Asaindoles

FIELD: medicine; pharmacology.

SUBSTANCE: invention refers to pharmaceutical formulation inhibiting protein kinase, containing inhibiting selective kinase compound amount of general formula (I): , where: R means aryl or indolyl, and the latter is optionally substituted with one or more groups selected from R4, -C(=O)-R, -C(=O)-OR5, -C(=O)-NY1Y2 and -Z2R; R2 means H; R3 means H; R4 means C1-C6 alkyl, optionally substituted with one substitute -C(=O)-NY1Y2; R5 means H; R7 means C1-C6 alkyl; R means C1-C6 alkyl; X1 means C-aryl, C-heteroaryl, such as pyridile or isoxasolyl, and the latter is optionally substituted with one or two C1-C6 alkyls, C-heterocycloalkyl, such as morpholinile or peperidynil, C-halogen, C-CN, C-OH, C-Z2R, C-C(=O)-OR5, C-NYlY2, C-C(=O)-NY1Y2; Y1 and Y2 means redardless H, aryl, C3-C6 cycloaryl, C1-C6 alkyl, optionally substituted with one group selected from phenyl, halogen, heterocyclil, such as morpholinile, phurile, hydroxyl, -C(=O)-OR5, OR7; or group-NY1Y2 can form morpholinile, peperidynil, optionally substituted with one or two substitutes selected from OH, C1-C6 alkyl; Z means O; where aryl as group or part of group means optionally substituted with one or two substitutes monocyclic aromatic C6carbocyclic fragment, where substitute is selected from halogen or C1-C6 alkoxy, C(=O)-OR5; except compounds: 4-chlorine-2-(4-tert-butylphenyl)-1H-pyrrole[2,3-b]pyridine, 2-(5-methoxy-1 -methyl-1 H-indole-3-il)-4-phenyl-1H- pyrrole[2,3-b]pyridine, 2-(5- methoxy-1 -methyl-1 H-indole-3-il)-1H- pyrrole[2,3-b] pyridine-4-carbonitrile, 4-chlorine-2-(5- methoxy-1 -methyl-1H-indole-3-il)-1H- pyrrole[2,3-b]pyridine, or 2-(5- methoxy-1H-indole-3-il)-1H- pyrrole[2,3-b]pyridine -4- carbonitrile.

EFFECT: application of compound for production of medicinal agent for inflammatory disease.

51 cl, 9 tbl, 148 ex

 

The present invention relates to substituted azaindole, to methods for their preparation, pharmaceutical compositions containing these compounds, and their pharmaceutical use in the treatment of painful conditions that can be controlled by inhibiting protein kinases.

Protein kinase involved in the acts of the transmission signals, which regulate the activation, growth and differentiation of cells in response to extracellular mediators and changing environment. Typically, these kinases are divided into several groups: those that preferentially phosphorylate serine and/or threonine residues, and those that preferentially phosphorylate the tyrosine residues [S.K. Hanks and T.Hunter, FASEB. J.,1995, 9, pages 576-596]. Serine/threonine kinases include, for example, isoforms of protein kinase C [A.C.Newton, J. Biol. Chem., 1995, 270, pages 28495:28498] and a group of cyclin-dependent kinases such as cdc2 [J.Pines, Trends in Biochemical Sciences, 1995, 18, pages 195-197]. Tyrosine kinase include, tightening of the membrane receptors of growth factors,such asepidermal growth factor receptor [S.Iwashita and M.Kobayashi, Cellular Signalling, 1992, 4, pages 123-132], and intracellular, preceptories kinases, such as p56tck, p59fYn, ZAP-70 and csk kinases [C.Chan et. al., Ann. Rev. Immuhol., 1994, 12, pages 555-592].

Excessive activity of protein kinases accompanies many diseases arising from abnormal cell functions. It can problemsarise directly or indirectly, for example, in the form of a denial of a corresponding control mechanism for kinase associated, for example, by mutation, over-expression or inappropriate activation of the enzyme, or in the form of excessive or insufficient production of cytokines or growth factors, which are also involved in the transduction of signals "above" or "below" kinase. In all these cases, it can be expected that selective inhibition of the kinase will have a positive effect.

Tyrosinekinase spleen (Syk) is a 72-kDa cytoplasmically proteincontaining, which is expressed in various hematopoietic cells and is an essential element in the series of cascades that bind receptors antigens with cellular reactions. Thus, Syk plays a Central role in transmitting signals to the high affinity IgE receptor, FcεRl, in the fat cells and signaling receptor antigen in T and B lymphocytes. Scheme of signal transduction characteristic of fat, T and B cells have common features. The receptor binding domains of the ligand does not have a specific activity of tyrosine kinase. However, they interact with the corresponding subunits that contain the activation fragment-based immunoreceptor tyrosine (ITAM) [M.Reth, Nature, 1989, 338, pages 383-384]. These fragments are present in βand γ subunit of the Fcε Rl, ξ-subunit of the T cell receptor (TCR) and IgGα IgGβ the subunits B cell receptor (BCR). [N.S.van Oers and A. Weiss, Seminars in Immunology, 1995, 7, pages 227-236]. After binding of antigen and polymerization ITAM residues fosfauriliruyutza proteinkinase Src family. Syk belong to a unique class tyrosinekinase that contain two homologous Src tandem, 2 (SH2) domain and a C-terminal catalytic domain. These SH2 domains bind with high affinity with ITAM, and this SH2-oposredstvovaniya Association of Syk with the activated receptor stimulates activity of Syk kinase and localizes Syk on the plasma membrane.

In mice with deficiency of Syk ingibirovany degranulation of mast cells, suggesting that this is important in order to create agents, stabilizing mast cells [P.S.Costello, Oncogene, 1996, 13, pages 2595-2605]. Similar studies have demonstrated a critical role for Syk in BCR and TCR signaling[A.M.Cheng, Nature, 1995, 378, pages 303-306, (1995) and D.H.Chu et al., Immunological Reviews, 1998, 165, pages 167-180]. In addition, Syk apparently involved in the survival of eosinophils in response to IL-5 and GM-CSF [S.Yousefi et al., J. Exp. Med., 1996, 183, pages 1407-1414]. Despite the key role of Syk in mast cells in the transmission of signals in BCR and T cells, very little is known about the mechanism by which Syk passes below the effectors. Two adaptronic protein BLNK (B cell linker protein SLP-65) and SLP-76, as b is lo shows are substrates for Syk in B cells and mast cells, respectively, and has been postulated that they associate with Syk located below effectors [M.Lshiai et al., Immunity, 1999, 10, pages 117-125 and L,R.Hendricks-Taylor et al., J.Biol. Chem, 1997, 272, pages 1363-1367]. In addition, Syk, seems to play an important role in the scheme of CD40 signaling, which plays an important role in the proliferation of B cells [M.Faris et al., J.Exp. Med., 1994, 179, pages 1923-1931].

In addition, Syk is involved in the activation of platelets stimulated due to the low affinity IgG receptor (Fc gamma RIIA) or stimulated collagen [F.Yanaga et al., Biochem. J., 1995, 311, (Pt. 2) pages 471-478].

Focal adhesion kinase (FAK) is preceptory receptor that is involved in the transduction schemes integrin-indirectly signal. FAK colocalizes with integrins at sites of focal contact and FAK activation, and its trainferrovie, as has been demonstrated for many types of cells, depends on the binding of integrins to their extracellular ligands. The results of several studies support the hypothesis that FAK inhibitors may be useful in the treatment of cancer. For example, FAK-deficient cells migrate poorly in response to chemotactically signals, and overexpression of C-terminal domain of FAK inhibits the proliferation of cells, as well as chemotactically migration (Sieg et al, J. Cell Science, 1999, 112, 2677-269; Richardson A. and Parsons, T., Cell, 1997, 97, 221-231); in addition, tumor cells treated with FAK antimyeloma oligonucleotide, lose the ability to attach, and undergo apoptosis (Xu et al, Cell Growth Differ. 1996, 4, 413-418). It was reported that FAK sverkhekspressiya for cancer of the prostate, breast, thyroid and lung. The level of FAK expression directly correlates with tumors demonstrating the most aggressive phenotype.

Angiogenesis, or the formation of new blood vessels by sprouting from pre-existing vascular system, is of great importance for embryonic development and organogenesis. Excessive neovascularization observed in rheumatoid arthritis, diabetic retinopathy and tumor growth (Folkman, Nat. Med., 1995, 1, 27-31). Angiogenesis is a complex multistage process that involves the activation, migration, proliferation and survival of endothelial cells. Intensive research in the field of angiogenesis of tumors in the last two decades has established a number of therapeutic targets, including kinases, proteases and integrins, which led to the discovery of many new anti-angiogenic agents, including receptor containing an embedded domain kinase (KDR, also known as VEGFR-2, the receptor-2 growth factor vascular endothelium)inhibitors, some of which are on toadie time are under clinical evaluation (Jekunen, et al., Cancer Treatment Rev. 1997, 23, 263-286.). Inhibitors of angiogenesis can be used as the basic, additional and even warning means when re-growth of malignant tumors.

Some proteins involved in the segregation of chromosomes and the Assembly of spindles were found in yeast and Drosophila. The destruction of these proteins leads to the violation of the segregation of chromosomes and the formation of a unipolar or destroyed spindles.These kinases are IplI and Aurora kinase from S.cerevisiae and Drosophila, respectively, which is necessary for the separation of centrosomes and segregation of chromosomes. One homologue of yeast Ipll man was recently cloned and characterized by different laboratories. This kinase, named Aurora2, or STK15 BTAK, belongs to the family of serine/trainingin. Bischoff et al. showed that Aurora2 is oncogenic and amplificated in colorectal cancers in humans (EMBO J, 1998, 17, 3052-3065). It has also been found, for example, for cancer, including epithelial tumors, such as breast cancer.

The receptor for insulin-like growth factor type 1 (IGF1R) is a transmembrane receptor tyrosine kinase that is associated mainly with IGF1, and IGF2 and insulin with lower affinity. The binding of IGF1 to its receptor leads to receptor oligomerization, activation tyrosinemia is s, intermolecular receptor autophosphorylation and phosphorylation of cellular substrates (the two main substrates are IRS1 and Shc). Ligand-activated IGF1R induce mitogenic activity in normal cells. In some clinical reports highlights the important role schema IGF-I in the development of tumors in humans: (i) overexpression of IGF-I-R is frequently found in various tumors (e.g. breast cancer, colon cancer, lung cancer, skin cancer, sarcoma) and is often associated with an aggressive phenotype; (ii) high concentrations of circulating IGF1 correlate well with the risk of prostate, lung and breast cancer; (iii) epidemiological studies consider IGF1 Aksisas a factor of predisposition in the pathogenesis of breast cancer and prostate [Baserga R. The IGF-I receptor in cancer research, Exp Cell Res. (1999) 253:1-6; Baserga R. The contradictions of the JGF1-Receptor, Oncogene (2000) 19: 5574-81; Khandwala HM. et al. The effects of IGFs on tumorigenesis and neoplastic growth, Endocrine Reviews (2000) 21:215-44; Adams TE et al. Structure and function of the IGF 1 R, CMLS (2000) 57: 1050-93].

In international patent application PCT/US/00/15181, filed June 2, 2000, revealed a series of 2-substituted benzimidazole, indoles, benzoxazoles and benzothiazoles, which reportedly can be used for inhibition of cell death.

The authors found a new group substituted azaindole, which have CE is different pharmaceutical properties, in particular the ability to inhibit protein kinases, more specifically, the ability to inhibit Syk kinase, Aurora2, KDR, FAK and IGF1R.

Thus, in one aspect the present invention relates to pharmaceutical compositions comprising compounds of General formula (I):

where

R1represents aryl or heteroaryl, each of which is optionally substituted by one or more groups selected from alkylenedioxy, alkenyl, alkenylacyl, quinil, aryl, cyano, halogen, hydroxy, heteroaryl, geterotsiklicheskie, nitro, R4, -C(=O)-R, -C(=O)-OR5, -C(=O)-NY1Y2, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2and Z2R;

R2is hydrogen, acyl, cyano, halogen, lower alkenyl, -Z2R4, -SO2NY3Y4, -NY1Y2or lower alkyl, optionally substituted Deputy selected from aryl, cyano, heteroaryl, geterotsiklicheskie, hydroxy, -Z2R4, -C(=O)-NY1Y2, -C(=O)-R, -CO2R8, -NY3Y4, -N(R6)-C(=O)-R, -N(R6)-C(=O)-NY1Y2, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2NY1 Y2and one or more halogen atoms;

R3represents hydrogen, aryl, cyano, halogen, heteroaryl, lower alkyl, -Z2R4, -C(=O)-OR5or-C(=O)-NY3Y4;

R4represents alkyl, cycloalkyl, cycloalkenyl, heteroseksualci or geterotsiklicheskikh, each of which is optionally substituted by a Deputy selected from aryl, cycloalkyl, cyano, halogen, heteroaryl, geterotsiklicheskie, -CHO (or a derivative of 5-, 6 - or 7-membered cyclic acetal), -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -Z3R7and one or more groups selected from hydroxy, alkoxy and carboxy;

R5represents hydrogen, alkyl, alkenyl, aryl, arylalkyl, heteroaryl or heteroaromatic;

R6represents hydrogen or lower alkyl;

R7represents alkyl, aryl, arylalkyl, cycloalkyl, cycloalkenyl, heteroaryl, heteroaromatic, heteroseksualci or geterotsiklicheskikh;

R8represents hydrogen or lower alkyl;

R represents aryl or heteroaryl; alkenyl; or alkyl, cycloalkyl, cycloalkenyl, heteroseksualci or geterotsiklicheskikh, each of which is optionally substituted by a Deputy selected is output from aryl, cycloalkyl, cyano, halogen, heteroaryl, geterotsiklicheskie, -CHO (or a derivative of 5-, 6 - or 7-membered cyclic acetal); -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -Z3R7and one or more groups selected from hydroxy, alkoxy and carboxy;

X1represents N, CH, C-aryl, C-heteroaryl, C-heteroseksualci, C-geteroseksualen, C-halogen, C-CN, C-R4C-NY1Y2C-OH, C-Z2R, C-C(=O)-R, C-C(=O)-OR5C-C(=O)-NY1Y2C-N(R8)-C(=O)-R, C-N(R6)-C(=O)-OR7C-N(R6)-C(=O)-NY3Y4C-N(R6)-SO2-NY3Y4C-N(R6)-SO2-R, C-SO2-NY3Y4C-NO2or-alkenyl or C-quinil, optionally substituted by one or more groups selected from aryl, cyano, halogen, hydroxy, heteroaryl, geterotsiklicheskie, nitro, -C(=O)-NY1Y2, -C(=O)-OR5, -NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4, -SO2-NY1Y2and Z2R4;

Y1and Y2independently represent hydrogen, alkenyl, aryl, cycloalkyl, heteroaryl or alkyl, optionally substituted by one or b is more groups, selected from aryl, halogen, heteroaryl, geterotsiklicheskie, hydroxy, -C(=O)-NY3Y4, -C(=O)-OR5, -NY3Y4, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4and OR7; or the group-NY1Y2may form a cyclic amine;

Y3and Y4independently represent hydrogen, alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl or heteroaromatic; or the group-NY3Y4may form a cyclic amine;

Z1represents O or S;

Z2represents O or S(O)n;

Z3represents O, S(O)n, NR6;

n means zero or an integer 1 or 2;

or their corresponding N-oxides, proletarienne forms, bioisostere acid, pharmaceutically acceptable salt or solvate (e.g., hydrates) of such compounds and their N-oxides, proletarienne forms and bioisostere acid; together with one or more pharmaceutically acceptable carriers or excipients.

In another aspect, the present invention relates to compounds of formula (I)as defined above, but excluding the compounds listed below:

2-phenyl-1H-pyrrolo[2,3-b]pyridine,

2-(4-bromophenyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine,

methyl ester of 4-(3-methyl-1H-pyrrolo[2,3-b]pyridine-2-yl)benzoic acid,

2-(4-chlorophenyl)-1H-p is Rolo[2,3-b]pyridine,

2-(4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine,

5-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

4-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

2-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine,

4-(3-methyl-1H-pyrrolo[2,3-b]pyridine-2-yl)benzoic acid,

2-(4-methoxyphenyl)-3-methyl-1H-pyrrolo[2,3-b]pyridine,

2-(4-were)-3-methyl-1H-pyrrolo[2,3-b]pyridine,

isopropyl ester of 4-(3-methyl-1H-pyrrolo{2,3-b]pyridine-2-yl)benzoic acid,

2-phenyl-3-methyl-1H-pyrrolo[2,3-b]pyridine,

5-bromo-2-phenyl-3-methyl-1H-pyrrolo[2,3-b]pyridine,

6-chloro-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

6-chloro-4-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

4-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-iceboxlogic,

2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-ylacetonitrile,

2-phenyl-3-prop-1-enyl-1H-pyrrolo[2,3-b]pyridine,

4-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-iceboxlogic,

dimethyl(2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-ylmethyl)amine,

2,2'-diphenyl-1H,1'H-[3,3']bi[pyrrolo(2,3-b]pyridinyl],

2-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-yl)acetamide", she

3-allyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

(2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-yl)acetonitrile,

2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde,

3-morpholine-4-ylmethyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine,

N-[2-(2-phenyl-1H-pyrrolo[2,3-b]pyridine-3-yl)ethyl]acetamide", she

6-phenyl-5H-pyrrolo[2,3-b]pyrazin,

6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin,

6-(4-chlorophenyl)-5H-pyrrolo[2,3-b]pyrazin,

6-(2-CHL is henyl)-5H-pyrrolo[2,3-b]pyrazin,

3-methyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin,

2-methyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin and

7-methyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin.

It is understood that in the description of the present invention, the term "compounds of the present invention", and equivalent expressions include compounds of General formula (1)as defined above, and the expression includes proletarienne form, pharmaceutically acceptable salt and solvate such as a hydrate, if appropriate to the context. Similar links to intermediate compounds, regardless of whether declared or not they include their salts and solvate, if it fits the context. In order to clarify, if it is in the context presents specific examples, but these examples are merely illustrative and are not intended to exclude other, if they match the context.

In the sense used above and hereinafter throughout the description of the invention, common terms, unless otherwise indicated, have the following meanings:

"Patient" includes both human and other mammals.

"Bioisostere acid" means a group that has a chemical or physical similarity and has similar biological properties with a carboxyl group (see Lipinski, Annual Reports in Medicinal Chemistry, 1986, 21, p 283 "Bioisosterism In Drug Design"; Yun, Hwdhak Sekye, 1993, 33, pages 576-579 "Application Of Bioisostrism To New Drug Design"; Zhao, Huaxue Tongbao, 1995, pages 34-38 "Bioisosteric Replacement and Development Of Lead Compounds In Drug Design"; Graham, Theochem, 1995, 343, pages 105-109 "Theoretical Studies Applied To Drug Design: ab initio Electronic Distributions In Bioisosteres"). Examples of suitable bioisostere acid include-C(=O)-NHOH, -C(=O)-CH2OH, -C(=O)CH2SH, -C(=O)-NH-CN, sulpho, phosphono, alkylsulphonyl, tetrazolyl, arylcarbamoyl, heteroarylboronic, N-methoxycarbonyl, 3-hydroxy-3-cyclobutene-1,2-dione, 3,5-dioxo-1,2,4-oxadiazolidine or heterocyclic phenols such as 3-hydroxyisoquinoline and 3-hydroxy-1-methylpyrazole.

"Acyl" means an H-CO - or alkyl-CO-group in which the alkyl group has the specified values.

"Acylamino" represents an acyl-NH-group, where the acyl has the specified values.

"Alkenyl" means an aliphatic hydrocarbon group containing a carbon-carbon double bond, which may be unbranched or branched, containing from about 2 to about 15 carbon atoms in the chain. Preferred alkeneamine groups contain from 2 to about 12 carbon atoms in the chain; and more preferably from 2 to about 6 carbon atoms (for example of 2-4 carbon atoms in the chain. The term "branched" in the sense in which it is used, and throughout the text means that one or more lower alkyl groups such as methyl, ethyl or propyl, are attached to a linear chain; in this case, the linear alkenylphenol goal is I. "Lower alkenyl" means from about 2 to about 4 carbon atoms in the chain, which may be unbranched or branched. Examples alkenyl groups include ethynyl, propenyl, n-butenyl, Isobutanol, 3-methylbut-2-enyl, n-pentenyl, heptenyl, octenyl, cyclohexylmethanol and decenyl.

"Alkenylacyl is alkenyl-O-group, where alkenyl has the above values. Examples of alkenylacyl include allyloxy.

"Alkoxy" means alkyl-O-group in which the alkyl group has the above values. Examples of alkoxygroup include deformedarse, methoxy, triptoreline, ethoxy, n-propoxy, isopropoxy, n-butoxy, heptox.

"Alkoxycarbonyl" means alkyl-O-CO-group in which the alkyl group has the above values. Examples alkoxycarbonyl groups include methoxy and etoxycarbonyl.

"Alkyl" means, unless otherwise specified, an aliphatic hydrocarbon group, which may be unbranched or branched chain, containing from about 1 to about 15 carbon atoms in the chain, optionally substituted by one or more halogen atoms. Specific alkyl groups contain from 1 to about 6 carbon atoms. "Lower alkyl" as a group or part of the lower alkoxy, the lower alkylthio, lower alkylsulfonyl or lower alkylsulfonyl group means, if no other in the of asani, aliphatic hydrocarbon group, which may be unbranched or branched chain, containing from 1 to about 4 carbon atoms in the chain. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 3-pentyl, heptyl, octyl, nonyl, decyl and dodecyl. Examples of alkyl groups substituted by one or more halogen atoms include trifluoromethyl.

"Alkylene" means aliphatic divalent radical derived from an unbranched or branched alkyl group in which the alkyl group has the above values. Examples alkilinity radicals include methylene, ethylene and trimethylene.

"Alkylenedioxy" means-O-alkylene-O-group in which alkylene has the above values. Examples of alkylenedioxy include methylenedioxy, Ethylenedioxy.

"Alkylsulfonyl" means alkyl-SO-group in which the alkyl group has the above values. Preferred alkylsulfonyl groups are those in which the alkyl group is a C1-4alkyl.

"Alkylsulfonyl" means an alkyl-SO2-the group in which the alkyl group has the above values. Preferred alkylsulfonyl groups are those in which the alkyl group is a C1-4alkyl.

"Alkylsulfonyl the sludge" means alkyl-SO 2-NH-C(=O)-group in which the alkyl group has the above values. Preferred alkylsulfonyl groups are those in which the alkyl group is a C1-4alkyl.

"Alkylthio" means alkyl-S-group in which the alkyl group has the above values. Examples of alkylthio groups include methylthio, ethylthio, isopropylthio, reptillia.

"Quinil" means an aliphatic hydrocarbon group containing a carbon-carbon triple bond, and this group may be unbranched or branched chain, containing from about 2 to about 15 carbon atoms in the chain. Preferred alkyline groups contain from 2 to about 12 carbon atoms in the chain; and more preferably from 2 to about 6 carbon atoms (for example of 2-4 carbon atoms in the chain. Examples etkinlik groups include ethinyl, PROPYNYL, n-butynyl, Isobutanol, 3-methylbut-2-inyl and n-pentenyl.

"Aroyl" means an aryl-CO-group in which the aryl group has the above values. Examples rolnych groups include benzoyl and 1 - and 2-naphtol.

"Aroylamino" means aroyl-NH-group, where aroyl has the above values.

"Aryl" as a group or part of a group denotes: (i) optionally substituted monocyclic or polycyclic aromatic carbocyclic fragment from about 6 to about 14 ATO is s carbon such as phenyl or naphthyl; or (ii) an optionally substituted partially saturated polycyclic aromatic carbocyclic fragment, in which aryl and cycloalkyl or cycloalkenyl group condensed together with the formation of a cyclic structure, such as tetrahydronaphthalene, ingenernoe or indanamine ring. Except when given other definitions, aryl groups can be substituted by one or more substituents of aryl groups which may be the same or different, where the expression "Deputy aryl group" includes, for example, acyl, acylamino, alkoxy, alkoxycarbonyl, alkylenedioxy, alkylsulfonyl, alkylsulfonyl, alkylthio, aroyl, aroylamino, aryl, arylalkyl, arylalkylamines, arylalkyl, aryloxy, aryloxyalkyl, arylsulfonyl, arylsulfonyl, aaltio, carboxy (or bioisostere acid), cyano, halogen, heteroaryl, heteroaryl, heteroaromatic, heteroaromatic, heteroaromatic, hydroxy, nitro, trifluoromethyl, -NY3Y4, -CONY3Y4, -SO2NY3Y4, -NY3-C(=O)alkyl, -NY3SO2alkyl or alkyl, optionally substituted aryl, heteroaryl, hydroxy, or-NY3Y4.

"Arylalkyl" means arylalkyl the group in which the aryl and alkyl fragments have the above values. predpochtitelnye arylalkyl groups contain From 1-4the alkyl fragment. Examples arylalkyl groups include benzyl, 2-phenethyl and naphthalenethiol.

"Arylalkyl" means arylalkyl-O-group in which kilakila the group has the above values. Examples of arylalkylamine include benzyloxy and 1 - or 2-naphthalenyloxy.

"Arylalkylamines" means arylalkyl-O-CO-group in which arylalkyl has the above values. Example arylalkylamines group is benzyloxycarbonyl.

"Arylalkyl" means arylalkyl-S-group in which kilakila the group has the above values. An example of arylalkyl group is benzylthio.

"Aryloxy" means aryl-O-group in which the aryl group have the above values. Examples of aryloxy include phenoxy, naphthoxy, each of which is optionally substituted.

"Aryloxyalkyl" means aryl-O-C(=O)-group in which the aryl group has the above values. Examples aryloxyalkyl groups include phenoxycarbonyl and mattoxicator.

"Arylsulfonyl" means aryl-SO-group in which the aryl group has the above values.

"Arylsulfonyl" means aryl-SO2-the group in which the aryl group has the above values.

"Arylcarbamoyl" means aryl-SO2-NH-C(=O)-group in which the aryl group who meet the above values.

"Aristeo" means an aryl-S-group in which the aryl group has the above values. Examples of aaltio groups include phenylthio, naphthylthio.

"Azaheterocycle" means an aromatic carbocyclic fragment containing from about 5 to about 10 ring members in which one member of the ring is a nitrogen, and the other member ring selected from carbon, oxygen, sulfur and nitrogen. Examples azaheterocyclic groups include benzimidazolyl, imidazolyl, indazolin, indolyl, ethenolysis, pyridyl, pyrimidinyl, pyrrolyl, chinoline, hintline and tetrahydrozoline.

"Cyclic amine" means a 3-8 membered monocyclic cycloalkyl ring system, where one of the carbon atoms of the ring substituted by nitrogen, and which (i) may further contain a group containing a heteroatom selected from O, S, SO2or NY7(where Y7represents hydrogen, alkyl, aryl, arylalkyl, -C(=O)-R7-C(=O)-OR7or-SO2R7); and (ii) may be condensed with an additional aryl (e.g. phenyl), heteroaryl (e.g., pyridium), heteroseksualnymi or cycloalkenyl rings with the formation of the bicyclic or tricyclic ring system. Examples of cyclic amines include pyrrolidine, piperidine, morpholine, piperazine, indoline, pyridorin, tetrahydroquinolin and similar groups.

"C is kloeckener" means a non-aromatic monocyclic or polycyclic ring system, containing at least one carbon-carbon double bond and containing from about 3 to about 10 carbon atoms. Examples of monocyclic cycloalkenyl rings include cyclopentenyl, cyclohexenyl and cycloheptenyl.

"Cycloalkyl" means a saturated monocyclic or bicyclic ring system containing from about 3 to about 10 carbon atoms, optionally substituted by oxo. Examples of monocyclic cycloalkyl rings include3-8cycloalkyl rings, such as cyclopropyl, cyclopentyl, cyclohexyl and cycloheptyl.

"Cycloalkenyl" means cycloalkylcarbonyl group, in which cycloalkenyl and alkyl fragments has the above values. Examples of monocyclic cycloalkenyl groups include cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl and cycloheptylmethyl.

"Halogen" means fluorine, chlorine, bromine or iodine. Preferred fluorine and chlorine.

"Heteroaryl" means heteroaryl-C(=O)-group in which the heteroaryl group has the above values. Examples of heteroaryl groups include pyridylcarbonyl.

"Heteroaromatic" means heteroaryl-NH-group in which the heteroaryl fragment has the above values.

"Heteroaryl" as a group or part of a group denotes: (i) optionally substituted aromatic monocyclic Il is polycyclic organic fragment, containing from about 5 to about 10 members in the ring, in which one or more ring members is(are) the element(s)different from carbon, for example nitrogen, oxygen or sulfur, (examples of such groups include groups benzimidazolyl, benzothiazolyl, furil, imidazolyl, indolyl, indolizinyl, isoxazolyl, izochinolina, isothiazoline, oxadiazolyl, pyrazinyl, pyridazinyl, pyrazolyl, pyridyl, pyrimidinyl, pyrrolyl, gasoline, chinoline, 1,3,4-thiadiazolyl, thiazolyl, tanila and triazolyl, optionally substituted by one or more groups of the aryl substituents as above, unless otherwise indicated); (ii) optionally substituted partially saturated polycyclic heteroeroticism fragment, in which the heteroaryl and cycloalkyl or cycloalkenyl group condensed with each other to form a cyclic structure (examples of such groups include pyridinoline group, optionally substituted by one or more substituents of aryl groups, as defined above, unless there are other definitions). Optional substituents include one or more substituents of aryl groups, as defined above, unless there are other definitions.

"Heteroaromatic" means heteroallyl the group in which the heteroaryl and alkyl fragments have the t values above. Preferred heteroallyl groups contain From1-4the alkyl fragment. Examples heteroarylboronic groups include pyridylmethyl.

"Heteroaromatics" means heteroallyl-O-group in which heteroallyl the group has the above values. Examples of heterokaryosis include optionally substituted, pyridyloxy.

"Heteroaromatic" means heteroaryl-O-group in which the heteroaryl group has the above values. Examples of heterokaryosis include optionally substituted, pyridyloxy.

"Heteroarylboronic" means heteroaryl-SO2-NH-C(=O)-group in which the heteroaryl group has the above values.

"Geteroseksualen" means cycloalkenyl group that contains one or more heteroatoms, or a group containing a heteroatom selected from O, S and NY7.

"Heteroseksualci" means: (i) cycloalkyl group containing from about 3 to 7 members in the ring which contains one or more heteroatoms or containing a heteroatom group selected from O, S and NY7and may be optionally substituted by oxo; (ii) partially saturated polycyclic heteroeroticism fragment, in which aryl (or heteroaryl) ring, each optionally substituted by one or more substituents of aryl GRU is p", and heterocytolysine group condensed together with the formation of cyclic structures. (Examples of such groups include groups Romania, dihydrobenzofuranyl, indolinyl and perindopril.)

"Geterotsiklicheskikh" means geterotsiklicheskikh group, in which heterocytolysine and alkyl fragments have the above values.

"Proletarienne form" means a compound that is converted in vivo as a result of metabolism (e.g., by hydrolysis) to a compound of formula (I), including its N-oxides. For example, ester compounds of formula (I)containing a hydroxy-group, by hydrolysis in vivo can be transformed into the original molecule. Alternatively, the ester compounds of formula (I)containing carboxypropyl, can be converted by hydrolysis in vivo to the original molecule.

Suitable esters of compounds of formula (I)containing a hydroxy-group, are for example acetates, citrates, lactates, tartratami, malonate, oxalates, salicylates, propionate, succinate, fumarate, maleate, methylene-bis-β-hydroxynaphthoate, 2,5-dihydroxybenzoate, 2-hydroxyethanesulfonic, di-p-toluoyltartaric, methansulfonate, econsultancy, bansilalpet, p-toluensulfonate, cyclohexylsulfamate and esters Hinn acid.

Suitable esters with which dinani formula (I), contains carboxypropyl are, for example, disclosed in the publication F.J.Leinweber, Drug Metab. Res., 1987, 18, page 379.

Suitable esters of compounds of formula (I)containing as carboxypropyl, and the hydroxy-group in the fragment-L1-Y include lactones formed by loss of water between the specified carboxy - and hydroxy groups. Examples of such lactones include caprolactone and butyrolactone.

A particularly suitable class of esters of compounds of formula (I)containing a hydroxy-group, can be obtained from fragments of acids selected from those disclosed Bundgaard et. al., J. Med. Chem., 1989, 32, page 2503-2507, and include substituted (aminomethyl)benzoate, such as dialkylaminomethyl, in which the two alkyl groups may be joined together and/or be interrupted by oxygen atom or optionally substituted nitrogen atom, for example alkilirovanny a nitrogen atom, especially (morpholinomethyl)benzoate, for example, 3 - or 4-(morpholinomethyl)benzoate, and (4-alkylpiperazine-1-yl)benzoate, for example, 3 - or 4-(4-alkylpiperazine-1-yl)benzoate.

In those cases where the compounds of the present invention contain carboxypropyl or enough acid bioisostere, you can get salt accessions grounds, which are easier and more convenient form for use; in practice, the use of salt forms are virtually equivalent is ispolzovanie form of the free acid. The Foundation that you can use to obtain the salts of joining bases, preferably include those that result from the joining of the free acid form pharmaceutically acceptable salts, i.e. salts, the cations of which are non-toxic to the patient in pharmaceutical doses of the salts, so that a favorable inhibiting effects inherent in the free bases are not impaired by side effects, which are attributed to the cations. Pharmaceutically acceptable salts, including salts derived from alkali and alkaline earth metals, in the scope of the present invention include those derived from the following bases: sodium hydride, sodium hydroxide, potassium hydroxide, calcium hydroxide, aluminum hydroxide, lithium hydroxide, magnesium hydroxide, zinc hydroxide, ammonia, Ethylenediamine, N-methylglucamine, lysine, arginine, ornithine, choline, N,N'-dibenziletilendiaminom, chloroprocaine, diethanolamine, procaine, N-benzilpenitsillinom, diethylamine, piperazine, Tris(hydroxymethyl)aminomethane, hydroxide of Tetramethylammonium etc.

Some of the compounds of the present invention are alkaline, and these compounds can be used in free base form or in the form of their pharmaceutically acceptable salts accession acid.

Salt accession Ki the lots are more convenient to use the form; in practice, use of the salt form is almost equivalent to using the form of the free base. Acids which can be used to obtain salt accession acid, preferably include those that result from the joining of the free base form of pharmaceutically acceptable salts, i.e. salts, the anions of which are non-toxic to the patient in pharmaceutical doses of the salts, so that a favorable inhibiting effects inherent in the free bases are not impaired by side effects, which are attributed to the anions. Although the preferred pharmaceutically acceptable salts of these basic compounds, all of salt accession acids are useful as sources of the form of the free bases, even if the particular salt itself is desired only as an intermediate product as, for example, if the salt get only for purposes of purification and identification, or when it is used as an intermediate connection when receiving a pharmaceutically acceptable salt ion exchange processes. Pharmaceutically acceptable salts within the scope of the present invention include salts derived from mineral acids and organic acids, and include hydrogenogenic, such as hydrochloride and hydrobromide, sulfates, phosphates, nitrates, sulfamate, acetates, citrates, and lactate is, the tartratami, malonate, oxalates, salicylates, propionate, succinate, fumarate, maleate, methylene-bis-β-hydroxynaphthoate, 2,5-dihydroxybenzoate, 2-hydroxyethanesulfonic, di-p-toluoyltartaric, methansulfonate, econsultancy, bansilalpet, p-toluensulfonate, cyclohexylsulfamate and salt Hinn acid.

Apart from the fact that salts of the present invention in and of themselves are useful as active compounds, they can be used for the purposes of cleaning compounds, for example, using the differences in the solubilities of the salts and the parent compounds, by-products and/or source of substances with well-known specialists of ways.

With reference to the above formula (I) below are the particular and preferred groups:

R1in particular may represent optionally substituted heteroaryl, especially optionally substituted azaheterocycle. Examples of optionally substituted azaheterocycle include indolyl, pyridyl, pyrrolyl, pyrazolyl, chinoline, ethenolysis, imidazolyl, indazoles, indolizinyl, tetrahydrozoline and indazolin. Optional substituents include one or more groups selected from alkylenedioxy, alkenyl, alkenylacyl, aryl, cyano, halogen, hydroxy, heteroaryl, geterotsiklicheskie, R4, -C(=O)-R, -C(=O)-OR5, -C(=O)-NY1Y2, -NY1Y2and-OR. R 1more preferably represents optionally substituted indolyl, optionally substituted indolizinyl or optionally substituted pyrrolyl. R1even more preferably represents optionally substituted indol-3-yl, indolin-1-yl, optionally substituted pyrrol-3-yl, optionally substituted indol-2-yl or optionally substituted pyrrol-2-yl.

R1may also be optionally substituted aryl, especially optionally substituted phenyl. Optional substituents include one or more groups selected from alkylenedioxy, halogen, heteroaryl, hydroxy, R4, -NY1Y2and-OR. R1even more preferably is 4-substituted phenyl, especially 4-tert-arylboronic.

R2may preferably be hydrogen.

R2can also preferable acyl.

R2may also preferably be a halogen.

R2may also preferably be lower alkyl, optionally substituted by cyano, halogen, hydroxy, heteroaryl, -C(=O)-NY1Y2, tetrazolyl, -C(=O)-R, -CO2R8, -NY3Y4, -N(R6)-C(=O)-R, -N(R6)-C(=O)-NY1Y2, -N(R6)-SO2-R7or-N(R6)-SO2-NY3Y4.

R2may also preferably be Isshi of alkenyl.

R3may preferably be hydrogen.

R3may also preferably represent optionally substituted aryl, especially optionally substituted phenyl.

R3may also preferably represent-C(=O)-OR5(for example, -C(=O)-OH).

R3may also preferably be lower alkyl (e.g. methyl).

X1may preferably be n

X1may also preferably be CH.

X1may also preferably be C-halogen, especially C-Cl.

X1may also preferably be C-CN.

X1may also preferably be C-OH.

X1may also preferably be C-aryl (e.g. C-phenyl).

X1may also preferably be C-heteroaryl, especially C-azaheterocycle (for example, C-pyridyl,

X1may also preferably be C-Z2R, especially C-lower alkoxy, more preferably C-OCH3.

X1may also preferably be C-C(=O)-OR5especially C-C(=O)-OH or C-C(=O)-OtBu.

X1may also preferably be With-C(=O)-NY1Y2especially With the-C(=O)-NH2C-C(=O)-NH-CH3,

,

especially predpochtite is) C-C(=O)-NH-C(CH 3)2-CH2OH.

X1may also preferably be C-NY1Y2,

X1may also preferably be C-geteroseksualen (for example,or

It should be understood that the present invention covers all appropriate combinations presented in this description of specific and preferred groups.

A particular variant of the present invention is a compound of formula (I)

where:

R1represents aryl or heteroaryl, each of which is optionally substituted by one or more groups selected from alkylenedioxy, alkenyl, alkenylacyl, quinil, aryl, hydroxy, heteroaryl, geterotsiklicheskie, -C(=O)-R, -C(=O)-NY1Y2, -N(R6)-C(=O)-R7, -N(R6)-C(=O)-NY3Y4, -N(R6)-C(=O)-OR7, -N(R6)-SO2-R7, -N(R6)-SO2-NY3Y4and-SO2-NY1Y2;

or N-oxide, Palekastro form, bioisostere acid, pharmaceutically acceptable salt or MES of such compound; or an N-oxide, Palekastro form or bioisostere acid such salt or MES.

The most preferred group of compounds of the present invention are the joint is of the formula (1a):

in which R2, R3and X1have the values indicated above; R9represents hydrogen, alkenyl or R4; R10is alkenylacyl, carboxy (or bioisostere acid), cyano, halogen, hydroxy, heteroaryl, R4, -C(=O)-R, -C(=O)-NY1Y2, -OR4, -N(R6)-C(=O)-R7, -N(R6)-SO2-R7or-NY1Y2; p is zero or an integer 1 or 2; and the remainderattached in position 1 or 3 of the indole ring; and their corresponding N-oxides, and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and their proletarienne form.

Preferred compounds of formula (1a)in which R2represents hydrogen.

Preferred compounds of formula (1a)in which R3represents hydrogen.

Preferred compounds of formula (1a), in which X1is:

(i) N;

(ii) CH;

(iii) C-aryl (e.g. C-phenyl);

(iv) C-heteroaryl, especially C-azaheterocycle (for example, C-pyridyl or;

(v) C-halogen (for example, C-Cl);

(vi) C-CN;

(vii) C-Z2R, preferably lower alkoxy (e.g.,-och3);

(viii) C-C(=O)-OR5preferably-C(=O)-OtBu;

(ix) C-C(=O)-NY1Y2(for example, C-C(=O)-NH-CH 3C-C(=O)-NH-CH2-CH2OH, C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or C-C(=O)-NH-CH2CH2OCH3especially C-C(=O)-NH-C(CH3)2-CH2OH; or

(x)-NY1Y2(for example,

,

especiallythe preferred. The compounds of formula (Ia)in which X1is N, C-H, C-CN,,or-C(=O)-NH-C(CH3)2-CH2OH is particularly preferred.

Preferred compounds of formula (1a)in which R9is:

(i) hydrogen;

(ii)1-4alkyl [e.g.,- CH3or-CH2CH3];

(iii)1-4alkyl, substituted by hydroxy [e.g.,- CH2OH, -CH2CH2OH or-CH2CH2CH-OH];

(iv)1-4alkyl, substituted-N(R6)C(=O)-R7[for example, -CH2CH2CH2NHC(=O)CH3];

(v)1-4alkyl, substituted-C(=O)-NY1Y2[for example,oror

(vi) cycloalkenyl, substituted by hydroxy [e.g.,preferred.Especially preferred compounds of formula (1a)in which R9represents hydrogen, -CH3or-CH2CH3.

Preferably the compounds of formula (1a), in which R10is:

(i) carboxy or bioisostere acid (for example,

(ii) hydroxy;

(iii) alkyl substituted carboxy [e.g.- CH2CH2CO2H];

(iv) alkyl substituted-N(R6)-SO2-R7[for example,

(v)alkyl, substituted-N(R6)-CO-NY3Y4[for example,

(vi) heteroaryl [for example,or pyridyl];

(vii) -OR4where R4is alkyl [e.g.,- OCH3];

(viii) OR4where R4represents alkyl or cycloalkyl substituted by one or more hydroxy groups [e.g.,- OCH2CH2OH, -OCH2CH2CH2OH, -OCH(CH3)CH2OH,

(ix) -OR4where R4represents alkyl substituted by one or more alkoxygroup [e.g.,- OCH(CH3)CH2OCH3];

(x) -OR4where R4represents alkyl or cycloalkyl substituted by one or more carboxyglutamic [e.g.,- OCH2CO2H, -OCH(CH3)CO2H,

(xi) -OR4where R4is cycloalkyl, substituted-C(=O)-NY1Y2[for example,or

(xii) -C(=O)-where R is alkyl [e.g., -C(=O)-CH3];

(xiii) -C(=O)-NY1Y2[for example, -CONH2, -CONHCH3, -CONHCH(CH2OH)2, -CONHCH2CH2OH, -CONHC(CH3)2CH2OH, -C(=O)-NH-CH2-C(CH3)2-OH, -C(=O)-NH-CH2-CH2-CO2H, -CONHCH2CH2OCH3, -CONHCH2CH2CONH2oror

(xiv) -N(R6)-C(=O)-R7[for example, -NHC(=O)CH3].

Especially preferred compounds of formula (1a)in which R10represents carboxy, pyridyl,or-CONHC(CH3)2CH2OH, -C(=O)-NH-CH2-C(CH3)2-OH, or-CONHCH2CH2OCH3.

If p is 1, R10preferably attached in position 5 or position 6, entailing rings. If p is 2, the groups R10preferably attached at positions 5 and 6 Intellinova rings.

A preferred group of compounds of the present invention are the compounds of formula (1a)in which R2is hydrogen; R3represents hydrogen; X1represents CH, C-aryl [e.g. C-phenyl], C-heteroaryl, [for example, C-pyridyl orC-halogen [e.g., C-Cl], C-CN, C-lower alkoxy [e.g., C-OCH3], C-C(=O)-OR5[for example, C-C(=O)-OtBu], C-C(=O)-NY1Y2[especially C-C(=O)-NH-CH3C-C(=O)-NH-CH2 -CH2OH], C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or-C(=O)-NH-CH2CH2OCH3more preferably C-C(=O)-NH-C(CH3)2-CH2OH] or C-NY1Y2[especially

R9is

(i) hydrogen;

(ii)1-4alkyl [e.g.,- CH3or-CH2CH3];

(iii)1-4alkyl, substituted by hydroxy [e.g.,- CH2OH, -CH2CH2OH or-CH2CH2CH2OH];

(iv)1-4alkyl, substituted-N(R6)C(=O)R7[for example, -CH2CH2CH2NHC(=O)CH3];

(v)1-4alkyl, substituted-C(=O)-NY1Y2[for example,or; or

(vi) cycloalkenyl, substituted hydroxy; R10is

(i) carboxy or bioisostere acid [for example,

(ii)hydroxy,

(iii) alkyl substituted carboxy [e.g., CH2CH2CO2N];

(iv) alkyl substituted-N(R6)-SO2-R7[for example,

(v) alkyl substituted by-N(R6)-CO-NY3Y4[for example,

(vi) heteroaryl [for example,or pyridyl];

(vii) -OR4where R4p is ecstasy alkyl [e.g., -OCH3];

(viii) OR4where R4represents alkyl or cycloalkyl substituted by one or more hydroxy groups [e.g.,- OCH2CH2OH, -OCH2CH2CH2OH, -OCH(CH3)CH2OH, -OCH2CH(OH)CH3,or-OCH2CH(OH)CH2OH];

(ix) -OR4where R4represents alkyl substituted by one or more alkoxygroup [e.g.,- OCH(CH3)CH2OCH3];

(x) -OR4where R4represents alkyl or cycloalkyl substituted by one or more carboxyglutamic [e.g.,- OCH2CO2H, -OCH(CH3)CO2H or;

(xi) -OR4where R4is cycloalkyl, substituted-C(=O)-NY1Y2[for example,or;

(xii) -C(=O)-R, where R is alkyl [e.g.,- C(=O)-CH3];

(xiii) -C(=O)-NY1Y2[for example, -CONH2, -CONHCH3, -CONHCH(CH2OH)2, -CONHCH2CH2OH, -CONHC(CH3)2CH2OH, -C(=O)-NH-CH2-C(CH3)2OH, -C(=O)-NH-CH2-CH2-CO2H, -CONHCH2CH2OCH3, -CONHCH2CH2CONH2oror

(xiv) -N(R6)-C(=O)-R7[for example, -NHC(=O)CH3]; R10attached in position 5 or position 6 Intellinova rings, if p oz is achet 1, group and R10attached in position 5 and 6 Intellinova rings, if p is 2; and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Another preferred group of compounds of the present invention are the compounds of formula (1a)in which R2is hydrogen; R3represents hydrogen; X1is N; R9is

(i) hydrogen,

(ii)1-4alkyl [e.g.,- CH3or-CH2CH3],

(iii)1-4alkyl, substituted by hydroxy [e.g.,- CH2OH, -CH2CH2OH or-CH2CH2CH2OH],

(iv)1-4alkyl, substituted-N(R6)C(=O)-R7[for example, -CH2CH2CH2NHC(=O)CH3],

(v)1-4alkyl, substituted-C(=O)-NY1Y2[for example,or

(vi) cycloalkenyl, substituted by hydroxy [e.g.,

R10is

(i) carboxy or bioisostere acid [for example,;

(ii)hydroxy;

(iii) alkyl substituted carboxy [e.g., CH2CH2CO2N];

(iv) alkyl substituted-N(R6)-SO2-R7[for example,;

(v) alkyl, someseni is-N(R 6)-CO-NY3Y4[for example,;

(vi) heteroaryl [for example,or pyridyl];

(vii) -OR4where R4is alkyl [e.g.,- OCH3];

(viii) OR4where R4represents alkyl or cycloalkyl substituted by one or more hydroxy groups [e.g.,- OCH2CH2OH, -och(CH3)CH2HE, -och2CH(OH)CH3,or-OCH2CH(OH)CH2OH];

(ix) -OR4where R4represents alkyl substituted by one or more alkoxygroup [e.g.,- OCH(CH3)CH2OCH3];

(x) -OR4where R4represents alkyl or cycloalkyl substituted by one or more carboxyglutamic [e.g.,- OCH2CO2H, -OCH(CH3)CO2H or;

(xi) -OR4where R4is cycloalkyl, substituted-C(=O)-NY1Y2[for example,;

(xii) -C(=O)-R, where R is alkyl [e.g.,- C(=O)-CH3];

(xiii) -C(=O)-NY1Y2[for example, -CONH2, -CONHCH3, -CONHCH(CH2)OH, -CONHCH2CH2OH, -CONHC(CH3)2CH2OH, -C(=O)-NH-CH2-C(CH3)2OH, -C(=O)-NH-CH2-CH2-CO2, -CONHCH2CH2OCH3, -CONHCH2CH2CONH2or or

(xiv) -N(R6)-C(=O)-R7[for example, -NHC(=O)CH3];

the group R10attached in position 5 or position 6 Intellinova rings, if p is 1, and the group R10attached in position 5 and 6 Intellinova rings, if p is 2; and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Another specific group of compounds of the present invention are the compounds of formula (Ib):

in which R2, R3, R9, R10X1and p have the above values, and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of compounds of formula (Ib) and their N-oxides and proletarienne form.

Preferred compounds of formula (1b)in which R2represents hydrogen.

Preferred compounds of formula (1b)in which R3represents hydrogen.

Preferred compounds of formula (1b)in which X1is:

(i) N;

(ii) CH;

(iii) C-aryl (e.g. C-phenyl);

(iv) C-heteroaryl, especially C-azaheterocycle (for example, C-pyridyl or;

(v) C-halogen (for example, C-Cl);

(vi) C-CN;

(vii) C-Z2R, preferably With ISSI alkoxy (for example, C-och3);

(viii) C-C(=O)-OR5preferably-C(=O)-OtBu;

(ix)C-C(=O)-NY1Y2(for example, C-C(=O)-NH-CH3C-C(=O)-NH-CH2-CH2OH, C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or C-C(=O)-NH-CH2CH2OCH3especially C-C(=O)-NH-C(CH3)2-CH2OH; or

,

especially. Especially preferred compounds of formula (1b)in which X1is N, C-H, C-CN,,or-C(=O)-NH-C(CH3)2-CH2OH.

Preferred compounds of formula (1b)in which R9represents hydrogen.

Preferred are also the compounds of formula (1b)in which R9is1-4alkyl [e.g.,-CH3].

Preferred compounds of formula (1b)in which p=0.

A preferred group of compounds of the present invention are the compounds of formula (1b)in which: R2is hydrogen; R3represents hydrogen; X1represents CH, C-aryl [e.g. C-phenyl], C-heteroaryl, [for example, C-pyridyl orC-halogen [e.g., C-Cl], C-CN, C-lower alkoxy [e.g., C-OCH3], C-C(=O)-OR5[for example, C-C(=O)-OtBu], C-C(=O)-NY1Y2[especially C-C(=O)-NH-CH3, -C(=O)-NH-CH 2-CH2OH], C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or-C(=O)-NH-CH2CH2OCH3more preferably C-C(=O)-NH-C(CH3)2-CH2OH, or a-NY1Y2[especially;

R9represents hydrogen or C1-4alkyl [e.g.,- CH3]; p is zero; and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Another preferred group of compounds of the present invention are the compounds of formula (1b)in which: R2is hydrogen; R3represents hydrogen; X1is N; R9represents hydrogen or C1-4alkyl [e.g.,- CH3]; p is zero; and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Another preferred group of compounds of the present invention are the compounds of formula (Ic):

in which R2, R3, R9, R10X1and p have the above values, and the remainderpreferably Ave is linked in position 2 or 3 of the pyrrole ring, and the group -(R10)pattached is preferably in position 4 or 5 of the pyrrole ring, and their corresponding N-oxides and proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of compounds of formula (1C) and their N-oxides and proletarienne form.

Preferred compounds of formula (1C), in which R2represents hydrogen.

Preferred compounds of formula (1C), in which R3represents hydrogen.

Preferred compounds of formula (1C), in which X1is:

(i) N;

(ii) CH;

(iii) C-aryl (e.g. C-phenyl);

(iv) C-heteroaryl, especially C-azaheterocycle (for example, C-pyridyl or.

(v) C-halogen (for example, C-Cl);

(vi) C-CN;

(vii) C-Z2R, preferably lower alkoxy (e.g.,-och3);

(viii) C-C(=O)-OR5preferably-C(=O)-OtBu;

(ix) C-C(=O)-NY1Y2(for example, C-C(=O)-NH-CH3C-C(=O)-NH-CH2-CH2OH, C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or C-C(=O)-NH-CH2CH2OCH3especially C-C(=O)-NH-C(CH3)2-CH2OH; or

(x)

,

especially. Especially preferred compounds of formula (1C), in which X1is N, C-H, C-CN, ,or-C(=O)-NH-C(CH3)2-CH2OH.

Preferred are also the compounds of formula (1C), in which R9is1-4alkyl [e.g.,- CH3].

A particular variant of the invention is represented by compounds of formula (1C), in which R9represents optionally substituted C1-4alkyl.

Preferred compounds of formula (1C), in which R=1.

Preferred compounds of formula (1C), in which R10represents aryl [e.g. phenyl].

A particular variant of the invention is represented by compounds of formula (1C), in which R10represents optionally substituted aryl or optionally substituted heteroaryl.

A preferred group of compounds of the present invention are the compounds of formula (1C), in which R2is hydrogen; R3represents hydrogen; X1represents CH, C-aryl [e.g. C-phenyl], C-heteroaryl, [for example, C-pyridyl orC-halogen [e.g., C-Cl], C-CN, C-lower alkoxy [e.g., C-OCH3], C-C(=O)-OR5[for example, C-C(=O)-OtBu], C-C(=O)-NY1Y2[especially C-C(=O)-NH-CH3C-C(=O)-NH-CH2-CH2OH, C-C(=O)-NH-CH2-CH(CH3)OH, C-C(=O)-NH-CH2-C(CH3)2-OH, C-C(=O)-NH-C(CH3)2-CH2OH or-C(=O)-NH-CH2CH2OCH3]more preferably C-C(=O)-H,-C(CH 3)2-CH2OH] or C-NY1Y2[especially;

R9is1-4alkyl [e.g.,- CH3]; R=1; R10represents aryl [e.g. phenyl], and the corresponding N-oxides, and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Another preferred group of compounds of the present invention are the compounds of formula (1C), in which R2is hydrogen; R3represents hydrogen; X1is N; R9is1-4alkyl [e.g.,- CH3]; p=1; R10represents aryl [e.g. phenyl], and the corresponding N-oxides and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

A particular variant of the present invention are compounds of formula (Ic), where R9is1-4alkyl, substituted alkoxy, or C1-4alkyl, substituted-NY1Y2; and R10is optionally substituted heteroaryl or optionally substituted aryl.

Another specific group of compounds of the present invention are the compounds of formula (Id):

in which R , R3, R10X1and p have the above values, and the corresponding N-oxides, and their proletarienne form; and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of formula (Id)in which R2is:

(i) hydrogen;

(ii) lower alkyl (e.g. methyl);

(iii) lower alkyl substituted-CONY1Y2(for example, -CH2CH2CONH2or-CH2CH2CONHCH3);

(iv) lower alkyl, substituted carboxy (e.g.,- CH2CH2CO2H);

(v) lower alkyl, substituted tetrazolium (for example,;

(vi) lower alkyl, substituted by hydroxy (e.g.,- CH2CH2CH2OH or-CH2CH2C(CH3)2OH);

(vii) lower alkyl, substituted-N(R6)-SO2-R7(for example, -CH2CH2CH2NHSO2CH3);

(viii) lower alkyl, substituted-N(R6)-C(=O)-R (for example, -CH2CH2CH2NHC(=O)CH3); or

(ix) lower alkyl, substituted-C(=O)-R (for example, -CH2CH2C(=O)CH3).

Preferred compounds of formula (Id)in which R3represents hydrogen.

Preferred compounds of formula (Id)in which X1is N.

Preferred compounds of formula (Id)in which p=1.

p> Preferred compounds of formula (Id)in which R10is alkyl [e.g., tert-butyl].

R10preferably attached in position 4.

A preferred group of compounds of the present invention are the compounds of formula (Id)in which: R2is:

(i) hydrogen;

(ii) lower alkyl (e.g. methyl);

(iii) lower alkyl substituted-CONY1Y2(for example, -CH2CH2CONH2or-CH2CH2CONHCH3);

(iv) lower alkyl, substituted carboxy (e.g.,- CH2CH2CO2H);

(v) lower alkyl, substituted tetrazolium (for example,;

(vi) lower alkyl, substituted by hydroxy (e.g.,- CH2CH2CH2OH or-CH2CH2C(CH3)2OH);

(vii) lower alkyl, substituted-N(R6)-SO2-R7(for example, -CH2CH2CH2NHSO2CH3);

(viii) lower alkyl, substituted-N(R6)-C(=O)-R (for example, -CH2CH2CH2NHC(=O)CH3); or

(ix) lower alkyl, substituted-C(=O)-R (for example, -CH2CH2C(=O)CH3);

R3represents hydrogen; X1is N; p=1; R10is alkyl [e.g., tert-butyl] and R10attached in position 4; and the corresponding N-oxides, and their proletarienne form; and pharmaceutically acceptable salts and Sol is wool (for example, hydrates) of such compounds and their N-oxides and proletarienne form.

Specific compounds of the present invention of formula (I) selected from the compounds formed as a result of the merger of the atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in the heteroaromatic ring of one of the fragments (B103-B116), are presented in table 2.

Specific compounds of the present invention of the formula (1a) selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in the five-membered ring of one of the fragments (B1 to B39 or B117-B123), are presented in table 2, and joining the carbon atom (C*) of the phenyl ring in one of the fragments (B1 to B39 or B117-B123), are presented in table 2, the oxygen atom (*O one of the fragments (C1-C19 or C79-C96), are presented in table 3.

Specific compounds of the present invention of the formula (1a) is also selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in the five-membered ring of one of the fragments (B1 to B39 or B117-B123), are presented in table 2, and joining the carbon atom (C*) of the phenyl ring in one of the fragments (B1 to B39 or B117-B123), predstavlennyh table 2, to the carbon atom (*C) one of the fragments (C20-C44, C47-C61, C65-C78 or C97), are presented in table 3.

Specific compounds of the present invention of the formula (1a) selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) five-membered ring of one of the fragments (B1 to B39), are presented in table 2, and joining the carbon atom (C*) of the phenyl ring in one of the fragments (B1 to B39), are presented in table 2, to one of the nitrogen atoms (*N) fragments (C45, C62 or C63) or hydrogen atom (*H, fragment C46), or fluorine atom (*F, fragment C64)presented in table 3.

Specific compounds of the present invention of the formula (1b) is selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in the five-membered ring of one of the pieces of indolizino (B40 or B41), are presented in table 2, and joining the carbon atom (C*) six-membered ring of one of the pieces of indolizine (B40 or B41), are presented in table 2, to (i) the oxygen atom (O) of one of the fragments (C1-C19 or C79-C96), (ii) the carbon atom (*C) one of the fragments (C20-C44, C47-C61, C65-C78 or C97), (iii) the nitrogen atom (*N) of one of the fragments (C45, C62 or C63), (iv) hydrogen atom (*H, fragment (C46))or (v) fluorine atom (*F, fragment C64)presented in table 3.

Specific compounds of the present invention of the formula (1b) is selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in the movie indolizine (B42), are presented in table 2.

Specific compounds of the present invention of the formula (1c) selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1-A87), are presented in table 1 to the carbon atom (*C) in one of the fragments of pyrrole (B43 B54), are presented in table 2.

Specific compounds of the present invention of the formula (1d) is selected from the compounds formed by joining the carbon atom (C*) of one of the pieces of azaindole (A1 or A29, A61 or A64-A66), are presented in table 1 to the carbon atom (*C) in one of the fragments (B55-B100) are presented in table 2.

tr>
Table 1
A1A2
A3A4
A5A6
A7A8
A9A10
A11A12
A13A14
A15A16
A17A18
A19A20
A21 A22
A23A24
A25A26
A27A28
A29A30
A31A32
A33A34
A35A36
A37A38
A39A40
A41A
A43A44
A45A46
AA48 motorway
AA50
A51 motorwayA52
A53A54
A55 A56
A57A58 motorway
A59A60
A61A62
A63A
A65A66
A67A68
AA70
A71A72
A73 motorwayA74
A75A76
AA
AA80
A81A82
AA
A85A86
87 motorway
Table 2
B1 B2
B3B4
B5B6
V7B8
B910
B11B12
B13B14
B15B16
B17B18
B19In20
B21B22
WIn 24
V25W
27B28
WB30
WV32
WW
W W
WW
WIn40
B41 contentW
WB44
WB46
B47W
W50
WW
WW
WW
WW
WB60
WW
WW
B65W
WW
W70
WW
B73W
WW
WW
WB80
WW
WW
WW
W W
WW
WB92
WW
B95B96
WW
99B100
WW
103W
WW
WW
WW
WW
WW
WW
WW
WW
W W
W
Table 3
C1*O-CH3C2
C3C4
C5C6
C7C8
C9C10*O-N
C11C12
C13C14
C15 C16
C17C18
C19C20
C21C22
C23C24
C25S
On 27S
SC30
A31C32)
SS
SC36
SS
SC40
C41S
SS
C45S*N.
SC48
SWith50
SC52
SS
SS
SC58
SC60
SS
S*NH2S*F
S*CNS
SS
SC70*CH2-NH-CO-CH3
S*CH2-NH2S
SS
SS
SC78
SS
SS
SS
SS
SS
SC90
SS
SS
SS*O-CF2H
S

Specific compounds of the present invention of formula (1) can be represented as the product of all combinations of each of the groups A1-87 Motorway in table 1, each of the groups B1-B13 in table 2 and each of the groups C1-s in table 3. Further particular compounds of the present invention of formula (1) can be represented as the product of all combinations of each of the groups A1-87 Motorway in table 1 and each of the groups B1-V in table 2.

<> For example, combinations that can be represented as A1-B1-C1, are the product of the combination of group A1 in table 1 and B1 in table 2 and C1 in table 3, namely,

further disclosed in example 1(a).

Specific compounds covered by this invention include all compounds that represent each of the combinations 87 motorway A1 to B1 to V-C1 to s and each of the combinations A1-87 Motorway-B1-U.

Specific compounds of the present invention are:

6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(3-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin;

7-isopropyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin;

6-(4-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin;

2-(4-bromophenyl)-1H-pyrrolo[2,3-b]pyrazin;

6-(4-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(3-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

2-(5H-pyrrolo[2,3-b]pyrazin-6-yl)quinoline;

3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)isoquinoline;

6-[1-methyl-1H-indol-5-yl]-5H-pyrrolo[2,3-b]pyrazin;

6-(5-methoxy-1-methyl-1H-indol-3-yl)-2-methyl-5H-pyrrolo[2,3-b]pyrazin;

3-methyl-6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-benzyl-5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-1H-pyrrol-2-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-indolizine-1-yl-5H-pyrrolo[2,3-b]pyrazin;

6-(3-methylindolin-1-yl)-5H-is irolo[2,3-b]pyrazin;

6-(1-methyl-2-phenyl-1H-pyrrol-4-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(5,6,7,8-tetrahydroquinolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-furan-3-yl-5H-pyrrolo[2,3-b]pyrazin;

dimethyl[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]amine;

6-(5-methoxy-1-methyl-1H-indol-3-yl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin;

6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-tert-butylphenyl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin;

6-(3,4-acid)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-AMINOPHENYL)-7-methyl-5H-pyrrolo[2,3-b]pyrazin;

6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin;

6-(1H-1-methyl-2-(methylthio)imidazole-5-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-[4-(tert-butyl)phenyl]-7-(prop-1-enyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(3-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-1H-pyrazole-4-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-methyl-5-phenyl-1H-pyrazole-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(pyridine-2-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(pyridine-4-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(3,4-dimetilfenil)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-trifloromethyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-AMINOPHENYL)-5H-pyrrolo[2,3-b]pyrazin;

6-(1-were-1H-pyrrol-3-yl)-5H-pyrrol the[2,3-b]pyrazin;

6-(1,5-dimethyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

6-(1,4-dimethyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

2-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol;

3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol;

2-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol;

6-(1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol;

3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]Propylamine;

3-[5-methoxy-3-(5H-pyrrolo(2,3-b]pyrazin-6-yl)indol-1-yl]Propylamine;

N-{3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propyl}ndimethylacetamide;

N-[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]ndimethylacetamide;

6-[1-(3-morpholine-4-ylpropyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin;

6-[1-(3-piperidine-1-ylpropyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin;

6-{1-[3-(pyridine-3-yloxy)propyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin;

1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-ol;

6-(2-chloro-5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde;

4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde;

[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]methanol;

[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]methanol;

[4-(5H-pyrrolo[2,3-b]pyrazin-6-ylphenyl]methanol;

6-(5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin;

2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-yl is the Thanon;

2-[5-methoxy-1-(2-morpholine-4-yl-2-oxoethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile;

[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid;

4-methoxy-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

4-methoxy-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

4-chloro-2-(4-tert-butylphenyl)-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine;

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol;

[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ylatason;

amide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acids;

methylamide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acids;

methylamide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-morpholine-4-retil)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

bis(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid is;

(2-hydroxy-1,1-bishydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-hydroxy-1-hydroxymethyl-1-methylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2,3-dihydroxypropyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

(2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid;

(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid;

(1H-[1,2,4]triazole-3-yl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid;

(2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid;

(2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N,N-dimethylpropanamide;

2-methoxyethylamine 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

2-Tien-2-ratelimit 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

2-f is acetylated 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

2-carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

(hydroxymethyl)carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

2-hydroxyethylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

methylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

dimethylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]morpholine-4-Ilkeston;

4-hydroxy-[1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]carbonitriding;

methylamide 3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]carboalumination acids;

3-hydroxypropylamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

methylamide 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid;

methylamide 3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid;

3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide;

3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide;

methylamide 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid;

(2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid;

(2-methoxyethyl)amide 3-[4-(3,5-dimethyl who isoxazolyl-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid;

(2-hydroxy-1,1-dimethylethyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid;

(2-hydroxy-2-methylpropyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid;

2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ylatason;

[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]acetic acid;

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propionic acid;

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid;

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol;

1-{1-(cyclobutanecarbonyl acid)-3-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarbonyl acid;

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid;

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]propionic acid;

1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid;

[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]acetic acid;

3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propionic acid;

3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]carboalumination acid;

3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid;

3-[4-(3,5-dim is telesocial-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid;

4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

3-(4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid;

3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid;

3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid;

2-(5-methoxy)-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

potassium 2-(5-methoxy)-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate;

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]ethanol;

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol;

{1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutyl}methanol;

2-(6-phenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)ethanol;

3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]carboalumination acid;

2-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]ethanol;

3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propan-1-ol;

3-{6-{4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propyl alcohol;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol;

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol;

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol

2-[1-methyl-5-(2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

2-[1-methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

2-[1-methyl-5-(1-methyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]Etalon;

2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

(S)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol;

(R)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol;

2-[5-(2-methoxy-1-methylethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

2-[1-methyl-5-(5-methyl[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

(R)-3-[6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol;

6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrolo[2,3-b]pyridine;

2-[5-(pyridin-4-yl)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile;

4-chloro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-methyl-1H-pyrrolo[2,3-b]pyridine;

2-(1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine;

2-(1-methyl-1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyrid is n;

4-chloro-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

5-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-6-ol;

2-(6-isopropoxy-5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

2-[5,6-dimethoxy-1-(2-morpholine-4-retil)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine;

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ylamine;

N-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methanesulfonamide;

N-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]ndimethylacetamide;

N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ml]methyl}Tien-2-ylsulphonyl;

{1-[5-(1-hydroxymethylcellulose)-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]cyclobutyl}methanol;

{1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutyl}methanol;

5-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-ml]ethyl-2H-tetrazol;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionitrile;

3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionamide;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid;

3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid;

3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid;

3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propan-1-ol;

ethyl ester of [2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]UKS the red acid;

2-methoxy-5-(5H-pyrrolo[2,3-b]pyridine-6-yl)phenol;

3-fluoro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine;

3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid;

ethyl 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-ml}propionate;

2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile;

6-(4-methylsulfinylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-methylsulfinylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)Propylamine;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}ndimethylacetamide;

amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}cyclopropylboronic acids;

N-(3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}of butyramide;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methoxyacetate;

amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-icarbonell acids;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-N'-propylacetic;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-N'-carbomethoxyamino;

N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}-N'-tetrahydropyran-2-Ilocano;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-N',N'-dieselmachine;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methanesulfonamide;

N-{3-(6-(4-tert-is utility)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-ylsulphonyl;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}dimethylisoxazol-4-ylsulphonyl;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-1-Mei-4-ylsulphonyl;

(2-hydroxy-1,1-dimethylethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

(2-hydroxy-1,1-dimethylethyl)amide 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]morpholine-4-ylmethanone;

3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide;

(2-hydroxy-1,1-dimethylethyl)amide 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

(2-methoxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid;

(2-hydroxy-2-methylpropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

(2-hydroxypropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

(2-hydroxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

(2-methoxyethyl)amide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid;

2-(1-ethyl-5-is ethoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid;

2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxamide;

3-[6-(4-(morpholine-4-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide;

6-(4-pyrrolidin-1-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-(furan-2-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazin;

6-(4-(3,5-dimethylisoxazol-4-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazin;

2-[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propan-2-ol;

1-[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]Etalon;

6-[4-(4-{2-morpholine-4-ileti}piperazine-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazin;

6-(4-piperazine-1-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin;

2-methyl-4-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]butane-2-ol;

[3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indol-5-yl]-methylamine;

2-{[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-(1-methylpiperazin)-4-yl}Etalon;

N-cyclobutyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-imidazol-1-ylpropyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-(2,5-dihydropyrrol-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

N-cyclohexyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-cyclopentyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-dimethylaminopropyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

methyl ester of 6-{2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetylamino}hexanoic acid;

1-[1,4']bipyridinyl-1'-yl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

N-(3,3-dimethylbutyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-ethoxypropan)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-(3,3-dimethylpiperidin-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(3-oxoazetidin-4-yl)ndimethylacetamide;

1-[4-(4-chlorophenyl)piperazine-1-yl]-2-(5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

1-(4-hydroxypiperidine-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-thiazolidin-3-ylatason;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-[4-(3-phenylalkyl)piperazine-1-yl]Etalon;

N-furan-2-ylmethyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-pyridin-4-retil)ndimethylacetamide;

N-cyclopropylmethyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-propylacetamide;

N-(1-cyclohexylethyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-methyl-N-pyridin-3-ylmethylene;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-(4-methotrimeprazine-1-yl)Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-phenylsulfanyl)ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)shall ndol-1-yl]-N-(4-(morpholine-4-ylphenyl)ndimethylacetamide;

N-cyclopropyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-(3-methylpiperazin-1-yl)Etalon;

N-(4-cyclohexylphenol)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-methylcyclohexyl)ndimethylacetamide;

N-cyclohexylmethyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-pyrrolidin-1-ylatason;

4-{2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetyl}piperazine-2-he;

4-{2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetyl}-3,3-dimethylpiperazine-2-he;

4-{2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetyl}-1-methylpiperazin-2-he;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-thiomorpholine-4-ylatason;

N-(2-hydroxy-2-phenylethyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-(2,6-dimethylmorpholine-4-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

N-(4-diethylaminomethyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-[2-(4-hydroxyphenyl)ethyl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(tetrahydrofuran-2-ylmethyl)ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-pyridin-2-elmet acetamid;

N-(1,2-dimethylpropyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-benzyloxypyridine-2-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-(5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-quinoline-3-ylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-quinoline-8-ylacetamide;

N-isoquinoline-5-yl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(3-methylbutyl)ndimethylacetamide;

N-isoquinoline-1-yl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-quinoline-2-ylacetamide;

1-(3,6-dihydro-2H-pyridine-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-[3-(4-methylpiperazin-1-yl)propyl]ndimethylacetamide;

N-(2-cyclohex-1-teletel)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-[2-(1H-indol-3-yl)ethyl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-[4-(tetrahydrofuran-2-carbonyl)piperazine-1-yl]Etalon;

N-adamantane-1-yl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(2-dimethylaminoethyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-methylacetamide;

1-(4-benzo[1,3]dioxol-5-iletileri-1-yl)-2-[5-methoxy-3-1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

1-[4-(4-Chlorobenzyl)piperazine-1-yl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-[4-(1-phenylethyl)piperazine-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-[4-(2-morpholine-4-retil)piperazine-1-yl]Etalon;

1-[4-(4-methoxyphenyl)piperazine-1-yl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-[3-(2-oxopyrrolidin-1-yl)propyl]ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-piperidine-1-ylatason;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-piperidine-1-retil)ndimethylacetamide;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-pyrrolidin-1-retil)ndimethylacetamide;

1-[4-(2-methoxyethyl)piperazine-1-yl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

1-[4-(2-dimethylaminoethyl)piperazine-1-yl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

N-isobutyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-[4-(4-tert-butylbenzyl)piperazine-1-yl]-2-[5-metiloksi-3-(1H-pyrrolo[2,3-b]pyridine-2-t)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(1-methyl-3-phenylpropyl)ndimethylacetamide;

N-(4-diethylamino-1-methylbutyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-benzyl-N-(2-hydroxyethyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)in the ol-1-yl]ndimethylacetamide;

1-{4-[2-(2-hydroxyethoxy)ethyl]piperazine-1-yl}-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

N-(1-hydroxymethyl-2-methylbutyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-benzyl-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-methylacetamide;

N-(2-methoxy-1-methylethyl)-2-[5-methoxy˜3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-hydroxypropyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

N-(3-methoxyphenyl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-(4-benzhydrylpiperazine-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

1-(4-benzylpiperazine-1-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(3-pyrrolidin-1-propyl)ndimethylacetamide;

N-(1-benzylpiperidine-4-yl)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

1-[4-(4-chloro-phenyl)-4-hydroxypiperidine-1-yl]-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

methyl ester 2-{2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetylamino}-3-methylpentanoic acids;

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-methylinosine-4-yl)ndimethylacetamide;

N-(2-benzylmethyl-1-hydroxymethylene)-2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]ndimethylacetamide;

[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]uksosn the Yu acid;

2-{[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]-1-cyclopropylamino}Etalon;

N-(3-ethoxypropan)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]ndimethylacetamide;

1-pyrrolidin-1-yl-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-(3,6-dihydro-2H-pyridine-1-yl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-methyl-4-{2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]acetyl}piperazine-2-he;

2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]-N-(tetrahydrofuran-2-ylmethyl)ndimethylacetamide;

1-(2,6-dimethylmorpholine-4-yl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]-1-thiomorpholine-4-ylatason;

1-(4-hydroxypiperidine-1-yl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-(3,3-dimethylpiperidin-1-yl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

4-{2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]acetyl}piperazine-2-he;

N-(1-methylbutyl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]ndimethylacetamide;

N-bicyclo[2,2,1]hept-2-yl-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]ndimethylacetamide;

N-[3-(4-methylpiperazin-1-yl)propyl]-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]ndimethylacetamide;

1-[4-(3-dimethylaminopropyl)piperazine-1-yl]-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-(4-methylpiperazin-1-yl)-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-[4-(4-chlorophenyl)-4-hydroxypiperidine-1-yl]-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

1-[4-(3-what hydroxyphenyl)piperazine-1-yl]-2-[2-(1H-pyrrolo[2,3-b]pyridine-2-yl)pyrrol-1-yl]Etalon;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]propionic acid;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-improper-1-it;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-phenylpropionamide;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-thiomorpholine-4-improper-1-it;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-(4-methylpiperazin-1-yl)propane-1-it;

3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(tetrahydrofuran-2-ylmethyl)propionamide;

N-(2-hydroxy-2-phenylethyl)-3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]propionamide;

N-(2-hydroxyethyl)-3-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]propionamide;

1-[4-(4-chlorophenyl)-4-hydroxypiperidine-1-yl]-2-[5-methoxy-2-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]Etalon;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-morpholine-4-yl-1H-pyrrolo[2,3-b]pyridine;

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-piperidine-1-yl-1H-pyrrolo[2,3-b]pyridine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]-(2-methoxyphenyl)amine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]orthotolidine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]-(3-methoxyphenyl)amine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]methacrylamide;

(4-forfinal)-[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

[2-(5-methodology the si-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]-(4-methoxyphenyl)amine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]partailly;

benzyl[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

(4-terbisil)-[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

(4-methoxybenzyl)-[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

(2-methoxyethyl)-[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

methyl ester of 3-[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-ylamino]benzoic acid;

cyclopropylmethyl[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]phenylamine;

butyl[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amine;

methylamide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid, or

tert-butyl ester 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid; and their corresponding N-oxides and proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the formula (1A) of the present invention for the inhibition of SYK are:

6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin, (compound denoted as A1-B1-C1), example 1(a);

6-(1-methyl-1H-indol-3-yl-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-B1-S), example 1(b);

3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol, (compound denoted as A1-B6-S), example 2(a);

3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol, (compound denoted as A1-B6-C1), example 2(b);

2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol, (compound denoted as A1-B5-C1), example 2(d);

6-(1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-B2-S), example 2(e);

N-{3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propyl}ndimethylacetamide, (compound denoted as A1-B7-C), example 4(a);

1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-ol, (compound denoted as A1-B1-C10), example 7;

[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]methanol; (compound denoted as A2-B4-C), example 9(C);

6-(5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-B2-C1), example 11;

2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-ylatason; (compound denoted as A1-B8-C1), example 12(a);

2-[5-methoxy-1-(2-morpholine-4-yl-2-oxoethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile; (compound denoted as A3-B8-C1), example 12(b);

4-methoxy-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A5-B1-C1), example 13(b);

4-methoxy-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine; (connected to the e, designated as A5-B2-C1), example 13(c);

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol, (compound denoted as A2-B1-C5), example 13(f);

amide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid; (compound denoted as A2-B1-C15), example 14(b);

methylamide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid; (compound denoted as A21-B1-C16), example 14(C);

(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid; (compound denoted as A2-B1-S), example 14(e);

(2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid; (compound denoted as A2-B1-C24), example 14(g);

amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid; (compound denoted as A2-B1-s), example 14(i);

(2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1-indole-5-carboxylic acid; (compound denoted as A2-B1-C31), example 14(m);

(2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid; (compound denoted as A2-B5-C), example 14(n);

(2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid; (compound denoted as A2-B18-C24), example 14(o);

(1H-[1,2,4]triazole-3-yl)am the d 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid; (compound denoted as A2-B1-s), example 14(q);

2-methoxyethylamine 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid; (compound denoted as A1-B1-C25), example 14(v);

2-hydroxyethylamide 1-methyl-1-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid; (compound denoted as A1-B1-S), example 14(aa);

methylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid; (compound denoted as A1-B1-C23), example 14(ab);

(2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A-B1-C25), example 14(am);

(2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid; (compound denoted as A-B2-C25), example 14(an);

(2-hydroxy-1,1-dimethylethyl)amide 3-[4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A3-B1-C31), example 14(ao);

(2-hydroxy-2-methylpropyl)amide 3-[4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A3-B1-s), example 14(ap);

[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]acetic acid, (compound denoted as A2-B1-C6), example 15(a);

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propionic acid; (compound, known the as A1-B1-C2) example 15(b);

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]CYCLOBUTANE-1-carboxylic acid; (compound denoted as A2-B1-C11), example 15(c);

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol, (compound denoted as A2-B1-C10), example 15(e);

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid; (compound denoted as A2-B18-s), example 15(g);

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]propionic acid; (compound denoted as A2-B1-C2), example 15(h);

1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid; (compound denoted as A1-B1-s), example 15(i);

3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A-B1-s), example 15(m);

3-[4-(3,5-methylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid; (compound denoted as A-B2-C), example 15(n);

4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A-B1-C1), example 15(o);

4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A-B2-C1), example 15(p);

3-(4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A5-B1-s), example 15(q);

3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-carboxylic acid; (compound denoted as A2-B2-C), example 15(s);

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]ethanol, (compound denoted as A2-B1-C3), example 16(a);

2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol, (compound denoted as A2-B1-C7), example 16(b);

{1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutyl}methanol; (compound denoted as A2-B1-C12), example 16(c);

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-C1), example 17(a);

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol; (compound denoted as A2-B1-C9), example 17(b);

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol, (compound denoted as A2-B1-C4), example 17(c);

3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol, (compound denoted as A2-B1-C5), example 17(d);

2-[1-methyl-5-(2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-C36), example 17(e);

2-[1-methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-s), example 17(f);

1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]Etalon; (compound denoted as A2-B1-C20), example 17(h);

2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B17-C1), the example 17(i);

(R)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol; (compound denoted as A2-B1-S), example 17(j);

(S)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol; (compound denoted as A2-B1-S), example 17(k);

2-[5-(2-methoxy-1-methylethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-C17), example 17(l);

2-[1-methyl-5-(5-methyl[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-S), example 17(m);

(R)-3-[6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol; (compound denoted as A2-B17-S), example 17(n);

6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol, (compound denoted as A2-B17-C10), example 17(o);

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A13-B1-C1), example 17(p);

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile; (compound denoted as A3-B1-C1), example 17(r);

4-chloro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A28-B1-C1), example 17(s);

2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A15-B1-C1), example 17(t);

4-chloro-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A28-B2-C1), example 17(y);

N-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]ndimethylacetamide; (compound denoted as A2-B1-C45), example 19(b);

{1-[5-(1-hydroxymethylcellulose)-3-(1H-pyrrolo[2,3-b]pyridine-2-yl-indol-1-yl]cyclobutyl}methanol; (compound denoted as A2-Q13-C12), example 20(a);

{1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutyl}methanol; (compound denoted as A1-B1-C13), example 20(b);

2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile; (compound denoted as A3-B2-C1), example 32;

(2-hydroxy-1,1-dimethylethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A68-B1-C1), example 40(a);

(2-hydroxy-1,1-dimethylethyl)amide 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A28-B1-C31), example 40(b);

(2-hydroxy-1,1-dimethylethyl)amide 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A68-B3-C1), example 40(e);

(2-hydroxy-2-methylpropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A70-B1-C1), example 40(g);

(2-hydroxypropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A85-B1-C1), example 40(h);

(2-hydroxyethyl)amide 2-(5-methoxy-1-methyl-1H and the Dol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A86-B1-C1), example 40(i);

(2-methoxyethyl)amide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A-B2-C1), example 40(j);

methylamide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A9-B2-C1), example 60;

tert-butyl ester 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; example 61;

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Particularly preferred compounds of the present invention of the formula (1A) for the inhibition of SYK are:

6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A28-B1-C1), example 1(a);

amide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid; (compound denoted as A2-B1-C15), example 14(b);

(2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A-B1-C25), example 14(am);

(2-hydroxy-2-methylpropyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A3-B1-s), example 14(ap);

3-[4-(3,5-dimethylisoxazol-4-yl)-1-pyrrolo(2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid; (compound denoted as A-B1-s), example 15(m);

3-[4-(3,5-methylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid; (compound denoted as A-B2-C), example 15(n);

4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A-B1-C1), example 15(o);

2-[1-methyl-5-(2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-C36), example 17(e);

2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile; (compound denoted as A3-B1-C1), example 17(r);

{1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutyl}methanol; (compound denoted as A1-B1-C13), example 20(b);

(2-hydroxy-1,1-dimethylethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A68-B1-C1), example 40(a);

(2-hydroxy-1,1-dimethylethyl)amide 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid; (compound denoted as A68-B3-C1), example 40(e);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the present invention of the formula (1b) for the inhibition of SYK are:

6-indolizine-1-yl-5H-pyrrolo[2,3-b]PI is asin; (compound denoted as A1-in40-S), example 1(p);

6-(3-methylindolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-B41 content-S), example 1(q);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the present invention of the formula (1c) for the inhibition of SYK are:

6-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-V), example 1(ad);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the present invention of the formula (1d) for the inhibition of SYK are:

6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-V), example 1(w);

6-(4-tert-butylphenyl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A29-V), example 1(x);

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide; (compound denoted as A33-V), example 14(t);

5-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]ethyl-2H-tetrazol; (compound denoted as A35-V), example 22;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionamide; (soy is inania, marked as A32-V), example 24;

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid; (compound denoted as A31-V), example 25(a);

3-[6-(4-tert-bctester)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propan-1-ol, (compound denoted as A30-V), example 26;

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}ndimethylacetamide; (compound denoted as A39-V), example 36(a);

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methanesulfonamide; (compound denoted as A38-V), example 39(a);

2-methyl-4-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]butane-2-ol, (compound denoted as A59-V), example 50;

4-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl-butane-2-he; (compound denoted as A58 motorway-V), example 51;

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the present invention of the formula (1A) for inhibition of Aurora2 are:

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid; (compound denoted as A2-B18-C28), example 15(g);

2-[1-methyl-5-(pyridin-4-yl)-1H-indol-3-yl]-4-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B1-C37), example 17(q);

N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}Tien-2-ilself named; (compound denoted as A2-B1-C69), example 19(c);

N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}-N'-tetrahydropyran-2-rocephine; (compound denoted as A2-B1-C74), example 37(c);

2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-N-(2-methylinosine-4-yl)ndimethylacetamide; (compound denoted as A2-B123-C1), example 53(cf);

[2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]-(2-methoxyphenyl)amine; (compound denoted as A87-B1-C1), example 59(b);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Preferred compounds of the present invention of the formula (1C) for inhibition of Aurora2 are:

6-(1-methyl-1H-pyrrol-2-yl)-5H-pyrrolo[2,3-b]pyrazin; (compound denoted as A1-V), example 1(Oh);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Compounds of the present invention of the formula (1A), in which the restattached in position 2 of the indole ring, and the compounds of formula 1(C), in which the restattached in position 2 of the pyrrole ring, demonstrating the selectivity ing is berbania against Aurora2.

Compounds of the present invention of the formula (1A), in which the rest(where R2is hydrogen, and X1represents CH) attached in position 3 of the indole ring, and the compounds of formula 1(C), in which the rest(where R2is hydrogen, and X1represents CH or N, especially N) attached in position 3 of the pyrrole ring, are preferred for inhibition of IGF1R.

Preferred compounds of the present invention of the formula (1A) for the inhibition of IGF1R are:

2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ylatason; (compound denoted as A2-B-C1), example 14(aq);

2-[5,6-dimethoxy-1-(2-morpholine-4-retil)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine, (compound denoted as A2-B-C1), example 1(ab);

methanesulfonate of 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine; example 21(g);

and the corresponding N-oxides and their proletarienne forms, and pharmaceutically acceptable salt and solvate (e.g., hydrates) of such compounds and their N-oxides and proletarienne form.

Compounds of the present invention exhibit useful pharmacological activity and accordingly they are included in the pharmaceutical compositions, and their use for the treatment of patients suffering from some of the violations the mi health. Thus, another aspect of the invention comprise compounds of the present invention and compositions containing them for use in therapy.

Compounds included within the scope of the present invention, inhibit the catalytic activity of the kinase in accordance with the tests presented in the literature and are described further in vitro studies, and the results of these tests are believed to correlate to pharmacological activity in humans and other mammals. So, in the following embodiment, the present invention proposed connection of the present invention and containing such compounds compositions for use in treating patients suffering from or predisposed to the state, which can be facilitated by the introduction of inhibitors of protein kinase (e.g., Syk, Aurora2, KDR, FAK and IGF1R). For example, this connection can be used for the treatment of inflammatory diseases, for example asthma: an inflammatory dermatoses (e.g., psoriasis, herpes dermatitis, eczema, and necrotizing cutaneous vasculitis, bullous diseases); allergic rhinitis and allergic conjunctivitis; chronic inflammation of the joints, including arthritis, rheumatoid arthritis and other conditions that accompany arthritis, such as rheumatoid spondylitis, gouty arthritis,traumatic arthritis, measles red is ha, psoriatic arthritis and osteoarthritis. Compounds of the present invention can also be used for the treatment of chronic obstructive pulmonary disease (COPD), acute synovitis, autoimmune diabetes, autoimmune encephalomyelitis, colitis, atherosclerosis, peripheral vascular disease, cardiovascular disease, multiple sclerosis, restenosis, myocarditis, B cell lymphoma, systemic lupus erythematosus,diseases of type "graft versus host",and other conditions associated with transplant rejection, cancer and tumors, such as colorectal tumors, prostate tumors, breast cancer, thyroid cancer, colon cancer, and lung), and inflammatory bowel disease. In addition, the compounds of the present invention can be used as antiangiogenic agents tumors.

A special variant of therapeutic methods of the present invention is the treatment of asthma.

Another special variant of therapeutic methods of the present invention is the treatment of psoriasis.

Another special variant of therapeutic methods of the present invention is the treatment of joint inflammation.

Another special variant of therapeutic methods of the present invention is the treatment of inflammatory diseases to which Chechnya.

Another special variant of therapeutic methods of the present invention is the treatment of cancer and tumors.

In accordance with another feature of the present invention, a method of treating a patient (human or animal)suffering from or susceptible to conditions that can facilitate the introduction of inhibitors of protein kinase (e.g., Syk, Aurora2, KDR, FAK and IGF1R), for example, such conditions, which are described below, which includes an introduction to the patient an effective amount of the compounds of the present invention or containing compound of the present invention compositions. The term "effective amount" means such amount of the compounds of the present invention, which is effective for inhibiting the catalytic activity of protein kinases such as Syk, Aurora2, KDR, FAK and IGF1R, which results in the desired therapeutic effect.

Note that given in the present description the term "treatment" should be considered as including the prevention and treatment of identified conditions.

In the scope of the present invention also includes compositions containing at least one of the compounds of the present invention together with a pharmaceutically acceptable carrier or excipient.

Compounds of the present invention can BBO is arranged in any suitable way. In practice, the compounds of the present invention typically can be entered parenteral, topical, rectal, oral or by inhalation, especially in the case of oral administration.

Compositions of the present invention can be obtained by conventional means, using one or more pharmaceutically acceptable adjuvants or excipients. Adjuvants include (among others), diluents, sterile aqueous medium and various non-toxic organic solvents. The composition can be in the form of tablets, pills, granules, powders, aqueous solutions or suspensions, injectable solutions, elixirs or syrups, and may contain one or more agents selected from the group comprising sweeteners, flavoring agents, fragrances, dyes or stabilizers to obtain pharmaceutically acceptable preparations. The choice of media and the content of the active substance in the carrier is usually defined in accordance with the solubility and chemical properties of the active compounds, the specific route of administration and conditions in pharmaceutical practice. For example, for the preparation of tablets can be used excipients, such as lactose, sodium citrate, calcium carbonate, dicalcium phosphate, and loosening agents, such as starch, alginic acid and certain complex silicates, together with nazyvausia agents, such as magnesium stearate, nutriceuticals and talc. For the preparation of capsules is convenient to use the lactose and high molecular weight glycols.

If you use a water suspension, they may contain emulsifying agents, or agents that facilitate the suspensions. You can also use diluents such as sucrose, ethanol, polyethylene glycol, glycerin and chloroform, or a mixture thereof.

For parenteral use of emulsions, suspensions or solutions of the products in accordance with the present invention in a vegetable oil such as sesame oil, peanut oil or olive oil or in aqueous-organic solutions, such as water and propylene glycol, in solutions of complex organic esters for injection, such as etiloleat, as well as in the form of sterile aqueous solutions of pharmaceutically acceptable salts. Solutions of salts of the products of the present invention is especially useful for introduction via intramuscular or subcutaneous injection. Aqueous solutions, including solutions of salts in pure distilled water can be used for intravenous injection, provided that their pH value is adjusted appropriately so that they are appropriately buffered and are isotonic with sufficient amount of glucose and chloride into three and that they are sterilized by heating, irradiation or filtration.

For external use you can use gels (water or alcohol based), creams or ointments containing compounds of the present invention. Compounds of the present invention may also be incorporated in a gel or matrix base for use in the patches that would provide adjustable flow connection through transdermally barrier.

For administration by inhalation the compounds of the present invention can be dissolved or suspended in a suitable carrier for use in spray or aerosol form of a suspension or solution, or can adsorb or absorb on suitable solid carrier for use in a dry powder inhaler.

Solid compositions for rectal injection include suppositories, created in accordance with known methods and containing at least one compound of the present invention.

The percentage of active ingredient in the composition of the present invention may vary, and it is necessary that it was the quantity that will provide the desired dose.

Obviously, multiple unit dosage forms can be entered about the same time. Used dose is determined by the physician, and it depends on the desired therapeutic EF the project, the method of administration and duration of treatment, and the patient's condition. For adults doses typically range from about 0.001 to about 50, preferably from about 0.001 to about 5 mg/kg of body weight per day by inhalation, from about 0.01 to about 100, preferably from 0.1 to 70, more preferably from 0.5 to 10 mg/kg of body weight per day by oral administration, and from about 0.001 to about 10, preferably from 0.01 to 1.0 mg/kg of body weight per day intravenously. In each case the dose is determined in accordance with the factors subject to treatment to a patient, such as age, weight, General health status, and other characteristics that may affect the efficacy of a drug.

Compounds of the present invention can enter as often as necessary to achieve the desired therapeutic effect. Some patients are able to respond quickly to high or low dose, and may be sufficient introduction of lower doses. For other patients may need longer treatment admission from 1 to 4 doses per day in accordance with the physiological requirements of each individual patient. Typically, active product can be administered orally 1 to 4 times a day. Of course, for some patients it will be necessary to prescribe no more than one or two doses per day.

Connect the means of the present invention can be obtained, using or adapting known methods, which involve methods that are still used, or the methods disclosed in the literature, such as disclosed R.C.Larock in Comprehensive Organic Transformations, VCH publishers, 1989.

When carrying out the following reactions may be necessary to protect reactive functional groups, for example hydroxy, amino, imino, thio or carboxypropyl, if their presence is necessary in the final product, to avoid their unwanted participation in the reactions. Conventional protective groups can be used in accordance with standard practice; see examples in T.W. Greene and P.G.M. Wuts in "Protective Groups in Organic Chemistry" John Wiley and Sons, 1991.

The compounds of formula (1), where R1, R2and R3have the above meanings, and X1represents N or CH, can be obtained by using or adapting the methods disclosed Davis et al., Tetrahedron, 1992, 48, page 939-952, for example:

(i) the interaction of the compounds of formula (III):

where R2and R3have the above values, X1represents N or CH, with a suitable base, such as sitedisability (or utility), in an inert solvent, such as tetrahydrofuran, and at a temperature of from about -26°C;

(ii) treatment of the resulting anion with NITRILES of the formula (IV):

R1CN(IV)

where R1has the above values at a temperature of from about -15°C to about room temperature.

This method is particularly suitable for obtaining the compounds of formula (I), where R1represents optionally substituted N-methylindol-3-yl, R2and R3represent hydrogen, X1represents N or CH.

The compounds of formula (I), where R1, R2, R3and X1have the above values, can also be obtained by using or adapting the method disclosed by Chang and Bag, J.Org.Chem., 1995, 21, pages 7030-7032, for example, the interaction of the compounds of formula (V):

where R1, R2, R3and X1have the above meanings, and X2represents halogen, preferably iodine atom or triflate group, with Bronevoy acid of formula (VI):

R1B(OH)2(VI)

where R1has the above values. The reaction accession convenient to carry out, for example, in the presence of a complex metal catalyst such as tetrakis(triphenylphosphine)palladium(0), and sodium bicarbonate, in aqueous dimethylformamide, at a temperature up to the boiling point of the reverse holodilny the om.

The compounds of formula (I), where R2, R3and X1have the above significance, and R1represents aryl or heteroaryl, substituted-NY1Y2can be achieved by interaction of the corresponding compounds in which R1represents aryl or heteroaryl, substituted-OSO2CF3with amines of the formula HNY1Y2. The reaction is conveniently carried out at a temperature of from about 200°C in a microwave oven.

The compounds of formula (I), where R2, R3and X1have the above significance, and R1represents aryl or heteroaryl, replaced by heteroaryl, can be obtained by the interaction of the corresponding compounds in which R1represents aryl or heteroaryl, substituted-OSO2CF3with heteroarylboronic acid. The reaction is conveniently carried out in the presence of sodium carbonate solution and tetrakis(triphenylphosphine)palladium[0], in an inert solvent, such as dioxane, and at a temperature of approximately 180°C in a microwave oven.

Compounds of the present invention can also be obtained by vzaimoprevrascheny other compounds of the present invention.

For example, the compounds of formula (I)containing carboxypropyl, can be obtained by hydrolysis of the corresponding esters. The hydrolysis is conveniently carried out as alkaline hydrolysis using a base such as the hydroxide is Christmas, metal, for example, lithium hydroxide, or carbonate of an alkali metal, for example potassium carbonate, in the presence of a mixture of water/organic solvent using an organic solvent, such as dioxane, tetrahydrofuran or methanol, at a temperature from about room temperature up to the boiling temperature under reflux. Hydrolysis of esters can also be carried out as an acid hydrolysis using an inorganic acid such as hydrochloric acid, in the presence of a mixture of water/inert organic solvent, using organic solvents such as dioxane or tetrahydrofuran, at a temperature of from about 50°C to about 80°C.

As another example, the compounds of formula (I)containing carboxypropyl, can be obtained by removing the reaction catalyzed by acid, tert-boutelou group corresponding tert-butyl esters, and using standard reaction conditions, for example, by reaction with triperoxonane acid at a temperature of about room temperature.

As another example, the compounds of formula (I)containing carboxypropyl, can be obtained by hydrogenation of the corresponding benzyl esters. The reaction can be carried out in the presence of ammonium formate and a suitable metal catalyst, for example palladium deposited on an inert novtel is, such as carbon, preferably in a solvent such as methanol or ethanol, and at a temperature of about the boiling temperature under reflux.

Alternative reaction can be carried out in the presence of a suitable metal catalyst, such as platinum or palladium, optionally deposited on an inert carrier such as carbon, preferably in a solvent such as methanol or ethanol.

As another example of the interconversion process the compounds of formula (I)containing a-C(=O)-NY1Y2the group can be obtained by reaction of a combination of compounds of formula (I)containing carboxypropyl, with an amine of the formula HNY1Y2getting amide bond using standard methods of combination reaction of peptides, for example the reaction mix in the presence of hexaflurophosphate O-(7-asobancaria-1-yl)-1,1,3,3-tetramethyluronium and triethylamine (or diisopropylethylamine) in tetrahydrofuran (or dimethylformamide) at room temperature. The reaction mix can also be carried out by the interaction of the compounds of formula (I)containing carboxylate, N-oxide hexaphosphate N-{(dimethylamino)(1H-1,2,3-triazolo[4,5-b]pyridine-1-yl)methylene}-N-methylmethanamine in the presence of a suitable base, such as diisopropylethylamine, in an inert solvent, such as dimethylformamide, and at temperaturescale room temperature with subsequent interaction with the amine of formula H-NY 1Y2(ammonium chloride can be used to obtain compounds of formula (I)containing a-C(=O)-NH2group). The reaction mix can also be carried out by the interaction of the compounds of formula (I)containing carboxypropyl, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethylethylenediamine in anhydrous dimethylformamide, followed by interaction with the amine of formula HNY1Y2in the presence of diisopropylethylamine.

As another example of the interconversion process the compounds of formula (I)containing a-CH2OH group, can be obtained by restoring the appropriate compounds of formula (I)containing the group-CHO or-CO2R7(where R7is lower alkyl). For example, restoring conveniently be carried out using a reaction with sociallyengaged, in an inert solvent, such as tetrahydrofuran, and at a temperature from about room temperature to about the boiling temperature under reflux.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-CO2Me, you can get:

(i) by treating compound of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, N-phenyltrimethylammonium in the presence of a suitable base, such as Treaty the amine, in an inert solvent, such as dichloromethane, at a temperature of about -78°C;

(ii) reaction of the resulting triflate with carbon monoxide in the presence of a suitable catalyst (e.g. palladium acetate), 1,3-bis(diphenylphosphino)propane, triethylamine and methanol, in an inert solvent, such as dimethylformamide, at a pressure of about 1 atmosphere and at a temperature of about room temperature.

This method is particularly suitable for producing compounds of formula (I), where R1represents 5-carboxymethyl-N-methylindol-3-yl.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-SO2NY1Y2you can get:

(i) by treating compound of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, N-phenyltrimethylammonium, as described above;

(ii) processing the received triflate tert-butylmercaptan in the presence of tert-butoxide sodium, palladium acetate, lithium chloride and R(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl in an inert solvent, such as toluene, and at a temperature of about 110-120°C;

(iii) the interaction of the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-StBu, with triperoxonane acid and acetate of mercury, an inert dissolve the Le, such as toluene, and at a temperature of about room temperature, followed by treatment with hydrogen sulphide;

(iv) the interaction of the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-SH, with chlorine with aqueous acetic acid at a temperature of about room temperature;

(v) the interaction of the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-SO2Cl, with an amine of the formula HNY1Y2.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted aryl (or heteroaryl), can be obtained by treating compound of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, N-phenyltrimethylammonium, as described above, followed by the interaction of the resulting triflate with complex ether aryl(or heteroaryl)Bronevoy acid in the presence of a suitable catalyst (e.g. tetrakis(triphenylphosphine)palladium and aqueous sodium bicarbonate, in an inert solvent, such as dimethylformamide, and at a temperature of about 120-150°C.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-C(=O)CH3,you can get treatment joint is of the formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, N-phenyltrimethylammonium, as described above, with the subsequent interaction of the resulting triflate with n-butylvinyl ether in the presence of a suitable catalyst (e.g. palladium acetate), 1,3-bis(diphenylphosphino)butane and triethylamine, in an inert solvent, such as dimethylformamide, and at a temperature of about 80°C.

As another example of the interconversion process the compounds of formula (I)containing the group-C(OH)CH3R12(where R12represents alkyl), can be obtained by treating compound of formula (1)containing the group-C(=O)CH3, a Grignard reagent, such as methylmagnesium, if R12represents methyl, in an inert solvent, such as tetrahydrofuran, and at a temperature of about room temperature.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, can be obtained by the interaction of the corresponding compounds of formula (I), where R1represents aryl or heteroaryl, substituted methoxy, with a Lewis acid, such as tribromide boron, in an inert solvent, such as dichloromethane, and at a temperature of from about 0°C to about room temperature.

Alternative compounds of formula (I), R 1represents aryl or heteroaryl, substituted hydroxy, can be obtained by the interaction of the corresponding compounds of formula (I), where R1represents aryl or heteroaryl, substituted benzyloxy, attributively in an inert solvent, such as acetonitrile and at a temperature of about 50°C.

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-OR (where R is optionally substituted alkyl, cycloalkyl, cycloalkenyl, heteroseksualci or geterotsiklicheskikh), can be obtained by alkylation of the corresponding compounds of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, the compound of the formula (VII):

RX3(VII)

where R has the above meanings, and X3represents a halogen, preferably a bromine atom, or a group of Totila, using standard alkylation conditions. The alkylation may for example be carried out in the presence of a base such as a carbonate of an alkali metal (e.g. potassium carbonate or cesium carbonate), alkali metal alkoxide (for example, tert-piperonyl potassium) or an alkali metal hydride (e.g. sodium hydride), in dimethylformamide or Dimity is the sulfoxide, at a temperature of from about 0°C to about 100°C.

Alternative compounds of formula (I), where R1represents aryl or heteroaryl, substituted-OR (where R is optionally substituted alkyl, cycloalkyl, cycloalkenyl, heteroseksualci or geterotsiklicheskikh), can be obtained by the interaction of the corresponding compounds of formula (I), where R1represents aryl or heteroaryl, substituted hydroxy, with an appropriate alcohol of formula (VIII):

ROH(VIII)

where R has the above meanings, in the presence of triarylphosphine, such as triphenylphosphine and dialkyl acetylenedicarboxylate, such as diisopropylperoxydicarbonate or diethylazodicarboxylate, in an inert solvent, such as toluene, and at a temperature of about room temperature. This method is particularly suitable for producing compounds of formula (I), where R1is heteroaryl, substituted-OR (where R is optionally substituted alkyl, cycloalkyl, cycloalkenyl, heteroseksualci or geterotsiklicheskikh).

As another example of the interconversion process the compounds of formula (I), where R1represents aryl or heteroaryl, substituted-OR (where R is propyl, substituted by hydroxy), can p in order to obtain the interaction of the corresponding compounds of formula (I), where R1represents aryl or heteroaryl, substituted-OR (where R is propenyl) with a borane and subsequent interaction with hydrogen peroxide. This method is particularly suitable for producing compounds of formula (I), where R1represents indolyl, substituted-OCH2CH(CH3)OH, and-OCH2CH2CH2OH.

As another example of the interconversion process the compounds of formula (I), where Rjrepresents aryl or heteroaryl, substituted-OR (where R represents a group of 1,3-dihydroxyacetone), can be obtained by the interaction of the corresponding compounds where R is alkenyl, with osmium tetroxide in the presence of N-oxide 4-methylmorpholine. The reaction is conveniently carried out in an inert solvent, such as acetone, and at a temperature of about room temperature.

As another example of the interconversion process the compounds of formula (1a), where R9represents alkyl, alkenyl, cycloalkyl, heteroseksualci or alkyl, substituted-C(=O)-NY1Y2, -OR7, -C(=O)-OR7, -NY1Y2can be obtained by alkylation of the corresponding compounds of the formula (1a), where R9is hydrogen, the corresponding halide of formula (IX):

R9X4(IX)

where R9the stand is made alkyl, alkenyl, cycloalkyl, heteroseksualci or alkyl, substituted-C(=O)NY1Y2, -OR7, -C(=O)-OR7, -NY1Y2and X4represents a halogen atom, preferably a bromine atom, using standard alkylation conditions, such as those described above.

As another example of the interconversion process the compounds of formula (I)containing a-N(R6)-C(=O)-NY3Y4group, where R6and Y3both represent hydrogen and Y4has the above values can be obtained by the interaction of the corresponding compounds of formula (I)containing an amino group, with an isocyanate of the formula O=C=NY4in an inert solvent, such as tetrahydrofuran, and at a temperature of about room temperature.

As another example of the interconversion process the compounds of formula (I)containing sulfoxide communication can be obtained by oxidation of corresponding compounds containing-S - link. For example, the oxidation is conveniently carried out using a reaction with peroxyketal, for example, 3-chloroperbenzoic acid, preferably in an inert solvent, for example dichloromethane, preferably at or near room temperature, or, alternatively, using sour peroxomonosulfate potassium in the environment, such as water, methanol, sauverny to about pH 5, at a temperature from about 0°C decanates temperature. This last method is preferred for compounds containing a group unstable to an acid environment.

As another example of the interconversion process the compounds of formula (I)containing sulfone communication can be obtained by oxidation of corresponding compounds containing-S - or sulfoxide communication. For example, the oxidation reaction is conveniently carried out by interaction with peroxyketal, for example, 3-chloroperbenzoic acid, preferably in an inert solvent, for example dichloromethane, preferably at or near room temperature.

As another example of the interconversion process the compounds of formula (I)containing a cyano, can be obtained by the interaction of the corresponding compounds of formula (I)containing a-C(=O)-NH2the group, with pentachloride phosphorus in the presence of triethylamine. This reaction is conveniently carried out in an inert solvent, such as tetrahydrofuran, and at a temperature of about the boiling temperature under reflux.

As another example of the interconversion process the compounds of formula (I)containing the group-C(=O)-NH2can be achieved by interaction of the corresponding compounds of formula (I)containing a cyano, and hydrogen peroxide in the presence of sodium hydroxide. The reaction is conveniently carried out in methanol at a temperature of about room t is mperature.

As another example of the interconversion process the compounds of formula (1)containing a group tetrazolyl, can be obtained by the interaction of the corresponding compounds of formula (I)containing a cyano, usedatabaseyou. The reaction is conveniently carried out in an inert solvent, such as toluene, and at a temperature of about the boiling temperature under reflux.

As another example of the interconversion process, compounds of formula (I), where R2represents fluorine, can be obtained by the interaction of the corresponding compounds of formula (I), where R2represents hydrogen, methylacrylamide (in an inert solvent, such as tetrahydrofuran, and at a temperature of approximately 0° (C) with subsequent interaction with bis(tetrafluoroborate) 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane at temperatures from about 0°C to about the boiling temperature under reflux.

As another example of the interconversion process the compounds of formula (I), where X1is C-NY1Y2(where Y1and Y2have the above values, and only one of the Y1and Y2represents hydrogen), can be obtained by the interaction of the corresponding compounds of formula (I), where X1represents halogen (e.g. chlorine), with an amine of the formula HNY1Y2(where Y1and Y2what have listed just above values) in the presence of cesium carbonate and Tris-(dibenzylideneacetone)diplegia(0), in an inert solvent, such as 1,2-dimethoxyethane, and at a temperature of about 80°C.

As another example of the interconversion process the compounds of formula (I), where X1is C-CN, can be obtained by the coupling of compounds of formula (I), where X1represents C-halogen, preferably C-C1, with cyanide zinc in the presence of zinc powder, compound [1'1-bis(diphenylphosphino)ferrocene] and dichloropalladium(II), dichloromethane (catalytic amount) and N,N-dimethylacetamide at a temperature of about 150°C.

As another example of the interconversion process the compounds of formula (I)containing the group-C(=O)-OR5(where R5has the above values), can be obtained by the interaction of the corresponding compounds of formula (I)containing the group-C(=O)-OH, with alcohols of the formula R5-OH. For example, if R5represents tert-butyl, the reaction is conveniently carried out in the presence of 1,1'-carbonyldiimidazole and 1,8-diazabicyclo[5,4,0]undec-7-ene at a temperature of about room temperature.

It should be noted that the compounds of the present invention may contain asymmetric centers. These asymmetric centers can independently be either R-or S-configuration. Professionals should be aware that some compounds of the present invention may also have geometric isomerism. Situatonniste, what the present invention includes individual geometrical isomers, stereoisomers and their mixtures, including racemic mixtures of the above compounds of formula (I). Such isomers can be distinguished from their mixtures using or adapting known methods, for example chromatographic methods, and recrystallization, or get them separately from the appropriate isomers of their intermediates.

In accordance with another feature of the present invention the salt of the accession of the acid compounds of the present invention can be obtained by the interaction of the free base with the appropriate acid using or adapting known methods. For example, salt accession acid of the present invention can be obtained either by dissolving the free base in water or in an aqueous solution of alcohol, or other suitable solvents containing the appropriate acid, and separating the salt by evaporating the solution, or by the interaction of the free base and acid in an organic solvent, and in this case, salt is produced directly or it can be obtained by concentrating the solution.

Salt accession acid compounds of the present invention can be regenerated from the salts by using or adapting known methods. For example, the parent compound of the present invention which can be regenerated from the salts accession acid treatment of their alkali, for example, aqueous sodium bicarbonate solution or aqueous ammonia solution.

Compounds of the present invention can be regenerated from their salts attaching grounds, using or adapting known methods. For example, the parent compound of the present invention can be regenerated from their salts accession grounds processing them with acid, for example hydrochloric acid.

Compounds of the present invention can be obtained or formed during the implementation of the method of the present invention in the form of a solvate (e.g. hydrate). Hydrates of the compounds of the present invention are conveniently obtained by recrystallization from a mixture of water/organic solvent using an organic solvent, such as dioxane, tetrahydrofuran or methanol.

In accordance with another feature of the present invention the salt of the accession of the bases of the compounds of the present invention can be obtained by the interaction of the free acid with an appropriate base, using or adapting known methods. For example, salts of joining the bases of the compounds of the present invention can be obtained either by dissolving the free acid in water or in an aqueous solution of ethanol or other suitable solvents containing the appropriate substrate and separating the salt by evaporating process is and, or by the interaction of the free acids and bases in an organic solvent, and in this case, salt is produced directly or it can be obtained by concentrating the solution.

Source materials and intermediate compounds can be obtained by using or adapting known methods, for example methods described in the comparative examples, or their obvious chemical equivalents.

The compounds of formula (IV), where R1has the above values can be obtained by the interaction of the corresponding compounds of formula (1):

R1-CHO(1)

where R1has the above values, with hydroxylaminopurine in an inert solvent, such as dimethylformamide, and at a temperature of about 150°C.

The compounds of formula (IV), where R1represented by formula (II):

where R10and p have the above significance, and R9represents alkyl, alkenyl, cycloalkyl or alkyl, substituted-C(=O)NY1Y2, -OR7, -C(=O)-OR7, -NY1Y2can be obtained by alkylation of the corresponding 1H-indoles of formula (IV), where R1represented by formula (II), where R10and p have the above significance, and R9represents hydrogen, with a corresponding(optionally substituted) alkyl-, alkenyl or cycloalkylation, using standard alkylation conditions. The alkylation may for example be carried out in the presence of a base such as a carbonate of an alkali metal, for example potassium carbonate, or alkali metal hydride, for example sodium hydride, in an inert solvent, such as dimethylformamide or dimethylsulfoxide, at a temperature from about room temperature to about 100°C.

The compounds of formula IV, where R1is 5,6,7,8-tetrahydroquinolin-1-yl, can be obtained: (i) interaction piperidine-2-carboxylic acid with formic acid and acetic anhydride at a temperature of about room temperature; (ii) processing the obtained sodium-1-formylpiperidine-2-carboxylate 4-toluensulfonate in an inert solvent, such as dichloromethane, and at a temperature of about room temperature; (iii) interaction with Acrylonitrile in the presence of triethylamine at a temperature of about room temperature.

The compounds of formula (1) where R1has the above values can be obtained by formirovanie the compounds of formula (2):

R1H(2)

where R1has the above values, using standard reaction conditions, for example reaction of familiabuilder Haq, the phosphorus oxychloride in dimethylformamide.

This technique is particularly suitable for obtaining the compounds of formula 1,where R1represents optionally substituted N-methylindol-3-yl.

The compounds of formula (V), where R2, R3and X1have the above meanings, and X2represents an iodine atom, can be obtained by ladirovannye the compounds of formula (3):

where R2, R3and X1have the above values. The reaction of the salt is conveniently done by using or adapting methods described Saulnier and Cribble, J.Org.Chem., 1982, 47, 1982, for example, by treating compound of formula (3) lifedisabilities in an inert solvent, such as tetrahydrofuran, and at a temperature of about -78°C with subsequent interaction of the resulting anion with iodine. This reaction can conveniently be with indole, which is protected NH, for example, a group of Totila.

The compounds of formula (3), where R2, R3and X1have the above values, can be obtained by cyclization of the compounds of formula (4):

where R2, R3and X1have the above values. The cyclization reaction can conveniently be in the presence of alkali metal alkoxide, such as ethoxide sodium, in an inert solvent, such as ethanol, and at a temperature of from about on the th temperature to about the boiling temperature under reflux.

The compounds of formula (3), where R3and X1has the above meaning and R2represents hydrogen, can be obtained by cyclization of the compounds of formula (5):

where R3and X1have the above values. The cyclization reaction is conveniently carried out in the presence of sodium amide, N-methyl-aniline production, and at a temperature of from about 120°C to about 200°C.

The compounds of formula (3), where R3and X1have the above significance, and R2represents methyl (or1-4alkyl, optionally substituted-Z1R4where Z1and R4have the above values), can be obtained by cyclization of the compounds of formula (6):

where R3and X1have the above values, R11represents hydrogen or C1-4alkyl, optionally substituted-Z1R4where Z1and R4have the above values) and X5represents a halogen atom, preferably a bromine atom, or triflate group. The cyclization reaction is conveniently carried out in the presence of a complex metal catalyst such as tetrakis(triphenylphosphine)palladium(0), tertiary amine, such as triethylamine, and triarylphosphine, such as triphenylphosphine, in an inert solvent, such as dimethylformamide, and at a temperature of about 6° C to about 120°C. This method is particularly suitable for obtaining the compounds of formula (3), where R3and X1have the above values, X1is N and R2represents-CH3.

The compounds of formula (3), where R3, R2and x1have the above values can be obtained: (i) the interaction of the compounds of formula (7):

where R3and X1have the above meanings, and X6represents a halogen atom, preferably an iodine atom, with acetylene formula (8):

R2C≡C-SiMe3(8)

where R2has the above meanings, in the presence of a complex metal catalyst such as chloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (II), lithium chloride and sodium carbonate, in an inert solvent, such as dimethylformamide, and at a temperature up to about 100°C;

(ii) disilylgermane.

The compounds of formula (4) where R2, R3and X1have the above values, can be obtained by the coupling of compounds of formula (9):

where R2, R3and X1have the above values, with a mixture of formic acid and acetic anhydride.

The compounds of formula (5) where R 3and X1have the above values, can be obtained by the interaction of the corresponding compounds of the formula (9) where R3and X1have the above significance, and R2represents hydrogen, triethylorthoformate in the presence of an acid catalyst such as hydrogen chloride in ethanol, and at a temperature from about room temperature to about the boiling temperature under reflux.

The compounds of formula (6), where R3, R11and X1have the above meanings, and X5represents a halogen atom, can be obtained by alkylation of compounds of formula (7), where R3X1and X6have the above values, the corresponding alkenylsilanes formula (10):

R11CH=CHCH2X7(10)

where R11has the above meanings, and X7represents a halogen atom, preferably bromine. The alkylation reaction is conveniently carried out in the presence of alkali metal hydride such as sodium hydride, in an inert solvent, such as tetrahydrofuran, and at a temperature of about room temperature.

The compounds of formula (7), where R3and X1have the above meanings, and X6represents a bromine atom, can be obtained by bromirovanii is soedineniya formula (11):

where R3and X1have the above values, in dimethyl sulfoxide.

The compounds of formula (7), where R3and X1have the above meanings, and X5represents an iodine atom, can be obtained by ladirovannye the compounds of formula (11), where R3and X1have the above values. The reaction of the salt is conveniently done by using or adapting the way W-W.Sy, Synth.Comm., 1992, 22, pages 3215-3219.

The compounds of formula (V), where R1, R2, R3and X1have the above meanings, and X5is triflate group, can be obtained by the coupling of compounds of formula (12):

where R2, R3and X1have the above values, with the anhydride triperoxonane acid in the presence of base of Changsa, in an inert solvent, such as dichloromethane, and at a temperature of approximately 0°C. This reaction is conveniently performed using indole with NH, protected, for example, toiley group.

The compounds of formula (12), where R2, R3and X1have the above values, can be obtained by the coupling of compounds of formula (13):

where R3and X1have the above values, with metallocarboranes acid, in an inert solvent, such as dichloromethane, and at a tempera what ur about 5° C. This reaction is conveniently performed using indole with NH, protected, for example, toiley group.

The compounds of formula (13), where R3and X1have the above values, can be obtained by the coupling of compounds of formula (14):

where R3and X1have the above values, with lifedisabilities, in an inert solvent, such as tetrahydrofuran, followed by interaction with dimethylformamide at a temperature of about -78°C. This reaction is conveniently performed using indole with NH, protected, for example, toiley group.

The compounds of formula (14), where R3and X1have the above values, can be obtained by the coupling of compounds of formula (7), where R3and X1have the above meanings, and X6is iodine, with trimethylsilylacetamide in the presence of a complex metal catalyst such as chloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (II), followed by disilylgermane.

The compounds of formula (14), where R3have the above meanings, and X1is C-Z2R (where Z2is O and R is alkyl), can be obtained by the coupling of compounds of formula (14), where R3have the above meanings, and X1represents C-halogen, preferably C-Cl, with an alcohol of the formula R-OH in p is outstay hydroxide of an alkali metal, such as sodium hydroxide. The reaction is conveniently carried out at elevated pressure and at a temperature of approximately 170°C.

The compounds of formula (14), where R3has the above meanings, and X1is C-OH, can be obtained by the coupling of compounds of formula (14), where R3has the above meanings, and X1represents C-halogen, preferably C-Cl, with an aqueous solution of an alkali metal such as sodium hydroxide solution. The reaction is conveniently carried out at elevated pressure and at a temperature of approximately 180°C.

The compounds of formula (14), where R3have the above meanings, and X1is C-Cl, can be obtained by oxidation of compounds of formula (14), where R3has the above meanings, and X1is C-H, 3-chloroperbenzoic acid, in an inert solvent, such as dichloromethane, and at a temperature of approximately 0°C, followed by interaction of the N-oxide pyrrolo[2,3-b]pyridine with phosphorus oxychloride while boiling under reflux.

The compounds of formula (14), where R3have the above meanings, and X1represents a group C-C(=O)-OR5(where R5have the above values), can be obtained by the interaction of the corresponding compounds of formula (I)containing the group-C(=O)-OH, with alcohols of the formula R5-OH. For example, if R5is t the et-butyl, the reaction is conveniently carried out in the presence of 1,1'-carbonyldiimidazole and 1,8-diazabicyclo[5,4,0]undec-7-ene at a temperature of about room temperature.

The compounds of formula (14), where R3has the above meanings, and X1is C-heteroaryl (for example,can be obtained by the coupling of compounds of formula (16):

where R3has the above values, with the corresponding heteroarylboronic acid (for example 3,5-dimethylisoxazol-4-Bronevoy acid) in the presence of tetrakis(triphenylphosphine)palladium(0) and aqueous sodium bicarbonate. The reaction is conveniently carried out in dimethylformamide at a temperature of about 110°C.

The compounds of formula (VI), where R1has the above values can be obtained by the coupling of compounds of formula (15):

R1X8(15)

where R1has the above meanings, and X8represents a halogen atom, preferably bromine, in the presence of tributylamine, with a suitable base, such as utility, in an inert solvent, such as tetrahydrofuran, and at a temperature of about -100°C.

The compounds of formula (VI), where R1have the above values can be obtained by processing the soybean is inane formula (15), where R1have the above meanings, and X8represents a group-HgOAc, borane, in an inert solvent, such as tetrahydrofuran, and at a temperature of about room temperature.

The compounds of formula (15), where R1is optionally substituted indol-3-yl and X8represents a bromine atom, can be obtained by the interaction of the optionally substituted indoles with bromine in an inert solvent, such as dimethylformamide, and at a temperature of about room temperature.

The compounds of formula (13), where R1is optionally substituted indol-3-yl and X8represents a group-HgOAc, you can get the optional interaction of substituted indolines with acetate of mercury in glacial acetic acid at a temperature of about room temperature.

Further, the present invention presents, but without limitation, examples which are only illustrative examples and comparative examples.

Spectra1H nuclear magnetic resonance (1H NMR) was recorded on a Varian Unity spectrometer ENOVA with an operating frequency of 400 MHz. In the spectra of nuclear magnetic resonance chemical shifts (δ) are expressed in ppm relative to tetramethylsilane. Abbreviations have the following meanings: s=singlet; d=doublet; t=triplet; m=multiplet; q=Quartet; DD=doublet of doublets; DDD=double doublet of doublets.

T) were as follows:

METHOD A: HPLC column YMC ODS-A (50 mm x 4 mm) operating conditions for gradient elution with mixtures of water and acetonitrile, (A) 95:5 and (B) 5:95, containing 0.1% formic acid, gradient mobile phase (0,00 min, 95%A:5%B; linear gradient to 100% B for 2 min; then save to 3.4 min); flow 2 ml/min and a part of about 200 μl/min is directed to a mass spectrometer; the volume of the sample 10-40 ál; built-in diode matrix (220-450 nm), built-in detector light scattering in pairs (ELS) ELS-temperature 50°C, increased 8-1,8 ml/minute; source temperature 150°C;

METHOD B: HPLC column Luna C18 (2) (3 micron) (30 mm x 4.6 mm) operates under gradient elution with mixtures of (A) water containing 0.1% triperoxonane acid, and (B) acetonitrile containing 0.1% triperoxonane acid as mobile phase with a gradient: 0,00 min, 95%A:5%B; 0,50 min, 95%A:5%B; 4,50 min, 5%A:95%B; 5,00 min, 5%A:95%B; 5,50 min, 95%A:5%B; flow 2 ml/min; part of about 200 μl/min is directed to a mass spectrometer; the volume of the sample 10-40 ál; built-in diode matrix (220˜450 nm), a built-in detector light scattering in pairs (ELS) ELS-temperature 50°C, increased 8-1,8 ml/minute; source temperature 150°C.

METHOD C: LC-MS analyses performed on the device Micromass model LCT associated with the device model HP 1100. The content of compounds determined using a HP model G1315A with photodiode Matri is the principal detector for the wavelength interval of 200-600 nm and Sedex model 65 detector light scattering in pairs. Mass spectra accumulate in the interval 180-800. The results analyzed using the software Micromass MassLynx. The separation is carried out on a column of Hypersil BDS C18, particle size 3 µm (50x4,6 mm)using elution with a linear gradient from 5 to 90% acetonitrile containing 0.05% (vol./about.) triperoxonane acid in water containing 0.05% (vol./about.) triperoxonane acid for 3.5 min, with a volumetric flow of 1 ml/min. While the full cycle, including the re-establishment of equilibrium in the column is 7 minutes.

METHOD D: Column Hypersil BDS C-18 (4.6 mm x 50 mm) with reversed phase; working conditions; gradient elution with mixtures of (A) water containing 0.05% triperoxonane acid, and (B) acetonitrile containing 0.05% triperoxonane acid, as a gradient mobile phase: (0,00 min 100%A:0%B; linear gradient to 100% B for 2 minutes; then support a 3.5 min); flow 1 ml/min; the flow, approximately 0.25 ml/min, put up in mass spectrometer, the volume of the sample 10 ál; Hewlett Packard Model HPI I00 Series UV detector with an operating wavelength of 200 nm; detector light scattering in pairs (ELS); temperature detection 46°C, a nitrogen pressure of 4 bar.

Conditions of treatment using high-performance liquid chromatography-mass spectrometry (LC-MS) switching the following:

the connection is cleaned by LC/MS using Waters FractionLynx consisting of Grady is nnogo pump, Waters model 600, regenerative pump, Waters model 515, charging pump reagent (Waters Reagent Manager), autoinjector Waters model 2700, two switches Rheodyne model LabPro, photodiode Waters model 996. 1/1000 stream is mixed with methanol (volumetric flow rate of 0.5 ml/min) and sent to the detector; this flow is again divided, 3/4 flow is directed to the detector device with a photodiode, and 1/4 in the mass spectrometer; the rest of the output from the column (999/1000) is sent to the collector fractions, usually where the flow is directed into the drain, if only the expected mass signal does not determine the FractionLynx software. Software FractionLynx contains molecular formula of expected connections and switches the system on a collection of connections, when there are mass signals corresponding to [M+H]+and [M+Na]+. In some cases (depending on the analytical results of LC-MS, if [M+2H]++detected as an intense ion), software FractionLynx additionally equipped with the calculated value of half of the molecular mass (MM/2), in these conditions, the system also switches to the collection, when the detected mass signals corresponding to [M+2H]++and [M+Na+H]++. Compounds collected in tared glass ampoules. After collecting the solvent is evaporated in a centrifugal evaporator Jouan model RC 10.10 or centrifuge Genevac evaporator model NTI the number of connections that determine, weighing capsules after evaporation of the solvent. The detector device, a mass spectrometer, Waters model ZMD and collector fractions Gilson model 204. The device is controlled using software Waters FractionLynx.

In another embodiment, the separation is carried out on two symmetric columns (Waters Symmetry (C18, 5 μm, 19x50 mm, No. in catalogue 186000210), and one column functions as a regenerator in a mixture of 95/5 (about./about.) water/acetonitrile containing 0.07 per cent triperoxonane acid (about./vol.), while the other is separating. Column elute with a linear gradient of acetonitrile containing 0.07 per cent (about./about.) triperoxonane acid in water containing 0.07 per cent (about./about.) triperoxonane acid; 5 to 95% (vol./about.) for 8 minutes at a volumetric flow of 10 ml/min At the outlet of the separation column, the flow is divided in the ratio of 1/1000, using a separating device LC Packing AccuRate.

Retention time for high-performance liquid chromatography (HPLC: RTvalue) is determined using (i) method a : column18Phenomenex (g,6 mm)using gradient elution with a mixture of acetonitrile and water with 0.1% triperoxonane acid as mobile phase (0-1 min, 5% acetonitrile; 1-12 min rise up to 95% acetonitrile; 12-14,95 min 95% acetonitrile; 14,95-15 min 0% acetonitrile); or the Way In, column YMC ODS-AQ (h mm) gradient elution smesa and acetonitrile and water with 0.1% formic acid as mobile phase [95/5/0,1%(a) to 5/95/0,1%(C)] when the volumetric flow rate of 0.4 ml/min); or the Way: 3 micron BDS C18Hypersil (g,6 mm), gradient elution with mixtures of acetonitrile and water with 0.1% formic acid as mobile phase [95/5/0,1% water/acetonitrile/formic acid for 0.1 minutes, linear gradient to 5/95/0,1% water/acetonitrile/formic acid, 2 minutes and save up to 3.5 min].

Values of RFfor thin-layer chromatography (TLC) determine, using plates silica Merck.

EXAMPLE 1

(a) 6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b] pyrazin. A1-B1-C1, the product of the combination of group A1 in table 1 and B1 in table 2 and C1 in table 3:

Stir the solution Diisopropylamine (59,9 ml) in tetrahydrofuran (1400 ml), at -15°C in nitrogen atmosphere is treated with a solution of n-utility in hexano (131 ml, 1.6 m) for 25 minutes while maintaining the temperature below -10°C. After stirring for 30 minutes, the mixture is treated with methylpyrazine (26,8 g) for 15 minutes, then stirred for 1 hour and then treated with a solution of 5-methoxy-1-methyl-1H-indol-3-carbonitrile [53 g, Comparative example 1(a)] in tetrahydrofuran (600 ml) over 1 hour, keeping the temperature below -10°C. the Reaction mixture is allowed to warm to room temperature for 2 hours, then left overnight and then treated with water (100 ml). The tetrahydrofuran is removed in VA is uuma and the resulting mixture was distributed between ethyl acetate (500 ml) and water (200 ml). Two layers are separated and the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers washed with water (500 ml), then evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane and methanol (19:1, vol/vol.), getting listed in the title compound (19,4 g) as a gray solid. TPL 270-272°C. MS: 279(MH+).

(b) 6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin, A1-B1-C46, the product of the combination of group A1 in table 1, B 1 in table 2 and C46 in table 3:

Acting analogously to example 1(a) above but using 1-methylindol-3-carbonitrile [Comparative example 2(b)], receive 6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 264-266°C. [Elemental analysis: C, 72,34; H, to 4.68; N, 22,28%. Calculated for C15H12N4: C 72,56; H, TO 4.87; N, 22,57%].

(c) 6-(3-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin, A1-B91, the product of the combination of group A1 in table 1 and B91 table 2:

Acting analogously to example 1(a) above but using 3-bromobenzonitrile receive 6-(3-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a colorless solid. TPL 247-249°C. MS: 276(MH+).

(d) 7-isopropyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin. A61-B100, the product of the combination of group A1 in table 1 and B100 in table 2:

Acting similarly, PR is a measure 1(a) above, but using 2-isobutylpyrazine and benzonitrile, get 7-isopropyl-6-phenyl-5H-pyrrolo[2,3-b]pyrazin in the form of a colorless solid. TPL 216-218°C. MS: 238(MH+).

(e) 6-(4-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B90, the product of the combination of group A1 in table 1 and B90 table 2:

Acting analogously to example 1(a) above but using 4-bromobenzonitrile receive 6-(4-bromophenyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a colorless solid. TPL 326-329°C. MS: 276 (MH+).

(f) 6-(4-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin A1-B87, the product of the combination of group A1 in table 1 and B87 table 2:

Acting analogously to example 1(a) above but using 2-(4-cyanophenyl)- 1,3-dioxane (obtained by the method of example 3a patent application U.S. No 5750723), get 6-(4-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 288-289°C. TLC: RF=0,34 (ethyl acetate/pentane : 1/1).

(g) 6-(3-[1,3]dioxane-2-ylphenyl-5H-pyrrolo[2,3-b]pyrazin A1-B88, the product of the combination of group A1 in table 1 and B88 table 2:

Acting analogously to example 1(a) above but using 2-(3-cyanophenyl)-1,3-dioxane (obtained by the method of example 3a patent application U.S. No 5750723), get 6-(3-[1,3]dioxane-2-ylphenyl-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 205-206°C. [Elementn the th analysis: C, 68,28; H, 5,46; N, 15,02%. Calculated for C16H15N3O2: C, 68,31; H, LOWER THAN THE 5.37; N, 14,94%].

(h) 2-(5H-pyrrolo[2,3-b]pyrazin-6-yl)quinoline. A1-B103, the product of the combination of group A1 in table 1 and B103 table 2:

Acting analogously to example 1(a) above but using 2-hinolincarbonova will receive 2-(5H-pyrrolo[2,3-b]pyrazin-6-yl)quinoline as a yellow solid. TPL 293-295°C. MS: 247(MH+). [Elemental analysis: C, 72,76; H, 3,82; N, 22,56%. Calculated for C16P15N3O2: 73,16; H, 4.09 TO; N, 22,56%].

(i) 3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)isoquinoline. A1-B104, the product of the combination of group A1 in table 1 and B104 table 2:

Acting analogously to example 1(a) above but using 3-ethinlestradiol receive 3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)isoquinoline as a green solid. TPL 281-285°C. MS: 247(MH+).

(j) 6-[1-methyl-1H-indol-5-yl]-5H-pyrrolo[2,3-b]pyrazin. A1-B65, the product of the combination of group A1 in table 1 and B65 table 2:

Acting analogously to example 1(a) above but using 1-methyl-1H-indol-5-carbonitrile [Comparative example 2(c)], get 6-[1-methyl-1H-indol-5-yl]-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 260-265°C. MS: 249(MH+).

(k) 6-(5-methoxy-1-methyl-1H-indol-3-yl)-2-methyl-5H-pyrrolo[2,3-b]pyrazin. A64-B1-C1, the product of the combination of group IV table 1, B1 in table 2 and C1 in table 3:

Acting analogously to example 1(a) above but using 2,6-dimethylpyrazine receive 6-(5-methoxy-1-methyl-1H-indol-3-yl)-2-methyl-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MS: 249(MH+).1H NMR [(CD3)2SO]: δ 12,2-12,3 (1H, CL); 8,54, 8,56 (each 1H, s); 7,50 (1H, d, J=8,9 Hz); 7,47 (1H, d, J=2.4 Hz); of 6.96 (1H, DD, J=8,9 and 2.4 Hz); 6,91 (1H, s); 3,91, and a 3.87 2.57 m) (each 3H, s).

(l) 3-methyl-6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A66-B1-C1, the product of the combination of group A66 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 1(a) above but using 2,5-dimethylpyrazine and 1-methyl-1H-indol-3-carbonitrile [Comparative example 2(c)], a 3-methyl-6-(1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 170-175°C. MS: 263(MH+).

(m) 6-(1-benzyl-5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B24-C1, the product of the combination of group A1 in table 1, B24 in table 2 and C1 in table 3:

Acting analogously to example 1(a) above but using 1-benzyl-5-methoxy-1H-indol-3-carbonitrile [Comparative example 2(g)]receive 6-(1-benzyl-5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 240-244°C. TLC: RF=0,5 (dichloromethane/methanol 19/1).

(n) 6-(1-methyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]Piras is N. A1-B54, the product of the combination of group A1 in table 1 and B54 table 2:

Acting analogously to example 1(a) above but using 1-methyl-1H-pyrrol-3-carbonitrile [Comparative example 2(i)], receive 6-(1-methyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 211-213°C. MS: 199(MH+).

(o) 6-(1-methyl-1H-pyrrol-2-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B53, the product of the combination of group A1 in table 1 and B53 table 2:

Acting analogously to example 1(a) above but using 1-methyl-1H-pyrrol-2-carbonitrile [Comparative example 2(j)], receive 6-(1-methyl-1H-pyrrol-2-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 208-209°C. MS: 199(MH+).

(p) 6-indolizine-1-yl-5H-pyrrolo[2,3-b]pyrazin. A1-B40-C46, the product of the combination of group A1 in table 1, B40 in table 2 and C46 in table 3:

Acting analogously to example 1(a) above but using indolizine-1-carbonitrile [Comparative example 5], get 6-indolizine-1-yl-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 224-225°C (decomposition). MS: 235(MH+).

(q) 6-(3-methylindolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B41-C46, the product of the combination of group A1 in table 1, B41 in table 2 and C46 in table 3:

Acting analogously to example 1(a) above but using 3-methylindoline the-1-carbonitrile [Comparative example 6], get 6-(3-methylindolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 233-235°C (decomposition). MS: 249(MH+).

(r) 6-(1-methyl-2-phenyl-1H-pyrrol-4-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B52, the product of the combination of group A1 in table 1 and B52 in table 2:

Acting analogously to example 1(a) above but using 1-methyl-5-phenyl-1H-pyrrol-3-carbonitrile [Comparative example 2(k)], receive 6-(1-methyl-2-phenyl-1H-pyrrol-4-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 221-222°C (decomposition). MS: 275(MH+).

(s) 6-(5,6,7,8-tetrahydroquinolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B111, the product of the combination of group A1 in table 1 and B111 table 2:

Acting analogously to example 1(a) above but using 5,6,7,8-tetrahydroquinolin-1-carbonitrile [Comparative example 8], get 6-(5,6,7,8-tetrahydroquinolin-1-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 236-238°C (decomposition). MS: 239(MH+).

(t) 6-furan-3-yl-5H-pyrrolo[2,3-b]pyrazin. A1-B107, the product of the combination of group A1 in table 1 and B107 table 2:

Acting analogously to example 1(a) above but using 3-furonitrile, get 6-furan-3-yl-5H-pyrrolo[2,3-b]pyrazin as an orange solid. MS: 186,79 (MH+). TLC: RF=0,45 (dichloromethane/methanol): 19/1).

(u)dimethyl[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]amine. A1-B61, the product of the combination of group A1 in table 1 and B61 table 2:

Acting analogously to example 1(a) above but using 4-N,N-dimethylaminobenzonitrile receive dimethyl[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]amine as a yellow solid. TPL 297-298°C. MS: 239(MH+).

(v) 6-(5-methoxy-1-methyl-1H-indol-3-yl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin. A29-B1-C1, the product of the combination of group A29 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example (a), but using ethylpyrazine receive 6-(5-methoxy-1-methyl-1H-indol-3-yl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 243-244°C. HPLC (method A): RT=6.73 x minutes

(w) 6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B55, the product of the combination of group A1 in table 1 and B55 in table 2:

Acting analogously to example 1 (a) above but using 4-tert-butylbenzonitrile receive 6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. LC-MS: Method B: RT=3,29 min, 252(MH+).

(x) 6-(4-tert-butylphenyl)-7-methyl-5H-pyrrolo[2,3-b]pyrazin A29-B55, the product of the combination of group A29 in table 1 and B55 in table 2:

Acting analogously to example 1(a) above but using 2-ethylpyrazine and 4-tert-butylbenzonitrile receive 6-(4-tert-butylphenyl)-7-IU the Il-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 213-214°C. MS: 266(MH+).

(y) 6-(3,4-acid)-5H-pyrrolo[2,3-b]pyrazin. A1-B71, the product of the combination of group A1 in table 1 and B71 table 2:

Acting analogously to example 1 (a) above but using 3,4-dimethoxybenzonitrile receive 6-(3,4-acid)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow-orange solid. TPL 212-214°C. MS: 256(MH+).

(z) 6-(4-AMINOPHENYL)-7-methyl-5H-pyrrolo[2,3-b]pyrazin. A29-B79, the product of the combination of group A29 in table 1 and B79 table 2:

Acting analogously to example 1(a) above but using 2-ethylpyrazine and 4-aminobenzonitrile receive 6-(4-AMINOPHENYL)-7-methyl-5H-pyrrolo[2,3-b]pyrazin in the form of a brown solid. TPL 330-332°C. MS: 225(MH+).

(aa) 6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin. A1-B63, the product of the combination of group A1 in table 1 and B63 in table 2:

Acting analogously to example 1(a) above but using 4-(1-methyl)ethoxybenzonitrile [Comparative example 51]receive 6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MC: 254(MH+). HPLC (method B): RT=1,64 minutes

(ab) 6-(1H-1-methyl-2-(methylthio)imidazole-5-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B110, the product of the combination of group A1 in table 1 and B1 in table 2:

Acting similarly, PR is a measure 1(a) above, but using 1H-5-cyano-1-methyl-2-(methylthio)imidazole [Comparative example 52]receive 6-(1H-1-methyl-2-(methylthio)imidazole-5-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 230°C. MS: 246(MH+).

(ac) 6-(1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin A1-B21, product of the combination of group A1 in table 1 and B21 in table 2:

Acting analogously to example 1(a) above but using 3-cyano-1-methyl-1H-indazol[Comparative example 56(a)], receive 6-(1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MS: 250(MH+), 248(MH-).1H NMR [(CD3)2SO]: δ at 12.5 and 12.6 (1H, CL); scored 8.38 (1H, d, J=2.4 Hz); 8,24 (d, 1H, J=7.9 Hz); 8,21 (s, 1H, J=2.4 Hz); 7,76 (d, 1H, J=8,1 Hz); of 7.48 (t, 1H); to 7.32 (t, 1H); 7.29 trend (s, 1H); 4,18 (s, 3H).

(ad) 6-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B43, the product of the combination of group A1 in table 1 and B43 in table 2:

Acting analogously to example 1(a) above but using 3-cyano-1-methyl-4-phenyl-1H-pyrrole [Comparative example 56(b)], receive 6-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of solids, TPL 195°C (decomposition). MS: 275(MH+).

(ae) 6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin. A1-B89, the product of the combination of group A1 in table 1 and B89 table 2:

Acting analogously to example 1(a) above but using 4-torbenson the reel, get 6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin as not quite white solid. MC: 213(MH+).1H NMR [(CD3)2SO]: δ to 12.3 (s, 1H); and 8.4 (d, 1H); or 8.2 (d, 1H); with 8.05 (d, 2H); to 7.4 (d, 2H); to 7.2 (s, 1H).

(af) 6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B77, the product of the combination of group A1 in table 1 and B77 in table 2:

Acting analogously to example 1(a) above but using 4-methoxybenzonitrile receive 6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin as not quite white solid. TPL 244-246°C. MS: 225(MH+).

(ag) 6-[4-(tert-butyl)phenyl)-7-(prop-1-enyl)-5H-pyrrolo[2,3-b]pyrazin. A43-B55, the product of the combination of group A43 in table 1 and B55 in table 2:

Acting analogously to example 1(a) above but using 4-(tert-butyl)benzonitrile and 4-(pyrazinyl)-1-butene [Comparative example 59]receive 6-[4-(tert-butyl)phenyl)-7-(prop-1-enyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 207-208°C. MS: 292(MH+).

(ah) 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B92, the product of the combination of group A1 in table 1 and B92 in table 2:

Acting analogously to example 1(a) above but using 4-(methylthio)benzonitrile receive 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MS: 242(MH+).1H NMR[(CD3)2SO]: δ 12,48 (1H, s); of 8.37(1H, C); 8,18 (1H, s); 7,98 (2H, d, J=7.9 Hz); 7,19 (2H, d, J=7.9 Hz); 7,11 (1H, s); 2,52 (3H, s).

(ai) 6-(3-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B62, the product of the combination of group A1 in table 1 and B62 table 2:

Acting analogously to example 1(a) above but using 3-methoxybenzonitrile receive 6-(3-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin as an orange solid. TPL 194-196°C. MS: 226(MH+).

(aj) 6-(1-methyl-1H-pyrazole-4-yl)-5H-pyrrolo[2,3-b]pyrazin A1-B108, the product of the combination of group A1 in table 1 and B108 table 2:

As a result of processing by the method similar to the method of example 1(a) above but using 1-methyl-4-canoperate (obtained according to the method of Yoshida in J.Het.Chem., 1995, 32, page 701), get 6-(1-methyl-1H-pyrazole-4-yl)-5H-pyrrolo[2,3-b]pyrazin as an orange solid. TPL 232-234°C. MS: 200(MH+).

(ak) 6-(1-methyl-5-phenyl-1H-pyrazole-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B109, the product of the combination of group A1 in table 1 and B109 table 2:

Acting analogously to example 1(a) above but using 1-methyl-3-cyano-5-phenylpyrazol [Comparative example 1(k)], receive 6-(1-methyl-5-phenyl-1H-pyrazole-3-yl)-5H-pyrrolo[2,3-b]pyrazin as an orange solid. TPL 222-223°C. HPLC RT=of 7.36 minutes

(al) 6-(pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-V, the product of the combination of group A1 in table 1 and B101 in Alice 2:

Acting analogously to example 1(a) above but using 2-cyanopyridine, get 6-(pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 234-235°C.1H NMR [(CD3)2SO]: δ 8,71 (1H, d, J=4,1 Hz); scored 8.38 (1H, s); 8,24 (1H, s); 8,17 (1H, d, J=8,2 Hz); to 7.93 (1H, t, J=8,2 Hz); 7,41 (1H, m); of 7.36 (1H, s).

(am) 6-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B102, the product of the combination of group A1 in table 1 and B102 table 2:

Acting analogously to example 1(a) above but using 4-cyanopyridine, get 6-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 324-326°C.1H NMR [(CD3)2SO]: δ 8,69 (2H, d, J=7,1 Hz); to 8.45 (1H, s); with 8.33 (1H, s); 8,00 (2H, d, 3=7,1 Hz); 7,47 (1H, s).

(an) 6-(3,4-dimetilfenil)-5H-pyrrolo[2,3-b]pyrazin. A1-B75, the product of the combination of group A1 in table 1 and B75 table 2:

Acting analogously to example 1(a) above but using 3,4-dimethylbenzonitrile receive 6-(3,4-dimetilfenil)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MS: 224 (MH+). HPLC: RT=2,4 minutes

(ao) 6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B78, the product of the combination of group A1 in table 1 and B78 table 2:

Acting analogously to example 1(a) above but using 4-hydroxybenzonitrile receive 6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin in the IDA pale yellow solid. MS: 212 (MH+).

(ap) 6-(4-trifloromethyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B76, the product of the combination of group A1 in table 1 and B76 table 2:

Acting analogously to example 1(a) above but using 4-cryptomaterial receive 6-(4-trifloromethyl)-5H-pyrrolo[2,3-b]pyrazin in the form of a pale orange solid. MS:280(MH+). RT=2,64 minutes

(aq) 6-(4-AMINOPHENYL)-5H-pyrrolo[2,3-b]pyrazin. A1-B79, the product of the combination of group A1 in table 1 and B79 table 2:

Acting analogously to example 1(a) above but using 4-aminobenzonitrile and subjecting the reaction product chromatography on silica gel, elwira a mixture of ethyl acetate and pentane, and then the ethyl acetate receive 6-(4-AMINOPHENYL)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. MS: 211,1(MH+). RT=2,12 minutes

(ar) 6-(1-methyl-2-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B 112, the product of the combination of group A1 in table 1 and B112 table 2:

Acting analogously to example 1(a) above but using 1-methyl-2-phenyl-1H-pyrrol-3-carbonitrile [Comparative example 56(c)], receive 6-(1-methyl-2-phenyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 210°C (decomposition). MS:EI (electron emission) (70 eV); m/z=274 M+(100%).

(as) 6-(1,2-dimethyl-1H-pyrrol-4-yl)-5H-pyrrolo[2,3-b]is irisin. A1-B113, the product of the combination of group A1 in table 1 and 113 B in table 2:

Acting analogously to example 1(a) above but using 1,5-dimethyl-1H-pyrrol-3-carbonitrile [Comparative example 56(d)], receive 6-(1,2-dimethyl-1H-pyrrol-4-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 253°C. [Elemental analysis: C, 67,60; H, of 5.68; N, 26,22%. Calculated for C12H12N4: C, 67,91; H, 5,70; N, 26,40%].

(at) 6-(1,4-dimethyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B114, the product of the combination of group A1 in table 1 and B114 table 2:

Acting analogously to example 1(a), but using 1,4-dimethyl-1H-pyrrol-3-carbonitrile [comparative example 56(e)]receive 6-(1,2-dimethyl-1H-pyrrol-3-yl)-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 210°C. MS: EI (70 eV); m/z=212 M+(100%).

(au) 2-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-1H-pyrrolo[2,3-b]pyrazin. A2-B43, the product of the combination of group A2 in table 1 and B43 in table 2:

Acting analogously to example 1(a)but using 3-methylpyridine and 3-cyano-1-methyl-4-phenyl-1H-pyrrole [Comparative example 56(b)], receive 2-(1-methyl-4-phenyl-1H-pyrrol-3-yl)-1H-pyrrolo[2,3-b]pyrazin in the form of a brown solid. TPL 140°C (decomposition). MS: EI (70 eV); m/z=273 M+(100%).

EXAMPLE 2

3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol A1-B6-C46, the product whom is inali group A1 in table 1, B6 in table 2 and C46 in table 3:

A solution of 6-{1-[3-(tert-butyldimethylsilyloxy)propyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazine [29 g, Comparative example 3(a)] in tetrahydrofuran (500 ml) under nitrogen atmosphere is treated with a solution of tetrabutylammonium in tetrahydrofuran (144 ml, 1.0m). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo. The residue is treated with water, getting a solid, which is filtered off, then washed with water and then dried, obtaining mentioned in the title compound (17.5 g) as a yellow-brown solid. TPL 220-221°C. MS: 293(MH+).

(b) 3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol. A1-B6-C1, the product of the combination of group A1 in table 1, B6 in table 2 and C1 in table 3:

Acting analogously to example 2(a) above but using 6-{1-[3-(tert-butyldimethylsilyloxy)propyl]-5-methoxy-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin [Comparative example 3(b)]}, receive 3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol as a yellow solid. TPL 225-228°C. MS: 323 (MH+). TLC: RF=0,16 (dichloromethane/methanol: 19/1.vol.).

(c) 2-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol, A1-B5-C46, the product of the combination of group A1 in table 1, B5 in table 2 and C46 in table 3:

Acting analogously to example 2(a) above but using 6-{1-[2-(tert-butyldimethylsilyloxy)ethyl]-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin [Comparative example 3(c)]will receive 2-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl)ethanol as a yellow solid. TPL 272-273°C. MS: 279(MH+).

(d) 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol, A1-B5-C1, the product of the combination of group A1 in table 1, B5 in table 2 and C1 in table 3:

Acting analogously to example 2(a) above but using 6-{1-[2-(tert-butyldimethylsilyloxy)ethyl]-5-methoxy-1H-indol-3-yl}-5H-pyrrolo[2,3-b]pyrazin [Comparative example 3(d)]will receive 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]ethanol as a gray solid. TPL 270-273°C. MS: 309,43 (MH+).

(e) 6-(1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B2-C46, the product of the combination of group A1 in table 1 and B2 in table 2 and C46 in table 3:

Acting analogously to example 2(a) above but using 6-[1-(2-trimethylsilylethynyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin [Comparative example 3(f)]receive 6-(1H-indol-3-yl)-5H-pyrrolo-[2,3-b]pyrazin as an orange solid.1H NMR [(CD3)2SO]: δ 12,54 (1H, CL); 8,32 (1H, d, J=2,8 Hz); of 8.27 (1H, s); 8,19 (1H, d, J=2,8 Hz); 8,12 (1H, m); 7,71 (1H, m), 7,30 (2H, m), 7,03 (1H, d, J=2.0 Hz).

EXAMPLE 3

(a) 3-[3-(5H-pyrrolo-6-yl)indol-1-yl]Propylamine. A1-23-C46, the product of the combination of group A1 in table 1, B23 in table 2 and C46 in table 3:

A solution of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indolyl]propane-1-ol [12 g, EXAMPLE 2(a)] and tetrabromide carbon (19.1 g) in dichloromethane (300 ml) at room temperature is treated with a solution of triphenylphosphine (12.9 g) in dichloromethane (100 ml) within 5 minutes After stirring at room temperature for 3 hours, the reaction mixture was filtered and the solid part was washed with small amounts of dichloromethane. The filtrate and the washing fraction is evaporated, obtaining a brown resin, which is mixed with liquid ammonia (about 80 ml) in a sealed autoclave and allowed to mix at room temperature for 18 hours. Then the autoclave is cooled to -78°C and then gently open. The ammonia is allowed to evaporate and the residue is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane, methanol and concentrated ammonia (900:100:7, Rev./about./vol.), getting listed in the title compound as a yellow solid (3 g). TPL 170°C.1H NMR [(CD3)2SO]: δ of 8.28 (1H, d, J=2.7 Hz); 8,18 (1H, s); 8,10, to 7.64 (each 1H, d, J=7,7 Hz); of 8.09 (1H, d, J=2.7 Hz); 7.29 trend, of 7.23 (each 1H, TD, J=7.1 and 1.0 Hz); 6,97 (1H, s); 4,32 (2H, t, J=7.0 Hz); to 2.57 (2H, t, J=6,5 Hz); 1,89 (2H, quintet, J=6.4 Hz).

(b) 3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]Propylamine. A1-B23-C1, the product of the combination of group A1 in table 1, B23 in table 2 and C1 in table 3:

Acting analogously to example 3(a) above but using 3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol [EXAMPLE 2(b)], receive 3-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]Propylamine as a yellow solid. TPL 95-100°C and 150-160°C. MS:322 (MH+). TLC: RF=0,2(dichloromethane/methanol/concentrated ammonia: 900/100/7 about./about./vol.).

EXAMPLE 4

(a) N-{3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl)propyl}ndimethylacetamide. A1-B7-C46, the product of the combination of group A1 in table 1, B7 in table 2 and C46 in table 3:

Acetylchloride (31 μl) is added dropwise to a solution of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]Propylamine [100 mg, EXAMPLE 3(a)], triethylamine (52,2 μl) and dichloromethane (20 ml) at room temperature under nitrogen atmosphere. After stirring for 24 hours at room temperature, the reaction mixture is evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane and methanol (9:1, vol/vol.), getting listed in the title compound (82 mg) as a yellow solid. TPL 260°C. MS: 334 (MH+).

(b) N-[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]ndimethylacetamide. A1-B80, the product of the combination of group A1 in table 1 and in table B80 2:

Acting analogously to example 4(a) above, but IP is by using 6-(4-AMINOPHENYL)-5H-pyrrolo[2,3-b]pyrazin [EXAMPLE 1(aq), but not Comparative example 1(aq)], receive N-[4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]ndimethylacetamide in the form of a yellow solid. MS: 253,1 (MH+), RT=2,3 minutes

EXAMPLE 5

(a) 6-[1-(3-morpholine-4-ylpropyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin. A1-B27-C46, the product of the combination of group A1 in table 1, B27 in table 2 and C46 in table 3:

A mixture of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propyl bromide [250 mg, Reference example 4], the research (0.5 ml), potassium carbonate (100 mg) and potassium iodide (2 cores) ethylmethylketone refluxed for 2 hours. The mixture is allowed to cool to room temperature for 16 hours, then evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane and methanol (9:1, vol/vol.), getting a yellow glassy mass, which is then triturated with ethyl acetate and pentane, getting mentioned in the title compound (40 mg) as a yellow solid. TPL 180-185°C. MS: 362 (MH+).

(b) 6-[1-(3-piperidine-1-ylpropyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin. A1-B26, the product of the combination of group A1 in table 1 and B26 table 2:

Acting analogously to example 5(a) above but using piperidine, get 6-[1-(3-piperidine-1-ylpropyl)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin in the form of a yellow solid. TPL 240°C. MS: 360 (MH+ ).

EXAMPLE 6

6-{1-[3-(pyridine-3-yloxy)propyl]-1H-indol-3-yl}-1-5H-pyrrolo[2,3-b]pyrazin. A1-B22-C46, the product of the combination of group A1 in table 1, B22 in table 2 and C46 in table 3:

The solution diisopropylcarbodiimide (269 mm) in tetrahydrofuran (0.5 ml) is added dropwise over 2 min to a solution of triphenylphosphine (359 mg) in tetrahydrofuran (2.5 ml) at 0°C in nitrogen atmosphere. After stirring at this temperature for 20 min, the mixture is treated with a solution of 3-hydroxypyridine (65 mg) in tetrahydrofuran (1 ml) for 1 minute, then a suspension of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]propan-1-ol [200 mg, EXAMPLE 2(a)] in tetrahydrofuran (2 ml). The mixture is left to warm to room temperature for 18 hours, then evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of ethyl acetate and methanol (9:1, vol/vol.), getting listed in the title compound (110 mg) as a yellow solid. TPL 208-209°C. MS: 370 (MH+).

EXAMPLE 7

1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-ol. A1-B1-C10, the product of the combination of group A1 in table 1 and B1 in table 2 and C10 in table 3:

A mixture of 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [200 mg, EXAMPLE 1(a)], Hydrobromic acid (48%, 500 μl) and glacial acetic acid (3 ml) is boiled with a back hall is dildocam within 14 hours. After cooling, the mixture is neutralized by adding a saturated solution of sodium bicarbonate. The obtained solid dark color is filtered and then dried, obtaining mentioned in the title compound (180 mg) as a black solid. TPL 289-290°C. MS: 264 (MH+).

EXAMPLE 8

6-(2-chloro-5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin. A1-B15-C1, the product of the combination of group A1 in table 1, B15 in table 2 and C1 in table 3:

A solution of 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [100 mg, EXAMPLE 1(a)] dimethoxyethane (25 ml), cooled to -78°C, treated with a solution of n-utility in hexano (172 μl, 2,5M). After stirring for 30 min the mixture was treated with 4-toluensulfonate (82 mg), and then left to slowly warm to room temperature and then evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane and methanol (19:1, vol/vol.), getting listed in the title compound (45 mg) as a black solid. MS: 313 (MH+).1H NMR [(CD3)2SO]: δ 12,20 (1H, s); 8,39 (1H, d, J=3 z); 8,21 (1H, d, J=3 Hz); rate of 7.54 (1H, d, J=9 z); 7,30 (1H, d, J=2 Hz); of 6.96 (1H, DD, J=9 and 2 Hz); at 6.84 (1H, d, J=2 Hz); 3,82 (3H, s); 3,81 (3H, ).

EXAMPLE 9

(a) 3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde. A1-B96, the product of the combination of group A1 in table 1 and B96 in table 2:

A solution of 6-(3-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazine [1.6 g, EXAMPLE 1(g)] in dichloromethane (50 ml) is treated triperoxonane acid (5 ml). The resulting mixture was refluxed for 6 hours, then allowed to cool overnight and then evaporated. The residue is triturated with diethyl ether, obtaining a solid yellow color, which is recrystallized from ethyl acetate, getting mentioned in the title compound (0.6 g) as a crystalline yellow solid. TPL 268-270°C. [Elemental analysis: C, 69,96; H, to 3.92; N, 18,69%. Calculated for C13H9N3O: C, 69,95; H, 4,06; N, 18,82%].

(b) the hydrate of 4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde, A1-B95, the product of the combination of group A1 in table 1 and B95 table 2:

Acting analogously to example 9(a) above but using 6-(4-[1,3]dioxane-2-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin [EXAMPLE 1(f)], get the hydrate of 4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde, in the form of a yellow solid. TPL>295°C. [Elemental analysis: C, 67,57; H, 4,33; N, 18,04%. Calculated for C13H9N3O·N2ABOUT: WITH, 67,23; H, 4,34; N, 18,09%].

(c) [3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl)methanol A1-B4-C46, the product of the combination of group A1 in table 1 and B4 in table 2 and C46 in table 3:

Acting analogously to example 9(a) above but using 6-[1-(2-trimetric animationtimer)-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazin [Comparative example 3(t)], get [3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl)methanol as a brown solid. TPL >320°C.1H NMR [(CD3)2SO]: δ 8,13(1H, s); of 7.90 (2H, s), of 7.75 (1H, d); to 7.50 (1H, d); 7,15-of 7.25 (2H, m), 6,85 (1H, s); ceiling of 5.60 (2H, s).

EXAMPLE 10

(a) [3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]methanol. A1-B98, the product of the combination of group A1 in table 1 and B98 table 2:

A suspension of 3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde [0,4G, EXAMPLE 9(a)] in ethanol (50 ml) is treated with sodium borohydride (200 mg). The mixture is allowed to mix at room temperature for 1 hour, then treated with water (10 ml) and then evaporated. The remaining solid is triturated with water (50 ml), receiving solid pale yellow color, which is washed with water and then recrystallized from methanol, getting mentioned in the title compound (0.35 g) as a yellow solid crystalline substances. TPL 225-226°C. [Elemental analysis: C, 68,72; H, to 4.73; N, 18,44%. Calculated for C13H11N3O: C, 69,32; H, TO 4.92; N, 18,65%].

(b) [4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]methanol.

A1-B97, the product of the combination of group A1 in table 1 and B97 table 2:

Acting analogously to example 10(a) above but using 4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)benzaldehyde [EXAMPLE 9(b)], receive [4-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]methanol as a yellow solid fuel is Dogo substances. TPL 284-285°C. [Elemental analysis: C, 68,61; H and 4.65; N, 18,28. Calculated for C13H11N3O: C, 69,32; H, TO 4.92; N, 18,65%].

EXAMPLE 11

6-(5-Methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin.

A1-B2-C1, the product of the combination of group A1 in table 1 and B1 in table 2 and C1 in table 3:

Chilled (-78°C) solution of 6-(1-benzyl-5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [50 mg, EXAMPLE 1(m)] in tetrahydrofuran (20 ml) is treated with liquid ammonia (20 ml), then sodium (100 mg). After stirring at -78°C for 30 min, the reaction mixture was left to slowly warm to room temperature, then treated with water (50 ml) and then extracted three times with ethyl acetate (50 ml). The combined extracts dried over sodium sulfate and then evaporated. The residue is triturated with diethyl ether, obtaining mentioned in the title compound (14 mg) as a brown solid. TPL 268-271°C. MS: 265,24 (MH+).

EXAMPLE 12

(a) 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-ylatason. A1-B8-C1, the product of the combination of group A1 in table 1, B8 in table 2 and C1 in table 3:

Mix a solution of 6-(5-methoxy-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [70 mg, EXAMPLE 11] in anhydrous dimethylformamide (10 ml) is treated with sodium hydride (to 21.6 mg, 60% dispersion in mineral oil). After premesis the tion for 30 min the mixture is treated with a solution of 4-(2-chloroacetyl)of the research (to 44.1 mg) in dimethylformamide (1 ml) and stirring is continued for another 3 hours. The reaction mixture was poured into water (20 ml) and then extracted three times with ethyl acetate (30 ml). The combined extracts dried over sodium sulfate and then evaporated. The residue is triturated with diethyl ether, obtaining mentioned in the title compound (55 mg) as a yellow solid. TPL 263-267°C. MS: 392,21 (MH+).

(b) 2-[5-methoxy-1-(2-morpholine-4-yl-2-oxoethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile. A3-B8-C1, the product of the combination of group A3 in table 1, B8 in table 2 and C1 in table 3:

Acting analogously to example 12(a) above but using 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [EXAMPLE 32], get 2-[5-methoxy-1-(2-morpholine-4-yl-2-oxoethyl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile in the form of a yellow solid. LC-MS: METHOD D: RT=3,55 min, 416 (MH+).

EXAMPLE 13

(a) [5-methoxy-3-(1H-pyrrolo[2,3-b]pyrazin-2-yl)indol-1-yl]acetic acid. A2-B25-C1, the product of the combination of group A2 in table 1, B25 in table 2 and C1 in table 3:

A mixture of ethyl ester of {5-methoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]indol-1-yl}acetic acid [4.61 in town, Comparative example 13(a)], methanol (250 ml) and aqueous potassium hydroxide (5 M, 25 ml) is refluxed for 7 hours. The methanol is removed under reduced pressure, the residue is treated in the water (20 ml) and the pH of the solution was adjusted to 7, adding concentrated hydrochloric acid. The obtained solid yellow filtered and subjected to flash chromatography on silica gel, elwira a mixture of ethyl acetate and methanol (7:3, vol/vol.), getting listed in the title compound (1,69 g) as a white solid. MS: 320(M-H+). HPLC (METHOD A): RT=6,67 minutes

(b) 4-methoxy-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A5-B1-C1, the product of the combination of group A5 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 13(a)but using 4-methoxy-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 2(l)], receive a 4-methoxy-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow-brown solid. TPL 288-289°C. MS: 307 (MH+).

(c) 4-methoxy-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A5-B2-C1, the product of the combination of group A5 in table 1 and B2 in table 2 and C1 in table 3:

Acting analogously to example 13(a)but using 4-methoxy-2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (Comparative example 39), receive a 4-methoxy-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow-brown solid. TPL 294-295°C. MS: 294 (MH+).

(d) 4-chloro-2-(4-tert-butylphenyl-1H-pyrrolo[2,3-b]pyridine. A28-B55, the product of the combination of group A28 in table 1 and B55 in table 2:

Acting analogously to example 13(a)but using 4-chloro-2-(4-tert-butylphenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 12(j)], obtain 4-chloro-2-(4-tert-butylphenyl)-1H-pyrrolo[2,3-b]pyridine in the form of a cream solid. TLC: RF=0,71 (ethyl acetate/heptane 1:1).1H NMR [(CD3)2SO]: δ to 12.52 (1H, s); 8,16 (1H, d, J=6,1 Hz); to 7.93 (2H, d, J=8.1 Hz); 7,50 (2H, d, J=8.1 Hz); 7,21 (1H, d, J=6,1 Hz); of 6.96 (1H, s); of 1.30 (9H, s).

(e) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine. A65-B1-C1, the product of the combination of group A65 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 13(a)but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-5-phenyl(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(j)], receive 2-(5-methoxy-1-methyl-1H-indol-3-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridine in the form of a cream solid. TPL 240-242°C. MS: 354 (MH+).

(f) 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol. A2-B1-C5, the product of the combination of group A2 in table 1 and B1 in table 2 and C5 in table 3:

Acting analogously to example 13 (a) above but using 1-{1-methyl-3-[1-toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propan-2-ol [Comparative example 79], receive[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-2-ol in the form of a cream solid. TPL 198-199°C. HPLC (Method A): RT=6,69 minutes

(g) [5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid. A2-B121-C1, the product of the combination of group A2 in table 1, B121 in table 2 and C1 in table 3:

Acting analogously to example 13(a), but using tert-butyl ester {5,6-dimethoxy-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]indol-1-yl}acetic acid [Comparative example 13(q)], receive [5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid in the form of solid khaki. [Elemental analysis: C, 60,28; H, 5,16; N, 10,85%. Calculated for C19H17N3O4·1,5 H2A: C, 60,31; H, 5,33; N, 11.11 PER CENT]. MS: EI (70 eV); m/z=351 M+·(100%).

EXAMPLE 14

(a) 2-{[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-yl}Etalon. A2-B8-C1, the product of the combination of group A2 in table 1, B8 in table 2 and C1 in table 3:

A suspension of [5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid [60 mg, EXAMPLE 13(a)] in anhydrous dimethylformamide (7 ml) is treated with N-oxide hexaphosphate N-{(dimethylamino)(1H-1,2,3-triazolo[4,5-b]pyridine-1-yl)methylene}-N-methylmethanamine (71 mg) and diisopropylethylamine (45 ál). After stirring at room temperature for 30 min add morpholine (18 μl) and the mixture is stirred at room temperature for another 12 hours. actuarial removed in vacuum and the residue suspended in saturated sodium bicarbonate solution. Precipitated precipitated solid is filtered off, then dried, obtaining mentioned in the title compound (10 mg) as a purple solid. TPL 243-247°C. MS: 391 (MH+).

(b) amide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid. A2-B1-C15, the product of the combination of group A2 in table 1 and B1 in table 2 and C15 in table 3:

Acting analogously to example 14(a) above but using 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid [EXAMPLE 15(c)] and ammonium chloride, get amide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid in the form of a solid pale purple color. TPL 267-268°C. MS: 361 (MH+)

(c) methylamide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid. A2-B1-C16, the product of the combination of group A2 in table 1 and B1 in table 2 and C16 in table 3:

Acting analogously to example 14(a) above but using 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid [EXAMPLE 15(c)] and methylamine, get methylamide 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid as a pale purple solid. TPL 249-250°C. MS: 315 (MN+).

(d) methylamide 1-methyl-3-(1H-PI is Rolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-V1-C23, the product of the combination of group A2 in table 1 and B1 in table 2 and C23 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and methylamine, get methylamide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a pale orange solid. TPL 186°C. MS: 304 (MH+).

(e) (2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C34, the product of the combination of group A2 in table 1 and B1 in table 2 and C34 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and ethanolamine, receive (2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 256-257°C. MS: 335 (MH+).

(f) (2-morpholine-4-retil)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid, A2-B1-C47, the product of the combination of group A2 in table 1 and B1 in table 2 and C47 table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and 2-aminoethylphosphonic, receive (2-morpholine-4-retil)amide 1-methyl-3-(1H-feast of the olo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a colourless solid substances. TPL 268-270°C. MS: 404 (MH+).

(g) (2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C24, the product of the combination of group A2 in table 1 and B1 in table 2 and C24 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and β-alaninemia, receive (2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as colorless solid. TPL 286-288°C. MS: 362 (MH+).

(h) bis(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C48, the product of the combination of group A2 in table 1 and B1 in table 2 and C48 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and diethanolamin receive bis(2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 230-232°C. MS: 379 (MH+).

(i) amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C29, the product of the combination of group A2 in table 1 and B1 in table 2 and C29 table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and ammonium chloride, get amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 330-332°C. MS: 291 (MH+).

(j) (2-hydroxy-1,1-bis-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C49, the product of the combination of group A2 in table 1 and B1 in table 2 and C49 table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and Tris(hydroxymethyl)aminomethan, receive (2-hydroxy-1,1-bis-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid in the form of yellow solid. TPL 205-206°C. MS: 395 (MH+).

(k) (2-hydroxy-1-hydroxymethyl-1-methylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C30, the product of the combination of group A2 in table 1 and B1 in table 2 and C30 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and 2-amino-2-methyl-1,3-propandiol, receive (2-hydroxy-1-hydroxymethyl-1-methylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 180-182°C. MS: 379 (MH+).

(l) (2,3-dihydroxypropyl)amide 1-methyl-3-(1H-p is Rolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid, A2-B1-C50, the product of the combination of group A2 in table 1 and B1 in table 2 and C50 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and 3-amino-1,2-propandiol, get (2,3-dihydroxypropyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 171-172°C. MS: 365 (MH+).

(m) (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-karbonovoi acid. A2-B1-C31, the product of the combination of group A2 in table 1 and B1 in table 2 and C31 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and 2-amino-2-methyl-1-propanol, receive (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 161-162°C. MS: 365 (MH+).

(n) (2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C33, the product of the combination of group A2 in table 1 and B1 in table 2 and C33 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(d)] and ser is Nol, receive (2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 178-179°C. MS: 365,41 (MH+).

(o) (2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid. A2-B18-C24, the product of the combination of group A2 in table 1, B18 in table 2 and C24 in table 3:

Acting analogously to example I4(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid [EXAMPLE 15(g)] and 3-aminopropionitrile, receive (2-carbamoylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid as a pale yellow solid. TPL 277-280°C. MS: 362(MH+).

(p) (2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid. A2-B18-C34, the product of the combination of group A2 in table 1, B18 in table 2 and C34 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid [EXAMPLE 15(g)] and ethanolamine, receive (2-hydroxyethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid as a brown solid. TPL 264-267°C. MS: 335 (MH+).

(q) (1H-[1,2,4]triazole-3-yl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid. A2-B18-C51, is the product of the combination of group A2 in table 1, B18 in table 2 and C51 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid [EXAMPLE 15(g)] and 1H-[1,2,4]triazole-3-ylamine, get (1H-[1,2,4]triazole-3-yl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid as a yellow solid. TPL 343-345°C. MS: 358 (MH+).

(r) (2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid. A2-B18-C33, the product of the combination of group A2 in table 1, B18 in table 2 and C33 in table 3:

Acting analogously to example 14(a) above but using 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid [EXAMPLE 15(g)] and serinol, receive (2-hydroxy-1-hydroxymethylation)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid as a light brown solid. TPL 247-249°C. MS: 365 (MH+).

(s) (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(5H-pyrrolo[2.3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C31, the product of the combination of group A1 in table 1 and B1 in table 2 and C31 in table 3:

Acting analogously to example 14(a)but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and 2-amino-2-methyl-1-propanol, receive (2-hydroxy-1,1-dimethyl what Teal)amide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-carboxylic acid as a yellow solid. TPL 210-214°C. MS: 364 (MH+).

(t) 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-N-methylpropionamide. A33-B55, the product of the combination of group A33 in table 1 and B55 in table 2:

As a result of processing by the method similar to the method of example 14(a) above but using 3-[6-(4-tert-butylphenyl-5H - pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [EXAMPLE 25(a)] and methylamine, receive 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-N-methylpropionamide as not quite white solid. TPL 222-228°C. MS: 337 (MH+).

(u) 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-N,N-dimethylpropanamide. A34-B55, the product of the combination of group A33 in table 1 and B55 in table 2:

Acting analogously to example 14(a) above but using 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [EXAMPLE 25(a)] and dimethylamine, receive 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-N,N-dimethylpropanamide as not quite white solid. TPL 203-204°C. MS: 351 (MH+).

(v) 2-methoxyethylamine 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C25, the product of the combination of group A1 in table 1 and B1 in table 2 and C25 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic what islote [EXAMPLE 15(i)] and 2-methoxyethylamine, get 2-methoxyethylamine 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as an orange solid. MS: 350(MH+). HPLC (Method C): RT=1,27 minutes

(w) 2-Tien-2-ratelimit 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C27, the product of the combination of group A1 in table 1 and B1 in table 2 and C27 table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and 2-Tien-2-ylethylamine will receive 2-Tien-2-ratelimit 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as a yellow solid. MS: 402 (MH+). HPLC (Method C): RT=1,45 minutes

(x) 2-foretelling 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C53, the product of the combination of group A1 in table 1 and B1 in table 2 and C53 table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [15(i)] and 2-foreteller will receive 2-foretelling 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as an orange solid. MS: 338 (MH+). HPLC (Method C): RT=1,30 minutes

(y) 2-carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C54, product combin, is of group A1 in table 1, B1 in table 2 and C54 table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and ethyl ester hydrochloride β-alanine, get 2-carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as an orange solid. MS : 392 (MH+). HPLC (Method C): RT=1,38 minutes

(z) (hydroxymethyl)carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C52, the product of the combination of group A1 in table 1 and B1 in table 2 and C52 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and the hydrochloride of the methyl ester of serine, get (hydroxymethyl)carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as an orange solid. MC: 394 (MH+). HPLC (Method C): RT=1,24 minutes

(aa) 2-hydroxyethylamide (1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C34, the product of the combination of group A1 in table 1 and B1 in table 2 and C34 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic KIS the GTC [EXAMPLE 15(i)] and ethanolamine, get 2-hydroxyethylamide (1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 171-173°C (decomposition). MC: 336 (MH+).

(ab) methylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C23, the product of the combination of group A1 in table 1 and B1 in table 2 and C23 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and methylamine, get methylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid in the form of a cream solid, MS: 304 (MH+).1H NMR [(CD3)2SO]: δ 8,64 (1H, CL); 8,59 (d, 1H, J=1.0 Hz); of 8.27 (d, 1H, J=2.4 Hz); 8,17 (s, 1H); 8,15 (d, 1H, J=2.4 Hz); of 7.82 (DD, 1H, J=1.0 Hz, 7.9 Hz); a 7.62 (d, 1H, J=7.9 Hz); 7,21 (s, 1H); of 3.96 (s, 3H); 2.82 from (s, 3H).

(ac) dimethylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid.

A1-B1-C55, the product of the combination of group A1 in table 1 and B1 in table 2 and C55 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and dimethylamine, get dimethylamide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as a yellow solid. MS: 320 (MH+).1H NMR [(CD3)2SO]: B4; compared to 8.26 (d, 1H, J=2.1 Hz); 8,18 (s, 1H); 8,15 (d, 1H, J=2.1 Hz); a 7.62 (d, J=8.1 Hz); 7,372 (DD, 1H, J=1.0 Hz and 8.1 Hz); 6,98 (s, 1H); of 3.94 (s, 3H); 3,05 (s, 6H).

(ad) [1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]morpholine-4-Ilkeston. A1-B1-C56, the product of the combination of group A1 in table 1 and B1 in table 2 and C56 table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and morpholine, get [1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]morpholine-4-Ilkeston in the form of a yellow solid, MS: 362 (MH+).

(ae) 4-hydroxy-[1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl]-1H-indol-5-yl]carbonitriding. A1-B1-C57, the product of the combination of group A1 in table 1 and B1 in table 2 and C57 table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 15(i)] and 4-hydroxypiperidine, receive a 4-hydroxy-[1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl]-1H-indol-5-yl]carbonitriding in the form of a yellow solid, MS: 376 (MN+), 398(MNa+).

(af) of methylamide 3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl)carboalumination acid. A1-B1-C26, the product of the combination of group A1 in table 1 and B1 in table 2 and C26 table 3:

Acting analogously to example 14 (a) above but using 3-[-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl]carboalumination acid [EXAMPLE 15(l)] and methylamine, get methylamide 3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yl)carboalumination acid as a yellow solid. MC: 377(MH+). HPLC (Method C): RT=1,20 minutes

(ag) 3-hydroxypropylamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C34, the product of the combination of group A1 in table 1 and B1 in table 2 and C34 in table 3:

Acting analogously to example 14 (a) above but using 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-carbonous acid [EXAMPLE 15(i)] and 3-hydroxypropylamino get a 3-hydroxypropylamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid as a yellow solid. MC: 350 (MH+). HPLC (Method C): RT=1,22 minutes

(ah) 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-N-methylpropionamide. A33-B63, the product of the combination of group A33 in table 1 and B63 in table 2:

Acting analogously to example 14(a) above but using 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid [EXAMPLE 25(b)] and methylamine, get 3-{6-[4-(1-methyl)ethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}-N-methylpropionamide in the form of a yellow solid, MS: 339 (MH+). HPLC (Method C): RT=1,49 minutes

(ai) 3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide. A33-B77, the product of the combination of group A33 in table 1 and 77 table 2:

Acting analogously to example 14(a) above but using 3-[6-(4-methoxyphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [EXAMPLE 25(d)] and methylamine, receive 3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide as not quite white solid.1H NMR [(CD3)2SO]: δ 12,0 (s, 1H); 8.3 (l, 1H); or 8.2 (d, 1H); 7.7 (d, 2H); and 7.1 (d, 2H); and 3.8 (s, 3H); 3,05 (t, 2H); 2,6 (t, 2H); 2,5 (s, 3H). MC: 310 (MH+).

(aj) 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide. A32-B63, the product of the combination of group A32 in table 1 and B63 in table 2:

Acting analogously to example 14(a) above but using 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid [EXAMPLE 25(b)] and ammonium chloride, get 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide in the form of a white solid. MS: 325 (MH+). HPLC (Method C): RT=1,44 minutes

(ak) 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide. A32-B78, the product of the combination of group A32 in table 1 and B78 table 2:

Acting analogously to example 14(a) above but using 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid [EXAMPLE 30] and ammonium chloride, get 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionamide in the form of a white solid MS: 283(MH+T=2,18 minutes

(al) 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide. A33-B89, the product of the combination of group A33 in table 1 and B89 table 2:

Acting analogously to example 14(a) above but using 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [EXAMPLE 25(c)] and methylamine, receive 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide as not quite white solid.1H NMR [(CD3)2SO]: δ 12,5 (s, 1H); and 8.4 (d, 1H), and 8.2 (d, 1H); 7,8 (d, 2H); to 7.4 (d, 2H); 3,1 (t, 2H); 2,6 (t, 2H), and 2.5 (s, 3H). MC: 298(MH+).

(am) (2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid. A83-B1-C25, the product of the combination of group A83 in table 1 and B1 in table 2 and C25 in table 3:

Acting analogously to example 14 (a) above but using 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid [EXAMPLE 15(m)] and 2-methoxyethylamine, receive (2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid in the form of solids. TPL 249-250°C. MS: 443 (M+).

(an) (2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid. A83-B2-C25, the product of the combination of group A83 in table 1 and B2 in table is 2 and C25 in table 3:

Acting analogously to example 14 (a) above but using 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid [EXAMPLE 15(n)] and 2-methoxyethylamine, receive (2-methoxyethyl)amide 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid as a white solid. TPL 274-275°SMS: 430 (MH+).

(ao) (2-hydroxy-1,1-dimethylethyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid. A3-B1-C31, the product of the combination of group A3 in table 1 and B1 in table 2 and C31 in table 3:

Acting analogously to example 14 (a) above but using 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid [EXAMPLE 15(r)] and 2-amino-2-methylpropanol, receive (2-hydroxy-1,1-dimethylethyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid in the form of solids. MS: 388 (MH+). HPLC (Method C): RT=2,81 minutes

(ap) (2-hydroxy-2-methylpropyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid. A3-B1-C97, the product of the combination of group A3 in table 1 and B1 in table 2 and C97 table 3:

Acting analogously to example 14 (a) above but using 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid [EXAMPLE 15(r)] and 3-amino-2-methyl-propanol (obtained by the method, described Cabelta et. al. Tetrahedron, 1995, 51 (6), 1817-1826), receive (2-hydroxy-2-methylpropyl)amide 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid as a yellow solid. LC-MS: METHOD D: RT=2,69 min, 388 (MH+).

(aq) 2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl-indol-1-yl]-1-morpholine-4-ylatason. A2-B118-C1, the product of the combination of group A2 in table 1, B118 in table 2 and C1 in table 3

Acting analogously to example 14(a), but using [5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]acetic acid [EXAMPLE 13(g)]will receive 2-[5,6-dimethoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ylatason in the form of a pale yellow solid. TPL 260°C (decomposition). TLC: RF=0?37 (dichloromethane/methanol, 9/1). MS: ESI, m/z=421 MH+.

EXAMPLE 15

(a) [1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]acetic acid. A2-B1-C6, the product of the combination of group A2 in table 1 and B1 in table 2 and C6 in table 3:

A solution of ethyl ester {1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}acetic acid [500 mg, Comparative example 15(b)] in methanol (25 ml) is treated with potassium hydroxide (5 n, 3 ml) and then refluxed for 16 hours. The solvent is removed under reduced pressure and the residue is treated with water (10 ml). pH speedboat to 7, adding acetic acid, and the resulting colorless solid is filtered off, then dried, obtaining mentioned in the title compound (170 mg) as colorless solids. TPL >300°C. MS: 322 (MH+).

(b) 2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propionic acid. A2-B1-C2, the product of the combination of group A2 in table 1 and B1 in table 2 and C2 in table 3:

Acting analogously to example 15(a) above but using ethyl ester 2-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propionic acid [Comparative example 15(c)]will receive 2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propionic acid as colorless solid. TPL 177-178°C. MS: 336 (MH+).

(c) 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]CYCLOBUTANE-1-carboxylic acid. A2-B1-C11, the product of the combination of group A2 in table 1 and B1 in table 2 and C11 in table 3:

Acting analogously to example 15(a) above but using ethyl ester 1-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarboxylic acid [Comparative example 15(d)], receive 1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]CYCLOBUTANE-1-carboxylic acid as colorless solid. TPL 168-169°C. MS: 362 (MH+).

(d) 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B1-C28, the product of the combination of group A2 in table 1 and B1 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ether 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid [Comparative example 19(a)], receive 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL >300°C. MS: 291 (MH+).

(e) 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol. A2-B1-C10, the product of the combination of group A2 in table 1 and B1 in table 2 and C10 in table 3:

Acting analogously to example 15(a) above but using 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-ol [Comparative example 14(a)], receive 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol as a yellow solid. TPL 199-200°C. MS: 264 (MH+).

(f) 1-{1-(cyclobutanecarbonyl acid)-3-[1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarbonyl acid. A2-B12-C11, the product of the combination of group A2 in table 1, B12 in table 2 and C11 in table 3:

Acting analogously to example 15(a) above but using ethyl ester 1-{1-(ethyl ether cyclobutanecarbonyl acid)-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridi the-2-yl]-1H-indol-5-yloxy}cyclobutanecarboxylic acid [Comparative example 23(d)], get 1-{1-(cyclobutanecarbonyl acid)-3-[1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarbonyl acid as a yellow solid. TPL 240°C (decomposition). MS: 444 (MH+).

(g) 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid. A2-B18-C28, the product of the combination of group A2 in table 1, B18 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ether 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-6-carboxylic acid, [Comparative example 13(g)], receive 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-6-carboxylic acid as a yellow solid. TPL 359-361°C. MC 292 (MH+).

(h) 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]propionic acid. A2-B1-C21, the product of the combination of group A2 in table 1 and B1 in table 2 and C21 in table 3:

Acting analogously to example 15(a) above but using ethyl ester 3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yl}propionic acid [Comparative example 38(a)], receive 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]propionic acid as a yellow solid. TPL 268-270°C. MS: 320 (MH+).

(i) 1-methyl-3-(5H-pyrrolo[2,3-b]pyridine-6-yl)-1H-indole-5-carboxylic acid. A1-B1-C28, the product of the combination of group A1 in the table 1, B1 in table 2 and C28 in table 3:

Acting analogously to example 15(a)but using methyl ether 1-methyl-3-(5H-pyrrolo[2,3-b)pyrazin-6-yl)-1H-indole-5-carboxylic acid [Comparative example 19(b)], receive 1-methyl-3-(5H-pyrrolo[2,3-b]pyridine-6-yl)-1H-indole-5-carboxylic acid as a brown solid. TPL 350°C. HPLC (METHOD A): RT=5,85 minutes

(j) [2-methoxy-5-(5H-pyrrolo[2,3-b]pyridine-6-yl)phenoxy]acetic acid. A1-B67, the product of the combination of group A1 in table 1 and B67 table 2:

Acting analogously to example 15 (a) above but using ethyl ester [2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]acetic acid [EXAMPLE 27], receive [2-methoxy-5-(5H-pyrrolo[2,3-b]pyridine-6-yl)phenoxy]acetic acid as a white solid. TPL 330-332°C. MS: 300 (MH+).

(k) 3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyridine-6-yl)phenyl]propionic acid. A32-B74, the product of the combination of group A32 in table 1 and B74 table 2:

Acting analogously to example 15 (a) above but using ethyl 3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propionate [Comparative example 38(b)], receive 3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyridine-6-yl)phenyl]propionic acid as an orange solid. TPL 269-271°C. MS: 311 (MH+).

(l) 3-[1-methyl-3-(5H-pyrrolo[2,3b]pyridine-6-yl)-1H-indol-5-yl]carboalumination acid. A1-B1-C58, the product of the combination of group A1 in table 1 and B1 in table 2 and C58 table 3:

Acting analogously to example 15 (a) above but using 2-carbomethoxyamino 1-methyl-3-(5H-pyrrolo[2,3-b]pyridine-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 14(y)] and sodium hydroxide, to obtain 3-[1-methyl-3-(5H-pyrrolo[2,3-b]pyridine-6-yl)-1H-indol-5-yl]carboalumination acid as an orange solid (35 mg). MS: 364 (MN+). HPLC (Method C): RT=1,24 minutes

(m) 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid, A83-B1-C28, the product of the combination of group A83 in table 1 and B1 in table 2 and C28 in table 3:

Acting analogously to example 15 (a) above but using methyl ester of 3-[4-(3,5-dimethylisoxazol-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid [Comparative example 13(m)], receive 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid as a yellow solid. TPL >305°C. LC-MS (METHOD D): RT=2.57 m min

(n) 3-[4-(3,5-dimethylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid. A83-B2-C28, the product of the combination of group A83 in table 1 and B2 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above, but using the methyl ester of 3-[4-(3,5-dimethylisoxazol-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid [Comparative example 12(l)], receive 3-[4-(3,5-methylisoxazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid as a yellow solid. TPL >300°C. MS: 373 (MH+).

(o) 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A83-B1-C1, the product of the combination of group A83 in table 1 and B1 in table and C1 in table 3:

Acting analogously to example 15 (a) above but using 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(m)], obtain 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 254-255°C. MS: 373 (MH+).

(p) 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A83-B2-C1, the product of the combination of group A83 in table 1 and B2 in table 2 and C1 in table 3:

Acting analogously to example 15 (a) above but using 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 12(m)], obtain 4-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 270-271°C. TLC: RF=0,29 (ethyl acetate/heptane, 4:1).

(q) 3-(4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-yl)1-methyl-1H-indole-5-carboxylic acid. A5-B1-C28, the product of combines and group A5 in table 1, B1 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ester of 3-[4-(methoxy-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1-methyl-1H-indole-5-carboxylic acid [Comparative example 2(q)], receive 3-(4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indol-5-carboxylic acid in the form of a pink solid. LC-MS: METHOD D: RT=2,39 min, MS: 322 (MH+).

(r) 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid. A3-B1-C28, the product of the combination of group A3 in table 1 and B1 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ester of 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid, [Comparative example 81], receive 3-(4-cyano-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid as a pink solid. HPLC (Method C): RT=2,89 min MS: 317 (MH+).

(s) - 3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid. A2-B2-C28, the product of the combination of group A2 in table 1 and B2 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ether 1-(toluene-4-sulfonyl)-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid [Comparative example 12 (p)], receive 3-(1H-what irolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid substances. TPL >300°C.1H NMR [(CD3)2SO]: δ 12,85-to 12.95 (1H, s); 12,10-12,00 (1H, s); 8,65 (1H, s); 8,31 (1H, DD); of 8.28 (1H, d); of 8.25 (1H, DD); a 7.85 (1H, DD); at 7.55 (1H, d); 7,30 (1H, m), 6,97 (1H, d).

(t) 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A67-B2-C1, the product of the combination of group A67 in table 1 and B2 in table 2 and C1 in table 3:

Acting analogously to example 15(a) above but using tert-butyl ester 2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [Comparative example 67(b)], receive 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid as a dark solid. MS: 308(MH+), TLC: RF=0,04 (ethyl acetate/heptane, 3:1).

(u) potassium 2-(5-methoxy)-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate, potassium salt (A2-B2-C28, the product of the combination of group A2 in table 1 and B2 in table 2 and C28 in table 3:

Acting analogously to example 15(a) above but using methyl ether 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indole-5-carboxylic acid [Comparative example 19(a)] and viparita the reaction mixture with subsequent suspendirovanie in a minimal volume of water, collecting the solids and drying at 60°C in vacuum, get potassium 2-(5-methoxy-1H-indole-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate. TLC: RF=0,00 (ethyl acetate/pentane, 2:3). H NMR [(CD3)2SO]: δ to 8.57 (1H, s); 8,10, (1H, DD); of 7.90 (3H,m), 7,33 (1H, d); 7,00 (1H, DD); to 6.75 (1H, d).

EXAMPLE 16

(a) 2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]ethanol. A2-B1-C3, the product of the combination of group A2 in table 1 and B1 in table 2 and C3 in table 3:

A solution of ethyl ester {1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}acetic acid [120 mg, Comparative example 15(b)] in anhydrous tetrahydrofuran (5 ml) is treated with lithium aluminum hydride (1,0M solution in tetrahydrofuran, 50 ml) at 0°C in nitrogen atmosphere. The mixture is left to warm to room temperature, then stirred for 3 hours and then carefully poured into water (75 ml). The mixture is extracted three times with ethyl acetate (25 ml). The combined organic extracts washed with saturated salt solution (75 ml), dried over sodium sulfate and then evaporated, getting mentioned in the title compound (45 mg) as colorless solids. TPL 209-210°C. MS: 308 (MH+).

(b) 2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol. A2-B1-C7, the product of the combination of group A2 in table 1 and B1 in table 2 and C7 in table 3:

Acting analogously to example 16(a) above but using ethyl ester 2-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}impregnated the new acid [Comparative EXAMPLE 15(c)], get 2-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol as a colourless solid. TPL 164-165°C. MS: 320 (MH+).

(c) {1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]cyclobutyl}methanol. A2-B1-C12, the product of the combination of group A2 in table 1 and B1 in table 2 and C12 in table 3:

Acting analogously to example 16(a) above but using ethyl ester 1-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarboxylic acid [Comparative example 15(d)]get {1-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-yloxy]cyclobutyl}methanol as colorless solid. TPL 144-146°C. MS: 348 (MH+). HPLC (METHOD A): RT=6,37 minutes

(d) 2-(6-phenyl-5H-pyrrolo[2,3-b]pyridin-7-yl)ethanol. A44-B100, the product of the combination of group A44 in table 1 and B100 in table 2:

Acting analogously to example 16(a) above but using (6-phenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)acetic acid [Comparative example 35], get 2-(6-phenyl-5H-pyrrolo[2,3-b]pyridin-7-yl)ethanol as a colorless solid. TPL 201-202°C. MS: 348 (MH+). HPLC (METHOD A): RT=6,37 minutes [Elemental analysis: C, 70,68; H, 5,77; N, 17,44%. Calculated for C13H11N3O: C, 70,28; H, OF 5.48; N, 17,56%].

(e) 2-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]ethanol. A1-B66, product combined the promotion of group A1 in table 1 and B66 table 2:

Acting analogously to example 16 (a) above but using ethyl ester [2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]acetic acid [EXAMPLE 27], get 2-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]ethanol as a yellow solid. TPL 203-205°C. MS: 286 (MH+).

(f) 3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propan-1-ol. A1-B73, the product of the combination of group A1 in table 1 and B73 table 2:

Acting analogously to example 16(a) above but using ethyl 3-[2-dimethylamino-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propionate [Comparative example 38(b)], receive 3-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenyl]propan-1-ol as a yellow solid. TPL 203-204°C. MS: 297 (MH+).

(g) 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propyl alcohol. A30-B63, the product of the combination of group A30 in table 1 and B63 in table 2:

Acting analogously to example 16 (a) above but using 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid [EXAMPLE 25(b)], receive 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propyl alcohol in the form of a yellow solid (7 mg). MS: 312 (MH+). HPLC (Method C): RT=2,9 minutes

EXAMPLE 17

(a) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A2-B1-C1, the product of the combination of group A2 in table is 1, B1 in table 2 and C1 in table 3:

A solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [1.45 g, Comparative example 13(b)] in methanol (100 ml) is treated with potassium hydroxide (5 n, 15 ml), then refluxed for 2 hours. The reaction mixture is cooled, then evaporated. The residue is treated with water (150 ml), the hard part is filtered off, then dried, obtaining mentioned in the title compound (0.75 g) as a yellow-brown solid. TPL 226-227 of the°C. MS: 278 (MH+).

(b) 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-methoxy]propane-1,2-diol, A2-B1-C9 product of the combination of group A2 in table 1 and B1 in table 2 and C9 in table 3:

Acting analogously to example 17(a) above but using 3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propane-1,2-diol [Comparative example 16], receive 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol as a colourless solid. TPL 202-203°C. MS: 338 (MH+).

(c) 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol. A2-B1-C4, the product of the combination of group A2 in table 1 and B1 in table 2 and C4 in table 3:

Acting analogously to example 17(a) above but using 3-{1-methyl-3-[1-(toluene-4-sulfon the l)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propan-1-ol [Comparative EXAMPLE 17], receive 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1-ol as a yellow solid. TPL 192-193°C. MS: 322 (MH+).

(d) 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propan-2-ol. A2-B1-C5, the product of the combination of group A2 in table 1 and B1 in table 2 and C5 in table 3:

Acting analogously to example 17(a) above but using 3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propan-2-ol [Comparative example 17], receive 3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-2-ol as a yellow solid. TPL 201-202°C. MS: 332 (MH+).

(e) 2-[1-methyl-5-(2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine. A2-B1-C36, the product of the combination of group A2 in table 1 and B1 in table 2 and C36 in table 3:

Acting analogously to example 17(a) above but using 2-[1-methyl-5-(1-tributylstannyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 20], get 2-[1-methyl-5-(2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 303°C. MS: 316 (MH+).

(f) 2-[1-methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine. A2-B1-C35, the product of the combination of group A2 in table 1 and B1 in table 2 and C35 in table 3:

Acting analogion the example 17(a) above, but using 2-[1-methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 21], get 2-[1-methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine as a beige solid. TPL 299-300°C (decomposition). MS: 330 (MH+).

(g) 2-[1-methyl-5-(1-methyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine

Acting analogously to example 17(a) above but using 2-[1-methyl-5-(1-methyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 21], get 2-[1-methyl-5-(1-methyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine as a beige solid. TPL 286-289°C (decomposition). MS: 330 (MH+).

(h) 1-[1-methyl-3-(1H-pyrrolo(2,3-b]pyridine-2-yl)-1H-indol-5-yl]alanon. A2-B1-C20, a product of the combination of group A2 in table 1 and B1 in table 2 and C20 in table 3:

Acting analogously to example 17(a) above but using 1-[1-methyl-3-{(1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl}-1H-indol-5-yl]alanon [Comparative example 22], receive 1-[1-methyl-3-(1H-pyrrolo(2,3-b]pyridine-2-yl)-1H-indol-5-yl]Etalon in the form of a beige the solids. TPL 210°C (decomposition). MS: 290 (MH+).

(i) 2-[5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A2-B17-C1, the product of the combination of group A2 in table 1, B1 7 in table 2 and C1 is table 3:

Acting analogously to example 17(a) above but using 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(d)]will receive 2-[5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a beige solid. TPL 283-285°C (decomposition). MS: 308 (MH+).1H NMR [(CD3)2SO]: δ of 11.75 (1H, s); 8,10 (1H, DD); a 7.85 (1H, DD); to 7.77 (1H, s); 7,41 (1H, s); 7,13 (1H, s); 7,00 (1H, DD); to 6.75 (1H, s), 3,85 (3H, s), of 3.84 (3H, s); of 3.80 (3H, s).

(j) (R)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol. A2-B1-C80, the product of the combination of group A2 in table 1 and B1 in table 2 and C80 table 3:

Acting analogously to example 17(a) above but using (R)-3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propane-1,2-diol [Comparative example 24(a)], get (R)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol as a colourless solid. TPL 182-185°C. MS: 338 (MH+).

(k) (S)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol. A2-B1-C79, the product of the combination of group A2 in table 1 and B1 in table 2 and C79 table 3:

Acting analogously to example 17(a) above but using (S)-3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propane-1,2-diol [Compare the local example 24(b)], receive (S)-3-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol as a colourless solid. TPL 153-156°C. MS: 338 (MH+).

(l) 2-[5-(2-methoxy-1-methylethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine. A2-B1-C17, the product of the combination of group A2 in table 1 and B1 in table 2 and C17 in table 3:

Acting analogously to example 17(a) above but using 2-[5-(2-methoxy-1-methylethoxy)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 25], get 2-[5-(2-methoxy-1-methylethoxy)-1-methyl-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 150-151°C. MS: 336 (MH+).

(m) 2-[1-methyl-5-(5-methyl[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine. A2-B1-C68, the product of the combination of group A2 in table 1 and B1 in table 2 and C68 in table 3

Acting analogously to example 17(a) above but using 2-[1-methyl-5-(5-methyl[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 27], get 2-[1-methyl-5-(5-methyl[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine in the form of a cream solid. TPL 290-294°C. MS: 330 (MN+)

(n) (R)-3-[6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol. A2-B17-C80, the product of the combination of group A2 in table 1, B17 in table 2 and C80 table 3:

Acting analogously to example 17(a) above but using (R)-3-{6-methoxy-1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}propane-1,2-diol [Comparative example 24(c)], get (R)-3-[6-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yloxy]propane-1,2-diol in the form of a cream solid. MS: 368 (MH+). HPLC (METHOD A): RT=5,81 minutes

(o) 6-methoxy-1-methyl-3-[1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol. A2-B17-C10, the product of the combination of group A2 in table 1, B17 in table 2 and C10 in table 3:

Acting analogously to example 17(a) above but using 2-(5-hydroxy-6-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 28], get 6-methoxy-1-methyl-3-[1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ol as a brown solid. MS: 294 (MH+). HPLC (METHOD A): RT=6,37 minutes

(p) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrolo[2,3-b]pyridine. A13-B1-C1, the product of the combination of group A13 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 17(a)but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 2(m)], receive 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-phenyl-1H-pyrrolo[2,3-b]pyridine as a yellow solid matter.1H NMR [(CD3)2SO]; δ to 1.98 (1H, C); 8,21 (1H, d, J=3.5 HZ); 7,94 (1H, s); 7,86 (2H, d, J=8,8 Hz); to 7.59 (2H, t, J=8,8 Hz); 7,47 (2H, m); 7,39 (1H, d, J=1.9 Hz); 7,17 (1H, d, J=3.5 Hz); 6,93 (1H, DD, J=8,8, 1.9 Hz); PC 6.82 (1H, s); 3,84 (3H, s); 3,82 (3H, s).

(q) 2-[1-methyl-5-(pyridin-4-yl)-1H-indol-3-yl]-4-1H-pyrrolo[2,3-b]pyridine. A2-B1-C37, the product of the combination of group A2 in table 1 and B1 in table 2 and C37 table 3:

Acting analogously to example 17(a)but using 2-[5-(pyridin-4-yl)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (Comparative example 60)will receive 2-[1-methyl-5-(pyridin-4-yl)-1H-indol-3-yl]-4-1H-pyrrolo[2,3-b]pyridine in the form of a yellow solid. TPL 325-330°C.1H NMR [(CD3)2SO]; δ 8,65 (2H, d, J=7.2 Hz); to 8.20 (1H, s); 8,15 (1H, m); 8,04 (1H, s); 7,88 (3H, m); 7,72 (2H, m), 7,03 (1H, t, J=7.2 Hz); of 6.96 (1H, s); 3,93 (3H, s).

(r) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile. A3-B1-C1, the product of the combination of group A3 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [Comparative example 13(h)]will receive 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile in the form of orange the solids. TPL 304-305°C.1H NMR [(CD3)2SO]; δ 12,60 (1H, s); 8,24 (1H, s); 8,07 (1H, s); to 7.50 (3H, m); of 6.96 (1H, d, J=8.6 Hz); to 6.88 (1H, s); 3,91 (3H, s); 3,86 (3H, s).

(s) 4-chloro-2-(5-methodology the si-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A28-B1-C1, the product of the combination of group A28 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 4-chloro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(i)], obtain 4-chloro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow brown solid. TPL 250-252°C. MS: 312 (MN+).

(t) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine. A15-B1-C1, the product of the combination of group A15 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-(pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 2(o)]will receive 2-(5-methoxy-1-methyl-1H-indol-3-yl)-4-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 248-249°C. MS: 355 (MH+).

(u) 2-(5-methoxy-1-methyl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine. A2-B20-C1, the product of the combination of group A2 in table 1, B20 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(5-methoxy-1-methyl-1H-indol-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 2(p)] and recrystallization of the reaction product of ethyl acetate and subsequent washing IER the silt ether get 2-(5-methoxy-1-methyl-1H-indol-2-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid crystalline substances. TPL 234-235°C.1H NMR [(CD3)2SO]; δ 12,15-12,10 (s, 1H); 8,275-8,225 (DD, 1H); 8,00-7,975 (DD, 1H); 7,475 was 7.45 (d, 1H); 7,125-7,075 (m, 2H); 6,925-of 6.90 (s, 1H); 6,875-6,825 (m, 2H); 3.95 to are 3.90 (s, 3H); 3,80-KZT 3,775 (s, 3H).

(v) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-methyl-1H-pyrrolo[2,3-b]pyridine. A84-B1-C1, the product of the combination of group A84 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-methyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(k)], receive 2-(5-methoxy-1-methyl-1H-indol-3-yl)-3-methyl-1H-pyrrolo[2,3-b]pyridine as a beige the solids. TPL 237°C. [Elemental analysis: C, 74,15; H, 6,10; N, 14,54%. Calculated for C18H17N3O: C, 74,21 ;H, 5,88; N, 14,42%].

(w) 2-(1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine, A2-B115, the product of the combination of group A2 in table 1 and B115 table 2:

Acting analogously to example 17(a) above but using 2-(1H-pyrrol-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 67(g)]will receive 2-(1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. TPL 240°C (decomposition). [Elemental analysis: C, 72,11; H, of 4.95; N, 22,94%. Calculated for C11H9N3: C, 72,33; H, EQUAL TO 4.97; N, 21,85%]. MS: EI (eV); m/z=183 M+(100%); 155 (30%).

(x) 2-(1-methyl-1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine. A2-B53, the product of the combination of group A2 in table the e 1 and B53 table 2:

Acting analogously to example 17(a)but using 2-(1-methyl-1H-pyrrol-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(l)]will receive 2-(1-methyl-1H-pyrrol-2-yl)-1H-pyrrolo[2,3-b]pyridine as a white solid. TPL 183°C. MS: EI (70 eV); m/z=197 M+(100%).

(y) 4-chloro-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine, A28-B2-C1, the product of the combination of group A28 in table 1 and B2 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 4-chloro-2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 12(h)], obtain 4-chloro-2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine in the form of solids. LC-MS: METHOD D: RT=was 2.76 min, 298 (MH+).

(z) 5-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-6-ol. A2-B119-C1, the product of the combination of group A2 in table 1, B119 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(6-hydroxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 83], get 5-methoxy-1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-6-ol in the form of not-quite-white solid substances. TPL 250°C, MS: EI (70 eV); m/z=293 M+(100%).

(aa) 2-(6-isopropoxy-5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A2-B120-C1, the product of the combination of group A2 in table 1, B120 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-(6-isopropoxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 84], get 2-(6-isopropoxy-5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine in the form of not-quite-white solid substances. TPL 216°C. MS: EI (70 eV); m/z=335 M+(100%); 293 (90%); 278 (35%).

(ab) 2-[5,6-dimethoxy-1-(2-morpholine-4-retil)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine. A2-B122-C1, the product of the combination of group A2 in table 1, B122 in table 2 and C1 in table 3:

Acting analogously to example 17(a) above but using 2-[5,6-dimethoxy-1-(2-morpholine-4-retil)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [Comparative example 13(r)]will receive 2-[5,6-dimethoxy-1-(2-morpholine-4-retil)-1H-indol-3-yl]-1H-pyrrolo[2,3-b]pyridine as a pale pink solid. TPL 218°C. MS: ESI, m/z=407 MH+.

EXAMPLE 18

1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ylamine. A2-B1-C63, the product of the combination of group A2 in table 1 and B1 in table 2 and C63 in table 3:

Mix a solution of tert-butyl methyl ether [1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]carbamino acid [0.2 g, Comparative example 30] in dichloromethane is treated triperoxonane acid (2 ml). After peremeci the project at room temperature for 16 hours, the reaction mixture is evaporated. The residue is suspended in a saturated solution of sodium bicarbonate (10 ml) and the resulting solid is filtered, then dried, obtaining mentioned in the title compound as a yellow solid. TPL 247-248°C. MS: 263 (MH+).

EXAMPLE 19

(a) N-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methanesulfonamide. A2-B1-C62, the product of the combination of group A2 in table 1 and B1 in table 2 and C62 in table 3:

A solution of 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-ylamine [52,4 mg, EXAMPLE 18] in dichloromethane (5 ml) is treated with triethylamine (30 μl), then methanesulfonanilide (17 μl). After stirring at room temperature for 16 hours, the reaction mixture was diluted with dichloromethane (10 ml), washed with water (10 ml), then washed with saturated salt solution (10 ml), dried over magnesium sulfate and then evaporated. The remaining solid is triturated with diethyl ether, obtaining mentioned in the title compound as a yellow solid. TPL p.223-224°C. MS: 341 (MH+).

(b) N-[1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]ndimethylacetamide. A2-B1-C45, the product of the combination of group A2 in table 1 and B1 in table 2 and C45 in table 3:

Acting analogously to example 19(a) above but using acetylchloride receive N-[1-methyl-3-(1H-pyrrolo[2,3-b]feast the DIN-2-yl)-1H-indol-5-yl]ndimethylacetamide in the form of a yellow solid. TPL 220-221°C. MS: 305 (MH+).

(c) N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}Tien-2-yl-sulfonamide. A2-B1-C69, the product of the combination of group A2 in table 1 and B1 in table 2 and C69 table 3:

Acting analogously to example 19(a) above but using [3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indol-5-yl]methylamine [EXAMPLE 52] and 2-thienylboronic receive N-{1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}Tien-2-ylsulphonyl in the form of a pale orange solid. TPL 226-227 of the°C.

EXAMPLE 20

(a) {1-[5-(1-hydroxymethylcellulose)-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]cyclobutyl}methanol. A2-B13-C12, the product of the combination of group A2 in table 1, B13 in table 2 and C12 in table 3:

Stir a solution of the ethyl ester of 1-{1-(ethyl ether cyclobutanecarbonyl acid)-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-yl]-1H-indol-5-yloxy}cyclobutanecarboxylic acid [0,54 g, Comparative example 23(d)] in tetrahydrofuran (50 ml) at 0°C in nitrogen atmosphere is treated dropwise with a solution of tetrahydroaluminate lithium in tetrahydrofuran (4.9 ml, 1.0m). After stirring for 2 hours at 0°C, the reaction mixture is left at room temperature for another 18 hours, then treated dropwise with water (20 ml) and then filtered through Hyflo Super Ge1®, diatomaceous earth is Yu. The filter cake is washed with ethyl acetate (20 ml), the two-phase filtrate is separated and the aqueous layer was extracted twice with ethyl acetate (25 ml). The combined organic phases are washed with saturated salt solution (25 ml), then dried over magnesium sulfate and then evaporated. The residue is triturated with diethyl ether and nerastvorimaya substance is subjected to flash chromatography on silica gel, elwira a mixture of dichloromethane and methanol (19:1, vol/vol.), getting listed in the title compound (0,19 g) as a cream solid. TPL 165-166°C. MS: 418 (MH+).

(b) {1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutyl}methanol. A1-B1-C13, the product of the combination of group A1 in table 1 and B1 in table 2 m C13 table 3:

Acting analogously to example 20(a) above but using ethyl ester {1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutanecarbonyl acid [Comparative example 15(e)]get {1-[1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indol-5-yloxy]cyclobutyl}methanol as a brown solid substances. TPL 267-271°C. MS: 349 (MH+).

EXAMPLE 21

(a) methanesulfonate 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine

Methansulfonate acid (70 μl) are added to a solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine [300 mg, EXAMPLE 17(a) in tetrahydrofuran (20 ml) at room temperature. The mixture is stirred for 45 min and the precipitate is filtered off, getting mentioned in the title compound (390 mg) as a yellow solid. TPL 256-257°C. [Elemental analysis: C, 57,60; H, of 4.77; N, 10,90%. Calculated for C13H11N3O: C, 57,90; H, 5,13;N, 11.25 PER CENT].

(b) methanesulfonate 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine

Acting analogously to example 21(a) above but using 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazin [EXAMPLE 1(a)], get methanesulfonate 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine in the form of a yellow solid. TPL 245-250°C. MS: 279 (MH+).

(c) methanesulfonate 2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ratanana

Acting analogously to example 21(a) above but using 2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ylatason [EXAMPLE 14(a)], get methanesulfonate 2-[5-methoxy-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)indol-1-yl]-1-morpholine-4-ratanana in the form of a yellow the solids. TPL 214-215°C. MS: 391 (MH+).

(d) methanesulfonate (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid

Acting analogously to example 21(a) above but using (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-PI is Rolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [EXAMPLE 14(m)], get methanesulfonate (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid as a yellow solid. TPL 190-192°C. MS: 363 (MH+).

(e) methanesulfonate 6-[5-(2-hydroxy-1,1-dimethylthiocarbamyl)-1-methyl-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazine

Acting analogously to example 21(a)but using (2-hydroxy-1,1-dimethylethyl)amide 1-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-1H-indole-5-carboxylic acid [EXAMPLE 14(s)], get methanesulfonate 6-[5-(2-hydroxy-1,1-dimethylthiocarbamyl)-1-methyl-1H-indol-3-yl]-5H-pyrrolo[2,3-b]pyrazine in brown the solids. TPL 240°C (decomposition).1H NMR [(CD3)2SO]; δ 8,50 (W, C); of 8.37 (1H, d, J=3.0 Hz); 8,32 (1H, d, J=3.0 Hz); 8,29 (1H, s); of 7.82 (1H, d, J=8,2 Hz); to 7.77 (1H, s); to 7.64 (1H, d, J=8,2 Hz); 7,20 (1H, s); of 3.95 (3H, s); 3,59 (2H, s); is 2.37 (3H with); to 1.38 (6H, s).

(f) methanesulfonate 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-ratanana

Acting analogously to example 21(a)but using 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-ylatason (EXAMPLE 12), get methanesulfonate 2-[5-methoxy-3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholine-4-ratanana. TPL 250°C.1H NMR [(CD3)2SO]; δ 8,32 (1H, s); by 8.22 (1H, s); 8,11 (1H, s); 7,50 (1H, s); 7,44 (1H, d, J=8,8 Hz);? 7.04 baby mortality (1H, s); 6,93 (1H, d, J=8,8 Hz); are 5.36 (2H, s); are 3.90 (3H, s); 3,61 8H, m); 2,31 (3H, s).

(g) methanesulfonate 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine

Acting analogously to example 21(a)but using 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine [EXAMPLE 17(i)], get methanesulfonate 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine.1H NMR [(CD3)2SO]; δ of 8.25 (2H, m); of 7.90 (1H, s); 7,42 (1H, s); 7,33 (1H, DD); 7,16 (1H, s);? 7.04 baby mortality (1H, s); are 3.90 (3H, s); of 3.85 (3H, s); a-3.84 (3H, s); a 2.36 (3H, s).

EXAMPLE 22

5-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]ethyl-2H-tetrazol. A35-B55, the product of the combination of group A35 in table 1 and B55 in table 2:

To a stirred solution of 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionitrile [0.2 g, EXAMPLE 23] in toluene (25 ml) at room temperature under nitrogen atmosphere add usedatabaseyou (0,61 ml). The reaction mixture is heated at 117°C. After 24 hours, add an additional aliquot usedatabaseyou (of 0.21 ml) and the reaction mixture is heated for another 24 hours. The reaction mixture was quenched with glacial acetic acid (44 ml) and stirred for 15 minutes before distributed between water and ethyl acetate. Two layers are separated and the organic fraction washed with water, dried over magnesium sulfate and then evaporated. The residue is subjected to flash chromatography on silica gel, elwira with ethyl acetate, olucha specified in the title compound (0.06 g) in the form of not-quite-white solid. MS: 348 (MH+). HPLC (Method B): RT=1,64 minutes

EXAMPLE 23

3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2H-propionitrile. A45-B55, the product of the combination of group A45 in table 1 and B55 in table 2:

To a solution of 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionamide [0.1 g, EXAMPLE 24] in tetrahydrofuran (15 ml) at room temperature is added triethylamine (1 ml) and phosphorus oxychloride (1 ml). The reaction mixture was refluxed for 30 min, then poured into 10% sodium bicarbonate solution. The mixture is extracted with ethyl acetate and the combined organic extracts washed with water, dried over magnesium sulfate and evaporated. The residue is subjected to flash chromatography on silica gel, elwira first with a mixture of ethyl acetate and pentane (1:1, vol/vol.), then with ethyl acetate, getting mentioned in the title compound as a white solid. TPL 215-216°C. MS:305 (MH+).

EXAMPLE 24

3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionamide. A32-B55, the product of the combination of group A32 in table 1 and B55 in table 2:

To a solution of 3-[6-(4-tertbutylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [0.51 g, EXAMPLE 25(a)] in dimethylformamide (15 ml) at room temperature under nitrogen atmosphere add tetrafluoroborate O-benzotriazol-1-yl-N,N,N',N'-tetramethylurea (054 g) and triethylamine (0,22 ml). Gaseous ammonia is bubbled through the solution for 5 min and sealed, the reaction mixture was allowed to stand at room temperature overnight. Then the solution was poured into water and extracted with ethyl acetate. The organic extracts washed with water and dried over sodium sulfate, getting mentioned in the title compound as a white solid without further purification. MS: 323 (MH+). HPLC (Method B): RT=4,49 minutes

EXAMPLE 25

(a) 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid. A31-B55, the product of the combination of group A31 in table 1 and B55 in table 2:

To a solution of dimethyl 1,1-in primary forms 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic 1,1-decollate [0.4 g, Comparative example 44(a)] in methanol (20 ml) is added 1N. the sodium hydroxide solution (4 ml). The reaction mixture is heated at 50°C for 6 hours, then allowed to stand at room temperature overnight. The solvent is removed by evaporation, then add 6N sulfuric acid solution (50 ml) and the reaction mixture is refluxed for 2 hours. After cooling, the pH of the solution was adjusted to 4 using 1N. the sodium hydroxide solution, and the precipitate is filtered off, dried in vacuum, obtaining mentioned in the title compound (0.26 g) in the form of not quite white is on solids without additional purification. TPL 274-275°C. MS: 324 (MH+).

(b) 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid. A31-B63, the product of the combination of group A31 in table 1 and B63 in table 2:

Acting analogously to example 25(a) but using dimethyl 1,1, in primary forms 3-[6-(4-(1-methyl)ethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic 1,1-decollate [Comparative example 44(b)], receive 3-{6-[4-(1-methyl)ethoxyphenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid as a yellow solid. MS: 326 (MN+). HPLC (Method C): RT=1,56 minutes

(c) 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid. A31-B89, the product of the combination of group A31 in table 1 and B89 table 2:

Acting analogously to example 25(a), but using dimethyl 1,1, in primary forms 3-{6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic 1,1-decollate [Comparative example 44(c)], receive 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid in the form of not-quite-white solid.1H NMR [(CD3)2SO]; δ to 12.3 (s, 1H); and 8.4 (d, 1H); or 8.2 (d, 1H); 7,8 (d, 2H); to 7.4 (d, 2H); 3,1 (t, 2H); and 2.7 (t, 2H). MC: 285 (MH+).

(d) 3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid. A31-B77, the product of the combination of group A31 in table 1 and B77 in table 2:

Acting analogously to example 25(a) above, but is using dimethyl 1,1, in primary forms 3-[6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic 1,1-decollate [comparative EXAMPLE 44(d)], receive 3-[6-(4-forfinal)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid in the form of not-quite-white solid.1H NMR [(CD3)2SO]; δ 12,0 (s, 1H); 8.3 (l, 1H); or 8.2 (d, 1H); 7.7 (d, 2H); and 7.1 (d, 2H); and 3.8 (s, 3H); 3,05 (t, 2H); 2,6 (t, 2H). MC: 297 (MH+).

EXAMPLE 26

3-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propan-1-ol. A30-B55, the product of the combination of group A30 in table 1 and B55 in table 2:

To a mixture of 4h. hydrochloric acid in dioxane and methanol (5 ml of 1:1, vol/about.) add 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic acid [0.02 g, EXAMPLE 25(a)] and the reaction mixture is allowed to mix at room temperature over night. After evaporation the residue is suspended in sodium bicarbonate solution (10%) and ethyl acetate. The phases are separated, the organic fraction washed with water and dried over sodium sulfate. After evaporation the residue is suspended in diethyl ether (50 ml). Add alumoweld lithium (0,12 ml of 1M solution in diethyl ether) and the suspension is refluxed for 2 hours. Add an additional aliquot of lithium aluminum hydride (0,12 ml of 1m solution in diethyl ether) and the reaction mixture is heated for a further 1 hour. The reaction is quenched with cold water (10%) solution of potassium hydrosulfate, which is added dropwise to the cessation of hydrogen evolution, resbala the tons of water and extracted with ether. The combined organic fractions washed with water, dried over sodium sulfate and subjected to flash chromatography on silica gel, elwira with ethyl acetate, getting mentioned in the title compound (0.035 g) in the form of not-quite-white solid. TPL 187-189°C. MS: 310 (MH+).

EXAMPLE 27

Ethyl ester of [2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenoxy]acetic acid. A1-B68, the product of the combination of group A1 in table 1 and B68 table 2:

To a solution of 2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenol [0.5 g, EXAMPLE 28] in dimethylformamide (10 ml) and cesium carbonate (0.67) d) add ethylchloride (0.025 g). The reaction mixture is heated at 50°C during the night. After cooling, the dimethylformamide is removed in vacuo and the residue distributed between ethyl acetate and water. The organic fraction is dried over sodium sulfate, evaporated and the residue is subjected to flash chromatography on silica gel, elwira of 2.5% methanol in dichloromethane. The product is then triturated with a mixture of ethyl acetate and pentane, getting mentioned in the title compound as a white solid. TPL 183-184°C. MS: 328 (MH+).

EXAMPLE 28

2-Methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)phenol. A1-B70, the product of the combination of group A1 in table 1 and B70 table 2:

To a solution of 6-(3-tert-butyldimethylsilyloxy-4-methoxy)phenyl-5H-p is Rolo[2,3-b]pyrazine [1.0 g, Comparative example 49] in tetrahydrofuran (50 ml) is added tetrabutylammonium fluoride (5,63 ml of 1m solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for 3 hours. The tetrahydrofuran is removed under reduced pressure and the residue suspended in water. The obtained solid product is filtered off and dried in vacuum, obtaining mentioned in the title compound as a white solid (0.56 g), which is used without further purification. MS: 242 (MH+). HPLC (Method B): RT=3,02 minutes

EXAMPLE 29

3-fluoro-2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine. A62-B1-C1, the product of the combination of group A62 in table 1 and B1 in table 2 and C1 in table 3:

A solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine [0.1 g, EXAMPLE 17(a)] in anhydrous tetrahydrofuran (4 ml), at 0°C, treated with methylmagnesium (0,042 ml) and after stirring for another 20 min at 0°C the mixture is treated with bis(tetrafluoroborate) 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane (0,13 g). The reaction mixture was stirred at room temperature for 4 hours, then incubated at room temperature overnight, then heated at 40°C for 4 hours, then heated at 80°C for 2 hours, then cooled to room temperature and partitioned between uh what racedata and water. The aqueous layer was extracted three times with ethyl acetate (25 ml). The combined extracts and an ethyl acetate layer after separation was washed with a saturated salt solution, dried over magnesium sulfate and then evaporated. The residue is triturated with ethyl acetate, getting mentioned in the title compound (0,057 g) as a white solid. TPL 248-250°C.1H NMR [(CD3)2SO]; δ 12,20 (1H, s); 8,24 (1H, m), 7,81 (1H, s); 7,79 (1H, d, J=9.6 Hz); 7,46 (1H, d, J=9.6 Hz); 7,27 (1H, s); to 7.18 (1H, DD, J=13,1, 6,0 Hz); 6.90 to (1H, d, J=9.6 Hz); 3,88 (3H, s); of 3.80 (3H, s).

EXAMPLE 30

3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid. A31-B78, the product of the combination of group A31 in table 1 and B78 table 2:

To a solution of dimethyl 1,1-in primary forms 3-[6-(4-(1-methyl)ethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic 1,1-acid [0,77 g, Comparative example 44(b)] in methanol (45 ml) is added 1N. the sodium hydroxide solution (7.7 ml). The reaction mixture is heated at 50°C for 6 hours, then leave at room temperature overnight. The solvent is removed by evaporation, add 6N sulfuric acid solution (20 ml) and the reaction mixture is refluxed for 12 hours. After cooling, the solution is alkalinized to pH4 4h. the sodium hydroxide solution obtained residue is filtered and dried in vacuum, obtaining specified in the header connection (0,42 g) is the form of a yellow solid, which is used without further purification. MS: 284 (MH+). HPLC (Method C): RT=2,3 minutes

EXAMPLE 31

Ethyl 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionate. A57-B78, the product of the combination of group A57 in table 1 and B78 table 2:

A solution of 3-{6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl}propionic acid (0.02 g) [EXAMPLE 30} in ethanol (2 ml) is treated with a catalytic amount of paratoluenesulfonyl acid. The mixture is refluxed for 4 hours, the solvent is removed by evaporation and the precipitate is filtered off. Then the hard part is placed in the ethyl acetate, the organic layer washed with water, saturated salt solution, dried over magnesium sulfate and evaporated, getting a solid yellow color, which is subjected to flash chromatography on silica gel, elwira with ethyl acetate, receiving specified in the header connection. MS: 298 (MH+). HPLC (Method C): RT=2,58 minutes

EXAMPLE 32 and COMPARATIVE EXAMPLE 100

2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile. A3-B2-C1, the product of the combination of group A3 in table 1 and B2 in table 2 and C1 in table 3:

Acting similarly to comparative example 12(a)but using 2-iodine-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [Comparative example 62(a)], receive 2-(5-methoxy-1H and the Dol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile in the form of a yellow solid. TPL 303-304°C, TLC RF=0,07 (ethyl acetate/heptane 1:1) and 2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [Comparative example, 100] as a brown solid. MS: 443(MH*). TLC: RF=of 0.38 (ethyl acetate/heptane 1:1).

EXAMPLE 33

6-(4-methylsulfinylphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B93, the product of the combination of group A1 in table 1 and B93 table 2

Stir a suspension of 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazine [0,2362 g, EXAMPLE 1(ah)] in dichloromethane (20 ml) is treated by TBA axonom (2,545 g). After 2 hours the resulting orange solution is evaporated. The residue is subjected to flash chromatography on silica gel, elwira mixture of methanol and dichloromethane (1:1, vol/vol.), getting listed in the title compound as a white solid. MS: 258 (MH+).1H NMR [(CD3)2SO]; δ 12,66 (1H, s); to 8.41 (1H, s); 8,24 (3H, m); of 7.82 (2H, d, J=8.7 Hz); 7,33 (1H, s); of 2.81 (3H, s).

EXAMPLE 34

6-(4-methylsulfinylphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B94, the product of the combination of group A1 in table 1 and B94 table 2

Stir a suspension of 6-(4-methylthiophenyl)-5H-pyrrolo[2,3-b]pyrazine [0.125 g, EXAMPLE 1(ah)] in dichloromethane (15 ml) is treated by TBA axonom (1.35 g). After 4 hours the reaction mixture is evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of methane is La and dichloromethane (1:1, about./vol.), getting listed in the title compound as a white solid. MS: 274 (MH+).1H NMR [(CD3)2SO]; δ 12,78 (1H, s); 8,44 (1H, s); 8,28 (3H, m); 8,04 (2H, d, J=8,8 Hz); 7,40 (1H, s); of 3.27(3H, s).

EXAMPLE 35

3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)Propylamine. A46-B55, the product of the combination of group A46 in table 1 and B55 in table 2

A solution of 3-[6-(4-tert-butylphenyl-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionamide [0.2 g, EXAMPLE 24] in anhydrous tetrahydrofuran (20 ml) is treated with a solution of lithium aluminum hydride in diethyl ether (5 ml, 1M). The solution was stirred at room temperature for 24 hours, then treated with water (20 ml). The mixture is filtered through celite, washed twice with ethyl acetate (20 ml). The combined filtrate and wash fractions washed with water, then with saturated salt solution, then dried over magnesium sulfate and then evaporated, getting mentioned in the title compound as a yellow solid (0.12 g). MS: 309 (MH+). HPLC (Method C): RT=2,54 minutes

EXAMPLE 36

(a) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}ndimethylacetamide. A39-B55, the product of the combination of group A39 in table 1 and B55 in table 2:

A solution of 3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)Propylamine (0,0324 mmol) [EXAMPLE 35] in tetrahydrofuran (1.5 ml) is treated with ACET what chloridum (0,0324 mmol) and triethylamine (0,0788 mmol). The solution was stirred at room temperature for 12 hours and then treated with water and ethyl acetate. The organic phase is dried over magnesium sulfate and then evaporated. The residue is subjected to flash chromatography on silica gel, elwira a mixture of ethyl acetate and methanol (9:1, vol/vol.), getting listed in the title compound as a yellow solid. MS: 351 (MH+). HPLC (Method C): RT=3,05 minutes

(b) Amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}cyclopropylboronic acid. A47-B55, the product of the combination of group A47 in table 1 and B55 in table 2:

Acting analogously to example 36(a) above but using cyclopropanecarbonitrile get amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}cyclopropylboronic acid in the form of a solid resinous yellow solid. MS: 377 (MH+). HPLC (Method C): RT=3,25 minutes

(c) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}of butyramide. A48-B55, the product of the combination of group A48 in table 1 and B55 in table 2:

Acting analogously to example 36(a) above but using n-butyrolactone receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}of butyrate in the form of a yellow resinous solid. MS: 379 (MH+). HPLC (Method C): RT=3,28 minutes

(d) N-{3-(6-(4-tert-b is terphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methoxyacetate. A49-B55, the product of the combination of group A49 in table 1 and B55 in table 2:

Acting analogously to example 36(a) above but using methoxyacetanilide receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methoxyacetate in the form of a white solid. MS: 381 (MH+). HPLC (Method C): RT=3,15 minutes

(e) Amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-icarbonell acid. A50-B55, the product of the combination of group A50 in table 1 and B55 in table 2:

Acting analogously to example 36(a) above but using Tien-2-ylcarbonyl get amide N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-icarbonell acid as a yellow solid. MS: 419 (MH+). HPLC (Method C): RT=3,28 minutes

EXAMPLE 37

(a) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b|pyrazin-7-yl)propyl}-N'-n-proprotein. A51-B55, the product of the combination of group A51 in table 1 and B55 in table 2:

A solution of 3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)Propylamine (0,0324 mmol) [EXAMPLE 35] in tetrahydrofuran (2 ml) is treated with n-propositionem (0,0324 mmol). The solution was stirred at room temperature for 12 hours and then treated with water (3 ml). The precipitate is filtered off, then washed with water and then dried in in the cosmology vacuum at 50° C, getting mentioned in the title compound as a beige solid. MS: 394 (MH+). HPLC (Method C): RT=3,25 minutes

b) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b|pyrazin-7-yl)propyl}-N'-carbomethoxyamino. A52-B55, the product of the combination of group A52 in table 1 and B55 in table 2:

Acting analogously to example 37(a) above but using utilizationfocused receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b|pyrazin-7-yl)propyl}-N'-carbomethoxyamino in the form of a yellow solid. MS: 437 (MH+). HPLC (Method C): RT=3,18 minutes

c) N-{1-methyl-[3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}-N'-tetrahydropyran-2-rocephine. A2-B1-C74, the product of the combination of group A2 in table 1 and B1 in table 2 and C74 table 3:

Acting analogously to example 37(a) above but using [3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indol-5-yl]methylamine [EXAMPLE 52] and tetrahydropyran-2-ilization receive N-{1-methyl-[3-(1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indol-5-yl]methyl}-N'-tetrahydropyran-2-Ilocano in the form of solids. TPL 229-231°C.

EXAMPLE 38

N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-N',N'-determation. A53-B55, the product of the combination of group A53 in table 1 and B55 in table 2:

A solution of 3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)impregnated the Amin [0,0324 mmol, EXAMPLE 35] in tetrahydrofuran (1.5 ml) is treated with diethylcarbamazine (0,0324 mmol) and triethylamine (0,0788 mmol). The solution was stirred at room temperature for 12 hours, add water and ethyl acetate. The layers are separated and the organic solution is dried over magnesium sulfate. The drying agent is filtered off and the solvent is evaporated. The residue is purified through column chromatography (silica gel, ethyl acetate then 10% methanol in ethyl acetate), obtaining mentioned in the title compound as a yellow solid. MS: 408 (MH+). HPLC (Method C): RT=3,43 minutes

EXAMPLE 39

(a) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}methanesulfonamide. A38-B55, the product of the combination of group A38 in table 1 and B55 in table 2:

A solution of 3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)Propylamine [0,0324 mmol, EXAMPLE 35] in tetrahydrofuran (1.5 ml) is treated with methanesulfonamide (0,0324 mmol) and triethylamine (0,0788 mmol). The solution was stirred at room temperature for 12 hours and add water and ethyl acetate. The layers are separated and the organic solution is dried over magnesium sulfate. The drying agent is filtered off and the solvent is evaporated. The residue is purified through column chromatography (silica gel, ethyl acetate then 10% methanol in ethyl acetate), obtaining specified in the header of the what begins as a yellow solid. MS: 387 (MH+). HPLC (Method C): RT=3,23 minutes

(b) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-ylsulphonyl. A50-B55, the product of the combination of group A50 in table 1 and B55 in table 2:

Acting analogously to example 39(a) above but using Tien-2-ylsulphonyl receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}Tien-2-ylsulphonyl in the form of a yellow solid. MS: 455 (MH-+). HPLC (Method C): RT=3,56 minutes

(c) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}dimethylisoxazol-4-ylsulphonyl. A54-B55, the product of the combination of group A54 in table 1 and B55 in table 2:

Acting analogously to example 39(a) above but using 3,5-dimethylisoxazol-4-ylsulphonyl receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}dimethylisoxazol-4-ylsulphonyl in the form of a gummy white solid. MS: 468 (MH+). HPLC (Method C): RT=3,55 minutes

(d) N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-1-Mei-4-ylsulphonyl. A56-B55, the product of the combination of group A56 in table 1 and B55 in table 2:

Acting analogously to example 39(a) above but using 1-Mei-4-ylsulphonyl receive N-{3-(6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)propyl}-1-methylimidazo the l-4-ylsulphonyl in the form of a gummy white solid. MS: 453 (MH+). HPLC (Method C): RT=3,13 minutes

EXAMPLE 40

(a) (2-hydroxy-1,1-dimethylethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A68-B1-C1, the product of the combination of group A68 in table 1 and B1 in table 2 and C1 in table 3:

A solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [32 mg, EXAMPLE 41(a)] in anhydrous dimethylformamide (10 ml) under nitrogen atmosphere is treated with diisopropylethylamine (35 μl), then hexaphosphate O-(7-asobancaria-1-yl)-1,1,3,3-tetramethyluronium (38 mg). After stirring at room temperature for 1 hour, the mixture is treated with a solution of 2-amino-2-methyl-1-propanol (10,5 μl) in anhydrous dimethylformamide (1 ml) and stirring is continued for another 2 hours. The reaction mixture is evaporated and the residue treated with saturated aqueous sodium bicarbonate (15 ml). The mixture is stirred for 1 hour and the resulting solid yellow filter, then well washed with water and dried at 100°C in vacuum, obtaining mentioned in the title compound (34 mg) as a yellow solid. TPL 210-212°C.

(b) (2-hydroxy-1,1-dimethylethyl)amide 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid. A28-B1-C31, the product of the combination of group A28 in table 1 and B1 in table 2 and C31 in table 3:

Acting analogously to example 40(a) above, but using a mixture of 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid and methyl ester of 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid [EXAMPLE 41(b)] and subjecting the crude reaction product chromatography on silica gel, elwira first, a mixture of ethyl acetate and heptane (85:15, vol/vol.), then with ethyl acetate, receive (2-hydroxy-1,1-dimethylethyl)amide 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid in the form of a reddish-gray solid. MS: 397, 399(M+). RT=4,038 minutes

(c) [2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]morpholine-4-ylmethanol. A12-B1-C1, the product of the combination of group A12 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using morpholine instead of 2-amino-2-methyl-1-propanol, receive [2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]morpholine-4-ylmethanol in the form of solids. TPL 259-260°C. MS: 391 (MH+).

(d) 3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide. A33-B78, the product of the combination of group A33 in table 1 and B78 table 2:

Acting analogously to example 40(a) above but using 3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]propionic what islote (EXAMPLE 30) and N-methylamine, receive 3-[6-(4-hydroxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide in the form of solids. MS: 297 (MH+).

(e) (2-hydroxy-1,1-dimethylethyl)amide 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A68-B3-C1, the product of the combination of group A68 in table 1, B3 in table 2 and C1 in table 3:

Acting analogously to example 40 (a) above but using 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid [EXAMPLE 41(c)], get (2-hydroxy-1,1-dimethylethyl)amide 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid a green solid. TPL 244-245°C. MS: 407 (MH+).

(f) (2-methoxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A69-B1-C1, the product of the combination of group A69 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using 2-{5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid [EXAMPLE 41(a)] and 2-methoxyethylamine, receive (2-methoxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid the form of a yellow solid. TPL 248-249°C. MS: 379 (MH+).

(g) (2-hydroxy-2-methylpropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A70-B1-C1, the product comb the nation group A70 in table 1, B1 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [EXAMPLE 41(a)] and 1-amino-2-methylpropan-2-ol (obtained by the method presented in the literature Cabella et. al. Tetrahedron, 1995, 51 (6), 1817-1826), receive (2-hydroxy-2-methylpropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid in the form of solids. LC-MS: METHOD D: RT=2,54 min, to 393.3 (MH+).

(h) (2-hydroxypropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic. A85-B1-C1. the product of the combination of group A85 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3,-b]pyridine-4-carboxylic acid [EXAMPLE 41(a)] and 1-aminopropan-2-ol, receive (2-hydroxypropyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid in the form of solids. LC-MS: METHOD D: RT=2,74 min, 379 (MH+).

(i) (2-hydroxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A86-B1-C1, the product of the combination of group A86 in table 1 and B1 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using 2-{5-methoxy-1-methyl-ningal-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [EXAMPLE 41(a)] and 2-aminoethanol, receive (2-hydroxyethyl)amide 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid in the form of solids. LC-MS: METHOD D: RT=2,22 min, 365 (MH+).

(j) (2-methoxyethyl)amide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A69-B2-C1, the product of the combination of group A69 in table 1 and B2 in table 2 and C1 in table 3:

Acting analogously to example 40(a) above but using 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [EXAMPLE 15(t)] and 2-methoxyethylamine, receive (2-methoxyethyl)amide 2-(5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid in the form of solids. LC-MS (METHOD D): RT=3,65 min, 365 (MH+).

EXAMPLE 41

(a) 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A67-B1-C1, the product of the combination of group A67 in table 1 and B1 in table 2 and C1 in table 3:

A solution of tert-butyl methyl ether 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [106 mg, Comparative example 2(n)] in methanol (10 ml) is treated with a solution of potassium hydroxide (1 ml, 5N.), then refluxed for 1 hour and then evaporated. The residue is treated with water (15 ml) and the mixture washed with ethyl acetate (10 ml). Then the pH of the aqueous solution was adjusted to 4 by adding chlorine is estevadeordal acid, and cooled on ice. The obtained solid yellow filtered off, well washed with water and then dried at 80°C in vacuum, obtaining mentioned in the title compound (33 mg) as a yellow solid. TPL >300°C. MS: 322 (MH+).

(b) 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid. A28-B1-C28, the product of the combination of group A28 in table 1 and B1 in table 2 and C28 in table 3; and methyl ester of 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid:

Acting analogously to example 41(a) above but using methyl ester of 3-(4-chloro-1-(toluene-4-sulfonyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-yl)-1H-indole-5-carboxylic acid [Comparative example 19(d)], receive a 60:40 mixture of 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid and methyl ester of 3-(4-chloro-1H-pyrrolo[2,3-b]pyridine-2-yl)-1-methyl-1H-indole-5-carboxylic acid in the form of not-quite-white solid. MS: 326 and 340(M+).

(c) 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid. A67-B3-C1, the product of the combination of group A67 in table 1, B3 in table 2 and C1 in table 3:

Acting analogously to example 41(a) above but using tert-butyl ester 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid [Cf is entrusted example 13(o)], get 2-(1-ethyl-5-methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid as a yellow-brown solid. MS: 336 (MH+). TLC: RF=0,24 (ethyl acetate/heptane, 1:1).

EXAMPLE 42

2-(5-Methoxy-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxamide. A10-B2-C1, the product of the combination of group A10 in table 1 and B2 in table 2 and C1 in table 3:

A suspension of 2-(5-methoxy-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile [0.25 g, Comparative example 67(e)] in methanol (25 ml) is treated with sodium hydroxide solution (1.5 g in 4 ml water). The mixture is cooled in a bath with ice and then treated by adding dropwise hydrogen peroxide (0.35 ml, 30%). After stirring at room temperature for 1 hour to the reaction mixture add an additional aliquot of hydrogen peroxide (0.3 ml) and stirring is continued for further 3 hours, then the reaction quenched by adding sodium metabisulfite to remove excess hydrogen peroxide. Then the reaction mixture was diluted with water (75 ml) and extracted twice with ethyl acetate (50 ml). The combined extracts are washed twice with saturated salt solution (30 ml), then dried over sodium sulfate and then evaporated. The remaining solid yellow subjected to chromatography on silica gel, elwira a mixture of ethyl acetate and dichloromethane (1:1, vol/vol.), receiving POS is e trituration with methanol and washing with diethyl ether specified in the title compound (50 mg) as a yellow solid. TPL >320°C. MS: 307 (MH+).

EXAMPLE 43

3-[6-(4-(morpholine-4-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide. A33-B59, the product of the combination of group A33 in table 1 and B59 table 2:

A mixture of 3-[6-(4-triftoratsetilatsetonom)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-N-methylpropionamide [30 mg, Comparative example 18(d)], acetonitrile (2 ml) and research (0.5 ml) is heated at 200°C in a microwave oven for 4 hours. Then the reaction mixture is evaporated and the residue triturated with ethyl acetate, getting mentioned in the title compound in the form of solids. MS: 429,1 (MH+).

EXAMPLE 44

6-(4-pyrrolidin-1-ylphenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B82, the product of the combination of group A1 in table 1 and B82 table 2:

A mixture of 6-(4-triftoratsetilatsetonom)-5H-pyrrolo[2,3-b]pyrazine [20 mg, Comparative EXAMPLE 18(e)], dioxane (3 ml) and pyrrolidine (0.2 ml) is heated at 200°C in a microwave swords for 1 hour. Then the reaction mixture is evaporated and the residue is subjected to chromatography on silica gel, elwira a mixture of ethyl acetate and heptane (1:1, vol/vol.), getting after trituration with a mixture of ethyl acetate and methanol specified in the title compound (1 mg) as a yellow solid. MS: 265,1 (MH+). RT=2,92 minutes

EXAMPLE 45

(a) 6-(4-(furan-2-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-100, the product of the combination of group A1 in table 1 and B100 in table 2:

A mixture of 6-(4-triftoratsetilatsetonom)-5H-pyrrolo[2,3-b]pyrazine [20 mg, Comparative example 18(e)], dioxane (2.5 ml), furan-2-Bronevoy acid (9.8 mg), sodium carbonate solution (0.06 ml, 2 BC) and tetrakis(triphenylphosphine)palladium[0] (4 mg) is heated at 180°C in a microwave oven for 40 minutes Then the reaction mixture is evaporated and the residue is subjected to chromatography on silica gel, elwira a mixture of ethyl acetate and pentane (1:1, vol/vol.), getting after trituration with a mixture of ethyl acetate and methanol specified in the title compound (7 mg) as a yellow solid. MS: 262,1(MH+). RT=3,05 minutes

(b) 6-(4-(3,5-dimethylisoxazol-4-yl)phenyl)-5H-pyrrolo[2,3-b]pyrazin. A1-B99, a product of the combination of group A1 in table 1 and B99 in table 2:

Acting analogously to example 45(a) above but using 3,5-dimethylisoxazol-4-Bronevoy acid and subjecting