DE10247271A1 - Use of new and known 7-(methyl or trifluoromethyl)-imidazo-(1,2-a)-pyridines as nitrogen monoxide synthase inhibitors useful e.g. for treating migraine, neurodegenerative diseases, inflammatory pain, diabetes or cancer - Google Patents

Abstract

Use of 7-(methyl or trifluoromethyl)-imidazo-(1,2-a)-pyridines (I) for the treatment of migraine, septic shock, neurodegenerative diseases (specifically multiple sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease), inflammatory pain, cerebral ischemia, diabetes, meningitis, arteriosclerosis, cancer diseases or wound healing deficiency. Use of 7-(methyl or trifluoromethyl)-imidazo-(1,2-a)-pyridines of formula (I) for the treatment of migraine, septic shock, neurodegenerative diseases (specifically multiple sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease), inflammatory pain, cerebral ischemia, diabetes, meningitis, arteriosclerosis, cancer diseases or wound healing deficiency. [Image] R1>Me or CF3; R2>alkyl, cycloalkyl, cycloalkylalkyl, optionally substituted (os) aryl, os heteroaryl, H, halo, CN, NO2, NH2, COR5>, COOH, COOR6>, OH or OR7>; R3>alkyl, cycloalkyl, cycloalkylalkyl, os aryl, os heteroaryl, os arylalkyl, os heteroarylalkyl, CH2OR8>, CH2SR8> or H; R4>H, alkyl, cycloalkyl, cycloalkylalkyl, os aryl, os heteroaryl, os arylalkyl, os heteroarylalkyl, 3-7C heterocyclyl or (3-7C) heterocyclylalkyl; R5>alkyl, cycloalkyl, cycloalkylalkyl, os aryl, os heteroaryl, os arylalkyl, os heteroarylalkyl or 3-7C heterocyclyl; R6>, R7>alkyl, cycloalkyl, cycloalkylalkyl, os aryl, os heteroaryl, os arylalkyl or os heteroarylalkyl; R8>alkyl, cycloalkyl, os aryl, os heteroaryl, os arylalkyl or os heteroarylalkyl; and provided that: (1) alkyl moieties have 1-8C and cycloalkyl moieties 3-8C unless specified otherwise; and (2) 2-(4-methoxy-phenyl)-7-methyl-IAP, 2,7-dimethyl-IAP, 7-methyl-IAP and 2-tert. butyl-7-methyl-IAP (where IAP = imidazo-(1,2-a)-pyridine) are excluded. An independent claim is included for (I), including their racemates, pure stereoisomers (specifically enantiomers or diastereomers), stereoisomer mixtures in all proportions, free acids or bases, salts and/or solvates (specifically hydrates), are new, provided that 2-(4-methoxyphenyl)-7-methyl-IAP; 2,7-dimethyl-IAP; 7-methyl-IAP; 2-tert. butyl-7-methyl-IAP; 2,5,7- or 2,3,7-trimethyl-IAP; 2,3,5,7-tetramethyl-IAP; 2-ethyl-7-methyl-IAP; 2-ethyl-5,7-dimethyl-IAP; 2,3-diethyl-7-methyl-IAP; 2,3-diethyl-5,7-dimethyl-IAP; 3-ethyl-2,7-dimethyl-IAP; 3-ethyl-2,7-dimethyl-IAP; 3-ethyl-2,5,7-trimethyl-IAP; 2-ethyl-3,7-dimethyl-IAP; and 2-ethyl-3,5,7-trimethyl-IAP are excluded. ACTIVITY : Antimigraine; Antibacterial; Immunosuppressive; Neuroprotective; Antiparkinsonian; Nootropic; Anticonvulsant; Antiinflammatory; Analgesic; Cerebroprotective; Antidiabetic; Antibacterial; Antiarteriosclerotic; Cytostatic; Vulnerary; Fungicide. MECHANISM OF ACTION : Nitrogen monoxide synthase inhibitor. 2,7-Dimethyl-imidazo-(1,2-a)-pyridin-3-ylmethyl)-dimethylamine (Ia) had IC50 4.015 MicroM for inhibition of nitrogen monoxide synthase in vitro.

Description

The present invention relates to substituted imidazo [1,2-a] pyridines and their physiologically tolerable salts, Process for their preparation, medicament containing these compounds and the use of substituted imidazo [1,2-a] pyridines for Manufacture of drugs.

Regulates nitrogen monoxide (NO) numerous physiological processes, including neurotransmission, relaxation and proliferation of smooth muscles, adhesion and Platelet aggregation as well as tissue injury and inflammation. by virtue of The multitude of signal functions turns nitric oxide into a A number of diseases have been linked, for example in Ignarro, L. J., Angew. Chem. (1999), 111, pages 2002-2013 and in F. Murad, Angew. Chem. Int. Ed. (1999), 111, pages 1976-1989. A important role in the therapeutic influence of these diseases plays that for responsible for the physiological formation of nitric oxide Enzyme, the nitric oxide synthase (NO synthase). So far identified three different isoforms of NO synthase, namely the two constitutive forms nNO synthase and eNO synthase as well the inducible form iNO synthase (A. J. Hobbs, A. Higgs, S. Moncada, Annu. Rev. Pharmacol. Toxicol. (1999), 39, pages 191-220; I. C. Green, P.-E. Chabrier, DDT (1999), 4, pages 47-49; P.-E. Chabrier et al., Cell. Mol. Life Sci. (1999), 55, pages 1029-1035).

The inhibition of NO synthase opens up new ones therapies for different Diseases related to nitric oxide (A. J. Hobbs et al., Annu. Rev. Pharmacol. Toxicol. (1999), 39, pages 191-220; I. C. Green, P.-E. Chabrier, DDT (1999), 4, pages 47-49; P.-E. Chabrier et al., Cell. Mol. Life Sci. (1999), 55, pages 1029-1035), such as migraines (L.L. Thomsen, J. Olesen, Clinical Neuroscience (1998), 5, pages 28-33; L.H. Lassen et al., The Lancet (1997), 349, 401-402), septic shock, neurodegenerative diseases such as multiple sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease, inflammation, inflammation pain, cerebral ischemia, Diabetes, meningitis and arteriosclerosis. In addition, the inhibition the NO synthase has an effect on wound healing, on tumors and on angiogenesis as well as non-specific immunity against Microorganisms cause (A.J. Hobbs et al., Annu. Rev. Pharmacol. Toxicol. (1999), 39, pages 191-220).

So far known active substances that inhibit the NO synthase, in addition to L-NMMA and L-NAME- i.e. Analogues of L-arginine, from the in vivo with the participation of NO synthase nitric oxide and citrulline are formed - i.a. S-methyl-L-citrulline, aminoguanidine, S-methylisourea, 7-nitroindazole and 2-mercaptoethylguanidine (A.J. Hobbs et al., Annu. Rev. Pharmacol. Toxicol. (1999), 39, pages 191-220).

An object of the present invention was therefore to provide new substances that act as inhibitors act on the nitrogen monoxide synthase. In particular should the medicines used to treat migraines, septic shock, neurodegenerative Diseases such as multiple sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease, inflammation, Inflammatory pain, cerebral ischemia, Diabetes, meningitis, arteriosclerosis, cancer, fungal diseases or are suitable for wound healing.

It has been found that substituted Imidazo [1,2-a] pyridines of the general formula I below as Inhibitors of nitrogen monoxide synthase act and in particular to treat migraines, septic Shock, neurodegenerative diseases, such as multiple sclerosis, Parkinson's disease, Alzheimer's or Huntington's disease, inflammation, Inflammatory pain, cerebral ischemia, Diabetes, meningitis, arteriosclerosis, cancer, fungal diseases or are suitable for wound healing.

The present invention therefore relates to substituted imidazo [1,2-a] pyridines of the general formula I,

The exact objects of the Invention and preferred embodiments are the claims too remove.

The term "C ₆ _ ₁₂ alkyl" includes within the meaning of the present invention acyclic saturated hydrocarbon residues which may be substituted, the branched or straight chained and unsubstituted or at least mono, having 6 to 12 carbon atoms. The C ₄ _ ₁₂ -alkyl radical is preferably selected from the group: hexyl, n-hexyl, 2-hexyl, heptyl, n-heptyl, octyl, n-octyl, nonyl, n-nonyl, decyl, n-decyl, Undecyl, n-undecyl, dodecyl or n-dodecyl.

For the purposes of the present invention, the term “C _5-12 alkyl” encompasses acyclic saturated hydrocarbon radicals which can be branched or straight-chain and can be unsubstituted or at least simply substituted, with 5 to 12 carbon atoms. The C ₅ _ ₁₂ alkyl radical is preferably selected from the group: pentyl, n-pentyl, isopentyl, neopentyl, hexyl, n-hexyl, 2-hexyl, heptyl, n-heptyl, octyl, n- Octyl, nonyl, n-nonyl, decyl, n-decyl, undecyl, n-undecyl, dodecyl or n-dodecyl.

For the purposes of the present invention, the term “C _4-12 alkyl” encompasses acyclic saturated hydrocarbon radicals which can be branched or straight-chain and can be unsubstituted or at least simply substituted, with 4 to 12 carbon atoms. Preferably, the C ₄ _ ₁₂ alkyl residue selected from the group: butyl, iso-butyl, n-butyl, sec-butyl, tert-butyl, pentyl, n-pentyl, iso-pentyl, neo-pentyl, Hexyl, n-hexyl, 2-hexyl, heptyl, n-heptyl, octyl, n-octyl, nonyl, n-nonyl, Decy1, n-decyl, undecyl, n-undecyl, dodecyl or n-dodecyl.

For the purposes of the present invention, the term “C ₃ _ ₁₂ alkyl” encompasses acyclic saturated hydrocarbon radicals which can be branched or straight-chain and can be unsubstituted or at least simply substituted, with 3 to 12 carbon atoms. The C ₃ _ ₁₂ -alkyl radical is preferably selected from the group: propyl, isopropyl, n-propyl, 2-propyl, butyl, isobutyl, n-butyl, sec-butyl, tert-butyl, Pentyl, n-pentyl, iso-pentyl, neo-pentyl, hexyl, n-hexyl, 2-hexyl, heptyl, n-heptyl, octyl, n-octyl, nonyl, n-nonyl, decyl, n-decyl, undecyl, n-undecyl, dodecyl or n-dodecyl.

For the purposes of the present invention, the term “C _1-6 alkyl radical” encompasses acyclic saturated or unsaturated hydrocarbon radicals which can be branched or straight-chain and can be unsubstituted or at least simply substituted, with 1 to 6 carbon atoms. That is, it is next to C _1-6 -Alkanylen also comprises C ₂ _ ₆ alkenyls and _C2-6 alkynyls, said alkenyls one carbon-carbon triple bond having at least one carbon-carbon double bond, which at least alkynyls. The C _1-6 -alkyl radical is preferably selected from the group consisting of methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso -Pentyl, neo-pentyl, n-hexyl, 2-hexyl, ethenyl (vinyl), ethynyl, propenyl (-CH ₂ CH = CH ₂ , -CH = CH-CH ₃ , -C (= CH ₂ ) -CH ₃ ), Propynyl (-CH-C≡CH, -C≡C-CH ₃ ), butenyl, butynyl, pentenyl, pentynyl, hexenyl and hexynyl.

For the purposes of the present invention, the term “C _1-12 -alkyl radical” encompasses acyclic saturated or unsaturated hydrocarbon radicals which can be branched or straight-chain as well as unsubstituted or at least monosubstituted, having 1 to 6 carbon atoms. That is, there are in addition also C _1-12 -Alkanylen C _2-12 alkenyls, and C ₂ _ ₁₂ includes alkynyls, said alkenyls carbon-carbon triple bond having at least one carbon-carbon double bond, which alkynyls at least one. Preferably, the C ₁ _ ₁₂ alkyl moiety is selected from the group methyl, ethyl, n-propyl, 2-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso -Pentyl, neo-pentyl, n-hexyl, 2-hexyl, n-octyl, ethenyl (vinyl), ethynyl, propenyl (-CH ₂ CH = CH ₂ , -CH = CH-CH ₃ , -C (= CH ₂ ) -CH ₃ ), propynyl (-CH-C≡CH, -C≡C-CH ₃ ), butenyl, butynyl, pentenyl, pentynyl, hexenyl, hexynyl, octenyl and octynyl.

mit p = 1, 2 oder 3, C(=S)C_1–6-Alkyl-Aryl, C(=O)-Heteroaryl, C(=S)-Heteroaryl, C(=O)-Heterocyclyl, C(=S)-Heterocyclyl, CO₂H, CO₂-Alkyl, CO-₂ Alkyl-Aryl, C(=O)NH₂, C(=O)NH-Alkyl, C(=O)NHAryl, C(=O)NH-Heterocyclyl, C(=O)N(Alkyl)₂, C(=O)N(Alkyl-Aryl)₂, C(=O)N(Alkyl-Heteroaryl)₂, C(=O)N(Heterocyclyl)₂, SO-Alkyl, SO₂-Alkyl, SO₂NH₂, SO₃H, Cycloalkyl, Aryl, Heteroaryl und Heterocyclyl ersetzt, wobei unter mehrfach substituierten C_1–6-Alkyl-Resten solche Reste zu verstehen sind, die entweder an verschiedenen Atomen oder an demselben Atom des C_1–6-Alkyl-Restes mehrfach, z.B. zwei- oder dreifach, substituiert sind, beispielsweise dreifach am gleichen Kohlenstoff-Atom wie im Falle von CF₃ oder -CH₂CF₃ oder an verschiedenen Atomen wie im Falle von -CH(OH)-CH=CH-CHCl₂. Die Mehrfachsubstitution kann mit dem gleichen oder mit verschiedenen Substituenten erfolgen. Sofern der Substituent selbst eine Alkylgruppe aufweist, ist diese bevorzugt ausgewählt aus der Gruppe Methyl, Ethyl, CH₂-OH und CF₃.If the C ₁ _ ₁₂ -alkyl radical is mono- or polysubstituted, one or more hydrogen radicals is (are) preferably selected by a substituent from the group F, Cl, Br, I, CN, NH ₂ , NH-alkyl, NH-aryl, NH-heteroaryl, NH-alkyl-aryl, NH-alkyl-heteroaryl, NH-heterocyclyl, NH-alkyl-OH, N (alkyl) ₂ , N (alkyl-aryl) ₂ , N (alkyl-heteroaryl) ₂ , N (heterocyclyl) ₂ , N (alkyl-OH) ₂ , NO, NO ₂ , SH, S-alkyl, S-aryl, S-heteroaryl, S-alkyl-aryl, S-alkyl-heteroaryl, S-heterocyclyl , S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-aryl, O-heteroaryl, O-alkyl-aryl, O-alkyl-heteroaryl, O-heterocyclyl, O-alkyl-OH, CHO , C (= O) C ₁ _ ₆ alkyl, C (= S) C ₁ _ ₆ alkyl, C (= O) aryl, C (= S) aryl, C (= O) C _1-6 alkyl aryl,

with p = 1, 2 or 3, C (= S) C _1-6 alkyl aryl, C (= O) heteroaryl, C (= S) heteroaryl, C (= O) heterocyclyl, C (= S) heterocyclyl, CO ₂ H, CO ₂ alkyl, CO ₂ alkyl aryl, C (= O) NH ₂ , C (= O) NH alkyl, C (= O) NHAryl, C (= O) NH-heterocyclyl, C (= O) N (alkyl) ₂ , C (= O) N (alkyl-aryl) ₂ , C (= O) N (alkyl-heteroaryl) ₂ , C (= O) N (heterocyclyl) ₂ , SO-alkyl, SO ₂ -alkyl, SO ₂ NH ₂ , SO ₃ H, cycloalkyl, aryl, heteroaryl and heterocyclyl, where poly-substituted C _1-6 alkyl radicals are to be understood as those radicals which either are different atoms or on the same atom of the C _1-6 alkyl radical are substituted several times, for example twice or three times, for example three times on the same carbon atom as in the case of CF ₃ or -CH ₂ CF ₃ or on different atoms such as in case of -CH (OH) -CH = CH-CHCl ₂ . The multiple substitution can take place with the same or with different substituents. If the substituent itself has an alkyl group, this is preferably selected from the group consisting of methyl, ethyl, CH ₂ -OH and CF ₃ .

The term "C _3-8 cycloalkyl radical" for the purposes of the present invention encompasses cyclic hydrocarbons having 3 to 8 carbon atoms, which may be saturated or unsaturated, unsubstituted or at least monosubstituted, with the bond of the cycloalkyl radical to the backbone of the general formula I can take place via any ring member of the cycloalkyl radical. The C _3-8 cycloalkyl radical is preferably selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl. The C ₃ _ ₈ cycloalkyl radical is a cyclohexyl radical is particularly preferred.

The term "aryl residue" means in the sense of the present Invention aromatic hydrocarbons that also with other saturated, at least partially unsaturated or aromatic ring systems can be condensed, wherein the binding of the aryl radical to the backbone of the general formula I via each any ring member of the aryl radical can take place. If the aryl residue has more than one substituent, these can be the same or different be and in any and possible position of the aryl residue available. The aryl radical is preferably selected from the group of unsubstituted or at least monosubstituted phenyl, anthracenyl, 1-naphthyl and 2-naphthyl. The aryl radical is particularly preferably selected from the group phenyl, 3-hydroxyphenyl, 3-methoxyphenyl, 2,3-dihydroxyphenyl, 2,3-dimethoxyphenyl and 1-naphthyl.

mit n = 1, 2 oder 3, C(=S)C_1–6-Alkyl-Aryl, C(=O)-Heteroaryl, C(=S)-Heteroaryl, C(=O)-Heterocyclyl, C(=S)-Heterocyclyl, CO₂H, CO₂-Alkyl, CO₂-Alkyl-Aryl, C(=O)NH₂, C(=O)NH-Alkyl, C(=O)NHAryl, C(=O)NH-Heterocyclyl, C(=O)N(Alkyl)₂, C(=O)N(Alkyl-Aryl)₂, C(=O)N(Alkyl-Heteroaryl)₂, C(=O)N(Heterocyclyl)₂, S(O)-Alkyl, S(O)-Aryl, SO₂-Alkyl, SO₂-Aryl, SO₂NH₂, SO₃H, CF₃, =O, =S; Alkyl, Cycloalkyl, Aryl, Heteroaryl und Heterocyclyl verstanden, wobei ein Substituent ggf. seinerseits substituiert sein kann. Die Mehrfachsubstitution erfolgt dabei mit gleichen oder unterschiedlichen Substituenten. Für "Aryl-Reste" sind besonders bevorzugte Substituenten ausgewählt aus der Gruppe F, CF₃, OH und O-CH₃. Für "Cycloalkyl-Reste" sind besonders bevorzugte Substituenten CO₂H oder CO₂Ethyl.If the C _3-8 cycloalkyl or the aryl radical is mono- or polysubstituted, we preferably include one or more, for example two, three or four times, substitution of one or more hydrogen atoms of the ring system with a substituent selected from the group Group F, Cl, Br, I, CN, NH ₂ , NH-alkyl, NH-aryl, NH-heteroaryl, NH-alkyl-aryl, NH-alkyl-heteroaryl, NH-heterocyclyl, NH-alkyl-OH, N ( Alkyl) ₂ , N (alkyl-aryl) ₂ , N (alkyl-heteroaryl) ₂ , N (heterocyclyl) ₂ , N (alkyl-OH) ₂ , NO, NO ₂ , SH, S-alkyl, S-cycloalkyl, S Aryl, S-heteroaryl, S-alkyl-aryl, S-alkyl-heteroaryl, S-heterocyclyl, S-alkyl-OH, S-alkyl-SH, OH, O-alkyl, O-cycloalkyl, O-aryl, O -Heteroaryl, O-alkyl-aryl, O-alkyl-heteroaryl, O-heterocyclyl, O-alkyl-OH, CHO, C (= O) C _1-6 alkyl, C (= S) C _1-6 alkyl , C (= O) aryl, C (= S) aryl, C (= O) -C _1-6 alkyl aryl,

with n = 1, 2 or 3, C (= S) C _1-6 alkyl aryl, C (= O) heteroaryl, C (= S) heteroaryl, C (= O) heterocyclyl, C (= S) heterocyclyl, CO ₂ H, CO ₂ alkyl, CO ₂ alkyl aryl, C (= O) NH ₂ , C (= O) NH alkyl, C (= O) NHAryl, C (= O) NH-heterocyclyl, C (= O) N (alkyl) ₂ , C (= O) N (alkyl-aryl) ₂ , C (= O) N (alkyl-heteroaryl) ₂ , C (= O) N (heterocyclyl) ₂ , S (O) alkyl, S (O) aryl, SO ₂ alkyl, SO ₂ aryl, SO ₂ NH ₂ , SO ₃ H, CF ₃ , = O, = S; Alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl understood, wherein a substituent may optionally be substituted in turn. The multiple substitution takes place with the same or different substituents. For "aryl radicals", particularly preferred substituents are selected from the group F, CF ₃ , OH and O-CH ₃ . For "cycloalkyl radicals", particularly preferred substituents are CO ₂ H or CO ₂ ethyl.

The term "heteroaryl" is used in the sense of the present invention for one 5-, 6- or 7-membered cyclic aromatic radical, which at least 1, possibly also 2, 3, 4 or 5 heteroatoms, wherein the heteroatoms can be the same or different and wherein the bond to the backbone of general formula I is via each any and possible Ring member of the heteroaryl residue can take place. If the heteroaryl residue has more than one substituent, these heteroaryl substituents be the same or different and in any and possible Position of the heteroaryl be present. The heterocycle can too with more saturated, at least partially unsaturated or aromatic ring systems. Preferred heteroatoms are selected from the group nitrogen, oxygen and sulfur. Preferably the heteroaryl residue is selected from the group of unsubstituted or at least monosubstituted Pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyridazinyl, Pyrimidinyl, pyrazinyl, pyranyl, indolyl, indazolyl, purinyl, pyrimidinyl, Indolizinyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, Phenazinyl and phenothiazinyl. Particularly preferred heteroaryl residues are selected from the group pyridin-2-yl, pyridin-3-yl, furan-2-yl, furan-3-yl, 5-hydroxymethylene-furan-2-yl, 5-nitro-furan-2-yl, 5- [1,3] dioxolane-furan-2-yl, 5-carboxylic acid-furan-2-yl, Thien-2-yl (2-thiophene), thien-3-yl (3-thiophene) and 5-carboxylic acid-2-thiophene (5-carboxylic acid thien-2-yl).

For the purposes of the present invention, the term “heterocyclyl” encompasses a 3-, 4-, 5-, 6- or 7-membered cyclic organic radical which has at least 1, optionally also 2, 3, 4 or 5 heteroatoms in the ring system, where the heteroatoms can be the same or different and the cyclic radical is saturated or unsaturated but not aromatic and can be unsubstituted or at least monosubstituted. Binding of the heterocyclyl radical to the basic structure of the general formula I can be carried out via any Ring member of the heterocyclyl radical take place. The heterocyclyl radical can also be part of a bi- or polycyclic system. Preferred heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur. The C _3-7 heterocyclyl radical is preferably selected from the group tetrahydrofuryl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, piperazinyl and morpholinyl.

If the compounds of the invention of the general formula I or their physiologically tolerable salts have at least one center of asymmetry, they can be in the form of their racemates, their pure enantiomers, their pure diastereomers or in form a mixture of at least two of the aforementioned stereoisomers available. You can also the substituted imidazo (1,2-a] pyridines of the general formula I also in the form of mixtures of their enantiomers or diastereomers. These mixtures can have respective stereoisomers in any mixing ratio. Chiral substituted imidazo [1,2-a] pyridines are preferred general formula I used in enantiomerically pure form.

For the purposes of this invention, alkyl or cycloalkyl radicals are also taken to mean saturated and unsaturated (but not aromatic), branched, unbranched and cyclic hydrocarbons, which can be unsubstituted or mono- or polysubstituted. Here, C _1-2 alkyl represents C1 or C2 alkyl, C _1-3 alkyl represents C1, C2 or C3 alkyl, C _1-4 alkyl represents C1, C2, C3 or C4 -Alkyl, C _1-5 -alkyl for C1-, C2-, C3-, C4- or C5-alkyl, C _1-6 -alkyl for C1-, C2-, C3-, C4-, C5- or C6- Alkyl, C _1-7 alkyl for C1, C2, C3, C4, C5, C6 or C7 alkyl, C _1-8 alkyl for C1, C2, C3, C4, C5, C6, C7 or C8 alkyl, C _1-10 alkyl for C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10 alkyl and C _1-10 alkyl for C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18 alkyl. Furthermore, C _3–4 -cycloalkyl stands for C3- or C4-cycloalkyl, C ₃ _ ₅ -cycloalkyl for C3-, C4- or C5-cycloalkyl, C ₃ _ ₆ -cycloalkyl for C3-, C4-, C5- or C6 -Cycloalkyl, C _3-7 -cycloalkyl for C3-, C4-, C5-, C6- or C7-cycloalkyl, C _3-8 -cycloalkyl for C3-C4-, C5-, C6-, C7- or C8-cycloalkyl , C _4-5 cycloalkyl for C4 or C5 cycloalkyl, C _4-6 cycloalkyl for C4, C5 or C6 cycloalkyl, C _4-7 cycloalkyl for C4, C5, C6 or C7 Cycloalkyl, C ₅ _ ₆ cycloalkyl for C5 or C6 cycloalkyl and C _5-7 cycloalkyl for C5, C6 or C7 cycloalkyl. With regard to cycloalkyl, the term also includes saturated cycloalkyls in which one or two carbon atoms have been replaced by a hetero atom, S, N or O. The term cycloalkyl also includes, in particular, one or more, preferably mono, unsaturated cycloalkyls without a hetero atom in the ring, as long as the cycloalkyl is not an aromatic system. The alkyl or cycloalkyl radicals are preferably methyl, ethyl, vinyl (ethenyl), propyl, allyl (2-propenyl), 1-propynyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, Pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, 1-methylpentyl, cyclopropyl, 2-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cycloheptyl, cyclooctyl, but also adamantyl, CHF ₂ , CF ₃ or CH ₂ OH as well as pyrazolinone, oxopyrazolinone, [1,4] dioxane or dioxolane.

Here, in connection with alkyl and cycloalkyl - as long as this is not expressly defined otherwise - the term substituted in the sense of this invention also means the substitution of at least one (possibly also several) hydrogen radicals by F, Cl, Br, I, NH ₂ , SH or OH, where “multiply substituted” or “substituted” is to be understood in the case of multiple substitution, that the substitution takes place both on different and on the same atoms several times with the same or different substituents, for example three times on the same carbon atom as in the case of CF ₃ or in different places as in the case of -CH (OH) -CH = CH-CHCl ₂ . F, Cl and OH are particularly preferred substituents here. With regard to cycloalkyl, the hydrogen radical can also be substituted by OC _1-3 alkyl or C _1-3 alkyl (in each case mono- or polysubstituted or unsubstituted), in particular methyl, ethyl, n-propyl, i-propyl, CF ₃ , methoxy or ethoxy.

Under the term (CH ₂ ) ₃ _ ₆ is -CH ₂ -CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ - and CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ -CH ₂ - to be understood, (CH ₂ ) _1-4 is -CH ₂ -, -CH ₂ -CH ₂ -, -CH ₂ - CH ₂ -CH ₂ - and -CH ₂ -CH ₂ -CH ₂ -CH ₂ - to be understood, (CH ₂ ) ₄ _ ₅ is -CH ₂ -CH ₂ -CH ₂ -CH ₂ - and -CH ₂ - CH ₂ -CH ₂ -CH ₂ -CH ₂ - to understand, etc.

Under an aryl residue, too Ring systems with at least one aromatic ring but without heteroatoms understood in even one of the rings. Examples are phenyl, Naphthyl, fluoranthenyl, fluorenyl, tetralinyl or indanyl, especially 9H-fluorenyl or anthracenyl residues that are unsubstituted or simple or can be substituted several times.

Be under a heteroaryl residue also heterocyclic ring systems with at least one unsaturated Ring understood that one or more heteroatoms from the group Contain nitrogen, oxygen and / or sulfur and also simple or can be substituted several times.

Examples from the group the heteroaryls furan, benzofuran, thiophene, benzothiophene, pyrrole, Pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phthalazine, Benzo-1,2,5 thiadiazole, benzothiazole, indole, benzotriazole, benzodioxolane, Benzodioxane, carbazole, indole and quinazoline are listed.

In connection with aryl and heteroaryl, substituted also means the substitution of aryl or heteroaryl with R ²³ , OR ^23, a halogen, preferably F and / or Cl, a CF ₃ , a CN, a NO ₂ , an NR ²⁴ R ²⁵ , a C _1-6 alkyl (saturated), a C _1-6 alkoxy, a C _3-8 cycloalkoxy, a C _3-8 cycloalkyl or a C _2-6 alkylene.

The radical R ^{23 stands} for H, a C _1-10 alkyl, preferably a C _1-6 alkyl, an aryl or heteroaryl or for an aryl bonded via a C _1-3 alkylene group or heteroaryl radical, where these aryl and heteroaryl radicals themselves may not be substituted with aryl or heteroaryl radicals,
the radicals R ²⁴ and R ²⁵ , the same or different, for H, a C _1-10 alkyl, preferably a C _1-6 alkyl, an aryl, a heteroaryl or a via a C _1-3 Aryl or heteroaryl radical bonded to alkylene group, where these aryl and heteroaryl radicals themselves may not be substituted by aryl or heteroaryl radicals,
or the radicals R ²⁴ and R ²⁵ together mean CH ₂ CH ₂ OCH ₂ CH ₂ , CH ₂ CH ₂ NR ²⁶ CH ₂ CH ₂ or (CH ₂ ) _3-6 , and
the radical R ^{26 is} H, a C _1-10 alkyl, preferably a C _1-6 alkyl, an aryl or heteroaryl radical or for an aryl bonded via a C _1-3 alkylene group or heteroaryl radical, where these aryl and heteroaryl radicals may not themselves be substituted with aryl or heteroaryl radicals.

The term salt is in mind this invention to understand any form of the active ingredient according to the invention, in which it assumes an ionic form or is charged and with is coupled to a counterion (a cation or anion) in solution located. This includes complexes of the active ingredient with others molecules and understand ions, especially complexes that are ionic Interactions are complex.

For the purposes of this invention, the term “physiologically acceptable salt” (in particular with cations or bases) is understood to mean salts of at least one of the compounds according to the invention - usually one (deprotonated) acid - as an anion with at least one, preferably inorganic, cation, which is physiologically - in particular Use in humans and / or mammals - are compatible. Particularly preferred are the salts of the alkali and alkaline earth metals but also with NH ₄ ⁺ , but especially (mono-) or (di-) sodium, (mono-) or (di-) potassium, magnesium or calcium salts.

For the purposes of this invention, the term “physiologically compatible salt” (in particular with anions or acids) is further understood to mean salts of at least one of the compounds according to the invention - mostly protonated, for example on nitrogen - as a cation with at least one anion which is physiologically - in particular when used in Humans and / or mammals - are compatible. In the sense of this invention, this is understood in particular to mean the salt formed with a physiologically compatible acid, namely salts of the respective active ingredient with inorganic or organic acids which are physiologically compatible - in particular when used in humans and / or mammals. Examples of physiologically acceptable salts of certain acids are salts of:
Hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, formic acid, acetic acid, oxa acid, succinic acid, malic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid, 1,1-dioxo-1,2-dihydro1b6-benzo [d] isothiazol-3- on (saccharic acid), monomethylsebacic acid, 5-oxo-proline, hexane-1-sulfonic acid, nicotinic acid, 2-, 3- or 4-aminobenzoic acid, 2,4,6-trimethyl-benzoic acid, a-lipoic acid, acetylglycine, acetylsalicylic acid, hippuric acid and / or aspartic acid. The hydrochloride salt is particularly preferred.

Suitable salts in the sense of this invention and in each use and each described Medicines are salts of the respective active ingredient with inorganic or organic acids and / or a sugar substitute such as saccharin, cyclamate or acesulfame. However, the hydrochloride is particularly preferred.

The production of the substituted Imidazo [1,2-a] pyridines of the general formula I can be prepared by customary, methods known to the person skilled in the art.

vorzugsweise in Lösung mit einer α-Halogencarbonylverbindung der allgemeinen Formel IV,

worin die Reste R³ und R⁴ die Bedeutung gemäß der allgemeinen Formel I haben und X für Halogen, vorzugsweise für Cl, Br oder I steht, unter Abspaltung von Wasser und Halogenwasserstoff.The compounds of the general formula I according to the invention are preferably prepared by reacting a substituted 2-aminopyridine of the general formula III, in which R ¹ and R ² are as defined in the general formula I given above,

preferably in solution with an α-halocarbonyl compound of the general formula IV,

wherein the radicals R ³ and R ^{4 have} the meaning according to the general formula I and X is halogen, preferably Cl, Br or I, with the elimination of water and hydrogen halide.

The method is advantageous for the preparation of the compounds of the general Formula I carried out under conditions in which water and / or Hydrogen halide preferably continuously from the reaction mixture be removed.

Hydrogen halide may be preferred by adding more soluble or more insoluble bound organic or inorganic bases and so from the reaction mixture be removed.

Water can be preferred by azeotropic Distillation or by adding desiccants or hygroscopic Substances are withdrawn from the reaction mixture.

The preparation of the compounds according to the invention of general formula I by the above method, with or without solvent, at temperatures above 100 ° C represents another possibility represents removing water from the reaction mixture.

Production is particularly preferred of the compounds of the invention of general formula I by reaction of substituted 2-aminopyridines general formula III with α-halocarbonyl compounds of the general formula IV, wherein X is Br, in boiling, anhydrous Ethanol.

Production is also preferred of the compounds of the invention of general formula I by reaction of substituted 2-aminopyridines general formula III with α-halocarbonyl compounds of the general formula IV, in which X represents Br or Cl, in boiling anhydrous di- and / or trichloromethane on the water separator.

The substituted 2-aminopyridines of the general formula IVI and the α-halocarbonyl compounds of the general Formula IV are generally available on the market or can be prepared according to customary methods known to the person skilled in the art can be produced.

The substituted imidazo [1,2-a] pyridines according to the invention of the general formula I can the process used to manufacture them both as free Base as well as salt can be isolated. The free base of each Compound of general formula I is usually after Implementation according to the above described inventive method and possibly subsequent Processing according to usual receive methods known to those skilled in the art. The so received or Free base of the respective compound formed in situ without isolation of the general formula I can then, for example by reaction with an inorganic or organic acid, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, p-toluenesulfonic acid, carbonic acid, formic acid, acetic acid, oxa acid, succinic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, or glutamic acid aspartic acid, be converted into the corresponding, physiologically acceptable salt.

The transfer of the respective connection of the general formula I can preferably also by moving the in a suitable organic solvent, e.g. Butane-on-2 (Methyl ethyl ketone), dissolved compound of general formula I as a free base with trimethylsilyl chloride (TMSCI) can be obtained.

If the substituted according to the invention Imidazo [1,2-a] pyridines of the general formula I by the production process according to the invention in the form of their racemates or other mixtures of their various Enantiomers and / or diastereomers is obtained, these can according to usual, processes known to the person skilled in the art are separated and, if necessary, isolated. Examples are chromatographic separation processes, in particular Liquid chromatography methods under normal pressure or under increased pressure, preferably MPLC and HPLC methods, as well as methods of the fractionated Called crystallization. You can especially single enantiomers, e.g. by means of HPLC on chiral Phase or by crystallization with chiral acids, for example (+) - tartaric acid, (-) - tartaric acid or (+) - 10-camphorsulfonic acid, formed diastereomeric salts are separated from each other.

Additional literature on the synthesis of α-halocarbonyl compounds. These references are fully part of this description:
Halogen carbonyls for cycloalkyl and N-heterocycles Fittkau, Siegfried; Jahreis, Guenther; Peters, Klaus; Ba laspiri, Lajos; JPCEAO; J. Prakt. Chem .; GE; 328; 4; 1986; 529-538; Kuroda, Satoru; Takamura, Fujiko; Tenda, Yoshiyuki; Itani, Hiromichi; Tomishima, Yasuyo; Akahane, Atsushi; Sakane, Kazuo; CPBTAL; Chem. Pharm. Bull .; EN; 49; 8th; 2001; 988-998;
For alkyl substitu. Halocarbonyls Winn, Martin; Geldern, Thomas W. von; Opgenorth, Terry J .; Jae, Hwan-Soo; Tasker, Andrew S .; et a1 .; JMCMAR; J. Med. Chem; EN; 39; 5; 1996; 1039-1048;
Sarel; Newman; JACSAT; J. Am. Chem. Soc .; 78; 1956; 5416.5418;

The connections are or appear toxicologically harmless.

Another subject of the present The invention is therefore a medicament containing at least one substituted one according to the invention C-Imidazo [1,2-a] pyridin-3-yl-methylamine or a substituted one C-imidazo [1,2-a] pyridin-3-yl-methylamine according to the above indicated general formula I, and optionally auxiliaries or other auxiliary substances.

Another subject of the present Invention is the use of at least one substituted one according to the invention C-Imidazo [1,2↔ a] pyridin-3-yl-methylamine or a substituted C-imidazo [1,2-a] pyridin-3-yl-methylamine according to the above indicated general formula I - if appropriate as an inhibitor of nitric oxide synthase - for the manufacture of a medicinal product to treat migraines, septic Shock, neurodegenerative diseases, such as multiple sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease, inflammation pain, cerebral ischemia, Diabetes, meningitis, arteriosclerosis, cancer or Wound healing.

The corresponding medicines can be taken as liquid, semi-solid or solid pharmaceutical forms, for example in the form of injection solutions, Drops, juices, Syrups, sprays, suspensions, granules, tablets, patches, capsules, Plasters, suppositories, Ointments, creams, lotions, gels, emulsions, aerosols or in multiparticulate form, for example in the form of pellets or granules, and can also be administered as such.

In addition to at least one substituted according to the invention C-Imidazo [1,2-a] pyridin-3-yl-methylamine General formula I usually contain the medicaments according to the invention more physiologically acceptable pharmaceutical excipients, which are preferably selected from the group of carrier materials, fillers, Solvents, diluents, surfactants Substances, dyes, preservatives, disintegrants, lubricants, Lubricants, flavors and binders.

The selection of the physiologically acceptable Auxiliaries and the amounts to be used depend on it whether the drug is oral, subcutaneous, parenteral, intravenous, intraperitoneal, intradermal, intramuscular, intranasal, buccal, rectal or local, for example on infections on the skin, mucous membranes and on the eyes to be applied. Suitable for oral application preparations in the form of tablets, coated tablets, capsules, Granules, pellets, drops, juices and syrups, for parenteral, topical and inhalation application solutions, Suspensions, easily reconstitutable dry preparations as well Sprays. Compounds according to the invention of the general formula I in a depot in dissolved form or in a plaster, if necessary with the addition of skin penetration promoting Appropriate percutaneous application preparations. Orally or preparations which can be used percutaneously can be the compounds according to the invention release the general formula I also delayed.

The manufacture of medicines takes place with the help of usual, means, devices, methods and processes known to the person skilled in the art, as described in "Remington's Pharmaceutical Sciences ", ed. A.R. Gennaro, 17th Ed., Mack Publishing Company, Easton, Pa. (1985), in particular in part 8, chapters 76 to 93. The corresponding Literature description is hereby introduced as a reference and is therefore considered part of the revelation.

The one to be administered to the patient The amount of the particular compound of general formula I can vary and is dependent, for example the weight or age of the patient and the type of application, the indication and the severity of the disease. Usually will 0.1 to 5000 mg / kg, preferably 1 to 500 mg / kg, particularly preferred 2 to 250 mg per kg body weight the patient of at least one compound of the general formula I applied.

molecular Pharmacology investigations:

The following are the ones for determination the nitric oxide synthase inhibition by the compounds of the invention of the general formula I used:

Nitric oxide synthase (NOS) assay

• (a) Inkubation der NO-Synthase mit markiertem Arginin als Substrat in einem Reaktionsgefäß,
• (b) Trennung des markierten Arginins von dem gegebenenfalls als Produkt der enzymatischen Reaktion entstandenen, markierten Citrullin zu einem Zeitpunkt, zu dem die Konzentration an Citrullin ansteigt,
• (c) Messung der Menge an jeweils abgetrenntem Arginin.

This assay allows the percentage inhibition of NO synthase by a compound of the general formula I according to the invention to be determined by measuring the NOS activity when the compound acts. NO synthase is mixed together with radioactively labeled arginine and the respective compound of general formula I under suitable conditions. After termination of the NO formation reaction too The amount of unreacted arginine is determined directly or indirectly at a predetermined point in time. The comparison of this amount with the amount of arginine remaining in a mixture of NOS and arginine without the addition of a compound of the general formula I and under otherwise identical conditions shows the percentage inhibition of NO synthase by the tested compound. This assay can be carried out as follows:

• (a) incubation of the NO synthase with labeled arginine as substrate in a reaction vessel,
• (b) separation of the labeled arginine from the labeled citrulline possibly formed as a product of the enzymatic reaction at a point in time at which the concentration of citrulline increases,
• (c) Measurement of the amount of arginine separated in each case.

The separation takes place via a Filter plate membrane.

This NOS assay is particularly suitable for a "High Throughput Screening" (HTS) on microtiter plates (MTP).

HTS-NOS Assay: General procedure

In this HTS-NOS assay is radioactive Arginine used as a substrate. Depending on Art the microtiter plate (MTP) in the range between 25 μl and 250 μl. Dependent on cofactors and coenzymes are added from the enzyme source used. The Incubate the approaches in this microtiter plate (assay MTP) according to step (a) at room temperature made and amounts to depending on the enzyme activity used (units) between 5 and 60 minutes. At the end of the incubation (step (a)) The plate is placed in a cell harvester, which with a MTP equipped which has a cation exchange membrane as a filter base (Filter MTP). All approaches the assay MTP are transferred to this filter MTP and via a cation exchange filter plate, sucked off a paper filter loaded with phosphate groups. The Filter MTP will subsequently washed with buffer or water. Using this approach the remaining substrate arginine on the cation exchanger bound while quantitatively washed out the enzymatically formed radioactive citrulline becomes. After drying the filter MTP and adding scintillation fluid the bound arginine can be counted on the scintillation counter. An uninhibited one NOS reaction is reflected in a low level of radioactivity. An inhibited enzyme reaction means that the radioactive arginine is not converted has been. This means, There is a high level of radioactivity on the filter.

used material

• - Arginine, L- [2,3,4- ³ H] monohydrochloride; Order No. NET-1123, from NEN
• - CaCl ₂ anhydrous; Order No. 2388.1000; Merck KGaA
• 1.4-dithiothreitol (DTT), order no. 708,984; ROCHE
• - Na ₂ EDTA dihydrate; Order No. 03680; FLUKA
• - HEPES, Best: -No. H-3375; SIGMA
• - NADPH, Tetrasodium salt; Order No. 1585363; ROCHE
• - TRIS; Order No. 93349; FLUKA

Enzyme preparation buffer: 50 mM Tris-HCl with 1 mM EDTA: The pH of the buffer was adjusted to 7.4 at 4 ° C.
Incubation buffer (medium): 50 mM HEPES with 1 mM EDTA; 1.25 mM CaCl ₂ and 1 mM dithiothreitol.
The pH of the buffer was adjusted to 7.4 at 25 ° C.
Washing medium: H ₂ O

enzyme preparation

Rat cerebelli were used as the starting tissue used. The animals were anesthetized and killed, the brain tissue, the cerebellum, was dissected out per rat cerebellum was 1 ml of enzyme preparation buffer (4 ° C) added, and digested with a Polytron homogenizer for 1 min at 6000 rpm. This was followed by centrifugation at 4 ° C. for 15 min at 20,000 g and then decanting off the supernatant and portioned freezing at -80 ° C (discarding the precipitate).

incubation:

i.A. = im Ansatz96-well MTP with a "well" capacity of ≤ 250 μl pipetting order were used: see Table 1: Table 1:

iA = in the approach

After the pipetting process was completed a lid on this MTP (assay MTP) placed. Incubation at 25 ° C (Room temperature (RT)) for 5-60 min, depending on the amount and activity of the enzyme used.

The content of the assay MTP was then transferred into a 96-well cation exchanger MTP (filter MTP) with the aid of a 96-well cell scanner and aspirated. This was followed by a single wash with 200 ml H ₂ O (from a tub).

Then the plate was at for 1 h 60 ° C in Drying cabinet dried. Then the bottom of the filter MTP exactly from below with a “back seal "sealed. Then 35 μl per well Pipette in the scintillator. Furthermore, the top of the plate with a “top seal "sealed. After a waiting time of 1 h, the plate was measured on the β counter.

In HTS operation, the incubation medium, NADPH and enzyme solution combined before the start of the pipetting step in order not to be time-consuming three separate pipetting operations.

The invention is explained below explained by examples. These explanations are only exemplary and limit the general idea of the invention not a.

Examples:

Example 1:

(2,7-Dimethyl-imidazo[1,2-α]pyridin-3-ylmethyl)-dimethyl-amin Synthesis of 2,7-dimethyl-imidazo [1,2-α] pyridin-3-ylmethyl) -dmethyl-amine

(2,7-dimethyl-imidazo [1,2-α] pyridin-3-ylmethyl) -dimethyl-amine

To 0.83 g of formaldehyde (formalin 37 %) and 1.30 ml of dimethylamine (40% in water) in 1.41 ml of glacial acetic acid was given at 0 ° C under nitrogen atmosphere 1.50 g of 2,7-dimethyl-imidazo [1,2-α] pyridine, heated the reaction mixture at 50 ° C for two hours and stirred overnight at a temperature of 20 to 25 ° C. For further cleaning the reaction mixture made alkaline with 10% sodium hydroxide solution and extracted with diethyl ether. The organic phases were combined and over Dried sodium sulfate. After removing the organic solvent 1.70 g of the crude product were obtained by distillation. To Purification by column chromatography 177 mg of the product were obtained as a colorless oil. 177 mg of the base were mixed with Diluted 1 ml ethyl methyl ketone and by adding 0.009 ml of water and 0.121 ml of chlorotrimethylsilane and then Stir overnight precipitated as hydrochloride. 170 mg of 2,7-dimethylimidazo [1,2-α] pyridin-3-ylmethyl) dimethylamine hydrochloride were obtained (correspond to 6.5% of the theoretical amount) as a colorless solid.

molecular Pharmacology Investigation:

The compounds prepared were tested in the HTS-NOS assay as described above. The inhibition of nitrogen monoxide synthase (10 μM) by the compounds according to the example is shown in Table 2 below: Table 2:

Claims (19)

Substituted imidazo [1,2-a] pyridines of the general formula I,

where each R ^{1 is} CH ₃ or CF ₃ , R ^{2 is} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C ₃ _ bonded via a C _1-8 alkylene group ₈ -cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, H, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , CO ₂ H, CO ₂ R ⁶ , OH or OR ⁷ , R ^{3 represents} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C ₃ _ ₈ bonded via a C _1-8 alkylene group Cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, CH ₂ SR ⁸ , CH ₂ OR ⁸ or N, R ⁴ is H, a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl radical, a C _3-7 heterocyclyl group, an unsubstituted or at least mono-substituted aryl or heteroaryl Rest, one via a C ₁ _ ₈ alky len-bonded group C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-7 heterocyclyl radical via a C _1-8 -alkylene group bonded unsubstituted or at least monosubstituted aryl or heteroaryl radical, R ⁵ represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 - Cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl bonded via a C _1-8 alkylene group radical, R ⁶ represents a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl moiety via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted bond via a C _1-8 alkylene group uated or at least monosubstituted aryl or heteroaryl radical, R ^{7 is} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C ₃ bonded via a C _1-8 alkylene group _ ₈ - Cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group, R ^{8 represents} a C _1-8 alkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group or for one C ₃ _ ₈ cycloalkyl radical, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates; with the proviso that the compounds - 2- (4-methoxy-phenyl) -7-methyl-imidazo [1,2-a] pyridine, - 2,7-dimethyl-imidazo [1,2-a] pyridine - 7th -Methyl-imidazo [1,2-a] pyridine - 2-tert-butyl-7-methyl-imidazo [1,2-a] pyridine, - 2,5,7-trimethyl-imidazo [1,2-a] pyridine - 2,3,7-trimethyl-imidazo [1,2-a] pyridine, 2,3,5,7-tetramethyl-imidazo [1,2-a] pyridine, 2-ethyl-7-methyl imidazo [1,2-a] pyridine, - 2-ethyl-5,7-dimethyl-imidazo [1,2-a] pyridine, - 2,3-diethyl-7-methyl-imidazo [1,2-a] pyridine, - 2,3-diethyl-5,7-dimethyl-imidazo [1,2-a] pyridine, - 3-ethyl-2,7-dimethyl-imidazo [1,2-a] pyridine, - 3-ethyl -2,5,7-trimethyl-imidazo [1,2-a] pyridine, 2-ethyl-3,7-dimethyl-imidazo [1,2-a] pyridine and - 2-ethyl-3,5,7 -Trimethyl-imidazo [1,2-a] pyridine are excluded from protection. Imidazo [1,2-a] pyridines according to Claim 1, characterized in that R ^{2 represents} H or CH ₃ and / or R ^{3 represents} N or CH ₃ . Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ^{1 is} CH ₃ or CF ₃ , R ^{2 is} CH ₃ , R ^{3 is} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, one via a C _1-8 - Alkylene group-bonded C ₃ _ ₈ cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, CH ₂ SR ⁸ , CH ₂ OR ⁸ or H, R ^{4 is} H, a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted radical or at least monosubstituted aryl or heteroaryl radical, a bonded via a C _1-8 -alkylene group C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-7 -heterocyclyl Radical, is an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group, R ^{5 is} a C _1-8 alky l radical, simply a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl group, an unsubstituted or at least substituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ^{6 stands} for a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C _3-8 cycloalkyl radical bonded via a C _1-8 alkylene group, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for one via a C _1-8 -Alkylene group-bound, unsubstituted or at least monosubstituted aryl or heteroaryl radical, R ^{7 is} a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl radical, one via a C _1-8 - Alkylene group-bonded C _3-8 cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or Heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ^{8 stands} for a C _1-8 alkyl radical, an unsubstituted or at least monosubstituted Aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group, or represents a C ₃ -C ₈ cycloalkyl radical, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates; with the proviso that the compounds - 2,5,7-trimethyl-imidazo [1,2-a] pyridine - 2,3,5,7-tetramethyl-imidazo [1,2-a] pyridine, - 2-ethyl -5,7-dimethyl-imidazo [1,2-a] pyridine, 2,3-diethyl-5,7-dimethyl-imidazo [1,2-a] pyridine, 3-ethyl-2,5,7 -Trimethyl-imidazo [1,2-a] pyridine, - 2-ethyl-3,5,7-trimethyl-imidazo [1,2-a] pyridine are excluded from protection. Imidazo [1,2-a] pyridines according to Claim 3, characterized in that R ^{3 represents} H or CH ₃ . Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ¹ is CH ₃ or CF _3, R ² is a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded _3- C ₈ -cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, N, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , CO ₂ H, CO ₂ R ⁶ , OH or OR ⁷ , R ^{3 represents} CH ₃ , R ^{4 represents} H, a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl- radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, a bonded via a C _1-8 -alkylene group C _3-8 cycloalkyl radical, a bonded via a C _1-8 -alkylene group C _{3 -7} heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group, R ^{5 represents} a C _1-8 alkyl radical, a C _{3- 8} -cycloalkyl radical, one bonded via a C _1-8 alkylene group C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least bonded via a C _1-8 alkylene group monosubstituted aryl or heteroaryl residue, R ⁶ is a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 - cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or via a C _1-8 -alkylene group bonded unsubstituted or at least monosubstituted aryl or heteroaryl radical, R ⁷ represents a C _{1 -8} alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted bond via a C _1-8 alkylene group uated or at least monosubstituted aryl or heteroaryl radical, R ^{8 is} a C _1-8 alkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, one via a C _1-8 alkylene group bound, unsubstituted or at least monosubstituted aryl or heteroaryl radical or a C _3-8 cycloalkyl radical, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates; with the proviso that the compounds - 2,3,7-trimethyl-imidazo [1,2-a] pyridine, - 2,3,5,7-tetramethyl-imidazo [1,2-a] pyridine, - 2- Ethyl-3,7-dimethyl-imidazo [1,2-a] pyridine and - 2-ethyl-3,5,7-trimethyl-imidazo [1,2-a] pyridine are excluded from protection. Imidazo [1,2-a] pyridines according to Claim 5, characterized in that R ^{2 represents} N or CH ₃ . Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ¹ is CH ₃ or CF _3, R ² is a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded _3- C ₈ -cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, H, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , CO ₂ H, CO ₂ R ^6, OH or oR ^7, R ³ represents a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl moiety via a C _1-8 -alkylene group bonded C _3-8 - Cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, CH ₂ SR ⁸ , CH ₂ OR ⁸ or H, R ^{4 is} a C ₃ _ ₈ alkyl radical, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2 , 2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl or octyl, each substituted one or more times or unsubstituted, branched or unbranched, or in each case optionally mono- or polysubstituted or unsubstituted, branched or unbranched, R ⁵ for a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, one via a C _{1- 8} alkylene group bonded C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for a via a C _1-8 alkylene group bound, unsubstituted or at least monosubstituted aryl or heteroaryl radical, R6 is a C _1-8 alkyl radical, a C _3-8 - Cycloalkyl radical, a C _3-8 cycloalkyl radical bonded via a C _1-8 alkylene group, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for one via a C _1-8 alkylene group bound, unsubstituted or at least monosubstituted aryl or heteroaryl radical, R ^{7 is} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, one bonded via a C _1-8 alkylene group C _3-8 - cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ⁸ for a C _1-8 -alkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, via a C ₁ _ ₈ alkylene group bonded unsubstituted or at least monosubstituted aryl or heteroaryl radical, or for egg a C _3-8 cycloalkyl radical, optionally in the form of its racemates, its pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates; with the proviso that the compound 2-tert-butyl-7-methylimidazo [1,2-a] pyridine is excluded from protection. Imidazo [1,2-a] pyridines according to Claim 7, characterized in that R2 represents H or CH ₃ and / or R ^{3 represents} H or CH ₃ . Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ¹ is Cl, R ² is a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C ₃ _ ₈ cycloalkyl Radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, H, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , CO ₂ H, CO ₂ R ⁶ , OH or oR ^7, R ³ represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, is an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, CH ₂ SR ⁸ , CH ₂ OR ⁸ or H, R ^{4 is} a C _1-6 alkyl radical, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3 -Methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, each substituted one or more times or unsubstituted, branched or unbranched, or in each case optionally substituted one or more times or unsubstituted, branched or unbranched; , R ⁵ represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, a C _{3- 7-} heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ^{6 represents} one C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl Radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ^{7 represents} a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical Radical, a C _3-8 cycloalkyl radical bonded via a C _1-8 alkylene group, an unsubstituted or at least one s monosubstituted aryl or heteroaryl radical or represents an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, R ^{8 represents} a C _1-8 alkyl radical, is an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group or is a C _3-8 cycloalkyl radical, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates. Imidazo [1,2-a] pyridines according to Claim 9, characterized in that R ^{2 represents} H or CH ₃ and / or R ^{3 represents} N or CH ₃ . Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ¹ is CH ₃ or CF _3, R 2 represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 Cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, N, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , CO ₂ H, CO ₂ R ^{6 is} OH or OR ⁷ , R ^{3 is} H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methyl, ethyl, methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3 -Methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, each substituted one or more times or unsubstituted, branched or unbranched, or in each case optionally substituted one or more times or unsubstituted, branched or unbranched; C _3-8 cycloalkyl, each mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; R ^{4 is} C _3-12 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methylethyl, propyl, i-propyl, n-propyl, 1,1-dimethylethyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2 -Methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl , Nonyl, decyl, undecyl, dodecyl, in each case mono- or polysubstituted or unsubstituted, branched or unbranched, or in each case optionally mono- or polysubstituted or unsubstituted, branched or unbranched; C _3-8 cycloalkyl, each mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; or a radical according to formula II,

where in each case n stands for a number between 0 and 6, m stands for a number between 0 and 6, 1 ≤ m + n ≤ 6, XO, S, SO, SO ₂ or NR ⁹ , R independently of one another for N, F, Br, I, Cl, OH, SH, NH ₂ , NO ₂ , CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , OCF ₃ , R ^{9 is} H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; preferably methyl, ethyl, propyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl , a C _3-8 cycloalkyl radical, preferably cyclopropyl, 2-methylcyclopropyl, cyclopropylmethyl, cyclobu tyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, cyclopentyl, cyclohexyl or cyclooctyl, an acyl radical (C (O) R ¹⁰ ) or a sulfonyl radical (S (O ₂ ) R ¹⁰ ), R10 is H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; or aryl, unsaturated or mono- or polysubstituted; stands, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates. Imidazo [1,2-a] pyridines according to Claim 11, characterized in that R ^{2 represents} H or CH ₃ and / or R ^{3 represents} H or CH ₃ . Imidazo [1,2-a] pyridines according to Claim 11 or 12, characterized in that R ⁴ for C _4-12 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; 1,1-dimethylethyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl , Pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, each one or substituted or unsubstituted, branched or unbranched, or in each case optionally substituted one or more times or unsubstituted, branched or unbranched; C ₃ _ ₈ -cycloalkyl, in each case mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; or a radical according to formula II, preferably R ^{4 is} C _5-12 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, in each case mono- or polysubstituted or unsubstituted, branched or unbranched, or in each case optionally mono- or polysubstituted or unsubstituted, branched or unbranched; C _3-8 cycloalkyl, each mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; or a radical of the formula II, in particular R ^{4 is} C _6-12 -alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl, nonyl, decyl, undecyl, Dodecyl, in each case mono- or polysubstituted or unsubstituted, branched or unbranched, or in each case optionally mono- or polysubstituted or unsubstituted, branched or unbranched; C _3-8 cycloalkyl, each mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; or a radical according to formula II. Substituted imidazo [1,2-a] pyridines of the general formula I,

wherein each R ^{1 is} CH ₃ or CF ₃ , R ^{2 is} CH ₃ , R ^{3 is} H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methyl, ethyl; Methylethyl, 1,1-dimethylethyl, propyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2 , 2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, in each case mono- or polysubstituted or unsubstituted, branched or unbranched, or in each case optionally substituted one or more times or unsubstituted, branched or unbranched; C ₃ _ ₈ -cycloalkyl, in each case mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; R ^{4 is} C _3-12 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; Methylethyl, propyl, i-propyl, n-propyl, 1,1-dimethylethyl, 2-methylpropyl, 1-methylpropyl, 1-ethylpropyl, butyl, i-butyl, n-butyl, tert-butyl, 1-methylbutyl, 2 -Methylbutyl, 3-methylbutyl, 2,2-dimethylbutyl, pentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl, heptyl, octyl , Nonyl, decyl, undecyl, dodecyl, in each case mono- or polysubstituted or unsubstituted, branched or unbranched, or in each case optionally mono- or polysubstituted or unsubstituted, branched or unbranched; C _3-8 cycloalkyl, each mono- or polysubstituted or unsubstituted, monounsaturated or saturated; Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, 2-methylcyclopropyl, cyclopropylmethyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, each substituted or unsubstituted; or a radical according to formula II,

where n stands for a number between 0 and 6, m stands for a number between 0 and 6, 1 ≤ m + n ≤ 6, XO, S, SO, SO ₂ or NR ⁹ , R independently of one another for H, F, Br, I, Cl, OH, SH, NH ₂ , NO ₂ , CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , OCF ₃ , R ^{9 is} H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; preferably methyl, ethyl, propyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl or hexyl , a C _3-8 cycloalkyl radical, preferably cyclopropyl, 2-methylcyclopropyl, cyclopropylmethyl, cyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, cyclobutylmethyl, cyclopentyl, cyclohexyl or cyclooctyl, an acyl radical (C (O) R ¹⁰ ) or one Sulfonyl radical (S (O ₂ ) R ¹⁰ ), R ^{10 is} H; C _1-6 alkyl, mono- or polysubstituted or unsubstituted, saturated or unsaturated, branched or unbranched; or aryl, unsaturated or mono- or polysubstituted; stands, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates. Imidazo [1,2-a] pyridines according to Claim 11, characterized in that R ^{3 represents} H or CH ₃ . Imidazo [1,2-a] pyridines according to one of Claims 1-8 and 11-15, characterized in that for R ⁴ C ₃ -C ₈ cycloalkyl is selected from C ₄ -C ₇ cycloalkyl or C ₅ -C _6- cycloalkyl, preferably C ₅ -C ₆ -cycloalkyl. Medicament containing at least one imidazo [1,2-a] pyridine according to one of claims 1 to 16 and optionally auxiliary substances. Use of a compound according to any one of claims 1 to 16 for the manufacture of a medicament for the treatment of migraine, septic Shock, neurodegenerative diseases, preferably multiples Sclerosis, Parkinson's disease, Alzheimer's disease or Huntington's disease, Inflammatory pain, cerebral ischemia, Diabetes, meningitis, arteriosclerosis, cancer or Wound healing. Use of a substituted imidazo [1,2-a] pyridine of the general formula I,

wherein each R ¹ is CH ₃ or CF _3, R ² is a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded _3- C ₈ -cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, H, F, Cl, Br, I, CN, NO ₂ , NH ₂ , C (= O) R ⁵ , C0 ₂ H, C0 ₂ R ^6, OH or oR ^7, R ³ represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 - Cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group, CH ₂ SR ⁸ , CH ₂ OR ⁸ or H, R ^{4 is} H, a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl Rest, one via a C _1-8 alky len-bonded group C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-7 heterocyclyl radical via a C _1-8 -alkylene group bonded unsubstituted or at least monosubstituted aryl or heteroaryl radical, R ⁵ represents a C _1-8 alkyl radical, a C _3-8 cycloalkyl radical via a C _1-8 -alkylene group bonded C _3-8 - Cycloalkyl radical, a C _3-7 heterocyclyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl bonded via a C _1-8 alkylene group radical, R ⁶ represents a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl moiety via a C _1-8 -alkylene group bonded C _3-8 cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubsti bonded via a C _1-8 alkylene group -substituted or at least monosubstituted aryl or heteroaryl radical, R ⁷ represents a C _1-8 alkyl radical, a C ₃ _ ₈ cycloalkyl radical, a bonded via a C _1-8 -alkylene group C ₃ _ ₈ -cycloalkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical or for an unsubstituted or at least monosubstituted aryl or heteroaryl radical which is bonded via a C _1-8 alkylene group, R ^{8 represents} a C _1-8 alkyl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical, an unsubstituted or at least monosubstituted aryl or heteroaryl radical bonded via a C _1-8 alkylene group or for one C ₃ _ ₈ cycloalkyl radical, optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of the stereoisomers, in particular the enantiomers or diastereomers any mixing ratio; in the form shown or in the form of their acids or their bases or in the form of their salts, in particular the physiologically tolerable salts, or in the form of their solvates, in particular the hydrates; for the manufacture of a medicament for the treatment of migraines, septic shock, neurodegenerative diseases, preferably multiple sclerosis, Parkinson's disease, Alzheimer's or Huntington's disease, inflammation pain, cerebral ischemia, diabetes, meningitis, arteriosclerosis, cancer or for wound healing with the proviso that the compounds, - 2- (4-methoxy-phenyl) -7-methyl-imidazo [1,2-a] pyridine, - 2,7-dimethyl-imidazo [1,2-a] pyridine - 7-methyl-imidazo [1,2-a] pyridine - 2-tert-butyl-7-methyl-imidazo [1,2-a] pyridine, are excluded from protection.