# US 2013/0158025 A1 · Novel compound acting as a cannabinoid receptor-1 inhibitor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0158025 A1 - Document ID: US20130158025A1 - Status: Published application - Kind: A1 - Application number: 13/819,601 - Filed: 2011-08-31 - Published: 2013-06-20 - Earliest claimed: 2010-08-31 - Assignees: Amorepacific Corporation - Inventors: Song Seok Shin; Yong Deog Hong; Kyoung Hee Byoun; Mi Young Park; Jin Kyu Choi; Yang Hui Park; Il Hong Bae; Yung Hyup Joo; Kyung Min Lim; Young Ho Park - Web page: https://patentgrep.com/patent/US20130158025A1 ## CPC - C07D 487/04: Ortho-condensed systems - A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants - A61P 3/04: Anorexiants; Antiobesity agents - A61P 3/06: Antihyperlipidemics - A61P 3/10: for hyperglycaemia, e.g. antidiabetics - A61P 9/00: Drugs for disorders of the cardiovascular system - A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure - A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis - A61P 9/12: Antihypertensives - A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives - A61P 25/00: Drugs for disorders of the nervous system - A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia - A61P 25/22: Anxiolytics - A61P 25/24: Antidepressants - A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia - A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] - A61P 35/00: Antineoplastic agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - A61K 31/519: ortho- or peri-condensed with heterocyclic rings - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract Disclosed is a novel compound acting as a cannabinoid receptor 1 inhibitor, a prodrug thereof, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof. The novel compound or the like is useful for preventing or treating diseases mediated by the cannabinoid receptor-1. ## Claims ### Claim 1 A compound of Chemical Formula 1, a prodrug thereof, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof: wherein R1 is selected from a group consisting of hydrogen, C1-C5 alkyl, haloalkyl, C1-C5 cycloalkyl and C1-C5 alkoxyalkyl; each of R2, R3, R4, R5 and R6 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy, C1-C5 alkoxy alkyl, halo C1-C3 alkyl, halo C1-C5 alkoxy, haloalkoxy C2-C5 alkenyl, C2-C5 alkenyl, alkynyl, carboxyl, C1-C5 alkylcarbonyl, C1-C5 alkoxycarbonyl, C1-C5 alkylcarbonylamino, C1-C5 alkylaminocarbonyl, C1-C5 alkylsulfanyl, C1-C5 alkylsulfonyl, C1-C5 alkoxysulfonyl, C1-C5 alkylsulfamoyl, aryl, aryl C1-C3 alkyl, aryl C1-C5 alkoxy, aminosulfonyl, C1-C5 alkylamino, C1-C5 alkylaminosulfonyl, C1-C5 alkylsulfonylamino, C1-C5 alkylthio, C3-C7 cycloalkylsulfonylaminophenyl, or two selected from R2 through R6 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; each of R7, R8, R9, R10 and R11 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, C1-C5 alkyl, C1-C5 alkoxy, halo C1-C3 alkyl, haloalkoxy C2-C5 alkenyl, C2-C5 alkenyl and alkynyl; and each of R12 and R13 is independently selected from a group consisting of hydrogen, C1-C5 alkyl, hydroxy C1-C5alkyl, C3-C7 cycloalkyl and halo C1-C5 alkyl, or R12 and R13 form a 5- to 7-membered ring together with the nitrogen atom which they are bound and the ring contains 0-2 N, O or S atoms or at least one substituent selected from a group consisting of hydrogen, hydroxy, hydroxy C1-C5 alkyl, C1-C5 alkoxy, C1-C5 alkoxy alkyl, halo C1-C5 alkyl, halo C1-C5 alkoxy and carboxyl. ### Claim 2 (depends on 1) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 1, wherein the compound is represented by Chemical Formula 2: wherein R1 is selected from a group consisting of hydrogen, C1-C5 alkyl, haloalkyl, C1-C5 cycloalkyl and C1-C5 alkoxyalkyl; each of R2, R3, R4, R5 and R6 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy, C1-C5 alkoxy alkyl, halo C1-C3 alkyl, halo C1-C5 alkoxy, haloalkoxy C2-C5 alkenyl, C2-C5 alkenyl, alkynyl, carboxyl, C1-C5 alkylcarbonyl, C1-C5 alkoxycarbonyl, C1-C5 alkylcarbonylamino, C1-C5 alkylaminocarbonyl, C1-C5 alkylsulfanyl, C1-C5 alkylsulfonyl, C1-C5 alkoxysulfonyl, C1-C5 alkylsulfamoyl, aryl, aryl C1-C3 alkyl, aryl C1-C5 alkoxy, aminosulfonyl, C1-C5 alkylamino, C1-C5 alkylaminosulfonyl, C1-C5 alkylsulfonylamino, C1-C5 alkylthio, C3-C7 cycloalkylsulfonylaminophenyl, or two selected from R2 through R6 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; each of R7, R8, R9, R10 and R11 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, C1-C5 alkyl, C1-C5 alkoxy, halo C1-C3 alkyl, haloalkoxy C2-C5 alkenyl, C2-C5 alkenyl and alkynyl; R14 is selected from a group consisting of hydrogen, hydroxy, hydroxy C1-C5 alkyl, C1-C5 alkoxy, C1-C5 alkoxy alkyl, halo C1-C5 alkyl, halo C1-C5 alkoxy and carboxyl; and n is an integer selected from 1 to 3. ### Claim 3 (depends on 1) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 1, wherein the compound is represented by Chemical Formula 3: wherein R1 is selected from a group consisting of methyl, ethyl, propyl, butyl, isobutyl, difluoromethyl, trifluoromethyl, cyclopropyl, ethoxymethyl, methoxymethyl and ethoxyethyl; each of R3, R4 and R5 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, hydroxymethyl, hydroxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl, acetylenyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetyl, methylsulfanyl, ethylsulfanyl, methylsulfonyl, methylsulfonylamino, cyclopropylaminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methylcarbonylamino, methylsulfamoyl, phenylmethyl, phenylethyl, phenylmethoxy, phenylacetyl, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylamino, diethylamino, cyclopropylamino and methylthio, or two selected from R3 through R5 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; and each of R8, R9 and R10 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, butyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, hydroxymethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl and acetylenyl. ### Claim 4 (depends on 3) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 3, wherein: R1 is selected from a group consisting of methyl, ethyl, propyl, butyl, isobutyl, trifluoromethyl, cyclopropyl, ethoxymethyl, methoxymethyl and ethoxyethyl; each of R3, R4 and R5 is independently selected from a group consisting of hydrogen, fluoro, chloro, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methoxy, ethoxy, propoxy, methylenedioxy, isopropoxy, hydroxymethyl, hydroxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl, acetylenyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetyl, methylsulfonyl, methylsulfamoyl, phenylmethyl, phenylethyl and methylthio, or two selected from R3 through R5 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; and each of R8, R9 and R10 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, butyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, hydroxymethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl and acetylenyl. ### Claim 5 (depends on 1) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 1, wherein the compound is selected from a group consisting of: {1-[7-(3-chloro-4-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-chloro-4-fluorophenyl)-3-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(3-fluoro-4-methylphenyl)-7-(3-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(2,4-difluorophenyl)-7-(3-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(3-fluoro-4-methylphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(2,4-difluorophenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-chloro-4-fluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,4-difluorophenyl-3-(3-fluoro-4-methyl-phenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-ethylphenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(3-ethylphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,5-difluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(3,4-difluorophenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-fluorophenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(3,4-difluorophenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo-1,3]dioxol-5-yl-7-(3,5-difluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,5-difluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl}-methanol, {1-[3-(4-methoxyphenyl)-2-trifluoromethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-3-(4-methoxyphenyl)-7-(3-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-(4-fluorophenyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-difluoromethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-2-ethoxymethyl-7-(3-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethyl-7-(4-fluorophenyl)-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-chlorophenyl)-2-ethyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethyl-7-(3-fluorophenyl)-3-p-tolylpyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-2-ethoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(3-chlorophenyl)-2-ethoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-(3-fluorophenyl)-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-m-tolyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-(3-fluorophenyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-(4-fluorophenyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-methoxymethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-butyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-ethoxymethyl-7-(3-methoxyphenyl)-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-ethoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-ethoxymethyl-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-ethoxymethyl-7-(3-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-ethoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, 2-{[3-(4-chlorophenyl)-2-methoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, 2-{[2-methoxymethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-fluorophenyl)-2-methoxymethyl-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(3-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(4-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-2-methoxymethyl-7-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-3-(5-(2-hydroxymethyl)pyrrolidin-1-yl)-2-(methoxymethyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-7-yl)benzonitrile, (S)-[{1-(2-methoxymethyl)-3-(methoxyphenyl)-7-(m-tolyl)-pyrazolo[1,5-a]-pyrimidin-5-yl}-pyrrolidin-2-yl]-methanol, (S)-{[1-(2-methoxymethyl)-7-(3-methoxyphenyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(2,4-difluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, [1-(3-benzo[1,3]dioxol-5-yl-2-methyl-7-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-pyrrolidin-2-yl]-methanol, {1-[3-(4-ethoxyphenyl)-2-methyl-7-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-methoxyphenyl)-2-methyl-7-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-(1-(7-(3,4-difluorophenyl)-3-(4-ethoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl)-pyrrolidin-2-yl)-methanol, {1-[2-methyl-3-(4-methylsulfanylphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,4-difluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,4-difluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,4-difluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3,4-difluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(3,4-difluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, [1-(2-methyl-7-phenyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl]-methanol, [1-[3-(4-difluoromethylphenyl)-7-(3-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-difluoromethylphenyl)-7-(3-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-difluoromethylphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-difluoromethylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-difluoromethylphenyl)-2-methyl-7-m-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-methoxyphenyl)-2-methyl-3-(4-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-ethylphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-ethylphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-methyl-3-(4-trifluoromethylphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-chlorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, [1-(2-methyl-3,7-di-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl)-pyrrolidin-2-yl]-methanol, {1-[7-(3-chlorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-chlorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol [1-(2-methyl-7-m-tolyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl)-pyrrolidin-2-yl]-methanol, {1-[7-(3-methoxyphenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-methoxyphenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(2-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(3-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-fluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-ethoxyphenyl)-7-(3-fluoromethylphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[2-methyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-methoxyphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(3-chlorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(4-vinylphenyl)-pyrazolo[1,5-a]-pyrrolidin-2-yl}-methanol, {1-[3-(4-ethoxyphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-fluoro-3-methylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(3-fluoro-4-methylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-ethoxyphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(4-propoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-biphenyl-4-yl-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(2,4-difluorophenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(4-ethylsulfanylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(4-butoxyphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(4-methylsulfanylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(4-benzoyloxyphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(3-trifluoromethoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(4-trifluoromethoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(4-ethylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[7-(4-fluorophenyl)-2-methyl-3-(4-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, 1-{4-[7-(4-fluorophenyl)-5-(2-hydroxymethyl-pyrrolidin-1-yl)-2-methyl-pyrazolo[1,5-a]pyrimidin-3-yl]phenyl}-ethanol, {1-[3-(4-tert-butylphenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-2-yl}-methanol, [1-(2-methyl-7-phenyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(3-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-methyl-7-m-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-benzo[1,3]dioxol-5-yl-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[7-(4-fluorophenyl)-3-(4-methoxyphenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, {1-[3-(4-chlorophenyl)-2-cyclopropyl-7-(3-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(4-chlorophenyl)-7-(3-chlorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3,7-bis-(4-chlorophenyl)-2-methyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(2,4-dichlorophenyl)-2-cyclopropyl-7-(2-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, {1-[3-(2,4-dichlorophenyl)-2-cyclopropyl-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[3-(4-chlorophenyl)-2-methyl-7-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}methanol, (S)-{1-[7-(2-fluorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[2-ethoxymethyl-3-(4-methoxyphenyl)-7-(3-tolyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[7-(3-chlorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidine-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[7-(4-chlorophenyl)-2-(methoxymethyl)-3-(4-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[3-(4-chlorophenyl)-2-(methoxymethyl)-7-(3-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[3-(4-chlorophenyl)-2-(methoxymethyl)-7-(3-methylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[2-butyl-7-(3-tolyl)-3-(4-tolyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[2-butyl-3-(p-tolyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol, (S)-{1-[2-propyl-3-(p-tolyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidine-5-yl]-pyrrolidin-2-yl}-methanol and (S)-{1-[2-propyl-7-(m-tolyl)-3-(p-tolyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-pyrrolidin-2-yl}-methanol. ### Claim 6 (depends on 1) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 1, wherein the compound is represented by Chemical Formula 4: wherein R1 is selected from a group consisting of methyl, ethyl, propyl, butyl, isobutyl, difluoromethyl, trifluoromethyl, cyclopropyl, ethoxymethyl, methoxymethyl and ethoxyethyl; each of R3, R4 and R5 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, hydroxymethyl, hydroxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl, vinyl, acetylenyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetyl, methylsulfanyl, ethylsulfanyl, methylsulfonyl, methylsulfonylamino, cyclopropylaminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methylcarbonylamino, methylsulfamoyl, phenylmethyl, phenylethyl, phenylmethoxy, phenylacetyl, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylamino, diethylamino, cyclopropylamino and methylthio, or two selected from R3 through R5 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; each of R8, R9 and R10 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, butyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, hydroxymethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl and acetylenyl; and each of R12 and R15 is independently selected from a group consisting of hydrogen, methyl, ethyl, propyl, methoxy, ethoxy and hydroxy. ### Claim 7 (depends on 6) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 6, wherein: R1 is selected from a group consisting of methyl, ethyl, propyl, butyl, isobutyl, trifluoromethyl, cyclopropyl, ethoxymethyl, methoxymethyl and ethoxyethyl; each of R3, R4 and R5 is independently selected from a group consisting of hydrogen, fluoro, chloro, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methoxy, ethoxy, propoxy, methylenedioxy, isopropoxy, hydroxymethyl, hydroxyethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl, acetylenyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetyl, methylsulfonyl, methylsulfamoyl, phenylmethyl, phenylethyl and methylthio, or two selected from R3 through R5 form a 5- to 7-membered ring fused with an aryl group together with the carbon atoms to which they are bound and the ring includes 0-2 double bonds and contains 0-2 N, O or S atoms; and each of R8, R9 and R10 is independently selected from a group consisting of hydrogen, fluoro, chloro, bromo, iodo, nitro, cyano, methyl, ethyl, propyl, butyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, hydroxymethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trifluoromethoxyvinyl and acetylenyl. ### Claim 8 (depends on 6) The compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 6, wherein the compound is selected from a group consisting of: 2-{[3-(4-methoxyphenyl)-2-methyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-benzo[1,3]dioxol-5-yl-2-ethoxymethyl-7-(3-methoxyphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[7-(3-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[7-(4-fluorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[7-(3-chlorophenyl)-2-methyl-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-amino}-ethanol, 2-[2-ethoxymethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[2-ethoxymethyl-7-(4-fluorophenyl)-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-amino}-ethanol, 2-{3-benzo[1,3]dioxol-5-yl-2-ethoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-benzo[1,3]dioxol-5-yl-7-(3-chlorophenyl)-2-ethoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[2-ethoxymethyl-7-(3-fluorophenyl)-3-p-tolyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[2-ethoxymethyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[2-butyl-3-p-tolyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-2-ethoxymethyl-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-2-ethoxymethyl-7-(3-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-2-ethoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-2-methoxymethyl-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-7-(4-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-7-(3-fluorophenyl)-2-methoxymethyl-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[2-methoxymethyl-3-(4-methoxyphenyl)-7-(3-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol, 2-{[3-(4-chlorophenyl)-2-ethoxymethyl-7-(4-fluorophenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-ethylamino}-ethanol and 2-{[3-(4-chlorophenyl)-2-methoxymethyl-7-(m-tolyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-methylamino}-ethanol. ### Claim 9 (canceled) ### Claim 10 (depends on 1) A method for preventing or treating a disease mediated by the cannabinoid receptor-1, comprising: administering to a subject in need thereof, the compound, the prodrug thereof, the isomer thereof, the pharmaceutically acceptable salt thereof, the hydrate thereof or the solvate thereof according to claim 1. ### Claim 11 (depends on 10) The method according to claim 10, wherein the disease mediated by the cannabinoid receptor-1 is at least one selected from a group consisting of inflammatory pain, psycopathy, anxiety, depression, attention deficiency, memory or cognitive disorder, neuropathic pain disorder, sexual dysfunction, impulse control disorder, obesity, neurological or obsessive eating disorder, cancer, morning sickness, nausea, gastric ulcer, diabetes, hypertension, hyperlipidemia, valvular heart disease, myocardial infarction, cardiomegaly and congestive heart failure. ### Claim 12 (depends on 10) The method according to claim 10, wherein the disease mediated by the cannabinoid receptor-1 is obesity. ### Claim 13 (depends on 12) The method according to claim 12, wherein the method prevents or treats obesity through control of appetite, facilitation of energy metabolism or regulation of processes related with fat metabolism. ### Claim 14 A method for preparing pyrazolo[1,5-a]pyrimidine having an aryl substituent bound at 7-position, comprising reacting aminopyrazole and a diketoester in a pyridine solvent, wherein at least one of the aminopyrazole and the diketoester contains an aryl group. ### Claim 15 (canceled)