migraine, cognitive diseases and dystonia-related dyskinesia A plurality of pharmaceutically acceptable adjuvants are preferred.

  Pain, particularly acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and disorders and / or diseases selected from the group consisting of pain selected from the group consisting of inflammatory pain, most particularly nerves Particularly preferred are at least one compound of general formula (I) and optionally one or more pharmaceutically acceptable adjuvants for the prevention and / or treatment of disabling pain.

  Also particularly preferred are at least one compound of general formula (I) and optionally one or more pharmaceutically acceptable adjuvants for the prevention and / or treatment of epilepsy.

In another aspect of the present invention, the present invention further relates to a general use for the preparation of a medicament for the prevention and / or treatment of disorders and / or diseases mediated at least in part by KCNQ2 / 3 K ⁺ channels. It relates to at least one compound of formula (I) and, if appropriate, one or more pharmaceutically acceptable auxiliaries.

  Pain, in particular acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and pain selected from the group consisting of inflammatory pain, epilepsy, urinary incontinence, anxiety, addiction, mania, bipolar disorder, At least one compound of general formula (I) for use in the preparation of a medicament for the prevention and / or treatment of disorders and / or diseases selected from the group consisting of migraine, cognitive diseases and dystonia-related dyskinesia And optionally, one or more pharmaceutically acceptable adjuvants are preferred.

  Pain, particularly acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and disorders and / or diseases selected from the group consisting of pain selected from the group consisting of inflammatory pain, most particularly nerves At least one compound of general formula (I) and optionally one or more pharmaceutically acceptable adjuvants for use in the preparation of a medicament for the prevention and / or treatment of disabling pain Is particularly preferred.

  Also particularly preferred are at least one compound of general formula (I) and optionally one or more pharmaceutically acceptable adjuvants for use in the preparation of a medicament for the prevention and / or treatment of epilepsy. preferable.

Another aspect of the invention is a disorder mediated at least in part by a KCNQ2 / 3 K ⁺ channel in a mammal comprising administering to the mammal an effective amount of at least one compound of general formula (I) / Or disease, preferably pain, preferably acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and inflammatory pain, epilepsy, urinary incontinence, anxiety, A method for the treatment and / or prevention of disorders and / or diseases selected from the group consisting of addiction, mania, bipolar disorder, migraine, cognitive illness and dystonia-related dyskinesia.

  Efficacy for pain has been demonstrated, for example, in the Bennett or Chung model (Bennett, GJ and Xie, YK, A peripheral monoeuropathies in the rate of affairs of affairs of oils in the world. Pain 1988, 33 (1), 87-107; Kim, SH and Chung, J. M., An animeral model for peripheral neuropathic produced by segmental spinnery 92. Year, Volume 50 (3 ), 355-363), by tail flick experiments (eg by D'Amour and Smith (J. Pharm. Exp. Ther. 72, 74 79 (1941)) or by the formalin test (eg D. Dubuisson et al., Pain 1977, Vol. 4, pp. 161-174) Efficacy against epilepsy can be demonstrated, for example, in the DBA / 2 mouse model (De Sarro et al., Naunyn-Schmiedeberg's Arch. Pharmacol. 2001). 363, 330-336).

The compounds of the present invention preferably have an EC ₅₀ value of 10000 nM or less or 8000 nM or less, more preferably 7000 nM or less or 6000 nM or less, still more preferably 5000 nM or less or 3000 nM or less, even more preferably 2000 nM or less or 1000 nM or less, 800 nM or less or 700 nM or less is even more preferred, 600 nM or less or 500 nM or less is even more preferred, 400 nM or less or 300 nM or less is even more preferred, 200 nM or less or 150 nM or less is most preferred, and 120 nM or less or 100 nM or less is especially preferred. Methods for determining EC ₅₀ values are known to those skilled in the art. EC ₅₀ values are preferably determined by fluorimetry, particularly preferably as described below under “Pharmacological experiments”.

  The present invention further provides methods for preparing the substituted compounds of the present invention.

  The chemicals and reaction components used in the reactions and schemes described below are either commercially available or in each case can be prepared by conventional methods known to those skilled in the art.

  The reactions described can each be carried out under conventional conditions that one skilled in the art is familiar with, for example, pressure or the order in which the components are added. Where appropriate, one skilled in the art can determine the optimal procedure under each condition by performing a simple preliminary test. The intermediates and final products obtained using the reactions described hereinabove are each purified and used, if desired and / or necessary, using conventional methods known to those skilled in the art. And / or isolated. Suitable purification methods are, for example, extraction methods and chromatographic methods such as column chromatography or preparative chromatography. All of the process steps described below and the respective purification and / or isolation of the intermediates or final products can be carried out partially or completely under an inert gas atmosphere, preferably under a nitrogen atmosphere.

  When the compound of the general formula (I) is obtained after its preparation in the form of a mixture of its stereoisomers, preferably in the form of its racemates or other mixtures of various enantiomers and / or diastereomers Alternatively, they can be separated using conventional methods known to those skilled in the art and, where appropriate, isolated. Examples include chromatographic separation methods at normal or high pressure, in particular liquid chromatography methods, preferably MPLC and HPLC methods, and fractional crystallization methods. These methods involve individual enantiomers formed by chiral stationary phase HPLC or by crystallization with chiral acids such as (+)-tartaric acid, (−)-tartaric acid or (+)-10-camphorsulfonic acid. Bodies, e.g. diastereomeric salts, can be separated from one another.

  Various, particularly preferred, embodiments of the first aspect of the invention apply to other aspects of the invention, in a similar manner, with modifications where appropriate.

  The compounds of the invention can be prepared as shown in the following reaction scheme:

When A ¹ , A ² , A ³ or A ⁴ represents CR ⁴ , a plurality of compounds of general formula SNS-001 having a large number of residues R ² and having a very wide substitution pattern of residues R ⁴ Synthesis and synthesis routes are known in the current expert literature. Previously unknown intermediates of general formula SNS-001, which have similar substitution patterns for residues R ² and R ⁴ as outlined below and whose synthesis has not been described in more detail, are these Can be generated by those skilled in the art according to any known method or by a combination of known methods.

In stage-01, the amino-ketone of the general formula SNS-01 is for example an acid chloride of the general formula Cl (C═O) —CH ₂ — (C═O) —O (Me / Et). According to methods known to the person skilled in the art, it can be converted into an amide of general formula SNS-02, for example by addition of a base, for example NEt ₃ .

  In stage-02, the amide-ketone of general formula SNS-02 can be prepared according to methods known to those skilled in the art, for example by addition of a base such as NaH or NaOEt in a suitable solvent such as EtOH. It can be cyclized to quinolone of SNS-03.

  In stage-03, a quinolone of general formula SNS-03 can be converted to a quinoline thione of general formula SNS-04 according to methods known to those skilled in the art, for example, by using Lawson's reagent.

In Stage-04, the quinoline thione of the general formula SNS-04 uses a compound of the general formula X-R ⁵ (wherein X represents a leaving group such as methylsulfonyl or a halide such as chlorine). Can be converted to 2-mercapto-quinoline of general formula SNS-06 according to methods known to those skilled in the art, for example by addition of a base, for example K ₂ CO ₃ or NEt ₃ .

In stage -05, quinolones of general formula SNS-03, according to methods known to those skilled in the art, for example, by the use of POCl ₃ reagents, Formula SNS-07 2-chloro - may be converted to quinoline.

In stage-06, 2-chloro-quinoline of general formula SNS-07 is, for example, a compound of general formula MSR ⁵ (wherein M represents a hydrogen atom or a metal, such as sodium or potassium). Can be converted to 2-mercapto-quinoline of general formula SNS-06, for example by addition of a base such as K ₂ CO ₃ or NEt ₃ according to methods known to those skilled in the art.

In stage-07, 2-chloro-quinoline of the general formula SNS-07 is, for example, a compound of the general formula M—O—R ⁵ , wherein M represents a hydrogen atom or a metal, such as sodium or potassium. Can be converted to 2-alkoxyoxy-quinoline of general formula SNS-05, for example by addition of a base such as NaH or NaOH, according to methods known to those skilled in the art.

In stage 08, the 2-chloro-quinoline of general formula SNS-07 is prepared using an amine of general formula HNR ⁷ R ⁸ according to methods known to those skilled in the art, for example by addition of a base, for example NEt ₃ It can be converted to 2-amino-quinoline of formula SNS-05.

Residues quinoline of the general formula ^{X-R 3} (wherein, or X is for forming an organometallic reagent, for example, MgBr, the MgCl or _Bu 3 Sn - In stage -09, 2-chloro formula SNS-07 Optionally in the presence of a suitable base such as NEt ₃ , DIPEA, K ₂ CO ₃ , Cs ₂ CO ₃ , NaOtBu or KOtBu, according to methods known to those skilled in the art in selected, appropriate coupling reagent, for _{example, Pd (PPh 3) 4,} Ni (dppp) by the addition of Cl ₂ or Fe _{(acac) 3,} generally ^{R 3} is bonded via a carbon atom type SNS- It can be converted to 09 2-alkyl-quinoline.

In stage-10, the quinolinone of general formula SNS-04 uses a compound of general formula X-R ⁶ (wherein X represents a leaving group such as methylsulfonyl or a halide such as chlorine) according to methods known to those skilled in the art, for example, a base, for _example, by the addition of _{Ag 2 CO 3, K 2 CO} 3 or NEt _3, the general formula SNS-06 of 2-alkoxy - may be converted to quinoline.

  In stage-11, the methyl or ethyl ester of general formula SNS-10 can be converted to the corresponding acid of general formula SNS-11 according to methods known to those skilled in the art, for example by use of a base, for example LiOH.

In stage-12, the acid of general formula SNS-11 uses an amine of general formula R ¹ —CH ₂ —NH ₂ and uses, for example, a suitable coupling reagent, eg, HATU, according to methods known to those skilled in the art. Can be converted to the amides of general formula I.

In stage -13 methyl or ethyl ester of general formula SNS-10 is an amine of general formula ^R 1 _{-CH 2} -NH 2, according to methods known to those skilled in the art, for example, a suitable coupling reagent, for example, By using trimethyl-alumina, it can be converted to the amide of general formula (I).

  The designation “equivalent” (“eq.”) Means molar equivalents, “RT” means room temperature (23 ± 7 ° C.), “M” is an indication of the concentration in mol / l, “Aq.” Means aqueous, “sat.” Means saturation, “sol.” Means solution, “conc.” Means concentrated.

Further abbreviations:
Brine Saturated aqueous sodium chloride solution Column chromatography on silica gel DCM Dichloromethane DMF N, N-dimethylformamide EtOAc Ethyl acetate h Time HATU O- (7-aza-benzotriazol-1-yl) -N, N, N ′, N '-Tetramethyluronium hexafluorophosphate m / z Mass to charge ratio LR Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4- Dithione)
min min MS mass spectrometry TEA triethylamine RM reaction mixture v / v volume in volume w / w weight in weight

  The yield of the prepared compound was not optimized. All temperatures were uncorrected. All starting materials not explicitly stated are commercially available (e.g. supplier details such as Acros, Avocado, Aldrich, Bachem, Fluka, Lancaster, Maybridge, Merck, Sigma, TCI, Oakwood etc.) MDL's Symyx (R) Available Chemicals Database, San Ramon, US or ACS's SciFinder (R) Database, Washington DC, US, respectively, or their synthesis is already accurate in the specialist literature (Experimental guidelines are described, for example, in Elsevier's Reaxys® Database, Amst, respectively. Rdam, NL or the ACS SciFinder (R) Database, Washington DC, can be found in US) or may be prepared using conventional methods known to those skilled in the art.

  The mixing ratio of the chromatographic solvent or eluent is specified in v / v.

All intermediate products and exemplary compounds were analytically characterized by ¹ H-NMR spectroscopy. In addition, mass spectrometry studies (MS, [M + H] ⁺ m / z) were performed on all exemplary compounds and selected intermediate products.

Synthesis of Exemplary Compounds Synthesis of Example 1: 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic Acid amide

a) Synthesis of ethyl 3- (2-acetyl-5- (trifluoromethyl) pyridin-3-ylamino) -3-oxopropanoate 1- (3-amino-5- (tri) in DCM (20 ml) To a solution of fluoromethyl) pyridin-2-yl) ethanone (0.87 g, 4.26 mmol, 1 eq) at 0 ° C. TEA (0.65 ml, 4.69 mmol, 1.1 eq) and ethyl 3-chloro- 3-Oxopropanoate (0.71 ml, 5.54 mmol, 1.3 eq) was added. The reaction mixture was stirred at room temperature for 3 hours. The mixture was then diluted with water (50 ml) and extracted with DCM (3 × 80 ml). The combined organic layers were washed with water (80 ml), dried over anhydrous Na ₂ SO ₄ , concentrated in vacuo and ethyl 3- (2-acetyl-5- (trifluoromethyl) pyridin-3-ylamino) -3 -Oxopropanoate (1.35 g, 4.24 mmol, 99%) was obtained and used in the subsequent reaction without further purification.

b) Synthesis of ethyl 2-hydroxy-4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate Ethyl 3- (2-acetyl-5- (trimethyl) in ethanol (15 ml) A cooled (ice water batch) suspension of fluoromethyl) pyridin-3-ylamino) -3-oxopropanoate (1.35 g, 4.24 mmol, 1 eq) is added to NaH (in oil, 60% w / w suspension). Suspension, 0.19 g, 4.66 mmol, 1.1 eq) was added in small portions. The reaction mixture was stirred at room temperature for 1 hour. The reaction was then quenched with water (20 ml) and the ethanol was distilled off. The residue was acidified with 5M aqueous HCl (pH˜4) and extracted with EtOAc (3 × 100 ml). The combined organic layers were washed with brine (100 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to give the crude product, which was triturated with DCM (2 × 30 ml) to give ethyl 2-hydroxy This resulted in -4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate (1.05 g, 3.50 mmol, 82%).

c) Synthesis of ethyl 2-chloro-4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate Ethyl 2-hydroxy-4-methyl-7- (trifluoromethyl) -1, To 5-naphthyridine-3-carboxylate (1.05 g, 3.50 mmol, 1 eq) was added POCl ₃ (11 ml) at room temperature and the reaction mixture was heated to reflux at 110 ° C. for 3 h. Then excess POCl ₃ was distilled off and the residue was diluted with EtOAc (50 ml). The mixture was washed with a saturated solution of NaHCO ₃ (50 ml), water (50 ml), brine (50 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to ethyl 2-chloro-4-methyl-7- (tri Fluoromethyl) -1,5-naphthyridine-3-carboxylate (0.98 g, 3.08 mmol, 88%) was obtained and used in the subsequent reaction without further purification.

d) Synthesis of ethyl 2- (ethylthio) -4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate Ethyl 2-chloro-4-methyl-7 in DMF (10 ml) - (trifluoromethyl) -1,5-naphthyridine-3-carboxylate (0.97 g, 3.05 mmol, 1 eq) was added, at room _{temperature, K 2 CO 3 (1.26g,} 9.15mmol, 3 Eq) and ethanethiol (0.66 ml, 9.15 mmol, 3 eq) were added. The mixture was stirred at 60 ° C. for 16 hours. The mixture was then diluted with water (80 ml) and extracted with EtOAc (3 × 80 ml). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to give the crude product, which was purified by CC (EtOAc / hexane 1: 9). , Ethyl 2- (ethylthio) -4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate (0.75 g, 2.18 mmol, 71%).

e) Synthesis of 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide Toluene (6 ml) To a solution of ethyl 2- (ethylthio) -4-methyl-7- (trifluoromethyl) -1,5-naphthyridine-3-carboxylate (0.20 g, 0.58 mmol, 1 eq) in , Me ₃ Al (2M solution in toluene, 1.16 ml, 2.32 mmol, 4 eq) and (3-fluorophenyl) methanamine (0.27 ml, 2.32 mmol, 4 eq) were added. The reaction mixture was stirred at 110 ° C. for 16 hours. The mixture was then diluted with water (50 ml) and extracted with EtOAc (3 × 40 ml). The combined organic layers were washed with 0.5 M aqueous HCl (60 ml), brine (60 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to give the crude product, which was obtained as CC (EtOAc / hexane 1 : 4) and purified by 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide ( Example 1) (0.14 g, 0.33 mmol, 57%). MS m / z [M + H] ^< +> 424.1.

Synthesis of Example 2: 2-Ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide

a) Synthesis of 2- (ethylthio) -4-methyl-1,7-naphthyridine-3-carboxylic acid Ethyl 2- (ethylthio) -4-methyl-1 in a mixture of THF (30 ml) and methanol (15 ml) , 7-naphthyridine-3-carboxylate [synthesized according to the method described for Example 1, Sections ad] (2.30 g, 8.33 mmol, 1 eq) at room temperature with water (7. A solution of LiOH.H ₂ O (3.50 g, 83.33 mmol, 10 eq) in 5 ml) was added. The resulting mixture was stirred at 75 ° C. for 5 hours. The solvent was then evaporated and the residue was washed with EtOAc (80 ml). The aqueous layer was acidified with 4M aqueous HCl (50 ml) and extracted with EtOAc (3 × 100 ml). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to 2- (ethylthio) -4-methyl-1,7-naphthyridine-3-carboxylic acid. The acid (0.85 g, 3.43 mmol, 41%) was obtained and used in subsequent reactions without further purification.

b) Synthesis of 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide 2- (ethylthio) in dry THF (12 ml) ) -4-methyl-1,7-naphthyridine-3-carboxylic acid (0.25 g, 1.01 mmol, 1 eq) in a solution of HATU (0.42 g, 1.11 mmol, 1.1 eq) and at room temperature. TEA (0.4 ml, 3.03 mmol, 3 eq) was added and the reaction mixture was stirred at room temperature for 15 minutes. 3-Fluorophenyl) methanamine (0.16 g, 1.26 mmol, 1.25 equiv) was added to the mixture at room temperature and the reaction mixture was stirred at room temperature for 1 hour. Thereafter, excess solvent was distilled off, and the residue was diluted with a saturated aqueous solution of NH ₄ Cl (50 ml). The aqueous portion was extracted with EtOAc (3 × 80 ml). The combined organic layers were washed with a saturated aqueous solution of NaHCO ₃ (50 ml), water (50 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to give the crude product, which was obtained as CC (acetone / hexane 2 9)) to 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide (Example 2) (0.18 g, 0.51 mmol, 50%). MS m / z [M + H] ^< +> 356.1.

Synthesis of Example 3: 2-Ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide

a) Synthesis of ethyl 2-mercapto-4-methyl-1,6-naphthyridine-3-carboxylate Ethyl 2-hydroxy-4-methyl-1 in a mixture of pyridine / toluene (1: 9 v / v, 15 ml) , 6-Naphthyridine-3-carboxylate [synthesized according to the method described for Example 1, Sections a and b] (0.35 g, 1.51 mmol, 1 equiv) in a solution of LR (2.44 g 6.03 mmol, 4 eq) was added and the reaction mixture was heated to reflux at 110 ° C. for 22 hours. The mixture was then cooled to room temperature and quenched with a saturated aqueous solution of NaHCO ₃ (5 ml). The aqueous portion was extracted with EtOAc (3 × 30 ml). The combined organic layers were washed with water (30 ml), brine (30 ml), dried over anhydrous Na ₂ SO ₄ and evaporated to give the crude product, which was purified by CC (methanol / DCM 1:99) This resulted in ethyl 2-mercapto-4-methyl-1,6-naphthyridine-3-carboxylate (0.22 g, 0.89 mmol, 59%).

b) Synthesis of ethyl 2- (ethylthio) -4-methyl-1,6-naphthyridine-3-carboxylate Ethyl 2-mercapto-4-methyl-1,6-naphthyridine-3- in dry DMF (5 ml) To a solution of carboxylate (0.22 g, 0.89 mmol, 1 eq) at 0 ° C. was added K ₂ CO ₃ (0.37 g, 2.66 mmol, 3 eq) followed by ethyl iodide (0 .41 g, 2.66 mmol, 3 eq) was added. The reaction mixture was stirred at room temperature for 1 hour. The mixture was then poured into ice water (10 ml) and extracted with EtOAc (3 × 20 ml). The combined organic layers were washed with water (20 ml), brine (20 ml) and dried over anhydrous Na ₂ SO ₄ to give the crude product, which was purified by CC (EtOAc / hexane 2: 3) to give ethyl. This gave 2- (ethylthio) -4-methyl-1,6-naphthyridine-3-carboxylate (0.18 g, 065 mmol, 73%).

c) Synthesis of 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide According to the method described for Example 1, section e. Ethyl 2- (ethylthio) -4-methyl-1,6-naphthyridine-3-carboxylate (0.20 g, 0.72 mmol, 1 eq) to 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl ] -4-Methyl- [1,6] naphthyridine-3-carboxylic acid amide (Example 3) (0.18 g, 0.51 mmol, 50%) was synthesized. MS m / z [M + H] ^< +> 356.1.

Synthesis of Example 4: 6-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-thieno [2,3-b] pyridine-5-carboxylic acid amide

a) Synthesis of ethyl 4-methyl-6- (trifluoromethylsulfonyloxy) thieno [2,3-b] pyridine-5-carboxylate Ethyl 6-hydroxy-4-methylthieno [2, in DCM (35 ml) 3-b] Pyridine-5-carboxylate [synthesized according to the method described for Example 1, sections a and b] (1.00 g, 4.21 mmol, 1 equiv) in a solution of TEA (1 .16 ml, 8.43 mmol, 2 eq) and trifluoromethanesulfonic anhydride (1.16 ml, 8.43 mmol, 2 eq) were added. The RM was stirred at room temperature for 2 hours. The mixture was then diluted with DCM (100 ml) and the organic layer was washed with saturated aqueous NaHCO ₃ (50 ml), water (50 ml) and brine (50 ml). The organic layer was dried over Na ₂ SO ₄ and evaporated under reduced pressure. The crude ethyl 4-methyl-6- (trifluoro-methyl-sulfonyloxy) thieno [2,3-b] pyridine-5-carboxylate (1.55 g, 4.21 mmol, 99%) is subjected to further purification. Used in subsequent reactions.

b) Synthesis of ethyl 6- (ethylthio) -4-methylthieno [2,3-b] pyridine-5-carboxylate Ethyl 4-methyl-6- (trifluoro-methyl-sulfonyloxy) in DMF (30 ml) To a solution of thieno [2,3-b] pyridine-5-carboxylate (1.84 g, 4.9 mmol, 1 eq) at room temperature, K ₂ CO ₃ (2.70 g, 19.6 mmol, 4 eq) and Ethanethiol (3.73 ml, 49.8 mmol, 10 eq) was added. The reaction mixture was stirred at 80 ° C. for 2 hours. The mixture was then diluted with water (50 ml) and extracted with EtOAc (2 × 50 ml). The combined organic layers were washed with water (50 ml), brine (50 ml), dried over Na ₂ SO ₄ and evaporated. The crude product was purified by CC (EtOAc / hexane 1:49) to give ethyl 6- (ethylthio) -4-methylthieno [2,3-b] pyridine-5-carboxylate (0.26 g, 0.92 mmol, 19%).

c) Synthesis of 6-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-thieno [2,3-b] pyridine-5-carboxylic acid amide described in Example 1, section e According to the method, from ethyl 6- (ethylthio) -4-methylthieno [2,3-b] pyridine-5-carboxylate (0.29 g, 1.01 mmol, 1 eq) to 6-ethylsulfanyl-N-[(3 -Fluorophenyl) -methyl] -4-methyl-thieno [2,3-b] pyridine-5-carboxylic acid amide (Example 4) (0.23 g, 0.64 mmol, 63%) was synthesized. MS m / z [M + H] ^< +> 361.1.

Synthesis of Example 5: 5-Ethoxy-N-[(3-fluorophenyl) -methyl] -7-methyl-2- (trifluoromethyl) -thieno [3,2-b] pyridine-6-carboxylic acid amide

a) Synthesis of ethyl 5-ethoxy-7-methyl-2- (trifluoromethyl) thieno [3,2-b] pyridine-6-carboxylate Suspension, mixture DCM (10 ml) and DMF (0.5 ml) N- (3-fluorobenzyl) -5-hydroxy-7-methyl-2- (trifluoromethyl) thieno [3,2-b] -pyridine-6-carboxamide (0.40 g, 1.31 mmol, 1 eq.) [Synthesized according to the method described for Example 1, sections a and b], at room temperature, Ag ₂ CO ₃ (0.90 g, 3.28 mmol, 2.5 eq) was added followed by , Ethyl iodide (0.54 ml, 6.55 mmol, 5 eq) was added. The resulting mixture was stirred at room temperature for 20 hours. The reaction mass was then filtered through celite. The filtrate was extracted with DCM and the DCM layer was concentrated in vacuo to give the crude product, which was purified by CC (EtOAc / Hexane 1:17) to give ethyl 5-ethoxy-7-methyl-2- (trifluoromethyl). ) Thieno [3,2-b] pyridine-6-carboxylate (0.37 g, 1.11 mmol, 84%).

b) Synthesis of 5-ethoxy-N-[(3-fluorophenyl) -methyl] -7-methyl-2- (trifluoromethyl) -thieno [3,2-b] pyridine-6-carboxylic acid amide Example 1 , Ethyl 5-ethoxy-7-methyl-2- (trifluoromethyl) thieno [3,2-b] pyridine-6-carboxylate (0.37 g, 1.11 mmol, 1 Equivalent) to 5-ethoxy-N-[(3-fluorophenyl) -methyl] -7-methyl-2- (trifluoromethyl) -thieno [3,2-b] pyridine-6-carboxylic acid amide (example 5) (0.20 g, 0.48 mmol, 44%) was synthesized. MS m / z [M + H] ^< +> 413.1.

Synthesis of further exemplary compounds Further example syntheses were carried out according to the methods already described. Table 1 shows which compounds were produced according to which method. It will be clear to those skilled in the art which educts and reagents were used in each case.

Pharmacological experimental method I. Fluorescence assay using voltage-sensitive dyes Human CHO-K1 cells expressing KCNQ2 / 3 channels are treated with DMEM-high glucose (Sigma Aldrich, D7777) containing 10% FCS (PAN Biotech, eg 3302-P270521), or A cell culture bottle (eg, containing MEM Alpha medium (1 ×, liquid, Invitrogen, 22571), 10% fetal calf serum (FCS) (Invitrogen, 10270-106, heat inactivated) and the required selective antibiotics (eg, Adhesive culture in an 80 cm ² TC flask, Nunc) at 37 ° C., 5% CO ₂ and 95% humidity.

Prior to seeding for measurement, cells were washed with 1 × DPBS buffer Ca ²⁺ / Mg ²⁺ free (eg, Invitrogen, # 14190-09) and Accutase (PAA Laboratories, L11-007) (at 37 ° C.). Peel from the bottom of the culture vessel by incubation with Accutase for 15 minutes). A CASY ™ cell counter (TCC model, Schaerfe System) is then used to determine the number of cells present and then 20,000-30,000 cells depending on the density optimization of the individual cell line. / Well / 100 μl of the described nutrient medium is applied to a Corning ™ CellBIND ™ type 96 well measuring plate (Flat Clear Bottom Black Polystyrene Microplates, # 3340). The incubation is then carried out for 1 hour at room temperature without gas treatment or humidity adjustment, followed by incubation for 24 hours at 37 ° C., 5% CO ₂ and 95% humidity.

Membrane potential assay kit (Red ™ Bulk format part R8123 from FLIPR, MDS Analytical Technologies ™), voltage sensitive fluorescent dye from one container, contents of red component A in one container, 200 ml cells Prepare by dissolving in external buffer (ES buffer, 120 mM NaCl, 1 mM KCl, 10 mM HEPES, 2 mM CaCl ₂ , 2 mM MgCl ₂ , 10 mM glucose; pH 7.4). After removing the nutrient medium, the cells are washed with 200 μl of ES buffer and then covered with a layer of 100 μl of dye solution prepared above and incubated at room temperature for 45 minutes while excluding light.

Fluorescence measurements are performed using a BMG Labtech FLUOstar ™, BMG Labtech NOVOstar ™ or BMG Labtech POLARstar ™ instrument (525 nm excitation, 560 nm emission, Bottom Read format). After the dye incubation, the desired concentration of 50 μl of test substance or 50 μl of ES buffer for control purposes is placed in a separate cavity of the assay plate and incubated for 30 minutes at room temperature, protected from light. Then, for a given, constant time, the fluorescence intensity of the dye was measured 5 minutes, to determine the fluorescence value F ₁ of each well in this way. 15 μl of 100 mM KCl solution (final concentration 92 mM) is then added to each well. The change in fluorescence is then measured (mainly 5-30 minutes) until all relevant measurements are obtained. In a given time after KCl application, in this case, to determine the fluorescence value F ₂ at the time of the fluorescence peak.

To calculate, the fluorescence intensity F ₂ is corrected for the fluorescence intensity F ₁ and the activity of the target compound (AF / F) against the potassium channel is determined as follows:

  To determine whether a substance has agonist activity,

を、対照ウェルの

Of the control well

と関連づけることができる。

Can be associated.

は、試験物質の代わりにウェルにバッファー溶液のみを添加することおよび蛍光強度の値Ｆ_１ｋを決定すること、上記のようにカリウムイオンを添加することおよび蛍光強度のＦ_２Ｋを測定することによって決定される。次いで、Ｆ_２ＫおよびＦ_１ｋを以下の通りに算出する。

Is determined by adding only the buffer solution to the well instead of the test substance and determining the fluorescence intensity value F _1k , adding potassium ions as described above and measuring the fluorescence intensity F _2K Is done. F _2K and F _1k are then calculated as follows.

  The substance is

の

of

との比較とは独立に、

Independently of comparison with

が、

But,

より大きい場合に、カリウムチャネルに対するアゴニスト活性を有し、標的化合物が、

Larger, has agonist activity on potassium channels and the target compound is

が容量依存的に増大する場合に、アゴニスト活性を有すると結論付けることが可能である。

It can be concluded that it has agonist activity when increases in a dose-dependent manner.

Calculation of EC ₅₀ and IC ₅₀ values is performed using 'Prism v4.0' software (GraphPad Software ™).

Method II. Low strength tail flick test (rat).
In the low-intensity tail flick test, the determination of the antinociceptive effect of the compounds of the invention towards acute nociceptive heat stimulation is determined by the method described by D'Amour and Smith (J. Pharm. Exp. Ther. Vol. 72, 74 79 (1941) (Non-Patent Document 17) is performed by measuring the escape reflex (tail flick) of the rat tail in response to a radial heat beam (Rhema Labtechnik, Hofheim, Germany analgesic meter; model For this purpose, rats were placed in a plexiglass restraint and focused on the back of the ridge with a low-intensity radial heat beam (48 ° C.) The stimulus intensity was approximately 7 seconds of pre-drug control escape Spinal up-regulation of acute nociceptive reflexes resulting in latency and therefore also mediated by the spinal cord A cut-off time of 30 seconds was applied to avoid tissue damage, male Sprague-Dawley rats (Janvier, Le Genest St. Isle, Frankreich) weighing 200-250 g were used. Ten rats per group were used, prior to administration of the compounds of the invention, the animals were pre-tested twice in the course of 5 minutes and the average of these measurements was calculated as the pre-test average. The anti-nociceptive effect was determined after 20, 40 and 60 minutes, calculated as the percentage of maximum possible effect (MPE [%]) based on the increase in tail escape latency according to the following formula: Represent:
MPE = [(T ₁ −T ₀ ) / (T ₂ −To)] * 100

Here, T ₀ is the control latency before administration of the compound, and T ₁ is the latency after administration of the compound. T ₂ is the cutoff time and MPE is the largest possible effect. This was made possible by using mutant analysis (repeated measurement ANOVA). It became possible to examine statistically significant differences between the compounds of the present invention and the vehicle group. The significance level was set as p ≦ 0.05.

Pharmacological data The pharmacological effects of the compounds of the invention were determined as described hereinbefore (pharmacological experiments, methods I and II, respectively).

  Corresponding pharmacological data is summarized in Table 2.

Claims (15)

Formula (I)

[Where:
A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
and,
When n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N,
R ¹ is unsubstituted or mono- or polysubstituted C _{1-10 -aliphatic} residue; in each case unsubstituted or mono- or polysubstituted, optionally in each case the same A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue which can be unsubstituted or mono- or polysubstituted linked via a C _{1-8 -aliphatic} group Via a C _{1-8 -aliphatic} group which in each case is unsubstituted or mono- or polysubstituted and optionally in each case can likewise be unsubstituted or mono- or polysubstituted Represents aryl or heteroaryl linked together,
R ² is F, Cl, Br, I, CN, CF ₃ , C (═O) H, NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, C (═O) —C _{1-4 -aliphatic} residue, C (= O) -O-C _1-4 -aliphatic residue, C (= O) -NH-C _1-4 -aliphatic residue, C (= O) -N (C _1-4 -aliphatic residue) ₂ , O-C _{1-4 -aliphatic} residue, OC (= O) -C _{1-4 -aliphatic} residue, S-C _{1- 4} - aliphatic _{residue, S (= O) 2 -C} 1~4 - aliphatic _{residue, S (= O) 2 -O} -C 1~4 - aliphatic residue _{(here, C 1 to 4} An aliphatic residue may in each case be unsubstituted or mono- or polysubstituted);
Via a C _{1-4 -aliphatic} group which in each case is unsubstituted or mono- or polysubstituted and optionally in each case can likewise be unsubstituted or mono- or polysubstituted Represents a linked C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue,
R ³ is an unsubstituted or mono- or polysubstituted C _{2-10 -aliphatic} residue; in each case unsubstituted or mono- or polysubstituted, optionally in each case Similarly a C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic, which may be unsubstituted or linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted. Represents a residue,
Or
S—R ⁵ , O—R ⁶ or N (R ⁷ R ⁸ )
Wherein R ⁵ and R ⁶ are unsubstituted or mono- or polysubstituted C _{1-10 -aliphatic} residues; in each case unsubstituted or mono- or polysubstituted, C _{3-10 -alicyclic} residues or 3-10 members optionally linked via a C _{1-8 -aliphatic} group which may optionally be optionally unsubstituted as well as mono- or polysubstituted A heteroalicyclic residue of
Provided that when R ⁵ and R ⁶ represent a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom. age,
R ⁷ is an unsubstituted or mono- or polysubstituted C _{1-10 -aliphatic} residue; in each case unsubstituted or mono- or polysubstituted, optionally in each case A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic ring, which may be unsubstituted or linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted Represents a residue,
Provided that when R ⁷ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ represents a C _{1-10 -aliphatic} residue which is unsubstituted or mono- or polysubstituted,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them form an unsubstituted or mono- or polysubstituted 3- to 10-membered heteroalicyclic residue;
Each R ⁴ is independently H, F, Cl, Br, I, CN, CF ₃ , CHF ₂ , CH ₂ F, OCF ₃ , OCHF ₂ , OCH ₂ F, SCF ₃ , O—C _1-4 -Fat. Represents a group residue, a C _1-4 -aliphatic residue or S (= O) ₂ -C _1-4 -aliphatic residue,
Here, the “aliphatic group” and “aliphatic residue” may in each case be branched or unbranched, saturated or unsaturated,
“Cycloaliphatic residue” and “heteroalicyclic residue” can in each case be saturated or unsaturated,
“Mono-substituted or poly-substituted” with respect to “aliphatic group”, “aliphatic residue”, “alicyclic residue” and “heteroalicyclic residue” respectively refers to the corresponding residue or group respectively. Independently of each other, F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) of one or more hydrogen atoms Group) ₂ , NH—C (═O) —C _1-4 aliphatic residue, N (C _1-4 aliphatic residue) —C (═O) —C _1-4 aliphatic residue, NH— S (= O) _{2- C1-4} aliphatic residue, N ( _C1-4 aliphatic residue) -S (= O) _{2- C1-4} aliphatic residue, = O, OH, OCF ₃ , O-C _{1-4 -aliphatic} residue, O-C (= O) -C _1-4 -aliphatic residue, SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, S _{(= O) 2 OH, S} (= O) 2 -C 1 ₄ - aliphatic _{residue, S (= O) 2 -O} -C 1~4 - aliphatic _{residue, S (= O) 2 -NH} (C 1~4 aliphatic residues), S (= O) _2- N (C _1-4 -aliphatic residue) ₂ , CN, CF ₃ , CHO, COOH, C _1-4 -aliphatic residue, C (═O) -C _{1-4 -aliphatic} residue , C (═O) —O—C _{1-4 -aliphatic} residue, C _{3-6 -alicyclic} residue, 3-7 membered heteroalicyclic residue, C (═O) NH ₂ , At least one substituent selected from the group consisting of C (═O) —NH (C _1-4 -aliphatic residue) and C (═O) —N (C _{1-4 -aliphatic} residue) ₂ For replacement with
“Monosubstituted or polysubstituted” with respect to “aryl” and “heteroaryl”, independently of each other with respect to the corresponding residues, are F, Cl, Br, I, NO _{2 of} one or more hydrogen atoms. , NH ₂ ,

, NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , NH—C (═O) —C _{1-4 -aliphatic} residue, N (C _{1 to 4} aliphatic _{residue) -C (=} O) -C 1~4 aliphatic _{residue, NH-S (= O)} 2 -C 1~4 aliphatic residue, _{N (C 1 to 4} aliphatic residue _{group) -S (= O) 2 -C} 1~4 aliphatic _{residue, OH, OCF 3, O-} C 1~4 - aliphatic _{residues, O-C (= O)} -C 1~4 - fat Group residue, SH, SCF ₃ , S—C _1-4 -aliphatic residue, S (═O) ₂ OH, S (═O) ₂ -C _1-4 -aliphatic residue, S (═O ) _2- O—C _1-4 -aliphatic residue, S (═O) ₂ —NH (C _1-4 -aliphatic residue), S (═O) ₂ —N (C _1-4 -fatty) _{Zokuzanmoto) 2, CN, CF 3,} C (= O) H, C (= O) OH, C 1~4 - aliphatic residue, C _{= O) -C} 1~4 - aliphatic _{residue, C (= O) -O-} C 1~4 - aliphatic _{residue, C 3 to 6} - cycloaliphatic residue, 3-7 membered heteroalicyclic Cyclic residues, benzyl, aryl, heteroaryl, C (═O) NH ₂ , C (═O) —NH (C _1-4 -aliphatic residue) and C (═O) —N (C _{1- 4} -aliphatic residue) regarding substitution with at least one substituent selected from the group consisting of ₂ ]
Represented by
Compounds in the form of individual single stereoisomers or mixtures of stereoisomers of any mixing ratio and / or in the form of free compounds, solvates and / or physiologically acceptable salts. A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
and,
When n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N,
R ¹ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} C _{1-10 -aliphatic} residues mono- or polysubstituted with at least one substituent selected from the group consisting of residues and C (═O) OH,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Alternatively, R ¹ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4- Aliphatic residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _At least one substituent selected from the group consisting of _{1-4 -aliphatic} residues, C (= O) OH, C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) —OH Or can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH _Can be linked via a C _{1-8 -aliphatic} group, which can be mono- or polysubstituted with substituents,
Alternatively, R ¹ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4- Aliphatic residue) ₂ , OH, O—C _1-4, aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4, aliphatic residue, CF ₃ , CN, C _1-4 - aliphatic _{residue, C (= O) OH,} C (= O) CH 3, C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C _3-6 -alicyclic residues, 3-7 membered heteroalicyclic residues,

Aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ can be mono- or polysubstituted with at least one substituent selected from the group consisting of C (═O) —OCH ₃ and C (═O) —OC ₂ H ₅ ;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
An aryl or heteroaryl residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue ), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} Linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from the group consisting of residues, CF ₃ , CN and C (═O) OH;
R ² is F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S—C _{1-4 -aliphatic} residue, O— _{Represents a} C _{1-4 -aliphatic} residue, wherein the C _{1-4 -aliphatic} residue may in each case be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , Can be mono- or poly-substituted with at least one substituent selected from the group consisting of CF ₃ and O—C _{1-4 -aliphatic} residues;
Or
R ² can be unsubstituted or mono- or polysubstituted in each case and optionally in each case can also be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF _{3, S-C 1~4} - aliphatic residue, _CF 3, CN and _C (= O) C 1~4 which may be mono- or polysubstituted with at least one substituent selected from the group consisting of OH _{-Represents a C3-6} -alicyclic residue or a 3-7 membered heteroalicyclic residue linked via an aliphatic group,
R ³ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} A _C2-10 -aliphatic residue mono- or polysubstituted with at least one substituent selected from the group consisting of a residue and C (= O) OH;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Or
R ³ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} Residue) ₂ , OH, = O, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1- C _{3-10 -alicyclic} residue or 3-10 membered hetero-monosubstituted or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues and C (= O) OH Indicates an alicyclic residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH _Can be linked via a C _{1-8 -aliphatic} group which can be mono- or polysubstituted by substituents,
Or
R ³ represents S—R ⁵ , O—R ⁶ or N (R ⁷ R ⁸ );
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) Group) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -In} each case represents a C1-10 _-aliphatic residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of an aliphatic residue and C (= O) OH;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Alternatively, R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1- 4} -aliphatic residue) ₂ , OH, ═O, O—C _1-4, aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4, aliphatic residue, CF ₃ , CN , C _{1-4 -aliphatic} residue, C (═O) —OH, C _{3-6 -alicyclic} residue and at least one selected from the group consisting of 3-7 membered heteroalicyclic residues Represents in each case a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with one substituent,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one selected from the group consisting of C (═O) OH Can be linked via a C _{1-8 -aliphatic} group which can be mono- or polysubstituted with substituents;
Provided that when R ⁵ or R ⁶ represents a 3 to 10 membered heteroalicyclic residue, the 3 to 10 membered heteroalicyclic residue is linked via a carbon atom. As a condition,
R ⁷ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} C _1- or poly-substituted with at least one substituent selected from the group consisting of a residue, C (═O) —O—C _1-4 -aliphatic residue and C (═O) OH _10- represents an aliphatic residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and unsubstituted O—C _1-4 -fatty. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Alternatively, R ⁷ is in each case unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _1-4- Aliphatic residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _1-4 aliphatic groups, C (═O) OH, C (═O) —O—C _1-4 aliphatic groups, C _{3-6 -alicyclic} residues and 3-7 membered A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of heteroalicyclic residues Show
Here, C _{1-4 -aliphatic} residues can in each case be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic.} May be mono- or polysubstituted with at least one substituent selected from the group consisting of residues;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) —OH Or can be polysubstituted,
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _{1-4 -aliphatic} residue, C (═O) —O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue Linked via a C _{1-8 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from the group consisting of a group and C (═O) OH;
Provided that when R ⁷ represents a 3-10 membered heteroalicyclic residue, the 3-10 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} A C _{1-10 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of a residue and C (═O) OH;
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Can be mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} Residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4- aliphatic _{residue, CF 3, CN, C 1~4} - aliphatic _{residue, C (= O) -OH,} C 3~6 - heterocycloaliphatic residues of alicyclic residues and 3-7 membered Forming a mono- or polysubstituted 3- to 10-membered heteroalicyclic residue with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
The 3-10 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them can optionally be fused with an aryl or heteroaryl, The aryl or heteroaryl residues so fused may be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _1-4 -aliphatic residue, respectively, for those moieties. Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O-C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S-C _{1-4 -aliphatic} residue , CF ₃ , CN, C _{1-4 -aliphatic} residues, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ , C _{3-6 -alicyclic} residue, 3-7 membered heteroalicyclic residue,

, Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can be mono- or polysubstituted with at least one substituent selected from the group consisting of
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
Benzyl, phenyl, thienyl, pyridyl, furyl, thiazolyl and oxazolyl can in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue Group), N (C _{1-4 -aliphatic} residue) ₂ , OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , SH, SCF ₃ , S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C (═O) CH ₃ , C (═O) C ₂ H ₅ can be mono- or polysubstituted with at least one substituent selected from the group consisting of C (═O) OCH ₃ and C (═O) OC ₂ H ₅ ,
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues may in each case be unsubstituted or F, Cl, Br, I, NO ₂ , NH ₂ , NH (C _{1-4 -aliphatic} residue), N (C _{1-4 -aliphatic} residue) ₂ , OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ S—C _{1-4 -aliphatic} residue, CF ₃ , CN, C _{1-4 -aliphatic} residue and at least one substituent selected from the group consisting of C (═O) OH or Can be polysubstituted,
Each R ⁴ is independently H, F, Cl, Br, I, CN, CF ₃ , CHF ₂ , CH ₂ F, OCF ₃ , OCHF ₂ , OCH ₂ F, SCF ₃ , OC ₄ -Fat. Represents a group residue, a C _1-4 -aliphatic residue or S (= O) ₂ -C _1-4 -aliphatic residue,
The compound according to claim 1, wherein n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents CR ⁴ , A ⁴ represents CR ⁴ ,
Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents CR ⁴ , and A ⁴ represents CR ⁴ .
Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents N, A ⁴ represents CR ⁴ ,
Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents CR ⁴ , A ⁴ represents N,
Or n represents ¹ , A ¹ represents N, A ² represents N, A ³ represents CR ⁴ and A ⁴ represents CR ⁴
Or n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents N, A ⁴ represents CR ⁴ ,
Or n represents ¹ , A ¹ represents N, A ² represents CR ⁴ , A ³ represents CR ⁴ and A ⁴ represents N,
Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents N, and A ⁴ represents CR ⁴ .
Or n represents ¹ , A ¹ represents CR ⁴ , A ² represents N, A ³ represents CR ⁴ , and A ⁴ represents N,
Alternatively, n represents ¹ , A ¹ represents CR ⁴ , A ² represents CR ⁴ , A ³ represents N, A ⁴ represents N, or n represents 0, and A ¹ represents CR. ⁴ , A ² represents CR ⁴ , A ³ represents S,
Or n represents 0, A ¹ represents N, A ² represents CR ⁴ , A ³ represents S,
Or, n represents 0, A ¹ represents S, A ² represents CR ⁴ , A ³ represents CR ⁴ ,
Or n represents 0, A ¹ represents S, A ² represents CR ⁴ and A ³ represents N. ^3. The compound according to claim 1, wherein A ³ represents N. R ² is F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue or O- _{Represents a} C _{1-4 -aliphatic} residue,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or consist of F, Cl, Br, I, ═O, OH and O—C _{1-4 -aliphatic} residues 4. A compound according to any one of claims 1 to 3, characterized in that it can be mono- or polysubstituted with at least one substituent selected from the group. The compound according to claim 1, wherein R ² represents a C _{1-4 -aliphatic} residue, preferably CH ₃ . Each ^{R 4} is independently characterized H, F, _Cl, Br, CN, to represent _{CF 3, OCF 3, CH 3} , OCH 3 or _{S (= O) 2 CH 3} , claim 5 The compound as described in any one of these. R ¹ represents a partial structure (T1)

[Where:
m represents 0, 1 or 2;
R ^1a and R ^1b each independently represent H, F, Cl, Br, I, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue,
R ^1c is at least selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{1-4 -aliphatic} residue which is mono- or polysubstituted by one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
R ^1c is in each case unsubstituted or from the group consisting of F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue at least one one substituent substituted or polysubstituted C _3-10 selected _- indicates heterocycloaliphatic residues of cycloaliphatic residue or 3-10 membered,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
R ^1c is in each case unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _1-4 -fatty _{Zokuzanmoto, C (= O) CH 3} , C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5 and _{C 3 to 6} - cycloaliphatic residue , Aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of 3-7 membered heteroalicyclic residues, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH obtain]
The compound according to any one of claims 1 to 6, characterized in that m represents 1 or 2,
R ^1a and R ^1b represent H,
At least R ^1c is unsubstituted or selected from the group consisting of F, Cl, Br, I, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{1-4 -aliphatic} residue which is mono- or polysubstituted by one substituent,
Or
In each case, at least selected from the group consisting of unsubstituted or F, Cl, Br, I, O—C _{1-4 -aliphatic} residues, CF ₃ and C _{1-4 -aliphatic} residues Represents a C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or poly-substituted with one substituent,
Or
m represents 0,
R ^1c is in each case unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _1-4 -fatty _{Zokuzanmoto, C (= O) CH 3} , C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue , An aryl or heteroaryl mono- or polysubstituted with at least one substituent selected from the group consisting of 3-7 membered heteroalicyclic residues, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3, C} 1~4 - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH 8. A compound according to claim 7, characterized in that it can be made. R ³ is unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _1-4- aliphatic residue, CF 3, _CN and C _{1 to 4 -} with at least one substituent selected from the group consisting of aliphatic residues mono- or polysubstituted C _{2 to 6 -} represents an aliphatic residue ,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or consist of F, Cl, Br, I, OH, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or polysubstituted with at least one substituent selected from the group;
Or
R ³ is in each case unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , (═O) — At least one substituent selected from the group consisting of O-C _{1-4 -aliphatic} residues, S-C _{1-4 -aliphatic} residues, CF ₃ , CN and C _{1-4 -aliphatic} residues. A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue, mono- or polysubstituted with
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or F, Cl, Br, I, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent selected from the group consisting of groups,
The C _{3-7 -alicyclic} residue or the 3-7 membered heteroalicyclic residue may in each case be optionally unsubstituted as well, or F, Cl, OH, ═O, Mono- or poly-substituted with at least one substituent selected from the group consisting of O-C _1-4 -aliphatic residues, OCF ₃ , SCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residues _Can be linked via a C _{1-4 -aliphatic} group which can be
Or
R ³ represents S—R ⁵ or O—R ⁶ ;
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SH, SCF ₃ , S—C _{1 to 4} - aliphatic residue, NH _{(C 1 to 4} - aliphatic _{residues), N (C 1~4} - aliphatic _residues) 2, CF ₃ and _{C 1 to 4} - the group consisting of aliphatic residues C _{1-8 -aliphatic} residues which are mono- or polysubstituted with at least one substituent selected from
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or consist of F, Cl, Br, I, OH, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or polysubstituted with at least one substituent selected from the group;
Or
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues In each case,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue can be a C _{1-4 -aliphatic} group, preferably likewise unsubstituted or F, Cl, OH , = O, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residue are mono-substituted or poly-substituted with at least one substituent selected from the group consisting of _Can be linked via a C _1-4 -aliphatic group which can be substituted;
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom. As a condition,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or F, Cl, Br, I, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1-4 -fatty. A C _{1-6 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or R ⁷ is in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1-4- A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues;
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue may be linked in each case, preferably a C _{1-4 -aliphatic} group, preferably likewise non- The group can be substituted or consists of F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residue Linked via a C _{1-4 -aliphatic} group which may be mono- or polysubstituted with at least one substituent selected from
Provided that when R ⁷ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ is unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN and C _{1-4 -aliphatic} residue. A C _{1-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of groups,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF Forming a 3-10 membered heteroalicyclic residue that is mono- or polysubstituted with at least one substituent selected from the group consisting of ₃ , CF ₃ , CN and C _1-4 -aliphatic residues; ,
Here, the C _{1-4 -aliphatic} residues in each case can be unsubstituted or consist of F, Cl, Br, I, OH, CF ₃ and O—C _{1-4 -aliphatic} residues Mono- or poly-substituted with at least one substituent selected from the group;
The 3 to 10 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them is optionally aryl or heteroaryl, preferably phenyl or pyridyl Can condense with
Here, the aryl or heteroaryl residues thus condensed can be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , respectively, for those moieties. , SCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue, C (═O) OH, C _3-6 alicyclic residue, 3-7 membered heteroalicyclic residue,

Monosubstituted or polysubstituted with at least one substituent selected from the group consisting of benzyl, phenyl, thienyl and pyridyl;
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
Benzyl, phenyl, thienyl and pyridyl may in each case be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ OCH ₃ , mono- or poly-substituted with at least one substituent selected from the group consisting of SCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue and C (═O) OH;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, OH, ═O, O—C _1-4 - aliphatic _{residue, OCF 3, CF 3, CN} , C 1~4 - may be mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH A compound according to any one of claims 1 to 8, characterized in that R ³ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{2-6 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of:
Or
In each case, it is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of:
Where the C _{1-4 -aliphatic} residue in each case can be unsubstituted or mono- or polysubstituted with OH or O—C _{1-4 -aliphatic} residues;
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue may in each case optionally be linked via a C _{1-4 -aliphatic} group,
Or
R ³ represents S—R ⁵ or O—R ⁶ ;
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic.} C _1-6 -aliphatic residues that are mono- or polysubstituted with at least one substituent selected from the group consisting of residues are shown in each case;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues In each case,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _3-6 -alicyclic residue or 3-7 membered heteroalicyclic residue in each case may be linked via an unsubstituted C _1-4 -aliphatic group;
Provided that when R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom. As a condition,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{1-6 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁷ is in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _1-4 -fatty. A C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of group residues,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue is in each case linked via an unsubstituted C _{1-4 -aliphatic} group;
When R ⁷ represents a 3-7 membered heteroalicyclic residue, provided that the 3-7 membered heteroalicyclic residue is linked via a carbon atom;
R ⁸ represents an unsubstituted C _{1-4 -aliphatic} residue,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF Forming a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₃ , CF ₃ , CN and C _1-4 -aliphatic residues ,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
The 3-7 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them may optionally be condensed with phenyl or pyridyl, thus condensed The phenyl or pyridyl residues may be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN, respectively, for those moieties. , C _{1-4 -aliphatic} residues, C (═O) OH, benzyl, phenyl and pyridyl can be mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least one selected from the group consisting of F, Cl, OH and O—C _{1-4 -aliphatic} residue Can be mono- or poly-substituted with one substituent,
Benzyl, phenyl and pyridyl may in each case be unsubstituted or F, Cl, OCH ₃ , OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ CH ₂ OCH ₃ , SCF ₃ , CF ₃ and C _1- 10. A compound according to any one of claims 1 to 9, characterized in that it can be mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues. A ¹ , A ² and A ³ independently of one another represent CR ⁴ , N, O, S or N (CH ₃ ),
A ⁴ represents CR ⁴ or N;
n represents 0 or 1,
However,
At least one of A ¹ , A ² , A ³ and A ⁴ does not represent CR ⁴ ;
and,
When n represents 0, exactly one of A ¹ , A ² and A ³ represents O, S or N (CH ₃ ), or when n represents ¹ , A ¹ , A ² and A ³ independently of one another represent CR ⁴ or N,
R ¹ represents a partial structure (T1)

[Where:
m represents 0, 1 or 2;
R ^1a and R ^1b each independently represent H, F, Cl, O—C _{1-4 -aliphatic} residue or C _{1-4 -aliphatic} residue,
R ^1c is unsubstituted or at least one substituent selected from the group consisting of F, Cl, O—C _1-4 aliphatic residue, CF ₃ and C _{1-4 -aliphatic} residue. Represents mono- or polysubstituted C _{1-4 -aliphatic} residues;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
R ^1c is at least 1 selected from the group consisting of unsubstituted or F, Cl, O—C _{1-4 -aliphatic} residue, CF ₃ and C _{1-4 -aliphatic} residue in each case. C _{3-10 -alicyclic} residue or 3-10 membered heteroalicyclic residue, mono- or polysubstituted with one substituent,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least selected from the group consisting of F, Cl, CF ₃ and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Or
R ^1c is in each case unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF ₃ , CN, C _{1-4 -aliphatic} residue, _{C (= O) CH 3,} C (= O) C 2 H 5, C (= O) OCH 3, C (= O) OC 2 H 5, C 3~6 - cycloaliphatic residue, 3-7 Represents aryl or heteroaryl mono- or poly-substituted with at least one substituent selected from the group consisting of a member heteroalicyclic residue, benzyl, phenyl, thienyl or pyridyl;
Here, benzyl, phenyl, thienyl and pyridyl can in each case be unsubstituted or F, Cl, Br, I, OH, O—C _1-4 -aliphatic residue, OCF ₃ , CF _3. CN, C _{1-4 -aliphatic} residue, C (═O) CH ₃ , C (═O) C ₂ H ₅ , C (═O) OCH ₃ and C (═O) OC ₂ H ₅ Mono- or poly-substituted with at least one substituent selected from the group;
C _{3-6 -alicyclic} residues and 3-7 membered heteroalicyclic residues can in each case be unsubstituted or F, Cl, Br, I, OH, ═O, O— C _{1 to 4} - aliphatic _{residue, OCF 3, CF 3 C 1~4} - mono- or polysubstituted with at least one substituent selected from the group consisting of aliphatic residues and C (= O) OH obtain]
Represents
R ² is F, Cl, Br, I, CN, CF ₃ , NO ₂ , OCF ₃ , SCF ₃ , C _1-4 -aliphatic residue, S-C _{1-4 -aliphatic} residue or O- _{Represents a} C _{1-4 -aliphatic} residue,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, ═O, OH and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
R ³ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue _Represents a C _{2-6 -aliphatic} residue which is mono- or polysubstituted with at least one substituent selected from the group consisting of:
Or
In each case, it is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{3-10 -alicyclic} residue or a 3-10 membered heteroalicyclic residue, mono- or polysubstituted with at least one substituent selected from the group consisting of:
Where the C _{1-4 -aliphatic} residue in each case can be unsubstituted or mono- or polysubstituted with OH or O—C _{1-4 -aliphatic} residues;
The C _{3-10 -alicyclic} residue or the 3-10 membered heteroalicyclic residue may in each case optionally be linked via a C _{1-4 -aliphatic} group,
Or
R ³ represents S—R ⁵ or O—R ⁶ ,
here,
R ⁵ and R ⁶ are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic.} C _{1-8 -aliphatic} residues which are mono- or polysubstituted with at least one substituent selected from the group consisting of residues are shown in each case;
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁵ and R ⁶ are in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1- A} C _{3-6 -alicyclic} residue or a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₄ -aliphatic residues In each case,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or 3-7 membered heteroalicyclic residue in each case may be linked via an unsubstituted C _{1-4 -aliphatic} group,
When R ⁵ or R ⁶ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is contingent on being linked via a carbon atom. ,
Or
R ³ represents N (R ⁷ R ⁸ ),
here,
R ⁷ is unsubstituted or from F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ and C _{1-4 -aliphatic} residue. A C _{1-8 -aliphatic} residue mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
Or
R ⁷ is in each case unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , C (═O) —O—C _{1-4 -} aliphatic residue, CF ₃ and C _{1-4 -} at least one substituent selected from the group consisting of aliphatic residues mono- or polysubstituted C _{3 to 6 -} cycloaliphatic residue A group or a 3-7 membered heteroalicyclic residue,
Here, the C _{1-4 -aliphatic} residue in each case may be unsubstituted or the group consisting of F, Cl, OH, OCF ₃ , CF ₃ and O—C _{1-4 -aliphatic} residue Mono- or poly-substituted with at least one substituent selected from
The C _{3-6 -alicyclic} residue or the 3-7 membered heteroalicyclic residue is in each case linked via an unsubstituted C _{1-4 -aliphatic} group;
Provided that when R ⁷ represents a 3-7 membered heteroalicyclic residue, the 3-7 membered heteroalicyclic residue is linked via a carbon atom,
R ⁸ represents an unsubstituted C _{1-4 -aliphatic} residue,
Or
R ⁷ and R ⁸ together with the nitrogen atom connecting them are unsubstituted or F, Cl, OH, ═O, O—C _1-4 -aliphatic residue, OCF ₃ , SCF Forming a 3-7 membered heteroalicyclic residue mono- or polysubstituted with at least one substituent selected from the group consisting of ₃ , CF ₃ , CN and C _1-4 -aliphatic residues ,
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or selected from the group consisting of F, Cl, OH, CF ₃ and O—C _{1-4 -aliphatic} residues. Mono- or poly-substituted with at least one substituent
The 3-7 membered heteroalicyclic residue formed by R ⁷ and R ⁸ together with the nitrogen atom connecting them may optionally be condensed with phenyl or pyridyl, thus condensed The phenyl or pyridyl residues may be unsubstituted or F, Cl, OH, O—C _1-4 -aliphatic residue, OCF ₃ , SCF ₃ , CF ₃ , CN, respectively, for those moieties. , C _{1-4 -aliphatic} residues, C (═O) OH, benzyl, phenyl and pyridyl can be mono- or polysubstituted with at least one substituent selected from the group consisting of:
Here, the C _{1-4 -aliphatic} residue in each case can be unsubstituted or at least one selected from the group consisting of F, Cl, OH and O—C _{1-4 -aliphatic} residues Can be mono- or poly-substituted with one substituent,
Benzyl, phenyl and pyridyl may in each case be unsubstituted or F, Cl, OCH ₃ , OCF ₃ , OCH ₂ CH ₂ OH, OCH ₂ CH ₂ OCH ₃ , SH, SCF ₃ , CF ₃ and C _May be mono- or polysubstituted with at least one substituent selected from the group consisting of _1-4 aliphatic groups;
1 to 10 characterized in that each R ⁴ independently represents H, F, Cl, Br, CN, CF ₃ , OCF ₃ , CH ₃ , OCH ₃ or S (═O) ₂ CH _3. The compound as described in any one of these. In the form of free compounds, solvates and / or physiologically acceptable salts,
1 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,5] naphthyridine-3-carboxylic acid amide;
2 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,5] naphthyridine-3-carboxylic acid amide;
3 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide;
4 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,6] naphthyridine-3-carboxylic acid amide;
5 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide;
6 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,7] naphthyridine-3-carboxylic acid amide;
7 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl- [1,8] naphthyridine-3-carboxylic acid amide;
8 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl- [1,8] naphthyridine-3-carboxylic acid amide;
9 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,8] naphthyridine-3-carboxylic acid amide;
10 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,8] naphthyridine-3-carboxylic acid amide;
11 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,6] naphthyridine-3-carboxylic acid amide;
12 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,6] naphthyridine-3-carboxylic acid amide;
13 2-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide;
14 2-ethylsulfanyl-N-[(4-fluorophenyl) -methyl] -4-methyl-7- (trifluoromethyl)-[1,5] naphthyridine-3-carboxylic acid amide;
15 5-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -7-methyl-thieno [3,2-b] pyridine-6-carboxylic acid amide;
16 6-ethylsulfanyl-N-[(3-fluorophenyl) -methyl] -4-methyl-thieno [2,3-b] pyridine-5-carboxylic acid amide;
17 5-ethoxy-N-[(3-fluorophenyl) -methyl] -7-methyl-2- (trifluoromethyl) -thieno [3,2-b] pyridine-6-carboxylic acid amide;
18 selected from the group comprising 6-ethoxy-N-[(3-fluorophenyl) -methyl] -4-methyl-2- (trifluoromethyl) -thieno [2,3-b] pyridine-5-carboxylic acid amide A compound according to any one of claims 1 to 11, characterized in that Claims 1 to 5 in the form of individual single stereoisomers or mixtures of stereoisomers in any mixing ratio and / or in the form of solvates and / or physiologically acceptable acid or base salts. At least one compound according to any one of 12;
A pharmaceutical composition optionally comprising at least one pharmaceutically acceptable adjuvant and / or optionally at least one further active ingredient. Preferably, pain, preferably acute pain, chronic pain, neuropathic pain, muscle, for use in the treatment and / or prevention of disorders and / or diseases mediated at least in part by KCNQ2 / 3 K ⁺ channels Selected from the group consisting of pain, visceral pain and inflammatory pain, epilepsy, urinary incontinence, anxiety, addiction, mania, bipolar disorder, migraine, cognitive illness and dystonia-related dyskinesia 13. A compound according to any one of claims 1 to 12 for use in the treatment and / or prevention of disorders and / or diseases. A disorder mediated at least in part by a KCNQ2 / 3 K ⁺ channel in a mammal comprising administering to the mammal an effective amount of at least one compound according to any one of claims 1-12; / Or disease, preferably pain, preferably acute pain, chronic pain, neuropathic pain, muscle pain, visceral pain and inflammatory pain, epilepsy, urinary incontinence, anxiety, dependence A method of treating and / or preventing a disorder and / or disease selected from the group consisting of symptom, mania, bipolar disorder, migraine, cognitive disease and dystonia-related dyskinesia.