# US 2019/0167593 A1 · Cyclohexene derivative or pharmaceutically acceptable salt thereof, and application of same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0167593 A1 - Document ID: US20190167593A1 - Status: Published application - Kind: A1 - Application number: 16/096,778 - Filed: 2017-04-27 - Published: 2019-06-06 - Earliest claimed: 2016-04-28 - Assignees: Guangzhou Henovcom Bioscience Co., Ltd. - Applicants: Guangzhou Henovcom Bioscience Co. Ltd - Inventors: Jiancun Zhang; Deyao Li; Hong Li; Kun Wang; Yan Liu; Yan Wu; Xing Tang; Jianbo Song - Web page: https://patentgrep.com/patent/US20190167593A1 ## CPC - A61K 9/19: lyophilised {, i.e. freeze-dried, solutions or dispersions (lyophilised products with subsequent particle size reduction A61K9/14; granules or pellets made by lyphilisation A61K9/1682; solid oral dosage forms made by lyophilisation A61K9/2095; lyophilisation additives A61K47/00)} - A61J 3/02: into the form of powders (pulverising in general B02C) - A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)} - A61K 31/451: having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine - A61K 47/02: Inorganic compounds - A61K 47/12: Carboxylic acids; Salts or anhydrides thereof - A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin - A61P 31/16: for influenza or rhinoviruses - C07D 211/56: Nitrogen atoms (nitro radicals C07D211/38) - 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) - A61J: CONTAINERS SPECIALLY ADAPTED FOR MEDICAL OR PHARMACEUTICAL PURPOSES; DEVICES OR METHODS SPECIALLY ADAPTED FOR BRINGING PHARMACEUTICAL PRODUCTS INTO PARTICULAR PHYSICAL OR ADMINISTERING FORMS; DEVICES FOR ADMINISTERING FOOD OR MEDICINES ORALLY; BABY COMFORTERS; DEVICES FOR RECEIVING SPITTLE - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract A cyclohexene derivative or pharmaceutically acceptable salt thereof and application thereof, which belongs to the technical field of pharmaceutical technology is provided. The cyclohexene derivative of formula I or pharmaceutically acceptable salt thereof is a new broad-spectrum anti-influenza compound, having a great inhibiting effect on influenza viruses, specifically, it has a high activity to virus strains which is drug-resistant to Oseltamivir, and may be used as a broad-spectrum anti-influenza NA inhibitor effective to Tamiflu drug-resistance, for treating the flu caused by influenza viruses, thereby it is a broad-spectrum anti-influenza drug. ## Claims ### Claim 1 A cyclohexene derivative of formula I or a pharmaceutically acceptable salt thereof: ### Claim 2 An injectable formulation of anti-influenza virus, wherein the injectable formulation comprises the compound of formula I or a pharmaceutically acceptable salt thereof as an active ingredient. ### Claim 3 (depends on 2) The injectable formulation of anti-influenza virus according to claim 2, wherein the pharmaceutically acceptable salt of the compound of formula I is lactate, hydrochloride, phosphate, acetate, malate, citrate, or aspartate. ### Claim 4 (depends on 3) The injectable formulation of anti-influenza virus according to claim 3, wherein the pharmaceutically acceptable salt is lactate and the mole ratio of the compound of formula I to lactic acid is from 1:1.5 to 1:2.5. ### Claim 5 (depends on 2) The injectable formulation of anti-influenza virus according to claim 2, wherein the injectable formulation is a sterile powder for injection and the sterile powder further comprises a pharmaceutically acceptable excipient. ### Claim 6 (depends on 5) The injectable formulation of anti-influenza virus according to claim 5, wherein the sterile powder for injection is a freeze-dried powder for injection, and the pharmaceutically acceptable excipient comprises a filler, the filler is at least one of mannitol, sorbitol, and sodium chloride, and the ratio by weight of the filler to the compound of formula I or a pharmaceutically acceptable salt thereof is from 0.19:1 to 1.9:1. ### Claim 7 (depends on 2) A method for preparing the injectable formulation of anti-influenza virus according to claim 2, comprising the following steps: an amount of the compound of formula I and an appropriate amount of water for injection were added, followed by an organic or inorganic acid such that the compound of formula I was reacted with the organic or inorganic acid completely and dissolved, a predetermined amount of a pharmaceutically acceptable excipient was subsequently added, mixed, then the water for injection was added until a predetermined volume was reached, and filtered to obtain the final product. ### Claim 8 (depends on 7) The method for preparing the injectable formulation of anti-influenza virus according to claim 7, comprising the following steps: preparation of solution: an amount of the compound of formula I and an appropriate amount of water for injection were added, followed by an organic or inorganic acid such that the compound of formula I was reacted with the organic or inorganic acid completely and dissolved, a predetermined amount of a pharmaceutically acceptable excipient was subsequently added, mixed, a predetermined amount of a pharmaceutically acceptable excipient was subsequently added, mixed, and filtered; and freeze-drying: the injectable solution prepared above was distributed and placed in a freeze-drying device, and freeze-dried to obtain the final product. ### Claim 9 (depends on 8) The method for preparing the injectable formulation of anti-influenza virus according to claim 8, wherein, in the step of solution preparation, the pharmaceutically acceptable excipient is sodium chloride added in a ratio by weight from 0.19:1 to 0.57:1 of the excipient and the compound of the formula I; in the step of freeze-drying, the freeze-drying was carried out according to the following processes: the temperature of shelves was set to −30 to −50° C., and maintained for 3 to 5 hours; vacuuming was then conducted, the temperature was gradually raised by 7 to 15° C. within 0.5 to 1.5 hours, and maintained for 1.5 to 2.5 hours; the temperature was then gradually raised by 7 to 15° C. within 0.5 to 1.5 hours, and maintained for 2 to 4 hours; the temperature was then gradually raised by 7 to 15° C. within 1.5 to 1.5 hours, and maintained for 2 to 4 hours; the temperature was then gradually raised up to 0° C. within 0.5 to 1.5 hours, and maintained for 1.5 to 2.5 hours; the temperature was then gradually raised up to 15 to 25° C. within 0.5 to 1.5 hours, and maintained for 1.5 to 2.5 hours; and the temperature was then gradually raised up to 35 to 45° C. within 0.5 to 1.5 hours, and maintained for 4 to 10 hours. ### Claim 10 (depends on 1) A method of anti-influenza virus in a subject in need thereof, comprising administering the cyclohexene derivative or a pharmaceutically acceptable salt thereof according to claim 1 in the preparation of a medicament.