# US 2021/0276985 A1 · Novel compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0276985 A1 - Document ID: US20210276985A1 - Status: Published application - Kind: A1 - Application number: 17/232,049 - Filed: 2021-04-15 - Published: 2021-09-09 - Earliest claimed: 2018-10-16 - Assignees: Autifony Therapeutics Limited - Applicants: Autifony Therapeutics Limited - Inventors: Giuseppe Alvaro; Agostino Marasco - Web page: https://patentgrep.com/patent/US20210276985A1 ## CPC - C07D 405/14: containing three or more hetero rings - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract Disclosed is a compound of formula (I): wherein R1 is H or methyl, R2 and R3 are both methyl, or R2 and R3, together with the carbon atom to which they are attached, are a spirocyclopropyl ring, R4 is methyl or ethyl, R5 is H or methyl, or R4 and R5, together with the carbon atom to which they are attached, form a C3-C4 spiro carbocyclyl. Also disclosed are methods for treating and/or preventing one or more diseases or disorders comprising administering to a subject an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt, solvate and/or derivative thereof. Additionally, methods using a compound of formula (I) to manufacture medicaments are provided. ## Claims ### Claim 1 A compound of formula (I): wherein: R1 is H or methyl; R2 and R3 are both methyl, or R2 and R3, together with the carbon atom to which they are attached, are a spirocyclopropyl ring; R4 is methyl or ethyl; R5 is H or methyl; or R4 and R5, together with the carbon atom to which they are attached, form a C3-C4 spiro carbocyclyl; or a salt and/or solvate and/or derivative thereof. ### Claim 2 (depends on 1) The compound according to claim 1 wherein R1 is H. ### Claim 3 (depends on 1) The compound according to claim 1 wherein R1 is methyl. ### Claim 4 (depends on 1) The compound according to claim 1, wherein R2 and R3, together with the carbon atom to which they are attached, are a spiro cyclopropyl ring. ### Claim 5 (depends on 1) The compound according to claim 1, wherein R2 is methyl and R3 is methyl ### Claim 6 (depends on 1) The compound according to claim 1, wherein R4 is methyl. ### Claim 7 (depends on 1) The compound according to claim 1, wherein R4 is ethyl. ### Claim 8 (depends on 1) The compound according to claim 1, wherein R5 is H. ### Claim 9 (depends on 1) The compound according to claim 1, wherein R5 is methyl. ### Claim 10 (depends on 1) The compound according to claim 1, wherein R4 and R5, together with the carbon atom to which they are attached, form a spirocyclopropyl. ### Claim 11 (depends on 1) The compound according to claim 1, wherein R4 and R5, together with the carbon atom to which they are attached, form a spirocyclobutyl. ### Claim 12 (depends on 1) The compound according to claim 1 selected from the group consisting of: 5,5-dimethyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione; 3-[5-[(3,3-dimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]-5,5-dimethyl-imidazolidine-2,4-dione; (5R)-5-ethyl-5-methyl-3-(5-spiro[2H-benzofuran-3,1′-cyclopropane]-4-yloxypyrazin-2-yl)imidazolidine-2,4-dione; 5,5-dimethyl-3-(5-spiro[2H-benzofuran-3,1′-cyclopropane]-4-yloxypyrazin-2-yl)imidazolidine-2,4-dione; (5R)-5-ethyl-5-methyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione; (5R)-3-[5-[(3,3-dimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]-5-ethyl-5-methyl-imidazolidine-2,4-dione; 5,5-dimethyl-3-[5-[(3,3,7-trimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]imidazolidine-2,4-dione; (5R)-5-ethyl-5-methyl-3-[5-[(3,3,7-trimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]imidazolidine-2,4-dione; (5R)-5-ethyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione; (5R)-5-ethyl-3-(5-spiro[2H-benzofuran-3,1′-cyclopropane]-4-yloxypyrazin-2-yl)imidazolidine-2,4-dione; (5R)-3-[5-[(3,3-dimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]-5-ethyl-imidazolidine-2,4-dione; (5R)-5-ethyl-3-[5-[(3,3,7-trimethyl-2H-benzofuran-4-yl)oxy]pyrazin-2-yl]imidazolidine-2,4-dione; 7-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]-5,7-diazaspiro[3.4]octane-6,8-dione; 6-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]-4,6-diazaspiro[2.4]heptane-5,7-dione; (5S)-5-ethyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione; and salts, solvates and derivatives thereof. ### Claim 13 (depends on 1) The compound according to claim 1 which is: 5,5-dimethyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione. ### Claim 14 (depends on 1) The compound according to claim 1 which is: (5R)-5-ethyl-3-[5-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyrazin-2-yl]imidazolidine-2,4-dione. ### Claim 15 (depends on 1) The compound according to claim 1 which is: (5R)-5-ethyl-3-(5-spiro[2H-benzofuran-3,1′-cyclopropane]-4-yloxypyrazin-2-yl)imidazolidine-2,4-dione. ### Claim 16 (depends on 1) A method for the prophylaxis or treatment of a disease or disorder selected from the group consisting of hearing disorders, schizophrenia, depression and mood disorders, bipolar disorder, substance abuse disorders, anxiety disorders, sleep disorders, hyperacusis and disturbances of loudness perception, Ménière's disease, disorders of balance, and disorders of the inner ear, impulse control disorder, personality disorders, attention-deficit/hyperactivity disorder, autism spectrum disorders, eating disorders, cognition impairment, ataxia, pain such as neuropathic pain, inflammatory pain and miscellaneous pain, Lewy body dementia and Parkinson's disease which comprises administering to a subject in need thereof an effective amount of a compound according to claim 1. ### Claim 17 (depends on 1) A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier or excipient. ### Claim 18 (depends on 1) A compound of formula (II) or (XVI): wherein R1, R2 and R3 are as defined in claim 1, and X is halo. ### Claim 19 (depends on 1) A compound of formula (IV): wherein R4 and R5 are as defined in claim 1, and Y is halo. ### Claim 20 (depends on 1) The compound according to claim 1, wherein the compound is administered orally once or twice per day at 2 to 400 mg per day, such as 2 to 300 mg per day, especially 5 to 250 mg per day.