Pyrrolopyridine compound and use thereof

Abstract

The present invention relates to a pyrrolopyridine compound and a use thereof, the compound having antiviral activity, particularly, a compound of chemical formula 1 having high selectivity and physiological activity against human immunodeficiency virus (HIV), or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof. [Chemical formula 1]

Description

Pyrrolopyridine compounds and their uses

[0001] The present invention relates to pyrrolopyridine compounds having antiviral activity, particularly compounds having high selectivity and physiological activity against human immunodeficiency virus (HIV), or pharmaceutically acceptable salts, stereoisomers, hydrates, solvates, tautomers or prodrugs thereof, and uses thereof.

[0002] Acquired Immunodeficiency Syndrome (AIDS) is caused by infection with the human immunodeficiency virus (HIV). There are two types of HIV, HIV-1 and HIV-2, and HIV-1 is the most prevalent type worldwide. Enzyme inhibitors have been developed to treat AIDS based on the mechanism of action of HIV. These enzyme inhibitors are classified into nucleoside reverse transcriptase inhibitors (NRTIs), protease inhibitors (PIs), fusion inhibitors, and integrase inhibitors based on their site of action.

[0003] Integrase inhibitors are classified into catalytic site inhibition and non-catalytic site inhibition depending on their mechanism of action. Research on catalytic site integrase inhibitors has been actively conducted, and three types of drugs have been developed and are commercially available, with raltegravir, developed in 2008, being a representative drug. On the other hand, the non-catalytic site integrase inhibition mechanism was introduced by Ziger Debyser et al. (Frauke Christ, Zeger Debyser et al., Nature Chemical Biology, 2010, Vol. 6, 442), and the development of inhibitors for this mechanism of action has been actively progressing.

[0004] In addition, various studies are underway to develop drugs that can effectively treat resistant viruses. These chemotherapeutic agents, known as Highly Active Anti-Retroviral Therapies (HAART), combine two to four drugs that inhibit different mechanisms of action, demonstrating significant life-extension benefits. However, despite these efforts, AIDS remains incurable, and drug toxicity and the emergence of resistance to existing treatments continue to necessitate the development of new treatments.

[0005] The object of the present invention is to provide a pyrrolopyridine compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, which exhibits an inhibitory effect on the proliferation of human immunodeficiency virus, particularly HIV-1.

[0006] Another object of the present invention is to provide a pharmaceutical composition for inhibiting, preventing or treating a virus, particularly a human immunodeficiency virus infection, comprising the pyrrolopyridine compound or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0007] Another object of the present invention is to provide a method for inhibiting, preventing or treating a virus, particularly a human immunodeficiency virus infection, comprising administering the pyrrolopyridine compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, to a subject in need thereof.

[0008] Another object of the present invention is to provide a use of the pyrrolopyridine compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, for inhibiting, preventing or treating virus infection, particularly human immunodeficiency virus infection.

[0009] As part of efforts to address the aforementioned technical challenges, the inventors of the present invention conducted extensive research to develop a new AIDS treatment. As a result, they discovered that a pyrrolopyridine compound with a novel skeleton exhibited an inhibitory effect on HIV proliferation, leading to the completion of the present invention. The method for solving the technical challenges of the present invention is as follows.

[0010] 1. A compound represented by the following chemical formula 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer, or prodrug thereof:

[0011] Chemical Formula 1

[0012]

[0013] Among the foods,

[0014] R1 is hydrogen, C 1-6 Alkyl, C 3-7 Cycloalkyl, C 1-6Selected from the group consisting of alkyloxy, halo and cyano;

[0015] R2 is hydrogen, C 1-20 Alkyl, C 1-6 Alkyl-O-(CH2) n -O-(CH2) n -, C 1-6 Alkyl-OC(O)O-(CH2) n -, substituted or unsubstituted C 3-7 Cycloalkyl-OC(O)O-(CH3)CH-, substituted or unsubstituted heterocyclyl-(CH2) n -, substituted or unsubstituted heteroaryl-(CH2) n -, and unsubstituted or C 1-6 Alkyl-substituted oxo-dioxolyl-(CH2) n - is selected from the group consisting of, wherein when the cycloalkyl, heterocyclyl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0016] R3 is C 1-6 Alkyl, C 1-6 Alkyloxy, and unsubstituted or substituted C 3-7 Selected from the group consisting of cycloalkyloxy, wherein said C 3-7 When cycloalkyloxy is substituted, the substituent is unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0017] R4 is hydrogen, halo, C 6-10 Aryloxy, C 6-10 Arylamino, unsubstituted or substituted C6-10 Unsubstituted or substituted C fused with aryl, and 4-7 membered heterocyclyl containing one or more heteroatoms in the ring 6-10 Selected from the group consisting of aryl, and the above C 6-10 When aryl is substituted, the substituents are thio, amino, halo, hydroxy, cyano C 1-6 C alkyl substituted with 1 to 3 halo atoms 1-6 Alkyl and C 1-6 At least one selected from the group consisting of alkyloxy;

[0018] R5 is hydrogen, C 3-7 Cycloalkyl or C 1-6 Alkyl, R6 is hydrogen, C 3-7 Cycloalkyl, C 1-6 Alkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)-, R8-(CH2) n -, or substituted or unsubstituted heteroaryl, or R5 and R6 are combined with each other to form C 3-7 It can be a cycloalkyl or a 4-7 membered heterocyclyl containing one or more heteroatoms in the ring, wherein when the heteroaryl is substituted, the substituent is an unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0019] R7 is hydrogen, C 3-7 Cycloalkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)- and R8-(CH2) n - is selected from the group consisting of;

[0020] R8 is hydrogen, halo, hydroxy, amino, azido, cyano, C substituted with 1 to 3 halo 1-6 Alkyl, C2-6 Alkenyl, C 2-6 alkynyl, C 1-6 Alkyloxy, (C 1-3 alkyl)NHC(O)-, (C 1-3 alkyl)2NC(O)-, HOOC-, (C 1-6 alkyl)-S-, (C 1-6 alkyl)-S(O)2-, carbamoyl, C 3-7 Selected from the group consisting of substituted or unsubstituted cycloalkyl, 4-7 membered substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein when said cycloalkyl, heterocyclyl, aryl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0021] n is an integer from 0 to 5.

[0022] 2. A pharmaceutical composition for inhibiting, preventing or treating viral infection, comprising the compound of the above 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0023] 3. A pharmaceutical composition for inhibiting, preventing or treating the above-mentioned virus infection, wherein the virus is human immunodeficiency virus (HIV).

[0024] 4. A method for inhibiting, preventing or treating a viral infection, comprising administering the compound of the above 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, to a subject in need thereof.

[0025] 5. A method for suppressing, preventing, or treating a viral infection according to the above 4, wherein the virus is human immunodeficiency virus (HIV).

[0026] 6. A use for inhibiting, preventing or treating viral infection, comprising the compound of the above 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0027] 7. Use for inhibiting, preventing or treating the above 6 virus infection, wherein the virus is human immunodeficiency virus (HIV).

[0028] According to the present invention, a pyrrolopyridine compound having high selectivity and physiological activity against viruses, particularly human immunodeficiency virus (HIV), or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, and a use thereof for inhibiting or treating viral infection are provided.

[0029] The pyrrolopyridine compound of the present invention, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof, has high selectivity and physiological activity against viruses, particularly human immunodeficiency virus (HIV), and low toxicity, and thus can be usefully used for the inhibition, prevention or treatment of virus, particularly human immunodeficiency virus (HIV) infection.

[0030] Definition of terms

[0031] Briefly explain the terms used in this specification.

[0032] The term "hydrate" means a compound of the present invention or a salt thereof comprising a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular forces.

[0033] The term "solvate" refers to a compound of the present invention or a salt thereof comprising a stoichiometric or non-stoichiometric amount of a solvent bound by non-covalent intermolecular forces. The solvent for the solvate may be any solvent that is volatile, non-toxic, and / or suitable for human administration.

[0034] The term "prodrug" refers to a substance that can be converted in vivo into the compound of formula 1 according to the present invention. Prodrugs are often used because, in some cases, they are easier to administer than the parent drug. For example, they may achieve physiological activity upon oral administration, whereas the parent drug may not. Prodrugs may also have improved solubility in pharmaceutical formulations compared to the parent drug. For example, a prodrug may be in the form of an ester ("prodrug") that facilitates passage through cell membranes, where aqueous solubility would be detrimental to mobility, but once in cells where aqueous solubility is beneficial, it is metabolically hydrolyzed to the active carboxylic acid. Another example of a prodrug is a short peptide (polyamino acid) linked to an acid group that is metabolically converted to reveal the active site.

[0035] The term "stereoisomer" refers to isomers that have the same chemical formula or molecular formula but are formed due to different spatial arrangements of atoms within the molecule. "Enantiomer" refers to an isomer that is not superimposable with its mirror image, like the relationship between right and left hands, and "diastereoisomer" refers to a stereoisomer that is not a mirror image relationship. All of these isomers and their mixtures, i.e., racemates, are also included in the scope of the present invention.

[0036] The term "alkyl" refers to straight, branched and cyclic aliphatic hydrocarbon groups, including both "saturated alkyl" and "unsaturated alkyl" having at least one double bond or triple bond moiety in the chain.

[0037] The term "aryl" refers to an aromatic ring group having 6 to 10 carbon atoms, "heterocyclyl" refers to a 3- to 7-membered ring group having at least one heteroatom selected from nitrogen (N), oxygen (O), and sulfur (S) atoms within the ring, and "heteroaryl" refers to a 5- to 10-membered heteroaromatic ring group having at least one heteroatom selected from nitrogen (N), oxygen (O), and sulfur (S) atoms within the ring, and a two- or three-ring group in which the 5- to 10-membered heteroaromatic ring group is fused with an aromatic ring group having 6 to 10 carbon atoms.

[0038] The contents of the present invention are described in detail below.

[0039] The first aspect of the present invention relates to a compound represented by the following chemical formula 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof:

[0040] Chemical Formula 1

[0041]

[0042] Among the foods,

[0043] R1 is hydrogen, C 1-6 Alkyl, C 3-7 Cycloalkyl, C 1-6 Selected from the group consisting of alkyloxy, halo and cyano;

[0044] R2 is hydrogen, C 1-20 Alkyl, C 1-6 Alkyl-O-(CH2) n -O-(CH2) n -, C 1-6 Alkyl-OC(O)O-(CH2) n -, substituted or unsubstituted C 3-7 Cycloalkyl-OC(O)O-(CH3)CH-, substituted or unsubstituted heterocyclyl-(CH2) n -, substituted or unsubstituted heteroaryl-(CH2) n -, and unsubstituted or C 1-6Alkyl-substituted oxo-dioxolyl-(CH2) n - is selected from the group consisting of, wherein when the cycloalkyl, heterocyclyl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0045] R3 is C 1-6 Alkyl, C 1-6 Alkyloxy, and unsubstituted or substituted C 3-7 Selected from the group consisting of cycloalkyloxy, wherein said C 3-7 When cycloalkyloxy is substituted, the substituent is unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0046] R4 is hydrogen, halo, C 6-10 Aryloxy, C 6-10 Arylamino, unsubstituted or substituted C 6-10 Unsubstituted or substituted C fused with aryl, and 4-7 membered heterocyclyl containing one or more heteroatoms in the ring 6-10 Selected from the group consisting of aryl, and the above C 6-10 When aryl is substituted, the substituents are thio, amino, halo, hydroxy, cyano C 1-6 C alkyl substituted with 1 to 3 halo atoms 1-6 Alkyl and C 1-6 At least one selected from the group consisting of alkyloxy;

[0047] R5 is hydrogen, C 3-7 Cycloalkyl or C 1-6Alkyl, R6 is hydrogen, C 3-7 Cycloalkyl, C 1-6 Alkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)-, R8-(CH2) n -, or substituted or unsubstituted heteroaryl, or R5 and R6 are combined with each other to form C 3-7 It can be a cycloalkyl or a 4-7 membered heterocyclyl containing one or more heteroatoms in the ring, wherein when the heteroaryl is substituted, the substituent is an unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0048] R7 is hydrogen, C 3-7 Cycloalkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)- and R8-(CH2) n - is selected from the group consisting of;

[0049] R8 is hydrogen, halo, hydroxy, amino, azido, cyano, C substituted with 1 to 3 halo 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 alkynyl, C 1-6 Alkyloxy, (C 1-3 alkyl)NHC(O)-, (C 1-3 alkyl)2NC(O)-, HOOC-, (C 1-6 alkyl)-S-, (C 1-6 alkyl)-S(O)2-, carbamoyl, C 3-7Selected from the group consisting of substituted or unsubstituted cycloalkyl, 4-7 membered substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein when said cycloalkyl, heterocyclyl, aryl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo;

[0050] n is an integer from 0 to 5.

[0051] In one specific example of the present invention, the compound of formula 1 is wherein R1 is hydrogen or C 1-6 It may be an alkyl compound.

[0052] In another specific example of the present invention, the compound of formula 1 is wherein R2 is hydrogen, C 1-20 Alkyl, C 1-6 Alkyl-OC(O)O-(CH2) n -, and unsubstituted or C 1-6 Alkyl-substituted oxo-dioxolyl-(CH2) n - may be a compound selected from the group consisting of.

[0053] In another specific example of the present invention, the compound of formula 1 is wherein R3 is C 1-6 Alkyl or C 1-6 It may be an alkyloxy compound.

[0054] In another specific example of the present invention, the compound of formula 1 is C, wherein R4 is hydrogen, or unsubstituted or substituted with one or more halo 6-10 It may be an aryl compound.

[0055] In another specific example of the present invention, the compound of formula 1 is wherein R5 is hydrogen or C 1-6Alkyl, R6 is hydrogen, C 1-6 Alkyl or unsubstituted heteroaryl, or R5 and R6 are combined to form C 3-7 It may be a compound that becomes a cycloalkyl.

[0056] In another specific example of the present invention, the compound of formula 1 is wherein R7 is hydrogen or R8-(CH2) n - and R8 is hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and when the aryl and heteroaryl are substituted, the substituents are each C 1-6 It may be a compound selected from the group consisting of alkyl and halo.

[0057] In the present invention, the C 6-10 Aryl can be phenyl or naphthyl.

[0058] In the present invention, the heterocyclyl may be selected from the group consisting of piperidinyl, piperazinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dioxanyl, tetrahydrofuranyl, and tetrahydropyranyl.

[0059] In the present invention, the heteroaryl may include, but is not limited to, quinolinyl, isoquinolinyl, phthalazinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, dioxoisoindolinyl, oxazolyl, isoxazolyl, oxadiazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, pyranyl, thiophenyl, 2-oxopyrrolidinyl, pyrazolyl, thiazolyl, isothiazolyl, etc., and C 6-10 Any two- or three-ring group consisting of a fusion of an aryl and a 5-6 membered heteroaryl or a fusion of two or more 5-6 membered heteroaryls is possible.

[0060] In the present invention, C fused with the heterocyclyl 6-10Aryl may be selected from the group consisting of chromanyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, tetrahydroquinolinyl and 2,3-dihydropyrano[4,3,2-de]quinolinyl, but is not limited thereto, and may be any two- or three-ring group in which a heterocyclyl and an aryl are fused as exemplified herein.

[0061] In the present invention, the halo may be selected from the group consisting of fluoro, chloro, bromo, and iodo.

[0062] The compound of the above chemical formula 1 according to the present invention may be selected from the group consisting of compounds having the following structure:

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] The second aspect of the present invention relates to a pharmaceutical composition for inhibiting, preventing or treating viral infection, comprising a compound of the above chemical formula 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0073] A third aspect of the present invention relates to a method for inhibiting, preventing or treating a viral infection, comprising administering to a subject in need thereof a compound of the above chemical formula 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0074] The fourth aspect of the present invention relates to a use for inhibiting, preventing or treating viral infection, comprising the compound of the above 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

[0075] In the present invention, the virus may be human immunodeficiency virus (HIV).

[0076] Example

[0077] The present invention is described in more detail below through examples. However, the following examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention solely to these examples.

[0078] Example 1: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-ethyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (Compound 1)

[0079]

[0080] [Step 1] Preparation of (2-amino-5-ethyl-4-methyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrol-3-yl)(4-chlorophenyl)methanone

[0081] (1-Methyl-1H-pyrazol-4-yl)methanamine hydrochloride (200 mg, 1.35 mmol) was dissolved in ethanol (2.7 mL), and diisopropylethylamine (0.592 ml, 3.39 mmol) and 4-chlorobenzoylacetonitrile (268 mg, 1.49 mmol) were sequentially added dropwise. After the temperature of the reaction solution was raised to 35–40°C, 3-bromopentan-2-one (0.25 ml, 2.03 mmol) was slowly added dropwise over 30 minutes. After the addition, the temperature of the reaction solution was maintained at 35–40°C and stirred for 3 hours. After the completion of the reaction, the temperature of the reaction solution was lowered to 10°C, and distilled water was added dropwise over 10 minutes. The aqueous layer was extracted three times with ethyl acetate and washed with a saturated ammonium chloride aqueous solution. The washed organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain the title compound (intermediate 1) (286.4 mg, 0.803 mmol, yield: 59.2%) as an orange oil.

[0082] LCMS: m / z 357.1 [M+H + ].

[0083] [Step 2] Preparation of ethyl 2-(4-(4-chlorophenyl)-2-ethyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate

[0084] Intermediate 1 (286.4 mg, 0.804 mmol) prepared in step 1 was dissolved in acetonitrile (1.6 mL, 0.5 M), and ethyl acetopyruvate (169 μL, 1.20 mmol) and 4 M dioxane hydrochloride solution (602 μL, 2.40 mmol) were sequentially added dropwise. The temperature of the reaction solution was raised to 65 °C and stirred for 12 hours. After completion of the reaction, the reaction solution was concentrated, the temperature was lowered to 0 °C, and ethyl acetate and 7 wt% sodium bicarbonate aqueous solution were added. After stirring for 10 minutes, the mixture was extracted three times with ethyl acetate at room temperature, and then 5 wt% sodium bicarbonate was added. The residue was washed with an aqueous solution. The washed organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain the title compound (Intermediate 2) (179.2 mg, 0.374 mmol, yield: 46.6%) as a white solid.

[0085] LCMS: m / z 479.1 [M+H + ].

[0086] [Step 3] Preparation of ethyl (S)-2-(4-(4-chlorophenyl)-2-ethyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate

[0087] Intermediate 2 (179.2 mg, 0.374 mmol) obtained in step 2 was dissolved in acetonitrile (1.25 mL), and triethylamine (104 μL, 0.747 mmol) was added dropwise. The reaction solution was cooled to -5°C, and formic acid (43 μL, 1.12 mmol) was slowly added dropwise. In another reactor, (pentamethylcyclopentadanyl)rhodium(III) dichloride dimer (10.99 mg, 0.018 mmol) and (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethanediamine (16.30 mg, 0.044 mmol) were dissolved in acetonitrile (400 μL), and the mixture was stirred for 10 minutes. While maintaining the internal temperature at 0~5℃, triethylamine (26.0μL, 0.187 mmol) was added and stirred for 1 hour, then added dropwise to the reaction solution. The reaction solution was reacted for 12 hours while maintaining the internal temperature at -5~5℃. The reaction solution was diluted with distilled water and extracted three times with ethyl acetate. The organic layer was dehydrated over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain the title compound (Intermediate 3) (87.7 mg, 0.182 mmol, yield: 48.8%) as a white solid.

[0088] LCMS: m / z 481.2 [M+H + ].

[0089] [Step 4] Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-ethyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

[0090] Intermediate 3 (87.7 mg, 0.182 mmol) obtained in step 3 was dissolved in dichloromethane (365 μL), and tert-butyl acetate (2.54 mL, 18.96 mmol) was added dropwise. The reaction solution was cooled to 0°C, and 70% perchloric acid (62.7 μL, 0.729 mmol) was slowly added dropwise over 1 hour. The temperature of the reaction solution was increased to 20°C and the mixture was reacted for 1 hour. After completion of the reaction, dichloromethane and a saturated aqueous sodium carbonate solution were added dropwise to the reaction solution, and the mixture was stirred for 20 minutes. The reaction solution was diluted with distilled water and extracted three times with dichloromethane. The extracted organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain compound 1 (64.5 mg, 0.12 mmol, yield: 65.9%) as a white solid.

[0091] LCMS: m / z 537.2 [M+H + ].

[0092] Example 2: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-ethyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (Compound 2)

[0093]

[0094] Compound 1 (64.5 mg, 0.120 mmol) was dissolved in tetrahydrofuran (480 μL) and methanol (120 μL) (4:1, 0.2 M), and sodium hydroxide (14.4 mg, 0.360 mmol) was added dropwise. The reaction solution was stirred at 40–45°C for 4 hours, after which sodium hydroxide (14.4 mg, 0.360 mmol) was additionally added dropwise, and the mixture was stirred for 2 hours. The reaction solution was concentrated, diluted with distilled water, and adjusted to pH 6–7 with 1 N aqueous hydrochloric acid solution. The aqueous layer was extracted twice with dichloromethane. The extracted organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain compound 2 (19.5 mg, 0.039 mmol, yield: 31.9%) as a white solid.

[0095] LCMS: m / z 509.2 [M+H + ].

[0096] Example 3: Preparation of (ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-9-((1-methyl-1H-pyrazol-4-yl)methyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetate (Compound 3)

[0097] Compound 3 (42.3 mg, 0.077 mmol, yield: 30.1%) as a white solid was prepared by reacting (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 2-bromocyclohexan-1-one as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0098] LCMS: m / z 549.2 [M+H + ].

[0099] Example 4: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-9-((1-methyl-1H-pyrazol-4-yl)methyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetic acid (Compound 4)

[0100] Compound 4 (33 mg, 0.063 mmol, yield: 34.3%) as a white solid was prepared from compound 3 (101.5 mg, 0.185 mmol) by a similar method to Example 2.

[0101] LCMS: m / z 521.2 [M+H + ].

[0102] Example 5: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (Compound 5)

[0103] Compound 5 (42.4 mg, 0.077 mmol, yield: 60.2%) as a white solid was prepared by reacting (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 3-chloro-4-methylpentan-2-one as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0104] LCMS: m / z 551.2 [M+H + ].

[0105] Example 6: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (Compound 6)

[0106] Compound 6 (23.7 mg, 0.045 mmol, yield: 65.2%) as a white solid was prepared from compound 5 (38.3 mg, 0.069 mmol) by a similar method to Example 2.

[0107] LCMS: m / z 523.1 [M+H + ].

[0108] Example 7: Preparation of ethyl (R)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (Compound 7)

[0109] [Step 1] Using (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 3-chloro-4-methylpentan-2-one as starting materials, a reaction was performed in a similar manner to steps 1 and 2 of Example 1 to prepare ethyl 2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate (133 mg, 0.270 mmol, yield: 38.3%) as a white solid.

[0110] LCMS: m / z 493.0 [M+H + ].

[0111] [Step 2] Using ethyl 2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate prepared in Step 1 and (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethanediamine, the reaction was carried out in a similar manner to Step 3 of Example 1 to give ethyl (R)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate as a white solid (36.2 mg, 0.073 mmol, yield: (51.5%) was manufactured.

[0112] LCMS: m / z 495.3 [M+H + ].

[0113] [Step 3] From ethyl (R)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (69.8 mg, 0.141 mmol) prepared in Step 2, a white solid compound 7 (46.3 mg, 0.084 mmol, yield: 59.6%) was prepared by reaction in a similar manner to Step 4 of Example 1.

[0114] LCMS: m / z 551.1 [M+H + ].

[0115] Example 8: Preparation of (R)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-isopropyl-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (Compound 8)

[0116] Compound 8 (8.8 mg, 0.017 mmol, yield: 20.03%) as a white solid was prepared from compound 7 (46.3 mg, 0.084 mmol) by a similar method to Example 2.

[0117] LCMS: m / z 523.2 [M+H + ].

[0118] Example 9: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-2-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (Compound 9)

[0119] Compound 9 (18 mg, 0.031 mmol, yield: 24.66%) as a white solid was prepared by reacting (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 1-chloro-1-(pyridin-3-yl)propan-2-one hydrochloride as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0120] LCMS: m / z 586.3 [M+H + ].

[0121] Example 10: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-2-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (Compound 10)

[0122] Compound 10 (11 mg, 0.020 mmol, yield: 64.2%) as a white solid was prepared from compound 9 (18 mg, 0.031 mmol) by a similar method to Example 2.

[0123] LCMS: m / z 558.2 [M+H + ].

[0124] Example 11: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-2-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (Compound 11)

[0125] Compound 11 (121.1 mg, 0.220 mmol, yield: 63.0%) as a white solid was prepared by reacting (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 3-bromohexan-2-one as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0126] LCMS: m / z 551.6 [M+H + ].

[0127] Example 12: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-3,6-dimethyl-1-((1-methyl-1H-pyrazol-4-yl)methyl)-2-propyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (Compound 12)

[0128] Compound 12 (36.3 mg, 0.069 mmol, yield: 31.6%) as a white solid was prepared from compound 11 (121.1 mg, 0.220 mmol) by a similar method to Example 2.

[0129] LCMS: m / z 523.6 [M+H + ].

[0130] Example 13: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-10-((1-methyl-1H-pyrazol-4-yl)methyl)-5,6,7,8,9,10-hexahydrocyclohepta[4,5]pyrrolo[2,3-b]pyridin-3-yl)acetate (Compound 13)

[0131] Compound 13 (139.5 mg, 0.248 mmol, yield: 70.6%) as a white solid was prepared by reacting (1-methyl-1H-pyrazol-4-yl)methanamine hydrochloride and 2-chlorocycloheptan-1-one as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0132] LCMS: m / z 563.3 [M+H + ].

[0133] Example 14: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-10-((1-methyl-1H-pyrazol-4-yl)methyl)-5,6,7,8,9,10-hexahydrocyclohepta[4,5]pyrrolo[2,3-b]pyridin-3-yl)acetic acid (Compound 14)

[0134] Compound 14 (66.1 mg, 0.124 mmol, yield: 49.9%) as a white solid was prepared from compound 13 (139.5 mg, 0.248 mmol) by a similar method to Example 2.

[0135] LCMS: m / z 535.2 [M+H + ].

[0136] Example 15: Preparation of ethyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-9-(3,4-difluorobenzyl)-2-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetate (Compound 15)

[0137] Compound 15 (67.8 mg, 0.117 mmol, yield: 65.5%) as a white solid was prepared by reacting (3,4-difluorophenyl)methanamine and 2-bromocyclohexan-1-one as starting materials in a similar manner to steps 1 to 4 of Example 1.

[0138] LCMS: m / z 581.2[M+H + ].

[0139] Example 16: Preparation of (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-9-(3,4-difluorobenzyl)-2-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetic acid (Compound 16)

[0140] Compound 16 (40.3 mg, 0.073 mmol, yield: 62.5%) as a white solid was prepared from compound 15 (67.8 mg, 0.117 mmol) by a similar method to Example 2.

[0141] LCMS: m / z 552.9 [M+H + ].

[0142] Example 17: Preparation of (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-9-((1-methyl-1H-pyrazol-4-yl)methyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetate (Compound 17)

[0143]

[0144] Compound 4 (9.3 mg, 0.018 mmol) was dissolved in N,N-dimethylformamide (59.5 μL), and 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one (2.92 μL, 0.027 mmol) and cesium carbonate (17.45 mg, 0.054 mmol) were sequentially added dropwise. The reaction solution was reacted at room temperature overnight. After completion of the reaction, the reaction solution was diluted with water, and the aqueous layer was extracted three times with ethyl acetate and washed with a saturated aqueous ammonium chloride solution. The washed organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain compound 17 (6.3 mg, 9.95 μmol, yield: 55.7%) as a colorless oil.

[0145] LCMS: m / z 633.2 [M+H + ].

[0146] Example 18: Preparation of ((methoxycarbonyl)oxy)methyl (S)-2-(tert-butoxy)-2-(4-(4-chlorophenyl)-2-methyl-9-((1-methyl-1H-pyrazol-4-yl)methyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-3-yl)acetate (Compound 18)

[0147] Compound 4 (9.3 mg, 0.018 mmol) and chloromethyl methyl carbonate (3.33 mg, 0.027 mmol) were reacted as starting materials in a similar manner to Example 17 to prepare compound 18 (3.2 mg, 5.25 μmol, yield: 29.4%) as a colorless oil.

[0148] LCMS: m / z 609.2 [M+H + ].

[0149] Experimental example

[0150] Experimental Example 1: HIV-1 (Wild Type) Inhibitory Effect and Cytotoxicity Test

[0151] To determine the inhibitory effect of the compound of the present invention on HIV-1 (Wild Type), the following experiment was conducted. MT-4 cells were used as host cells, and the NL4-3 strain of HIV-1 was used as the virus strain. The virus and cells were mixed in the presence of the compound of the present invention and incubated for 6 days. The antiviral effect was measured as the percentage reduction in viral cytopathic effect (CPE), and the compound cytotoxicity was assessed by XTT dye reduction. The results are shown in Table 1 below.

[0152]

[0153] The present invention has been described in detail through examples. However, it should be apparent to those skilled in the art that these specific descriptions are merely preferred embodiments and that the scope of the present invention is not limited by these examples. Therefore, the actual scope of the present invention is defined by the appended claims and their equivalents.

Claims

1. A compound represented by the following chemical formula 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer, or prodrug thereof: Chemical Formula 1 Among the foods, R1 is hydrogen, C 1-6 Alkyl, C 3-7 Cycloalkyl, C 1-6 Selected from the group consisting of alkyloxy, halo and cyano; R2 is hydrogen, C 1-20 Alkyl, C 1-6 Alkyl-O-(CH2) n -O-(CH2) n -, C 1-6 Alkyl-OC(O)O-(CH2) n -, substituted or unsubstituted C 3-7 Cycloalkyl-OC(O)O-(CH3)CH-, substituted or unsubstituted heterocyclyl-(CH2) n -, substituted or unsubstituted heteroaryl-(CH2) n - and unsubstituted or C 1-6 Alkyl-substituted oxo-dioxolyl-(CH2) n - is selected from the group consisting of, wherein when the cycloalkyl, heterocyclyl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo; R3 is C 1-6 Alkyl, C 1-6 Alkyloxy, and unsubstituted or substituted C 3-7 Selected from the group consisting of cycloalkyloxy, wherein said C 3-7 When cycloalkyloxy is substituted, the substituent is unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo; R4 is hydrogen, halo, C 6-10 Aryloxy, C 6-10 Arylamino, unsubstituted or substituted C 6-10 Unsubstituted or substituted C fused with aryl, and 4-7 membered heterocyclyl containing one or more heteroatoms in the ring 6-10 Selected from the group consisting of aryl, and the above C 6-10 When aryl is substituted, the substituents are thio, amino, halo, hydroxy, cyano C 1-6 C alkyl substituted with 1 to 3 halo atoms 1-6 Alkyl and C 1-6 At least one selected from the group consisting of alkyloxy; R5 is hydrogen, C 3-7 Cycloalkyl or C 1-6 Alkyl, R6 is hydrogen, C 3-7 Cycloalkyl, C 1-6 Alkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)-, R8-(CH2) n -, or substituted or unsubstituted heteroaryl, or R5 and R6 are combined with each other to form C 3-7 It can be a cycloalkyl or a 4-7 membered heterocyclyl containing one or more heteroatoms in the ring, wherein when the heteroaryl is substituted, the substituent is an unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 At least one selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo; R7 is hydrogen, C 3-7 Cycloalkyl, (C 1-6 alkyl)-OC(O)-, (C 1-6 Alkyl)-C(O)- and R8-(CH2) n - is selected from the group consisting of; R8 is hydrogen, halo, hydroxy, amino, azido, cyano, C substituted with 1 to 3 halo 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 alkynyl, C 1-6 Alkyloxy, (C 1-3 alkyl)NHC(O)-, (C 1-3 alkyl)2NC(O)-, HOOC-, (C 1-6 alkyl)-S-, (C 1-6 alkyl)-S(O)2-, carbamoyl, C 3-7 Selected from the group consisting of substituted or unsubstituted cycloalkyl, 4-7 membered substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein when said cycloalkyl, heterocyclyl, aryl and heteroaryl are substituted, they are each unsubstituted C 1-6 C substituted with alkyl, halo, amino or hydroxy 1-6 Alkyl, C 1-6 which may be substituted with one or more substituents selected from the group consisting of alkyloxy, cyano, carboxy, amino, nitro, azido, hydroxy, carbamoyl, thio and halo; n is an integer from 0 to 5.

2. In the first paragraph, R1 is hydrogen or C 1-6 An alkyl compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

3. In the first paragraph, R2 is hydrogen, C 1-20 Alkyl, C 1-6 Alkyl-OC(O)O-(CH2) n -, and unsubstituted or C 1-6 Alkyl-substituted oxo-dioxolyl-(CH2) n A compound selected from the group consisting of -, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

4. In the first paragraph, R3 is C 1-6 Alkyl or C 1-6 An alkyloxy compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

5. In the first paragraph, R4 is hydrogen, or C unsubstituted or substituted with one or more halo 6-10 An aryl compound, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

6. In the first paragraph, R5 is hydrogen or C 1-6 Alkyl, R6 is hydrogen, C 1-6 Alkyl or unsubstituted heteroaryl, or R5 and R6 are combined to form C 3-7 A compound which is a cycloalkyl, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

7. In the first paragraph, R7 is hydrogen or R8-(CH2) n - and R8 is hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and when the aryl and heteroaryl are substituted, the substituents are each C 1-6 A compound comprising at least one selected from the group consisting of alkyl and halo, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

8. In the first paragraph, the C 6-10 Aryl is phenyl or naphthyl; said heterocyclyl is selected from the group consisting of piperidinyl, piperazinyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, dioxanyl, tetrahydrofuranyl and tetrahydropyranyl; said heteroaryl is selected from the group consisting of quinolinyl, isoquinolinyl, phthalazinyl, quinazolinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, dioxoisoindolinyl, oxazolyl, isoxazolyl, oxadiazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, pyranyl, thiophenyl, 2-oxopyrrolidinyl, pyrazolyl, thiazolyl and isothiazole; C fused with said heterocyclyl 6-10 A compound wherein aryl is selected from the group consisting of chromanyl, 3,4-dihydro-2H-benzo[b][1,4]oxazinyl, tetrahydroquinolinyl and 2,3-dihydropyrano[4,3,2-de]quinolinyl, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

9. In paragraph 1, the compound of formula 1 is a compound selected from the group consisting of compounds having the following structure, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof:

10. A pharmaceutical composition for inhibiting, preventing or treating viral infection, comprising a compound of formula 1 according to paragraph 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

11. A pharmaceutical composition for inhibiting, preventing or treating a viral infection, wherein the virus in paragraph 10 is human immunodeficiency virus (HIV).

12. A method for inhibiting, preventing or treating a viral infection, comprising administering to a subject in need thereof a compound of formula 1 according to paragraph 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof.

13. A method for inhibiting, preventing or treating a viral infection in claim 12, wherein the virus is human immunodeficiency virus (HIV).

14. Use of the compound of formula 1 according to paragraph 1, or a pharmaceutically acceptable salt, stereoisomer, hydrate, solvate, tautomer or prodrug thereof for inhibiting, preventing or treating viral infection.

15. In the 14th paragraph, the use for suppressing, preventing or treating viral infection, wherein the virus is human immunodeficiency virus (HIV).

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