Abstract:
A method of treatment or prophylaxis of SSAO-mediated complications in mammals including humans, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):  
                         
 
     in which R 1 , R 2 , R 3  and R 4  are as described in the specification.

Description:
CROSS REFERENCE TO RELATED APPLICATIONS  
       [0001]    This application claims priority from Swedish Patent Application No. 0004101-2, filed Nov. 9, 2000, and U.S. Provisional Patent Application Serial No. 60/252,156, filed Nov. 20, 2000. These applications are incorporated herein by reference in their entirety. 
     
    
     
       FIELD OF INVENTION  
         [0002]    The present invention relates to use of 4-alkyl-5-alkoxycarbonyl-4, 5, 6, 7-tetrahydroimidazo[4,5-c] pyridine derivatives for the manufacture of medicaments for, or treatment or prophylaxis of semicarbazide-sensitive amine oxidase (SSAO)-mediated complications.  
         BACKGROUND OF INVENTION  
         [0003]    Semicarbazide-sensitive amine oxidase, SSAO, is a monoamine oxidase that recently has been suggested to be responsible for microvascular complications in diabetic patients. Nephropathy, neuropathy and retinopathy represent the end results of microvascular complications in both insulin dependent diabetes mellitus (IDDM) and non-insulin dependent diabetes mellitus (NIDDM). Heart attack, angina, strokes, amputations, blindness and renal failure are clinical events that represent the end point of the clinical study. Endothelial cells dysfunction may precede the diabetic state of complications. The SSAO enzyme is located in the vascular smooth muscles, retina, kidney and the cartilage tissues, and in the circulating blood (Yu, P. H. Deamination of methylamine and angiopathy; toxicity of formaldehyde, oxidative stress and relevance to protein glycoxidation in diabetes.  J. Neural. Transm. Suppl.,  1998, 52, 201) and has been found to be overactive in diabetic patients (Ekblom, J. Potential therapeutic value of drugs inhibiting semicarbazide-sensitive amine oxidase: vascular cytoprotection in diabetes mellitus.  Pharmacol. Res.,  1998, 37, 87). SSAO oxidizes a primary amine into the corresponding aldehyde with the help of the non-proteogenic amino acid topaquinone (Scheme 1). Oxidation of the aminophenol form of topaquinone into the quinone form, in order to close the catalytic cycle, is catalyzed by Cu(II), present in the active site of the enzyme. Hydrogen peroxide and ammonia are produced. The general catalytic cycle is very similar to the one observed for other monoamine oxidases (Scheme 1). The higher activity of SSAO as well as the higher concentration of its natural substrates, methylamine and aminoacetone, in diabetic patients, would lead to a higher production of formaldehyde, methylglyoxal and hydrogen peroxide. These products are known to be highly cytotoxic for the endothelial cell layer and might lead to the observed microvascular complication in diabetic patients (Yu, P. H. Deamination of methylamine and angiopathy; toxicity of formaldehyde, oxidative stress and relevance to protein glycoxidation in diabetes.  J. Neural. Transm. Suppl.,  1998, 52, 201). The inhibition of SSAO-mediated reactions is therefore a strategy that could be beneficial for a variety of pathological conditions.  
           [0004]    Scheme 1: SSAO&#39;s catalytic cycle. The active site is represented schematically by the topaquinone residue as well as by a basic amino acid residue B −  essential for the activity.  
                         
 
         SUMMARY OF THE INVENTION  
         [0005]    According to the invention a method of treatment or prophylaxis of SSAO-mediated complications in mammals including humans is provided. In one aspect, the invention relates to a method of treatment or prophylaxis of SSAO-mediated complications in mammals including humans, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of Formula (I):  
                         
 
           [0006]    or a pharmaceutically acceptable salt thereof, wherein  
           [0007]    R 1  is  
           [0008]    (a) H, or  
           [0009]    (b) CONH—R 5 ;  
           [0010]    R 2  is  
           [0011]    (a) COOR 5 ,  
           [0012]    (b) COR 5 ,  
           [0013]    (c) CONH—R 5 ,  
           [0014]    (d) CSNH—R 5 , or  
           [0015]    (e) H;  
           [0016]    R 3  is  
           [0017]    (a) H,  
           [0018]    (b) C 1-8  alkyl, or  
           [0019]    (c) (CH 2 ) n Ar;  
           [0020]    R 4  is  
           [0021]    (a) H,  
           [0022]    (b) Ar, or  
           [0023]    (c) C 1-8  alkyl; and  
           [0024]    R 5  is  
           [0025]    (a) H,  
           [0026]    (b) (CH 2 ) n Ar,  
           [0027]    (c) (CH 2 ) n OAr,  
           [0028]    (d) C 1-8  alkyl containing 0-2 oxygen atoms and optionally substituted with 0-5 halogen atoms, or  
           [0029]    (e) a polyether chain having the formula (CH 2 ) x O(CH 2 ) y O(CH 2 ) z CH 3 ;  
           [0030]    n is an integer 0 to 4;  
           [0031]    m is an integer 0 to 2;  
           [0032]    x and y are integers 2 to 4;  
           [0033]    z is an integer 0 to 3;  
           [0034]    Ar is phenyl, 1-naphthyl or 2-naphthyl, unsubstituted optionally mono-or poly-substituted with electrodonating groups, halogen, C 1-6  alkyl, CF 3 , hydroxyl, C 1-6  alkoxyl, OCF 3 , CN, NO 2 , phenyloxyl, benzyloxyl, optionally substituted phenyl, alkylsulfonyl, C 1-6  alkenyl, —NH 2 , R 7 NH—, R 7 , R 7 N—, C 1-6  alkylcarboxyl, formyl, C 1-6  alkyl-CO—NH—, aminocarbonyl (R R 7 —N—CO—), SR 7  wherein R 7  is simultaneously or alternatively H or C 1-6  alkyl; cynnamoyl, unsubstituted or optionally substituted benzyl; 1,1-diphenylethyl, a monocyclic or bicyclic heterocyclic ring (furyl, pyrrolyl, triazolyl, diazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyrazinyl, thienyl, imidazolyl, pyrazolyl, indolyl, quinolinyl, isoquinolinyl, benzofuryl, benzothienyl, benzoxadiazolyl which are unsubstituted or optionally mono or di-substituted with halogen, C 1-6  alkyl); 2, or 3, or 4-pyridyl or a 5 to 7-membered unsaturated or partially or completely saturated heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur where nitrogen containing heterocycles may contain H or C 1-6  alkyl or CF 3 —CO— at the nitrogen atoms where such a substitution is allowed.  
           [0035]    In another aspect, the method comprises administering to a patient (e.g., mammal, human) in need of such treatment a therapeutically effective amount of a compound of Formula (I):  
                         
 
           [0036]    or a pharmaceutically acceptable salt thereof, wherein  
           [0037]    R 1  is  
           [0038]    (a) H, or  
           [0039]    (b) CONH—R 5 ;  
           [0040]    R 2  is  
           [0041]    (a) COOR 5 ,  
           [0042]    (b) COR 5 ,  
           [0043]    (c) CONH—R 5 , or  
           [0044]    (d) CSNH—R 5 ;  
           [0045]    R 3  is  
           [0046]    (a) H,  
           [0047]    (b) C 1-8  alkyl, or  
           [0048]    (C) (CH 2 ) n Ar;  
           [0049]    R 4  is  
           [0050]    (a) H,  
           [0051]    (b) Ar, or  
           [0052]    (c) C 1-8  alkyl; and  
           [0053]    R 5  is  
           [0054]    (a) H,  
           [0055]    (b) (CH 2 ) n Ar,  
           [0056]    (c) (CH 2 ) n OAr,  
           [0057]    (d) C 1-8  alkyl, or  
           [0058]    (e) a polyether chain having the formula (CH 2 ) x O(CH 2 ) y O(CH 2 ) z CH 3 ;  
           [0059]    n is an integer 0 to 4;  
           [0060]    m is an integer 0 to 2;  
           [0061]    x and y are integers 2 to 4;  
           [0062]    z is an integer 0 to 3;  
           [0063]    Ar is phenyl, 1-naphthyl or 2-naphthyl, unsubstituted optionally mono-or poly-substituted with halogen, C 1-6  alkyl, CF 3 , hydroxyl, C 1-6  alkoxyl, OCF 3 , CN, NO 2 , phenyloxyl, benzyloxyl, optionally substituted phenyl, alkylsulfonyl, C 1-6  alkenyl, —NH 2 , R 7 NH—, R 7 , R 7 N—, C 1-6  alkylcarboxyl, formyl, C 1-6  alkyl-CO—NH—, aminocarbonyl (R 7 , R 7 —N—CO—), SR 7  wherein R 7  is simultaneously or alternatively H or C 1-6  alkyl; cynnamoyl, unsubstituted or optionally substituted benzyl; 1,1-diphenylethyl, a monocyclic or bicyclic heterocyclic ring (furyl, pyrrolyl, triazolyl, diazolyl, oxazolyl, thiazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyrazinyl, thienyl, imidazolyl, pyrazolyl, indolyl, quinolinyl, isoquinolinyl, benzofuryl, benzothienyl, benzoxadiazolyl which are unsubstituted or optionally mono or di-substituted with halogen, C 1-6  alkyl); 2, or 3, or 4-pyridyl or a 5 to 7-membered unsaturated or partially or completely saturated heterocyclic ring each containing 1 to 4 heteroatoms selected from oxygen, nitrogen or sulfur where nitrogen containing heterocycles may contain H or C 1-6  alkyl or CF 3 —CO— at the nitrogen atoms where such a substitution is allowed.  
           [0064]    Another aspect of the invention relates to methods of inhibiting SSAO activity in a mammal, including humans, comprising administering to a patient (e.g., mammal, human) in need of such treatment a therapeutically effective amount of a compound of any of the formulae delineated herein, including those of Formula I and those delineated in the tables herein. In another aspect, the methods of inhibiting SSAO activity using compounds delineated herein are useful in instances (e.g., treatment or prevention of diseases, including those herein) where modulation (e.g., downregulation, or control of overproduction) of abnormal levels of SSAO or overactive levels of SSAO in the subject (e.g., patient, mammal, human) are present.  
           [0065]    The term “C 1-8  alkyl” denotes a saturated or unsaturated, straight, branched or cyclic alkyl group having from 1 to 8 carbon atoms. Examples of said C 1-8  alkyl include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl, and straight- and branched-chain pentyl, hexyl, septyl and octyl, optionally substituted with 0-5 halogen atoms.  
           [0066]    The term “halogen” shall mean fluorine, chlorine, or bromine.  
           [0067]    Electrodonating groups (e.g., electron-donating groups) are known in the art, including in J. March, Advanced Organic Chemistry, 2 nd  Ed., McGraw-Hill Book Company, New York, (1977), and subsequent editions thereof.  
         DETAILED DESCRIPTION OF THE INVENTION  
         [0068]    According to the present invention it has been found that 4-alkyl-5-alkoxycarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c] pyridine derivatives of Formula (I) are potent compounds for inhibiting SSAO-mediated reactions. 4-alkyl-5-alkoxycarbonyl-4,5,6,7-tetrahydroimidazo[4,5-c] pyridine derivatives are known from GB 2 158 440 and U.S. Pat. No. 4,223,146. In the GB application the compounds are disclosed to have anti-viral activity. The compounds in the U.S. patent are useful as antiulcer agents and as inhibitors of gastric secretion.  
           [0069]    In Formula (I) preferred substituents are as follows:  
           [0070]    R 1  is H, CO—NH2, R 3  is C 1-3  alkyl or benzyl and R 2  is COOR 5  and R 5  is  
           [0071]    1) H or a linear, branched or cyclic C 1-8  alkyl which can be saturated or not, containing 0-2 oxygen atoms and optionally substituted with 0-5 halogen atoms;  
           [0072]    2) (CH 2 ) n Ar, where n 0-3 and Ar is a phenyl group or a phenyl group substituted with electrodonating groups and/or halogen atoms.  
           [0073]    Preferred compound of Formula (I) are:  
           [0074]    benzyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate;  
           [0075]    benzyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate;  
           [0076]    benzyl 4-propyl-1 ,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate;  
           [0077]    2,2,2-trichloroethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate; and  
           [0078]    benzyl (4S,6S)-6-(aminocarbonyl)-4-ethyl-1,4,6,7-tetrahydro -5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate.  
           [0079]    The compounds of the Formula (I) can form acid addition salts with acids such as conventional pharmaceutically acceptable acids, for example maleic, hydrochloric, hydrobromic, phosphoric, acetic, fumaric, salicylic, citric, lactic, mandelic, tartaric and methanesulfonic.  
           [0080]    Compounds of Formula (I) may also form solvates such as hydrates and the invention also extends to these forms. When referred to herein, it is understood that the term “compound of Formula (I)” also includes these forms.  
           [0081]    Certain compounds of Formula (I) are capable of existing in stereoisomeric forms including diastereomers and enantiomers and the invention extends to each of these stereoisomeric forms and to mixtures thereof including racemates. The different stereoisomeric forms may be separated one from the other by the usual methods. Any given isomer may be obtained by stereospecific or asymmetric synthesis. The invention also extends to any tautomeric forms and mixtures thereof.  
           [0082]    Preferably the compounds of Formula (I) are used for treatment or prophylaxis of SSAO mediated vascular complications and for insulin dependent diabetes mellitus and non-insulin dependent diabetes mellitus.  
           [0083]    The compounds used in the invention are prepared according to known methods. The compounds can be prepared as follows:  
                         
 
                         
 
           [0084]    The starting materials are commercially available or can be prepared following known procedures.  
           [0085]    According to the present invention the compounds for treatment of SSAO mediated complications can conveniently be administered in a pharmaceutical composition containing the compound in combination with a suitable excipient. Such pharmaceutical compositions can be prepared by methods and contain excipients which are well known in the art. A generally recognized compendium of such methods and ingredients is Remington&#39;s Pharmaceutical Sciences by E. W. Martin (Mark Publ. Co., 15 th  Ed., 1975). The compounds and compositions can be administered orally, parenterally (for example, by intravenous, intraperitoneal or intramuscular injection), topically, or rectally.  
           [0086]    Useful dosages of the compounds of Formula (I) can be determined by comparing their in vitro activity, and in vivo activity in animal models. Methods for the extrapolation of effective dosages in mice, and other animals, to humans are known in the art; for example, see U.S. Pat. No. 4,938,949.  
           [0087]    The compound can be administered in unit dosage form; for example, containing about 0.05 mg to about 500 mg, conveniently about 0.1 mg to about 250 mg, most conveniently, about 1 mg to about 150 mg of active ingredient per unit dosage form. The desired dose may be presented in a single dose or as divided doses administered at appropriate intervals. The compositions can be administered orally, sublingually, transdermally, or parenterally at dose levels of about 0.01 to about 150 mg/kg, preferably about 0.1 to about 50 mg/kg, and more preferably about 0.1 to about 30 mg/kg of mammal body weight.  
           [0088]    All references cited herein, whether in print, electronic, computer readable storage media or other form, are expressly incorporated by reference in their entirety, including but not limited to, abstracts, articles, journals, publications, texts, treatises, internet web sites, databases, patents, and patent publications.  
           [0089]    The invention will now be illustrated with the following examples, which however, are for illustrative purposes are not intended to limit the scope of the invention.  
           [0090]    The following abbreviations are used:  
           [0091]    aq: aqueous; br: broad; DIPEA: diisopropylethylamine; DMAP: 4-(N,N-dimethylamino)pyridine; ECAO:  Esterichia Coli  amine oxidase; EDC.HCl: N-ethyl-N′-3(dimethylamino)propylcarbodiimide hydrochloride; EI: electron impact; eq: equivalent; EtOAc: ethyl acetate; HOBt: hydroxybenzotriazol; HTS: high throughput screening;; Mp: melting point; HRMS: high resolution mass spectrum; org: organic; RP—HPLC: reversed-phase high pressure liquid chromatography; SAR: structure activity relationship; sat: saturated; TLC: thin layer chromatography.  
           [0092]    Experimental:  
           [0093]    Solvents were purchased from Merck or Riedel-de Haen. Chemicals and reagents were purchased from Aldrich, Lancaster or Fluka. The buffer solution (pH 9) was bought from Merck (catalogue number 1.09461.1000, boric acid/KCl/NaOH). TLCs were run using Silicagel60 F 254  plates purchased from Merck. TLCs were analysed by UV or stained with a solution of KMnO 4  in water. Flash chromatography was run using Silicagel 60 (230-400 mesh) from Merck. Parallel flash chromatography was run on a Foxy-200 system from Isco Inc. with 108-disposable columns for FC from Isco Inc. RP—HPLCs were run on a Gilson system, using a 119 UV-detector (214 nm or 254 nm), a 805 manometric module, a 305- and a 306-pumps and a Vydac C 18 -column (218TP1022); H 2 O+0.1% TFA/CH 3 CN were used as eluents. Mps were measured with a Gallenkamp apparatus and were uncorrected. NMR spectra were recorded on a Varian Inova 400 instrument. (EI)-MS spectra were recorded on a JMS SX-102A mass spectrometer (Jeol, Tokyo, Jpn) at 70 eV or on an Autospec-oaTOF Micromass Manchester instrument at 70 eV. HRMS spectra were recorded on a LCT Micromass instrument with flow injection-electrospray positive mode; quaternary ammonium salts were used as references. Reactions were followed by MS, using a Platform I Micromass instrument, Manchester, with an electrospray positive and negative mode flow injection. Elemental analysis was run on an Elementar Vario EL instrument.  
           [0094]    General Procedure I (GPI):  
           [0095]    A solution of histidine or histamine, NaOH and aldehyde was prepared in water and MeOH, and was heated under reflux for 24 h. After cooling the solution to room temperature, then to 0° C., aq. conc. HCl was added. See the specific examples for the work-up procedures.  
           [0096]    General Procedure II (GPII):  
           [0097]    A solution of tetrahydroimidazopyridine and K 2 CO 3  in CHCl 3  and water was cooled to 0° C. The chloroformate, resp. the acyl chloride was added dropwise. The mixture was stirred for 24 h while warming up to room temperature. The phases were separated, the org. phase dried over Na 2 SO 4  and the solvent removed under reduced pressure. The residue was dissolved or suspended in MeOH (3 mL/mmol of starting material) and aq. 1M NaOH (2 mL/mmol of starting material) was added. After 1 h, the mixture was worked-up and purified, see specific examples.  
           [0098]    Carboxylic Acid Intermadiate (Scheme 2)  
           [0099]    (4S,6S)-4-Ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic Acid:  
           [0100]    According to GPI with histidine (15.5 g, 0.100 mol), NaOH (24 g, 0.60 mol), water (100 mL), MeOH (400 mL) and propionaldehyde (20 mL, 0.276 mol). The solution was then acidified to pH 7-8 with aq. conc. HCl (60 mL) and the solvent was removed under reduced pressure. After drying the residue thoroughly under high vacuum, the oil was triturated with hot EtOH and filtered (3×). The filtrate was evaporated under reduced pressure and the residue crystallized from EtOH/water. (4S,6S)-4-Ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid was isolated as a white powder (6.44 g, 33%).  1 H-NMR and NOE-measurement showed a cis/trans ratio of 9:1. Mp=242-4° C.  1 H—NMR (400 MHz, D 2 O; only cis-stereoisomer described): δ=7.75 (s, 1H); 4.43 (m, br., 1H); 4.05 (dd, J 1 =12.1 Hz, J 2 =5.2 Hz, 1H); 3.81 (dd, J 1 =16.5 Hz, J 2 =5.3 Hz, 1H); 3.00 (ddd, J 1 =16.5 Hz, J 2 =12.1 Hz, J 3 =2.4 Hz, 1H); 2.27 (m, 1H); 1.91 (m, 1H); 1.14 (t, J=7.6 Hz, 3H).  13 C—NMR (100 MHz, D 2 O): δ=173.28 (s); 137.27 (d); 129.83 (s); 124.10 (s); 57.98 (d); 56.20 (d); 25.17 (t); 23.79 (t); 9.51 (q). MS (EI): m/z=194 (M + —H 2 , 2%); 166 (61%); 148 (9%); 120 (100%); 107 (10%); 93 (10%). HRMS: Calc. for C 9 H 13 N 3 O 2 : M + =195.1008; found: M + =195.0000.  
           [0101]    Intermediate 2 (Scheme 2)  
           [0102]    (4S,6S)-5-[(Benzyloxy)carbonyl]-4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic Acid:  
           [0103]    A solution of (4S,6S)-4-Ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid (500 mg, 2.56 mmol) in an aq. buffer solution at pH 9 (5 mL) and dioxane (1 mL) was cooled to 0° C. Benzyl chloroformate (0.845 mL, 5.64 mmol) was added dropwise over 1 min. The pH was maintained between 7 and 9 by adding from time to time aq. 1M NaOH (total amount: about 5 mL). The mixture was stirred overnight while the temperature rose slowly to room temperature. The final pH was equal to 6.5 and an oily precipitate was lying in the bottom of the flask. This oily precipitate was decanted, dissolved in CHCl 3  and the solution dried over MgSO 4 . After filtration, the filtrate was evaporated under reduced pressure. The residue was diluted in MeOH (20 mL) and aq. 1M NaOH was added (10 mL). This solution was stirred at room temperature overnight and the pH was brought to 7 with aq. 1M HCl. The solvent was removed under reduced pressure and the residue dried under high vacuum. The dried residue was purified by RP—HPLC(C 18 -column, 95% H 2 O→75% H 2 O over 10 min→0% H 2 O over 10 min). The acid was obtained as a foam (224 mg, 40%).  1 H—NMR (400 MHz, CD 3 OD): δ=8.15 (s, br., 1H); 7.40-7.23 (m, 5H); 5.46 (s, br., 1H); 5.21 (s, br., 3H); 2.83 (dd, J 1 =15.6 Hz, J 2 =6.1 Hz, 1H); 1.79 (s, br., 2H); 1.05 (s, br., 3H). MS (pos. ionisation): m/z=330 (MH + ). 
       
    
    
     EXAMPLE 1  
       [0104]    4-Methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine Dihydrochloride:  
         [0105]    According to GPI with histamine dihydrochloride (12.1 g, 0.109 mol), NaOH (10.9 g, 0.272 mol), water (100 mL), MeOH (450 mL) and acetaldehyde (15.5 mL, 0.276 mol). The solution was acidified to pH&lt;1 with aq. conc. HCl and the solvent was removed under reduced pressure. The residue was thoroughly dried under high vacuum. The resulting oil was triturated with MeOH (1×150 mL, 2×50 mL) and filtered. The filtrate was evaporated under reduced pressure and the residue dried under high vacuum. This residue was then suspended in  i PrOH and this suspension refluxed for 1 h. After allowing it to cool to room temperature, the mixture was filtered and the precipitate dried under high vacuum. The product was obtained as a brown powder that was not purified further (21.2 g, 90%).  1 H—NMR (400 MHz, D 2 O): δ=8.70 (s, br., 1H); 3.76 (m, br., 1H); 3.53 (m, br., 1H); 3.09 (s, br., 2H); 1.69 (s, br., 3H).  
       EXAMPLE 2  
       [0106]    4-Ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine Dihydrochloride:  
         [0107]    According to GPI with histamine dihydrochloride (20.0 g, 0.109 mol), NaOH (19.6 g, 0.49 mol), water (100 mL), MeOH (450 mL) and propionaldehyde (20.0 mL, 0.276 mol). The reaction mixture was acidified to pH&lt;1 with aq. conc. HCl (200 mL) and the solvent was removed under reduced pressure. The residue was dried thoroughly under high vacuum and the resulting oil triturated with MeOH (1×150 mL and 2×50 mL). The filtrate was evaporated under reduced pressure and the residue dried under high vacuum. The resulting oil was triturated with EtOH (1×50 mL and 2×15 mL) and filtered. The precipitate was dried under high vacuum. 4-Ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride was obtained as a colorless powder (5.38 g, 22%).  1 H—NMR (400 MHz, CD 3 OD): δ=8.95 (s, 1H); 4.69-4.61 (m, 1H); 3.80-3.70 (m, 1H); 3.55-3.46 (m, 1H); 3.20-3.02 (m, 2H); 2.31-2.15 (m, 1H); 2.05-1.92 (m, 1H); 1.15 (t, J=7.8 Hz, 3H).  13 C—NMR (100 MHz, D 2 O): δ=134.70 (d); 124.98 (s); 123.72 (s); 53.26 (d); 40.59 (t); 24.41 (t); 18.11 (t); 8.88 (q). MS (EI): m/z=151 (M + , 1%); 150 (2%); 122 (100%); 107 (5%); 95 (13%); 80 (3%). HRMS: calc. for C 8 H 13 N 3 : M + =151.1158; found: 151.1109.  
       EXAMPLE 3  
       [0108]    4-Propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine Dihydrochloride:  
         [0109]    According to GPI with histamine dihydrochloride (20.0 g, 0.109 mol), NaOH (19.6 g, 0.49 mol), water (100 mL), MeOH (450 mL) and butyraldehyde (24.9 mL, 0.278 mol). The reaction mixture was acidified to pH&lt;1 with aq. conc. HCl (200 mL) and the solvent was removed under reduced pressure. The residue was dried thoroughly under high vacuum and the resulting oil triturated with MeOH (1×150 mL and 2×50 mL). The filtrate was evaporated under reduced pressure and the residue dried under high vacuum. The resulting oil was triturated with EtOH (1×50 mL and 2×15 mL) and filtered. The precipitate was dried under high vacuum. 4-Propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride was obtained as a colorless powder (20.9 g, 80%).  1 H—NMR (400 MHz, CD 3 OD): δ=8.99 (s, 11H); 4.75 (dd, J 1 =9.0 Hz, J 2 =4.4 Hz, 1H); 3.82-3.73 (m, 1H); 3.59-3.50 (m, 1H); 3.24-3.05 (m, 2H); 2.21-2.10 (m, 1H); 2.04-1.90 (m, 1H); 1.70-1.52 (m, 2H); 1.07 (t, J=7.8 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=136.13 (d); 126.43 (s); 125.61 (s); 53.05 (d); 41.79 (t); 34.41 (t); 19.45 (t); 19.30 (t); 14.01 (q). MS (EI): m/z=165 (M + , 1%); 164 (2%); 135 (2%); 122 (100%); 95 (12%); 80 (2%); 68 (5%).  
       EXAMPLE 4  
       [0110]    4-Phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine Dihydrochloride:  
         [0111]    According to GPI with histamine (10.0 g, 90 mmol), NaOH (9.0 g, 225 mol), water (90 mL), MeOH (365 mL) and benzaldehyde (23.1 mL, 0.23 mol). The reaction mixture was acidified to pH&lt;1 with aq. conc. HCl (165 mL) and the solvent was removed under reduced pressure. The residue was dried thoroughly under high vacuum and the resulting oil triturated with hot  i PrOH (150 mL). The mixture was filtered and the precipitate washed with cold  i PrOH (2×30 mL). The filtrate was heated to reflux and hexane (210 mL) added slowly, whereas a precipitate formed. The mixture was cooled to room temperature, then to −18° C. The precipitate was filtered and dried. 4-Phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride was obtained as a yellow powder that contained 0.7 eq of  i PrOH (14.1 g, 12.2 g of product, 50%).  1 H—NMR (400 MHz, CD 3 OD): δ=8.96 (s, 1H); 7.6-7.3 (m, 5H); 5.99 (s, 1H); 3.75-3.60 (m, 2H); 3.38-3.30 (m, 1H); 3.20 (dt, J 1 =16.6 Hz, J 2 =5.5 Hz, 1H).  13 C—NMR (100 MHz, D 2 O): δ=135.25 (s); 131.33 (d); 129.84 (d); 129.45 (d); 126.47 (s); 122.81 (s); 55.45 (d); 40.18 (t); 18.17 (t). MS (EI): m/z=199 (M + , 5%); 170 (100%); 122 (89%); 91 (3%). HRMS; Calc. for C 12 H 13 N 3 : M + =199.1107; found: 199.1109.  
       EXAMPLE 5  
       [0112]    4-Benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine Dihydrochloride (3):  
         [0113]    According to GPI with histamine dihydrochloride (20.0 g, 0.109 mol), NaOH (19.6 g, 0.49 mol), water (100 mL), MeOH (450 mL) and phenacetaldehyde (36 mL, 0.276 mol). The reaction mixture was acidified to pH&lt;1 with aq. conc. HCl (50 mL) and the solvent was removed under reduced pressure. The residue was dried thoroughly under high vacuum and the resulting oil triturated with MeOH (1×150 mL and 2×50 mL). The filtrate was evaporated under reduced pressure and the residue dried under high vacuum. The resulting oil was triturated with  i PrOH and filtered. The precipitate was dried under high vacuum. 4-Benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride was obtained as a colorless powder that still contained 1 eq.  i PrOH (31.9 g, 25 g of product, 96%).  1 H—NMR (400 MHz, D 2 O): δ=8.76 (s, 1H); 7.52-7.43 (m, 3H); 7.40-7.35 (m, 2H); 5.07 (dd, J 1 =9.1 Hz, J 2 =5.7 Hz, 1H); 3.76 (dt, J 1 =13.1 Hz, J 2 =5.2 Hz, 1H); 3.63 (dd, J 1 =14.4 Hz, J 2 =5.6 Hz, 1H); 3.53 (ddd, J 1 =13.9 Hz, J 2 =7.6 Hz, J 3 =6.1 Hz, 1H); 3.24 (dd, J 1 =14.2 Hz, J 2 =9.3 Hz, 1H); 3.16 (dd, J 1 =12.9 Hz, J 2 =7.8 Hz, 1H).  
       EXAMPLE 6  
       [0114]    Methyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0115]    According to GPII, starting from 4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.38 mmol), K 2 CO 3  (690 mg, 5.00 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and methyl chloroformate (0.39 mL, 5.0 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Methyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (270 mg, 58%). R f =0.30 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.52 (s, 1H); 4.99 (s, br., 1H); 4.30 (s, br., 1H); 3.71 (s, 3H); 3.15 (td, br., J 1 =11.7 Hz, J 2 =3.7 Hz, 1H); 2.67 (m, 1H); 2.54 (dd, J 1 =15.6 Hz, J 2 =4.2 Hz, 1H); 1.88 (d, J 1 =6.8 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=157.47 (s); 135.38 (d); 134.32 (s); 126.41 (s); 53.37 (q); 49.43 (d); 38.71 (t); 23.50 (t); 19.28 (q). MS (EI): m/z=195 (M + , 11%); 180 (100%); 136 (10%); 120 (16%); 107 (22%). HRMS: Calc. for C 9 H 13 N 3 O 2 : M + =195.1008; found: 195.1010.  
       EXAMPLE 7  
       [0116]    Benzyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0117]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (1.00 g, 4.48 mmol), K 2 CO 3  (1.24 g, 9.0 mmol), CHCl 3  (10 mL), H 2 O (8 mL) and benzyl chloroformate (1.36 mL, 9.0 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-8.5 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure. Twice successively, the residue was treated with aq. 1M HCl and the solvent removed under reduced pressure. The residue was then suspended in aq. 1M HCl (15 mL) and washed with Et 2 O (2×). The aq. phase was evaporated under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→0% H 2 O over 20 min. Benzyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (590 mg, 33%).  1 H—NMR (400 MHz, CD 3 OD): δ=8.75 (s, 1H); 7.42-7.27 (m, 5H); 5.19 (s, br., 3H); 4.46 (m, br., 1H); 3.25 (m, br., 1H); 2.78 (m, br., 1H); 2.69 (dd, J 1 =15.4 Hz, J 2 =3.4 Hz, 1H); 1.00 (s, br., 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=134.09 (d); 129.46 (d); 129.19 (d); 68.90 (t); 52.60 (d); 38.25 (t); 28.04 (t); 10.86 (q). MS (EI): m/z=285 (M + , 0.4%); 256 (45%); 194 (34%); 150 (5%); 120 (9%); 107 (5%); 91 (100%). HRMS: Calc. for C 16 H 19 N 3 O 2 : M + =285.1477; found: 285.1471. Elemental analysis: Calc. for C 16 H 19 N 3 O 2 .C 2 HF 3 O 2 .H 2 O: C 51.8%, H 5.3%, N 10.6%; found: C 52.0%, H 4.9%, N 9.8%.  
       EXAMPLE 8  
       [0118]    Benzyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0119]    According to GPII, starting from 4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (800 mg, 2.54 mmol), K 2 CO 3  (737 mg, 5.33 mmol), CHCl 3  (6 mL), H 2 O (5 mL) and benzyl chloroformate (0.80 mL, 5.33 mmol). After basic treatment for 1 h the mixture was acidified to pH 8 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O 0% H 2 O over 20 min). Benzyl 4-phenyl-1,4,6,7-tetrahydro -5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (291 mg, 25%) that contained 0.65 eq. H 2 O according to the elemental analysis. t R =11.26 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.83 (s, 1H); 7.48-7.27 (m, 10H); 6.48 (s, br., 1H); 5.26 (d, br., J=10.8 Hz, 1H); 5.18 (d, J=12.0 Hz, 1H); 4.38 (d, br., J=12.2 Hz, 1H); 3.20 (ddd, J 1 =15.9 Hz, J 2 =11.2 Hz, J 3 =4.6 Hz, 1H); 2.96-2.78 (m, 2H).  13 C—NMR (100 MHz, CD 3 OD): δ=139.04 (s); 137.49 (s); 134.91 (d); 129.89-128.98 (several peaks, d and s); 127.85 (s); 69.11 (t); 54.16 (d); 38.12 (t); 22.24 (t). MS (EI): m/z=333 (M + , 9%); 242 (89%); 212 (4%); 198 (61%); 169 (27%); 91 (100%). Elemental analysis: Calc. for C 20 H 19 N 3 O 2 .C 2 HF 3 O 2 .⅔H 2 O: C 57.5%, H 4.7%, N 9.1%; found: C 57.5%, H 4.4%, N 9.1%.  
       EXAMPLE 9  
       [0120]    Benzyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0121]    According to GPII, starting from 4-benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.74 mmol), K 2 CO 3  (507 mg, 3.67 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and benzyl chloroformate (0.55 mL, 3.67 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Benzyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (225 mg, 42%). R f =0.31 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.57 (s, 1H); 7.23, 7.15 and 7.03 (m, 10H, rot.); 5.33, 5.25, 5.08 and 4.95 (m, 2H, rot.); 4.84 and 4.60 (d, J=12.2 Hz, 1H, rot.); 4.81 and 4.17 (dd, J 1 =13.2 Hz and 13.7 Hz, J 2 =5.4 Hz and 4.6 Hz, 1H, rot.); 3.24-2.90 (m, 3H, rot.); 2.83-2.33 (m, 2H, rot.).  13 C—NMR (100 MHz, CD 3 OD): δ=157.24 and 156.95 (s, rot.); 139.24 and 138.79 (s, rot.); 137.46 (s); 135.51 and 135.46 (d, rot.); 130.44 (d); 129.39, 129.24, 129.13, 129.01, 128.93, 128.83 and 128.72 (3×d, rot.); 127.36 (d); 68.31 and 68.17 (t, rot.); 55.24 and 54.53 (d, rot.); 40.96 and 40.20 (t, rot.); 39.73 and 38.97 (t, rot.); 23.39 and 22.88 (t, rot.). MS (EI): m/z=256 (M + —C 7 H 7 , 26%); 212 (22%); 91 (100%). HRMS: Calc. for C 21 H 21 N 3 O 2 : M + =347.1634; found: 347.1603.  
       EXAMPLE 10  
       [0122]    Benzyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0123]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (600 mg, 2.52 mmol), K 2 CO 3  (720 mg, 5.2 mmol), CHCl 3  (6 mL), H 2 O (5 mL) and benzyl chloroformate (0.78 mL, 5.2 mmol). After basic treatment for 1 h the mixture was acidified to pH 8.5 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (3×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (85% H 2 O→0% H 2 O over 20 min). Benzyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam that was crystallised from Et 2 O (276 mg, 27%). Mp =166-7° C. t R =8.46 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.74 (s); 7.42-7.27 (m, 5H); 5.31 (m, br., 1H); 5.18 (s, br., 2H); 4.44 (m, br., 1H); 3.25 (m, br., 1H); 2.78 (m, br., 1H); 2.68 (dd, J 1 =15.6 Hz, J 2 =3.4 Hz, 1H); 1.76 (m, 2H); 1.44 (m, br., 2H); 0.98 (m, br., 3H).  13 C—NMR (100 MHz, CD 3 OD); δ=156.92 (s); 134.08 (d); 130-128 (several peaks, s and d); 68.93 (t); 51.13 (d); 38.15 (t); 36.74 (t); 22.16 (t); 20.27 (t); 14.07 (q). MS (EI): m/z=300 (M+H + , 20%); 256 (51%); 212 (60%); 208 (28%); 192 (3%); 164 (16%); 120 (12%); 91 (100%). Elemental analysis: Calc. for C 17 H 21 N 3 O 2 .C 2 HF 3 O 2 : C 55.2%, H 5.4%, N 10.2%; found C 55.1%, H 5.1%, N 10.0%.  
       EXAMPLE 11  
       [0124]    Methyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0125]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (600 mg, 2.68 mmol), K 2 CO 3  (778 mg, 5.63 mmol), CHCl 3  (6 mL), H 2 O (4 mL) and methyl chloroformate (0.436 mL, 5.63 mmol). After basic treatment for 1 h the mixture was acidified to pH 8 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O over 5 min then 40% H 2 O over 10 min). Methyl 4-ethyl -1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (71 mg, 8%).  1 H-NMR (400 MHz, CD 3 OD): δ=8.78 (s, 1H); 4.19 (s, br., 1H); 4.43 (s, br., 1H); 3.75 (s, 3H); 3.22 (m, br., 1H); 2.79 (m, 1H); 2.69 (m, 1H); 1.86 (m, 2H); 1.03 (t, J=7.6 Hz, 3H).  13 C—NMR (100 MHz, d 6 -DMSO, at 70° C.): δ=157.77 (s); 134.06 (d); 129.55 (s); 127.63 (s); 53.74 (q); 52.52 (d); 38.09 (t); 27.92 (t); 22.00 (t); 10.81 (q). MS (EI): m/z=209 (M + , 4%); 180 (100%); 150 (4%); 120 (54%); 107 (11%); 94 (15%); 93 (20%); 59 (76%). HRMS: Calc. for C 10 H 15 N 3 O 2 : M + =209.1164; found: 209.1171.  
       EXAMPLE 12  
       [0126]    Methyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0127]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (600 mg, 2.52 mmol), K 2 CO 3  (720 mg, 5.2 mmol), CHCl 3  (6 mL), H 2 O (4 mL) and methyl chloroformate (0.40 mL, 5.2 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→40% H 2 O over 15 min). Methyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (134 mg, 16%).  1 H-NMR (400 MHz, CD 3 OD): δ=8.78 (s); 5.29 (s, br., 1H); 4.39 (s, br., 1H); 3.73 (s, 3H); 3.25 (s, br., 1H); 2.80 (m, 1H); 2.70 (dd, J 1 =15.9 Hz, J 2 =3.9 Hz, 1H); 1.79 (m, 1H); 1.46 (m, 1H); 1.00 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, d 6 -DMSO, at 70° C.); δ=155.23 (s); 132.46 (d); 127.74 (s); 125.32 (s); 52.35 (q); 49.05 (d); 36.45 (t); 34.90 (t); 20.49 (t); 18.23 (t); 13.12 (q). MS (EI): m/z=223 (M + , 2%); 194 (0.5%); 192 (1%); 180 (100%); 164 (1%); 148 (1%); 121 (6%); 120 (13%); 107 (4%). HRMS: Calc. for C 11 H 17 N 3 O 2 : M + =223.1321; found: 223.1323.  
       EXAMPLE 13  
       [0128]    Methyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0129]    According to GPII, starting from 4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (800 mg, 2.54 mmol), K 2 CO 3  (737 mg, 5.33 mmol), CHCl 3  (8 mL), H 2 O (5 mL) and methyl chloroformate (0.412 mL, 5.33 mmol). After basic treatment for 1 h the mixture was acidified to pH 8 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→40% H 2 O over 15 min). Methyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (506 mg, 54%) that contained 1 eq water according to the elemental analysis.  1 H—NMR (400 MHz, CD 3 OD): δ=8.84 (s); 7.47-7.24 (m, 5H); 6.46 (s, br., 1H); 4.34 (d, br., J=11.2 Hz, 1H); 3.79 (s, 3H); 3.18 (ddd, J 1 =15.9 Hz, J 2 =11.2 Hz, J 3 =4.6 Hz, 1H); 2.96-2.86 (m, 1H); 2.82 (dd, J 1 =15.6 Hz, J 2 =3.7 Hz, 1H).  13 C—NMR (100 MHz, d 6 -DMSO, at 70° C.): δ=154.83 (s); 138.18 (s); 133.75 (d); 128.33 (d); 127.99 (d); 127.26 (d); 127.15 (s); 125.44 (s); 52.56 (q); 52.26 (d); 36.58 (t); 20.64 (t). MS (EI): m/z=257 (M + , 100%); 242 (27%); 226 (7%); 198 (22%); 180 (67%); 121 (6%); 120 (11%). HRMS: Calc. for C 14 H 15 N 3 O 2 : M + =257.1164; found: 257.1164. Elemental analysis: Calc. for C 14 H 15 N 3 O 2 .C 2 HF 3 O 2 .H 2 O: C 49.4%, H 4.7%, N 10.8%; found: C 49.8%, H 4.8%, N 10.4%.  
       EXAMPLE 14  
       [0130]    4-Ethyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine Trifluoroacetate:  
         [0131]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (600 mg, 2.68 mmol), K 2 CO 3  (778 mg, 5.63 mmol), CHCl 3  (6 mL), H 2 O (4 mL) and phenoxyacetyl chloride (0.78 mL, 5.6 mmol). After basic treatment for 1 h the mixture was acidified to pH 9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (3×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (85% H 20 →0% H 2 O over 20 min). 4-Ethyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate was obtained as foam (490 mg, 46%) that contained 1.5 eq. H 2 O according to the elemental analysis. t R =5.95 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.72 (s, 1H); 7.25 (t, J=7.3 Hz, 2H); 7.08-6.82 (m, 3H); 5.61 (dd, J 1 =9.3 Hz, J 2 =4.6 Hz, 0.9H, 1 st  rot.); 4.90-4.70 (m, 2 and 0.2H, 2 nd  rot.); 4.25 (dd, J 1 =14.4 Hz, J 2 =5.2 Hz, 0.9H, 1 st  rot.); 3.52 (ddd, J 1 =14.9 Hz, J 2 =12.0 Hz, J 3 =4.4 Hz, 0.9H, 1 st  rot.); 3.17 (m, 0.1H, 2 nd  rot.); 2.93 (m, 1H); 2.76 (m, 1H); 1.10 and 0.97 (t, J=7.3 Hz, 3H, 2 rot.).  3 C—NMR (100 MHz, CD 3 OD): δ=170.08 (s); 159.18 (s); 134.29 (d); 130.48 (d); 129.34 (s); 127.20 (s); 122.60 (d); 115.62 (d); 68.03 (t); 50.38 (d); 39.47 (t); 27.75 (t); 22.86 (t); 10.80 (q). MS (EI): m/z=285 (M + , 15%); 256 (60%); 192 (43%); 178 (4%); 150 (13%); 135 (20%); 107 (45%); 77 (100%). HRMS: Calc. for C 96 H 19 N 3 O 2 : M + =285.1477; found: 285.1472. Elemental analysis: Calc. for C 16 H 19 N 3 O 2 .C 2 HF 3 O 2 .{fraction (3/2)}H 2 O: C 50.7%, H 5.4%, N 9.8%; found: C 50.6%, H 5.6%, N 9.4%.  
       EXAMPLE 15  
       [0132]    4-Propyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c] pyridine Trifluoroacetate:  
         [0133]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (600 mg, 2.52 mmol), K 2 CO 3  (720 mg, 5.2 mmol), CHCl 3  (6 mL), H 2 O (4 mL) and phenoxyacetyl chloride (0.72 mL, 5.2 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (80% H 2 O 0% H 2 O over 20 min. 4-Propyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate was obtained as foam (307 mg, 30%) that contained 1.5 eq. H 2 O according to elemental analysis. t R =6.36 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.74 (s, 1H); 7.30-7.10 (m, 2H); 6.99-6.85 (m, 3H); 5.70 (t, J=7.1 Hz, 0.9H, 1 st  rot.); 4.97-4.71 (m, 2H and 0.2H, 2 nd  rot.); 4.27 (dd, J 1 =14.6 Hz, J 2 =5.4 Hz, 0.9H, 1 st  rot.); 3.54 (ddd, J 1 =15.3 Hz, J 2 =11.7 Hz, J 3 =4.2 Hz, 0.9H, 1 st  rot.); 3.19 (m, 0.1H, 2 nd  rot.); 2.94 (ddd, J 1 =16.9 Hz, J 2 =11.7 Hz, J 3 =5.4 Hz, 0.9H, 1st rot.); 2.78 (dd, J 1 =16.1 Hz, J 2 =3.7 Hz, 0.9H, 1 st  rot.); 2.70 (m, 0.2H, 2 nd  rot.); 1.88 (m, 0.11H, 2 nd  rot.); 1.80 (m, 0.9H, 1 st  rot.); 1.52 (m, 0.1H, 2 nd  rot.); 1.39 (m, 0.9H, 1 st  rot.); 1.00 and 0.95 (t, J=7.5 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD); δ=170.04 (s); 134.29 (d); 130.49 (d); 129.57 (s); 127.16 (s); 122.63 (d); 115.65 (d); 68.08 (t); 48.86 (d); 39.39 (t); 36.71 (t); 22.89 (t); 20.19 (t); 14.18 (q). MS (EI): m/z=299 (M + , 21%); 256 (100%); 206 (64%); 192 (4%); 135 (23%); 120 (40%); 107 (39%); 93 (15%). HRMS: Calc. for C 17 H 21 N 3 O 2 : M + =299.1634; found: 299.1630. Elemental analysis: Calc. for C 17 H 21 N 3 O 2 .C 2 HF 3 O 2 .{fraction (3/2)}H 2 O: C 51.8%, H 5.7%, N 9.5%; found: C 51.9%, H 5.6%, N 9.2%.  
       EXAMPLE 16  
       [0134]    4-Phenyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine Trifluoroacetate:  
         [0135]    According to GPII, starting from 4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (800 mg, 2.54 mmol), K 2 CO 3  (737 mg, 5.33 mmol), CHCl 3  (8 mL), H 2 O (6 mL) and phenoxyacetyl chloride (0.74 mL, 5.33 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (85% H 2 O 0% H 2 O over 20 min). 4-Phenyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate was obtained as foam (400 mg, 35%). t R =6.93 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.85 (s, 1H); 7.46-7.23 (m, 7H); 7.00-6.86 (m, 3H); 4.96-4.76 (m, 3H); 4.20 (dd, J 1 =14.4 Hz, J 2 =4.9 Hz, 1H); 3.45 (m, 11H); 3.06 (m, 11H); 2.91 (d, J=15.6 Hz, 11H).  13 C—NMR (100 MHz, d 6 -DMSO): δ=166.72 (s); 157.72 (s); 138.00 (s); 134.10 (d); 129.27 (d); 128.62 (d); 128.32 (d); 127.77 (d); 127.42 (s); 124.84 (s); 120.89 (d); 114.52 (d); 65.93 (t); 49.70 (d); 37.73 (t); 21.59 (t). MS (EI): m/z=333 (M + , 77%); 256 (4%); 240 (100%); 226 (13%); 198 (56%); 169 (48%); 135 (3%); 122 (8%); 120 (12%); 94 (19%); 77 (73%). HRMS: Calc. for C 20 H 19 N 3 O 2 : M + =333.1477; found: 333.1475.  
       EXAMPLE 17  
       [0136]    Cyclopentyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0137]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.78 mmol), K 2 CO3 (517 mg, 3.74 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and cyclopentyl chloroformate (511 mg, 3.74 mmol). After basic treatment for 1 h the mixture was acidified to pH 9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (3×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→65% H 2 O over 10 min→0% H 2 O over 10 min). Cyclopentyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (174 mg, 26%). t R =10.14 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.75 (s); 5.17 (s, br., 1H); 5.12 (t, J=5.4 Hz, 1H); 3.21 (s, br., 1H); 2.76 (m, 1H); 2.68 (dd, J 1 =14.9 Hz, J 2 =3.4 Hz, 1H); 1.95-1.58 (m, 1H); 1.02 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=157.00 (s); 134.08 (d); 129.71 (s); 127.70 (s); 80.44 (d); 52.48 (d); 37.72 (t); 33.78 (t); 27.86 (t); 24.61 (t); 22.00 (t); 10.95 (q). MS (EI): m/z=263 (M + , 4%); 234 (48%); 194 (12%); 178 (12%); 166 (100%); 122 (33%); 120 (14%); 107 (5%), 93 (5%). HRMS: Calc. for C 14 H 21 N 3 O 2 : M + =263.1634; found: 263.1595.  
       EXAMPLE 18  
       [0138]    Cyclopentyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0139]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.68 mmol), K 2 CO3 (487 mg, 3.53 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and cyclopentyl chloroformate (482 mg, 3.53 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→65% H 2 O over 10 min→0% H 2 O over 10 min). Cyclopentyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (106 mg, 27%). t R =10.97 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.75 (s, 1H); 5.25 (m, br., 1H); 5.11 (s, br., 1H); 4.38 (m, br., 1H); 3.22 (m, br., 1H); 2.77 (m, br., 1H); 2.68 (dd, J 1 =15.9 Hz, J 2 =4.4 Hz, 1H); 1.95-1.58 (m, 10H); 1.46 (m, 12H); 1.00 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=134.05 (d); 129.87 (s); 127.67 (s); 80.47 (d); 51.03 (d); 38.10 (t); 36.99 (t); 33.79 (t); 24.59 (t); 21.91 (t); 20.34 (t); 14.12 (q). MS (EI): m/z=277 (M + , 1%); 234 (32%); 208 (9%); 192 (10%); 166 (74%); 164 (7%); 150 (4%); 135 (5%); 122 (36%); 120 (49%); 95 (15%); 69 (100%). HRMS: Calc. for C 15 H 23 N 3 O 2 : M + =277.1790; found: 277.1780.  
       EXAMPLE 19  
       [0140]    Cyclopentyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0141]    According to GPII, starting from 4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.59 mmol), K 2 CO3 (461 mg, 3.34 mmol), CHCl 3  (5 mL), H 2 O (2.5 mL) and cyclopentyl chloroformate (456 mg, 3.34 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by RP—HPLC (95% H 2 O→65% H 2 O over 10 min→0% H 2 O over 10 min). Cyclopentyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (162 mg, 24%) that contained 1 eq. H 2 O according to the elemental analysis. t R =10.35 min.  1 H—NMR (400 MHz, CD 3 OD): δ=8.83 (s, 1H); 7.43-7.35 (m, 3H); 7.32-7.27 (m, 2H); 6.44 (s, br., 1H); 5.16 (s, br., 1H); 4.34 (s, br., 1H); 3.18 (m, 1H); 2.91 (dd, J 1 =16.1 Hz, J 2 =5.9 Hz, 1H); 2.83 (dd, J 1 =16.4 Hz, J 2 =4.9 Hz, 1H); 1.97-1.56 (m, 8H).  13 C—NMR (100 MHz, CD 3 OD): δ=139.24 (s); 134.90 (d); 129.90 (d); 129.84 (d); 129.43 (s); 128.89 (d); 127.38 (s); 80.75 (d); 54.01 (d); 38.01 (t); 33.84 (t); 33.71 (t); 24.58 (t); 22.18 (t). MS (EI): m/z=311 (M + , 56%); 242 (100%); 226 (24%); 198 (91%); 169 (72%); 166 (39%); 122 (13%). HRMS: Calc. for C 18 H 21 N 3 O 2 : M + =311.1634; found: 311.1625. Elemental analysis: Calc. for C 18 H 21 N 3 O 2 .C 2 HF 3 O 2 H 2 O: C 54.2%, H 5.5%, N 9.5%; found: C 54.1%, H 5.4%, N 9.4%.  
       EXAMPLE 20  
       [0142]    4-Fluorophenyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0143]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.78 mmol), K 2 CO 3  (517 mg, 3.74 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and 4-fluorophenyl chloroformate (0.49 mL, 3.7 mmol). After basic treatment for 1 h the mixture was acidified to pH 9 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (3×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure, the residue taken in aq. 1 M HCl and washed with Et 2 O(1×). The aq. phase was evaporated under reduced pressure and the residue was purified by RP—HPLC (90% H 2 O→65% H 2 O over 10 min→5% H 2 O over 10 min). 4-Fluorophenyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (64 mg, 9%). t R =9.21 min.  1 H-NMR (400 MHz, CD 3 OD): δ=8.80 (s, 1H); 7.12 (m, 4H); 5.81 (m, br., 1H); 4.55 (m, br., 1H); 3.44 (m, br., 1H); 2.97 (m, br., 1H); 2.81 (m, br., 1H); 1.96 (m, br., 2H); 1.12 (m, br., 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=161.44 (sd, J F =182 Hz); 155.77 (s); 148.38 (s); 134.25 (d); 129.36 (s); 127.63 (s); 124.33 (d); 116.76 (sd, J F =17 Hz); 53.01 (d); 38.31 (t); 27.62 (t); 22.39 (t); 10.84 (q). MS (EI): m/z=289 (M + , 6%); 260 (100%); 178 (77%); 122 (12%); 120 (12%); 112 (7%); 95 (15%). HRMS: Calc. for C 15 H 16 FN 3 O 2 : M + =289.1227; found: 289.1228.  
       EXAMPLE 21  
       [0144]    4-Fluorophenyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate Trifluoroacetate:  
         [0145]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.68 mmol), K 2 CO 3  (487 mg, 3.53 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and 4-fluorophenyl chloroformate (0.47 mg, 3.6 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by FC (MeOH/CHCl 3  2:98→5:95→10:90→1:1). 4-Fluorophenyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (92 mg, 18%). R f =0.20 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CDCl 3 ): δ=7.80 (s, br., 1H); 7.03 (m, br., 4H); 7.23 and 4.93 (m, 1H, rot.); 4.45 and 4.36 (m, 1H, rot.); 3.43-3.09 (m, 1H); 2.88-2.76, 2.69-2.46 and 2.32-2.18 (m, 2H, rot.); 1.93-1.33 (m, 2H, rot.); 0.98-0.87 (m, 3H, rot.).  13 C—NMR (100 MHz, CDCl 3 ): δ=159.93 (sd, J F =182 Hz); 154.43 (s); 147.15 (s); 134.15 (d); 123.09 (d); 115.88 (dd, J F =18 Hz); 53.16 and 52.58 (d, rot.); 38.96 and 38.74 (t, rot.); 37.01 and 36.64 (t, rot.); 23.36 and 22.27 (t, rot.); 19.67 and 19.34 (t, rot.); 14.34 and 14.18 (q, rot.). MS (EI): m/z=303 (M + , 2%); 260 (100%); 224 (5%); 208 (7%); 150 (19%); 122 (17%); 112 (10%). HRMS: Calc. for C 16 H 18 FN 3 O 2 : M + =303.1383; found: 303.1392.  
       EXAMPLE 22  
       [0146]    Methoxy-ethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0147]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.78 mmol), K 2 CO 3  (517 mg, 3.74 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and methoxyethyl chloroformate (518 mg, 3.74 mmol). After basic treatment for 1 h the mixture was acidified to pH 9 with aq. 1M HCl. The reaction mixture was extracted with CHCl 3  (3×) and the combined org. phases were dried over Na 2 SO 4 . The residue was purified by FC (MeOH/CHCl 3  2:98→5:95→10:90). Methoxy-ethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (98 mg, 22%) that contained 0.5 eq. H 2 O according to the elemental analysis. R f =0.05 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.55 (s, 1H); 5.00 (s, br., 1H); 4.35 (m, br., 1H); 4.24 (s, br., 2H); 3.60 (s, br., 2H); 3.35 (s, br., 3H); 3.18 (s, br., 1H); 2.71 (ddd, J 1 =16.4 Hz, J 2 =12.0 Hz, J 3 =5.6 Hz, 1H); 2.53 (dd, J 1 =15.4 Hz, J 2 =3.4 Hz, 1H); 1.89 (m, 1H); 1.71 (m, 1H); 1.00 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=157.50 (s); 135.22 (d); 133.67 (s); 126.64 (s); 71.86 (t); 65.80 (t); 59.06 (q); 54.81 (d); 39.18 and 38.88 (t, rot.); 28.49 and 28.27 (t, rot.); 23.59 and 23.07 (t, rot.); 11.14 (q). MS (EI): m/z=253 (M + , 6%); 224 (100%); 194 (4%); 166 (7%); 150 (3%); 122 (38%). HRMS: Calc. for C 12 H 19 N 3 O 3 : M + =253.1426; found: 253.1421. Elemental analysis: Calc. for C 12 H 19 N 3 O 3 .½H 2 O: C 54.95%, H 7.68%, N 16.07%; found: C 55.07%, H 7.81%, N 15.78%.  
       EXAMPLE 23  
       [0148]    Methoxyethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate: According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (400 mg, 1.68 mmol), K 2 CO 3  (487 mg, 3.53 mmol), CHCl 3  (4 mL), H 2 O (2 mL) and methoxyethyl chloroformate (490 mg, 3.53 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by FC (MeOH/CHCl 3  2:98→5:95→10:90). Methoxyethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (87 mg, 20%) that contained 0.25 eq. H 2 O according to the elemental analysis. R f =0.25 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.51 (s, 1H); 5.08 (s, br., 1H); 4.32 (m, br., 1H); 4.23 (m, br., 2H); 3.59 (s, br., 2H); 3.36 and 3.34 (s, 3H, rot.); 3.17 (m, br., 1H); 2.70 (ddd, J 1 =16.1 Hz, J 2 =12.0 Hz, J 3 =5.6 Hz, 1H); 2.53 (dd, J 1 =15.4 Hz, J 2 =3.2 Hz, 1H); 1.79 (m, 1H); 1.70 (m, 1H); 1.45 (m, 2H); 0.97 (t, J=7.6 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=157.44 (s); 135.22 (d); 133.93 (s); 126.82 (s); 71.84 (t); 65.79 (t); 59.05 (q); 53.30 (d); 39.10 and 38.80 (t, rot.); 37.71 and 37.46 (t, rot.); 23.59 and 23.06 (t, rot.); 20.49 (t); 14.41 (q). MS (EI): m/z=267 (M + , 7%); 224 (100%); 208 (6%); 192 (7%); 180 (12%); 166 (11%); 122 (62%). HRMS: Calc. for C 13 H 21 N 3 O 3 : M + =267.1581; found: 267.1582. Elemental analysis: Calc. for C 13 H 21 N 3 O 3 .¼H 2 O: C 57.44%, H 7.97%, N 15.52%; found: C 57.28%, H 8.11%, N 15.22%.  
       EXAMPLE 24  
       [0149]    Methoxyethyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0150]    According to GPII, starting from 4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.59 mmol), K 2 CO 3  (461 mg, 3.34 mmol), CHCl 3  (6 mL), H 2 O (4 mL) and methoxyethyl chloroformate (462 mg, 3.34 mmol). After basic treatment for 1 h the mixture was acidified to pH 8-9 with aq. 1 M HCl. The reaction mixture was extracted with CHCl 3  (4×) and the combined org. phases were dried over Na 2 SO 4 . The solvent was removed under reduced pressure and the residue purified by FC (MeOH/CHCl 3  2:98→5:95→10:90). Methoxyethyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (267 mg, 56%). R f =0.26 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.62 (s, 1H); 7.30 (m, 5H); 6.30 (s, br., 1H); 4.29 (m, br., 2H); 3.65 (m, br., 2H); 3.38 (s, 3H); 3.09 (m, 1H); 2.82 (m, br., 1H); 2.65 (m, br., 1H).  13 C-NMR (100 MHz, CD 3 OD): δ=157.09 (s); 141.43 (s); 135.89 (d); 131.30 (s); 129.25 (d); 129.03 (d); 128.77 (d); 128.34 (s); 77.81 (t); 65.99 (t); 59.08 (q); 56.09 (d); 38.95 and 38.81 (t, rot.); 23.51 and 23.07 (t, rot.). MS (EI): m/z=301 (M + , 24%); 242 (26%); 198 (41%); 115 (10%); 88 (11%). HRMS: Calc. for C 16 H 19 N 3 O 3 : M + =301.1426; found: 301.1419.  
       EXAMPLE 25  
       [0151]    Benzyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0152]    According to GPII, starting from 4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.38 mmol), K 2 CO 3  (690 mg, 5.00 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and benzyl chloroformate (0.75 mL, 5.0 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Benzyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (193 mg, 30%). Rf=0.25 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.51 (s, 11H); 7.38-7.52 (m, 5H); 5.13 (m, br., 3H); 4.33 (d, br., J=10 Hz, 1H); 3.16 (t, br., J=11.2 Hz, 1H); 2.66 (m, br., 1H); 2.54 (d, br., J=12.9 Hz, 1H); 1.38 (d, J=6.8 Hz, 3H).  13 C—NMR (100 MHz, CDCl 3 ): δ=155.43 and 155.12 (s, rot.); 136.49 (s); 134.00 (d); 132.85 (s); 128.45 (d); 127.98 (d); 127.67 (d); 125.94 and 124.83 (s, rot.); 67.30 (t); 48.36 (d); 37.81 (t); 23.19 and 22.51 (t, rot.); 19.56 and 19.14 (q, rot.). MS (EI): m/z=271 (M + , 0.5%); 256 (6%); 180 (82%); 136 (16%); 108 (14%); 91 (100%). HRMS: Calc. for C 15 H 17 N 3 O 2 : M + =271.1321; found: 271.1308.  
       EXAMPLE 26  
       [0153]    Benzyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0154]    According to GPII, starting from 4-benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.74 mmol), K 2 CO 3  (507 mg, 3.67 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and benzyl chloroformate (0.55 mL, 3.67 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Benzyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (225 mg, 42%). R f =0.31 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.57 (s, 1H); 7.23, 7.15 and 7.03 (m, 10H, rot.); 5.33, 5.25, 5.08 and 4.95 (m, 2H, rot.); 4.84 and 4.60 (d, J=12.2 Hz, 1H, rot.); 4.81 and 4.17 (dd, J 1 =13.2 Hz and 13.7 Hz, J 2 =5.4 Hz and 4.6 Hz, 1H, rot.); 3.24-2.90 (m, 3H, rot.); 2.83-2.33 (m, 2H, rot.).  13 C-NMR (100 MHz, CD 3 OD): δ=157.24 and 156.95 (s, rot.); 139.24 and 138.79 (s, rot.); 137.46 (s); 135.51 and 135.46 (d, rot.); 130.44 (d); 129.39, 129.24, 129.13, 129.01, 128.93, 128.83 and 128.72 (3×d, rot.); 127.36 (d); 68.31 and 68.17 (t, rot.); 55.24 and 54.53 (d, rot.); 40.96 and 40.20 (t, rot.); 39.73 and 38.97 (t, rot.); 23.39 and 22.88 (t, rot.). MS (EI): m/z=256 (M + —C 7 H 7 , 26%); 212 (22%); 91 (100%). HRMS: Calc. for C 21 H 21 N 3 O 2 : M + =347.1634; found: 347.1603.  
       EXAMPLE 27  
       [0155]    4-Methyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]Pyridine:  
         [0156]    According to GPII, starting from 4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.38 mmol), K 2 CO 3  (690 mg, 5.00 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and phenoxyacetyl chloride (0.69 mL, 5.0 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). 4-Methyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine was obtained as foam (28 mg, 5%). R f =0.12 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.55 and 7.53 (s, 1H, rot.); 7.26 (t, J=7.1 Hz, 2H); 6.99-6.90 (m, 3H); 5.45 and 5.05 (q, J=6.6 Hz, 1H, rot.); 4.95-4.77 (m, 3H); 4.73 and 4.14 (dd, J 1 =13.4 Hz and 14.2 Hz, J 2 =5.4 Hz and 5.1 Hz, 1H, rot.); 3.46 and 3.12 (ddd, J 1 =12.0 Hz and 12.9 Hz, J 2 =12.0 Hz and 12.9 Hz, J 3 =4.2 Hz and 4.9 Hz, 1H, rot.); 2.88-2.54 (m, 2H, rot.); 1.54 and 1.41 (d, J=6.6 Hz and 6.8 Hz, 3H, rot.).  13 C—NMR (100 MHz, CDCl 3 ): δ=166.41 and 166.91 (s); 157.83 (s); 134.29 (d); 129.74 (d); 121.86 (d); 114.74 and 114.63 (d, rot.); 68.18 and 67.47 (t, rot.); 50.15 and 46.78 (d, rot.); 39.81 and 35.94 (t, rot.); 24.03 and 22.04 (t, rot.); 20.52 and 18.91 (q, rot.). MS (EI): m/z=271 (M + , 20%); 194 (1%); 178 (100%); 164 (10%); 135 (15%); 107 (44%); 94 (15%).  
       EXAMPLE 28  
       [0157]    Allyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0158]    According to GPII, starting from 4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.38 mmol), K 2 CO 3  (690 mg, 5.00 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and allyl chloroformate (0.53 mL, 5.0 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Allyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (284 mg, 54%). R f =0.30 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.53 (s, 1H); 6.00-5.85 (m, 1H); 5.29 (ddd, J 1 =17.2 Hz, J 2 =3.2 Hz, J 3 =1.7 Hz, 1H), 5.19 (ddd, J 1 =10.5 Hz, J 2 =2.8 Hz, J 3 =1.3 Hz, 1H); 5.11 (d, br., J=6.4 Hz, 1H); 4.60 (dd, J 1 =3.9 Hz, J 2 =1.2 Hz, 2H); 4.33 (dd, J 1 =13.4 Hz, J 2 =4.9 Hz, 1H); 3.16 (m, br., 1H); 2.68 (m, 1H); 2.55 (ddd, J 1 =15.4 Hz, J 2 =4.2 Hz, J 3 =1.0 Hz, 1H); 1.39 (d, J=6.8 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=156.58 (s); 135.40 (d); 134.31 (s); 134.09 (d); 126.31 (s); 117.73 (t); 67.25 (t); 49.39 (d); 38.71 (t); 23.57 and 23.24 (t, rot.); 19.54 and 19.16 (q, rot.). MS (EI): m/z=221 (M + , 2%); 206 (27%); 180 (100%); 136 (30%); 120 (30%); 107 (38%). HRMS: Calc. for C 11 H 15 N 3 O 2 : M + =221.1164; found: 221.1160.  
       EXAMPLE 29  
       [0159]    Allyl 4-ethyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0160]    According to GPII, starting from benzyl-4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate (500 mg, 2.23 mmol), K 2 CO 3  (646 mg, 4.68 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and allyl chloroformate (0.50 mL, 4.7 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→15:85 over 25 min). Allyl 4-ethyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (2.2 mg, 0.4%). The low yield is probably due to a leak during the FC. R f =0.15 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.52 (s, 1H); 5.95 (m, 1H); 5.29 (dd, J 1 =17.3 Hz, J 2 =1.2 Hz, 1H); 5.20 (dd, J 1 =10.5 Hz, J 2 =1.2 Hz, 1H); 4.99 (m, br., 1H); 4.60 (d, J=5.1 Hz, 2H); 4.34 (dd, J 1 =13.4 Hz, J 2 =4.6 Hz, 1H); 3.19 (m, br., 1H); 2.70 (dddd, J 1 =15.6 Hz, J 2 =12.0 Hz, J 3 =5.6 Hz, J 4 =1.2 Hz, 1H); 2.53 (ddd, J 1 =15.4 Hz, J 2 =4.2 Hz, J 3 =1.0 Hz, 1H); 1.88 (dddd, J 1 =15.1 Hz, J 2 =15.1 Hz, J 3 =7.6 Hz, J 4 =4.6 Hz, 1H); 1.71 (m, 1H); 0.99 (t, J=7.6 Hz, 3H). MS (EI): m/z=235 (M + , 2%); 206 (100%); 194 (16%); 178 (5%); 162 (38%); 150 (4%). HRMS: Calc. for C 12 H 17 N 3 O 2 : M + =235.1321; found: 235.1330.  
       EXAMPLE 30  
       [0161]    Allyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0162]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.10 mmol), K 2 CO 3  (609 mg, 4.40 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and allyl chloroformate (0.47 mL, 4.4 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Allyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (68 mg, 13%). R f =0.20 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.51 (s, 1H); 5.96 (m, 1H); 5.29 (d, br., J=17.3 Hz, 1H); 5.19 (dd, J 1 =10.5 Hz, J 2 =1.2 Hz, 1H); 5.09 (s, br., 1H); 4.60 (m, 2H); 4.32 (d, br., J=13.4 Hz, 1H); 3.19 (d, br., J=11.5 Hz, 1H); 2.70 (m, 1H); 2.55 (dd, J 1 =15.4 Hz, J 2 4.2 Hz, 1H); 1.79 (m, 1H); 1.70 (m, 1H); 1.45 (m, 2H); 0.96 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=157.43 (s); 135.38 (d); 134.26 (s); 134.14 (d); 126.51 (s); 118.02 and 117.75 (t, rot.); 67.36 (t); 53.46 and 53.30 (d, rot.); 39.10 and 38.81 (t, rot.); 37.71 and 37.45 (t, rot.); 23.62 and 22.97 (t, rot.); 20.51 (t); 14.34 (q). MS (EI): m/z=249 (M + , 1%); 206 (44%); 192 (2%); 162 (13%); 135 (4%); 120 (34%); 107 (7%). HRMS: Calc. for C 13 H 19 N 3 O 2 : M + =249.1477; found: 249.1468.  
       EXAMPLE 31  
       [0163]    2,2,2-Trichloroethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0164]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.23 mmol), K 2 CO 3  (646 mg, 4.68 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and 2,2,2-trichloroethyl chloroformate (0.64 mL, 4.68 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). 2,2,2-Trichloroethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (168 mg, 23%). R f =0.16 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.53 (s, 1H); 5.05 (m, 1H); 4.97-4.72 (m, 2H); 4.39 (m, 1H); 3.25 (m, 1H); 2.76 (m, 1H); 2.58 (dd, J 1 =15.4 Hz, J 2 =3.9 Hz, 1H); 1.93 (m, 1H); 1.75 (m, 1H); 1.03 (m, 3H, rot.).  13 C—NMR (100 MHz, CD 3 OD): δ=155.57 (s); 135.38 (d); 76.22 and 76.02 (t, rot.); 55.53 (d); 39.47 (t); 28.57 and 28.23 (t, rot.); 23.70 and 22.89 (t, rot.); 11.40 and 11.11 (q, rot.). MS (EI): m/z=325, 327, 329 (M + , 2%); 296, 298, 300 (100%); 262 (3%); 178 (19%); 166 (14%); 133 (17%); 122 (38%); 120 (38%); 107 (9%). HRMS: Calc. for 10 C 11 H 14 C 13 N 3 O 2 : M+325.0152; found: 325.0148.  
       EXAMPLE 32  
       [0165]    Allyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate: According to GPII, starting from 4-benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.74 mmol), K 2 CO 3  (507 mg, 3.67 mmol), CHCl 3  15 (6 mL), H 2 O (3 mL) and allyl chloroformate (0.39 mL, 3.67 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). Allyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (63 mg, 12%). R f =0.31 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.59 (s, 1H); 7.29-6.94 (m, 5H); 5.86 and 5.69 (m, 1H, rot.); 5.32 and 5.23 (m, 1H, rot.); 5.23-5.12 (m, 1H); 5.04 (d, br., J=12.7 Hz, 1H); 4.49 and 4.29 (m, 2H, rot.); 4.18 and 4.03 (dd, J 1 =13.4 Hz and 12.7 Hz, J 2 =4.9 Hz and 4.4 Hz, 1H, rot.); 3.24-2.38 (m, 5H, rot.).  13 C—NMR (100 MHz, CD 3 OD): δ=157.06 and 156.80 (s, rot.); 139.33 and 138.83 (s, rot.); 135.52 (d); 134.08, 133.78 and 133.49 (2×s, rot.); 130.47 (d); 129.21 and 129.12 (d, rot.); 127.54 and 127.32 (d, rot.); 117.67 and 117.55 (t, rot.); 67.17 (t); 55.19 and 54.45 (d, rot.); 40.99 and 40.24 (t, rot.); 39.65 and 38.85 (t, rot.); 23.36 and 22.92 (t, rot.). MS (EI): m/z=297 (M + , 0.05%); 240 (3%); 22 (14%); 206 (100%); 162 (21%); 120 (21%); 91 (50%). HRMS: Calc. for C 17 H 19 N 3 O 2 : M + =297.1477; found: 297.1448.  
       EXAMPLE 33  
       [0166]    2,2,2-Trichloroethyl -4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0167]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.10 mmol), K 2 CO 3  (609 mg, 4.40 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and 2,2,2-trichloroethyl chloroformate (0.61 mL, 4.4 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→15:85 over 25 min). 2,2,2-Trichloroethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam that still contained 0.2 eq. H 2 O according to the elemental analysis (196 mg, 27%). R f =0.25 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.53 (s, 1H); 5.15 (m, br., 1H); 4.85 (m, 2H); 4.36 (m, 1H); 3.26 (m, 1H); 2.76 (m, 1H); 2.58 (d, J=15.4 Hz, 1H); 2.30 (d, J=15.1 Hz, 1H); 1.83 (m, 1H); 1.73 (m, 1H); 1.47 (m, 2H); 0.98 (t, J=7.3 Hz, 1H).  13 C—NMR (100 MHz, CD 3 OD): δ=155.53 (s); 135.38 (d); 76.23 and 76.02 (t, rot.); 54.15 and 53.90 (s, rot.); 51.78 and 51.61 (d, rot.); 39.42 and 39.04 (t, rot.); 37.84, 37.37, 37.11 and 36.64 (t, rot.); 23.70, 22.86, 22.27 and 21.56 (t, rot.); 20.74, 20.60, 20.49 and 20.34 (t, rot.); 14.51, 14.45, 14.22 and 14.27 (q, rot.). MS (EI): m/z=296, 298 and 300 (100%); 262 (4%); 208 (10%); 192 (16%); 166 (24%); 137 (17%); 122 (38%); 95 (25%). HRMS: Calc. for C 12 H 16 C 13 N 3 O 2 : M + =339.0308; found: 339.0318. Elemental analysis: Calc. for C 12 H 16 C 13 N 3 O 2 .⅕H 2 O: C 41.87%, H 4.80%, N 12.21%; found: C 41.87%, H 4.84%, N 11.81%.  
       EXAMPLE 34  
       [0168]    2,2,2-Trichloroethyl -4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine -5-carboxylate: According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.10 mmol), K 2 CO 3  (609 mg, 4.40 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and 2,2,2-trichloroethyl chloroformate (0.61 mL, 4.4 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1 M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→15:85 over 25 min). 2,2,2-trichloroethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam that still contained 0.2 eq. H 2 O according to the elemental analysis (196 mg, 27%). R f =0.25 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=7.53 (s, 1H); 5.15 (m, br., 1H); 4.85 (m, 2H); 4.36 (m, 1H); 3.26 (m, 1H); 2.76 (m, 1H); 2.58 (d, J=15.4 Hz, 1H); 2.30 (d, J=15.1 Hz, 1H); 1.83 (m, 1H); 1.73 (m, 1H); 1.47 (m, 2H); 0.98 (t, J=7.3 Hz, 1H).  13 C—NMR (100 MHz, CD 3 OD): δ=155.53 (s); 135.38 (d); 76.23 and 76.02 (t, rot.); 54.15 and 53.90 (s, rot.); 51.78 and 51.61 (d, rot.); 39.42 and 39.04 (t, rot.); 37.84, 37.37, 37.11 and 36.64 (t, rot.); 23.70, 22.86, 22.27 and 21.56 (t, rot.); 20.74, 20.60, 20.49 and 20.34 (t, rot.); 14.51, 14.45, 14.22 and 14.27 (q, rot.). MS (EI): m/z=296, 298 and 300 (100%); 262 (4%); 208 (10%); 192 (16%); 166 (24%); 137 (17%); 122 (38%); 95 (25%). HRMS: Calc. for C 12 H 16 C 13 N 3 O 2 : M + =339.0308; found: 339.0318. Elemental analysis: Calc. for C 12 H 16 C 13 N 3 O 2 .⅕H 2 O: C 41.87%, H 4.80%, N 12.21%; found: C 41.87%, H 4.84%, N 11.81%.  
       EXAMPLE 35  
       [0169]    2,2,2-Trichloroethyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine -5-carboxylate:  
         [0170]    According to GPII, starting from 4-benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 1.74 mmol), K 2 CO 3  (507 mg, 3.67 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and 2,2,2-trichloroethyl chloroformate (0.51 mL, 3.7 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→15:85 over 25 min 2,2,2-trichloroethyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (211 mg, 31%). R f =0.22 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): 6 =7.61 (s, 1H); 7.27-7.07 (m, 5H); 5.86 and 5.12 (m, 1H, rot.); 4.79-4.63 (m, 1.5H, rot.); 4.83-4.16 (m, 1.5H, rot.); 3.28-3.22 (m, 1H, rot.); 3.20-2.85 (m, 2H, rot.); 2.73-2.63 (m, 1H, rot.); 2.49 and 2.20 (dd, J=15.4 Hz and 15.6 Hz, J 2 =3.2 Hz and 3.9 Hz, 1H, rot.).  13 C—NMR (100 MHz, CD 3 OD): δ=155.32, 155.13 and 154.98 (s, rot.); 138.94, 138.66, 138.25 and 138.07 (s, rot.); 135.69 and 135.60 (d, rot.); 130.62 and 130.51 (d, rot.); 129.34, 129.21 and 129.06 (d, rot.); 127.69, 127.58 127.45 and 127.39 (d, rot.); 75.97 and 75.88 (t, rot.); 55.41 and 55.13 (s, rot.); 52.84 and 52.70 (d, rot.); 40.89, 40.26 and 40.18 (t, rot.); 39.88, 39.70, 39.50 and 39.29 (t, rot.); 23.42, 22.74, 22.06 and 21.53 (t, rot.). MS (EI): m/z 387 (M + , 0.3%); 296, 298 and 300 (100%); 262 (4%); 226 (2%); 166 (22%); 122 (35%). HRMS: Calc. for C 16 H 16 C 13 N 3 O 2 : M + =387.0308; found: 387.0318. Elemental analysis: Calc. for C 16 H 16 C 13 N 3 O 2 : C 49.44%, H 4.15%, N 10.81%; found: C 49.53%, H 4.29%, N 10.36%.  
       EXAMPLE 36  
       [0171]    4-Ethyl-5-(4-nitrobenzyl)-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0172]    According to GPII, starting from 4-ethyl-4,5,6,7-tetrahydro-1H-imidazo [4,5-c]pyridine dihydrochloride (500 mg, 2.23 mmol), K 2 CO 3  (646 mg, 4.68 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and old 4-nitrophenyl chloroformate (1.01 g, 4.68 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). 4-Ethyl-5-(4-nitrobenzyl)-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (23 mg, 4%). R f =0.11 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=8.17 (d, J=8.8 Hz, 2H); 7.62 (d, J=8.8 Hz, 2H); 7.51 (s, 1H); 3.88 (d, J=14.4 Hz, 1H); 3.74 (d, J=14.4 Hz, 1H); 3.43 (t, J=6.1 Hz, 1H); 3.11 (m, 1H); 2.77 (m, 2H); 2.46 (dt, J 1 =15.4 Hz, J 2 =4.5 Hz, 1H); 1.78 (m, 2H); 0.89 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CD 3 OD): δ=149.30 (s); 148.35 (s); 134.81 (d); 130.54 (d); 124.23 (d); 60.23 (d); 57.61 (t); 46.45 (t); 27.43 (t); 20.98 (t); 10.72 (q). MS (EI): m/z=286 (M + , 0.4%); 257 (100%); 241 (1%); 227 (1%); 211 (8%); 136 (4%); 122 (7%); 120 (11%). HRMS: Calc. for C 15 H 20 N 4 O 2 : M + =286.1430; found: 286.1436.  
       EXAMPLE 37  
       [0173]    5-(4-Nitrobenzyl)-4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate:  
         [0174]    According to GPII, starting from 4-propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride (500 mg, 2.10 mmol), K 2 CO 3  (609 mg, 4.40 mmol), CHCl 3  (6 mL), H 2 O (3 mL) and old 4-nitrophenyl chloroformate (949 mg, 4.40 mmol). The reaction was carried out in a parallel fashion in a test-tube closed with a screwed tap and stirred in a Stem-stirrer. The basic treatment was carried out in MeOH (6 mL) and aq. 1M NaOH (4 mL). After 1 h the mixture was acidified with aq. 1 M HCl (3 mL). The reaction mixture was evaporated in a speed-vac overnight. The residue was triturated with CHCl 3  and filtered several times. The combined org. phases were evaporated in a speed-vac. The residue was purified by parallel FC with a gradient pump (MeOH/CHCl 3  0:100→0:100 for 5 min, then→1:3 over 25 min). 5-(4-Nitrobenzyl)-4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate was obtained as foam (88 mg, 14%). Rf=0.24 (MeOH/CHCl 3  1:9).  1 H—NMR (400 MHz, CD 3 OD): δ=8.14 (d, J=8.8 Hz, 2H); 7.58 (d, J=8.8 Hz, 2H); 7.50 (s, 1H); 3.83 (d, J=14.4 Hz, 1H); 3.74 (d, J=14.4 Hz, 1H); 3.49 (t, J=5.9 Hz, 1H); 3.12 (m, 1H); 2.85-2.70 (m, 2H); 2.44 (ddd, J 1 =15.9 Hz, J 2 =5.1 Hz, J 3 =3.9 Hz, 1H); 1.69 (m, 2H); 1.39 (m, 2H); 0.82 (t, J=7.3 Hz, 3H).  13 C—NMR (100 MHz, CDCl 3 ): δ=148.03 (s); 147.07 (s); 133.47 (d); 132.38 (s); 129.28 (d); 126.14 (s); 123.53 (d); 57.83 (d); 56.83 (t); 45.02 (t); 36.37 (t); 20.00 (t); 19.40 (t); 14.31 (q). MS (EI): m/z=299 (M—H + , 0.5%); 257 (100%); 241 (1%); 211 (9%); 136 (4%); 122 (3%); 120 (9%); 106 (3%); 90 (8%). Elemental analysis: Calc. for C 16 H 22 N 4 O 2 : C 63.56%, H 7.33%, N 17.06%; found: C 63.00%, H 7.32%, N 17.17%.  
       EXAMPLE 38  
       [0175]    Benzyl (4S,6S)-4-ethyl-6-[(isobutylamino)-carbonyl]-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate: (4S,6S)-5-[(Benzyloxy)carbonyl]-4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (99 mg, 0.30 mmol) was dissolved in DMF (2 mL). EDC.HCl (63 mg, 0.33 mmol), HOBt (45 mg, 0.33 mmol), DMAP (cat. amount) and isobutylamine (70 μL, 0.70 mmol) were added. The solution was stirred for 24 h. After removing the solvent under reduced pressure, the residue was purified by RP—HPLC (95% H 2 O→65% H 2 O over 10 min→0% H 2 O over 10 min). Benzyl (4S,6S)-4-ethyl-6-[(isobutylamino)-carbonyl]-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (38.8 mg, 34%).  1 H—NMR (400 MHz, CDCl 3 ): δ=8.46 (s, 1H); 7.43-7.31 (m, 5H); 6.50 (s, br., 1H); 5.36 (s, br., 1H); 5.24 (s, br., 3H); 3.35 (d, J=16.4 Hz, 1H); 3.05 (dt, J 1 =19.8 Hz, J 2 =6.7 Hz, 1H); 2.90 (s, br., 1H); 2.82 (dd, J 1 =16.4 Hz, J 2 =6.8 Hz, 1H); 1.87-1.74 (m, br., 1H); 1.69 (s, br., 1H); 1.61 (m, 1H); 0.86 (s, br., 9H).  13 C—NMR (100 MHz, CDCl 3 ): δ=170.82 (s); 157.60 (s); 135.30 (s); 133.16 (d); 128.70 (d); 126.47 (s); 124.79 (s); 69.03 (t); 51.88 (d); 50.73 (d); 47.32 (t); 28.16 (d and t); 20.33 (t); 20.21 (q); 10.97 (q). MS (EI): m/z=384 (M + , 11%); 355 (20%); 311 (15%); 284 (6%); 249 (7%); 194 (3%); 150 (8%); 122 (9%); 91 (100%). HRMS: Calc. for C 21 H 28 N 4 O 3 : M + =384.2161; found: 384.2172.  
       EXAMPLE 39  
       [0176]    Benzyl (4S,6S)-6-(aminocarbonyl)-4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate: To a solution of (4S,6S)-5-[(Benzyloxy)carbonyl]-4-ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (80 mg, 0.24 mmol) in DMF (2 mL) were added NH 3 /dioxane (0.5M, 1.5 mL, 0.75 mmol), EDC.HCl (48 mg, 0.25 mmol), HOBt (34 mg, 0.25 mmol) and DMAP (cat. amount). The solution was stirred overnight and the solvent removed under reduced pressure. The residue was dried under high vacuum and purified by RP—HPLC (95% H 2 O→65% H 2 O over 10 min→0% H 2 O over 10 min). Benzyl (4S,6S)-6-(aminocarbonyl) -4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate was obtained as foam (32.6 mg, 40%).  1 H—NMR (400 MHz, CD 3 OD): 6 8.76 (s, 1H); 7.47-7.21 (m, 5H); 5.48 (s, br., 1H); 5.33-5.10 (m, br., 3H); 3.24 (dd, J 1 =16.1 Hz, J 2 =0.7 Hz, 1H); 2.83 (ddd, J 1 =16.4 Hz, J 2 =6.8 Hz, J 3 =1.7 Hz); 1.90-1.73 (m, 2H); 1.06 (s, br., 3H). MS (EI): m/z=328 (M + , 4%); 284 (2%); 210 (6%); 193 (14%); 176 (3%); 107 (6%); 91 (100%). HRMS: Calc. for C 17 H 20 N 4 O 3 : M + =328.1535; found: 328.1523.  
         [0177]    SSAO Activity Assays  
         [0178]    All assays were performed at room temperature with SSAO purified from human umbilical cord arteries. The enzyme activity was measured with two different methods, based on the detection of either hydrogen peroxide or the aldehyde that is formed from SSAO catalysis of its main substrates, primary amines.  
         [0179]    Hydrogen Peroxide Detection  
         [0180]    This method is based on the horseradish peroxidase catalyzed hydrogen peroxide oxidation of 10-acetyl-3,7-dihydroxyphenoxazine (Molecular Probes A-65 50), that yields a highly fluorescent product, resorufin. Briefly, 10 mM stock solution of substance in DMSO is serially diluted in 0.05 M sodium-potassium phosphate buffer. These dilutions are mixed with benzylamine (SSAO substrate) and a reagent solution consisting of SSAO enzyme, horse radish peroxidase (HRP) and 10-acetyl-3,7-dihydroxyphenoxazine. The final concentrations in the assay volume are 104 μM benzylamine, 219 μM 10-acetyl-3,7-dihydroxyphenoxazine, 1.1 U/ml HRP and a dilution of the SSAO preparation of {fraction (1/600)}. After two hours of incubation in flat-bottomed polystyrene microtiter plates, the fluorescence is measured at 560 ex/590 em. The inhibition is measured as % decrease of the signal compared to a control containing dilution of DMSO only (no substance).  
         [0181]    Aldehyde Detection  
         [0182]    SSAO activity is measured as increase of aldehyde formed from SSAO degradation of primary amines. Briefly, in conical glass centrifuge tubes,  14 C-labeled benzylamine is mixed with substance dilutions (from 10 mM stock solution in DMSO) in 0.05 M sodium-potassium phosphate buffer (pH 7.8). Enzyme, also diluted in phosphate buffer, is added and incubation is performed at room temperature for 60 minutes. The reaction is stopped with 1 M HCl. The formed (1 4 C-labeled) aldehyde is separated from the likewise 1 4 C-labeled benzylamine through extraction with toluene:ethyl acetate and then transferred to liquid scintillation vials for measurement of radioactivity in a beta counter. The final concentrations in the assay volume are 150 μM benzylamine (0.037 MBq/μmol), and a dilution of the SSAO preparation of {fraction (1/150)}.The inhibition is measured as % decrease of the signal compared to control containing dilution of DMSO only (no substance).  
         [0183]    Biological Activity  
         [0184]    The compounds shown in Tables 2 and 3 were tested for biological activity, determined as percent inhibition of SSAO at 12 μM concentration of the test compounds. The compounds were shown to inhibit SSAO to from 10 to 97%.  
                             TABLE 2                                                                                  Compound   R 3     R 5                 4-Methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride   Me   H       4-Ethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride   Et   H       4-Propyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride   Pr   H       4-Phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride   Ph   H       4-Benzyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine dihydrochloride   Bn   H       Methyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Me   Me—OCO—       Methyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Et   Me—OCO—       Methyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Pr   Me—OCO—       Methyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Ph   Me—OCO—       Benzyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Me   Bn—OCO—       Benzyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Et   Bn—OCO—       Benzyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Pr   Bn—OCO—       Benzyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Ph   Bn—OCO—       Benzyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Bn   Bn—OCO—       4-Methyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine   Me   PhOCH 2 CO—       4-Ethyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate   Et   PhOCH 2 CO—       4-Propyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate   Pr   PhOCH 2 CO—       4-Phenyl-5-(phenoxyacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine trifluoroacetate   Ph   PhOCH 2 CO—       Cyclopentyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Et   Cyclopentyl-OCO—       Cyclopentyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Pr   Cyclopentyl-OCO—       Cyclopentyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Ph   Cyclopentyl-OCO—       4-Fluorophenyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Et   4F-Ph—OCO—       4-Fluorophenyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Pr   4F-Ph—OCO—       4-Fluorophenyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate   Ph   4F-Ph—OCO—       Methoxyethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Et   MeO(CH 2 ) 2 —OCO—       Methoxyethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Pr   MeO(CH 2 ) 2 —OCO—       Methoxyethyl 4-phenyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Ph   MeO(CH 2 ) 2 —OCO—       Allyl 4-methyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Me   CH 2 ═CHCH 2 —OCO—       Allyl 4-ethy1-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Et   CH 2 ═CHCH 2 —OCO—       Allyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Pr   CH 2 ═CHCH 2 —OCO—       Allyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Bn   CH 2 ═CHCH 2 —OCO—       2,2,2-Trichloroethyl 4-ethyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Et   Cl 3 CCH 2 —OCO—       2,2,2-Trichloroethyl 4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Pr   Cl 3 CCH 2 —OCO—       2,2,2-Trichloroethyl 4-benzyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Bn   Cl 3 CCH 2 —OCO—       4-Ethyl-5-(4-nitrobenzyl)-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Et   4-NO 2 —Ph—CH 2 —OCO—       5-(4-Nitrobenzyl)-4-propyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate   Pr   4-NO 2 —Ph—CH 2 —OCO—                  
 
         [0185]    [0185]                         TABLE 3                                                                                  Compound   R 1                 Benzyl(4S,6S)-4-ethyl-6-[(isobutyl-   i-Bu—       amino)-carbonyl]-1,4,6,7-tetra-       hydro-5H-imidazo[4,5-c]pyridine-5-carboxylate trifluoroacetate       Benzyl(4S,6S)-6-(aminocarbonyl)-4-ethyl-1,4,6,7-tetra-   H       hydro-5H-imidazo[4,5-c]pyridine-5-carboxylate-tri-       fluoroacetate