# US 11,299,465 B2 · Carboxylic acid compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,299,465 B2 - Document ID: US11299465B2 - Status: Granted - Kind: B2 - Application number: 16/736,660 - Filed: 2020-01-07 - Published: 2020-10-08 - Granted: 2022-04-12 - Earliest claimed: 2012-05-18 - Assignees: Sumitomo Dainippon Pharma Co., Ltd. - Applicants: Sumitomo Dainippon Pharma Co., Ltd. - Inventors: Seiji Hori; Futoshi Hasegawa; Daisuke Urabe; Hirotaka Kurebayashi - Web page: https://patentgrep.com/patent/US11299465B2 ## CPC - C07D 239/48: Two nitrogen atoms - A61P 11/00: Drugs for disorders of the respiratory system - A61P 11/02: Nasal agents, e.g. decongestants - A61P 11/06: Antiasthmatics - A61P 17/00: Drugs for dermatological disorders - A61P 27/02: Ophthalmic agents - A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics - A61P 31/04: Antibacterial agents - A61P 31/14: for RNA viruses - A61P 31/18: for HIV - A61P 35/00: Antineoplastic agents - A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07D 239/47: One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine - C07D 239/49: with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim - C07D 403/10: linked by a carbon chain containing aromatic rings - C07D 403/12: linked by a chain containing hetero atoms as chain links - A61K 31/505: Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim - A61K 31/506: not condensed and containing further heterocyclic rings - Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change - Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups - 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) - Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The present disclosure concerns at least one entity chosen from compounds of Formula (I) and pharmaceutically acceptable salts thereof: wherein the variable groups X, R1, R2, R3 m, n and p are as defined herein. The present disclosure also relates to methods for the preparation of at least one such entity, and intermediates useful in the preparation thereof, to pharmaceutical compositions containing at least one such entity, to the use of at least one such entity in the preparation of medicaments, and to the use of at least one such entity in the treatment of conditions such as, for example, allergic diseases, autoimmune diseases, viral diseases, and cancer. ## Claims ### Claim 1 A method of treating cancer in a subject in need thereof comprising: administering to said subject a therapeutically effective amount of at least one compound selected from a group consisting of: 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-difluoroethyl)amino)acetic acid, 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-triflooroethyl)amino)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid, and (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid, and pharmaceutically acceptable salts of any on the foregoing, wherein the cancer is chosen from bladder cancer, head and neck cancer, prostate cancer, breast cancer, lung cancer, renal carcinoma, ovarian cancer, colon carcinoma, skin cancer, osteosarcoma, and a lymphoproliferative tumor. ### Claim 2 (depends on 1) The method according to claim 1, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid, and pharmaceutically acceptable salts of any of the foregoing. ### Claim 3 (depends on 1) The method according to claim 1, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 4 (depends on 1) The method according to claim 1, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 5 (depends on 1) The method according to claim 1, wherein the cancer is chosen from bladder cancer, head and neck cancer, lung cancer, renal carcinoma, skin cancer, and a lymphoproliferative tumor. ### Claim 6 (depends on 5) The method according to claim 5, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid, and pharmaceutically acceptable salts of any of the foregoing. ### Claim 7 (depends on 5) The method according to claim 5, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 8 (depends on 5) The method according to claim 5, wherein the at least one compound is selected from the group consisting of: (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 9 A method of treating asthma, COPD, allergic rhinitis, allergic conjunctivitis, atopic dermatitis, hepatitis B, hepatitis C, HIV, HPV, Mycobacterium avium, leishmaniasis, or dermatosis in a subject in need thereof comprising: administering to said subject a therapeutically effective amount of at least one compound selected from: 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-difluoroethyl)amino)acetic acid, 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-triflooroethyl)amino)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid, and pharmaceutically acceptable salts of any of the foregoing. ### Claim 10 (depends on 9) The method according to claim 9, wherein the at least one compound is selected from (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid, (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid, and pharmaceutically acceptable salts of any of the foregoing. ### Claim 11 (depends on 9) The method according to claim 9, wherein the at least one compound is selected from (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-diflooroethyl)amio)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 12 (depends on 9) The method according to claim 9, wherein the at least one compound is selected from (S)-2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2,2-trifluoroethyl)amino)acetic acid and pharmaceutically acceptable salts thereof. ### Claim 13 (depends on 5) The method according to claim 5, wherein the cancer is bladder cancer. ### Claim 14 (depends on 5) The method according to claim 5, wherein the cancer is head and neck cancer. ### Claim 15 (depends on 5) The method according to claim 5, wherein the cancer is lung cancer. ### Claim 16 (depends on 5) The method according to claim 5, wherein the cancer is renal carcinoma. ### Claim 17 (depends on 5) The method according to claim 5, wherein the cancer is skin cancer. ### Claim 18 (depends on 5) The method according to claim 5, wherein the cancer is a lymphoproliferative tumor.