KR20080021077A - Chemical compounds - Google Patents

Abstract

The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: Formula (I) where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKF) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention. ® KIPO & WIPO 2008

Description

Compound {CHEMICAL COMPOUNDS}

The present invention relates to certain indole carboxamide compounds, which are inhibitors of kinase activity. More specifically, the compound is an IKK2 inhibitor. These compounds are useful for the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, particularly for the treatment and prevention of disorders mediated by IKK2 mechanisms, including inflammatory and tissue regeneration disorders. Such disorders include rheumatoid arthritis, asthma and COPD (chronic obstructive pulmonary disease).

An important large family of enzymes is the protein kinase enzyme family. Currently, about 500 different protein kinases are known. However, since 3-4% of the human genome is a code for the formation of protein kinases, there may be thousands of kinases that are distinct and separate within the human body. Protein kinase will catalyze the phosphorylation of various proteins in the amino acid side chains by passing γ- phosphate of ATP-Mg ^{2 +} complex of the amino acid side chain. Since these enzymes regulate most of the signaling process inside the cell, they govern cell function, growth, differentiation and destruction (apoptosis) through the reversible phosphorylation of the hydroxyl groups of serine, threonine and tyrosine residues in proteins. Studies have demonstrated that protein kinases are important regulators of numerous cellular functions, including signal transduction, transcriptional regulation, cell motility and cell division. It has also been demonstrated that many oncogenes encode protein kinases, suggesting that kinases play a role in oncogenesis. These processes are often highly regulated by complex interlocking pathways in which each kinase itself is regulated by one or more kinases. Thus, abnormal or inappropriate protein kinase activity may be a cause of disease states associated with such abnormal kinase activity. Due to their physiological relevance, diversity and ubiquity, protein kinases have become one of the most important and widely studied family of enzymes in biochemical and medical research.

The protein kinase family of enzymes is typically classified into two main subgroups: protein tyrosine kinases and protein serine / threonine kinases, depending on the amino acid residues they phosphorylate. Serine / threonine kinases (PSTKs) include cyclic AMP- and cyclic GMP-dependent protein kinases, calcium and phospholipid dependent protein kinases, calcium- and calmodulin-dependent protein kinases, casein kinases, cell division cycle protein kinases, and the like. do. These kinases are typically cytoplasmic or associate with the particulate fraction of cells, perhaps by anchoring proteins. Aberrant protein serine / threonine kinase activity has been suspected of being associated with or associated with a number of pathologies such as rheumatoid arthritis, psoriasis, septic shock, bone loss, many cancers, and other proliferative diseases. Thus, serine / threonine kinases and the signal transduction pathways they are part of are important targets for drug design. Tyrosine kinases phosphorylate tyrosine residues. Tyrosine kinases play an equally important role in cell regulation. These kinases include a number of receptors for molecules such as growth factors and hormones, including epidermal growth factor receptors, insulin receptors, platelet derived growth factor receptors, and the like. Studies have shown that many tyrosine kinases are transmembrane proteins with receptor domains located outside the cell and kinase domains inside. In addition, a number of studies are underway to identify modulators of tyrosine kinases.

Nuclear factor κB (NF-κB) belongs to the group closely related to the dimeric transcription factor complex consisting of various combinations of Rel / NF-κB groups of polypeptides. This group consists of five individual gene products of mammals: RelA (p65), NF-κB1 (p50 / p105), NF-κB2 (p49 / p100), c-Rel and RelB, all of which are heterologous It is possible to form dimers or homodimers. These proteins share 300 highly homologous amino acid "Rel homology domains" that contain DNA binding and dimerization domains. At the C-terminal end of the Rel homology domain, the nuclear translocation sequence is important for carrying NF-κB from the cytoplasm to the nucleus. In addition, p65 and cRel have a potent transactivation domain at their C-terminal ends.

The activity of NF-κB is regulated by interaction with members of the inhibitor IκB family of proteins. This interaction effectively blocks the nucleus position sequence in the NF-κB protein and thus prevents the migration of dimers to the nucleus. A wide variety of stimuli probably activate NF-κB through multiple signal transduction pathways. Bacterial products (LPS), some viruses (HIV-1, HTLV-1), inflammatory cytokines (TNFα, IL-1), environmental and oxidative stress, and DNA damaging agents. But apparently common to all stimuli is phosphorylation and subsequent degradation of IκB. IκB is phosphorylated at two N-terminal serines by recently identified IκB kinases (IKK-α and IKK-β). IKK-β is also known as IKK2. Site-directed mutagenesis studies indicate that these phosphorylations are critical for subsequent activation of NF-κB in that once phosphorylation is indicated to degrade proteins via the ubiquitin-proteasome pathway. Freed from IκB, the active NF-κB complexes can be translocated into the nucleus where they bind in a selective manner to the gene-specific enhancer sequences of interest. Genes regulated by NF-κB include many cytokines and chemokines, cell adhesion molecules, acute phase proteins, immunoregulatory proteins, eicosanoid metabolizing enzymes and anti-apoptotic genes.

NF-κB includes cytokines (eg TNF, IL-1β, IL-6 and IL-8), cell adhesion molecules (eg ICAM and VCAM), and inducible nitric oxide synthase (iNOS) It is well known that it plays an important role in the regulated expression of numerous pro-inflammatory mediators. It is well known that such mediators play a role in the recruitment of leukocytes at the site of inflammation and iNOS can lead to organ destruction in some inflammatory and autoimmune diseases.

The importance of NF-κB in inflammatory disorders is further reinforced by studies of airway inflammation, including asthma, where NF-κB has been shown to be activated. Such activation may underlie the increased cytokine production and leukocyte infiltration characteristic of the disorder. Inhaled steroids are also known to reduce airway hyperresponsiveness and inhibit inflammatory responses in asthmatic airways. In light of recent findings on glucocorticoid inhibition of NF-κB, it can be inferred that these effects are mediated through the inhibition of NF-κB.

Further evidence for the role of NF-κB in inflammatory disorders is presented from rheumatic synovial membrane studies. Normally NF-κB exists as an inactive cytoplasmic complex, but recent immunohistochemical studies have shown that NF-κB is present in the nucleus and therefore active in cells comprising the rheumatic synovial membrane. In addition, NF-κB has been demonstrated to be activated in human lubricating cells in response to stimulation with TNF-α or IL-1β. This distribution may be the underlying mechanism for increased cytokine and eicosanoid production that is characteristic of the tissue. Rosshak, A. K., et al., J. Biol. Chem., 271, 31496-31501 (1996). Expression of IKK-β was observed in synovial cells in rheumatoid arthritis patients, and gene transfer studies demonstrated a central role of IKK-β in the production of stimulated inflammatory mediators in these cells. Aupperele et al. J. Immunology 1999. 163: 427-433 and Aupperle et al. J. Immunology 2001; 166: 2705-11. More recently, intraarticular administration of predominant-negative IKKβ inhibits adjuvant-induced arthritis in rats, while intraarticular administration of wild type IKK-β adenovirus constructs has been shown to cause edema of the foot. Tak et al. Arthritis and Rheumatism 2001, 44: 1897-1907.

NF-κB / Rel and IκB proteins also appear to play an important role in neoplastic transformation and metastasis. Group members are involved in cell transformation in vitro and in vivo as a result of overexpression, gene amplification, gene rearrangement or translocation. In addition, rearrangement and / or amplification of genes encoding these proteins is observed in 20-25% of some human lymphoid tumors. In addition, NF-κB is activated by oncogenic ras, which is most commonly deleted in human tumors, and interference with NF-κB activation inhibits ras mediated cell transformation. In addition, the role of NF-κB in the regulation of apoptosis has been reported to enhance the role of these transcription factors in the regulation of tumor cell proliferation. TNF, ionizing radiation, and DNA damaging agents have all been demonstrated to activate NF-κB, which leads to upregulated expression of some anti-apoptotic proteins. Conversely, inhibition of NF-κB has been demonstrated to enhance apoptosis-killing by these agents in some tumor cell types. Since this probably represents the main mechanism of tumor cell resistance to chemotherapy, inhibitors of NF-κB activation may be useful chemotherapy agents either alone or as adjuvant therapy. Recent reports have linked NF-κB as a regulator of cytokine-induced muscle breakdown as well as inhibitors of skeletal cell differentiation (Guttridge et al. Science; 2000; 289: 2363-2365) and also as novel cancer therapy It supported the potential of NF-κB inhibitors.

Several NF-κB inhibitors are described in C. Wahl, et al. J. Clin. Invest. 101 (5), 1163-1174 (1998), R. R. W. Sullivan, et al. J. Med. Chem. 41, 413-419 (1998), J. Pat. W. Pierce, et al. J. Biol. Chem. 272, 21096-21103 (1997).

The marine natural product hymenialdisine is known to inhibit NF-κB. Rosshak, A., et al., JPET, 283, 955-961 (1997). Breton, J. J and Chabot-Fletcher, M. C., JPET, 282, 459-466 (1997).

See also patents for aminothiophene inhibitors of IKK2 (Callahan, et al., WO 2002030353); Patent [Baxter, et al., WO 2001058890], patent [Faull, et al., WO 2003010158]; Patent (Griffiths, et al., WO 2003010163); Patent [Fancelli, et al., WO 200198290]; Patent [Granetto, et al., WO 2003037886]; For imidazole inhibitors of IKK2 (Callahan, et al., WO 200230423); Patent for anilinophenylpyrimidine inhibitors of IKK2 [Kois, et al., WO 2002046171]; For [beta] -carboline inhibitors of IKK2 [Ritzeler, et al., WO 2001068648], patent [Ritzeler, et al., EP 1134221]; Patent [Nielsch, et al. DE 19807993; Patent (Ritzeler, et al., EP 1209158); For indole inhibitors of IKK2 (Ritzeler, et al., WO 2001030774); Patent for benzimidazole inhibitors of IKK2 (Ritzeler, et al., DE 19928424); Patent [Ritzeler et al., WO 2001000610]; Patent (Ritzeler, et al., WO 2004022553); Patent for aminopyridine inhibitors of IKK2 [Lowinger, et al., WO 2002024679]; Patent (Murata, et al., WO 2002024693); Patent [Murata, et al., WO 2002044153]; Patent for aminopyrimidine inhibitors of IKK2 [Bollbuck, et al., WO 2004089913]; Patent for pyrazole inhibitors of IKK2 [Bergmanis, et al., WO 2003024935]; Patent (Metz, et al., WO 2003024936); Patent [Geng et al., WO 2003027075]; Patent [Stealey, et al., WO 2003035625]; Patent [Xu, et al., WO 200307076]; Patent [Lennon, et al., WO 2003095430]; Patents for pyrazinone inhibitors of IKK2 [Boys, et al., WO 2005035527]; For pyrazolaquinazolin inhibitors of IKK2 [Beaulieu, et al., WO 2002028860]; Patent [Burke et al., WO 2002060386], patent [Burke, et al. US 20030022898; For thiophene tricyclic inhibitors of IKK2 (Belema, et al., WO 2003084959); Patents for pyrazolopurine inhibitors of IKK2 [Qiu, et al., WO 2004075846]; Patents for oxazolo and thiazolo pyridine inhibitors of IKK2 [Pitts, et al., WO 2004106293]; For quinoline inhibitors of IKK2 (Browner, et al., WO2002041843); Patent [Browner, et al., US 20020161004]; Patents for pyridylcyanoguanidine inhibitors of IKK2 (Bjorkling, et al., WO 2002094813); Patents [Binderup et al., WO 2002094322] and patents [Madsen, et al., WO 200294265]; For thienopyridine inhibitors of IKK2 (Cywin, et al., WO 2003103661); Patent, Liu, et al., WO 2005035537; A patent has been applied for a benzothiophene inhibitor of IKK2 [Chen et al., WO 2005012283]. The natural products staurosporine, quercetin, K252a and K252b have proven to be IKK2 inhibitors (Peet, GW and Li, JJ Biol. Chem., 274, 32655-32661 (1999) and literature [ Wisniewski, D., et al., Analytical Biochem. 274, 220-228 (1999). Inhibitors of synthesis of IKK2 have also been described (see Burke, et al. J. Biol. Chem., 278, 1450-1456 (2003)), Murata, et al., Bioorg. Med. Chem. Lett., 13, 913-198 (2003), Murata, et al., Bioorg. Med. Chem. Lett., 14, 4013-4017 (2004), and Murata, et al., Bioorg. Med. Chem. Lett., 14, 4019-4022 (2004)] describes IKK2 inhibitors.

Thus, attempts have been made to produce compounds that inhibit IKK2 activity, and many such compounds have been disclosed in the art. However, given the number of pathological responses mediated by IKK2, there is a continuing need for inhibitors of IKK2 that can be used to treat various conditions.

We have discovered novel indole carboxamide compounds, which are inhibitors of kinase activity, in particular inappropriate IKK2 activity. Such indole carboxamide derivatives are thus useful for the treatment of inappropriate kinases, especially disorders associated with inappropriate IKK2 activity, in particular inflammatory and tissue regeneration disorders, in particular rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease); Osteoarthritis, osteoporosis and fibrotic disease; Skin diseases including psoriasis, atopic dermatitis and ultraviolet (UV) -induced skin damage; Autoimmune diseases including systemic lupus erythematosus, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue and organ rejection, Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, Hodgkin's disease Useful for the treatment and prevention of disease conditions mediated by cancer, cachexia, inflammation associated with infection and several viral infections, including AIDS, adult respiratory distress syndrome, and IKK2 mechanisms including capillary dilatation ataxia Do.

<Overview of invention>

The present invention relates to novel indole carboxamide derivatives. In particular, the present invention relates to compounds according to formula (I) and pharmaceutically acceptable salts thereof.

In the formula,

R1, R2, R3, U and V are defined below.

Compounds of the invention are inhibitors of IKK2 and may be useful for the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma and COPD (chronic obstructive pulmonary disease). Accordingly, the present invention also relates to pharmaceutical compositions comprising the compounds of the present invention. The invention also relates to a method of inhibiting IKK2 activity using a compound of the invention or a pharmaceutical composition comprising a compound of the invention and a method of treating a disorder associated with IKK2 activity.

The present invention relates to a compound according to formula (I) or a pharmaceutically acceptable salt thereof.

<Formula I>

In the formula,

기이고;R1 is -XYZ or

Group;

X is phenyl, heteroaryl, 1,2,3,4-tetrahydronaphthalenyl or 2,3-dihydro-1H-indenyl, wherein said phenyl, heteroaryl, 1,2,3,4-tetra Hydronaphthalenyl and 2,3-dihydro-1H-indenyl are 1) halo, 2) nitro, 3) cyano, 4) -NR 7 R 8, 5) C ₁ -C ₆ -alkyl, 6) CHO, 7 ) Is optionally substituted with one or two substituents each independently selected from CONH ₂ and 8) -OR ₄ , wherein said C ₁ -C ₆ -alkyl is optionally substituted with one —NR 4 R 5 group;

Y is a bond or C ₁ -C ₆ alkylene, wherein C ₁ -C ₆ alkylene is 1) C ₁ -C ₃ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, Optionally substituted with one or two substituents each independently selected from 3) methoxy, 4) hydroxy and 5) heteroaryl;

Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents;

R 2 is selected from 1) H, 2) fluoro and 3) chloro;

R 3 is selected from 1) H, 2) fluoro and 3) chloro;

R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group;

R5 is 1) H, 2) C ₅ -C ₆ -heterocycloalkyl, 3) -CO ₂ Et, 4) C ₁ -C ₆ -alkoxy, 5) C ₃ -C ₇ -cycloalkyl, 6) C ₁ -C ₆ -alkyl, 7) -SO ₂ R 10 and 8) -C (O) R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 3 selected from R ₆ Optionally substituted with 4 substituents;

R6 is respectively 1) -NR7R8, 2) -SO ₂ R7, 3) -CONH ₂ , 4) -CF ₃ , 5) -CN, 6) -CO ₂ R7, 7) -OCH ₂ CH ₂ OR7, 8) -SR5, 9) C ₃ -C ₄ alkenyl, 10) OH, 11) C ₁ -C ₆ -alkoxy, 12) heteroaryl, 13) C ₃ -C ₇ -cycloalkyl, 14) phenyl, 15) hetero Independently selected from cycloalkyl and 16) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9;

R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl;

R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4;

R9 is 1) hydroxy, 2) -OMe, 3) nitro, 4) C ₁ -C ₆ -alkyl, 5) NH ₂ , 6) halo, 7) CF ₃ , 8) C ₁ -C ₆ -alkoxy And 9) independently from CN;

R10 is 1) H, 2) C ₁ -C ₆ -alkyl, 3) phenyl, 4) C ₃ -C ₇ -cycloalkyl, 5) heteroaryl, 6) C ₁ -C ₆ -heteroaryl and 7) hetero Selected from cycloalkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with one or two substituents each independently selected from C ₃ -C ₇ -cycloalkyl and -S-R 7, wherein said heterocycloalkyl is Optionally substituted with one -C (O) R7 group, wherein the phenyl, heteroaryl and C ₁ -C ₆ -heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11;

Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo;

U is a bond, C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene;

V is phenyl, 5- or 6-membered heteroaryl, 5-7 membered heterocycloalkyl, C ₅ -C ₇ cycloalkyl or C ₅ -C ₇ cycloalkenyl, each of which is —N (R 7) S (O) _m R12, -S (O) _m N (R7) R12, -S (O) _m R12 or -C (O) R12;

m is 1 or 2;

R12 is C ₁ -C ₆ -alkyl, C ₃ -C ₇ cycloalkyl, C ₁ -C ₆ -alkyl-C ₃ -C ₇ -cycloalkyl or C ₁ -C ₆ -alkyl-phenyl.

One embodiment of the invention

R 1 is a -XYZ group;

X is phenyl or heteroaryl, wherein the phenyl and heteroaryl are 1) halo, 2) nitro, 3) cyano, 4) -NR 7 R 8, 5) C ₁ -C ₆ -alkyl, 6) CHO, 7) CONH ₂ and 8) optionally substituted with one or two substituents each independently selected from -OR ₄ , wherein said C ₁ -C ₆ -alkyl is optionally substituted with one —NR 4 R 5 group;

Y is a bond or C ₁ -C ₆ alkylene, wherein C ₁ -C ₆ alkylene is 1) C ₁ -C ₃ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, Optionally substituted with one or two substituents each independently selected from 3) methoxy, 4) hydroxy and 5) heteroaryl;

Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4 Optionally substituted with 1 or 2 substituents each independently selected from hydroxy and 5) heteroaryl;

R 2 is selected from 1) H, 2) fluoro and 3) chloro;

R 3 is selected from 1) H, 2) fluoro and 3) chloro;

R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group;

R5 is 1) H, 2) C ₁ -C ₆ -alkoxy, 3) C ₃ -C ₇ -cycloalkyl, 4) C ₁ -C ₆ -alkyl, 5) -SO ₂ R 10 and 6) -C (O Is selected from R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are optionally substituted with 1 to 3 substituents selected from R ₆ ;

Each R6 is 1) -NR7R8, 2) -SO ₂ R7, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl, 8) heterocycloalkyl and 9) independently selected from halo, wherein the heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9;

R 7 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

R 8 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

Are each from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ , 7) C ₁ -C ₆ -alkoxy and 8) CN Independently selected;

R 10 is selected from 1) H, 2) C ₁ -C ₆ -alkyl, 3) phenyl, 4) C ₃ -C ₇ -cycloalkyl and 5) heteroaryl, wherein said C ₁ -C ₆ -alkyl is C Optionally substituted with one or two substituents each independently selected from ₃ -C ₇ -cycloalkyl and -S-R7, said heterocycloalkyl is optionally substituted with one -C (O) R7 group; Said phenyl and heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11;

Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo;

U is a bond, C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene;

V is phenyl, 5- or 6-membered heteroaryl, 5-7 membered heterocycloalkyl, C ₅ -C ₇ cycloalkyl or C ₅ -C ₇ cycloalkenyl, each of which is —N (R 7) S (O) _m R12, -S (O) _m N (R7) R12, -S (O) _m R12 or -C (O) R12;

m is 1 or 2;

R12 is C ₁ -C ₆ -alkyl, C ₃ -C ₇ cycloalkyl, C ₁ -C ₆ -alkyl-C ₃ -C ₇ -cycloalkyl or C ₁ -C ₆ -alkyl-phenyl

Compound according to formula (I) or a pharmaceutically acceptable salt thereof.

Another embodiment of the invention

기이고;R1 is -XYZ or

Group;

X is phenyl, heteroaryl, 1,2,3,4-tetrahydronaphthalenyl or 2,3-dihydro-1H-indenyl;

Y is a bond or C ₁ -C ₆ alkylene;

Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents;

R 2 is H;

R 3 is H;

R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group;

R5 is 1) H, 2) C ₅ -C ₆ -heterocycloalkyl, 3) -CO ₂ Et, 4) C ₁ -C ₆ -alkoxy, 5) C ₃ -C ₇ -cycloalkyl, 6) C ₁ -C ₆ -alkyl, 7) -SO ₂ R 10 and 8) -C (O) R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 3 selected from R ₆ Optionally substituted with 4 substituents;

R6 is respectively 1) -NR7R8, 2) -SO ₂ R7, 3) -CONH ₂ , 4) -CF ₃ , 5) -CN, 6) -CO ₂ R7, 7) -OCH ₂ CH ₂ OR7, 8) -SR5, 9) C ₃ -C ₄ alkenyl, 10) OH, 11) C ₁ -C ₆ -alkoxy, 12) heteroaryl, 13) C ₃ -C ₇ -cycloalkyl, 14) phenyl, 15) hetero Independently selected from cycloalkyl and 16) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9;

R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl;

R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4;

Each R 9 is 1) hydroxy, 2) -OMe, 3) nitro, 4) C ₁ -C ₆ -alkyl, 5) NH ₂ , 6) halo, 7) CF ₃ , 8) C ₁ -C ₆ -alkoxy And 9) independently from CN;

R 10 is 1) H, 2) C ₁ -C ₆ -alkyl, 3) phenyl, 4) C ₃ -C ₇ -cycloalkyl, 5) heteroaryl, 6) C ₁ -C ₆ -heteroaryl and 7) hetero Selected from cycloalkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with one or two substituents each independently selected from C ₃ -C ₇ -cycloalkyl and -S-R 7, wherein said heterocycloalkyl is Optionally substituted with one -C (O) R7 group, wherein the phenyl, heteroaryl and C ₁ -C ₆ -heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11;

Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo;

U is a bond;

V is 5-7 membered heterocycloalkyl substituted with -S (O) _m R12;

m is 1 or 2;

R12 is C ₁ -C ₆ -alkyl

Compound according to formula (I) or a pharmaceutically acceptable salt thereof.

Another embodiment of the invention

R 1 is a -XYZ group;

X is phenyl or heteroaryl;

Y is a bond or C ₁ -C ₆ alkylene;

Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4 Optionally substituted with 1 or 2 substituents each independently selected from hydroxy and 5) heteroaryl;

R 2 is H;

R 3 is H;

R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group;

R5 is 1) H, 2) C ₁ -C ₆ -alkoxy, 3) C ₃ -C ₇ -cycloalkyl, 4) C ₁ -C ₆ -alkyl, 5) -SO ₂ R 10 and 6) -C (O Is selected from R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are optionally substituted with 1 to 3 substituents selected from R ₆ ;

Each R6 is 1) NR7R8, 2) SO ₂ R7, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl, 8) heterocycloalkyl and 9) Independently selected from halo, wherein the heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9;

R 7 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

R 8 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

Are each from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ , 7) C ₁ -C ₆ -alkoxy and 8) CN Independently selected;

R 10 is selected from 1) H, 2) C ₁ -C ₆ -alkyl, 3) phenyl, 4) C ₃ -C ₇ -cycloalkyl and 5) heteroaryl, wherein said C ₁ -C ₆ -alkyl is C Optionally substituted with one or two substituents each independently selected from ₃ -C ₇ -cycloalkyl and -S-R7, wherein said heterocycloalkyl is optionally substituted with one -C (O) R7 group, said phenyl and hetero Aryl is optionally substituted with 1 to 2 substituents selected from R 11;

Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo;

U is a bond;

V is 5-7 membered heterocycloalkyl substituted with -S (O) _m R12

m is 1 or 2;

R12 is C ₁ -C ₆ -alkyl

Compound according to formula (I) or a pharmaceutically acceptable salt thereof.

Another embodiment of the invention

R 1 is a -XYZ group;

X is 2- or 3-thiophenyl;

Y is a bond or C ₁ -C ₄ alkylene;

Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents;

R 2 is H;

R 3 is H;

R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group;

R 5 is selected from 1) C ₃ -C ₇ -cycloalkyl and 2) C ₁ -C ₆ -alkyl, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 1 selected from R ₆ ; Optionally substituted with 3 substituents;

R6 is 1) -NR7R8, 2) -CONH ₂ , 3) -CN, 4) -OCH ₂ CH ₂ OR7, 5) C ₃ -C ₄ alkenyl, 6) OH, 7) C ₁ -C _6- Alkoxy, 8) heteroaryl, 9) C ₃ -C ₇ -cycloalkyl, 10) phenyl, 11) heterocycloalkyl and 12) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl Is optionally substituted with 1 to 2 substituents selected from R 9;

R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl;

R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4;

Each R 9 is independently selected from 1) C ₁ -C ₆ -alkyl;

U is a bond;

V is 4-piperidinyl substituted with —S (O) ₂ R 12;

R12 is ethyl or isopropyl

Compound according to formula (I) or a pharmaceutically acceptable salt thereof.

이고 R12가 에틸 또는 이소프로필인 화학식 I에 따른 화합물이다.Another embodiment of the invention is a UV group

And R12 is ethyl or isopropyl.

Another embodiment of the invention is a compound of formula II or a pharmaceutically acceptable salt thereof.

In the formula,

R 13 is —NR 14 R 15 or heterocycloalkyl, wherein the heterocycloalkyl is 1) selected from C ₁ -C ₆ -alkyl optionally substituted with one OR 14 group, 2) hydroxy, 3) methoxy and 4) heteroaryl Optionally substituted with 4 or 2 substituents;

R14 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxyl or 1 methoxy group;

R 15 is selected from 1) H, 2) methoxy, 3) C ₃ -C ₇ cycloalkyl and 4) C ₁ -C ₆ -alkyl, wherein said C ₃ -C ₇ cycloalkyl and C ₁ -C _6- Alkyl is optionally substituted with 1 to 3 substituents selected from R 16;

R16 is each from 1) -NR17R18, 2) -SO ₂ R17, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl and 8) heterocycloalkyl Independently selected, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 3 substituents selected from R 19;

R17 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

R18 is selected from 1) H and 2) C ₁ -C ₃ -alkyl;

R 19 is selected from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ and 7) C ₁ -C ₆ -alkoxy;

n is 1 to 3.

Specific examples of the compounds of the present invention include the following:

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperazinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({methyl [2- (methylsulfonyl) ethyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

5- (3-{[[2- (dimethylamino) ethyl] (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(4- {2-[(2-hydroxyethyl) oxy] ethyl} -1-piperazinyl) methyl ] Phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[3- (hydroxymethyl) -1-piperidinyl] methyl} phenyl) -1H-indole-7- Carboxamides;

5- [3-({bis [2- (methyloxy) ethyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

5- {3-[(2,6-dimethyl-4-morpholinyl) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (1,3-thiazol-2-yl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (2-thienyl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-2-phenylethyl) (methyl) amino] methyl} phenyl) -1H-indole- 7-carboxamide;

5- (3-{[ethyl (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3-[(cyclopentylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [3-({[(3,4-dihydroxyphenyl) methyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2- (hydroxymethyl) -3-methylbutyl] amino} methyl) phenyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-1-methylethyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(trans-4-hydroxycyclohexyl) amino] methyl} phenyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[({[1- (1-piperidinyl) cyclohexyl] methyl} amino) methyl] phenyl} -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2-hydroxypropyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

5- {3-[(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- (3-{[(1-ethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

5- [4- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

5- {3-[(cyclopropylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3-[(cyclobutylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- (1-{[3- (dimethylamino) propyl] sulfonyl} -4-piperidinyl) -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(2-methylpropyl) amino] -2,3-dihydro-1H-inden-5-yl} -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {8-[(2-methylpropyl) amino] -5,6,7,8-tetrahydro-2-naphthalenyl} -1H-indole-7-carboxamide;

5- (5-{[(2-cyanoethyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1,2,3,4-tetrahydro-7-isoquinolinyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides;

5- (3-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-{[(2,2,2-trifluoroethyl) amino] methyl} -1,3-thiazole-4 -Yl) -1H-indole-7-carboxamide;

5- (3-cyano-5-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methyl-4-piperidinyl) amino] methyl} -3-thienyl) -1H- Indole-7-carboxamide;

5- (5-{[(2-cyanoethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide;

5- (5-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (phenylsulfonyl) ethyl] amino} methyl) -3-thienyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-phenyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (1-piperidinylmethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H-indole-7-carboxamide;

5- (5-{[(2R) -2- (aminocarbonyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethyl sulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide;

5- (5-{[(2S) -2- (dimethylamino) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (1- {2- [4- (dimethylamino) -1-piperidinyl] ethyl} -1H-pyrazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidi Nil] -1H-indole-7-carboxamide;

5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- [3,4-bis (methyloxy) -5- (4-morpholinylmethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -1H- Indole-7-carboxamide;

5- [3-{[(2,2-dimethylpropyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(2-hydroxyethyl) (methyl) amino] methyl} -4,5-bis (methyloxy) phenyl ] -1H-indole-7-carboxamide;

5- [3,4-bis (methyloxy) -5- (1-pyrrolidinylmethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- {4-[(dimethylamino) methyl] -2,3-dihydro-1-benzofuran-6-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(1-methylethyl) amino] methyl} -2,3-dihydro-1-benzofuran-6- Yl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) -2,3-dihydro-1-benzofuran-6-yl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[1-methyl-2- (methyloxy) ethyl] amino} methyl) -2-thienyl] -1H Indole-7-carboxamide;

5- (5-{[(2-cyanoethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2,2,2-trifluoroethyl) amino] methyl} -3-pyridinyl) -1H- Indole-7-carboxamide;

5- {3-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[[2- (diethylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

5- (5-{[butyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide;

5- (5-{[[2- (dimethylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- (5-{[[3- (dimethylamino) propyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- (5-{[cyclopentyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (pentyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (phenylmethyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-hydroxyethyl) (methyl) amino] methyl} -3-thienyl) -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (2-pyridinyl) ethyl] amino} methyl) -3-thienyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-furanylmethyl) (methyl) amino] methyl} -3-thienyl) -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (4-pyridinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methyl {[1- (1-methylethyl) -3-pyrrolidinyl] methyl} amino) methyl]- 3-thienyl} -1 H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-thienylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [1- (2-thienyl) ethyl] amino} methyl) -3-thienyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (3-thienylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} -3-thienyl)- 1H-indole-7-carboxamide trifluoroacetate;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (3-pyridinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamide trifluoroacetate;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (4-pyrimidinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (methyloxy) ethyl] amino} methyl) -3-thienyl] -1H-indole- 7-carboxamide;

5- {3-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methylethyl) amino] methyl} -3- thienyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (3-pyridinyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide;

5- (5-{[2- (1,1-dimethylethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {5-[(2-ethyl-1-pyrrolidinyl) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (2-methylpropyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (1-methylethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide;

5- (5-{[cyclohexyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (2-methylpropyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide;

5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide;

3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7 Carboxamides;

5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7 Carboxamides;

3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -5- [5-({methyl [2- (methyloxy) ethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(propylamino) methyl] -3-thienyl} -1H-indole-7-carboxamide;

5- {5-[(diethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[(2R, 5R) -2,5-dimethyl-1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide;

5- {5-[(cyclopropylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {5-[(cyclobutylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {5-[(dimethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[(cyclopentylmethyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- {5-[(cyclopentylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(phenylmethyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} -3-thienyl) -1H Indole-7-carboxamide;

5- {5-[(butylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2R) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4- [2- (methylamino) ethyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4- [2- (propylamino) ethyl] phenyl} -1H-indole-7-carboxamide;

5- {4- [2- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} -3- [1- (ethyl Sulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(4-pyridinylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- (4-{[(cyclopentylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- {4- [2- (acetylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4- {2-[(methylsulfonyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide;

5- (4- {2-[(cyclobutylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (4- {2-[(cyclohexylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {2-[(methylsulfonyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide;

5- (3- {2-[(cyclohexylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-piperazinyl) -3-pyridinyl] -1H-indole-7-carboxamide trifluoroacetate ;

5- [6- (4-ethyl-1-piperazinyl) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- (4-{[(1-ethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[(cyclopentylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[(cyclobutylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {4-[(diethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1S) -2-hydroxy-1-methylethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1R) -2-hydroxy-1-methylethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(2R) -2-hydroxypropyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[2-hydroxy-1- (hydroxymethyl) ethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(1-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1R) -1-methylpropyl] amino} methyl) phenyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1S) -1-methylpropyl] amino} methyl) phenyl] -1H-indole-7-carbox amides;

5- {4-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(propanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- (4-{[(cyclopropylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (4-{[(cyclobutylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-thienylacetyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- [4-({[(1S) -1,2-dimethylpropyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- {4-[(butanoylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-methylpropanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(3-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- (4-{[(ethylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (4-{[(butylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1-methylethyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-carbox amides;

5- (6-amino-2-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1H-pyrazol-1-yl) phenyl] -1H-indole-7-carboxamide;

5- [4- (dimethylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (3-aminophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} -1H-indole-7- Carboxamides;

5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

5- {5-[(cyclopropylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (5-{[(2,2-dimethylpropyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- (5-{[(cyclopropylmethyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[2- (methyloxy) ethyl] amino} methyl) -3-pyridinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (methyloxy) propyl] amino} methyl) -3-pyridinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (4-morpholinylmethyl) -3-pyridinyl] -1H-indole-7-carboxamide;

5- {5-[(ethylamino) methyl] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {5-[(dimethylamino) methyl] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -3-pyridinyl} -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-pyridinyl) -1H-indole-7-carbox amides;

5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(pentylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2S) -2-methylbutyl] amino} methyl) -2-thienyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

5- {5-[(butylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[2- (methyloxy) ethyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides;

5- {5-[(cyclopentylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(3-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -3-pyridinyl) -1H-indole-7-carbox amides;

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

5- [5-({[3- (ethyloxy) propyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides;

5- (5-{[(cyclohexylmethyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[({3-[(1-methylethyl) oxy] propyl} amino) methyl] -2-thienyl} -1H-indole-7-carboxamide;

5- [5-({[2- (ethyloxy) ethyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (propyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides;

5- (5-{[(3,3-dimethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) -2-thienyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(hexylamino) methyl] -2-thienyl} -1 H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylsulfonyl) amino] phenyl} -1H-indole-7-carboxamide;

5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-pyrrolidinyl) -4-pyridinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (4-morpholinyl) -4-pyridinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-[(2-methylpropyl) amino] -4-pyridinyl} -1H-indole-7-carboxamide;

5- {2-[(2,2-dimethylpropyl) amino] -4-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (propylamino) -4-pyridinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) -2-thienyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-methylpropyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

5- {4-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(1S) -1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(1R) -1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -2- Thienyl] -1 H-indole-7-carboxamide;

5- (4-{[(2R, 5R) -2,5-dimethyl-1-pyrrolidinyl] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2S) -2-methyl-1-pyrrolidinyl] methyl} -3-thienyl) -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2R) -2-methyl-1-pyrrolidinyl] methyl} -3-thienyl) -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [1- (1-pyrrolidinyl) propyl] -3-thienyl} -1H-indole-7-carbox amides;

5- {5-[(dimethylamino) methyl] -3-thienyl} -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carbox amides;

5- [5- (aminomethyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {2-[(2-methylpropyl) amino] ethyl} -3-thienyl) -1H-indole-7- Carboxamides;

5- {5- [2- (dimethylamino) ethyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-pyrrolidinyl) -3-pyridinyl] -1H-indole-7-carboxamide;

5- {6- [ethyl (methyl) amino] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [6- (dimethylamino) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (propylamino) -3-pyridinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {6-[(1-methylethyl) amino] -3-pyridinyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (4-morpholinyl) -3-pyridinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -3-thienyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -3-thienyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -3-thienyl] -1H-indole-7-carboxamide;

5- {5-[(ethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(1R) -2-hydroxy-1-methylethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide;

3--7-carboxamide which is 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-piperidinylmethyl) -3-thienyl] -1H-;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (4-morpholinylmethyl) -3-thienyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -3-furanyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -2-thienyl] -1H-indole-7-carboxamide;

5- {5-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(propylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide;

5- {5-[(diethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides;

5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-furanyl) -1H-indole-7-carbox amides;

5- (5-{[(cyclopentylmethyl) amino] methyl} -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -3-furanyl] -1H-indole-7-carboxamide;

5- {5-[(diethylamino) methyl] -3-furanyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [2-methyl-1- (1-pyrrolidinyl) propyl] -3-thienyl} -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamides;

5- {1- [2- (dimethylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {1- [2- (1-pyrrolidinyl) ethyl] -1H-pyrazol-4-yl} -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {1- [2- (4-morpholinyl) ethyl] -1H-pyrazol-4-yl} -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H Indole-7-carboxamide;

5- {1- [2- (butylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- {1- [2- (cyclobutylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- [1- (2-{[2- (diethylamino) ethyl] amino} ethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(1-methylethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-methylpropyl) amino] ethyl} -1H-pyrazol-4-yl) -1H- Indole-7-carboxamide;

5- (1- {2-[(cyclopentylmethyl) amino] ethyl} -1H-pyrazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (methyloxy) -3- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide ;

5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (methyloxy) -3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4- (methyl oxy) phenyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-[(methylamino) methyl] -4- (methyloxy) phenyl] -1H-indole-7-carboxamide;

5- [3-{[(2,2-dimethylpropyl) amino] methyl} -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-hydroxyethyl) (methyl) amino] ethyl} -1H-pyrazol-4-yl ) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-fluoro-3-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- {3,5-bis [(methylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-fluoro-3-({[2-hydroxy-1- (hydroxymethyl) ethyl] amino} methyl) phenyl ] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-fluoro-3-({[(1S) -2-hydroxy-1-methylethyl] amino} methyl) phenyl ] -1H-indole-7-carboxamide;

5- {3-[(cyclopropylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3-[(cyclobutylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide;

5- {3,5-bis [(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3,5-bis [(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-piperidinyl) phenyl] -1H-indole-7-carboxamide;

5- {3- [1- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3- [1- (dimethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- {3-[(ethylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

5- {3-[(cyclobutylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3-[(dimethylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [1- (methylamino) ethyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1-[(1-methylethyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide;

5- {3- [1- (cyclobutylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [1- (1-pyrrolidinyl) ethyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (3-thiomorpholinyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (2-piperazinyl) -2-thienyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (4-morpholinyl) -3-pyridazinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-pyrrolidinyl) -3-pyridazinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(5-methyl-2-furanyl) methyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

5- (3-{[(2,2-dimethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2-methylbutyl] amino} methyl) phenyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1R) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide;

5- [3-({[(1S) -1,2-dimethylpropyl] amino} methyl) -5-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl) -5-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(1-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -2-methylbutyl] amino} methyl) phenyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(1R) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole-7-carboxamide;

5- (3-{[(2,2-dimethylpropyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

5- (3-{[(cyclopropylmethyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

5- (3-{[(cyclopentylmethyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} phenyl)- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[2- (methyloxy) ethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[3- (methyloxy) propyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-furanylmethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(3-methylbutyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(5-methyl-2-furanyl) methyl] amino} methyl) phenyl]- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-pyrrolidinyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

5- (5-{[(2,2-dimethylpropyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl) -2-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

5- (5-{[(cyclopropylmethyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5-({[2- (methyloxy) ethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5-({[3- (methyloxy) propyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-methyl-2-pyrrolidinyl) phenyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {2-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide ;

5- {3- [2- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [2- (propylamino) ethyl] phenyl} -1H-indole-7-carboxamide;

5- {3- [2- (dimethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- {3- [2- (dipropylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [3-({[2- (3,5-dimethyl-1H-pyrazol-1-yl) ethyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidi Nil] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (4-morpholinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-{[(2-methylpropyl) amino] methyl} -1,3-thiazol-4-yl) -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-pyrrolidinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-piperidinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides;

5- {2-[(dimethylamino) methyl] -1,3-thiazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- (2-{[ethyl (methyl) amino] methyl} -1,3-thiazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide;

5- (3-cyano-5-{[(2-methylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- {3-cyano-5-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(methylsulfonyl) amino] phenyl} -1H-indole-7-carboxamide;

5- [4- (acetylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [3- (acetylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide;

5- {3-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- {3-[(butanoylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(4-fluorophenyl) carbonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- (3-{[(cyclopentylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- (3-{[(2-ethylbutanoyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (3-{[(1-benzothien-2-ylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- [3-({[(1-acetyl-4-piperidinyl) carbonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1-methyl-1H-pyrrol-2-yl) carbonyl] amino} methyl) phenyl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(3-methyl-2-butenyl) amino] methyl} phenyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(heptanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(octanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpentanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(3-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylacetyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(hexanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- (3-{[(cyclobutylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (3-{[(cyclopropylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(propanoylamino) methyl] phenyl} -1H-indole-7-carboxamide;

5- (3-{[(cyclopentylacetyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[3- (methylthio) propanoyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1-methylethyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-carbox amides;

5- (3-{[(cyclopropylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- [3-({[(2,5-dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- [3-({[(4-bromophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- [3-({[(4-chlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(3-fluorophenyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

5- [3-({[(2-chlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides;

5- [3-({[(2,5-dichloro-3-thienyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- [3-({[(2-chloro-6-methylphenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(5-fluoro-2-methylphenyl) sulfonyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide;

5- [3-({[(1,2-dimethyl-1H-imidazol-4-yl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(propylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

5- (3-{[(butylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(phenylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(4-fluorophenyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide;

5- [3-({[(4-bromo-2-ethylphenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

5- (3-{[(1-benzothien-3-ylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide;

5- {3-[({[4- (1,1-dimethylethyl) phenyl] sulfonyl} amino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

5- [3-({[(3,4-difluorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide;

5- (3-{[(ethylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

5- (3-{[(2,1,3-benzoxadiazol-4-ylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(tetrahydro-3-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide;

5- {4-[(cyclopentylsulfonyl) amino] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-methyl-2-oxo-1-piperazinyl) phenyl] -1H-indole-7-carboxamide ;

5- [6- (4-acetyl-1-piperazinyl) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methyloxy) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methyloxy) amino] methyl} phenyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[4- (1-pyrrolidinyl) -1-piperidinyl] methyl} -3-thienyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2S) -2- (trifluoromethyl) -1-pyrrolidinyl] methyl} -3-thier Nil) -1H-indole-7-carboxamide;

5- (5-{[(2R) -2- (hydroxymethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl]- 4-piperidinyl} -1H-indole-7-carboxamide;

5- (5-{[(3S) -3-hydroxy-1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-pipe Lidinyl} -1H-indole-7-carboxamide;

5- (5-{[cyclopentyl (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole- 7-carboxamide;

5- (5-{[(2-hydroxyethyl) (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide;

5- (5-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-pipe Lidinyl} -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-propen-1-yl) amino] methyl} -3-thienyl) -1H-indole -7-carboxamide;

5- (5-{[[(3,5-dimethyl-1H-pyrazol-4-yl) methyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1 H-indole-7-carboxamide;

5- (5-{[(cyanomethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methylpropyl) amino] methyl} -3 thienyl) -1H-indole-7-car Boxamide;

5- (5-{[[2- (ethyloxy) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

5- (5-{[cyclobutyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3-thienyl]- 1H-indole-7-carboxamide;

5- (5-{[(1,1-dimethylethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[3- (trifluoromethyl) -1-piperidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide;

5- (5-{[(cyclopropylmethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides;

5- (5-{[[2- (acetylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1R, 2R) -2-hydroxycyclopentyl] (methyl) amino] methyl} -3-thie Nil) -1H-indole-7-carboxamide;

5- (5-{[(1,1-dimethylpropyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[((2S) -2-hydroxypropyl] (methyl) amino] methyl} -3-thienyl)- 1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [(2R) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[{2-[(2-hydroxyethyl) oxy] ethyl} (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1- {methyl [2- (methyloxy) ethyl] amino} ethyl) -3-thienyl] -1H- Indole-7-carboxamide;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {1- [methyl (propyl) amino] ethyl} -3-thienyl) -1H-indole-7-carbox amides;

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide; And

5- (5-{[(1,1-dioxydotetrahydro-3-thienyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4- Piperidinyl] -1 H-indole-7-carboxamide;

Or pharmaceutically acceptable salts thereof.

Terms and Definitions

"Alkyl" refers to a saturated hydrocarbon chain having a certain number of constituent atoms. For example, C ₁ -C ₆ alkyl represents an alkyl group having 1 to 6 constituent atoms. Alkyl groups may be optionally substituted with one or more substituents as defined herein. Alkyl groups may be straight or branched. Representative branched alkyl groups have 1, 2, or 3 branches. Alkyl includes methyl, ethyl, propyl (n-propyl and isopropyl), butyl (n-butyl, isobutyl, and t-butyl), pentyl (n-pentyl, isopentyl, and neopentyl), and hexyl .

Alone or in other groups (eg, C ₁ -C ₆ alkylene-heteroaryl, C ₁ -C ₆ alkylene-heterocycloalkyl, C ₁ -C ₆ alkylene-C ₄ -C ₇ Cycloalkyl, and C ₁ -C ₆ alkylene-C ₅ -C ₇ When used to form cycloalkenyl groups), "alkylene" refers to a saturated divalent hydrocarbon chain having a certain number of constituent atoms. For example, C ₁ -C ₆ alkylene represents an alkylene group having 1 to 6 constituent atoms. The alkylene group may be optionally substituted with one or more substituents as defined herein. The alkylene group may be straight or branched. Representative branched alkylene groups have 1, 2, or 3 branches. Alkylene is methylene, ethylene, propylene (n-propylene and isopropylene), butylene (n-butylene, isobutylene, and t-butylene), pentylene (n-pentylene, isopentylene, and neo Pentylene), and hexylene.

"Alkenyl" refers to an unsaturated hydrocarbon chain having a certain number of constituent atoms and having at least one carbon-carbon double bond in the chain. For example, C ₂ -C ₆ alkenyl represents an alkenyl group having 2 to 6 constituent atoms. In some embodiments, an alkenyl group has one carbon-carbon double bond in the chain. In another embodiment, the alkenyl group has more than one carbon-carbon double bond in the chain. Alkenyl groups may be optionally substituted with one or more substituents as defined herein. Alkenyl groups may be straight or branched. Representative branched alkenyl groups have 1, 2, or 3 branches. Alkenyl includes ethylenyl, propenyl, butenyl, pentenyl, and hexenyl.

"Alkenylene" refers to an unsaturated divalent hydrocarbon chain having a certain number of constituent atoms and having at least one carbon-carbon double bond in the chain. For example, C ₂ -C ₆ alkenylene represents an alkenylene group having 2 to 6 constituent atoms. In some embodiments, an alkenylene group has one carbon-carbon double bond in the chain. In another embodiment, the alkenylene group has more than one carbon-carbon double bond in the chain. Alkenylene groups may be optionally substituted with one or more substituents as defined herein. Alkenylene groups may be straight or branched. Representative branched alkenylene groups have 1, 2, or 3 branches. Alkenyl includes ethylenylene, propenylene, butenylene, pentenylene, and hexenylene.

"Alkynylene" refers to an unsaturated divalent hydrocarbon chain having a certain number of constituent atoms and having at least one carbon-carbon triple bond in the chain. For example, C ₂ -C ₆ alkynylene represents an alkynylene group having 2 to 6 constituent atoms. In some embodiments, an alkynylene group has one carbon-carbon triple bond in the chain. In another embodiment, the alkynylene group has more than one carbon-carbon triple bond in the chain. For clarity, unsaturated divalent hydrocarbon chains having at least one carbon-carbon triple bond in the chain and at least one carbon-carbon double bond in the chain are alkynylene groups. Alkynylene groups may be optionally substituted with one or more substituents as defined herein. Alkynylene groups may be straight or branched. Representative branched alkynylene groups have 1, 2, or 3 branches. Alkynylene includes ethylinylene, propynylene, butynylene, pentynylene, and hexynylene.

"Aryl" refers to an aromatic hydrocarbon ring. The aryl group is a monocyclic ring system or a bicyclic ring system. Monocyclic aryl rings represent phenyl. Bicyclic aryl rings represent rings and naphthyls in which phenyl is fused to a cycloalkyl or cycloalkenyl ring having 5, 6, or 7 constituent atoms. Aryl groups may be optionally substituted with one or more substituents as defined herein.

"Cycloalkyl" refers to a saturated hydrocarbon ring having a certain number of constituent atoms. Cycloalkyl groups are monocyclic ring systems. For example, C ₃ -C ₆ cycloalkyl is a cycloalkyl group having 3 to 6 constituent atoms. Cycloalkyl groups may be optionally substituted with one or more substituents as defined herein. Cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

"Cycloalkenyl" refers to an unsaturated hydrocarbon ring having a certain number of constituent atoms and having carbon-carbon double bonds in the ring. For example, C ₃ -C ₆ cycloalkenyl is a cycloalkenyl group having 3 to 6 constituent atoms. In some embodiments, cycloalkenyl groups have one carbon-carbon double bond in the ring. In another embodiment, the cycloalkenyl group has more than one carbon-carbon double bond in the ring. However, cycloalkenyl rings are not aromatic. Cycloalkenyl groups are monocyclic ring systems. Cycloalkenyl groups may be optionally substituted with one or more substituents as defined herein. Cycloalkenyls include cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl.

"Enantiomerically enriched" refers to a product in which the excess of the enantiomer is greater than zero. For example, enantiomeric abundance refers to products in which the excess of enantiomers is greater than 50% ee, 75% ee, and 90% ee.

"Enantiomeric excess" or "ee" refers to the excess of one enantiomer over another as a percentage. As a result, the excess of enantiomers is 0 (0% ee) because both enantiomers are present in the same amount in the racemate mixture. However, if one enantiomer is as rich as 95% of the product, the excess of enantiomer is 90% ee (amount of rich enantiomer, 95% to amount of other enantiomer, 5% limit value) )would.

"Enantiomerically pure" refers to a product in which the excess of the enantiomer is at least 99% ee.

"Half-life" refers to the time required for half the amount of a substance to be converted to another chemically distinct species in vitro or in vivo.

"Halo" refers to halogen radical fluoro, chloro, bromo, or iodo.

"Haloalkyl" refers to an alkyl group wherein one or more hydrogen atoms attached to constituent atoms in the alkyl group have been replaced with halo. Haloalkyl includes trifluoromethyl.

"Heteroaryl" refers to an aromatic ring containing 1 to 4 heteroatoms as constituent atoms in the ring. Heteroaryl groups containing more than one heteroatom may contain different heteroatoms. Heteroaryl groups may be optionally substituted with one or more substituents as defined herein. Heteroaryl groups are monocyclic ring systems or are fused, spiro, or bridged bicyclic ring systems. Monocyclic heteroaryl rings have 5 or 6 constituent atoms. Bicyclic heteroaryl rings have 7 to 11 constituent atoms. A bicyclic heteroaryl ring is a ring that forms a spiro or bridged bicyclic ring system to which a phenyl and monocyclic heterocycloalkyl ring is attached and fused, and a monocyclic heteroaryl ring and a monocyclic cycloalkyl, cyclo Alkenyl, heterocycloalkyl, or heteroaryl rings include rings attached to form a fused, spiro, or bridged bicyclic ring system. Heteroaryl is pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, furanyl, furazanyl, thienyl, triazolyl, pyridinyl, pyrimidinyl, pyridazinyl, Pyrazinyl, triazinyl, tetrazinyl, indolyl, isoindoleyl, indolinyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pterridinyl, cinnaolinyl , Benzimidazolyl, benopyranyl, benzoxazolyl, benzofuranyl, isobenzofuranyl, benzothiazolyl, benzothienyl, furypyridinyl, and naphthyridinyl.

"Heteroatom" refers to a nitrogen, sulfur, or oxygen atom.

"Heterocycloalkyl" refers to a saturated or unsaturated ring containing 1 to 4 heteroatoms as constituent atoms in the ring. However, heterocycloalkyl rings are not aromatic. Heterocycloalkyl groups containing more than one heteroatom may contain different heteroatoms. Heterocycloalkyl groups may be optionally substituted with one or more substituents as defined herein. Heterocycloalkyl groups are monocyclic ring systems having 4 to 7 constituent atoms. In some embodiments, heterocycloalkyl is saturated. In another embodiment, heterocycloalkyl is unsaturated but not aromatic. Heterocycloalkyl is pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl, pyranyl, tetrahydropyranyl, dihydropyranyl, tetrahydrothienyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, piperididi Neil, homopiperidinyl, piperazinyl, morpholinyl, thiamorpholinyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, 1,3-oxati Olanyl, 1,3-oxatianyl, 1,3-ditianyl, and azetidinyl.

"Component atom" refers to an atom or atoms that form a chain or a ring. When there is more than one constituent atom in the chain and ring, each constituent atom is covalently bonded to adjacent constituent atoms in the chain or ring. The atoms that make up the substituent on a chain or ring are not constituent atoms in the chain or ring.

“Optionally substituted” means that the group (eg, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, or heteroaryl) is substituted with one or more substituents as defined herein Or unsubstituted. "Substituted" with respect to the group indicates that the hydrogen atom attached to the constituent atoms in the group has been replaced. The term "substituted" follows the permitted valences of the substituents and substituents to which such substitutions are substituted, and the substitution is a stable compound (ie, a compound in which no conversion occurs spontaneously, eg by rearrangement, cyclization, or elimination) It should be understood that it implies that In some embodiments, a single atom may be substituted with more than one substituent as long as such substitutions follow the allowed valences of the atom. Suitable substituents are defined herein for each substituted or optionally substituted group.

"Pharmaceutically acceptable" means that such compounds meet reasonable benefit / risk ratios suitable for use in contact with human and animal tissues within the scope of normal medical judgment and without excessive toxicity, irritation, or other problems or complications. , Substances, compositions, and dosage forms.

The symbols and conventions used herein used in the methods, schemes and examples are consistent with those used in modern scientific literature, such as the Journal of the American Chemical Society or the Journal of Biological Chemistry. Standard single letter or three letter abbreviations are generally used to name amino acid residues that are presumed to be L-configuration, unless otherwise noted. Unless otherwise stated, all starting materials were obtained from commercial suppliers and used without further purification. Specifically, the following abbreviations may be used throughout the Examples and throughout this specification.

g (grams); mg (milligrams);

L (liters); mL (milliliters);

Μl (microliters); psi (lbs per square inch);

M (molarity); mM (millimolar);

i.v. (Intravenous); Hz (hertz);

MHz (megahertz); mol (mol);

mmol (millimoles); rt (room temperature);

min (minutes); h (hours);

mp (melting point); TLC (Thin Layer Chromatography);

Tr (ret. Time); RP (reverse phase);

MeOH (methanol); i-PrOH (isopropanol);

TEA (triethylamine); TFA (trifluoroacetic acid);

TFAA (trifluoroacetic anhydride);

THF (tetrahydrofuran);

DMSO (dimethylsulfoxide); AcOEt (ethyl acetate);

DME (1,2-dimethoxyethane); DCM (dichloromethane);

DCE (dichloroethane); DMF (N, N-dimethylformamide);

DMPU (N, N'-dimethylpropyleneurea);

CDI (1,1-carbonyldiimidazole);

IBCF (isobutyl chloroformate);

HOAc (acetic acid);

HOSu (N-hydroxysuccinimide); HOBT (1-hydroxybenzotriazole);

mCPBA (meta-chloroperbenzoic acid);

EDC (1- [3-dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride);

BOC (tert-butyloxycarbonyl); FMOC (9-fluorenylmethoxycarbonyl);

DCC (dicyclohexylcarbodiimide);

CBZ (benzyloxycarbonyl);

Ac (acetyl); atm (atm);

TMSE (2- (trimethylsilyl) ethyl); TMS (trimethylsilyl);

TIPS (triisopropylsilyl); TBS (t-butyldimethylsilyl);

DMAP (4-dimethylaminopyridine); BSA (bovine serum albumin);

ATP (adenosine triphosphate);

HRP (horseradish peroxidase);

DMEM (Dulbecco's modified Eagle medium);

HPLC (high pressure liquid chromatography);

BOP (bis (2-oxo-3-oxazolidinyl) phosphinic chloride);

TBAF (tetra-n-butylammonium fluoride);

HBTU (O-benzotriazol-1-yl-N, N, N ', N'-tetramethyluronium hexafluoro phosphate);

HEPES (4- (2-hydroxyethyl) -1-piperazine ethane sulfonic acid);

DPPA (diphenylphosphoryl azide);

fHNO ₃ (Fuming HNO ₃ );

EDTA (ethylenediaminetetraacetic acid);

TMEDA (N, N, N ', N'-tetramethyl-1,2-ethanediamine);

NBS (N-bromosuccinimide);

HATU (O- (7abenzobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate);

DIPEA (diisopropylethylamine);

Imes (1,3-bis (2,4,6-trimethylphenyl) imidazolium chloride);

dppf (1,1'-bis (diphenylphosphino) ferrocene);

MDAP (Mass Indicating AutoPrep);

CH ₃ CN (acetonitrile);

EtOAc (ethyl acetate); And

NIS (N-iodosuccinimide).

The ethers mentioned are all diethyl ethers and brine represents a saturated aqueous solution of NaCl.

Compounds according to formulas (I) and (II) may contain one or more asymmetric centers (also referred to as chiral centers) and may therefore exist as individual enantiomers, diastereomers, or other stereoisomeric forms, or as mixtures thereof. have. Chiral centers such as chiral carbon atoms may also be present in substituents such as alkyl groups. If the stereochemistry of the chiral centers present in Formulas I and II, or in any of the chemical structures exemplified herein, is not specified, the structure is intended to include any stereoisomer and all mixtures thereof. Thus, compounds according to formulas (I) and (II) containing one or more chiral centers can be used as racemic mixtures, enantiomerically rich mixtures, or as individual enantiomerically pure stereoisomers.

Individual stereoisomers of compounds according to formulas (I) and (II) containing one or more asymmetric centers can be separated by methods known to those skilled in the art. For example, such separation can be accomplished by (1) formation of diastereomeric salts, complexes or other derivatives; (2) by selective reaction with stereoisomer-specific reagents, for example by enzymatic oxidation or reduction; Or (3) in a chiral environment, for example by gas-liquid or liquid chromatography, on a chiral support such as silica to which a chiral ligand is bound or in the presence of a chiral solvent. Those skilled in the art will appreciate that when the desired stereoisomer is converted to another chemical by one of the above separation procedures, subsequent steps are required to release the desired form. Alternatively, certain stereoisomers may be synthesized by asymmetric synthesis using optically active reagents, substrates, catalysts or solvents, or by converting one enantiomer to another by asymmetric transformation.

The compounds according to formulas (I) and (II) may also contain double bonds or other geometrically asymmetric centers. If the stereochemistry of the geometrically asymmetric center present in Formulas (I) and (II), or in any of the chemical structures exemplified herein, is not specified, the construct is a trans (E) geometric isomer, a cis (Z) geometric isomer and all of these It is intended to include mixtures. Similarly, all tautomeric forms are included in Formulas I and II, whether such tautomers are present in equilibrium or predominantly in one form.

Those skilled in the art will appreciate that pharmaceutically acceptable salts of the compounds according to formulas (I) and (II) may be prepared. Indeed, in some embodiments of the invention, pharmaceutically acceptable salts of the compounds according to formulas (I) and (II), because such salts impart greater stability or solubility to the molecule, thereby facilitating formulation into dosage forms. It may be preferred over each free base or free acid. The present invention therefore also relates to pharmaceutically acceptable salts of the compounds according to formulas (I) and (II).

As used herein, the term "pharmaceutically acceptable salts" refers to salts that have the desired biological activity of the compound and exhibit minimal unwanted toxic effects. These pharmaceutically acceptable salts may be prepared in situ during the final isolation and purification of the compounds, or may be prepared by separately reacting the purified compound in free acid or free base form with a suitable base or acid, respectively.

In some embodiments, compounds according to Formulas (I) and (II) may contain acidic functional groups. Suitable pharmaceutically acceptable salts include salts of these acidic functional groups. Representative salts include pharmaceutically acceptable metal salts (eg, sodium, potassium, lithium, calcium, magnesium, aluminum, and zinc salts); Carbonates and bicarbonates of pharmaceutically acceptable metal cations (eg, sodium, potassium, lithium, calcium, magnesium, aluminum, and zinc); Aliphatic amines, aromatic amines, aliphatic diamines, and hydroxy alkylamines (eg, methylamine, ethylamine, 2-hydroxyethylamine, diethylamine, triethylamine, ethylenediamine, ethanolamine, diethanolamine, And cyclohexylamine), and pharmaceutically acceptable organic primary, secondary, and tertiary amines.

In some embodiments, the compounds according to formulas (I) and (II) may contain basic functional groups and may therefore be treated with appropriate acids to form pharmaceutically acceptable acid addition salts. Suitable acids include pharmaceutically acceptable inorganic acids and pharmaceutically acceptable organic acids. Representative pharmaceutically acceptable acid addition salts include hydrochloride, hydrobromide, nitrate, methylnitrate, sulphate, bisulfate, sulfamate, phosphate, acetate, trifluoroacetate, hydroxyacetate, phenylacetate, propio Nates, butyrates, isobutyrates, valerates, maleates, hydroxymaleates, acrylates, fumarates, maleates, tartrates, citrate, salicylates, p-aminosalicylates, glycolates, lactates, Heptanoate, phthalate, oxalate, succinate, benzoate, o-acetoxybenzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, methoxybenzoate, mandelate, tannate , Formate, stearate, ascorbate, palmitate, oleate, blood Bait, pamoate, malonate, laurate, glutarate, glutamate, estoleate, methanesulfonate (mesylate), ethanesulfonate (sylate), 2-hydroxyethanesulfonate, benzenesulfonate (vesil Rate), p-amino benzenesulfonate, p-toluenesulfonate (tosylate), and naphthalene-2-sulfonate.

As used herein, the term "compound of the invention" refers to both compounds according to formulas (I) and (II) and their pharmaceutically acceptable salts.

The compounds of the present invention may exist in solid or liquid form. In the solid state, the compounds of the present invention may exist in crystalline or amorphous form, or mixtures thereof. For compounds of the present invention present in crystalline form, those skilled in the art will understand that pharmaceutically acceptable solvates may be formed in which solvent molecules are incorporated into the crystal lattice during crystallization. Solvates may include non-aqueous solvents such as ethanol, isopropanol, DMSO, acetic acid, ethanolamine, and ethyl acetate, or may include water as a solvent incorporated into the crystal lattice. Solvates in which the solvent incorporated into the crystal lattice is water are typically referred to as “hydrates”. Hydrates include stoichiometric hydrates as well as compositions containing varying amounts of water. The present invention includes all such solvates.

Those skilled in the art will also understand that some compounds of the present invention, including their various solvates, present in crystalline form may exhibit polymorphism (ie, the ability to exhibit different crystalline structures). These different crystalline forms are typically known as "polymorphs". The present invention includes all such polymorphs. Polymorphs have the same chemical composition, but the packing, geometry and other technical characteristics of the crystalline solid state are different. Thus, polymorphs can have different physical properties (eg, shape, density, hardness, deformability, stability, and dissolution properties). Polymorphs typically exhibit different melting points, IR spectra, and X-ray powder diffraction patterns, which can be used for material identification. Those skilled in the art will understand that different polymorphs can be prepared, for example, by changing or adjusting the reaction conditions or reactants used in the preparation of the compounds. For example, changes in temperature, pressure, or solvent can produce polymorphs. Also, under certain conditions, one polymorph can spontaneously convert to another polymorph.

<Compound Preparation>

The compounds of the present invention can be prepared by a variety of methods including standard chemistry. Any of the above defined variables will continue to have the meanings defined above unless otherwise stated. Exemplary general synthetic methods are described below, and then certain compounds of the invention have been prepared in the Examples paragraph.

Compounds of formulas (I) and (II) can be prepared, for example, according to schemes 1, 2 and 3 described below.

Conditions: a) (BOC) ₂ O, THF; b) s-BuLi, ClCO ₂ Me, TMEDA, Et ₂ O; c) N-bromosuccinimide, methylene chloride; d) TFA; e) MnO ₂ , THF; f) LiOH, MeOH, water; g) R 1 B (OR) ₂ , Imes-HCl, Pd (OAc) ₂ , dioxane / water; h) HATU, NH ₃ , DMF; i) RCHO (or) RC (O) R ', NaOMe, MeOH; j) Pd (OH) ₂ , H ₂ , HOAc, EtOH; k) R 4 Cl, TEA, methylene chloride (or) (R 4) ₂ O, DMAP, methylene chloride.

Scheme 1 wherein R 2 and R 3 are H, F, or Cl, U is a bond or C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene, and V is C ₅ -C ₇ cycloalkyl or C _5- General schemes for the preparation of compounds according to formulas (I) and (II) which are C ₇ cycloalkenyl or heterocycloalkyl or heterocycloalkenyl are shown. Scheme 1 also shows a general scheme for the preparation of compounds according to formulas (I) and (II), wherein U is C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene and V is aryl or heteroaryl. In Scheme 1, R 1 is as defined above unless defined otherwise. Indolin 1 described as starting material is commercially available. The reaction conditions are as described in the above schemes, but one of ordinary skill in the art will understand that some variations of the reaction conditions and / or reactants used are possible.

Treatment of indolin 1 with di-tertbutyl dicarbonate in a suitable solvent such as THF or methylene chloride yields the desired BOC protected product. The desired conversion to bromide 2 can also be achieved through lithiation with sec-butyllithium in the presence of TMEDA and quenching with methyl chloroformate, followed by bromination with N-bromosuccinimide. The bromide 2 is treated with trifluoroacetic acid, and the resulting indolin is then treated with manganese dioxide to oxidize with indole, followed by hydrolysis of the methyl ester with acid to give the desired carboxylic acid 3. Introduction of the substituent R1 can be achieved through transition metal mediated coupling with an appropriate catalyst and coupling partner. As an example of such a conversion, for condition "g" of Scheme 1, boronic acid esters or boronic acids in the presence of Pd (OAc) ₂ , Imes-HCl, and Cs ₂ CO ₃ in 1,4-dioxane and water Suzuki cross-coupling reaction can be completed. The preparation of primary carboxamide 4 can be completed through the reaction of carboxylic acid with ammonia in the presence of HATU. The conversion from 4 to 5 incorporating UV groups is carried out by reacting with an appropriate aldehyde or ketone precursor to UV. The conversion can be completed in both basic or acidic conditions. If the UV groups are fully saturated, subsequent reduction of the intermediate product will produce the desired product 5. As an example of such a reduction, for condition "j" in Scheme 1, the hydrogenation reaction in the presence of Pd (OH) ₂ completes the conversion to 5. If UV and / or R1 contains suitable protecting groups, removal of the protecting groups under suitable conditions and further conversion to other products can be achieved. Subsequent conversion of the amine functionality of the UV group to R4 sulfonamide or amide can be carried out with the appropriate sulfonyl or acid chloride or acid anhydride of R4. Those skilled in the art will understand that upon conversion of R 4 to sulfonamides or amides, further work on the resulting product to R 4 may be required. Such operations may include, but are not limited to, proper protecting and functional group manipulations, and reaction with amine / alcohol R5.

Conditions: a) R 1 B (OR) ₂ , Imes-HCl, Pd (OAc) ₂ , dioxane / water; b) HATU, NH ₃ , DMF; c) N-iodosuccinimide, methylene chloride; d) VUB (0R) ₂ , Pd (PPh ₃ ) ₄ , Cs ₂ CO ₃ , 1,4-dioxane, water; e) R ₂ Cl, TEA, methylene chloride (or) (R ₂ ) ₂ O, DMAP, methylene chloride.

Scheme 2 shows a general scheme for the preparation of compounds according to Formulas I and II, wherein U is a bond and V is aryl or heteroaryl. In Scheme 2, R 1 is as defined above unless defined otherwise. Indolecarboxylic acid 3 described as starting material is obtained as described in Scheme 1. The reaction conditions are as described in the above schemes, but one of ordinary skill in the art will understand that some variations of the reaction conditions and / or reactants used are possible.

Those skilled in the art will appreciate that if the substituents described herein are incompatible with the synthetic methods described herein, the substituents may be protected with appropriate protecting groups that are stable to the reaction conditions. The protecting group may be removed at an appropriate point in the reaction sequence to provide the desired intermediate or compound of interest. Suitable protecting groups and methods for protecting and deprotecting various substituents using such suitable protecting groups are well known to those skilled in the art (see, eg, T. Greene and P. Wuts, Protecting Groups in Chemical Synthesis (3rd ed.)). , John Wiley & Sons, NY (1999)]. In some cases, substituents may be specifically selected to be reactive under the reaction conditions employed. Under these circumstances, the reaction conditions convert the selected substituents into other substituents that are useful as intermediate compounds or are the desired substituents of the target compound.

<How to use>

Compounds of the present invention are inhibitors of IKK2. These compounds may be useful for the treatment of disorders in which the underlying pathology is due (at least in part) to inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, inflammatory bowel disease, asthma, and COPD (chronic obstructive pulmonary disease). . “Inappropriate IKK2 Activity” refers to any IKK2 activity that deviates from the normal IKK2 activity expected in a particular patient. Inappropriate IKK2 activity can take the form of, for example, an abnormal increase in activity, or a timing or regulation of IKK2 activity. Such inappropriate activity can result from, for example, overexpression or mutation of protein kinases leading to inappropriate or unregulated activation. Thus, in another aspect, the present invention relates to a method of treating such a disorder.

Such disorders include inflammatory and tissue regeneration disorders, in particular rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease); Osteoarthritis, osteoporosis and fibrotic disease; Skin diseases including psoriasis, atopic dermatitis and ultraviolet (UV) -induced skin damage; Cancers including systemic lupus erythematosus, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, autoimmune diseases including tissue and organ rejection, Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, Hodgkin's disease, Cachexia, some viral infections including infection-related inflammation and acquired immunodeficiency syndrome (AIDS), adult respiratory distress syndrome, and capillary dilatation ataxia.

The method of treatment of the present invention comprises administering to a patient in need thereof a safe and effective amount of a compound according to formulas (I) and (II) or a pharmaceutically acceptable salt thereof. Individual embodiments of the present invention include methods of treating any one of the above disorders by administering to a patient in need thereof a safe and effective amount of a compound according to Formulas (I) and (II) or a pharmaceutically acceptable salt thereof. .

As used herein with reference to a disorder, “treat” includes: (1) ameliorating or preventing one or more biological signs of the disorder, or (2) (a) leading to, or causing, the disorder. At least one point in the biological cascade or (b) interfere with one or more biological signs of the disorder, (3) alleviate one or more symptoms or effects associated with the disorder, or (4) the disorder or By slowing the progress of one or more biological signs of the disorder.

As indicated above, "treatment" of a disorder includes prevention of the disorder. Those skilled in the art will understand that "prevention" is not an absolute term. In medicine, “prevention” is understood to denote prophylactic administration of drugs to substantially reduce the likelihood or severity of the disorder or their biological manifestations, or to delay the onset of such disorders or their biological manifestations. do.

As used herein with reference to a compound of the present invention or other pharmaceutically active agent, a “safe and effective amount” is an amount sufficient to treat a patient's symptoms, within the scope of normal medical judgment, with serious side effects (reasonable benefit Low enough to avoid / in risk ratio). Safe and effective amounts of a compound may include the particular compound selected (eg, taking into account the potency, efficacy, and half-life of the compound); Selected route of administration; The disorder to be treated; The severity of the disorder to be treated; The age, size, weight, and physical condition of the patient being treated; History of the patient being treated; Duration of treatment; The nature of the accompanying therapy; Desired therapeutic effect; And similar factors, but can nevertheless typically be determined by one skilled in the art.

As used herein, “patient” refers to a human or other animal.

The compounds of the present invention can be administered by any suitable route of administration, including systemic and topical administration. Systemic administration includes oral administration, parenteral administration, transdermal administration, rectal administration, and administration by inhalation. Parenteral administration means a route of administration other than by enteral, transdermal, or inhalation, which is typically by injection or infusion. Parenteral administration includes intravenous, intramuscular, and subcutaneous injections or infusions. Inhalation refers to administration inhaled into the patient's lungs, either through the oral cavity or through the nasal cavity. Topical administration includes application to the skin as well as intraocular, ear, vaginal, and intranasal administration.

The compounds of the present invention may be administered once or according to dosing regimens in which different doses are administered at various time intervals over a given period of time. For example, the dosage may be administered one, two, three, or four times daily. Dosages may be administered indefinitely until a desired therapeutic effect is achieved or to sustain the desired therapeutic effect. Appropriate dosage regimens for the compounds of the present invention depend on the pharmacokinetic properties of the compounds, such as absorption, distribution, and half-life, which can be determined by one skilled in the art. In addition, appropriate dosing regimens for the compounds of the invention, including the duration over which such therapies are administered, include, within the knowledge and judgment of those skilled in the art, the disorder to be treated, the severity of the disorder to be treated, the age and physical condition of the patient being treated, the patient being treated Depends on the medical history, the nature of the therapy involved, the desired therapeutic effect, and similar factors. Those skilled in the art will also understand that appropriate dosing regimens may require adjustment over time or as the patient responds to the dosing regimen as the patient's needs change.

Typical daily dosages may vary depending upon the particular route of administration chosen. Typical daily dosages for oral administration range from 0.001 mg to 50 mg per kg of total body weight.

In addition, the compounds of the present invention may be administered as prodrugs. As used herein, a “prodrug” of a compound of the invention is a functional derivative of a compound that, when administered to a patient, eventually releases the compound of the invention in vivo. Those skilled in the art will appreciate that by administering a compound of the invention as a prodrug, (a) changing the onset of action of the compound in vivo; (b) changing the duration of action of the compound in vivo; (c) changes in the transport or distribution of the compound in vivo; (d) changes in the solubility of the compound in vivo; And (e) overcoming or overcoming side effects or other difficulties facing the compound. Typical functional derivatives used for the preparation of prodrugs include compound changes that cleave chemically or enzymatically in vivo. Such variations, including the preparation of phosphates, amides, esters, thioesters, carbonates, and carbamates, are well known to those skilled in the art.

The invention also provides a compound of the invention for use in medical treatment, and in particular in the treatment of disorders mediated by IKK2 activity. Thus, in a further aspect, the present invention relates to the use of a compound according to formulas (I) and (II) or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for the treatment of disorders characterized by inadequate IKK2 activity.

Certain disorders characterized by inappropriate IKK2 activity include inflammatory and tissue regeneration disorders, in particular rheumatoid arthritis, inflammatory bowel disease, asthma and COPD (chronic obstructive pulmonary disease); Osteoarthritis, osteoporosis and fibrotic disease; Skin diseases including psoriasis, atopic dermatitis and ultraviolet (UV) -induced skin damage; Cancers including systemic lupus erythematosus, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, autoimmune diseases including tissue and organ rejection, Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, Hodgkin's disease , Cachexia, some viral infections including infection-associated inflammation and acquired immunodeficiency syndrome (AIDS), adult respiratory distress syndrome, and capillary dilatation ataxia (as a result of inhibition of protein kinase IKK2).

<Composition>

The compounds of the present invention will not necessarily be, but will generally be formulated into pharmaceutical compositions prior to administration to a patient. Accordingly, another aspect of the present invention relates to a pharmaceutical composition comprising a compound of the present invention and one or more pharmaceutically acceptable excipients.

The pharmaceutical compositions of the present invention may be prepared and packaged in bulk form from which a safe and effective amount of a compound of the present invention may be extracted, which may then be given to the patient, for example in powder or syrup. Alternatively, the pharmaceutical compositions of the present invention may be prepared and packaged in unit dosage forms, wherein each physically distinct unit contains a safe and effective amount of a compound of the present invention. When prepared in unit dosage form, the pharmaceutical compositions of the invention typically contain, for example, 0.5 mg to 1 g, or 1 mg to 700 mg, or 5 mg to 100 mg of a compound of the invention.

Pharmaceutical compositions of the invention typically contain one compound of the invention. However, in some embodiments, the pharmaceutical compositions of the present invention contain more than one compound of the present invention. For example, in some embodiments the pharmaceutical composition of the present invention contains two compounds of the present invention. In addition, the pharmaceutical compositions of the present invention may optionally further comprise one or more additional pharmaceutically active compounds.

As used herein, "pharmaceutically acceptable excipient" means a pharmaceutically acceptable material, composition or vehicle included to impart form or hardness to a pharmaceutical composition. Each excipient is compatible with other ingredients of the pharmaceutical composition to avoid interactions that, when administered to a patient when mixed, will substantially reduce the efficacy of the compounds of the invention and may result in pharmaceutically unacceptable pharmaceutical compositions. There must be In addition, each excipient must of course be high enough to be pharmaceutically acceptable.

Compounds of the invention and pharmaceutically acceptable excipients or excipients will typically be formulated in dosage forms adapted to be administered to a patient via the desired route of administration. For example, the dosage form may be (1) for oral administration, such as tablets, capsules, caplets, pills, troches, powders, syrups, elixirs, suspensions, solutions, emulsions, sachets, and casses (cachet); (2) for parenteral administration, such as sterile solutions, suspensions, and powders (for reconstitution); (3) for transdermal administration, such as transdermal patches; (4) for rectal administration, such as suppositories; (5) for inhalation such as aerosols, solutions, and dry powders; And (6) for topical administration, such as creams, ointments, lotions, solutions, pastes, sprays, foams, and gels.

Appropriate pharmaceutically acceptable excipients will vary depending upon the particular dosage form selected. In addition, suitable pharmaceutically acceptable excipients may be selected depending on the specific function they can perform in the composition. For example, some pharmaceutically acceptable excipients may be selected due to their ability to facilitate the preparation of homogeneous dosage forms. Some pharmaceutically acceptable excipients may be selected due to their ability to facilitate the preparation of stable dosage forms. Some pharmaceutically acceptable excipients may be selected because of the ability of the compound or compounds of the present invention to be administered to a patient to facilitate delivery or transport from one organ, or from any part of the body, to another organ, or to another part of the body. have. Some pharmaceutically acceptable excipients may be selected due to their ability to enhance patient compliance.

Suitable pharmaceutically acceptable excipients are diluents, fillers, binders, disintegrants, lubricants, lubricants, granulating agents, coatings, wetting agents, solvents, cosolvents, suspending agents, emulsifiers, sweeteners, flavoring agents, flavor masking agents Excipients such as colorants, antidegradants, humectants, chelating agents, plasticizers, viscosity enhancers, antioxidants, preservatives, stabilizers, surfactants, and buffers. Those skilled in the art will appreciate that some pharmaceutically acceptable excipients may function in more than one function and may function separately depending on how much excipient is present in the formulation and what other ingredients are present in the formulation.

Those skilled in the art have the knowledge and skills to select appropriate amounts of suitable pharmaceutically acceptable excipients for use in the present invention. In addition, there are a variety of materials available to those of skill in the art that pharmaceutically acceptable excipients are disclosed and that may be useful in selecting an appropriate pharmaceutically acceptable excipient. Examples are Remington's Pharmaceutical Sciences (Mack Publishing Company), The Handbook of Pharmaceutical Additives (Gower Publishing Limited), and The Handbook of Pharmaceutical Excipients (the American Pharmaceutical Association and the Pharmaceutical Press). .

Pharmaceutical compositions of the present invention are prepared using techniques and methods known to those skilled in the art. Several methods commonly used in the art are described in Remington's Pharmaceutical Sciences (Mack Publishing Company).

In one aspect, the invention relates to a solid oral dosage form, such as a tablet or capsule, comprising a safe and effective amount of a compound of the invention and a diluent or filler. Suitable diluents and fillers include lactose, sucrose, dextrose, mannitol, sorbitol, starch (eg corn starch, potato starch, and pre-gelatinized starch), cellulose and its derivatives (eg microcrystalline cellulose), Calcium sulfate, and dibasic calcium phosphate. Oral solid dosage forms may further comprise a binder. Suitable binders include starch (eg corn starch, potato starch, and starch-starch), gelatin, gum arabic, sodium alginate, alginic acid, tragacanth, guar gum, povidone, and cellulose and derivatives thereof (eg , Microcrystalline cellulose). Oral solid dosage forms may further comprise a disintegrant. Suitable disintegrants include crospovidone, sodium starch glycolate, croscarmelose, alginic acid, and carboxymethyl cellulose sodium. Oral solid dosage forms may further comprise a lubricant. Suitable glidants include stearic acid, magnesium stearate, calcium stearate, and talc.

If appropriate, dosage unit formulations for oral administration may be microencapsulated. The composition can also be prepared to prolong or sustain the release, for example by coating or interposing particulate material in a polymer, wax, or the like.

The compounds of the invention can also be coupled with soluble polymers as targetable drug carriers. Such polymers may include polyvinylpyrrolidone, pyran copolymers, polyhydroxypropylmethacrylamide-phenol, polyhydroxyethylaspartamidephenol, or polyethyleneoxidepolylysine substituted with palmitoyl moiety. In addition, the compounds of the present invention are, for example, cross-linked or amphiphilic block air of polylactic acid, polylepsilone caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacrylates and hydrogels. And may be coupled with a biodegradable polymer species useful for achieving controlled release of the drug, such as coalescence.

In another aspect, the invention relates to a liquid oral dosage form. Oral liquids such as solutions, syrups and elixirs can be prepared in dosage unit form such that a given amount contains a predetermined amount of a compound of the present invention. Syrups can be prepared by dissolving the compounds of the invention in suitably flavored aqueous solutions, while elixirs are prepared by using a non-toxic alcoholic vehicle. Suspensions can be formulated by dispersing the compound of the invention in a non-toxic vehicle. Solubilizers such as ethoxylated isostearyl alcohol and polyoxy ethylene sorbitol ethers and flavoring additives such as emulsifiers, preservatives, peppermint oil or natural sweeteners or saccharin or other artificial sweeteners may also be added.

In another aspect, the invention relates to a dosage form adapted to be administered to a patient by inhalation. For example, the compounds of the present invention can be inhaled into the lungs as dry powders, aerosols, suspensions, or solutions.

Dry powder compositions for delivery to the lungs by inhalation typically comprise a compound of the invention as finely divided powder and one or more pharmaceutically acceptable excipients as finely divided powder. Pharmaceutically acceptable excipients which are particularly suitable for use in dry powders are known to those skilled in the art and include lactose, starch, mannitol, and mono-, di- and polysaccharides.

The dry powder may be administered to the patient via a reservoir dry powder inhaler (RDPI) having a reservoir suitable for storing multiple (non-quantitative) medications in dry powder form. RDPI typically includes a means for metering each medical dose from the reservoir to the delivery location. For example, the metering means may comprise a metering cup, the metering cup being moveable to a second position such that the cup is available to the patient by inhalation with a metered dose of medication at a first location where the drug can be filled from the reservoir. Do.

Alternatively, the dry powder may be provided in a blister pack for use in capsules (eg gelatin or plastic), cartridges or multi-dose dry powder inhaler (MDPI). MDPI is an inhaler in which a drug is contained in a multi-dose pack containing (or transporting) a number of defined doses (or portions thereof) of the drug. When dry powder is provided in a blister pack, it comprises a plurality of blisters for the reception of a medicament in dry powder form. The blisters are typically arranged in a conventional manner to facilitate the release of medication from the blisters. For example, blisters may generally be arranged in a circular manner on a disc shaped blister pack, or the blisters may be elongate in shape, including, for example, strips or tapes. Capsules, cartridges, or blisters may each contain, for example, 20 μg to 10 mg of a compound of the present invention.

Aerosols can be formed by suspending or dissolving the compounds of the present invention in a liquefied propellant. Suitable propellants include halogenated carbons, hydrocarbons and other liquefied gases. Representative propellants include trichlorofluoromethane (propellant 11), dichlorofluoromethane (propellant 12), dichlorotetrafluoroethane (propellant 114), tetrafluoroethane (HFA-134a), 1,1-difluoro Ethane (HFA-152a), difluoromethane (HFA-32), pentafluoroethane (HFA-12), heptafluoropropane (HFA-227a), perfluoropropane, perfluorobutane, perfluoro Pentane, butane, isobutane, and pentane. Aerosols comprising a compound of the invention will typically be administered via a metered dose inhaler (MDI). Such devices are known to those skilled in the art.

Aerosols are additional pharmaceutically acceptable excipients typically used with MDI, such as surfactants, to improve the physical stability of the formulation, to improve valve performance, to improve solubility, or to improve taste. , Lubricants, cosolvents and other excipients.

In addition, suspensions and solutions comprising the compounds of the present invention can be administered to a patient via a nebulizer. Solvents or suspending agents used for spraying may be any pharmaceutically acceptable such as water, aqueous saline, alcohols or glycols (eg, ethanol, isopropyl alcohol, glycerol, propylene glycol, polyethylene glycol, etc.) or mixtures thereof. May be liquid. Saline solutions utilize salts with little or no pharmacological activity after administration. Organic salts such as alkali metal or ammonium halogen salts (e.g., sodium chloride, potassium chloride) or organic salts such as potassium, sodium and ammonium salts, or organic acids such as, for example, ascorbic acid, citric acid, acetic acid, tartaric acid, etc. Can be used for

Other pharmaceutically acceptable excipients may be added to the suspension or solution. Compounds of the invention include inorganic acids (eg, hydrochloric acid, nitric acid, sulfuric acid and / or phosphoric acid); Organic acids (eg, ascorbic acid, citric acid, acetic acid, tartaric acid, etc.); Complexing agents (eg, EDTA or citric acid and salts thereof); Or by the addition of antioxidants (eg vitamin E or ascorbic acid). These may be used alone or together to stabilize the compounds of the present invention. Preservatives such as benzalkonium chloride or benzoic acid and salts thereof may be added. Surfactants may especially be added to improve the physical stability of the suspension. These include lecithin, dioctylsulfosuccinate, oleic acid and sorbitan esters.

Pharmaceutical compositions adapted for transdermal administration may be present as discrete patches intended to remain in intimate contact with the epidermis of the patient for an extended period of time. For example, the active ingredient can be delivered via iontophoresis from a patch, as generally described in Pharmaceutical Research, 3 (6), 318 (1986).

Pharmaceutical compositions adapted for topical administration may be formulated as ointments, creams, suspensions, lotions, powders, solutions, pastes, gels, sprays, aerosols or oils.

For the treatment of the eye or other external tissues (eg mouth and skin), the composition can be applied as a topical ointment or cream. When formulated in ointments, the compounds of the present invention can be used with paraffin or water-miscible ointment bases. Alternatively, the compounds of the present invention may be formulated in creams with an oil-in-water cream base or a water-in-oil base.

Pharmaceutical compositions adapted for intranasal administration wherein the carrier is a solid comprise coarse powders, eg 20 to 500 micrometers in particle size, which are administered by rapid inhalation through the nasal cavity from a container containing powder close to the nose. Suitable compositions wherein the carrier is a liquid for administration as a nasal spray or as a nasal drop are included aqueous or oil solutions of the compounds of the present invention.

Pharmaceutical compositions adapted for parenteral administration include aqueous and non-aqueous sterile injectable solutions which may contain antioxidants, buffers, bacteriostatics, and solutes that make the agent and the blood of the subject administered isotonic; And aqueous and non-aqueous sterile suspensions which may include suspending agents and thickening agents. The composition may be provided in unit-dose or multi-dose containers, such as, for example, sealed ampoules and vials, and in a lyophilized state requiring only the addition of a sterile liquid carrier (eg, water for injection) immediately before use. Can be archived. Instant injection solutions and suspensions can be prepared from sterile powders, granules and tablets.

The following examples illustrate the invention. These examples are not intended to limit the scope of the present invention but to provide those skilled in the art with guidance on preparing and using the compounds, compositions, and methods of the present invention. While particular embodiments of the invention have been described, those skilled in the art will understand that various changes and improvements can be made without departing from the spirit and scope of the invention.

The ethers mentioned are all diethyl ethers and brine represents a saturated aqueous solution of NaCl. Unless otherwise stated, all temperatures are expressed in degrees Celsius (Celsius). Unless otherwise noted, all reactions were performed at room temperature under inert atmosphere.

¹ H NMR spectra were recorded using a Brookr DPX400, Brooker DPX250, Brooker AC400 or Varian Inova 400. Chemical displacements are expressed in parts per million (ppm, δ units). The cracking pattern describes the identifiable multiplicity: s (single peak), d (double peak), t (triple peak), q (quad peak), quint (triple peak), m (multiple peak) , br (broad peak).

Low-discrimination mass spectra (MS) were recorded using a JOEL JMS-AX505HA, JOEL SX-102 or SCIEX-APIiii spectrometer, and LC-MS was Waters ZQ or PE Scix Single Quadrupole Quadrupole) were recorded using LC / MS API-150 spectrometer.

Preparative HPLC is carried out on an HPLC ABZ + 5 μm column (10 cm × 21.2 mm id) where the material is gradient eluted with 0.1% formic acid in water and 0.05% formic acid in acetonitrile at a flow rate of 8 ml / min and UV detection at 254 nm. The method of purification by high performance liquid chromatography is shown.

Unless stated otherwise, silica flash column chromatography and Combiflash represent purification of materials using Redisp pre-filled silica flash columns on an ISCO sq 16x machine with the solvent system described.

Reversed phase HPLC method A represents a method of purification by high performance liquid chromatography on an HPLC S-5 μm column (75 × 30 mm i.d.) gradient gradient eluted with the solvent system described and UV detection at 254 nm.

Reverse phase HPLC method B is a method for purification by high performance liquid chromatography on an HPLC Luna C18 (2) 100A column (50 × 21.2 mm id) gradient gradient eluting with a solvent system describing the material and UV detection at 254 nm. Indicates.

LC-MS Experimental Conditions of PE Cyx Single Quadrupole LC / MS API-150:

Liquid Chromatograph:

System: Shimadzu LC system with SCL-10A controller and dual UV detectors

Automated sample injector: Leap CTC with Valco six-hole injector

Column: Aquasil / Aquasil (C18 4 x 1 mm)

Injection volume (μl): 2.0

Solvent A: H ₂ O, 0.02% TFA

Solvent B: MeCN, 0.018% TFA

Gradient: linear

Channel A: UV 214 nm

Channel B: ELS

step Minutes Duration (minutes) Flow rate (μl / min) Solvent A Solvent B 0 0.00 0.00 300.00 95.00 5.00 One 0.00 0.01 300.00 95.00 5.00 2 0.01 3.20 300.00 10.00 90.00 3 3.21 1.00 300.00 10.00 90.00 4 4.21 0.10 300.00 95.00 5.00 5 4.31 0.40 300.00 95.00 5.00

Mass spectrometer: PE Cyx single quadrupole LC / MS API-150

Polarity: positive

Detection mode: profile

<Intermediate>

Intermediate 1: 1,1-dimethylethyl 2,3- Dehydro -1H-indole-1- Carboxylate

Indolin (10 g, 84 mmol) was dissolved in tetrahydrofuran (100 mL) and di-tert-butylcarbonate (22 g, 0.1 mol) was added. The mixture was stirred at room temperature under inert nitrogen atmosphere for 16 hours. Tetrahydrofuran was removed in vacuo and the crude product was purified by vacuum distillation to give the title compound (15.1 g) as a clear, soft red oil which, upon standing (temperature: 160-162 ° C., pressure 1-0.1 mmHg) Crystallized.

Intermediate 2: 1- (1,1-dimethylethyl) 7- methyl  2,3- Dehydro -1H-indole-1,7- Dicarboxylate

1,1-dimethylethyl 2,3-dihydro-1H-indole-1-carboxylate (5 g, 22.8 mmol) and N, N, N ', N'-tetramethyl-1,2-ethanediamine ( 4.6 mL, 30.5 mmol) was dissolved in dry diethyl ether (300 mL) and cooled to −78 ° C. in an acetone / dry ice bath. sec-butyl lithium (1.4 M solution in cyclohexane, 17.6 mL, 24.6 mmol) was added dropwise over 10 minutes and the reaction was stirred at this temperature for 90 minutes. Methyl chloroformate (8.8 mL, 10.8 g, 0.1 mol) was added to the mixture and the reaction was allowed to warm to room temperature over 1 hour. Water was carefully added to the mixture and the organic layer was separated and washed three times with more water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (4.91 g) as a sticky yellow solid.

Intermediate 3: 1- (1,1-dimethylethyl) 7- methyl  5- Bromo -2,3- Dehydro -1H-indole-1,7- Dicarboxylate

1- (1,1-dimethylethyl) 7-methyl 2,3-dihydro-1H-indole-1,7-dicarboxylate (3.1 g, 11.2 mmol) and N-bromosuccinimide (2.0 g , 11.2 mmol) was dissolved in dry dichloromethane (100 mL) and stirred for 16 h at room temperature under a nitrogen atmosphere. The reaction was partitioned into sodium hydroxide solution (2 M), separated and washed with more sodium hydroxide solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo to provide the title compound as a sticky red solid (3.55 g).

Intermediate 4: methyl  5- Bromo -2,3- Dehydro -1H-indole-7- Carboxylate

1- (1,1-dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1H-indole-1,7-dicarboxylate (9 g, 25 mmol) was converted to trifluoroacetic acid ( 6 mL) and stirred at rt for 16 h. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer was washed twice with sodium hydroxide solution until the aqueous layer was pH> 7. The organic layer was then concentrated in vacuo to give the title compound as a brown solid (6.5 g).

Intermediate 5: methyl  5- Bromo -1H-indole-7- Carboxylate

Methyl 5-bromo-2,3-dihydro-1H-indole-7-carboxylate (6.5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL). Activated manganese idealized (5 μm particle size, 22 g, 0.25 mol) was added and the mixture was stirred at rt for 16 h. An additional 22 g of activated manganese dioxide was added and the reaction stirred for 96 hours. The reaction was then filtered through celite and concentrated in vacuo to give the title compound (5.1 g) as a beige solid.

Intermediate 6: 5- Bromo -1H-indole-7- Carboxylic acid

5-bromo-1H-indole-7-carboxylate (5 g, 19.7 mmol) was dissolved in methanol (200 mL) and a solution of lithium hydroxide (0.99 g, 41 mmol) in water (10 mL) was added. . The mixture was heated at reflux for 50 h. Methanol was removed under vacuum and the residue was diluted with aqueous hydrochloric acid (2 M). The resulting precipitate was filtered and dried on a heated vacuum pistol to give the title compound as a beige solid (4.7 g).

Intermediate 7: 5- Bromo -1H-indole-7- Carboxamide

To a solution of 5-bromo-1H-indole-7-carboxylic acid (10.0 g, 42 mmol) in CH ₂ Cl ₂ (100 mL) at room temperature, EDC (9.66 g, 50.4 mmol), HOBt (6.81 g, 50.4 mmol) and NH ₃ (2.0 M in MeOH, 84 mL, 168 mmol) were added. The reaction mixture was stirred at rt for 16 h. The solvent was evaporated and the residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous layer was extracted with ethyl acetate (100 mL × 2) and the combined organic phases were dried over MgSO ₄ and concentrated to give crude product (10 g, 98%). The crude product was used directly in the next step without further purification.

LC / MS: m / z 240.0 (M + H), 1.95 min.

Intermediate 8: 1,1-dimethylethyl 4- [7- ( Aminocarbonyl ) -5- Bromo -1H-indol-3-yl] -3,6- Dihydro -1 (2H)- Pyridinecarboxylate

To a solution of 5-bromo-1H-indole-7-carboxamide (10 g, 41.84 mmol) in methanol (5 mL), 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate ( 684 mg, 3.42 mmol) and sodium methoxide (0.5 M in THF, 13.7 mL, 6.84 mmol) were added. The reaction mixture was stirred at reflux for 16 h. All solvents were evaporated under reduced pressure. The residue was partitioned between ethyl acetate (100 mL) and water (100 mL). The combined organic phases were dried over MgSO ₄ , concentrated under reduced pressure and purified by flash column chromatography (ethyl acetate / hexane, 1/1) to give the desired product (7.4 g, 43%).

LC / MS: m / z 420.0 (M + H), 2.35 min.

Intermediate 9: 1,1-dimethylethyl 4- [7- ( Aminocarbonyl ) -5- Bromo -1H-indol-3-yl] -1-piperidine Carboxylate

1,1-dimethylethyl 4- [7- (aminocarbonyl) -5-bromo-1H-indol-3-yl] -3,6-dihydro-1 (2H) -pyridine in ethanol (600 mL) To a solution of carboxylate (7.41 g, 17.64 mmol), platinum oxide (200 mg, 5%) was added. The reaction mixture was hydrogenated for 16 h under H ₂ atmosphere. The resulting mixture was filtered through celite and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (ethyl acetate / hexane, 1: 4 → 2: 1 v / v) to give the desired product (3.6 g, 48%).

LC-MS: m / z 422.0 (M + H), 2.25 mins.

Intermediate 10: 5- Bromo -3- (4- Piperidinyl ) -1H-indole-7- Carboxamide

1,1-dimethylethyl 4- [7- (aminocarbonyl) -5-bromo-1H-indol-3-yl] -1-piperidinecarboxylate (1.56 g, 3.7 in methanol) To a solution of mmol), HCl in dioxane (4 M, 35.5 mL) was added. The reaction mixture was stirred at rt for 2 h. The solvent was evaporated under reduced pressure and the resulting residue was partitioned between ethyl acetate (50 mL) and 5% aqueous NaOH (50 mL). The aqueous layer was washed with ethyl acetate (2 x 50 mL) and the combined organic phases were dried over MgSO ₄ and concentrated under reduced pressure to give the desired product (685 mg, 58%) which was used in the next step without further purification.

LC-MS: m / z 322.0 (M + H), 1.45 min.

Intermediate 11: 5- Bromo -3- [1- ( Ethanesulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Ethanesulfonyl chloride (4.5 mL, 47.4 mmol) was added 5-bromo-3- (4-piperidinyl) -1H-indole-7-carboxamide hydrochloride (8.49 g, 23.7 mmol in DMF (80 mL). ) And triethylamine (13.2 mL, 94.7 mmol) were added dropwise at 0 ° C. (bath temperature). The reaction mixture was stirred at 0 ° C. for 45 minutes and then poured into a 2: 1 mixture of EtOAc / H ₂ O (300 mL). The resulting precipitate was filtered off, washed with EtOAc (2 × 50 mL) and left to stand. EtOAc / H ₂ O 2 layer was separated and the aqueous layer was extracted with EtOAc (2 × 100 mL). The combined organic layers were washed with saturated NaCl (1 × 100 mL), dried (MgSO ₄ ), filtered and concentrated under reduced pressure. The crude product was combined with the isolated precipitate and washed with MeOH (1 × 10 mL) to give 8.19 g (83%) of the title compound.

Alternatively, the title compound could be prepared as follows:

To 5-bromo-3- (4-piperidinyl) -1H-indole-7-carboxamide (900 mg, 2.8 mmol) in CH ₂ Cl ₂ (10 mL) at 0 ° C., ethanesulfonyl chloride ( 0.8 mg, 8.4 mmol) and triethylamine (1.6 mL, 11.2 mmol) were added. The reaction mixture was stirred at 0 ° C. for 30 minutes, after which the mixture was partitioned between CH ₂ Cl ₂ and water. The aqueous phase was extracted with CH ₂ Cl ₂ (50 mL × 2) and the combined organic phases were dried over MgSO ₄ and concentrated under reduced pressure. The resulting residue was purified by solid phase extraction on 500 mg aminopropyl column (International Sorbent Technologies) eluting with chloroform (30 mL x 2) and ethyl acetate (50 mL) to give 800 mg of the title compound. (69%) was provided.

LC / MS: m / z 414.0 (M + H), 2.2 min.

Intermediate 12: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5 [3- ( Hydroxymethyl ) Phenyl ] -1H-indole-7-carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20.0 mg, in dioxane / H ₂ O (2 mL / 0.7 mL) 0.048 mmol), K ₃ PO ₄ (21.0 mg, 0.096 mmol) and [3- (hydroxymethyl) phenyl] boronic acid (30.0 mg, 0.193 mmol) were bubbled with argon for 5 minutes and then Pd (PPh ₃ ) ₄ (5.0 mg, 0.0048 mmol) was added. The reaction mixture was heated at 160 ° C. for 20 minutes in a microwave reactor (Smith synthesizer). The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine (10 mL), dried over MgSO ₄ , concentrated and purified by reverse phase HPLC method A (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (9.7 mg, 46% ).

Intermediate 13: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Formylphenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (hydroxymethyl) phenyl] -1H-indole-7-carboxamide (52.0 mg, in THF (10 mL), 0.120 mmol), MnO ₂ (360.0 mg, 3.5 mmol) was added at ambient temperature. The resulting suspension was stirred overnight, filtered through celite and the solids washed with THF (3 × 10 mL). The filtrate was concentrated to give the title compound (51.0 mg, 98%), which was used without purification in the next step.

LC / MS: m / z 440.4 (M + H), retention time: 1.97 minutes.

Intermediate 14: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- ( Hydroxymethyl ) Phenyl ] -1H-indole-7-car Lebox Arm De

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20.0 mg, in dioxane / H ₂ O (2 mL / 0.7 mL) 0.048 mmol), K ₃ PO ₄ (21.0 mg, 0.096 mmol) and [4- (hydroxymethyl) phenyl] boronic acid (30.0 mg, 0.193 mmol) were bubbled with argon for 5 minutes and then Pd (PPh ₃ ) ₄ (5.0 mg, 0.0048 mmol) was added. The reaction mixture was heated at 160 ° C. for 20 minutes in a microwave reactor (Smith Synthesizer). The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine (10 mL), dried over MgSO ₄ , filtered, concentrated and purified by reverse phase HPLC A (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (6.4 mg , 30%).

LC / MS: m / z 442.4 (M + H), retention time: 1.78 minutes.

Intermediate 15: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4- Formylphenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (hydroxymethyl) phenyl] -1H-indole-7-carboxamide (25 mg, in THF (5 mL) 0.058 mmol), MnO ₂ (160.0 mg, 1.73 mmol) was added at ambient temperature. The resulting suspension was stirred overnight, filtered through celite and the solids washed with THF (3 × 10 mL). The filtrate was concentrated to give the title compound (15 mg, 58%), which was used without purification in the next step.

LC / MS: m / z 440.4 (M + H), retention time: 2.02 minutes.

Intermediate 16: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan 2-yl) -1H-indole-7- Carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (1.0 g, 2.42 mmol), bis (pinacole) in DME (15.0 mL) To a solution of ito) diborane (2.45 g, 9.66 mmol) and potassium carbonate (2.10 g, 21.8 mmol), after degassing for 5 minutes, Pd ₂ Cl ₂ (dppf) was added. The mixture was then heated at 130 ° C. for 11000 seconds under microwaves. The reaction mixture was then diluted with EtOAc (300 mL) and H ₂ O (100 mL) and the solids were filtered off. The organic layer was then washed with H ₂ O (3 × 80 mL) and brine. The organic layer was dried over MgSO ₄ and concentrated. DCM (40 mL) was then added to remove any byproducts to give 2.4 g of the title compound.

LC / MS: m / z 462.3 (M + H), retention time: 2.03 minutes.

Intermediate 17: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5- Formyl -2- Thienyl ) -1H-indole-7- Carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (200 mg) in dioxane (4.5 mL) and H ₂ O (1.5 mL) , 0.49 mmol) in [5- (hydroxymethyl) -2-thienyl] boronic acid (232 mg, 1.47 mmol), potassium carbonate (406 mg, 2.94 mmol) and tetrakis (triphenylphosphine) palladium (0) (57 mg, 0.049 mmol) was added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. Aqueous workup with EtOAc / H ₂ O gave 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (hydroxymethyl) -2-thienyl] -1H-indole-7 -447 mg of carboxamide was provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (hydroxymethyl) -2-thienyl] -1H-indole-7-carboxamide in THF (5.0 mL) To a solution of (200 mg, 0.46 mmol) was added MnO ₂ (1.21 g, 13.9 mmol). The mixture was stirred at rt for 3 h. The reaction mixture was filtered through celite to give 100 mg (48.8%) of the title compound.

LC / MS: m / z 446.2 (M + H), retention time: 2.27 minutes.

Intermediate 18: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4- Formyl -2- Thienyl ) -1H-indole-7- Carboxamide

To a solution of 3-thiophenecarbaldehyde (3.0 g, 26.8 mmol) in DCM (54 mL) was added aluminum trichloride (8.37 g, 63 mmol) at 0 ° C. The reaction was then heated to reflux and bromine (1.6 mL, 30.28 mmol) was added dropwise. After addition, the reaction mixture was stirred at reflux for 4 hours. After cooling to rt, cooled H ₂ O (100 mL) was added and extracted with DCM (2 × 100 mL). The combined organic layers were washed with NaHCO ₃ and dried. This was purified by flash chromatography to give 3.62 g (71%) of 5-bromo-3-thiophenecarbaldehyde.

3- [1- (ethylsulfonyl) -4- in a solution of 5-bromo-3-thiophencarbaldehyde (250 mg, 1.29 mmol) in dioxane (4.5 mL) and H ₂ O (1.5 mL). Piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (200 mg, 0.43 mmol ), Potassium carbonate (250 mg, 2.58 mmol) and tetrakis (triphenylphosphine) palladium (0) (56 mg, 0.049 mmol) were added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. Then treated with EtOAc and H ₂ O to afford the crude product. Then treated with MeOH (10 mL) and the solids were filtered and collected to give 310 mg of the desired title compound.

LC / MS: m / z 446.4 (M + H), retention time: 1.94 minutes.

Intermediate 19: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5- Formyl -3- Thienyl ) -1H-indole-7- Carboxamide

To a solution of 4-bromo-2-thiophencarbaldehyde (1.0 g, 4.48 mmol) in DME (16 mL) bis (pinacolato) diborane (1.48 g, 5.82 mmol), KOAc (1.14 g, 5.11 mmol) and Pd ₂ Cl ₂ (dppf) (106 mg, .448 mmol). The reaction was carried out at 150 ° C. for 20 minutes under microwave. The solvent was concentrated and aqueous worked up with EtOAc and H ₂ O. The compound was purified by flash chromatography using hexane and EtOAc to afford 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-thiophencarb 1.8 g of aldehyde was provided.

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (909 mg) in dioxane (7.5 mL) and H ₂ O (2.5 mL) , 2.2 mmol) in 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-thiophencarbaldehyde (1.57 g, 6.6 mmol) ), Potassium carbonate (1.82 g, 13.2 mmol), and tetrakis (triphenylphosphine) palladium (0) (30 mg, .22 mmol) were added. The reaction was heated at 150 ° C. for 20 minutes under microwave. The mixture was then concentrated to dryness. EtOAc (50 mL) was added to the residue and washed with brine. The precipitate formed between water and the organic layer was filtered and collected as a brown solid to give 874 mg (89%) of the title compound.

LC / MS: m / z 446.4 (M + H), retention time: 1.93 minutes.

Intermediate 20: 5- Bromoisoindolin

2.O g (13.6 mmol) of phthalimide was placed in a dried 50 mL two-necked round bottom flask equipped with an addition funnel and CaCl ₂ dry tube. The flask was then cooled to 0 ° C. in a salt and ice bath. An ice cooled mixture of concentrated sulfuric acid and fuming nitric acid (1: 1 v / v) was added slowly with constant stirring. The mixture was then stirred for 30 minutes at 0 ° C. and slowly warmed to room temperature with stirring over 1 hour. The reaction mixture was then poured on ice. The solid product was filtered and dried to give 1.6 g (61.3%) of 5-nitro-1H-isoindole-1,3 (2H) -dione as a yellow solid.

To a solution of 5-nitro-1H-isoindole-1,3 (2H) -dione (1.0 g, 5.2 mmol) in dry THF (15 mL) was added 10% Pd / C (0.2 g). The mixture was hydrogenated at 30-40 psi for 17 hours. The crystals were filtered off and the filtrate was evaporated in vacuo to give 0.5 g (59.3%) of 5-amino-1H-isoindole-1,3 (2H) -dione as a yellow solid.

Of 5-amino-1H-isoindole-1,3 (2H) -dione (1.O g, 6.2 mmol) dissolved in sulfuric acid solution ( ₂ mL concentrated H ₂ SO ₄ in 7.5 mL H ₂ O) at 0 ° C. To the stirred solution, ice cooled sodium nitrite solution (0.8 g in 2 mL of H ₂ O) was added dropwise. After stirring for 45 min at 0 ° C., CuBr (3.4 g, 23.7 mmol) and HBr [48%] (13.6 mL, 4 vol. Wrt CuBr) were added at the same temperature. The resulting mixture was stirred at 80 ° C. for 8 hours and then poured onto flake ice. The solid was filtered, washed with ice cold water and then thoroughly dried to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3 (2H) -dione as a brown solid.

In a dried 50 mL three necked round bottom flask equipped with a reflux condenser and an addition funnel was placed BH ₃ -THF (16O mL) containing dry THF (50 mL). The mixture was cooled to 0 ° C. To this cooled solution 5-bromo-1H-isoindole-1,3 (2H) -dione (8.O g, 35.4 mmol) in dry THF (100 mL) was added slowly and warmed to room temperature. After 10 minutes the mixture was refluxed for 16 hours at room temperature. The reaction mixture was then cooled to 0 ° C. and quenched with methanol. (Note: active bubble generation will occur). 20-3O mL of 2N HCl was added and the mixture was refluxed for 1 hour. The mixture was cooled, basified with NaOH solution and extracted with ethyl acetate. The combined organic extracts were washed with water, saturated NaCl solution, dried over Na ₂ SO ₄ and concentrated in vacuo. To the crude product in MeOH (15O mL), Et ₃ N (12 mL) and di-tert-butyl dicarbonate (13.8 g, 63.23 mmol) were added and stirred at rt for 16 h. The reaction mixture was then concentrated in vacuo. The crude product was diluted with CH ₂ Cl ₂ (20 mL), washed with water, saturated NaCl solution and dried over Na ₂ SO ₄ . The crude product was purified by column chromatography using 20% ethyl acetate in hexane as eluent to give a colorless solid. Dioxane-HCl was added thereto at room temperature and stirred for 10 minutes, and the solid obtained was filtered and dried to give 3.O g (42.8%) of 5-bromoisoindolin hydrochloride salt as a gray solid.

Intermediate 21: 5- Bromo -3- (4- Piperidinyl ) -1H-indole-7- Carboxamide Hydrochloride

4 M solution of HCl in dioxane (194 mL) was added 1,1-dimethylethyl 4- [7- (aminocarbonyl) -5-bromo-1H-indol-3-yl]-in methanol (50 mL). To a solution of 1-piperidinecarboxylate (10 g, 23.7 mmol). The reaction mixture was stirred at rt for 4 h and the solvent was evaporated under reduced pressure to give the title compound (9.5 g), which was used without further purification in the next step.

LC-MS: m / z 322.4 (M + H), 1.40 min.

Intermediate 22: 5- Bromo -3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

Triethylamine (2.6 mL, 18.7 mmol) was added to a solution of 5-bromo-3- (4-piperidinyl) -1H-indole-7-carboxamide hydrochloride in DMF (15 mL) at 0 ° C. It was. The mixture was stirred at rt for 10 min and 2-propanesulfonyl chloride (1.04 mL, 9.32 mmol) was added. Then stirred for an additional 30 minutes, and the reaction mixture was diluted with 1: 1 EtOAc / H ₂ O (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with saturated NaCl (1 × 100 mL), dried (MgSO ₄ ) and concentrated under reduced pressure. The crude product was washed with MeOH (2 × 10 mL) to give the title compound (1.5 g, 75%).

LC / MS: m / z 427.8 (M + H), 1.98 min.

Intermediate 23: 5- (5- Formyl -3- Thienyl ) -3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

The boronate ester used to prepare the title compound was prepared in the same six separate batches according to the following procedure: 4-bromo-2-thiophencarbaldehyde (1.0 g, 4.48 mmol) in DME (20 mL). To a solution of bis (pinacolato) diborane (1.48 g, 5.82 mmol), KOAc (1.14 g, 5.11 mmol) and Pd ₂ Cl ₂ (dppf) (106 mg, 0.448 mmol) were added. The reaction was carried out at 150 DEG C for 20 minutes under Smith microwave. Six reactions were combined and concentrated under reduced pressure. The residue was taken up in EtOAc (200 mL) and H ₂ O (50 mL). The layers were separated and the organic layer was washed with saturated NaCl (1 × 50 mL), dried (Na ₂ SO ₄ ) and concentrated under reduced pressure. The crude product was purified by flash chromatography eluting with hexanes / EtOAc to afford 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-thiophenecar. Brothaldehyde (5 g, 78%) was provided.

5-bromo-3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide (428 mg, 1 mmol), 4- (4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2-thiophencarbaldehyde (960 mg, 4 mmol), Cs ₂ CO ₃ (800 mg, 2.46 mmol ), And a solution of Pd (PPh ₃ ) ₄ (100 mg, 0.0865 mmol) were heated at 160 ° C. for 20 minutes under Smith microwave. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was washed with MeOH (1 x 5 mL) to give the title compound (395 mg, 86%).

LC / MS: m / z 460.4 (M + H), 1.98 min.

<Example>

Example  1: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1- Piperidinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (15.0 mg, 0.034 mmol) in DCM (2 mL) To the solution of piperidine (4.0 ul, 0.04 mmol) was added. The reaction solution was stirred at ambient temperature for 1 hour and then NaBH (OAc) ₃ (23.0 mg, 0.109 mmol) was added. The resulting mixture was stirred overnight at ambient temperature, then the solvent was removed under reduced pressure. The resulting residue was dissolved in 1.2 mL of DMSO and all undissolved solids were filtered off. The DMSO solution of the crude product was purified by reverse phase HPLC (H ₂ O / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (8.8 mg, 50.5%).

LC / MS: m / z 509.4 (M + H), retention time: 1.87 minutes.

Example  2: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1- Piperazinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (15.0 mg, 0.034 mmol), piperazine (3.5 mg, 0.04 mmol) and NaBH (OAc) ₃ (23.0 mg, 0.102 mmol) were reacted to give the title compound (3.4 mg, 19.7%).

LC / MS: m / z 510.2 (M + H), retention time: 1.43 minutes.

Example  3: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (4- Morpholinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (15.0 mg, 0.034 mmol), morpholine (3.5 ul, 0.04 mmol) and NaBH (OAc) ₃ (23.0 mg, 0.102 mmol) were reacted to give the title compound (7.5 mg, 43%).

LC / MS: m / z 511.2 (M + H), retention time: 1.58 minutes.

Alternatively, Example 3 could be prepared as follows:

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (1.5 mL) and methanol (1.5 mL) To a solution of (20 mg, 0.046 mmol) was added morpholine (0.070 mL, 0.276 mmol) and 1 drop of acetic acid. The mixture was stirred at rt for 2 h and then sodium borohydride (11 mg, 0.276 mmol) was added. After 30 minutes the mixture was poured into an SCX cartridge (5.0 g) and the cartridge was flushed with EtOAc (10.0 mL) and MeOH (10.0 mL). The product was eluted with a 2 M solution of NH ₃ / MeOH (10.0 mL) and then concentrated. The residue was dissolved in dimethyl sulfoxide (1.0 mL) and purified by Gilson preparative HPLC to give the title compound (17.6 mg, 75%).

Example  4: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({methyl [2- ( Methylsulfonyl ) Ethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (42.0 mg, 0.096 mmol), N-methyl-2- (methylsulfonyl) ethanamine (12.0 mg, 0.087 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.261 mmol) were reacted to give the title compound (15.1 mg, 28.0%). Provided.

LC / MS: m / z 561.2 (M + H), retention time: 1.58 minutes.

Example  5: 5- (3-{[[2- (dimethylamino) ethyl] ( methyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (45.0 mg, 0.101 mmol) in DCM (2 mL) To the solution of was added N, N, N'-trimethyl-1,2-ethanediamine (116 ul, 0.90 mmol). The reaction solution was stirred at ambient temperature for 1 hour and then NaBH (OAc) ₃ (69 mg, 0.326 mmol) was added. The resulting mixture was stirred overnight at ambient temperature and additional NaBH (OAc) ₃ (128 mg, 0.606 mmol) was added. The reaction was stirred for a further 2 hours, after which the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (16.0 mg, 29.6%).

LC / MS: m / z 526.8 (M + H), retention time: 1.28 minutes.

Example  6: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3-[(4- {2-[(2- Hydroxyethyl ) Oxy ] Ethyl} -1- Piperazinyl ) methyl ] Phenyl } -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2-{[2- (1-piperazinyl) ethyl] oxy} ethanol (150 mg, 0.87 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted with the title compound (16.7 mg). , 25%).

LC / MS: m / z 598.4 (M + H), retention time: 1.48 minutes.

Example  7: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[3- ( Hydroxymethyl )-One- Piperidinyl ] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 3-piperidinylmethanol (98.9 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted to give the title compound (10.2 mg, 17%).

LC / MS: m / z 539.4 (M + H), retention time: 1.52 minutes.

Example  8: 5- [3-({bis [2- ( Methyloxy ) Ethyl] amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2- (methyloxy) -N- [2- (methyloxy) ethyl] ethanamine (114.3 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted with the title compound ( 10.5 mg, 16%).

LC / MS: m / z 557.6 (M + H), retention time: 1.62 minutes.

Example  9: 5- {3-[(2,6-dimethyl-4- Morpholinyl ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2,6-dimethylmorpholine (98.9 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted to give the title compound (19.6 mg, 32%).

LC / MS: m / z 539.2 (M + H), retention time: 1.75 minutes.

Example  10: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[2- (1,3-thiazol-2-yl) -1- Pyrrolidinyl ] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2- (2-pyrrolidinyl) -1,3-thiazole (132.4 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted with the title compound (20.0 mg, 30.4 %).

LC / MS: m / z 578.6 (M + H), retention time: 1.57 minutes.

Example  11: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[2- (2- Thienyl )-One- Pyrrolidinyl ]methyl} Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2- (2-thienyl) pyrrolidine (132.4 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted to give the title compound (20.0 mg, 30.4%). .

LC / MS: m / z 577.4 (M + H), retention time: 1.78 minutes.

Example  12: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2-hydroxy-2- Phenylethyl )-( methyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), 2- (methylamino) -1-phenylethanol (129.9 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted to give the title compound (22.1 mg, 36.6%). .

LC / MS: m / z 575.4 (M + H), retention time: 1.66 minutes.

Example  13: 5- (3-{[ethyl ( methyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50.0 mg, 0.112 mmol), N-methylethanamine (50.7 mg, 0.86 mmol) and NaBH (OAc) ₃ (58.0 mg, 0.303 mmol) were reacted to give the title compound (11.5 mg, 21%).

LC / MS: m / z 483.4 (M + H), retention time: 1.57 minutes.

Example  14: 5- [3- ( Aminomethyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7-carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30.0 mg, in dioxane / H ₂ O (2 mL / 0.7 mL) 0.072 mmol), Cs ₂ CO ₃ (95 mg, 0.290 mmol) and 1- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] Argon was bubbled into a solution of methanamine (82 mg, 0.350 mmol) for 5 minutes and then Pd (PPh ₃ ) ₄ (7.5 mg, 0.0072 mmol) was added. The reaction mixture was heated at 160 ° C. for 20 minutes in a microwave reactor (Smith Synthesizer). The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine (10 mL), dried over MgSO ₄ , filtered, concentrated and purified by reverse phase HPLC method A (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (2.7 mg). , 8.5%).

LC / MS: m / z 441.4 (M + H), retention time: 1.54 minutes.

Example  15: 5- {3-[( Cyclopentylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 5, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (45 mg, 0.101 mmol), cyclopentylamine (90 uL, 0.090 mmol) and NaBH (OAc) ₃ (197 mg, 0.93 mmol) were reacted to give the title compound (33.0 mg, 64%).

LC / MS: m / z 509.4 (M + H), retention time: 1.64 minutes.

Example  16: 5- [3-({[(3,4- Dihydroxyphenyl ) methyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol in dichloroethane (2 mL) To a solution of) 4- (aminomethyl) -1,2-benzenediol (12.1 mg, 0.087 mmol) was added. The reaction solution was stirred at ambient temperature for 10 minutes and then NaBH (OAc) ₃ (58 mg, 0.261 mmol) was added. The resulting mixture was shaken overnight at ambient temperature, after which the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (7.4 mg, 12%).

LC / MS: m / z 563.2 (M + H), retention time: 1.67 minutes.

Example  17: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(3- Thienylmethyl ) Amino] methyl } Phenyl) -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), 1- (3-thienyl) methanamine (9.83 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted to give the title compound (4.7 mg, 7.8%).

LC / MS: m / z 537.2 (M + H), retention time: 1.62 minutes.

Example  18: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(1R) -1- ( Hydroxymethyl )-2- Methylpropyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), (2R) -2-amino-3-methyl-1-butanol (10.2 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted with the title compound (14.9 mg, 25% ).

LC / MS: m / z 527.6 (M + H), retention time: 1.48 minutes.

Example  19: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2-hydroxy-1- Methylethyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), 2-amino-1-propanol (6.5 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted to give the title compound (3.4 mg, 6.0%).

LC / MS: m / z 499.6 (M + H), retention time: 1.46 minutes.

Example  20: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(trans-4- Hydroxycyclohexyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), trans-4-aminocyclohexanol (10 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted to give the title compound (6.0 mg, 9.8%).

LC / MS: m / z 539.2 (M + H), retention time: 1.54 minutes.

Example  21: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3-[({[1- (1- Piperidinyl ) Cyclohexyl ] methyl } Amino) methyl ] Phenyl } -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), 1- [1- (1-piperidinyl) cyclohexyl] methanamine (17 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted to give the title compound (18.7 mg , 27%).

LC / MS: m / z 620.6 (M + H), retention time: 1.6 minutes.

Example  22: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(2S) -2-hydroxypropyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 16, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), (2S) -1-amino-2-propanol (6.5 mg, 0.087 mmol) and NaBH (OAc) ₃ (58 mg, 0.261 mmol) were reacted to give the title compound (13.1 mg, 23%). .

LC / MS: m / z 499.6 (M + H), retention time: 1.46 minutes.

Example  23: 5- {3-[( Ethylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (0.5 mL) and methanol (0.5 mL) To a solution of (20 mg, 0.045 mmol) was added ethylamine (130 uL, 0.27 mmol). The mixture was stirred at rt for 1 h and then sodium borohydride (10 mg, 0.27 mmol) was added. The reaction was stirred at ambient temperature overnight and the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (13.2 mg, 63%).

LC / MS: m / z 469.4 (M + H), retention time: 1.54 min.

Example  24: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3-[( Propylamino ) methyl ] Phenyl } -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (0.7 mL) and methanol (0.7 mL) To a solution of (20 mg, 0.046 mmol) was added propylamine (22 uL, 0.27 mmol) and one drop of acetic acid. The mixture was stirred at rt for 1 h and then sodium borohydride (10 mg, 0.27 mmol) was added. The reaction was stirred at ambient temperature overnight and the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (22.1 mg, 99%).

LC / MS: m / z 483.2 (M + H), retention time: 1.58 minutes.

Example  25: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(1- Methylethyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

According to the general procedure of Example 24, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (20 mg, 0.045 mmol), isopropylamine (23 uL, 0.27 mmol) and NaBH ₄ (10 mg, 0.27 mmol) were reacted to give the title compound (11.5 mg, 53%).

LC / MS: m / z 483.2 (M + H), retention time: 1.52 minutes.

Example  26: 5- (3-{[(1-ethylpropyl) amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (20 mg, 0.045 mmol), 3-pentanamine (32 uL, 0.27 mmol) and NaBH ₄ (10 mg, 0.27 mmol) were reacted to give the title compound (18.5 mg, 80%).

LC / MS: m / z 511.4 (M + H), retention time: 1.66 minutes.

Example  27: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (1- Piperidinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (40 mg, 0.09 mmol), piperidine (0.009 mL, 0.09 mmol) and NaBH (OAc) ₃ (58 mg, 0.27 mmol) were reacted to give the title compound (8 mg, 17.5%).

LC / MS: m / z 509.4 (M + H), retention time: 1.71 minutes.

Example  28: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3-[( Methylamino ) methyl ] Phenyl } -1H-indole-7- Carboxamide

According to the general procedure of Example 24, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (20 mg, 0.045 mmol), methylamine (130 uL, 0.27 mmol) and NaBH ₄ (10 mg, 0.27 mmol) were reacted to give the title compound (17.0 mg, 83%).

LC / MS: m / z 455.2 (M + H), retention time: 1.48 minutes.

Example  29: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (4- Morpholinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol), morpholine (18 uL, 0.206 mmol) and NaBH (OAc) ₃ (290 mg, 1.37 mmol) were reacted to give the title compound (2.1 mg, 13%).

LC / MS: m / z 511.4 (M + H), retention time: 1.63 minutes.

Example  30: 5- [4- ( Aminomethyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7-carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30.0 mg, in dioxane / H ₂ O (1.5 mL / 0.5 mL) 0.072 mmol), argon was bubbled in a solution of Cs ₂ CO ₃ (95 mg, 0.290 mmol) and [4- (aminomethyl) phenyl] boronic acid (55 mg, 0.290 mmol) for 5 minutes, and then Pd (PPh ₃ ) ₄ (7.5 mg, 0.0072 mmol) was added. The reaction mixture was heated at 160 ° C. for 20 minutes in a microwave reactor (Smith Synthesizer). The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine (10 mL), dried over MgSO ₄ , filtered, concentrated and purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (9.8 mg, 31 %).

LC / MS: m / z 424.4 (M-NH 2), retention time: 1.48 minutes.

Example  31: 5- {3-[( Cyclopropylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.113 mmol) in DCM (2 mL) To the solution of cyclopropanamine (19.3 mg, 0.339 mmol) was added. The reaction solution was stirred for 30 min at ambient temperature, then HOAc (1 drop) and NaBH (OAc) ₃ (75 mg, 0.545 mmol) were added. The resulting mixture was stirred overnight at ambient temperature, then the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water / CH ₃ CN, 0.1% TFA 10-90%) to give the title compound (18.2 mg, 34%).

LC / MS: m / z 481.2 (M + H), retention time: 1.52 minutes.

Example  32: 5- {3-[( Cyclobutylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

According to the general procedure of Example 31, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.113 mmol), cyclobutanamine (24.1 mg, 0.339 mmol) and NaBH (OAc) ₃ (75 mg, 0.545 mmol) were reacted to give the title compound (19.3 mg, 35%).

LC / MS: m / z 495.6 (M + H), retention time: 1.55 minutes.

Example  33: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3-[(2- Methylpropyl ) Amino] -2,3-dihydro-1H- Inden -5-yl} -1 H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3.0 mL) and H ₂ O (1.0 mL) 6-bromo-2,3-dihydro-1H-indene-1- in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (200 mg, 0.434 mmol) Warm (274 mg, 1.30 mmol) and potassium carbonate (360 mg, 2.60 mmol) were added in a microwave tube. The reaction mixture was degassed for 5 minutes, then tetrakis (triphenylphosphine) palladium (0) (50 mg, 0.043 mmol) was added. The reaction was then heated at 160 ° C. for 30 minutes under microwave. The reaction was then filtered and the solid was dissolved in EtOAc and H ₂ O. The organic layer was separated and concentrated. The crude residue was purified by Gilson preparative HPLC to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-oxo-2,3-dihydro-1H-inden-5-yl ) -1H-indole-7-carboxamide was obtained.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-oxo-2,3-dihydro-1H-indene-5- in EtOH (2 mL) and acetic acid (200 μl) In a solution of yl) -1H-indole-7-carboxamide (45 mg, 0.097 mmol) 2-methyl-1-propanamine (170 μl, 1.93 mmol) and sodium cyanoborohydride (20 mg, 0.291 mmol ) Was added. The resulting mixture was reacted at 150 ° C. for 40 minutes in a CEM microwave tube. Purification by Gilson preparative HPLC gave 4.5 mg (8.9%) of the title compound.

LC / MS = m / z 523.4 [M + H] Retention time: 1.72.

Example  34: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {8-[(2- Methylpropyl ) Amino] -5,6,7,8-te T Lahydro-2- Naphthalenyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3.0 mL) and H ₂ O (1.0 mL) 7-bromo-3,4-dihydro-1 (2H) -naph in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (200 mg, 0.434 mmol) Talenone (292 mg, 1.30 mmol) and potassium carbonate (360 mg, 2.60 mmol) were added in a microwave tube. The reaction mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (50 mg, 0.043 mmol) was added. The reaction was then heated at 160 ° C. for 30 minutes under microwave. The reaction was then filtered and the solid was dissolved in EtOAc and H ₂ O. The organic layer was separated and concentrated. The crude residue was purified by Gilson preparative HPLC to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (8-oxo-5,6,7,8-tetrahydro-2-naph Tallenyl) -1H-indole-7-carboxamide was obtained.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (8-oxo-5,6,7,8-tetrahydro-2- in EtOH (2 mL) and acetic acid (0.2 mL) To a solution of naphthalenyl) -1H-indole-7-carboxamide (40 mg, 0.08 mmol) 2-methyl-1-propanamine (140 μl, 1.6 mmol) and sodium cyanoborohydride (15 mg, 0.24 mmol) was added. The resulting mixture was reacted at 150 ° C. for 40 minutes in a CEM microwave tube. Purification by Gilson preparative HPLC gave 3.2 mg (7.5%) of the title compound.

LC / MS = m / z 537.4 [M + H] Retention time: 1.71.

Example  35: 5- (5-{[(2- Cyanoethyl ) Amino] methyl }-2- Fluorophenyl ) -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3.0 mL) and H ₂ O (1.0 mL) 3-bromo-4-fluorobenzaldehyde (264 mg, 1.30 mmol) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (200 mg, 0.434 mmol) and K ₂ CO ₃ (360 mg, 2.60 mmol) was added in a microwave tube. The reaction mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (48 mg, 0.043 mmol) was added. The reaction was heated at 160 ° C. for 30 minutes under microwave. The organic layer was separated and concentrated. The residue was dissolved in MeOH until the solid precipitated, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-formylphenyl) -1H-indole- 7-carboxamide was obtained.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (2 mL) and methanol (1 mL) To a solution of 7-carboxamide (40 mg, 0.087 mmol) was added 3-aminopropanenitrile (53 μl, 0.524 mmol) and 1 drop of acetic acid. The reaction mixture was stirred at rt for 48 h. Sodium borohydride (20 mg, 0.524 mmol) was then added and reacted for 30 minutes at room temperature. Purification by Gilson preparative HPLC gave 14.4 mg (32.4%) of the title compound.

LC / MS = m / z 512.2 [M + H] Retention time: 1.45.

Example  36: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2- Fluoro -5-{[(2,2,2- T Rifluoroethyl) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (4 mL) and methanol (2 mL) To a solution of 7-carboxamide (20 mg, 0.04 mmol) was added 2 drops of acetic acid and 2,2,2-trifluoroethanamine (23 μl, 0.26 mmol). The resulting mixture was stirred overnight. All solvents were evaporated and dissolved in dimethyl sulfoxide (1 mL). Purification by Gilson preparative HPLC gave 5.2 mg (24.0%) of the title compound.

LC / MS = m / z 541.4 [M + H] Retention time: 1.67.

Example  37: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (1,2,3,4- Tetrahydro -7- this Soquinollinyl) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (1 mL) 7-bromo-1,2,3,4-tetrahydroisoquinoline (97 mg) in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol) , 0.39 mmol) and potassium carbonate (108 mg, 0.78 mmol) were added. The mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (15 mg, 0.013 mmol) was added. The resulting mixture was reacted at 160 ° C. for 30 minutes in a CEM microwave tube. The organic layer was separated and concentrated. The resulting residue was dissolved in dimethyl sulfoxide (1 mL) and purified by Gilson preparative HPLC to give 3.5 mg (5.7%) of the title compound.

LC / MS = m / z 467.2 [M + H] Retention time: 1.48.

Example  38: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2,2,2- Trifluoroethyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (200 mg) in dioxane (3.0 mL) and H ₂ O (1.0 mL) (3-formylphenyl) boronic acid (317 mg, 1.93 mmol) and Cs ₂ CO ₃ (315 mg, 0.97 mmol) were added to a solution of 0.483 mmol) in a microwave tube. The reaction mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (48 mg, 0.043 mmol) was added. The reaction was heated at 160 ° C. for 30 minutes under microwave. The organic layer was separated and concentrated. The residue was dissolved in MeOH until the solid precipitated, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide Obtained.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (2 mL) and methanol (1 mL) (40 mg, 0.09 mmol) and 2 drops of acetic acid were added to a solution of 2,2,2-trifluoroethylamine (78 μl, 0.55 mmol). The mixture was then stirred overnight. Then sodium borohydride (20.8 mg, 0.55 mmol) was added and the mixture was stirred for 30 minutes. The resulting mixture was concentrated and dissolved in dimethyl sulfoxide and then purified by Gilson preparative HPLC to give 29.4 mg (62.5%) of the title compound.

LC / MS = m / z 523.2 [M + H] Retention time: 1.66.

Example  39: 5- (3-{[(2-amino-2- Oxoethyl ) ( methyl ) Amino] methyl } Phenyl ) -3- [1- ( on Tilsulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (3 mL) and methanol (1.5 mL) To a solution of (44 mg, 0.1 mmol) and N ² -methylglycineamide (76 mg, 0.6 mmol) 3 drops of acetic acid were added. The mixture was stirred overnight. Sodium triacetoxyborohydride (134 mg, 0.6 mmol) was added and stirred overnight. The resulting reaction was quenched with sodium bicarbonate (2 mL) and brine (2 mL). The organic layer was then collected and concentrated. The resulting residue was then purified by Gilson preparative HPLC to give 13 mg (25.4%) of the title compound.

LC / MS = m / z 512.6 [M + H] Retention time: 1.20.

Example  40: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2-{[(2,2,2- On trifluoro Til) amino] methyl } -1,3-thiazol-4-yl) -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) acetic acid (3 drops) and 2,2,2-trifluoroethanamine (120 μl, 1.5 mmol) was added. The reaction was stirred overnight. Sodium triacetoxyborohydride (335 mg, 1.5 mmol) was then added and the reaction stirred for 6 hours. Then quenched with sodium bicarbonate to 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -Yl) -1H-indole-7-carboxamide was obtained.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) N-[(4-bromo-1,3-thiazol-2-yl) in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (46 mg, 0.1 mmol) Methyl] -2,2,2-trifluoroethanamine (30 mg, 0.11 mmol) and potassium carbonate (83 mg, 0.6 mmol) were added. The resulting mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (11 mg, 0.01 mmol) was added. The mixture was reacted at 160 ° C. for 20 minutes in a CEM microwave tube. The organic layer was separated and concentrated. The resulting residue was purified by Gilson preparative HPLC to give 25 mg (47.2%) of the title compound.

LC / MS = m / z 530.2 [M + H] Retention time: 1.94.

Example  41: 5- (3- Cyano -5-{[(2,2,2- Trifluoroethyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxa in dioxane (2.0 mL, 0.7 mL) 3-bromo-5-formylbenzonitrile (68 mg, 0.3 mmol) and K ₂ CO _{3 in} a solution of borola-2-yl) -1H-indole-7-carboxamide (46 mg, 0.1 mmol) (83 mg, 0.6 mmol) was added in a microwave tube. The reaction mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (11 mg, 0.01 mmol) was added. The reaction was heated at 160 ° C. for 20 minutes under microwave. Then purified by Gilson preparative HPLC to give 5- (3-cyano-5-formylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide Provided.

5- (3-cyano-5-formylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- in dichloromethane (3 mL) and methanol (1 mL) To a solution of 7-carboxamide (52 mg, 0.11 mmol) was added 20 drops of acetic acid and 2,2,2-trifluoroethanamine (53 μl, 0.66 mmol). The mixture was stirred for 48 hours, then sodium triacetoxyborohydride (140 mg, 0.66 mmol) was added. The mixture was then stirred for 48 hours. The resulting reaction was quenched with sodium bicarbonate and brine was added. The organic layer was separated and purified by Gilson preparative HPLC to give 3.6 mg (6.0%) of the title compound.

LC / MS = m / z 548.2 [M + H] Retention time: 1.88.

Example  42: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (1- methyl -4- Piperi Diyl) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (2 mL) ( To 50 mg, 0.11 mmol) was added N, 1-dimethyl-4-piperidinamine (128.22 mg, 1.0 mmol), 2 drops of acetic acid and reacted overnight. Sodium triacetoxyborohydride (212 mg, 1 mmol) was added and reacted overnight at room temperature. Purification by Gilson preparative HPLC gave 8 mg (13.0%) of the title compound.

LC / MS = m / z 558.4 [M + H] Retention time: 1.32 minutes.

Example  43: 5- (5-{[(2- Cyanoethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N, 1-dimethyl-4-piperidinamine in place of 3- (methylamino) propanenitrile (84.12 mg, 1.0 mmol), and the title compound is 3- [1- (ethylsulfonyl) -4-piperidi General procedure for Nyl] -5- (5-{[methyl (1-methyl-4-piperidinyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide triple fluoroacetate Prepared according to yield 24 mg (42.5%) of the title compound.

LC / MS = m / z 514.4 [M + H] Retention time: 1.55 minutes.

Example  44: 5- (5-{[(2-amino-2- Oxoethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (ethylsulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N, 1-dimethyl-4-piperidinamine in place of N ² -methylglycinamide (88.11 mg, 1.0 mmol), and the title compound is 3- [1- (ethylsulfonyl) -4-piperidinyl] According to the general procedure for -5- (5-{[methyl (1-methyl-4-piperidinyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate To give 19 mg (33.3%) of the title compound.

LC / MS = m / z 518.2 [M + H] Retention time: 1.43 minutes.

Example  45: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({methyl [2- ( Phenylsulfonyl ) Ethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the N, 1-dimethyl-4-piperidinamine with N-methyl-2- (phenylsulfonyl) ethanamine (199.27 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methyl-4-piperidinyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoro Prepared according to the general procedure for acetate to give 30 mg (47.3%) of the title compound.

LC / MS = m / z 629.4 [M + H] Retention time: 1.57 minutes.

Example  46: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(2- Phenyl -One- Pyrrolidinyl ) methyl ] -3-T on Nil} -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.11 mmol), was added 2-phenylpyrrolidine (147 mg, 1.0 mmol). The reaction mixture was then reacted at 120 ° C. for 10 minutes under microwave. Then sodium triacetoxyborohydride (220 mg, 1.0 mmol) was added and the reaction was allowed to react overnight at room temperature. Purification by Gilson preparative HPLC gave 14.0 mg (22%) of the title compound.

LC / MS = m / z 577.2 [M + H] Retention time: 1.65 minutes.

Example  47: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[2- (1- Piperidinylmethyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace the 2-phenylpyrrolidine with 1- (2-pyrrolidinylmethyl) piperidine (168.3 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl ] -5- {5-[(2-phenyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide prepared according to the general procedure for 21 mg of the title compound ( 32%) was obtained.

LC / MS = m / z 598.4 [M + H] Retention time: 1.34.

Example  48: 5- (5-{[(2R) -2- ( Aminocarbonyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- [1- (in Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2-phenylpyrrolidine with D-prolineamide (114 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[( Prepared according to the general procedure for 2-phenyl-1-pyrrolidinyl) methyl] -3-thienyl} -1 H-indole-7-carboxamide to give 14 mg (23%) of the title compound.

LC / MS = m / z 544.2 [M + H] Retention time: 1.39.

Example  49: 5- (5-{[(3S) -3- (dimethylamino) -1- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2-phenylpyrrolidine with (2R) -N, N-dimethyl-2-pyrrolidineamine (114 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4- The title compound prepared according to the general procedure for piperidinyl] -5- {5-[(2-phenyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide 11 mg (18%) were obtained.

LC / MS = m / z 544.2 [M + H] Retention time: 1.36.

Example  50: 5- (1- {2- [4- (dimethylamino) -1- Piperidinyl ] Ethyl} -1H- Pyrazole -4-yl) -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (750 μl) and H ₂ O (250 μl) Sodium carbonate (53 mg, 0.50 mmol) and 4-bromo-1- (2) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (40 mg, 0.090 mmol) -Chloroethyl) -1H-pyrazole (26 mg, 0.126 mmol) was added. The reaction mixture was flushed under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) was added. The reaction was heated at 120 ° C. for 20 minutes under microwave. It was then diluted with EtOAc (10 mL), filtered through celite and then aqueous work up. The compound was purified by Gilson preparative HPLC to give 5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H 10 mg (24%) of indole-7-carboxamide was provided.

5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- in tetrahydrofuran (500 uL) To a solution of indole-7-carboxamide (33 mg, 0.071 mmol) was added N, N-dimethyl-4-piperidinamine (100 μl, 0.71 mmol) and sodium iodide (5 mg, 0.018 mmol). The resulting mixture was reacted in a microwave tube at 130 ° C. for 2 hours. Aqueous washing with EtOAc and water, organic layer was isolated and all solvent was removed. It was then purified by Gilson preparative HPLC to give 7.0 mg (14.7%) of the title compound.

LC / MS = m / z 556 [M + H] Retention time: 1.23 minutes.

Example  51: 5- [3-[(dimethylamino) methyl ] -4,5-bis ( Methyloxy ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (9.0 mL) and H ₂ O (3.0 mL) Sodium carbonate (690 mg, 6.51 mmol) and 5-bromo-2,3- in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (500 mg, 1.09 mmol) Bis (methyloxy) benzaldehyde (7.95 mg, 3.25 mmol) was added. The reaction mixture was flushed under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (63 mg, 0.054 mmol) was added. The reaction was then heated at 120 ° C. for 30 minutes under microwave. All solvents were then concentrated and washed with EtOAc and H ₂ O. The desired compound is then precipitated and filtered to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4,5-bis (methyloxy) phenyl] -1H 322 mg (59%) of indole-7-carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4,5-bis (methyloxy) phenyl] -1H-indole-7- in methanol (2 mL) To a solution of carboxamide (30 mg, 0.06 mmol) was added zinc chloride (5 mg, 0.03 mmol), sodium cyanoborohydride (5 mg, 0.06 mmol) and dimethylamine (100 μl, 0.30 mmol). The mixture was stirred at room temperature for 2 hours and then reacted at 100 ° C. for 30 minutes under microwave. The resulting mixture was purified by Gilson preparative HPLC to give 11 mg (34.7%) of the title compound.

LC / MS = m / z 529 [M + H] Retention time: 1.67 minutes.

Example  52: 5- [3,4- Vis ( Methyloxy ) -5- (4- Morpholinylmethyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace the dimethylamine with morpholine (20 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [1- ( Prepared according to the general procedure for ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 8.0 mg (23.4%) of the title compound.

LC / MS = m / z 571 [M + H] Retention time: 1.59 minutes.

Example  53: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-{[(1- Methylethyl ) Amino] methyl } -4,5-bis ( Methyloxy ) Phenyl ] -1H-indole-7- Carboxamide

Replace the dimethylamine with 2-propanamine (20 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [1 Prepared according to the general procedure for-(ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 15 mg (46.1%) of the title compound.

LC / MS = m / z 543 [M + H] Retention time: 1.59 minutes.

Example  54: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-{[(1- Methylethyl ) Amino] methyl } -4,5-bis ( Methyloxy ) Phenyl ] -1H-indole-7- Carboxamide

Replace the dimethylamine with 40% by weight methylamine (50 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 6 mg (19.4%) of the title compound.

LC / MS = m / z 515 [M + H] Retention time: 1.46 minutes.

Example  55: 5- [3-{[(2,2-dimethylpropyl) amino] methyl } -4,5-bis ( Methyloxy ) Phenyl ] -3- [1- (on Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the dimethylamine with (2,2-dimethylpropyl) amine (20 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to afford 10 mg (29.2%) of the title compound.

LC / MS = m / z 571 [M + H] Retention time: 1.75 minutes.

Example  56: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-{[(2- Hydroxyethyl ) ( methyl ) Amino] methyl } -4,5-bis ( Methyloxy ) Phenyl ] -1H-indole-7- Carboxamide

Replace the dimethylamine with 2- (methylamino) ethanol (20 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3 Prepared according to the general procedure for-[1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to afford 10 mg (29.8%) of the title compound.

LC / MS = m / z 559 [M + H] Retention time: 1.54 minutes.

Example  57: 5- [3,4- Vis ( Methyloxy ) -5- (1- Pyrrolidinylmethyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace the dimethylamine with pyrrolidine (50 μl, 0.30 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [1- Prepared according to the general procedure for (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 13 mg (39.1%) of the title compound.

LC / MS = m / z 555 [M + H] Retention time: 1.61 minutes.

Example  58: 5- {4-[(dimethylamino) methyl ] -2,3- Dehydro -One- Benzofuran -6-yl} -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (113 mg) in dioxane (9.0 mL) and H ₂ O (3.0 mL) , 0.274 mmol) sodium carbonate (174 mg, 1.64 mmol) and 6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -2,3- Dihydro-1-benzofuran-4-carbaldehyde (150 mg, 0.547 mmol) was added. The reaction mixture was flushed under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (16 mg, 0.014 mmol) was added. The reaction was heated at 120 ° C. for 30 minutes under microwave. All solvents were then concentrated and purified by flash chromatography using DCM and MeOH to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formyl-2,3-dihydro 120 mg (91%) of 1-benzofuran-6-yl) -1H-indole-7-carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formyl-2,3-dihydro-1-benzofuran-6-yl) -1H in methanol (2 mL) In a solution of indole-7-carboxamide (20 mg, 0.042 mmol), dimethylamine (3 μl, 0.050 mmol), zinc chloride (3 mg, 0.021 mmol) and sodium cyanoborohydride (4 mg, 0.062 mmol) ) Was added. The mixture was reacted under microwave at 100 ° C. for 1 hour and then all solvents were removed. The residue was washed with EtOAc and water. All solvents were removed and purified by Gilson preparative HPLC to give 6.0 mg (19.6%) of the title compound.

LC / MS = m / z 525 [M + H] Retention time: 1.56 minutes.

Example  59: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(1- Methylethyl ) Amino] methyl } -2,3-D He Draw-1- Benzofuran -6-yl) -1H-indole-7- Carboxamide

Replace the dimethylamine with 2-propanamine (3 mg, 0.050 mmol) and replace the title compound with 5- {4-[(dimethylamino) methyl] -2,3-dihydro-1-benzofuran-6-yl} Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 9.0 mg (28.6%) of the title compound.

LC / MS = m / z 511 [M + H] Retention time: 1.58 minutes.

Example  60: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (4- Morpholinylmethyl ) -2,3- Dehydro -One- Benzofuran -6-yl] -1H-indole-7- Carboxamide

Replace the dimethylamine with 2,2-dimethyl-1-propanamine (4 mg, 0.050 mmol) and replace the title compound with 5- {4-[(dimethylamino) methyl] -2,3-dihydro-1-benzo 8.0 mg (24.1%) of the title compound prepared according to the general procedure for furan-6-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide Obtained.

LC / MS = m / z 554 [M + H] Retention time: 1.71 minutes.

Example  61: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[1- methyl -2-( Methyloxy ) Ethyl] amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

[5-({[1-methyl-2- (methyloxy) ethyl] amino} methyl) -2-thienyl] boronic acid (60 mg, 0.262 mmol) was transferred to a CEM microwave tube containing methanol. Metonol was evaporated under N ₂ stream. Here 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (80 mg, 0.19 mmol), potassium carbonate (160 mg, 1.16 mmol ), Tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol), dioxane (1.5 mL), and water (0.5 mL) were added. The vial was capped and reacted at 150 ° C. for 30 minutes under CEM microwaves. This solution was loaded into a 2 g SCX SPE cartridge primed with 3 mL of methanol. The cartridge was then eluted sequentially with water (3 mL), methanol (9 mL), and 2 M NH ₃ (6 mL) in MeOH. The NH ₃ fraction in MeOH was dried at 40 ° C. under N ₂ stream. The crude product was dissolved in dimethyl sulfoxide (1 mL), purified on Agilent MDAP and UV (230 nm) and MS detection. The desired fractions were passed through two successive 500 mg Pharmasil CHQAX cartridges primed with 1 mL methanol and 1 mL water. The solvent was evaporated at 60 ° C. under a stream of N ₂ to give 34.7 mg (34%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.32 minutes.

Example  62: 5- (5-{[(2- Cyanoethyl ) Amino] methyl } -3- Pyridinyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

5- (bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.072 mmol) in 3-({[5- (4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amino) propanenitrile (24.8 mg, 0.086 mmol) was added. To this mixture was added dioxane (0.75 mL), followed by a solution of potassium carbonate (60 mg, 0.434 mmol) and SK-CC02-A (4.4 mg, 0.007 mmol) in water (0.25 mL). The vial was capped and reacted at 150 ° C. for 30 minutes under CEM microwaves. The reaction was loaded into a 2 g SCX SPE cartridge primed with 3 mL of methanol. The cartridge was then eluted sequentially with water (3 mL), methanol (9 mL), and 2 M NH ₃ (6 mL) in MeOH. The NH ₃ fraction in MeOH was dried at 40 ° C. under N ₂ stream. The crude product was purified on Agilent MDAP and UV (230 nm) and MS detected. The desired fractions were passed through a 5 g CHQAX cartridge primed with 4 mL methanol and 4 mL water. The solvent was evaporated at 65 ° C. under a stream of N ₂ to give 6.2 mg (17.4%) of the title compound.

LC / MS = m / z 495 [M + H] Retention time: 1.29 minutes.

Example  63: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2,2,2- Trifluoroethyl ) Amino] methyl } -3- Pyridinyl ) -1H-indole-7- Carboxamide

3-({[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amino) propanenitrile 2,2 , 2-trifluoro-N-{[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} ethanamine (24.3 mg, 0.077 mmol) instead of the title compound 5- (5-{[(2-cyanoethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl)- Prepared according to the general procedure for 4-piperidinyl] -1H-indole-7-carboxamide to give 8.3 mg (22.0%) of the title compound.

LC / MS = m / z 524 [M + H] Retention time: 1.55 minutes.

Example  64: 5- {3-[(dimethylamino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (45 mg, 0.10 mmol) in DMSO (2 mL) To a solution of 2 M dimethylamine (500 μl, 1.0 mmol) in THF was added. The reaction mixture was stirred at rt for 5 h, then sodium triacetoxyborohydride (220 mg, 1.04 mmol) was added. The reaction was then stirred overnight. The compound was purified by Gilson preparative HPLC to give 9.0 mg (19.2%) of the title compound.

LC / MS = m / z 469 [M + H] Retention time: 1.55 minutes.

Example  65: 5- (5-{[ethyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (2 mL) ( To a solution of 50 mg, 0.11 mmol) was added N-methylethanamine (59.1 mg, 1.0 mmol), 2 drops of acetic acid and reacted overnight. Sodium triacetoxyborohydride (212 mg, 1 mmol) was added and reacted overnight at room temperature. Purification by Gilson preparative HPLC gave 20.0 mg (33.2%) of the title compound.

LC / MS = m / z 489 [M + H] Retention time: 1.50 minutes.

Example  66: 5- (5-{[[2- ( Diethylamino )ethyl]( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced with N, N-diethyl-N'-methyl-1,2-ethanediamine (130 mg, 1.0 mmol) and the title compound was replaced with 5- (5-{[ethyl (methyl) amino ] Methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure 30.0 mg (44.5%) were obtained.

LC / MS = m / z 560 [M + H] Retention time: 1.41 minutes.

Example  67: 5- (5-{[butyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced with butyl (methyl) amine (87 mg, 1.0 mmol) and the title compound was replaced with 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 10 mg (15.8%) of the title compound.

LC / MS = m / z 517 [M + H] Retention time: 1.61 minutes.

Example  68: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (propyl) amino] Me Tyl} -3-thienyl) -1H-indole-7- Carboxamide Trifluoroacetate

The title compound was replaced with 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [replacing N-methylethanamine with methyl (propyl) amine (73 mg, 1.0 mmol). Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 20.0 mg (32.4%) of the title compound.

LC / MS = m / z 503 [M + H] Retention time: 1.54 minutes.

Example  69: 5- (5-{[[2- (dimethylamino) ethyl] ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (ethylsulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced by [2- (dimethylamino) ethyl] methylamine (102 mg, 1.0 mmol) and the title compound was 5- (5-{[ethyl (methyl) amino] methyl} -3-thier. Yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 26.0 mg (40.3%) of the title compound Obtained.

LC / MS = m / z 532 [M + H] Retention time: 1.48 minutes.

Example  70: 5- (5-{[[3- (dimethylamino) propyl] ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (in Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced by [3- (dimethylamino) propyl] methylamine (116 mg, 1.0 mmol) and the title compound was 5- (5-{[ethyl (methyl) amino] methyl} -3-thier. Yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 21.0 mg (31.8%) of the title compound Obtained.

LC / MS = m / z 546 [M + H] Retention time: 1.49 minutes.

Example  71: 5- (5-{[cyclopentyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethyl sulfo Nil) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

Replace N-methylethanamine with cyclopentyl (methyl) amine (99 mg, 1.0 mmol), and substitute the title compound 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- Prepared according to the general procedure for [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 5.0 mg (7.78%) of the title compound.

LC / MS = m / z 529 [M + H] Retention time: 1.65 minutes.

Example  72: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl ( Pentyl ) Amino] Me Teal} -3- tea Enyl) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced with methyl (pentyl) amine (101 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 19.0 mg (29.5%) of the title compound.

LC / MS = m / z 531 [M + H] Retention time: 161 minutes.

Example  73: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (2- Methylpropyl ) Amino] Me Teal} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace title compound with 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl)-by replacing N-methylethanamine with methyl (2-methylpropyl) amine (87 mg, 1.0 mmol). Prepared according to the general procedure for 3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 3.0 mg (4.8%) of the title compound. .

LC / MS = m / z 517 [M + H] Retention time: 1.61 minutes.

Example  74: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl ( Phenylmethyl ) Amino] methyl} -3-ti on Nil) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced by methyl (phenylmethyl) amine (121 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- Prepared according to the general procedure for [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 15 mg (22.6%) of the title compound.

LC / MS = m / z 551 [M + H] Retention time: 1.67 minutes.

Example  75: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Hydroxyethyl ) ( Me Til) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced by 2- (methylamino) ethanol (75 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3 Prepared according to the general procedure for-[1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 27.0 mg (43.6%) of the title compound.

LC / MS = m / z 505 [M + H] Retention time: 1.46 minutes.

Example  76: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({methyl [2- (2- Pyridinyl ) Ethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced with methyl [2- (2-pyridinyl) ethyl] amine (75 mg, 1.0 mmol) and the title compound was 5- (5-{[ethyl (methyl) amino] methyl} -3 5.0 mg (7.36) of the title compound prepared according to the general procedure for -thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate %) Was obtained.

LC / MS = m / z 566 [M + H] Retention time: 1.59 minutes.

Example  77: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Furanylmethyl ) ( methyl ) Amino] methyl} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine instead of 1- (2-furanyl) -N-methylmethanamine (111 mg, 1.0 mmol) to give the title compound 5- (5-{[ethyl (methyl) amino] methyl} 19.0 mg of the title compound, prepared according to the general procedure for -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate (29.0%) was obtained.

LC / MS = m / z 541 [M + H] Retention time: 1.59 minutes.

Example  78: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (4- Pyridinylmethyl ) Amino] methyl} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced with methyl (4-pyridinylmethyl) amine (122 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl). Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 31.0 mg (46.6%) of the title compound. It was.

LC / MS = m / z 552 [M + H] Retention time: 1.37 minutes.

Example  79: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(methyl {[1- (1- Methylethyl ) -3-p role Ridinil] methyl } Amino) methyl ] -3- Thienyl } -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced with methyl {[1- (1-methylethyl) -3-pyrrolidinyl] methyl} amine (156 mg, 1.0 mmol) and the title compound was replaced with 5- (5-{[ethyl ( Methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate according to the general procedure To give 21.0 mg (30.0%) of the title compound.

LC / MS = m / z 586 [M + H] Retention time: 1.43 minutes.

Example  80: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (2- Thienylmethyl ) Amino] Me Teal} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced by methyl (2-thienylmethyl) amine (127 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl). Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 26.0 mg (38.8%) of the title compound. It was.

LC / MS = m / z 557 [M + H] Retention time: 1.72 minutes.

Example  81: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({methyl [1- (2- Thienyl ) Ethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the N-methylethanamine with methyl [1- (2-thienyl) ethyl] amine (141 mg, 1.0 mmol) and replace the title compound with 5- (5-{[ethyl (methyl) amino] methyl} -3 6.0 mg (8.76) of the title compound prepared according to the general procedure for -thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate %) Was obtained.

LC / MS = m / z 571 [M + H] Retention time: 1.78 minutes.

Example  82: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (3- Thienylmethyl ) Amino] Me Teal} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced by methyl (3-thienylmethyl) amine (127 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl). Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to afford 7.0 mg (10.4%) of the title compound. It was.

LC / MS = m / z 557 [M + H] Retention time: 1.78 minutes.

Example  83: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl ( Tetrahydro -2H-pyran-4-yl Me Til) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine was replaced with methyl (tetrahydro-2H-pyran-4-ylmethyl) amine (129 mg, 1.0 mmol) and the title compound was 5- (5-{[ethyl (methyl) amino] methyl}. 11.0 mg of the title compound, prepared according to the general procedure for 3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate (16.4%) was obtained.

LC / MS = m / z 559 [M + H] Retention time: 1.63 minutes.

Example  84: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (3- Pyridinylmethyl ) Amino] methyl} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced with methyl (3-pyridinylmethyl) amine (122 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl). Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 9.5 mg (14.3%) of the title compound. It was.

LC / MS = m / z 552 [M + H] Retention time: 1.56 minutes.

Example  85: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (4- Pyrimidinylme Til) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-methylethanamine is replaced with methyl (4-pyrimidinylmethyl) amine (123 mg, 1.0 mmol), and the title compound is 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl Prepared according to the general procedure for) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 4.0 mg (6.0%) of the title compound. Obtained.

LC / MS = m / z 555 [M + H] Retention time: 1.65 minutes.

Example  86: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({methyl [2- ( Methyloxy ) Ethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (5 mL) ( To a solution of 884 mg, 1.98 mmol) methyl [2- (methyloxy) ethyl] amine (1.86 g, 21 mmol) and HOAc (2 mL, 35 mmol) were added. The reaction was stirred at rt overnight and sodium triacetoxyborohydride (212 mg, 1 mmol) was added. Stirring continued for 1 hour, and CHCl ₃ (50 mL) was added. The mixture was filtered, CHCl ₃ was concentrated under reduced pressure and the crude product / DMSO solution was purified by Gilson preparative HPLC to give the title compound (590 mg, 47%).

LC / MS = m / z 519 [M + H] Retention time: 1.50 minutes.

Example  87: 5- {3-[(dimethylamino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (45 mg, 0.1 mmol) in DMSO (2 mL) To a solution of 2 M methylamine (500 μl, 1.0 mmol) in THF was added and stirred at room temperature for 5 hours. To the mixture was then added sodium triacetoxyborohydride (220 mg, 1.0 mmol) and stirred overnight. Purification by Gilson preparative HPLC gave 9.0 mg (15.4%) of the title compound.

LC / MS = m / z 469 [M + H] Retention time: 1.55 minutes

Example  88: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (1- Methylethyl ) Amino] Me Teal} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (46.0 mg in DMSO (2.0 mL) , 0.1 mmol) was added N-methyl-2-propanamine (73.1 mg, 1.0 mmol). The reaction mixture was then reacted at 160 ° C. for 10 minutes under microwave. Then sodium triacetoxyborohydride (220 mg, 1.0 mmol) was added and the reaction was reacted overnight at room temperature. Purification by Gilson preparative HPLC gave 24.0 mg (44.2%) of the title compound.

LC / MS = m / z 543 [M + H] Retention time: 1.70 minutes.

Example  89: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(2-propyl-1- Pyrrolidinyl ) methyl ] -3- Thienyl } -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.11 mmol) was added 2-propylpyrrolidine (113 mg, 1.0 mmol). The reaction mixture was then reacted at 120 ° C. for 10 minutes under microwave. Then sodium triacetoxyborohydride (220 mg, 1.0 mmol) was added and the reaction was reacted overnight at room temperature. Purification by Gilson preparative HPLC gave 21.0 mg (38.7%) of the title compound.

LC / MS = m / z 543 [M + H] Retention time: 1.70 minutes.

Example  90: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[2- (3- Pyridinyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace the 2-propylpyrrolidine with 3- (2-pyrrolidinyl) pyridine (148 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5 13.0 mg (22.5%) of the title compound, prepared according to the general procedure for-{5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide Obtained.

LC / MS = m / z 578 [M + H] Retention time: 1.52 minutes.

Example  91: 5- (5-{[2- (1,1-dimethylethyl) -1- Pyrrolidinyl ] methyl } -3- Thiethyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-propylpyrrolidine with 2- (1,1-dimethylethyl) pyrrolidine (127 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl ] -5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide prepared according to the general procedure for 11.0 mg ( 16.4%) was obtained.

LC / MS = m / z 557 [M + H] Retention time: 1.65 minutes.

Example  92: 5- {5-[(2-ethyl-1- Pyrrolidinyl ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace 2-propylpyrrolidine with 2-ethylpyrrolidine (99.0 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- Prepared according to the general procedure for [(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide to give 15.0 mg (28.4%) of the title compound.

LC / MS = m / z 529 [M + H] Retention time: 1.66 minutes.

Example  93: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[2- (2- Methylpropyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-propylpyrrolidine with 2- (2-methylpropyl) pyrrolidine (127 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl]- 7.0 mg (10.4% of the title compound), prepared according to the general procedure for 5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide ) Was obtained.

LC / MS = m / z 557 [M + H] Retention time: 1.74 minutes.

Example  94: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[2- (1- Methylethyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace the 2-propylpyrrolidine with 2- (1-methylethyl) pyrrolidine (113 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl]- 16.0 mg (29.5%) of the title compound prepared according to the general procedure for 5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide ) Was obtained.

LC / MS = m / z 543 [M + H] Retention time: 1.61 minutes.

Example  95: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({(2S) -2-[( Methyloxy ) methyl ] -1-pyrrolidinyl} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide

Replace 2-propylpyrrolidine with (2S) -2-[(methyloxy) methyl] pyrrolidine (115 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4- The title compound prepared according to the general procedure for piperidinyl] -5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide 22.0 mg (40.4%) were obtained.

LC / MS = m / z 544 [M + H] Retention time: 1.44 minutes.

Example  96: 5- (5-{[cyclohexyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

Replace 2-propylpyrrolidine with cyclohexyl (methyl) amine (113 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- Prepared according to the general procedure for [(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide to give 15.0 mg (27.6%) of the title compound.

LC / MS = m / z 543 [M + H] Retention time: 1.64 minutes.

Example  97: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[2- (2- Methylpropyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace the 2-propylpyrrolidine with 2- (2-methylpropyl) pyrrolidine (127 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl]- 12.0 mg (21.6%) of the title compound prepared according to the general procedure for 5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7-carboxamide ) Was obtained.

LC / MS = m / z 557 [M + H] Retention time: 1.74 minutes.

Example  98: 5- (5-{[ethyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.11 mmol) was added 2 drops of acetic acid, ethyl (methyl) amine (59 mg, 1.0 mmol) and stirred at room temperature for 5 hours. Then sodium triacetoxyborohydride (212 mg, 1.0 mmol) was added thereto and reacted overnight. Purification by Gilson preparative HPLC gave 30.0 mg (61.4%) of the title compound.

LC / MS = m / z 489 [M + H] Retention time: 1.50 minutes.

Example  99: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (propyl) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace the 2-propylpyrrolidine with methyl (propyl) amine (73 mg, 1.0 mmol) and replace the title compound with 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- Prepared according to the general procedure for [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide to give 32.0 mg (63.7%) of the title compound.

LC / MS = m / z 503 [M + H] Retention time: 1.54 minutes.

Example  100: 3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -5- (5-{[methyl (propyl) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

5- (5-formyl-3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-car in DMSO (2.0 mL) To a solution of voxamide (46 mg, 0.10 mmol) was added 2 drops of acetic acid, methyl (propyl) amine (73 mg, 1.0 mmol) and stirred at room temperature for 5 hours. Then sodium triacetoxyborohydride (212 mg, 1.0 mmol) was added thereto and reacted overnight. Purification by Gilson preparative HPLC gave 25.0 mg (39.6%) of the title compound.

LC / MS = m / z 517 [M + H] Retention time: 1.61 minutes.

Example  101: 5- (5-{[ethyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

Replace the methyl (propyl) amine with ethyl (methyl) amine (59 mg, 1.0 mmol) and replace the title compound with 3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -5- 8.0 mg (15.9%) of the title compound prepared according to the general procedure for (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate Obtained.

LC / MS = m / z 503 [M + H] Retention time: 1.59 minutes.

Example  102: 3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -5- [5-({methyl [2- ( Methyloxy ) Ethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide

Replace the methyl (propyl) amine with methyl [2- (methyloxy) ethyl] amine (89 mg, 1.0 mmol) and replace the title compound with 3- {1-[(1-methylethyl) sulfonyl] -4-pipe Prepared according to the general procedure for lidinyl} -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate to give the title compound 37.0 mg (69.4%) was obtained.

LC / MS = m / z 533 [M + H] Retention time: 1.58 minutes.

Example  103: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Methylamino ) methyl ]-2- Thienyl } -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-2-thienyl) -1H-indole-7-carboxamide (35 mg in DMSO (1.0 mL) , 0.078 mmol) was added acetic acid (3 drops), 2M methylamine (0.24 mL, 0.471 mmol) in THF, and reacted for 3 hours. Sodium triacetoxyborohydride (100 mg, 0.471 mmol) was added and the reaction stirred overnight. All solvents were removed in vacuo and purified by Gilson preparative HPLC. The non-pure desired fractions were concentrated under reduced pressure and loaded into a 500 mg SCX SPE cartridge primed with 10 mL of methanol. The cartridge was then eluted sequentially with 2 M NH ₃ (10 mL × 2) in MeOH. The NH ₃ fractions in MeOH were concentrated to give 7.3 mg (20%) of the title compound.

LC / MS = m / z 459.6 [M + H] Retention time: 1.25 minutes.

Example  104: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(2- methyl -One- Pyrrolidinyl ) Methyl] -3-T on Nil} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-2-thienyl) -1H-indole-7-carboxamide (50 mg) in DMSO (3.0 mL) , 0.112 mmol) was added acetic acid (3 drops), 2-methylpyrrolidine (0.12 mL, 1.12 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (238 mg, 1.12 mmol) was then added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 17 mg (30%) of the title compound.

LCMS: 515.4 (M + H), retention time: 1.60 minutes.

Example  105: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Methylpropyl ) Amino] Me Teal} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (4 drops), (2-methylpropyl) amine (0.17 mL, 1.68 mmol), and sodium triacetoxyborohydride (356 mg, 1.68 mmol) was reacted. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 15 mg (27%) of the title compound.

LCMS: 503.4 (M + H), retention time: 1.60 minutes.

Example  106: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Propylamino ) methyl ] -3- Thienyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops), (2-methylpropyl) amine (0.17 mL, 1.68 mmol) and sodium triacetoxyborohydride (356 mg, 1.68 mmol) was reacted. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 15 mg (27%) of the title compound.

LCMS: 489 (M + H), retention time: 1.61 minutes.

Example  107: 5- {5-[( Diethylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) To a solution of, 0.11 mmol) was added acetic acid (3 drops), diethylamine (0.12 mL, 1.12 mmol) and stirred at rt for 4 h. Sodium triacetoxyborohydride (238 mg, 1.12 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 7.0 mg (13%) of the title compound.

LCMS: 501.4 (M + H), retention time: 1.51 minutes.

Example  108: 5- (5-{[(2R, 5R) -2,5-dimethyl-1- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops), (2R, 5R) -2,5-dimethylpyrrolidine (151 mg, 1.123 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 27 mg (46%) of the title compound.

LCMS: 529.4 (M + H), retention time: 1.64 min.

Example  109: 5- {5-[( Cyclopropylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.11 mmol) was added acetic acid (5 drops) and cyclopropylamine (0.12 mL, 1.68 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (356 mg, 1.68 mmol) was then added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 8.0 mg (10%) of the title compound.

LCMS: 487.2 (M + H), Retention times: 1.64 minutes and 1.68 minutes.

Example  110: 5- {5-[( Cyclobutylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl ) -4-p Fe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg) in DMSO (2.0 mL) , 0.11 mmol) was added acetic acid (4 drops) and cyclobutylamine (0.15 mL, 1.68 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (356 mg, 1.68 mmol) was then added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (10%) of the title compound.

LCMS: 501.4 (M + H), retention time: 1.51 minutes.

Example  111: 5- {5-[(dimethylamino) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formyl-2-thienyl) -1H-indole-7-carboxamide (300 mg in DMSO (4 mL) , 0.67 mmol) was added a solution of 2M dimethylamine (3.36 mL, 6.7 mmol) in THF. The reaction was stirred at rt for 7 h and sodium triacetoxyborohydride (1.42 g, 6.7 mmol) was added. Stirring was continued overnight at room temperature. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give the title compound (205 mg, 64%).

LCMS: 475.2 (M + H), retention time: 1.51 minutes.

Example  112: 5- (5-{[( Cyclopentylmethyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethyl alcohol Ponyl) -4-P Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops) and (cyclopentylmethyl) amine (112 mg, 1.123 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 8.0 mg (14%) of the title compound.

LCMS: 529.4 (M + H), retention times: 1.61 minutes and 1.64 minutes.

Example  113: 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl ) -3- Thienyl ] -3- [1- (on Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops), (2R) -3-methyl-2-butanamine (98 mg, 1.123 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (10%) of the title compound.

LCMS: 517.2 (M + H), retention time: 1.65 minutes.

Example  114: 5- {5-[( Cyclopentylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg) in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops) and cyclopentanamine (0.11 mL, 1.123 mmol) and reacted for 4 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction was reacted overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (6.0%) of the title compound.

LCMS: 515.6 (M + H), retention time: 1.38 minutes.

Example  115: 5- (5-{[( Cyclopropylmethyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops) and 1-cyclopropylmethanamine (0.10 mL, 1.123 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (10%) of the title compound.

LCMS: 501.4 (M + H), retention time: 1.53 minutes.

Example  116: 5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl ) -3- Thienyl ] -3- [1- (on Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops), (2S) -3-methyl-2-butanamine (98 mg, 1.123 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 8.0 mg (15%) of the title compound.

LCMS: 517.2 (M + H), retention time: 1.65 minutes.

Example  117: 5- (5-{[(2,2-dimethylpropyl) amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (3 drops), (2,2-dimethylpropyl) amine (0.13 mL, 1.123 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 4.0 mg (7%) of the title compound.

LCMS: 517.2 (M + H), retention times: 1.68 minutes and 1.71 minutes.

Example  118: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[( Phenylmethyl ) Amino] Me Tyl} -3-thienyl) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg) in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (5 drops) and (phenylmethyl) amine (0.14 mL, 1.123 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (8%) of the title compound.

LCMS: 537.2 (M + H), retention time: 1.68 minutes.

Example  119: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[(2S)- Tetrahydro 2-fu la Nilmethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in dichloromethane (3.0 mL) and methanol (1.5 mL) To a solution of -carboxamide (50 mg, 0.112 mmol) is added acetic acid (5 drops), 1-[(2S) -tetrahydro-2-furanyl] methanamine (0.12 mL, 1.123 mmol), 6 The reaction was carried out for hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction mixture was stirred at rt overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 23 mg (8%) of the title compound.

LCMS: 531.4 (M + H), retention time: 1.58 minutes.

Example  120: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[( Tetrahydro -2H-pyran-4- Work Methyl) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (5 drops) and (tetrahydro-2H-pyran-4-ylmethyl) amine (130 mg, 1.123 mmol) and reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 7.0 mg (11%) of the title compound.

LCMS: 545.4 (M + H), retention time: 1.52 minutes.

Example  121: 5- {5-[( Butylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in dichloromethane (3.0 mL) and methanol (1.5 mL) To a solution of carboxamide (50 mg, 0.112 mmol) was added 5 drops of acetic acid, butylamine (0.11 mL, 1.123 mmol) and reacted for 6 hours. Sodium borohydride (43 mg, 1.123 mmol) was then added and stirred at rt overnight. All solvents were removed in vacuo and dissolved in DMSO (1.0 mL). Purification by reverse phase Gilson preparative HPLC gave 5.0 mg (10%) of the title compound.

LCMS: 503.4 (M + H), retention time: 1.63 minutes.

Example  122: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[(2R)- Tetrahydro 2-fu la Nilmethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg) in DMSO (2.0 mL) , 0.112 mmol) was added acetic acid (5 drops), 1-[(2R) -tetrahydro-2-furanyl] methanamine (130 mg, 1.123 mmol), and the reaction mixture was reacted for 6 hours. Sodium triacetoxyborohydride (238 mg, 1.123 mmol) was added and the reaction stirred overnight. Then additional 1-[(2R) -tetrahydro-2-furanyl] methanamine (130 mg, 1.123 mmol) was added, followed by sodium triacetoxyborohydride after 6 hours. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (8.0%) of the title compound.

LCMS: 531.4 (M + H), retention time: 1.50 minutes.

Example  123: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({(2S) -2-[( Methyloxy ) Me Tyl] -1-pyrrolidinyl} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in dichloromethane (3.0 mL) and methanol (1.5 mL) To a solution of carboxamide (50 mg, 0.112 mmol) was added 5 drops of acetic acid, (2S) -2-[(methyloxy) methyl] pyrrolidine (129 mg, 1.123 mmol) and 6 hours at room temperature. Reacted for a while. Sodium borohydride (43 mg, 1.123 mmol) was then added and the reaction stirred overnight at room temperature. The reaction mixture was purified by reverse phase Gilson preparative HPLC to give 8.0 mg (13%) of the title compound.

LCMS: 545.2 (M + H), Retention time: 1.62 minutes and 1.66 minutes.

Example  124: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({(2R) -2-[( Methyloxy ) methyl ] -1-pyrrolidinyl} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in dichloromethane (3.0 mL) and methanol (1.5 mL) To a solution of carboxamide (50 mg, 0.112 mmol) was added acetic acid (5 drops), (2R) -2-[(methyloxy) methyl] pyrrolidine (129 mg, 1.123 mmol) and 6 at room temperature. Stir for hours. Sodium borohydride (43 mg, 1.123 mmol) was then added and the reaction stirred overnight at room temperature. The mixture was purified by reverse phase Gilson preparative HPLC to give 5.0 mg (13%) of the title compound.

LCMS: 545.2 (M + H), Retention time: 1.62 minutes and 1.66 minutes.

Example  125: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4- [2- ( Methylamino )ethyl] Phenyl } -1H-indole-7- Carboxamide

To a solution of 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (200 mg, 0.48 mmol) in dioxane and H ₂ O [ 4- (cyanomethyl) phenyl] boronic acid (232 mg, 0.144 mmol), potassium carbonate (400 mg, 2.88 mmol), and tetrakis (triphenylphosphine) palladium (0) (30 mg, 0.048 mmol) Added. The solution was stirred and heated at 160 ° C. for 40 minutes under microwave. The reaction was diluted with EtOAc and H ₂ O and filtered to give yellow crystals as the desired product. The solution was washed with brine and H ₂ O and then EtOAc was concentrated. MeOH was added to the residue, which precipitated the desired product which was then washed again with MeOH to give 5- [4- (cyanomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-pipe Ridinyl] -1H-indole-7-carboxamide was provided.

To 5- [4- (cyanomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (78 mg, 0.173 mmol) in DCM A 1.5 M diisobutylaluminum hydride solution (240 mL, 0.346 mmol) in toluene was added at 0 ° C. The reaction was stirred at 0 ° C. for 20 minutes. The reaction was then quenched with saturated KNa tartrate solution. Two layers were filtered off and the solid was the desired product. In addition, the organic layer was concentrated to give the desired compound 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (2-oxoethyl) phenyl] -1H-indole-7-carboxamide Was provided, which was taken without further purification.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (2-oxoethyl) phenyl] -1H-indole-7 in methanol (5 mL) and methylene chloride (5 mL) To a solution of carboxamide (50 mg, 0.11 mmol) was added 2 M methylamine (0.4 mL) in tetrahydrofuran followed by 1 drop of acetic acid at room temperature. The reaction was stirred at rt for 2 h and then sodium triacetoxyborohydride (200 mg, 0.94 mmol) was added. The reaction was stirred overnight. Purification by flash chromatography then gave 10 mg (19.4%) of the title compound.

LC / MS = m / z 469.4 [M + H] Retention time: 1.63 minutes.

Example  126: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4- [2- ( Propylamino )ethyl] Phenyl } -1H-indole-7- Carboxamide

Replace the methylamine with 2M propylamine (0.4 mL) in tetrahydrofuran and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4- [2- (methyl Prepared according to the general procedure for amino) ethyl] phenyl} -1 H-indole-7-carboxamide to give 15 mg (27.5%) of the title compound.

LC / MS = m / z 497.6 [M + H] Retention time: 1.63 minutes.

Example  127: 5- {4- [2- ( Ethylamino )ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (2-oxoethyl) phenyl] -1H-indole-7 in methanol (5 mL) and methylene chloride (5 mL) To a solution of carboxamide (50 mg, 0.11 mmol) was added 2 M ethylamine (0.4 mL) in tetrahydrofuran followed by 1 drop of acetic acid at room temperature. The reaction was stirred at rt for 2 h and then sodium triacetoxyborohydride (200 mg, 0.94 mmol) was added. The reaction was stirred overnight. It was then purified by flash chromatography to give 15 mg (28.3%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.57 minutes.

Example  128: 5- {4-[({[1- (1,1-dimethylethyl) -3- methyl -1H- Pyrazole -5-yl] carbonyl} amino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of [4- (aminomethyl) phenyl] boronic acid (145 mg, 0.966 mmol) in DMF (2 mL) 1- (1,1-dimethylethyl) -3-methyl-1H-pyrazole-5-carr Bonyl chloride (290 mg, 1.45 mmol) and triethylamine (403 μl, 2.90 mmol) were added. The reaction was stirred for 2 hours. It was then quenched and partitioned between EtOAc and H ₂ O and the organic layer was concentrated to {4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl } Amino) methyl] phenyl} boronic acid.

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (50 mg, 0.120) in dioxane (1 mL) and water (0.4 mL) In a solution of mmol) potassium carbonate (74 mg, 0.484 mmol) and {4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino ) Methyl] phenyl} boronic acid (153 mg, 0.483 mmol) was added. The reaction mixture was stirred and bubbled with argon for 5 minutes, followed by chloro (di-2-norbornylphosphino) (2-dimethylaminomethylferrocen-1-yl) palladium (II) (7 mg, 0.012 mmol). Added. The reaction was stirred for 10 minutes and then heated to 150 ° C. The reaction was evaporated and purified by Gilson preparative HPLC to give 5 mg (5.8%) of the title compound.

LC / MS = m / z 605.4 [M + H] Retention time: 2.14 minutes.

Example  129: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(4- Pyridinylcarbonyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

{4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} boronic acid (4-{[(4 -Pyridinylcarbonyl) amino] methyl} phenyl) boronic acid (124 mg, .480 mmol) replaced the title compound with 5- {4-[({[1- (1,1-dimethylethyl) -3 -Methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide tri Prepared according to the general procedure for fluoroacetate to give 30 mg (45.8%) of the title compound.

LC / MS = m / z 537 [M + H] Retention time: 2.04 minutes.

Example  130: 5- (4-{[( Cyclopentylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

{4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} boronic acid (4-{[(cyclo Instead of pentylcarbonyl) amino] methyl} phenyl) boronic acid (119 mg, 0.480 mmol) the title compound was replaced with 5- {4-[({[1- (1,1-dimethylethyl) -3-methyl- 1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate Prepared according to the general procedure for 30 mg (47%) of the title compound was obtained.

LC / MS = m / z 537 [M + H] Retention time: 2.04 minutes.

Example  131: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(2- Furanylcarbonyl ) Amino] methyl} Phenyl ) -1H-indole-7- Carboxamide

{4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} boronic acid (4-{[(2 -Furanylcarbonyl) amino] methyl} phenyl) boronic acid (118 mg, 0.480 mmol), replacing the title compound with 5- {4-[({[1- (1,1-dimethylethyl) -3- Methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluor Prepared according to the general procedure for low acetate to give 16 mg (25%) of the title compound.

LC / MS = m / z 535.5 [M + H] Retention time: 1.99 minutes.

Example  132: 5- (4- {2-[( Cyclobutylcarbonyl ) Amino] ethyl} Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

N- [2- (4-bromophenyl) ethyl] acetamide was replaced by N- [2- (4-bromophenyl) ethyl] cyclobutanecarboxamide (100 mg, 0.324 mmol) to afford the title compound. According to the general procedure for 5- {4- [2- (acetylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide Prepared. Purification by flash chromatography gave 28 mg (48.3%) of the title compound.

LC / MS = m / z 537.2 [M + H] Retention time: 1.99 minutes.

Example  133: 5- (4- {2-[( Cyclohexylcarbonyl ) Amino] ethyl} Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Substitute N- [2- (4-bromophenyl) ethyl] acetamide with N- [2- (4-bromophenyl) ethyl] cyclohexanecarboxamide (100 mg, 0.324 mmol) to give the title compound. According to the general procedure for 5- {4- [2- (acetylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide Prepared. Purification by flash chromatography gave 32 mg (52.5%) of the title compound.

LC / MS = m / z 565.4 [M + H] Retention time: 2.14 minutes.

Example  134: 5- (3- {2-[( Cyclohexylcarbonyl ) Amino] ethyl} Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

N- [2- (4-bromophenyl) ethyl] acetamide was replaced with N- [2- (3-bromophenyl) ethyl] cyclohexanecarboxamide (100 mg, 0.324 mmol) to afford the title compound. According to the general procedure for 5- {4- [2- (acetylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide Prepared. The concentrated reaction mixture was purified by Gilson preparative HPLC and then refined by flash chromatography to provide the title compound.

LC / MS = m / z 565.2 [M + H] Retention time: 2.16 minutes.

Example  135: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- (1- Piperazinyl ) -3- Pipe Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (100 mg) in dioxane (1.0 mL) and H ₂ O (0.8 mL) , 0.241 mmol) cesium carbonate (314 mg, 0.964 mmol) and [6- (4-{[(1,1-dimethylethyl) oxy] carbonyl} -1-piperazinyl) -3-pyridinyl ] Boronic acid (297 mg, 0.964 mmol) was added. The reaction mixture was stirred and then tetrakis (triphenylphosphine) palladium (0) (28 mg, 0.024 mmol) was added. The reaction was heated at 160 ° C. for 20 minutes under microwave. The mixture was concentrated and taken up in EtOAc (10 mL) and H ₂ O (5.0 mL). The compound was purified by Gilson preparative HPLC to give 1,1-dimethylethyl 4- (5- {7- (aminocarbonyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -5-yl} -2-pyridinyl) -1-piperazincarboxylate and 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-piperazinyl) 129 mg (44%) of 3-pyridinyl] -1H-indole-7-carboxamide was provided.

1,1-dimethylethyl 4- (5- {7- (aminocarbonyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-5- in methanol (0.3 mL) To a solution of yl-2--2-pyridinyl) -l piperazinecarboxylate (130 mg, 0.218 mmol) was added 4M HCl (0.3 mL) in dioxane. The reaction was heated at 50 ° C. and stirred for 3 hours. The reaction mixture was concentrated and neutralized on an SCX cartridge primed with CH ₂ Cl ₂ , then MeOH and collected with ammonia in MeOH. 20 mg of the desired fractions were concentrated and purified using MDAP HPLC to give 9.4 mg (7%) of the title compound.

LC / MS = m / z 497.2 [M + H] Retention time: 1.45 minutes.

Example  136: 5- [6- (4-ethyl-1- Piperazinyl ) -3- Pyridinyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-piperazinyl) -3-pyridinyl] -1H-indole-7-carboxamide in dichloromethane ( To a solution of 40 mg, 0.081 mmol) acetaldehyde (7 mg, 0.162 mmol) and sodium triacetoxyborohydride (100 mg, 0.472 mmol) were added. The reaction was stirred at rt overnight. The reaction mixture was then concentrated and dissolved in EtOAc and H ₂ O. The salts were filtered and the organic layer was concentrated and purified by Gilson preparative HPLC to give 39 mg (92%) of the title compound.

LC / MS = m / z 525.6 [M + H] Retention time: 1.44 minutes.

Example  137: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (1- Piperidinylmethyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide (40 mg, 0.09 mmol) in dichloromethane Piperidine (9 μl, 0.09 mmol) was added. The reaction was stirred for 1 hour and then sodium triacetoxyborohydride (58 mg, 0.27 mmol) was added. The reaction mixture was stirred at rt overnight. The mixture was then concentrated and purified by Gilson preparative HPLC to give 8.0 mg (14%) of the title compound.

LC / MS = m / z 509.4 [M + H] Retention time: 1.71 minutes.

Example  138: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1- Piperidinylmethyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (2 mL) and acetic acid (1 drop) To a solution of (50 mg, 0.114 mmol) was added piperidine (46 μl, 0.456 mmol). The reaction was stirred at rt for 2 h and then sodium triacetoxyborohydride (75 mg, 0.342 mmol) was added. The reaction was then stirred for an additional 3 hours. The mixture was then purified by Gilson preparative HPLC to give 36 mg (61%) of the title compound.

LC / MS = m / z 509.4 [M + H] Retention time: 1.80 minutes.

Example  139: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4-[( Methylamino ) methyl ] Fe Nil} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carbohydrate in dichloromethane (12 mL), methanol (2 mL) and acetic acid To a solution of voxamide (20 mg, 0.045 mmol) was added methylamine (20 μl, 0.54 mmol) in THF. The reaction mixture was stirred at rt for 2 h and then sodium triacetoxyborohydride (10.3 mg, 0.270 mmol) was added. The mixture was then stirred for an additional 3 hours and then the mixture was concentrated and purified by Gilson preparative HPLC to give 6 mg (10%) of the title compound.

LC / MS = m / z 454.6 [M + H] Retention time: 1.23 minutes.

Example  140: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(1- Methylethyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (900 μl) and acetic acid (2 drops) 40 mg, 0.09 mmol) was added 2-propanamine (93 μl, 1.08 mmol). After 2 hours sodium triacetoxyborohydride (172 mg, 0.81 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 30 mg (69%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.56 minutes.

Example  141: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4-[( Propylamino ) methyl ] Fe Nil} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (900 μl) and acetic acid (2 drops) To a solution of 20 mg, 0.045 mmol) propylamine (45 μl, 1.08 mmol) was added. After 2 hours sodium triacetoxyborohydride (172 mg, 0.81 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 21.1 mg (74%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.54 minutes.

Example  142: 5- (4-{[(1-ethylpropyl) amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (900 μl) and acetic acid (2 drops) To a solution of 40 mg, 0.09 mmol) 3-pentanamine (108 μl, 1.08 mmol) was added. After 2 hours sodium triacetoxyborohydride (172 mg, 0.81 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 34.5 mg (74%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.69 minutes.

Example  143: 5- {4-[( Cyclopentylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Pipe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (900 μl) and acetic acid (2 drops) To the solution of 40 mg, 0.09 mmol) cyclopentylamine (108 μl, 1.08 mmol) was added. After 2 hours sodium triacetoxyborohydride (172 mg, 0.81 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 11.1 mg (20%) of the title compound.

LC / MS = m / z 509.4 [M + H] Retention time: 1.66 minutes.

Example  144: 5- {4-[( Cyclobutylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (900 μl) and acetic acid (2 drops) To a solution of 40 mg, 0.091 mmol) cyclobutylamine (94 μl, 1.08 mmol) was added. After 2 hours, sodium triacetoxyborohydride (120 mg, 1.10 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 26.3 mg (59%) of the title compound.

LC / MS = m / z 495.4 [M + H] Retention time: 1.37 minutes.

Example  145: 5- {4-[( Ethylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Solution of 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide (20 mg, 0.046 mmol) in DMSO and acetic acid To this was added ethylamine (32 μl, 0.547 mmol). After 2 hours, sodium triacetoxyborohydride (120 mg, 1.10 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 11.5 mg (55%) of the title compound.

LC / MS = m / z 469.4 [M + H] Retention time: 1.52 minutes.

Example  146: 5- {4-[(dimethylamino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 N-dimethylamine (170 μl, 0.342 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 28.9 mg (54%) of the title compound.

LC / MS = m / z 469.4 [M + H] Retention time: 1.52 minutes.

Example  147: 5- {4-[( Diethylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 diethylamine (36 μl, 0.342 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 37.6 mg (67%) of the title compound.

LC / MS = m / z 497.6 [M + H] Retention time: 1.52 minutes.

Example  148: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (4- Morpholinylmethyl ) Phenyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 morpholine (30 μl, 0.342 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 40.3 mg (70%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.53 minutes.

Example  149: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (1- Pyrrolidinylmethyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 cyclopentylamine (28 μl, 0.342 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 20.1 mg (36%) of the title compound.

LC / MS = m / z 495.4 [M + H] Retention time: 1.58 minutes.

Example  150: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({[(1S) -2-hydroxy-1-methylethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 (2S) -2-amino-1-propanol (56 μl, 0.745 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 25.9 mg (15%) of the title compound.

LC / MS = m / z 499.6 [M + H] Retention time: 1.54 minutes.

Example  151: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({[(1R) -2-hydroxy-1-methylethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 (2R) -2-amino-1-propanol (56 μl, 0.745 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 29.6 mg (53%) of the title compound.

LC / MS = m / z 499.6 [M + H] Retention time: 1.47 minutes.

Example  152: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({[(2R) -2-hydroxypropyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DMSO (3 mL) and acetic acid (50 mg, 0.114 (2R) -1-amino-2-propanol (56 μl, 0.745 mmol) was added to the solution. After 2 hours sodium triacetoxyborohydride (290 mg, 1.36 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 14.7 mg (26%) of the title compound.

LC / MS = m / z 499.6 [M + H] Retention time: 1.46 minutes.

Example  153: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({[2-hydroxy-1- ( Hide Oxymethyl) ethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

2 in a solution of 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide (40 mg, 0.091 mmol) in DMSO -Amino-1,3-propanediol (50 mg, 0.55 mmol) and acetic acid (1 drop) were added. After 2 hours sodium triacetoxyborohydride (232 mg, 1.10 mmol) was added. The reaction mixture was stirred overnight. The compound was purified by Gilson preparative HPLC to give 15.9 mg (28%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.45 minutes.

Example  154: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(1- Methylbutyl ) Amino] methyl} Fe Nil) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol) in DMSO (3.0 mL) To a solution of 1-2-pentanamine (324 μl, 2.74 mmol) and acetic acid (1 drop) were added. After 2 hours sodium triacetoxyborohydride (290 mg, 1.10 mmol) was added. The reaction mixture was stirred overnight. The compound was then filtered and concentrated. Thereafter, it was purified by Gilson preparative HPLC to give 9.5 mg (13%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.66 minutes.

Example  155: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(1R) -1- Methylpropyl ] Amino} methyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol) in DMSO (2.0 mL) To a solution of (2R) -2-butanamine (69 μl, 0.684 mmol) and acetic acid (1 drop) were added. After 2 hours sodium triacetoxyborohydride (0.435 mg, 2.05 mmol) was added. The reaction mixture was stirred overnight. The compound was then filtered and concentrated. It was then purified by Gilson preparative HPLC to give 18.6 mg (33%) of the title compound.

LC / MS = m / z 497.6 [M + H] Retention time: 1.70 minutes.

Example  156: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Methylpropyl ) Amino] methyl } Phenyl) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole in DCM (1.5 mL), MeOH (1.5 mL), and acetic acid (4 drops) To a solution of -7-carboxamide (50 mg, 0.114 mmol) was added 2-methyl-1-propanamine (137 μl, 1.37 mmol) and stirred at room temperature. After 2 hours, sodium borohydride (23 mg, 0.684 mmol) was added and the reaction mixture was purified by SCX cartridge to give 47.8 mg (85%) of the title compound.

LC / MS = m / z 497.2 [M + H] Retention time: 1.69 minutes.

Example  157: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(1S) -1- Methylpropyl ] Amino} methyl) Phenyl ] -1H-indole-7- Carboxamide  acetate

Replace the 2-methyl-1-propanamine with (2S) -2-butanamine (138 μl, 1.37 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5 Prepared according to the general procedure for-(3-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-carboxamide to give 43.2 mg (76%) of the title compound.

LC / MS = m / z 497.4 [M + H] Retention time: 1.84 minutes.

Example  158: 5- (4-{[( Cyclopropylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace acetyl chloride with cyclopropanecarbonyl chloride (14 μl, 1.37 mmol) and replace the title compound with 5- {4-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4- Prepared according to the general procedure for piperidinyl] -1 H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 19.1 mg (28%) of the title compound.

LC / MS = m / z 509.2 [M + H] Retention time: 1.86 minutes.

Example  159: 5- (4-{[( Cyclobutylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

Replace acetyl chloride with cyclobutanecarbonyl chloride (17 μl, 1.37 mmol) and replace the title compound with 5- {4-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4- Prepared according to the general procedure for piperidinyl] -1 H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 20.2 mg (28%) of the title compound.

LC / MS = m / z 523.2 [M + H] Retention time: 1.94 minutes.

Example  160: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(2- Thienylacetyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

Replace acetyl chloride with (3Z) -3- (methylthio) -3,5-hexadienoyl chloride (18 μl, 1.37 mmol) and replace the title compound with 5- {4-[(acetylamino) methyl] phenyl}. Prepared according to the general procedure for -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 13.5 mg (18%) of the title compound.

LC / MS = m / z 565.2 [M + H] Retention time: 1.98 minutes.

Example  161: 5- [4-({[(1S) -1,2-dimethylpropyl] amino} methyl ) Phenyl ] -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carbox in DCM (1.5 mL), MeOH (1.5 mL) and acetic acid To a solution of amide (40 mg, 0.091 mmol) was added (2S) -3-methyl-2-butanamine (128 μl, 1.10 mmol) and stirred at room temperature for 2 hours. Sodium borohydride (19 mg, 0.546 mmol) was then added and stirred for 48 hours. The compound was then purified by Gilson preparative HPLC to give 5.8 mg (12%) of the title compound.

LC / MS = m / z 511.2 [M + H] Retention time: 1.76 minutes.

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (50 mg) in dioxane (1 mL) and H ₂ O (0.4 mL) , 0.121 mmol) was added potassium carbonate (74 mg, 0.484 mmol) and (4 {[(methylsulfonyl) amino] methyl} phenyl) boronic acid (110 mg, 0.50 mmol). The reaction mixture was stirred and bubbled with argon for 5 minutes and then chloro (di-2-norbornylphosphino) (2-dimethylaminomethylferrocen-1-yl) palladium (II) (7 mg, 0.012 mmol) was added. Added. The reaction was then stirred and heated at 160 ° C. under microwave for 10 minutes. The mixture was concentrated and purified by Gilson preparative HPLC to give 34.3 mg (55%) of the title compound.

LC / MS = m / z 519.4 [M + H] Retention time: 1.77 minutes.

Example  162: 5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl ) Phenyl ] -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carbox in DCM (1.5 mL), MeOH (1.5 mL) and acetic acid To a solution of amide (50 mg, 0.114 mmol) was added (2R) -3-methyl-2-butanamine (160 μl, 1.37 mmol) and stirred at room temperature for 2 hours. Sodium borohydride (19 mg, 0.546 mmol) was then added and stirred for 48 hours. The compound was then purified by Gilson preparative HPLC to give 50 mg (86%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.65 minutes.

Example  163: 5- (6-amino-2- Pyridinyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7-car Lebox Arm De Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane- in dioxane (5 mL) To a solution of 2-yl) -1H-indole-7-carboxamide (83 mg, 0.18 mmol) 6-bromo-2-pyridinamine (93 mg, 0.54 mmol), potassium carbonate in water (1.5 mL) (149 mg, 1.08 mmol) and chloro (di-2-norbornylphosphino) (2-dimethylaminomethylferrocen-1-yl) palladium (II) (19 mg, 0.031 mmol) were added. The reaction was heated at 150 ° C. for 20 minutes under microwave. The reaction mixture was then concentrated and aqueous extracted. The organic layer was then concentrated and purified by mass directed autoprep HPLC to give 22.3 mg (29%) of the title compound.

LC / MS = m / z 428.6 [M + H] Retention time: 1.34 minutes.

Example  164: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1H- Pyrazole -1 day) Phenyl ] -1H-indole-7- Carboxamide

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20 mg, 0.048 mmol) in [3- (1H-pyrazole-1 A solution of potassium carbonate (20 mg) in -yl) phenyl] boronic acid (36 mg, 0.193 mmol), dioxane (2.8 mL) and water (1.2 mL) was added. To this mixture was added chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (3 mg, 0.005 mmol). The resulting mixture was reacted for 10 minutes at 160 ° C. under CEM microwaves and then concentrated at 80 ° C. under a nitrogen stream (dry chamber). The crude product was partitioned between water (2 mL) and CH ₂ Cl ₂ (2 mL). The layers were separated by hydrophobic frit and the aqueous layer was extracted with CH ₂ Cl ₂ (2 × 2 mL). The organic layers were combined and concentrated at 80 ° C. under a nitrogen stream. Dimethyl sulfoxide (0.8 mL) was added to the residue, sonicated for 10 seconds, filtered through the presence and then filtered through a 0.2 μm filter. The crude product was purified on Agilent MDAP using a Zorbax Eclipse XDB 610 21.2 x 50 mm column to give 2.3 mg (10%) of the title compound.

LC / MS = m / z 478.2 [M + H] Retention time: 2.05 minutes.

Example  165: 5- [4- (dimethylamino) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7-car Lebox Arm De

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (40 mg, 0.097 mmol), dioxane (2.8 mL) in a CEM microwave tube And a solution of potassium carbonate (40 mg, 0.289 mmol) in water (1.2 mL). To this mixture was added [4- (dimethylamino) phenyl] boronic acid (65 mg, 0.386 mmol) and chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (1 mg, 0.002 mmol) was added. The vial was capped and the reaction reacted at 160 ° C. for 10 minutes under CEM microwaves. The reaction was concentrated at 80 ° C. under a stream of nitrogen. The crude product was dissolved in dimethyl sulfoxide (1 mL) and purified by eluting with dimethyl sulfoxide (4 mL) through a 1 g silica SPE cartridge. Dimethyl sulfoxide was concentrated for 3 h at 65 ° C. in Genevac, and the residue was reconstituted in dimethyl sulfoxide (1 mL) and filtered through Acrodisc. The solution of the crude product was then purified on Agilent MDAP (UV 214 screened). The purified product was passed through a polymer-bound carbonate SPE cartridge to yield 2.7 mg (6.2%) of the title compound.

LC / MS = m / z 455.2 [M + H] Retention time: 1.71 minutes.

Example  166: 5- (3- Aminophenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7-carboxamide

In a CEM microwave tube 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (40 mg, 0.0965 mmol), potassium carbonate (80 mg, 0.578 mmol) and (3-aminophenyl) boronic acid sulfate (145 mg, 0.386 mmol) were added. The mixture is taken up in water (1.2 mL) and dioxane (2.8 mL) and chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (1 mg, 0.002 mmol) was added. The mixture was then reacted at 150 ° C. for 10 minutes under CEM microwaves. Ethyl acetate (2 mL) was added and the layers separated. The aqueous layer was washed with ethyl acetate (1 x 2 mL). The organic layers were combined, concentrated under nitrogen stream and dissolved in dimethyl sulfoxide (0.89 mL) and trifluoroacetic acid (0.15 mL). This solution of crude product was subjected to 9 minutes at 20 mL / min with a linear gradient of 30% CH ₃ CN / H ₂ O (0.1% TFA) to 70% CH ₃ CN / H ₂ O (0.1% TFA) on an Agilent MDAP. Purification by eluting over. To the HPLC fractions containing the product was added saturated K ₂ CO ₃ (1 mL) solution, 1 M solution of sodium hydroxide (1 mL) and ethyl acetate (2 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 2 mL). The organic layers were combined, filtered through a magnesium sulfate plug and concentrated under a stream of nitrogen to give 14.9 mg (36%) of the title compound.

LC / MS = m / z 427.2 [M + H] Retention time: 1.39 minutes.

Example  167: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(2- methyl -One- Pyrrolidinyl ) methyl ] -2-T on Nil} -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} -1H-indole-7- {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} boronic acid used to prepare carboxamides was prepared in three separate batches using the procedure shown below:

Batch 1: NaBH (OAc) ₃ (271 mg, 1.28 mmol), HOAc (0.07 mL) and 2-methylpyrrolidine (0.043 mL, 0.42 mmol) in CH ₂ Cl ₂ (4 mL) in a ₂ -drum vial To a solution of (5-formyl-2-thienyl) boronic acid (100 mg, 0.64 mmol). The vial was capped and the reaction stirred at room temperature for 15 hours. The reaction mixture was loaded directly into a 2 g SCX cartridge (pre-equilibrated with MeOH) eluting sequentially with MeOH (12 mL) and a 2 M solution of NH ₃ / MeOH (8 mL). Fractions containing boronic acid crude product were concentrated under N ₂ stream and dried under high vacuum to give 45 mg of crude product. The crude product was taken up in saturated NaHCO ₃ (2 mL) and extracted with EtOAc (3 × 2 mL) to give 6.6 mg of crude {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} boronic acid Provided.

Batch 2: NaBH (OAc) ₃ (271 mg, 1.28 mmol), HOAc (0.07 mL) and 2-methylpyrrolidine (0.043 mL, 0.42 mmol) were added in a 2-drum vial 1: 1 CH ₂ Cl ₂ / Me0H. To a solution of (5-formyl-2-thienyl) boronic acid (100 mg, 0.64 mmol) in (4 mL). The vial was capped and the reaction stirred at room temperature for 15 hours. The reaction mixture was loaded directly into a 2 g SCX cartridge (pre-equilibrated with MeOH), sequentially eluting with a 2 M solution of MeOH (12 mL) and NH ₃ / MeOH (8 mL). Fractions containing boronic acid crude product were concentrated under N ₂ stream and dried under high vacuum to give 45 mg of crude product. The crude product was taken up in saturated NaHCO ₃ (2 mL) and extracted with EtOAc (3 × 2 mL) to give 5 mg of crude {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} boronic acid Provided.

Batch 3: solution of (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol) in MeOH (1 mL) in a 2-drum vial in 2-methylpyrrolidine (0.033 mL, 0.32 mmol) Was added. The vial was capped and the reaction stirred at room temperature for 2 hours. NaCNBH ₃ (40 mg, 0.64 mol) was added and stirring was continued for 19 hours. The reaction mixture was loaded directly into a 2 g SCX cartridge (pre-equilibrated with MeOH), sequentially eluting with a 2 M solution of MeOH (12 mL) and NH ₃ / MeOH (9 mL). Fractions containing boronic acid crude product were concentrated under N ₂ stream and dried under high vacuum to give 45 mg of crude product. The crude product was taken up in saturated NaHCO ₃ (2 mL) and extracted with EtOAc (3 × 2 mL) to give 7.8 mg of crude {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} boronic acid Provided. The crude boronic acid from the above 3 reactions was collected and 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -2- Continued use in the preparation of thienyl} -1H-indole-7-carboxamide (three batches of {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} boronic acid Final weight after collection was 19 mg).

5-Bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (36 mg, 0.0862 mmol) solution, {5-[(2-methyl- 1-pyrrolidinyl) methyl] -2-thienyl} boronic acid (19 mg, 0.0862 mmol) and potassium carbonate (71 mg, 0.517 mmol) were combined in a CEM microwave tube. To this mixture was added water (0.25 mL), dioxane (0.75 mL) and tetrakis (triphenylphosphine) palladium (0) (10 mg, 0.009 mmol). The vial was capped and reacted at 150 ° C. for 20 minutes under CEM microwaves. Tetrakis (triphenylphosphine) palladium (0) (10 mg, 0.009 mmol) was added to the reaction and reacted at 150 ° C. for 20 minutes under microwave. Additional tetrakis (triphenylphosphine) palladium (0) (10 mg, 0.009 mmol) was added and the reaction heated at 150 ° C. for an additional 20 minutes under CEM microwaves. The reaction mixture was pre-equilibrated with a 2 g SCX cartridge (pre-equilibrated with 3 mL H ₂ O), sequentially with water (3 mL), MeOH (9 mL) and a 2 M solution of NH ₃ / MeOH (9 mL). Filtered through. Fractions containing the crude product solution were concentrated under a stream of nitrogen and the residue was taken up in DMSO (3 mL). This DMSO solution of crude product, 10% for 1 min by 20 mL 1 min CH ₃ CN / H by ₂ O (0.1% TFA), followed by 10% over an 8-minute _{CH 3 CN / H 2 O (} 0.1% TFA ) Eluted with a linear gradient of 95% CH ₃ CN / H ₂ O (0.1% TFA) and held at final concentration for 30 seconds to allow for three pieces on an Agilent MDAP (Gorbox Eclipse XDB-C18 column: 21.2 x 50 mm) Purification as separate injections (1 mL each). The two fractions containing the product were filtered through a 500 mg Parmasil CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA (using two columns per fraction) and 40 ° C. under a nitrogen stream. Concentration in gave 13 mg (29.3%) of the title compound.

LC / MS = m / z 515.6 [M + H] Retention time: 1.62 minutes.

Example  168: 5- {5-[( Ethylamino ) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

To prepare 5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide The {5-[(ethylamino) methyl] -2-thienyl} boronic acid used was prepared as follows: A 2 M solution of ethylamine (0.16 mL, 0.32 mmol) in THF was prepared in a 2-drum vial with MeOH ( To a solution of (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol) in 1 mL). The vial was capped and the reaction stirred at room temperature for 2 hours. NaCNBH ₃ (40 mg, 0.64 mmol) was added and stirring continued for 17 hours. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (6 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated under a nitrogen stream to give 47 mg of crude {5-[(ethylamino) methyl] -2-thienyl} boronic acid.

5-bromo-3- [1- (ethylsulfonyl) -4- in a CEM microwave tube containing {5-[(ethylamino) methyl] -2-thienyl} boronic acid (47 mg, 0.254 mmol) Piperidinyl] -1H-indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol), dioxane (1.5 mL), H ₂ O (0.5 mL) and tetrakis ( Triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) was added. The reaction was heated at 150 ° C. for 30 minutes under CEM microwave (which was stopped 30 minutes before due to excessive build-up). The reaction mixture was poured into a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluted with a 2 M solution of H ₂ O (3 mL), MeOH (9 mL) and NH ₃ / MeOH (6 mL). Filtered through. The NH ₃ / MeOH fraction was dried at 40 ° C. under a stream of nitrogen, the crude product was dissolved in dimethyl sulfoxide (1 mL) and 10% CH ₃ CN / H ₂ O (0.1% TFA) at 20 mL per minute for 1 minute. Eluted with a linear gradient of 10% CH ₃ CN / H ₂ O (0.1% TFA) to 95% CH ₃ CN / H ₂ O (0.1% TFA) over 8 minutes and held at final concentration for 30 seconds Purification on Agilent MDAP (Zorbox Eclipse XDB-C18 column: 21.2 x 50 mm). Fractions containing product were filtered through a 500 mg Parmasil CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA (using 2 columns per fraction) and concentrated at 60 ° C. under a stream of nitrogen to give the title compound 8.8 mg (10%).

LC / MS = m / z 429.8 [M + H] Retention time: 1.25 minutes.

Example  169: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(1- Methylethyl ) Amino] methyl} -2- Thienyl ) -1H-indole-7- Carboxamide

5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indol-7-carboxamide for general According to the procedure, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), isopropylamine (0.027 mL, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) were reacted to give a crude ( 41 mg of 5-{[(1-methylethyl) amino] methyl} -2-thienyl) boronic acid were provided. Then crude (5-{[(1-methylethyl) amino] methyl} -2-thienyl) boronic acid was added 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H. Reaction with indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) 74 mg (37%) were given.

LC / MS = m / z 430.2 [M + H] Retention time: 1.29 minutes.

Example  170: 5- {5-[( Cyclopropylamino ) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

General procedure for 5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), cyclopropylamine (0.022 mL, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) to react the crude {5 63 mg of [(cyclopropylamino) methyl] -2-thienyl} boronic acid were provided. The crude {5-[(cyclopropylamino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 -Carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) to react the title compound, which is not pure Provided. The title compound, which was not pure, was again purified by Agilent MDAP following the procedure shown in Example 5 and isolated as the free base to give 6.8 mg (7.2%) of the title compound.

LC / MS = m / z 430.2 [M + H] Retention time: 1.62 minutes.

Example  171: 5- (5-{[(2,2-dimethylpropyl) amino] methyl }-2- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

General procedure for 5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (2,2-dimethylpropyl) amine (0.037 mL, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) Was reacted to give 73 mg of crude (5-{[(2,2-dimethylpropyl) amino] methyl} -2-thienyl) boronic acid. Then crude (5-{[(2,2-dimethylpropyl) amino] methyl} -2-thienyl) boronic acid was converted to 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] Reacted with -1H-indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) 21 mg (21%) of the title compound were provided.

LC / MS = m / z 430.2 [M + H] Retention time: 1.45 minutes.

Example  172: 5- (5-{[( Cyclopropylmethyl ) Amino] methyl }-2- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

General procedure for 5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (cyclopropylmethyl) amine (0.027 mL, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) 73 mg of crude (5-{[(cyclopropylmethyl) amino] methyl} -2-thienyl) boronic acid were provided. The crude (5-{[(cyclopropylmethyl) amino] methyl} -2-thienyl) boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Reaction with indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) to give the title compound 19.1 mg (20%).

LC / MS = m / z 430.2 [M + H] Retention time: 1.33 minutes.

Example  173: 5- (5-{[( Cyclopropylmethyl ) Amino] methyl } -3- Pyridinyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (Cyclopropylmethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} used to prepare the The amine was prepared as follows: (cyclopropylmethyl) amine (0.011 mL, 0.129 mmol) was prepared in 5- (4,4,5,5-tetramethyl-1,3 in MeOH (1 mL) in a 2-drum vial. To a solution of, 2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol). The vial was capped and the reaction stirred at room temperature for 17 hours. NaCNBH ₃ (16 mg, 0.258 mmol) was added and stirring continued for 30 h. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (6 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated under nitrogen stream to afford crude (cyclopropylmethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3 21 mg of pyridinyl] methyl} amine was provided.

(Cyclopropylmethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine (21 mg, 0.0725 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), di in a CEM microwave tube containing A solution of potassium carbonate (60 mg, 0.434 mmol) in oxane (0.75 mL), H ₂ O (0.25 mL) and chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) was added. The reaction was heated under CEM microwave at 150 ° C. for 30 minutes. The reaction mixture was poured into a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluted with a 2 M solution of H ₂ O (3 mL), MeOH (6 mL) and NH ₃ / MeOH (9 mL). Filtered through. The NH ₃ / MeOH fractions are dried at 40 ° C. under a stream of nitrogen, with 10% CH ₃ CN / H ₂ O (0.1% TFA) for 1 minute at 20 mL per minute, followed by 10% CH ₃ CN / over 8 minutes. Agilent MDAP (Gorbox Eclipse XDB-C18 column: 21.2) eluting with a linear gradient of H ₂ O (0.1% TFA) to 95% CH ₃ CN / H ₂ O (0.1% TFA) and holding at final temperature for 30 seconds. x 50 mm). Fractions containing product were filtered through a 2 g Parmasil CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA and concentrated at 65 ° C. under a stream of nitrogen to afford the title compound which was not pure. Repurification on Agilent MDAP as indicated above provided 25 mg (70%) of the title compound.

LC / MS = m / z 496.6 [M + H] Retention time: 1.35 minutes.

Example  174: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[2- ( Methyloxy ) Ethyl] amino} methyl) -3- Pyridinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , [2- (methyloxy) ethyl] amine (0.011 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give [2- (methyloxy) ethyl] {[5- (4,4, 19 mg of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine were provided. Crude [2- (methyloxy) ethyl] {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} The amine is 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol ) And chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) to give 15 mg (46%) of the title compound. It was.

LC / MS = m / z 500.6 [M + H] Retention time: 1.52 minutes.

Example  175: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[3- ( Methyloxy ) Propyl] amino} methyl ) -3- Pyridinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , [3- (methyloxy) propyl] amine (0.013 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give [3- (methyloxy) propyl] {[5- (4,4, 22 mg of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine were provided. Crude [3- (methyloxy) propyl] {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} The amine is 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol ) And chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) to give 31 mg (83%) of the title compound. It was.

LC / MS = m / z 514.4 [M + H] Retention time: 1.46 minutes.

Example  176: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (4- Morpholinylmethyl ) -3- Pyridinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , Morpholine (0.011 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give 4-{[5- (4,4,5,5-tetramethyl-1,3,2-dioxa 28 mg of borol-2-yl) -3-pyridinyl] methyl} morpholine was provided. The crude 4-{[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} morpholine is then substituted with 5-bromo. -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) and chloro-2- Reaction with (dimethylaminomethyl) -ferrocen-1-yl- (dinorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) gave 15.8 mg (43%) of the title compound.

LC / MS = m / z 512.2 [M + H] Retention time: 1.38 minutes.

Example  177: 5- {5-[( Ethylamino ) methyl ] -3- Pyridinyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , 2M solution of ethylamine in THF (0.065 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give crude ethyl {[5- (4,4,5,5-tetramethyl-1,3 19 mg of, 2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine was provided. Then crude ethyl {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine is replaced with 5-bromo-3 -[1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) and chloro-2- (dimethyl Reaction with aminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) gave 12.3 mg (36%) of the title compound.

LC / MS = m / z 470.4 [M + H] Retention time: 1.44 minutes.

Example  178: 5- {5-[(dimethylamino) methyl ] -3- Pyridinyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol ), 2 M solution of dimethylamine in THF (0.065 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give dimethyl {[5- (4,4,5,5-tetramethyl-1, 23 mg of 3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine was provided. Crude dimethyl {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine is then substituted with 5-bromo-3 -[1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) and chloro-2- (dimethyl Reaction with aminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) gave 5.4 mg (16%) of the title compound.

LC / MS = m / z 470.6 [M + H] Retention time: 1.35 minutes.

Example  179: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(2- methyl -One- Pyrrolidinyl ) methyl ] -3-p Reedy Nil} -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , 2-methylpyrrolidine (0.013 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) reacted to give 3-[(2-methyl-1-pyrrolidinyl) methyl] -5- (4 25 mg of 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine was provided. Then crude 3-[(2-methyl-1-pyrrolidinyl) methyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) and Reaction with chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) gave 6 mg (16%) of the title compound.

LC / MS = m / z 512.6 [M + H] Retention time: 1.67 minutes.

Example  180: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Methylpropyl ) Amino] methyl } -3- Pyridinyl ) -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , Isobutylamine (0.013 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give crude (2-methylpropyl) {[5- (4,4,5,5-tetramethyl-1,3 21 mg of, 2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine was provided. Then crude (2-methylpropyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) and Reaction with chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) gave 12.5 mg (35%) of the title compound.

LC / MS = m / z 498.2 [M + H] Retention time: 1.38 minutes.

Example  181: 5- (5-{[(2,2-dimethylpropyl) amino] methyl } -3- Pyridinyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide According to the general procedure for 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) , (2,2-dimethylpropyl) amine (0.015 mL, 0.129 mmol) and NaCNBH ₃ (16 mg, 0.258 mmol) were reacted to give crude (2,2-dimethylpropyl) {[5- (4,4,5, 25 mg of 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine were provided. Then crude (2,2-dimethylpropyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine To 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 mg, 0.0723 mmol), potassium carbonate (60 mg, 0.434 mmol) And chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine) palladium (II) (4.4 mg, 0.00723 mmol) to give 12.7 mg (34%) of the title compound. .

LC / MS = m / z 512.4 [M + H] Retention time: 1.51 minutes.

Example  182: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Methylbutyl ) Amino] methyl } -2-T on Nil) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox {5-[(ethylamino) methyl] -2-thienyl} boronic acid used to prepare the amide was prepared as follows: (5-formyl-2-thienyl) boron in MeOH (0.5 mL) A solution of acid (50 mg, 0.32 mmol) and a solution of NaCNBH ₃ (40 mg, 0.64 mmol) in MeOH (0.5 mL) were added to (2-methylbutyl) amine (28 mg, 0.32 mmol) in a 2-drum vial. It was. The vial was capped and the reaction stirred at room temperature for 20 hours. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (6 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated under a nitrogen stream to give 43 mg of crude (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) boronic acid.

5-bromo-3- [1- (ethyl) in a CEM microwave tube containing crude (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) boronic acid (43 mg, 0.188 mmol) Sulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol), dioxane (1.5 mL), H ₂ O (0.5 mL) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) were added. The reaction was heated at 150 ° C. for 30 minutes under CEM microwaves. The reaction mixture was passed through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of H ₂ O (3 mL), MeOH (9 mL) and NH ₃ / MeOH (6 mL). Filtered. The NH ₃ / MeOH fraction was dried at 40 ° C. under a stream of nitrogen, the crude product was dissolved in dimethyl sulfoxide (1 mL) and 10% CH ₃ CN / H ₂ O (0.1% TFA) at 20 mL per minute for 1 minute. Eluted with a linear gradient of 10% CH ₃ CN / H ₂ O (0.1% TFA) to 95% CH ₃ CN / H ₂ O (0.1% TFA) over 8 minutes and held at final concentration for 30 seconds Purification on Agilent MDAP (Zorbox Eclipse XDB-C18 column: 21.2 x 50 mm). Fractions containing product were filtered through a 2 g Parmasil CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA and concentrated at 50 ° C. under a nitrogen stream to give 16.2 mg (17%) of the title compound. It was.

LC / MS = m / z 430.4 [M + H] Retention time: 1.75 minutes.

Example  183: 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl )-2- Thienyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [(1R) -1,2-dimethylpropyl] amine (28 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 30 mg of crude [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-thienyl] boronic acid was replaced with 5-bromo-3- [1- (ethylsulfonyl) -4- Piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) to give 20.5 mg (30%) of the title compound.

LC / MS = m / z 430.4 [M + H] Retention time: 1.75 minutes.

Example  184: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Pentylamino ) methyl ] -2-thienyl} -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for amides, react (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), pentylamine (29 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) To give 45 mg of crude {5-[(pentylamino) methyl] -2-thienyl} boronic acid. The crude {5-[(pentylamino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Reacted with carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) to give 20.7 mg of the title compound ( 20%).

LC / MS = m / z 430.6 [M + H] Retention time: 1.75 minutes.

Example  185: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[(2S) -2- Methylbutyl ] Amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [(2S) -2-methylbutyl] amine (28 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 43 mg of crude [5-({[(2S) -2-methylbutyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[(2S) -2-methylbutyl] amino} methyl) -2-thienyl] boronic acid was replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidi Nil] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol ) Gave 37.6 mg (39%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.67 minutes.

Example  186: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(1- Methylbutyl ) Amino] methyl } -2-T on Nil) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (1-methylbutyl) amine (29 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 43 mg of crude (5-{[(1-methylbutyl) amino] methyl} -2-thienyl) boronic acid. The crude (5-{[(1-methylbutyl) amino] methyl} -2-thienyl) boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Reaction with indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) 35.2 mg (60%) of the title compound were provided.

LC / MS = m / z 430 [M + H] Retention time: 1.62 minutes.

Example  187: 5- {5-[( Butylamino ) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, react (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), butylamine (24 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) To give 49 mg of crude {5-[(butylamino) methyl] -2-thienyl} boronic acid. The crude {5-[(butylamino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Reaction with carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) to give 27.2 mg of the title compound ( 24%).

LC / MS = m / z 430 [M + H] Retention time: 1.56 minutes.

Example  188: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[2- ( Methyloxy ) Ethyl] amino}  methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [2- (methyloxy) ethyl] amine (24 mg, 0.32 mmol) and NaCNBH ₃ ( 40 mg, 0.64 mmol) were reacted to give 42 mg of crude [5-({[2- (methyloxy) ethyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[2- (methyloxy) ethyl] amino} methyl) -2-thienyl] boronic acid was added 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) Reaction with gave the title compound which was not pure. The title compound, which was not pure, was purified as 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H- Repurification using HPLC and workup of ammonium hydroxide SPE as shown in the preparation of indole-7-carboxamide gave 15 mg (15%) of the title compound.

LC / MS = m / z 430.2 [M + H] Retention time: 1.33 minutes.

Example  189: 5- {5-[( Cyclopentylamino ) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), cyclopentylamine (28 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) were added. The reaction gave 48 mg of crude {5-[(cyclopentylamino) methyl] -2-thienyl} boronic acid. The crude {5-[(cyclopentylamino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 -Carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) to give the title compound 93.5 mg (85%) was provided.

LC / MS = m / z 430.4 [M + H] Retention time: 1.64 minutes.

Example  190: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(3- Methylbutyl ) Amino] methyl } -2-T on Nil) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (3-methylbutyl) amine (28 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 46 mg of crude (5-{[(3-methylbutyl) amino] methyl} -2-thienyl) boronic acid. The crude (5-{[(3-methylbutyl) amino] methyl} -2-thienyl) boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Reaction with indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (4 mg, 0.003 mmol) 38.3 mg (37%) of the title compound were provided.

LC / MS = m / z 430.4 [M + H] Retention time: 1.75 minutes.

Example  191: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(1- Methylethyl ) Amino] methyl } -3-p Reedy Nil) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -3-pyridinyl) -1H-indole-7-carbox (Cyclopropylmethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl used to prepare the amide } Amines were prepared as follows: Isopropylamine (0.011 mL, 0.129 mmol) was prepared in 5- (4,4,5,5-tetramethyl-1,3,2 in MeOH (1 mL) in a 2-drum vial. -Dioxaborolan-2-yl) -3-pyridinecarbaldehyde (30 mg, 0.129 mmol) was added to the solution. NaCNBH ₃ (16 mg, 0.258 mmol) was then added, the vial was capped and the reaction stirred at rt for 24 h. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (6 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated under nitrogen stream to afford crude (1-methylethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 22 mg of 3-pyridinyl] methyl} amine was provided.

(1-methylethyl) {[5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -3-pyridinyl] methyl} amine (22 mg, 0.080 mmol) in a CEM microwave tube containing 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (50 mg, 0.121 mmol), K ₂ CO ₃ (100 mg, 0.724 mmol), dioxane (1.5 mL), H ₂ O (0.5 mL) and chloro-2- (dimethylaminomethyl) -ferrocen-1-yl- (dinonorbornylphosphine Palladium (II) (7.3 mg, 0.012 mmol) was added. The reaction was heated at 150 ° C. for 30 minutes under CEM microwaves. The reaction mixture was poured into a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluted with a 2 M solution of H ₂ O (3 mL), MeOH (6 mL) and NH ₃ / MeOH (9 mL). Filtered through. The NH ₃ / MeOH fractions are dried at 50 ° C. under a stream of nitrogen, 20 mL per minute with 10% CH ₃ CN / H ₂ O (0.1% TFA) for 1 minute, followed by 10% CH ₃ CN / over 8 minutes. Agilent MDAP (Gorbox Eclipse XDB-C18 column: 21.2) eluted with a linear gradient of H ₂ O (0.1% TFA) to 95% CH ₃ CN / H ₂ O (0.1% TFA) and held at final concentration for 30 seconds. x 100 mm). Fractions containing product were filtered through a 2 g Parmasil CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA and concentrated at 50 ° C. under a stream of nitrogen to give 27.2 mg (70%) of the title compound. It was.

LC / MS = m / z 484 [M + H] Retention time: 1.25 minutes.

Example  192: 5- (5-{[(2- Ethylbutyl ) Amino] methyl }-2- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox {5-[(ethylamino) methyl] -2-thienyl} boronic acid used to prepare the amide was prepared as follows: (5-formyl-2-thienyl) boron in MeOH (0.5 mL) A solution of acid (50 mg, 0.32 mmol) and a solution of NaCNBH ₃ (40 mg, 0.64 mmol) in MeOH (0.5 mL) were added to (2-ethylbutyl) amine (32 mg, 0.32 mmol) in a 2-drum vial. It was. The vial was capped and the reaction stirred at room temperature for 20 hours. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (6 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated under a nitrogen stream to give 48 mg of crude (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) boronic acid.

5-Bromo- in dioxane (1.75 mL) in a CEM microwave tube containing crude (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) boronic acid (48 mg, 0.199 mmol) A solution of 3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ in H ₂ O (0.25 mL) ( 130 mg, 0.942 mmol) and tetrakis (triphenylphosphinepalladium) (0) (9 mg, 0.0079 mmol) were added. The reaction was heated at 150 ° C. for 30 minutes under CEM microwaves. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH), sequentially eluting with a 2 M solution of MeOH (3 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was dried at 50 ° C. under a stream of nitrogen, the crude product was dissolved in dimethyl sulfoxide (1.1 mL) and 10% CH ₃ CN / H ₂ O (0.1% TFA) at 20 mL per minute for 1 minute. Eluted with a linear gradient of 10% CH ₃ CN / H ₂ O (0.1% TFA) to 95% CH ₃ CN / H ₂ O (0.1% TFA) over 8 minutes and held at final concentration for 30 seconds Purification on Agilent MDAP (Zorbox Eclipse XDB-C18 column: 21.2 x 100 mm). Fractions containing the product were filtered through a 2 g Parmasyl CHQAX column (polymer bound ammonium hydroxide; United Chemical Technologies) to remove TFA and concentrated at 50 ° C. under a stream of nitrogen to provide the title compound as not pure. The crude title compound was re-purified on Agilent MDAP as indicated above and free basified on an ammonium hydroxide column to give 8.5 mg (10%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.72 minutes.

Example  193: 5- [5-({[3- ( Ethyloxy ) Propyl] amino} methyl )-2- Thienyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [3- (ethyloxy) propyl] amine (34 mg, 0.32 mmol) and NaCNBH ₃ ( 40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[3- (ethyloxy) propyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[3- (ethyloxy) propyl] amino} methyl) -2-thienyl] boronic acid was added 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) Reaction with gave 8.1 mg (10%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.62 minutes.

Example  194: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[3- ( Methyloxy ) Propyl] amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [3- (methyloxy) propyl] amine (29 mg, 0.32 mmol) and NaCNBH ₃ ( 40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] boronic acid was replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) Reacted with The crude product is 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 One purification on Agilent MDAP using the procedure shown in the preparation of the carboxamide gave 7.6 mg (9%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.50 minutes.

Example 195: 5- (5 - {[(cyclohexylmethyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl di-carbonyl] -1H- indole- 7 -carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (cyclohexylmethyl) amine (37 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 30 mg of crude (5-{[(cyclohexylmethyl) amino] methyl} -2-thienyl) boronic acid. The crude (5-{[(cyclohexylmethyl) amino] methyl} -2-thienyl) boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Reaction with indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol). The crude product is 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Purification once on Agilent MDAP using the procedure shown in the preparation of -carboxamide. The purified product was washed with a 20: 4: 1 mixture of hexanes / EtOAc / MeOH (2.5 mL), taken up in EtOAc (2 mL) and washed with saturated K ₂ CO ₃ (1 mL). The organic layer was concentrated to give 4.7 mg (6%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.82 minutes.

Example  196: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[({3-[(1- Methylethyl ) Oxy ] Propyl} amino) methyl ]-2- Thienyl } -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), {3-[(1-methylethyl) oxy] propyl} amine (38 mg, 0.32 mmol ), And NaCNBH ₃ (40 mg, 0.64 mmol) to give 30 mg of crude {5-[({3-[(1-methylethyl) oxy] propyl} amino) methyl] -2-thienyl} boronic acid Provided. The crude {5-[({3-[(1-methylethyl) oxy] propyl} amino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl)- 4-piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol), and tetrakis (triphenylphosphine) palladium (0) ( 9 mg, 0.0079 mmol). 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox After twice purification on Agilent MDAP as shown in the preparation of the amide, the crude title compound was washed with a 20: 4: 1 mixture of hexanes / EtOAc / MeOH (2.5 mL) to give 7.6 mg (9%) of the title compound. Provided.

LC / MS = m / z 430 [M + H] Retention time: 1.62 minutes.

Example  197: 5- [5-({[2- ( Ethyloxy ) Ethyl] amino} methyl )-2- Thienyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [2- (ethyloxy) ethyl] amine (30 mg, 0.32 mmol) and NaCNBH ₃ ( 40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[2- (ethyloxy) ethyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[2- (ethyloxy) ethyl] amino} methyl) -2-thienyl] boronic acid was replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) Reacted with The crude product is 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 One purification on Agilent MDAP using the procedure shown for preparation of carboxamide gave 6 mg (7%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.66 minutes.

Example  198: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[3- ( Propyloxy ) Propyl] amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for Ami, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [3- (propyloxy) propyl] amine (38 mg, 0.32 mmol) and NaCNBH ₃ ( 40 mg, 0.64 mmol) were reacted to give 30 mg of crude [5-({[3- (propyloxy) propyl] amino} methyl) -2-thienyl] boronic acid. Then crude [5-({[3- (propyloxy) propyl] amino} methyl) -2-thienyl] boronic acid was added 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) Reacted with The crude product is 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Purification twice on Agilent MDAP using the procedure shown in the preparation of -carboxamide. The purified product was washed with a 20: 4: 1 mixture of hexanes / EtOAc / MeOH (2.5 mL), taken up in EtOAc (2 mL) and washed with saturated K ₂ CO ₃ (1 mL). The organic layer was concentrated to give 1.4 mg (2%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.66 minutes.

Example  199: 5- (5-{[(3,3- Dimethylbutyl ) Amino] methyl }-2- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), (3,3-dimethylbutyl) amine (32 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) was reacted to give 30 mg of crude (5-{[(3,3-dimethylbutyl) amino] methyl} -2-thienyl) boronic acid. Then crude (5-{[(3,3-dimethylbutyl) amino] methyl} -2-thienyl) boronic acid was converted to 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) Reaction gave 4.5 mg (5%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.79 minutes.

Example  200: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[(1S) -1,2,2- Trimethylpropyl ] Amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), [(1S) -1,2,2-trimethylpropyl] amine (32 mg, 0.32 mmol ) And NaCNBH ₃ (40 mg, 0.64 mmol) give 30 mg of crude [5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) -2-thienyl] boronic acid It was. Then crude [5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) -2-thienyl] boronic acid was replaced with 5-bromo-3- [1- (ethylsulfonyl)- 4-piperidinyl] -1H-indole-7-carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol) gave 10.3 mg (12%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.62 minutes.

Example  201: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Hexylamino ) methyl ]-2- Thienyl } -1H-indole-7- Carboxamide

5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox According to the general procedure for the amide, react (5-formyl-2-thienyl) boronic acid (50 mg, 0.32 mmol), hexylamine (33 mg, 0.32 mmol) and NaCNBH ₃ (40 mg, 0.64 mmol) To give 30 mg of crude {5-[(hexylamino) methyl] -2-thienyl} boronic acid. The crude {5-[(hexylamino) methyl] -2-thienyl} boronic acid was then replaced with 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- It was reacted with carboxamide (65 mg, 0.157 mmol), K ₂ CO ₃ (130 mg, 0.942 mmol) and tetrakis (triphenylphosphine) palladium (0) (9 mg, 0.0079 mmol). The crude product is 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 One purification on Agilent MDAP using the procedure shown in the preparation of carboxamides gave 13 mg (16%) of the title compound.

LC / MS = m / z 430.6 [M + H] Retention time: 1.92 minutes.

Example  202: 5- [2- (dimethylamino) -4- Pyridinyl ] -3- [1- ( Ethylsulfonyl )-4- Piperi Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

Dimethyl in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-4-pyridinyl) -1H-indole-7-carboxamide (40 mg, 0.093 mmol) Amine (1 mL, 0.015 mmol) and DMF (0.3 mL) were added. The resulting mixture was reacted at 180 ° C. for 1 hour under microwave. All solvents were evaporated and the mixture was then purified by Gilson preparative HPLC to give 18.2 mg (34.4%) of the title compound.

LC / MS = m / z 456.2 [M + H] Retention time: 1.54 minutes.

Example  203: 5- {6- [ethyl ( methyl ) Amino] -3- Pyridinyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with pyrrolidine (1 mL) and replace the title compound with 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] Prepared according to the general procedure for -1H-indole-7-carboxamide trifluoroacetate to give 48.9 mg (27.1%) of the title compound.

LC / MS = m / z 482.2 [M + H] Retention time: 1.62 minutes.

Example  204: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (4- Morpholinyl )-4- Pipe Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with morpholine (1 mL) and replace the title compound with 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl]- Prepared according to the general procedure for 1H-indole-7-carboxamide trifluoroacetate to give 12 mg (21.1%) of the title compound.

LC / MS = m / z 498.6 [M + H] Retention time: 1.47 minutes.

Example  205: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {2-[(2- Methylpropyl ) Amino] -4- blood Ridinyl} -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with 2-methyl-1-propanamine (1 mL) and replace the title compound with 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4 Prepared according to the general procedure for -piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 11.1 mg (20%) of the title compound.

LC / MS = m / z 484.2 [M + H] Retention time: 1.68 minutes.

Example  206: 5- {2-[(2,2-dimethylpropyl) amino] -4- Pyridinyl } -3- [1- ( Ethyl sulfo Nil) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with 2,2-dimethyl-1-propanamine (1 mL) and replace the title compound with 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) Prepared according to the general procedure for -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 9 mg (15.8%) of the title compound.

LC / MS = m / z 498.6 [M + H] Retention time: 1.75 minutes.

Example  207: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- ( Propylamino )-4- Pipe Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with propylamine (1 mL) and replace the title compound with 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl]- Prepared according to the general procedure for 1H-indole-7-carboxamide trifluoroacetate to give 18.2 mg (33.5%) of the title compound.

LC / MS = m / z 470.4 [M + H] Retention time: 1.57 minutes.

Example  208: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4-[( Methylamino ) methyl ] -2-thienyl} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formyl-2-thienyl) -1H-indole-7 in methylene chloride (2 mL) and methanol (1 mL) To a solution of carboxamide (45 mg, 0.1 mmol) 2 M methylamine (0.5 mL) was added. The reaction mixture was stirred at rt for 5 h and then sodium tetrahydridoborate (37.83 mg, 1 mmol) was added. The resulting mixture was stirred at rt overnight. The solvent was concentrated and purified by Gilson preparative HPLC to give 16.8 mg (29.2%) of the title compound.

LC / MS = m / z 461.6 [M + H] Retention time: 1.40 minutes.

Example  209: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (1- Pyrrolidinylmethyl ) -2-thienyl] -1 H-indole-7- Carboxamide Trifluoroacetate

Replace the 2 M methylamine with pyrrolidine (0.083 mL) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl]- Prepared according to the general procedure for 2-thienyl} -1H-indole-7-carboxamide trifluoroacetate to give 14.8 mg (24.1%) of the title compound.

LC / MS = m / z 470.4 [M + H] Retention time: 1.57 minutes.

Example  210: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[(2- Methylpropyl ) Amino] methyl }-2- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2 M methylamine with 2-methyl-1-propanamine (0.1 mL) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methyl Prepared according to the general procedure for amino) methyl] -2-thienyl} -1H-indole-7-carboxamide trifluoroacetate to give 15.4 mg (25%) of the title compound.

LC / MS = m / z 503.2 [M + H] Retention time: 1.42 minutes.

Example  211: 5- {4-[(dimethylamino) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2 M methylamine with dimethylamine (0.5 mL) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl] -2 Prepared according to the general procedure for -thienyl} -1H-indole-7-carboxamide trifluoroacetate to give 9 mg (15.3%) of the title compound.

LC / MS = m / z 475.2 [M + H] Retention time: 1.27 minutes.

Example  212: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(1S) -1- (1- Pyrrolidinyl ) Ethyl] -3-T on Nil} -1H-indole-7- Carboxamide

Sodium cya to 5- (5-acetyl-3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (10 mg, 0.02 mmol) Novohydride (7.5 mg, 0.12 mmol) and pyrrolidine (0.03 mL, 0.30 mmol) were added. The resulting mixture was reacted at 150 ° C. for 40 minutes under microwave. All solvents were evaporated and the crude product was partitioned between ethyl acetate (1.5 mL) and 1 M sodium hydroxide (0.2 mL). The reaction was purified by SFC to provide the title compound as 100% pure chiral construct.

LC / MS = m / z 515.4 [M + H] Retention time: 1.54 minutes.

Example  213: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[(1R) -1- (1- Pyrrolidinyl ) Ethyl] -3- Thienyl } -1H-indole-7- Carboxamide

Sodium cya to 5- (5-acetyl-3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (10 mg, 0.02 mmol) Novohydride (7.5 mg, 0.12 mmol) and pyrrolidine (0.03 mL, 0.30 mmol) were added. The resulting mixture was reacted at 150 ° C. for 40 minutes under microwave. All solvents were evaporated and the crude product was partitioned between ethyl acetate (1.5 mL) and 1 M sodium hydroxide (0.2 mL). The reaction was purified by SFC to provide the title compound as 100% pure chiral construct.

LC / MS = m / z 515.4 [M + H] Retention time: 1.54 minutes.

Example  214: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({[3- ( Methyloxy ) Propyl] amino} methyl )-2- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

5-[(1Z) -1- (ethenylthio) -4-oxo-1-buten-1-yl] -3- [1- (ethylsulfonyl) in methylene chloride (2 mL) and methanol (1 mL) 3 drops of acetic acid and 3- (methyloxy) -1-propanamine (89.14 mg, 1 mmol) in a solution of) -4-piperidinyl] -1H-indole-7-carboxamide (45 mg, 0.1 mmol) ) Was added. The resulting mixture was stirred for 6 hours, then sodium borohydride (37.83 mg, 1 mmol) was added. The reaction was stirred at rt overnight. The solvent was evaporated and the mixture was then purified by Gilson preparative HPLC to give 23.7 mg (37.5%) of the title compound.

LC / MS = m / z 519.4 [M + H] Retention time: 1.69 minutes.

Example  215: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4-({(2S) -2-[( Methyloxy ) Me Teal] -1- Pyrrolidinyl } methyl )-2- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 3- (methyloxy) -1-propanamine with (2S) -2-[(methyloxy) methyl] pyrrolidine (115.18 mg, 1 mmol) and replace the title compound with 3- [1- (ethylsul Ponyl) -4-piperidinyl] -5- [4- ({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7-carboxamide trifluoroacetate Prepared according to the general procedure for 3 mg (4.6%) of the title compound was obtained.

LC / MS = m / z 545.2 [M + H] Retention time: 1.78 minutes.

Example  216: 5- (4-{[(2R, 5R) -2,5-dimethyl-1- Pyrrolidinyl ] methyl }-2- Thienyl ) -3- [1- (in Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

In place of 3- (methyloxy) -1-propanamine, the title compound is replaced by 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[3- (methyloxy) Prepared according to the general procedure for propyl] amino} methyl) -2-thienyl] -1H-indole-7-carboxamide trifluoroacetate to give 6.4 mg (10%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.69 minutes.

Example  217: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2S) -2- methyl -One- Pyrrolidinyl ] Methyl} -3- Thienyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (10 mL) ( To 600 mg, 1.348 mmol) was added 20 drops of acetic acid and (2S) -1,2-dimethylpyrrolidine (1.37 mL, 13.483 mmol). The resulting mixture was stirred at rt for 6 h, then sodium triacetoxyborohydride (2.858 g, 13.483 mmol) was added. The reaction was stirred at rt overnight and then purified by SFC. This compound was separated by RTP CASS group. Fraction of enantiomer # 1 was 99.7% pure chiral construct which gave 119.9 mg (17.3%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.56 minutes.

Example  218: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2R) -2- methyl -One- Pyrrolidinyl ] Methyl} -3- Thienyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (10 mL) ( To a solution of 600 mg, 1.35 mmol) 20 drops of acetic acid and 2-methylpyrrolidine (1.37 mL, 13.5 mmol) were added. The resulting mixture was stirred at rt for 6 h, then sodium triacetoxyborohydride (2.86 g, 13.5 mmol) was added. The reaction was stirred at rt overnight and then purified by Gilson preparative HPLC. This compound was then separated to provide the title compound as a 98.6% pure chiral construct.

LC / MS = m / z 515.4 [M + H] Retention time: 1.56 minutes.

Example  219: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5- [1- (1- Pyrrolidinyl ) Propyl] -3-thienyl} -1 H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (4.5 mL) and H ₂ O (1.5 mL) 1- (4-bromo-2-thienyl) -1-propanone in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (250 mg, 0.541 mmol) (356 mg, 1.62 mmol), potassium carbonate (447 mg, 3.24 mmol) and tetrakis (triphenylphosphine) palladium (0) (64 mg, 0.055 mmol) were added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. Aqueous workup with EtOAc and H ₂ O was followed by addition of MeOH (20 mL) to the crude product. The desired product precipitated out and was filtered to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-propanoyl-3-thienyl) -1H-indole-7-carbox 110 mg (43%) of amide were provided.

In 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-propanoyl-3-thienyl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol) Sodium cyanoborohydride (49.2 mg, 0.78 mmol), pyrrolidine (0.2 mL, 1.95 mmol), ethanol (3 mL) and acetic acid (0.4 mL) were added. The resulting mixture was reacted at 150 ° C. for 30 minutes under microwave. All solvents were evaporated and the mixture was purified by Gilson preparative HPLC to give 12 mg (14.4%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.65 minutes.

Example  220: 5- {5-[(dimethylamino) methyl ] -3- Thienyl } -3- {1-[(1- Methylethyl ) Sulfo Nil] -4-piperidinyl} -1 H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (2 mL) ( To 50 mg, 0.11 mmol) was added 3 drops of acetic acid and trimethylamine (0.55 mL, 1.1 mmol). The resulting mixture was stirred at rt for 6 h, then sodium triacetoxyborohydride (233 mg, 1 mmol) was added. It was then stirred overnight at room temperature and then purified by Gilson preparative HPLC to give 29.4 mg (44.3%) of the title compound.

LC / MS = m / z 489.4 [M + H] Retention time: 1.32 minutes.

Example  221: 5- [5- ( Aminomethyl ) -3- Thienyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in methylene chloride (2 mL) and methanol (1 mL) To a solution of carboxamide (50 mg, 0.11 mmol) was added ammonium acetate (84.7 mg, 1.1 mmol) and sodium cyanoborohydride (4.84 mg, 0.077 mmol). The resulting mixture was stirred at rt overnight. All solvents were evaporated and the mixture was purified by Gilson preparative HPLC to give 1.8 mg (2.9%) of the title compound.

LC / MS = m / z 447.2 [M + H] Retention time: 1.53 minutes.

Example  222: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5- {2-[(2- Methylpropyl ) Amino] ethyl} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of [2- (4-bromo-2-thienyl) ethyl] amine (100 mg, 0.48 mmol) in DCM (2.0 mL) and MeOH (1.0 mL) acetic acid (3 drops) and 2-methylpropanal (105 mg, 1.44 mmol) was added. The reaction was stirred overnight at room temperature and then sodium borohydride (53.3 mg, 1.44 mmol) was added. After reacting for 1 hour, the mixture was treated with EtOAc and brine. The organic layer was then dried and concentrated to give 80 mg (64%) of [2- (4-bromo-2-thienyl) ethyl] (1-methylethyl) amine.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (3 mL) and water (1 mL) [2- (4-bromo-2-thienyl) ethyl] (1-methyl) in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (139 mg, 0.3 mmol) Ethyl) amine (50 mg, 0.2 mmol), potassium carbonate (82.8 mg, 0.6 mmol) and tetrakis (triphenylphosphine) palladium (0) (22 mg, 0.019 mmol) were added. The resulting mixture was reacted at 150 ° C. for 20 minutes under microwave. All solvents were evaporated and the mixture was purified by Gilson preparative HPLC to give 18 mg (9.5%) of the title compound.

LC / MS = m / z 517.2 [M + H] Retention time: 1.68 minutes.

Example  223: 5- {5- [2- (dimethylamino) ethyl] -3- Thienyl } -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

To a solution of [2- (4-bromo-2-thienyl) ethyl] amine (100 mg, 0.48 mmol) in DCM (2.0 mL) and MeOH (1.0 mL) acetic acid (3 drops) and formaldehyde (H ₂ 37% in 0) (105 mg, 1.44 mmol) was added. The reaction was stirred at rt overnight then sodium borohydride (53.3 mg, 1.44 mmol) was added. After reacting for 1 hour, the mixture was treated with EtOAc and brine. The organic layer was then dried and concentrated to give 50 mg (44%) of 2- (4-bromo-2-thienyl) -N, N-dimethylethanamine.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (3 mL) and water (1 mL) 2- (4-bromo-2-thienyl) -N, N-dimethylethane in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (139 mg, 0.345 mmol) Amine (50 mg, 0.23 mmol), potassium carbonate (82.8 mg, 0.69 mmol) and tetrakis (triphenylphosphine) palladium (0) (22 mg, 0.019 mmol) were added. The resulting mixture was reacted at 150 ° C. for 20 minutes under microwave. All solvents were evaporated and the mixture was purified by Gilson preparative HPLC to give 12 mg (5.8%) of the title compound.

LC / MS = m / z 489.2 [M + H] Retention time: 1.54 minutes.

Example  224: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- (1- Pyrrolidinyl ) -3- Pipe Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (110 mg) in dioxane (2.0 mL) and H ₂ O (0.7 mL) , 0.27 mmol) in (6-fluoro-3-pyridinyl) boronic acid (151 mg, 1.08 mmol), potassium carbonate (298 mg, 2.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (31 mg, 0.026 mmol) was added. The reaction was performed at 150 ° C. for 20 minutes under microwave. The reaction was then treated with EtOAc and brine and purified by flash chromatography to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole 50 mg (43%) of -7-carboxamide were provided.

Blood in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole-7-carboxamide (25 mg, 0.058 mmol) Rollidine (3 mL) was added. The resulting mixture was reacted at 100 ° C. for 30 minutes under microwave. All excess pyrrolidine was evaporated and then purified by Gilson preparative HPLC to give 25 mg (72.4%) of the title compound.

LC / MS = m / z 482.2 [M + H] Retention time: 1.67 minutes.

Example  225: 5- {6- [ethyl ( methyl ) Amino] -3- Pyridinyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (110 mg) in dioxane (2.0 mL) and H ₂ O (0.7 mL) , 0.27 mmol) in (6-fluoro-3-pyridinyl) boronic acid (151 mg, 1.08 mmol), potassium carbonate (298 mg, 2.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (31 mg, 0.026 mmol) was added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. The reaction was then treated with EtOAc and brine and purified by flash chromatography to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole 50 mg (43%) of -7-carboxamide were provided.

Dimethyl in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole-7-carboxamide (40 mg, 0.093 mmol) Amine (1 mL) and DMF (0.3 mL) were added. The resulting mixture was reacted at 200 ° C. for 1 hour under microwave. The resulting mixture was washed with water. Ethyl acetate was added and the organic layer was evaporated and purified by Gilson preparative HPLC to give 34.4 mg (63.4%) of the title compound.

LC / MS = m / z 470 [M + H] Retention time: 1.50 minutes.

Example  226: 5- [6- (dimethylamino) -3- Pyridinyl ] -3- [1- ( Ethylsulfonyl )-4- Piperi Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (110 mg) in dioxane (2.0 mL) and H ₂ O (0.7 mL) , 0.27 mmol) in (6-fluoro-3-pyridinyl) boronic acid (151 mg, 1.08 mmol), potassium carbonate (298 mg, 2.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (31 mg, 0.026 mmol) was added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. The reaction was then treated with EtOAc and brine and purified by flash chromatography to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole 50 mg (43%) of -7-carboxamide were provided.

Dimethyl in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole-7-carboxamide (50 mg, 0.116 mmol) Amine (1 mL) and DMF (0.3 mL) were added. The resulting mixture was reacted under microwave for 1 hour at 200 ° C. and purified by Gilson preparative HPLC to give 8.4 mg (12.7%) of the title compound.

LC / MS = m / z 456.2 [M + H] Retention time: 1.39 minutes.

Example  227: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- ( Propylamino ) -3- Pipe Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (110 mg) in dioxane (2.0 mL) and H ₂ O (0.7 mL) , 0.27 mmol) in (6-fluoro-3-pyridinyl) boronic acid (151 mg, 1.08 mmol), potassium carbonate (298 mg, 2.16 mmol) and tetrakis (triphenylphosphine) palladium (0) (31 mg, 0.026 mmol) was added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. The reaction was then treated with EtOAc and brine and purified by flash chromatography to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole 50 mg (43%) of -7-carboxamide were provided.

Propyl in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (6-fluoro-3-pyridinyl) -1H-indole-7-carboxamide (50 mg, 0.116 mmol) Amine (1 mL) and DMF (0.3 mL) were added. The resulting mixture was reacted under microwave for 5 hours at 200 ° C. and purified by Gilson preparative HPLC to give 24.5 mg (36.2%) of the title compound.

LC / MS = m / z 470.2 [M + H] Retention time: 1.49 minutes.

Example  228: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {6-[(1- Methylethyl ) Amino] -3- Pyridinyl } -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with 2-propanamine (64.3 mg, 1 mmol) and replace the title compound with 5- {6- [ethyl (methyl) amino] -3-pyridinyl} -3- [1- (ethylsulfonyl) Prepared according to the general procedure for -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 9.8 mg (14.5%) of the title compound.

LC / MS = m / z 470.4 [M + H] Retention time: 1.52 minutes.

Example  229: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- (4- Morpholinyl ) -3- Pyridinyl ] -1H-indole-7- Carboxamide

Replace the dimethylamine with morpholine (1 mL) and replace the title compound with 5- {6- [ethyl (methyl) amino] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidi Prepared according to the general procedure for nil] -1H-indole-7-carboxamide trifluoroacetate to give 40.1 mg (69.5%) of the title compound.

LC / MS = m / z 498.6 [M + H] Retention time: 1.44 minutes.

Example  230: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Methylamino ) methyl ] -3-thienyl} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in methanol (1.5 mL) and methylene chloride (1.5 mL) To a solution of carboxamide (20 mg, 0.045 mmol) was added methylamine (0.13 mL). The resulting mixture was stirred at rt for 2 h and then sodium tetrahydridoborate (9.18 mg, 0.27 mmol) was added. It was stirred at rt for 1 h. All solvents were evaporated and then purified by Gilson preparative HPLC to give 12.4 mg (48%) of the title compound.

LC / MS = m / z 461.4 [M + H] Retention time: 1.48 minutes.

Example  231: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(1- Methylethyl ) Amino] methyl} -3-ti on Nil) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in methanol (0.5 mL) and methylene chloride (1 mL) To a solution of carboxamide (30 mg, 0.067 mmol) was added 2-propanamine (23.8 mg, 0.402 mmol). The resulting mixture was stirred for 2.5 hours, then sodium tetrahydridoborate (15.2 mg, 0.402 mmol) was added. The reaction was stirred at rt for 1 h. All solvents were evaporated and then purified by Gilson preparative HPLC to give 19.5 mg (48.3%) of the title compound.

LC / MS = m / z 489.2 [M + H] Retention time: 1.54 minutes.

Example  232: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- Pyrrolidinylmethyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in methanol (0.5 mL) and methylene chloride (1 mL) To a solution of -carboxamide (30 mg, 0.067 mmol) was added pyrrolidine (85 mg, 1.195 mmol). The resulting mixture was stirred for 1.5 h, then sodium triacetoxyborohydride (85 mg, 0.402 mmol) was added. The reaction was stirred at rt for 2 h. All solvents were evaporated and then purified by Gilson preparative HPLC to give 22.5 mg (54.6%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.52 minutes.

Example  233: 5- {5-[( Ethylamino ) methyl ] -3- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Pipe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7 in methanol (3 mL) and methylene chloride (3 mL) To a solution of carboxamide (30 mg, 0.067 mmol) was added ethylamine (0.2 mL, 0.402 mmol). After 2 hours sodium tetrahydridoborate (27 mg, 0.402 mmol) was added and the mixture was allowed to stand for 1 hour. All solvents were evaporated and then purified by Gilson preparative HPLC to give 15 mg (38%) of the title compound.

LC / MS = m / z 475.4 [M + H] Retention time: 1.52 minutes.

Example  234: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({[(1R) -2-hydroxy-1- Methyl ethyl ] Amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate  (salt)

Replace the ethylamine with (2R) -2-amino-1-propanol (0.031 mL, 0.402 mmol) and replace the title compound with 5- {5-[(ethylamino) methyl] -3-thienyl} -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 16.2 mg (39.1%) of the title compound.

LC / MS = m / z 505.4 [M + H] Retention time: 1.42 minutes.

Example  235: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- Piperidinylmethyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (2 mL) ( To a solution of 30 mg, 0.067 mmol) piperidine (70 mg, 0.670 mmol) was added. The resulting mixture was left for 2 hours, then sodium triacetoxyborohydride (142 mg, 0.670 mmol) was added. The mixture was stirred at rt overnight and then purified by Gilson preparative HPLC to give 16.2 mg (38.5%) of the title compound.

LC / MS = m / z 514.8 [M + H] Retention time: 1.37 minutes.

Example  236: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (4- Morpholinylmethyl ) -3-thienyl] -1 H-indole-7- Carboxamide Trifluoroacetate

Replace title of piperidine with morpholine (70 mg, 0.670 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl Prepared according to the general procedure for) -3-thienyl] -1H-indole-7-carboxamide trifluoroacetate to give 6.3 mg (14.9%) of the title compound.

LC / MS = m / z 517 [M + H] Retention time: 1.54 minutes.

Example  237: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Methylamino ) methyl ] -3-furanyl} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3.0 mL) and H ₂ O (1.0 mL) 4-bromo-2-furancarbaldehyde (58 mg, 0.33 mmol) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (50 mg, 0.11 mmol) , Potassium carbonate (89.8 mg, 0.66 mmol) and tetrakis (triphenylphosphine) palladium (0) (14 mg, 0.012 mmol) were added. The reaction was heated at 150 ° C. under microwave for 20 minutes to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-furanyl) -1H-indole-7- 58 mg of carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-furanyl) -1H-indole-7-carboxamide (20.6 mg in DMSO (0.5 mL) , 0.05 mmol) was added methylamine (0.24 mL, 0.5 mmol) in 2 M tetrahydrofuran. The resulting mixture was reacted for 6 hours and then sodium triacetoxyborohydride was added. Purification by Gilson preparative HPLC gave 5.5 mg (32.8%) of the title compound.

LC / MS = m / z 459.4 [M + H] Retention time: 1.42 minutes.

Example  238: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5- [1- (1- Pyrrolidinyl ) Ethyl] -3- Thienyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (9 mL) and H ₂ O (3 mL) 1- (4-bromo-2-thienyl) ethanone (400 mg) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (300 mg, 0.65 mmol) , 1.95 mmol), potassium carbonate (538 mg, 3.90 mmol) and tetrakis (triphenylphosphine) palladium (0) (70 mg, 0.060 mmol) were added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. Aqueous workup with EtOAc and H ₂ O was followed by addition of MeOH (3 mL) to the crude product. The desired product precipitated out and was filtered to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-propanoyl-3-thienyl) -1H-indole-7-carr 230 mg (77%) of boxamide was provided.

5- (5-acetyl-3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbine in DMF (0.8 mL) and acetic acid (0.2 mL) To a solution of voxamide (50 mg, 0.11 mmol) was added pyrrolidine (30.92 mg, 0.44 mmol) and N, N-dimethylformamide (30 mg, 0.44 mmol). The reaction mixture was reacted at 150 ° C. for 20 minutes under microwave. The product was then purified twice by Gilson preparative HPLC to give 3.7 mg (5.3%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.62 minutes.

Example  239: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- Pyrrolidinylmethyl )-2- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-2-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (0.5 mL) ( 40 mg, 0.09 mmol) was added 2 M pyrrolidine (0.074 mL, 0.90 mmol). The resulting mixture was left for 6 hours and then sodium triacetoxyborohydride (233 mg, 9.90 mmol) was added. It was then left to stand for 2 hours and then purified by Gilson preparative HPLC to give 6.5 mg (11.7%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.62 minutes.

Example  240: 5- {5-[(dimethylamino) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- Piperidi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-2-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (0.5 mL) ( 35 mg, 0.09 mmol) was added 2 M dimethylamine (0.4 mL, 0.90 mmol). The resulting mixture was left for 6 hours and then sodium triacetoxyborohydride (233 mg, 9.90 mmol) was added. It was then left to stand for 2 hours and then purified by Gilson preparative HPLC to give 17.8 mg (33.6%) of the title compound.

LC / MS = m / z 475.2 [M + H] Retention time: 1.53 minutes.

Example  241: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5-[( Propylamino ) methyl ] -2-T on Nil} -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2 M dimethylamine with propylamine (0.064 mL, 0.90 mmol) and replace the title compound with 5- {5-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) Prepared according to the general procedure for -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to yield 8.9 mg (16.4%) of the title compound.

LC / MS = m / z 487.2 [M + H] Retention time: 1.80 minutes.

Example  242: 5- {5-[( Diethylamino ) methyl ]-2- Thienyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2 M dimethylamine with diethylamine (0.081 mL, 0.90 mmol) and replace the title compound with 5- {5-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl Prepared according to the general procedure for) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 16.6 mg (29.9%) of the title compound.

LC / MS = m / z 502.0 [M + H] Retention time: 1.71 minutes.

Example  243: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Methylpropyl ) Amino] Me Teal} -2- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-2-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (0.5 mL) ( 30 mg, 0.09 mmol) was added 2-methyl-1-propanamine (0.068 mL, 0.90 mmol). The resulting mixture was left for 6 hours and then sodium triacetoxyborohydride (233 mg, 9.90 mmol) was added. It was then left to stand for 2 hours and then purified by Gilson preparative HPLC to give 2.7 mg (4.9%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.79 minutes.

Example  244: 5- (5-{[(2,2-dimethylpropyl) amino] methyl } -3- Furanil ) -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3.0 mL) and H ₂ O (1.0 mL) 4-bromo-2-furancarbaldehyde (58 mg, 0.33 mmol) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (50 mg, 0.11 mmol) , Potassium carbonate (89.8 mg, 0.66 mmol) and tetrakis (triphenylphosphine) palladium (0) (14 mg, 0.012 mmol) were added. The reaction was heated at 150 ° C. under microwave for 20 minutes to afford 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-furanyl) -1H-indole-7- 58 mg of carboxamide were provided.

Dimethyl in 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-furanyl) -1H-indole-7-carboxamide (60 mg, 0.14 mmol) 2,2-Dimethyl-1-propanamine (60 mg, 0.14 mmol) in sulfoxide (0.5 mL) was added. The resulting mixture was allowed to stand for 6 hours and then sodium triacetoxyborohydride (233 mg, 9.90 mmol) was added. It was then left for 2 hours and then purified by Gilson preparative HPLC to give 23.8 mg (27.7%) of the title compound.

LC / MS = m / z 501.1 [M + H] Retention time: 1.67 minutes.

Example  245: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2- Methylpropyl ) Amino] Me Teal} -3- Furanil ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2,2-dimethyl-1-propanamine with 2-methyl-1-propanamine (102.4 mg, 1.4 mmol) and replace the title compound with 5- (5-{[(2,2-dimethylpropyl) amino]. Methyl} -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for the title compound 31.7 mg (37.7%) were obtained.

LC / MS = m / z 487.2 [M + H] Retention time: 1.44 minutes.

Example  246: 5- (5-{[( Cyclopentylmethyl ) Amino] methyl } -3- Furanil ) -3- [1- ( Ethyl alcohol Ponyl) -4-P Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

Replace 2,2-dimethyl-1-propanamine with 1-cyclopentylmethanamine (137 mg, 1.4 mmol) and replace the title compound with 5- (5-{[(2,2-dimethylpropyl) amino] methyl}. 22 mg of the title compound prepared according to the general procedure for -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate (25.1%) was obtained.

LC / MS = m / z 513.4 [M + H] Retention time: 1.59 minutes.

Example  247: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- Pyrrolidinylmethyl ) -3-furanyl] -1 H-indole-7- Carboxamide Trifluoroacetate

Replace 2,2-dimethyl-1-propanamine with pyrrolidine (99.6 mg, 1.4 mmol) and replace the title compound with 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3- 6 mg (7.2%) of the title compound prepared according to the general procedure for furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate ) Was obtained.

LC / MS = m / z 485.2 [M + H] Retention time: 1.50 minutes.

Example  248: 5- {5-[( Diethylamino ) methyl ] -3- Furanil } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2,2-dimethyl-1-propanamine with 2 M diethylamine (102.4 mg, 1.4 mmol) and replace the title compound with 5- (5-{[(2,2-dimethylpropyl) amino] methyl}-. 10.1 mg of the title compound prepared according to the general procedure for 3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate ( 12%) was obtained.

LC / MS = m / z 487.4 [M + H] Retention time: 1.50 minutes.

Example  249: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- Pyrrolidinylmethyl ) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (12 mL) and H ₂ O (4 mL) In a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (500 mg, 1.1 mmol) 2-bromo-1,3-thiazole-5-carbaldehyde ( 634 mg, 3.3 mmol), potassium carbonate (898 mg, 8.8 mmol) and tetrakis (triphenylphosphine) palladium (0) (210 mg, 0.181 mmol) were added. The reaction was carried out at 150 ° C. for 20 minutes under microwave. Aqueous workup gave the crude product. The reaction was then repeated at 150 ° C. under microwave for 30 minutes to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-1,3-thiazol-2-yl) -1H-indole-7-carboxamide was provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-1,3-thiazol-2-yl) -1H-indole- in dimethyl sulfoxide (1 mL) To a solution of 7-carboxamide (25 mg, 0.06 mmol) was added pyrrolidine (0.05 mL, 0.60 mmol). The resulting mixture was stirred at rt for 6 h and then sodium triacetoxyborohydride (160 mg, 0.60 mmol) was added. The resulting mixture was stirred overnight and then purified by Gilson preparative HPLC to give 6.3 mg (17.1%) of the title compound.

LC / MS = m / z 502.2 [M + H] Retention time: 1.35 minutes.

Example  250: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {5- [2- methyl -1- (1- Pyrrolididi Nil) propyl] -3- Thienyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (3 mL) and H ₂ O (1 mL) Potassium carbonate (89.8 mg, 0.66 mmol), 1- (4-bromo-) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (50 mg, 0.11 mmol) 2-thienyl) -2-methyl-1-propanone (87 mg, 0.33 mmol) and tetrakis (triphenylphosphine) palladium (0) (14 mg, 0.012 mmol) were added. The reaction was reacted at 150 ° C. for 20 minutes under microwave, followed by aqueous workup with EtOAc and H ₂ O. The reaction was then concentrated, treated with 1 N NaOH and extracted with EtOAc. The compound was purified by flash chromatography using DCM and MeOH to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (2-methylpropanoyl) -3-thienyl ] -1H-indole-7-carboxamide was provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (2-methylpropanoyl) -3-thienyl]-in EtOH (1.5 mL) and acetic acid (0.2 mL) To a solution of 1H-indole-7-carboxamide (40 mg, 0.02 mmol) was added sodium cyanoborohydride (7.5 mg, 0.12 mmol) and pyrrolidine (0.03 mL, 0.3 mmol). The resulting mixture was reacted at 150 ° C. for 40 minutes under microwave. All solvents were then evaporated, basified in sodium hydroxide and extracted with ethyl acetate. It was then purified by Gilson preparative HPLC to give 13 mg of the title compound.

LC / MS = m / z 543.4 [M + H] Retention time: 1.71 minutes.

Example  251: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (1- Pyrrolidinylmethyl ) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-formyl-1,3-thiazol-4-yl) -1H-indole-7- in DMSO (2 mL) To a solution of carboxamide (42 mg, 0.094 mmol) was added pyrrolidine (0.08 mL, 0.940 mmol). The resulting mixture was stirred at rt for 6 h and then sodium triacetoxyborohydride was added. The mixture was stirred at rt overnight and then purified by Gilson preparative HPLC to give 15.1 mg (26.1%) of the title compound.

LC / MS = m / z 502.4 [M + H] Retention time: 1.54 minutes.

Example  252: 5- {1- [2- (dimethylamino) ethyl] -1 H- Pyrazole -4-yl} -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H- Indole-7-carboxamide (40 mg, 0.084 mmol), [2- (4-bromo-1H-pyrazol-1-yl) ethyl] dimethylamine (27 mg, 0.126 mmol) and sodium carbonate (53 mg, 0.5 mmol) was suspended in dioxane (750 μl) and water (250 μl). It was flushed with argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) was added. The resulting mixture was reacted for 20 minutes at 120 ° C. under microwaves and then diluted with EtOAc (10 mL). The mixture was filtered through celite and aqueous washed. It was then purified by Gilson preparative HPLC to give 6 mg (15%) of the title compound.

LC / MS = m / z 473.4 [M + H] Retention time: 1.48 minutes.

Example  253: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {1- [2- (1- Pyrrolidinyl Ethyl] -1 H- Pyrazole -4-yl} -1 H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (750 μl) and H ₂ O (250 μl) Sodium carbonate (53 mg, 0.50 mmol) and 4-bromo-1- (2) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (40 mg, 0.090 mmol) -Chloroethyl) -1H-pyrazole (26 mg, 0.126 mmol) was added. The reaction mixture was flushed under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) was added. The reaction was heated at 120 ° C. for 20 minutes under microwave. Then diluted with EtOAc (10 mL), filtered through celite and then aqueous workup. The compound was purified by Gilson preparative HPLC to give 5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H 10 mg (24%) of indole-7-carboxamide was provided.

5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ( Tetrahydrofuran (500 μl) was added to a solution of 33 mg, 0.071 mmol), pyrrolidine (60 μl, 0.710 mmol) and sodium iodide (5 mg, 0.018 mmol). This mixture was reacted under microwave for 2 hours at 130 ° C. and washed with EtOAc and water. The organic layer was then isolated and all solvent removed. It was then purified by Gilson preparative HPLC to give 11 mg (25%) of the title compound.

LC / MS = m / z 499.6 [M + H] Retention time: 1.34 minutes.

Example  254: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {1- [2- (4- Morpholinyl Ethyl] -1 H- Pyrazole -4-yl} -1 H-indole-7- Carboxamide Trifluoroacetate

The title compound was substituted with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {1- [2- (1-pipe), replacing pyrrolidine with morpholine (70 μl, 0.71 mmol) Prepared according to the general procedure for rolidinyl) ethyl] -1H-pyrazol-4-yl} -1H-indole-7-carboxamide trifluoroacetate to give 15 mg (34%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.46 minutes.

Example  255: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (1- {2-[(2- Hydroxyethyl ) Amino] ethyl} -1H- Pyrazole -4-yl) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (750 μl) and H ₂ O (250 μl) Sodium carbonate (53 mg, 0.50 mmol) and 4-bromo-1- (2) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (40 mg, 0.090 mmol) -Chloroethyl) -1H-pyrazole (26 mg, 0.126 mmol) was added. The reaction mixture was flushed under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.004 mmol) was added. The reaction was heated at 120 ° C. for 20 minutes under microwave. It was then diluted with EtOAc (10 mL), filtered through celite and then aqueous work up. The compound was purified by Gilson preparative HPLC to give 5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H 10 mg (24%) of indole-7-carboxamide was provided.

5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- in tetrahydrofuran (1 mL) A solution of indole-7-carboxamide (20 mg, 0.043 mmol), 2-aminoethanol (26 mg, 0.43 mmol) and sodium iodide (5 mg, 0.022 mmol) was reacted under microwave at 130 ° C. for 2 hours. Tetrahydrofuran was then removed and the mixture was aqueous washed with EtOAc and water. The organic layer was then separated and all solvents removed. The mixture was then purified by Gilson preparative HPLC to give 8 mg (31%) of the title compound.

LC / MS = m / z 489.2 [M + H] Retention time: 1.40 minutes.

Example  256: 5- {1- [2- ( Butylamino Ethyl] -1 H- Pyrazole -4-yl} -3- [1- ( Ethyl sulfo Nil) -4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with 1-butanamine (31 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2- [ Prepared according to the general procedure for (2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate 7 mg (26%) of the title compound. ) Was obtained.

LC / MS = m / z 499.4 [M + H] Retention time: 1.39 minutes.

Example  257: 5- {1- [2- ( Cyclobutylamino Ethyl] -1 H- Pyrazole -4-yl} -3- [1- ( Ethylsulfonyl )-4- Piperidinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with cyclobutanamine (31 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[( 2-hydroxyethyl) amino] ethyl} -1 H-pyrazol-4-yl) -1 H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 10 mg (38%) of the title compound. Obtained.

LC / MS = m / z 501.4 [M + H] Retention time: 1.48 minutes.

Example  258: 5- [1- (2-{[2- ( Diethylamino ) Ethyl] amino} ethyl) -1H- Pyrazole -4-yl] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with N, N-diethyl-1,2-ethanediamine (50 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl]- According to the general procedure for 5- (1- {2-[(2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate To give 12 mg (42%) of the title compound.

LC / MS = m / z 545.2 [M + H] Retention time: 1.25 minutes.

Example  259: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (1- {2-[(1- Methylethyl ) Amino] ethyl} -1H- Pyrazole -4-yl) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with 2-propanamine (25 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2- [ Prepared according to the general procedure for (2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate 9 mg (35%) of the title compound ) Was obtained.

LC / MS = m / z 487.2 [M + H] Retention time: 1.47 minutes.

Example  260: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (1- {2-[(2- Methylpropyl ) Amino] ethyl} -1H- Pyrazole -4-yl) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with 2-methyl-1-propanamine (31 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- Prepared according to the general procedure for {2-[(2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate to give the title compound 8 mg (30%) was obtained.

LC / MS = m / z 501.2 [M + H] Retention time: 1.45 minutes.

Example  261: 5- (1- {2-[( Cyclopentylmethyl ) Amino] ethyl} -1H- Pyrazole -4-yl) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2-aminoethanol with cyclopentanamine (37 mg, 0.43 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[( 2-hydroxyethyl) amino] ethyl} -1 H-pyrazol-4-yl) -1 H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 11 mg (40%) of the title compound. Obtained.

LC / MS = m / z 513.4 [M + H] Retention time: 1.47 minutes.

Example  262: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- ( Methyloxy ) -3- (1- Pyrroly Dimethylmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

2- (methyloxy) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl in dioxane (19 mL) and H ₂ O (6.3 mL) 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (963 mg, 2.33 mmol) in a solution of benzaldehyde (610 mg, 2.33 mmol) ) And sodium carbonate (1.48 g, 13.9 mmol) were added. After flushing with argon for 10 minutes, tetrakis (triphenylphosphine) palladium (0) (134 mg, 0.166 mmol) was added. The reaction was heated at 120 ° C. for 120 min under microwave. The compound was purified by flash chromatography using DCM and MeOH to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4- (methyloxy) phenyl] -1H 632 mg (58%) of indole-7-carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4- (methyloxy) phenyl] -1H-indole-7-carboxamide in methanol (5 mL) (50 mg, 0.107 mmol), a solution of pyrrolidine (45 μl, 0.214 mmol), zinc chloride (10 mg, 0.054 mmol) and sodium cyanoborohydride (7 mg, 0.107 mmol) at room temperature for 2 hours. Stirred. To this mixture was added 0.1 normal solution (2 mL) of sodium hydroxide in water. Methanol was then evaporated. The aqueous phase was extracted three times with EtOAc (5 mL). The organic phase was then washed twice with brine (5 mL). After that all solvent was removed. The mixture was purified by Gilson preparative HPLC to give 9 mg (13%) of the title compound.

LC / MS = m / z 525.6 [M + H] Retention time: 1.67 minutes.

Example  263: 5- [3-[(dimethylamino) methyl ]-4-( Methyloxy ) Phenyl ] -3- [1- ( Ethyl sulfo Nil) -4-piperidinyl] -1 H-indole-7- Carboxamide Trifluoroacetate

2- (methyloxy) -5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl in dioxane (19 mL) and H ₂ O (6.3 mL) 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (963 mg, 2.33 mmol) in a solution of benzaldehyde (610 mg, 2.33 mmol) ) And sodium carbonate (1.48 g, 13.9 mmol) were added. After flushing with argon for 10 minutes, tetrakis (triphenylphosphine) palladium (0) (134 mg, 0.166 mmol) was added. The reaction was heated at 120 ° C. for 120 min under microwave. The compound was purified by flash chromatography using DCM and MeOH to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4- (methyloxy) phenyl] -1H 632 mg (58%) of indole-7-carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-formyl-4- (methyloxy) phenyl] -1H-indole-7-carboxamide in methanol (5 mL) (50 mg, 0.214 mmol), a solution of dimethylamine (107 μl, 0.214 mmol), zinc chloride (10 mg, 0.054 mmol) and sodium cyanoborohydride (7 mg, 0.107 mmol) was stirred at room temperature for 2 hours It was. To this mixture was added 0.1 normal solution (2 mL) of sodium hydroxide in water. Methanol was then evaporated. The aqueous phase was extracted three times with EtOAc (5 mL). The organic phase was then washed twice with brine (5 mL). All solvents were then removed. The mixture was purified by Gilson preparative HPLC to give 4 mg (6.1%) of the title compound.

LC / MS = m / z 499.4 [M + H] Retention time: 1.56 minutes.

Example  264: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- ( Methyloxy ) -3- (4- Morpholinylme Teal) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with morpholine (20 μl, 0.214 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl ) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure to yield 12 mg (17%) of the title compound.

LC / MS = m / z 541.6 [M + H] Retention time: 1.69 minutes.

Example  265: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-{[(1- Methylethyl ) Amino] methyl} -4- (meth Til-Ock city) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with 2-propanamine (15 μl, 0.214 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3- [1- (ethyl Prepared according to the general procedure for sulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to afford 16 mg (24%) of the title compound.

LC / MS = m / z 513.2 [M + H] Retention time: 1.62 minutes.

Example  266: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-[( Methylamino ) methyl ] -4- (Me Til-Ock city) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with methylamine (50 μl, 0.214 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl Prepared according to the general procedure for) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 10 mg (16%) of the title compound.

LC / MS = m / z 485.2 [M + H] Retention time: 1.57 minutes.

Example  267: 5- [3-{[(2,2-dimethylpropyl) amino] methyl }-4-( Methyloxy ) Phenyl ] -3- [1- (ethylsulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the dimethylamine with 2,2-dimethyl-1-propanamine (20 μl, 0.214 mmol) and replace the title compound with 5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3 Prepared according to the general procedure for-[1- (ethylsulfonyl) -4piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to afford 11 mg (16%) of the title compound.

LC / MS = m / z 541.2 [M + H] Retention time: 1.77 minutes.

Example  268: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (1- {2-[(2- Hydroxyethyl ) ( methyl ) Amino] ethyl} -1H- Pyrazole -4-yl) -1H-indole-7- Carboxamide

5- [1- (2-chloroethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- in tetrahydrofuran (1 mL) A solution of indole-7-carboxamide (30 mg, 0.065 mmol), 2- (methylamino) ethanol (500 μl, 6.5 mmol) and sodium iodide (3 mg, 0.016 mmol) at 130 ° C. under microwave for 2 hours. Reacted. The resulting mixture was aqueous worked up. It was then purified by Gilson preparative HPLC to give 9 mg (17%) of the title compound.

LC / MS = m / z 503.2 [M + H] Retention time: 1.40 minutes.

Example  269: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {4- Fluoro -3-[( Methylamino ) methyl ] Phenyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-fluoro-3-formylphenyl) -1H-indole- in dichloromethane (1 mL) and methanol (1 mL) To a solution of 7-carboxamide (16.0 mg, 0.035 mmol) was added 2 M methylamine (105 μL, 0.21 mmol) and 1 drop of acetic acid in THF. This mixture was stirred for 3 hours. Sodium tetrahydridoborate (8.4 mg, 0.21 mmol) was added and the mixture was stirred for 1 hour. The resulting mixture was concentrated and dissolved in dimethyl sulfoxide (1.5 mL). It was then purified by Gilson preparative HPLC to give 6.4 mg (31.2%) of the title compound.

LC / MS = m / z 473.4 [M + H] Retention time: 1.50 minutes.

Example  270: 5- {3,5-bis [( Methylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Pipe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

5- (3,5-diformylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- in dichloromethane (1 mL) and methanol (1 mL) To a solution of carboxamide (10 mg, 0.2 mmol) was added methylamine (64 μl, 0.128 mmol) and one drop of acetic acid. The resulting mixture was stirred for 3 hours at room temperature and then sodium tetrahydridoborate (5.1 mg, 0.128 mmol) was added. It was stirred for 1 h and then concentrated and purified by Gilson preparative HPLC to give 3 mg (23.4%) of the title compound.

LC / MS = m / z 498.6 [M + H] Retention time: 1.17 minutes.

Example  271: 5- {3-[( Ethylamino ) methyl ]-4- Fluorophenyl } -3- [1- ( Ethylsulfonyl ) -4-p Fe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-fluoro-3-formylphenyl) -1H-indole- in dichloromethane (1 mL) and methanol (1 mL) To a solution of 7-carboxamide (35 mg, 0.076 mmol) was added 2 M ethylamine (230 μl, 0.46 mmol) and 1 drop of acetic acid. The mixture was stirred at rt for 1 h and then tetrahydrofuran (1 mL) was added. The mixture was stirred for 30 minutes and then sodium tetrahydridoborate (17.5 mg, 0.46 mmol) was added. The resulting mixture was stirred for an additional hour, concentrated and purified by Gilson preparative HPLC to give 20 mg (43.8%) of the title compound.

LC / MS = m / z 487.4 [M + H] Retention time: 1.46 minutes.

Example  272: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- Fluoro -3-({[2-hydroxy-1- (hy Doxymethyl ) Ethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroa Catetate (salt)

Replace the ethylamine with 2-amino-1,3-propanediol (42 mg, 0.46 mmol) and replace the title compound with 5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 21 mg (42.7%) of the title compound.

LC / MS = m / z 533.2 [M + H] Retention time: 1.39 minutes.

Example  273: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- Fluoro -3-({[(1S) -2-hydroxy-1- Methylethyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate  (salt)

Replace the ethylamine with (2S) -2-amino-1-propanol (37 mg, 0.46 mmol) and replace the title compound with 5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- Prepared according to the general procedure for [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 26 mg (54.2%) of the title compound.

LC / MS = m / z 517.2 [M + H] Retention time: 1.44.

Example  274: 5- {3-[( Cyclopropylamino ) methyl ]-4- Fluorophenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the ethylamine with cyclopropylamine (32 mg, 0.46 mmol) and replace the title compound with 5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) Prepared according to the general procedure for -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 23 mg (49.4%) of the title compound.

LC / MS = m / z 499.6 [M + H] Retention time: 1.75 minutes.

Example  275: 5- {3-[( Cyclobutylamino ) methyl ]-4- Fluorophenyl } -3- [1- ( Ethyl alcohol Ponyl) -4-P Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the ethylamine with cyclobutanamine (39 mg, 0.46 mmol) and replace the title compound with 5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) Prepared according to the general procedure for -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 20 mg (42%) of the title compound.

LC / MS = m / z 513.2 [M + H] Retention time: 1.58 minutes.

Example  276: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1- Pyrrolidinylmethyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (0.5 mL) and methanol (0.5 mL) To a solution of (33 mg, 0.74 mmol) was added pyrrolidine (32 mg, 0.444 mmol) and 1 drop of acetic acid. The mixture was stirred for 2 minutes, then sodium tetrahydridoborate (17.8 mg, 0.444 mmol) was added. It was then stirred overnight, then concentrated and purified by Gilson preparative HPLC to give 9.7 mg (21.5%) of the title compound.

LC / MS = m / z 495.4 [M + H] Retention time: 1.67 minutes.

Example  277: 5- {3,5-bis [( Ethylamino ) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Pipe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

5- (3,5-diformylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- in dichloromethane (1.5 mL) and methanol (1.5 mL) To a solution of carboxamide (27 mg, 0.058 mmol) was added ethylamine (31.4 mg, 0.696 mmol) and one drop of acetic acid. The resulting mixture was stirred for 2 hours and then sodium tetrahydridoborate (13.2 mg, 0.348 mmol) was added. It was stirred for an additional 50 minutes and then purified by Gilson preparative HPLC to give 20 mg (53.9%) of the title compound.

LC / MS = m / z 526.6 [M + H] Retention time: 1.41 minutes.

Example  278: 5- {3,5-bis [(dimethylamino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formyl-5-mercaptophenyl) -1H-indole- in dichloromethane (1.5 mL) and methanol (1.5 mL) To a solution of 7-carboxamide (34 mg, 0.058 mmol) was added dimethylamine (31.4 mg, 0.696 mmol) and one drop of acetic acid. The resulting mixture was stirred at rt for 2 h and then sodium tetrahydridoborate (13.2 mg, 0.348 mmol) was added. It was stirred for an additional 30 minutes and then purified by Gilson preparative HPLC to give 11 mg (29.6%) of the title compound.

LC / MS = m / z 526.6 [M + H] Retention time: 1.27 minutes.

Example  279: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (2- Piperidinyl ) Phenyl ] -1H-indole-7-car Lebox Arm De Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (2 mL) and H ₂ O (0.7 mL) 2- (3-chlorophenyl) piperidine (46 mg, 0.2 mmol) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (46 mg, 0.1 mmol) Was added. Potassium carbonate (55 mg, 0.4 mmol), also degassed for 5 minutes, then tetrakis (triphenylphosphine) palladium (0) (5 mg, 0.5 mmol) was added. The resulting mixture was reacted at 160 ° C. for 30 minutes under 300 W CEM microwaves, after which the solids were filtered off. The solvent was evaporated and the solution was purified by Gilson preparative HPLC to give 13.2 mg (21.7%) of the title compound.

LC / MS = m / z 495.4 [M + H] Retention time: 1.76.

Example  280: 5- {3- [1- ( Ethylamino )ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

5- (3-acetylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 in N, N-dimethylformamide (0.8 mL) and acetic acid (0.2 mL) A solution of carboxamide (50 mg, 0.11 mmol), ethylamine (19.9 mg, 0.441 mmol) and sodium cyanoborohydride (30 mg, 0.441 mmol) was reacted at 150 ° C. for 20 minutes under microwave. The reaction was purified by Gilson preparative HPLC to give 20.6 mg (39%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.67.

Example  281: 5- {3- [1- (dimethylamino) ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperi Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

5- (3-acetylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (50 mg, 0.11 mmol), dimethylamine (220 μl, 0.44 mmol) and sodium cyanoborohydride (30 mg, 0.44 mmol) were dissolved in N, N-dimethylformamide (400 μl) and acetic acid (100 μl). The resulting mixture was reacted at 150 ° C. for 20 minutes under a Smith 150 W microwave. The reaction was purified by Gilson preparative HPLC to give 14.6 mg (22.2%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.63.

Example  282: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3- Fluoro -5-[( Methylami furnace) Me Teal] Phenyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (1.5 mL) and methanol (1.5 mL) To a solution of 7-carboxamide (32 mg, 0.07 mmol) was added 2 M methylamine (210 μL, 0.42 mmol) and 1 drop of acetic acid in THF. The resulting mixture was stirred for 3 hours at room temperature and then sodium tetrahydridoborate (15 mg, 0.42 mmol) was added. The mixture was stirred for 1 hour, concentrated and purified by Gilson preparative HPLC to give 30 mg (73.1%) of the title compound.

LC / MS = m / z 473.6 [M + H] Retention time: 1.73 minutes.

Example  283: 5- {3-[( Ethylamino ) methyl ] -5- Fluorophenyl } -3- [1- ( Ethylsulfonyl ) -4-p Fe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2 M ethanamine (210 ul, 0.42 mmol) in THF, and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5 Prepared according to the general procedure for-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 6.5 mg (15.5%) of the title compound.

LC / MS = m / z 487.4 [M + H] Retention time: 1.64 minutes.

Example  284: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3- Fluoro -5-[( Profile Mino) methyl ] Phenyl } -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with propylamine (21 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(methyl Prepared according to the general procedure for amino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 31 mg (72%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.54.

Example  285: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(1- In methyl Til) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2-propanamine (21 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5- [ Prepared according to the general procedure for (methylamino) methyl] phenyl} -1H-yndol-7-carboxamide trifluoroacetate to give 28.5 mg (66.2%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.53 minutes.

Example  286: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(2- Methylpropyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2-methyl-1-propanamine (21 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro Prepared according to the general procedure for -5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to afford 10 mg (22.7%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.72 minutes.

Example  287: 5- {3-[( Cyclobutylamino ) methyl ] -5- Fluorophenyl } -3- [1- ( Ethyl alcohol Ponyl) -4-P Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with cyclobutylamine (21.5 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5- [ Prepared according to the general procedure for (methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 33 mg (75.2%) of the title compound.

LC / MS = m / z 513.2 [M + H] Retention time: 1.50 minutes.

Example  288: 5- {3-[(dimethylamino) methyl ] -5- Fluorophenyl } -3- [1- ( Ethyl sulfo Nil) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2M dimethylamine (210 ul, 0.42 mmol) in THF, and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5 Prepared according to the general procedure for-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 33.7 mg (80.2%) of the title compound.

LC / MS = m / z 487.2 [M + H] Retention time: 1.43 minutes.

Example  289: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5- (1- Pyrrolididi Nilmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methanamine with pyrrolidine (20.4 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[( Prepared according to the general procedure for methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to afford 18 mg (41%) of the title compound.

LC / MS = m / z 513.4 [M + H] Retention time: 1.63 minutes.

Example  290: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5- (4- Morpoli Nilmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with morpholine (22 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(methyl Prepared according to the general procedure for amino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 22.9 mg (50.9%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.47 minutes.

Example  291: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5- (1- Piperidi Nilmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with piperidine (22 mg, 0.42 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[( Prepared according to the general procedure for methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 13.4 mg (29.9%) of the title compound.

LC / MS = m / z 527.6 [M + H] Retention time: 1.62.

Example  292: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3- [1- ( Methylamino )ethyl] Fe Nil} -1H-indole-7- Carboxamide Trifluoroacetate

Methylamine in a solution of 5- (3-acetylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20 mg, 0.044 mmol) in ethanol Hydrochloride salt and 1 drop of concentrated hydrochloride were added. The mixture was reacted for 10 minutes at 100 ° C. under CEM microwaves, and then sodium tetrahydridoborate was added. The resulting mixture was reacted at 50 ° C. for 5 minutes under CEM microwaves and then all solvents were evaporated. It was again dissolved in dimethyl sulfoxide and then purified by Gilson preparative HPLC to give 16.5 mg (64.4%) of the title compound.

LC / MS = m / z 469.4 [M + H] Retention time: 1.45 minutes.

Example  293: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- {1-[(1- Methylethyl ) Amino] ethyl} phenyl) -1H-indole-7- Carboxamide Trifluoroacetate

5- (3-acetylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 in N, N-dimethylformamide (0.8 mL) and acetic acid (0.2 mL) To a solution of -carboxamide (20 mg, 0.044 mmol) was added 2-propanamine (75 μL, 0.88 mmol) and sodium cyanoborohydride (6 mg, 0.09 mmol). The resulting mixture was reacted at 70 ° C. for 1 hour under Smith microwave. The solid was filtered and then purified by Gilson preparative HPLC to give 19.4 mg (72.2%) of the title compound.

LC / MS = m / z 497.4 [M + H] Retention time: 1.44 minutes.

Example  294: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- {1-[(2- Methylpropyl ) Amino] ethyl} Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

5- (3-acetylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (30 in ethanol (1.2 mL) and acetic acid (0.3 mL) (30) (2-methylpropyl) amine (101 mg, 1.98 mmol) and sodium cyanoborohydride (13.5 mg, 0.198 mmol) were added to a solution of mg, 0.066 mmol). The resulting mixture was reacted at 70 ° C. for 1 hour under Smith microwave. All solvents were evaporated and the solids dissolved using dimethyl sulfoxide. It was then purified by Gilson preparative HPLC to give 22.7 mg (55.1%) of the title compound.

LC / MS = m / z 511.2 [M + H] Retention time: 1.52 minutes.

Example  295: 5- {3- [1- ( Cyclobutylamino )ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2-methylpropyl) amine with cyclobutylamine (101 mg, 1.98 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1 Prepared according to the general procedure for-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate to give 29.1 mg (70.8%) of the title compound.

LC / MS = m / z 509.4 [M + H] Retention time: 1.52 minutes.

Example  296: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3- [1- (1- Pyrrolidinyl ) Ethyl] phenyl} -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2-methylpropyl) amine with pyrrolidine (101 mg, 1.98 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1 Prepared according to the general procedure for-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate to give 29.2 mg (71%) of the title compound.

LC / MS = m / z 509.4 [M + H] Retention time: 1.49 minutes.

Example  297: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (3- Thiomorpholinyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (1.5 mL) and water (0.5 mL) 3- (3-chlorophenyl) thiomorpholine (84 mg, 0.39 mmol) and carbonic acid in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol) Potassium (107.6 mg, 0.78 mmol) was added. The mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (14.0 mg, 0.013 mmol) was added. The resulting mixture was reacted at 160 ° C. for 30 minutes under microwave. The solid was filtered off and all solvent was evaporated. The resulting solution was redissolved in dichloromethane and water was removed using a separator. The mixture was concentrated to give an organic solvent and then purified by Gilson preparative HPLC to give 7.4 mg (11%) of the title compound.

LC / MS = m / z 513.4 [M + H] Retention time: 1.54.

Example  298: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (2- Piperazinyl )-2- Tier Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (1.5 mL) and water (0.5 mL) 2- (5-bromo-2-thienyl) piperazine (102 mg, 0.39) in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol) mmol) and potassium carbonate (108 mg, 0.78 mmol) were added. The mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (15.0 mg, 0.013 mmol) was added. The resulting mixture was reacted at 160 ° C. for 30 minutes under microwave. The solid was filtered off and all solvent was evaporated. The resulting solution was redissolved in dichloromethane and water was removed using a separator. The mixture was concentrated to give an organic solvent and then purified by Gilson preparative HPLC to give 29.1 mg (36.4%) of the title compound.

LC / MS = m / z 502.4 [M + H] Retention time: 1.31.

Example  299: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (2- Piperazinyl ) Phenyl ] -1H-indole-7-car Lebox Arm De Trifluoroacetate

Replace the 2- (5-bromo-2-thienyl) piperazine with 2- (4-bromophenyl) piperazine (94 mg, 0.39 mmol) and replace the title compound with 3- [1- (ethylsulfonyl ) -4-piperidinyl] -5- [5- (2-piperazinyl) -2-thienyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 20.5 mg (25.9%) of compound were obtained.

LC / MS = m / z 496.4 [M + H] Retention time: 1.25.

Example  300: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (2- Piperazinyl ) Phenyl ] -1H-indole-7-car Lebox Arm De Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (1.5 mL) and water (0.5 mL) 2- (3-chlorophenyl) piperazine (63.7 mg, 0.325 mmol) and potassium carbonate in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol) (90 mg, 0.650 mmol) was added. The mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (12 mg, 0.011 mmol) was added. The resulting mixture was reacted at 160 ° C. for 30 minutes under microwave. The solid was filtered off and all solvent was evaporated. The resulting solution was redissolved in dichloromethane and water was removed using a separator. The mixture was concentrated to give an organic solvent and then purified by Gilson preparative HPLC to give 21.7 mg (27.4%) of the title compound.

LC / MS = m / z 496.4 [M + H] Retention time: 1.28 minutes.

Example  301: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- (4- Morpholinyl ) -3- Pipe Dazinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2- (3-chlorophenyl) piperazine with 4- (6-chloro-3-pyridazinyl) morpholine (65 mg, 0.325 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) 3.1 mg (3.9) of the title compound prepared according to the general procedure for -4-piperidinyl] -5- [3- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide trifluoroacetate %) Was obtained.

LC / MS = m / z 499.6 [M + H] Retention time: 1.57 minutes.

Example  302: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [6- (1- Pyrrolidinyl ) -3- Pipe Dazinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2- (3-chlorophenyl) piperazine with 3-chloro-6- (1-pyrrolidinyl) pyridazine (60 mg, 0.325 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) 4.1 mg (5.3) of the title compound prepared according to the general procedure for -4-piperidinyl] -5- [3- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide trifluoroacetate %) Was obtained.

LC / MS = m / z 483.2 [M + H] Retention time: 1.44 minutes.

Example  303: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {2-[( Methylamino ) methyl ] Fe Nil} -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2- (3-chlorophenyl) piperazine with 1- (2-bromophenyl) -N-methylmethanamine (65 mg, 0.325 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) 14.6 mg (19.8) of the title compound prepared according to the general procedure for -4-piperidinyl] -5- [3- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide trifluoroacetate %) Was obtained.

LC / MS = m / z 455.0 [M + H] Retention time: 1.57 minutes.

Example  304: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Thienylmethyl ) Amino] methyl } Phenyl) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (2 mL) and methanol (2 mL) To a solution of (44 mg, 0.1 mmol) was added 1- (2-thienyl) methanamine (33.6 mg, 0.6 mmol) and 1 drop of acetic acid. The mixture was stirred for 2 hours and then sodium tetrahydridoborate (22.8 mg, 0.6 mmol) was added. The resulting mixture was stirred for 1 hour. It was then concentrated and again dissolved in dimethyl sulfoxide (3 mL). Then purification by Gilson preparative HPLC gave 41.7 mg (74.5%) of the title compound.

LC / MS = m / z 537.2 [M + H] Retention time: 1.81 minutes.

Example  305: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(5- methyl -2- Furanil ) Me Til] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1- (2-thienyl) methanamine with 1- (5-methyl-2-furanyl) methanamine (32 mg, 0.6 mmol) and replace the title compound with 3- [1- (ethylsulfonyl)- Prepared according to the general procedure for 4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate and titled 29.3 mg (54.7%) of compound were obtained.

LC / MS = m / z 535.2 [M + H] Retention time: 1.74 minutes.

Example  306: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(2R)- Tetrahydro 2-fu la Nilmethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1- (2-thienyl) methanamine with 1-[(2R) -tetrahydro-2-furanyl] methanamine (31.5 mg, 0.6 mmol) and replace the title compound with 3- [1- (ethylsul According to the general procedure for poly (yl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate To give 36.9 mg (70.3%) of the title compound.

LC / MS = m / z 525.6 [M + H] Retention time: 1.63 minutes.

Example  307: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(2S)- Tetrahydro 2-fu la Nilmethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1- (2-thienyl) methanamine with 1-[(2S) -tetrahydro-2-furanyl] methanamine (31.5 mg, 0.6 mmol) and replace the title compound with 3- [1- (ethylsul According to the general procedure for poly (yl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate To give 39.2 mg (74.7%) of the title compound.

LC / MS = m / z 525.6 [M + H] Retention time: 1.61 minutes.

Example  308: 5- (3-{[(2,2-dimethylpropyl) amino] methyl } Phenyl ) -3- [1- ( Ethyl sulfo Nil) -4- blood Ferridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1- (2-thienyl) methanamine with 2,2-dimethyl-1-propanamine (30.6 mg, 0.6 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidi Nil] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure for 30.4 mg of the title compound ( 59.5%) was obtained.

LC / MS = m / z 511.4 [M + H] Retention time: 1.69 minutes.

Example  309: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Methylbutyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (2 mL) and methanol (1 mL) To (44 mg, 0.1 mmol) was added 2-methyl-1-butanamine (52 mg, 0.6 mmol) and 1 drop of acetic acid. The mixture was stirred for 2 hours and then sodium tetrahydridoborate (22.8 mg, 0.6 mmol) was added. The resulting mixture was stirred for 1 hour. It was then concentrated and again dissolved in dimethyl sulfoxide (3 mL). Then purification by Gilson preparative HPLC gave 28.4 mg (55.6%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.71.

Example  310: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(2S) -2- Methylbutyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

The title compound was replaced by 3- [1- (ethylsulfonyl) -4-piperidi, replacing 2-methyl-1-butanamine with (2S) -2-methyl-1-butanamine (52 mg, 0.6 mmol). Nile] -5- (3-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide prepared according to the general procedure for 30 mg (58.7%) of the title compound. It was.

LC / MS = m / z 511.4 [M + H] Retention time: 1.68.

Example  311: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(1R) -1,2,2- Trimethylpropyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

Replace the 2-methyl-1-butanamine with (2R) -3,3-dimethyl-2-butanamine (60 mg, 0.6 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4- 24.5 mg (46.7%) of the title compound prepared according to the general procedure for piperidinyl] -5- (3-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide Obtained.

LC / MS = m / z 525.6 [M + H] Retention time: 1.67.

Example  312: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[(2S)- Tetrahydro -2- Furanylmethyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (2 mL) and methane (1 mL) To a solution of 7-carboxamide (40 mg, 0.087 mmol) was added 1-[(2S) -tetrahydro-2-furanyl] methanamine (53 mg, 0.525 mmol) and two drops of acetic acid. The resulting mixture was stirred for 2 hours at room temperature and then sodium tetrahydridoborate (20 mg, 0.525 mmol) was added. The mixture was stirred for 30 minutes, concentrated and purified by Gilson preparative HPLC to give 26.6 mg (46.6%) of the title compound.

LC / MS = m / z 543.4 [M + H] Retention time: 1.60 minutes.

Example  313: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[(2R)- rim Trahydro-2- Furanylmethyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Substitute 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1-[(2R) -tetrahydro-2-furanyl] methanamine (53 mg, 0.525 mmol) to give the title compound 3 -[1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl]- Prepared according to the general procedure for 1H-indole-7-carboxamide trifluoroacetate to give 27.1 mg (47.4%) of the title compound.

LC / MS = m / z 543.4 [M + H] Retention time: 1.58 minutes.

Example  314: 5- [3-({[(1S) -1,2-dimethylpropyl] amino} methyl ) -5- Fluorophenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with (2S) -3-methyl-2-butanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- ( Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7 Prepared according to the general procedure for carboxamide trifluoroacetate to give 19.3 mg (42%) of the title compound.

LC / MS = m / z 529.6 [M + H] Retention time: 1.65.

Example  315: 5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl ) -5- Fluorophenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with (2R) -3-methyl-2-butanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- ( Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7 Prepared according to the general procedure for carboxamide trifluoroacetate to give 19.5 mg (34.9%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.82 minutes.

Example  316: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(1- Methyl Lofil) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 2-butanamine (37 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-pipe Ridinyl] -5- [3-fluoro-5- ({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide trifluoroacetate Prepared according to the general procedure for the yield of 27.7 mg (50.6%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.63 minutes.

Example  317: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1] was substituted for 1-[(2S) -tetrahydro-2-furanyl] methanamine with (2S) -3,3-dimethyl-2-butanamine (52 mg, 0.525 mmol). -(Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole Prepared according to the general procedure for -7-carboxamide trifluoroacetate to give 19.8 mg (34.7%) of the title compound.

LC / MS = m / z 543.4 [M + H] Retention time: 1.78 minutes.

Example  318: 3- [1- ( Ethylsulfonyl )- Piperidinyl ] -5- [3- Fluoro -5-({[(2S) -2- Methylbutyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace 1-[(2S) -tetrahydro-2-furanyl] methanamine with (2S) -2-methyl-1-butanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- ( Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7 Prepared according to the general procedure for carboxamide trifluoroacetate to give 23.3 mg (41.7%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.62 minutes.

Example  319: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(2- Methyl Til) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 2-methyl-1-butanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide Prepared according to the general procedure for trifluoroacetate to give 30.5 mg (54.5%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.73 minutes.

Example  320: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[(1R) -1,2,2-trimethylpropyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1] was substituted for 1-[(2S) -tetrahydro-2-furanyl] methanamine with (2R) -3,3-dimethyl-2-butanamine (52 mg, 0.525 mmol). -(Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole Prepared according to the general procedure for -7-carboxamide trifluoroacetate to give 24.9 mg (43.6%) of the title compound.

LC / MS = m / z 543.4 [M + H] Retention time: 1.73 minutes.

Example  321: 5- (3-{[(2,2-dimethylpropyl) amino] methyl } -5- Fluorophenyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 2,2-dimethyl-1-propanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsul Ponyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-car Prepared according to the general procedure for boxamide trifluoroacetate to afford 14 mg (25%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.79 minutes.

Example  322: 5- (3-{[( Cyclopropylmethyl ) Amino] methyl } -5- Fluorophenyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1-cyclopropylmethanamine (37 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4 -Piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide trifluor Prepared according to the general procedure for low acetate to give 21.1 mg (38.7%) of the title compound.

LC / MS = m / z 513.4 [M + H] Retention time: 1.69 minutes.

Example  323: 5- (3-{[( Cyclopentylmethyl ) Amino] methyl } -5- Fluorophenyl ) -3- [1- (in Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1-cyclopentylmethanamine (52 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4 -Piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide trifluor Prepared according to the general procedure for low acetate to give 21.6 mg (37.9%) of the title compound.

LC / MS = m / z 541.4 [M + H] Retention time: 1.82 minutes.

Example  324: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[( Tetrahi Dro-2H-pyran-4- Methyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3-substitute the title compound by replacing 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1- (tetrahydro-2H-pyran-4-yl) methanamine (60 mg, 0.525 mmol) [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H Prepared according to the general procedure for -indole-7-carboxamide trifluoroacetate to give 40.1 mg (68.7%) of the title compound.

LC / MS = m / z 557.4 [M + H] Retention time: 1.54 minutes.

Example  325: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(2- Thienyl Methyl) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1- (2-thienyl) methanamine (59 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsul Ponyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-car Prepared according to the general procedure for boxamide trifluoroacetate to give 24.4 mg (41.9%) of the title compound.

LC / MS = m / z 555.4 [M + H] Retention time: 1.67 minutes.

Example  326: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[2- ( methyl Oxy) ethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 2- (methyloxy) ethanamine (39 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide Prepared according to the general procedure for trifluoroacetate to give 31 mg (56.5%) of the title compound.

LC / MS = m / z 517.2 [M + H] Retention time: 1.52 minutes.

Example  327: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[3- ( methyl Oxy) propyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 3- (methyloxy) -1-propanamine (46 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethyl Sulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7- Prepared according to the general procedure for carboxamide trifluoroacetate to give 27.3 mg (48.7%) of the title compound.

LC / MS = m / z 531.4 [M + H] Retention time: 1.54 minutes.

Example  328: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(2- Furanylmethyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1- (2-furanyl) methanamine (50 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsul Ponyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-car Prepared according to the general procedure for boxamide trifluoroacetate to give 24.8 mg (43.7%) of the title compound.

LC / MS = m / z 539.4 [M + H] Retention time: 1.63 minutes.

Example  329: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- Fluoro -5-{[(3- Methylbutyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 3-methyl-1-butanamine (45 mg, 0.525 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide Prepared according to the general procedure for trifluoroacetate to give 27.6 mg (49.4%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.67 minutes.

Example  330: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- Fluoro -5-({[(5- methyl 2-fu la Neil) methyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 1-[(2S) -tetrahydro-2-furanyl] methanamine with 1- (5-methyl-2-furanyl) methanamine (58 mg, 0.525 mmol) and replace the title compound with 3- [1 -(Ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole Prepared according to the general procedure for -7-carboxamide trifluoroacetate to give 28.3 mg (48.8%) of the title compound.

LC / MS = m / z 553.6 [M + H] Retention time: 1.78 minutes.

Example  331: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Methylpropyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (2 mL) and methanol (1 mL) To a solution of (50 mg, 0.114 mmol) was added 2-methyl-1-propanamine (70 μl, 0.683 mmol) and two drops of acetic acid. The mixture was stirred at rt for 2 h and then sodium tetrahydridoborate (26 mg, 0.683 mmol) was added. After 30 minutes the mixture was concentrated and dissolved in dimethyl sulfoxide (2 mL) and purified by Gilson preparative HPLC to give 19.8 mg (61%) of the title compound.

LC / MS = m / z 497.4 [M + H] Retention time: 1.57.

Example  332: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (2- Pyrrolidinyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (1 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (70 mg, 0.151 mmol), 2- (3- iodophenyl) pyrrolidine (70 mg, 0.456 mmol) and potassium carbonate A solution of (126 mg, 0.910 mmol) was degassed for 5 minutes and tetrakis (triphenylphosphine) palladium (0) (17 mg, 0.015 mmol) was added. The mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The organic layer was then separated and concentrated. It was then dissolved in dimethyl sulfoxide (1 mL) and purified by Gilson preparative HPLC to give 48 mg (59.5%) of the title compound.

LC / MS = m / z 481.0 [M + H] Retention time: 1.47.

Example  333: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {2- Fluoro -5-[( Methylami furnace) methyl ] Phenyl } -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (2 mL) and methanol (1 mL) To a solution of 7-carboxamide (40 mg, 0.087 mmol) was added methanamine (262 μl, 0.524 mmol) and one drop of acetic acid. After stirring at room temperature for 2 hours, sodium tetrahydridoborate (20 mg, 0.524 mmol) was added and left to stand for 30 minutes. The mixture was then purified by Gilson preparative HPLC to give 12.3 mg (58.6%) of the title compound.

LC / MS = m / z 473.4 [M + H] Retention time: 1.55.

Example  334: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {2- Fluoro -5-[( Profile Mino) Me Teal] Phenyl } -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with propylamine (44 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(methyl Prepared according to the general procedure for amino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 15.4 mg (61.5%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.55.

Example  335: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2- Fluoro -5-{[(2- Methyl Lofil) amino] methyl } Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2-methyl-1-propanamine (53 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro Prepared according to the general procedure for -5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 15 mg (62.9%) of the title compound.

LC / MS = m / z 515.4 [M + H] Retention time: 1.55.

Example 336: 5- (5-{[(2,2-dimethylpropyl) amino] methyl } -2- fluorophenyl ) -3- [1- ( ethyl sulfonyl) -4- piperidinyl ]- 1H-indole-7 -carboxamide Trifluoroacetate

Replace the methaneamine with 2,2-dimethyl-1-propanamine (46 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2- Prepared according to the general procedure for fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 14.3 mg (64.3%) of the title compound.

LC / MS = m / z 530.2 [M + H] Retention time: 1.59.

Example  337: 5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl )-2- Fluorophenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with (2S) -3-methyl-2-butanamine (46 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- { Prepared according to the general procedure for 2-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 17.3 mg (64.3%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.69.

Example  338: 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl )-2- Fluorophenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with (2R) -3-methyl-2-butanamine (46 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- { Prepared according to the general procedure for 2-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 15 mg (64.3%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.70.

Example  339: 5- (5-{[( Cyclopropylmethyl ) Amino] methyl }-2- Fluorophenyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with 2-methyl-1-butanamine (38 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro Prepared according to the general procedure for -5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 16.2 mg (62.7%) of the title compound.

LC / MS = m / z 513.4 [M + H] Retention time: 1.57.

Example  340: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- Fluoro -5- (1- Pyrrolididi Nilmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methanamine with pyrrolidine (44 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[( Prepared according to the general procedure for methylamino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 10 mg (62.7%) of the title compound.

LC / MS = m / z 513.4 [M + H] Retention time: 1.62.

Example  341: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- Fluoro -5- (4- Morpoli Nilmethyl) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methaneamine with morpholine (45 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(methyl Prepared according to the general procedure for amino) methyl] phenyl} -1H-indole-7-carboxamide trifluoroacetate to give 15 mg (64.3%) of the title compound.

LC / MS = m / z 529.4 [M + H] Retention time: 1.52.

Example  342: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- Fluoro -5-({[2- ( methyl Oxy) ethyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-formylphenyl) -1H-indole- in dichloromethane (2 mL) and methanol (1 mL) To a solution of 7-carboxamide (40 mg, 0.087 mmol) was added 2- (methyloxy) ethanamine (54 μl, 0.524 mmol) and one drop of acetic acid. After stirring at room temperature over the weekend, sodium tetrahydridoborate (20 mg, 0.524 mmol) was added and left to stand for 30 minutes. The mixture was then purified by Gilson preparative HPLC to give 11.4 mg (63%) of the title compound.

LC / MS = m / z 517.2 [M + H] Retention time: 1.57.

Example  343: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- Fluoro -5-({[3- ( methyl Oxy) propyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the 2- (methyloxy) ethanamine with 3- (methyloxy) -1-propanamine (53 μl, 0.524 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl ] -5- [2-fluoro-5-({[2- (methyloxy) ethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide trifluoroacetate prepared according to the general procedure This gave 15 mg (64.5%) of the title compound.

LC / MS = m / z 531.4 [M + H] Retention time: 1.60.

Example  344: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (1- methyl -2- Pyrrolidinyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-pyrrolidinyl) phenyl] -1H-indole-7-carboxamide in dichloromethane (2 mL) 2 drops of acetic acid were added to a solution of 20 mg, 0.04 mmol), formaldehyde (9.5 mL, 0.125 mmol) and sodium triacetoxyborohydride. The resulting mixture was stirred at rt overnight. All solvents were evaporated and the product redissolved in dimethyl sulfoxide (1 mL). The mixture was then separated twice by Gilson preparative HPLC to give 8.9 mg (60.9%) of the title compound.

LC / MS = m / z 495.4 [M + H] Retention time: 1.54.

Example  345: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3- {2-[(2- Methylpropyl ) Amino] ethyl} Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxide (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol), [2- (3-bromophenyl) ethyl] (2-methylpropyl) amine (100 mg , 0.39 mmol) and potassium carbonate (108 mg, 0.780 mmol). The resulting mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (14 mg, 0.013 mmol) was added. It was reacted at 160 ° C. for 20 minutes under CEM microwaves. The reaction was then purified by Gilson preparative HPLC to give 44 mg (62.5%) of the title compound.

LC / MS = m / z 511.2 [M + H] Retention time: 1.79.

Example  346: 5- {3- [2- ( Ethylamino )ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (40.4 mg, 0.09 mmol), 2- (3-bromophenyl) -N-ethylethanamine (60 mg, 0.263 mmol) And a solution of potassium carbonate (72 mg, 0.526 mmol) was degassed for 5 minutes. To this was added tetrakis (triphenylphosphine) palladium (0) (11 mg, 0.009 mmol). The resulting mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The reaction was then purified by Gilson preparative HPLC to give 38.6 mg (59.7%) of the title compound.

LC / MS = m / z 482.8 [M + H] Retention time: 1.54.

Example  347: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- {3- [2- ( Propylamino ) Ethyl] phenyl} -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (25 mg, 0.055 mmol), potassium carbonate (46 mg, 0.33 mmol) and [2- (3-bromophenyl) ethyl] A solution of propylamine (40 mg, 0.165 mmol) was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (7 mg, 0.006 mmol) was added. The resulting mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The reaction was then separated using Gilson preparative HPLC to give 17.6 mg (61%) of the title compound.

LC / MS = m / z 497.4 [M + H] Retention time: 1.97.

Example  348: 5- {3- [2- (dimethylamino) ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperi Denyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (60 mg, 0.13 mmol), potassium carbonate (108 mg, 0.78 mmol) and 2- (3-bromophenyl) -N, A solution of N-dimethylethanamine (90 mg, 0.39 mmol) was degassed for 5 minutes, then tetrakis (triphenylphosphine) palladium (0) (15 mg, 0.013 mmol) was added. The resulting mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The reaction was then separated using Gilson preparative HPLC to give 30 mg (59.7%) of the title compound.

LC / MS = m / z 483.2 [M + H] Retention time: 1.60.

Example  349: 5- {3- [2- ( Dipropylamino )ethyl] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Pipe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carboxamide (66 mg, 0.14 mmol), potassium carbonate (120 mg, 0.86 mmol) and (2-phenylethyl) dipropylamine (120 mg , 0.43 mmol) was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (15 mg, 0.014 mmol) was added. The resulting mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The reaction was then separated using Gilson preparative HPLC to yield 9 mg (65.3%) of the title compound.

LC / MS = m / z 455.0 [M + H] Retention time: 1.55.

Example  350: 5- [3-({[2- (3,5-dimethyl-1H-) Pyrazole -1-yl) ethyl] amino} methyl ) Fe Nil] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide in dichloromethane (3 mL) and methanol (1.5 mL) To a solution of (44 mg, 0.1 mmol), 2- (3,5-dimethyl-1H-pyrazol-1-yl) ethanamine (105 mg, 0.6 mmol) was added 3 drops of acetic acid. The resulting mixture was stirred overnight and then sodium triacetoxyborohydride (134 mg, 0.6 mmol) was added. This mixture was stirred overnight. The resulting mixture was quenched with sodium bicarbonate (2 mL) and brine (2 mL) and the organic layer collected and concentrated. The reaction was then separated using Gilson preparative HPLC to give 26 mg (67.7%) of the title compound.

 LC / MS = m / z 563.2 [M + H] Retention time: 1.51.

Example  351: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (4- Morpholinylmethyl ) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) was added morpholine (13Oul, 1.5 mmol) and 3 drops of AcOH. . The mixture was stirred for 12 h and then Na (OAc) ₃ BH (0.335 g, 1.5 mmol) was added. After 6 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL). The organic layer was separated and concentrated to give 200 mg (76%) of 4-[(4-bromo-1,3-thiazol-2-yl) methyl] morpholine.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indol-7-carboxamide (46 mg, 0.1 mmol), 4-[(4-bromo-1,3-thiazol-2-yl) methyl] A solution of morpholine (79 mg, 0.3 mmol) and potassium carbonate (83 mg, 0.6 mmol) was degassed for 5 minutes and then triacetoxyborohydride (11 mg, 0.1 mmol) was added. This mixture was reacted at 160 ° C. for 20 minutes under CEM microwaves. The organic layer was collected and concentrated. The residue was redissolved in dimethyl sulfoxide (1 mL) and then purified by Gilson preparative HPLC to give 26.6 mg (63.2%) of the title compound.

LC / MS = m / z 518.2 [M + H] Retention time: 1.49.

Example  352: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2-{[(2- Methylpropyl ) Amino] methyl } -1,3-thiazol-4-yl) -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) waso-propyl amine (152 ul, 1.5 mmol) and 3 drops of AcOH Added. The mixture was stirred for 12 h, then Na (OAc) ₃ BH (0.335 g, 1.5 mmol) was added. After 6 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL). The organic layer was separated and concentrated to give 145 mg (58%) of the title compound.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) -Dioxaborolan-2-yl) -1H-indole-7-carbaldehyde (46 mg, 0.1 mmol), 2-methyl-1-propanamine (70 mg, 0.3 mmol) and potassium carbonate (83 mg, 0.6 mmol) was added triacetoxyborohydride (11 mg, 0.01 mmol). The solution was degassed for 5 minutes and then reacted at 160 ° C. for 20 minutes under CEM microwaves. The organic layer was separated and concentrated. It was then purified by Gilson preparative HPLC to give 24 mg (61.8%) of the title compound.

LC / MS = m / z 504.2 [M + H] Retention time: 1.43.

Example  353: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (1- Pyrrolidinylmethyl ) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamide

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) was added pyrrolidine (124 ul, 1.5 mmol) and 3 drops of AcOH. It was. The mixture was stirred for 12 h, then Na (OAc) ₃ BH (0.335 g, 1.5 mmol) was added. After 6 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL). The organic layer was separated and concentrated to give 200 mg (82%) of the title compound.

Replace the 2-methyl-1-propanamine with pyrrolidine (74 mg, 0.3 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2- { 6.3 mg of the title compound prepared according to the general procedure for [(2-methylpropyl) amino] methyl} -1,3-thiazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate 50%) was obtained.

LC / MS = m / z 500.4 [M + H] Retention time: 1.22.

Example  354: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (1- Piperidinylmethyl ) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamide

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) was added piperidine (15O ul, 1.5 mmol) and 3 drops of AcOH. It was. The mixture was stirred for 12 h, then Na (OAc) ₃ BH (0.335 g, 1.5 mmol) was added. After 6 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL). The organic layer was separated and concentrated to give 166 mg (64%) of the title compound.

Replace the 2-methyl-1-propanamine with piperidine (78 mg, 0.3 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2- { Prepared according to the general procedure for [(2-methylpropyl) amino] methyl} -1,3-thiazol-4-yl) -1H-indole-7-carboxamide trifluoroacetate, 15.5 mg ( 51.6%).

LC / MS = m / z 517.4 [M + H] Retention time: 1.29.

Example  355: 5- {2-[(dimethylamino) methyl ] -1,3-thiazol-4-yl} -3- [1- ( Ethyl sulfo Nil) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) was added dimethyl amine (2.0 M, 3.0 mL) and 3 drops of AcOH. . The mixture was stirred for 48 hours, then Na (0Ac) ₃ BH (1.33 g, 6.0 mmol) was added. After 12 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL) and a separator was used to obtain a DCM organic layer. The organic layer was concentrated to give 90 mg (40%) of the desired product.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (2 mL) and water (0.7 mL) In a solution of dioxaborolan-2-yl) -1H-indole-7-carboxamide (46 mg, 0.1 mmol), dimethylamine (69 mg, 0.3 mmol) and potassium carbonate (83 mg, 0.6 mmol) Triacetoxyborohydride (12 mg, 0.01 mmol) was added. This mixture was degassed for 5 minutes. The mixture was then reacted at 160 ° C. for 20 minutes under microwave. The organic layer was separated and concentrated. It was then purified by Gilson preparative HPLC to give 23 mg (59%) of the title compound.

LC / MS = m / z 474.4 [M + H] Retention time: 1.20.

Example  356: 5- (2-{[ethyl ( methyl ) Amino] methyl } -1,3-thiazol-4-yl) -3- [1- ( Ethyl alcohol Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) N-methylethanamine (47O ul, 6.0 mmol) and 3 drops of AcOH Was added. The mixture was stirred for 48 h and then Na (OAc) ₃ BH (1.33 g, 6.0 mmol) was added. After 12 hours, the mixture was quenched with saturated NaHCO ₃ (4.0 mL) and brine (3.0 mL) and a separator was used to obtain a DCM organic layer. The organic layer was concentrated to give 160 mg (68%) of the title compound.

Replace the dimethylamine with ethyl (methyl) amine (73 mg, 0.3 mmol) and replace the title compound with 5- {2-[(dimethylamino) methyl] -1,3-thiazol-4-yl} -3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 25 mg (60.4%) of the title compound.

LC / MS = m / z 490.4 [M + H] Retention time: 1.25.

Example  357: 5- (3- Cyano -5-{[(2- Methylpropyl ) Amino] methyl } Phenyl ) -3- [1- ( ethyl Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

To a solution of 3-formylbenzonitrile (1.0 g, 7.6 mmol) in TFA (4.0 mL) was added dropwise concentrated H ₂ SO ₄ (6.0 mL) under argon atmosphere at 0 ° C. and then NBS was added in small portions. The mixture was allowed to warm slowly to room temperature and then stirred under argon atmosphere for 12 hours. When the reaction was complete, the mixture was poured into ice-H ₂ O (80 mL), PdCl ₂ (117 mg, 0.658 mmol), the solids collected and dried overnight under vacuum to yield 3-bromo-5-formylbenzamide 1.50 g (86%) was provided.

LC / MS = m / z 228.2 [M + H] Retention time: 1.37.

PdCl ₂ (117 mg, 0.658 mmol) was added to a solution of 3-bromo-5-formylbenzamide (1.5 g, 6.58 mmol) in H ₂ O (50.0 mL) and MeCN (50.0 mL). The mixture was stirred at rt for 72 h and additional portions of H ₂ O (100 mL) and MeCN (100 mL), followed by PdCl ₂ (100 mg, 0.56 mol). The mixture was stirred for a further 12 h and concentrated. The residue was dissolved in EtOAc (200 mL), washed with brine (3 × 50.0 mL), dried over Na ₂ SO _4, concentrated and purified by chromatography (10% EtOAc in hexane) to 3-bromo- 550 mg (40%) of 5-formylbenzonitrile were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3 in dioxane (2.0 mL) and H ₂ O (0.7 mL) 3-bromo-5-formylbenzonitrile (68 mg, 0.3 mmol) in a solution of, 2-dioxaborolan-2-yl) -1H-indole-7-carboxamide (46 mg, 0.1 mmol) And potassium carbonate (83 mg, 0.6 mmol). The mixture was degassed for 5 minutes and then tetrakis (triphenylphosphine) palladium (0) (12 mg, 0.01 mmol) was added. The mixture was reacted at 160 ° C. for 20 minutes under microwave. The compound was purified by Gilson preparative HPLC to give 5- (3-cyano-5-formylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox Provided amide.

5- (3-cyano-5-formylphenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- in dichloromethane (3 mL) and methanol (1 mL) To a solution of 7-carboxamide (47 mg, 0.1 mmol) was added a few drops of acetic acid and methyl (2-methylpropyl) amine (64 μl, 0.6 mmol). The mixture was stirred overnight, then 20 drops of acetic acid and sodium triacetoxyborohydride (0.6 mmol) were added. The reaction was mixed for 4 hours, then methyl (2-methylpropyl) amine (64 μl, 0.6 mmol) and sodium triacetoxyborohydride (0.6 mmol) were added. The mixture was stirred overnight and then quenched with sodium bicarbonate and brine. The organic layer was separated and concentrated by SOX cartridge. Subsequent separation using Gilson preparative HPLC gave 10.3 mg (63.6%) of the title compound.

LC / MS = m / z 522.4 [M + H] Retention time: 1.65.

Example  358: 5- {3- Cyano -5-[(dimethylamino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the methyl (2-methylpropyl) amine with trimethylamine (300 μl, 0.3 mmol) and replace the title compound with 5- (3-cyano-5-{[(2-methylpropyl) amino] methyl} phenyl)- Prepared according to the general procedure for 3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide trifluoroacetate to give 10.5 mg (61%) of the title compound. .

LC / MS = m / z 494.4 [M + H] Retention time: 1.48.

Example  359: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3- (4- Morpholinylmethyl ) Fe Nil] -1H-indole-7- Carboxamide Trifluoroacetate

In a solution of 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (80 mg, 0.181 mmol) in DCM Pauline (50 μl, 0.545 mmol) was added. The reaction was stirred at rt for 30 min and then sodium triacetoxyborohydride (120 mg, 0.545 mmol) was added. The reaction was allowed to react overnight at room temperature and then concentrated. The compound was purified by Gilson preparative HPLC to give 28.6 mg (25%) of the title compound.

LC / MS = m / z 511.4 [M + H] Retention time: 1.48 minutes.

Example  360: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(4- Fluorophenyl ) Carbonyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} acetamide to 4-fluoro-N-{[3 -(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} benzamide (125 mg, 0.352 mmol), replacing the title compound with 5- Prepared according to the general procedure for {3-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 18.3 mg (27%) of the title compound.

LC / MS = m / z 563.1 [M + H] Retention time: 2.07 minutes.

Example  361: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Furanylcarbonyl ) Amino] methyl} Phenyl ) -1H-indole-7- Carboxamide Trifluoroacetate

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} acetamide to N-{[3- (4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} -2-furancarboxamide (115 mg, 0.352 mmol), replacing the title compound with 5- Prepared according to the general procedure for {3-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 8.1 mg (12%) of the title compound.

LC / MS = m / z 535 [M + H] Retention time: 1.89 minutes.

Example  362: 5- (3-{[( Cyclopentylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethyl sulfo Nil) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} acetamide to N-{[3- (4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} cyclopentanecarboxamide (116 mg, 0.352 mmol), replacing the title compound with 5- {3 Prepared according to the general procedure for-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The compound was purified by Gilson preparative HPLC to give 9.2 mg (14%) of the title compound.

LC / MS = m / z 535 [M + H] Retention time: 1.89 minutes.

Example  363: 5- (3-{[(1- Benzothiene -2- Ilcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to N-{[3- (4,4 Instead of 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} -1-benzothiophene-2-carboxamide (57 mg, 0.144 mmol), General procedure for 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide It was prepared according to. The compound was purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 601.2 [M + H] Retention time: 2.18 minutes.

Example  364: 5- [3-({[(1-acetyl-4- Piperidinyl ) Carbonyl] amino} methyl ) Phenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to 1-acetyl-N-{[3- Instead of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} -4-piperidinecarboxamide (56 mg, 0.144 mmol) The title compound is generally prepared for 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide Prepared according to the procedure. The compound was purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 594.4 [M + H] Retention time: 1.87 minutes.

Example  365: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(1- methyl -1H-pyrrole-2-yl) carbonyl] amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to 1-methyl-N-{[3- Instead of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} -1H-pyrrole-2-carboxamide (49 mg, 0.144 mmol) The title compound was then prepared for 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide Prepared according to the general procedure. The compound was purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 548.4 [M + H] Retention time: 2.02 minutes.

Example  366: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[(2- Thienylacetyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to N-{[3- (4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} -2- (2-thienyl) acetamide (51 mg, 0.144 mmol) in place of The compound was subjected to the general procedure for 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide Prepared accordingly. The compound was purified by mass directed autoprep HPLC to give 10.3 mg (18.2%) of the title compound.

LC / MS = m / z 565.2 [M + H] Retention time: 1.95 minutes.

Example  367: 5- (3-{[( Cyclobutylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to N-{[3- (4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} cyclobutanecarboxamide (45 mg, 0.144 mmol), replacing the title compound with 3- [1 Prepared according to the general procedure for-(ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide. The compound was purified by mass directed autoprep HPLC to give 4.3 mg (8%) of the title compound.

LC / MS = m / z 523.4 [M + H] Retention time: 1.90 minutes.

Example  368: 5- (3-{[( Cyclopropylcarbonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

N-{[3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} pentanamide to N-{[3- (4,4 , 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] methyl} cyclopropanecarboxamide (43 mg, 0.144 mmol), replacing the title compound with 3- [ Prepared according to the general procedure for 1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide. The compound was purified by mass directed autoprep HPLC to give 5.5 mg (11%) of the title compound.

LC / MS = m / z 509.2 [M + H] Retention time: 1.85 minutes.

Example  369: 5- (3-{[( Cyclopropylsulfonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl ) -4-piperidinyl] -1 H-indole-7- Carboxamide

5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox in DMF (1.0 mL) and DCM (1.0 mL) To a solution of amide (35 mg, 0.079 mmol) was added cyclopropanesulfonyl chloride (11 mg, 0.079 mmol) and DIEA (14 μl, 0.079 mmol). The reaction was stirred at rt overnight. The compound was purified by Gilson preparative HPLC to give 7.2 mg (17%) of the title compound.

LC / MS = m / z 545.4 [M + H] Retention time: 1.94 minutes.

Example  370: 5- [3-({[(2,5- Dichlorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox in DMF (1.0 mL) and DCM (1.0 mL) To a solution of amide (40 mg, 0.096 mmol) was added 2,5-dichlorobenzenesulfonyl chloride (86 mg, 0.352 mmol) and DIEA (62 μl, 0.352 mmol). The reaction was stirred at rt for 6 h. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 6.6 mg (11%) of the title compound.

LC / MS = m / z 649.2 [M + H] Retention time: 2.25 minutes.

Example  371: 5- [3-({[(4- Bromophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 4-bromobenzenesulfonyl chloride (90 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl) sulfonyl ] Amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide according to the general procedure. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 19.4 mg (31%) of the title compound.

LC / MS = m / z 659.4 [M + H] Retention time: 2.20 minutes.

Example  372: 5- [3-({[(4- Chlorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with (2E, 4E) -5-chloro-2,4,6-heptatriene-2-sulfonyl chloride (80 mg, 0.352 mmol) to give the title compound 5 -[3-({[(2,5-dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Prepared according to the general procedure for voxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 7.5 mg (13%) of the title compound.

LC / MS = m / z 615.2 [M] Retention time: 2.19 minutes.

Example  373: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(3- Fluorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with 3-fluorobenzenesulfonyl chloride (69 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl) sulfonyl Prepared according to the general procedure for] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 7.3 mg (13%) of the title compound.

LC / MS = m / z 599.2 [M + H] Retention time: 2.15 minutes.

Example  374: 5- [3-({[(2- Chlorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with 2-chlorobenzenesulfonyl chloride (74 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl) sulfonyl] Prepared according to the general procedure for amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 17.3 mg (29%) of the title compound.

LC / MS = m / z 615.2 [M] Retention time: 2.15 minutes.

Example  375: 5- [3-({[(2,5- Dichloro -3- Thienyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with 2,5-dichloro-3-thiophensulfonyl chloride (86 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5- Prepared according to the general procedure for dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 16.7 mg (27%) of the title compound.

LC / MS = m / z 655.2 [M] Retention time: 2.24 minutes.

Example  376: 5- [3-({[(2- Chloro -6- Methylphenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- (on Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Instead of 2,5-dichlorobenzenesulfonyl chloride with 2-chloro-6-methylbenzenesulfonyl chloride (86 mg, 0.352 mmol), the title compound was replaced with 5- [3-({[(2,5-dichlorophenyl ) Sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 17.9 mg (30%) of the title compound.

LC / MS = m / z 629.4 [M] Retention time: 2.19 minutes.

Example  377: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(5- Fluoro -2- Methylphenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 5-fluoro-2-methylbenzenesulfonyl chloride (86 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5 -Dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide according to the general procedure. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 613.2 [M + H] Retention time: 2.18 minutes.

Example  378: 5- [3-({[(1,2-dimethyl-1H- Imidazole -4- days) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride (69 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2 Prepared according to the general procedure for, 5-dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide It was. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 1.9 mg (3.3%) of the title compound.

LC / MS = m / z 599.2 [M + H] Retention time: 1.76 minutes.

Example  379: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[( Phenylsulfonyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with benzenesulfonyl chloride (62 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl) sulfonyl] amino} methyl ) Phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide according to the general procedure. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 13.4 mg (24%) of the title compound.

LC / MS = m / z 581.6 [M + H] Retention time: 2.10 minutes.

Example  380: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [3-({[(4- Fluorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 4-fluorobenzenesulfonyl chloride (69 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl) sulfonyl Prepared according to the general procedure for] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 11.5 mg (20%) of the title compound.

LC / MS = m / z 599.2 [M + H] Retention time: 2.10 minutes.

Example  381: 5- [3-({[(4- Bromo -2- Ethylphenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 4-bromo-2-ethylbenzenesulfonyl chloride (100 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichloro Phenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 2.7 mg (4%) of the title compound.

LC / MS = m / z 687.6 [M] Retention time: 2.38 minutes.

Example  382: 5- (3-{[(1- Benzothiene -3- Sulfonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace 2,5-dichlorobenzenesulfonyl chloride with 1-benzothiophen-3-sulfonyl chloride (82 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl ) Sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 3.9 mg (6%) of the title compound.

LC / MS = m / z 637.4 [M + H] Retention time: 2.19 minutes.

Example  383: 5- {3-[({[4- (1,1-dimethylethyl) Phenyl ] Sulfonyl } Amino) methyl ] Phenyl } -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 4- (1,1-dimethylethyl) benzenesulfonyl chloride (82 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5 -Dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide according to the general procedure. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to give 15.6 mg (26%) of the title compound.

LC / MS = m / z 637.4 [M + H] Retention time: 2.35 minutes.

Example  384: 5- [3-({[(3,4- Difluorophenyl ) Sulfonyl ] Amino} methyl ) Phenyl ] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 3,4-difluorobenzenesulfonyl chloride (75 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2,5-dichlorophenyl ) Sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 617.2 [M + H] Retention time: 2.16 minutes.

Example  385: 5- (3-{[(2,1,3- Benzoxadiazole -4- Sulfonyl ) Amino] methyl } Phenyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2,5-dichlorobenzenesulfonyl chloride with 2,1,3-benzoxadiazol-4-sulfonyl chloride (77 mg, 0.352 mmol) and replace the title compound with 5- [3-({[(2 Prepared according to the general procedure for, 5-dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide It was. The reaction mixture was then concentrated and purified by Gilson preparative HPLC to provide the title compound.

LC / MS = m / z 623.4 [M + H] Retention time: 2.10 minutes.

Example  386: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[( Tetrahydro -3- Furanylcarbonyl ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

To a solution of tetrahydro-3-furancarboxylic acid (17 mg, 0.144 mmol) in DCM (2.0 mL) was added pyridine (3 drops) and oxalyl chloride (18 mg, 0.144 mmol). The reaction mixture was stirred at rt overnight. The mixture was then added to 5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- in DMF (1.0 mL) and DIEA (33 μl, 0.192 mmol). Indole-7-carboxamide (40 mg, 0.096 mmol) was added. The reaction mixture was stirred at rt overnight. The reaction mixture was concentrated under nitrogen and purified by Gilson preparative HPLC to give 5.3 mg (10%) of the title compound.

LC / MS = m / z 539.2 [M + H] Retention time: 1.80 minutes.

Example  387: 5- {4-[( Cyclopentylsulfonyl ) Amino] Phenyl } -3- [1- ( Ethylsulfonyl )-4-[ Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Chloro (di-2-norbornylphosph) in 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20 mg, 0.048 mmol) Pino) (2-dimethylaminomethylferrocen-1-yl) palladium (II) (10 mg, 0.016 mmol), potassium carbonate (13.4 mg, 0.097 mmol), and dioxane (3 mL) and H ₂ O (1 mL ) Was added N- [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] cyclopentanesulfonamide (34 mg, 0.097 mmol). . The reaction mixture was heated at 160 ° C. for 10 minutes under microwave. The reaction mixture was concentrated under nitrogen and purified by Gilson preparative HPLC to give 8.6 mg (32%) of the title compound.

LC / MS = m / z 559.2 [M + H] Retention time: 2.00 minutes.

Example  388: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [4- (4- methyl -2-oxo-1- Piperazinyl ) Phenyl] -1H-indole-7- Carboxamide

Dioxane (3.0 mL) and H ₂ O in 5-bromo-3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide (20 mg, 0.048 mmol) 4-methyl-1- [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -2-piperazinone in (1.0 mL) ( 31 mg, 0.097 mmol), potassium carbonate (13 mg, 0.097 mmol) and chloro (di-2-norbornylphosphino) (2-dimethylaminomethylferrocen-1-yl) palladium (II) (10 mg, 0.016 mmol) was added. The reaction mixture was reacted at 160 ° C. for 10 minutes under microwave. The reaction mixture was heated at 160 ° C. for 10 minutes under microwave. The reaction mixture was concentrated under nitrogen and purified by Gilson preparative HPLC. The desired fractions in CH ₃ CN and H ₂ O were treated with saturated potassium carbonate to neutralize the salt and then concentrated to give 1.9 mg (8%) of the title compound.

LC / MS = m / z 524.6 [M + H] Retention time: 1.49 minutes.

Example  389: 5- [6- (4-acetyl-1- Piperazinyl ) -3- Pyridinyl ] -3- [1- ( Ethylsulfonyl ) -4-p Fe Ridinyl] -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-piperazinyl) -3-pyridinyl] -1H-indole-7-carboxamide in dichloromethane ( To a solution of 40 mg, 0.080 mmol) was added acetyl chloride (7 μL, 0.096 mmol) and DIEA (11.6 μL, 0.12 mmol) at 0 ° C. The reaction mixture was reacted at 0 ° C. to room temperature for 0.5 h and then quenched with H ₂ O. The compound was purified by MDAP HPLC to give 7 mg (40%) of the title compound.

LC / MS = m / z 539.4 [M + H] Retention time: 1.27 minutes.

Example  390: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (4-{[( Methyloxy ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-formylphenyl) -1H-indole-7-carboxamide in DCM (1.5 mL) and MeOH (1.5 mL) ( To a solution of 50 mg, 0.114 mmol) was added O-methylhydroxylamine (114 mg, 1.71 mmol). The reaction was stirred overnight. The solvent was then concentrated and purified by Gilson preparative HPLC to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methyloxy) imino] methyl} phenyl) -1H 38 mg (76%) of indole-7-carboxamide were provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methyloxy) imino] methyl} phenyl) -1H in DCM (3.0 mL) and MeOH (3.0 mL) To a solution of indole-7-carboxamide (21.5 mg, 0.046 mmol) was added dropwise HCl in 1,4-dioxane at 0 ° C. to maintain pH = 4. Sodium cyanoborohydride (29 mg, 0.46 mmol) was then added and stirred at rt overnight. In addition to sodium cyanoborohydride (45 mg, 0.72 mmol), HCl in additional 1,4-dioxane was added to maintain pH = 4. The reaction mixture was then stirred over 48 hours. At 0 ° C. additional HCl in 1,4-dioxane was added to maintain pH = 4 and stirred until reaching room temperature. The mixture was quenched with H ₂ O. Then DCM was added for aqueous workup and the mixture was concentrated. The residue was then taken up in DCM and purified on an SCX SPE cartridge to give 15.2 mg (70%) of the title compound.

LC / MS = m / z 471.6 [M + H] Retention time: 1.67 minutes.

Example  391: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (3-{[( Methyloxy ) Amino] methyl } Phenyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-formylphenyl) -1H-indole-7-carboxamide (50 mg, 0.114 mmol) in DMSO (3.0 mL) To a solution of O-methylhydroxylamine (57 mg, 0.684 mmol) was added. The reaction was stirred overnight. Additional O-methylhydroxylamine (0.342 mmol) was added to the reaction mixture and stirred for 48 hours. The solvent was then concentrated and purified by Gilson preparative HPLC to give 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methyloxy) imino] methyl} phenyl) -1H 29.8 mg (56%) of indole-7-carboxamide was provided.

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methyloxy) imino] methyl} phenyl) -1H in DCM (3.0 mL) and MeOH (3.0 mL) To a solution of indole-7-carboxamide (58 mg, 0.123 mmol) was added HCl in 1,4-dioxane at 0 ° C. to maintain pH = 4. Sodium cyanoborohydride (176 mg, 3.69 mmol) was then added and stirred for 48 hours overnight. The compound was purified by Gilson preparative HPLC to give 20.0 mg (89%) of the title compound.

LC / MS = m / z 471.6 [M + H] Retention time: 1.75 minutes.

Example  392: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[4- (1- Pyrrolidinyl ) -1-piperidinyl] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (50 mg in DMSO (2.0 mL) , 0.112 mmol) was added 4- (1-pyrrolidinyl) piperidine (173 mg, 1.12 mmol) and acetic acid (5 drops). After 6 hours, sodium triacetoxyborohydride (238 mg, 1.12 mmol) was added and the reaction stirred overnight. The reaction mixture was purified by Gilson preparative HPLC to give 17.0 mg (26%) of the title compound.

LC / MS = m / z 584.4 [M + H] Retention time: 1.38 minutes.

Example  393: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[(2S) -2- ( Trifluoromethyl )-1-p Lolly Neil] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7- in DCM (3.0 mL) and MeOH (1.5 mL) To a solution of carboxamide (50 mg, 0.112 mmol) was added (2S) -2- (trifluoromethyl) pyrrolidine (156 mg, 1.12 mmol) and acetic acid (5 drops). After stirring for 6 hours at room temperature, sodium borohydride (43 mg, 1.12 mmol) was added and the reaction stirred overnight at room temperature. The reaction mixture was purified by Gilson preparative HPLC to give 5.0 mg (8%) of the title compound.

LC / MS = m / z 569.4 [M + H] Retention time: 2.37 minutes.

Example  394: 5- (5-{[(2R) -2- ( Hydroxymethyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- {1-[(1-meth Teal ethyl) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

5- (5-formyl-3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-car in DMSO (2 mL) To a solution of voxamide (25 mg, 0.054 mmol) was added (2R) -2-pyrrolidinylmethanol (101.15 mg, 1 mmol) and two drops of acetic acid. The resulting mixture was stirred at rt for 4 h and then sodium triacetoxyborohydride (212 mg, 0.54 mmol) was added. The mixture was allowed to react overnight. It was then purified by Gilson preparative HPLC to give 20.5 mg (69.7%) of the title compound.

LC / MS = m / z 546 [M + H] Retention time: 1.47 minutes.

Example  395: 5- (5-{[(3S) -3-hydroxy-1- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

Replace (2R) -2-pyrrolidinylmethanol with (3S) -3-pyrrolidinol (90.13 mg, 1.20 mmol) and replace the title compound with 5- (5-{[(2R) -2- (hydroxy Methyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide Prepared according to the general procedure for 12.8 mg (53.1%) of the title compound.

LC / MS = m / z 532 [M + H] Retention time: 1.45 minutes.

Example  396: 5- (5-{[cyclopentyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- {1-[(1- Methylethyl ) Sulfonyl] -4- Piperidinyl } -1H-indole-7- Carboxamide

(2R) -2-pyrrolidinylmethanol with N-methylcyclopentanamine (90.13 mg, 1.20 mmol), and the title compound was replaced with 5- (5-{[(2R) -2- (hydroxymethyl)- General for 1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide Prepared according to the procedure to give 10 mg (54.3%) of the title compound.

LC / MS = m / z 544.2 [M + H] Retention time: 1.65 minutes.

Example  397: 5- (5-{[(2- Hydroxyethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- {1-[(1- Methylethyl ) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

Replace (2R) -2-pyrrolidinylmethanol with 2- (methylamino) ethanol (90.13 mg, 1.20 mmol) and replace the title compound with 5- (5-{[(2R) -2- (hydroxymethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1 H-indole-7-carboxamide Prepared according to the general procedure to give 8 mg (51.9%) of the title compound.

LC / MS = m / z 520 [M + H] Retention time: 1.44 minutes.

Example  398: 5- (5-{[(2-amino-2- Oxoethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- {1-[(1-meth Teal ethyl) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

Replace (2R) -2-pyrrolidinylmethanol with N2-methylglycinamide (90.13 mg, 1.200 mmol) and replace the title compound with 5- (5-{[(2R) -2- (hydroxymethyl) -1 General procedure for -pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide Prepared according to yield 15 mg (53.2%) of the title compound.

LC / MS = m / z 520 [M + H] Retention time: 1.44 minutes.

Example  399: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[methyl (2- Propene -1-yl) amino] methyl} -3- Thienyl ) -1H-indole-7- Carboxamide

Allylamine (0.034 mL, 0.449 mmol) and HOAc (0.026 mL, 0.449 mmol) were added to 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- in DMSO (0.5 mL) in a 1-dram vial. To a solution of (5-formyl-3- thienyl) -1H-indole-7-carboxamide (20 mg, 0.0449 mmol). NaBH (OAc) ₃ (95 mg, 0.449 mmol) was then added, the vial was capped and the reaction stirred at rt for 15 h. NaCNBH ₃ (28 mg, 0.449 mmol) and MeOH were added and the reaction stirred for an additional 4 hours. 37 wt% aqueous formaldehyde solution (0.069 mL, 0.898 mmol) was added and the reaction stirred for an additional 1 hour. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL of MeOH) eluting with a 2 M solution of MeOH (3 mL) and NH ₃ / MeOH (9 mL). The NH ₃ / MeOH fraction was concentrated at 50 ° C. under a stream of nitrogen and the residue was dissolved in DMSO (1 mL) and 10% CH ₃ CN / H ₂ O (0.1% NH ₄ over 15 minutes at 20 mL per minute). OH) → purified on Gilson HPLC (Xbridge Prep C18 column: 19 × 100 mm) eluting with a linear gradient of 70% CH ₃ CN / H ₂ O (0.1% NH ₄ OH). Fractions containing the title compound were concentrated at 50 ° C. under a nitrogen stream to give 5.2 mg (23%) of the title compound.

LC / MS = m / z 501.4 [M + H] Retention time: 1.48 minutes.

Example  400: 5- (5-{[[(3,5-dimethyl-1H- Pyrazole -4- days) methyl ] ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (1.0 mL) ( To 45 mg, 100 μmol) was added 1- (3,5-dimethyl-1H-pyrazol-4-yl) -N-methylmethanamine (320 μmol) and 2-3 drops of glacial acetic acid. The resulting mixture was stirred overnight. After 18 hours, sodium triacetoxyborohydride (200 mg, 1000 μmol) was added. The mixture was stirred for 1.5 h and then purified by Gilson preparative HPLC to give 6.24 mg (11.0%) of the title compound.

LC / MS = m / z 569.3 [M + H] Retention time: 1.42 minutes.

Example  401: 5- (5-{[( Cyanomethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 1- (3,5-dimethyl-1H-pyrazol-4-yl) -N-methylmethanamine with (methylamino) acetonitrile (320 μmol) and replace the title compound with 5- (5-{[[ (3,5-dimethyl-1H-pyrazol-4-yl) methyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl]- Prepared according to the general procedure for 1H-indole-7-carboxamide to yield 6.36 mg (12.7%) of the title compound.

LC / MS = m / z 430 [M + H] Retention time: 1.70 minutes.

Example  402: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl] -5- (5-{[methyl (1- Methylpropyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (1 mL) To 45 mg, 0.1 mmol) was added 2-butanamine (1 mmol), 1-2 drops of acetic acid and sodium triacetoxyborohydride (211 mg, 1 mmol). The resulting mixture was capped and stirred for 18 hours, then sodium cyanoborohydride (62 mg, 1 mmol) in methanol (0.5 mL) was added. It was stirred for 3 hours and then formaldehyde (37% in water) (1.5 mL) was added. It was purified through an SCX (2 g) cartridge eluting with methanol followed by NH ₃ in methanol. Further purification by Gilson preparative HPLC (XBridge C18 column; P / N 186002978) using a gradient of 10% acetonitrile to 70% acetonitrile (0.1% NH ₄ OH) in water 14.4 mg (27.9%) of the title compound Provided.

LC / MS = m / z 517.3 [M + H] Retention time: 1.58 minutes.

Example  403: 5- (5-{[[2- ( Ethyloxy )ethyl]( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

The title compound was replaced with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {instead of 2-butanamine added with 2- (ethyloxy) ethanamine (1 mmol). Prepared according to the general procedure for [methyl (1-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide to give 6.1 mg (11.5%) of the title compound.

LC / MS = m / z 533.2 [M + H] Retention time: 1.57 minutes.

Example  404: 5- (5-{[cyclobutyl ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- ( Ethyl alcohol Ponyl) -4-P Peridi Nil] -1H-indole-7- Carboxamide Trifluoroacetate

The title compound was replaced with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-), replacing the added 2-butanamine with cyclobutylamine (1 mmol). Prepared according to the general procedure for methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide to give 3.7 mg (5.9%) of the title compound.

LC / MS = m / z 515.3 [M + H] Retention time: 1.64 minutes.

Example  405: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({2-[( Methyloxy ) methyl ] -1-p Lolly Neil} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the added 2-butanamine with 2-[(methyloxy) methyl] pyrrolidine (1 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- Prepared according to the general procedure for (5-{[methyl (1-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide to give 5 mg (7.6%) of the title compound. It was.

LC / MS = m / z 545.3 [M + H] Retention time: 1.65 minutes.

Example  406: 5- (5-{[(1,1-dimethylethyl) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (in Tilsule Ponyyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

The title compound was replaced with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {instead of 2-butanamine added with 2-methyl-2-propanamine (1 mmol). Prepared according to the general procedure for [methyl (1-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide to give 10.9 mg (17.3%) of the title compound.

LC / MS = m / z 517.3 [M + H] Retention time: 1.61 minutes.

Example  407: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[3- ( Trifluorome Teal) -1- Piperidinyl ] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Instead of 2-butanamine added with 3- (trifluoromethyl) piperidine (1 mmol), the title compound was replaced with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- ( Prepared according to the general procedure for 5-{[methyl (1-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide to give 5.4 mg (7.8%) of the title compound. It was.

LC / MS = m / z 583.3 [M + H] Retention time: 1.73 minutes.

Example  408: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] ( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Vial containing (2R) -2-amino-1-propanol (90.13 mg, 1.2 mmol) in 3- [1- (ethylsulfonyl) -4-piperidi in DMSO (300 μl) and acetic acid (50 μl) Neyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (30 mg, 0.067 mmol) was added. The resulting mixture was shaken for 5 minutes and then sodium triacetoxyborohydride (250 mg, 1.20 mmol) in DMSO (800 μl) was added. The mixture was shaken overnight. Sodium cyanoborohydride (79 mg, 1.20 mmol) in methanol (300 μl) was then added and stirred for 48 h. Formaldehyde (100 μl) was then added. The reaction was then stirred for 1 hour before the 2 g SCX crude cartridge was separated. The solid was then filtered and the solution concentrated and the purification on a 5 g SCX cartridge eluting with ammonia in MeOH was repeated. The ammonia fraction in collected MeOH was concentrated and separated using Gilson preparative HPLC to give 18.6 mg (43.9%) of the title compound.

LC / MS = m / z 519.3 [M + H] Retention time: 1.49 minutes.

Example  409: 5- (5-{[( Cyclopropylmethyl ) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2R) -2-amino-1-propanol with (cyclopropylmethyl) amine (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- ( 5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate (salt) Prepared according to the general procedure for 6.2 mg (14.7%) of the title compound.

LC / MS = m / z 515.3 [M + H] Retention time: 1.61 minutes.

Example  410: 5- (5-{[[2- ( Acetylamino )ethyl]( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (in Tilsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2R) -2-amino-1-propanol with N- (2-aminoethyl) acetamide (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate Prepared according to the general procedure for (salt) to give 13.6 mg (30.8%) of the title compound.

LC / MS = m / z 546.2 [M + H] Retention time: 1.47 minutes.

Example  411: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[(1R, 2R) -2- Hydroxy Cyclopentyl] ( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2R) -2-amino-1-propanol with (1R, 2R) -2-aminocyclopentanol (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidi Nil] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide tri Prepared according to the general procedure for fluoroacetate (salt) to yield 9.6 mg (21.8%) of the title compound.

LC / MS = m / z 545.3 [M + H] Retention time: 1.54 minutes.

Example  412: 5- (5-{[(1,1-dimethylpropyl) ( methyl ) Amino] methyl } -3- Thienyl ) -3- [1- (in Teal Sulfonyl) -4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace the (2R) -2-amino-1-propanol with (1,1-dimethylpropyl) amine (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl]- 5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoroacetate ( Preparation) gave 13.1 mg (30.3%) of the title compound.

LC / MS = m / z 531.3 [M + H] Retention time: 1.65 minutes.

Example  413: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[(2S) -2-hydroxypropyl] ( Me Til) amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

Replace the (2R) -2-amino-1-propanol with (2S) -1-amino-2-propanol (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl ] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluoro Prepared according to the general procedure for acetate (salt) to give 15.3 mg (36.1%) of the title compound.

LC / MS = m / z 519.3 [M + H] Retention time: 1.49 minutes.

Example  414: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5-({methyl [(2R)- Tetrahydrate Rho-2-furanylmethyl] amino} methyl ) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2R) -2-amino-1-propanol with [(2R) -tetrahydro-2-furanylmethyl] amine (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4 -Piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carbox Prepared according to the general procedure for amide trifluoroacetate (salt) to give 15.5 mg (35.1%) of the title compound.

LC / MS = m / z 545.3 [M + H] Retention time: 1.58 minutes.

Example  415: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[{2-[(2- Hydroxyethyl ) Oxy] ethyl} ( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

(2R) -2-amino-1-propanol with 2-[(2-aminoethyl) oxy] ethanol (1.20 mmol) and the title compound with 3- [1- (ethylsulfonyl) -4-piperidi Nil] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide trifluor Prepared according to the general procedure for roacetate (salt) to give 17.2 mg (38.7%) of the title compound.

LC / MS = m / z 549.5 [M + H] Retention time: 1.48 minutes.

Example  416: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [5- (1- {methyl [2- ( Methyloxy ) Ethyl] amino} ethyl) -3- Thienyl ] -1H-indole-7- Carboxamide Trifluoroacetate

5- (5-acetyl-3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbohydrate in EtOH (2.0 mL) and AcOH (0.2 mL) To a solution of boxamide (46 mg, 0.1 mmol) was added methyl [2- (methyloxy) ethyl] amine (200 μl, 2.0 mmol) and sodium cyanoborohydride (50 mg, 0.8 mmol). The mixture was reacted at 120 ° C. for 2 hours under microwave. Additional methyl [2- (methyloxy) ethyl] amine (100 μl, 1.0 mmol) and sodium cyanoborohydride (25 mg, 0.4 mmol) were added and reacted for additional 3 hours at 120 ° C. under microwave. Then methyl [2- (methyloxy) ethyl] amine (100 μl, 2.0 mmol) and sodium cyanoborohydride (25 mg, 0.4 mmol) were added again and reacted for an additional 3 hours at 120 ° C. under microwave. I was. All solvents were concentrated and purified by Gilson preparative HPLC to give 20 mg (38%) of the title compound.

LC / MS = m / z 533.2 [M + H] Retention time: 1.46 minutes.

Example  417: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5- {1- [methyl (propyl) amino] ethyl} -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroacetate

5- (5-acetyl-3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbohydrate in EtOH (2.0 mL) and AcOH (0.2 mL) To a solution of boxamide (46 mg, 0.1 mmol) was added N-methyl-1-propanamine (200 μl, 2.0 mmol) and sodium cyanoborohydride (50 mg, 0.8 mmol). The mixture was reacted at 120 ° C. for 120 minutes under microwave. Additional N-methyl-1-propanamine (100 μl, 1.0 mmol) and sodium cyanoborohydride (25 mg, 0.4 mmol) were added and reacted for an additional 3 hours at 120 ° C. under microwave. All solvents were concentrated, dissolved in DMSO and the solids filtered. It was then purified by Gilson preparative HPLC to give 18 mg (35%) of the title compound.

LC / MS = m / z 517.2 [M + H] Retention time: 1.52 minutes.

Example  418: 5- (2,3- Dehydro -1H- Isoindole -5-day) -S- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4,4,5,5-tetramethyl-1,3,2 in dioxane (0.75 mL) and water (0.25 mL) 5-bromo-2,3-dihydro-1H-isoindole hydrochloride (130) in a solution of -dioxaborolan-2-yl) -1H-indole-7-carboxamide (150 mg, 0.325 mmol) mg, 0.651 mmol) and cesium carbonate (636 mg, 1.952 mmol) were added. The reaction mixture was kept under argon for 10 minutes and then tetrakis (triphenylphosphine) palladium (0) (19 mg, 0.016 mmol) was added. The resulting mixture was heated at 150 ° C. for 20 minutes under microwave. The mixture was then purified by HPLC to give 11 mg of the title compound.

LC / MS = m / z 453 [M + H] Retention time: 1.33 minutes.

Example  419: 5- (2-ethyl-2,3- Dehydro -1H- Isoindole -5-day) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

5- (2,3-dihydro-1H-isoindol-5-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- in MeOH (1 mL) To a solution of carboxamide (20 mg, 0.044 mmol) was added acetaldehyde (6 mg, 0.133 mmol), sodium cyanoborohydride (6 mg, 0.088 mmol) and zinc chloride (6 mg, 0.044 mmol). The resulting mixture was heated at 100 ° C. for 30 minutes under microwave. The mixture was then concentrated, filtered and purified by Gilson preparative HPLC to give 8.2 mg of the title compound.

LC / MS = m / z 481 [M + H] Retention time: 1.40 minutes.

Example  420: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (1- Methylethyl ) -2,3- Dehydro -1H-this postmark Dol-5-yl] -1H-indole-7- Carboxamide

5- (2,3-dihydro-1H-isoindol-5-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- in MeOH (0.5 mL) To a solution of carboxamide (30 mg, 0.066 mmol) was added 2-propanone (12 mg, 0.198 mmol), sodium cyanoborohydride (8 mg, 0.133 mmol) and zinc chloride (9 mg, 0.066 mmol). It was. The resulting mixture was heated at 100 ° C. for 30 minutes under microwave. The mixture was then concentrated, filtered and purified by Gilson preparative HPLC to give 0.8 mg of the title compound.

LC / MS = m / z 495.5 [M + H] Retention time: 1.56 minutes.

Example  421: 5- [2- (1,2-dimethylpropyl) -2,3- Dehydro -1H- Isoindole -5-day] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

The title compound was replaced by 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- instead of 2-propanone with 3-methyl-2-butanone (17 mg, 0.198 mmol). Prepared according to the general procedure for (1-methylethyl) -2,3-dihydro-1H-isoindol-5-yl] -1H-indol-7-carboxamide to give 14.6 mg of the title compound.

LC / MS = m / z 523 [M + H] Retention time: 1.55 minutes.

Example  422: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- [2- (1- Methylpropyl ) -2,3- Dehydro -1H-this postmark Dol-5-yl] -1H-indole-7- Carboxamide

The title compound was substituted with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-methyl), replacing 2-propanone with 2-butanone (14 mg, 0.198 mmol). Prepared according to the general procedure for ethyl) -2,3-dihydro-1H-isoindol-5-yl] -1H-indol-7-carboxamide to give 14.6 mg of the title compound.

LC / MS = m / z 509 [M + H] Retention time: 1.48 minutes.

Example  423: 5- [2- (1-ethylpropyl) -2,3- Dehydro -1H- Isoindole -5-day] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

The title compound was substituted with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-methyl), replacing 2-propanone with 3-pentanone (17 mg, 0.198 mmol). Prepared according to the general procedure for ethyl) -2,3-dihydro-1H-isoindol-5-yl] -1H-indol-7-carboxamide to give 13.8 mg of the title compound.

LC / MS = m / z 523 [M + H] Retention time: 1.58 minutes.

Example  424: 5- (2- Cyclopentyl -2,3- Dehydro -1H- Isoindole -5-day) -3- [1- ( Ethylsulfonyl ) -4-p Peridi Nil] -1H-indole-7- Carboxamide

Replace the 2-propaneone with cyclopentanone (17 mg, 0.198 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-methylethyl Prepared according to the general procedure for) -2,3-dihydro-1H-isoindole-5-yl] -1H-indole-7-carboxamide to yield 4.8 mg of the title compound.

LC / MS = m / z 521 [M + H] Retention time: 1.54 minutes.

Example  425: 5- [2- ( Cyclopropylmethyl ) -2,3- Dehydro -1H- Isoindole -5-day] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2-propane with cyclopropanecarbaldehyde (14 mg, 0.198 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1- Prepared according to the general procedure for methylethyl) -2,3-dihydro-1H-isoindol-5-yl] -1H-indole-7-carboxamide to give 10.8 mg of the title compound.

LC / MS = m / z 507 [M + H] Retention time: 1.47 minutes.

Example  426: 5- [2- (2,2-dimethylpropyl) -2,3- Dehydro -1H- Isoindole -5-day] -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide

Replace the 2-propanone with 2,2-dimethylpropanal (17 mg, 0.198 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- ( Prepared according to the general procedure for 1-methylethyl) -2,3-dihydro-1H-isoindol-5-yl] -1H-indol-7-carboxamide to give 12.7 mg of the title compound.

LC / MS = m / z 523 [M + H] Retention time: 1.60 minutes.

Example  427: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2- methyl -2,3- Dehydro -1H- Isoindole -5-yl) -1H-indole-7- Carboxamide

The title compound was substituted with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-methylethyl), replacing 2-propanone with formaldehyde (6 mg, 0.198 mmol). Prepared according to the general procedure for -2,3-dihydro-1H-isoindol-5-yl] -1H-indol-7-carboxamide to give 1.2 mg of the title compound.

LC / MS = m / z 467 [M + H] Retention time: 1.37 minutes.

Example  428: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (2-{[( Phenylsulfonyl ) Amino] carbonyl} -2,3- Dehydro -1H- Isoindole -5-yl) -1H-indole-7- Carboxamide

5- (2,3-dihydro-1H-isoindol-5-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- in DMSO (1.0 mL) To a solution of carboxamide (30 mg, 0.066 mmol) was added benzenesulfonyl isocyanate (15 mg, 0.079 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was purified by Gilson preparative HPLC to give 15.5 mg of the title compound.

LC / MS = m / z 637 [M + H] Retention time: 1.94 minutes.

Example  429: 5- (5-{[(2R) -2- ( Aminocarbonyl )-One- Pyrrolidinyl ] methyl } -3- Thienyl ) -3- {1-[(1-meth Teal ethyl) Sulfonyl ]-4- Piperidinyl } -1H-indole-7- Carboxamide

5- (5-formyl-3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-car in DMSO (2 mL) To a solution of boxamide (25 mg, 0.054 mmol) was added D-prolineamide (114 mg, 1 mmol) and two drops of acetic acid. The resulting mixture was stirred at rt for 4 h and then sodium triacetoxyborohydride (212 mg, 1.0 mmol) was added. The mixture was allowed to react overnight. Purification by Gilson preparative HPLC gave 20.4 mg of the title compound.

LC / MS = m / z 557 [M + H] Retention time: 1.56 minutes.

Example  430: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[2- ( Ethylthio )ethyl]( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

5- (5-formyl-3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-car in DMSO (2 mL) [2- (ethylthio) ethyl] amine (105 mg, 1 mmol), acetic acid (50 μl) and sodium triacetoxyborohydride (212 mg, 1.0 mmol) in a solution of boxamide (40 mg, 0.09 mmol) Was added. The resulting mixture was stirred overnight. To the mixture was added sodium cyanoborohydride (80 mg, 1.2 mmol) and stirred overnight followed by addition of formaldehyde (100 μl, 1.2 mmol). The mixture was then stirred for an additional 3 hours. Then purification by Gilson preparative HPLC gave 7.0 mg of the title compound.

LC / MS = m / z 550 [M + H] Retention time: 1.68 minutes.

Example  431: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[{2-[(2- Hydroxyethyl ) Thio Ethyl} ( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace [2- (ethylthio) ethyl] amine with 2-[(2-aminoethyl) thio] ethanol (121 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4- According to the general procedure for piperidinyl] -5- (5-{[[2- (ethylthio) ethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide To give 16.0 mg of the title compound.

LC / MS = m / z 566 [M + H] Retention time: 1.52 minutes.

Example  432: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[2-hydroxy-1- ( Hydroxymethyl )ethyl]( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide

Replace [2- (ethylthio) ethyl] amine with 2-amino-1,3-propanediol (91 mg, 1.0 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidi Nil] -5- (5-{[[2- (ethylthio) ethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide according to the general procedure for 15.0 mg of the title compound were obtained.

LC / MS = m / z 535 [M + H] Retention time: 1.44 minutes.

Example  433: ethyl [(4- {7- ( Aminocarbonyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indol-5-yl} -2- Thienyl ) methyl ] Methylcarbamate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -3-thienyl} -1H-indole-7-carbine in DMF (1.0 mL) To a solution of boxamide (50 mg, 0.11 mmol) was added triethylamine (0.06 mL, 0.44 mmol) and ethyl chloridocarbonate (0.021 mL, 0.22 mmol) at 0 ° C. The resulting mixture was reacted for 30 minutes and then purified on Gilson preparative HPLC to give 31.4 mg (53.5%) of the title compound.

LC / MS = m / z 533.2 [M + H] Retention time: 2.06 minutes.

Example  434: ethyl N-[(4- {7- ( Aminocarbonyl ) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indol-5-yl} -2- Thienyl ) methyl ] -N- Methylglycinate

3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide in dimethyl sulfoxide (1.0 mL) ( To 45 mg, 100 μmol) was added ethyl N-methyl glycinate (320 μmol) and 2-3 drops of glacial acetic acid. The resulting mixture was stirred overnight. After 18 hours, sodium triacetoxyborohydride (200 mg, 1000 μmol) was added. The mixture was stirred for 1.5 h and then purified by Gilson preparative HPLC to give 16.5 mg (30.0%) of the title compound.

LC / MS = m / z 547.1 [M + H] Retention time: 1.55 minutes.

Example  435: 3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] ( methyl ) Amino] methyl } -3- Thienyl ) -1H-indole-7- Carboxamide Trifluoroa Catetate (salt)

Vial containing (2S) -2-amino-1-propanol (91 mg, 1.2 mmol) in 3- [1- (ethylsulfonyl) -4-piperidi in DMSO (300 μl) and acetic acid (50 μl) Neyl] -5- (5-formyl-3-thienyl) -1H-indole-7-carboxamide (30 mg, 0.067 mmol) was added. The resulting mixture was shaken for 5 minutes and then sodium triacetoxyborohydride (250 mg, 1.20 mmol) in DMSO (800 μl) was added. The mixture was shaken overnight. Sodium cyanoborohydride (79 mg, 1.20 mmol) in methanol (300 μl) was then added and stirred for 48 h. Formaldehyde (100 μl) was then added. Then, after stirring for 1 hour, 2 g SCX cartridge was separated. The solid was then filtered off, the solution was concentrated and purification on a 5 g SCX cartridge eluting with ammonia in MeOH was repeated. The ammonia fraction in collected MeOH was concentrated and separated using Gilson preparative HPLC to give 18.7 mg of the title compound.

LC / MS = m / z 519.3 [M + H] Retention time: 1.49 minutes.

Example  436: 5- (5-{[(1,1- Dioxydotetrahydro -3- Thienyl ) ( methyl ) Amino] Me Teal} -3- tea Enyl) -3- [1- ( Ethylsulfonyl )-4- Piperidinyl ] -1H-indole-7- Carboxamide Trifluoroacetate

Replace (2S) -2-amino-1-propanol with (1,1-dioxydotetrahydro-3-thienyl) amine (1.20 mmol) and replace the title compound with 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3-thienyl) -1H-indole-7- Prepared according to the general procedure for carboxamide trifluoroacetate to give 9.3 mg of the title compound.

LC / MS = m / z 579 [M + H] Retention time: 1.54 minutes.

<Biological data>

IKK2  analysis

Recombinant human IKKβ (1-737 residues) is expressed as a C-terminal GST-tagged fusion protein in baculovirus and its activity is time-resolved fluorescence resonance energy transfer. : TR-FRET) assay. In brief, IKK2 (final 0.5-5 nM) diluted in assay buffer (1 mM CHAPS pH 7.4 containing 50 mM HEPES, 10 mM MgCl ₂ , 1 mM DTT, and 0.01 w / v% BSA) was used at various concentrations of the compound. Or to wells containing DMSO vehicle (final 1.7%). The reaction was initiated by adding GST-IB substrate (final 25 nM) / ATP (final 1 μM) in a total volume of 6 μl. The reaction was incubated for 15 minutes at room temperature and then the anti-phosphoseline-IB-32 / 36 monoclonal antibody 12C2 (Wallac OY, Turku, Finland) labeled with W-1024 europium chelate (Wallac OY, Turku, Finland) 50 mM EDTA containing buffer (100 mM HEPES pH 7.4) containing Bellley's Cell Signaling Technology and APC-labeled anti-GST antibody (Prozyme, San Lindo, CA) Was terminated by adding 3 μl of detection reagent in 150 mM NaCl, 50 mM EDTA and 0.01 w / v% BSA) and the reaction was further incubated for 60 minutes at room temperature. The degree of phosphorylation of GST-IB was determined using a BMG Rubystar plate reader (BMG Labtech, Aylesbury, UK) of a specific 665 nm energy transition signal relative to the reference Europium 620 nm signal. It was measured as a ratio.

result

Examples 1-31, 33, 35-51, 53-58, 60-97, 100-116, 118-121, 123-137, 139-163, 165-172, 174-197, 199-220, 222- The compounds of 242, 244 to 276, 279 to 330, 332 to 358, 360 to 385, 387 to 402, 404 to 419, 421 to 426, and 428 to 436 were tested for activity against IKK2 and in these examples It was found to be an inhibitor of IKK2. These compounds had a pIC ₅₀ of 5.0 or more. Examples 277 and 278 were also tested for activity against IKK2 and these two compounds were found to have a pIC ₅₀ of less than 5.0.

Monocyte analysis

The effects of IKK-β inhibition on cytokine production stimulated by human monocytes were evaluated as follows: Monocytes were isolated from heparin added whole blood by Ficoll gradient and then using MACS magnetic cell separation beads. CD14 + cells were purified. Isolated monocytes were then attached to 96-well culture plates at 1 × 10 ⁶ cells / mL in RPMI 1640 10% FBS (JRH Biosciences, Lenexa KS) for 2 hours. Test compounds were added to the wells 30 minutes before stimulation to a final vehicle concentration of 0.1% DMSO. Monocytes were activated by the addition of 200 ng / mL of endotoxin (LPS; E. coli serotype 026: B6) (Sigma, St. Louis, MO) and at 37 ° C. for 24 hours Incubated. Cell-free supernatants were analyzed for ELN-α by ELISA or Alphascreen. ELISA was performed using a Pharmingen matched pair Ab, and alphascreens were alphascreen receptors and donor beads from Perkin Elmer, and anti-human from R & D Systems. TNF and biotin treated anti-human TNF Abs were used. Cell viability was determined by 10% trypan blue exclusion.

result

Certain embodiments of the invention have been tested in monocyte assays. Examples 1 to 3, 5 to 13, 16 to 23, 25 to 31, 33, 37, 42 to 44, 61, 65 to 69, 71 to 73, 75 to 78, 83, 86 to 89, 92, 96, 100 to 117, 119 to 121, 123 to 127, 129 to 131, 139, 141, 144, 151, 154-157, 160-164, 166-167, 169-172, 182, 191, 208 to 214, 216 to 220, 222, 223, 227, 230 to 248, 250, 251, 269, 271, 273 to 276, 279 to 83, 285 to 90, 292 to 296, 298, 304 to 327, 329, 332 to 337, 342, 343, 346, 348, 353, 356 to 358, 361, 366 to 368, 370 to 373, 376, 380, 382, 391, 394-397, 399-404, 406, 408, 409, 412, 417-419, 432, 434, and 435 were found to have an IC50 of less than 2 μM in this analysis.

Examples 4, 15, 24, 34 to 36, 50, 70, 118, 128, 132 to 134, 136, 137, 140, 143, 146 to 148, 153, 158, 159, 165, 168, 192 to 194, 196, 197, 200 to 207, 224, 249, 253 to 262, 270, 272, 299 to 303, 330, 338 to 341, 360, 362, 363, 365, 374, 375, 377 to 379, 381, 383, 385, 388-390, 392, and 393 did not inhibit more than 65% at 1 μM (highest test dose).

Examples 39, 40, 45-49, 58-60, 62, 63, 74, 79-81, 84, 85, 90, 91, 94, 95, 97, 173-181, 184-190, 195, 198, 328, 345, 347, 349-353, 345, 355, 429-431, 433, and 436 exhibited less than 60% inhibition at 300 nM.

Monocyte analysis yielded inconsistent results for Examples 38, 64, 82, 215, 297, 344, 364, and 369.

Claims (22)

A compound of formula (I) or a pharmaceutically acceptable salt, solvate or polymorph thereof. <Formula I>

In the formula, R1 is -XYZ or

Group; X is phenyl, heteroaryl, 1,2,3,4-tetrahydronaphthalenyl or 2,3-dihydro-1H-indenyl, wherein said phenyl, heteroaryl, 1,2,3,4-tetra Hydronaphthalenyl and 2,3-dihydro-1H-indenyl are 1) halo, 2) nitro, 3) cyano, 4) -NR 7 R 8, 5) C ₁ -C ₆ -alkyl, 6) CHO, 7 ) Is optionally substituted with one or two substituents each independently selected from CONH ₂ and 8) -OR ₄ , wherein said C ₁ -C ₆ -alkyl is optionally substituted with one —NR 4 R 5 group; Y is a bond or C ₁ -C ₆ alkylene, wherein C ₁ -C ₆ alkylene is 1) C ₁ -C ₃ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, Optionally substituted with one or two substituents each independently selected from 3) methoxy, 4) hydroxy and 5) heteroaryl; Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents; R 2 is selected from 1) H, 2) fluoro and 3) chloro; R 3 is selected from 1) H, 2) fluoro and 3) chloro; R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group; R5 is 1) H, 2) C ₅ -C ₆ -heterocycloalkyl, 3) -CO ₂ Et, 4) C ₁ -C ₆ -alkoxy, 5) C ₃ -C ₇ -cycloalkyl, 6) C ₁ -C ₆ -alkyl, 7) -SO ₂ R 10 and 8) -C (O) R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 3 selected from R ₆ Optionally substituted with 4 substituents; R6 is respectively 1) -NR7R8, 2) -SO ₂ R7, 3) -CONH ₂ , 4) -CF ₃ , 5) -CN, 6) -CO ₂ R7, 7) -OCH ₂ CH ₂ OR7, 8) -SR5, 9) C ₃ -C ₄ alkenyl, 10) OH, 11) C ₁ -C ₆ -alkoxy, 12) heteroaryl, 13) C ₃ -C ₇ -cycloalkyl, 14) phenyl, 15) hetero Independently selected from cycloalkyl and 16) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9; R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl; R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4; R9 is 1) hydroxy, 2) -OMe, 3) nitro, 4) C ₁ -C ₆ -alkyl, 5) NH ₂ , 6) halo, 7) CF ₃ , 8) C ₁ -C ₆ -alkoxy And 9) independently from CN; R 10 is selected from 1) C ₁ -C ₆ -alkyl, 2) phenyl, 3) C ₃ -C ₇ -cycloalkyl, 4) heteroaryl, 5) C ₁ -C ₆ -heteroaryl and 6) heterocycloalkyl Wherein the C ₁ -C ₆ -alkyl is substituted with 1 to 2 substituents each independently selected from C ₃ -C ₇ -cycloalkyl and -S-R 7, and the heterocycloalkyl is 1 -C (O Optionally substituted with a R7 group, said phenyl, heteroaryl and C ₁ -C ₆ -heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11; Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo; U is a bond, C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene; V is phenyl, 5- or 6-membered heteroaryl, 5-7 membered heterocycloalkyl, C ₅ -C ₇ cycloalkyl or C ₅ -C ₇ cycloalkenyl, each of which is —N (R 7) S (O) _m R12, -S (O) _m N (R7) R12, -S (O) _m R12 or -C (O) R12; m is 1 or 2; R12 is C ₁ -C ₆ -alkyl, C ₃ -C ₇ cycloalkyl, C ₁ -C ₆ -alkyl-C ₃ -C ₇ -cycloalkyl or C ₁ -C ₆ -alkyl-phenyl. The method of claim 1, R 1 is a -XYZ group; X is phenyl or heteroaryl, wherein the phenyl and heteroaryl are 1) halo, 2) nitro, 3) cyano, 4) -NR 7 R 8, 5) C ₁ -C ₆ -alkyl, 6) CHO, 7) CONH ₂ and 8) optionally substituted with one or two substituents each independently selected from -OR ₄ , wherein said C ₁ -C ₆ -alkyl is optionally substituted with one —NR 4 R 5 group; Y is a bond or C ₁ -C ₆ alkylene, wherein C ₁ -C ₆ alkylene is 1) C ₁ -C ₃ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, Optionally substituted with one or two substituents each independently selected from 3) methoxy, 4) hydroxy and 5) heteroaryl; Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4 Optionally substituted with 1 or 2 substituents each independently selected from hydroxy and 5) heteroaryl; R 2 is selected from 1) H, 2) fluoro and 3) chloro; R 3 is selected from 1) H, 2) fluoro and 3) chloro; R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group; R5 is 1) H, 2) C ₁ -C ₆ -alkoxy, 3) C ₃ -C ₇ -cycloalkyl, 4) C ₁ -C ₆ -alkyl, 5) -SO ₂ R 10 and 6) -C (O Is selected from R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are optionally substituted with 1 to 3 substituents selected from R ₆ ; Each R6 is 1) -NR7R8, 2) -SO ₂ R7, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl, 8) heterocycloalkyl and 9) independently selected from halo, wherein the heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9; R 7 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; R 8 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; Are each from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ , 7) C ₁ -C ₆ -alkoxy and 8) CN Independently selected; R 10 is selected from 1) C ₁ -C ₆ -alkyl, 2) phenyl, 3) C ₃ -C ₇ -cycloalkyl and 4) heteroaryl, wherein said C ₁ -C ₆ -alkyl is C ₃ -C ₇ Substituted with 1 to 2 substituents each independently selected from -cycloalkyl and -S-R7, said heterocycloalkyl optionally substituted with one -C (O) R7 group; Said phenyl and heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11; Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo; U is a bond, C ₁ -C ₆ alkylene or C ₂ -C ₆ alkenylene; V is phenyl, 5- or 6-membered heteroaryl, 5-7 membered heterocycloalkyl, C ₅ -C ₇ cycloalkyl or C ₅ -C ₇ cycloalkenyl, each of which is —N (R 7) S (O) _m R12, -S (O) _m N (R7) R12, -S (O) _m R12 or -C (O) R12; m is 1 or 2; R12 is C ₁ -C ₆ -alkyl, C ₃ -C ₇ cycloalkyl, C ₁ -C ₆ -alkyl-C ₃ -C ₇ -cycloalkyl or C ₁ -C ₆ -alkyl-phenyl Compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. The method of claim 1, R1 is -XYZ or

Group; X is phenyl, heteroaryl, 1,2,3,4-tetrahydronaphthalenyl or 2,3-dihydro-1H-indenyl; Y is a bond or C ₁ -C ₆ alkylene; Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents; R 2 is H; R 3 is H; R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group; R5 is 1) H, 2) C ₅ -C ₆ -heterocycloalkyl, 3) -CO ₂ Et, 4) C ₁ -C ₆ -alkoxy, 5) C ₃ -C ₇ -cycloalkyl, 6) C ₁ -C ₆ -alkyl, 7) -SO ₂ R 10 and 8) -C (O) R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 1 selected from R ₆ ; Optionally substituted with 3 substituents; R6 is respectively 1) -NR7R8, 2) -SO ₂ R7, 3) -CONH ₂ , 4) -CF ₃ , 5) -CN, 6) -CO ₂ R7, 7) -OCH ₂ CH ₂ OR7, 8) -SR5, 9) C ₃ -C ₄ alkenyl, 10) OH, 11) C ₁ -C ₆ -alkoxy, 12) heteroaryl, 13) C ₃ -C ₇ -cycloalkyl, 14) phenyl, 15) hetero Independently selected from cycloalkyl and 16) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9; R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl; R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4; Each R 9 is 1) hydroxy, 2) -OMe, 3) nitro, 4) C ₁ -C ₆ -alkyl, 5) NH ₂ , 6) halo, 7) CF ₃ , 8) C ₁ -C ₆ -alkoxy And 9) independently from CN; R 10 is selected from 1) C ₁ -C ₆ -alkyl, 2) C ₃ -C ₇ -cycloalkyl, 3) heteroaryl, 4) C ₁ -C ₆ -heteroaryl and 5) heterocycloalkyl, wherein C ₁ -C ₆ -alkyl is substituted with 1 to 2 substituents each independently selected from C ₃ -C ₇ -cycloalkyl and -S-R 7, wherein said heterocycloalkyl is optionally substituted with 1 -C (O) R 7 group Substituted, said phenyl, heteroaryl and C ₁ -C ₆ -heteroaryl are optionally substituted with 1 to 2 substituents selected from R 11; Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo; U is a bond; V is 5-7 membered heterocycloalkyl substituted with -S (O) _m R12; m is 1 or 2; R12 is C ₁ -C ₆ -alkyl Compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. The method of claim 1, R 1 is a -XYZ group; X is phenyl or heteroaryl; Y is a bond or C ₁ -C ₆ alkylene; Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with one OR 4 group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4 Optionally substituted with 1 or 2 substituents each independently selected from hydroxy and 5) heteroaryl; R 2 is H; R 3 is H; R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group; R5 is 1) H, 2) C ₁ -C ₆ -alkoxy, 3) C ₃ -C ₇ -cycloalkyl, 4) C ₁ -C ₆ -alkyl, 5) -SO ₂ R 10 and 6) -C (O Is selected from R 10, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are optionally substituted with 1 to 3 substituents selected from R ₆ ; Each R6 is 1) -NR7R8, 2) -SO ₂ R7, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl, 8) heterocycloalkyl and 9) independently selected from halo, wherein the heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 2 substituents selected from R 9; R 7 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; R 8 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; Are each from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ , 7) C ₁ -C ₆ -alkoxy and 8) CN Independently selected; R 10 is selected from 1) C ₁ -C ₆ -alkyl, 2) phenyl, 3) C ₃ -C ₇ -cycloalkyl and 4) heteroaryl, wherein said C ₁ -C ₆ -alkyl is C ₃ -C ₇ Substituted with one or two substituents each independently selected from -cycloalkyl and -S-R7, said heterocycloalkyl is optionally substituted with one -C (O) R7 group, and said phenyl and heteroaryl are selected from R11 Optionally substituted with 1 to 2 substituents; Each R 11 is independently selected from 1) H, 2) C ₁ -C ₆ -alkyl and 3) halo; U is a bond; V is 5-7 membered heterocycloalkyl substituted with -S (O) _m R12; m is 1 or 2; R12 is C ₁ -C ₆ -alkyl Compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. The method of claim 1, R 1 is a -XYZ group; X is 2- or 3-thiophenyl; Y is a bond or C ₁ -C ₄ alkylene; Z is —NR 4 R 5 or heterocycloalkyl, wherein the heterocycloalkyl is 1) C ₁ -C ₆ -alkyl optionally substituted with 1 OR 4 or 1 heterocycloalkyl group, 2) C ₃ -C ₇ -cycloalkyl, 3) methoxy, 4) -CONH ₂ , 5) hydroxy, 6) heteroaryl, 7) CF ₃ , 8) phenyl, 9) heterocycloalkyl and 10) N (CH ₃ ) ₂ , each independently selected from 1 Optionally substituted with 4 or 2 substituents; R 2 is H; R 3 is H; R 4 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxy or 1 methoxy group; R 5 is selected from 1) C ₃ -C ₇ -cycloalkyl and 2) C ₁ -C ₆ -alkyl, wherein said C ₃ -C ₇ -cycloalkyl and C ₁ -C ₆ -alkyl are 1 to 1 selected from R ₆ ; Optionally substituted with 3 substituents; R6 is 1) -NR7R8, 2) -CONH ₂ , 3) -CN, 4) -OCH ₂ CH ₂ OR7, 5) C ₃ -C ₄ alkenyl, 6) OH, 7) C ₁ -C _6- Alkoxy, 8) heteroaryl, 9) C ₃ -C ₇ -cycloalkyl, 10) phenyl, 11) heterocycloalkyl and 12) halo, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl Is optionally substituted with 1 to 2 substituents selected from R 9; R 7 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) phenyl; R 8 is selected from 1) H, 2) C ₁ -C ₃ -alkyl and 3) -C (O) R 4; Each R 9 is independently selected from 1) C ₁ -C ₆ -alkyl; U is a bond; V is 4-piperidinyl substituted with —S (O) ₂ R 12; R12 is ethyl or isopropyl Compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. The method of claim 1 wherein the UV group is

And R12 is ethyl or isopropyl, or a pharmaceutically acceptable salt, solvate or polymorph thereof. 2. A compound according to claim 1, or a pharmaceutically acceptable salt, solvate or polymorph thereof, which is a compound of formula II. <Formula II>

In the formula, R 13 is —NR 14 R 15 or heterocycloalkyl, wherein the heterocycloalkyl is 1) selected from C ₁ -C ₆ -alkyl optionally substituted with one OR 14 group, 2) hydroxy, 3) methoxy and 4) heteroaryl Optionally substituted with 4 or 2 substituents; R14 is selected from 1) H and 2) C ₁ -C ₆ -alkyl, wherein said C ₁ -C ₆ -alkyl is optionally substituted with 1 hydroxyl or 1 methoxy group; R 15 is selected from 1) H, 2) methoxy, 3) C ₃ -C ₇ cycloalkyl and 4) C ₁ -C ₆ -alkyl, wherein said C ₃ -C ₇ cycloalkyl and C ₁ -C _6- Alkyl is optionally substituted with 1 to 3 substituents selected from R 16; R16 is each from 1) -NR17R18, 2) -SO ₂ R17, 3) OH, 4) methoxy, 5) heteroaryl, 6) C ₃ -C ₇ -cycloalkyl, 7) phenyl and 8) heterocycloalkyl Independently selected, wherein said heteroaryl, cycloalkyl, phenyl and heterocycloalkyl are optionally substituted with 1 to 3 substituents selected from R 19; R17 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; R18 is selected from 1) H and 2) C ₁ -C ₃ -alkyl; R 19 is selected from 1) hydroxy, 2) nitro, 3) C ₁ -C ₆ -alkyl, 4) NH ₂ , 5) halo, 6) CF ₃ and 7) C ₁ -C ₆ -alkoxy; n is 1 to 3. The method of claim 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperazinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({methyl [2- (methylsulfonyl) ethyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- (3-{[[2- (dimethylamino) ethyl] (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(4- {2-[(2-hydroxyethyl) oxy] ethyl} -1-piperazinyl) methyl ] Phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[3- (hydroxymethyl) -1-piperidinyl] methyl} phenyl) -1H-indole-7- Carboxamides; 5- [3-({bis [2- (methyloxy) ethyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 5- {3-[(2,6-dimethyl-4-morpholinyl) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (1,3-thiazol-2-yl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (2-thienyl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-2-phenylethyl) (methyl) amino] methyl} phenyl) -1H-indole- 7-carboxamide; 5- (3-{[ethyl (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(cyclopentylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3-({[(3,4-dihydroxyphenyl) methyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2- (hydroxymethyl) -3-methylbutyl] amino} methyl) phenyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-1-methylethyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(trans-4-hydroxycyclohexyl) amino] methyl} phenyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[({[1- (1-piperidinyl) cyclohexyl] methyl} amino) methyl] phenyl} -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2-hydroxypropyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- {3-[(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (3-{[(1-ethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- [4- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- {3-[(cyclopropylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(cyclobutylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- (1-{[3- (dimethylamino) propyl] sulfonyl} -4-piperidinyl) -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(2-methylpropyl) amino] -2,3-dihydro-1H-inden-5-yl} -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {8-[(2-methylpropyl) amino] -5,6,7,8-tetrahydro-2-naphthalenyl} -1H-indole-7-carboxamide; 5- (5-{[(2-cyanoethyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1,2,3,4-tetrahydro-7-isoquinolinyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides; 5- (3-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-{[(2,2,2-trifluoroethyl) amino] methyl} -1,3-thiazole-4 -Yl) -1H-indole-7-carboxamide; 5- (3-cyano-5-{[(2,2,2-trifluoroethyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methyl-4-piperidinyl) amino] methyl} -3-thienyl) -1H- Indole-7-carboxamide; 5- (5-{[(2-cyanoethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide; 5- (5-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (phenylsulfonyl) ethyl] amino} methyl) -3-thienyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-phenyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (1-piperidinylmethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H-indole-7-carboxamide; 5- (5-{[(2R) -2- (aminocarbonyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide; 5- (5-{[(2S) -2- (dimethylamino) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (1- {2- [4- (dimethylamino) -1-piperidinyl] ethyl} -1H-pyrazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidi Nil] -1H-indole-7-carboxamide; 5- [3-[(dimethylamino) methyl] -4,5-bis (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- [3,4-bis (methyloxy) -5- (4-morpholinylmethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -1H- Indole-7-carboxamide; 5- [3-{[(2,2-dimethylpropyl) amino] methyl} -4,5-bis (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(2-hydroxyethyl) (methyl) amino] methyl} -4,5-bis (methyloxy) phenyl ] -1H-indole-7-carboxamide; 5- [3,4-bis (methyloxy) -5- (1-pyrrolidinylmethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- {4-[(dimethylamino) methyl] -2,3-dihydro-1-benzofuran-6-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(1-methylethyl) amino] methyl} -2,3-dihydro-1-benzofuran-6- Yl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) -2,3-dihydro-1-benzofuran-6-yl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[1-methyl-2- (methyloxy) ethyl] amino} methyl) -2-thienyl] -1H Indole-7-carboxamide; 5- (5-{[(2-cyanoethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2,2,2-trifluoroethyl) amino] methyl} -3-pyridinyl) -1H- Indole-7-carboxamide; 5- {3-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[[2- (diethylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 5- (5-{[butyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide; 5- (5-{[[2- (dimethylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- (5-{[[3- (dimethylamino) propyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- (5-{[cyclopentyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (pentyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (phenylmethyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-hydroxyethyl) (methyl) amino] methyl} -3-thienyl) -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (2-pyridinyl) ethyl] amino} methyl) -3-thienyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-furanylmethyl) (methyl) amino] methyl} -3-thienyl) -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (4-pyridinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methyl {[1- (1-methylethyl) -3-pyrrolidinyl] methyl} amino) methyl]- 3-thienyl} -1 H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-thienylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [1- (2-thienyl) ethyl] amino} methyl) -3-thienyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (3-thienylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} -3-thienyl)- 1H-indole-7-carboxamide trifluoroacetate; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (3-pyridinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7- Carboxamide trifluoroacetate; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (4-pyrimidinylmethyl) amino] methyl} -3-thienyl) -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [2- (methyloxy) ethyl] amino} methyl) -3-thienyl] -1H-indole- 7-carboxamide; 5- {3-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methylethyl) amino] methyl} -3-thienyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-propyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (3-pyridinyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide; 5- (5-{[2- (1,1-dimethylethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {5-[(2-ethyl-1-pyrrolidinyl) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (2-methylpropyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (1-methylethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide; 5- (5-{[cyclohexyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[2- (2-methylpropyl) -1-pyrrolidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide; 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide; 3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -5- (5-{[methyl (propyl) amino] methyl} -3-thienyl) -1H-indole-7 Carboxamides; 5- (5-{[ethyl (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7 Carboxamides; 3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -5- [5-({methyl [2- (methyloxy) ethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -3-thienyl} -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(propylamino) methyl] -3-thienyl} -1H-indole-7-carboxamide; 5- {5-[(diethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[(2R, 5R) -2,5-dimethyl-1-pyrrolidinyl] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide; 5- {5-[(cyclopropylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {5-[(cyclobutylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {5-[(dimethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[(cyclopentylmethyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- {5-[(cyclopentylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[(cyclopropylmethyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(phenylmethyl) amino] methyl} -3-thienyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} -3-thienyl) -1H Indole-7-carboxamide; 5- {5-[(butylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({(2R) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3- Thienyl] -1 H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4- [2- (methylamino) ethyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4- [2- (propylamino) ethyl] phenyl} -1H-indole-7-carboxamide; 5- {4- [2- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[({[1- (1,1-dimethylethyl) -3-methyl-1H-pyrazol-5-yl] carbonyl} amino) methyl] phenyl} -3- [1- (ethyl Sulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(4-pyridinylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (4-{[(cyclopentylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- {4- [2- (acetylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4- {2-[(methylsulfonyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide; 5- (4- {2-[(cyclobutylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (4- {2-[(cyclohexylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {2-[(methylsulfonyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide; 5- (3- {2-[(cyclohexylcarbonyl) amino] ethyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-piperazinyl) -3-pyridinyl] -1H-indole-7-carboxamide trifluoroacetate ; 5- [6- (4-ethyl-1-piperazinyl) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- (4-{[(1-ethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[(cyclopentylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[(cyclobutylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {4-[(diethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1S) -2-hydroxy-1-methylethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1R) -2-hydroxy-1-methylethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(2R) -2-hydroxypropyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[2-hydroxy-1- (hydroxymethyl) ethyl] amino} methyl) phenyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(1-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1R) -1-methylpropyl] amino} methyl) phenyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1S) -1-methylpropyl] amino} methyl) phenyl] -1H-indole-7-carbox amides; 5- {4-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(propanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- (4-{[(cyclopropylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (4-{[(cyclobutylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-thienylacetyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- [4-({[(1S) -1,2-dimethylpropyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- {4-[(butanoylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-methylpropanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(3-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- (4-{[(ethylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (4-{[(butylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[(1-methylethyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-carbox amides; 5- (6-amino-2-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1H-pyrazol-1-yl) phenyl] -1H-indole-7-carboxamide; 5- [4- (dimethylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (3-aminophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -2-thienyl} -1H-indole-7- Carboxamides; 5- {5-[(ethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 5- {5-[(cyclopropylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- (5-{[(cyclopropylmethyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 5- (5-{[(cyclopropylmethyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[2- (methyloxy) ethyl] amino} methyl) -3-pyridinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (methyloxy) propyl] amino} methyl) -3-pyridinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (4-morpholinylmethyl) -3-pyridinyl] -1H-indole-7-carboxamide; 5- {5-[(ethylamino) methyl] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {5-[(dimethylamino) methyl] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(2-methyl-1-pyrrolidinyl) methyl] -3-pyridinyl} -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-pyridinyl) -1H-indole-7-carbox amides; 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-pyridinyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(pentylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(2S) -2-methylbutyl] amino} methyl) -2-thienyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 5- {5-[(butylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[2- (methyloxy) ethyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides; 5- {5-[(cyclopentylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(3-methylbutyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -3-pyridinyl) -1H-indole-7-carbox amides; 5- (5-{[(2-ethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 5- [5-({[3- (ethyloxy) propyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides; 5- (5-{[(cyclohexylmethyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[({3-[(1-methylethyl) oxy] propyl} amino) methyl] -2-thienyl}- 1H-indole-7-carboxamide; 5- [5-({[2- (ethyloxy) ethyl] amino} methyl) -2-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[3- (propyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides; 5- (5-{[(3,3-dimethylbutyl) amino] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) -2-thienyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(hexylamino) methyl] -2-thienyl} -1 H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylsulfonyl) amino] phenyl} -1H-indole-7-carboxamide; 5- [2- (dimethylamino) -4-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-pyrrolidinyl) -4-pyridinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (4-morpholinyl) -4-pyridinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-[(2-methylpropyl) amino] -4-pyridinyl} -1H-indole-7-carboxamide; 5- {2-[(2,2-dimethylpropyl) amino] -4-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (propylamino) -4-pyridinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-[(methylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) -2-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(2-methylpropyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 5- {4-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(1S) -1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(1R) -1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({[3- (methyloxy) propyl] amino} methyl) -2-thienyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-({(2S) -2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -2- Thienyl] -1 H-indole-7-carboxamide; 5- (4-{[(2R, 5R) -2,5-dimethyl-1-pyrrolidinyl] methyl} -2-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2S) -2-methyl-1-pyrrolidinyl] methyl} -3-thienyl) -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2R) -2-methyl-1-pyrrolidinyl] methyl} -3-thienyl) -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [1- (1-pyrrolidinyl) propyl] -3-thienyl} -1H-indole-7-carbox amides; 5- {5-[(dimethylamino) methyl] -3-thienyl} -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carbox amides; 5- [5- (aminomethyl) -3-thienyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {2-[(2-methylpropyl) amino] ethyl} -3-thienyl) -1H-indole-7- Carboxamides; 5- {5- [2- (dimethylamino) ethyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-pyrrolidinyl) -3-pyridinyl] -1H-indole-7-carboxamide; 5- {6- [ethyl (methyl) amino] -3-pyridinyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [6- (dimethylamino) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (propylamino) -3-pyridinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {6-[(1-methylethyl) amino] -3-pyridinyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (4-morpholinyl) -3-pyridinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -3-thienyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(1-methylethyl) amino] methyl} -3-thienyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -3-thienyl] -1H-indole-7-carboxamide; 5- {5-[(ethylamino) methyl] -3-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({[(1R) -2-hydroxy-1-methylethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-piperidinylmethyl) -3-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (4-morpholinylmethyl) -3-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(methylamino) methyl] -3-furanyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [1- (1-pyrrolidinyl) ethyl] -3-thienyl} -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -2-thienyl] -1H-indole-7-carboxamide; 5- {5-[(dimethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5-[(propylamino) methyl] -2-thienyl} -1H-indole-7-carboxamide; 5- {5-[(diethylamino) methyl] -2-thienyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -2-thienyl) -1H-indole-7-carbox amides; 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2-methylpropyl) amino] methyl} -3-furanyl) -1H-indole-7-carbox amides; 5- (5-{[(cyclopentylmethyl) amino] methyl} -3-furanyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -3-furanyl] -1H-indole-7-carboxamide; 5- {5-[(diethylamino) methyl] -3-furanyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1-pyrrolidinylmethyl) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {5- [2-methyl-1- (1-pyrrolidinyl) propyl] -3-thienyl} -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-pyrrolidinylmethyl) -1,3-thiazol-2-yl] -1H-indole-7- Carboxamides; 5- {1- [2- (dimethylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {1- [2- (1-pyrrolidinyl) ethyl] -1H-pyrazol-4-yl} -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {1- [2- (4-morpholinyl) ethyl] -1H-pyrazol-4-yl} -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-hydroxyethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H Indole-7-carboxamide; 5- {1- [2- (butylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- {1- [2- (cyclobutylamino) ethyl] -1H-pyrazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- [1- (2-{[2- (diethylamino) ethyl] amino} ethyl) -1H-pyrazol-4-yl] -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(1-methylethyl) amino] ethyl} -1H-pyrazol-4-yl) -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-methylpropyl) amino] ethyl} -1H-pyrazol-4-yl) -1H- Indole-7-carboxamide; 5- (1- {2-[(cyclopentylmethyl) amino] ethyl} -1H-pyrazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (methyloxy) -3- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide ; 5- [3-[(dimethylamino) methyl] -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (methyloxy) -3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-{[(1-methylethyl) amino] methyl} -4- (methyloxy) phenyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-[(methylamino) methyl] -4- (methyloxy) phenyl] -1H-indole-7-carboxamide; 5- [3-{[(2,2-dimethylpropyl) amino] methyl} -4- (methyloxy) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (1- {2-[(2-hydroxyethyl) (methyl) amino] ethyl} -1H-pyrazol-4-yl ) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {4-fluoro-3-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- {3,5-bis [(methylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(ethylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-fluoro-3-({[2-hydroxy-1- (hydroxymethyl) ethyl] amino} methyl) phenyl ] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4-fluoro-3-({[(1S) -2-hydroxy-1-methylethyl] amino} methyl) phenyl ] -1H-indole-7-carboxamide; 5- {3-[(cyclopropylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(cyclobutylamino) methyl] -4-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- {3,5-bis [(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3,5-bis [(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-piperidinyl) phenyl] -1H-indole-7-carboxamide; 5- {3- [1- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3- [1- (dimethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- {3-[(ethylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-fluoro-5-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 5- {3-[(cyclobutylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(dimethylamino) methyl] -5-fluorophenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [1- (methylamino) ethyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1-[(1-methylethyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {1-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide; 5- {3- [1- (cyclobutylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [1- (1-pyrrolidinyl) ethyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (3-thiomorpholinyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (2-piperazinyl) -2-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-piperazinyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (4-morpholinyl) -3-pyridazinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [6- (1-pyrrolidinyl) -3-pyridazinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(5-methyl-2-furanyl) methyl] amino} methyl) phenyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 5- (3-{[(2,2-dimethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2-methylbutyl] amino} methyl) phenyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1R) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2R) -tetrahydro-2-furanylmethyl] amino} methyl) phenyl] -1H-indole-7-carboxamide; 5- [3-({[(1S) -1,2-dimethylpropyl] amino} methyl) -5-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 5- [3-({[(1R) -1,2-dimethylpropyl] amino} methyl) -5-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(1-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(1S) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(2S) -2-methylbutyl] amino} methyl) phenyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-methylbutyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(1R) -1,2,2-trimethylpropyl] amino} methyl) phenyl] -1H-indole-7-carboxamide; 5- (3-{[(2,2-dimethylpropyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 5- (3-{[(cyclopropylmethyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 5- (3-{[(cyclopentylmethyl) amino] methyl} -5-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(tetrahydro-2H-pyran-4-ylmethyl) amino] methyl} phenyl)- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[2- (methyloxy) ethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[3- (methyloxy) propyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(2-furanylmethyl) amino] methyl} phenyl) -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-fluoro-5-{[(3-methylbutyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-fluoro-5-({[(5-methyl-2-furanyl) methyl] amino} methyl) phenyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (2-pyrrolidinyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {2-fluoro-5-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-fluoro-5-{[(2-methylpropyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 5- (5-{[(2,2-dimethylpropyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 5- [5-({[(1S) -1,2-dimethylpropyl] amino} methyl) -2-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 5- [5-({[(1R) -1,2-dimethylpropyl] amino} methyl) -2-fluorophenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 5- (5-{[(cyclopropylmethyl) amino] methyl} -2-fluorophenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5- (1-pyrrolidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5-({[2- (methyloxy) ethyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2-fluoro-5-({[3- (methyloxy) propyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-methyl-2-pyrrolidinyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3- {2-[(2-methylpropyl) amino] ethyl} phenyl) -1H-indole-7-carboxamide; 5- {3- [2- (ethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3- [2- (propylamino) ethyl] phenyl} -1H-indole-7-carboxamide; 5- {3- [2- (dimethylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3- [2- (dipropylamino) ethyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3-({[2- (3,5-dimethyl-1H-pyrazol-1-yl) ethyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidi Nil] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (4-morpholinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (2-{[(2-methylpropyl) amino] methyl} -1,3-thiazol-4-yl) -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-pyrrolidinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [2- (1-piperidinylmethyl) -1,3-thiazol-4-yl] -1H-indole-7- Carboxamides; 5- {2-[(dimethylamino) methyl] -1,3-thiazol-4-yl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- (2-{[ethyl (methyl) amino] methyl} -1,3-thiazol-4-yl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide; 5- (3-cyano-5-{[(2-methylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- {3-cyano-5-[(dimethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(methylsulfonyl) amino] phenyl} -1H-indole-7-carboxamide; 5- [4- (acetylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3- (acetylamino) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- {3-[(acetylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- {3-[(butanoylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(4-fluorophenyl) carbonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpropanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (3-{[(cyclopentylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(pentanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- (3-{[(2-ethylbutanoyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (3-{[(1-benzothien-2-ylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- [3-({[(1-acetyl-4-piperidinyl) carbonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1-methyl-1H-pyrrol-2-yl) carbonyl] amino} methyl) phenyl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(3-methyl-2-butenyl) amino] methyl} phenyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(heptanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(octanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylpentanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(3-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylacetyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(hexanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-methylbutanoyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (3-{[(cyclobutylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (3-{[(cyclopropylcarbonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(propanoylamino) methyl] phenyl} -1H-indole-7-carboxamide; 5- (3-{[(cyclopentylacetyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[3- (methylthio) propanoyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(1-methylethyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-carbox amides; 5- (3-{[(cyclopropylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3-({[(2,5-dichlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- [3-({[(4-bromophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- [3-({[(4-chlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(3-fluorophenyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- [3-({[(2-chlorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 5- [3-({[(2,5-dichloro-3-thienyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- [3-({[(2-chloro-6-methylphenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(5-fluoro-2-methylphenyl) sulfonyl] amino} methyl) phenyl] -1H-indole- 7-carboxamide; 5- [3-({[(1,2-dimethyl-1H-imidazol-4-yl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl ] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(propylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (3-{[(butylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(phenylsulfonyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(4-fluorophenyl) sulfonyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- [3-({[(4-bromo-2-ethylphenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 5- (3-{[(1-benzothien-3-ylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-car Boxamide; 5- {3-[({[4- (1,1-dimethylethyl) phenyl] sulfonyl} amino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 5- [3-({[(3,4-difluorophenyl) sulfonyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole- 7-carboxamide; 5- (3-{[(ethylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- (3-{[(2,1,3-benzoxadiazol-4-ylsulfonyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(tetrahydro-3-furanylcarbonyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 5- {4-[(cyclopentylsulfonyl) amino] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-methyl-2-oxo-1-piperazinyl) phenyl] -1H-indole-7-carboxamide ; 5- [6- (4-acetyl-1-piperazinyl) -3-pyridinyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (4-{[(methyloxy) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(methyloxy) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[4- (1-pyrrolidinyl) -1-piperidinyl] methyl} -3-thienyl)- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[(2S) -2- (trifluoromethyl) -1-pyrrolidinyl] methyl} -3-thier Nil) -1H-indole-7-carboxamide; 5- (5-{[(2R) -2- (hydroxymethyl) -1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl]- 4-piperidinyl} -1H-indole-7-carboxamide; 5- (5-{[(3S) -3-hydroxy-1-pyrrolidinyl] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-pipe Lidinyl} -1H-indole-7-carboxamide; 5- (5-{[cyclopentyl (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole- 7-carboxamide; 5- (5-{[(2-hydroxyethyl) (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-piperidinyl} -1H-indole-7-carboxamide; 5- (5-{[(2-amino-2-oxoethyl) (methyl) amino] methyl} -3-thienyl) -3- {1-[(1-methylethyl) sulfonyl] -4-pipe Lidinyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (2-propen-1-yl) amino] methyl} -3-thienyl) -1H-indole -7-carboxamide; 5- (5-{[[(3,5-dimethyl-1H-pyrazol-4-yl) methyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1 H-indole-7-carboxamide; 5- (5-{[(cyanomethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[methyl (1-methylpropyl) amino] methyl} -3-thienyl) -1H-indole-7-car Boxamide; 5- (5-{[[2- (ethyloxy) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 5- (5-{[cyclobutyl (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide ; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({2-[(methyloxy) methyl] -1-pyrrolidinyl} methyl) -3-thienyl]- 1H-indole-7-carboxamide; 5- (5-{[(1,1-dimethylethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[3- (trifluoromethyl) -1-piperidinyl] methyl} -3-thienyl) -1H Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide; 5- (5-{[(cyclopropylmethyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 5- (5-{[[2- (acetylamino) ethyl] (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1R, 2R) -2-hydroxycyclopentyl] (methyl) amino] methyl} -3-thie Nil) -1H-indole-7-carboxamide; 5- (5-{[(1,1-dimethylpropyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole -7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[((2S) -2-hydroxypropyl] (methyl) amino] methyl} -3-thienyl)- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5-({methyl [(2R) -tetrahydro-2-furanylmethyl] amino} methyl) -3-thienyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[{2-[(2-hydroxyethyl) oxy] ethyl} (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [5- (1- {methyl [2- (methyloxy) ethyl] amino} ethyl) -3-thienyl] -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5- {1- [methyl (propyl) amino] ethyl} -3-thienyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (5-{[[(1S) -2-hydroxy-1-methylethyl] (methyl) amino] methyl} -3- Thienyl) -1H-indole-7-carboxamide; or 5- (5-{[(1,1-dioxydotetrahydro-3-thienyl) (methyl) amino] methyl} -3-thienyl) -3- [1- (ethylsulfonyl) -4- Piperidinyl] -1H-indole-7-carboxamide Phosphorus compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. The method of claim 1, 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperazinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({methyl [2- (methylsulfonyl) ethyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- (3-{[[2- (dimethylamino) ethyl] (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7- Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(4- {2-[(2-hydroxyethyl) oxy] ethyl} -1-piperazinyl) methyl ] Phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[3- (hydroxymethyl) -1-piperidinyl] methyl} phenyl) -1H-indole-7- Carboxamides; 5- [3-({bis [2- (methyloxy) ethyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 5- {3-[(2,6-dimethyl-4-morpholinyl) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (1,3-thiazol-2-yl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[2- (2-thienyl) -1-pyrrolidinyl] methyl} phenyl) -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-2-phenylethyl) (methyl) amino] methyl} phenyl) -1H-indole- 7-carboxamide; 5- (3-{[ethyl (methyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(cyclopentylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- [3-({[(3,4-dihydroxyphenyl) methyl] amino} methyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7 Carboxamides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-thienylmethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2- (hydroxymethyl) -3-methylbutyl] amino} methyl) phenyl]- 1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(2-hydroxy-1-methylethyl) amino] methyl} phenyl) -1H-indole-7-car Boxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(trans-4-hydroxycyclohexyl) amino] methyl} phenyl) -1H-indole-7-carbox amides; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[({[1- (1-piperidinyl) cyclohexyl] methyl} amino) methyl] phenyl} -1H- Indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3-({[(2S) -2-hydroxypropyl] amino} methyl) phenyl] -1H-indole-7-car Boxamide; 5- {3-[(ethylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(propylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- (3-{[(1-methylethyl) amino] methyl} phenyl) -1H-indole-7-carboxamide; 5- (3-{[(1-ethylpropyl) amino] methyl} phenyl) -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(methylamino) methyl] phenyl} -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [4- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- [4- (aminomethyl) phenyl] -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- [3- (4-morpholinylmethyl) phenyl] -1H-indole-7-carboxamide; 5- {3-[(cyclopropylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 5- {3-[(cyclobutylamino) methyl] phenyl} -3- [1- (ethylsulfonyl) -4-piperidinyl] -1H-indole-7-carboxamide; 3- (1-{[3- (dimethylamino) propyl] sulfonyl} -4-piperidinyl) -5- [4- (1-piperidinylmethyl) phenyl] -1H-indole-7-carbox amides; or 3- [1- (ethylsulfonyl) -4-piperidinyl] -5- {3-[(2-methylpropyl) amino] -2,3-dihydro-1H-inden-5-yl} -1H Indole-7-carboxamide Phosphorus compounds, or pharmaceutically acceptable salts, solvates or polymorphs thereof. A pharmaceutical composition comprising a compound according to claim 1 and at least one pharmaceutically acceptable excipient. A method of treating a disorder mediated by inappropriate IKK2 activity, comprising administering a safe and effective amount of a compound according to claim 1 to a patient in need of treatment for a disorder mediated by inappropriate IKK2 activity. . 12. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is rheumatoid arthritis, inflammatory bowel disease, asthma, COPD (chronic obstructive pulmonary disease), osteoarthritis, osteoporosis, psoriasis, atopic dermatitis, ultraviolet (UV) -induced skin injury. , Systemic lupus erythematosus, multiple sclerosis, psoriatic arthritis, ankylosing spondylitis, tissue rejection, organ rejection, Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, Hodgkin's disease, Cachexia, inflammation associated with infection, certain viral infections including acquired immunodeficiency syndrome (AIDS), adult respiratory distress syndrome, and capillary dilatation ataxia. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is inflammatory or tissue regeneration impaired. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is rheumatoid arthritis, asthma or COPD. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is rheumatoid arthritis. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is asthma. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is COPD. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is selected from the group consisting of Alzheimer's disease, stroke, atherosclerosis, restenosis, diabetes, glomerulonephritis, osteoarthritis, osteoporosis, and capillary ataxia. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is an autoimmune disease. The method of claim 19, wherein the autoimmune disease is systemic lupus erythematosus, multiple sclerosis, psoriatic arthritis or ankylosing spondylitis. The method of claim 11, wherein the disorder mediated by inappropriate IKK2 activity is cancer or cachexia. The method of claim 21, wherein the cancer is Hodgkin's disease.