# US 10,501,416 B2 · Cationic lipid > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,416 B2 - Document ID: US10501416B2 - Status: Granted - Kind: B2 - Application number: 16/307,202 - Filed: 2017-06-22 - Published: 2019-07-18 - Granted: 2019-12-10 - Earliest claimed: 2016-06-24 - Assignees: Eisai R&D Management Co., Ltd. - Applicants: Eisai R&D Management Co., Ltd. - Inventors: Yuta Suzuki; Yoshinori Takahashi - Web page: https://patentgrep.com/patent/US10501416B2 ## CPC - C07D 211/62: attached in position 4 - A61K 31/7105: Natural ribonucleic acids, i.e. containing only riboses attached to adenine, guanine, cytosine or uracil and having 3'-5' phosphodiester links - A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids - A61K 47/28: Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid - A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14) - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07D 209/52: condensed with a ring other than six-membered - C07D 211/36: 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 241/04: having no double bonds between ring members or between ring members and non-ring members - A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers - A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones - 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 provides a cationic lipid which is able to be used for nucleic acid delivery to the cytoplasm. A cationic lipid according to the present invention is, for example, a compound represented by formula (1a) or a pharmaceutically acceptable salt thereof. (In formula (1a), each of L1 and L2 independently represent an alkylene group having 3-10 carbon atoms; each of R1 and R2 independently represent an alkyl group having 4-22 carbon atoms or an alkenyl group having 4-22 carbon atoms; X1 represents a single bond or —CO—O—; and ring P represents one of formulae (P-1) to (P-5).) (In formulae (P-1) to (P-5), R3 represents an alkyl group having 1-3 carbon atoms.) ## Claims ### Claim 1 A compound represented by formula (1a) below or a pharmaceutically acceptable salt thereof: wherein L1 and L2 independently represent an alkylene group having 3 to 10 carbon atoms; R1 and R2 independently represent an alkyl group having 4 to 22 carbon atoms or an alkenyl group having 4 to 22 carbon atoms; X1 represents a single bond or —CO—O—; and the ring P represents any of formulae (P-1) to (P-5) below: wherein R3 represents an alkyl group having 1 to 3 carbon atoms. ### Claim 2 (depends on 1) The compound according to claim 1 represented by formula (1) or a pharmaceutically acceptable salt thereof: wherein L1 and L2 independently represent an alkylene group having 3 to 10 carbon atoms; R1 and R2 independently represent an alkyl group having 4 to 22 carbon atoms or an alkenyl group having 4 to 22 carbon atoms; and X1 represents a single bond or —CO—O—. ### Claim 3 (depends on 1) The compound according to claim 1, selected from the group consisting of compounds represented by formulae (A1) to (A22) below, or a pharmaceutically acceptable salt thereof: ### Claim 4 (depends on 1) The compound according to claim 1 represented by formula (A1) below, or a pharmaceutically acceptable salt thereof: ### Claim 5 (depends on 1) The compound according to claim 1, represented by formula (A2) below, or a pharmaceutically acceptable salt thereof: ### Claim 6 (depends on 1) The compound according to claim 1 represented by formula (A3) below, or a pharmaceutically acceptable salt thereof: ### Claim 7 (depends on 1) The compound according to claim 1, represented by formula (A4) below, or a pharmaceutically acceptable salt thereof: ### Claim 8 (depends on 1) The compound according to claim 1, represented by formula (A5) below, or a pharmaceutically acceptable salt thereof: ### Claim 9 (depends on 1) The compound according to claim 1, represented by formula (A9) below, or a pharmaceutically acceptable salt thereof: ### Claim 10 (depends on 1) The compound according to claim 1, represented by formula (A12) below, or a pharmaceutically acceptable salt thereof: ### Claim 11 (depends on 1) The compound according to claim 1, represented by formula (A15) below, or a pharmaceutically acceptable salt thereof: ### Claim 12 (depends on 1) The compound according to claim 1, represented by formula (A20) below, or a pharmaceutically acceptable salt thereof: ### Claim 13 (depends on 1) A lipid complex comprising: (I) the compound according to claim 1 or a pharmaceutically acceptable salt thereof; and (II) at least one lipid selected from the group consisting of a neutral lipid, a polyethylene glycol-modified lipid and a sterol. ### Claim 14 (depends on 1) A composition comprising: (I) the compound according to claim 1 or a pharmaceutically acceptable salt thereof; (II) at least one lipid selected from the group consisting of a neutral lipid, a polyethylene glycol-modified lipid and a sterol; and (III) a nucleic acid. ### Claim 15 (depends on 1) A method for producing a composition, the method comprising: the step of mixing a polar organic solvent-containing aqueous solution containing (I) the compound according to claim 1 or a pharmaceutically acceptable salt thereof, and (II) at least one lipid selected from the group consisting of a neutral lipid, a polyethylene glycol-modified lipid and a sterol with an aqueous solution containing (III) a nucleic acid to obtain a mixed solution; and the step of reducing a content percentage of the polar organic solvent in the mixed solution.