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WO 2017/058594 Al 6 April 2017 (06.04.2017) W P O PCT

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WO 2017/058594 Al 6 April 2017 (06.04.2017) W P O PCT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/058594 Al 6 April 2017 (06.04.2017) W P O PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 409/12 (2006.01) A23L 33/10 (201 6.01) kind of national protection available): AE, AG, AL, AM, A61K 31/4155 (2006.01) A61Q 19/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 8/49 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, PCT/US20 16/052777 KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, (22) International Filing Date: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 2 1 September 2016 (21 .09.201 6) OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (25) Filing Language: English TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (26) Publication Language: English ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 62/236,080 1 October 201 5 (01. 10.2015) US kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant: SENOMYX, INC. [US/US]; 4767 Nexus TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, Centre Drive, San Diego, CA 92121 (US). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: PATRON, Andrew, P.; 4767 Nexus Centre LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Drive, San Diego, CA 92121 (US). NONCOVICH, Alain; SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, 4767 Nexus Centre Drive, San Diego, CA 92121 (US). GW, KM, ML, MR, NE, SN, TD, TG). UNG, Jane; 4767 Nexus Centre Drive, San Diego, CA 9212 1 (US). DAVIS, Timothy; 4767 Nexus Centre Drive, Declarations under Rule 4.17 : San Diego, CA 92121 (US). FOTSING, Joseph, R.; 4767 — as to applicant's entitlement to apply for and be granted a Nexus Centre Drive, San Diego, CA 92121 (US). patent (Rule 4.1 7(H)) PRIEST, Chad; 4767 Nexus Centre Drive, San Diego, CA 9212 1 (US). TACHDJIAN, Catherine; 4767 Nexus — as to the applicant's entitlement to claim the priority of the Centre Drive, San Diego, CA 92121 (US). earlier application (Rule 4.1 7(in)) (74) Agent: CHRISTENSEN, Michael, R.; Knobbe, Martens, Published: Olson & Bear, LLP, 2040 Main Street, 14th Floor, Irvine, — with international search report (Art. 21(3)) CA 92614 (US). o o (54) Title: COMPOUNDS USEFUL AS MODULATORS OF TRPM8 (57) Abstract: The present disclosure relates to compounds which are useful as cooling sensation compounds. COMPOUNDS USEFUL AS MODULATORS OF TRPM8 RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Provisional Application No. 62/236,080, filed October 1, 2015, which is incorporated herein by reference in its entirety. BACKGROUND Field [0002] The present invention relates to compounds useful as cooling agents. Background Description [0003] Modulators of the Melastatin Transient Receptor Potential Channel 8 (TRPM8) are known to have a cooling effect. TRPM8 is a channel involved in the chemesthetic sensation, such as cool to cold temperatures as well as the sensation of known cooling agents, such as Menthol and Icilin. However, many of the currently known TRPM8 modulators have deficiencies with regard to strength and/or duration of effect, skin and/or mucosa irritation, odor, taste, solubility, and/or toxicity. SUMMARY [0004] The present disclosure relates to compounds useful as cooling agents. In some embodiments, the compounds are modulators of TRPM8. Some embodiments include compounds, ingestible compositions, personal care products, and pharmaceutical compositions, and the use and preparation thereof. In particular, some embodiments, relate to specific pyrazolyl and thiophenyl substituted acetamide compounds as disclosed herein. me embodiments include a compound selected or a salt or solvate thereof j 00 In some embodiments the compound can have the structure , or a salt thereof. In some embodiments the compound has the structure or a salt thereof some embodiments the compound can have the structure or a sa thereof. [0009] In some embodiments the compound can have the structure , or a salt thereoi 0010] In some embodiments the compound can have the structure [0011] In some embodiments, a composition is provided, comprising any one of the above compounds and at least one carrier [0012] In some embodiments, the composition can be an ingestible composition or personal care product [0013] In some embodiments, the composition can be a food or beverage. [0014] In some embodiments, the composition can be a topical personal care product. [0015] In some embodiments, the composition can be in form of a solid, semi solid, plaster, solution, suspension, lotion, cream, foam, gel, paste, or emulsion. [0016] In some embodiments, a compound disclosed herein in the composition can be in a concentration ranging from about 0.0001 ppm to 100,000 ppm [0017] In some embodiments, the compound disclosed herein in the composition can be in a concentration ranging from about 1 ppm to 500 ppm [0018] In some embodiments, the composition can be a textile product or a packaging material [0019] Some embodiments include a method of modulating transient receptor potential channel melastatin member 8 (TRPM8) comprising contacting the receptor with a compound of the present disclosure, or a salt or solvate thereof. In some embodiments, the compound can be a TRPM8 receptor agonist. [0020] Some embodiments include a method of modulating the cooling sensation of a composition comprising combining the composition with a compound of the present disclosure, or a salt or solvate thereof, to form a modified composition. [0021] Some embodiments include a method of inducing a cooling sensation in a human or animal comprising contacting the human or animal with a compound of the present disclosure, or a salt or solvate thereof. DETAILED DESCRIPTION [0022] Some embodiments provide a compound selected from the compounds listed in Table 1, or a salt thereof. [0023] In some embodiments, the compound can have the structure of Compound or a salt thereof : [0024] In some embodiments, the compound can have the structure of Compound 102, or a salt there [0025] In some embodiments, the compound can have the staicture of Compound 103, or a salt thereof: [0026] In some embodiments, the compound can have the structure of Compound 104, or a salt thereof: [0027] In some embodiments, the compound can have the structure of Compound 105, or a salt thereof: 8 ] In some embodiments, a composition is provided, comprising any one Compounds 101-105 and at least one carrier. [0029] In some embodiments, a personal product is provided comprising a compound selected from Compounds 101-105, or a salt thereof. [0030] In some embodiments, the composition comprising a compound selected from Compounds 101-105 can be an ingestible composition or a personal care composition. [0031] In some embodiments, the composition comprising a compound selected from Compounds 101-105 can be an ingestible composition that is a food or beverage [0032] In some embodiments, the composition comprising a compound selected from Compounds 101-105 can be a topical personal care product. [0033] In some embodiments, the composition comprising a compound selected from Compounds 101-105 can be in form of a solid, semi-solid, plaster, solution, suspension, lotion, cream, foam, gel, paste, emulsion, or a combination thereof. [0034] In some embodiments, the composition can comprise a compound selected from Compounds 101-105 in a concentration ranging from about 0.0001 ppm to 100,000 ppm. [0035] In some embodiments, the composition can comprise a compound selected from Compounds 101-105 in a concentration ranging from about 1 ppm to 500 ppm. [0036] In some embodiments, the composition comprising a compound selected from Compounds 101-105 can be a textile product or a packaging material. [0037] In some embodiments, a method of modulating transient receptor potential channel melastatin member 8 (TRPM8) is provided, comprising contacting the receptor with a compound comprising a compound selected fr o Compounds 101-105, or a salt or solvate thereof. In some embodiments, the method can be in vitro or in vivo. In some embodiments of the method of modulating TRPM8, the compound comprising a compound selected from Compounds 101-105 can be a TRPM8 receptor agonist. [0038] In some embodiments, a method of modulating the cooling sensation of a composition is provided, comprising combining the composition with a compound selected from Compounds 101-105, or a salt or solvate thereof, to form a modified composition. [0039] In some embodiments, a method of inducing a cooling sensation in a human or animal is provided, comprising contacting the human or animal with a compound selected from Compounds 101-105, or a salt or solvate thereof. Definitions [0040] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by o e of ordinary skill in the art to which this disclosure belongs. All patents, applications, published applications, and other publications are incorporated by reference in their entirety. In the event that there is a plurality of definitions for a term herein, those in this section prevail unless stated otherwise.
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