# US 11,440,896 B2 · Aminoalkyl compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,440,896 B2 - Document ID: US11440896B2 - Status: Granted - Kind: B2 - Application number: 16/965,972 - Filed: 2019-02-05 - Published: 2021-02-11 - Granted: 2022-09-13 - Earliest claimed: 2018-02-06 - Assignees: Daiichi Sankyo Company, Limited - Applicants: Daiichi Sankyo Company, Limited - Inventors: Keisuke Suzuki - Web page: https://patentgrep.com/patent/US11440896B2 ## CPC - C07D 309/04: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms - C07D 309/06: Radicals substituted by oxygen atoms - A61K 9/7023: {Transdermal patches and similar drug-containing composite devices, e.g. cataplasms (galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006)} - A61K 9/7053: {obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene} - A61P 25/04: Centrally acting analgesics, e.g. opioids - A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] - A61P 35/00: Antineoplastic agents - C07D 309/08: 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 - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - 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) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract The present invention directs to provide a novel compound for treating and/or preventing pain, having excellent skin permeation and reduced skin irritation. The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof (R1: a methyl group or other like group, R2: a fluorine atom or other like group, R3: a methyl group or other like group, R4: a methyl group or other like group, R5: a methyl group or other like group) ## Claims ### Claim 1 A compound of formula (I) or a pharmaceutically acceptable salt thereof: wherein: R1 is a hydrogen atom or a methyl group; R2 is a hydrogen atom or a fluorine atom; R3 is a hydrogen atom or a methyl group; R4 is a hydrogen atom or a methyl group; and R5 is a hydrogen atom or a methyl group. ### Claim 2 (depends on 1) The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R1 is a hydrogen atom. ### Claim 3 (depends on 1) The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R2 is a hydrogen atom. ### Claim 4 (depends on 1) The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R3 is a hydrogen atom. ### Claim 5 (depends on 1) The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R4 and R5 are hydrogen atoms. ### Claim 6 (depends on 1) The compound according to claim 1 or a pharmaceutically acceptable salt thereof selected from the group consisting of: 3-[(3R*,4R*)-3-(Dimethylaminomethyl)tetrahydropyran-4-yl[phenol; 3-[(4R*,5R*)-5-(Dimethylaminomethyl)-2,2-dimethyltetrahydropyran-4-yl[phenol; 3-[(3R*,4R*)-3-(Dimethylaminomethyl)tetrahydropyran-4-yl[-5-methylphenol; 3-[(3R*,4R*)-3-(Dimethylaminomethyl)tetrahydropyran-4-yl[-2-methylphenol; 3-[3-Dimethylaminomethyl-4-fluorotetrahydropyran-4-yl[-phenol; and pharmaceutically acceptable salts thereof. ### Claim 7 3-[(3R*,4R*)-3-(Dimethylaminomethyl)tetrahydropyran-4-yl[phenol, or a pharmaceutically acceptable salt thereof. ### Claim 8 3-[(3R,4R)-3-(Dimethylaminomethyl)tetrahydropyran-4-yl[phenol, or a pharmaceutically acceptable salt thereof. ### Claim 9 (depends on 1) A pharmaceutical composition comprising the compound according to claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient. ### Claim 10 (depends on 9) The pharmaceutical composition according to claim 9, wherein the composition is in the form of a patch. ### Claim 11 (depends on 9) A method for treating pain in a subject, comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition according to claim 9. ### Claim 12 (depends on 11) The method according to claim 11, wherein the composition is in the form of a patch. ### Claim 13 (depends on 11) The method according to claim 11, wherein the subject is a human. ### Claim 14 (depends on 11) The method according to claim 11, wherein the pain is cancer pain and/or chronic non-cancer pain. ### Claim 15 (depends on 7) A pharmaceutical composition comprising the compound according to claim 7 or a pharmaceutically acceptable salt as an active ingredient. ### Claim 16 (depends on 15) The pharmaceutical composition according to claim 15, wherein the composition is in the form of a patch. ### Claim 17 (depends on 15) A method for treating pain in a subject, comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition according to claim 15. ### Claim 18 (depends on 17) The method according to claim 17, wherein the composition is in the form of a patch. ### Claim 19 (depends on 17) The method according to claim 17, wherein the subject is a human. ### Claim 20 (depends on 17) The method according to claim 17, wherein the pain is cancer pain and/or chronic non-cancer pain. ### Claim 21 (depends on 8) A pharmaceutical composition comprising the compound according to claim 8 or a pharmaceutically acceptable salt as an active ingredient. ### Claim 22 (depends on 21) The pharmaceutical composition according to claim 21, wherein the composition is in the form of a patch. ### Claim 23 (depends on 21) A method for treating pain in a subject, comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition according to claim 21. ### Claim 24 (depends on 23) The method according to claim 23, wherein the composition is in the form of a patch. ### Claim 25 (depends on 23) The method according to claim 23, wherein the subject is a human. ### Claim 26 (depends on 23) The method according to claim 23, wherein the pain is cancer pain and/or chronic non-cancer pain.