Pyrrolo[3,2-b]pyridine derivatives and method of producing said derivatives

FIELD: chemistry.

SUBSTANCE: present invention pertains to novel pyrrolo[3,2-b]pyridine derivatives of formula I , where values of radicals R1-R5 are given in the description. The invention also covers pharmaceutically acceptable salts of these compounds, methods of producing these compounds and pharmaceutical compositions containing these compounds. Pyrrolo[3,2-b]pyridine derivatives and their pharmaceutically acceptable salts can provide proton pump reversible inhibitory effect.

EFFECT: obtaining novel pharmaceutically acceptable salts which can provide proton pump reversible inhibitory effect.

5 cl, 2 tbl, 289 ex

 

The technical field

The present invention relates to new derivatives pyrrolo[3,2-b]pyridine or pharmaceutically acceptable salts, which have excellent inhibitory activity against the secretion of gastric acid, to processes for their preparation and pharmaceutical compositions comprising them.

The level of technology

Disease peptic ulcer occurs when enhanced by the action of aggressive factors contributing to the secretion of gastric acid, or when the protective factors of the gastric mucosa weakened. For the treatment of peptic ulcer disease has been used a variety of drugs, such as antacids, anticholinergic agents, antagonists of N2receptors and proton pump inhibitors. The emergence of omeprazole a proton pump inhibitor newly initiated research activities in this field.

However, it is noted that the inhibition of the proton pump with omeprazole is irreversible, which entails long-term inhibition of the secretion of gastric acid, which can cause side effects. Accordingly, made various attempts to develop a reversible proton pump inhibitor. For example, in WO 98/37080 (AstraZeneca AB), WO 00/17200 (Byk Gulden Lomberg Chem.) and U.S. patent No. 4450164 (Schering Corporation) discloses derivatives of imidazopyridine is as reversible proton pump inhibitors. Further, in European patent No. 775120 (Yuhan Corp.) disclosed derivatives of pyrimidine.

Disclosure of invention

The technical problem

The present invention provides new derivatives of pyrrolo[3,2-b]pyridine or pharmaceutically acceptable salts, which have excellent inhibitory effect on the proton pump and have the ability to provide a reversible inhibition of the proton pump.

Technical solution

According to one aspect of the present invention is derived pyrrolo[3,2-b]pyridine or its pharmaceutically acceptable salt.

Further, according to another aspect of the present invention provides a method of deriving pyrrolo[3,2-b]pyridine or its pharmaceutically acceptable salt.

Further, according to another aspect of the present invention is provided a pharmaceutical composition comprising a derivative pyrrolo[3,2-b]pyridine or its pharmaceutically acceptable salt as an active ingredient and a pharmaceutically acceptable carrier.

The best way of carrying out the invention

In accordance with one aspect of the present invention provides a compound of formula (I) or its pharmaceutically acceptable salt:

in which

R1represents the t hydrogen; linear or branched C1-C6alkyl group, optionally substituted by one or more substituents selected from the group consisting of C1-C5alkoxy, hydroxy, C3-C7cycloalkyl, acetoxy,2-C6alkenylacyl,1-C3alkoxycarbonyl, amino, optionally substituted by one or two1-C3alkilani, cyano, naphthyl, pyridyl, oxiranyl, oxazolidinone, isoxazolyl, optionally substituted by one or more1-C3alkilani, 1,3-DIOXOLANYL and 2,3-dihydrobenzo[1,4]dioxine; linear or branched C2-C6alkenylphenol group; a linear or branched C2-C6alkylamino group; or a benzyl group, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C3of alkyl, C1-C3alkoxy, cyano, C1-C3alkoxycarbonyl, trifter-C1-C3of alkyl,

R2represents a linear or branched C1-C6alkyl group,

R3represents a linear or branched C1-C6alkyl group, optionally substituted hydroxy,

R4represents hydrogen; a linear or branched C1-C6alkyl group; halogen; cyano; hydroxycarbonyl; Amin is carbonyl; or3-C7cycloalkylcarbonyl,

R5represents 1,2,3,4-tetrahydroisoquinoline group, optionally substituted by one or more Halogens or With1-C5alkilani; benzyloxy, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C5of alkyl, C1-C5alkoxy, trifter-C1-C3of alkyl, amino group, optionally substituted by one or two substituents selected from the group consisting of C1-C5alkoxycarbonyl, and benzyl, optionally substituted with halogen; phenyl group, optionally substituted by one or more Halogens; fenoxaprop, optionally substituted by one or more halogen; pyridyl-C1-C3alkoxygroup; or peperoncino, and

n represents 1 or 2.

Among the compounds of formula (I) or their pharmaceutically acceptable salts of the present invention preferred are compounds in which:

R1represents hydrogen; a linear or branched C1-C6alkyl group; C1-C3alkyl group, substituted by one or more substituents selected from the group consisting of methoxy, hydroxy, cyclopropyl, cyclobutyl, acetoxy, vinyloxy, methoxycarbonyl, dimethylamino, cyano, naphthyl of pyridyl, oxiranyl, oxazolidinone, dimethylisoxazole, 1,3-DIOXOLANYL and 2,3-dihydrobenzo[1,4]dioxine; linear or branched C2-C6alkenylphenol group; a linear or branched C2-C6alkylamino group; or a benzyl group, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C3of alkyl, C1-C3alkoxy, cyano, methoxycarbonyl and trifloromethyl,

R2represents a methyl group,

R3represents a methyl group or hydroxymethylene group,

R4represents hydrogen; a methyl group; halogen; cyano; hydroxycarbonyl; aminocarbonyl; or cyclopropanecarbonyl;

R5represents 1,2,3,4-tetrahydroisoquinoline; 6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline; benzyloxy substituted by one or more substituents selected from the group consisting of halogen, C1-C5of alkyl, C1-C5alkoxy and trifloromethyl; an amino group substituted by one or two tert-butoxycarbonylamino or formentelli; florfenicol group; perperoglou; pyridyloxy; or piperonylic; and

n represents 1 or 2.

Compounds of the present invention can be in the form of a pharmaceutically acceptable non-toxic salts. Non-toxic salts may be included in the CE which I accepted an acid additive salt, used in the field of anti-ulcer agents such as salts derived from inorganic acids such as hydrochloric acid, Hydrobromic acid, sulfuric acid, sulfamic acid, phosphoric acid or nitric acid, and organic acids such as acetic, propionic, succinic, glycolic, stearic, citric, maleic, malonic, methansulfonate, tartaric, malic, phenylacetic, glutamic, benzoic, salicylic, 2-acetoxybenzoic, fumaric, camphorsulfonic, benzolsulfonat, p-toluensulfonate, oxalic acid or triperoxonane acid. Such acid additive salts can be obtained in accordance with any of the conventional ways.

The present invention covers its volume method for obtaining compounds of formula (I) or its pharmaceutically acceptable salt according to the following scheme 1:

Scheme 1

in which R1, R2, R3, R4, R5and n have the meanings given above and X represents halogen.

In particular, the compound of formula (I) or its pharmaceutically acceptable salt can be obtained using a method which includes the interaction of the compounds of formula (II) with R5-Obtaining the compounds of formula (III), the interaction with the organisations of the formula (III) with the compound of the formula (IV) with a compound of formula (Ia) and interaction of the compounds of formula (Ia) with R 1-X with obtaining the compounds of formula (I).

In the process of scheme 1 the compounds of formula (II) and (IV) are commercially available. The interaction of formula (II) and R5-N can be carried out in the presence of a base such as sodium hydride, tert-piperonyl potassium carbonate, sodium or potassium hydroxide. Further, the reaction may be carried out in an organic solvent such as anhydrous tetrahydrofuran and N,N-dimethylformamide, at room temperature or while heating, for example at a temperature of 40°C=140°C.

The cyclization reaction of the compounds of formula (III) and compounds of formula (IV) can be carried out in an organic solvent, such as anhydrous tetrahydrofuran. Further, the reaction may be carried out at a temperature of -78°C To -20°C or at room temperature.

The compound of formula (Ia) is subjected to interaction with R1's obtaining the compounds of formula (I). The reaction of compounds of formula (Ia) and R1-X can be carried out in the presence of a base such as sodium hydride or tert-piperonyl potassium. Further, the reaction may be carried out in an organic solvent, such as tetrahydrofuran or N,N-dimethylformamide, at room temperature or at 40°C-100°C. to increase the reaction rate and/or reactive output, you can use a catalytic amount of 18-crown-6.

In accordance with another is one aspect of the present invention the compound of formula (IC) or its pharmaceutically acceptable salt may be obtained in accordance with the following scheme 2:

Scheme 2

in which R1, R2, R4and R5have the meanings given above.

In particular, the compound of formula (IC) or its pharmaceutically acceptable salt can be obtained using a method which involves the hydrolysis of compounds of formula (Ib) gidrolizuut agent, such as lithium hydroxide, in the presence of ammonium cerium nitrate (IV) and acetic acid.

In accordance with another aspect of the present invention the compound of formula (Ig) or its pharmaceutically acceptable salt can be obtained using a method which involves reacting the compounds of formula (Id) with copper cyanide (CuCN) to obtain the compounds of formula (Ie); the hydrolysis of compounds of formula (Ie) to obtain the compounds of formula (If); and the interaction of the compounds of formula (If) with the compound of the formula (V) to obtain the compounds of formula (Ig) according to the following scheme 3:

Scheme 3

in which R1, R2, R3, R5and X have the meanings defined above, and R6and R7represent independently from each other hydrogen or C3-C7cycloalkyl group.

In the process of scheme 3, the compound of formula (Ie) can be obtained by boiling the compounds of formula (Id) and Ziani the and copper (CuCN) in an organic solvent, for example N,N-dimethylformamide.

The compound of formula (Ie) hydrolyzing in an acidic or alkaline conditions to obtain compounds of formula (If). The hydrolysis reaction can be carried out using a solution of potassium hydroxide at a temperature of 50°C.-100°C.

The reaction of compounds of formula (If) and the compounds of formula (V) may be carried out in the presence of a condensing agent, for example N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) or 1-hydroxy-7-isobenzofuranone (HOBT). The reaction mix may be carried out in an organic solvent, for example dichloromethane or N,N-dimethylformamide.

The present invention further includes a pharmaceutical composition comprising a therapeutically effective amount of any of compounds of the formula (I)defined above, or its pharmaceutically acceptable salt and a pharmaceutically acceptable carrier. The compound of formula (I) or its pharmaceutically acceptable salt can be used for the prevention and treatment of gastrointestinal inflammatory diseases and associated with gastric acid diseases of mammals, including humans, such as gastritis, gastric ulcer, duodenal ulcer, reflux esophagitis and the syndrome of Zollinger-Ellison. In addition, the compounds of the present invention and their salts can be used for treatment of other gastrointestinal disorders, when the cat is older desirable gastric antisecretory effect for example, in patients with gastrinom and in patients with acute upper gastrointestinal bleeding. Compounds of the present invention and their salts can also be used for patients in situations of intensive care and before - and posioperating to prevent acid aspiration and stress ulceration.

Compositions of the present invention can include additives, such as lactose or corn starch, and lubricating agents such as magnesium stearate, emulsifiers, suspendresume agents, stabilizers and isotonic agents. If necessary, can be added sweetening agents and/or flavoring or flavoring agents.

Compositions of the present invention can be administered orally or parenterally, including intravenous, intraperitoneally, subcutaneous, rectal and local techniques. Therefore, the composition of the present invention may be included in various forms, such as tablets, capsules, aqueous solutions or suspensions. In the case of tablets for oral use are usually added carriers, such as lactose, corn starch, and lubricating agents, e.g. magnesium stearate. In the case of capsules for oral administration as a diluent can be used lactose and/or dried corn starch. When peroral the utilisation of required water suspension, the active ingredient can be combined with emulsifying and/or suspenders agents. If you can add some sweetening and/or flavoring or flavoring agents. For intramuscular, intraperitoneal, subcutaneous and intravenous use is usually prepared sterile solutions of the active ingredient, and should appropriately be installed and supererogate pH solutions. For intravenous use should regulate the total concentration of dissolved substances in order to make the preparation isotonic. Compositions of the present invention can be in the form of an aqueous solution containing pharmaceutically acceptable carriers, such as saline, at pH 7.4. Solutions can be administered in intramuscular blood flow using local injection of the bolus.

Compounds of the present invention can be administered to the patient in an effective amount in the range of from about 0.1 mg/kg to about 500 mg/kg / day. Of course, the dosage may vary depending on the patient's age, weight, susceptibility or symptoms.

The following examples are provided only for illustration purposes and are not intended to limit the scope of the invention.

Obtaining 1. 2-(3-Nitropyridine-4-yl)-1,2,3,4-tetrahydroisoquinoline

Stage 1: 4-Chloro-3-nitropyridine

<> 4-Hydroxy-3-nitropyridine (10.0 g, 71,38 mmol) was added to 100 ml of phosphorus oxychloride, and then was heated under reflux with stirring for 1 hour. The reaction mixture was concentrated under reduced pressure. The resulting residue was added to 500 ml of ice water and the mixture is then neutralized 2n. the sodium hydroxide solution. The reaction mixture was extracted with methylene chloride (300 ml). The separated organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to obtain specified in the title compounds as a pale yellow solid (9.2 grams, 92,0%).

TLC; n-hexane/ethyl acetate = 2/1 (vol./vol.); Rf=0,5

1H-NMR (CDCl3) ∆ 9,12 (c, 1H), 8,69 (d, 1H), 7,55 (d, 1H).

Stage 2: 2-(3-Nitropyridine-4-yl)-1,2,3,4-tetrahydroisoquinoline

Sodium hydride (60%, 386,4 mg, to 9.66 mmol) at 0°C was added to a solution of 1,2,3,4-tetrahydroisoquinoline (of 1.06 ml, with 8.05 mmol) in N,N-dimethylformamide (30 ml) and was stirred for 10 minutes at the same temperature. To the reaction mixture were added 4-chloro-3-nitropyridine (1,124 g, to 7.09 mmol), obtained in stage 1, and the mixture was stirred for 2 hours at room temperature, the mixture was diluted with water (10 ml) and ethyl acetate (100 ml)and then washed twice with water (100 ml). The separated organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to receive the receiving specified in the title compound as a yellow solid (1.13 g, 89.3 per cent).

TLC; n-hexane/ethyl acetate = 2/1 (vol./vol.); Rf=0.3 to

1H-NMR (CDCl3) δ 8,86 (c, 1H), at 8.36 (d, 2H), 7,22 (m, 3H), 7,12 (m, 1H), of 6.96 (d, 1H), 4,35 (c, 2H), 3,53 (t, 2H), 3,03 (t, 2H).

Getting 2. 4-(4-Forbindelse)-3-nitropyridine

4-Chloro-3-nitropyridine (2.0 g, br12.62 mmol)obtained in stage 1 get 1, was added to a suspension of 4-fermentelos alcohol (2,04 ml, 18,92 mmol), potassium carbonate (1,74 g, br12.62 mmol) and potassium hydroxide (2.38 g, 50,48 mmol) in anhydrous toluene (100 ml). To the reaction mixture was added a catalytic amount of Tris[2-(2-methoxyethoxy)ethyl]amine and the mixture is then stirred for 1 hour at room temperature. The reaction mixture was filtered and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/1, (about./about.)) obtaining specified in the title compound as a white solid (2.5 g, 86,3%).

TLC; n-hexane/ethyl acetate = 2/1; Rf=0,4

1H-NMR (CDCl3) δ 8,57 (c, 1H), 7,28 (m, 3H), 7,16 (m, 2H), 6,70 (d, 1H), of 5.05 (c, 2H).

Getting 3. tert-Butyl ether (2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

Stage 1: 4-(4-terbisil)-(3-nitropyridine-4-yl)Amin

Sodium carbonate (3,20 g, 30,27 mmol) and 4-forbindelsen (2,14 ml, 18,92 mmol) was added to a solution of 4-chloro-3-nitropyridine (3.0 g, 18,92 mmol)obtained in stage 1 receive the Oia 1, in 30 ml of anhydrous N,N-dimethylformamide, and then the reaction mixture was stirred for 1 hour at 80°C. the Reaction mixture was diluted with a mixture of water (10 ml) and ethyl acetate (100 ml)and then washed twice with water (100 ml). The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain specified in the title compound as a yellow solid (3,01 g, 83.5 per cent).

1H-NMR (CDCl3) δ 8,60 (c, 1H), 7,29 (m, 3H), 7,18 (m, 2H), 6,70 (d, 1H), 5,20 (c, 2H).

Step 2: tert-Butyl ether (4-terbisil)-(3-nitropyridine-4-yl)carbamino acid

Di-tert-BUTYLCARBAMATE (8,13 g, 37,25 mmol) and N,N-dimethylaminopyridine of 2.27 g, 18,63 mmol) was added to a solution of (4-terbisil)-(3-nitropyridine-4-yl)amine (of 3.07 g, 12,42 mmol)obtained in stage 1, in 100 ml of tetrahydrofuran, and then the reaction mixture was stirred for 24 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/1, (about./about.)) obtaining specified in the title compound as a yellow oil (2.9 g, 75,6%).

1H-NMR (CDCl3) δ 8,60 (c, 1H), 7,29 (m, 3H), 7,18 (m, 2H), 6,70 (d, 1H), 5,10 (c, 2H), 1,3 (c, 9H).

Step 3: tert-Butyl ether (2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

tert-Butyl ester (4-ft is benzyl)-(3-nitropyridine-4-yl)carbamino acid (10.2 g), obtained in stage 2, was dissolved in anhydrous tetrahydrofuran (200 ml) under nitrogen atmosphere. 1-Methyl-1-propenylboronic (0,5M in tertrahydrofuran ring solution, 110 ml, 130,5 mmol) was added at -78°C. to the solution, which was stirred for 5 hours at -20°C. To the reaction mixture were added 20 ml of 20% solution of ammonium chloride and the mixture then was extracted twice with ethyl acetate (200 ml). The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methanol=10/1, (about./about.)) obtaining specified in the title compounds as a pale yellow solid (3.8 g, 28.9 percent).

1H-NMR (CDCl3) δ 8,31 (d, 1H), 8,12 (c, 1H), 7,40 (m, 1H), 7,18 (d, 2H), to 7.09 (d, 2H), and 3.16 (c, 3H), 2,53 (c, 3H), 2,48 (c, 3H), 1.41 to (c, 9H).

Example 1. Hydrochloride of 1-(4-Chlorobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 2-(2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline

2-(3-Nitropyridine-4-yl)-1,2,3,4-tetrahydroisoquinoline (5 g, 19,58 mmol)obtained in the obtaining 1, was dissolved in anhydrous tetrahydrofuran (200 ml) under nitrogen atmosphere. 1-Methyl-1-propenylboronic (0,5M in tertrahydrofuran ring solution, 80 ml, 117,5 mmol) was added at -78°C. to the solution which was then stirred for 5 hours at -20°C. To the reaction mixture were added 20 ml of 20% solution of ammonium chloride and the mixture then was extracted twice with ethyl acetate (200 ml). The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methylene chloride/methanol=10/10/1, (about./about./about.)) obtaining specified in the title compounds as a pale yellow solid (2.1 g, 25.3 per cent).

1H-NMR (CDCl3) δ compared to 8.26 (d, 1H), to 7.77 (c, 1H), 7,19 (m, 4H), 6,59 (d, 1H), 4,46 (c, 2H), to 3.64 (t, 2H), 3.04 from (t, 2H), 2,41 (c, 3H), 2,30 (c, 3H).

Stage 2: the Hydrochloride of 1-(4-Chlorobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

2-(2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline (30 mg, to 0.108 mmol), obtained in stage 1, tert-piperonyl potassium (13,6 mg, rate £ 0.162 mmol) and a catalytic amount of 18-crown-6 was added to dry tetrahydrofuran (2 ml). To the reaction mixture were added 4-chlorobenzylchloride (0,09 ml, rate £ 0.162 mmol) and the mixture was then stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methylene chloride/methanol=10/10/1, (about./about./vol.), was dissolved in ethyl acetate (1 ml)and then saturated with gaseous hydrogen chloride. The resulting precipitate was filtered to obtain specified in the title compound as a white solid washes the VA (6.9 mg, 15,8%).

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,17 (m, 5H), 6,98 (m, 1H), 6.89 in (m, 1H), 6,54 (d, 2H), 5,51 (c, 2H), 4,39 (c, 2H), 3,57 (c, 2H), 2,93 (d, 2H), 2,59 (c, 3H), 2,25 (c, 3H).

Examples 2 through 29

The connections defined in the headers of examples 2-29, were obtained using the same procedures as in stage 2 of example 1, using 2-(2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline obtained in stage 1 of example 1, and 2-(methyl bromide)naphthalene, 2-methyl bromide-1,3-dioxolane, (methyl bromide)cyclopropane, 2-pomatoleios ether, benzylbromide, allylbromide, 3-methoxybenzylamine, 2-formanilide, 4-methoxybenzylamine, 1-iodopropane, 3-methylbenzylamine, iodata, 2-(2-bromacil)-1,3-dioxolane, 2-methyl bromide-1,4-benzodioxane, 4-bromo-2-methyl-2-butene, 4-methyl bromide-3,5-dimethylisoxazole, 2-chlorobenzylchloride, 1-Bromeliaceae, bromatologia ester, 4-tert-butylbenzylamine, (methyl bromide)CYCLOBUTANE, 3-cyanobenzaldehyde, Bromeliaceae, 2,4-dimethylbenzylamine, 4-methoxycarbonylbenzyl, 2-(bromacil)vinyl ether, 1-bromo-2-methylpropane or epibromohydrin.

Example 2. Hydrochloride of 1-(2-naphthylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,82 (m, 1H), 7,73 (m, 1H), 7,65 (m, 1H), 7,50 (m, 2H), to 7.15 (m, 5H), 6,78 (m, 2H), 5,67 (s, 2H), 4,43 (s, 2H)and 3.59 (m, 2H), 2,88 (m, 2H), 2,64 (s, 3H), of 2.35 (s, 3H); (yield: 78.9 per cent).

Example 3. Hydrochloride of 1-(13-dioxolane-2-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.30 to (d, 1H), 7,21 (m, 3H), 7,14 (m, 2H), a 4.83 (t, 1H), 4,74 (m, 4H), 3,85 (m, 3H), at 3.35 (m, 2H), 3,05 (m, 3H), at 2.59 (s, 3H), of 2.50 (s, 3H); (output: 86,3%).

Example 4. Hydrochloride of 1-cyclopropylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (d, 1H), 7,22 (m, 3H), 7,11 (m, 2H), 4,54 (d, 2H), 4,14 (s, 2H), 3,70 (m, 2H), is 3.08 (m, 2H), 2,54 (s, 2H), 2,41 (s, 3H), of 2.35 (s, 3H), or 0.83 (m, 1H), 0,32 (m, 2H), and 0.08 (m, 2H); (output: 69,8%).

Example 5. Hydrochloride of 1-(2-methoxyethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,22 (m, 3H), 7,11 (m, 2H), of 4.44 (m, 4H), 3,66 (m, 2H), 3,38 (m, 2H), 3,07 (c, 3H), 2.50 each (c, 3H), 2,42 (c, 3H); (output: 78,6%).

Example 6. Hydrochloride of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (m, 1H), 7,18 (m, 4H), 7,02 (m, 5H), 6,93 (m, 1H), 5.56mm (c, 2H), 4,37 (c, 2H), of 3.56 (m, 2H), 2,98 (m, 2H), 2,59 (c, 3H), 2,25 (c, 3H); (yield: 68.7 per cent).

Example 7. Hydrochloride of 1-allyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ compared to 8.26 (c, 1H), 7,20 (m, 3H), to 6.88 (m, 1H), 6,67 (m, 1H), 5,88 (d, 2H), to 5.66 (m, 1H), 4,49 (c, 2H), 4,33 (d, 1H), 4,25 (d, 1H), 3,63 (c, 2H), 3,05 (c, 2H), 2,55 (c, 3H), 2,42 (c, 3H); (output: 73,5%).

Example 8. Hydrochloride of 1-(3-methoxybenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (m, 1H), 7,03 (m, 4H), 6,86 (m, 3H), of 6.20 (m, 2H), 5,58 (c, 2H), to 4.52 (c, 2H), 3,68 (c, 3H), of 3.45 (m, 2H), 2.95 and (m, 2H), 2,55 (c, 3H), 234 (c, 3H); (output: 77,0%).

Example 9. Hydrochloride of 1-(2-terbisil)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,00 (m, 4H), 6,91 (m, 4H), 6,86 (m, 1H), 6,39 (c, 1H), 5,63 (c, 2H), 4,47 (m, 2H), 3,63 (m, 2H), 2,96 (m, 2H), 2,53 (c, 3H), 2,47 (c, 3H); (output: 74,5%).

Example 10. Hydrochloride of 1-(4-methoxybenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.27 (d, 1H), 7,32 (m, 3H), 7,00 (m, 3H), 6,77 (m, 3H), 5,51 (c, 2H), 4,55 (m, 2H), of 3.77 (c, 3H), of 2.97 (m, 4H), 2,45 (c, 3H), 2,33 (c, 3H); (yield: 86.9 per cent).

Example 11. Hydrochloride of 1-propyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,12 (m, 5H), 4,56 (c, 2H), 4,33 (t, 2H), 3,32 (m, 2H), 2,80 (m, 2H), 2,34 (c, 3H), 2,28 (c, 3H), of 1.98 (m, 2H), 1,53 (d, 3H); (output: 78,0%).

Example 12. Hydrochloride of 1-(3-methylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,42 (d, 1H), 6,92 (m, 4H), 6.87 in (m, 1H), 6.48 in (m, 4H), 5,66 (c, 2H), 4,59 (m, 2H), and 3.72 (m, 2H), is 3.08 (m, 2H), 2,64 (c, 3H), 2,48 (c, 3H), 2,10 (c, 3H); (output: 75,6%).

Example 13. Hydrochloride of 1-ethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,29 (d, 1H), 7.23 percent (m, 4H), of 7.00 (d, 1H), 4,56 (d, 2H), 4,32 (m, 2H), to 3.67 (m, 2H), is 3.08 (m, 2H), 2,59 (c, 3H), 2,48 (c, 3H), of 1.06 (t, 3H); (output: 77,0%).

Example 14. Hydrochloride of 1-[2-(1,3-dioxolane-2-yl)ethyl]-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 7,17 (m, 4H), 7,10 (c, 1H), a 4.83 (m, 2H), 4,39 (c, 2H), 4,01 (m, 1H), 3,57 (c, 2H), 3,12 (m, 4H), of 2.93 (m, 2H), 2,56 (c, 3H), 2,47 (c, 3H), 1,89 (m, 2H); (output: 58,4%).

Example 15. Hydrochloride of 1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 7,16 (m, 4H), 7,10 (m, 4H), 5,41 (c, 2H), 4,21 (c, 2H), 4,01 (m, 4H), 3,69 (c, 2H), 2,93 (m, 2H), 2.57 m (c, 3H), 2,48 (c, 3H); (output: 58,6%).

Example 16. Hydrochloride of 1-(3-methylbutan-2-yl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,51 (m, 4H), 7,10 (c, 1H), a 4.86 (d, 2H), 4,39 (c, 2H), 4,10 (m, 1H), only 3.57 (m, 2H), 2.95 and (m, 2H), 2,56 (c, 3H), 2,35 (c, 3H), 1,89 (c, 6H); (yield: 78.5 per cent).

Example 17. Hydrochloride of 1-(3,5-dimethylisoxazol-4-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,19 (m, 3H), to 6.88 (m, 2H), 5.40 to (c, 2H), 4,40 (c, 2H), 3,49 (m, 2H), 3,03 (m, 2H), 2,58 (c, 3H), 2,32 (c, 3H), 1.91 a (c, 3H), 1,65 (c, 3H); (yield: 57.8 per cent).

Example 18. Hydrochloride of 1-(2-Chlorobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,21 (m, 4H), 6,98 (m, 6H), 5,66 (c, 2H), 4,82 (c, 2H), 4,54 (m, 2H), 3,51 (m, 2H), 2,54 (c, 3H), 2,33 (c, 3H); (output: 75,4%).

Example 19. Hydrochloride of 1-methoxycarbonylethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.09 (m, 1H), 7,21 (m, 5H), of 4.45 (m, 4H), 4,11 (m, 4H), 3,83 (m, 2H), 3,07 (c, 3H), 2,65 (c, H), 2,55 (c, 3H); (yield: 83.0 per cent).

Example 20. Hydrochloride of 1-methoxymethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.30 to (m, 1H), 7.23 percent (m, 3H), 6,98 (m, 2H), 5,524 (c, 2H), 4,55 (c, 2H), with 3.89 (m, 2H), 3,48 (m, 2H), 3,09 (c, 3H), 2,53 (c, 3H), 2.50 each (c, 3H); (output: 69,3%).

Example 21. Hydrochloride of 1-(4-tert-butylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (c, 1H), 7,20 (m, 4H), of 6.99 (m, 4H), 5,65 (c, 2H), 4,51 (c, 2H), of 3.77 (m, 2H), 3,06 (m, 2H), 2,59 (c, 3H), 2,32 (c, 3H), 1.27mm (c, 9H); (output: 72,0%).

Example 22. Hydrochloride of 1-cyclobutylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,27 (c, 1H), 7,17 (m, 3H), 7,00 (m, 2H), 4,45 (c, 2H), 4,27 (c, 2H), 3,70 (m, 2H), to 3.09 (m, 2H), 2.57 m (c, 3H), 2,465 (c, 3H), 2,84 (m, 1H), of 1.66 (m, 4H), USD 1.43 (m, 2H); (yield: 83.5 per cent).

Example 23. Hydrochloride of 1-(3-cyanobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 7,79 is 7.50 (m, 5H), of 7.48 (m, 2H), 7,21 (m, 3H), 5,61 (c, 2H), and 4.40 (m, 2H), 3,51 (m, 2H), 2,96 (m, 2H), 2,43 (c, 3H), 2,36 (c, 3H); (output: 58,4%).

Example 24. Hydrochloride of 1-ethoxycarbonylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (m, 1H), 7,11-to 7.09 (m, 5H), to 5.21 (c, 2H), 4,46 (c, 2H), 3,74 (c, 3H), 3,47 (m, 2H), of 3.07 (m, 2H), 2,58 (c, 3H), of 2.51 (c, 3H); (output: 66,8%).

Example 25. Hydrochloride of 1-(2,4-dimethylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]p ridine

1H-NMR (CDCl3) δ scored 8.38 (m, 1H), to 7.09 (m, 6H), 6,40 (m, 1H), 6,02 (c, 1H), 5,46 (m, 2H), 4,20 (m, 2H), 3,53 (m, 2H), 2,97 (m, 2H), 2,65 (c, 3H), 2,28 (c, 3H), 1.77 in (c, 6H); (yield: 78.5 per cent).

Example 26. Hydrochloride of 1-(4-methoxycarbonylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,21 (d, 1H), 7,98 (d, 1H), 7,20 (m, 4H), 6,98 (m, 4H), ceiling of 5.60 (c, 2H), 4,68 (c, 2H), 3,67 (c, 3H), 3,05 (m, 2H), 2,88 (m, 2H), 2,34 (c, 3H), 2,28 (c, 3H); (output: 65,0%).

Example 27. Hydrochloride of 1-(2-vinyloxyethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,50 (m, 4H), 7,10 (c, 1H), 4,80 (d, 2H), 4.72 in (c, 2H), 4,23 (m, 1H), 3,78 (m, 2H), 3,60 (m, 2H), 3,49 (m, 2H), 2,93 (m, 2H), 2,35 (c, 3H), 2,28 (c, 3H); (yield: 48.7 percent).

Example 28. Hydrochloride of 1-isobutyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,38 (m, 4H), 7,14 (c, 1H), 4,89 (c, 2H), 4.75 in (d, 2H), 3,69 (m, 2H), 2,98 (m, 2H), 2,58 (c, 3H), 2,55 (c, 3H), 1,99 (m, 1H), 1.57 in (d, 6H); (output: 75,1%).

Example 29. Hydrochloride of 1-oxiranylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), of 7.48 (m, 4H), 7,12 (c, 1H), 5,11 (c, 2H), 4,89 (c, 2H), 3,68 (m, 2H), 3,60 (m, 2H), 3,55 (m, 1H), 2,89 (m, 2H), 2,58 (c, 3H), 2,55 (c, 3H); (output: 57,4%).

Example 30. Hydrochloride of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-3-hydroxymethyl-2-methyl-1H-pyrrolo[3,2-b]pyridine

The compound obtained in example 6 (501,1 mg of 1.23 mmol), was treated with solution b is sodium carbonate to obtain 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (433,6 mg, 1.18 mmol). Ammonium cerium nitrate (IV) (1,94 g, 3.54 mmol) was added at room temperature to a solution of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (433,6 mg, 1.18 mmol) in acetic acid (10 ml). The reaction mixture was stirred for 4 hours at 55°C, cooled to room temperature, poured into water, and then extracted with ethyl acetate. The resulting organic layer was washed with a saturated solution of sodium chloride, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in methanol (20 ml). 2n. the lithium hydroxide (5.0 ml) was added to the solution which was then stirred for 1 hour at room temperature. The reaction mixture was neutralized 1H. hydrochloric acid, concentrated under reduced pressure to remove methanol, and then was extracted with ethyl acetate. The resulting organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to obtain 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-3-hydroxymethyl-2-methyl-1H-pyrrolo[3,2-b]pyridine, which was then dissolved in ethyl acetate. The solution was saturated with gaseous hydrogen chloride, and then filtered to obtain specified in the connection header in the IDA white solid (69 mg, 13,9%).

1H-NMR (CDCl3) δ is 8.75 (d, 1H), 7,95 (d, 1H), 7,13 (m, 4H), 6,74 (m, 5H), 5,79 (c, 2H), 4,14 (m, 2H), 3,26 (m, 2H), 4,10 (c, 2H), 2,80 (m, 2H), 2,34 (c, 3H).

Example 31. 2-(2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline

Stage 1: 6-Fluoro-1-methyl-2-(3-nitropyridine-4-yl)-1,2,3,4-tetrahydroisoquinoline

In accordance with the same procedures as in stage 2 get 1, except for using 6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline received in accordance with the method described in WO 94/14795 got mentioned in the title compound as a pale yellow solid. (Output: 85,3%) the Product was used in the next stage without additional purification.

Stage 2: 2-(2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline

In accordance with the same procedures as in stage 1 of example 1, except using 6-fluoro-1-methyl-2-(3-nitropyridine-4-yl)-1,2,3,4-tetrahydroisoquinoline obtained at stage 1 has been specified in the title compound as white solids (yield: 15.7 percent).

1H-NMR (CDCl3) δ 10,23 (c, 1H), 8,51 (d, 1H), 7,87 (d, 1H), 7,21 (m, 2H), 7,06 (c, 1H), 4,36 (c, 2H), 3,37 (t, 1H), 3,14 (t, 2H), 2,37 (d, 3H), 2,53 (c, 3H), 2.23 to (c, 3H).

Example 32. Hydrochloride of 2-(1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline

In accordance with the same procedures that stud and 2 of example 1, except for using 2-(2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline obtained in stage 2 of example 31, and benzylbromide got mentioned in the title compound as white solids (yield: 65.8 per cent).

1H-NMR (CDCl3) δ of 8.50 (d, 1H), to 7.84 (d, 1H), 7,53 (m, 5H), 7,20 (m, 2H),? 7.04 baby mortality (c, 1H), 4,36 (c, 2H), 3,35 (t, 1H), 3,12 (t, 2H), 2,34 (d, 3H), 2.40 a (c, 3H), 2,35 (c, 3H).

Example 33. Hydrochloride of 1-(4-Chlorobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 7-(4-Forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

4-(4-Forbindelse)-3-nitropyridine (4.8 g, 19,34 mmol)obtained in the obtaining 2, was dissolved in anhydrous tetrahydrofuran (200 ml) under nitrogen atmosphere. 1-Methyl-1-propenylboronic (0,5M in tertrahydrofuran ring solution, 116 ml, 58,02 mmol) was added at -78°C. to the solution which was then stirred for 5 hours at -20°C. To the reaction mixture was added a 20% solution of ammonium chloride (20 ml) and the mixture then was extracted twice with ethyl acetate (200 ml). The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methylene chloride/methanol=10/10/1, (about./about./about.)) obtaining specified in the title compounds as a pale yellow solid (2,45 g, 28.3 per cent).

<> 1H-NMR (CDCl3) δ 8,29 (d, 1H), 7,97 (c, 1H), 7,43 (m, 2H), 7,10 (m, 2H), 6,60 (d, 1H), 5,18 (c, 2H), 2,39 (c, 3H), 2,30 (c, 3H).

Stage 2: the Hydrochloride of 1-(4-Chlorobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

7-(4-Forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (25 mg, 0,105 mmol)obtained in stage 1, tert-piperonyl potassium (13,6 mg, 0,163 mmol) and a catalytic amount of 18-crown-6 was added to dry tetrahydrofuran (2 ml). To the reaction mixture were added 4-chlorobenzylchloride (0,089 ml, 0,160 mmol) and the mixture was then stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methylene chloride/methanol=10/10/1, (about./about./vol.), was dissolved in ethyl acetate (1 ml)and then saturated with gaseous hydrogen chloride. The resulting precipitate was filtered to obtain specified in the title compound as a white solid (6.9 mg, 15.8 per cent).

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 7,24 (d, 2H), 7,03 (m, 4H), 6.87 in (c, 1H), of 6.52 (d, 2H), 5,50 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H).

Examples 34 to 62

The connections defined in the headers of examples 34-62, were obtained using the same procedures as in step 2 of example 33, using 7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 1 of example 33, 4-methylbenzylamine, 4-br is methylethylbenzene, 4-tert-butylbenzylamine, 2-(methyl bromide)naphthalene, 2-(methyl bromide)vinyl ether, 2-methyl bromide-1,3-dioxolane, 3-formanilide, 2,5-dimethylbenzylamine, 4-methyl bromide-3,5-dimethylisoxazole, 3-chlorobenzylchloride, 2-chloromethylpyridine, 6-chloromethyl-2,3-dihydrobenzo[1,4]dioxin-3-cyanobenzaldehyde, epibromohydrin, 3-chloromethylpyridine, allylbromide, 1-iodine-2-methylpropane, propylbromide, 3-methoxybenzylamine, 3-methylbenzylamine, benzylbromide, (methyl bromide)CYCLOBUTANE, 4-bromo-2-methyl-2-butene, methyl-3-bromopropionate, 4-methoxybenzylamine, 2-formanilide, (methyl bromide)cyclopropane, 2-pomatoleios ether or 1-iodopropane.

Example 34. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (d, 1H), 7,01 (m, 6H), 6,59 (m, 3H), 5,68 (c, 2H), 5,35 (c, 2H), 2,64 (c, 3H), 2,33 (c, 3H), 1,90 (c, 3H); (yield: 68.7 per cent).

Example 35. Hydrochloride methyl ester 4-[7-(4-forbindelse)-2,3-dimethyl-pyrrolo[3,2-b]pyridine-1-ylmethyl]benzoic acid

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), of 8.06 (d, 1H), 7,94 (m, 2H), 7,60 (d, 1H), was 7.08 (m, 4H), of 6.71 (m, 2H), 5,59 (c, 2H), 5,23 (c, 2H), 3,93 (c, 3H), 2,62 (c, 3H), 2,38 (c, 3H); (output: 63,4%).

Example 36. Hydrochloride of 1-(4-tert-butylbenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,29 (d, 2H), 6,99 (m, 4H), 6.90 to (c, 1H), 6,61 (c, 2H), ceiling of 5.60 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H), 1.32 to (c, 9H); (output: 58,4%).

the example 37. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(naphthalene-2-ylmethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,50 (m, 4H), 7,20 (m, 4H), 7,01 (m, 4H), 5,42 (c, 2H), 5,33 (c, 2H), 2,48 (c, 3H), 2,33 (c, 3H); (yield: 59.4 per cent).

Example 38. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(2-vinyloxyethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,12 (c, 1H), 7,52 (m, 2H), 7,16 (m, 2H), 6,95 (c, 1H), 5,41 (c, 2H), 5.40 to (c, 2H), 4,43 (c, 2H), 3,90 (c, 2H), 2,48 (c, 3H), 2,37 (c, 3H); (yield: 48.7 percent).

Example 39. Hydrochloride of 1-(1,3-dioxolane-2-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,47 (m, 4H), 7,12 (c, 1H), 5,68 (c, 2H), to 4.98 (d, 2H), 4,58 (m, 1H), 4,10 (m, 4H), 2,68 (c, 3H), 2,59 (c, 3H); (yield: 53.2 per cent).

Example 40. Hydrochloride of 1-(3-terbisil)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (t, 1H), 7.24 to 6,91 (m, 7H), to 6.39 (m, 2H), 5,52 (c, 2H), 5,24 (c, 2H), 2,59 (c, 3H), 2,38 (c, 3H); (output: 68,3%).

Example 41. Hydrochloride of 1-(2,5-dimethylbenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (d, 1H), 7,05 (m, 7H), 5,76 (c, 1H), 5,41 (c, 2H), 5,15 (c, 2H), 2,70 (c, 3H), 2,54 (c, 3H), 2.13 and (c, 3H), 1,99 (c, 3H); (output: 53,0%).

Example 42. Hydrochloride of 1-(3,5-dimethylisoxazol-4-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,46 (c, 1H), 7,13 (m, 4H), 6,97 (c, 1H), and 5.30 (c, 4H), 2,59 (c, 3H), 2,32 (c, 3H), 1,75 (c, 3H), 1,71 (c, 3H); (yield: 78.4 per cent).

Example 43. Hydrochloride of 1-(3-Chlorobenzyl)-7-(4-fluoro what ensilage)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (c, 1H), 7,39 (d, 1H), 7,24 (m, 1H), 7,12 (m, 1H), 6,95 (m, 5H), 6,02 (c, 1H), 5,58 (c, 2H), 5,18 (c, 2H), 2.63 in (c, 3H), 2,36 (c, 3H); (output: 81,0%).

Example 44. Hydrochloride of 1-(pyridine-2-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,29 (d, 2H), 6,99 (m, 4H), 6.90 to (c, 1H), 6,61 (c, 2H), ceiling of 5.60 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (yield: 82.3 per cent).

Example 45. Hydrochloride of 1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,43 (c, 1H), of 7.48 (m, 3H), 7,19 (m, 2H), 6,86 (m, 2H), 6,74 (c, 1H), lower than the 5.37 (c, 2H), 4,42 (c, 2H), 3,76 (d, 2H)and 3.59 (d, 2H), 2,53 (c, 3H), 2,46 (c, 3H); (yield: 67.0 per cent).

Example 46. Hydrochloride of 1-(3-cyanobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,42 (c, 1H), to 7.59 (m, 2H), 7,38 (m, 2H), 7,14 (m, 4H), 7,00 (c, 1H), of 5.53 (c, 2H), 5,22 (c, 2H), 2,74 (c, 3H), 2.40 a (c, 3H); (output: 83,2%).

Example 47. Hydrochloride of 1-oxiranylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), of 7.48 (m, 4H), 7,13 (c, 1H), 5,68 (c, 2H), 4,89 (c, 2H), 3,98 (m, 1H), 3.33 and (m, 2H), 2,59 (c, 3H), 2.50 each (c, 3H); (output: 65,4%).

Example 48. Hydrochloride of 1-(pyridine-3-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), a 7.85 (m, 4H), 7,47 (m, 4H), 7,12 (c, 1H), 5,68 (c, 2H), 5,12 (c, 2H), 2,68 (c, 3H), 2,59 (c, 3H); (output: 54,0%).

Example 49. Hydrochloride of 1-allyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

H-NMR (CDCl3) δ 8,43 (d, 1H), 7,47 (m, 3H), 7,00 (m, 2H), of 5.84 (m, 1H), 5,48 (c, 2H), 5,22 (d, 1H), 5,14 (c, 2H), 4,55 (d, 1H), 2,58 (c, 3H), 2.40 a (c, 3H); (output: 79,0%).

Example 50. The hydrochloride of 7-(4-forbindelse)-1-isobutyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,25 (m, 5H), 5,68 (c, 2H), around 4.85 (d, 2H), 2,56 (c, 3H), 2,33 (c, 3H), of 1.78 (m, 1H), 1,58 (d, 6H); (output: 86,0%).

Example 51. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(prop-2-inyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 3H), 7,53 (m, 2H), 7,16 (m, 2H), 6,94 (c, 1H), 5,41 (c, 2H), 5,12 (c, 2H), 2,56 (c, 3H), 2.50 each (c, 3H), 2,38 (c, 1H); (output: 58,6%).

Example 52. The hydrochloride of 7-(4-forbindelse)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,20 (m, 3H), 7,00 (m, 3H), 6,91 (c, 1H), 6.22 per (c, 2H), 5,54 (c, 2H), from 5.29 (c, 2H), 3.72 points (c, 3H), 2.63 in (c, 3H), 2.40 a (c, 3H); (output: 71,5%).

Example 53. The hydrochloride of 7-(4-forbindelse)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H),? 7.04 baby mortality (m, 1H), 7,01 (m, 5H), 6,83 (c, 1H), 6,47 (c, 1H), 6,44 (m, 1H), 5,52 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H), 2.26 and (c, 3H); (yield: 88.5 percent).

Example 54. Hydrochloride of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 7,29 (m, 3H), 7,01 (m, 4H), 6,84 (c, 1H), 6,66 (m, 2H), 5.56mm (c, 2H), 5,22 (c, 2H), 2,61 (c, 3H), 2,38 (c, 3H); (yield:89.3 per cent).

Example 55. Hydrochloride of 1-cyclobutylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 7,50 (m, 2H),7,18 (m, 3H), lower than the 5.37 (c, 2H), 4,28 (c, 2H), 2,54 (m, 1H), 2,55 (c, 3H), 2,45 (c, 3H), 1,79 (m, 3H), 1.57 in (m, 3H); exit; 78,6%).

Example 56. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(3-methyl-2-butene-2-yl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,43 (m, 2H), 7,14 (m, 2H), 6,85 (c, 1H), are 5.36 (c, 2H), 5,04 (m, 1H), 4,94 (c, 2H), 2,54 (c, 3H), 2,39 (c, 3H), 1,58 (c, 6H); (output: 59,8%).

Example 57. Hydrochloride of 1-[2-(methoxycarbonyl)ethyl]-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), of 7.48 (m, 2H), 7,12 (m, 2H), 6,93 (c, 1H), 5,39 (c, 2H), 4,51 (c, 2H), 4,23 (c, 2H), 2,55 (c, 3H), 2,45 (c, 3H), 1,95 (c, 3H); (yield: 67.9 percent).

Example 58. The hydrochloride of 7-(4-forbindelse)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,11 (c, 2H), 7,01 (m, 2H), to 6.80 (m, 3H), of 6.61 (d, 2H), 5,49 (c, 2H), 5.25 in (c, 2H), 3,79 (c, 3H), 2,59 (c, 3H), 2,38 (c, 3H); (yield: 78.4 per cent).

Example 59. Hydrochloride of 1-(2-terbisil)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,43 (c, 1H), 7,53 (m, 2H), 7,27 (m, 1H), 7,05 (m, 4H), 6,23 (m, 2H), 5,61 (c, 2H), and 5.30 (c, 2H), 2.63 in (c, 3H), 2.49 USD (c, 3H); (output: 86,3%).

Example 60. Hydrochloride of 1-cyclopropylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,50 (m, 2H), 7,24 (c, 1H), 7,10 (m, 2H), of 5.84 (c, 2H), 5,10 (c, 2H), 2,54 (c, 3H), 2,35 (c, 3H), 0,78 (m, 1H), and 0.62 (m, 2H), 0,17 (m, 2H); (yield: 79.6%of).

Example 61. The hydrochloride of 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 838 (c, 1H), 7,46 (m, 2H), 7,18 (m, 2H), 6,91 (c, 1H), are 5.36 (c, 2H), of 4.44 (c, 2H), 3,51 (c, 2H), 3,19 (c, 3H), 2,54 (c, 3H), 2,43 (c, 3H); (output: 69,0%).

Example 62. The hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), of 7.48 (m, 2H), 7,17 (m, 2H), 6.89 in (c, 1H), 5,34 (c, 2H), 4,17 (t, 2H), 2,54 (c, 3H), 2.40 a (c, 3H), of 1.66 (m, 2H), 0,72 (t, 3H); (yield: 78.5 per cent).

Example 63. Methanesulfonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

The compound obtained in example 54 (219 mg, of 0.58 mmol), was treated with saturated sodium bicarbonate solution to obtain 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (200 mg, 0.55 mmol). Methansulfonate acid (0,034 ml, 0.55 mmol) was added at room temperature to a solution of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (200 mg, 0.55 mmol) in 10 ml of ethyl acetate. The reaction mixture was stirred for 24 hours at the same temperature. The resulting solid was filtered to obtain specified in the title compounds as white solids (yield: 89.7%of it).

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 7,29 (m, 3H), 7,01 (m, 4H), 6,84 (c, 1H), 6,66 (m, 2H), 5.56mm (c, 2H), 5,22 (c, 2H), 2,61 (c, 3H), 2,38 (c, 3H).

Examples 64 to 71

The connections defined in the headers of examples 64-71, were obtained using the same procedures as in example 63, using 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained education is odoi connection obtained in example 54, saturated sodium bicarbonate solution, and benzosulfimide acid, p-toluensulfonate acid, nitric acid, sulfuric acid, maleic acid, phosphoric acid, malonic acid or Hydrobromic acid.

Example 64. Bansilalpet 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,67 (c, 1H), 8,01 (c, 2H), 7,38 (c, 3H), 7,26 (m, 4H), 6,98 (m, 3H), 6.87 in (d, 1H), 6,65 (c, 2H), 5,55 (c, 2H), total of 5.21 (c, 2H), 2,44 (c, 3H), 2,36 (c, 3H); (output: 95,8%).

Example 65. p-Toluensulfonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,68 (c, 1H), to $ 7.91 (d, 2H), 7,27 (m, 4H), 7,18 (d, 2H), 6,99 (m, 3H), 6.87 in (d, 1H), 6,66 (d, 2H), 5,55 (c, 2H), total of 5.21 (c, 2H), 2,44 (c, 3H), 2,36 (c, 6H); (output: 88,4%).

Example 66. Nitrate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,53 (c, 1H), 7,29 (m, 4H), 7,00 (m, 4H), to 6.88 (d, 1H), 6,68 (c, 2H), 5,58 (c, 2H), 5.25 in (c, 2H), 2,42 (c, 3H), 2,38 (c, 3H); (yield: 79.8 per cent).

Example 67. Sulfate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,45 (c, 1H), 7,25 (c, 6H), 7,11 (t, 2H), 6,78 (c, 2H), 5,61 (c, 2H), 5,44 (c, 2H), 2,36 (c, 3H), 2,28 (c, 3H); (yield: 86.9 per cent).

Example 68. Maleate of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ to 8.62 (d, 1H), 7,28 (m, 4H), of 6.99 (m, 3H), at 6.84 (d, 1H), 6,67 (c, 2H), 6,38 (c, 2H), 5,57 (c, 2H), 5,22 (c, 2H), 2,44 (c, 3H), 2,38 (c, 3H); (yield: 95.4 percent).

Example 69. ofat 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,02 (c, 1H), to 7.09 (m, 5H), to 6.95 (m, 2H), 6,70 (c, 1H), 6,64 (c, 2H), 5,43 (c, 2H), 5,09 (c, 2H), 2,14 (c, 3H), 2,08 (c, 3H); (output: 85,8%).

Example 70. Malonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,58 (d, 1H), 7,28 (m, 4H), 7,00 (m, 3H), PC 6.82 (d, 1H), 6,68 (c, 2H), 5,58 (c, 2H), 5,22 (c, 2H), 3,32 (c, 2H), 2,44 (c, 3H), 2,38 (c, 3H); (yield: 91.2 per cent).

Example 71. The hydrobromide of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 7,29 (m, 4H), 7,00 (m, 3H), 6,92 (d, 1H), 6,66 (c, 2H), 5.56mm (c, 2H), 5.25 in (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (yield: 79.8 per cent).

Example 72. Hydrochloride of 1-allyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(4-Chlorobenzoyloxy)-3-nitropyridine

In accordance with the same procedures as described in the getting 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 4-chlorobenzylamino alcohol, has been specified in the title compound as white solids (yield: 78,0%).

1H-NMR (CDCl3) δ 9,04 (c, 1H), to 8.62 (d, 1H), 7,40 (m, 4H),? 7.04 baby mortality (d, 1H), 5,28 (d, 1H).

Stage 2: 7-(4-Chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(4-chlorobenzoyloxy)-3-nitropyridine obtained at stage 1 has been specified in the title compound as a white solid substances is a (output: 23,8%).

1H-NMR (CDCl3) δ of 8.28 (d, 1H), 8,02 (c, 1H), 7,38 (m, 4H), to 6.58 (d, 1H), 5,19 (c, 2H), 2.40 a (c, 3H), 2,30 (c, 3H).

Stage 3: the Hydrochloride of 1-allyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in step 2 of example 33, except for using 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and allylbromide got mentioned in the title compound as white solids (yield: 75.3%of).

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,44 (d, 2H), 7,38 (d, 2H), 6,85 (d, 1H), by 5.87 (m, 1H), 5,33 (c, 2H), 5,14 (d, 1H), 4,93 (c, 2H), 4.53-in (d, 1H), 2,56 (c, 3H), 2,38 (c, 3H).

Examples 73 to 97

The connections defined in the headers of examples 73-97, were obtained using the same procedures as in step 2 of example 33, using 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 72, and benzylbromide, bromatologia ether, 2-cyanobenzaldehyde, 2-chlorobenzylchloride, bromoacetonitrile, 4-triftormetilfosfinov, 4-tert-butylbenzylamine, 4-chloromethylpyridine, 5-chloromethyl-2-oxazolidinone, 2,5-dimethylbenzylamine, methylpropanoate, 4-bromo-2-methyl-2-butene, 2-Bromeliaceae, 2-pomatoleios ether, 2-methyl bromide-1,3-dioxolane, 4-chlorobenzylamino, 2-ftorangidridy, iodata, 4-formanilide, 3-methoxybenzylamine, 4-formanilide, methyl-4-(methyl bromide)benzoate, 3-methylben is inflorida, 4-methylbenzylamine or (methyl bromide)cyclopropane.

Example 73. Hydrochloride of 1-benzyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,30 (m, 5H), 6,98 (d, 2H), at 6.84 (d, 1H), of 6.68 (d, 2H), 5,57 (c, 2H), 5,23 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (yield: 69.5 per cent).

Example 74. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,45 (m, 4H), 6,97 (d, 1H), 5,61 (c, 2H), 5.40 to (c, 2H), 3,17 (c, 3H), 2,55 (c, 3H), 2.49 USD (c, 3H); (output: 67,3%).

Example 75. Hydrochloride of 1-(2-cyanobenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.40 (d, 1H), to 7.64 (d, 1H), 7,42 (m, 3H), of 6.96 (m, 3H), 6,32 (c, 1H), 5,75 (c, 2H), 5,23 (c, 2H), 2,62 (c, 3H), 2,39 (c, 3H); (output: 75,4%).

Example 76. Hydrochloride of 1-(2-Chlorobenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 7,41 (d, 2H), 7,25 (m, 3H), 7,14 (m, 1H), 6.90 to (m, 3H), 5,59 (c, 2H), 5,18 (c, 2H), 2.63 in (c, 3H), 2,36 (c, 3H); (output: 68,4%).

Example 77. Hydrochloride of 1-cyanomethyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), of 7.48 (m, 4H), 7,03 (c, 1H), 5,44 (c, 2H), 5,26 (c, 2H), 2,53 (c, 6H); (output: 54,1%).

Example 78. The hydrochloride of 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1-(4-trifloromethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 7,53 (d, 2H), 7,29 (d, 2H), 6,99 (d, 2H), 6,88 (c, 1H), 6,76 (d, 2H), 5,59 (c, 2H), 5,20 (c, 2H), 2,61 (c, 3H), 2,38 (c, 3H); (yield: 68.7 per cent).

Example 79. Guide klorid 1-(4-tert-butylbenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 7,28 (m, 4H), 6,98 (d, 2H), for 6.81 (c, 1H), 6,62 (d, 2H), of 5.53 (c, 2H), 5,23 (c, 2H), 2,59 (c, 3H), 2,38 (c, 3H), 1,30 (c, 9H); (output: 58,9%).

Example 80. The hydrochloride of 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1-(pyridine-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,51 (d, 1H), to 8.41 (c, 1H), 7,34 (d, 2H), 7,01 (d, 2H), 6,86 (c, 1H), 6,58 (c, 2H), of 5.53 (c, 2H), 5,16 (c, 2H), 2,62 (c, 3H), 2,38 (c, 3H); (output: 68,0%).

Example 81. Hydrochloride 5-[7-(4-chlorobenzoyloxy)-2,3-dimethyl-pyrrolo[3,2-b]pyridine-1-ylmethyl]oxazolidin-2-it

1H-NMR (CDCl3) δ 9,27 (c, 1H), 8,32 (c, 1H), 7,52 (m, 3H), 6.87 in (c, 1H), 5,45 (c, 2H), 5,02 (c, 1H), 4,86 (c, 1H), of 3.77 (m, 2H), 3,63 (m, 1H), 2,50 (c, 6H); (output: 61,1%).

Example 82. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2,5-dimethylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,21 (m, 3H), was 7.08 (m, 2H), at 6.84 (d, 2H), 5,67 (c, 1H), 5,41 (c, 2H), 5,14 (c, 2H), 2.63 in (c, 3H), 2,35 (c, 3H), 2,17 (c, 3H), 2,01 (c, 3H); (output: 59,8%).

Example 83. Hydrochloride methyl ester [7-(4-chlorobenzoyloxy)-2,3-dimethyl-pyrrolo[3,2-b]pyridine-1-yl]acetic acid

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,45 (d, 2H), was 7.36 (d, 2H), 6,88 (c, 1H), 5,32 (c, 2H), 5,03 (c, 2H), 3,65 (c, 3H), 2,56 (c, 3H), 2,36 (c, 3H); (output: 63,3%).

Example 84. The hydrochloride of 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1-(3-methylbut-2-enyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,41 (m, 4H), 6,85 (d, 1H), 5,39 (c, 2H), of 5.05 (m, 1H), 4.95 points (d, 2H), 2,54 (c, 3H), 2,32 (c, 3H), 1.41 to (c, 6H); (output: 58,6%).

Example 85. Hydrochloride of 1-(2-acetoxyethyl)-7-(4-chlorobenzoyloxy-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,45 (m, 4H), 6,92 (d, 1H), 5,38 (c, 2H), 4,59 (d, 2H), 4.25 in (d, 2H), 2,62 (c, 3H), 2,45 (c, 3H), 2.06 to (c, 3H); (yield: 77.6 per cent).

Example 86. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (d, 1H), to 7.59 (m, 4H), 6,93 (d, 1H), 5,34 (c, 2H), 4,40 (c, 2H), 3,47 (c, 2H), 3,21 (c, 3H), 2,55 (c, 3H), 2,46 (c, 3H); (output: 77,0%).

Example 87. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(1,3-dioxolane-2-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.28 (d, 1H), 7,44 (m, 4H), 6,86 (d, 1H), 5,38 (c, 2H), 5,09 (m, 1H), 4.53-in (c, 2H), 3,76 (c, 2H), 3,60 (c, 2H), 2,58 (c, 3H), 2,46 (c, 3H); (output: 58,4%).

Example 88. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,30 (m, 4H),? 7.04 baby mortality (d, 2H), 6,88 (c, 1H), 6,60 (d, 2H), 5,51 (c, 2H), 5,23 (c, 2H), 2,59 (c, 3H), 2,37 (c, 3H); (output: 85,3%).

Example 89. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 7,28 (m, 3H), of 6.99 (m, 4H), 6.73 x (c, 1H), 6,13 (c, 1H), 5,62 (c, 2H), and 5.30 (c, 2H), 2,61 (c, 3H), 2,38 (c, 3H); (output: 86,0%).

Example 90. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,33 (c, 1H), 7,44 (m, 4H), 6.89 in (c, 1H), 5,38 (c, 2H), 4,35 (m, 2H), 2,53 (c, 3H), 2,42 (c, 3H), of 1.29 (t, 3H); (output: 88,3%).

Example 91. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,37 (d, 2H), ,06 (d, 2H), 6,99 (d, 2H), 6.87 in (c, 1H), 6,64 (c, 2H), 5,52 (c, 2H), 5,24 (c, 2H), 2,59 (c, 3H), 2,38 (c, 3H); (output: 81,1%).

Example 92. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,39 (m, 1H), 7,27 (c, 1H), 7,18 (t, 1H), 7,00 (d, 2H), PC 6.82 (d, 2H), from 6.22 (d, 2H), 5,52 (c, 2H), 5,22 (c, 2H), of 3.77 (c, 3H), 2,59 (c, 3H), 2,37 (c, 3H); (yield: 79.8 per cent).

Example 93. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 7,29 (m, 3H), 7,02 (m, 3H), 6.87 in (c, 1H), 6,40 (t, 2H), of 5.53 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (yield: 80.1%of).

Example 94. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-methoxycarbonylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 7,94 (d, 2H), 7,28 (d, 2H), 7,00 (d, 2H), 6,85 (c, 1H), 6,70 (d, 2H), 5,59 (c, 2H), 5,19 (c, 2H), 3,93 (c, 3H), 2,61 (c, 3H), 2,37 (c, 3H); (yield: 78.9 per cent).

Example 95. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,27 (d, 2H), 7,18 (t, 1H), 7,10 (d, 1H), 6,97 (d, 2H), 6,82 (c, 1H), 6.48 in (m, 2H), of 5.53 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H), 2,22 (c, 3H); (yield: 75.3%of).

Example 96. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 7,27 (d, 2H), was 7.08 (d, 2H), 7,01 (d, 2H), for 6.81 (c, 1H), 6,56 (d, 2H), 5,52 (c, 2H), 5,23 (c, 2H), 2,59 (c, 3H), 2,37 (c, 3H), 2,34 (c, 3H); (output: 78,8%).

Example 97. The hydrochloride of 7-(4-chlorobenzoyloxy)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]feast is Dina

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,44 (m, 4H), 6.89 in (d, 1H), are 5.36 (c, 2H), 4,22 (d, 2H), 2,55 (c, 3H), 2,44 (c, 3H), 1,10 (m, 1H), 0,48 (d, 2H), 0,20 (d, 2H); (output: 88.1 per cent).

Example 98. Hydrochloride of 1-allyl-7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(Benzo[1,3]dioxol-5-ylethoxy)-3-nitropyridine

In accordance with the same procedures as described in the getting 2, except for using 4-chloro-3-nitropyridine (3.0 g, 18,92 mmol) obtained in stage 1 get 1, and piperonyl alcohol (of 3.45 ml, 18,92 mmol)were specified in the title compound as a yellow solid (is 3.08 g, 88.6 per cent).

1H-NMR (CDCl3) δ 9,02 (c, 1H), at 8.60 (d, 1H), 7,06 (d, 1H), 6,91 (t, 2H), at 6.84 (d, 1H), 5,99 (c, 2H), total of 5.21 (c, 2H).

Stage 2: 7-(Benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(benzo[1,3]dioxol-5-ylethoxy)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 28,9%).

1H-NMR (CDCl3) δ of 8.28 (d, 1H), 7,94 (c, 1H), 6,94 (m, 2H), PC 6.82 (d, 1H), 6,60 (d, 1H), 5,99 (c, 2H), 5,11 (c, 2H), 2,39 (c, 3H), 2,21 (c, 3H).

Stage 3: the Hydrochloride of 1-allyl-7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in step 2 of example 33, except for using 7-(benzo is[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine, obtained in stage 2, and allylbromide got mentioned in the title compound as white solids (yield: 53.8 per cent).

1H-NMR (CDCl3) δ 8,33 (c, 1H), 6,86 (m, 4H), 6,03 (c, 2H), 5,90 (m, 1H), 5,27 (c, 2H), 5,15 (d, 1H), 4,96 (c, 2H), 4,56 (d, 1H), 2,56 (c, 3H), 2,39 (c, 3H).

Examples with 99 of 121

The connections defined in the headers of examples 99-121, were obtained using the same procedures as in step 2 of example 33, using 7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 98, and 2-pomatoleios ether, 2-methyl bromide-1,3-dioxolane, 2-formanilide, 4-tert-butylbenzylamine, methylpropanoate, 4-chloromethyl-3,5-dimethylisoxazole, 5-chloromethyl-2-oxazolidinone, 2-chlorobenzylchloride, 4-triftormetilfullerenov, 2-bromoethanol, bromatologia ether, 2,5-dimethylbenzylamine, 4-methoxycarbonylbenzyl, 4-bromo-2-methyl-2-butene, 3-methylbenzylamine, 4-methylbenzylamine, benzylbromide, 3-ftorangidridy, iodata, 4-ftorangidridy, 3-methoxybenzylamine, 1-bromo-2-methylpropane or (methyl bromide)cyclopropane.

Example 99. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (c, 1H), 6.87 in (m, 4H), 6,03 (c, 2H), 5,28 (c, 2H), 4,46 (c, 2H), 3,55 (c, 2H), 3,21 (c, 3H), 2,53 (c, 3H), 2.40 a (c, 3H); (output: 59,6%).

Example 100. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)1-([1,3]-dioxolane-2-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 6,93 (m, 4H), 6,01 (c, 2H), from 5.29 (d, 2H), 5,13 (m, 1H), 4,55 (c, 2H), 3,78 (d, 2H), 3,60 (d, 2H), 2,53 (c, 3H), 2,32 (c, 3H); (output: 61,4%).

Example 101. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (m, 1H), 7,07 (m, 3H), PC 6.82 (m, 1H), 6.73 x (d, 1H), is 6.61 (d, 1H), 6,39 (c, 1H), 6,221 (m, 1H), 5,99 (c, 2H), 5,61 (c, 1H), 5,15 (c, 2H), 2,60 (c, 3H), 2,29 (c, 3H); (output: 58,8%).

Example 102. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-tert-butylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (c, 1H), 7,30 (m, 2H), 6,79 (m, 2H), only 6.64 (m, 3H), to 6.43 (c, 1H), 5,99 (c, 2H), of 5.53 (c, 2H), 5,15 (c, 2H), 2,58 (c, 3H), 2,38 (c, 3H), 1,29 (c, 9H); (yield: 83.0 per cent).

Example 103. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-methoxycarbonylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 6,95 (m, 4H), 6,03 (c, 2H), 5.25 in (c, 2H), of 5.05 (c, 2H), 3,69 (c, 3H), 2,55 (c, 3H), 2,44 (c, 3H); (output: 68,1%).

Example 104. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3,5-dimethylisoxazol-4-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (c, 1H), 6,95 (m, 3H), of 6.71 (c, 1H), 6,00 (c, 2H), 5,34 (c, 2H), 5,24 (c, 2H), 2,56 (c, 3H), 2,35 (c, 3H), 1,81 (c, 3H), 1,64 (c, 3H); (output: 74,0%).

Example 105. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-oxazolidinone-5-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 6,93 (m, 4H), 6,01 (c, 2H), 5,28 (c, 2H), 4,89 (c, 2H), 3,84 (m, 2H), only 3.57 (m, 1H), of 2.51 (c, 3H), 2,48 (c, 3H); (output: 65,4%.

Example 106. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,40 (d, 1H), 6,93 (m, 1H), 6,85 (m, 3H), of 6.71 (d, 1H), 6,54 (m, 1H), 6,24 (c, 1H), 5,99 (c, 2H), 5,58 (c, 2H), 5,08 (c, 2H), 2,62 (c, 3H), 2,36 (c, 3H); (yield: 73.2 per cent).

Example 107. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1-(4-trifloromethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,52 (d, 2H), 6,77 (m, 4H), to 6.57 (d, 1H), 6,44 (c, 1H), 6,00 (c, 2H), ceiling of 5.60 (c, 2H), 5,12 (c, 2H), 2,61 (c, 3H), 2,39 (c, 3H); (yield: 83.5 per cent).

Example 108. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-hydroxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,03 (m, 2H), 6.89 in (m, 2H), 6,03 (c, 2H), 5,33 (t, 2H), of 4.44 (t, 2H), a 3.87 (m, 2H), 2,53 (c, 3H), 2.49 USD (c, 3H); (output: 46,5%).

Example 109. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 6,95 (m, 2H), to 6.88 (m, 2H), 6,04 (c, 2H), 5,62 (c, 2H), are 5.36 (c, 2H), 3,19 (c, 3H), 2,55 (c, 3H), 2,48 (c, 3H); (output: 79,5%).

Example 110. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2,5-dimethylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (c, 1H), 6,94 (m, 2H), 6,69 (m, 1H), 6,52 (c, 1H), 6,21 (c, 1H), 6,01 (c, 1H), 5,99 (c, 2H), 5,65 (c, 1H), and 5.30 (c, 2H), total of 5.21 (c, 2H), 5,06 (c, 2H), 2.63 in (c, 3H), 2,31 (c, 3H), 2,11 (c, 3H), 2,05 (c, 3H); (output: 63,5%).

Example 111. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-methoxycarbonylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-a]pyridine

1H-NMR (CDCl3) δ 8,33 (c, 1H), 7,93 (c, 1H), 6,95 (m, 3H), of 6.65 (m, 3H), 6,38 (c, 1H), 5,99 (c, 2H), 5,61 (c, 2H), 5,13 (c, 2H), 3,91 (c, 3H), of 2.51 (c, 3H), 2,39 (c, 3H); (output: 65,0%).

Example 112. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-methylbut-2-enyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,29 (c, 1H), 6,88 (m, 5H), 6,01 (c, 2H), from 5.29 (c, 2H), 5,04 (t, 1H), 4,96 (d, 2H), 2,53 (c, 3H), 2,39 (c, 3H), 1.70 to (c, 3H), 1,62 (c, 3H); (yield: 74.1 per cent).

Example 113. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,16 (t, 1H), to 7.09 (d, 1H), 6,78 (m, 2H), only 6.64 (d, 1H), 6,44 (m, 3H), 5,99 (c, 2H), 5,54 (c, 2H), 5,16 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H), and 2.27 (c, 3H); (output: 66,8%).

Example 114. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), was 7.08 (d, 2H), to 6.88 (m, 2H), 6,63 (m, 3H), 6.42 per (c, 1H), 5,99 (c, 2H), 5,52 (c, 2H), 5,16 (c, 2H), 2,58 (c, 3H), 2,47 (c, 3H), 2,32 (c, 3H); (output: 66,0%).

Example 115. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,33 (c, 1H), 7,28 (m, 3H), for 6.81 (c, 1H), 6,72 (m, 3H), 6,60 (d, 1H), gold 6.43 (c, 1H), 5,99 (c, 2H), 5,57 (c, 2H), 5,15 (c, 2H), 2,59 (c, 3H), 2,38 (c, 3H); (output: 70,5%).

Example 116. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), 6,99 (t, 2H), to 6.88 (m, 2H), 6,65 (c, 1H), 6,41 (m, 3H), 6,01 (c, 2H), of 5.53 (c, 2H), 5,14 (c, 2H), 2,60 (c, 3H), 2,31 (c, 3H); (output: 69,8%).

u> Example 117. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (d, 1H), 6.87 in (m, 5H), 6,03 (c, 2H), from 5.29 (c, 2H), 4,35 (m, 2H), 2,53 (c, 3H), 2,42 (c, 3H), of 1.30 (t, 3H); (yield: 73.3 per cent).

Example 118. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H),? 7.04 baby mortality (m, 3H), 6.87 in (m, 1H), 6,76 (m, 3H), 6,55 (c, 1H), 6,00 (c, 2H), 5,52 (c, 2H), 5,16 (c, 2H), 2,59 (c, 3H), 2,38 (c, 3H); (yield: 72.1 per cent).

Example 119. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 6,91 (m, 3H), of 6.65 (m, 2H), 6,45 (c, 1H), 6,24 (m, 2H), 6,02 (c, 2H), 5.40 to (c, 2H), 5,13 (c, 2H), 3.72 points (c, 3H), 2,62 (c, 3H), 2,36 (c, 3H); (yield: 73.2 per cent).

Example 120. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-isobutyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ to 8.41 (d, 1H), 6,93 (m, 4H), 6,03 (c, 2H), 5.25 in (c, 2H), 4,03 (c, 2H), 2.63 in (c, 3H), 2.40 a (c, 3H), 1,99 (m, 1H), 0.67 and (c, 6H); (yield: 80.3 per cent).

Example 121. Hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 6,93 (c, 2H), 6.87 in (d, 2H), 6,04 (c, 2H), 5,28 (c, 2H), 4,23 (d, 2H), 2,55 (c, 3H), 2,44 (c, 3H), 1,11 (m, 1H), 0,49 (d, 2H), 0,22 (d, 2H); (output: 72,5%).

Example 122. 7-(4-Forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

The compound obtained in example 61 (2.1 g, 6.05 mmol), was treated with a saturated solution Bica is bonate sodium obtaining specified in the title compounds as white solids (yield: 99.4 per cent).

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,47 (c, 2H), 7,16 (t, 2H), 6,91 (d, 1H), 5,39 (c, 2H), of 4.44 (c, 2H), 3,51 (c, 2H), 3,19 (c, 3H), 2,52 (c, 3H), 2,43 (c, 3H).

Example 123. Methanesulfonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

0,039 ml Methanesulfonic acid was added at room temperature to a solution of 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (200 mg, 0,609 mmol)obtained in example 122, in 10 ml of ethyl acetate, and then was stirred for 24 hours at the same temperature. The resulting solid was filtered to obtain specified in the title compounds as white solids (yield: 85.1%)are.

1H-NMR (DMSO-d6) δ 8,48 (c, 1H), to 7.64 (c, 2H), 7,33 (m, 3H), 5,55 (c, 2H), 4,47 (c, 2H), 3,52 (c, 2H), 3,11 (c, 3H), 2,43 (c, 3H), 2,32 (c, 3H), 2.26 and (c, 3H).

Examples 124 through 133

The connections defined in the headers of examples 124-133, were obtained using the same procedures as in example 123, using 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in example 122, and benzosulfimide acid, p-toluensulfonate acid, nitric acid, sulfuric acid, maleic acid, phosphoric acid, malonic acid, campolongo acid, oxalic acid or Hydrobromic acid.

Example 124. Bansilalpet 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,50 (c, 1H), 7,63 (m, 4H), 7,31 (c, 6H), 5,55 (c, 2H), 4,47 (c, 2H), 3,52 (c, 2H), 3,11 (c, 3H), 2,43 (c, 3H), 2.26 and (c, 3H); (yield: 92.3 per cent).

Example 125. p-Toluensulfonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,50 (c, 1H), 7,63 (c, 2H), (c, 3H), 7,46 (d, 2H), 7,32 (m, 3H), 7,12 (d, 2H), 5,55 (c, 2H), 4,47 (c, 2H), 3,52 (c, 2H), 3,11 (c, 3H), 2,43 (c, 3H), 2,28 (c, 3H), 2.26 and (c, 3H); (yield: 95.4 percent).

Example 126. Nitrate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,48 (c, 1H), to 7.64 (c, 2H), 7,32 (m, 3H), 5,55 (c, 2H), 4,47 (c, 2H), 3,52 (c, 2H), 3,11 (c, 3H), 2,43 (c, 3H), 2.26 and (c, 3H); (output: 88,4%).

Example 127. Sulfate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,24 (c, 1H), 7,41 (c, 2H), was 7.08 (m, 3H), 5,31 (c, 2H), 4,24 (c, 2H), 3.33 and (c, 2H), 2,88 (c, 3H), 2,20 (c, 3H), 2,03 (c, 3H); (yield: 89.4 per cent).

Example 128. Maleate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,44 (c, 1H), 7,63 (c, 2H), 7,30 (m, 3H), 6,05 (c, 2H), 5,52 (c, 2H), 4,46 (c, 2H), 3,51 (c, 2H), 3,11 (c, 3H), 2,42 (c, 3H), 2,25 (c, 3H); (output: 96,5%).

Example 129. Phosphate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,14 (c, 1H), 7,58 (c, 2H), 7,28 (m, 2H), 6,86 (c, 1H), 5,31 (c, 2H), 4,39 (c, 2H), 3,55 (c, 2H), 3,11 (c, 3H), 2,34 (c, 3H), 2,18 (c, 3H); (output: 88,2%).

Example 130. Malonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H is the Mr (DMSO-d 6) δ 8,23 (c, 1H), 7,60 (c, 2H), 7,29 (m, 2H), 6,98 (c, 1H), lower than the 5.37 (c, 2H), 4,40 (c, 2H), 3,56 (c, 2H), 3,11 (c, 3H), 3.04 from (c, 2H), 2,36 (c, 3H), 2,20 (c, 3H); exit; 79,9%).

Example 131. Champoulet 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,48 (d, 1H), to 7.64 (c, 2H), 7,32 (m, 3H), 5,55 (c, 2H), 4,47 (c, 2H), 3,52 (c, 2H), 3,11 (c, 3H), 2,89 (d, 1H), 2,68 (m, 1H), 2,43 (c, 3H), 2,36 (d, 1H), 2.26 and (c, 3H), 2,20 (c, 1H), 1,92 (c, 1H), of 1.84 (m, 2H), 1.28 (in m, 2H), 1.04 million (c, 3H), 0,73 (c, 3H); (yield: 86.9 per cent).

Example 132. Oxalate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,33 (c, 1H), to 7.61 (c, 2H), 7,28 (m, 2H), 7,12 (c, 1H), 5,44 (c, 2H), 4,43 (c, 2H), 3,51 (c, 2H), 3,11 (c, 3H), 2,34 (c, 3H), 2,16 (c, 3H); (yield: 95.2 percent).

Example 133. The hydrobromide 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) of 8.37 δ (c, 1H), 7,53 (c, 2H), 7,21 (m, 3H), of 5.45 (c, 2H), 4,36 (c, 2H), 3,41 (d, 2H), 3.00 and (c, 3H), 2,33 (c, 3H), 2,16 (c, 3H); (yield: 75.8 per cent).

Example 134. The hydrochloride of 7-(2,4-dichloraniline)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(2,4-Dichloraniline)-3-nitropyridine

In accordance with the same procedures as described in the getting 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 2,4-amyl-metacresol got mentioned in the title compound as white solids (yield: 89.3 per cent).

1H-NMR (CDCl3) δ 9,05 (c, 1H), at 8.60 (d, 1H), 7,13 (d, 1H), from 5.29(d, 1H).

Stage 2: 7-(2,4-Dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(2,4-dichloraniline)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 28.6 per cent).

1H-NMR (CDCl3) δ 8,29 (d, 1H), 8,01 (c, 1H), 7,52 (m, 3H), 6,53 (d, 1H), 5,18 (c, 2H), 2,41 (c, 3H), 2,31 (c, 3H).

Stage 3: the Hydrochloride of 7-(2,4-dichloraniline)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 1 of example 33, except for using 7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and bromatologia ether has been specified in the title compound as white solids (yield: 58,9%).

1H-NMR (CDCl3) δ scored 8.38 (d, 1H), 7,54 (m, 2H), 7,51 (m, 2H), 5,61 (c, 2H), 5,50 (c, 2H), 3,17 (c, 3H), 2,56 (c, 3H), 2.49 USD (c, 3H).

Examples from 135 through 143

The connections defined in the headers of examples 135-143, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 134, and 4-bromo-2-methyl-2-butene, benzylbromide, iodata, Bromeliaceae, (methyl bromide)cyclopropane, 4-ftorangidridy, 3-methoxybenzylamine, 2-is libuniversal or 4-tert-butylbenzylamine.

Example 135. The hydrochloride of 7-(2,4-dichloraniline)-2,3-dimethyl-1-(3-methylbut-2-enyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,52 (c, 1H), 7,43 (m, 3H), ceiling of 5.60 (c, 2H), 5,14 (t, 1H), 4,80 (c, 2H), 2,55 (c, 3H), 2,41 (c, 3H), 1,59 (c, 6H); (output: 75,9%).

Example 136. Hydrochloride of 1-benzyl-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,43 (c, 3H), 7,11 (m, 2H), 6.89 in (m, 1H), 6,67 (m, 2H), 5,58 (c, 2H), 5,32 (c, 2H), 2,64 (c, 3H), 2,41 (c, 3H); (yield: 86.4 per cent).

Example 137. The hydrochloride of 7-(2,4-dichloraniline)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,55 (c, 1H), 7,52 (d, 1H), 7,43 (d, 1H), 6,93 (d, 1H), 5,45 (c, 2H), 4,34 (m, 2H), 2,58 (c, 3H), 2,42 (c, 3H), of 1.11 (t, 3H); (output: 75,9%).

Example 138. The hydrochloride of 7-(2,4-dichloraniline)-1-methoxycarbonylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,54 (c, 1H), 7,39 (m, 2H), 6.89 in (c, 1H), 5.40 to (c, 2H), 5,04 (c, 2H), 3,61 (c, 3H), 2.57 m (c, 3H), 2,36 (c, 3H); (output: 69,7%).

Example 139. Hydrochloride of 1-cyclopropylmethyl-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ to 8.41 (d, 1H), 7,60 (m, 2H), 7,52 (m, 1H), 7,38 (m, 1H), 5,45 (c, 2H), 4,33 (d, 2H), 2,56 (c, 3H), 2,47 (c, 3H), 1,11 (m, 1H), 0,48 (m, 2H), 0,19 (m, 2H); (yield: 78.3%of).

Example 140. The hydrochloride of 7-(2,4-dichloraniline)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.40 (d, 1H), 7,44 (c, 1H), 7,19 (m, 2H), 6.90 to (m, 3H), 6,38 (m, 2H), 5,52 (c, 2H), 5,32 (c, 2H), 2,61 (c, 3H), 2,39 (c, 3H); (output: 75,5%)

Example 141. The hydrochloride of 7-(2,4-dichloraniline)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,42 (c, 1H), 7,13 (m, 3H), 6,86 (m, 3H), 6,20 (c, 1H), 5,52 (c, 2H), 5,31 (c, 2H), 3,70 (c, 3H), 2,55 (c, 3H), 2,38 (c, 3H); (output: 78,6%).

Example 142. Hydrochloride of 1-(2-Chlorobenzyl)-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (d, 1H), 7,38 (c, 1H), 7,31 (m, 2H), 7,14 (m, 2H), at 6.84 (d, 2H), 6,01 (d, 1H), 5,57 (d, 2H), 5,26 (c, 2H), 2.63 in (c, 3H), 2,36 (c, 3H); (output: 58,5%).

Example 143. Hydrochloride of 1-(4-tert-butylbenzyl)-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,43 (c, 1H), 7.23 percent (m, 2H), 7,10 (c, 1H), 6,92 (m, 2H), 6,60 (d, 2H), from 5.29 (c, 2H), 5,33 (c, 2H), 2,61 (c, 3H), 2,44 (c, 3H), 1.28 (in c, 9H); (yield: 68.8 per cent).

Example 144. Hydrochloride of 1-benzyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(3-Methylbenzylamino)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 3-methylbenzylamino alcohol has been specified in the title compound as yellow solid (yield: 89,8%).

1H-NMR (CDCl3) δ 9,03 (c, 1H), to 8.62 (d, 1H), 7,45 (m, 4H), to 7.09 (d, 1H), 5,35 (d, 1H), 1,53 (c, 3H).

Stage 2: 7-(3-Methylbenzylamino)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that stage Primera 33, except for using 4-(3-methylbenzylamino)-3-nitropyridine obtained at stage 1 has been specified in the title compound as a pale yellow solid (yield: 28.3 per cent).

1H-NMR (CDCl3) δ 8,29 (d, 1H), 8,01 (c, 1H), 7,40 (m, 4H), to 6.58 (d, 1H), 5,23 (c, 2H), 2.40 a (c, 3H), 2,30 (c, 3H), 1.55V (c, 1H).

Stage 3: the Hydrochloride of 1-benzyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(3-methylbenzylamino)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and benzylbromide got mentioned in the title compound as white solids (yield: 89.3 per cent).

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,20 (m, 3H), 6.89 in (d, 2H), for 6.81 (d, 1H), 6,72 (d, 2H), 5,59 (c, 2H), 5,23 (c, 2H), 2,60 (c, 3H), 2,32 (c, 3H), 2,24 (c, 3H).

Examples from 145 to 159

The connections defined in the headers of examples 145-159, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(3-methylbenzylamino)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 144, and itatani, 3-formanilide, 4-chlorobenzylchloride, 3-methylbenzylamine, 2-chloromethylpyridine, 2,5-dimethylbenzylamine, 4-tert-butylbenzylamine, 4-bromo-2-methyl-2-butene, 1-iodopropane, (methyl bromide)cyclopropane, allylbromide, 4-methylbenzylamine, 2-pomatoleios ether, 4-Forbes is chloride or 3-methoxybenzylamine.

Example 145. Hydrochloride of 1-ethyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (c, 1H), 7,34 (m, 4H), 6,86 (d, 1H), lower than the 5.37 (c, 2H), to 4.38 (m, 2H), 2,53 (c, 3H), 2,42 (c, 3H), 2.40 a (c, 3H), of 1.29 (t, 3H); (output: 69,0%).

Example 146. Hydrochloride of 1-(3-terbisil)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,18 (m, 3H), 6,97 (m, 3H), 6,83 (d, 1H), only 6.64 (m, 2H), 5,54 (c, 2H), 5,23 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H), 2,30 (c, 3H); (output: 58,9%).

Example 147. Hydrochloride of 1-(4-Chlorobenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,19 (m, 4H), 6.90 to (m, 3H), of 6.61 (d, 2H), 5,57 (c, 2H), 5,22 (c, 2H), 2,59 (c, 3H), 2,37 (c, 3H), 2,30 (c, 3H); (output: 51,4%).

Example 148. Hydrochloride of 2,3-dimethyl-1-(3-methylbenzyl)-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,34 (m, 1H), 7,14 (m, 2H), to 7.09 (d, 1H), 6,91 (m, 3H), 6,50 (m, 2H), 5.56mm (c, 2H), 5.25 in (c, 2H), 2,59 (c, 3H), 2.40 a (c, 3H), 2,37 (c, 3H), and 2.27 (c, 3H); (output: 63,3%).

Example 149. Hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-(pyridine-2-ylmethyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,18 (m, 3H), 6,97 (m, 3H), 6,83 (d, 1H), only 6.64 (m, 2H), 5,54 (c, 2H), 5,23 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H), 2,30 (c, 3H); (yield: 85.4 percent).

Example 150. Hydrochloride of 1-(2,5-dimethylbenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,33 (m, 1H), 7,16 (m, 2H), 6,99 (m, 2H), 6,79 (m, 3H), 5,44 (c, 2H), 5,15 (c, 2H), 2.63 in (c, 3H), 2.40 a (c, 3H), and 2.27 (c, 6H), 2.00 in (c, 3H); (output: 72,0%).

Example 151. Hydrochloride of 1-(4-tert-butylbenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,34 (m, 4H), 7,19 (d, 1H), 6,97 (c, 1H), 6.87 in (m, 1H), 6,65 (d, 1H), 5.56mm (c, 2H), 5.25 in (c, 2H), 2,59 (c, 3H), 2,54 (c, 3H), 2,37 (c, 3H), 1,29 (c, 9H); (yield: 80.1%of).

Example 152. Hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-(3-methylbut-2-enyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.40 (d, 1H), 7,31 (m, 4H), 5.40 to (c, 2H), total of 5.21 (m, 1H), 4,99 (c, 2H), 2.57 m (c, 3H), 2,38 (c, 6H), 1,81 (c, 6H); (output: 74,6%).

Example 153. Hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-propyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 7,34 (m, 4H), 6,88 (c, 1H), 5,33 (c, 2H), 4,20 (t, 2H), 2.40 a (c, 3H), 2,30 (c, 3H), 2,17 (c, 3H), 1.69 in (m, 2H), 0.75 in (t, 3H); (yield: 78.2 per cent).

Example 154. Hydrochloride of 1-cyclopropylmethyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,34 (m, 4H), 6.89 in (d, 1H), 5,35 (c, 2H), 4,13 (d, 2H), 2,56 (c, 3H), 2,45 (c, 3H), 2,41 (c, 3H), of 1.13 (m, 1H), 0,48 (m, 2H), 0,22 (m, 2H); (yield: 66.9 per cent).

Example 155. Hydrochloride of 1-allyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,31 (m, 3H), 6,85 (d, 1H), 5,90 (m, 1H), 5,35 (c, 2H), 5,15 (d, 1H), equal to 4.97 (c, 2H), 4,57 (d, 1H), 2.57 m (c, 3H), 2,39 (c, 6H); (output: 72,3%).

Example 156. Hydrochloride of 2,3-dimethyl-1-(4-methylbenzyl)-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (d, 1H), 7,19 (m, 2H), to 7.09 (d, 2H), 6,92 (m, 3H), 6,62 (d, 2H), 5,55 (c, 2H), 5.25 in (c, 2H), 258 (c, 3H), 2,37 (c, 3H), and 2.27 (c, 3H), and 2.27 (c, 3H); (yield: 93.5 per cent).

Example 157. Hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,34 (m, 4H), 6.87 in (d, 1H), are 5.36 (c, 2H), 4,47 (m, 2H), 3,50 (m, 2H), 3,20 (c, 3H), 2,54 (c, 3H), 2,44 (c, 3H), 2.40 a (c, 3H); (output: 86,3%).

Example 158. Hydrochloride of 1-(4-terbisil)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (t, 1H), 7,20 (m, 3H), 7,00 (m, 3H), 6,85 (d, 1H), 6.42 per (m, 2H), 5,55 (c, 2H), 5,23 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H), 2,29 (c, 3H); (output: 91,0%).

Example 159. Hydrochloride of 1-(3-methoxybenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,33 (m, 1H), 7,17 (m, 2H), 6,91 (c, 2H), for 6.81 (d, 2H), 6,27 (c, 1H), 5.56mm (c, 2H), 5,24 (c, 2H), 3,70 (c, 3H), 2,52 (c, 3H), 2.49 USD (c, 3H), 2,17 (c, 3H); (yield: 88.5 percent).

Example 160. Hydrochloride of 1-(3-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(2-Ethoxybenzyl)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 2-ethoxybenzyl alcohol has been specified in the title compound as yellow solid (yield: 65.9%of).

1H-NMR (CDCl3) δ 9,04 (c, 1H), to 8.62 (d, 1H), 7,32 (m, 4H),? 7.04 baby mortality (d, 1H), 5,33 (d, 1H), 2,87 (m, 2H), 1,2 (t, 3H).

Stage 2: 7-(2-Ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(2-ethoxybenzyl)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 25.5 per cent).

1H-NMR (CDCl3) δ 8.30 to (d, 1H), 8,01 (c, 1H), 7,25 (m, 4H), to 6.58 (d, 1H), and 5.30 (c, 2H), 3,12 (m, 2H), 2,41 (c, 3H), 2.26 and (c, 3H), of 1.21 (t, 3H).

Stage 3: the Hydrochloride of 1-(3-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 and 3-chlorobenzylamino got mentioned in the title compound as white solids (yield: 79.8 per cent).

1H-NMR (CDCl3) δ compared to 8.26 (d, 1H), 7,88 (d, 1H), 7.23 percent (m, 3H),? 7.04 baby mortality (t, 3H), 6,97 (d, 4H), 6,63 (m, 2H), 5,28 (m, 2H), 3,01 (c, 3H), 2,36 (c, 3H), 2,33 (c, 3H).

Examples c 161 on 178

The connections defined in the headers of examples 161-178, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 160, and (methyl bromide)cyclopropane, 2-pomatoleios ether (methyl bromide)CYCLOBUTANE, allylbromide, iodata, 3,4-dichlorobenzaldehyde, 2-methoxybenzylamine, 2-chlorobenzylchloride, 2-formanilide, 1-iodine is Rapana, 4-methoxybenzylamine, 4-chlorobenzylchloride, 3-methylbenzylamine, 4-methylbenzylamine, 4-formanilide, 2-methyl bromide-1,3-dioxolane, 3-methoxybenzylamine or 3-ftorangidridy.

Example 161. Hydrochloride of 1-cyclopropylmethyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (t, 1H), 7,39 (m, 2H), of 6.96 (m, 3H), 5,44 (c, 2H), 4,23 (d, 2H), 4,12 (m, 2H), 2,55 (c, 3H), 2,43 (c, 3H), of 1.41 (t, 3H), of 1.12 (m, 1H), 0,43 (m, 2H), 0,20 (m, 2H); (yield: 82.5 per cent).

Example 162. The hydrochloride of 7-(2-ethoxybenzyl)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (t, 1H), was 7.36 (m, 2H), of 6.96 (m, 3H), of 5.45 (c, 2H), of 4.45 (t, 2H), 4,11 (m, 2H), 3,54 (t, 2H), 3,17 (c, 3H), 2,52 (c, 3H), 2,42 (c, 3H), of 1.40 (t, 3H); (yield: 78.4 per cent).

Example 163. Hydrochloride of 1-cyclobutylmethyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (c, 1H), 7,39 (m, 2H), 6,97 (m, 3H), of 5.45 (c, 2H), 4,30 (c, 2H), 4,12 (d, 2H), 2.63 in (m, 1H), 2,54 (c, 3H), 2,41 (c, 3H), 1.77 in-of 1.55 (m, 6H), 1,25 (t, 3H); (output: 69,7%).

Example 164. Hydrochloride of 1-allyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (d, 1H), was 7.36 (m, 2H), 6,97 (m, 3H), to 5.58 (m, 1H), 5,49 (c, 2H), 5,11 (d, 1H), equal to 4.97 (c, 2H), br4.61 (d, 1H), 4,12 (m, 2H), 2,55 (c, 3H), 2,38 (c, 3H), of 1.42 (t, 3H); (output: 51,0%).

Example 165. The hydrochloride of 7-(2-ethoxybenzyl)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.30 to (t, 1H), 7,37 (d, 1H), 6,98 (m, 3H), 5,46 (c, 2H), 4,36 (m, 2H), 4,12 (m, 2H), 2,53 (c, 3H), 2.40 a (c, 3H),of 1.40 (t, 3H), of 1.28 (t, 3H); (output: 65,8%).

Example 166. Hydrochloride of 1-(3,4-dichlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,38 (m, 2H), 6,99 (t, 2H), 6.89 in (t, 2H), 6,78 (c, 1H), 6.42 per (d, 1H), 5,48 (c, 2H), 5,32 (c, 2H), 3,99 (m, 2H), 2,53 (c, 3H), 2,35 (c, 3H), of 1.29 (t, 3H); (output: 74,0%).

Example 167. The hydrochloride of 7-(2-ethoxybenzyl)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,21 (m, 3H), PC 6.82 (m, 5H), of 6.02 (d, 1H), 5,58 (c, 2H), and 5.30 (c, 2H), 3,98 (m, 2H), 3,76 (c, 3H), 2,58 (c, 3H), 2,31 (c, 3H), of 1.32 (t, 3H); (output: 63,5%).

Example 168. Hydrochloride of 1-(2-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (t, 1H), was 7.36 (d, 1H), 7,21 (m, 2H), 7,10 (t, 1H), 6,92 (d, 1H), PC 6.82 (d, 1H), 6.75 in (c, 2H), 6,02 (d, 2H), 5,64 (c, 2H), and 5.30 (c, 2H), 3.96 points (m, 2H), 2,60 (c, 3H), 2,33 (c, 3H), of 1.31 (t, 3H); (yield: 74.2 per cent).

Example 169. The hydrochloride of 7-(2-ethoxybenzyl)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,30 (m, 1H), of 6.96 (m, 4H), 6,85 (m, 3H), 6,24 (t, 1H), 5,65 (c, 2H), 5,35 (c, 2H), 4,01 (m, 2H), 2,58 (c, 3H), 2,35 (c, 3H), of 1.34 (t, 3H); (output: 63,0%).

Example 170. The hydrochloride of 7-(2-ethoxybenzyl)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,39 (m, 2H), 7,00 (m, 3H), 5,43 (d, 2H), 4,21 (m, 2H), 4,11 (m, 2H), 2,54 (c, 3H), 2.40 a (c, 3H), 1,58 (m, 2H), 1.39 in (m, 3H), 0.74 and (m, 3H); (yield: 68.8 per cent).

Example 171. The hydrochloride of 7-(2-ethoxybenzyl)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine/p>

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,32 (m, 1H), of 6.96 (m, 4H), 6,77 (d, 2H), only 6.64 (d, 2H), 5,52 (c, 2H), are 5.36 (c, 2H), Android 4.04 (m, 2H), 3,81 (c, 3H), 2,56 (c, 3H), 2,36 (c, 3H), of 1.34 (t, 3H); (output: 84,0%).

Example 172. Hydrochloride of 1-(4-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,35 (m, 1H), 7,19 (d, 2H), 6,94 (d, 1H), 6.87 in (d, 1H), 6,60 (d, 1H), 5,52 (c, 2H), 5,33 (c, 2H), 3,98 (m, 2H), 2,59 (c, 3H), 2,36 (c, 3H), of 1.31 (t, 3H); (output: 75,0%).

Example 173. The hydrochloride of 7-(2-ethoxybenzyl)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,30 (m, 1H), 7,15 (m, 2H), 7,11 (m, 1H), 6,92 (m, 2H), 6.87 in (m, 1H), of 6.49 (m, 2H), 5,50 (c, 2H), 5,35 (c, 2H), 4,01 (m, 2H), 2,58 (c, 3H), 2,47 (c, 3H), 2,29 (c, 3H), of 1.34 (t, 3H); (yield: 83.0 per cent).

Example 174. The hydrochloride of 7-(2-ethoxybenzyl)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.30 to (d, 1H), 7,52 (m, 1H), 7,05 (d, 2H), to 6.88 (m, 4H), 6,62 (d, 2H), 5,55 (c, 2H), 5,35 (c, 2H), was 4.02 (m, 2H), 2,58 (c, 3H), 2,35 (c, 3H), 2,31 (c, 3H), of 1.34 (t, 3H); (output: 75,0%).

Example 175. Hydrochloride of 1-(4-terbisil)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 7,34 (t, 1H), 6,93 (m, 6H), to 6.67 (t, 2H), of 5.53 (c, 2H), 5,34 (c, 2H), 4,01 (m, 2H), 2.57 m (c, 3H), 2,36 (c, 3H), of 1.32 (t, 3H); (output: 64,0%).

Example 176. Hydrochloride of 1-(1,3-dioxolane-2-ylmethyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,86 (c, 1H), 8,33 (m, 1H), 7,42 (m, 2H), 6,95 (m, 2H), 5,48 (d, 2H), 5,10 (m, 1H), 4.53-in (d, 2H), 4,11 (m, 2H), 3,71 (m, 4H), 2,52 (c, 3H) 2,45 (c, 3H), of 1.40 (m, 3H); (output: 75,4%).

Example 177. The hydrochloride of 7-(2-ethoxybenzyl)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,31 (m, 1H), 7,16 (t, 1H), 6,92 (d, 2H), 6,84 (m, 3H), 6,26 (c, 2H), 5,57 (c, 2H), 5,35 (c, 2H), 4,01 (m, 2H), 3,68 (c, 3H), 2.57 m (c, 3H), 2,35 (c, 3H), of 1.34 (t, 3H); (output: 79,5%).

Example 178. Hydrochloride of 1-(3-terbisil)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,33 (t, 1H), 7,19 (m, 1H), 6,94 (t, 3H), 6,85 (m, 2H), to 6.43 (m, 2H), 5,55 (c, 2H), 5,34 (c, 2H), 3,99 (m, 2H), 2,59 (c, 3H), 2,36 (c, 3H), of 1.34 (t, 3H); (yield: 86.7 per cent).

Example 179. Hydrochloride of 1-cyclobutylmethyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(3,5-Deferasirox)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 3.5-differenziava alcohol has been specified in the title compound as yellow solid (yield: 78,0%).

1H-NMR (CDCl3) δ 9,06 (c, 1H), 8,73 (c, 1H), 8,65 (d, 1H), 7,40 (c, 1H), 7,35 (c, 1H),? 7.04 baby mortality (d, 1H), 5,28 (d, 1H).

Stage 2: 7-(3,5-Deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(3,5-deferasirox)-3-nitropyridine obtained at stage 1 has been specified in the header of the connection in the view of the white solids (yield: 20.4 percent).

1H-NMR (CDCl3) δ 8,75 (c, 1H), 8,66 (d, 1H), 8,01 (c, 1H), 7,40 (c, 1H), 7,35 (c, 1H),? 7.04 baby mortality (d, 1H), 5,28 (d, 1H), 2,11 (c, 3H), 2,35 (c, 3H).

Stage 3: Hydrochloride 1-cyclobutylmethyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and (methyl bromide)CYCLOBUTANE got mentioned in the title compound as white solids (yield: 70,5%).

1H-NMR (CDCl3) δ at 8.36 (c, 1H), 7,02 (m, 2H), 6,91 (m, 1H), PC 6.82 (m, 1H), are 5.36 (c, 2H), 4,35 (d, 2H), to 2.67 (m, 1H), 2,55 (c, 3H), 2,44 (c, 3H), at 1.73 (m, 2H), 1,67 (m, 2H).

Examples with 180 199

The connections defined in the headers of examples 180-199, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 179, and (methyl bromide)cyclopropane, 2-pomatoleios ether, 1-iodopropane, 4-chlorobenzylchloride, 4-ftorangidridy, iodata, 3,4-dichlorobenzaldehyde, iodomethane, 2-chlorobenzylchloride, 3,4-dimethoxybenzaldehyde, 2-methoxybenzylamine, 2-formanilide, 3-chlorobenzylchloride, 4-methoxybenzaldehyde, 3-methoxybenzaldehyde, benzylbromide, 4-methylbenzylamine, 2-chloromethylpyridine, 3-chloromethylpyridine or 2-chloro-N,N-dimethylethylamine is drochloride.

Example 180. Hydrochloride of 1-cyclopropylmethyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H),? 7.04 baby mortality (m, 2H), 6.89 in (m, 2H), 5,39 (c, 2H), 4,34 (d, 2H), 2.57 m (c, 3H), 2,47 (c, 3H)and 1.15 (m, 1H), 0,56 (m, 2H), 0,27 (m, 2H); (output: 86,0%).

Example 181. Hydrochloride 7-(3,5-deferasirox)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (d, 1H), 7,02 (d, 2H), 6.89 in (m, 2H), 5,33 (c, 2H), 4.53-in (t, 2H)and 3.59 (t, 2H), 3.27 to (c, 3H), 2,55 (c, 3H), 2,43 (c, 3H); (output: 75,6%).

Example 182. Hydrochloride 7-(3,5-deferasirox)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,01 (d, 2H), 6,91 (m, 1H), 6,83 (m, 1H), 5,35 (c, 2H) , 4,24 (t, 2H), 2,55 (c, 3H), 2,43 (c, 3H), at 1.73 (m, 2H), or 0.83 (t, 3H); (output: 58,7%).

Example 183. Hydrochloride of 1-(4-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (s, 1H), 7,37 (m, 1H), 7,03 (d, 1H), 6,85 (t, 1H), 6,59 (m, 4H), 5.56mm (c, 2H), 5,23 (c, 2H), 2,53 (c, 3H), 2,39 (c, 3H); (output: 63,3%).

Example 184. Hydrochloride 7-(3,5-deferasirox)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (d, 1H), 7,06 (m, 2H), 6,84 (m, 2H), 6,59 (c, 2H), 6.42 per (m, 2H), 5,85 (c, 2H), 5,24 (c, 2H), 2,54 (c, 3H), 2.40 a (c, 3H); (yield: 71.2 percent).

Example 185. Hydrochloride 7-(3,5-deferasirox)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (c, 1H), 6,99 (c, 2H), 6.89 in (m, 1H), PC 6.82 (m, 1H), 5,38 (c, 2H), and 4.40 (m, 2H), 2,55 (c, 3H), 2,44 (c, 3H), of 1.27 (t, 3H); (yield: 83.6 percent).

Example 16. Hydrochloride 7-(3,5-deferasirox)-1-(3,4-dichlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,40 (c, 1H), 7,49 (m, 1H), PC 6.82 (m, 2H), 6,65 (d, 2H), 6,50 (m, 2H), 5,49 (c, 2H), 5,24 (c, 2H), 2,54 (c, 3H), 2,39 (c, 3H); (output: 65,1%).

Example 187. Hydrochloride 7-(3,5-deferasirox)-1,2,3-trimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (t, 1H), 7,00 (d, 2H), 6,91 (t, 1H), for 6.81 (c, 1H), lower than the 5.37 (c, 2H), 4.00 points (c, 3H), 2,55 (c, 3H), 2,43 (c, 3H); (output: 75,6%).

Example 188. Hydrochloride of 1-(2-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.40 (t, 1H), 7,43 (m, 2H), 7,16 (m, 1H), for 6.81 (m, 2H), 6,46 (c, 2H), 6,03 (m, 1H), 5,61 (c, 2H), 5,16 (c, 2H), 2,60 (c, 3H), 2,39 (c, 3H); (output: 63,8%).

Example 189. Hydrochloride 7-(3,5-deferasirox)-1-(3,4-dimethoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 7,98 (d, 1H), to 7.61 (d, 1H), 7,01 (d, 2H), 6,91 (c, 4H), 6,82 (c, 2H), 5,71 (c, 2H), 5,64 (c, 2H), 3,81 (c, 3H), 2,34 (c, 3H), and 2.27 (c, 3H); (output: 72,5%).

Example 190. Hydrochloride 7-(3,5-deferasirox)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 7.92 (d, 1H), 7,56 (d, 1H), 7,38 (m, 1H), 7,21 (t, 1H), 6,97 (m, 2H), 6.75 in (t, 1H), return of 6.58 (d, 1H), from 6.22 (d, 1H), 5,78 (c, 2H), 5,67 (c, 2H), 3,89 (c, 3H), 2,25 (c, 3H), 2,17 (c, 3H); (output: 64,2%).

Example 191. Hydrochloride 7-(3,5-deferasirox)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (c, 1H), was 7.36 (m, 1H), 7,05 (m, 3H), for 6.81 (m, 2H), 6,56 (d, 2H), 5,63 (c, 2H), and 5.30 (c, 2H), 2,56 (c, 3H), 2,39 (c, 3H); (output: 58,4%).

Example 192. Hydrochloride of 1-(3-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (d, 1H), 7.23 percent (m, 1H), 6,847 (m, 3H), 6,72 (c, 1H), 6,61 (m, 2H), of 6.52 (m, 1H), 5.56mm (c, 2H), 5,19 (c, 2H), 2.63 in (c, 3H), 2.40 a (c, 3H); (yield: 85.4 percent).

Example 193. Hydrochloride 7-(3,5-deferasirox)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), 6,91 (m, 4H), only 6.64 (m, 4H), 5,54 (c, 2H), 5,24 (c, 2H), of 3.73 (c, 3H), 2,61 (c, 3H), 2,39 (c, 3H); (output: 65,3%).

Example 194. Hydrochloride 7-(3,5-deferasirox)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 7.97 (d, 1H), to 7.64 (d, 1H), 7,19 (t, 1H), 6.89 in (d, 1H), 6,78 (d, 1H), 6,56 (m, 2H), 6,46 (c, 2H), 5,76 (c, 2H), 5,68 (c, 2H), 3,76 (c, 3H), 2,35 (c, 3H), 2,31 (c, 3H); (output: 69,4%).

Example 195. Hydrochloride of 1-benzyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (d, 1H), 7,42 (m, 4H), to 6.80 (m, 4H), 6,55 (d, 1H), ceiling of 5.60 (c, 2H), 5.25 in (c, 2H), 2,62 (c, 3H), 2,45 (c, 3H); (yield: 80.9 per cent).

Example 196. Hydrochloride 7-(3,5-deferasirox)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (USS, 1H), 7,10 (m, 3H), 6,79 (m, 2H), 6,59 (m, 3H), 5.56mm (c, 2H), 5,22 (c, 2H), 2,59 (c, 3H), 2.40 a (c, 3H), 2,32 (c, 3H); (yield: 91.5 per cent).

Example 197. Hydrochloride of 1-(pyridine-2-ylmethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,33 (USS, 1H), 7,14 (m, 3H), 6.87 in (m, 2H), 6,54 (m, 3H), of 5.53 (c, 2H), 5,24 (c, 2H), 2.40 a (c, 3H), 2,32 (c, 3H); (yield: 85.4 percent).

Por the measures 198. Hydrochloride of 1-(pyridine-3-ylmethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) of 8.37 δ (USS, 1H), 8,01 (c, 1H), 7,14 (m, 2H), 6,94 (m, 2H), 6,32 (m, 3H), 5,54 (c, 2H), 5,35 (c, 2H), 2,39 (c, 3H), 2,28 (c, 3H); (output: 75,6%).

Example 199. Hydrochloride of 1-(2,2-dimethylaminoethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,45 (USS, 1H), 8,01 (c, 1H), 7,87 (m, 2H), 6,94 (d, 1H), 5,35 (c, 2H), 4,35 (d, 2H), 4,01 (d, 2H), 2,88 (c, 6H), 2,84 (m, 2H), 2,39 (c, 3H), 2,28 (c, 3H); (yield: 66.3 per cent).

Example 200. Hydrochloride of 2,3-dimethyl-1-(4-methylbenzyl)-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(4-Triftormetilfosfinov)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 4-triftormetilfosfinov alcohol has been specified in the title compound as yellow solid (yield: 89.5 per cent).

1H-NMR (CDCl3) δ 9,03 (c, 1H), 8,66 (d, 1H), 7,38 (m, 4H), 7,02 (d, 1H), from 5.29 (d, 1H).

Stage 2: 7-(4-Triftormetilfosfinov)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(4-triftormetilfosfinov)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 29.5 per cent).

1 H-NMR (CDCl3) δ of 8.28 (d, 1H), 8,01 (c, 1H), was 7.36 (m, 4H), to 6.57 (d, 1H), 5,20 (c, 2H), 2,41 (c, 3H), 2,31 (c, 3H).

Stage 3: Hydrochloride of 2,3-dimethyl-1-(4-methylbenzyl)-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(4-triftormetilfosfinov)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and 4-methylbenzylamine got mentioned in the title compound as white solids (yield: 88.6 per cent).

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,55 (d, 2H), 7,16 (m, 2H), 7,13 (d, 2H), for 6.81 (m, 1H), return of 6.58 (d, 2H), 5,55 (c, 2H), 5,32 (c, 2H), 2,61 (c, 3H), 2,38 (c, 3H), 2,35 (c, 3H).

Examples 201 to 208

The connections defined in the headers of examples 201-208, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-triftormetilfosfinov)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 200, and 3-methoxybenzylamine, 2-chlorobenzylchloride, iodata, 4-chlorobenzylchloride, (methyl bromide)cyclopropane, 4-methoxybenzaldehyde, 3-formanilide or 3,4-dichlorobenzaldehyde.

Example 201. Hydrochloride of 1-(3-methoxybenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (t, 1H), 7,55 (d, 2H), 7,18 (m, 3H), 6,83 (d, 2H), 6.22 per (c, 2H), 5,54 (c, 2H), and 5.30 (c, 2H), 3,70 (c, 3H), 2,60 (c, 3H), 2,38 (c, 3H); (output: 89,0%).

Example 202. Hydrochloride of 1-(2-x is orbenin)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (d, 1H), 7,54 (d, 2H), 7,37 (d, 1H), 7,11 (m, 3H), 6,83 (m, 2H), 6,03 (d, 1H), 5,61 (c, 2H), 5,26 (c, 2H), 2,62 (c, 3H), 2,37 (c, 3H); (output: 75,4%).

Example 203. Hydrochloride of 1-ethyl-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (d, 1H), of 7.75 (d, 2H), a 7.62 (d, 2H), 6.89 in (c, 1H), 5,48 (c, 2H), to 4.38 (m, 2H), 2,54 (c, 3H), 2,43 (c, 3H), of 1.33 (t, 3H); (output: 63,8%).

Example 204. Hydrochloride of 1-(4-Chlorobenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.37 (d, 1H), 7,60 (d, 2H), 7,38 (m, 2H), 7,24 (m, 2H), 6,86 (m, 1H), 6,60 (d, 2H), 5,50 (c, 2H), 5,31 (c, 2H), 2,60 (c, 3H), 2,37 (c, 3H); (output: an 85.2%).

Example 205. Hydrochloride of 1-cyclopropylmethyl-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,08 (d, 2H), to 7.99 (d, 1H), 7,37 (m, 2H), 6,45 (c, 1H), 5.25 in (c, 1H), 4,59 (m, 1H), to 4.41 (m, 1H), 4,15 (d, 1H), 2,53 (c, 3H), 2,47 (c, 3H), of 1.34 (m, 1H), 0,72 (d, 1H), and 0.61 (d, 1H), 0,35 (m, 2H); (output: 77,4%).

Example 206. Hydrochloride of 1-(4-methoxybenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (d, 1H), 7,58 (d, 2H), 6,94 (m, 3H), at 6.84 (m, 2H), 6,79 (m, 2H), 6,60 (d, 2H), 5,52 (c, 2H), from 5.29 (c, 2H), 3,78 (c, 3H), 2,60 (c, 3H), 2,38 (c, 3H); (output: 65,4%).

Example 207. Hydrochloride of 1-(3-terbisil)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ scored 8.38 (d, 1H), 7,56 (d, 2H), 7,15 (d, 2H), 7,032 (m, 3H), 6,83 (m, 1H), from 6.22 (m, 1H), 5,62 (c, 2H), 5,24 (c, 2H), 2,62 (c, 3H), 2,39 (c, 3H); (yield: 68.7 per cent).

Primer. Hydrochloride of 1-(3,4-dichlorobenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,40 (c, 1H), to 7.64 (d, 2H), 7,32 (m, 4H), 6,88 (c, 1H), 6,79 (c, 1H), gold 6.43 (d, 1H), 5,48 (c, 2H), 5,22 (c, 2H), 2,61 (c, 3H), 2,39 (c, 3H); (yield: 74.2 per cent).

Example 209. Hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(Pyridine-3-ylethoxy)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 3-pyridylcarbinol got mentioned in the title compound as yellow solid (yield: 78.5 per cent).

1H-NMR (CDCl3) δ 9,06 (c, 1H), 8,70 (c, 1H), 8,65 (m, 2H), 7,87 (m, 1H), 7,39 (m, 1H), 7,10 (d, 2H), 5,32 (c, 2H).

Stage 2: 2,3-Dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(pyridine-3-ylethoxy)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 18.4 per cent).

1H-NMR (CDCl3) a total of 8.74 δ (c, 1H), 8,64 (c, 1H), 8.30 to (c, 1H), 8,04 (USS, 1H), 7,79 (d, 1H), 7,35 (d, 1H), 6,63 (c, 1H), and 5.30 (c, 2H), 2.40 a (c, 3H), 2,31 (c, 3H).

Stage 3: the Hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used to study the 2 of example 33, except for using 2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and benzylbromide got mentioned in the title compound as white solids (yield: 78.4 per cent).

1H-NMR (DMSO-d6) δ 8,59 (c, 2H), of 8.37 (c, 1H), 7,78 (c, 1H), 7,53 (c, 1H), 7,21 (c, 1H), 7,10 (c, 3H), 6,64 (c, 2H), 5,57 (c, 2H), 5,47 (c, 2H), 2,25 (c, 3H), 2,14 (c, 3H).

Examples from 210 through 214

The connections defined in the headers of examples 210-214, were obtained using the same procedures that were used in stage 2 of example 33, using 2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 209, and 1-iodopropane, 1-iodine-2-methylpropane, allylbromide, 2-pomatoleios ether or (methyl bromide)CYCLOBUTANE.

Example 210. Hydrochloride of 2,3-dimethyl-1-propyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,72 (c, 1H), 8,55 (c, 1H), 8,27 (d, 1H), 8,08 (d, 1H), 7,53 (c, 1H), 7,15 (d, 1H), 5,43 (c, 2H), of 3.97 (t, 2H), 2,20 (c, 3H), 2.06 to (c, 3H), of 1.35 (m, 2H), 0,39 (t, 3H); (yield: 78.5 per cent).

Example 211. Hydrochloride of 1-isobutyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,75 (c, 1H), 8,58 (c, 1H), 8,31 (d, 1H), 8,10 (d, 1H), 7,56 (c, 1H), 7,18 (d, 1H), 5,44 (c, 2H), 3,86 (d, 2H), 2,22 (c, 3H), 2,10 (c, 3H), of 1.74 (m, 1H), 0,39 (d, 6H); (output: 69,8%).

Example 212. Hydrochloride of 1-allyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,92 (c, H), 8,79 (c, 1H), 8,51 (d, 1H), 8,31 (c, 1H), 7,80 (c, 1H), 7,37 (c, 1H), 5,97 (m, 1H), 5,370 (c, 2H), 5,08 (d, 1H), 5,01 (c, 2H), 4,56 (c, 1H), 2,50 (c, 3H), 2,32 (c, 3H); (output: 57,9%).

Example 213. Hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 9,00 (c, 1H), 8,84 (c, 1H), 8,49 (d, 1H), 8,43 (d, 1H), 7,88 (c, 1H), 7,37 (d, 1H), 5,71 (c, 2H), 4,49 (c, 2H), 3,50 (d, 2H), 3,12 (c, 3H), 2,44 (c, 3H), 2,31 (c, 3H); (yield: 78.4 per cent).

Example 214. Hydrochloride of 1-cyclobutylmethyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,99 (c, 1H), 8,81 (c, 1H), and 8.50 (d, 1H), of 8.37 (c, 1H), 7,82 (c, 1H), 7,39 (d, 1H), 5,69 (c, 2H), 4,33 (d, 2H), 2,61 (m, 1H), 2,44 (c, 3H), 2,30 (c, 3H), of 1.66 (m, 6H); (yield: 83.4%of).

Example 215. Hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(Pyridine-2-ylethoxy)-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 2-pyridylcarbinol got mentioned in the title compound as yellow solid (yield: 68,3%).

1H-NMR (CDCl3) δ 9,06 (c, 1H), 8,61 (m, 2H), 7,78 (m, 1H), to 7.64 (d, 1H), 7,31 (m, 1H), 7,15 (d, 1H), 5,41 (c, 2H).

Stage 2: 2,3-Dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-(pyridine-2-ylethoxy)-3-nitropyridine, Paul is obtained in stage 1, got mentioned in the title compound as white solids (yield: 21.5 per cent).

1H-NMR (CDCl3) δ 8,64 (c, 1+1H), compared to 8.26 (d, 1H), 7,73 (t, 1H), of 7.48 (d, 1H), 7,29 (c, 1H), 6,63 (d, 1H), 5.40 to (c, 2H), 2,43 (c, 3H), 2,33 (c, 3H).

Stage 3: the Hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and benzylbromide got mentioned in the title compound as white solids (yield: 78.4 per cent).

1H-NMR (DMSO-d6) δ 8,59 (c, 1H), of 8.47 (d, 1H), 7,78 (t, 1H), 7,42 (t, 1H), 7,31 (d, 1H), 7,24 (c, 3H), 7,19 (d, 1H), 6.89 in (c, 2H), 5,72 (c, 2H), 5,62 (c, 2H), 2.40 a (c, 3H), 2,33 (c, 3H).

Examples 216 and 217

The connections defined in the headers of examples 216 and 217, were obtained using the same procedures that were used in stage 2 of example 33, using 2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 215, and 1-iodopropane or 2-pomatoleios ether.

Example 216. Hydrochloride of 2,3-dimethyl-1-propyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,59 (c, 1H), scored 8.38 (d, 1H), of 7.90 (t, 1H), 7.62mm (d, 1H), 7,41 (c, 1H), 7,27 (d, 1H), 5,59 (c, 2H), is 4.21 (t, 2H), 2,37 (c, 3H), 2,22 (c, 3H), of 1.57 (m, 2H), and 0.61 (t, 3H); (output: 63,8%).

Example 217. Hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(pyridi the-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,65 (c, 1H), 8,44 (d, 1H), of 7.96 (t, 1H), to 7.67 (d, 1H), 7,47 (c, 1H), 7,32 (d, 1H), 5,69 (c, 2H), 4,55 (c, 2H), 3,60 (c, 2H), 3,19 (c, 3H), 2,45 (c, 3H), 2,29 (c, 3H); (yield: 79.8 per cent).

Example 218. 7-(4-Bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-Bromobenzylamine-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 4-bromobenzylamine alcohol has been specified in the title compound as yellow solid (yield: 78.9 per cent).

1H-NMR (CDCl3) δ 9,04 (c, 1H), to 8.62 (d, 1H), 7,56 (d, 2H), 7,34 (d, 2H),? 7.04 baby mortality (d, 1H), 5,26 (c, 2H).

Stage 2: 7-(4-Bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-bromobenzylamine-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 15.8 percent).

1H-NMR (CDCl3) δ of 8.28 (d, 1H), 8,21 (USS, 1H), 7,52 (d, 2H), 7,31 (d, 2H), 6,56 (d,1H), 5,16 (c, 2H), 2,39 (c, 3H), 2,30 (c, 3H).

Examples 219 to 230

The connections defined in the headers of examples 219-230, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 218, and benzylbromide, allylbromide-formanilide, 3-formanilide, 3-methylbenzylamine, 4-methylbenzylamine, 2-ftorangidridy, 3-chlorobenzenamine, (methyl bromide)CYCLOBUTANE, 1-iodine-2-methylpropane, 1-iodopropane or 2-methoxybenzylamine.

Example 219. Hydrochloride of 1-benzyl-7-(4-bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (t, 1H), 7,43 (d, 1H), 7,29 (m, 3H), 6,91 (d, 2H), for 6.81 (d, 1H), to 6.67 (d, 2H), 5,57 (c, 2H), 5,20 (c, 2H), 2,60 (c, 3H), 2,32 (c, 3H); (output: 48,9%).

Example 220. 1-Allyl-7-(4-bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (t, 1H), 7,60 (d, 2H), 7,33 (d, 2H), to 6.88 (d, 1H), 5,88 (m, 1H), 5,33 (c, 2H), 5,14 (d, 1H), 4,94 (d, 2H), 4,54 (d, 1H), 2,56 (c, 3H), 2,32 (c, 3H); (output: 58,8%).

Example 221. The hydrochloride of 7-(4-bromobenzylamine)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,47 (d, 2H), of 6.96 (m, 4H), 6.87 in (d, 1H), 6,63 (m, 2H), total of 5.21 (c, 2H), 5,23 (c, 2H), 2,59 (c, 3H), 2,37 (c, 3H); (output: 65,3%).

Example 222. The hydrochloride of 7-(4-bromobenzylamine)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (t, 1H), 7,47 (d, 2H), 7,22 (m, 1H), 7,01 (m, 3H), 6.90 to (d, 1H), 6,41 (t, 2H), of 5.53 (c, 2H), 5,22 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (output: 78,0%).

Example 223. The hydrochloride of 7-(4-bromobenzylamine)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (DMSO-d6) δ 8,29 (d, 1H), 7,31 (d, 2H), 7,06 (d, 1H), 6,92 (m, 3H), 6,85 (m, 1H), 6.48 in (c, 1H), 6,32 (d, 1H), 5.40 to (c, 2H), 5,27 (c, 2H), 2,19 (c, 3H), 2,12 (c, 3H), 1,99 (c, 3H); (output: 63,3%).

Example 224. Hydrochlorid-(4-bromobenzylamine)-2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,43 (d, 2H), 7,07 (d, 2H), 6,93 (d, 2H), PC 6.82 (d, 1H), return of 6.58 (d, 2H), of 5.53 (c, 2H), 5,22 (c, 2H), 2,59 (c, 3H), 2,37 (c, 3H), 2,32 (c, 3H); (yield: 78.9 per cent).

Example 225. The hydrochloride of 7-(4-bromobenzylamine)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (t, 1H), 7,43 (d, 2H), 7,30 (d, 1H), 7,03 (m, 2H), 6,92 (d, 2H), 6,83 (d, 1H), 6,23 (t, 1H), 5,61 (c, 2H), total of 5.21 (c, 2H), 2,60 (c, 3H), 2,38 (c, 3H); (output: 68,0%).

Example 226. The hydrochloride of 7-(4-bromobenzylamine)-1-(3-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (t, 1H), 7,49 (d, 1H), 7,27 (c, 1H), 7,20 (m, 1H), 6,98 (d, 2H), to 6.88 (d, 1H), of 6.71 (c, 1H), 6,46 (d, 1H), 5,54 (c, 2H), 5,24 (c, 2H), 2,60 (c, 3H), 2,33 (c, 3H); (yield: 68.8 per cent).

Example 227. The hydrochloride of 7-(4-bromobenzylamine)-1-cyclobutylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8.34 per (USS, 1H), 7,63 (d, 2H), 7,38 (d, 2H), to 6.88 (d, 1H), 5,34 (c, 2H), 4,30 (d, 2H), 2,54 (c, 3H), 2,38 (c, 3H), 1.77 in (m, 3H), of 1.66 (m, 4H); (yield: 55.4 per cent).

Example 228. The hydrochloride of 7-(4-bromobenzylamine)-1-isobutyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,39 (t, 1H), 7,63 (d, 2H), 7,38 (d, 2H), of 6.96 (d, 1H), lower than the 5.37 (c, 2H), Android 4.04 (d, 2H), 2,55 (c, 3H), 2,42 (c, 3H), of 1.81 (m, 1H), 0,71 (d, 6H); (output: 70,0%).

Example 229. The hydrochloride of 7-(4-bromobenzylamine)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ with 8.33 (t, 1H), to 7.61 (d, 2H), 7,38 (d, 2H), 7,01 (d, 1H), 5,38 (c, 2H), or 4.31 (t, 2H), 2,52 (c, 3H), 2,41 (c, 3H), 1,67 (m, 2H), 0.75 in (t, 3H); (yield: 65.5 per cent).

Example 230. The hydrochloride of 7-(4-bromobenzylamine)-1-(2-methoxime the ZIL)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,35 (t, 1H), 7,41 (d, 2H), 6,84 (m, 6H), 5,97 (d, 1H), 5,68 (c, 2H), 5,14 (c, 2H), 3.75 to (c, 3H), 2,60 (c, 3H), 2,25 (c, 3H); (output: 78,0%).

Example 231. Hydrochloride of 1-benzyl-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-Isopropylbenzylamine-3-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 4-chloro-3-nitropyridine obtained in stage 1 get 1, and 4-isopropylbenzyl alcohol has been specified in the title compound as white solids (yield: 67,8%).

1H-NMR (CDCl3) δ 9,02 (c, 1H), 8,59 (d, 1H), 7,37 (d, 2H), 7,28 (d, 2H), 7,07 (d, 1H), 5,28 (c, 2H), 2,90 (m, 1H), 1.26 in (d, 6H).

Stage 2: 7-(4-Isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-isopropylbenzylamine-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 25.8 per cent).

1H-NMR (CDCl3) δ 8,31 (d, 1H), 7,20 (m, 2H), 7,05 (d, 2H), PC 6.82 (d, 1H), 5,23 (c, 2H), 2,90 (m, 1H), 2,54 (c, 3H), 2,35 (c, 3H), of 1.24 (d, 6H).

Stage 3: the Hydrochloride of 1-benzyl-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-p is Rolo[3,2-b]pyridine, obtained in stage 2, and benzylbromide got mentioned in the title compound as white solids (yield: 78.5 per cent).

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,27 (m, 3H), 7,16 (d, 2H), 7,00 (d, 2H), 6,83 (d, 1H), 6,67 (m, 2H), 5,57 (c, 2H), 5,22 (c, 2H), 2.91 in (m, 1H), 2,59 (c, 3H), 2,37 (c, 3H), 1.26 in (d, 6H).

Examples 232 240

The connections defined in the headers of examples 232-240, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 231, 4-formanilide, 3-methylbenzylamine, 3-formanilide, 4-methylbenzylamine, 2-methoxybenzylamine, 3-chlorobenzamide, 2-ftorangidridy, (methyl bromide)CYCLOBUTANE or 1-iodopropane.

Example 232. Hydrochloride of 1-(4-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,20 (m, 2H), 7,05 (d, 2H), 6,93 (t, 2H), 6,86 (d, 1H), 6,62 (m, 2H), 5,52 (c, 2H), 5,23 (c, 2H), 2,93 (m, 1H), 2,58 (c, 3H), 2,37 (c, 3H), of 1.27 (d, 6H); (yield: 85.4 percent).

Example 233. The hydrochloride of 7-(4-isopropylbenzylamine)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,17 (m, 3H), 7,10 (d, 1H), 7,02 (d, 2H), 6,83 (d, 1H), 6,50 (c, 1H), 6,47 (d, 1H), 5,55 (c, 2H), 5,24 (c, 2H), 2,92 (m, 1H), 2,59 (c, 3H), 2,37 (c, 3H), 2.26 and (c, 3H), 1.26 in (d, 6H); (yield: 65.7 per cent).

Example 234. Hydrochloride of 1-(3-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridi is and

1H-NMR (CDCl3) δ 8,35 (t, 1H), 7,19 (m, 3H), 7,01 (m, 3H), 6,86 (d, 1H), 6,39 (m, 2H), of 5.53 (c, 2H), total of 5.21 (c, 2H), 2,92 (m, 1H), 2,59 (c, 3H), 2,37 (c, 3H), of 1.25 (d, 6H); (yield: 78.4 per cent).

Example 235. The hydrochloride of 7-(4-isopropylbenzylamine)-2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,17 (d, 2H), 7,07 (d, 2H), 7,01 (d, 2H), 6,83 (d, 1H), 6,59 (d, 2H), 5,54 (c, 2H), 5,24 (c, 2H), 2,92 (m, 1H), 2,58 (c, 3H), 2,37 (c, 3H), 2,33 (c, 3H), of 1.28 (d, 6H); (yield: 84.2 per cent).

Example 236. The hydrochloride of 7-(4-isopropylbenzyl)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,29 (m, 1H), 7,12 (d, 2H), 6.89 in (m, 3H), 6,79 (m, 2H), 6,01 (d, 1H), 5,55 (c, 2H), 5,18 (c, 2H), of 3.73 (c, 3H), 2,89 (m, 1H), 2,59 (c, 3H), 2,33 (c, 3H), of 1.24 (d, 6H); (yield: 65.7 per cent).

Example 237. Hydrochloride of 1-(3-Chlorobenzyl)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ at 8.36 (t, 1H), 7,20 (m, 2H), 7,05 (d, 2H), 6,93 (t, 2H), 6,86 (d, 1H), 6,62 (m, 2H), 5,52 (c, 2H), 5,23 (c, 2H), 2.91 in (m, 1H), 2,58 (c, 3H), 2,37 (c, 3H), of 1.27 (d, 6H); (output: 74,5%).

Example 238. Hydrochloride of 1-(2-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ a 8.34 (t, 1H), 7,35-of 6.96 (m, 7H), at 6.84 (d, 1H), 6,23 (t, 1H), 5,63 (c, 2H), 5,23 (c, 2H), 2,88 (m, 1H), 2,59 (c, 3H), 2,36 (c, 3H), of 1.25 (d, 6H); (output: 63,8%).

Example 239. Hydrochloride of 1-cyclobutylmethyl-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,40 (d, 2H), 7,33 (d, 2H), to 6.88 (d, 1H), 5,34 (c, 2H), 4,29 (d, 1H), 2,98 (m, 1H), 2.63 in (m, 1H), 2,53 (c,3H), 2,40 (c, 3H), 1.77 in-and 1.56 (m, 7H), of 1.28 (d, 6H); (output: 81,0%).

Example 240. The hydrochloride of 7-(4-isopropylbenzyl)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,32 (t, 1H), 7,38 (d, 2H), 7,30 (m, 2H), to 6.88 (d, 1H), 5,33 (c, 2H), 4,20 (t, 2H), 2,97 (m, 1H), 2,53 (s, 3H), 2,39 (c, 3H), by 1.68 (m, 2H), 1.28 (in d, 6H), of 0.71 (t, 3H); (yield: 78.5 per cent).

Example 241. Hydrochloride of 1-benzyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-Pertenece-3-nitropyridine

Sodium hydride (7.2 g, 180,4 mmol) was slowly added at 0°C. to a solution of 4-terfenol (17.11 per bbl g, 152,6 mmol) in 200 ml of N,N-dimethylformamide, and then the reaction mixture was stirred for 30 minutes at room temperature. To the reaction mixture at 0°C was added 4-chloro-3-nitropyridine (22,0 g, 138,8 mmol)obtained in stage 1 get 1, and the mixture was stirred for 1 hour at room temperature, diluted with 200 ml of ethyl acetate, and then washed three times with 200 ml of water. The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain specified in the title compounds as a pale yellow solid (25,2 g, with 76.8%).

1H-NMR (CDCl3) δ 9,13 (c, 1H), to 8.57 (d, 1H), 7,15 (m, 4H), 6,76 (d, 1H).

Stage 2: 7-(4-Pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures as in stage 1 of example 33, except for using 4-perfino the C-3-nitropyridine, received at stage 1 has been specified in the title compound as white solids (yield: 18.5 per cent).

1H-NMR (CDCl3) δ by 8.22 (d, 1H), 7,99 (USS, 1H), was 7.08 (m, 4H), 6,38 (d, 1H), 2,55 (c, 3H), 2,32 (c, 3H).

Stage 3: the Hydrochloride of 1-benzyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and benzylbromide got mentioned in the title compound as white solids (yield: 63.8 per cent).

1H-NMR (CDCl3) δ of 8.27 (t, 1H), 7,31 (m, 3H), 7,13 (t, 2H), 6.87 in (m, 4H), 6,44 (d, 1H), 5,71 (c, 2H), 2,64 (c, 3H), 2,47 (c, 3H).

Examples 242 and 243

The connections defined in the headers of examples 242 and 243, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 241, and allylbromide or (methyl bromide)CYCLOBUTANE.

Example 242. Hydrochloride of 1-allyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.25 (t, 1H), 7,20 for 7.12 (m, 4H), 6,47 (d, 1H), 6,04 (m, 1H), 5,22 (d, 1H), 5,10 (d, 2H), 4.72 in (d, 1H), 2,61 (c, 3H), 2,46 (c, 3H); (yield: 73.3 per cent).

Example 243. Hydrochloride of 1-cyclobutylmethyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ by 8.22 (t, 1H), 7.23 percent-7,17 (m, 4H, 6.42 per (d, 1H), 4,50 (d, 2H), 2,74 (m, 1H), 2,58 (c, 3H), 2,48 (c, 3H), 1.91 a to 1.76 (m, 7H); (yield: 83.4%of).

Example 244. Hydrochloride tert-butyl ether (2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

Tert-butyl ether (2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid (20 mg, 0.089 mmol), obtained in the obtaining 3, tert-piperonyl potassium (10,6 mg, 0,143 mmol)and a catalytic amount of 18-crown-6 was added to dry tetrahydrofuran (2 ml). To the reaction mixture were added 1-iodopropane (0,089 ml, 0,130 mmol) and the mixture was then stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methylene chloride/methanol=10/10/1, (about./about./vol.), was dissolved in ethyl acetate (1 ml)and then saturated with gaseous hydrogen chloride. The resulting precipitate was filtered to obtain specified in the title compounds as white solids (16,3 mg, 58.6 per cent).

1H-NMR (CDCl3) δ 8,32 (d, 1H), 7,38 (m, 1H), 7,15 (d, 2H), 7,03 (d, 2H), from 5.29 (m, 2H), 4,35 (m, 2H), 3,40 (m, 2H), and 3.16 (c, 3H), 2,53 (c, 3H), 2,48 (c, 3H), 1.41 to (c, 9H).

Examples 245 253

The connections defined in the headers of examples 245-253, were obtained using the same procedures used in example 244, using tert-butyl ether (2,3-dimethyl-1H-pyrrol the[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid, received in receiving 3, and 2-pomatoleios ether (methyl bromide)cyclopropane, iodata, benzylbromide, 3-formanilide, 3-methoxybenzylamine, 4-methoxybenzaldehyde, 3-methylbenzylamine or 4-methylbenzylamine.

Example 245. Hydrochloride tert-butyl ether [2,3-dimethyl-1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,32 (d, 1H), 7,38 (m, 1H), 7,15 (d, 2H), 7,03 (d, 2H), from 5.29 (m, 2H), 4,35 (m, 2H), 3,40 (m, 2H), and 3.16 (c, 3H), 2,53 (c, 3H), 2,48 (c, 3H), 1.41 to (c, 9H); (yield: 75.8 per cent).

Example 246. Hydrochloride tert-butyl ether (2,3-dimethyl-1-cyclopropylmethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ of 8.27 (t, 1H), 7,06 (m, 2H), 6,98 (m, 2H), of 6.68 (m, 1H), 5,32 (m, 2H), 4,20 (m, 2H), 2,64 (c, 3H), 2,55 (c, 3H), 1,42 (c, 9H), of 0.97 (m, 1H), 0,55 (m, 2H), and 0.28 (m, 2H); (output: 63,8%).

Example 247. Hydrochloride tert-butyl ether (2,3-dimethyl-1-ethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,29 (m, 1H), 7,11 (t, 2H), 6,99 (t, 2H), 6,70 (m, 1H), 5,28 (m, 2H), 4,28 (m, 2H), 4,17 (m, 2H), 2,62 (c, 3H), 2.50 each (c, 3H), 1,34 (c, 9H), of 1.18 (t, 3H); (output: 58,4%).

Example 248. Hydrochloride tert-butyl ester 1-benzyl-(2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,30 (m, 2H), 7,02 (m, 2H), 6,98 (m, 2H), 6,62 (m, 3H), of 5.45 (m, 4H), 2,62 (c, 3H), 2,38 (c, 3H), 1.41 to (c, 9H); (output: 75,0%).

Example 249. Hydrochl the reed tert-butyl ether [2,3-dimethyl-1-(3-terbisil)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,35 (t, 1H), 7,00 (m, 3H), 6,91 (m, 2H), 6,70 (m, 2H), 6,37 (m, 2H), 5,48 (m, 4H), 2,67 (c, 3H), 2,36 (c, 3H), 1.41 to (c, 9H); (output: 63,3%).

Example 250. Hydrochloride tert-butyl ether [2,3-dimethyl-1-(3-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,22 (m, 1H), 7,02 (m, 2H), 6,92 (m, 2H), 6,80 (d, 1H), 6,66 (m, 1H), 6,17 (c, 2H), 5,44 (m, 2H), 4,96 (USS, 2H), of 3.73 (c, 3H), 2,66 (c, 3H), 2,38 (c, 3H), 1,34 (c, 9H); (output; 58,8%).

Example 251. Hydrochloride tert-butyl ether [2,3-dimethyl-1-(4-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,03 (m, 2H), 6,99 (m, 2H), for 6.81 (m, 3H), 6,55 (d, 2H), 5,43 (m, 4H), 3,79 (c, 3H), 2,55 (c, 3H), 2.40 a (c, 3H), 1,30 (c, 9H); (output: 75,0%).

Example 252. Hydrochloride tert-butyl ether [2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8,31 (t, 1H), 7,18 (m, 1H), 7,15 (m, 1H), to 7.09 (m, 2H), of 6.96 (m, 2H), only 6.64 (m, 1H), 6,44 (c, 1H), 6,37 (m, 1H), 5,50 (m, 4H), 2.63 in (c, 3H), 2,41 (c, 3H), 2,24 (c, 3H), 1,31 (c, 9H); (output: 63,8%).

Example 253. Hydrochloride tert-butyl ether [2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid

1H-NMR (CDCl3) δ 8.30 to (t, 1H), to 7.09 (d, 2H), 7,02 (m, 3H), 6,91 (t, 2H), only 6.64 (d, 2H), of 5.45 (m, 4H), 2,56 (c, 3H), 2,41 (c, 3H), 2,34 (c, 3H), 1,16 (c, 9H); (output: 61,0%).

Example 254. The hydrochloride of N-(1-allyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbesall is on

Stage 1: Hydrochloride tert-butyl methyl ether (1-allyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid

In accordance with the same procedures used in example 244, except for using tert-butyl ether (2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid, obtained in the obtaining 3, and allylbromide got mentioned in the title compound as white solids (yield: 88.6 per cent). The product was used in subsequent reactions without further purification.

Stage 2: the Hydrochloride of N-(1-allyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

A solution of the hydrochloride tert-butyl methyl ether (1-allyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid (101,3 mg)obtained in stage 1, in ethyl acetate (10 ml) was saturated with gaseous hydrogen chloride, and then stirred for 1 hour at room temperature. The resulting precipitate was filtered and then dried to obtain specified in the title compounds as white solids (35,3 mg, 44.1 per cent).

1H-NMR (CDCl3) δ to $ 7.91 (t, 1H), 7,11 (m, 2H), 6.48 in (c, 1H), 6.48 in (m, 1H), 6.35mm (m, 1H), 6,11 (m, 1H), 5,26 (d, 1H), of 5.05 (c, 2H), 4,71 (d, 1H), 4,56 (d, 2H), 2,42 (c, 3H), 2,28 (c, 3H).

Examples with 255 on 263

The connections defined in the headers of examples 255-263, were obtained using the same procedures that you used the example 244 and/or stage 2 of example 254, using tert-butyl ether (2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid, obtained in the obtaining 3, and (methyl bromide)cyclopropane, 2-pomatoleios ether, 3-methoxybenzylamine, 4-methoxybenzylamine, iodata, 1-iodopropane, benzylbromide, 3-formanilide or 4-methylbenzylamine.

Example 255. The hydrochloride of N-(1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ 7,87 (t, 1H), 7,38 (m, 2H), was 7.08 (t, 2H), 6,59 (c, 1H), 6,27 (d, 1H), 4,63 (d, 2H), 4,39 (d, 2H), 2,37 (c, 3H), 2,32 (c, 3H), 1.04 million (m, 1H), 0,54 (m, 2H), 0,24 (m, 2H); (output: 53,8%).

Example 256. The hydrochloride of N-[1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ of 8.04 (t, 1H), 7,71 (t, 1H), 7,34 (m, 2H), 7,10 (t, 2H), 6,40 (d, 1H), 4,49 (d, 2H), 4,39 (t, 2H, in), 3.75 (t, 2H), 3,19 (c, 3H), 2,47 (c, 3H), 2,35 (c, 3H); (output: 48,3%).

Example 257. The hydrochloride of N-[1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ 8,02 (c, 1H), 7,20 (m, 1H), 6,95 (t, 2H), 6,85 (m, 2H), 6,37 (d, 2H), 6,25 (c, 1H), ceiling of 5.60 (c, 1H), 5,49 (c, 2H), 4,27 (c, 2H), 3,65 (c, 3H), 2,53 (c, 3H), 2.40 a (c, 3H); (output: 55,1%).

Example 258. The hydrochloride of N-[1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ 7,94 (c, 1H), 6,93 (t, 2H), 6,85 (m, 2H), 6,76 (c, 3H), 6,18 (c, 1H), of 5.89 (c, 1H), 5,51 (c, 2H), 4,29 (c, 2H), 3,78 (c, 3H), of 2.51 (c, 3H), 2.40 a (c, 3H); (output: 44,2%).

Example 259. The hydrochloride of N-(1-the Teal-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) to 7.77 δ (c, 1H), 7,34 (c, 2H), 7,03 (t, 2H), 6.87 in (c, 1H), to 6.19 (c, 1H), 4,66 (c, 2H), to 4.52 (c, 2H), 2,35 (c, 3H), 2,34 (c, 3H), of 1.28 (t, 3H); (output: 65,3%).

Example 260. The hydrochloride of N-(2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ a 7.85 (t, 1H), was 7.36 (m, 2H), 7,07 (t, 2H), 6,36 (c, 1H), 6,21 (d, 1H), 4,60 (d, 2H), 4,30 (t, 2H), 2,38 (c, 3H), 2,33 (c, 3H), 1,72 (m, 2H), from 0.84 (t, 3H); (yield: 70.8 per cent).

Example 261. The hydrochloride of N-(1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ 8,00 (t, 1H), 7,33 (m, 2H), 6,93 (t, 2H), for 6.81 (m, 4H), 6,23 (d, 1H), ceiling of 5.60 (m, 1H), of 5.53 (c, 2H), 4.26 deaths (d, 2H), 2,54 (c, 3H), 2.40 a (c, 3H); (yield: 89.3 per cent).

Example 262. The hydrochloride of N-[1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ 7,88 (c, 1H), 7,21 (m, 1H), 6,99 (t, 1H), 6,91 (t, 2H), 6,83 (m, 1H), 6,65 (d, 1H), 6,50 (d, 1H), 6,23 (c, 1H), 6,14 (c, 1H), 5,70 (c, 2H), 4,35 (c, 2H), 2.49 USD (c, 3H), 2,39 (c, 3H); (output: 77,5%).

Example 263. The hydrochloride of N-[1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ 7,97 (c, 1H), 7,07 (d, 2H), 6,92 (t, 2H), for 6.81 (d, 2H), 6.73 x (d, 2H), 6,20 (c, 1H), 5,75 (c, 1H), 5,51 (c, 2H), 4,27 (c, 2H), 2,53 (c, 3H), 2.40 a (c, 3H), 2,34 (c, 3H); (output: 69,3%).

Example 264. Hydrochloride of 1-benzyl-7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine

Step 1: 2,3-Dimethyl-4-nitropyridine-N-oxide

30% hydrogen Peroxide (100 ml) was added to a solution of 2,3-lutidine (2 g) in 50 ml of acetic acid, which peremeshivayu for 12 hours at 90°C, and then the reaction mixture was concentrated under reduced pressure. The resulting residue was added to a mixture (30 ml) of concentrated sulfuric acid and nitric acid (7:3). The reaction mixture was heated under reflux for 3.5 hours, cooled to room temperature and then added to ice water. The reaction mixture was podslushivaet the sodium hydroxide solution was extracted with methylene chloride, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was recrystallized with ethanol to obtain 2.4 g specified in the title compounds as a pale yellow solid.

Stage 2: 2,3-Dimethyl-4-nitropyridine

2,3-Dimethyl-4-nitropyridine-N-oxide (75,6 g, 0.45 mol), obtained in stage 1, was dissolved in 300 ml of methylene chloride. The solution for 30 minutes at -15°C To -20°C was slowly added a solution of trichloride phosphorus (44 ml) in methylene chloride (60 ml). The reaction mixture was stirred for 15 minutes at the same temperature and further stirred for 15 minutes at room temperature. The reaction mixture was cooled to -78°C. To the reaction mixture were added 50 ml of water and the mixture was neutralized with sodium hydroxide solution, and then extracted with methylene chloride. The separated organic layer was dried with anhydrous sulfate m is fester and then concentrated under reduced pressure to obtain specified in the title compounds as a pale yellow solid (65 g, 95%).

1H-NMR (CDCl3) δ 2,43 (c, 3H), 2,66 (c, 3H), 7,43 (d, 1H), 8,55 (d, 1H).

Stage 3: 2,3-Dimethyl-4-hydroxy-5-nitropyridine

Anhydrous potassium acetate (49 g, 0.5 mol) was added to a solution of 2,3-dimethyl-4-nitropyridine (45.6 g, 0.3 mol), obtained in stage 2, 300 ml of acetic anhydride and then heated under reflux with stirring for 16 hours. The reaction mixture was cooled to room temperature, and then thereto was added 400 ml of anhydrous ether. The reaction mixture was stirred for 1 hour, filtered through celite, and then concentrated under reduced pressure to obtain 4-acetoxy-2,3-dimethylpyridine (45 g, 91%). The resulting residue was added to 250 ml of water, was heated under reflux with stirring for 4 hours and then left overnight at room temperature. The reaction mixture was concentrated under reduced pressure to get a 32.6 g of 2,3-dimethyl-4-hydroxypyridine in liquid form. The liquid product was dissolved in 120 ml of concentrated sulfuric acid and heated to 60°C. To the reaction mixture for 45 minutes was slowly added a mixture of 90% nitric acid (40 ml) and sulfuric acid (30 ml) maintaining the temperature at 60°C-65°C. the Reaction mixture was heated for 2 hours at 65°C, then for 30 minutes at 75°C. the Reaction mixture was cooled to room temperature and C is added to the ice water. The resulting solution was brought to pH 5-6 with ammonium hydroxide to obtain a pale yellow solid. The resulting solid was filtered, washed with cold water and then dried at 80°C-90°C To produce 34,5 g specified in the connection header.

1H-NMR (CDCl3) δ 2,54 (c, 3H), 2,87 (c, 3H), 9,35 (c, 1H).

Stage 4: 2,3-Dimethyl-4-chloro-5-nitropyridine

2,3-Dimethyl-4-hydroxy-5-nitropyridine (26,8 g, 0.16 mol) obtained in stage 3, was added to 85 ml of phosphorus oxychloride. To the reaction mixture was added pentachloride phosphorus (33,3 g, 0.16 mol) and the mixture was then heated under reflux with stirring for 2 hours. The reaction mixture was left overnight at room temperature, added to ice water, brought to pH 5 28% ammonium hydroxide, and then was extracted with ether. The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated to obtain 28,3 g specified in the connection header.

1H-NMR (CDCl3) δ 2,47 (c, 3H), 2,66 (c, 3H), 8,77 (c, 1H).

Stage 5: 4-(4-Forbindelse)-2,3-dimethyl-5-nitropyridine

According to the same procedures that were used in obtaining the 2, except for using 2,3-dimethyl-4-chloro-5-nitropyridine (1.0 g, are 5.36 mmol)obtained in stage 4, have been specified in the title compound as a pale yellow oil (yield: 85.4 percent).

1H-NMR (CDCl3) δ 8,80 (s, 1H), 7,43 (m, 2H),? 7.04 baby mortality (m, 2H), 4,99 (s, 2H), has 2.56 (s, 3H), 2,19 (s, 3H).

Stage 6: 7-(4-Forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 1 of example 33, except for using 4-(4-forbindelse)-2,3-dimethyl-5-nitropyridine obtained at stage 5, has been specified in the title compound as white solids (yield: 23.4 per cent).

1H-NMR (CDCl3) δ 7,31 (m, 2H), 6,67 (m, 2H), 5,48 (c, 2H), 4,78 (c, 2H), 3.04 from (c, 3H), 2,70 (c, 3H), 2,33 (c, 3H), 2,25 (c, 3H).

Stage 7: the Hydrochloride of 1-benzyl-7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 6 has been specified in the title compound as white solids (yield: 85.1%)are.

1H-NMR (CDCl3) δ 7,27 (m, 3H), to 7.09 (m, 4H), to 6.67 (m, 2H), 5,499 (c, 2H), 4,77 (c, 2H), 3,05 (c, 3H), 2,69 (c, 3H), 2,32 (c, 3H), 2,28 (c, 3H).

Examples 265 and 266

The connections defined in the headers of examples 265 and 266 were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 6 of example 264, and 1-iodopropane or 2-pomatoleios ether.

Example 265 Hydrochloride 1-propyl-7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 7,41 (m, 2H), 7,14 (m, 2H), 5,07 (c, 2H), was 4.02 (t, 2H), 3,03 (c, 3H), 2.63 in (c, 3H), 2,38 (c, 3H), 2,34 (c, 3H, 0,18 (m, 2H), 0,72 (t, 3H); (output: 66,4%).

Example 266. The hydrochloride of 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 7,39 (m, 2H), 7,15 (m, 2H), 5,11 (c, 2H), 4,29 (c, 2H), 3,47 (c, 2H), and 3.16 (c, 3H), 3.04 from (c, 3H), 2,64 (c, 3H), 2,41 (c, 3H), 2,36 (c, 3H); (output: 77,4%).

Example 267. The hydrochloride of N-(1-allyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

Step 1: tert-Butyl ether (4-terbisil)-(2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)carbamino acid

In accordance with the same procedures that were used in obtaining 3, except for using 2,3-dimethyl-4-chloro-5-nitropyridine obtained in stage 4 of example 264, and 4-forbindelsen got mentioned in the title compound as white solids (yield: 12.4 per cent).

1H-NMR (CDCl3) δ 8,31 (d, 1H), 8,12 (c, 1H), 7,40 (m, 1H), 7,18 (d, 2H), to 7.09 (d, 2H), and 3.16 (c, 3H), 2,53 (c, 3H), 2,48 (c, 3H), 1.41 to (c, 9H).

Stage 2: the Hydrochloride of N-(1-allyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

In accordance with the same procedures used in example 244 and/or in stage 2 of example 254, except for using tert-butyl ester (4-terbisil)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)carbamino acid, obtained in stage 1, and allylbromide floor is made is specified in the title compound as white solids (yield: 58.5 per cent).

1H-NMR (CDCl3) δ 7,06 (t, 2H), of 6.96 (t, 2H), 5,77 (m, 1H), 5,12 (m, 2H), 4,704 (m, 3H), or 4.31 (m, 1H), 2.95 and (c, 3H), 2,68 (c, 3H), 2.40 a (c, 3H), 1,67 (c, 3H).

Examples from 268 in 271

The connections defined in the headers of examples 268-271, were obtained using the same procedures used in example 244 and/or in stage 2 of example 254, using tert-butyl ester (4-terbisil)-(2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)carbamino acid, obtained in stage 1 of example 267, and benzylbromide, (methyl bromide)cyclopropane, 1-iodopropane or 2-pomatoleios ether.

Example 268. The hydrochloride of N-(1-benzyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ 7,56 (m, 4H), from 7.24 (m, 2H), was 7.08 (t, 1H), 6,94 (t, 1H), 6,76 (d, 1H), 5,52 (d, 1H), 5,24 (d, 1H), 5,02 (d, 1H), 4,18 (d, 1H), 2,90 (c, 3H), 2,62 (c, 3H), 2,30 (c, 3H), 1.70 to (c, 3H); (output: 75,6%).

Example 269. The hydrochloride of N-(1-cyclopropylmethyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ 7,01 (t, 2H), 6,94 (t, 2H), 5,22 (d, 1H), 4,19 (m, 2H), 3,86 (m, 2H), 2,88 (c, 3H), 2,69 (c, 3H), 2.49 USD (c, 3H), 1,65 (c, 3H), of 0.97 (m, 1H), 0,53 (m, 1H), 0,44 (m, 1H), 0,25 (USS, 1H); (yield: 45.9 per cent).

Example 270. The hydrochloride of N-(1-propyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen

1H-NMR (CDCl3) δ 7.03 is (t, 2H), 6,95 (t, 2H), 5,19 (d, 1H), 4,27 (d, 1H), a 4.03 (m, 1H), 3,90 (m, 1H), 2.95 and (c, 3H), 2,67 (c, 3H), 2,45 (c, 3H), 1,67 (c, 3H), of 1.55 (m, 2H), from 0.88 (t, 3H); (yield: 74.1 per cent).

Example 271. The hydrochloride of N-[1-(2-metakit the l)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen

1H-NMR (CDCl3) δ 7.03 is (d, 2H), 6,94 (t, 2H), 5,20 (d, 1H), 4.26 deaths (d, 2H), 4,21 (d, 1H), 3,47 (d, 2H), 3.15 in (c, 3H), 2,92 (c, 3H), 2,66 (c, 3H), 2,47 (c, 3H), 1,63 (c, 3H); (output: 65,3%).

Example 272. 6-Bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 3-Bromo-5-nitropyridine-4-ol

4-Hydroxy-3-nitropyridine (40 g, 0,285 mol) was added to 200 ml of water, and then back at the room temperature was slowly added bromine (18,44 ml, 0.36 mol). The reaction mixture was stirred under heating for 2 hours at 50°C and then cooled to room temperature. The resulting residue was filtered off, washed with water and then dried to obtain specified in the title compounds as a pale yellow solid (49,8 g, 87.8 per cent). The product was used in the next stage without additional purification.

Stage 2: 3-Bromo-4-chloro-5-nitropyridine

3-Bromo-5-nitropyridine-4-ol (49,8 g, 0,227 mol), obtained in stage 1, was slowly added at 0°C to 200 ml of trichloride phosphorus. At the same temperature there was slowly added N,N-diethylaniline (34,65 ml, 0,227 mol). The reaction mixture was heated under reflux with stirring for 2 hours, and then concentrated under reduced pressure. The resulting residue was added to ice water, and then was extracted with 300 ml of ether. The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated, propanganda pressure, giving 32,4 g specified in the title compounds as a pale yellow solid. The product was used in the next stage without additional purification.

Stage 3: 3-Bromo-4-(4-forbindelse)-5-nitropyridine

In accordance with the same procedures that were used in obtaining the 2, except for using 3-bromo-4-chloro-5-nitropyridine (1.0 g, is 4.21 mmol), obtained in stage 2, has been specified in the title compound as white solids (yield: 78.3%of).

1H-NMR (CDCl3) δ 8,75 (c, 1H), compared to 8.26 (c, 1H), 7,43 (m, 2H),? 7.04 baby mortality (m, 2H), 5,04 (c, 2H).

Stage 4: 6-Bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 1 of example 33, except for using 3-bromo-4-(4-forbindelse)-5-nitropyridine (1.28 g, 3,91 mmol), obtained in stage 3, has been specified in the title compound as white solids (yield: 18.3 percent).

1H-NMR (CDCl3) δ 8,43 (c, 1H), 7,71 (c, 1H), 7,40 (m, 2H), 7,06 (m, 2H), 5,22 (c, 2H), 2,30 (c, 3H), 2,24 (c, 3H).

Examples 273, 275

The connections defined in the headers of examples 273-275, were obtained using the same procedures that were used in stage 2 of example 33, using 6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 4 of example 272, and benzylbromide, 1-iodopropane or 2-pomatoleios ether.

When the EP 273. Hydrochloride of 1-benzyl-6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,66 (c, 1H), 7,31 (m, 3H), 7,12 (m, 2H), 7,01 (t, 2H), 6,65 (USS, 2H), 5,50 (c, 2H), 5,11 (c, 2H), 2,61 (c, 3H), 2,11 (c, 3H); (output: 45,3%).

Example 274. The hydrochloride of 6-bromo-7-(4-forbindelse)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,60 (c, 1H), 7,45 (m, 2H), 7,14 (t, 2H), 5,44 (c, 2H), 4,01 (t, 2H), 2,55 (c, 3H), 2,41 (c, 3H), of 1.59 (m, 2H), 0,70 (t, 3H); (output: 65,3%).

Example 275. The hydrochloride of 6-bromo-7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,60 (c, 1H), 7,44 (m, 2H), 7,14 (t, 2H), 5,47 (c, 2H), 4,28 (t, 2H), 3,44 (t, 2H), 3,17 (c, 3H), 2,55 (c, 3H), 2.40 a (c, 3H); (output, with 45.8%).

Example 276. 1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Hydrochloride of 1-benzyl-6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in example 273, neutralized with a saturated solution of sodium carbonate to obtain 1-benzyl-6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (1.4 g, 3,18 mmol). A solution of 1-benzyl-6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine (1.4 g, 3,18 mmol) and copper cyanide (I) (700 mg, 7,52 mmol) in anhydrous N,N-dimethylformamide (30 ml) was heated under reflux for 48 hours, and then cooled to room temperature. To the reaction mixture were added ethyl acetate and the mixture is then filtered to remove n the soluble solids. To the resulting solution was added water and the solution was then extracted with ethyl acetate. The resulting organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methanol=10/1, (about./vol.), giving 278 mg specified in the title compound as a white solid.

1H-NMR (CDCl3) δ 8,54 (c, 1H), 7,28 (m, 3H), 7,11 (m, 2H), 7,05 (t, 2H), 6,45 (c, 2H), 5,43 (c, 2H), total of 5.21 (c, 2H), 2,53 (c, 3H), 2,12 (c, 3H).

Example 277. 1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carboxamide

1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (500 mg, of 1.30 mmol)obtained in example 276, diluted with a mixture of ethanol (8 ml) and water (2 ml). To the reaction mixture was added potassium hydroxide (650 mg, 13,0 mmol) and the mixture was then heated under reflux for 2 hours. To the reaction mixture were added water and the mixture was then extracted with ethyl acetate. The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methanol=10/1, (about./about.)) to obtain 350 mg specified in the title compound as a white solid.

1H-NMR (CDCl3) δ 8,32 (c, 1H), 7,33(m, 3H), 7,21 (m, 2H), 7,12 (t, 2H), 6.35mm (c, 2H), 5,43 (c, 2H), total of 5.21 (c, 2H), 4,01 (USS, 2H), 2,41 (c, 3H), 2.23 to (c, 3H).

Example 278. The hydrochloride of 7-(4-forfinal)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

Stage 1: 4-(4-Forfinal)-3-nitropyridine

4-Chloro-3-nitropyridine (3 g, to 18.9 mmol), obtained in stage 1 get 1, 4-ftorhinolonovy acid (2.9 g, 20,79 mmol), tetrakis(triphenylphosphine)palladium(0) (2.1 g, 1,89 mmol) and potassium carbonate (7.8 g, of 56.7 mmol) suspended in 120 ml of 1,4-dioxane. The resulting suspension was heated under reflux with stirring for 24 hours, filtered through celite, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, giving 1,76 g specified in the title compounds as a pale yellow solid.

1H-NMR (CDCl3) δ is 9.09 (c, 1H), 8,82 (d, 1H), 7,40 (d, 1H), 7,34 (m, 2H), 7,20 (m, 2H).

Stage 2: 7-(4-Forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 1 of example 33, except for using 4-(4-forfinal)-3-nitropyridine obtained at stage 1 has been specified in the title compound as white solids (yield: 14.8 percent). The product was used in the next stage without additional purification.

Stage 3: the Hydrochloride of 7-(4-forfinal)-1-(2-methoxyethyl)-2,3-dimethyl-1H-PI is Rolo[3,2-b]pyridine

In accordance with the same procedures that were used in stage 2 of example 33, except for using 7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2, and 2-pomatoleios ether has been specified in the title compound as white solids (yield: 82.3 per cent).

1H-NMR (CDCl3) δ 8,43 (t, 1H), 7,44 (m, 2H), 7,28 (m, 2H), 7,13 (d, 1H), 4.00 points (t, 2H), is 3.08 (t, 2H), 3,05 (c, 3H), 2,64 (c, 3H), 2.50 each (c, 3H).

Examples from 279 to 287

The connections defined in the headers of examples 279-287, were obtained using the same procedures that were used in stage 2 of example 33, using 7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine obtained in stage 2 of example 278, and (methyl bromide)cyclopropane, 3-formanilide, iodata, 1-iodopropane, 3-methoxybenzylamine, 4-methylbenzylamine, 4-formanilide, allylbromide or 3-chlorobenzylamino.

Example 279. The hydrochloride of 7-(4-forfinal)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ to 8.45 (t, 1H), 7,45 (m, 2H), 7,28 (m, 2H), 7,15 (d, 1H), 3,76 (d, 2H), 2,67 (c, 3H), 2,52 (c, 3H), and 0.62 (m, 1H), 0,30 (m, 2H), 0,11 (m, 2H); (output: 66,0%).

Example 280. The hydrochloride of 7-(4-forfinal)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,48 (t, 1H), 7,17 (m, 1H), 7,11 (m, 3H), 7,03 (t, 2H), 6,95 (t, 1H), 6,11 (t, 2H), 5,03 (c, 2H), 2,73 (c, 3H), 2,42 (c, 3H); (output: 78,0%).

Example 281. Hydrochloride of 1-ethyl-7-(4-forfinal)-2,3-di is ethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,44 (t, 1H), 7,46 (m, 2H), 7,28 (m, 2H), 7,13 (d, 1H), 3,83 (kV, 2H), 2,65 (c, 3H), 2,48 (c, 3H), of 0.92 (t, 3H); (yield: 65.5 per cent).

Example 282. The hydrochloride of 7-(4-forfinal)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,44 (t, 1H), 7,45 (m, 2H), 7,29 (m, 2H), 7,13 (d, 1H, in), 3.75 (t, 2H), 2,65 (c, 3H), 2.50 each (t, 3H), 2,47 (c, 3H), of 0.85 (m, 2H); (output: 66,2%).

Example 283. The hydrochloride of 7-(4-forfinal)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,46 (t, 1H), to 7.09 (m, 4H), 7,01 (t, 2H), 6,76 (d, 1H), 5,91 (c, 2H), 4,99 (c, 2H), 3,69 (c, 3H), 2,71 (c, 3H), 2,41 (c, 3H); (output: 70,5%).

Example 284. The hydrochloride of 7-(4-forfinal)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,46 (t, 1H), 7,10 (m, 3H), 7,03 (m, 3H), to $ 7.91 (d, 1H), 4,98 (c, 2H), 4,71 (c, 2H), 2,38 (c, 3H), 2.40 a (c, 3H), 2,29 (c, 3H); (yield: 63.9 per cent).

Example 285. The hydrochloride of 7-(4-forfinal)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.47 (t, 1H), 7,12 (m, 3H), 7,01 (t, 2H), 6.89 in (t, 2H), 6.30-in (m, 2H), 5,01 (c, 2H), 2,72 (c, 3H), 2,42 (c, 3H); (output: 72,5%).

Example 286. Hydrochloride of 1-allyl-7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ of 8.47 (t, 1H), 7,38 (m, 2H), 7,22 (m, 2H), 7,13 (d, 1H), 5,54 (m, 1H), 5,09 (d, 1H), 4,36 (c, 2H), 4,32 (d, 1H), 2,67 (c, 3H), 2,44 (c, 3H); (output: 66,5%).

Example 287. Hydrochloride of 1-(3-Chlorobenzyl)-7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine

1H-NMR (CDCl3) δ 8,48 (t, 1H), 7,20 (m, 1H), to 7.09 (m, 6H), 6.35mm (c, 1H), 6,17 (d, 1H), 5,02 (c, 2H), 2,73 (c, 3H), 2,43 (c, 3); (yield: 78.8 per cent).

Example 288. 1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid

1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (500 mg, of 1.30 mmol)obtained in example 276, diluted with a mixture of ethanol (8 ml) and water (2 ml). To the solution was added potassium hydroxide (650 mg, 13,0 mmol) and the mixture was then heated under reflux for 24 hours. To the reaction mixture were added water and the mixture was then extracted with ethyl acetate. The separated organic layer was dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methanol=5/1, (about./about.)) to obtain 280 mg of the indicated in the title compound as a white solid.

1H-NMR (DMSO-d6) δ 10,7 (USS, 1H), 8,33 (c, 1H), 7,35 (m, 3H), 7,25 (m, 2H), 7,11 (t, 2H), 6,45 (c, 2H), 5,33 (c, 2H), 5,11 (c, 2H), 2,42 (c, 3H), 2,28 (c, 3H).

Example 289. 1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-N-cyclopropyl-1H-pyrrolo[3,2-b]pyridine-6-carboxamide

1-Benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid (24,16 mg, 0,056 mmol)obtained in example 288, hydrate of 1-hydroxybenzotriazole (11.4 mg, of 0.085 mmol), hydrochloride of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (16,3 mg of 0.085 mmol), diisopropylethylamine (0,029 ml, has 0.168 mmol) and cyclopropylamine (5,8 μl,0,084 mmol) was dissolved in dichloromethane (1 ml). The resulting solution was stirred for 2 hours at room temperature, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate/methanol=10/1, (about./about.)) obtaining specified in the title compound as a white solid (12.3 mg, 58%).

1H-NMR (DMSO-d6) δ 8.34 per (c, 1H), was 7.36 (m, 3H), 7,28 (m, 2H), 7,15 (t, 2H), 6,55 (c, 2H), 5,38 (c, 2H), 5,11 (c, 2H), 4,24 (d, 2H), 2,42 (c, 3H), 2,28 (c, 3H), 1,38 (m, 1H), 0,78 (m, 2H), 0,14 (m, 2H).

The test example 1. Inhibitory effect on the activity (N+/To+-ATPase) proton pump

1-1. Preparation of vesicles gastric proton pump

Fundic region of the pig containing parietal and peptic cells were scraped off using a glass. The collected cells are suspended in 10 ml of 0,25M sucrose buffer and homogenized using a tight-fitted Teflon glass homogenizer. The homogenate was centrifugally for 35 minutes at 8000 rpm and the precipitate was discarded. The supernatant was additionally centrifuged for 75 minutes at 25000 rpm the Resulting residue re-suspended in sucrose buffer (10 ml), and then the suspension was placed on a discontinuous density gradients consisting of 0,25M sucrose buffer and environment to highlight, containing 9%Ficoll (mass./mass.). After centrifugation for 3 hours and 15 minutes at 100000g material on the surface of the partition sucrose buffer and Ficoll solution was collected and then centrifuged for 40 min at 100000g. The resulting residue re-suspended in 1 ml of 5 mm Hepes/Tris buffer (pH 6,1). Material liofilizirovanny and kept at -70°C and used as the enzyme source in the in vitro enzyme reaction analysis of the proton pump.

1-2. Measurement of inhibitory effect on the activity (N+/K+-ATPase) proton pump

The inhibitory activity of the compounds of the present invention on the activity of the proton pump was investigated in 96-well pad. In this analysis, To+specific N+/K+-ATPase activity was calculated based on the difference between the activity of N+/K+-ATPase with K+and without+the ions. 96-hole tablet, 1% dimethyl sulfoxide (DMSO) in buffer was added to the negative and positive control groups and the diluted compounds of the present invention in the buffer was added to the test group. All analyses were performed in 100 µl reaction volume at room temperature, and gastric vesicles pigs before use and kept in ice. At the beginning of the reaction to negative and positive control groups and to each concentric and compounds in the tested group was added 10 μl of the reaction buffer, containing 1% DMSO. Then liofilizovannye vesicles in 5 mm Pipes/Tris buffer (pH 6,1) pre-incubated in the presence of different concentrations of the tested compounds. After 5 min incubation of the positive and negative buffers were added respectively to the previous reaction mixture. As a substrate to the reaction buffer was added ATP and incubated for 30 minutes at 37°C. the Enzymatic activity was stopped by the addition of the colorimetric reagent (2× malachite green, 1× ammonium molybdate, 1× polyvinyl alcohol, 2× H2About), and measured the number of monophosphate (PI) in the reaction mixture at 620 nm using a microplate counter (Genios Pro, TECAN). The difference between getting Pi with K+and without K+took over stimulated K+H+/K+-ATPase activity. The value of the IC50the tested compounds were calculated on the basis of each inhibitory values of compounds using the method of Litchfield-Wilcoxon (J. Pharmacol. Exp. Ther. (1949) 96, 99). The results are shown in table 1.

2,44
Table 1
ExampleIC50(µm)ExampleIC50(µm)
1 0,6521,06
30,6450,32
60,2070,22
80,4490,33
100,69120,97
130,80140,53
153,81160,19
23to 2.29330,65
340,23351,09
371,26381,31
390,22400,19
50542,30
550,07560,57
570,27580,23
610,10620,11
640,05650,06
660,05670,05
680,06690,06
700,04710,06
720,03730,04

741,08791,59
802,8781 1,25
824,70833,82
840,39850,17
860,05870,16
880,67890,34
900,14910,46
920,05930,05
940,89950,52
960,13970,09
980,62990,63
1002,821011,01
1131,42 1140,07
1150,131160,15
1170,721180,46
1190,231200,12
1210,321220,02
1230,061240,05
1250,051260,05
1270,041280,05
1290,041300,04
1310,061320,05
1330,061340,54
135 0,151360,05
1370,061380,46
1390,021400,08
1410,091440,24
1450,531463,15
1473,451531,03
1540,241550,57
1560,611570,57
1580,321590,88
1610,581621,15
1631,011643,00

1770,291780,84
1790,571800,83
1814,711823,88
1831,211841,07
1950,681960,38
2000,602010,68
2183,282190,06
2200,052210,18
2220,062231,21
2240,122250,62
2260,45 2270,09
2280,032290,07
2540,212550,55
2562,082601,21
261to 2.062631,45
264of 3.072681,25

As shown in table 1, the compounds of the present invention have excellent inhibitory effect on H+/K+-ATPase in stomach.

The test example 2. Inhibitory effect on the basal secretion of gastric acid in rats with a bandaged pylorus is preserved (gatekeeper)

The test of inhibitory effect of compounds of the present invention on the basal secretion of gastric acid was performed in rat models according to the method of Shay (Shay, Y., et al., 1945, Gastroenterology, 5, 43-61). Male rats Sprague Dawley (SD)(body weight 200±10 g) were divided into 3 groups (n=5) and were subjected to fasting for 24 hours with free access to water. The control group was administered peror the flax only 0.5% methylcellulose, while other groups were administered orally with compound suspended in 0.5% solution of methylcellulose, in doses of 1, 3 and 10 mg/kg/5 ml for one hour prior to ligation of the pylorus is preserved.

Under ether anesthesia, the abdomen of the rat was cut with a knife and then pylorus bandaged. After 5 hours after ligation, animals were killed and collected the contents of the stomach. Ingested content was centrifuged at 1000g for 10 minutes to obtain gastric juice. Measured total acid output 0,01H. NaOH volume (mkacf./ml) for automatic titration of gastric juice to a pH of 7.0 and was calculated indices ED50the tested compounds using the method of Litchfield-Wilcoxon. % Inhibition activity was calculated using the following equation, the results are shown in table 2.

% Inhibitory activity of the test compounds = (total acid output in the control group the total acid output in the group treated with test compounds)/total acid output in the control group ×100

Table 2
ExampleED50(mg/kg)
502,4
542,3
551,3
613,0
621,6
722,0
732,5
861,1
972,0
1391,6

As can be seen from table 2, the compounds of the present invention exhibit a strong inhibitory activity relative to the basal secretion of gastric acid in rats with a bandaged pylorus is preserved.

The test example 3. Reversible inhibition of H+/K+-ATPase of gastric pigs

3-1. Preparation of gastric vesicles

Gastric vesicles were prepared from fundic mucosa of pigs using the method Saccomani et al. (Saccomani G, Stewart HB, Shqw D, Lewin M and Sachs G, Characterization of gastric mucosal membranes. IX. Fractionation and purification of K-ATPase-containing vesicles with the reception zonal centrifugation and free-flow electrophoresis. Biochem. Biophy. Acta (BBA) - Biomembranes 465, 311-330, 1977). This material liofilizirovanny and stored at -70°C. the protein Content of gastric vesicles was determined by the Bradford method with what ispolzovaniem bovine serum albumin as standard (Bradford MM, A rapid and sensitive method for quantitative determination microgramme quantities of protein using the principle of binding protein-dye. Anal Biochem. 72, 248-254, 1976).

3-2. Determination of reversible inhibition H+/K+-ATPase of gastric pigs

The activity of H+/K+-ATPase in microsomal pigs (liofilizovannye vesicles) was measured using inorganic phosphate released from ATP using the one-step method colorimetric detection at a concentration at which the compound had a 50% inhibition of the proton pump (Chan KM, Delfert D, Junger and KD, Direct colorimetric analysis of the activity of CA2+-stimulated ATPase. Anal Biochem, 157, 375-380, 1986). The mode of action of the tested compounds on the H+/K+-ATPase was investigated by the method of Washout (Beil W, Staar U, and Sewing KF, Substituted thieno[3,4-d]imidazoles, a new group of H+/K+-ATPase inhibitors. The differentiation inhibiting characteristics from the characteristics of omeprazole. Eur. J. Pharmacol., 187, 455-67, 1990).

Liofilizovannye vesicles in a solution of 5 mm Pipes/Tris buffer pre-incubated in the presence of the test compounds (compounds of examples 50, 64 and 94) in the concentration at which it has a 50% inhibition of the proton pump. To the previous reaction buffer was added to 2 mm MgCl2, 50 mm KCl, 5 the km of Valinomycin and 0.5 mm ATP, and then incubated for 30 minutes at 37°C. H+/K+-ATPase activity was measured using the method of colorimetric detection, and then the test sample was centrifuged at 100000×g for 1 hour. Vesicles in the prototype was present in the form of granules. The supernatant was replaced with the same buffer containing no test compound. The prototype pre-incubated for 5 minutes at room temperature, and then incubated additionally for 30 minutes at 37°C. H+/K+-ATPase activity was measured using the method of colorimetric detection. Analyzed the H+/K+-ATPase activity in the test sample before washing and after washing in comparison with the activity in the untreated group.

In the compounds of examples 50, 64 and 94 inhibited H+/K+-ATPase activity by 50% to leaching and is not inhibited H+/K+-ATPase activity after washing; gastric H+/K+-ATPase activity under the action of the compounds of examples 50, 64 and 94 fully regenerated to the level of the untreated group after washing. These results confirmed that the compounds of formula (I) showed reversible inhibition of gastric H+/K+-ATPase.

1. The compound of formula (I) or the pharmaceutically priemysel:

in which R1represents hydrogen; a linear or branched C1-C6alkyl group,
optionally substituted by one or more substituents selected from
group consisting of C1-C5alkoxy, hydroxy, C3-C7cycloalkyl, acetoxy,2-C6alkenylacyl, C1-C3alkoxycarbonyl, amino, optionally substituted by one or two1-C3alkilani, cyano, naphthyl, pyridyl, oxiranyl, oxazolidinone, isoxazolyl, optionally substituted by one or more C1-C3alkilani, 1,3-DIOXOLANYL and 2,3-dihydrobenzo[1,4]dioxine; linear or branched C2-C6alkenylphenol group; a linear or branched C2-C6alkylamino group; or a benzyl group, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C3of alkyl, C1-C3alkoxy, cyano, C1-C3alkoxycarbonyl, trifter-C1-C3of alkyl,
R2represents a linear or branched C1-C6alkyl group,
R3represents a linear or branched C1-C6alkyl group, optionally substituted hydroxy,
R4represents hydrogen; a linear or branched C1 6alkyl group; halogen; cyano; hydroxycarbonyl; aminocarbonyl; or (C3-C7cycloalkylcarbonyl,
R5represents 1,2,3,4-tetrahydroisoquinoline group, optionally substituted by one or more Halogens or With1-C5alkilani; benzyloxy, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C5of alkyl, C1-C5alkoxy, trifter-C1-C3of alkyl, amino group, optionally substituted by one or two substituents selected from the group consisting of C1-C5alkoxycarbonyl and benzyl, optionally substituted with halogen; phenyl group, optionally substituted by one or more Halogens; fenoxaprop, optionally substituted by one or more halogen; pyridyl-C1-CCalkoxygroup; or peperoncino,
provided that when R5is benzyloxy that in position 4 is not substituted or substituted with halogen, position 2 and 6 of the specified group cannot be substituted With1-C5-alkyl; and n represents 1 or 2.

2. The compound or its pharmaceutically acceptable salt according to claim 1, in which
R1represents hydrogen; a linear or branched C1-C6alkyl group;
C1-C3alkyl group, substituted by one or more substituents selected from the group consisting of methoxy, hydroxy, cyclopropyl, cyclobutyl, acetoxy, vinyloxy, methoxycarbonyl, dimethylamino, cyano, naphthyl, pyridyl, oxiranyl, oxazolidinone, dimethylisoxazole, 1,3-DIOXOLANYL and 2,3-dihydrobenzo[1,4]dioxine; linear or branched C2-C6alkenylphenol group; a linear or branched C2-C6alkylamino group; or a benzyl group, optionally substituted by one or more substituents selected from the group consisting of halogen, C1-C3of alkyl, C1-C3alkoxy, cyano, methoxycarbonyl and trifloromethyl,
R2represents a methyl group;
R3represents a methyl group or hydroxymethylene group;
R4represents hydrogen; a methyl group; halogen; cyano; hydroxycarbonyl; aminocarbonyl; or cyclopropanecarbonyl;
R5represents 1,2,3,4-tetrahydroisoquinoline; 6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline; benzyloxy substituted by one or more substituents selected from the group consisting of halogen, C1-C5of alkyl, C1-C5alkoxy and trifloromethyl; an amino group substituted by one or two tert-butoxycarbonylamino or formentelli; florfenicol group; perperoglou; piediluco the si; or piperonylic;
provided that when R5is benzyloxy that in position 4 is not substituted or substituted with halogen, position 2 and 6 of the specified group cannot be substituted With1-C5-alkyl; and n represents 1 or 2.

3. The compound or its pharmaceutically acceptable salt according to claim 1, which is selected from the group consisting of
hydrochloride of 1-(4-Chlorobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-(2-naphthylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(1,3-dioxolane-2-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-methoxyethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-(3-methoxybenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-(2-terbisil)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-(4-methoxybenzyl)-7-(1,2,3,4-tetrahydroxy the Olin-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-propyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-methylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1 H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-ethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-[2-(1,3-dioxolane-2-yl)ethyl]-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-methylbutan-2-yl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3,5-dimethylisoxazol-4-ylmethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-methoxycarbonylethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-methoxymethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-tert-butylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-cyanobenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-p is Rolo[3,2-b]pyridine;
hydrochloride of 1-ethoxycarbonylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,4-dimethylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-methoxycarbonylbenzyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-vinyloxyethyl)-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-isobutyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-oxiranylmethyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(1,2,3,4-tetrahydroisoquinoline-2-yl)-3-hydroxymethyl-2-methyl-1H-pyrrolo[3,2-b]pyridine;
2-(2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline;
hydrochloride of 2-(1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-6-fluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline;
hydrochloride of 1-(4-Chlorobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride methyl ester 4-[7-(4-forbindelse)-2,3-dimethyl-pyrrolo[3,2-b]pyridine-1-ylmethyl]benzoic acid;
hydrochloride of 1-(4-tert-butylbenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-fermentelos is)-2,3-dimethyl-1-(naphthalene-2-ylmethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(2-vinyloxyethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(1,3-dioxolane-2-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-terbisil)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,5-dimethylbenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3,5-dimethylisoxazol-4-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-Chlorobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(pyridine-2-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-cyanobenzyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-oxiranylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(pyridine-3-ylmethyl)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-1-isobutyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(prop-2-inyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-a]pyridine;
hydrochloride of 7-(4-forbindelse)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-(3-methyl-2-butene-2-yl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-[2-(methoxycarbonyl)ethyl]-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-terbisil)-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine;
methansulfonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
benzosulfimide 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
p-toluensulfonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
nitrate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
sulfate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
maleate of 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2b]pyridine;
phosphate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
malonate 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrobromide 1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-cyanobenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyanomethyl-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1-(4-trifloromethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-tert-butylbenzyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-2,3-dimethyl-1-(pyridine-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 5-[7-(4-chlorobenzoyloxy)-2,3-dimethyl-pyrrolo[3,2-b] pyridine-1-ylmethyl]oxazolidin-2-it;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2,5-dimethylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
the methyl ester hydrochloride [7-(4-chlorobenzoyloxy)-2,3-dimethyl-pyrrolo[3,2-b]pyridine-1-yl]acetic acid;
hydrochloride of 7-(4-chlorobenzoyloxy)-2,-dimethyl-1-(3-methylbut-2-enyl)-1H-pyrrolo [3,2-b]pyridine;
hydrochloride of 1-(2-acetoxyethyl)-7-(4-chlorobenzoyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(1,3-dioxolane-2-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-methoxycarbonylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-chlorobenzoyloxy)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
Hydra is chloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(1,3-dioxolane-2-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-tert-butylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-methoxycarbonylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3,5-dimethylisoxazol-4-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-oxazolidinone-5-ylmethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1-(4-trifloromethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2-hydroxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(2,5-dimethylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-methoxycarbonylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-methylbut-2-enyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine is;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-isobutyl-2,3-dimethyl-1H-pyrrolo [3,2-b]pyridine;
hydrochloride 7-(benzo[1,3]dioxol-5-ylethoxy)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
methansulfonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
benzosulfimide 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
p-toluensulfonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
nitrate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
sulfate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
maleate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-spiralo[3,2-b]pyridine;
phosphate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
malonate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
campanulata 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
oxalate 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrobromide 7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-1-methoxymethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-2,3-dimethyl-1-(3-methylbut-2-enyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-1-methoxycarbonylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(2,4-dichloraniline)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-tert-butylbenzyl)-7-(2,4-dichloraniline)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochl the reed 1-benzyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-ethyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-terbisil)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-Chlorobenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-1-(3-methylbenzyl)-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-(pyridine-2-ylmethyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,5-dimethylbenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-tert-butylbenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-(3-methylbut-2-enyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-7-(3-methylbenzylamino)-1-propyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-1-(4-methylbenzyl)-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-terbisil)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-methoxybenzyl)-2,3-dimethyl-7-(3-methylbenzylamino)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-Harb nil)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3,4-dichlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzoate)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-Chlorobenzyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(3-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-dioxolane-2-ylmethyl)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(2-ethoxybenzyl)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-terbisil)-7-(2-ethoxybenzoate)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(3,4-dichlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1,2,3-trimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(3,4-dimethoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(2-terbisil)-2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridine;
g is drochloride 1-(3-Chlorobenzyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b] pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(3,5-deferasirox)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(pyridine-2-ylmethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(pyridine-3-ylmethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2,2-dimethylaminoethyl)-7-(3,5-deferasirox)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-1-(4-methylbenzyl)-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-methoxybenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-Chlorobenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-ethyl-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-Chlorobenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclopropylmethyl-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-methoxybenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-Torben who yl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3,4-dichlorobenzyl)-2,3-dimethyl-7-(4-triftormetilfosfinov)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-1-propyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-isobutyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-2,3-dimethyl-7-(pyridine-3-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 2,3-dimethyl-1-propyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-methoxyethyl)-2,3-dimethyl-7-(pyridine-2-ylethoxy)-1H-pyrrolo[3,2-b]pyridine;
7-(4-bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(4-bromobenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(4-bromobenzylamine)-2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(4-bromobenzylamine)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-(2-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-(3-Chlorobenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-cyclobutylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-isobutyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-bromobenzylamine)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(4-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-isopropylbenzylamine)-2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-isopropylbenzylamine)-2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-isopropylbenzyl)-1-(2-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-Chlorobenzyl)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(2-terbisil)-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(4-isopropylbenzylamine)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride 7-(4-isopropylbenzyl)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-cyclobutylmethyl-7-(4-pertenece)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride tert-butyl ether (2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(2-methoxyethyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether (2,3-dimethyl-1-cyclopropylmethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether (2,3-dimethyl-1-ethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid;
hydrochloride tert-butyl methyl ether (1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(3-terbisil)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(3-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(4-methoxybenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(3-methylbenzyl)-1H-pyrrolo[3,2-b]is iridin-7-yl]-(4-terbisil)carbamino acid;
hydrochloride tert-butyl ether [2,3-dimethyl-1-(4-methylbenzyl)-1H-pyrrolo[3,2-b]pyridin-7-yl]-(4-terbisil)carbamino acid;
the hydrochloride of N-(1-allyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-(1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-[1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
the hydrochloride of N-[1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
the hydrochloride of N-[1-(4-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
the hydrochloride of N-(1-ethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-(2,3-dimethyl-1-propyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-(1-benzyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-[1-(3-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
the hydrochloride of N-[1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
hydrochloride of 1-benzyl-7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-propyl-7-(4-forbindelse)-1-(2-methoxyethyl)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forbindelse)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine;
the hydrochloride of N-(1-allyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridine-yl)-4-forbindelsen;
the hydrochloride of N-(1-benzyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-(1-cyclopropylmethyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-(1-propyl-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl)-4-forbindelsen;
the hydrochloride of N-[1-(2-methoxyethyl)-2,3,5,6-tetramethyl-1H-pyrrolo[3,2-b]pyridin-7-yl]-4-forbindelsen;
6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-benzyl-6-bromo-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 6-bromo-7-(4-forbindelse)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 6-bromo-7-(4-forbindelse)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile;
1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carboxamide;
hydrochloride of 7-(4-forfinal)-1-(2-methoxyethyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forfinal)-1-cyclopropylmethyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forfinal)-1-(3-terbisil)-2,3-Dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-ethyl-7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forfinal)-1-propyl-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forfinal)-1-(3-methoxybenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydroch oride 7-(4-forfinal)-1-(4-methylbenzyl)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 7-(4-forfinal)-1-(4-terbisil)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-allyl-7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
hydrochloride of 1-(3-Chlorobenzyl)-7-(4-forfinal)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine;
1-benzyl-7-(4-forbindelse)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carboxylic acid; and
1-benzyl-7-(4-forbindelse)-2,3-dimethyl-N-cyclopropyl-1H-pyrrolo[3,2-b]pyridine-6-carboxamide.

4. The method of obtaining the compounds of formula (I) or its pharmaceutically acceptable salt, including
the interaction of the compounds of formula (II) with R5-H with obtaining the compounds of formula (III),
the interaction of the compounds of formula (III) with the compound of the formula (IV) with a compound of formula (Ia), and
the interaction of the compounds of formula (Ia) with R1-X with obtaining the compounds of formula (I):


where R1, R2, R3, R4, R5and n have the meanings given in claim 1; and X represents halogen.

5. Pharmaceutical composition having inhibitory activity against proton pump comprising a therapeutically effective amount of any of compounds of the formula (I) or its pharmaceutically acceptable salt according to claim 1, and pharmaceutically acceptable nose is tel.



 

Same patents:

FIELD: medicine.

SUBSTANCE: invention refers to compounds having anxiolytic and antidepressant activity, which are derivatives of the formula 1 (a-b), or formula 2 (a-b) at that compounds of formula 2 (a-b) are intermediate products in synthesis of compounds of the formula , where R-Cl is a compound 1a or R'=COOC2H5 - compound 1b, , where R=COOC2H5 and R'=C1 - compound 2a; R=R-COOC2H5 - compound 2b.

EFFECT: obtaining new biologically active compounds that differ from analogues as intended in low toxicity and lack of side effects.

5 cl, 3 ex, 5 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula I and their pharmaceutically acceptable salts. The disclosed compounds have CDK1 and/or CDK2 kinase inhibiting activity. In formula R1 is selected from hydrogen, hydroxy-lower alkyl, C3-C6 cycloalkyl and R2-(X)n; X is selected from lower alkylene, hydroxy-lower alkylene, lower cycloalkylene or lower alkanoyloxy-lower alkylene; R2 is and is selected from phenyl and a 5- or 6-member heteroaromatic ring containing 1 or 2 heteroatoms selected from a group consisting of sulphur and nitrogen; R5 and R6 are independently selected from a group consisting of hydrogen, lower alkyl, halogen and lower alkoxy; and n equals 0 or 1.

EFFECT: design of a pharmaceutical composition for treating and preventing diseases whose condition can be improved by inhibiting CDK1 and/or CDK2 kinase, containing an effective amount of formula I compounds.

47 cl, 19 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds of formula I. In general formula I A is C or N; B, D and E independently represent CR4, NR5, N, O or S; and a ring containing groups A, B, D, E, selected from thienyl, furan, imidazole, oxazole, isothiazole, thiazole, pyrrol, pyrazole; provided that: b) when A is N, not any of B, D, E can be O or S; and c) when A is C, B is CR4 and one of D or E is N or NR5, when any of D or E cannot be NR5 or N; G is N or C; R1 represents one or more substitutes selected from H, Ra halogen, -OH and -ORa; R2 represents one or more substitutes selected from H, halogen and C1-6-alkyl, and also one of substitutes R2 can be -ORb' , -NRb' Rb', -SRb', -SORb', -SO2Rb', -SO2NRb' Rb'; R3 is H, or Cy, selected from phenyl optionally substituted with one or more substitutes selected from Rc , where Rc independently represents halogen, -ORg', where Rg' independently represents a Rg group, where Rg is C1-6-alkyl; each R4 independently represents H, Re, halogen, -CORe', -CO2Re', -CONRe'Re', -NRe'Re'; R5 independently represents H, Re, -CORe, -CONReRe, -SORe or -SO2Re; each Ra independently represents C1-6-alkyl or halogen- C1-6-alkyl; each R independently represents C1-6-alkyl optionally substituted with one or more substitutes selected from Rd and Rf; each Rb' independently represents H or Rb; each Rc independently represents halogen, -ORg', -CONRg'Rg', -NRg'Rg'; Rd is Cy optionally substituted with one or more Rf substitutes; each Rc independently represents C1-6-alkyl optionally substituted with one or more substitutes selected from Rc and Cy*, or Re is Cy, where any of the groups Cy or Cy* can optionally be substituted with one or more substitutes selected from Rc and Rg ; each Re' independently represents H or Re; each Rf independently represents a halogen, -ORh', -CO2Rh; each Rg independently represents Rd or C1-6-alkyl optionally substituted with one or more substitutes selected from Rd and Rf; each Rg' independently represents H or Rg; each Rh independently represents C1-6-alkyl, halogen-C1-6-alkyl or hydroxy- C1-6-alkyl; each Rh' independently represents H or Rh; and Cy or Cy* given in definitions above is a partially saturated, saturated or aromatic 3-7-member monocyclic carbocyclic ring which optionally contains 1-2 heteroatoms selected from N and O, and where the ring or rings can be bonded to the remaining part of the molecule through a carbon or nitrogen atom.

EFFECT: obtaining formula I compounds with p38-kinase inhibitory properties which can be used in making drugs for treating such diseases as tumour immune and autoimmune diseases etc.

21 cl, 10 dwg, 8 tbl, 57 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds of formula where L1 and L2 independently denote a bond, -S-, -NH- or unsubstituted C1-C5alkylene; A1 denotes a 6-member substituted aryl or unsubstituted heteroaryl; A2 denotes aryl or heteroaryl; R1 denotes halogen, -OR5, -NR6R7, -C(Z)R8, -S(O)wR9, -CN, -NO2, -S(O)2NH2, alkyl, aryl or heteroaryl; X1 denotes -C(R2)=, -C(R2)(R3)-, -N(R4)- or -O-; R2 and R3 independently denote hydrogen, -OR5 or alkyl; R4 denotes hydrogen or alkyl; Z denotes O or NH; w is integer from 0 to 2; R5 independently denotes hydrogen or alkyl; R6 and R7 independently denote hydrogen, -S(O)2R11 alkyl or heteroalkyl; R11 denotes hydrogen or alkyl; R8 independently denotes hydrogen, -NR14R15, -OR16, heteroalkyl or cycloalkyl; R14, R15 and R16 independently denote hydrogen, alkyl, cycloalkyl, heteroalkyl or heterocycloalkyl; R9 independently denotes hydrogen or alkyl; and where R6 and R7, R14 and R15 independently and optionally together with the nitrogen atom to which they are bonded form a substituted or unsubstituted heterocycloalkyl. The invention also relates to a method of modulating protein kinase activity, as well as to use of compounds in paragraph 1 and a pharmaceutical composition based on the said compounds.

EFFECT: new compounds which can be useful in treating diseases mediated by kinase activity are obtained and described.

47 cl, 2 ex, 40 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to benzazepin derivatives of formula (I), where R1 is unsubstituted cyclobutyl, R2 is 3-pyrazinyl, substituted CON(H)(Me) or 2-pyridinyl-M-pyrrolidinyl, where the said pyrrolidinyl group is substituted with a =O group; which is: methylamide 5-(3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy) pyrazine-2-carboxylic acid

or 1-{6-[(3-cyclbutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinyl}-2-pyrrolidinone

EFFECT: obtaining compounds which have affinity to histamine H3 receptor and pharmaceutical compositons containing said compounds.

11 cl, 288 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula

,

where the carbon atom denoted * is in R- or S-configuration; X is a concentrated bicyclic carbocycle or heterocycle selected from a group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, indazolyl, indolyl, benzooxazolyl, benzothiazolyl, indenyl, indanyl, dihydrobenzocycloheptenyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, quinoxalinyl, 2H-chromenyl, imidazo[1.2-a]pyridinyl, pyrazolo[1.5-a]pyridinyl, and condensed bicyclic carbocycle or condensed bicyclic heterocycle, optionally substituted with substitutes (1 to 4) which are defined below for R14; R1 is H, C1-C6-alkyl, C3-C6-cyclalkyl, C1-C3-alkyl, substituted OR11, -NR9R10 or -CN; R2 is H, C1-C6-alkyl, or gem-dimethyl; R3 is H, -OR11, C1-C6-alkyl or halogen; R4 is H, halogen, -OR11, -CN, C1-C6-alkyl, C1-C6-alkyl, substituted -NR9R10, C3-C6-cycloalkyl, substituted -NR9R10, C(O)R12; or R4 is morpholinyl, piperidinyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, isoxazolyl, pyrrolidinyl, piperazinyl, 2-oxo-2H-pyridinyl, [1.2.4]triazolo[4.3-a]pyridinyl, 3-oxo-[1.2.4]triazolo[4.3-a]pyridinyl, quinoxalinyl, which are optionally substituted with substitutes (1 to 4) which are defined below for R14; R5 is H or C1-C6-alkyl; R6 is H, C1-C6-alkyl, or -OR11; R7 is H; R8 is H, -OR9, C1-C6-alkyl, -CN; R9 is H or C1-C4-alkyl; R10 is H or C1-C4-alkyl; or R9 and R10 taken together with the nitrogen atom to which they are bonded form morpholine; R11 is H, C1-C4-alkyl; R12 is C1-C6-alkyl; R14 in each case is independently selected from a substitute selected from a group consisting of halogen, -OR11, -NR11R12, C1-C6-alkyl, which is optionally substituted with 1-3 substitutes, in each case independently selected from a group consisting of C1-C3-alkyl, aryl; or to pharmaceutically acceptable salts thereof. The invention also relates to a pharmaceutical composition, to a method of obtaining formula (I) compounds, as well as to a method of treating disorders.

EFFECT: obtaining new biological active compounds having norepinephrine, dopamine and serotonin reuptake selective inhibitory activity.

90 cl, 162 ex, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula (I) and their pharmaceutically acceptable salts of formula (I) where n equals 0, 1 or 2, A is a five- or six-member aromatic ring which optionally contains one or two heteroatoms independently selected from nitrogen, oxygen or sulphur, B is a 5-9-member ring containing 0 or 1 double bonds and optionally contains an additional heteroatom selected from nitrogen and oxygen; where the ring optionally contains one or two substitutes independently selected from a group comprising C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkyl, carboxy, cyano, hydroxy, hydroxy-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, (NR4R5)-carbonyl or oxo; R1 is selected from -C(O)NR4R5 - CO2R4, 5-tetrazolyl, cyano; each R2 is independently selected from a group comprising C1-C6-alkyl, amino, benzyloxy, halogen, hydroxyl; R3 is a 5-7-member cycloalkyl ring; values of the rest of the radicals are given in the formula of invention. The invention also relates to a method for synthesis of the said compounds, a method of inhibiting HCV replicon function and a method of inhibiting functioning of the HCV NS5B protein.

EFFECT: wider field of use of the compounds.

16 cl, 4 tbl, 29 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel condensed heterocylic protein kinase modulators of formula I where L1 and L2 independently denote a bond, and R1 and R2 denote a substituted or unsubstituted heteroaryl or a substituted or unsubstituted aryl, as well as to pharmaceutical compositions containing such compounds, and methods of using the compounds to prepare medicine for diseases mediated by protein kinase activity.

EFFECT: increased effectiveness of using the compounds.

24 cl, 20 tbl, 24 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds selected from compounds of formulae Ia, lb and Ic, which have protein kinase activity on kinase selected from CDKs, Aurora, Jak2. Rock, CAMKI, FLT3, Tie2, TrkB, FGFR3 and KDR, abnormal activity of which is observed in pathological conditions such as nonmalignant and malignant proliferative diseases. In compounds of formulae , and : n equals 0 or 1, R1 is selected from a group comprising halogen, C1-C6alkyl, C1-C6alkoxy, halogen-substituted CpC6alkyl and halogen-substituted C1-C6alkoxy, R2 is selected from a group comprising phenyl, 6-member heteroaryl containing 1-2 nitrogen atoms in the heteroaryl ring as heteroatoms, and phenyl(C0-C4)alkyl, where the said phenyl and heteroaryl in R2 are optionally substituted with 1-3 radicals independently selected from a group comprising halogen, C1-C6alkyl, C1-C6alkoxy, halogen-substituted C1-C6alkyl, halogen-substituted C1-C6alkoxy, -S(O)0-2R5, -COOR5 and -NR5C(O)R6, where R5 is selected from C1-C6alkyl, and R6 is selected from phenyl, where the said phenyl in R6 is optionally substituted with 1-3 radicals independently selected from a group comprising C1-C6alkyl, C1-C6alkoxy, halogen-substituted C1-C6alkyl and halogen-substituted C1-C6alkoxy, X is selected from CR7 and N, where R7 is selected from hydrogen or C1-C6alkyl.

EFFECT: increased effectiveness of using the compounds.

7 cl, 3 dwg, 1 tbl, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to tetrahydropyridoindole derivatives of general formula , where R1, R2, R3 and R4 independently represent hydrogen; C1-C5alkyl, which can be optionally substituted and represents trifluoromethyl if C1-C5alkyl is substituted; C1-C3alkoxy or halogen, and R5 is C1-C6alkylcarbonyl, C1-C5alkylcarbamoyl, C1-C5alkoxycarbonyl, C2-C5alkenylcarbonyl, C3-C6cycloalkylcarbonyl, C3-C6cycloalkyl(C1-C3)alkylcarbonyl, C3-C6cycloalkylcarbamoyl, C3-C6cycloalkylthiocarbamoyl, phenylcarbonyl or phenyl(C1-C3)alkylcarbonyl, where the phenyl residue in these two groups contains one, two, three or four substitutes, independently selected from a group comprising C1-C4alkyl, C1-C3alkoxy, halogen, trifluoromethyl and trifluoromethoxy, monosubstituted with a C3-C6cycloalkyl group, or monosubstituted with a phenyl group which in turn is substituted with a C1-C3alkyl group; phenyl(C1-C3)alkoxycarbonyl, phenylcarbamoyl or phenylthiocarbamoyl (where these two groups are optionally independently monosubstituted with a C1-C5alkyl group or halogen atoms); phenyl(C1-C3)alkylcarbamoyl, phenyl(C1-C3)alkylthiocarbamoyl, biphenylcarbamoyl, naphthylcarbonyl, naphthyl(C1-C3)alkylcarbonyl or naphthylcarbamoyl (where the naphthyl residues in these three groups are optionally monosubstituted with substitutes independently selected from a group comprising C1-C3alkyl, C1-C3alkoxy and halogen); fluorenylcarbonyl, optionally substituted with an oxo group, fluorenyl(C1-C3)alkoxycarbonyl; or 5-9-member heteroarylcarbonyl groups containing one or two heteroatoms, independently selected from a group comprising oxygen, nitrogen and sulphur, where the said groups can be substituted with one or two groups independently selected from C1-C3alkyl and halogen, provided that if R1, R2, R3, R4 are hydrogen, R5 is not ethoxycarbonyl or tert-butoxycarbonyl, or salt thereof. The invention also relates to a pharmaceutical composition based on the compound of formula I and to use of the compound in preparing a medicinal agent.

EFFECT: obtaining novel tetrahydropyridoindole derivatives which have CRTH2 receptor antagonistic activity.

14 cl, 14 tbl, 171 ex

FIELD: medicine.

SUBSTANCE: invention relates to medications and deals with medicinal substance for inhibition of helicobacter-like erosion-ulcerous injuries of stomach mucosa, which contains as active component in efficient amount 9-(2-diethylaminoethyl)-2-phenyl-imidaso[1,2-a]benzimidasol dinitrate of formula I .

EFFECT: invention is aimed at extension of means for inhibition of helicobacter-like erosion-ulcerous injuries of stomach mucosa.

1 tbl

FIELD: medicine.

SUBSTANCE: invention belongs to chemical and pharmaceutical industry, notably to design of plant-origin enterosorbent. Enterosorbent are granules, containing peat moss Sphagnum fuscum. Granules are produced by Sphagnum fuscum grass sod disintegration up to particles 0,1-0,3 mm which are subsequently mixed with 10% aqueous low molecular polyvinylpyrrolidone, granulated, dried and granulated again up to granules humidity not higher 30-35%.

EFFECT: produced by this method enterosorbent is low-toxic.

2 tbl

FIELD: food industry.

SUBSTANCE: invention concerns nutrient composition which contains at least carbohydrate, lipid, protein and mineral, and is liquid or semi-solid. Based on the volume particle's middle size (d 50) is from 5 to 100 micron in nutrient composition. Water insoluble particles contain protein as main component which is brought to insoluble condition by divalent cation. Viscosity of the nutrient composition is from 400 till 7000 MPas at 25°C. Nutrient composition may contain protein as main component which is brought to insoluble condition by divalent cation. The protein mass ratio according to total molar concentration of divalent ions which forms water insoluble particles is from 1.5 till 3 g/moll.

EFFECT: invention allows getting composition with high protein content, good immunity to heating and high storage stability.

24 cl, 5 dwg, 20 tbl, 11 ex

FIELD: medicine.

SUBSTANCE: invention refers to medicine, namely to experimental pharmacology and gastroenterology and concerns prevention of gastroesophageal reflux in experiment. Gastroesophageal reflux is modelled by single introduction of methylene blue into an animal's cardiac orifice. The preliminary introduction of the preparation L-NAME in a dose 1-5 mg/kg inhibits the development of gastroesophageal reflux.

EFFECT: method prevents the development of gastroesophageal reflux in experiment within a week after the single introduction of L-NAME in said dosage range.

3 ex

FIELD: medicine.

SUBSTANCE: method involves introduction to a mammal of therapeutically effective amount of a compound exhibiting properties of antagonist of A2B receptor of the following formula: , where R1 and R2 independently represent lower alkyl, R3 represents hydrogen, X represents pyrazolene, Y represents lower alkylene, and Z represents phenyl or pyridyl which can be substituted with trifluoromethyl. Besides the invention covers a pharmaceutical composition.

EFFECT: accelerated wound healing in a mammal.

7 cl, 6 dwg, 2 tbl, 22 ex

FIELD: chemistry.

SUBSTANCE: invention provides novel pyrrolo[2,3-c]pyridine derivatives of formula (I), where radicals R1, R2, R3, R4 and R5 are as indicated in paragraph 1 of the formula of invention, or their pharmaceutically acceptable salts, as well as methods of producing the said compounds and a pharmaceutical composition having proton pump inhibiting effect.

EFFECT: novel compounds which exhibit excellent proton pump inhibiting effect and can have reversible proton pump inhibiting effect are obtained and described.

6 cl, 927 ex, 2 tbl

FIELD: medicine.

SUBSTANCE: offered oral compositions containing irreversible inhibitor of proton pump of gastric N+/K +-adenosinetriphosphatase (PPI) as an inhibitor for suppression of gastric juice secretion, and an activator of parietal cells in a gastric lumen - one or more carboxylic acids chosen from the group as follows: maleic acid, succinic acid, citric acid, pyruvate, fumarate,α-ketoglutarate, succinyl-CoA and oxa-loacetate (versions), a related kit and method to suppress gastric juice secretion.

EFFECT: intensified antiacid activity of PPI in stomach ensured by the declared compositions.

25 cl, 5 dwg, 3 ex

Triazole derivative // 2383536

FIELD: chemistry.

SUBSTANCE: described are novel triazole derivatives with general formula where values of radicals are given in the formula of invention, a pharmaceutical composition containing said derivatives, and a method of treating autoimmune diseases. Compounds with general formula (1) and their pharmaceutically acceptable salts have inhibition effect on S1P and its Edg-1 receptor (S1P1).

EFFECT: possibility of use as a pharmaceutical product.

43 cl, 10 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to novel pyrrolo[3,2-c]pyridine derivatives of formula (I) or their pharmaceutically acceptable salts in which R1 is hydrogen; straight or branched C1-C6alkyl group optionally substituted with one or more substitutes selected from a group consisting of C1-C5alkoxy, hydroxyl, C3-C7 cycloalkyl, C1-C3 alkylthiazolyl and 1,3-dioxolanyl; straight or branched C2-C6 alkenyl group; straight or branched C2-C6 alkynyl group; C3-C7cycloalkyl group; or benzyl group optionally substituted with one or more substitutes selected from a group consisting of halogen, C1-C3alkyl and C1-C3alkoxy, R2 is a straight or branched C1-C6 alkyl group, R3 is hydrogen; straight or branched C1-C6 alkyl group; straight or branched C2-C6alkenyl group; or a benzyl group optionally substituted with one or more halogens, and R4 is 1,2,3,4-tetrahydroisoquinolinyl group; a benzyloxy group optionally substituted with one or more halogens; or an amine group substituted with one or two substitutes selected from a group consisting of hydrogen, straight or branched C1-C5alkylcarbonyl, phenoxycarbonyl, benzyl, optionally substituted with one or more halogens, and benzoyl, optionally substituted with one or more halogens, as well as to method of producing said compounds and a pharmaceutical composition with inhibitory effect on a proton pump containing these compounds.

EFFECT: new compounds are obtained and described, which exhibit excellent inhibitory effect on a proton pump and can provide reversible inhibitory effect on a proton pump.

7 cl, 82 ex, 2 tbl

FIELD: medicine.

SUBSTANCE: invention refers to production of biologically active additives for prevention and assisted treatment of gastritis, duodenitis and colitis of various aetiologies, and peptic ulcer disease. The composition of the herbal biologically active additive for prevention and assisted therapy of gastrointestinal diseases contains the following components, wt fractions: liquid linseed extract 7000-8000; shelf fungus extract 130-170; camomile extract 40-50; licorice extract 20-25; calcium carbonate 400-600; magnesium carbonate 280-360; magnesium oxide 245-250; sodium hydrocarbonate 50-100; sorbite 1300-1700; starch 130-170; carboxymethyl cellulose 110-160; potassium sorbate 12-17; nisin 1-2; an aromatiser 5-15; water up to 15000.

EFFECT: composition expresses antacidic action, improves condition of upper digestive mucosa and differs for good tolerance.

3 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to compounds of formula I and their pharmaceutically acceptable salts. The disclosed compounds have CDK1 and/or CDK2 kinase inhibiting activity. In formula R1 is selected from hydrogen, hydroxy-lower alkyl, C3-C6 cycloalkyl and R2-(X)n; X is selected from lower alkylene, hydroxy-lower alkylene, lower cycloalkylene or lower alkanoyloxy-lower alkylene; R2 is and is selected from phenyl and a 5- or 6-member heteroaromatic ring containing 1 or 2 heteroatoms selected from a group consisting of sulphur and nitrogen; R5 and R6 are independently selected from a group consisting of hydrogen, lower alkyl, halogen and lower alkoxy; and n equals 0 or 1.

EFFECT: design of a pharmaceutical composition for treating and preventing diseases whose condition can be improved by inhibiting CDK1 and/or CDK2 kinase, containing an effective amount of formula I compounds.

47 cl, 19 ex

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