WO2022070048A1 - Novel amide derivatives - Google Patents

Novel amide derivatives Download PDF

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Publication number
WO2022070048A1
WO2022070048A1 PCT/IB2021/058878 IB2021058878W WO2022070048A1 WO 2022070048 A1 WO2022070048 A1 WO 2022070048A1 IB 2021058878 W IB2021058878 W IB 2021058878W WO 2022070048 A1 WO2022070048 A1 WO 2022070048A1
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WIPO (PCT)
Prior art keywords
methyl
ethyl
naphthalen
benzamide
amino
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Application number
PCT/IB2021/058878
Other languages
French (fr)
Inventor
Rajiv Sharma
Sameer Agarwal
Original Assignee
Cadila Healthcare Limited
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Publication date
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Publication of WO2022070048A1 publication Critical patent/WO2022070048A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/52—Y being a hetero atom
    • C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
    • C07C311/55—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to acyclic carbon atoms
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    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
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    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
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    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to novel compounds of the general formula (I) their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers and polymorphs.
  • the invention also relates to processes for the preparation of the compounds of invention, pharmaceutical compositions containing the compounds and their use as the compounds of the invention belong to the family of papain-like protease (PLpro) modulators.
  • the present invention thus relates to novel papain-like protease (PLpro) modulators and their use in the treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated like severe acute respiratory syndrome (SARS), Middle east respiratory syndrome (MERS), Spanish flu, COVID19 (Coronavirus disease 2019), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus.
  • SARS-CoV-2 severe acute respiratory syndrome coronavirus 2
  • SARS-CoV-2 the causative agent for COVID-19
  • SARS-CoV-2 the causative agent for COVID-19
  • SARSCoV-2 encodes for a papain-like protease (PLpro) that is likely responsible for cleavage of the CoV viral poly-peptide.
  • the PLpro is also responsible for suppression of host innate immune responses by virtue of its ability to reverse host ubiquitination and ISGylation events.
  • the biochemical activity of SARS-CoV-2 PLpro against ubiquitin and ISG15 substrates was evaluated revealing that the protease has a marked reduction in its ability to process K48 linked Ub substrates compared to its counterpart in SARS-CoV. Additionally, its substrate activity more closely mirrors that of the PLpro from the Middle East respiratory syndrome coronavirus and prefers ISG15s from certain species including humans.
  • the papain-like protease PLpro is an essential coronavirus enzyme required for processing viral polyproteins to generate a functional replicase complex and enable viral spread. PLpro is also implicated in cleaving proteinaceous post-translational modifications on host proteins as an evasion mechanism against host anti-viral immune responses. (Nature Microbiology 2020, 5, 536-544).
  • the novel coronavirus Severe Acute Respiratory Syndrome Coronavirus 2 (SARS– CoV-2) is the cause of the current worldwide outbreak of the respiratory disease COVID- 19.
  • COVID-19 generally has less severe symptoms and a lower case-fatality rate, but is transmitted more rapidly compared to the related coronaviruses causing the Severe Acute Respiratory Syndrome (SARS) outbreak in 2003.
  • SARS-CoV-2 genome shares high sequence identity with SARS-CoV.
  • Both viruses critically rely on the activity of viral proteases: the main protease (Mpro/3CLpro in non-structural protein 5 (nsp5)) and the papain-like protease (PLpro, a part of nsp3) to generate a functional replicase complex and enable viral spread.
  • SCoV-PLpro also acts as a protease for ubiquitin and ISG15, known regulators of host innate immune pathways, and inhibition of SCoV-PLpro was shown to block SARS-CoV replication.
  • a Series of Novel and Reversible Inhibitors for the Severe Acute Respiratory Syndrome-Coronavirus Papain-Like Protease has been disclosed in J Med Chem. 2009 August 27; 52(16): 5228–5240. Wipo patent application No.
  • WO2010022355 disclosed certain class of compounds as papain-Like Protease (PLpro) inhibitors for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).
  • PLpro papain-like protease
  • SARS severe acute respiratory syndrome
  • MERS Middle East respiratory syndrome
  • COVID19 Coronavirus disease 2019 (COVID19)
  • inventions of the present invention are useful as therapeutics in the treatment of a variety of pathological conditions including (but not limited to) viral diseases or conditions.
  • PLpro papain-like protease
  • the present invention discloses novel compounds as defined by the general formula (I) that are papain-like protease (PLpro) modulators for the prevention and treatment of disease states mediated by papain-like protease (PLpro) as well as treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated.
  • the compounds of the present invention are useful in the treatment of human or animal body, by inhibition of papain-like protease (PLpro).
  • the compounds of this invention are therefore suitable for the prevention and treatment of disease states mediated by papain-like protease (PLpro).
  • An embodiment of the present invention provides novel compounds represented by the general formula (I), their tautomeric forms, their enantiomers, their diastereoisomers, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutical compositions containing them or their mixtures thereof.
  • PLpro papain-like protease
  • PLpro papain-like protease
  • compound of formula (I) of the present invention may be used in combination with one or more suitable pharmaceutically active agents.
  • a process for preparing the novel compounds of the present invention is provided.
  • the present invention relates to the compounds of the general formula (I) their tautomeric forms, their stereoisomers, their enantiomers, their pharmaceutically acceptable salts, and pharmaceutical compositions containing them wherein, ‘A’ is selected from unsubstituted or substituted (C 3 -C 7 )cycloalkyl, aryl, heteroaryl heterocyclyl, bridged or spiro ring system having optionally one or more than one heteroatoms; ‘B’ is selected from unsubstituted or substituted (C 3 -C 7 )cycloalkyl, aryl, heteroaryl heterocyclyl, bridged, fused bi- or tri- cyclic ring systems or spiro ring system having optionally one or more than one heteroatoms; Each of R 1 and R 2 at each occurrence independently represents hydrogen, halogen, haloalkyl, cyano, amine, optionally substituted groups selected from (C 1 -C 6 )
  • alkyl group examples include but not limited to methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert. -butyl, pentyl, hexyl etc.
  • alkyl also includes cycloalkyl groups, and combinations of linear or branched alkyl chains combined with cycloalkyl structures. When no number of carbon atoms is specified, C 1-6 is intended.
  • Substituted alkyl includes alkyl substituted with one or more moieties selected from the group consisting of halo ⁇ e.g., CI, F, Br, and I); halogenated alkyl ⁇ e.g., CF 3 , 2-Br-ethyl, CH 2 F, CH 2 CI, CH 2 CF 3 , or CF 2 CF 3 ); hydroxyl; amino; carboxylate; carboxamido; alkylamino; arylamino; alkoxy; aryloxy; nitro; azido; cyano; thio; sulfonic acid; sulfate; phosphonic acid; phosphate; and phosphonate as well as those described under the definition of ‘Optionally substituted’.
  • halo ⁇ e.g., CI, F, Br, and I
  • halogenated alkyl ⁇ e.g., CF 3 , 2-Br-ethyl, CH 2 F, CH 2
  • alkenyl means carbon chains which contain at least one carbon-carbon double bond, and which may be linear or branched or combinations thereof, unless the carbon chain is defined otherwise.
  • alkenyl include but not limited to vinyl, allyl, isopropenyl, hexenyl, pentenyl, heptenyl, 1 -propenyl, : 2-butenyl, 2-methyl -2-butenyl etc.
  • the term alkenyl also includes cycloalkenyl groups and combinations of linear, branched and cyclic structures. When no number of carbon atoms is specified, C 2-6 ) is intended.
  • Alkynyl means carbon chains which contain at least one carbon-carbon triple bond, and which may be linear or branched or combinations thereof. Examples of alkynyl include ethynyl, propargyl, 3-methyl- l -pentynyl etc. When no number of carbon atoms is specified, is intended.
  • carbocycle or “carbocyclic residue” is intended to mean any stable monocyclic or bicyclic or tricyclic ring, any of which may be saturated, partially unsaturated, or aromatic.
  • carbocycles include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane (decalin), [2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl (tetralin).
  • carbocycle is intended to include, wherever applicable, the groups representing cycloalkyl, phenyl and other saturated, partially saturated or aromatic residues;
  • cycloalkyl and cycloalkenyl refers to optionally substituted, saturated and unsaturated mono-cyclic, bicyclic or tricyclic carbon groups.
  • the cycloalkyl or cycloalkenyl group may have a specified number of carbon atoms, for example, C 3 -C 7 cycloalkyl or cycloalkenyl includes within its scope a carbocyclic group having 3, 4, 5 or 6 carbon atoms.
  • substituents may be selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclohexadienyl and the like.
  • Substituted cycloalkyl or cycloalkenyl includes substitutions with one or more moieties selected from the group consisting of halo (e.g. , CI, F, Br, and I); halogenated alkyl (e.g.
  • alkoxy refers to the straight or branched chain alkoxides of the number of carbon atoms specified.
  • aryl or “aromatic” group used either alone or in combination with other radicals is selected from a suitable aromatic system containing one, two or three rings wherein such rings may be attached together in a pendant manner or may be fused, more preferably the groups are selected from phenyl, naphthyl, tetrahydronaphthyl, indane, biphenyl, and the like;
  • Heterocyclyl means a saturated, partially saturated or unsaturated aromatic or non- aromatic mono, bi or tricyclic radicals, containing one or more heteroatoms selected from nitrogen, sulfur and oxygen, further optionally including the oxidized forms of sulfur, namely SO & SO 2 .
  • Heterocyclyl systems may be attached to another moiety via any number of carbon atoms or heteroatoms of the radical and may be both saturated and unsaturated.
  • heterocycles include tetrahydrofuran (THF), dihydrofuran, 1,4-dioxane, morpholine, 1,4-dithiane, piperazine, piperidine, 1,3-dioxolane, imidazoline, imidazolidine, pyrrolidine, pyrroline, tetrahydropyran, dihydropyran, oxathiolane, dithiolane, 1 ,3-dioxane, 1 ,3-dithiane, oxathiane, thiomorpholine, etc.
  • THF tetrahydrofuran
  • dihydrofuran 1,4-dioxane
  • morpholine 1,4-dithiane
  • piperazine piperidine
  • 1,3-dioxolane imidazo
  • heterocycloalkyl refers to a heterocyclic group as defined above connected to an alkyl group as defined above;
  • heterocyclyl means 4- to 7-membered saturated or partially saturated heterocyclic ring, 7- to 14-membered bicyclic heterocyclic ring system, fused heterocyclic ring system, bridged or spiro ring system having optionally one or more than one heteroatoms selected from nitrogen, sulfur and oxygen, further optionally including the oxidized forms of sulfur, namely SO & SO 2.
  • heteroaryl or “heteroaromatic” group used either alone or in combination with other radicals is selected from suitable single or fused mono, bi or tricyclic aromatic heterocyclic radicals containing one or more hetero atoms selected from O, N or S, more preferably the groups are selected from pyridyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, isothiazolyl, imidazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, benzofuranyl, benzothienyl, indolinyl, indolyl, azaindolyl, azaindolinyl, pyrazolopyrimidinyl, azaquinazolinyl, pyridofuranyl, pyridothienyl, thienopyrimidyl, quinolinyl,
  • the halogen atoms are all the same as one another.
  • the “haloalkoxy” group is selected from suitable haloalkyl, as defined above, directly attached to an oxygen atom, more preferably groups selected from fluoromethoxy, chloromethoxy, fluoroethoxy, chloroethoxy and the like; In certain other embodiment in which two or more hydrogen atoms are replaced with halogen atoms, the halogen atoms are not all the same as one another.
  • “Aryloxyalkyl” means an alkyl radical substituted with aryloxy group as defined herein.
  • Aryloxyaryl means an aryl radical substituted with aryloxy group as defined herein.
  • Aryloxyheteroaryl means a heteroaryl radical substituted with aryloxy group as defined herein.
  • Halo/ Halogen refers to fluorine, chlorine, bromine, iodine. Chlorine and fluorine are generally preferred. Suitable groups and substituents on the groups may be selected from those described anywhere in the specification.
  • substituted as used herein, means that any one or more hydrogen on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound.
  • substituted means that any one or more hydrogens on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound.
  • “Pharmaceutically acceptable salts” refer to derivatives of the disclosed compounds wherein the parent compound is modified by making acid or base salts thereof. Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of the basic residues.
  • Such conventional non-toxic salts include, but are not limited to, those derived from inorganic and organic acids selected from 1 , 2-ethanedisulfonic, 2- acetoxybenzoic, 2-hydroxyethanesulfonic, acetic, ascorbic, benzenesulfonic, benzoic, bicarbonic, carbonic, citric, edetic, ethane disulfonic, ethane sulfonic, fumaric, glucoheptonic, gluconic, glutamic, glycolic, glycollyarsanilic, hexylresorcinic, hydrabamic, hydrobromie hydrochloric hydroiodide hydroxymaleic hydroxynaphthoic isethionic lactic, lactobionic, -lauryl sulfonic, maleic, malic, mandelic, methanesulfonic, napsylic, nitric, oxalic, pamoic, pantothenic, pheny
  • optionally substituted alkyl' means either 'alkyl' or 'substituted alkyl'.
  • an optionally substituted group includes an unsubstituted group.
  • structures depicted herein are also meant to include compounds which differ only in the presence of one or more isotopically enriched atoms.
  • Particularly useful compounds may be selected from but not limited to the following:
  • TNF ⁇ Tumor necrosis factor alpha
  • the novel compounds of the present invention can be prepared using the reactions and techniques described below, together with conventional techniques known to those skilled in the art of organic synthesis, or variations thereon as appreciated by those skilled in the art.
  • the reactions can be performed in solvents appropriate to the reagents and materials employed and suitable for the transformations being affected. Preferred methods include, but not limited to those described below, where all symbols are as defined earlier unless and otherwise defined below.
  • the compounds of the general formula (I) can be prepared as described in schemes below along with suitable modifications/variations which are well within the scope of a person skilled in the art.
  • Example-1 Preparation of (R)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
  • Intermediate-1 Preparation of (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5- nitrobenzamide
  • 2-methyl-5-nitrobenzoic acid 0.6 g, 3.31 mmol
  • (R)-1-(naphthalen-1-yl)ethan-1-amine 0.567 g, 3.31 mmol
  • EDC 0.794 g, 4.14 mmol
  • HOBT 0.634 g, 4.14 mmol
  • DIPEA 2.256 ml, 12.92 mmol
  • reaction mixture was stirred under nitrogen atmosphere at 25 °C for 17 h. Completion of reaction checked by TLC. The reaction was concentrated in vacuo and diluted with water, solid was filtered and washed it with water. Crude product was directly used in next step without further purification.
  • Example-13 2-methyl-5-((S)-2-(methylsulfonamido)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide
  • IR (KBr): 3257, 1670, 1535, 1311, 1149, 979, 800, 777 cm -1 ;
  • MS (TOF): m/z (%) 537.2180 (40%) (M+H) + , 535.2018 (100%) (M-H).
  • PLpro inhibition assay To determine IC50 values of potential PLpro inhibitors, ISG15-AMC (R & D system) was used as substrate of PLpro and the release of AMC was measured by increase of fluorescence (Ex./Em.380/460 nm with 5 nm bandwidth) on 96-well microplate reader (Tecan M1000 Pro).
  • the viral load is measured in throat and nasal swabs at various treatment days and in lung at termination. Blood samples are collected for the evaluation of various cytokine and biochemical parameters. At termination, all animals are sacrificed, necropsies is conducted; gross observations are noted, and tissue samples is obtained from the lungs and other vital organs or histopathological examination. The anti- viral activity is evaluated based on the difference in viral load and change in various blood, clinical, and histological parameters observed in test compound-treated animals Vs. Placebo-treated animals.
  • the compounds of formula (I) or pharmaceutical compositions containing them are useful as a medicament for the inhibition of Papain-Like protease (PLpro) activity and suitable for humans and other warm blooded animals, and may be administered either by oral, topical or parenteral administration.
  • the compounds of the present invention are formulated with conventional carriers and excipients, which will be selected in accord with ordinary practice. Tablets will contain excipients, glidants, fillers, binders and the like.
  • Aqueous formulations are prepared in sterile form and when intended for delivery by other than oral administration generally will be isotonic. All formulations will optionally contain excipients such as those set forth in the “Handbook of Pharmaceutical Excipients” (1986).
  • the formulations, both for veterinary and for human use, of the invention comprise at least one active ingredient, as above defined, together with one or more acceptable carriers therefore and optionally other therapeutic ingredients, particularly those additional therapeutic ingredients as discussed herein.
  • the carrier(s) must be “acceptable” in the sense of being compatible with the other ingredients of the formulation and physiologically innocuous to the recipient thereof.
  • Formulations of the present invention suitable for oral administration may be presented as discrete units such as capsules, cachets or tablets each containing a predetermined amount of the active ingredient: as a powder or granules: as a solution or a suspension in an aqueous or non-aqueous liquid: or as an oil-in-water liquid emulsion or a water-in-oil liquid emulsion.
  • the active ingredient may also be administered as a bolus, electuary or paste.
  • Pharmaceutical formulation according to the present invention comprise a combination according to the invention together with one or more pharmaceutically acceptable carriers or excipients and optionally other therapeutic agents.
  • Pharmaceutical formulations containing the active ingredient may be in any form suitable for the intended method of administration.
  • aqueous or oil suspensions dispersible powders or granules, emulsions, hard or soft capsules, syrups or elixirs
  • One or more compounds of the invention are administered by any route appropriate to the condition to be treated. Suitable routes include oral, rectal, nasal, pulmonary, topical (including buccal and sublingual), vaginal and parenteral (including subcutaneous, intramuscular, intravenous, intradermal, intrathecal and epidural), and the like. It will be appreciated that the preferred route may vary with for example the condition of the recipient.
  • a pharmaceutical composition comprising the compounds of the present invention may comprise a suitable binder, suitable bulking agent &/or diluent and any other suitable agents as may be necessary.
  • the pharmaceutical composition may be suitably coated with suitable coating agents.
  • the compounds of the present invention, formula (I), may be used alone or in any combination with one or more other therapeutic agents which a skilled medical practitioner can easily identify.
  • Such other therapeutic agent may be selected depending on the type of disease being treated, the severity, other medications being taken by the patients etc, like severe acute respiratory syndrome (SARS), Middle East respiratory syndrome (MERS), Spanish flu, COVID19 (Coronavirus disease 2019), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus.
  • compound of formula (I) of the present invention may be used in combination with one or more suitable pharmaceutically active agents selected from following therapeutic agents in any combination.
  • Inhibitors of interleukin-1 ⁇ e.g.
  • Rilonacept Canakinumab and Anakinra
  • immune suppressants eg Dexamethasone Methotrexate, Mercaptopurine, Cyclophosphamide
  • metabolic disorders drugs eg., glucocorticoids, non-steroidal anti-inflammatory drugs, Gasdermin D inhibitors (e.g., Necrosulfonamide); Cox-2 specific inhibitors, TNF- ⁇ binding proteins (e.g.,Infliximab, Etanercept), Interferon-13, Interferon, Interleukin-2, antihistamines, beta-agonist, BTK inhibitors, anticolinergics, anti-cancer agents; anti-viral drugs, for example: Remdesivir, Lopinavir/Ritonavir, Favipiravir, Tamiflu; anti-malarial agents, for example: Choloroquinone, Hydroxyl Chloroquinone; or their suitable pharmaceutically acceptable salts.
  • TNF- ⁇ binding proteins e.g.,Inf
  • Non-Alcoholic Steato- Hepatitis and fibrosis drugs
  • anticancer antibiotics, for example Azithromycin; hormones, Aromatase inhibitors, Colchicine, Anticoagulants, antibodies, cytokines, anti-IL6 drugs; Antiparasitics; vaccines; Interferons; drug conjugates; Drugs originally developed for SARS (ACE2 protein decoy); Intravenous vitamin C; inhibitors of mitogen-activated protein kinase signaling (ex: BAY 43-9006); Syk inhibitors; mTOR inhibitors; antibodies (Rituxan); and BCR/ABL antagonist.
  • Compositions of the invention are also used in combination with other active ingredients.
  • the other active therapeutic agent is active against Arenaviridae virus infections, particularly Lassa virus and Junin virus infections.
  • Non-limiting examples of these other active therapeutic agents are Ribavirin, Favipiravir (also known as T-705 or Avigan),T-705 monophosphate, T-705 diphosphate, T-705 triphosphate, ST- 193, and mixtures thereof.
  • the compounds and compositions of the present invention are also intended for use with general care provided patients with Arenaviridae viral infections, including parenteral fluids (including dextrose saline and Ringer's lactate) and nutrition, antibiotic (including Metronidazole and Cephalosporin antibiotics, such as Ceftriaxone and Cefuroxime) and/or antifungal prophylaxis, fever and pain medication, antiemetic (such as Metoclopramide) and/or antidiarrheal agents, vitamin and mineral supplements (including Vitamin C or/and K and zinc sulfate), anti-inflammatory agents (such as Ibuprofen), pain medications, and medications for other common diseases in the patient population, such anti-malarial agents (including Artemether and Artesunate-lumefantrine combination therapy), typhoid (including quinolone antibiotics, such as Ciprofloxacin, macrolide antibiotics, such as Azithromycin, cephalosporin antibiotics, such as Ceftri

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Abstract

The present invention relates to novel compounds of the general formula (I) their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers and polymorphs. The invention also relates to processes for the preparation of the compounds of invention, pharmaceutical compositions containing the compounds and their use as the compounds of the invention belong to the family of papain-like protease (PLpro) modulators. The present invention thus relates to novel papain-like protease (PLpro) modulators and their use in the treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated like severe acute respiratory syndrome (SARS), Middle east respiratory syndrome (MERS), Spanish flu, COVID19 (Coronavirus disease 2019), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus. Formula (I)

Description

NOVEL AMIDE DERIVATIVES FIELD OF THE INVENTION The present invention relates to novel compounds of the general formula (I) their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers and polymorphs. The invention also relates to processes for the preparation of the compounds of invention, pharmaceutical compositions containing the compounds and their use as the compounds of the invention belong to the family of papain-like protease (PLpro) modulators. The present invention thus relates to novel papain-like protease (PLpro) modulators and their use in the treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated like severe acute respiratory syndrome (SARS), Middle east respiratory syndrome (MERS), Spanish flu, COVID19 (Coronavirus disease 2019), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus. BACKGROUND OF THE INVENTION Severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the causative agent for COVID-19, is a novel human betacoronavirus that is rapidly spreading worldwide. As a betacoronavirus, SARSCoV-2 encodes for a papain-like protease (PLpro) that is likely responsible for cleavage of the CoV viral poly-peptide. The PLpro is also responsible for suppression of host innate immune responses by virtue of its ability to reverse host ubiquitination and ISGylation events. The biochemical activity of SARS-CoV-2 PLpro against ubiquitin and ISG15 substrates was evaluated revealing that the protease has a marked reduction in its ability to process K48 linked Ub substrates compared to its counterpart in SARS-CoV. Additionally, its substrate activity more closely mirrors that of the PLpro from the Middle East respiratory syndrome coronavirus and prefers ISG15s from certain species including humans. (Proc Natl Acad Sci 2008, vol.105, no.42, 16119–16124; ACS Infectious Diseases, 2020, 6, 8, 2099-2109). The papain-like protease PLpro is an essential coronavirus enzyme required for processing viral polyproteins to generate a functional replicase complex and enable viral spread. PLpro is also implicated in cleaving proteinaceous post-translational modifications on host proteins as an evasion mechanism against host anti-viral immune responses. (Nature Microbiology 2020, 5, 536-544). The novel coronavirus Severe Acute Respiratory Syndrome Coronavirus 2 (SARS– CoV-2) is the cause of the current worldwide outbreak of the respiratory disease COVID- 19. COVID-19 generally has less severe symptoms and a lower case-fatality rate, but is transmitted more rapidly compared to the related coronaviruses causing the Severe Acute Respiratory Syndrome (SARS) outbreak in 2003. The SARS-CoV-2 genome shares high sequence identity with SARS-CoV. Both viruses critically rely on the activity of viral proteases: the main protease (Mpro/3CLpro in non-structural protein 5 (nsp5)) and the papain-like protease (PLpro, a part of nsp3) to generate a functional replicase complex and enable viral spread. SCoV-PLpro also acts as a protease for ubiquitin and ISG15, known regulators of host innate immune pathways, and inhibition of SCoV-PLpro was shown to block SARS-CoV replication. (J Virol 2005, 79, 15189-15198; Methods in molecular biology (Clifton, N.J.) 2015, 1282, 1-23; The EMBO Journal (2020) 39: e106275; Antiviral Res (2015) 115: 21 – 38 A Series of Novel and Reversible Inhibitors for the Severe Acute Respiratory Syndrome-Coronavirus Papain-Like Protease has been disclosed in J Med Chem. 2009 August 27; 52(16): 5228–5240. Wipo patent application No. WO2010022355 disclosed certain class of compounds as papain-Like Protease (PLpro) inhibitors for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS). We herein disclose novel compounds of general formula (I) which are papain-like protease (PLpro) modulators for the prevention and treatment of disease states mediated by papain-like protease (PLpro) or conditions in which SARS-CoV, SARS-CoV2 virus is implicated, including severe acute respiratory syndrome (SARS), Middle East respiratory syndrome (MERS), Spanish flu, Coronavirus disease 2019 (COVID19), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus. More particularly, embodiments of the present invention are useful as therapeutics in the treatment of a variety of pathological conditions including (but not limited to) viral diseases or conditions. SUMMARY OF THE INVENTION The present invention discloses novel compounds as defined by the general formula (I) that are papain-like protease (PLpro) modulators for the prevention and treatment of disease states mediated by papain-like protease (PLpro) as well as treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated. The compounds of the present invention are useful in the treatment of human or animal body, by inhibition of papain-like protease (PLpro). The compounds of this invention are therefore suitable for the prevention and treatment of disease states mediated by papain-like protease (PLpro). EMBODIMENT(S) OF THE INVENTION An embodiment of the present invention provides novel compounds represented by the general formula (I), their tautomeric forms, their enantiomers, their diastereoisomers, their stereoisomers, their pharmaceutically acceptable salts and pharmaceutical compositions containing them or their mixtures thereof. In another embodiment of the present invention is provided pharmaceutical compositions containing compounds of the general formula (I), their tautomeric forms, their enantiomers, their diastereoisomers, their stereoisomers, their pharmaceutically acceptable salts, or their mixtures in combination with suitable carriers, solvents, diluents and other media normally employed in preparing such compositions. In a further embodiment is provided the use of compounds of the present invention as papain-like protease (PLpro) modulators, by administering a therapeutically effective and non-toxic amount of compounds of general formula (I) or their pharmaceutically acceptable compositions to the mammals. In a still further embodiment compound of formula (I) of the present invention may be used in combination with one or more suitable pharmaceutically active agents. In another further embodiment is provided a process for preparing the novel compounds of the present invention. DESCRIPTION OF THE INVENTION Accordingly, the present invention relates to the compounds of the general formula (I)
Figure imgf000004_0001
their tautomeric forms, their stereoisomers, their enantiomers, their pharmaceutically acceptable salts, and pharmaceutical compositions containing them wherein, ‘A’ is selected from unsubstituted or substituted (C3-C7)cycloalkyl, aryl, heteroaryl heterocyclyl, bridged or spiro ring system having optionally one or more than one heteroatoms; ‘B’ is selected from unsubstituted or substituted (C3-C7)cycloalkyl, aryl, heteroaryl heterocyclyl, bridged, fused bi- or tri- cyclic ring systems or spiro ring system having optionally one or more than one heteroatoms; Each of R1 and R2 at each occurrence independently represents hydrogen, halogen, haloalkyl, cyano, amine, optionally substituted groups selected from (C1-C6)alkyl, (C2- C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, N(C3-C8)cycloalkyl, (C1- C6)alkylSO2(C1-C6)alkyl, (C1-C6)alkylN(C1-C6)alkyl, (C1-C6)alkylN(C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl, benzyl, thiol, mercaptoalkyl, SO2(C1-C6)alkyl, SO2(C3-C7)cycloalkyl, SO2-aryl, SO2-heterocyclyl, (C1-C6)thioalkyl, (C1-C6)thioalkoxy, (C1-C6)alkylSO2NH2, -CONH2, -CO(C1-C6)alkyl, -CO(C1-C6)haloalkyl, -CO-aryl, -CO- heteroaryl, -CO-heterocyclyl, heterocyclyl, fused, bridged or spiro ring system having optionally one or more than one heteroatoms; Each of R3, R4 , R5, R6 at each occurrence independently represents hydrogen, halogen, haloalkyl, cyano, nitro, amide, sulphonamide, acyl, hydroxyl, optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C7)cycloalkyl, (C1- C6)alkoxy, SO2(C1-C6)alkyl, thiol, mercapto alkyl benzyl, aryl, heteroaryl, heterocyclyl, bridged or spiro ring system having optionally one or more than one heteroatoms; Alternatively R3 and A forms together may form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group consisting of N, O, CO, and S(O)q; q = 1-3; Alternatively R4 or R5 and A forms together may form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group consisting of N, O, CO, and S(O)r; r = 1-2.; Each of V, W, X, Y, Z at each occurrence is independently selected from a bond, hydrogen, N, S, SO, SO2, O, CO, OH, NH, S(O)N-R7, O-R7, N-R7; unsubstituted or substituted (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C7)cycloalkyl, aryl, heteroaryl and heterocyclyl, wherein R7 at each occurrence independently represents hydrogen, hydroxyl, halogen, nitro, cyano, haloalkyl, optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, (C2-C6) alkenyl, (C2-C6)alkynyl, SO2(C1-C6)alkyl, thiol, thioalkyl, thio-alkoxy, SO2(C1-C6)alkyl, SO(C1-C6)alkyl, benzyl, aryl, heteroaryl, heterocyclyl, fused cyclic ring systems or spiro ring system; Alternatively V, W, X, Y, Z wherever possible together may form a 3- to 8-membered aryl or heterocyclic ring having optionally one or more than one hetero atoms selected from the group consisting of N, CO, O, CO, and S(O)t; t = 1-2.; m, n, o, p is independently selected from integer 0-4; When any of above defined group is substituted the substitutions on them may be selected from those described above or may be selected from hydrogen, halogen, hydroxy, cyano, halo, haloalkyl, haloalkyloxy, alkylthio (C1-C6)alkyl, (C2-C6)alkenyl, (C2- C6)alkynyl, (C3-C10)cycloalkyl, C1-C6 alkoxy, aryl, heterocyclyl, heteroaryl, -COR11, - CSR11, C(O)OR11, C(O)-R11, -C(O)-NR11R12, -C(S)-NR11R12, -SO2R11 group, wherein each of R11 and R12 is independently selected from hydrogen, optionally substituted group selected from (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl groups; In a preferred embodiment, the groups, radicals described above may be selected from: "Alkyl", as well as other groups having the prefix "alk", such as alkoxy and alkanoyl, means a carbon chain which may further be substituted with an oxygen atom as is well understood by a skilled artisan, which may further be either linear or branched, and combinations thereof, unless the carbon chain is defined otherwise. Examples of alkyl group include but not limited to methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert. -butyl, pentyl, hexyl etc. Where the specified number of carbon atoms permits e.g. from C3-10, the term alkyl also includes cycloalkyl groups, and combinations of linear or branched alkyl chains combined with cycloalkyl structures. When no number of carbon atoms is specified, C1-6 is intended. Substituted alkyl includes alkyl substituted with one or more moieties selected from the group consisting of halo {e.g., CI, F, Br, and I); halogenated alkyl {e.g., CF3, 2-Br-ethyl, CH2F, CH2CI, CH2CF3, or CF2CF3); hydroxyl; amino; carboxylate; carboxamido; alkylamino; arylamino; alkoxy; aryloxy; nitro; azido; cyano; thio; sulfonic acid; sulfate; phosphonic acid; phosphate; and phosphonate as well as those described under the definition of ‘Optionally substituted’. "Alkenyl" means carbon chains which contain at least one carbon-carbon double bond, and which may be linear or branched or combinations thereof, unless the carbon chain is defined otherwise. Examples of alkenyl include but not limited to vinyl, allyl, isopropenyl, hexenyl, pentenyl, heptenyl, 1 -propenyl,: 2-butenyl, 2-methyl -2-butenyl etc. Where the specified number of carbon atoms permits, e.g., from C5-10, the term alkenyl also includes cycloalkenyl groups and combinations of linear, branched and cyclic structures. When no number of carbon atoms is specified, C2-6) is intended. "Alkynyl" means carbon chains which contain at least one carbon-carbon triple bond, and which may be linear or branched or combinations thereof. Examples of alkynyl include ethynyl, propargyl, 3-methyl- l -pentynyl etc. When no number of carbon atoms is specified, is intended. The “thioalkyl” group used either alone or in combination with other radicals, denotes an alkyl group, as defined above, attached to a group of formula –SR’, (sulfur and its oxidized forms) where R’ represents hydrogen, alkyl or aryl group, e.g. thiomethyl, methylthiomethyl, phenylthiomethyl and the like, which may be optionally substituted. As used herein, "carbocycle" or "carbocyclic residue" is intended to mean any stable monocyclic or bicyclic or tricyclic ring, any of which may be saturated, partially unsaturated, or aromatic. Examples of such carbocycles include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane (decalin), [2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl (tetralin). In a broader perspective, the term carbocycle is intended to include, wherever applicable, the groups representing cycloalkyl, phenyl and other saturated, partially saturated or aromatic residues; The terms "cycloalkyl" and "cycloalkenyl" refers to optionally substituted, saturated and unsaturated mono-cyclic, bicyclic or tricyclic carbon groups. Where appropriate, the cycloalkyl or cycloalkenyl group may have a specified number of carbon atoms, for example, C3-C7 cycloalkyl or cycloalkenyl includes within its scope a carbocyclic group having 3, 4, 5 or 6 carbon atoms. Examples of such substituents may be selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclohexadienyl and the like. Substituted cycloalkyl or cycloalkenyl includes substitutions with one or more moieties selected from the group consisting of halo (e.g. , CI, F, Br, and I); halogenated alkyl (e.g. , CF3, 2-Br-ethyl, CH2F, CH2CI, CH2CF3, or CF2CF3); hydroxyl; amino; carboxylate; carboxamido; alkylamino; arylamino; alkoxy; aryloxy; nitro; azido; cyano; thio; sulfonic acid; sulfate; phosphonic acid; phosphate; and phosphonate as well as those described under the definition of ‘Optionally substituted’. The "alkoxy" refers to the straight or branched chain alkoxides of the number of carbon atoms specified. The “aryl” or “aromatic” group used either alone or in combination with other radicals, is selected from a suitable aromatic system containing one, two or three rings wherein such rings may be attached together in a pendant manner or may be fused, more preferably the groups are selected from phenyl, naphthyl, tetrahydronaphthyl, indane, biphenyl, and the like; “Heterocyclyl” means a saturated, partially saturated or unsaturated aromatic or non- aromatic mono, bi or tricyclic radicals, containing one or more heteroatoms selected from nitrogen, sulfur and oxygen, further optionally including the oxidized forms of sulfur, namely SO & SO2. Heterocyclyl systems may be attached to another moiety via any number of carbon atoms or heteroatoms of the radical and may be both saturated and unsaturated. Examples of heterocycles include tetrahydrofuran (THF), dihydrofuran, 1,4-dioxane, morpholine, 1,4-dithiane, piperazine, piperidine, 1,3-dioxolane, imidazoline, imidazolidine, pyrrolidine, pyrroline, tetrahydropyran, dihydropyran, oxathiolane, dithiolane, 1 ,3-dioxane, 1 ,3-dithiane, oxathiane, thiomorpholine, etc. The term "heterocycloalkyl" refers to a heterocyclic group as defined above connected to an alkyl group as defined above; In one embodiment “heterocyclyl means 4- to 7-membered saturated or partially saturated heterocyclic ring, 7- to 14-membered bicyclic heterocyclic ring system, fused heterocyclic ring system, bridged or spiro ring system having optionally one or more than one heteroatoms selected from nitrogen, sulfur and oxygen, further optionally including the oxidized forms of sulfur, namely SO & SO2. The “heteroaryl” or “heteroaromatic” group used either alone or in combination with other radicals, is selected from suitable single or fused mono, bi or tricyclic aromatic heterocyclic radicals containing one or more hetero atoms selected from O, N or S, more preferably the groups are selected from pyridyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, isothiazolyl, imidazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, benzofuranyl, benzothienyl, indolinyl, indolyl, azaindolyl, azaindolinyl, pyrazolopyrimidinyl, azaquinazolinyl, pyridofuranyl, pyridothienyl, thienopyrimidyl, quinolinyl, pyrimidinyl, pyrazolyl, quinazolinyl, pyridazinyl, triazinyl, benzimidazolyl, benzotriazolyl, phthalazynil, naphthylidinyl, purinyl, carbazolyl, phenothiazinyl, phenoxazinyl, benzoxazolyl, benzothiazolyl and the like; The term "haloalkyl "means an alkyl structure in which at least one hydrogen is replaced with a halogen atom. In certain embodiments in which two or more hydrogen atoms are replaced with halogen atoms, the halogen atoms are all the same as one another. the “haloalkoxy” group is selected from suitable haloalkyl, as defined above, directly attached to an oxygen atom, more preferably groups selected from fluoromethoxy, chloromethoxy, fluoroethoxy, chloroethoxy and the like; In certain other embodiment in which two or more hydrogen atoms are replaced with halogen atoms, the halogen atoms are not all the same as one another. "Aryloxyalkyl" means an alkyl radical substituted with aryloxy group as defined herein. "Aryloxyaryl" means an aryl radical substituted with aryloxy group as defined herein. "Aryloxyheteroaryl" means a heteroaryl radical substituted with aryloxy group as defined herein. "Halo/ Halogen" refers to fluorine, chlorine, bromine, iodine. Chlorine and fluorine are generally preferred. Suitable groups and substituents on the groups may be selected from those described anywhere in the specification. The term "substituted," as used herein, means that any one or more hydrogen on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound. The term "substituted," as used herein, means that any one or more hydrogens on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound. "Pharmaceutically acceptable salts" refer to derivatives of the disclosed compounds wherein the parent compound is modified by making acid or base salts thereof. Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of the basic residues. Such conventional non-toxic salts include, but are not limited to, those derived from inorganic and organic acids selected from 1 , 2-ethanedisulfonic, 2- acetoxybenzoic, 2-hydroxyethanesulfonic, acetic, ascorbic, benzenesulfonic, benzoic, bicarbonic, carbonic, citric, edetic, ethane disulfonic, ethane sulfonic, fumaric, glucoheptonic, gluconic, glutamic, glycolic, glycollyarsanilic, hexylresorcinic, hydrabamic, hydrobromie hydrochloric hydroiodide hydroxymaleic hydroxynaphthoic isethionic lactic, lactobionic, -lauryl sulfonic, maleic, malic, mandelic, methanesulfonic, napsylic, nitric, oxalic, pamoic, pantothenic, phenylacetic, phosphoric, polygalacturonic, propionic, salicyclic, stearic, subacetic, succinic, sulfamic, sulfanilic, sulfuric, tannic, tartaric, and toluenesulfonic.
The term 'optional' or ‘optionally' means that the subsequent described event or circumstance may or may not occur, and the description includes instances where the event or circumstance occur and instances in which it does not. For example, optionally substituted alkyl' means either 'alkyl' or 'substituted alkyl'. Further an optionally substituted group includes an unsubstituted group.
Unless otherwise stated in the specification, structures depicted herein are also meant to include compounds which differ only in the presence of one or more isotopically enriched atoms.
Particularly useful compounds may be selected from but not limited to the following:
5-((S)-2,3-diaminopropanamido)-N-((R)-1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1- carbonyl)benzamide;
(R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide;
(R)-5-(2-aminoacetamido)-N-(l-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1- carbonyl)benzamide;
(R)-5-amino-N-(l-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide;
(S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide;
(R)- 1 -isopropyl-N -(4-methyl-3-(((R)- 1 -(naphthalen- 1 - yl)ethyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide;
(R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide;
(S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide;
(S)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide;
5-(2-aminoacetamido)-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2- methy Ibenzamide ;
5-acetamido-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2-methylbenzamide;
5-amino-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2-methylbenzamide;
5-((S)-2,3-diaminopropanamido)-2-methyl-N-((S)-1-(naphthalen-1-yl)ethyl)benzamide; (S)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinolin-5-ylmethyl)benzamide; 5-(2-aminoacetamido)-2-methyl-N-(quinolin-5-ylmethyl)benzamide; 2-methyl-N-(quinolin-5-ylmethyl)-5-ureidobenzamide; 5-acetamido-2-methyl-N-(quinolin-5-ylmethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinoxalin-2-ylmethyl)benzamide; 5-(2-aminoacetamido)-2-methyl-N-(quinoxalin-2-ylmethyl)benzamide; 2-methyl-N-(quinoxalin-2-ylmethyl)-5-ureidobenzamide; 5-acetamido-2-methyl-N-(quinoxalin-2-ylmethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinolin-2-ylmethyl)benzamide; 5-(2-aminoacetamido)-2-methyl-N-(quinolin-2-ylmethyl)benzamide; 2-methyl-N-(quinolin-2-ylmethyl)-5-ureidobenzamide; N-(2-(1H-indol-3-yl)ethyl)-5-amino-2-methylbenzamide; N-(2-(1H-indol-3-yl)ethyl)-5-(2-aminoacetamido)-2-methylbenzamide; N-(2-(1H-indol-3-yl)ethyl)-2-methyl-5-ureidobenzamide; N-(2-(1H-indol-3-yl)ethyl)-5-acetamido-2-methylbenzamide; (R)-5-acetamido-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-2-(dimethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-(dimethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-(dimethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-(methylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-5-(2-aminoacetamido)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; 5-((S)-2,3-diaminopropanamido)-N-((R)-1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl) benzamide; 3-(2-aminoacetamido)-N-(imidazo[1,2-a]pyridin-2-ylmethyl)benzamide; 3-amino-N-(imidazo[1,2-a]pyridin-2-ylmethyl)benzamide; (R)-5-(4-aminobutanamido)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)-2-propoxybenzamide; (R)-2-isopropoxy-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-(2-aminoacetamido)-N-(1-(naphthalen-1-yl)ethyl)-6-(propoxymethyl)benzamide; (R)-2-(2-aminoacetamido)-6-(hydroxymethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-((S)-2,3-diaminopropanamido)-6-(isopropoxymethyl)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-3-(2-aminoacetamido)-2-(hydroxymethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-3-(2-aminoacetamido)-2-(isobutoxymethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-2-(propoxymethyl)-3-ureidobenzamide; (R)-N1-(2-(2-hydroxyethoxy)ethyl)-N3-(1-(naphthalen-1-yl)ethyl)isophthalamide; (R)-N2-(4-aminobutyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-N2-(2-aminoethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-N2-(2-(2-hydroxyethoxy)ethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6- dicarboxamide; 5-((S)-2,3-diaminopropanamido)-2-fluoro-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(4-aminobutanamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-1H-benzo[d]imidazole-5-carboxamide; N-((1H-indol-5-yl)methyl)-5-(2-aminoacetamido)-2-methylbenzamide; 5-(2-aminoacetamido)-N-(imidazo[1,5-a]pyridin-1-ylmethyl)-2-methylbenzamide; 5-acetamido-N-(benzo[d]thiazol-2-ylmethyl)-2-methylbenzamide; 5-(2-aminoacetamido)-N-(benzo[d]thiazol-2-ylmethyl)-2-methylbenzamide; 5-amino-N-(benzo[d]thiazol-2-ylmethyl)-2-methylbenzamide; (S)-N-(benzo[d]thiazol-2-ylmethyl)-5-(2,3-diaminopropanamido)-2-methylbenzamide; 5-((S)-2-amino-3-(dimethylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((S)-3-acetamido-2-aminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 5-((S)-2-amino-3-benzamidopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 5-((S)-3-amino-2-(dimethylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 5-((S)-2-acetamido-3-aminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 5-((S)-3-amino-2-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-2- carboxamide; (S)-1,4-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-l)ethyl)carbamoyl)phenyl) piperazine-2-carboxamide; 5-((S)-3-amino-2-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(quinolin-4-yl) ethyl)benzamide; 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(quinolin-5-yl) ethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-N-(indolizin-2-ylmethyl)-2-methylbenzamide; 5-((S)-2,3-diaminopropanamido)-2-(ethoxymethyl)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 5-((S)-2,3-diaminopropanamido)-2-(hydroxymethyl)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 5-((S)-2,3-diaminopropanamido)-2-(isopropoxymethyl)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-3-ylamino)benzamide; (R)-2-methyl-5-((5-methylthiophen-2-yl)amino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrazin-2-ylamino)benzamide; (R)-5-((5-amino-4-methylthiophen-2-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-5-(3,3-dimethylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3,3-dimethylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(4-fluorophenyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(4-fluorophenyl)thioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-allylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-allylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(4-aminophenyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(2-aminoethyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(2-aminoethyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-oxopiperidin-1-yl)benzamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)nicotinamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-oxopyridin-1(2H)-yl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-2-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrimidin-2-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(thiophen-2-ylamino)benzamide;; (R)-5-((5-aminothiophen-2-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-3-(4-(3-(trifluoromethyl)phenyl)piperazine-1-carbonyl) benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-3-(piperazine-1-carbonyl)benzamide; (R)-3-(4-glycylpiperazine-1-carbonyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-3-(4-propylpiperazine-1-carbonyl)benzamide; 2-amino-N-(3-(1-((R)-1-(naphthalen-1-yl)ethyl)-3-oxopiperidin-4-yl)phenyl)acetamidep; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2-carboxamide; 1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2- carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(methylsulfonyl) azepane-2-carboxamide; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2- carboxamide; (S)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2- carboxamide; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2- carboxamide; (R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azepane-2- carboxamide; 5-((azepan-2-ylmethyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-5-(((1-methylazepan-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 2-methyl-5-(((1-(methylsulfonyl)azepan-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((((S)-azepan-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; 5-((((R)-azepan-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; 5-((S)-2,3-diaminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(but-2-yn-1-yloxy)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; N-(2-(1H-indol-3-yl)ethyl)-5-amino-2-methylbenzamide; 5-acetamido-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-2-methylbenzamide; (R)-5-(2-aminoacetamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2,3-diaminopropanamido)-2-fluoro-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; (R)-5-(but-2-yn-1-ylamino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(di(but-2-yn-1-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-aminopropanamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(thiazol-2-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrimidin-2-ylamino)benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)-5-ureidobenzamide; (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-5-(2-aminoacetamido)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-2-methyl-5-(3-(methylsulfonyl)ureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-3-ylamino)benzamide; (R)-5-(di(pyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-amino-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide; N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methyl-5-ureidobenzamide; 5-(2-aminoacetamido)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide; (S)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(2,3-diaminopropanamido)-2- methylbenzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(propylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-2-ylamino)benzamide; (R)-5-(di(pyridin-2-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-aminopropanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(4-aminobutanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-guanidino-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-oxoimidazolidin-1-yl)benzamide; (R)-2-methyl-5-((2-(methylamino)ethyl)amino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-l)ethyl)carbamoyl)phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-1-isopropyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1- (methylsulfonyl)pyrrolidine-2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2- (methylamino)ethyl)pyrrolidine-2-carboxamide; (S)-1-acetyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl)pyrrolidine-2-carboxamide; 2-methyl-5-((((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-5-(methyl(((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-((dimethylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((2-(dimethylamino)ethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((3-(methylamino)propyl)amino)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-amino-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((pyrrolidin-3-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-5-(((1-methylpyrrolidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1 yl) ethyl)benzamide 2,2,2-trifluoroacetate; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-3- carboxamide 2,2,2-trifluoroacetate; 1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-3- carboxamide 2,2,2-trifluoroacetate; tert-butyl ((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-1- oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-3-carboxamide 2,2,2-trifluoroacetate; (R)-1-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-3- carboxamide 2,2,2-trifluoroacetate; (R)-5-((azetidin-3-ylmethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-5-((2-(methyl(((R)-pyrrolidin-2-yl)methyl)amino)ethyl)amino)-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-(dimethylamino)-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-5-((2-(methyl(2-(methylamino)ethyl)amino)ethyl)amino)-N-(1-(naphthalen- 1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-aminoethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((S)-3-((S)-2-oxopyrrolidin-3-yl)-2-(2,2,2- trifluoroacetamido)propanamido)benzamide; 5-((S)-2-(dimethylamino)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; tert-butyl(R)-2-(((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-l)ethyl)carbamoyl)phenyl) amino)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)piperidine-1- carboxylate; tert-butyl((S)-1-((1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl)carbamoyl)-3-azabicyclo[3.1.0]hexan-3-yl)-3,3-dimethyl-1-oxobutan-2- yl)carbamate; (1R,2S,5S)-3-((R)-2-amino-3,3-dimethylbutanoyl)-6,6-dimethyl-N-(4-methyl-3-(((R)-1- (naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3-azabicyclo[3.1.0]hexane-2-carboxamide 2,2,2-trifluoroacetate; (R)-3-(but-2-yn-1-yloxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-3-(2-(2-methoxyethoxy)ethoxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide 5-((S)-2-aminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; tert-butyl ((R)-4-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-4- oxobutan-2-yl)carbamate; methyl (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoate; (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoic acid; 5-((R)-3-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-N1-(2-(2-hydroxyethoxy)ethyl)-N3-(1-(naphthalen-1-yl) ethyl) isophthalamide; methyl (R,E)-4-(3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzamido)but-2- enoate; (R)-5-acetamido-N1-(1-(naphthalen-1-yl)ethyl)-N3-propylisophthalamide; (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)isophthalamide; (R)-5-(3-allylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide ; (R)-5-(3-(4-fluorophenyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(4-fluorophenyl)thioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-3-acetamido-2-aminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; N,N'-((S)-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-3- oxopropane-1,2-diyl)diacetamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide2,2,2- trifluoroacetate; (R)-4-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide2,2,2- trifluoroacetate (R)-5-(3,3-dimethylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(3-methylureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2,3-bis(dimethylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); 5-((S)-2,3-bis(isopropylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); (R)-5-(3-(2-aminoethyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-(methylthio)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4yl) methylsulfonamido) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4-yl) cyclopropanesulfonamido) benzamide; (R)-N-(4-(ethylamino)-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate; (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-1- carboxamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-1- carboxamide; (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)thiophene-2-carboxamide; (R)-5-(2-(4-(4-fluorophenyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-2-methyl-5-(2-(4-methyl-1,4-diazepan-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl) methyl) amino) benzamide dihydrochloride; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2- 1)methyl)amino)benzamide; (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4-diazepane- 1-carboxamide; (R)-5-(2-(4-(2-hydroxyethyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-4-(2-hydroxyethyl)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) piperazine-1-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-2-carboxamide; 5-((S)-2-amino-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 2-methyl-5-(((2-methylazetidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; (S)-2-(hydroxymethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)pyrrolidine-1-carboxamide; 5-((azetidin-2-ylmethyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis (2,2,2-trifluoroacetate); 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl)amino)benzamide; (R)-2-methyl-5-(((1-methylpiperidin-4-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide; 5-(3-((1r,4R)-4-hydroxycyclohexyl)ureido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((S)-2-(dimethylamino)-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(3-(piperidin-4-ylmethyl)ureido)benzamide; (R)-2-methyl-5-(((3-methyloxetan-3-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl) benzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide methanesulfonate; tert-butyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino) methyl)pyrrolidine-1-carboxylate; ethyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) amino) methyl) pyrrolidine-1-carboxylate; 5-((R)-2-amino-3-((R)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl) ethyl)benzamide; (1R,2S,5S)-3-((S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl)-6,6-dimethyl-N-(4- methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3-azabicyclo[3.1.0]hexane-2- carboxamide; tert-butyl (1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1 yl)ethyl) carbamoyl)p henyl)carbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate; (1R,2S,5S)-6,6-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl)-3-azabicyclo[3.1.0]hexane-2-carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hemimalonate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide benzenesulfonate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide ethanesulfonate; (R)-5-acetamido-2-methyl-N-(1-phenylethyl)benzamide; 5-((S)-2-amino-3,3-dimethylbutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 1-acetyl-N-((R)-1-(naphthalen-2-yl)ethyl)pyrrolidine-2-carboxamide; 5-amino-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2-methylbenzamide; (R)-2-isopropoxy-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)-2-propoxybenzamide; 5-amino-N-(imidazo[1,2-a]pyridin-2-ylmethyl)-2-methylbenzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate; (R)-N1-(2-aminoethyl)-N3-(1-(naphthalen-1-yl)ethyl)isophthalamide; (R)-5-amino-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-chloro-5-((R)-2,3-diaminopropanamido)-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)tetrahydro-2H-pyran-4- carboxamide; (R)-5-(cyclohexanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((1-methylethyl)sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-(dimethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-4- carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-2- carboxamide 2,2,2-trifluoroacetate; (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl)methyl) amino) benzamide 2,2,2-trifluoroacetate; 5-((R)-2,3-diaminopropanamido)-2-(methylamino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; (R)-5-acetamido-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperazin-2-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperidin-3-ylmethyl)amino)benzamide bis (2,2,2-trifluoroacetate); 2-methyl-5-(methyl(((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((S)-1-(naphthalen-1- yl) ethyl)benzamide; 5-(((1,4-dimethylpiperazin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-5-(methyl((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-3- carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate; 1,4-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 2-carboxamide bis(2,2,2-trifluoroacetate); 1,4-diacetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 2-carboxamide; 1,4-bis(cyclopropylsulfonyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)piperazine-2-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4-bis (methylsulfonyl) piperazine-2-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-4-(methylsulfonyl) piperazine-2-carboxamide 2,2,2-trifluoroacetate; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl)methyl) amino) benzamide 2,2,2-trifluoroacetate; 4-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 2-carboxamide bis(2,2,2-trifluoroacetate); 2-methyl-5-((((S)-1-(methylsulfonyl)pyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-
1-yl)ethyl)benzamide;
5-((((S)-1-(cyclopropylsulfonyl)pyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1- (naphthalen- 1 -yl)ethyl)benzamide;
(S)-1-acetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-
2-carboxamide;
(S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)- 1 -(methylsulfonyl) pyrrolidine-2-carboxamide;
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((l-(((S)-pyrrolidin-2-yl)methyl)piperidin-4- yl)amino)benzamide bis(2,2,2-trifluoroacetate);
4-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-2- carboxamide bis(2,2,2-trifluoroacetate);
(S)-1-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate;
(S)-1-ethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine- 2-carboxamide 2,2,2-trifluoroacetate;
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((l-(((R)-pyrrolidin-2-yl)methyl)piperidin-4- yl)amino)benzamide bis(2,2,2-trifluoroacetate);
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl)methyl) amino) benzamide;
5-((R)-3-amino-2-((((S)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N-((R)-1-
(naphthalen- 1 -yl)ethyl)benzamide tris(2,2,2-trifluoroacetate);
5-((R)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N-((R)-1-
(naphthalen- 1 -yl)ethyl)benzamide tris(2,2,2-trifluoroacetate);
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl)methyl)amino) benzamide dihydrochloride;
2-methyl-5-((((S)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethy l)benzamide ;
(R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate;
2-methyl-5-(((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethy l)benzamide ;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide; 2-methyl-5-((((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethy l)benzamide ;
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-piperidin-2-yl)methyl)amino) benzamide 2,2,2-trifluoroacetate;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 2,2,2-trifluoroacetate;
2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethy l)benzamide ;
2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-piperidin-2-yl)methyl)amino) benzamide 2,2,2-trifluoroacetate
(R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine- 2-carboxamide 2,2,2-trifluoroacetate;
2-methyl-5-(((4-methylpiperazin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate;
(S)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine- 2-carboxamide; tert-butyl(R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) carbamoyl)piperidine- 1 -carboxylate;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide;
2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethy l)benzamide ;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hydrochloride; ethyl(R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) carbamoyl) piperidine- 1 -carboxylate;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide phosphate;
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2-(methylamino) ethyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate);
(R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(((R)-pyrrolidin- 2-yl) methyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate);
(S)-1-(2-hydroxyethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2,2,2- trifluoroacetyl)piperidine-2-carboxamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 4-methylbenzenesulfonate; (R)-5-hydroxy-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; tert-butyl ((R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-2- oxo-1-phenylethyl)carbamate (R)-5-(2-amino-2-methylpropanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide N-(2-(1H-indol-3-yl)ethyl)-5-acetamido-2-methylbenzamide; N-(2-(1H-indol-3-yl)ethyl)-5-(2-aminoacetamido)-2-methylbenzamide; (R)-N2-(2-(2-hydroxyethoxy)ethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6- dicarboxamide; (R)-N2-(4-aminobutyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-N2-(2-aminoethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-5-((N,N-dimethylsulfamoyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide; (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide; (R)-2-methyl-5-(morpholine-4-sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((4-methylpiperazine)-1-sulfonamido)-N-(1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidine-1-sulfonamido)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((N-phenylsulfamoyl)amino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperazine-1-sulfonamido)benzamide 2,2,2- trifluoroacetate; 2-methyl-5-(methylsulfonoamidimidamido)-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; 5-(((N-acetylacetamido)(methyl)(oxo)-l6-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl) ethyl)benzamide; ethyl (methyl((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)(oxo)- 16-sulfaneylidene)carbamate; 5-(((dimethylamino)(methyl)(oxo)-l6-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide; 5-((4-cyanophenyl)sulfonoamidimidamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-(2-(dimethylamino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((4-fluorobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((4-cyanobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((4-(trifluoromethyl) benzyl)amino)benzamide; (R)-5-((6-aminopyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(((5-methylthiophen-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-3-ylmethyl)amino)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(((1-methyl-1H-pyrrol-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-((6-hydroxypyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-((cyclopropylmethyl)amino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-(2-(isoindolin-2-yl)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(((1H-imidazol-5-yl)methyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-6-amino-3-methyl-N-(1-(naphthalen-1-yl)ethyl)picolinamide; (R)-3-methyl-N-(1-(naphthalen-1-yl)ethyl)-6-(piperidin-4-ylamino)picolinamide 2,2,2- trifluoroacetate; 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((((R)-pyrrolidin-2-yl)methyl) amino) picolinamide 2,2,2-trifluoroacetate; 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((R)-pyrrolidine-2-carboxamido) picolinamide 2,2,2-trifluoroacetate; (R)-6-amino-5-methyl-N-(1-(naphthalen-1-yl)ethyl)picolinamide; 5-(((S)-2,3-diaminopropyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-3-amino-2-(dimethylamino)propyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-2-amino-3-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine- 2-carboxamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine- 2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine- 2-carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrazine-2-carboxamide; (R)-5-(cyclopropanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2-amino-3-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl) ethyl)benzamide 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; 5-((S)-3-amino-2-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinolin-2-ylmethyl)benzamide bis(2,2,2- trifluoroacetate); 5-((S)-3-amino-2-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl) benzamide 2,2,2-trifluoroacetate; 5-((S)-2,4-diaminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis (2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidin-4-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((tetrahydro-2H-pyran-4-yl) amino) benzamide; (R)-5-((9H-purin-6-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridine-3-sulfonamido)benzamide; 5-((S)-2,6-diaminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-((S)-2-amino-3-(pyridine-3-sulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen- 1-yl)ethyl)benzamide; 5-((S)-2-amino-3-((3,5-difluorophenyl)sulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((1-(methylsulfonyl)piperidin-4-yl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl)amino)benzamide bis (2,2,2-trifluoroacetate); N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)- 3-oxopropyl)piperazine-2-carboxamide tris(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-4-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); N-(4-methyl-3-((quinolin-4-ylmethyl)carbamoyl)phenyl)piperazine-2-carboxamide bis (2,2,2-trifluoroacetate); 5-((S)-2-amino-3-(1H-imidazol-4-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2-amino-3-(1H-indol-3-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2-amino-3-((N,N-dimethylsulfamoyl)amino)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide 2,2,2-trifluoroacetate; N-(4-((isopropylamino)methyl)-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-2-carboxamide tris(2,2,2-trifluoroacetate); (R)-5-amino-2-((isopropylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl) benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperazin-1-yl)acetamido)benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperidin-1-yl)acetamido)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(2-morpholinoacetamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyrrolidin-1-yl)acetamido)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(methyl(1-methylpiperidin-4-yl)amino)-N-(1-(naphthalen-1-yl) ethyl) benzamide; (R)-5-amino-2-((dibutylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2- trifluoroacetate); (R)-5-amino-2-(aminomethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2- trifluoroacetate); N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)- 3-oxopropyl)piperidine-4-carboxamide bis(2,2,2-trifluoroacetate); (S)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (S)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; (R)-5-(2-aminoacetamido)-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-5-((((R)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (R)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide; (R)-5-(1-aminocyclopropane-1-carboxamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; 5-((S)-2-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; 5-((R)-2-amino-2-phenylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide; (R)-N-((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-1- oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)piperidine-2-carboxamide 2,2,2- trifluoroacetate; 2-methyl-5-((S)-2-(methylsulfonamido)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide 5-((R)-2-amino-2-cyclohexylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide. or pharmaceutically acceptable salts of any of the compounds above. Following is a list of abbreviations used in the description of the preparation of the compounds of the present invention: µg: microgram 1H NMR : Proton nuclear magnetic resonance bs: broad singlet CDC13: Deuterated chloroform CHC13: Chloroform d: doublet DAMP: damage‐associated molecular pattern; DBU: 1,8-Diazabicyclo(5.4.0)undec-7-ene DCM: Dichloromethane dd: doublet of doublet DMAC: N,N-(Dimethylacetamide) DMAP: 4-(Dimethylamino) pyridine DMF: N,N-Dimethyl formamide DMSO: Dimethyl sulfoxide dt: doublet of triplet EDTA: Ethylenediaminetertraacetic acid EtOAc: Ethyl acetate EtOH: Ethanol HCl(g): Hydrogen chloride (gas) IL1β: Interleukin 1 beta K2CO3: Potassium carbonate m: multiplet MeOH: Methanol mmol: millimoles MS: Mass spectrum N2: Nitrogen Na2CO3: Sodium carbonate ng: nanogram NIS: N-iodosuccinimide PAMP: pathogen‐associated molecular pattern; PMA = Phorbol 12-myristate 13-acetate POCI3: Phosphorylchloride RM: reaction mixture r.t, RT: room temperature s: singlet t: Triplet td: triplet of doublet THF: Tetrahydrofuran TLC: Thin layer chromatography TLR: Toll‐like receptor. TNF α: Tumor necrosis factor alpha General Process for Preparation The novel compounds of the present invention can be prepared using the reactions and techniques described below, together with conventional techniques known to those skilled in the art of organic synthesis, or variations thereon as appreciated by those skilled in the art. The reactions can be performed in solvents appropriate to the reagents and materials employed and suitable for the transformations being affected. Preferred methods include, but not limited to those described below, where all symbols are as defined earlier unless and otherwise defined below. The compounds of the general formula (I) can be prepared as described in schemes below along with suitable modifications/variations which are well within the scope of a person skilled in the art. Scheme 1
Figure imgf000032_0001
wherein each of A, B, V, W, X, Y, Z, R1, R2, R3, R4, R5 and R6 are as defined earlier. Compounds 1 and 2 are commercially available or can be prepared by variety of methods familiar to those skilled in art. Compounds 1 and 2 on treatment with suitable coupling reagents like HATU, HBTU, etc under suitable conditions and appropriate solvents provided compound (3) (ref. Synthesis 2003, 15, 2321-24). Compound (3) on hydrogenation under suitable conditions in presence of catalyst like palladium on charcoal and appropriate solvent provided compound (4). Compound (4) on treatment with various substituted side chain under suitable conditions in presence of catalyst or any other suitable reagent and appropriate solvent resulted in compound of formula (I). Specific reaction conditions, solvents and other parameters necessary for carrying out the process steps as described above are well within the capabilities of a person skilled in the art. The invention is further illustrated by the following non-limiting examples which describe the preferred way of carrying out the present invention. These are provided without limiting the scope of the present invention in any way. 1H NMR spectral data given in the examples (vide infra) are recorded using a 400 MHz spectrometer (Bruker AVANCE-400) and reported in δ scale. Until and otherwise mentioned the solvent used for NMR is CDCl3 using TMS as the internal standard. Example-1 Preparation of (R)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide Intermediate-1: Preparation of (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5- nitrobenzamide
Figure imgf000033_0001
To a solution of 2-methyl-5-nitrobenzoic acid (0.6 g, 3.31 mmol) in DCM (20 ml), (R)-1-(naphthalen-1-yl)ethan-1-amine (0.567 g, 3.31 mmol), EDC (0.794 g, 4.14 mmol), HOBT (0.634 g, 4.14 mmol) and DIPEA (2.256 ml, 12.92 mmol) were added one by one and reaction mixture was stirred under N2 atm. at 25 °C for 17 h. Completion of reaction checked by TLC. The reaction was concentrated in vacuo and diluted with water, solid was filtered and washed it with water. Crude product was purified by column chromatography (ethyl acetate : n-hexane) (gradient) to yield, (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5- nitrobenzamide (1.06 g, 3.17 mmol, 96 % yield). 1H NMR (400 MHz, DMSO-d6): δ = 8.24 (d, J = 8.4 Hz, 1H), 8.16 – 8.12 (m ,2H), 7.93 (d, J = 8.0 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.64 – 7.48 (m, 4H), 7.38 (d, J = 8.4 Hz, 1H), 6.18 – 6.09 (m, 2H), 2.55 (s, 3H), 1.86 (d, J = 6.4 Hz, 3H); MS (TOF): m/z (%) = 335.1386 (100%) (M+H)+. Intermediate-2: Preparation of (R)-5-amino-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000033_0002
To a solution of (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-nitrobenzamide (0.98 g, 2.93 mmol) in Methanol (40 ml) and Ethyl acetate (40 ml) was added Pd/C (0.312 g, 2.93 mmol) and stirred under H2 atm. at 25 °C for 17 h. Completion of reaction checked by TLC. The reaction was carefully filtered through celite pad and concentrated in vacuo. Crude product was purified by preparative HPLC to yield, (R)-5-amino-2-methyl-N-(1- (naphthalen-1-yl)ethyl)benzamide (0.823 g, 2.68 mmol, 92 % yield). 1H NMR (400 MHz, DMSO-d6): δ = 8.26 (d, J = 8.4 Hz, 1H), 7.91 (d, J = 7.6 Hz, 1H), 7.82 (d, J = 8.4 Hz, 1H), 7.61 – 7.54 (m, 3H), 7.52 – 7.46 (m, 1H), 6.97 (d, J = 7.6 Hz, 1H), 6.63 – 6.59 (m, 2H), 6.17 – 6.10 (m, 1H), 5.97 (d, J = 8.4 Hz, 1H), 2.32 (s, 3H), 1.81 (d, J = 6.4 Hz, 3H); MS (TOF): m/z (%) = 305.1639 (100%) (M+H)+. Example 1 Preparation of (R)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000034_0001
To a solution of Boc-glycine (0.058 g, 0.329 mmol) in DCM (5.0 ml) was added (R)- 5-amino-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide (0.1 g, 0.329 mmol), 1-(3- Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.079 g, 0.411 mmol), HOBT (0.063 g, 0.411 mmol) and DIPEA (0.224 ml, 1.285 mmol). Reaction mixture was stirred under nitrogen atmosphere at 25 °C for 17 h. Completion of reaction checked by TLC. The reaction was concentrated in vacuo and diluted with water, solid was filtered and washed it with water. Crude product was directly used in next step without further purification. To solution of tert-butyl(R)-(2-((4-methyl-3-((1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)amino)-2-oxoethyl)carbamate (0.130 g, 0.282 mmol) in DCM (15.0 ml) added TFA (0.217 ml, 2.82 mmol) at 10°C.The reaction was warmed to r.t. & stirred further for 3h. The reaction mixture was concentrated in vacuo to give product. The crude product was purified by prep. HPLC to yield, (R)-5-(2-aminoacetamido)-2-methyl-N- (1-(naphthalen-1-yl)ethyl)benzamide (35 mg, 0.096 mmol, 34 % yield). 1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 7.6 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.61 (m, 2H), 7.60 – 7.49 (m, 4H), 7.15 (d, J = 8.0 Hz, 1H), 5.94 - 5.90 (m, 1H), 3.26 (s, 2H), 2.22 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 362.1849 (100%) (M+H)+, 360.1736 (100%) (M+H)+. Using appropriate starting materials and suitable modifications of the process described in example 1, including suitable addition and/or deletion of steps as may be necessary which are well within the scope of a person skilled in the art, the following compounds were prepared in an analogues manner. Example-2 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide
Figure imgf000034_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.86 (d, J = 8.0 Hz, 1H), 8.54 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.40 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.29 (d, J = 2.0 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 5.95 – 5.88 (m, 1H), 5.81 (s, 2H), 2.18 (s, 3H), 1.61 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 348.1723(100%) (M+H)+. Example-3 5-((S)-2,3-diaminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000035_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.65 – 7.50 (m, 6H), 7.17 (d, J = 8.4 Hz, 1H), 3.62 – 3.59 (m, 1H), 3.12 – 3.07 (m, 1H), 2.84 – 2.79 (m, 1H), 2.32 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 391.2129(100%) (M+H)+, 389.2018 (30%) (M+H)+. Example-4 (R)-5-(but-2-yn-1-yloxy)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000035_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.88 (d, J=8.0Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.96 (d, J=7.2Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.63 - 7.50 (m, 4H), 7.15 (d, J=8.4Hz, 1H), 6.95 - 6.90 (m, 2H), 5.94 - 5.86 (m, 1H), 4.73 (d, J=2.0Hz, 2H), 2.21 (s, 3H), 1.82 (t, J=2.0Hz, 3H), 1.58 (d, J=7.2Hz, 3H); MS (ESI): m/z (%) = 358.178 (100%) (M+H)+. Example-5 N-(2-(1H-indol-3-yl)ethyl)-5-amino-2-methylbenzamide
Figure imgf000035_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.81 (s, 1H), 8.18 (t, J=6.0Hz, 1H), 7.57 (d, J=7.6Hz, 1H), 7.34 (d, J=8.0Hz, 1H), 7.19 (d, J=2.4Hz, 1H), 7.09 - 6.91 (m, 2H), 6.85 (d, J=8.0Hz, 1H), 6.54 - 6.49 (m, 2H), 4.95 (s, 2H), 3.50 - 3.45 (m, 2H), 2.91 (t, J=7.2Hz, 2H), 2.12 (s, 3H); MS (ESI): m/z (%) = 294.159 (100%) (M+H)+. Example-6 5-acetamido-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-2-methylbenzamide
Figure imgf000036_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.99 (s, 1H), 9.74 (s, 1H), 7.65 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.20 (d, J = 8.4 Hz, 1H), 7.00 (s, 1H), 2.98 (t, J=7.2 Hz, 4H), 2.85 (t, J=7.2 Hz, 4H), 2.50 (s, 3H), 2.00 (m, 7H); MS (ESI): m/z (%) = 349.18 (100%) (M+H)+. Example-7 (R)-5-(2-aminoacetamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000036_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.98 (d, J = 7.6 Hz, 1H), 8.22 (d, J = 8.2 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.81 (dd, J1 = 2.8 Hz, J2 = 6.4 Hz, 1H), 7.92 – 7.75 (m, 1H), 7.63 – 7.49 (m, 4H), 7.23 (t, J = 9.2 Hz, 1H), 5.93 – 5.89 (m, 1H), 3.28 (s, 2H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 366.1867 (100%) (M+H)+. Example-8 5-((S)-2,3-diaminopropanamido)-2-fluoro-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000036_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.98 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 8.4 Hz, 1H), 8.01 – 7.93 (m, 1H), 7.85 – 7.83 (m, 2H), 7.79 – 7.74 (m, 1H), 7.63 – 7.49 (m, 4H), 7.25 – 7.20 (m, 1H), 4.37 – 4.29 (m, 1H), 3.35 – 3.28 (m, 2H), 3.10 – 3.07 (m, 1H), 2.86 – 2.80 (m, 1H), 2.70 – 2.65 (m, 1H), 2.37 – 2.30 (m, 1H), 1.58 (d, J = 7.2 Hz, 3H), 1.30 – 1.25 (m, 2H); MS (TOF): m/z (%) = 395.2260 (60%) (M+H)+, 427.1906 (100%) (M+Na)+. Example-9 5-((R)-2-amino-2-cyclohexylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000037_0001
MS (TOF): m/z (%) = 444.2712 (100%) (M+H)+, 442.2501 (100%) (M-H). Example-10 (R)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide
Figure imgf000037_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.92 (d, J = 7.6 Hz, 1H), 8.67 (s, 1H), 8.22 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 6H), 7.15 (t, J = 9.2 Hz, 1H), 5.92 – 5.87 (m, 1H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 352.1416 (100%) (M+H)+; IR (KBr): v = 3414, 3302, 1660, 1616, 1541, 1496, 1213, 775 cm-1. Example-11 (R)-5-(but-2-yn-1-ylamino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000037_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.79 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.96 (d, J = 8.0 Hz, 1H), 6.61 – 6.56 (m, 2H), 5.92 – 5.83 (m, 2H), 3.79 (s, 2H), 2.13 (s, 3H), 1.73 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 357.2419 (100%) (M+H)+; IR (KBr): v = 3277, 1633, 1608, 1504, 1446, 1315, 1240, 798, 775 cm-1. Example-12 (R)-5-(di(but-2-yn-1-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000038_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.83 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.65 – 7.49 (m, 4H), 7.07 (d, J = 8.0 Hz, 1H), 6.88 (d, J = 9.2 Hz, 2H), 5.92 – 5.89 (m, 1H), 4.04 (s, 4H), 2.19 (s, 3H), 1.74 (s, 6H), 1.59 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 409.2798 (100%) (M+H)+; IR (KBr): v = 3277, 1629, 1606, 1527, 1502, 1330, 1261, 1172, 798, 777 cm-1. Example-13 2-methyl-5-((S)-2-(methylsulfonamido)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000038_0002
IR (KBr): = 3257, 1670, 1535, 1311, 1149, 979, 800, 777 cm-1 ; MS (TOF): m/z (%) = 537.2180 (40%) (M+H)+, 535.2018 (100%) (M-H). Example-14 (R)-5-(3-aminopropanamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000038_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.97 (d, J = 7.2 Hz, 1H), 8.22 (d, J = 8.8 Hz, 1H), 7.97 (d, J = 9.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.75 – 7.70 (m, 2H), 7.63 – 7.49 (m, 5H), 7.24 (t, J = 9.2 Hz, 1H), 5.93 – 5.87 (m, 1H), 2.84 (t, J = 6.8 Hz, 2H), 2.39 (t, J = 6.8 Hz, 2H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 380.1926 (100%) (M+H)+ , 378.1673 (70%) (M-1)-; IR (CHCl3): v = 3452, 2371, 3049, 1641, 1525, 1490, 1409, 1336, 1219, 1014, 800 cm-1. Example-15 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(thiazol-2-ylamino)benzamide
Figure imgf000039_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.23 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 7.2 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.65 – 7.50 (m6H), 7.25 (d, J = 3.6 Hz, 1H), 7.16 (d, J = 8.4 Hz, 1H), 6.90 (d, J = 3.6 Hz, 1H), 5.96 – 5.89 (m, 1H), 2.22 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 388.1455 (100%) (M+H)+, 386.1340 (100%) (M-1)-; IR (KBr): v = 3269, 3055, 1631, 1604, 1523, 1498, 1440, 1342, 1199, 1139, 777 cm-1. Example-16 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrimidin-2-ylamino)benzamide
Figure imgf000039_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.62 (s, 1H), 8.89 (d, J = 8.0 Hz, 1H), 8.46 (d, J = 4.8 Hz, 2H), 8.27 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.76 – 7.68 (m, 2H), 7.67 – 7.50 (m, 4H), 7.13 (d, J = 8.4 Hz, 1H), 6.83 (t, J = 4.8 Hz, 1H), 5.96 – 5.89 (m, 1H), 2.21 (s, 3H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 383.1815 (100%) (M+H)+, 381.1588 (100%) (M-1)-; IR (KBr): v = 3265, 3041, 1637, 1581, 1527, 1446, 1415, 1236, 1178, 796, 775 cm-1. Example-17 (R)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)-5-ureidobenzamide
Figure imgf000039_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.45 (d, J = 8.0 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 9.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 7.40 – 7.36 (m, 2H), 6.81 – 6.79 (m, 1H), 5.95 – 5.87 (m, 1H), 5.69 (s, 2H), 2.95 (br s, 4H), 1.66 – 1.57 (m, 7H); MS (TOF): m/z (%) = 403.2096 (100%) (M+H)+, 401.2010 (70%) (M-1)-; IR (KBr): v = 3279, 3292, 3197, 2970, 2868, 1647, 1631, 1502, 1359, 1240 cm-1. Example-18 (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide
Figure imgf000040_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.74 (s, 1H), 9.2 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.64 (d, J = 6.8 Hz, 1H), 7.60 – 7.47 (m, 5H), 6.75 (d, J = 8.8 Hz, 1H), 5.93 – 5.89 (m, 1H), 3.01 (s, 4H), 1.98 (s, 3H), 1.69 – 1.64 (m, 4H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 402.2148 (100%) (M+H)+, 400.2062 (100%) (M-1)-; IR (KBr): v = 3267, 3049, 2970, 2872, 1637, 1533, 1504, 1483, 1408, 1313 cm-1. Example-19 (R)-5-(2-aminoacetamido)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl) benzamide
Figure imgf000040_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.17 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 9.2 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.64 (d, J = 6.8 Hz, 1H), 7.59 – 7.49 (m, 6H), 6.76 (d, J = 8.2 Hz, 1H), 5.93 – 5.89 (m, 1H), 3.24 (s, 2H), 3.02 (br s, 4H), 1.76 – 1.62 (m, 4H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 417.2260 (100%) (M+H)+, 415.2114 (100%) (M-1)-; IR (KBr): v = 3273, 2960, 2860, 1618, 1544, 1508, 1498, 1411, 1234, 800 cm-1. Example-20 (R)-2-methyl-5-(3-(methylsulfonyl)ureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000040_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.84 (d, J = 8.0 Hz, 1H), 8.53 (br s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.64 – 7.41 (m, 6H), 7.03 (d, J = 8.4 Hz, 1H), 5.94 – 5.89 (m, 1H), 2.95 (s, 3H), 2.16 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 426.1475 (100%) (M+H)+, 424.1299 (100%) (M-1)-; IR (KBr): v = 3238, 3051, 2931, 1712, 1598, 1537, 1448, 1323, 1236, 1143, 968 cm-1. Example-21 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-3-ylamino)benzamide
Figure imgf000041_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.91 (d, J = 8.0 Hz, 1H), 8.39 – 8.33 (m, 2H), 8.24 (d, J = 9.2 Hz, 1H), 8.03 (d, J = 4.0 Hz, 1H), 7.95 (d, J = 9.2 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.44 (m, 5H), 7.25 – 7.22 (m, 1H), 7.14 (d, J = 8.4 Hz, 1H), 7.08 – 7.03 (m, 2H), 5.95 – 5.87 (m, 1H), 2.22 (s, 3H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 382.1929 (100%) (M+H)+, 380.1751 (100%) (M-1)-; IR (KBr): v = 3273, 2980, 1647, 1573, 1541, 1498, 1483, 1431, 1327, 800, 777 cm-1. Example-22 (R)-5-(di(pyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000041_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.90 (d, J = 8.0 Hz, 1H), 8.28 – 8.26 (m, 4H), 8.16 – 8.14 (m, 1H), 7.95 – 7.93 (m, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.56 – 7.49 (m, 3H), 7.46 – 7.42 (m, 3H), 7.36 – 7.33 (m, 2H), 7.24 (d, J = 8.0 Hz, 1H), 7.07 (dd, J1 = 2.4 Hz, J2 = 8.0 Hz, 1H), 7.02 (d, J = 2.4 Hz, 1H), 5.89 – 5.81 (m, 1H), 2.27 (s, 3H), 1.38 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 459.2186 (100%) (M+H)+, 457.2010 (100%) (M-1)-; IR (KBr): v = 3244, 3034, 1643, 1571, 1531, 1477, 1427, 1301, 798, 779, 707 cm-1. Example-23 5-amino-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide
Figure imgf000041_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.56 (t, J = 6.4 Hz, 1H), 6.88 – 6.84 (m, 3H), 6.80 (dd, J1 = 1.6 Hz, J2 = 8.0 Hz, 1H), ), 6.56 (d, J = 2.4 Hz, 1H), 5.52 (dd, J1 = 2.4 Hz, J2 = 8.0 Hz, 1H), 5.99 (s, 2H), 4.98 (s, 2H), 4.29 (d, J = 6.0 Hz, 1H), 2.12 (s, 3H); MS (TOF): m/z (%) = 285.1364 (100%) (M+H)+, 283.1199 (80%) (M-1)-; IR (KBr): v = 3225, 3334, 3253, 2897, 1635, 1533, 1500, 1487, 1440, 1303, 1251, 1041, 923 cm-1. Example-24 N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methyl-5-ureidobenzamide
Figure imgf000042_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.68 (s, 1H), 8.53 (s, 1H), 7.35 (s, 2H), 7.08 (d, J = 8.4 Hz, 1H), 6.89 (d, J = 10.8 Hz, 2H), 6.81 (d, J = 7.6 Hz, 1H), 5.99 (s, 2H), 5.82 (s, 2H), 4.32 (d, J = 5.6 Hz, 2H), 2.21 (s, 3H); MS (TOF): m/z (%) = 325.1688 (100%) (M+H)+, 326.1159 (100%) (M-1)-; IR (KBr): v = 3427, 3373, 3236, 1645, 1612, 1514, 1504, 1442, 1255, 1300, 1255, 1188 cm-1. Example-25 5-(2-aminoacetamido)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide
Figure imgf000042_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.72 (t, J = 6.0 Hz, 1H), 7.61 – 7.59 (m, 2H), 7.17 – 7.15 (m, 1H), 6.89 – 6.86 (m, 2H), 6.81 – 6.79 (m, 1H), 6.00 (s, 2H), 4.33 (d, J = 6.4 Hz, 2H), 3.27 (s, 2H), 2.25 (s, 3H); MS (TOF): m/z (%) = 342.1436 (100%) (M+H)+, 340.1311 (100%) (M-1)-; IR (KBr): v = 3250, 3053, 2922, 1697, 1639, 1544, 1489, 1404, 1253, 1043, 925 cm-1. Example-26 (S)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(2,3-diaminopropanamido)-2- methylbenzamide
Figure imgf000042_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.73 (t, J = 6.0 Hz, 1H), 7.63 – 7.59 (m, 2H), 7.17 (d, J = 8.4 Hz, 2H), 6.89 – 6.86 (m, 2H), 6.81 (dd, J1 = 1.6 Hz, J2 = 8.0 Hz, 1H), 6.00 (s, 2H), 4.33 (d, J = 6.0 Hz, 2H), 3.36 – 3.33 (m, 2H), 2.70 – 2.65 (m, 1H), 2.29 (s, 3H); MS (TOF): m/z (%) = 371.1721 (70%) (M+H)+, 369.1604 (100%) (M-1)-. Example-27 (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(propylamino)benzamide
Figure imgf000043_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 7.6 Hz, 1H), 8.22 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.91 (d, J = 2.4 Hz, 1H), 6.67 (dd, J1 = 2.4 Hz, J2 = 8.4 Hz, 1H), 5.92 – 5.88 (m, 1H), 4.38 (br s, 2H), 2.91 – 2.90 (m, 2H), 1.58 (d, J = 6.8 Hz, 3H), 1.50 (q, J = 7.2 Hz, 2H), 0.87 (t, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 348.2039 (100%) (M+H)+; IR (KBr): v = 3282, 2966, 2926, 1629, 1595, 1510, 1305, 1240, 1159 cm-1. Example-28 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-2-ylamino)benzamide
Figure imgf000043_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.56 (br s, 1H), 8.88 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.08 (d, J = 4.8 Hz, 1H), 7.98 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.72 – 7.70 (m, 1H), 7.65 – 7.51 (m, 6H), 7.20 (d, J = 8.4 Hz, 1H), 6.94 (d, J = 8.8 Hz, 1H), 6.83 (d, J = 6.0 Hz, 1H), 5.97 – 5.90 (m, 1H), 2.26 (s, 3H), 1.59 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 382.1906 (100%) (M+H)+; IR (KBr): v = 3041, 2976, 2924, 1678, 1651, 1600, 1537, 1197, 1134, 831 cm-1. Example-29 (R)-5-(di(pyridin-2-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000043_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.93 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 9.2 Hz, 1H), 8.18 (dd, J1 = 3.6 Hz, J2 = 6.4 Hz, 1H), 7.95 (dd, J1 = 3.6 Hz, J2 = 6.4 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.70 – 7.65 (m, 2H), 7.57 – 7.45 (m, 4H), 7.24 (d, J = 8.0 Hz, 1H), 7.07 – 7.01 (m, 4H), ), 6.98 (d, J = 8.4 Hz, 1H), 5.90 – 5.83 (m, 1H), 2.29 (s, 3H), 1.56 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 459.2175 (100%) (M+H)+, 457.2131 (10%) (M-1)-; IR (KBr): v = 3255, 3049, 2924, 2850, 2173, 1639, 1585, 1527, 1465, 1425, 1319, 1273 cm-1. Example-30 (R)-5-(3-aminopropanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000044_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.14 (s, 1H), 8.90 (d, J = 7.6 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.14 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 2.87 (t, J = 6.8 Hz, 2H), 2.44 (t, J = 7.2 Hz, 2H), 2.21 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 376.1988 (100%) (M+H)+, 374.1874 (60%) (M-1)-; IR (KBr): v = 2365, 3049, 2974, 1633, 1612, 1525, 1398, 1338, 1120 cm-1. Example-31 (R)-5-(4-aminobutanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000044_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.07 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.14 (d, J = 8.4 Hz, 1H), 5.96 – 5.89 (m, 1H), 2.63 (t, J = 7.2 Hz, 2H), 2.35 (t, J = 7.2 Hz, 2H), 2.21 (s, 3H), 1.71 (quin, J = 7.2 Hz, 2H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 390.2170 (100%) (M+H)+, 388.2028 (100%) (M-1)-; IR (KBr): v = 3292, 3051, 2972, 1635, 1610, 1541, 1535, 1406, 1312, 1136 cm-1. Example-32 (R)-N-((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-1- oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)piperidine-2-carboxamide 2,2,2- trifluoroacetate
Figure imgf000045_0001
IR (KBr): = 3257, 1666, 1537, 1300, 1199, 1178, 1132, 800, 779 cm-1 ; MS (TOF): m/z (%) = 570.3069 (100%) (M+H)+. Example-33 5-((R)-2-amino-2-phenylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000045_0002
IR (KBr): v = 3255, 3049, 1633, 1597, 1533, 1492, 1313, 798, 777, 493 cm-1 ; MS (TOF): m/z (%) = 438.2244 (100%) (M+H)+, 436.2030 (100%) (M-H). Example-34 (R)-5-guanidino-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000045_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.85 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.2 Hz, 2H), 7.86 (d, J = 8.4 Hz, 2H), 7.63 – 7.50 (m, 4H), 7.24 (d, J = 8.4 Hz, 1H), 7.11 (d, J = 2.0 Hz, 1H), 7.07 (dd, J1 = 2.0 Hz, J2 = 8.4 Hz, 1H), 5.94 – 5.87 (m, 1H), 2.28 (s, 3H), 1.61 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 347.1849 (100%) (M+H)+; IR (KBr): v = 3049, 2976, 1631, 1535, 1402, 1336, 1257, 1120, 800, 777 cm-1. Example-35 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-oxoimidazolidin-1-yl)benzamide
Figure imgf000045_0004
1H NMR (400 MHz, DMSO-d6): δ = 8.88 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.46 (m, 6H), 7.15 (d, J = 8.4 Hz, 1H), 6.94 (s, 1H), 5.95 – 5.88 (m, 1H), 3.83 (t, J = 8.4 Hz, 2H), 3.40 (t, J = 8.4 Hz, 2H), 2.21 (s, 3H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 374.1867 (100%) (M+H)+; IR (KBr): v = 3269, 3120, 1697, 1635, 1606, 1539, 1504, 1483, 1429, 1257 cm-1. Example-36 (R)-2-methyl-5-((2-(methylamino)ethyl)amino)-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000046_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.78 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 7.2 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.93 (d, J = 8.0 Hz, 1H), 6.55 – 6.52 (m, 2H), 5.89 – 5.87 (m, 1H), 5.52 (s, 1H), 3.08 (br s, 2H), 2.69 (t, J = 6.0 Hz, 2H), 2.32 (s, 3H), 2.12 (s, 3H), 1.56 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 362.2184 (100%) (M+H)+; IR (CHCl3): v = 3288, 3007, 1610, 1510, 1450, 1398, 1336, 1255, 1215, 1122, 1010 cm-1. Example-37 (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000046_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.23 (s, 1H), 9.30 (br s, 1H), 8.93 (d, J = 8.0 Hz, 2H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.63 – 7.50 (m, 6H), 7.24 (d, J = 8.4 Hz, 1H), 5.94 (t, J = 7.6 Hz, 1H), 3.27 (br s, 2H), 2.37 – 2.29 (m, 1H), 2.25 (s, 3H), 2.14 – 2.03 (m, 2H), 1.87 – 1.82 (m, 1H), 1.67 (s, 3H), 1.59 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 416.3078 (100%) (M+H)+; IR (KBr): v = 3255, 3051, 2980, 1670, 1597, 1541, 1450, 1371, 1199, 1176, 1130 cm-1. Example-38 (S)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000047_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.15 (s, 1H), 9.80 – 9.9 (m, 1H), 8.93 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 7.6 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.62 – 7.50 (m, 6H), 7.24 (d, J = 8.4 Hz, 1H), 5.94 (quin, J = 7.2 Hz, 1H), 3.24 – 3.21 (m, 1H), 2.80 (d, J = 4.8 Hz, 3H), 2.33 – 2.05 (m, 5H), 2.15 – 2.05 (m, 1H), 1.87 – 1.82 (m, 1H), 1.67 (s, 3H), 1.59 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 430.3264 (100%) (M+H)+; IR (KBr): v = 3251, 3049, 2978, 1670, 1541, 1541, 1496, 1197, 1176, 1126, 798 cm-1. Example-39 (S)-1-isopropyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide
Figure imgf000047_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.77 (s, 1H), 8.90 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.15 (d, J = 8.0 Hz, 1H), 5.93 – 5.90 (m, 1H), 3.20 – 3.18 (m, 1H), 2.81 – 2.78 (m, 1H), 2.58 – 2.56 (m, 1H), 2.20 (s, 3H), 2.03 – 2.00 (m, 1H), 1.75 – 1.65 (m, 3H), 1.59 (d, J = 6.8 Hz, 3H), 1.22 (s, 3H), 0.99 – 0.84 (m, 6H). MW = 457.61; MS (TOF): m/z (%) = 458.3450 (100%) (M+H)+; IR (KBr): v = 3255, 3047, 2970, 2927, 2872, 1645, 1508, 1448, 1402, 1176, 1124 cm-1; Example-40 (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1- (methylsulfonyl)pyrrolidine-2-carboxamide
Figure imgf000047_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.38 (s, 1H), 8.94 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.64 – 7.49 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 5.93 (quin, J = 7.6 Hz, 1H), 3.64 – 3.49 (m, 1H), 3.47 – 3.41 (m, 1H), 3.03 (s, 3H), 2.21 (s, 3H), 1.97 – 1.94 (m, 4H), 1.61 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 494.2922 (100%) (M+H)+; IR (KBr): v = 3338, 2978, 1778, 1651, 1514, 1321, 1145, 1074, 1002 cm-1. Example-41 (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2- (methylamino)ethyl)pyrrolidine-2-carboxamide
Figure imgf000048_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.45 (s, 1H), 8.92 (d, J = 8.4 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.74 – 7.71 (m, 1H), 7.63 – 7.49 (m, 5H), 7.14 (d, J = 8.0 Hz, 1H), 3.29 – 3.25 (m, 1H), 2.80 – 2.65 (m, 2H), 2.58 – 2.55 (m, 2H), 2.44 – 2.33 (m, 2H), 2.27 (s, 3H), 2.04 – 1.97 (m, 1H), 1.88 (s, 3H), 1.79 – 1.67 (m, 4H), 1.59 (d, J = 7.2 Hz, 3H), 1.16 (s, 3H); MS (TOF): m/z (%) = 473.3580 (100%) (M+H)+; IR (KBr): v = 3278, 2970, 2802, 1672, 1618, 1560, 1512, 1448, 1408, 1176 cm-1. Example-42 (S)-1-acetyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide
Figure imgf000048_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.20 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.47 (m, 6H), 7.13 (d, J = 8.4 Hz, 1H), 5.94 (quin, J = 7.6 Hz, 1H), 3.58 – 3.53 (m, 2H), 2.20 (s, 3H), 2.13 – 2.06 (m, 1H), 1.97 (s, 3H), 1.95 – 1.81 (m, 3H), 1.58 (s, 3H), 1.47 (s, 3H); MS (TOF): m/z (%) = 458.3277 (30%) (M+H)+; IR (KBr): v = 3288, 2964, 2929, 1631, 1525, 1409, 1174, 1155, 1033 cm-1. Example-43 2-methyl-5-((((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000049_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 7.2 Hz, 1H), 8.25 (d, J = 7.2 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.62 – 7.51 (m, 4H), 6.92 (d, J = 7.2 Hz, 1H), 6.62 – 6.59 (m, 2H), 5.90 (br s, 1H), 5.60 (br s, 1H), 2.99 – 2.91 (m, 4H), 2.12 (s, 3H), 1.76 – 1.69 (m, 4H), 1.57 – 1.56 (m, 3H), 1.18 (s, 3H); MS (ESI): m/z (%) = 402.10 (100%) (M+H)+; IR (CHCl3): v = 3016, 2978, 1610, 1510, 1450, 1400, 1336, 1215 cm-1. Example-44 2-methyl-5-(methyl(((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1- (naphthalen-1-yl) ethyl)benzamide
Figure imgf000049_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.78 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.64 – 7.48 (m, 4H), 6.98 (d, J = 8.0 Hz, 1H), 6.75 – 6.72 (m, 2H), 5.90 (quin, J = 7.2 Hz, 1H), 3.30 – 3.20 (m, 2H), 2.92 – 2.79 (m, 2H), 2.15 (s, 3H), 1.89 (s, 3H), 1.76 – 1.66 (m, 3H), 1.58 – 1.56 (m, 4H), 1.46 – 1.40 (m, 1H), 1.04 (s, 3H); MS (ESI): m/z (%) = 416.05 (100%) (M+H)+; IR (CHCl3): v = 3016, 2976, 1606, 1508, 1450, 1398, 1215, 750 cm-1. Example-45 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000049_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.47 (m, 4H), 6.91 (d, J = 8.4 Hz, 1H), 6.62 – 6.57 (m, 2H), 5.89 (quin, J = 7.2 Hz, 1H), 4.98 – 4.97 (m, 1H), 2.99 – 2.78 (m, 4H), 2.15 (s, 3H), 2.12 (s, 3H), 1.84 – 1.83 (m, 1H), 1.69 – 1.62 (m, 2H), 1.57 (d, J = 6.8 Hz, 3H), 1.50 – 1.45 (m, 1H), 0.92 (s, 3H); MS (ESI): m/z (%) = 416.05 (100%) (M+H)+; IR (CHCl3): v = 3292, 2970, 2926, 1749, 1645, 1610, 1514, 1450, 1377, 1215, 1012 cm-1. Example-46 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000050_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.47 (m, 4H), 6.98 (d, J = 8.4 Hz, 1H), 6.70 – 6.65 (m, 2H), 5.92 – 5.88 (m, 1H), 3.25 (d, J = 15.2 Hz, 1H), 3.13 (d, J = 15.2 Hz, 1H), 2.88 – 2.84 (m, 2H), 2.20 (s, 3H), 2.15 (s, 3H), 1.79 – 1.72 (m, 2H), 1.64 – 1.56 (m, 5H), 1.45 – 1.38 (m, 1H), 0.9 (s, 3H); MS (TOF): m/z (%) = 430.2893 (100%) (M+H)+; IR (CHCl3): v = 3016, 2978, 1705, 1647, 1606, 1508, 1450, 1373, 1215, 1089, 744 cm-1. Example-47 (R)-5-amino-2-((dimethylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000050_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.42 (d, J = 7.6 Hz, 1H), 8.90 (br s, 1H), 8.22 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.67 (d, J = 6.8 Hz, 1H), 7.63 – 7.51 (m, 3H), 7.18 (d, J = 8.4 Hz, 1H), 6.93 (d, J = 2.4 Hz, 1H), 6.40 (dd, J1 = 2.4 Hz, J2 = 8.0 Hz, 1H), 5.94 (quint, J = 7.2 Hz, 1H), 4.16 – 4.13 (m, 1H), 3.94 – 3.92 (m, 1H), 2.72 (d, J = 5.2 Hz, 3H), 2.56 (d, J = 5.2 Hz, 3H), 1.63 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 348.2640 (100%) (M+H)+, IR (KBr): v = 3346, 3230, 3041, 1670, 1633, 1600, 1543, 1197, 1174, 1126, 798 cm-1. Example-48 (R)-5-((2-(dimethylamino)ethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000050_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.92 (d, J = 8.0 Hz, 1H), 6.56 – 6.52 (m, 2H), 5.89 (quin, J = 7.2 Hz, 1H), 5.33 (br s, 1H), 3.06 (br s, 2H), 2.41 (t, J = 6.8 Hz, 2H), 2.17 (s, 6H), 2.12 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 376.2401 (100%) (M+H)+. Example-49 (R)-2-methyl-5-((3-(methylamino)propyl)amino)-N-(1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000051_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.4 Hz, 1H), 8.39 (br s, 2H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.96 (d, J = 8.4 Hz, 1H), 6.65 – 6.54 (m, 2H), 5.90 (quin, J = 7.2 Hz, 1H), 3.07 (t, J = 6.8 Hz, 2H), 2.96 (br s, 2H), 2.56 (br s, 3H), 2.13 (br s, 3H), 1.81 (quin, J = 6.8 Hz, 2H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 376.2453 (100%) (M+H)+. Example-50 (R)-5-((2-amino-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000051_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 – 7.82 (m, 4H), 7.63 – 7.49 (m, 4H), 6.97 (d, J = 8.8 Hz, 1H), 6.65 (s, 2H), 5.91 (quin, J = 7.2 Hz, 1H), 3.15 (s, 2H), 2.13 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H), 1.25 (s, 6H); MS (TOF): m/z (%) = 376.2394 (100%) (M+H)+. Example-51 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((pyrrolidin-3-ylmethyl) amino) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000051_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.0 Hz, 3H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.95 (d, J = 8.8 Hz, 1H), 6.56 (s, 2H), 5.90 (t, J = 7.2 Hz, 1H), 3.29 – 3.24 (m, 2H), 3.15 – 3.13 (m, 1H), 3.05 (d, J = 6.8 Hz, 2H), 2.90 – 2.87 (m, 1H), 2.12 (s, 3H), 2.07 – 2.04 (m, 1H), 1.66 – 1.61 (m, 1H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 388.2392 (100%) (M+H)+. Example-52 2-methyl-5-(((1-methylpyrrolidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1 yl) ethyl) benzamide 2,2,2-trifluoroacetate
Figure imgf000052_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.69 (br s, 1H), 8.77 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.97 – 6.93 (m, 1H), 6.54 (s, 2H), 5.90 (quin, J = 7.2 Hz, 1H), 3.72 – 3.66 (m, 1H), 3.63 – 3.56 (m, 2H), 3.40 – 3.30 (m, 1H), 3.16 – 3.00 (m, 4H), 2.87 – 2.85 (m, 3H), 2.12 (s, 3H), 2.07 – 2.04 (m, 1H), 1.84 – 1.80 (m, 1H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 402.2546 (100%) (M+H)+. Example-53 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-3- carboxamide 2,2,2-trifluoroacetate
Figure imgf000052_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.26 (s, 1H), 8.90 (d, J = 8.4 Hz, 3H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.62 – 7.49 (m, 6H), 7.18 (d, J = 8.0 Hz, 1H), 5.93 (quin, J = 7.2 Hz, 1H), 3.28 – 3.23 (m, 3H), 2.29 – 2.20 (m, 4H), 2.07 – 1.98 (m, 1H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 402.2180 (100%) (M+H)+; IR (CHCl3): v = 3251, 2976, 1670, 1637, 1597, 1450, 1199, 1178, 1130, 833, 798, 777 cm-1. Example-54 1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) pyrrolidine-3-carboxamide 2,2,2-trifluoroacetate
Figure imgf000053_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.25 (s, 1H), 10.06 – 9.83 (m, 1H), 8.90 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 6H), 7.19 (d, J = 8.4 Hz, 1H), 5.93 (quin, J = 7.2 Hz, 1H), 3.78 (br s, 1H), 3.59 (br s, 1H), 3.21 (br s, 1H), 3.10 (br s, 1H), 2.88 (s, 3H), 2.23 (s, 3H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 416.2340 (100%) (M+H)+; IR (CHCl3): v = 3263, 3041, 1668, 1597, 1539, 1494, 1452, 1338, 1199, 1178, 1126, 831 cm-1. Example-55 tert-butyl ((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) amino)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate
Figure imgf000053_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.01 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.67 (br s, 1H), 7.62 – 7.49 (m, 6H), 7.22 (d, J = 8.0 Hz, 1H), 7.17 (d, J = 8.0 Hz, 1H), 5.93 (quin, J = 7.2 Hz, 1H), 4.12 – 4.11 (m, 1H), 3.17 – 3.12 (m, 2H), 2.33 – 2.29 (m, 1H), 2.22 (s, 3H), 2.14 – 2.12 (m, 1H), 2.01 – 1.98 (m, 1H), 1.74 – 1.69 (m, 1H), 1.58 (d, J = 6.8 Hz, 3H), 1.53 – 1.51 (m, 1H), 1.38 (s, 9H); MS (TOF): m/z (%) = 559.1594 (100%)+; IR (ATR): v = 3365, 3305, 3059, 2976, 2929, 1676, 1656, 1635, 1508, 1492, 1149, 1055 cm-1. Example-56 (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-3- carboxamide 2,2,2-trifluoroacetate
Figure imgf000053_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.18 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.80 (br s, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 7.6 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.62 – 7.50 (m, 6H), 7.19 (d, J = 8.4 Hz, 1H), 5.93 (quin, J = 7.2 Hz, 1H), 4.09 (br s, 4H), 3.73 ( i J 84 H 1H) 223 ( 3H) 159 (d J 68 H 3H) MS (TOF) / (%) 3882021 (100%) (M+H-TFA)+; IR (ATR): v = 3246, 3047, 2978, 1670, 1597, 1448, 1411, 1199, 1178, 1130, 777 cm-1. Example-57 (R)-1-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine- 3-carboxamide 2,2,2-trifluoroacetate
Figure imgf000054_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.23 (s, 1H), 9.90 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.62 – 7.50 (m, 6H), 7.20 (d, J = 8.4 Hz, 1H), 5.93 (quin, J = 7.2 Hz, 1H), 4.43 – 4.03 (m, 4H), 3.68 – 3.62 (m, 1H), 2.84 (s, 3H), 2.24 (s, 3H), 1.59 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 402.2184 (100%) (M+H-TFA)+; IR (ATR): v = 3261, 3045, 2980, 1670, 1597, 1544, 1496, 1197, 1178, 1126, 779 cm-1. Example-58 (R)-5-((azetidin-3-ylmethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000054_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.4 Hz, 1H), 8.58 (br s, 2H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 6.95 (d, J = 8.8 Hz, 1H), 6.54 – 6.53 (m, 2H), 5.90 (quin, J = 7.2 Hz, 1H), 4.09 (br s, 4H), 3.24 (d, J = 7.2 Hz, 2H), 3.02 – 2.94 (m, 1H), 2.12 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 374.2239 (100%) (M+H-2TFA)+; IR (ATR): v = 3246, 3047, 2978, 2875, 1668, 1610, 1510, 1338, 1176, 1126 cm-1. Example-59 2-methyl-5-((2-(methyl(((R)-pyrrolidin-2-yl)methyl)amino)ethyl)amino)-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000054_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.16 (br s, 1H), 8.76 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.99 – 6.97 (m, 1H), 6.62 (d, J = 8.0 Hz, 2H), 5.91 (quin, J = 7.2 Hz, 1H), 4.05 (br s, 2H), 3.35 (br s, 3H), 3.24 (br s, 3H), 3.17 (br s, 2H), 2.76 (br s, 3H), 2.14 (s, 4H), 1.98 – 1.93 (m, 1H), 1.89 – 1.82 (m, 1H), 1.65 – 1.60 (1H), 1.58 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 445.2986 (100%) (M+H-2TFA)+; IR (ATR): v = 3018, 1670, 1212, 1512, 1454, 1213, 1136, 748 cm-1. Example-60 (R)-5-((2-(dimethylamino)-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000055_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.64 – 7.49 (m, 4H), 6.91 (d, J = 8.0 Hz, 1H), 6.61 – 6.56 (m, 2H), 5.89 (quin, J = 7.2 Hz, 1H), 4.97 (s, 1H), 2.89 (s, 2H), 2.61 (s, 6H), 2.12 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H), 1.03 (s, 6H); MS (ESI): m/z (%) = 404.2718 (100%)+; IR (ATR): v = 3288, 3047, 2974, 2870, 2362, 1637, 1608, 1508 cm-1. Example-61 (R)-2-methyl-5-((2-(methyl(2-(methylamino)ethyl)amino)ethyl)amino)-N-(1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000055_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J = 8.0 Hz, 2H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 5H), 7.01 – 6.96 (m, 1H), 6.61 – 6.59 (m, 2H), 5.92 (quin, J = 7.2 Hz, 1H), 3.41 –3.26 (m, 10H), 2.61 (s, 4H), 2.14 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 419.2821 (100%) (M+H-TFA)+; IR (CHCl3): v = 3296, 3018, 1672, 1612, 1213, 1134, 750, 721 cm-1. Example-62 (R)-5-((2-aminoethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000056_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.78 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.93 – 6.91 (m, 1H), 6.55 – 6.52 (m, 2H), 5.90 (quin, J = 7.2 Hz, 1H), 5.66 (br s, 1H), 3.06 (t, J = 6.0 Hz, 2H), 2.76 (br s, 2H), 2.12 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 348.2100 (100%) (M+H)+; IR (ATR): v = 3296, 3047, 2976, 2927, 2846, 1635, 1535, 1496, 1404, 1342, 1174, 769 cm-1. Example-63 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((S)-3-((S)-2-oxopyrrolidin-3-yl)-2- (2,2,2-trifluoroacetamido)propanamido)benzamide
Figure imgf000056_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.27 (s, 1H), 8.94 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H), 7.62 – 7.49 (m, 6H), 7.18 (d, J = 8.4 Hz, 1H), 5.92 (quin, J = 6.4 Hz, 1H), 4.47 – 4.43 (m, 1H), 3.23 – 2.68 (m, 2H), 2.44 – 2.33 (m, 1H), 2.22 (s, 3H), 2.20 – 2.09 (m, 2H), 1.81 – 1.71 (m, 2H), 1.58 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 555.2232 (100%) (M+H)+; IR (ATR): v = 3271, 3051, 2180, 1683, 1637, 1597, 1541, 1450, 1184, 1157 cm-1. Example-64 5-((S)-2-(dimethylamino)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)- 1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000056_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.92 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.69 – 7.67 (m, 1H), 7.63 – 7.49 (6H), 7.15 (d, J = 8.4 Hz, 1H), 5.92 (quin, J = 7.2 Hz, 1H), 3.32 (t, J = 7.2 Hz, 2H), 3.15 – 3.10 (m, 2H), 2.27 (s, 6H), 2.21 (s, 3H), 2.12 – 2.06 (m, 2H), 1.65 – 1.59 (m, 1H), 1.58 (d, J = 6.8 Hz, 3H), 1.50 – 1.49 (m, 1H); MS (ESI): m/z (%) = 487.2711 (100%) (M+H)+; IR (ATR): v = 3248, 3051, 2974, 2931, 2873, 1678, 1633, 1537, 1494, 1454, 1271, 800, 777 cm-1. Example-65 tert-butyl (R)-2-(((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) amino)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)piperidine- 1-carboxylate
Figure imgf000057_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.11 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.0 Hz, 2H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 8H), 7.69 (s, 1H), 7.62 – 7.49 (m, 6H), 7.17 (d, J = 8.8 Hz, 1H), 5.92 (quin, J = 6.8 Hz, 1H), 4.5 (br s, 2H), 3.80 – 3.75 (m, 1H), 3.18 – 3.09 (m, 3H), 2.22 (s, 4H), 2.11 - 2.06 (m, 3H), 1.76 – 1.70 (m, 1H), 1.58 (m, 7H), 1.37 – 1.24 (m, 11H); MS (ESI): m/z (%) = 670.1252 (80%) (M+H)+, 570.1087 (100%) (M+H-Boc)+; IR (ATR): v = 3284, 2929, 2870, 1693, 1639, 1529, 1452, 1408, 1365, 1323, 1271, 1161 cm-1. Example-66 tert-butyl ((S)-1-((1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl)carbamoyl)phenyl)carbamoyl)-3-azabicyclo[3.1.0]hexan-3-yl)-3,3-dimethyl-1- oxobutan-2-yl)carbamate
Figure imgf000057_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.20 (s, 1H), 8.93 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.48 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 6.67 (d, J = 9.2 Hz, 1H), 5.92 (quin, J = 7.2 Hz, 1H), 4.39 (s, 1H), 4.08 (d, J = 9.2 Hz, 1H), 3.96 (d, J = 10.4 Hz, 1H), 3.87 – 3.86 (m, 1H), 2.20 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H),1.54 – 1.51 (m, 1H), 1.36 (s, 9H), 1.26 (br s, 1H), 1.03 (s, 3H), 0.94 – 0.86 (m, 12H); MS (ESI): m/z (%) = 655.3845 (40%) (M+H)+, 555.3335 (100%) (M+H- Boc)+; IR (ATR): v = 3311, 3277, 2873, 1720, 1689, 1647, 1629, 1612, 1496, 1446, 1168 cm-1. Example-67 (1R,2S,5S)-3-((R)-2-amino-3,3-dimethylbutanoyl)-6,6-dimethyl-N-(4-methyl-3-(((R)- 1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3-azabicyclo[3.1.0]hexane-2- carboxamide 2,2,2-trifluoroacetate
Figure imgf000058_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.33 (s, 1H), 8.93 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 8.01 (br s, 2H), 7.98 (d, J = 7.6 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.62 – 7.48 (m, 6H), 7.17 (d, J = 8.4 Hz, 1H), 5.92 (quin, J = 7.2 Hz, 1H), 4.39 (s, 1H), 3.91 – 3.84 (m, 2H), 3.73 – 3.70 (m, 1H), 2.21 (s, 3H), 1.58 (d, J = 6.8 Hz, 4H), 1.44 (d, J = 8.0 Hz, 1H), 1.05 (s, 12H), 0.99 (s, 3H); MS (ESI): m/z (%) = 555.3342 (100%) (M+H-TFA)+, 667.3100 (80%) (M-H)-; IR (ATR): v = 2964, 1676, 1637, 1452, 1201, 1180, 1136, 798, 779, 721cm-1. Example-68 5-((S)-2-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000058_0002
IR (KBr): v = 3248, 2972, 1629, 1597, 1529, 1492, 1400, 1336, 1313, 1203, 1118, 798, 777, 650 cm-1 ; MS (TOF): m/z (%) = 390.2290 (100%) (M+H)+, 388.2029 (100%) (M- H). Example-69 (R)-3-(but-2-yn-1-yloxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000058_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.86 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.58 (dd, J =6.8 Hz, J = 1.6 Hz , 1H), 7.56 – 7.47 (m, 5H), 7.23 (d, J = 7.6 Hz, 1H), 5.98 – 5.94 (m, 1H), 4.80 (d, J = 2.4 Hz, 2H), 2.15 (s, 3H), 1.82 (s, 3H), 1.62 (d, J = 7.2 Hz, 3H); IR (KBr): v = 1624, 1498, 1338, 1236, 1118, 1020, 10006, 798, 775, 441 cm-1; MS (TOF): m/z (%) = 358.1794 (100%) (M+H)+. Example-70 (R)-3-(2-(2-methoxyethoxy)ethoxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000059_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.86 (d, J = 7.6 Hz, 1H), 8.20 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 (dd, J =6.8 Hz, 1H), 7.59 – 7.49 (m, 3H), 7.45 – 7.44 (m, 2H), 7.22 (d, J = 8.0 Hz, 1H), 5.98 – 5.94 (m, 1H), 4.15 (d, J = 4.8 Hz, 2H), 3.77 (d, J = 4.4 Hz, 2H), 3.62 – 3.60 (m, 2H), 3.47 – 3.44 (m, 2H), 3.24 (s, 3H), 2.19 (s, 3H), 1.62 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 408.2162(100%) (M+H)+. Example-71 5-((S)-2-aminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000059_0002
FTIR: v = 3265, 2956, 2927, 1631, 1527, 1398, 1336, 798, 777, 468 cm-1 ; MS (TOF): m/z (%) = 418.2587 (100%) (M+H)+; 416.2349 (100%) (M-1). Example-72 tert-butyl ((R)-4-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) amino)-4-oxobutan-2-yl)carbamate
Figure imgf000059_0003
IR (KBr): v = 3277, 1687, 1622, 1529, 1172, 1058, 777 cm-1 ; MS (TOF): m/z (%) = 390.2267 (100%) (M-Boc+H)+, 512.2548 (80%) (M+Na)+, 488.2554 (40%) (M-H). Example-73 methyl (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoate
Figure imgf000060_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.29 (s, 1H), 9.23 (d, J = 7.6 Hz, 1H), 8.45 (s, 1H), 8.21 – 8.17 (m, 3H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 (d, J = 6.8 Hz, 1H), 7.60 – 7.50 (m, 3H), 5.98 – 5.95 (m, 1H), 3.88 (s, 3H), 2.07 (s, 3H), 1.63 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1724, 1531, 1448, 1263, 1220, 1031, 800, 777, 758, 538 cm- 1; MS (TOF): m/z (%) = 391.1617 (100%) (M+H)+, 389.1518 (100%) (M-1). Example-74 (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoic acid
Figure imgf000060_0002
1H NMR (400 MHz, DMSO-d6): δ = 13.2 (brs, 1H), 10.25 (s, 1H), 9.21 (d, J = 8.0 Hz, 1H), 8.41 (s, 1H), 8.21 – 8.16 (m, 3H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.64 (d, J = 6.8 Hz, 1H), 7.60 – 7.49 (m, 3H), 6.00 – 5.93 (m, 1H), 2.09 (m, 3H), 1.61 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 377.1474 (100%) (M+H)+, 375.1341 (100%) (M-1). Example-75 5-((R)-3-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000060_0003
IR (KBr): v cm-1 = 3253, 3045, 1633, 1595, 1535, 1496, 1400, 1336, 800, 777 cm-1 ; MS (TOF): m/z (%) = 390.2271 (100%) (M+H)+, 388.2033 (100%) (M-H). Example-76 (R)-5-acetamido-N1-(2-(2-hydroxyethoxy)ethyl)-N3-(1-(naphthalen-1-yl) ethyl) isophthalamide
Figure imgf000061_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.20 (s, 1H), 9.26 (d, J = 8.0 Hz, 1H), 8.52 (t, J = 5.2 Hz, 1H), 8.21 (d, J = 8.4 Hz, 1H), 8.18 (m, 3H), 8.10 (m, 1H), 7.97 – 7.95 (m, 2H), 7.85 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 7.2 Hz, 1H), 7.59 – 7.49 (m, 3H), 5.96 – 5.98 (m, 1H), 4.70 – 4.57 (m, 1H), 3.55 – 3.49 (m, 4H), 3.46 – 3.40 (m, 4H), 2.06 (s, 3H), 1.63 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 464.2168 (100%) (M+H)+, 462.2025 (80%) (M-1). Example-77 methyl (R,E)-4-(3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzamido)but- 2-enoate
Figure imgf000061_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.22 (s, 1H), 9.05 (d, J = 8.0 Hz, 1H), 8.87 (t, J = 5.2 Hz, 1H), 8.22 – 8.20 (m, 2H), 8.12 (s, 1H), 8.00 – 7.95 (m, 2H), 7.85 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 6.8 Hz, 1H), 7.60 – 7.50 (m, 3H), 7.85 (dt, J = 8.0 Hz, J = 4.8 Hz, 1H), 5.99 – 5.91 (m, 2H), 4.08 (s, 2H), 3.66 (m, 3H), 2.06 (m, 3H), 1.63 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1705, 1643, 1531,. 1274, 1174, 777 cm-1; MS (TOF): m/z (%) = 474.2021 (100%) (M+H)+, 472.1905 (100%) (M-1). Example-78 (R)-5-acetamido-N1-(1-(naphthalen-1-yl)ethyl)-N3-propylisophthalamide
Figure imgf000061_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.18 (s, 1H), 9.02 (d, J = 8.0 Hz, 1H), 8.49 (d, J = 5.2 Hz, 1H), 8.21 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H), 8.09 (s, 1H), 7.95 (dd, J = 8.8 Hz, J = 12 Hz 2H) 785 (d J = 84 Hz 1H) 765 (d J = 68 Hz 1H) 760 749 (m 3H) 598 – 5.95 (m, 1H), 3.24 – 3.19 (m, 2H), 2.06 (m, 3H), 1.62 (d, J = 7.2 Hz, 3H), 1.56 – 1.50 (m, 2H), 0.89 (t, J = 7.6 Hz, 3H); MS (TOF): m/z (%) = 418.2109 (100%) (M+H)+, 416.1974 (100%) (M-1). Example-79 (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)isophthalamide
Figure imgf000062_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.18 (s, 1H), 8.96 (d, J = 8.0 Hz, 1H), 8.22 – 8.19 (m, 2H), 8.11 (s, 1H), 8.01 (s, 1H), 7.97 – 7.94 (m, 2H), 7.85 (d, J = 8.0 Hz, 1H), 7.66 (d, J = 6.8 Hz, 1H), 7.59 – 7.44 (m, 4H), 5.96 – 5.94 (m, 1H), 2.06 (m, 3H), 1.63 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 376.1653 (100%) (M+H)+, 374.1513 (100%) (M-1). Example-80 (R)-5-(3-allylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000062_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.86 (d, J = 8.0 Hz, 1H), 8.54 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.39 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.30 (d, J = 2.0 Hz, 1H), 7.07 (d, J = 8.4 Hz, 1H), 6.21 (t, J = 5.6 Hz, 1H), 5.93 – 5.81 (m, 2H), 5.18 – 5.12 (m, 1H), 5.06 (dd, J = 10.4 Hz, J = 1.6 Hz, 1H), 3.73 – 3.70 (m, 2H), 2.18 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v = 3246, 1631, 1541, 1234, 775, 439 cm-1; MS (TOF): m/z (%) = 388.2231 (100%) (M+H)+. Example-81 (R)-5-(3-(4-fluorophenyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000062_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.90 (d, J = 8.0 Hz, 1H), 8.69 (s, 1H), 8.65 (s, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.50 (m, 4H), 7.47 – 7.42 (m, 3H), 7.36 (dd, J = 2.4 Hz, 1H), 7.14 – 7.09 (m, 3H), 5.94 – 5.91 (m, 1H), 2.21 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1635, 1546, 1506, 1203, 775, 466 cm-1; MS (TOF): m/z (%) = 442.2366(100%) (M+H)+, 440.2044 (40%) (M-1). Example-82 (R)-5-(3-(4-fluorophenyl)thioureido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000063_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.18 (s, 1H), 9.70 (s, 1H), 8.89 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.39 (m, 8H), 7.19 – 7.15 (m, 3H), 5.95 – 5.88 (m, 1H), 2.27 (s, 1H), 1.58 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1637, 1506, 1213, 777, 503 cm-1; MS (TOF): m/z (%) = 458.1762 (100%) (M+H)+, 456.1492 (10%) (M-1). Example-83 (R)-5-(3-cyclohexylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000063_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.84 (d, J = 8.0 Hz, 1H), 8.30 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.35 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 7.28 (d, J = 2.0 Hz, 1H), 7.05 (d, J = 8.4 Hz, 1H), 6.00 (d, J = 7.6 Hz, 1H), 5.93 – 5.89 (m, 1H); IR (KBr): v = 3228, 1635, 1616, 1502, 1224, 1122, 775, 665 cm-1; MS (TOF): m/z (%) = 430.2551 (100%) (M+H)+. Example-84 (R)-5-(3-cyclohexylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000063_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.38 (s, 1H), 8.83 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 5H), 7.43 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.32 (d, J = 2.0 Hz, 1H), 7.15 (d, J = 8.0 Hz, 1H), 5.94 – 5.87 (m, 1H), 4.09 – 3.90 (m, 1H), 2.26 (s, 3H), 1.89 – 1.83 (m, 2H), 1.69 – 1.63 (m, 2H), 1.58– 1.57 (m, 5H), 1.44 – 1.11 (m, 5H); IR (KBr): v = 2927, 1525, 1317, 1253, 798, 777 -1 MS (TOF) / (%) = 4462327 (100%) (M+H)+ Example-85 (R)-5-(3-benzylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000064_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.65 (s, 1H), 8.84 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.4 Hz, 1H), 8.17 (brs, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.61 – 7.47 (m, 4H), 7.43 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.34 – 7.33 (m, 5H), 7.27 – 7.24 (m, 1H), 7.18 (d, J = 8.4 Hz, 1H), 5.95 – 5.88 (m, 1H), 4.75 – 4.72 (m, 2H), 2.26 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3278, 1633, 1541, 1523, 1240, 775, 731 cm-1; MS (TOF): m/z (%) = 454.1915 (100%) (M+H)+, 452.1624 (20%) (M-1). Example-86 (R)-5-(3-benzylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000064_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.85 (d, J = 8.0 Hz, 1H), 8.59 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.40 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.35 – 7.22 (m, 6H), 7.07 (d, J = 8.4 Hz, 1H), 6.57 (t, J = 6.0 Hz, 1H), 5.95 – 5.88 (m, 1H), 4.29 (d, J = 6.0 Hz, 2H), 2.19 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3242, 1622, 1539, 1496, 1234, 773, 696 cm-1; MS (TOF): m/z (%) = 438.2448 (100%) (M+H)+, 436.2171 (5%) (M-1). Example-87 5-((S)-3-acetamido-2-aminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000064_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.52 (s, 1H), 8.92 (d, J = 8.4 Hz, 1H), 8.28 – 8.24 (m, 4H), 8.17 (d, J = 5.6 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.36 – 7.47 (m, 6H), 7.21 (d, J = 8.8 Hz, 1H), 5.97 – 5.90 (m, 1H), 3.94 – 3.98 (m, 1H), 3.58 – 3.44 (m, 2H), 2.25 (s, 3H), 1.87 (s, 3H), 1.83 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3255, 1664, 1541, 1494, 1199, 1180, 1134, 752, 721 cm-1; MS (TOF): m/z (%) = 433.2188 (100%) (M+H)+, 431.1837 (70%) (M-1). Example-88 N,N'-((S)-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-3- oxopropane-1,2-diyl)diacetamide
Figure imgf000065_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.04 (s, 1H), 8.90 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.90 (d, J = 5.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.15 (d, J = 8.4 Hz, 1H), 5.94 – 5.91 (m, 1H), 4.45 – 4.40 (m, 1H), 3.34 (t, J = 5.6 Hz, 2H), 2.22 (s, 3H), 1.87 (s, 3H), 1.79 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v =3265, 1637, 1533, 1201, 1176, 1136, 800, 777, 437 cm-1; MS (TOF): m/z (%) = 475.2280 (100%) (M+H)+, 473.1958 (100%) (M-1). Example-89 (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000065_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.18 (d, J = 8.0 Hz, 1H), 7.95 (dd, J = 8.0 Hz, J = 1.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.47 (m, 4H), 7.06 (d, J = 8.0 Hz, 1H), 6.92 (d, J = 2.4 Hz, 1H), 6.77 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 6.42 (d, J = 2.0 Hz, 1H), 5.84 – 5.79 (m, 1H), 3.30 – 3.24 (m, 1H), 3.17 – 3.12 (m, 1H), 3.07 – 3.06 (m, 2H), 1.66 – 1.63 (m, 4H), 1.54 (d, J = 6.8 Hz, 3H); IR (KBr): v 3255, 1597, 1541, 1448, 1199, 1178, 1132, 779, 721 cm-1; MS (TOF): m/z (%) = 388.2002 (50%) (M+H)+, 386.1909 (80%) (M-1). Example-90 (R)-4-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000066_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.15 (d, J = 8.0 Hz, 1H), 7.93 (dd, J = 8.0 Hz, J = 1.6 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.59 – 7.46 (m, 5H), 6.63 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H), 6.42 (d, J = 2.0 Hz, 1H), 5.83 – 5.79 (m, 1H), 3.29 – 3.23 (m, 1H), 3.19 – 3.13 (m, 1H), 2.96 – 2.50 (m, 2H), 1.67 – 1.59 (m, 4H), 1.53 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3334, 1597, 1452, 1199, 1176, 1134, 777 cm-1; MS (TOF): m/z (%) = 388.2007 (50%) (M+H)+, 386.1929 (100%) (M-1). Example-91 (R)-5-(3,3-dimethylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000066_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.83 (d, J = 8.0 Hz, 1H), 8.30 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (dd, J = 8.0 Hz, J = 1.2Hz,1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.45 (m, 5H), 7.41 (d, J = 2.4 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 5.95 – 5.88 (m, 1H), 2.91 (s, 6H), 2.19 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1635, 1525, 1402, 1184, 777, 441 cm- 1; MS (TOF): m/z (%) = 376.2009 (100%) (M+H)+, 374.1900 (20%) (M-1). Example-92 (R)-2-methyl-5-(3-methylureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000066_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.84 (d, J = 8.0 Hz, 1H), 8.51 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (dd, J = 8.8 Hz, J = 1.2Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.41 ( dd, J = 8.0 Hz , J = 2.4 Hz, 1H), 7.29 (d, J = 2.0 Hz, 1H), 7.05 (d, J = 8.4 Hz, 1H), 5.96 – 5.88 (m, 2H), 2.56 (d, J = 2.4 Hz, 3H), 2.18 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v = 3257, 1647, 1633, 1610, 1525, 1242, 796, 771, 665 cm-1; MS (TOF): m/z (%) = 362.1855 (100%) (M+H)+, 360.1755 (20%) (M-1). Example-93 5-((S)-2,3-bis(dimethylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000067_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.22 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.64 – 7.49 (m, 6H), 7.25 – 7.12 (m, 1H), 5.95 – 5.91 (m, 1H), 3.78 – 3.74 (m, 1H), 3.29 – 3.25 (m, 1H), 2.80 (s, 6H), 2.39 (s, 6H), 2.23 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 447.2734 (100%) (M+H)+, 445.2596 (100%) (M-1). Example-94 5-((S)-2,3-bis(isopropylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000067_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.76 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.64 – 7.49 (m, 6H), 7.23 (d, J = 8.4 Hz, 1H), 5.97 – 5.90 (m, 1H), 3.42 – 3.39 (m, 2H), 3.34 – 3.04 (m, 2H), 2.25 (s, 3H), 1.59 (d, J = 6.8 Hz, 3H), 1.26 – 1.19 (m, 12H); IR (KBr): v = 1668, 1598, 1197, 1132, 798, 721 cm-1; MS (TOF): m/z (%) = 475.3033 (100%) (M+H)+, 473.2914 (100%) (M-1). Example-95 (R)-5-(3-(2-aminoethyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000067_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.08 (s, 1H), 8.85 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 7.38 – 7.35 (m, 2H), 7.04 (d, J = 8.4 Hz, 1H), 6.89 – 6.86 (m, 1H), 5.95 – 5.87 (m, 1H), 3.17 – 3.11 (m, 2H), 2.86 (t, J = 6.0 Hz, 2H), 2.17 (s, 3H), 1.56 (d, J = 7.2 Hz, 3H); IR (KBr): v = 3257, 1541, 1494, 1404, 1238, 1178, 777, 651 cm-1; MS (TOF): m/z (%) = 391.2120 (100%) (M+H)+ 3892020 (10%) (M 1) Example-96 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000068_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.78 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.64 – 7.47 (m, 4H), 6.97 (d, J = 8.4 Hz, 1H), 6.70 – 6.65 (m, 2H), 5.94 – 5.83 (m, 1H), 3.29 – 3.27 (m, 1H), 3.11 – 3.08 (m, 1H), 2.87 – 2.84 (m, 1H), 2.43 – 2.37 (m, 2H), 2.19 (s, 3H), 2.16 (s, 3H), 1.91 (s, 3H), 1.76 – 1.71 (m, 1H), 1.64 – 1.56 (m, 4H), 1.43 – 1.37 (m, 1H), 0.83 (s, 3H); MS (ESI): m/z (%) = 430.4 (100%) (M+H)+. Example-97 (R)-2-(methylthio)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide
Figure imgf000068_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.98 (d, J = 8.0 Hz, 1H), 8.94 (s, 1H), 8.23 (d, J = 8.4 Hz, 1H), 8.20 – 8.18 (m, 2H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.65 – 7.48 (m, 4H), 7.35 (d, J = 8.4 Hz, 1H), 7.28 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 7.16 (d, J = 2.4 Hz, 1H), 6.91 – 6.90 (m, 2H), 5.92 – 5.85 (m, 1H), 2.39 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 414.3 (100%) (M+H)+. Example-98 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4-yl) methylsulfonamido) benzamide
Figure imgf000068_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.00 (d, J = 8.0 Hz, 1H), 8.45 (d, J = 1.6 Hz, 1H), 8.44 (d, J = 1.6 Hz, 1H), 8.21 (d, J = 8.8 Hz, 1H), 7.96 (dd, J = 8.0 Hz, J = 1.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.59 – 7.49 (m, 4H), 7.40 – 7.37 (m, 2H), 7.33 (d, J = 1.6 Hz, 1H), 7.11 (d, J = 1.6 Hz, 1H), 7.10 (d, J = 1.6 Hz, 1H), 5.93 – 5.89 (m, 1H), 3.44 (s, 3H), 2.34 (s, 3H), 1.61 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 460.1683 (100%) (M+H)+. Example-99 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4-yl) cyclopropanesulfonamido) benzamide
Figure imgf000069_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.00 (d, J = 8.0 Hz, 1H), 8.47 – 8.48 (m, 2H), 8.23 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.36 (m, 4H), 7.41 – 7.36 (m, 2H), 7.33 (d, J = 1.2 Hz, 1H), 7.19 – 7.11 (m, 1H), 5.95 – 5.88 (m, 1H), 3.44 – 3.17 (m, 1H), 2.34 (s, 3H), 1.61 (d, J = 6.8 Hz, 3H), 1.09 – 1.06 (m, 2H), 1.04 – 0.97 (m, 2H); IR (KBr): v = 1647, 1589, 1490, 1357, 1157, 779, 707, 574, 528 cm-1; MS (TOF): m/z (%) = 486.1856 (M+H)+, 484.1698 (M-1). Example-100 (R)-N-(4-(ethylamino)-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000069_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.29 (s, 1H), 9.37 (s, 1H), 8.88 (d, J = 7.6 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 6H), 6.67 (d, J = 8.8 Hz, 1H), 5.94 – 5.91 (m, 1H), 4.28 – 4.23 (m, 1H), 3.37 – 3.19 (m, 2H), 3.08 (d, J = 6.8 Hz, 2H), 2.43 – 2.33 (m, 1H), 1.98 – 1.90 (m, 3H), 1.59 (d, J = 7.2 Hz, 3H), 1.14 (t, J = 7.2 Hz, 3H); MS (ESI): m/z (%) = 431.3 (100%) (M+H)+, 429.3 (10%) (M-1). Example-101 (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-1-carboxamide
Figure imgf000070_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.83 (d, J = 8.0 Hz, 1H), 8.52 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 5H), 7.40 (d, J = 2.4 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 5.96 – 5.88 (m, 1H), 3.42 (t, J = 4.8 Hz, 4H), 2.29 (t, J = 4.8 Hz, 4H), 2.19 (s, 6H), 1.57 (d, J = 7.2 Hz, 3H); MS (ESI): m/z (%) = 431.3(100%) (M+H)+, 429.4 (20%) (M-1). Example-102 (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-1- carboxamide
Figure imgf000070_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.82 (d, J = 8.0 Hz, 1H), 8.47 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.44 (m, 5H), 7.40 (d, J = 2.0 Hz, 1H), 7.06 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.35 (t, J = 4.8 Hz, 4H), 2.70 (t, J = 4.8 Hz, 4H), 2.19 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): ^ = 1631, 1529, 1408, 1249, 1037, 800, 777 cm-1;MS (ESI): m/z (%) = 417.3 (100%) (M+H)+, 415.3 (20%) (M-1). Example-103 (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000070_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.72 (s, 1H), 8.99 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.15 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.09 (s, 2H), 2.53 – 2.49 (m, 4H), 2.36 – 2.33 (m, 4H), 2.21 (s, 3H), 2.17 (s, 3H), 1.56 (d, J = 6.8 Hz, 3H); IR (KBr): ^ = 1634, 1521, 1215, 1136, 746, 665 cm-1;MS (ESI): m/z (%) = 445.4 (100%) (M+H)+, 443.3 (10%) (M- 1). Example-104 (R)-5-amino-N-(1-(naphtalen-1-yl)ethyl)thiophene-2-carboxamide
Figure imgf000071_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.36 (d, J = 8.0 Hz, 1H), 8.17 (d, J = 8.4 Hz, 1H), 7.94 (d, J = 8.4 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.60 – 7.48 (m, 4H), 7.45 (d, J = 4.0 Hz, 1H), 6.20 (s, 2H), 5.86 – 5.82 (m, 1H), 5.81 (d, J = 4.0 Hz, 1H), 1.56 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3313, 1604, 1462, 1271, 1139, 798, 775, 443 cm-1; MS (ESI): m/z (%) = 297.1 (100%) (M+H)+. Example-105 (R)-5-(2-(4-(4-fluorophenyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1- yl) ethyl)benzamide
Figure imgf000071_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.79 (s, 1H), 8.89 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.65 – 7.49 (m, 6H), 7.15 (d, J = 8.4 Hz, 1H), 7.07 – 7.03 (m, 2H), 6.97 – 6.94 (m, 2H), 5.93 – 5.89 (m, 1H), 3.17 (s, 2H), 3.15 – 3.13 (m, 4H), 2.65 – 2.67 (m, 4H), 2.22 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v = 1647, 1508, 1452, 1232, 11380, 815, 777, 532 cm-1; MS (ESI): m/z (%) = 525.4 (100%) (M+H)+, 523.4 (10%) (M-1). Example-106 (R)-2-methyl-5-(2-(4-methyl-1,4-diazepan-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000071_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.72 (s, 1H), 8.89 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.15 (d, J = 8.0 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.25 (s, 2H), 2.78 – 2.76 (m, 4H), 2.60 – 2.56 (m, 4H), 2.27 (s, 3H), 2.21 (s, 3H), 1.77 – 1.73 (m, 2H), 1.58 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 459.4 (100%) (M+H)+, 457.4 (10%) (M-1). Example-107 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl)methyl) amino) benzamide dihydrochloride
Figure imgf000072_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.45 (s, 1H), 9.04 (s, 1H), 8.83 (d, J = 8.4 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.64 – 7.49 (m, 4H), 6.99 (d, J = 8.8 Hz, 1H), 6.68 – 6.67 (m, 2H), 5.94 – 5.87 (m, 2H), 3.66 – 3.65 (m, 1H), 3.41 – 3.28 (m, 2H), 3.20 – 3.06 (m, 2H), 2.14 (s, 3H), 2.09 – 1.96 (m, 1H), 1.94 – 1.82 (m, 2H), 1.70 – 1.61 (m, 1H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 2623, 1637, 1533, 1448, 1334, 802, 777, 534, 449 cm-1; MS (TOF): m/z (%) = 388.2384 (100%) (M+H)+, 386.2236 (100%) (M-1). Example-108 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl)methyl) amino) benzamide
Figure imgf000072_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.91 (d, J = 8.0 Hz, 1H), 6.56 – 6.52 (m, 2H), 5.93 – 5.86 (m, 1H), 5.46 (d, J = 5.2 Hz, 1H), 3.27 – 3.19 (m, 1H), 2.99 – 2.87 (m, 2H), 2.86 – 2.75 (m, 2H), 2.12 (s, 3H), 1.85 – 1.77 (m, 1H), 1.74 – 1.60 (m, 2H), 1.56 (d, J = 6.8 Hz, 3H), 1.41 – 1.32 (m, 1H); IR (KBr): v = 1637, 1608, 1508, 1338, 1244, 1122, 798, 777, 437 cm-1; MS (TOF): m/z (%) = 388.2385 (100%) (M+H)+, 386.2244 (100%) (M-1). Example-109 (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4- diazepane-1-carboxamide
Figure imgf000072_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.82 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 8.22 (s, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.47 (m, 5H), 7.43 (d, J = 2.0 Hz, 1H), 7.06 (d, J = 8.0 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.53 – 3.48 (m, 5H), 2.50 – 2.46 (m, 2H), 2.26 (s, 3H), 2.19 (s, 3H), 1.84 – 1.76 (m, 2H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3244, 1635, 1527, 1408, 1300, 1240, 1014, 800, 779, 650, 443 cm-1; MS (ESI): m/z (%) = 445.15 (100%) (M+H)+, 467.15 (100%) (M+Na), 443.15(100%) (M-1). Example-110 (R)-5-(2-(4-(2-hydroxyethyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1- yl) ethyl)benzamide
Figure imgf000073_0001
1H NMR (400 MHz, DMSO-d6) D2O-X: δ = 8.85 (d, J = 8.0 Hz, 1H), 8.23 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.2 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.61 – 7.48 (m, 4H), 7.43 – 7.39 (m, 2H), 7.06 (d, J = 8.0 Hz, 1H), 5.92 – 5.88 (m, 1H), 3.56 (s, 2H), 3.50 (t, J = 6.4 Hz, 3H), 3.40 (t, J = 4.8 Hz, 3H), 2.42 – 2.39 (m, 6H), 2.18 (s, 3H), 1.56 (t, J = 7.2 Hz, 3H); IR (KBr): v = 1637, 1523, 1398, 1309, 1126, 997, 800, 777, 950, 441 cm-1; MS (TOF): m/z (%) = 475.3504 (100%) (M+H)+. Example-111 (R)-4-(2-hydroxyethyl)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl)piperazine-1-carboxamide
Figure imgf000073_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.84 (d, J = 8.4 Hz, 1H), 8.52 (s, 1H), 8.24 (d, J = 8.8 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.45 (m, 5H), 7.40 (d, J = 2.0 Hz, 1H), 7.07 (d, J = 8.8 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.52 (t, J = 6.4 Hz, 2H), 3.41 (t, J = 5.2 Hz, 4H), 2.41 (t, J = 4.8 Hz, 6H), 2.19 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 1633, 1529, 1411, 1242, 999, 777, 559 cm-1; MS (TOF): m/z (%) = 461.3322 (100%) (M+H)+. Example-112 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-2- carboxamide
Figure imgf000074_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.84 (s, 1H), 8.88 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.68– 7.50 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 4.25 – 4.21 (m, 1H), 3.59 – 3.53 (m, 1H), 3.27 – 3.22 (m, 1H), 2.58 – 2.51 (m, 1H), 2.28 – 2.23 (m, 4H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 388.2022 (100%) (M+H)+, 386.1872 (40%) (M-1). Example-113 5-((S)-2-amino-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000074_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.66 – 7.50 (m, 6H), 7.14 (d, J = 8.0 Hz, 1H), 5.96 – 5.89 (m, 1H), 3.58 – 3.49 (m, 2H), 3.38 – 3.37 (m, 1H), 2.22 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3286, 1637, 1525, 1408, 1338, 1056, 775, 659, 439 cm- 1; MS (TOF): m/z (%) = 392.1981 (100%) (M+H)+, 390.1819 (100%) (M-1). Example-114 2-methyl-5-(((2-methylazetidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000074_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.88 (s, 1H), 8.78 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.96 (d, J = 7.6 Hz, 1H), 6.68 – 6.66 (m, 2H), 5.92 – 5.89 (m, 1H), 5.86 – 5.83 (m, 1H), 3.85 – 3.71 (m, 2H), 3.49 – 3.46 (m, 1H), 3.40 – 3.37 (m, 1H), 2.41 – 2.32 (m, 1H), 2.19 – 2.13 (m, 4H), 1.57 (d, J = 7.2 Hz, 3H), 1.55 (s, 3H); IR (KBr): v = 2970, 2922, 1637, 1608, 1508, 1336, 1259, 1120, 1037, 800, 777, 731 cm-1; MS (TOF): m/z (%) = 388.2394 (100%) (M+H)+. Example-115 (S)-2-(hydroxymethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)pyrrolidine-1-carboxamide
Figure imgf000075_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.83 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 7.44 – 4.39 (m, 2H), 7.07 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 3.93 – 3.92 (m, 2H), 3.49 – 3.45 (m, 1H), 3.42 – 3.35 (m, 3H), 2.19 (s, 3H), 1.89 – 1.80 (m, 2H), 1.78 – 1.77 (m, 2H), 1.57 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 432.2296 (100%) (M+H)+, 454.2113 (40%) (M+Na). Example-116 5-((azetidin-2-ylmethyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000075_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J = 8.0 Hz, 1H), 8.60 (s, 1H), 8.59 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.97 (d, J = 8.0 Hz, 1H), 6.61 (d, J = 2.4 Hz, 1H), 6.59 (s, 1H), 5.94 – 5.87 (m, 1H), 4.44 – 4.46 (m, 1H), 3.94 – 3.87 (m, 1H), 3.82 – 3.78 (m, 1H), 3.55 – 3.49 (m, 1H), 3.39 – 3.33 (m, 1H), 2.44 – 2.37 (m, 1H), 2.28 – 2.21 (m, 1H), 2.14 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 2974, 1670, 1608, 1510, 1450, 1197, 1176, 1128, 798, 777, 719, 439 cm-1; MS (TOF): m/z (%) = 374.2240 (100%) (M+H)+. Example-117 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen- 1-yl)ethyl)benzamide
Figure imgf000075_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.73 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 8.95 (d, J = 7.6 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.90 (d, J = 8.0 Hz, 1H), 6.62 (d, J = 2.0 Hz, 1H), 6.58 (dd, J = 8.0 Hz, J = 2.4 Hz, 1H), 5.92 – 5.85 (m, 1H), 498 (s 1H) 299 – 289 (m 2H) 281 – 278 (m 1H) 251 – 250 (m 1H) 215 (s 3H) 2.12 (s, 3H), 1.87 – 1.84 (m, 1H), 1.70 – 1.62 (m, 2H), 1.57 (d, J = 6.8 Hz, 3H), 1.50 – 1.43 (m, 1H), 0.92 (s, 3H); IR (KBr): v = 3282, 1608, 1529, 1508, 1396, 1259, 1118, 800, 777, 437 cm-1; MS (TOF): m/z (%) = 416.2756 (100%) (M+H)+. Example-118 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl) amino) benzamide
Figure imgf000076_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.89 (d, J = 8.0 Hz, 1H), 6.52 – 6.48 (m, 2H), 5.91 – 5.87 (m, 1H), 5.95 – 5.57 (m, 1H), 2.94 – 2.91 (m, 2H), 2.83 (t, J = 5.6 Hz, 2H), 2.11 (s, 3H), 1.66 – 1.63 (m, 2H), 1.56 (d, J = 7.2 Hz, 3H), 1.07 – 1.00 (m, 2H); IR (KBr): v = 2920, 1637, 1608, 1508, 1446, 1338, 1259, 1118, 800, 777, 4374 cm-1; MS (TOF): m/z (%) = 402.2551 (100%) (M+H)+. Example-119 (R)-2-methyl-5-(((1-methylpiperidin-4-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000076_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.89 (d, J = 8.0 Hz, 1H), 6.52 – 6.48 (m, 2H), 5.91 – 5.87 (m, 1H), 5.95 (t, J = 6.0 Hz, 1H), 2.85 (t, J = 6.0 Hz, 1H), 2.78 – 2.75 (m, 2H), 2.15 (s, 3H), 2.11 (s, 3H), 1.85 – 1.80 (m, 2H), 1.71 – 1.68 (m, 2H), 1.56 (d, J = 7.2 Hz, 3H), 1.51 – 1.42 (m, 1H), 1.24 – 1.15 (m, 2H); IR (KBr): v = 2920, 2779, 1637, 1610, 1510, 1338, 1274, 1259, 1101, 1022, 800, 777, 439 cm-1; MS (TOF): m/z (%) = 416.2706 (100%) (M+H)+. Example-120 5-(3-((1r,4R)-4-hydroxycyclohexyl)ureido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000076_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.83 (d, J = 8.0 Hz, 1H), 8.30 (s,1H), 8.24 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 4H), 7.34 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.28 (d, J = 2.0 Hz, 1H), 7.05 (d, J = 8.4 Hz, 1H), 5.95 – 5.87 (m, 2H), 3.42 – 3.36 (m, 2H), 2.18 (s, 3H), 1.83 – 1.73 ( m, 4H), 1.57 (d, J = 6.8 Hz, 3H), 1.27 – 1.01 (m, 4H); MS (TOF): m/z (%) = 446.2440 (100%) (M+H)+, 468.2262 (75%) (M+Na). Example-121 5-((S)-2-(dimethylamino)-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl) ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000077_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.60 (s, 1H), 9.76 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.23 – 7.19 (m, 1H), 5.97 – 5.90 (m, 1H), 5.73 (s, 1H), 4.04 – 3.96 (m, 3H), 2.93 (s, 6H), 2.25 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 420.1964 (100%) (M+H)+, 418.1715(100%) (M-1). Example-122 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(3-(piperidin-4-ylmethyl) ureido) benzamide
Figure imgf000077_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.85 (s, 1H), 8.82 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 4H), 7.38 – 7.33 (m, 2H), 7.04 (d, J = 8.4 Hz, 1H), 6.61 (t, J = 5.6 Hz, 1H), 5.93 – 5.87 (m, 1H), 3.04 – 3.01 (m, 2H), 2.95 (t, J = 6.4 Hz, 2H), 2.58 – 2.54 (m, 1H), 2.17 (s, 3H), 1.64 – 1.61 ( m, 2H), 1.57 (d, J = 7.2 Hz, 3H), 1.56 – 1.45 (m, 2H), 1.15 – 1.06 (m, 2H); IR (KBr): v = 3261, 1544, 1400, 1234, 1076, 800, 777, 650, 489 cm-1; MS (TOF): m/z (%) = 445.2610 (100%) (M+H)+. Example-123 (R)-2-methyl-5-(((3-methyloxetan-3-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000078_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.96 – 6.92 (m, 1H), 6.64 – 6.59 (m, 2H), 5.92 – 5.86 (m, 2H), 5.74 – 5.68 (m, 1H), 4.39 (d, J = 6.0 Hz, 2H), 4.22 (d, J = 5.6 Hz, 2H), 2.96 (s, 2H), 2.13 (s, 3H), 1.56 (d, J = 6.8 Hz, 3H), 1.31 (s, 3H); IR (KBr): v = 2968, 1664, 1637, 1610, 1452, 1178, 972, 798, 777, 719 cm-1; MS (TOF): m/z (%) = 389.2028 (100%) (M+H)+. Example-124 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide methanesulfonate
Figure imgf000078_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.49 (s, 1H), 8.93 (d, J = 8.0 Hz, 2H), 8.79 – 8.76 (m, 1H), 8.25 (d, J = 8.4 Hz, 4H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.22 (d, J = 8.4 Hz, 1H), 5.95 – 5.91 (m, 1H), 3.91 – 3.27 (m, 1H), 3.02 – 2.97 (m, 1H), 2.32 (s, 3H), 2.25 (s, 3H), 2.22 – 2.18 (m, 1H), 1.85 – 1.82 (m, 1H), 1.74 – 1.72 (m, 1H), 1.62 – 1.51(m, 6H); MS (TOF): m/z (%) = 416.2361 (100%) (M+H)+ (without salt), 510.2059 (M-1)(salt). Example-125 tert-butyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) amino)methyl)pyrrolidine-1-carboxylate
Figure imgf000078_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.76 – 8.70 (m, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.2 Hz, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.63 – 7.48 (m, 4H), 6.89 – 6.87 (m, 1H), 6.65 – 6.58 (m, 2H), 5.90 – 5.87 (m, 1H), 5.79 – 5.77 (m, 1H), 3.89 – 3.86 (m, 1H), 3.27 – 3.21 (m, 3H), 2.80 – 2.83 (m, 1H), 2.10 – 2.09 (m, 3H), 1.91 – 1.76 (m, 4H), 1.56 (d, J = 4.8 Hz, 3H), 1.43 (s, 9H); IR (KBr): v = 2972, 1672, 1610, 1510, 1392, 1365, 1251, 1166, 1107, 800, 777, 534 cm-1; MS (TOF): m/z (%) = 488.2359 (100%) (M+H)+. Example-126 ethyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino) methyl)pyrrolidine-1-carboxylate
Figure imgf000079_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 – 8.70 (m, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 8.4 Hz, 1H), 7.66 – 7.48 (m, 4H), 6.91 (d, J = 8.4 Hz, 1H), ), 6.68 – 6.60 (m, 2H), 5.91 – 5.87 (m, 1H), 5.82 – 5.80 (m, 1H), 4.08 – 3.95 (m, 2H), 3.90 – 3.87 (m, 1H), 3.29 – 3.27 (m, 3H), 2.85 – 2.83 (m, 1H), 2.11 – 2.09 (m, 3H), 1.91 – 1.76 (m, 4H), 1.56 (d, J = 6.8 Hz, 3H), 1.19 (t, J = 7.2 Hz, 3H); IR (KBr): v = 2974, 1676, 1643, 1610, 1508, 1417,1334, 1111, 800, 777, 532 cm-1; MS (TOF): m/z (%) = 460.3636 (100%) (M+H)+. Example-127 5-((R)-2-amino-3-((R)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000079_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.90 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.96 (dd, J = 8.0 Hz, J = 2.0 Hz, 1H), 7.66 – 7.50 (m, 7H), 7.15 (d, J = 8.4 Hz, 1H), 5.96 – 5.89 (m, 1H), 3.37 – 3.30 (m, 1H), 3.20 – 3.10 (m, 3H), 2.47 – 2.41 (m, 1H), 2.22 (s, 3H), 2.20 – 2.16 (m, 1H), 1.87 – 1.79 (m, 1H), 1.69 – 1.60 (m, 1H), 1.57 (d, J = 6.8 Hz, 3H), 1.53 – 1.57 (m, 1H); IR (KBr): v = 3047, 1668, 1597, 1537, 1494, 1398, 1336, 1205, 800, 777, 651, 439 cm-1; MS (TOF): m/z (%) = 459.24117 (100%) (M+H)+, 457.2249(10%) (M-1). Example-128 (1R,2S,5S)-3-((S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl)-6,6-dimethyl- N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3-azabicyclo [3.1.0] hexane-2-carboxamide
Figure imgf000079_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.24 (s, 1H), 9.39 (d, J = 8.4 Hz, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.62 – 7.48 (m, 6H), 7.15 (d, J = 8.4 Hz, 1H), 5.94 – 5.90 (m, 1H), 4.45 (d, J = 8.4 Hz, 1H), 4.39 (s, 1H), 3.95 – 3.91 (m, 1H), 3.77 – 3.74 (m, 1H), 2.21 (s, 3H), 1.58 – 1.57 (m, 4H), 1.40 (d, J = 7.6 Hz, 1H), 1.03 (s, 3H), 1.01 (s, 9H), 0.89 (s, 3H); MS (TOF): m/z (%) = 651.3152 (100%) (M+H)+, 649.3000 (80%) (M-1). Example-129 tert-butyl (1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1 yl)ethyl) carbamoyl)phenyl)carbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
Figure imgf000080_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.15 – 10.12 (m, 1H), 8.91 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (dd, J = 8.0 Hz, J = 2.4 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 5.95 – 5.91 (m, 1H), 4.14 – 4.06 (m, 1H), 3.62 – 3.58 (m, 1H), 3.29 – 3.26 (m, 1H), 2.22 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H), 1.45 – 1.41 (m, 1H), 1.37 – 1.33 (m, 5H), 1.26 (s, 5H), 1.02 (s, 3H), 0.96 – 0.94 (m, 3H); IR (KBr): v = 3302, 2972, 2034, 1660, 1523, 1417, 1392, 1170, 1138, 881, 777 cm-1; MS (TOF): m/z (%) = 542.3018 (70%) (M+H)+, 442.2493 (100%) (M- Boc+H)+, 540.2868 (10%) (M-1). Example-130 (1R,2S,5S)-6,6-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)-3-azabicyclo[3.1.0]hexane-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000080_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.76 (s, 1H), 8.93 (d, J = 8.0 Hz, 1H), 9.36 – 8.98 (m, 2H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.63 – 7.50 (m, 6H), 7.24 (d, J = 8.4 Hz, 1H), 5.96 – 5.92 (m, 1H), 4.17 (m, 1H), 3.68 – 3.63 (m, 1H), 3.18 – 3.15 (m, 1H), 2.26 (s, 3H), 1.80 – 1.77 (m, 2H), 1.57 (d, J = 6.8 Hz, 3H), 1.08 (s, 3H), 1.06 (s, 3H); MS (TOF): m/z (%) = 442.2512 (100%) (M+H)+, 440.2345 (20%) (M-1). Example-131 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hemimalonate
Figure imgf000081_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.49 (s, 1H), 8.94 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.49 (m, 6H), 7.22 (d, J = 8.0 Hz, 1H), 5.95 – 5.91 (m, 1H), 3.97 – 3.76 (m, 1H), 3.29 – 3.26 (m, 1H), 3.00 – 2.98 (m, 1H), 2.84 (s, 1H), 2.25 (s, 3H), 2.20 – 2.17 (m, 1H), 1.85 – 1.82 (m, 1H), 1.74 – 1.72 (m, 1H), 1.64 – 1.57 (m, 6H); MS (TOF): m/z (%) = 416.2348 (100%) (M+H-MA)+, 414.2246 (10%) (M-1-MA). Example-132 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide benzenesulfonate
Figure imgf000081_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.47 (s, 1H), 8.95 – 8.89 (m, 2H), 8.82 – 8.77 (m, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.44 (m, 8H), 7.34 – 7.28 (m, 3H), 7.22 (d, J = 8.4 Hz, 1H), 5.95 – 5.90 (m, 1H), 3.96 – 3.87 (m, 1H), 3.30 – 3.27 (m, 1H), 2.99 – 2.97 (m, 1H), 2.25 (s, 3H), 2.21 – 2.18 (m, 1H), 1.84 – 1.87 (m, 1H), 1.74 – 1.72 (m, 1H), 1.65 – 1.50 (m, 6H); MS (TOF): m/z (%) = 416.2342 (100%) (M+H-BSA)+, 457.2249(10%) (M-1-BSA). Example-133 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide ethanesulfonate
Figure imgf000082_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.5 (s, 1H), 8.95 – 8.93 (m, 2H), 8.81 – 8.74 (m, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.63 – 7.49 (m, 6H), 7.22 (d, J = 8.4 Hz, 1H), 5.96 – 5.89 (m, 1H), 3.30 – 3.27 (m, 1H), 2.99 – 2.97 (m, 1H), 2.44 – 2.38 (m, 3H), 2.25 (s, 3H), 2.22 – 2.18 (m, 1H), 1.90 – 1.88 (m, 1H), 1.85 – 1.82 (m, 1H), 1.74 – 1.57 (m, 6H), 1.11 – 1.05 (m, 3H); MS (TOF): m/z (%) = 416.2341 (100 %) (M+H-ESA)+, 414.2198 (10 %) (M-1-ESA). Example-134 (R)-5-acetamido-2-methyl-N-(1-phenylethyl)benzamide
Figure imgf000082_0002
1H NMR (400 MHz, DMSO-d6): δ =9.95 (s, 1H), 8.71 (d, J = 8.0 Hz, 1H), 7.58 (d, J1 = 2.4 Hz, 1H), 7.56 (d, J2 = 2.0 Hz, 1H), 7.48 (d, J = 2.0 Hz, 1H), 7.36 (m, 4H), 7.24 (t, J = 7.2 Hz, 1H), 7.13 (d, J = 8.4 Hz, 1H), 5.11 (m, 1H), 2.20 (s, 3H), 2.02 (s, 3H), 1.41 (d, J = 7.2 Hz, 3H). MS (ESI): m/z (%) = 297.15 (100%) (M+1). Example-135 5-((S)-2-amino-3,3-dimethylbutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000082_0003
IR (KBr): v = 3253, 2964, 1635, 1541, 1508, 1398, 1180, 777 cm-1 ; MS (TOF): m/z (%) = 418.2583 (100%) (M+H)+, 416.2345 (100%) (M-H). Example-136 1-acetyl-N-((R)-1-(naphthalen-2-yl)ethyl)pyrrolidine-2-carboxamide
Figure imgf000082_0004
1H NMR (400 MHz, DMSO-d6): δ =8.35 (d, J = 8.0 Hz, 1H), 8.07 (s, 1H), 7.94(m, 1H), 7.83 (m, 1H), 7.52 (m, 4H), 1.94 (s, 2H), 1.71 (s, 1H), 1.52 (d, J = 6.8 Hz, 1H), 1.46 (d, J=6.82 Hz, 2H) MS (ESI): m/z (%) = 311.17 (100%) (M+1). Example-137 5-amino-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2-methylbenzamide
Figure imgf000083_0001
1H NMR (400 MHz, DMSO-d6): δ =8.27 (t, J = 5.6 Hz, 1H), 6.97 (d, J = 10.4 Hz, 1H), 6.82 (t, J = 4.4 Hz, 1H), 6.48 (d, J = 2.4 Hz, 2H), 8.27 (t, J = 5.6 Hz, 1H) , 4.95 (s, 2H), 4.31 (q, J = 5.2 Hz, 2H) ), 2.88 (t, J = 7.2 Hz, 4H), 2.79 (t, J = 7.2 Hz, 4H), 2.12 (d, J = 10.4 Hz, 3H), 1.95 (m, 1H). MS (ESI): m/z (%) = 321.21 (100%) (M+1). Example-138 (R)-2-isopropoxy-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000083_0002
1H NMR (400 MHz, DMSO-d6): δ =8.71 (t, J = 7.6 Hz, 1H), 8.16 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.87 (d, J = 8.0 Hz, 2H), 7.63 (d, J = 6.8 Hz, 1H) , 7.58 (m, 1H), 7.52 (m, 1H), 7.33 (d, J = 3.2 Hz, 1H), 7.10 (d, J = 8.8 Hz, 1H), 7.02 (d, J = 3.2 Hz, 1H), 5.93 (t, J = 7.2 Hz, 1H), 4.57 (m, 1H), 3.73 (s, 3H), 1.63 (d, J = 6.8 Hz, 3H), 1.10 (d, J =6.0 Hz, 3H), 0.98 (d, J = 6.0 Hz, 3H) MS (ESI): m/z (%) = 364.21 (100%) (M+1). Example-139 (R)-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)-2-propoxybenzamide
Figure imgf000083_0003
1H NMR (400 MHz, DMSO-d6): δ =8.65 (d, J = 7.6 Hz, 1H), 8.17 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 1.2 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 6.8 Hz, 1H) , 7.54 (m, 3H), 7.32 (d, J = 2.8 Hz, 1H), 7.03 (m, 2H), 5.93 (t, J = 6.8 Hz, 1H), 5.76 (s, 1H), 3.83 (m, 2H), 3.73 (s, 3H), 1.62 (d, J = 7.2 Hz, 3H), 1.54 (m, 2H), 0.76 (d, J =7.6 Hz, 3H), MS (ESI): m/z (%) = 364.21 (100%) (M+1). Example-140 5-amino-N-(imidazo[1,2-a]pyridin-2-ylmethyl)-2-methylbenzamide
Figure imgf000084_0001
1H NMR (400 MHz, DMSO-d6): δ =8.54 (d, J =1.2 Hz, 1H), 8.01 (s, 1H), 7.53 (d, J = 0.8 Hz, 1H), 7.24 (m, 1H), 7.02 (d, J = 2.4 Hz, 1H), 6.95 (d, J = 8.4 Hz, 1H), 6.90 (t, J = 1.2 Hz, 1H) , 6.66 (d, J = 2.4 Hz, 1H), 5.36 (s, 2H), 5.12 (s, 2H), 2.34 (s, 3H), MS (ESI): m/z (%) = 282.15 (100%) (M+2). Example-141 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate
Figure imgf000084_0002
1H NMR (400 MHz, DMSO-d6): δ =10.56 (s,1H), 9.33 (s, 1H), 8.93 (d, J =8.4 Hz, 1H), 8.68 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.59 (m, 4H), 7.52 (m, 2H), 7.23 (t, J = 7.6 Hz, 1H), 5.93 (t, J = 7.6 Hz, 1H), 4.31 (s, 1H), 3.28 (s, 3H), 1.29 (m, 1H), 2.25 (s, 3H), 1.94 (d, J = 2.4 Hz, 3H), 1.58 (d, J = 7.2 Hz, 3H), MS (ESI): m/z (%) = 402.21 (100%) (M+1). Example-142 (R)-N1-(2-aminoethyl)-N3-(1-(naphthalen-1-yl)ethyl)isophthalamide
Figure imgf000084_0003
1H NMR (400 MHz, DMSO-d6): δ =9.11 (d, J =8.0 Hz, 1H), 8.66 (d, J =5.6 Hz, 1H), 8.36 (t, J = 1.6 Hz, 1H), 8.22 (d, J =8.4 Hz, 1H), 8.03 (d, J =1.6 Hz, 1H), 7.96 (t, J = 1.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 6.8 Hz, 1H) , 7.55 (m, 5H), 5.98 (t, J = 7.2 Hz, 1H), 3.32 (d, J =6.0 Hz, 2H), 2.76 (t, J =6.0 Hz, 2H), 1.63 (d, J =6.8 Hz, 3H), MS (ESI): m/z (%) = 362.18 (100%) (M+1). Example-143 (R)-5-amino-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000085_0001
1H NMR (400 MHz, CDCl3-d1): δ = 8.26 (d, J = 8.4 Hz, 1H), 7.91 (dd, J = 7.6 Hz, 2H), 7.82 (d, J = 8.4 Hz, 1H), 7.61 – 7.54 (m, 3H), 7.52 – 7.46 (m, 1H), 6.936 (d, 1H), 6,68 (q, 2H), 6.49 (d, 1H), 5.92 (t, 2H), 4.68 – 4.58 (q, 1H), 2.79 (d, J = 6 Hz, 2H), 1.72 (m, 3H), 0.887 (dd, J = 8.4 Hz, 6H); MS (TOF): m/z (%) = 362.222 (100%) (M+H)+. Example-144 (R)-5-(2-aminoacetamido)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000085_0002
1H NMR (400 MHz, DMSO-d6): δ =9.10 (d, J =8.0 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.74 (d, J =2.4 Hz, 1H), 7.72 (m, 1H), 7.64 (d, J =7.2 Hz, 1H), 7.50 (m, 3H), 7.41 (d, J =8.8 Hz, 2H), 5.91 (m, 1H), 3.39 (s, 2H), 1.90 (s, 3H), 1.23 (d, J = 5.6 Hz, 3H). MS (ESI): m/z (%) = 382.13 (100%) (M+1); Example-145 2-chloro-5-((R)-2,3-diaminopropanamido)-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000085_0003
1H NMR (400 MHz, DMSO-d6): δ =9.10 (d, J =8.0 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.74 (d, J =2.4 Hz, 1H), 7.72 (d, J =2.8 Hz, 1H), 7.64 (d, J =7.2 Hz, 1H), 7.58 (d, J =1.6 Hz, 1H), 7.52 (m, 2H), 7.41 (d, J =1.2 Hz, 2H), 3.30 (q, J =4.8 Hz, 2H), 2.82 (d, J =4.8 Hz, 1H), 2.64 (q, J =7.2 Hz, 1H), 1.88 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H),MS (ESI): m/z (%) = 411.15 (100%) (M+1). Example-146 (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)tetrahydro-2H- pyran-4-carboxamide
Figure imgf000086_0001
1H NMR (400 MHz, DMSO-d6): δ =9.91 (s, 1H), 8.88 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.0 Hz, 1H), 7.95 (d, J = 7.2 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.62 (m, 3H), 7.51 (m, 3H), 7.13 (d, J =8.4 Hz, 1H), 5.92 (m, 1H), 3.90 (d, J =2.4 Hz, 4H), 3.33 (m, 3H), 2.21 (s, 3H), 1.68 (m, 4H), 1.57 (d, J = 7.2 Hz, 3H), MS (ESI): m/z (%) = 415.19 (100%) (M-1). Example-147 (R)-5-(cyclohexanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000086_0002
1H NMR (400 MHz, DMSO-d6): δ =8.94 (d, J =8.0 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 7.16 (d, J =2.0 Hz, 2H), 5.91 (d, J =7.2 Hz, 1H), 2.95 (m,1H), 2.21 (s, 3H), 2.05 (m,2H), 1.76 (d, J =3.6 Hz, 2H), 1.57 (d, J = 6.8 Hz, 3H), 1.40 (m, 2H), 1.14 (m, 3H),MS (ESI): m/z (%) = 451.20 (100%) (M+1). Example-148 (R)-2-methyl-5-((1-methylethyl)sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000086_0003
1H NMR (400 MHz, DMSO-d6): δ =8.93 (d, J =8.0 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.61 (m, 2H), 7.52 (m, 3H), 7.14 (m, 4H), 3.20 (m,1H), 2.20 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H), 1.23 (d, J = 1.6 Hz, 6H), 1.05 (d, J = 6.8 Hz, 1H),MS (ESI): m/z (%) = 411.17 (100%) (M+1). Example-149 (R)-5-(2-aminoacetamido)-2-(dimethylamino)-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000086_0004
1H NMR (400 MHz, DMSO-d6): δ =10.12 (d, J =8.0 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.95 (q, J = 7.2 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.74 (d, J =2.4 Hz, 1H), 7.56 (m, 4H), 7.21 (d, J =8.8 Hz, 1H), 5.95 (m, 1H), 3.26 (s, 2H), 2.57 (s, 6H), 1.90 (s, 2H), 1.62 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 391.21 (100%) (M+1). Example-150 (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-4- carboxamide
Figure imgf000087_0001
1H NMR (400 MHz, DMSO-d6): δ =9.96 (s, 1H), 8.89 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.59 (m, 3H), 7.52 (m, 3H), 7.13 (d, J =8.4 Hz, 1H), 5.92 (t, J = 7.2 Hz, 1H), 4.40 (m, 3H), 3.89 (m, 4H), 3.10 (m, 4H), 2.92 (m, 4H), 2.24 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 416 (M+1). Example-151 2-methyl-5-((((R)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000087_0002
1H NMR (400 MHz, CDCl3-d1): δ = 8.75 (d, J = 7.2 Hz, 1H), 8.25 (d, J = 8 Hz, 1H), 7.96 (d, J = 8.1 Hz, 1H), 7.84 – 7.82 (m, J = 8 Hz, 1H), 7.63 – 7.49 (m, 4H), 6.91 (d, J = 8 Hz, 1H), 6.61 – 6.57 (t, 2H), 5.91 – 5.87 (t, J = 7.6 Hz 1H), 5.23 (s, 1H), 2.89 (s, 3H), 1.36 (dd, J = 4.4 Hz, 1H); 2.20 (s, 4H), 1.72 (d, J = 7.2 Hz, 4H), 1.68 (m,3H),1.44 (m, 2H), 1.23 (s, 3H); MS (TOF): m/z (%) = 402.25 (100%) (M+H)+; UPLC (% Purity) = 91.73 % Example-152 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-2- carboxamide 2,2,2-trifluoroacetate
Figure imgf000087_0003
1H NMR (400 MHz, DMSO-d6): δ =10.59 (s, 1H), 8.91 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.85 (d, J =8.4 Hz, 1H), 7.62 (m, 3H), 7.57 (d, J =2.0 Hz, 1H), 7.51 (d, J =8.0 Hz, 2H), 7.23 (d, J =4.8 Hz, 1H), 5.93 (m, 1H), 4.12 (d, J =7.6 Hz, 1H), 3.89 (s, 1H), 3.84 (s, 1H), 3.38 (d, J =11.2 Hz, 3H), 3.10 (m, 3H), 2.25 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 417.22 (100%) (M+1); Free base Example-153 (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide
Figure imgf000088_0001
1H NMR (400 MHz, DMSO-d6): δ =9.12 (d, J =8.0 Hz, 1H), 9.03 (s, 1H), 8.21 (d, J =8.0 Hz, 3H), 7.95 (d, J = 8.0 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 7.42 (d, J =8.8 Hz, 1H), 7.26 (d, J =2.4 Hz, 1H), 7.13 (d, J =2.8 Hz, 1H), 6.93 (d, J =6.0 Hz, 2H), 5.89 (m, 1H), 1.90 (s, 2H), 1.58 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 402.13 (100%) (M+1). Example-154 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl) methyl) amino) benzamide 2,2,2-trifluoroacetate
Figure imgf000088_0002
1H NMR (400 MHz, DMSO-d6): δ =8.76 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.83 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 6.91 (d, J =8.0 Hz, 1H), 6.56 (t, J =2.4 Hz, 1H), 6.52 (d, J =2.4 Hz, 1H), 5.89 (t, J =7.6 Hz, 1H), 5.61 (s, 1H), 3.26 (d, J =6.8 Hz, 1H), 2.97 (d, J =8.0 Hz, 2H), 2.82 (m, 2H), 2.11 (s, 3H), 1.86 (t, J =7.6 Hz, 6H), 1.68 (m, 2H), 1.56 (d, J =6.8 Hz, 3H), 1.41 (m,1H). MS (ESI): m/z (%) = 388.23 (100%) (M+1); Free Base +1 Example-155 5-((R)-2,3-diaminopropanamido)-2-(methylamino)-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide 2,2,2-trifluoroacetate
Figure imgf000088_0003
1H NMR (400 MHz, DMSO-d6): δ =10.40 (s, 1H), 8.82 (d, J =7.6 Hz, 1H), 8.35 (s, 3H), 8.20 (d, J =8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J =8.0 Hz, 1H), 7.69 (d, J = 88 Hz 1H) 761 (m 2H) 755 (m 2H) 664 (d J =92 Hz 1H) 421 (t J = 52 Hz 1H), 3.45 (m, 1H), 3.23 (m, 1H), 2.73 (s, 3H), 1.59 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 406.22 (M+1). Example-156 (R)-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide
Figure imgf000089_0001
1H NMR (400 MHz, CDCl3-d1): δ = 8.87 (d, 1H), 8.85 (s, 1H), 8.74 (d, 1H), 8.21 (s, 2H), 8.08 (d, 1H), 7.94 (d, 1H), 7.822 (d, 1H), 7.610 (m, 4H), 7.4 (d, 3H), 7.17 (d, 1H), 6.72 (d, 1H); 6.68 (d, 2H), 5.95(m, 1H), 3.3 (d, 3H), 1.85 (d, 3H), 1.46 (d, 3H); MS (TOF): m/z (%) = 411.2184 (M+H)+; UPLC (% Purity) = 94.53 % Example-157 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperazin-2-ylmethyl) amino) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000089_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.77 (d, J =2.0 Hz, 1H), 8.24 (d, J =8.8 Hz, 1H), 7.95 (d, J = 4.0 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 6.99 (d, J =8.4 Hz, 1H), 6.63 (d, J =2.4 Hz, 2H), 6.54 (s, 1H), 5.91 (m, 1H), 3.30 (s, 4H), 3.11 (m, 3H), 3.02 (m, 2H), 2.14 (s, 3H), 1.60 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 403.24 (100%) (M+1); Free base Example-158 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperidin-3-ylmethyl)amino) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000089_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J = 4.4 Hz, 1H), 8.58 (d, J = 10 Hz, 1H), 8.24 (d, J = 8.4 Hz, 2H), 7.95 (d, J =8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.53 (m, 3H), 6.91 (d, J = 8.4 Hz, 1H), 6.55 (s, 1H), 6.52 (d, J = 2.4 Hz, 2H), 5.88 (m, 1H), 3.24 (m, 2H), 2.95 (t, J = 6.0 Hz, 2H), 2.81 (m, 1H), 2.72 (m, 1H), 2.12 (s, 3H), 1.95 (t, J = 2.8 Hz, 1H), 1.80 (m, 2H), 1.50 (d, J = 4.0 Hz, 4H), 1.12 (m, 1H). MS (ESI): m/z (%) = 402.25 (100%) (M+1). Example-159 2-methyl-5-(methyl(((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((S)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000090_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.25 (d, J =8.4 Hz, 1H), 8.23 (d, J =8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.84 (d, J =8.0 Hz, 1H), 7.61 (d, J =6.8 Hz, 1H), 7.55 (m, 2H), 7.47 (d, J =7.6 Hz, 1H), 6.99 (d, J =8.0 Hz, 2H), 6.66 (d, J =2.4 Hz, 1H), 6.63 (d, J =2.8 Hz, 1H), 5.90 (m, 1H), 3.50 (d, J =4.4 Hz, 1H), 3.04 (q, J =7.2 Hz, 1H), 2.93 (m, 4H), 2.33 (m, 2H), 2.24 (m, 3H), 2.21 (s, 3H), 2.05 (m, 2H), 1.80 (m, 1H), 1.52 (m, 5H0, 1.48 (m, 1H). MS (ESI): m/z (%) = 416.26 (100%) (M+1). Example-160 5-(((1,4-dimethylpiperazin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000090_0002
1H NMR (400 MHz, DMSO-d6): δ =8.0 (d, J = 2.8 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.60 (m, 1H), 7.52 (m,3H), 7.01 (t, J = 3.6 Hz, 1H), 6.63 (t, J = 2.4 Hz, 1H), 5.91 (t, J = 7.2 Hz, 1H), 3.63 (m, 1H), 3.1 (m, 2H), 2.87 (s, 3H), 2.60 (s, 2H), 2.25 (d, J = 2.4 Hz, 4H), 2.16 (s, 4H), 2.09 (d, J= 12 Hz, 4H), 1.89 (s, 4H), 1.57 (d, J = 1.6 Hz, 1H). MS (ESI): m/z (%) = 445.4 (100%) (M+1). Example-161 2-methyl-5-(methyl((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl) ethyl)benzamide
Figure imgf000090_0003
1H NMR (400 MHz, DMSO-d6): δ =8.80 (qd, J = 6.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.60 (m, 1H), 7.54 (m,3H), 6.99 (d, J = 8.4 Hz, 1H), 6.63 (d, J = 2.8 Hz, 1H), 6.57 (t, J = 2.8 Hz, 1H), 5.90 (s, 1H), 3.16 (m, 2H), 2.87 (s, 3H), 2.15 (s, 3H), 2.10 (s, 3H), 1.68 (m, 1H), 1.58 (d, J = 6.0 Hz, 5H), 1.39 (m, 1H), 0.93 (m, 1H). MS (ESI): m/z (%) = 430.3 (100%) (M+1). Example-162 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-3- carboxamide 2,2,2-trifluoroacetate
Figure imgf000091_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 8.0 Hz, 1H), 8.60 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 6.8 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.60 (m, 4H), 7.52 (d, J = 6.8 Hz, 2H), 7.16 (d, J = 8.4 Hz, 1H), 5.93 (d, J = 7.2 Hz, 1H), 3.33 (s, 1H), 3.30 (s, 1H), 3.20 (d, J = 13.2 Hz, 1H), 3.06 (m, 1H), 2.93 (s, 1H), 2.79 (m, 1H), 2.22 (s, 3H), 2.01 (d, J = 4.4 Hz, 1H), 1.83 (d, J = 10.4 Hz, 1H), 1.64 (t, J = 6.4 Hz, 2H), 1.57 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 416.3 (100%) (M+1). Example-163 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate
Figure imgf000091_0002
1H NMR (400 MHz, DMSO-d6): δ =10.55 (s, 1H), 9.30 (s, 1H), 8.92 (d, J = 8.0 Hz, 1H), 8.68 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.60 (m, 6H), 7.22 (d, J = 8.4 Hz, 1H), 5.93 (d, J = 7.6 Hz, 1H), 2.36 (m, 2H), 2.25 (s, 3H), 1.94 (d, J = 2.4 Hz, 1H), 1.58 (d, J =7.2 Hz, 5H). MS (ESI): m/z (%) = 402.3 (100%) (M+1). Example-164 1,4-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperazine-2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000091_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.40 (s, 1H), 8.91 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J =8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.56 (m, 6H), 7.27 (s, 1H), 7.20 (d, J = 8.4 Hz, 1H), 5.93 (d, J = 7.2 Hz, 1H), 3.30 (m, 7H), 2.69 (m, 4H), 2.24 (s, 3H), 1.58 (d, J =7.2 Hz, 3H); MS (ESI): m/z (%) = 445.15 (100%) (M+1). Example-165 1,4-diacetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperazine-2-carboxamide
Figure imgf000092_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.94 (d, J = 6.8 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J =7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.52 (m, 6H), 7.14 (m, 1H), 5.92 (m, 1H), 4.51 (d, J = 11.6 Hz, 1H), 4.23 (m, 2H), 4.13 (d, J = 12.4 Hz, 1H), 3.79 (d, J = 2.8 Hz, 2H), 3.42 (d, J = 4.0 Hz, 1H), 2.20 (d, J = 6.4 Hz, 3H), 2.09 (d, J = 8.4 Hz, 2H), 2.01 (d, J = 2.4 Hz, 1H), 1.95 (d, J = 12.4 Hz, 3H), 1.57 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 499.5 (100%) (M-1). Example-166 1,4-bis(cyclopropylsulfonyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl)piperazine-2-carboxamide
Figure imgf000092_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.15 (s, 1H), 8.97 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J =7.2 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.40 (m, 7H), 7.18 (d, J = 8.4 Hz, 1H), 5.92 (t, J = 6.4 Hz, 1H), 4.61 (s, 1H), 4.06 (d, J = 12.8 Hz, 1H), 3.83 (d, J = 12 Hz, 1H), 3.63 (d, J = 12.4 Hz, 2H), 2.94 (m, 1H), 2.63 (m, 3H), 2.21 (d, J = 6.4 Hz, 3H), 1.57 (d, J =6.8 Hz, 3H), 1.02 (m, 4H), 0.91 (s, 5H), MS (ESI): m/z (%) = 623.4 (100%) (M-1). Example-167 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4-bis (methylsulfonyl) piperazine-2-carboxamide
Figure imgf000092_0003
1H NMR (400 MHz, DMSO-d6): δ =10.17 (s, 1H), 8.97 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.54 (m, 6H), 7.19 (t, J = 8.8 Hz, 1H), 5.92 (t, J = 6.8, 1H), 4.62 (s, 1H), 4.04 (d, J = 12.8 Hz, 1H), 3.20 (d, J = 4.0 Hz, 1H), 3.02 (s, 3H), 2.91 (d, J = 1.2 Hz, 3H), 2.85 (d, J =4.0 Hz, 1H), 2.21 (d, J = 5.2 Hz, 3H), 1.57 (d, J =6.8 Hz, 3H); MS (ESI): m/z (%) = 571.00 (100%) (M-1). Example-168 N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-4-(methylsulfonyl) piperazine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000093_0001
1H NMR (400 MHz, DMSO-d6): δ =10.77 (s, 1H), 9.38 (s, 1H), 8.94 (s, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.53 (m, 6H), 6.95 (d, J = 8.4 Hz, 1H), 7.24(d, J = 8.8 Hz, 1H), 5.94 (s, 1H), 4.20 (m, 1H), 4.08 (m, 1H), 3.64 (m, 1H), 3.12 (m, 1H), 3.09 (m, 2H), 3.05 (s, 3H), 2.26 (s, 3H), 1.57 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 495.20 (100%) (M+1). Example-169 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl) methyl) amino) benzamide 2,2,2-trifluoroacetate
Figure imgf000093_0002
1H NMR (400 MHz, DMSO-d6): δ =8.95 (s, 1H), 8.77 (d, J = 8.4 Hz, 1H), 8.42 (s, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.54 (m, 4H), 6.97 (d, J = 8.0 Hz, 1H), 6.60 (d, J = 2.4 Hz, 2H), 5.91 (m, 1H), 5.75 (s, 1H), 3.63 (d, J = 5.2 Hz, 2H), 3.26 (m, 4H), 2.14 (s, 3H), 2.07 (m, 1H), 1.91 (m, 2H), 1.68 (m, 1H), 1.57 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 388.23 (100%) (M+1). Example-170 4-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000093_0003
1H NMR (400 MHz, DMSO-d6): δ =10.63 (s, 1H), 8.93 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.55 (m, 6H), 7.24 (t, J = 7.6 Hz, 1H), 5.93 (s, 1H), 4.12 (s, 2H), 3.41 (m, 2H), 3.12 (m, 3H), 2.78 (m, 1H), 2.55 (d, J = 1.6 Hz, 3H), 1.57 (d, J = 6.8 Hz, 3H), 1.11 (s, 6H). MS (ESI): m/z (%) = 459.27 (100%) (M+1). Example-171 2-methyl-5-((((S)-1-(methylsulfonyl)pyrrolidin-2-yl)methyl)amino)-N-((R)-1- (naphthalen-1-yl) ethyl)benzamide
Figure imgf000094_0001
1H NMR (400 MHz, DMSO-d6): δ =8.72 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.2 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 7.2 Hz, 1H), 7.54 (m, 3H), 6.93 (d, J = 8.4 Hz, 1H), 6.64 (d, J = 2.0 Hz, 1H), 6.59 (d, J = 2.0 Hz, 1H), 5.88 (m, 1H), 3.78 (d, J = 3.2 Hz, 1H), 3.26 (m, 3H), 2.91 (d, J = 4.0 Hz, 3H), 2.12 (s, 3H), 1.83 (m, 4H), 1.55 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 488.15 (100%) (M+Na). Example-172 5-((((S)-1-(cyclopropylsulfonyl)pyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000094_0002
1H NMR (400 MHz, DMSO-d6): δ =8.73 (d, J = 7.6 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.64 (d, J = 7.2 Hz, 1H), 7.54 (m, 6H), 6.92 (d, J = 8.0 Hz, 1H), 6.63 (d, J = 2.0 Hz, 1H), 6.59 (d, J = 2.0 Hz, 1H), 5.88 (d, J = 7.2 Hz, 1H), 3.91 (s, 1H), 3.37 (m, 1H), 3.28 (m, 1H), 2.93 (t, J = 3.2 Hz, 1H), 2.74 (t, J = 5.2 Hz, 1H), 2.12 (s, 3H), 1.88 (d, J = 4.4 Hz, 4H), 1.55 (d, J = 6.8 Hz, 3H), 0.95 (t, J = 4.0 Hz, 4H). MS (ESI): m/z (%) = 492.22 (100%) (M+1). Example-173 (S)-1-acetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide
Figure imgf000094_0003
1H NMR (400 MHz, DMSO-d6): δ =9.97 (s, 1H), 8.93 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.54 (m, 6H), 7.14 (d, J = 8.4 Hz, 1H), 3.58 (m, 1H), 3.52 (m, 1H), 2.21 (s, 3H), 2.12 (m, 1H), 1.99 (s, 3H), 1.89 (m, 1H0, 1.83 (s, 1H), 1.57 (d, J = 6.8 Hz, 3H). MS (ESI): m/z (%) = 444.30 (100%) (M+1). Example-174 (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1- (methylsulfonyl) pyrrolidine-2-carboxamide
Figure imgf000095_0001
1H NMR (400 MHz, DMSO-d6): δ =9.91 (s, 1H), 8.93 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 6H), 7.16 (d, J = 8.4 Hz, 1H), 5.92 (t, J = 7.2 Hz, 1H), 4.28 (d, J = 3.6 Hz, 1H), 3.47 (m, 1H), 3.38 (m, 1H), 2.98 (s, 3H), 2.21 (s, 4H), 1.92 (m, 3H), 1.57 (d, J = 7.2 Hz, 3H). MS (ESI): m/z (%) = 480.27 (100%) (M+1). Example-175 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((1-(((S)-pyrrolidin-2-yl)methyl) piperidin-4-yl)amino)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000095_0002
1H NMR (400 MHz, DMSO-d6): δ =9.71 (s, 1H), 9.21 (s, 1H), 8.98 (s, 1H), 8.78 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 4H), 6.95 (d, J = 8.4 Hz, 1H), 6.58 (d, J = 6.8 Hz, 2H), 5.90 (t, J = 7.2 Hz, 1H), 3.67 (m, 1H), 3.45 (m, 3H), 3.26 (s, 3H), 2.13 (s, 4H), 1.97 (m, 2H), 1.88 (m, 1H), 1.69 (m, 1H), 1.56 (d, J =7.2 Hz, 4H). MS (ESI): m/z (%) = 471.39 (100%) (M+1). Example-176 4-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000095_0003
1H NMR (400 MHz, DMSO-d6): δ =10.63 (s, 1H), 8.93 (d, J = 6.4 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 6.8 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.54 (m, 6H), 7.23 (d, J = 8.4 Hz, 1H), 4.17 (t, J = 9.2 Hz, 1H), 3.35 (m, 1H), 2.25 (m, 3H), 1.57 (d, J = 7.2 Hz, 3H). MS (ESI): m/z (%) = 431.31 (100%) (M+1). Example-177 (S)-1-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000096_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.76 (s, 1H), 9.41 (s, 1H), 8.93 (d, J =8.4 Hz, 1H), 8.24 (d, J =8.4 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.86 (d, J =8.0 Hz, 1H), 7.54 (m, 6H), 7.24 (d, J =8.4 Hz, 1H), 5.93 (d, J =7.2 Hz, 1H), 4.30 (d, J =8.8 Hz, 1H), 3.60 (m, 5H), 3.28 (m, 1H), 2.25 (s, 3H), 2.02 (m, 2H), 1.89 (m, 1H), 1.58 (d, J =6.8 Hz, 3H), 1.24 (q, J =6.8 Hz, 6H). MS (ESI): m/z (%) = 444.35 (100%) (M+1). Example-178 (S)-1-ethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000096_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.72 (s, 1H), 9.57 (s, 1H), 8.92 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.0 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.86 (d, J =8.0 Hz, 1H), 7.56 (m, 6H), 7.23 (d, J =8.4 Hz, 1H), 5.94 (t, J =7.6 Hz, 1H), 4.21 (q, J =7.2 Hz, 1H), 3.65 (d, J = 4.8 Hz, 1H) , 3.27 (m, 1H), 3.18 (m, 2H), 2.25 (s, 3H), 2.11 (m, 1H), 1.94 (m, 2H), 1.56 (d, J =6.8 Hz, 3H), 1.21 (t, J =7.2 Hz, 3H). MS (ESI): m/z (%) = 430.33 (100%) (M+1). Example-179 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((1-(((R)-pyrrolidin-2-yl)methyl) piperidin-4-yl)amino)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000096_0003
1H NMR (400 MHz, DMSO-d6): δ =9.71 (s, 1H), 9.22 (s, 1H), 8.98 (s, 1H), 8.77 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.95 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 4H), 6.95 (d, J = 8.8 Hz, 1H), 6.58 (d, J = 6.8 Hz, 1H), 5.90 (t, J = 7.2 Hz, 1H), 3.97 (m, 2H), 3.45 (m, 3H), 3.26 (m, 3H), 2.13 (s, 5H), 1.98 (m, 1H), 1.88 (m, 1H), 1.69 (m, 1H), 1.56 (d, J =7.2 Hz, 4H). MS (ESI): m/z (%) = 471.40 (100%) (M+1). Example-180 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl) methyl) amino) benzamide
Figure imgf000097_0001
1H NMR (400 MHz, DMSO-d6): δ =8.76 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.83 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 6.91 (d, J =8.0 Hz, 1H), 6.54 (d, J =2.0 Hz, 1H), 6.53 (d, J =2.8 Hz, 1H), 5.89 (m, 1H), 5.57 (m, 1H), 3.23 (m, 2H), 2.82 (m, 2H), 2.11 (s, 3H), 1.88 (s, 3H), 1.79 (m, 3H), 1.70 (m, 2H), 1.56 (d, J =6.8 Hz, 3H), 1.38 (m,1H). MS (ESI): m/z (%) = 388.23 (100%) (M+1); Free Base +1 Example-181 5-((R)-3-amino-2-((((S)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide tris(2,2,2-trifluoroacetate)
Figure imgf000097_0002
1H NMR (400 MHz, DMSO-d6): δ =10.58 (s, 1H), 8.97 (d, J= 8.0 Hz, 1H), 8.24 (d, J= 8.4 Hz, 1H), 7.97 (d, J= 7.6 Hz, 1H), 7.86 (d, J= 8.4 Hz, 1H), 7.52 (m, 6H), 7.23 (t, J= 4.8 Hz, 2H), 4.02 (d, J= 5.6 Hz, 3H), 3.57 (m, 2H), 3.18 (t, J= 7.2 Hz, 2H), 3.06 (m, 1H), 2.95 (m, 1H), 2.82 (m, 1H), 2.61 (m, 1H), 2.25 (s, 4H), 1.98 (m, 1H), 1.83 (m, 3H), 1.58 (d, J =6.8 Hz, 3H). MS (LC-MS): m/z (%) = 474.5 (100%) (M+1). Example-182 5-((R)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide tris(2,2,2-trifluoroacetate)
Figure imgf000097_0003
1H NMR (400 MHz, DMSO-d6): δ =10.58 (s, 1H), 8.92 (d, J= 8.0 Hz, 1H), 8.24 (d, J= 8.4 Hz, 1H), 7.97 (d, J= 6.8 Hz, 1H), 7.86 (d, J= 8.0 Hz, 1H), 7.55 (m, 6H), 7.23 (t, J= 8.4 Hz, 2H), 7.12 (s, 1H), 7.00 (s, 1H), 4.04 (s, 1H), 3.19 (t, J= 7.2 Hz, 1H), 2.97 (d, J= 5.6 Hz, 1H), 2.75 (m, 2H), 2.25 (s, 3H), 2.01 (m, 1H), 1.88 (m, 2H), 1.58 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 474.19 (100%) (M+1). Example-183 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl) methyl) amino) benzamide dihydrochloride
Figure imgf000098_0001
1H NMR (400 MHz, DMSO-d6): δ =9.45 (s, 1H), 9.05 (s, 1H), 8.83 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.8 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J =8.4 Hz, 1H), 7.55 (m, 4H), 6.99 (d, J =8.8 Hz, 1H), 6.68 (d, J =6.8 Hz, 2H), 5.90 (t, J =7.6 Hz, 1H), 3.64 (m, 1H), 3.38 (m, 1H), 3.32 (d, J =5.6 Hz, 1H), 3.17 (s, 3H), 2.14 (s, 3H), 2.05 (m, 1H), 1.89 (m, 2H), 1.65 (m, 1H), 1.57 (d, J =7.2 Hz, 3H). MS (ESI): m/z (%) = 388.23 (100%) (M+1); Free Base +1 Example-184 2-methyl-5-((((S)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000098_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.83 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 6.90 (d, J =8.4 Hz, 1H), 6.57 (d, J =2.0 Hz, 2H), 6.53 (d, J =2.4 Hz, 1H), 5.89 (t, J =7.2 Hz, 1H), 5.34 (t, J =8.4 Hz, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.84 (m, 1H), 2.33 (m, 1H), 2.26 (s, 3H), 2.12 (s, 4H), 1.87 (d, J =4.8 Hz, 3H), 1.63 (m, 2H), 1.56 (d, J =6.8 Hz, 4H). MS (ESI): m/z (%) = 402.25 (100%) (M+1) Example-185 (R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000098_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.66 (s, 1H), 9.79 (s, 1H), 8.93 (d, J =8.4 Hz, 1H), 8.25 (d, J =8.4 Hz, 1H), 7.97 (d, J =7.6 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.55 (m, 6H) 723 (d J =84 Hz 1H) 594 (t J =72 Hz 1H) 421 (m 1H) 361 (m 2H) 317 (m 2H), 2.87 (m, 3H), 2.55 (m, 1H), 2.25 (s, 3H), 1.94 (m, 2H), 1.58 (d, J =6.8 Hz, 3H). MS (ESI): m/z (%) = 416.23 (100%) (M+1). Example-186 2-methyl-5-(((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000099_0001
1H NMR (400 MHz, DMSO-d6): δ =8.10 (d, J = 8.4 Hz, 1H), 7.91 (d, J = 7.6 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 7.52 (m, 4H), 7.01 (t, J = 8.4 Hz, 1H), 6.68 (d, J = 2.4 Hz, 1H), 6.49 (d, J = 2.4 Hz, 1H), 5.81 (q, J = 7.2 Hz, 1H), 3.31 (m, 2H), 2.95 (d, J = 2.4 Hz, 2H), 2.73 (s, 1H), 2.67 (d, J = 8.8 Hz, 3H), 2.48 (m, 1H), 2.07 (s, 3H), 1.86 (s, 6H), 1.70 (m, 1H), 1.62 (d, J = 6.8 Hz, 3H), 1.46 (m, 1H), 1.02 (m, 1H). MS (ESI): m/z (%) = 416.27 (100%) (M+1). Example-187 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide
Figure imgf000099_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.69 (s, 1H), 8.87 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 6H), 7.14 (d, J = 8.0 Hz, 1H), 5.92 (t, J = 7.6 Hz, 1H), 3.23 (d, J = 2.8 Hz, 1H), 2.96 (d, J = 12.8 Hz, 1H), 2.53 (d, J = 5.2 Hz, 1H), 2.21 (s, 3H), 1.90 (s, 3H), 1.79 (t, J = 8.8 Hz, 2H), 1.57 (d, J = 6.8 Hz, 3H), 1.50 (d, J = 10.8 Hz, 1H), 1.36 (m, 3H). MS (ESI): m/z (%) = 416.23 (100%) (M+1). Example-188 2-methyl-5-((((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000099_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J =8.0 Hz, 1H), 8.24 (d, J =8.4 Hz, 1H), 7.95 (d, J = 7.6 Hz, 1H), 7.83 (d, J =8.0 Hz, 1H), 7.55 (m, 4H), 6.90 (d, J =8.4 Hz, 1H), 658 (d J =24 Hz 1H) 654 (d J =24 Hz 1H) 589 (m 1H) 535 (t J =56 Hz 1H) 320 (m, 1H), 2.96 (m, 1H), 2.83 (m, 1H), 2.33 (m, 1H), 2.27 (s, 3H), 2.12 (m, 4H), 1.87 (m, 2H), 1.64 (m, 2H), 1.56 (d, J =6.8 Hz, 4H).MS (ESI): m/z (%) = 402.22 (100%) (M+1). Example-189 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-piperidin-2-yl) methyl) amino) benzamide 2,2,2-trifluoroacetate
Figure imgf000100_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J = 8.4 Hz, 1H), 8.54 (d, J = 11.6Hz, 1H), 8.24 (d, J = 8.4 Hz, 2H), 7.96 (d, J =8.0 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 8H), 6.97 (d, J = 8.0 Hz, 1H), 6.61 (d, J = 2.4 Hz, 1H), 6.58 (d, J = 2.8 Hz, 1H), 5.90 (m, 2H), 3.25 (q, J = 8.0 Hz, 2H), 3.15 (t, J = 5.2 Hz, 2H), 2.86 (q, J = 10.8 Hz, 1H), 2.14 (s, 3H), 1.89 (d, J = 12.8 Hz, 1H), 1.74 (d, J = 12 Hz, 1H), 1.57 (d, J = 6.8 Hz, 4H), 1.40 (m, 2H). MS (ESI): m/z (%) = 402.25 (100%) (M+1). Example-190 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 2,2,2-trifluoroacetate
Figure imgf000100_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.51 (s, 1H), 8.98 (d, J = 10.4 Hz, 1H), 8.94 (d, J = 8.0 Hz, 1H), 8.79 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.55 (m, 6H), 7.23 (t, J = 8.4 Hz, 1H), 5.93 (m, 1H), 3.87 (t, J = 9.6 Hz, 1H), 3.28 (d, J = 12.8 Hz, 1H), 2.97 (d, J = 11.6 Hz, 1H), 2.25 (s, 3H), 2.19 (d, J = 12.4 Hz, 1H), 1.83 (d, J = 12.0 Hz, 1H), 1.74 (d, J = 14 Hz, 1H), 1.64 (m, 1H), 1.58 (d, J =6.8 Hz, 4H), 1.51 (m, 1H). MS (ESI): m/z (%) = 416.18 (100%) (M+1). Example-191 2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000100_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H) 795 (d J 72 H 1H) 783 (d J 84 H 1H) 755 ( 4H) 690 (d, J = 8.0 Hz, 1H), 6.55 (m, 2H), 5.89 (m, 1H), 3.16 (m, 2H), 2.95 (m, 1H), 2.77 (d, J = 11.6 Hz, 1H), 2.19 (s, 3H), 2.12 (s, 3H), 2.03 (m, 2H), 1.90 (s, 3H), 1.65 (d, J = 8.8 Hz, 2H), 1.56 (d, J = 6.8 Hz, 3H), 1.45 (m, 2H), 1.37 (m, 1H), 1.20 (m, 1H). MS (ESI): m/z (%) = 416.27 (100%) (M+1). Example-192 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-piperidin-2-yl) methyl) amino) benzamide 2,2,2-trifluoroacetate
Figure imgf000101_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.96 (s, 1H), 8.13 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.56 (m, 5H), 6.82 (t, J = 8.0 Hz, 1H), 6.63 (d, J = 7.2 Hz, 1H), 6.30 (d, J = 8.0 Hz, 1H), 5.27 (s, 1H), 4.92 (s, 1H), 4.28 (d, J =12.0 Hz, 1H), 4.03 (q, J = 7.2 Hz, 2H), 3.74 (s, 3H), 3.30 (d, J = 9.2 Hz, 3H), 2.33 (s, 4H), 1.99 (s, 1H), 1.18 (t, J = 6.8 Hz, 1H). MS (ESI): m/z (%) = 402.25 (100%) (M+1). Example-193 (R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000101_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.72 (s, 1H), 9.82 (s, 1H), 8.93 (d, J = 8.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.86 (d, J = 8.4 Hz, 1H), 7.55 (m, 7H), 7.24 (t, J = 3.2 Hz, 1H), 5.93 (m, 1H), 3.84 (m, 1H), 3.11 (m, 2H), 2.72 (s, 3H), 2.25 (s, 3H), 2.10 (d, J = 5.6 Hz, 1H), 1.82 (m, 2H), 1.70 (m, 2H), 1.58 (d, J = 6.8 Hz, 3H), 1.44 (m, 1H). MS (ESI): m/z (%) = 430.25 (100%) (M+1). Example-194 2-methyl-5-(((4-methylpiperazin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000101_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J = 8.4 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 4H), 6.98 (d, J = 8.4 Hz, 1H), 6.61 (t, J = 2.4 Hz, 1H), 5.91 (m, 1H), 3.32 (m, 4H), 3.12 (m, 2H), 2.66 (d, J = 7.6 Hz, 3H) 214 (s 3H) 157 (d J = 68 Hz 3H) MS (ESI): m/z (%) = 41726 (100%) (M+1) Example-195 (S)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperidine-2-carboxamide
Figure imgf000102_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.70 (s, 1H), 8.88 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.13 (d, J =8.0 Hz, 1H), 5.92 (m, 1H), 2.88 (m, 1H), 2.50 (m, 1H), 2.21 (s, 3H), 2.13 (s, 3H), 1.99 (m, 1H), 1.91 (s, 1H), 1.73 (t, J =8.8 Hz, 2H), 1.57 (d, J =7.2 Hz, 6H), 1.22 (m, 1H). MS (ESI): m/z (%) = 430.24 (100%) (M+1). Example-196 tert-butyl (R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) carbamoyl) piperidine-1-carboxylate
Figure imgf000102_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.93 (s, 1H), 8.91 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.0 Hz, 1H), 7.96 (d, J = 7.6 Hz, 1H), 7.84 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.15 (d, J =8.4 Hz, 1H), 5.92 (m, 1H), 2.21 (s, 3H), 2.05 (m, 1H), 1.65 (m, 2H), 1.57 (d, J =6.8 Hz, 4H), 1.37 (m, 1H). MS (ESI): m/z (%) = 416 (100%) (M+1), DeBoc. Example-197 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide
Figure imgf000102_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.68 (s, 1H), 8.87 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.55 (m, 7H), 7.13 (d, J = 8.0 Hz, 1H), 5.92 (m, 1H), 3.23 (d, J = 6.8 Hz, 2H), 2.96 (d, J = 12.8 Hz, 1H), 2.58 (d, J = 12.8 Hz, 2H), 1.89 (s, 4H), 1.78 (m, 3H), 1.57 (d, J =6.8 Hz, 3H), 1.50 (m, 1H), 1.36 (m, 4H). MS (ESI): m/z (%) = 416.23 (100%) (M+1). Example-198 2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000103_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J = 7.2 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.55 (m, 4H), 6.90 (d, J = 8.0 Hz, 1H), 6.57 (d, J = 2.4 Hz, 1H), 6.53 (d, J = 8.4 Hz, 1H), 5.89 (t, J = 7.6 Hz, 1H), 5.29(s, 1H), 3.17 (m, 2H), 2.77 (m, 1H), 2.19 (s, 3H), 2.11 (d, J = 8.4 Hz, 3H), 2.02 (m, 2H), 1.90 (s, 4H), 1.65 (d, J = 8.8 Hz, 2H), 1.56 (d, J = 6.8 Hz, 3H), 1.49 (m, 2H), 1.38 (m, 1H), 1.19 (m, 1H). MS (ESI): m/z (%) = 416.27 (100%) (M+1). Example-199 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hydrochloride
Figure imgf000103_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.85 (s, 1H), 9.41 (d, J = 10 Hz, 1H), 8.95 (d, J = 8.0 Hz, 1H), 8.78 (d, J = 10.4 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.55 (m, 6H), 7.20 (d, J = 8.0 Hz, 1H), 5.93 (d, J = 7.2 Hz, 1H), 3.26 (d, J = 12 Hz, 1H), 3.17 (s, 1H), 2.96 (t, J = 9.6 Hz, 1H) 2.24 (s, 4H), 1.82 (m, 1H), 1.72 (m, 1H), 1.65 (m, 1H), 1.57 (d, J =7.2 Hz, 3H), 1.52 (m, 1H). MS (ESI): m/z (%) = 416.23 (100%) (M+1). Example-200 ethyl (R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) carbamoyl) piperidine-1-carboxylate
Figure imgf000103_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.96 (s, 1H), 8.89 (d, J = 8.0 Hz, 1H), 8.24 (d, J = 8.8 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.55 (m, 7H), 7.14 (d, J = 8.4 Hz, 1H), 5.92 (t, J =7.2 Hz, 1H), 2.21 (s, 3H), 2.09 (m, 1H), 1.91 (s, 1H), 1.65 (m, 2H), 1.57 (d, J = 6.8 Hz, 4H), 1.31 (m, 2H), 1.18 (m, 3H). MS (ESI): m/z (%) = 488.25 (100%) (M+1). Example-201 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide phosphate
Figure imgf000104_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.62 (s, 1H), 8.95 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.55 (m, 6H), 7.18 (d, J = 8.4 Hz, 1H), 3.74 (d, J = 8.8 Hz, 1H), 3.17 (t, J = 6.0Hz, 1H), 2.85 (m, 1H), 2.23 (s, 3H), 2.07 (m, 1H), 1.91 (s, 2H), 1.80 (m, 1H), 1.65 (s, 1H), 1.57 (d, J =6.8 Hz, 4H), 1.52 (d, J =9.2 Hz, 2H). MS (ESI): m/z (%) = 416.19 (100%) (M+1). Example-202 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2- (methylamino) ethyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000104_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.45 (s, 1H), 8.90 (d, J =8.0 Hz, 1H), 8.46 (s, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.86 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.20 (t, J =10.6 Hz, 1H), 5.93 (t, J =7.2 Hz, 1H), 3.22 (s, 2H), 2.56 (s, 3H), 2.24 (s, 3H), 2.01 (m, 1H), 1.71 (m, 3H), 1.57 (d, J =6.8 Hz, 3H), 1.39 (m, 1H); MS (ESI): m/z (%) = 473.29 (100%) (M+1). Example-203 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(((R)- pyrrolidin-2-yl)methyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000104_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.41 (s, 1H), 9.11 (s, 1H), 8.89 (d, J =7.6 Hz, 1H), 8.41 (s, 1H), 8.25 (d, J =8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.86 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.20 (t, J =4.8 Hz, 1H), 5.93 (t, J =7.2 Hz, 1H), 3.84 (s, 3H), 3.16 (s, 3H), 2.24 (s, 3H), 1.98 (m, 2H), 1.84 (m, 2H), 1.71 (m, 2H), 1.57 (d, J =7.2 Hz, 4H), 1.51 (m, 2H), 1.37 (m, 1H); MS (ESI): m/z (%) = 499.35 (100%) (M+1). Example-204 (S)-1-(2-hydroxyethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)piperidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000105_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.70 (s, 1H), 9.78 (s, 1H), 8.94 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.4 Hz, 1H), 7.97 (d, J = 8.0 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.22 (t, J =8.0 Hz, 1H), 5.93 (t, J =7.2 Hz, 1H), 5.31 (s, 1H), 4.03 (s, 1H0, 3.78 (m, 2H), 3.62 (m, 1H), 3.16 (s, 3H), 2.25 (s, 3H), 2.15 (m, 1H), 1.75 (m, 4H), 1.58 (d, J =6.8 Hz, 3H), 1.47 (t, J =6.8 Hz, 1H). MS (ESI): m/z (%) = 460.26 (100%) (M+1). Example-205 (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2,2,2- trifluoroacetyl)piperidine-2-carboxamide
Figure imgf000105_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.16 (s, 1H), 8.92 (d, J =8.0 Hz, 1H), 8.25 (d, J =8.4 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (d, J =8.0 Hz, 1H), 7.55 (m, 6H), 7.17 (t, J =8.0 Hz, 1H), 5.92 (t, J =7.2 Hz, 1H), 3.83 (d, J =13.2 Hz, 1H), 2.22 (s, 4H), 1.81 (m, 2H), 1.68 (m, 1H), 1.58 (d, J =6.8 Hz, 3H), 1.41 (m, 2H); MS (ESI): m/z (%) = 512.21 (100%) (M+1). Example-206 (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 4-methylbenzenesulfonate
Figure imgf000105_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.49 (s, 1H), 8.93 (d, J = 8.0 Hz, 2H), 8.79 (d, J = 9.6 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.55 (m, 9H), 7.22 (d, J = 8.4 Hz, 1H), 7.11 (d, J = 8.0 Hz, 2H), 5.93 (t, J = 7.2 Hz, 1H), 3.87 (t, J = 9.6 Hz, 1H), 3.28 (t, J = 13.2Hz, 1H), 2.99 (m, 1H), 2.25 (s, 3H), 2.19 (m, 1H), 1.83 (m, 1H), 1.73 (m, 1H), 1.63 (m, 1H), 1.57 (d, J =6.8 Hz, 4H), 1.04 (d, J = 6.8 Hz, 3H); MS (ESI): m/z (%) = 416.23 (100%) (M+1). Example-207
Figure imgf000106_0001
(R)-5-hydroxy-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide 1H NMR (400 MHz, DMSO-d6): δ = 9.35 (s, 1H), 8.83 (d, J=8.0Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.62 - 7.49 (m, 4H), 7.00 (d, J=7.6Hz, 1H), 6.32 - 6.69 (m, 2H), 5.90 (t, J=7.2Hz, 1H), 2.16 (s, 1H), 1.57 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 306.147 (100%) (M+H)+. Example-208 tert-butyl ((R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino)-2-oxo-1-phenylethyl)carbamate
Figure imgf000106_0002
IR (KBr): v = 3288, 1672, 1643, 1525, 1494, 1365, 1242, 1163, 844, 777, 698, 557 cm-1 ; MS (TOF): m/z (%) = 438.2240 (60%) (M-Boc+H)+, 536.2559 (100%) (M-H). Example-209 (R)-5-(2-amino-2-methylpropanamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000106_0003
IR (KBr): v = 3259, 2979, 1631, 1527, 1496, 1396, 1182, 798, 777, 650 cm-1 ; MS (TOF): m/z (%) = 390.2285 (100%) (M+H)+, 388.2030 (100%) (M-H). Example-210
Figure imgf000106_0004
N-(2-(1H-indol-3-yl)ethyl)-5-acetamido-2-methylbenzamide 1H NMR (400 MHz, DMSO-d6): δ = 10.82 (s, 1H), 9.94 (s, 1H), 8.34 (t, J=5.6Hz, 1H), 7.58 - 7.50 (m, 3H), 7.34 (d, J=8.0Hz, 1H), 7.20 (s, 1H), 7.14 - 6.97 (m, 3H), 3.53 - 3.48 (m, 2H), 2.93 (d, J=7.6Hz, 2H), 2.22 (s, 3H), 2.03 (s, 3H); MS (TOF): m/z (%) = 336.169 (100%) (M+H)+. Example-211
Figure imgf000107_0001
N-(2-(1H-indol-3-yl)ethyl)-5-(2-aminoacetamido)-2-methylbenzamide 1H NMR (400 MHz, DMSO-d6): δ = 10.82 (s, 1H), 8.34 (t, J=5.6Hz, 1H), 7.60 - 7.57 (m, 3H), 7.34 (d, J=8.0Hz, 1H), 7.21 (d, J=2.0Hz, 1H), 7.15 (d, J=8.0Hz, 1H), 7.09 - 7.05 (m, 1H), 7.01 - 6.97 (m, 1H), 3.54 - 3.48 (m, 2H), 2.28 (s, 2H), 2.93 (t, J=7.2Hz, 2H), 2.23 (s, 3H); MS (TOF): m/z (%) = 351.180 (100%) (M+H)+. Example-212
Figure imgf000107_0002
(R)-N2-(2-(2-hydroxyethoxy)ethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6- dicarboxamide1H NMR (400 MHz, DMSO-d6): δ = 9.51 (d, J=8.4Hz, 1H), 9.43 - 9.42 (m, 1H), 8.24 - 8.14 (m, 4H), 7.96 (d, J=7.6Hz, 1H), 7.87 (d, J=8.0Hz, 1H), 7.69 (d, J=6.8Hz, 1H), 7.61 - 7.51 (m, 3H), 6.07 (t, J=7.6Hz, 1H), 4.64 (t, J=5.6Hz, 1H), 3.62 - 3.45 (m, 8H), 1.74 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 408.2096 (100%) (M+H)+. Example-213
Figure imgf000107_0003
(R)-N2-(4-aminobutyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide 1H NMR (400 MHz, DMSO-d6): δ = 9.61 (d, J=8.4Hz, 1H), 9.49 (t, J=6.0Hz, 1H), 8.24 - 8.13 (m, 4H), 7.97 - 7.95 (m, 1H), 7.86 (d, J=8.0Hz, 1H), 7.70 (d, J=7.2Hz, 1H), 7.61 - 7.52 (m, 3H), 6.07 (t, J=7.6Hz, 1H), 3.42 - 3.34 (m, 2H), 2.69 (t, J=6.8Hz, 2H), 1.74 (d, J=7.2Hz, 3H), 1.63 - 1.58 (m, 2H), 1.55 - 1.49 (m, 2H); MS (TOF): m/z (%) = 391.2193 (100%) (M+H)+. Example-214
Figure imgf000108_0001
(R)-N2-(2-aminoethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide1 1H NMR (400 MHz, DMSO-d6): δ = 9.84 (t, J=5.6Hz, 1H), 9.72 (d, J=8.4Hz, 1H), 8.25 - 8.14 (m, 4H), 7.96 (d, J=8.0Hz, 1H), 7.85 (d, J=8.4Hz, 1H), 7.73 (d, J=6.8Hz, 1H), 7.61 - 7.53 (m, 3H), 6.08 (t, J=7.6Hz, 1H), 3.53 - 3.43 (m, 2H), 2.86 (t, J=6.4Hz, 2H), 1.73 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 363.1804 (100%) (M+H)+. Example-215
Figure imgf000108_0002
(R)-5-((N,N-dimethylsulfamoyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide 1H NMR (400 MHz, DMSO-d6): δ = 9.85 (bs, 1H), 8.93 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 7.97 (d, J=8.4Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.63 - 7.49 (m, 4H), 7.14 - 7.10 (m, 3H), 5.95 - 5.88 (m, 1H), 2.68 (s, 6H), 2.20 (s, 3H), 1.57 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 412.1683 (100%) (M+H)+. Example-216
Figure imgf000108_0003
(R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide 1H NMR (400 MHz, DMSO-d6): δ = 9.79 (bs, 1H), 8.97 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 7.97 (d, J=8.0Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.62 - 7.49 (m, 4H), 7.14 - 7.07 (m, 3H), 5.95 - 5.88 (m, 1H), 3.15 - 3.12 (m, 4H), 2.21 (s, 3H), 1.73 - 1.70 (m, 4H), 1.58 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 438.1833 (100%) (M+H)+. Example-217
Figure imgf000108_0004
(R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide 1H NMR (400 MHz, DMSO-d6): δ = 10.09 (bs, 1H), 9.13 (d, J=8.0Hz, 1H), 8.22 (d, J=8.4Hz, 1H), 7.97 (d, J=7.6Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.64 - 7.49 (m, 4H), 7.41 (d, J=8.4Hz, 1H), 7.23 - 7.20 (m, 1H), 7.13 (d, J=2.4Hz, 1H), 5.92 - 5.85 (m, 1H), 3.17 - 3.14 (m, 4H), 1.75 - 1.72 (m, 4H), 1.57 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 458.1292 (100%) (M+H)+. Example-218 (R)-2-methyl-5-(morpholine-4-sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000109_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.96 (bs, 1H), 8.92 (d, J=8.0Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.97 (d, J=7.6Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.62 - 7.49 (m, 4H), 7.15 - 7.12 (m, 3H), 5.95 - 5.88 (m, 1H), 3.52 - 3.49 (m, 4H), 3.05 - 3.03 (m, 4H), 2.22 (s, 3H), 1.58 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 454.1786 (100%) (M+H)+. Example-219 (R)-2-methyl-5-((4-methylpiperazine)-1-sulfonamido)-N-(1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000109_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.18 (s, 1H), 9.70 (bs, 1H), 8.93 (d, J=8.4Hz, 1H), 8.23 (d, J=8.0Hz, 1H), 7.97 (d, J=8.0Hz, 1H), 7.86 (d, J=8.4Hz, 1H), 7.63 - 7.50 (m, 4H), 7.18 - 7.13 (m, 3H), 5.95 - 5.90 (m, 1H), 3.66 - 3.42 (m, 4H), 3.10 - 2.94 (m, 4H), 2.74 (s, 3H), 2.22 (s, 3H), 1.58 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 467.2097 (100%) (M+H)+. Example-220 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidine-1-sulfonamido)benzamide
Figure imgf000109_0003
1H NMR (400 MHz, DMSO-d6): δ = 9.82 (bs, 1H), 8.90 (d, J=8.4Hz, 1H), 8.24 (d, J=8.0Hz, 1H), 7.96 (d, J=8.4Hz, 1H), 7.85 (d, J=8.4Hz, 1H), 7.62 - 7.48 (m, 4H), 7.15 - 7.10 (m, 3H), 5.95 - 5.88 (m, 1H), 3.06 - 3.05 (m, 4H), 2.21 (s, 3H), 1.57 (d, J=6.8Hz, 3H), 1.52 140 (m 6H); MS (TOF): m/z (%) = 4521992 (100%) (M+H)+ Example-221 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((N-phenylsulfamoyl)amino)benzamide
Figure imgf000110_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.22 - 10.19 (m, 2H), 8.65 (d, J=8.4Hz, 1H), 8.23 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.61 - 7.48 (m, 4H), 7.26 - 7.22 (m, 2H), 7.146.96 (m, 6H), 5.93 - 5.88 (m, 1H), 2.17 (s, 3H), 1.56 (d, J=7.6Hz, 3H); MS (TOF): m/z (%) = 460.1686 (100%) (M+H)+. Example-222 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperazine-1-sulfonamido)benzamide 2,2,2-trifluoroacetate
Figure imgf000110_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.17 (s, 1H), 8.93 (d, J=8.0Hz, 1H), 8.78 (s, 2H), 8.23 (d, J=8.4Hz, 1H), 7.97 (d, J=8.0Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.63 - 7.50 (m, 4H), 7.18 - 7.14 (m, 3H), 5.95 - 5.88 (m, 1H), 3.30 - 3.27 (m, 4H), 3.09 - 3.08 (m, 4H), 2.22 (s, 3H), 1.58 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 453.1950 (100%) (M+H)+. Example-223 2-methyl-5-(methylsulfonoamidimidamido)-N-((R)-1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000110_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.82 - 8.79 (m, 1H), 8.24 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.63 - 7.49 (m, 4H), 7.00 - 6.92 (m, 3H), 6.65 (bs, 2H), 5.92 - 5.88 (m, 1H), 3.09 (s, 3H), 2.17 (s, 3H), 1.56 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 382.1582 (100%) (M+H)+. Example-224 5-(((N-acetylacetamido)(methyl)(oxo)-16-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000111_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.95 (d, J=8.0Hz, 1H), 8.24 (d, J=8.8Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.67 - 7.51 (m, 6H), 8.35 (d, J=8.0Hz, 1H), 5.96 - 5.76 (m, 1H), 3.62 - 3.60 (m, 3H), 2.34 - 2.33 (m, 3H), 1.93 - 1.89 (m, 6H), 1.63 (d, J=6.4Hz, 3H); MS (TOF): m/z (%) = 466.1791 (100%) (M+H)+. Example-225 ethyl (methyl((4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) amino) (oxo)-l6-sulfaneylidene)carbamate
Figure imgf000111_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.03 (bs, 1H), 8.95 (d, J=7.6Hz, 1H), 8.24 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.85 (d, J=7.6Hz, 1H), 7.63 - 7.49 (m, 4H), ), 7.22 - 7.16 (m, 3H), 5.95 - 5.88 (m, 1H), 3.97 (q, J=7.2Hz, 2H), 3.27 (s, 3H), 2.24 (s, 3H), 1.58 (d, J=6.8Hz, 3H), 1.15 (t, J=7.2Hz, 3H); MS (TOF): m/z (%) = 454.1800 (70%) (M+H)+. Example-226 5-(((dimethylamino)(methyl)(oxo)-l6-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000111_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.84 (d, J=8.0Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.62 - 7.49 (m, 4H), 7.01 - 6.88 (m, 3H), 5.91 - 5.88 (m, 1H), 3.00 (s, 3H), 2.74 (s, 6H), 2.18 (s, 3H), 1.56 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 410.1899 (100%) (M+H)+. Example-227 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide
Figure imgf000112_0001
1H NMR (400 MHz, DMSO-d6): δ = 10.12 (s, 1H), 8.91 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 8.05 (d, J=5.2Hz, 2H), 7.96 (d, J=8.8Hz, 1H), 7.85 (d, J=8.4Hz, 1H), 7.62 - 7.49 (m, 6H), 7.16 (d, J=8.4Hz, 1H), 6.92 - 6.84 (m, 1H), 6.53 (d, J=5.6Hz, 2H), 5.95 - 5.92 (m, 1H), 3.94 (d, J=6.0Hz, 2H), 2.33 (s, 3H), 1.57 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 439.3 (100%) (M+H)+. Example-228 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide
Figure imgf000112_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.12 (s, 1H), 8.91 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 8.05 (d, J=5.2Hz, 2H), 7.96 (d, J=8.8Hz, 1H), 7.85 (d, J=8.4Hz, 1H), 7.62 - 7.49 (m, 6H), 7.16 (d, J=8.4Hz, 1H), 6.92 - 6.84 (m, 1H), 6.53 (d, J=5.6Hz, 2H), 5.95 - 5.92 (m, 1H), 3.94 (d, J=6.0Hz, 2H), 2.33 (s, 3H), 1.57 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 439.3 (100%) (M+H)+. Example-229 5-((4-cyanophenyl)sulfonoamidimidamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000112_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.83 - 8.81 (m, 1H), 8.23 (d, J=8.0Hz, 1H), 8.08 - 8.02 (m, 4H), 7.96 (d, J=8.4Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.61 - 7.50 (m, 4H), 7.00 - 6.92 (m, 3H), 5.93 - 5.86 (m, 1H), 2.16 (s, 3H), 1.56 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 469.2 (100%) (M+H)+. Example-230 (R)-5-(2-(dimethylamino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000113_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.75 (s, 1H), 8.80 (d, J=8.0Hz, 1H), 8.25 (d, J=8.4Hz, 1H), 7.96 (d, J=8.4Hz, 1H), 7.85 (d, J=8.4Hz, 1H), 7.66 - 7.49 (m, 6H), 7.14 (d, J=8.4Hz, 1H), 5.94 - 5.90 (m, 1H), 3.05 (s, 2H), 2.26 (s, 6H), 2.22 (s, 3H), 1.58 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 390.3 (100%) (M+H)+. Example-231 (R)-5-((4-fluorobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000113_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J=8.0Hz, 1H), 8.22 (d, J=8.4Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.60 - 7.47 (m, 4H), 7.37 - 7.34 (m, 3H), 7.14 - 7.10 (m, 2H), 6.88 (d, J=8.4Hz, 1H), 6.57 (d, J=2.4Hz, 1H), 6.50 - 6.47 (m, 1H), 6.25 - 6.22 (m, 1H), 5.94 - 5.84 (m, 1H), 4.23 (d, J=6.0Hz, 1H), 2.10 (s, 3H), 1.55 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 413.2 (100%) (M+H)+. Example-232 (R)-5-((4-cyanobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000113_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J=8.4Hz, 1H), 8.21 (d, J=7.6Hz, 1H), 7.96 (d, J=7.2Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.77 (d, J=8.0Hz, 2H), 7.58 - 7.41 (m, 6H), 6.88 (d, J=8.0Hz, 1H), 6.55 (d, J=2.4Hz, 1H), 6.46 - 6.44 (m, 1H), 6.40 - 6.37 (m, 1H), 5.91 - 5.84 (m, 1H), 4.36 (d, J=6.0Hz, 2H), 2.10 (s, 3H), 1.54 (d, J=7.2Hz, 3H); ESI-MS: m/z (%) = 420.0 (100%) (M+H)+. Example-233 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((4-(trifluoromethyl) benzyl) amino) benzamide
Figure imgf000114_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J=8.0Hz, 1H), 8.22 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.83 (d, J=8.0Hz, 1H), 6.67 (d, J=8.0Hz, 2H), 7.58 - 7.46 (m, 6H), 6.88 (d, J=8.4Hz, 1H), 6.57 (d, J=2.4Hz, 1H), 6.48 - 6.46 (m, 1H), 6.39 - 6.36 (m, 1H), 5.89 - 5.84 (m, 1H), 4.36 (d, J=6.0Hz, 2H), 2.10 (s, 3H), 1.54 (d, J=7.2Hz, 3H); ESI-MS: m/z (%) = 463.0 (100%) (M+H)+. Example-234 (R)-5-((6-aminopyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000114_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.82 (d, J=8.0Hz, 1H), 8.22 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.83 (d, J=8.0Hz, 1H), 7.75 (d, J=2.4Hz, 1H), 7.62 - 7.47 (m, 5H), 7.24 - 7.21 (m, 1H), 6.96 (d, J=8.4Hz, 1H), 6.73 - 6.67 (m, 2H), 6.47 (d, J=8.8Hz, 1H), 5.90 - 5.87 (m, 1H), 5.69 (bs, 2H), 2.14 (s, 3H), 1.55 (d, J=7.2Hz, 3H); ESI-MS: m/z (%) = 397.10 (100%) (M+H)+. Example-235 (R)-2-methyl-5-(((5-methylthiophen-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000114_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.75 (d, J=8.0Hz, 1H), 8.23 (d, J=8.4Hz, 1H), 7.96 (d, J=8.4Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.62 - 7.48 (m, 4H), 6.90 (d, J=8.0Hz, 1H), 6.77 (d, J=3.2Hz, 1H), 6.62 - 6.55 (m, 3H), 6.16 (t, J=6.0Hz, 1H), 5.92 - 5.85 (m, 1H), 4.33 (d, J=6.0Hz, 2H), 2.36 (s, 3H), 2.11 (s, 3H), 1.55 (d, J=6.8Hz, 3H); ESI-MS: m/z (%) = 415.10 (100%) (M+H)+. Example-236 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-3-ylmethyl)amino)benzamide 2,2,2- trifluoroacetate
Figure imgf000115_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.77 - 8.68 (m, 3H), 8.23 - 8.19 (m, 2H), 7.97 - 7.94 (m, 1H), 7.84 (d, J=8.0Hz, 1H), 7.78 - 7.75 (m, 1H), 7.59 - 7.48 (m, 4H), 6.92 (d, J=8.4Hz, 1H), 6.59 - 6.52 (m, 2H), 5.91 - 5.84 (m, 1H), 4.42 (s, 2H), 2.11 (s, 3H), 1.55 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 396.2030 (100%) (M+H)+ Example-237 (R)-2-methyl-5-(((1-methyl-1H-pyrrol-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000115_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.63 - 7.49 (m, 4H), 6.92 (d, J=8.0Hz, 1H), 6.67 - 6.61 (m, 3H), 5.96 - 5.80 (m, 4H), 4.13 (d, J=5.2Hz, 2H), 3.56 (s, 3H), 2.12 (s, 3H), 1.56 (d, J=7.2Hz, 3H); ESI-MS: m/z (%) = 398.2204 (30%) (M+H)+. Example-238 (R)-5-((6-hydroxypyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000115_0003
1H NMR (400 MHz, DMSO-d6): δ = 11.30 (bs, 1H), 8.83 (d, J=8.0Hz, 1H), 8.22 (d, J=8.4Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.60 - 7.46 (m, 5H), 7.36 - 7.28 (m, 1H), 7.16 - 7.15 (m, 1H), 6.99 (d, J=8.0Hz, 1H), 6.67 - 6.63 (m, 2H), 6.38 (d, J=9.6Hz, 1H), 5.92 - 5.87 (m, 1H), 2.15 (s, 3H), 1.55 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 398.1827 (100%) (M+H)+. Example-239 (R)-5-(2-((cyclopropylmethyl)amino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000116_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.90 (bs, 1H), 8.91 (d, J=8.4Hz, 1H), 8.25 (d, J=8.4Hz, 1H), 7.97 (d, J=8.0Hz, 1H), 7.85 (d, J=8.0Hz, 1H), 7.63 - 7.49 (m, 6H), 7.15 (d, J=8.4Hz, 1H), 5.94 - 5.90 (m, 1H), 2.42 (d, J=6.4Hz, 2H), 2.22 (s, 3H), 1.91 (s, 2H), 1.58 (t, J=6.8Hz, 3H), 0.92 - 0.88 (m, 1H), 0.44 - 0.39 (m, 2H), 0.13 - 0.09 (m, 2H); MS (TOF): m/z (%) = 416.3028 (100%) (M+H)+. Example-240 (R)-5-(2-(isoindolin-2-yl)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide
Figure imgf000116_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.89 (s, 1H), 8.88 (d, J=8.0Hz, 1H), 8.25 (d, J=8.4Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.68 - 7.48 (m, 6H), 7.27 - 7.13 (m, 5H), 5.95 - 5.88 (m, 1H), 4.05 (s, 4H), 3.54 (s, 2H), 2.22 (s, 3H), 1.57 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 464.2854 (100%) (M+H)+. Example-241 (R)-5-(((1H-imidazol-5-yl)methyl)amino)-2-methyl-N-(1-(naphthalen-1-yl) ethyl) benzamide
Figure imgf000116_0003
1H NMR (400 MHz, DMSO-d6): δ = 11.88 (bs, 1H), 8.76 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.83 (d, J=8.0Hz, 1H), 7.62 - 7.49 (m, 5H), 6.91 - 6.89 (m, 2H), 6.65 - 6.58 (m, 2H), 5.93 - 5.85 (m, 1H), 5.78 - 5.75 (m, 1H), 4.12 (d, J=5.2Hz, 2H), 2.11 (s, 3H), 1.56 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 385.1992 (100%) (M+H)+. Example-242 (R)-6-amino-3-methyl-N-(1-(naphthalen-1-yl)ethyl)picolinamide
Figure imgf000117_0001
1H NMR (400 MHz, DMSO-d6): δ = 8.72 (d, J=8.4Hz, 1H), 8.19 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.86 (d, J=8.4Hz, 1H), 7.63 - 7.49 (m, 4H), 7.29 (d, J=8.4Hz, 1H), 6.52 (d, J=8.4Hz, 1H), 5.94 (s, 2H), 5.91 - 5.84 (m, 1H), 2.32 (s, 3H), 1.61 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 306.1892 (100%) (M+H)+. Example-243 (R)-3-methyl-N-(1-(naphthalen-1-yl)ethyl)-6-(piperidin-4-ylamino)picolinamide 2,2,2-trifluoroacetate
Figure imgf000117_0002
1H NMR (400 MHz, DMSO-d6): δ = 8.71 (d, J=8.0Hz, 1H), 8.51 (bs, 1H), 8.45 (bs, 1H), 8.21 (d, J=8.4Hz, 1H), 7.97 (d, J=7.6Hz, 1H), 7.86 (d, J=8.0Hz, 1H), 7.64 - 7.48 (m, 4H), 7.35 (d, J=8.8Hz, 1H), 6.75 (bs, 1H), 6.60 (d, J=8.4Hz, 1H), 5.90 - 5.82 (m, 1H), 3.92 - 3.79 (m, 1H), 3.33 - 3.22 (m, 2H), 3.01 - 2.84 (m, 2H), 2.31 (s, 3H), 2.09 - 1.99 (m, 2H), 1.62 (d, J=6.8Hz, 3H), 1.57 - 1.49 (m, 2H); MS (TOF): m/z (%) = 389.2330 (100%) (M+H)+. Example-244 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((((R)-pyrrolidin-2-yl) methyl) amino) picolinamide 2,2,2-trifluoroacetate
Figure imgf000117_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.94 (bs, 1H), 8.86 (bs, 1H), 8.73 (d, J=8.4Hz, 1H), 8.22 (d, J=8.4Hz, 1H), 7.97 (d, J=7.6Hz, 1H), 7.87 (d, J=8.0Hz, 1H), 7.65 - 7.50 (m, 4H), 7.39 (d, J=8.4Hz, 1H), 6.94 (bs, 1H), 6.66 (d, J=8.4Hz, 1H), 5.94 - 5.87 (m, 1H), 3.73 - 3.72 (m, 1H), 3.60 - 3.56 (m, 1H), 3.45 - 3.40 (m, 1H), 3.08 - 3.00 (m, 2H), 2.28 (s, 3H), 1.94 - 1.75 (m, 3H), 1.66 - 1.57 (m, 4H); MS (TOF): m/z (%) = 389.2336 (100%) (M+H)+. Example-245 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((R)-pyrrolidine-2-carboxamido) picolinamide 2,2,2-trifluoroacetate
Figure imgf000118_0001
1H NMR (400 MHz, DMSO-d6): δ = 11.16 (bs, 1H), 9.34 (bs, 1H), 8.89 (d, J=8.4Hz, 1H), 8.69 (bs, 1H), 8.23 (d, J=8.4Hz, 1H), 8.04 (d, J=8.4Hz, 1H), 7.97 (d, J=7.6Hz, 1H), 7.87 (d, J=8.0Hz, 1H), 7.78 (d, J=8.4Hz, 1H), 7.64 - 7.50 (m, 4H), 5.95 (t, J=7.2Hz, 1H), 4.50 - 4.30 (m, 1H), 3.28 - 3.27 (m, 2H), 2.39 - 2.33 (m, 4H), 1.95 - 1.85 (m, 3H), 1.62 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 403.2141 (100%) (M+H)+. Example-246 (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000118_0002
1H NMR (400 MHz, DMSO-d6): δ = 10.21 (s, 1H), 9.27 – 9.24 (m, 1H), 8.91 (d, J = 8.0 Hz, 2H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 – 7.50 (m, 6H), 7.23 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 5.97 – 5.90 (m, 1H), 3.29 – 3.26 (m, 2H), 2.33 – 2.32 (m, 1H), 2.25 (s, 3H), 2.12 – 2.08 (m, 2H), 1.92 – 1.79 (m, 1H), 1.67 (s, 3H), 1.58 (d, J = 7.2 Hz, 3H); MS (TOF): m/z (%) = 416.2332(100%) (M+H)+, 414.2235 (20%) (M-H). Example-247 5-(((S)-2,3-diaminopropyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000118_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.76 (d, J=8.0Hz, 1H), 8.24 (d, J=8.0Hz, 2H), 8.18 (bs, 4H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.63 - 7.45 (m, 4H), 6.99 (d, J=8.4Hz, 1H), 6.63 - 6.61 (m, 2H), 5.95 - 5.88 (m, 1H), 3.52 - 3.50 (m, 1H), 3.32 - 3.30 (m, 2H), 3.20 - 3.16 (m, 1H), 3.12 - 3.06 (m, 1H), 2.14 (s, 3H), 1.57 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 377.2342 (100%) (M+H)+ (Free base). Example-248 5-(((S)-3-amino-2-(dimethylamino)propyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000119_0001
1H NMR (400 MHz, D2O): δ = 8.21 (d, J=8.4Hz, 1H), 7.94 (d, J=7.6Hz, 1H), 7.83 (d, J=8.0Hz, 1H), 7.61 - 7.47 (m, 4H), 7.08 (d, J=8.4Hz, 1H), 6.84 (d, J=8.0Hz, 1H), 6.76 (s, 1H), 5.91 - 5.86 (m, 1H), 3.67 - 3.64 (m, 2H), 3.48 - 3.33 (m, 2H), 3.03 - 3.00 (m, 1H), 2.85 (s, 3H), 2.74 (s, 6H), 2.16 (s, 3H), 1.58 (d, J=6.8Hz, 3H); MS (TOF): m/z (%) = 419.2785 (100%) (M+H)+ (Free base). Example-249 5-(((S)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000119_0002
1H NMR (400 MHz, DMSO d6): δ = 8.74 (d, J=8.4Hz, 1H), 7.24 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.63 - 7.49 (m, 4H), 6.96 (d, J=8.4Hz, 1H), 6.58 - 6.56 (m, 2H), 5.93 - 5.89 (m, 1H), 3.56 - 3.55 (m, 1H), 3.22 - 3.19 (m, 3H), 3.09 - 2.77 (m, 6H), 2.13 (s, 3H), 2.03 - 1.83 (m, 3H), 1.64 - 1.61 (m, 1H), 1.57 (d, J=7.2Hz, 3H); MS (TOF): m/z (%) = 460.3069 (100%) (M+H)+ (Free base). Example-250 5-(((S)-2-amino-3-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000119_0003
1H NMR (400 MHz, DMSO-d6): δ = 8.78 (d, J=8.0Hz, 1H), 8.24 (d, J=8.4Hz, 1H), 7.96 (d, J=8.0Hz, 1H), 7.84 (d, J=8.0Hz, 1H), 7.63 - 7.48 (m, 4H), 6.91 (d, J=8.4Hz, 1H), 6.56 - 6.53 (m, 2H), 5.93 - 5.88 (m, 1H), 3.29 - 3.24 (m, 1H), 3.06 - 3.02 (m, 1H), 2.96 - 2.87 (m, 4H), 2.67 - 2.54 (m, 3H), 2.46 - 2.43 (m, 1H), 2.12 (s, 3H), 1.88 - 1.64 (m, 3H), 1.56 (d, J=7.2Hz, 3H), 1.43 - 1.37 (m, 1H); MS (TOF): m/z (%) = 460.1982 (40%) (M+H)+ (Free base). Example-251 (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000120_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.99 (s, 1H), 8.96 - 8.91 (m, 3H), 8.25 (d, J=8.4Hz, 1H), 7.97 (d, J=8.0Hz, 1H), 7.86 (d, J=8.4Hz, 1H), 7.64 - 7.51 (m, 6H), 7.23 (d, J=8.4Hz, 1H), 5.97 - 5.90 (m, 1H), 3.25 - 3.05 (m, 2H), 2.25 - 2.14 (m, 4H), 1.96 - 1.90 (m, 1H), 1.73 - 1.37 (m, 10H); MS (TOF): m/z (%) = 430.1767(100%) (M+H)+ (Free base). Example-252 (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperidine-2-carboxamide
Figure imgf000120_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.73 (s, 1H), 8.88 (d, J=8.0Hz, 1H), 8.25 (d, J=8.0Hz, 1H), 7.96 (d, J=7.6Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.66 - 7.50 (m, 6H), 7.15 - 7.13 (m, 1H), 5.95 - 5.88 (m, 1H), 2.85 - 2.82 (m, 1H), 2.67 - 2.61 (m, 1H), 2.30 - 2.15 (m, 4H), 1.59 - 1.57 (m, 4H), 1.33 - 1.10 (m, 7H); MS (TOF): m/z (%) = 430.2506(100%) (M+H)+. Example-253 (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate
Figure imgf000120_0003
1H NMR (400 MHz, DMSO-d6): δ = 10.00 (s, 1H), 8.95 - 8.91 (m, 3H), 8.25 (d, J=8.4Hz, 1H), 7.98 - 7.96 (m, 1H), 7.85 (d, J=8.0Hz, 1H), 7.64 - 7.51 (m, 6H), 7.23 (d, J=8.4Hz, 1H), 5.95 - 5.92 (m, 1H), 3.25 - 3.05 (m, 2H), 2.25 - 2.21 (m, 4H), 2.00 - 1.90 (m, 1H), 1.70 - 1.57 (m, 9H), 1.50 - 1.35 (m, 1H); MS (TOF): m/z (%) = 430.2510 (100%) (M+H)+ (Free base). Example-254 (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrazine-2- carboxamide
Figure imgf000121_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.79 (s, 1H), 9.30 (s, 1H), 8.93 (s, 2H), 7.82 (s, 1H), 8.27 (d, J=12 Hz, 1H), 7.84-7.98 (m, 4H), 7.53-7.66 (m, 4H), 7.23 (d, J=8 Hz, 1H), 5.90-6.00 (m, 1H), 2.26 (s, 3H), 1.58 (d, J = 6.8 Hz, 3H); MS (TOF): m/z (%) = 411.1991 (100%) (M+H)+. Example-255 (R)-5-(cyclopropanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000121_0002
1H NMR (400 MHz, DMSO3-d4): δ = 9.69 (s, 1H), 8.93 (d, J=8 Hz, 2H), 8.24 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.85 (d, J=8 Hz, 4H), 7.49-7.63 (m, 4H), 7.16-7.19 (m, 3H), 5.90-6.00 (m, 1H), 2.50-2.59 (m, 1H), 2.22 (s, 3H), 1.58 (d, J = 8 Hz, 3H), 0.91-0.93 (m, 4H); IR (KBr): v = 1635, 1490, 1143, 777; MS (TOF): m/z (%) = 409.1822 (100%) (M+H)+. Example-256 5-((S)-2-amino-3-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000121_0003
1H NMR (400 MHz, DMSO3-d4): δ = 8.87 (d, J=8 Hz, 1H), 8.25 (d, J=8.4 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.50-7.66 (m, 6H), 7.16 (d, J= 8.4 Hz, 1H), 5.90-5.94 (m, 1H), 3.43-3.46 (m, 1H), 3.29-3.38 (m, 1H), 3.06-3.08 (m, 1H), 2.67-2.68 (m, 1H), 2.53 (s, 3H), 1.57 (d, J = 8 Hz, 3H), 0.91-0.94 (m, 4H); MS (TOF): m/z (%) = 493.1904 (100%) (M+H)+. Example-257 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen- 1-yl) ethyl)benzamide
Figure imgf000122_0001
1H NMR (400 MHz, DMSO3-d4): δ = 8.90 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.96 (d, J=7.2 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.50-7.67 (m, 6H), 7.16 (d, J=8Hz, 1H), 5.90-5.92 (m, 1H), 3.42-3.45 (m, 1H), 3.23-3.33 (m, 1H), 3.04-3.07 (m, 1H), 2.91 (s, 3H), 2.22 (s, 3H), 1.57 (d, J = 6.8 Hz, 3H); IR (KBr): v = 3290, 1683, 1641, 1614, 1541, 1298, 1145, 1124, 769; MS (TOF): m/z (%) = 469.1893 (100%) (M+H)+. Example-258 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide
Figure imgf000122_0002
1H NMR (400 MHz, DMSO3-d4): δ = 8.93 (d, J=8.4 Hz, 1H), 8.80 (s, 1H), 8.24 (d, J=8.4 Hz, 1H), 8.16-8.18 (m, 2H), 7.96 (d, J=7.6Hz, 1H), 7.85 (d, J=8 Hz, 1H), 7.49-7.85 (m, 4H), 7.09-7.21 (m, 3H), 6.87-6.88 (m, 2H), 5.91-5.93 (m, 1H), 2.33 (s, 3H), 1.58 (d, J = 8 Hz, 3H); IR (KBr): v = 3277, 1641, 1593, 1523, 1496, 1348, 991, 771; MS (TOF): m/z (%) = 382.1894 (100%) (M+H)+. Example-259 5-((S)-3-amino-2-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000122_0003
1H NMR (400 MHz, DMSO3-d4): δ = 8.91 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 7.49-7.62 (m, 6H), 7.16 (d, J=8Hz, 1H), 5.90-5.94 (m, 1H), 3.90-3.93 (m, 1H), 2.80-2.85 (m, 2H), 2.22 (s, 3H), 1.56 (d, J = 6.8 Hz, 3H), 0.92-0.88 (m, 4H), 0.70-0.78 (m, 1H); IR (KBr): v = 3261, 1537, 1323, 1301, 1143, 777; MS (TOF): m/z (%) = 495.2045 (100%) (M+H)+; 493.1899 (100%) (M+H)+. Example-260 (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinolin-2-ylmethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000123_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.76 (s, 1H), 8.95 (t, J=6 Hz, 1H), 8.39 (d, J=8 Hz, 2H), 7.99-8.01 (m, 2H), 7.55-7.68 (m, 5H), 7.26-7.29 (m, 1H), 4.74 (d, J=8 Hz, 2H), 4.27-4.30 (m, 1H), 3.32-3.39(m,2), 3.04-3.07 (m, 1H), 2.33 (s, 3H); MS (TOF): m/z (%) = 378.1919 (35%) (M+H)+; 376.1797(35%) (M-H). Example-261 (R)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide
Figure imgf000123_0002
1H NMR (400 MHz, DMSO-d6): δ = 9.48 (s, 1H), 8.86 (d, J = 8.0 Hz, 1H), 8.25 (d, J = 8.4 Hz, 1H), 7.96 (dd, J = 7.6 Hz, J = 1.2 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.67 – 7.49 (m, 7H), 7.15 – 7.12 (m, 1H), 5.93 – 5.90 (m, 1H), 3.14 – 3.09 (m, 1H), 2.24 (s, 3H), 2.21 (s, 3H), 2.05 – 2.00 (m, 1H), 1.77 – 1.68 (m, 3H), 1.58 (d, J = 6.8 Hz , 3H), 1.15 (s, 3H); IR (KBr): v = 3275, 1643, 1510, 1180, 1124, 800, 777, 509 cm-1; MS (ESI): m/z (%) = 430.3 (100%) (M+H)+, 428.2 (40%) (M-H). Example-262 5-((S)-3-amino-2-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen- 1-yl)ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000124_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.29 (s, 1H), 8.91 (d, J=8 Hz, 1H), 8.25 (d, J=8 Hz, 1H), 7.84-7.98 (m, 4H), 7.61-7.63 (m, 2H), 7.51-7.57 (m, 6H), 7.19-7.21 (m, 1H), 5.90-5.95 (m, 1H), 4.10-4.20 (m, 1H), 3.32-3.33 (m, 1H), 3.02 (s, 4H), 2.24 (s, 3H), 1.58 (d, J = 8 Hz, 3H); MS (TOF): m/z (%) = 469.1900 (100%) (M+H)+; 467.1779 (100%) (M- H)-. Example-263 5-((S)-2,4-diaminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000124_0002
1H NMR (400 MHz, DMSO3-d4): δ = 10.60 (bs, 1H), 8.92 (d, J=8 Hz, 1H), 8.41 (d, J=8 Hz, 1H), 8.25 (d, J=8 Hz, 1H), 8.11 (d, J=8 Hz, 2H), 7.97 (d, J=8 Hz, 2H), 7.49- 7.73 (m, 6H), 7.23 (d, J=8 Hz, 1H), 5.90-5.97 (m, 1H), 3.95-4.05 (m, 1H), 2.84-2.90 (m, 1H), 2.33 (s, 3H), 2.05-2.09 (m, 2H), 1.57 (d, J=7.2 Hz, 3H); MS (TOF): m/z (%) = 405.2282 (100%) (M+H)+. Example-264 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidin-4-ylamino)benzamide
Figure imgf000124_0003
1H NMR (400 MHz, DMSO3-d4): δ = 8.75 (d, J=8 Hz, 1H), 8.24 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.48-7.62 (m, 4H), 6.89 (d, J=8 Hz, 1H), 6.50- 6.53(m, 2H), 5.90-6.00 (m, 1H), 5.41 (d, J=8 Hz, 1H), 2.98-3.10 (m, 1H), 2.58-2.67 (m, 2H), 2.50-2.51 (m, 2H), 2.10 (s, 3H), 1.82-1.85 (m, 2H), 1.55 (d, J=7.2 Hz, 3H), 1.17-1.24 (m, 3H); IR (KBr): v = 2929, 1639, 1608, 1510, 1255, 800, 777; MS (TOF): m/z (%) = 388.2390 (100%) (M+H)+. Example-265 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((tetrahydro-2H-pyran-4- yl)amino)benzamide
Figure imgf000125_0001
1H NMR (400 MHz, DMSO3-d4): δ = 8.76 (d, J=8 Hz, 1H), 8.23 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.48-7.62 (m, 4H), 6.91 (d, J=8.8 Hz, 1H), 6.50-6.53(m, 2H), 5.85-5.95 (m, 1H), 5.55 (m, 1H), 3.84-3.86 (m, 2H), 3.38-3.41 (m, 2H), 2.11 (s, 3H), 1.82-1.85 (m, 2H), 1.56 (d, J=6.8 Hz, 3H), 1.32-1.34 (m, 2H); IR (KBr): v = 2922, 1637, 1608, 1508, 1134, 1085, 800, 777; MS (TOF): m/z (%) = 389.2226 (100%) (M+H)+. Example-266 (R)-5-((9H-purin-6-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000125_0002
1H NMR (400 MHz, DMSO3-d4): δ = 13.16 (s, 1H), 9.80 (s, 1H), 8.90 (d, J=8 Hz, 1H), 8.34 (s, 1H), 8.27 (d, J=8 Hz, 2H), 7.93-7.98 (m, 4H), 7.51-7.67 (m, 4H), 7.17 (d, J=8 Hz, 1H), 5.90-5.92 (m, 1H), 2.33 (s, 3H), 1.58 (d, J=8 Hz, 3H); IR (KBr): v = 3271, 1627, 1489, 1303, 769; MS (TOF): m/z (%) = 423.1927 (100%) (M+H)+. Example-267 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridine-3-sulfonamido)benzamide
Figure imgf000125_0003
1H NMR (400 MHz, DMSO3-d4): δ = 10.50 (bs, 1H), 8.88 (m, 2H), 8.77-8.78 (m, 1H), 8.00-8.19 (m, 4H), 7.50-7.60 (m, 5H), 7.02-7.10 (m, 3H), 5.86-5.90 (m, 1H), 2.33 (s, 3H), 1.55 (d, J=8 Hz, 3H); IR (KBr): v = 1633, 1492, 1323, 1166, 1107, 777; MS (TOF): m/z (%) = 446.1539 (80%) (M+H)+. Example-268 5-((S)-2,6-diaminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000126_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.53 (bs, 1H), 8.91 (d, J=8 Hz, 1H), 8.24- 8.26 (m, 3H), 7.85-7.98 (m, 2H),7.49-7.74 (m, 9H), 5.92-5.95 (m, 1H), 3.89-3.92 (m, 1H), 2.74-2.77 (m, 2H), 2.33 (s, 3H), 1.79-1.89 (m, 2H), 1.28-1.79 (m, 5H), 1.24-1.28 (m, 2H); IR (KBr): v = 1670, 1635, 1199, 1182, 11323, 798; MS (TOF): m/z (%) = 433.2596 (100%) (M+H)+. Example-269 5-((S)-2-amino-3-(pyridine-3-sulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000126_0002
1H NMR (400 MHz, DMSO3-d4): δ = 8.87 (d, J=8Hz, 1H), 8.25 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.55-7.64 (m, 8H), 7.15 (d, J=8 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 6.60-6.80 (bs, 1H), 5.75-5.77 (m, 1H), 3.10-3.33 (m, 1H), 2.60-2.66 (m, 1H), 2.50-2.55 (m, 1H), 2.22 (s, 3H), 1.57 (d, J=7.2 Hz, 3H); IR (KBr): v = 1624, 1521, 1139, 1097, 777; MS: m/z (%) = 570.4 (100%) (M-H)-. Example-270 5-((S)-2-amino-3-((3,5-difluorophenyl)sulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide
Figure imgf000126_0003
1H NMR (400 MHz, DMSO3-d4): δ = 8.88 (d, J=8Hz, 1H), 8.25 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.49-7.63 (m, 9H), 7.15 (d, J=8 Hz, 1H), 5.91- 5.93 (m, 1H), 3.33-3.41 (m, 1H), 3.07-3.09 (m, 1H), 2.91-2.94 (m, 1H), 2.33 (s, 3H), 1.57 (d, J=7.2 Hz, 3H); IR (KBr): v = 1604, 1521, 1438, 1296, 1155, 1124, 777; MS: m/z (%) = 567.3 (100%) (M+H)+. Example-271 (R)-2-methyl-5-((1-(methylsulfonyl)piperidin-4-yl)amino)-N-(1-(naphthalen-1- yl)ethyl)benzamide
Figure imgf000127_0001
1H NMR (400 MHz, DMSO3-d4): δ = 8.77 (d, J=8 Hz, 1H), 8.24 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.84 (d, J=8 Hz, 1H), 7.51-7.61 (m, 4H), 6.92 (d, J=8 Hz, 1H), 6.50- 6.55(m, 2H), 5.87-5.91 (m, 1H), 5.51 (d, J=8 Hz, 1H), 3.48-3.51 (m, 2H), 2.85-2.90 (m, 6H), 2.11 (s, 3H), 1.94-1.97 (m, 2H), 1.56 (d, J=8 Hz, 3H), 1.41-1.43 (m, 2H); IR (KBr): v = 3323, 1641, 1321, 1147, 779; MS : m/z (%) = 466.3 (100%) (M+H)+. Example-272 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl) amino) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000127_0002
1H NMR (400 MHz, DMSO3-d4): δ = 8.74 (d, J=8Hz, 1H), 8.53-8.56 (m, 1H), 8.24 (d, J=8Hz, 2H), 7.96 (d, J=8Hz, 1H), 7.83-7.86 (m, 1H), 7.48-7.63 (m, 5H), 6.92 (d, J=8Hz, 1H), 6.53-6.54 (m, 2H), 5.88-5.91 (m, 1H), 3.27-3.30 (m, 2H), 2.78-2.91 (m, 4H), 2.33 (s, 3H), 1.77-1.87 (m, 3H), 1.56 (d, J=8Hz, 3H), 1.24-1.30 (m, 2H); IR (KBr): v = 1666, 1197, 1176, 1126, 798, 777; MS : m/z (%) = 402.4 (100%) (M+H)+. Example-273 N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) amino)-3-oxopropyl)piperazine-2-carboxamide tris(2,2,2-trifluoroacetate)
Figure imgf000128_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.56 (d, J=8Hz, 1H), 8.92 (d, J=8Hz, 1H), 8.23-8.26 (m, 3H), 7.97 (d, J=8Hz, 1H), 7.86 (d, J=8Hz, 1H), 7.49-7.63 (m, 6H), 7.20-7.23 (m, 1H), 5.90-5.98 (m, 1H), 4.01-4.03 (m, 1H), 3.91-3.97 (m, 2H), 2.83-2.95 (m, 4H), 2.33 (s, 3H), 1.57 (d, J=8Hz, 3H); IR (KBr): v = 1666, 1182, 1128, 798 cm -1; MS : m/z (%) = 469.1893 (100%) (M+H)+; Example-274 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-4-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000128_0002
1H NMR (400 MHz, DMSO3-d4): δ = 8.71-8.77 (m, 3H), 8.21 (d, J=8Hz, 1H), 7.94- 7.97 (m, 2H), 7.83 (d, J=8Hz, 2H), 7.47-7.59 (m, 4H), 6.90 (d, J=8Hz, 1H), 6.55 (s, 1H), 6.45-6.54 (m, 1H), 5.85-5.91 (m, 1H), 5.83 (s, 2H), 2.33 (s, 3H), 1.56 (d, J=8Hz, 3H); IR (KBr): v = 1668, 1639, 1608, 1504, 1197, 1178, 1126, 779; MS: m/z (%) = 369.3 (100%) (M+H)+. Example-275 N-(4-methyl-3-((quinolin-4-ylmethyl)carbamoyl)phenyl)piperazine-2-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000128_0003
1H NMR (400 MHz, DMSO3-d4): δ = 10.78 (s, 1H), 9.05 (t, J=6Hz, 1H), 8.90 (d, J=4.4Hz, 1H), 8.32 (d, J=8Hz, 1H), 8.11 (d, J=8Hz, 1H), 7.71-7.88 (m, 2H), 7.52-7.62 (m, 3H), 7.26-7.29 (m, 1H), 5.00 (s, 2H), 4.29-4.31 (m, 1H), 3.89-3.93 (m, 1H), 3.44-3.53 (m, 2H), 3.23-3.29 (m, 3H), 3.47 (s, 3H); IR (KBr): v = 1660, 1178, 1124, 833, 796, 721; MS : m/z (%) = 404.3 (100%) (M+H)+. Example-276 5-((S)-2-amino-3-(1H-imidazol-4-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000129_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.57 (s, 1H), 8.92 (d, J=8Hz, 1H), 8.84 (bs, 1H), 8.65-8.80 (bs, 2H), 8.24 (d, J=8Hz, 1H), 7.84-7.96 (m, 2H), 7.47-7.62 (m, 6H), 7.38 (s, 1H), 7.13-7.26 (m, 1H), 5.91-5.95 (m, 1H), 4.23-4.26 (m, 1H), 3.17-3.31 (m, 2H), 2.67 (s, 3H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1666, 1199, 1132, 798, 721; MS : m/z (%) = 442.10 (100%) (M+H)+. Example-277 5-((S)-2-amino-3-(1H-indol-3-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000129_0002
1H NMR (400 MHz, DMSO3-d4): δ = 10.55 (s, 1H), 10.51 (s, 1H), 8.92 (d, J=8Hz, 1H), 8.20-8.26 (m, 4H), 7.97 (d, J=8Hz, 1H), 7.66 (d, J=8Hz, 1H), 7.49-7.63 (m, 6H), 7.43 (s, 1H), 7.37 (d, J=8Hz, 1H), 7.20-7.24 (m, 2H), 6.98-7.11 (m, 2H), 5.92-5.96 (m, 1H), 4.11 (bs, 1H), 3.29-3.43 (m, 2H), 2.57 (s, 3H), 1.57 (d, J=8Hz, 3H); IR (KBr): v = 1668, 1512, 1494, 1199, 1182, 1134, 798, 777; MS : m/z (%) = 491.00 (100%) (M+H)+. Example-278 5-((S)-2-amino-3-((N,N-dimethylsulfamoyl)amino)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000129_0003
1H NMR (400 MHz, DMSO3-d4): δ = 10.56 (s, 1H), 8.94 (d, J=8Hz, 1H), 8.24-8.32 (m, 4H), 7.97 (d, J=8Hz, 1H), 7.86 (d, J=8Hz, 1H), 7.47-7.63 (m, 7H), 7.24 (d, J=8Hz, 1H), 5.90-5.97 (m, 1H), 3.98 (bs, 1H), 3.41-3.43 (m, 1H), 2.66 (s, 6H), 2.43 (s, 3H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1672, 1494, 1323, 1201, 1138, 800, 779, 721; MS : m/z (%) = 498.50 (100%) (M+H)+. Example-279 (R)-5-(1-aminocyclopropane-1-carboxamido)-2-methyl-N-(1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate
Figure imgf000130_0001
1H NMR (400 MHz, DMSO-d6): δ = 9.31 (s, 1H), 8.88 (d, J = 8.0 Hz, 1H), 8.53 (s, 3H), 8.25 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 8.8 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.62 – 7.35 (m, 6H), 7.20 (d, J = 8.4 Hz, 1H), 5.97 – 5.90 (m, 1H), 2.24 (s, 3H), 1.65 (t, J = 7.6 Hz, 2H), 1.58 (d, J = 6.8 Hz, 3H), 1.34 (t, J = 7.2 Hz, 2H); MS (TOF): m/z (%) = 388.2032 (100%) (M+H)+. Example-280 N-(4-((isopropylamino)methyl)-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) piperazine-2-carboxamide tris(2,2,2-trifluoroacetate)
Figure imgf000130_0002
1H NMR (400 MHz, D2O-d1): δ = 8.15 (d, J=8Hz, 1H), 7.92 (d, , J=8Hz, 1H), 7.83 (d, J=8Hz, 1H), 7.60 (s, 1H), 7.42-7.58 (m, 6H), 5.81-5.83 (m, 1H), 4.29-4.33 (m, 1H), 3.99- 4.03 (m, 1H), 3.77-3.89 (m, 2H), 3.15-3.60 (m, 2H), 3.26-3.43(m, 3H), 3.06-3.09 (m, 1H), 1.64 (d, J=8Hz, 3H), 1.07 (d, J=8Hz, 3H), 1.00 (d, J=8Hz, 3H); IR (KBr): v = 1668, 1199, 1180, 1128, 798, 721; MS(QTOF) : m/z (%) = 474.2829 (100%) (M+H)+. Example-281 (R)-5-amino-2-((isopropylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000130_0003
1H NMR (400 MHz, DMSO3-d4): δ = 10.30 (bs, 1H), 8.17 (d, J=8Hz, 1H), 7.96 (d, J=8Hz, 1H), 7.49-7.63 (m, 4H), 6.98 (d, J=8Hz, 1H), 6.90 (s, 1H), 6.57-6.59 (m, 1H), 5.90-5.94 (m, 1H), 5.36 (s, 2H), 3.54-3.57 (m, 2H), 1.63 (d, J=8Hz, 3H), 0.84-0.91 (m, 6H); MS : m/z (%) = 362.20 (100%) (M+H)+. Example-282 (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl) benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000131_0001
1H NMR (400 MHz, DMSO3-d4): δ = 9.92 (s, 1H), 8.90 (d, J=8Hz, 1H), 8.25 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.85 (d, J=8Hz, 1H), 7.49-7.63 (m, 6H), 7.16-7.18 (m, 1H), 5.89-5.93 (m, 1H), 3.45 (bs, 2H), 3.07 (bs, 4H), 2.79 (s, 3H), 2.61 (bs, 2H), 2.33 (s, 3H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1666, 1525, 1197, 1176, 1126, 833, 798, 779, 719; MS (QTOF) : m/z (%) = 445.2562 (100%) (M+H)+. Example-283 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperazin-1-yl)acetamido)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000131_0002
1H NMR (400 MHz, DMSO3-d4): δ = 9.95 (s, 1H), 8.90 (d, J=8Hz, 1H), 8.72 (bs, 2H), 8.25 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.85 (d, J=8Hz, 1H), 7.49-7.63 (m, 6H), 7.13-7.26 (m, 1H), 5.91-5.95 (m, 1H), 3.40 (bs, 2H), 2.87 (bs, 4H), 2.23 (s, 3H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1670, 1527, 1448, 1199, 1178, 1128, 798, 777, 721; MS (QTOF) : m/z (%) = 431.2401 (100%) (M+H)+. Example-284 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperidin-1-yl)acetamido)benzamide 2,2,2-trifluoroacetate
Figure imgf000131_0003
1H NMR (400 MHz, DMSO3-d4): δ = 10.62 (s, 1H), 9.70 (bs, 1H), 8.93 (d, J=8Hz, 1H), 8.23 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.87 (d, J=8Hz, 1H), 7.49-7.62 (m, 6H), 7.14-7.27 (m, 1H), 5.90-5.97 (m, 1H), 4.09 (s, 2H), 3.90-3.99 (m, 2H), 3.10 (bs, 2H), 2.41 (s, 3H), 1.70-1.90 (m, 4H), 1.58 (d, J=8Hz, 3H), 1.51 (bs, 1H); IR (KBr): v = 1670, 1598, 1550, 1199, 1176, 1128, 798, 779; MS(QTOF) : m/z (%) = 430.2445 (100%) (M+H)+. Example-285 (R)-2-methyl-5-(2-morpholinoacetamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000132_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.56 (bs, 1H), 8.93 (d, J=8Hz, 1H), 8.25 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.85 (d, J=8Hz, 1H), 7.46-7.63 (m, 6H), 7.15-7.27 (m, 1H), 5.90-5.97 (m, 1H), 4.07 (bs, 2H), 3.97 (bs, 4H), 3.25 (bs, 4H), 2.23 (s, 3H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1668, 1199, 1178, 1126, 798, 779, 719; MS (QTOF) : m/z (%) = 432.2247 (100%) (M+H)+. Example-286 (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyrrolidin-1-yl) acetamido) benzamide 2,2,2-trifluoroacetate
Figure imgf000132_0002
1H NMR (400 MHz, DMSO3-d4): δ = 10.58 (s, 1H), 10.07 (bs, 1H), 8.93 (d, J=8Hz, 1H), 8.25 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.86 (d, J=8Hz, 1H), 7.50-7.63 (m, 6H), 7.14-7.27 (m, 1H), 5.90-5.97 (m, 1H), 4.22 (s, 2H), 3.81-3.89 (m, 2H), 3.49 (bs, 2H), 2.33 (s, 3H), 1.80-1.93 (m, 4H), 1.56 (d, J=8Hz, 3H); IR (KBr): v = 1670, 1598, 1544, 1197, 1176, 1128, 779; MS(QTOF) : m/z (%) = 416.2289 (100%) (M+H)+. Example-287 (R)-2-methyl-5-(methyl(1-methylpiperidin-4-yl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide
Figure imgf000132_0003
1H NMR (400 MHz, DMSO3-d4): δ = 8.80 (d, J=8 Hz, 1H), 8.24 (d, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 7.64 (d, J=8 Hz, 1H), 7.49-7.62 (m, 4H), 7.00 (d, J=8 Hz, 1H), 6.73- 6.76(m, 1H), 6.67 (s, 1H), 5.87-5.91 (m, 1H), 3.33-3.50 (m, 2H), 2.81-2.82(m, 2H), 2.60 (s, 3H), 2.18 (s, 3H), 2.15 (s, 3H), 1.92-1.95 (m, 2H), 1.68-1.72 (m, 2H), 1.51-1.59 (m, 5H); IR (KBr): v = 2935, 1639, 1604, 1506, 1274, 798, 777; MS (TOF): m/z (%) = 416.2657 (100%) (M+H)+. Example-288 (R)-5-amino-2-((dibutylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate)
Figure imgf000133_0001
1H NMR (400 MHz, DMSO3-d4): δ = 9.60 (d, J=8Hz, 1H), 9.05 -9.10 (bs, 1H), 8.20 (d, J=8Hz, 1H), 7.97 (d, J=8Hz, 1H), 7.86 (d, J=8Hz, 1H), 7.51-7.64 (m, 4H), 7.12- 7.25 (m, 1H), 6.88 (s, 1H), 6.68-6.70 (m, 1H), 5.88-5.91 (m, 1H), 5.70-5.80 (bs, 1H), 4.10- 4.11 (m, 1H), 3.97-3.99 (m, 1H), 2.83-2.98 (m, 4H), 1.54-1.62 (m, 5H), 1.20-1.32 (m, 4H), 1.05-1.09 (m, 2H), 0.82-0.85 (m, 3H), 0.60-0.70 (m, 3H); MS (TOF): m/z (%) = 432.2976 (100%) (M+H)+. Example-289 (R)-5-amino-2-(aminomethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2- trifluoroacetate)
Figure imgf000133_0002
1H NMR (400 MHz, DMSO3-d4): δ = 9.27 (d, J=8Hz, 1H), 8.20 (d, J=8Hz, 1H), 7.96 (d, J=8Hz, 1H), 7.84 (d, J=8Hz, 1H), 7.53-7.63 (m, 4H), 7.14 (d, J=8Hz, 1H), 6.87 (s, 1H), 6.70 (d, J=8Hz, 1H), 5.89-5.91 (m, 1H), 3.80-3.81 (m, 2H), 1.59 (d, J=8Hz, 3H); IR (KBr): v = 1670, 1637, 1541, 1180, 1130, 798, 777, 721; MS : m/z (%) = 320.1 (100%) (M+H)+. Example-290 N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino)-3-oxopropyl)piperidine-4-carboxamide bis(2,2,2-trifluoroacetate)
Figure imgf000134_0001
1H NMR (400 MHz, DMSO3-d4): δ = 10.53 (s, 1H), 8.93 (d, J=8Hz, 1H), 8.62 (bs, 1H), 8.33-8.45 (m, 6H), 7.97 (d, J=8Hz, 1H), 7.86 (d, J=8Hz, 1H), 7.45-7.63 (m, 6H), 7.14- 7.19 (m, 1H), 5.90-5.95 (m, 1H), 4.00 (bs, 1H), 3.60-3.80 (m, 2H), 3.22-3.26 (m, 2H), 2.85- 2.86 (m, 2H), 2.33 (s, 3H), 1.61-1.82 (m, 4H), 1.58 (d, J=8Hz, 3H); IR (KBr): v = 1668, 1537, 1199, 1180, 1130, 798, 779, 721; MS (QTOF) : m/z (%) = 502.2789 (100%) (M+H)+; UPLC (% Purity) = 93.29%. Example-291 (S)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000134_0002
1H NMR (400 MHz, DMSO-d1): δ = 8.8 (d, J = 8 Hz, 1H), 8.26 (s, 1H), 8.25 (s, 1H), 7.7 – 7.62 (m, 2H), 7.59 – 7.46 (m, 2H), 7.40 (m, 1H), 7.2 (d, 1H), 5.90 (dd, 1H),3.345 (dd,2H), 2.18 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v = 3269, 3051, 2976, 2924, 1639, 1608, 1531, 1396, 1338, 1257, 769 cm-1; MS (TOF): m/z (%) = 362.1855 (100%) (M+H)+. Example-292 (S)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide
Figure imgf000134_0003
1H NMR (400 MHz, CDCl3-d1): δ = 8.8 (d, J = 8 Hz, 1H), 8.5 (s, 1H), 8.25 (d, J = 7.9 Hz, 1H), 7.97 – 7.62 (m, 1H), 7.59 – 7.46 (m, 1H), 7.59 – 7.40 (m, 4H), 7.39 (d, 1H), 7.29 (s, 1H), 7.04 (d, 2H), 2.18 (s, 3H), 1.57 (d, J = 7.2 Hz, 3H); IR (KBr): v = 3431, 2162, 1639, 1614, 1508 , 1396, 1274, 855, 842, 748, 665 cm-1; MS (TOF): m/z (%) = 348.2158 (100%) (M+H)+. Example-293 (R)-5-(2-aminoacetamido)-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000135_0001
1H NMR (400 MHz, DMSO-d1): δ = 8.8 (s, 1H), 8.22 (s, 1H ), 8.20 (s, 1H), 7.8 (m, 2H), 7.59 – 7.46 (m, 3H), 7.40 (m, 3H), 6.64-6.62 (d, j=8.4 Hz 1H),5.94 (d,j=7.2 Hz,1H) 3.44 (d, 2H), 8.99(dd,j=8.8 Hz,2H) 1.60-1.58 (d, j=7.2 Hz,3H), 0.912(s, 6H); IR (KBr): v = 3292, 3051, 2957, 2868, 2158, 1637, 1597, 1508, 1467, 1413, 1301, 1234, 889, 775, cm-1; MS (TOF): m/z (%) = 419.24 (100%) (M+H)+. Example-294 (R)-5-amino-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide
Figure imgf000135_0002
1H NMR (400 MHz, CDCl3-d1): δ = 8.26 (d, J = 8.4 Hz, 1H), 7.91 (dd, J = 7.6 Hz, 2H), 7.82 (d, J = 8.4 Hz, 1H), 7.61 – 7.54 (m, 3H), 7.52 – 7.46 (m, 1H), 6.97 (d, J = 7.6 Hz, 1H), 6.63 – 6.59 (m, 2H), 6.17 – 6.10 (m, 1H), 5.97 (d, J = 8.4 Hz, 1H),2.99 (m 2H), 1.24 (m, J = 7.2 Hz, 3H); IR (KBr): v = 3429, 3279, 1633, 1604, 1520, 1494, 1338, 1249, 877, 815, 796, 688 cm-1; MS (TOF): m/z (%) = 334.19 (100%) (M+H)+. Biological Activity: In-vitro assays: PLpro inhibition assay: To determine IC50 values of potential PLpro inhibitors, ISG15-AMC (R & D system) was used as substrate of PLpro and the release of AMC was measured by increase of fluorescence (Ex./Em.380/460 nm with 5 nm bandwidth) on 96-well microplate reader (Tecan M1000 Pro). 20 µl solution containing different concentration of NCEs (0-30 µM) diluted in assay buffer with 1% final DMSO and 10 µl of ubiquitin-AMC (75 nM) were aliquoted into 96 well plate and reaction was initiated by addition of 20 μl of PLpro-SARS- CoV2 (1 nM) to the well. Initial velocities of AMC-release were normalized against to DMSO control. IC50 values calculated by Dose- response – Inhibition function in Graphpad Prism with [inhibitor] vs normalized response equation. The invitro PLpro inhibition assay activity (IC50) for representative compounds are listed in Table 1. Table 1
Figure imgf000136_0001
Figure imgf000137_0001
Figure imgf000138_0001
Antiviral activity assay: For deriving anti-viral potency in Vero E6 cells (ATCC® CRL-1586), the cells were seeded at 10,000 cells per well in 96-well plates and incubated for 24 hrs at 37ºC in 5% CO2 containing humidified chamber to settle. NCEs were dissolved in DSMO and serially diluted in DMSO to achieve 1000x final concentration (range 0-300 µM). Cells were infected with SARS-CoV2 at MOI = 0.01 in PBS for 30 min at 37ºC. Viral inoculum was removed, and cells were washed with pre-warmed PBS for 5 minutes. Complete growth medium containing dilutions of NCEs or vehicle (DMSO, final 1%) was added to the wells. Cells were incubated at 37ºC. At 48 hrs post infection, the supernatants were harvested, viral RNA isolated and subjected to qPCR analysis. E-gene and RdRp gene probes were used to quantify the viral particle in samples and percentage reduction was deduced using comparative Ct method. The DRC was plotted with the help of Graphpad Prism software and IC50s were calculated. The invitro anti-viral activity (IC50) for representative compounds are listed in Table 2. Table 2
Figure imgf000138_0002
Figure imgf000139_0001
For cytotoxicity evaluation of NCEs, Vero E6 cells were seeded at a density of 15,000 cells/well a tissue culture treated clear-bottom 96-well plate and incubated at 37° C in 5% CO2 containing humidified chamber overnight. Medium was removed, and serial dilutions of drug in medium were added to each well. Cell viability was determined using MTT at 48 hrs. In vivo efficacy studies: Animal Model for Screening Antiviral Activity against SARS-CoV-2: The hamsters or mice are infected with the SARS-CoV-2 virus, and animals are treated with test comps for seven to fifteen days. The animals are observed for mortality, clinical signs, body weight and lung function. The viral load is measured in throat and nasal swabs at various treatment days and in lung at termination. Blood samples are collected for the evaluation of various cytokine and biochemical parameters. At termination, all animals are sacrificed, necropsies is conducted; gross observations are noted, and tissue samples is obtained from the lungs and other vital organs or histopathological examination. The anti- viral activity is evaluated based on the difference in viral load and change in various blood, clinical, and histological parameters observed in test compound-treated animals Vs. Placebo-treated animals. The compounds of formula (I) or pharmaceutical compositions containing them are useful as a medicament for the inhibition of Papain-Like protease (PLpro) activity and suitable for humans and other warm blooded animals, and may be administered either by oral, topical or parenteral administration. The compounds of the present invention are formulated with conventional carriers and excipients, which will be selected in accord with ordinary practice. Tablets will contain excipients, glidants, fillers, binders and the like. Aqueous formulations are prepared in sterile form and when intended for delivery by other than oral administration generally will be isotonic. All formulations will optionally contain excipients such as those set forth in the “Handbook of Pharmaceutical Excipients” (1986). While it is possible for the active ingredients to be administered alone it may be preferable to present them as pharmaceutical formulations. The formulations, both for veterinary and for human use, of the invention comprise at least one active ingredient, as above defined, together with one or more acceptable carriers therefore and optionally other therapeutic ingredients, particularly those additional therapeutic ingredients as discussed herein. The carrier(s) must be “acceptable” in the sense of being compatible with the other ingredients of the formulation and physiologically innocuous to the recipient thereof. Formulations of the present invention suitable for oral administration may be presented as discrete units such as capsules, cachets or tablets each containing a predetermined amount of the active ingredient: as a powder or granules: as a solution or a suspension in an aqueous or non-aqueous liquid: or as an oil-in-water liquid emulsion or a water-in-oil liquid emulsion. The active ingredient may also be administered as a bolus, electuary or paste. Pharmaceutical formulation according to the present invention comprise a combination according to the invention together with one or more pharmaceutically acceptable carriers or excipients and optionally other therapeutic agents. Pharmaceutical formulations containing the active ingredient may be in any form suitable for the intended method of administration. When used for oral use for example tablets, troches, lozenges, aqueous or oil suspensions, dispersible powders or granules, emulsions, hard or soft capsules, syrups or elixirs may be prepared. One or more compounds of the invention (herein referred to as the active ingredients) are administered by any route appropriate to the condition to be treated. Suitable routes include oral, rectal, nasal, pulmonary, topical (including buccal and sublingual), vaginal and parenteral (including subcutaneous, intramuscular, intravenous, intradermal, intrathecal and epidural), and the like. It will be appreciated that the preferred route may vary with for example the condition of the recipient. An advantage of the compounds of this invention is that they are orally bioavailable and can be dosed orally. The quantity of active component, that is, the compounds of Formula (I) according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application method, the potency of the particular compound and the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition. Thus, a pharmaceutical composition comprising the compounds of the present invention may comprise a suitable binder, suitable bulking agent &/or diluent and any other suitable agents as may be necessary. Optionally, the pharmaceutical composition may be suitably coated with suitable coating agents. The compounds of the present invention, formula (I), may be used alone or in any combination with one or more other therapeutic agents which a skilled medical practitioner can easily identify. Such other therapeutic agent may be selected depending on the type of disease being treated, the severity, other medications being taken by the patients etc, like severe acute respiratory syndrome (SARS), Middle East respiratory syndrome (MERS), Spanish flu, COVID19 (Coronavirus disease 2019), hepatitis C virus, chikungunya virus, influenza A virus, herpes simplex virus type 1 and Japanese encephalitis virus. In one of the embodiments compound of formula (I) of the present invention may be used in combination with one or more suitable pharmaceutically active agents selected from following therapeutic agents in any combination. Inhibitors of interleukin-1β (e.g. Rilonacept Canakinumab and Anakinra); immune suppressants (eg Dexamethasone Methotrexate, Mercaptopurine, Cyclophosphamide), metabolic disorders drugs, glucocorticoids, non-steroidal anti-inflammatory drugs, Gasdermin D inhibitors (e.g., Necrosulfonamide); Cox-2 specific inhibitors, TNF-α binding proteins (e.g.,Infliximab, Etanercept), Interferon-13, Interferon, Interleukin-2, antihistamines, beta-agonist, BTK inhibitors, anticolinergics, anti-cancer agents; anti-viral drugs, for example: Remdesivir, Lopinavir/Ritonavir, Favipiravir, Tamiflu; anti-malarial agents, for example: Choloroquinone, Hydroxyl Chloroquinone; or their suitable pharmaceutically acceptable salts. Further examples for use in combination with Non-Alcoholic Steato- Hepatitis (NASH) and fibrosis drugs; anticancer; antibiotics, for example Azithromycin; hormones, Aromatase inhibitors, Colchicine, Anticoagulants, antibodies, cytokines, anti-IL6 drugs; Antiparasitics; vaccines; Interferons; drug conjugates; Drugs originally developed for SARS (ACE2 protein decoy); Intravenous vitamin C; inhibitors of mitogen-activated protein kinase signaling (ex: BAY 43-9006); Syk inhibitors; mTOR inhibitors; antibodies (Rituxan); and BCR/ABL antagonist. Compositions of the invention are also used in combination with other active ingredients. For the treatment of Arenaviridae virus infections, preferably, the other active therapeutic agent is active against Arenaviridae virus infections, particularly Lassa virus and Junin virus infections. Non-limiting examples of these other active therapeutic agents are Ribavirin, Favipiravir (also known as T-705 or Avigan),T-705 monophosphate, T-705 diphosphate, T-705 triphosphate, ST- 193, and mixtures thereof. The compounds and compositions of the present invention are also intended for use with general care provided patients with Arenaviridae viral infections, including parenteral fluids (including dextrose saline and Ringer's lactate) and nutrition, antibiotic (including Metronidazole and Cephalosporin antibiotics, such as Ceftriaxone and Cefuroxime) and/or antifungal prophylaxis, fever and pain medication, antiemetic (such as Metoclopramide) and/or antidiarrheal agents, vitamin and mineral supplements (including Vitamin C or/and K and zinc sulfate), anti-inflammatory agents (such as Ibuprofen), pain medications, and medications for other common diseases in the patient population, such anti-malarial agents (including Artemether and Artesunate-lumefantrine combination therapy), typhoid (including quinolone antibiotics, such as Ciprofloxacin, macrolide antibiotics, such as Azithromycin, cephalosporin antibiotics, such as Ceftriaxone, or aminopenicillins, such as Ampicillin), or shigellosis. While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention.

Claims

We claim: 1. Compound having the structure of general formula (I)
Figure imgf000142_0001
their tautomeric forms, their stereoisomers, their enantiomers, their pharmaceutically acceptable salts, and pharmaceutical compositions containing them wherein, ‘A’ is selected from unsubstituted or substituted (C3-C7)cycloalkyl, aryl, heteroaryl heterocyclyl, bridged or spiro ring system having optionally one or more than one heteroatoms; ‘B’ is selected from unsubstituted or substituted (C3-C7)cycloalkyl, aryl, heteroaryl heterocyclyl, bridged, fused bi- or tri- cyclic ring systems or spiro ring system having optionally one or more than one heteroatoms; each of R1 and R2 at each occurrence independently represents hydrogen, halogen, haloalkyl, cyano, amine, optionally substituted groups selected from (C1-C6)alkyl, (C2- C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, N(C3-C8)cycloalkyl, (C1- C6)alkylSO2(C1-C6)alkyl, (C1-C6)alkylN(C1-C6)alkyl, (C1-C6)alkylN(C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl, benzyl, thiol, mercaptoalkyl, SO2(C1-C6)alkyl, SO2(C3- C7)cycloalkyl, SO2-aryl, SO2-heterocyclyl, (C1-C6)thioalkyl, (C1-C6)thioalkoxy, (C1- C6)alkylSO2NH2, -CONH2, -CO(C1-C6)alkyl, -CO(C1-C6)haloalkyl, -CO-aryl, -CO- heteroaryl, -CO-heterocyclyl, heterocyclyl ,fused, bridged or spiro ring system having optionally one or more than one heteroatoms; each of R3, R4 , R5, R6 at each occurrence independently represents hydrogen, halogen, haloalkyl, cyano, nitro, amide, sulphonamide, acyl, hydroxyl, optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C7)cycloalkyl, (C1-C6)alkoxy, SO2(C1-C6)alkyl, thiol, mercapto alkyl benzyl, aryl, heteroaryl, heterocyclyl, bridged or spiro ring system having optionally one or more than one heteroatoms; Alternatively R3 and A forms together may form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group consisting of N, O, CO, and S(O)q; q = 1-3; Alternatively R4 or R5 and A forms together may form a 4 to 7 membered saturated or partially saturated ring containing from 0-2 additional heteroatoms selected from the group consisting of N, O, CO, and S(O)r; r = 1-2.; each of V, W, X, Y, Z at each occurrence is independently selected from a bond, hydrogen, N, S, SO, SO2, O, CO, OH, NH, S(O)N-R7, O-R7, N-R7; unsubstituted or substituted (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C7)cycloalkyl, aryl, heteroaryl and heterocyclyl, wherein R7 at each occurrence independently represents hydrogen, hydroxyl, halogen, nitro, cyano, haloalkyl, optionally substituted groups selected from (C1-C6)alkyl, (C1-C6)alkoxy, (C3-C7)cycloalkyl, (C2-C6) alkenyl, (C2-C6)alkynyl, SO2(C1-C6)alkyl, thiol, thioalkyl, thio-alkoxy, SO2(C1-C6)alkyl, SO(C1-C6)alkyl, benzyl, aryl, heteroaryl, heterocyclyl, fused cyclic ring systems or spiro ring system; Alternatively V, W, X, Y, Z wherever possible together may form a 3- to 8-membered aryl or heterocyclic ring having optionally one or more than one hetero atoms selected from the group consisting of N, CO, O, CO, and S(O)t; t = 1-2.; m, n, o, p is independently selected from integer 0-4. 2. The compound as claimed in claim 1, wherein when any of the group is substituted, the substitutions are selected from hydrogen, halogen, hydroxy, cyano, halo, haloalkyl, haloalkyloxy, alkylthio (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3- C10)cycloalkyl, C1-C6 alkoxy, aryl, heterocyclyl, heteroaryl, -COR11, -CSR11, C(O)OR11, C(O)-R11, -C(O)-NR11R12, -C(S)-NR11R12, -SO2R11 group, wherein each of R11 and R12 is independently selected from hydrogen, optionally substituted group selected from (C1- C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl groups. 3. A compound as claimed in claim 1 selected from the group comprising of: (R)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; 5-((S)-2,3-diaminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(but-2-yn-1-yloxy)-2methyl-N-(1-(naphtalen-1-yl)ethyl)bemzamide; N-(2-(1H-indol-3-yl)ethyl)-5-amino-2-methylbenzamide; 5-acetamido-N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-2-methylbenzamide; (R)-5-(2-aminoacetamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2,3-diaminopropanamido)-2-fluoro-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; (R)-5-(but-2-yn-1-ylamino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(di(but-2-yn-1-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-aminopropanamido)-2-fluoro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(thiazol-2-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrimidin-2-ylamino)benzamide; (R)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)-5-ureidobenzamide; (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-5-(2-aminoacetamido)-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidin-1-yl)benzamide; (R)-2-methyl-5-(3-(methylsulfonyl)ureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-3-ylamino)benzamide; (R)-5-(di(pyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-amino-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide; N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methyl-5-ureidobenzamide; 5-(2-aminoacetamido)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylbenzamide; (S)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(2,3-diaminopropanamido)-2- methylbenzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(propylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-2-ylamino)benzamide; (R)-5-(di(pyridin-2-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-aminopropanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(4-aminobutanamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-guanidino-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-oxoimidazolidin-1-yl)benzamide; (R)-2-methyl-5-((2-(methylamino)ethyl)amino)-N-(1-(naphthalen-1-yl) ethyl) benzamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl) ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-1-isopropyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl)pyrrolidine-2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1- (methylsulfonyl)pyrrolidine-2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2- (methylamino)ethyl)pyrrolidine-2-carboxamide; (S)-1-acetyl-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) pyrrolidine-2-carboxamide; 2-methyl-5-((((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-5-(methyl(((S)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen- 1-yl)ethyl)benzamide; 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((((S)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-((dimethylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((2-(dimethylamino)ethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-2-methyl-5-((3-(methylamino)propyl)amino)-N-(1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-amino-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((pyrrolidin-3-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-5-(((1-methylpyrrolidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1 yl)ethyl) benzamide 2,2,2-trifluoroacetate; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-3- carboxamide 2,2,2-trifluoroacetate; 1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine- 3-carboxamide 2,2,2-trifluoroacetate; tert-butyl ((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) amino)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-3- carboxamide 2,2,2-trifluoroacetate; (R)-1-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-3- carboxamide 2,2,2-trifluoroacetate; (R)-5-((azetidin-3-ylmethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-5-((2-(methyl(((R)-pyrrolidin-2-yl)methyl)amino)ethyl)amino)-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-(dimethylamino)-2-methylpropyl)amino)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-5-((2-(methyl(2-(methylamino)ethyl)amino)ethyl)amino)-N-(1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-((2-aminoethyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((S)-3-((S)-2-oxopyrrolidin-3-yl)-2- (2,2,2-trifluoroacetamido)propanamido)benzamide; 5-((S)-2-(dimethylamino)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)- 1-(naphthalen-1-yl)ethyl)benzamide; tert-butyl (R)-2-(((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)amino)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)piperidine-1- carboxylate; tert-butyl ((S)-1-((1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)carbamoyl)-3-azabicyclo[3.1.0]hexan-3-yl)-3,3-dimethyl-1- oxobutan-2-yl)carbamate; (1R,2S,5S)-3-((R)-2-amino-3,3-dimethylbutanoyl)-6,6-dimethyl-N-(4-methyl-3-(((R)- 1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3-azabicyclo[3.1.0]hexane-2-carboxamide 2,2,2-trifluoroacetate; (R)-3-(but-2-yn-1-yloxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-3-(2-(2-methoxyethoxy)ethoxy)-4-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide 5-((S)-2-aminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; tert-butyl ((R)-4-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl)amino)-4-oxobutan-2-yl)carbamate; methyl (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoate; (R)-3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzoic acid; 5-((R)-3-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-acetamido-N1-(2-(2-hydroxyethoxy)ethyl)-N3-(1-(naphthalen-1-yl)ethyl) isophthalamide; methyl (R,E)-4-(3-acetamido-5-((1-(naphthalen-1-yl)ethyl)carbamoyl)benzamido)but- 2-enoate; (R)-5-acetamido-N1-(1-(naphthalen-1-yl)ethyl)-N3-propylisophthalamide; (R)-5-acetamido-N-(1-(naphthalen-1-yl)ethyl)isophthalamide; (R)-5-(3-allylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide ; (R)-5-(3-(4-fluorophenyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-(4-fluorophenyl)thioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-cyclohexylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylthioureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(3-benzylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-3-acetamido-2-aminopropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide 2,2,2-trifluoroacetate; N,N'-((S)-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-3- oxopropane-1,2-diyl)diacetamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide 2,2,2- trifluoroacetate; (R)-4-amino-N-(1-(naphthalen-1-yl)ethyl)-2-(pyrrolidine-1-carbonyl)benzamide 2,2,2- trifluoroacetate (R)-5-(3,3-dimethylureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(3-methylureido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2,3-bis(dimethylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-((S)-2,3-bis(isopropylamino)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-(3-(2-aminoethyl)ureido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-(methylthio)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4-yl)methylsulfonamido) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(N-(pyridin-4-yl) cyclopropanesulfonamido)benzamide; (R)-N-(4-(ethylamino)-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine- 2-carboxamide 2,2,2-trifluoroacetate; (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 1-carboxamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-1- carboxamide; (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-5-amino-N-(1-(naphthalen-1-yl)ethyl)thiophene-2-carboxamide; (R)-5-(2-(4-(4-fluorophenyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-5-(2-(4-methyl-1,4-diazepan-1-yl)acetamido)-N-(1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl)methyl) amino)benzamide dihydrochloride; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl) methyl)amino)benzamide; (R)-4-methyl-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4- diazepane-1-carboxamide; (R)-5-(2-(4-(2-hydroxyethyl)piperazin-1-yl)acetamido)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-4-(2-hydroxyethyl)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)piperazine-1-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)azetidine-2- carboxamide; 5-((S)-2-amino-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; 2-methyl-5-(((2-methylazetidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide ; (S)-2-(hydroxymethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl)pyrrolidine-1-carboxamide; 5-((azetidin-2-ylmethyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-((((R)-1,2-dimethylpyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl)amino)benzamide; (R)-2-methyl-5-(((1-methylpiperidin-4-yl)methyl)amino)-N-(1-(naphthalen-1- yl)ethyl)benzamide; 5-(3-((1r,4R)-4-hydroxycyclohexyl)ureido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 5-((S)-2-(dimethylamino)-3-hydroxypropanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(3-(piperidin-4-ylmethyl) ureido) benzamide; (R)-2-methyl-5-(((3-methyloxetan-3-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide methanesulfonate; tert-butyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) amino) methyl)pyrrolidine-1-carboxylate; ethyl (S)-2-(((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino) methyl)pyrrolidine-1-carboxylate; 5-((R)-2-amino-3-((R)-2-oxopyrrolidin-3-yl)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (1R,2S,5S)-3-((S)-3,3-dimethyl-2-(2,2,2-trifluoroacetamido)butanoyl)-6,6-dimethyl-N- (4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-3- azabicyclo[3.1.0]hexane-2-carboxamide; tert-butyl (1R,2S,5S)-6,6-dimethyl-2-((4-methyl-3-(((R)-1-(naphthalen-1 yl)ethyl) carbamoyl)phenyl)carbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate; (1R,2S,5S)-6,6-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl)-3-azabicyclo[3.1.0]hexane-2-carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hemimalonate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide benzenesulfonate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide ethanesulfonate; (R)-5-acetamido-2-methyl-N-(1-phenylethyl)benzamide; 5-((S)-2-amino-3,3-dimethylbutanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 1-acetyl-N-((R)-1-(naphthalen-2-yl)ethyl)pyrrolidine-2-carboxamide; 5-amino-N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)methyl)-2-methylbenzamide; (R)-2-isopropoxy-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-methoxy-N-(1-(naphthalen-1-yl)ethyl)-2-propoxybenzamide; 5-amino-N-(imidazo[1,2-a]pyridin-2-ylmethyl)-2-methylbenzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate; (R)-N1-(2-aminoethyl)-N3-(1-(naphthalen-1-yl)ethyl)isophthalamide; (R)-5-amino-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-chloro-5-((R)-2,3-diaminopropanamido)-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)tetrahydro-2H-pyran- 4-carboxamide; (R)-5-(cyclohexanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((1-methylethyl)sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(2-aminoacetamido)-2-(dimethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-4- carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine-2- carboxamide 2,2,2-trifluoroacetate; (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2- yl)methyl)amino)benzamide 222-trifluoroacetate; 5-((R)-2,3-diaminopropanamido)-2-(methylamino)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; (R)-5-acetamido-2-chloro-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperazin-2-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((piperidin-3-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-5-(methyl(((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((S)-1-(naphthalen- 1-yl)ethyl)benzamide; 5-(((1,4-dimethylpiperazin-2-yl)methyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; 2-methyl-5-(methyl((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-3- carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrrolidine-2- carboxamide 2,2,2-trifluoroacetate; 1,4-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-2-carboxamide bis(2,2,2-trifluoroacetate); 1,4-diacetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-2-carboxamide; 1,4-bis(cyclopropylsulfonyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl)piperazine-2-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1,4-bis (methylsulfonyl) piperazine-2-carboxamide; N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-4-(methylsulfonyl) piperazine-2-carboxamide 2,2,2-trifluoroacetate; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-pyrrolidin-2-yl)methyl) amino) benzamide 2,2,2-trifluoroacetate; 4-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) piperazine-2-carboxamide bis(2,2,2-trifluoroacetate); 2-methyl-5-((((S)-1-(methylsulfonyl)pyrrolidin-2-yl)methyl)amino)-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; 5-((((S)-1-(cyclopropylsulfonyl)pyrrolidin-2-yl)methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (S)-1-acetyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl )phenyl) pyrrolidine-2-carboxamide; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1- (methylsulfonyl) pyrrolidine-2-carboxamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((1-(((S)-pyrrolidin-2-yl)methyl) piperidin-4-yl)amino)benzamide bis(2,2,2-trifluoroacetate); 4-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperazine- 2-carboxamide bis(2,2,2-trifluoroacetate); (S)-1-isopropyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-1-ethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((1-(((R)-pyrrolidin-2-yl)methyl) piperidin-4-yl)amino)benzamide bis(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl)methyl) amino)benzamide; 5-((R)-3-amino-2-((((S)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N-((R)- 1-(naphthalen-1-yl)ethyl)benzamide tris(2,2,2-trifluoroacetate); 5-((R)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propanamido)-2-methyl-N-((R)- 1-(naphthalen-1-yl)ethyl)benzamide tris(2,2,2-trifluoroacetate); 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-pyrrolidin-2-yl)methyl) amino)benzamide dihydrochloride; 2-methyl-5-((((S)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; 2-methyl-5-(((1-methylpiperidin-3-yl)methyl)amino)-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide; 2-methyl-5-((((R)-1-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((S)-piperidin-2-yl)methyl) amino) benzamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 2,2,2-trifluoroacetate; 2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; 2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-5-((((R)-piperidin-2-yl)methyl) amino)benzamide 2,2,2-trifluoroacetate (R)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate; 2-methyl-5-(((4-methylpiperazin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; (S)-1-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperidine-2-carboxamide; tert-butyl (R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) carbamoyl)piperidine-1-carboxylate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide; 2-methyl-5-((((R)-1-methylpiperidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide hydrochloride; ethyl (R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) carbamoyl) piperidine-1-carboxylate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide phosphate; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2- (methylamino)ethyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate); (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(((R)- pyrrolidin-2-yl)methyl)piperidine-2-carboxamide bis(2,2,2-trifluoroacetate); (S)-1-(2-hydroxyethyl)-N-(4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)piperidine-2-carboxamide 2,2,2-trifluoroacetate; (S)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)-1-(2,2,2- trifluoroacetyl)piperidine-2-carboxamide; (R)-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)piperidine-2- carboxamide 4-methylbenzenesulfonate; (R)-5-hydroxy-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; tert-butyl ((R)-2-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) amino)-2-oxo-1-phenylethyl)carbamate (R)-5-(2-amino-2-methylpropanamido)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide N-(2-(1H-indol-3-yl)ethyl)-5-acetamido-2-methylbenzamide; N-(2-(1H-indol-3-yl)ethyl)-5-(2-aminoacetamido)-2-methylbenzamide; (R)-N2-(2-(2-hydroxyethoxy)ethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6- dicarboxamide; (R)-N2-(4-aminobutyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-N2-(2-aminoethyl)-N6-(1-(naphthalen-1-yl)ethyl)pyridine-2,6-dicarboxamide; (R)-5-((N,N-dimethylsulfamoyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide; (R)-2-chloro-N-(1-(naphthalen-1-yl)ethyl)-5-(pyrrolidine-1-sulfonamido)benzamide; (R)-2-methyl-5-(morpholine-4-sulfonamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((4-methylpiperazine)-1-sulfonamido)-N-(1-(naphthalen-1-yl)ethyl) benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidine-1-sulfonamido)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((N-phenylsulfamoyl)amino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperazine-1-sulfonamido)benzamide 2,2,2-trifluoroacetate; 2-methyl-5-(methylsulfonoamidimidamido)-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; 5-(((N-acetylacetamido)(methyl)(oxo)-l6-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; ethyl (methyl((4-methyl-3-(((R)-1-(naphthalen-1- yl)ethyl)carbamoyl)phenyl)amino)(oxo)-l6-sulfaneylidene)carbamate; 5-(((dimethylamino)(methyl)(oxo)-l6-sulfaneylidene)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyridin-4-ylamino) acetamido) benzamide; 5-((4-cyanophenyl)sulfonoamidimidamido)-2-methyl-N-((R)-1-(naphthalen-1-yl) ethyl)benzamide; (R)-5-(2-(dimethylamino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((4-fluorobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-((4-cyanobenzyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((4-(trifluoromethyl) benzyl) amino) benzamide; (R)-5-((6-aminopyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(((5-methylthiophen-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-3-ylmethyl)amino)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(((1-methyl-1H-pyrrol-2-yl)methyl)amino)-N-(1-(naphthalen-1-yl) ethyl)benzamide; (R)-5-((6-hydroxypyridin-3-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-(2-((cyclopropylmethyl)amino)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-5-(2-(isoindolin-2-yl)acetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-(((1H-imidazol-5-yl)methyl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl) benzamide; (R)-6-amino-3-methyl-N-(1-(naphthalen-1-yl)ethyl)picolinamide; (R)-3-methyl-N-(1-(naphthalen-1-yl)ethyl)-6-(piperidin-4-ylamino)picolinamide 2,2,2- trifluoroacetate; 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((((R)-pyrrolidin-2-yl)methyl) amino) picolinamide 2,2,2-trifluoroacetate; 3-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)-6-((R)-pyrrolidine-2-carboxamido) picolinamide 2,2,2-trifluoroacetate; (R)-6-amino-5-methyl-N-(1-(naphthalen-1-yl)ethyl)picolinamide; 5-(((S)-2,3-diaminopropyl)amino)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-3-amino-2-(dimethylamino)propyl)(methyl)amino)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-3-amino-2-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-(((S)-2-amino-3-((((R)-pyrrolidin-2-yl)methyl)amino)propyl)amino)-2-methyl-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) piperidine-2-carboxamide; (S)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) piperidine-2-carboxamide 2,2,2-trifluoroacetate; (R)-N-(4-methyl-3-((1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)pyrazine-2- carboxamide; (R)-5-(cyclopropanesulfonamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; 5-((S)-2-amino-3-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide 5-((S)-2-amino-3-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; 5-((S)-3-amino-2-(cyclopropanesulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (S)-5-(2,3-diaminopropanamido)-2-methyl-N-(quinolin-2-ylmethyl)benzamide bis(2,2,2-trifluoroacetate); 5-((S)-3-amino-2-(methylsulfonamido)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2,4-diaminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(piperidin-4-ylamino)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((tetrahydro-2H-pyran-4-yl)amino) benzamide; (R)-5-((9H-purin-6-yl)amino)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridine-3-sulfonamido)benzamide; 5-((S)-2,6-diaminohexanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); 5-((S)-2-amino-3-(pyridine-3-sulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; 5-((S)-2-amino-3-((3,5-difluorophenyl)sulfonamido)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-((1-(methylsulfonyl)piperidin-4-yl)amino)-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((piperidin-4-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl)phenyl) amino)-3-oxopropyl)piperazine-2-carboxamide tris(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-((pyridin-4-ylmethyl)amino)benzamide bis(2,2,2-trifluoroacetate); N-(4-methyl-3-((quinolin-4-ylmethyl)carbamoyl)phenyl)piperazine-2-carboxamide bis(2,2,2-trifluoroacetate); 5-((S)-2-amino-3-(1H-imidazol-4-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2-amino-3-(1H-indol-3-yl)propanamido)-2-methyl-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2-amino-3-((N,N-dimethylsulfamoyl)amino)propanamido)-2-methyl-N-((R)-1- (naphthalen-1-yl)ethyl)benzamide 2,2,2-trifluoroacetate; N-(4-((isopropylamino)methyl)-3-(((R)-1-(naphthalen-1-yl)ethyl) carbamoyl) phenyl) piperazine-2-carboxamide tris(2,2,2-trifluoroacetate); (R)-5-amino-2-((isopropylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-2-methyl-5-(2-(4-methylpiperazin-1-yl)acetamido)-N-(1-(naphthalen-1-yl)ethyl) benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperazin-1-yl)acetamido)benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(piperidin-1-yl)acetamido)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(2-morpholinoacetamido)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-(2-(pyrrolidin-1-yl)acetamido)benzamide 2,2,2-trifluoroacetate; (R)-2-methyl-5-(methyl(1-methylpiperidin-4-yl)amino)-N-(1-(naphthalen-1- yl)ethyl)benzamide; (R)-5-amino-2-((dibutylamino)methyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2-trifluoroacetate); (R)-5-amino-2-(aminomethyl)-N-(1-(naphthalen-1-yl)ethyl)benzamide bis(2,2,2- trifluoroacetate); N-((S)-2-amino-3-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl) amino)-3-oxopropyl)piperidine-4-carboxamide bis(2,2,2-trifluoroacetate); (S)-5-(2-aminoacetamido)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)benzamide; (S)-2-methyl-N-(1-(naphthalen-1-yl)ethyl)-5-ureidobenzamide; (R)-5-(2-aminoacetamido)-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; (R)-5-amino-2-(isobutylamino)-N-(1-(naphthalen-1-yl)ethyl)benzamide; 2-methyl-5-((((R)-2-methylpyrrolidin-2-yl)methyl)amino)-N-((R)-1-(naphthalen-1- yl)ethyl)benzamide; (R)-2-(ethylamino)-N-(1-(naphthalen-1-yl)ethyl)-5-(pyridin-4-ylamino)benzamide; (R)-2-methyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide 2,2,2-trifluoroacetate; (R)-1,2-dimethyl-N-(4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl) phenyl) pyrrolidine-2-carboxamide; (R)-5-(1-aminocyclopropane-1-carboxamido)-2-methyl-N-(1-(naphthalen-1- yl)ethyl)benzamide 2,2,2-trifluoroacetate; 5-((S)-2-aminobutanamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl)benzamide; 5-((R)-2-amino-2-phenylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide; (R)-N-((S)-1-((4-methyl-3-(((R)-1-(naphthalen-1-yl)ethyl)carbamoyl)phenyl)amino)-1- oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)piperidine-2-carboxamide 2,2,2- trifluoroacetate; 2-methyl-5-((S)-2-(methylsulfonamido)-3-((S)-2-oxopyrrolidin-3-yl)propanamido)-N- ((R)-1-(naphthalen-1-yl)ethyl)benzamide 5-((R)-2-amino-2-cyclohexylacetamido)-2-methyl-N-((R)-1-(naphthalen-1-yl)ethyl) benzamide. 4. A pharmaceutical composition comprising a therapeutically effective amount of a compound of Formula (I) as claimed in any of the preceding claims and optionally one or more pharmaceutically acceptable carriers, diluents or excipients. 5. A method of treating diseases medicated by the papain-like protease (PLpro) as well as treatment of diseases or conditions in which SARS-CoV, SARS-CoV2 is implicated which comprising administering to a patient in need thereof an effective amount of a compound of Formula (I) as claimed in any of the preceding claims or its suitable pharmaceutical composition. 6. The use of compounds of formula (I) or its pharmaceutical compositions as claimed in any of the preceding claim suitable for treatment of diseases for the prevention and treatment of disease states mediated by papain-like protease (PLpro). 7. A pharmaceutical composition as claimed in claim 1 wherein the compound of formula (I) of the present invention may be used in combination with one or more suitable pharmaceutically active agents selected from following therapeutic agents in any combination selected from Inhibitors of interleukin-1β, immune-suppressants, metabolic disorders drugs, glucocorticoids, non-steroidal anti-inflammatory drugs, Gasdermin D inhibitors, Cox-2 specific inhibitors, TNF-α binding proteins, Interferon-13, Interferon, Interleukin-2, antihistamines, beta-agonist, BTK inhibitors, anticolinergics, anti-cancer agents, anti-viral drugs, anti-malarial agents or their suitable pharmaceutically acceptable salts. Further examples for use in combination with Non-Alcoholic Steato-Hepatitis (NASH) and fibrosis drugs, anticancer, antibiotics, hormones, Aromatase inhibitors, Colchicine, Anticoagulants, antibodies, cytokines, anti-IL6 drugs, Antiparasitics, vaccines, Interferons; drug conjugates, Drugs originally developed for SARS (ACE2 protein decoy), Intravenous vitamin C, inhibitors of mitogen-activated protein kinase signaling, Syk inhibitors, mTOR inhibitors, antibodies and BCR/ABL antagonist, Ribavirin, Favipiravir, T-705 monophosphate, T-705 diphosphate, T-705 triphosphate, ST- 193, and mixtures thereof, antibiotics and/or antifungal prophylaxis, fever and pain medication, antiemetic and/or antidiarrheal agents, vitamin and mineral supplements, anti-inflammatory agents, pain medications and medications for other common diseases in the patient population, anti-malarial agent or combination thereof.
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US11834441B2 (en) 2019-12-06 2023-12-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
US11919887B2 (en) 2019-12-06 2024-03-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
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WO2023223055A1 (en) * 2022-05-20 2023-11-23 Infex Therapeutics Limited Anti-viral compounds
WO2024040496A1 (en) * 2022-08-25 2024-02-29 清华大学 Antiviral compound, and preparation method therefor and use thereof
WO2024040497A1 (en) * 2022-08-25 2024-02-29 清华大学 Antiviral compound, preparation method therefor and use thereof
WO2024072794A1 (en) * 2022-09-26 2024-04-04 Rectify Pharmaceuticals, Inc. Pyridine carboxamide compounds and their use in treating medical conditions
WO2024074849A1 (en) 2022-10-07 2024-04-11 Tocris Cookson Limited Proteolysis-targeting chimeras against the papain-like protease of sars-cov-2
WO2024121779A1 (en) 2022-12-09 2024-06-13 Pfizer Inc. Papain-like protease (plpro) inhibitors
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