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WO 2016/179157 Al 10 November 2016 (10.11.2016) P O P C T

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WO 2016/179157 Al 10 November 2016 (10.11.2016) P O P C T (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 2016/179157 Al 10 November 2016 (10.11.2016) P O P C T (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A61K 31/404 (2006.01) A61P 29/00 (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 16/030540 KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, (22) International Filing Date: MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, 3 May 20 16 (03.05.2016) 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, TN, (25) Filing Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 62/157,092 5 May 2015 (05.05.2015) US GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: CARAFE DRUG INNOVATION, LLC TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [US/US]; 7 Deer Park Drive, Suite C-2, Monmouth Junc DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, tion, NJ 08852 (US). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors: CARSON, John, R.; 551 Rittenhouse GW, KM, ML, MR, NE, SN, TD, TG). Boulevard, Morristown, PA 19403 (US). RAFFA, Robert, B.; 4 Racer Lane, Morristown, PA 19401 (US). CARSON, Declarations under Rule 4.17 : Kenneth, G.; 96 Herrontown Road, Princeton, NJ 08540 — as to applicant's entitlement to apply for and be granted a (US). patent (Rule 4.1 7(H)) (74) Agents: ROSEDALE, Jeffrey, H. et al; Baker & — as to the applicant's entitlement to claim the priority of the Hostetler LLP, 2929 Arch Street, Cira Centre, 12th Floor, earlier application (Rule 4.1 7(in)) Philadelphia, PA 19 104-2891 (US). Published: (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, — with international search report (Art. 21(3)) (54) Title: SUBSTITUTED 5-HYDROXYOXINDOLES AND THEIR USE AS ANALGESICS AND FEVER REDUCERS (57) Abstract: The present invention provides com pounds and compositions which are useful in methods for modulating pain and fevers in a subject. These com pounds are of the structure of formula (I), wherein Rx- R4, X, Y, and Z are defined herein, or a pharmaceutic - ally acceptable salt, solvate, or prodrug thereof to the subject. In one embodiment, the compound is 5-hy- droxy- 7-methyloxindole . (I) SUBSTITUTED 5-HYDROXYOXINDOLES AND THEIR USE AS ANALGESICS AND FEVER REDUCERS CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims the benefit of the priority of US Provisional Patent Application No. 62/157,092, filed May 5, 2015, which is incorporated by reference. FIELD OF THE INVENTION [0002] The disclosed invention is in the field of compounds for treating pain and reducing fever. BACKGROUND [0003] N-(4-Hydroxyphenyl)acetamide (acetaminophen, paracetamol, APAP) is a very widely used and effective pain relieving agent. It occupies a therapeutic niche between the highly efficacious opioid class and the non-steroidal anti-inflammatory drugs (NSAIDs, COX-l/COX- 2). It lacks the typical side effects of the opioids (physical dependence, constipation, CNS) as well as the side effects associated with NSAIDs (gastrointestinal irritation, cardiovascular). Though lacking the efficacy of the opioids and the anti-inflammatory effects of NSAIDs, when used at recommended doses by appropriate subjects, acetaminophen would seem to be an almost side effect free pain relieving drug. The issue with acetaminophen is that, when used at high doses or in subjects with compromised liver function, it can cause liver damage. Furthermore, in conjunction with the high doses needed for pain relief, the potential toxicity also points to significant unmet medical need in terms of therapeutic index. [0004] Even after over a century of use, there is no universally accepted mechanism. Mechanistic possibilities include interaction with the peroxidase site on the COX enzyme, action on the endocannabinoid system, indirect interaction with serotonergic pathways, action on TRP channels and indirect interaction with opioid pathways. Lack of certainty of acetaminophen' s mechanism makes finding a safer alternative drug a challenge. [0005] While the mechanism of action of acetaminophen remains unclear, the primary mechanism for its toxic effects is well understood. See, Scheme 1. At high doses, acetaminophen I undergoes oxidation to a reactive quinoneimine II which is able to react with tissue sulfhydryl groups (BioNuSH) to provide compound III with resulting cytotoxicity. I ill Scheme 1 [0006] Thus, there is a need for compounds for treating pain, while avoiding the toxic effects of acetaminophen. The invention is directed to these and other important needs. SUMMARY [0007] In one aspect, a method for treating pain in a subject is provided and includes administering an effective amount of a compound of the structure of formula (I), wherein R -R4, X, Y, and Z are defined herein, or a pharmaceutically acceptable salt, solvate, or prodrug thereof to the subj ect. [0008] In another aspect, a method for reducing fever in a subject is provided and includes administering an effective amount of a compound of the structure of formula (I), wherein R -R4, X, Y, and Z are defined herein, or a pharmaceutically acceptable salt, solvate, or prodrug thereof to the subj ect. [0009] In a further aspect, a composition is provided and contains (a) one or more pharmaceutically acceptable excipient; and (b) about 1000 mg or less of a compound of the structure of formula (I), wherein R -R4, X, Y, and Z are defined herein, or a pharmaceutically acceptable salt, solvate, or prodrug thereof. [0010] In yet another aspect, a kit is provided and contains (a) about 1000 mg or less of a compound of the structure of formula (I), wherein R -R4, X, Y, and Z are defined herein, or a pharmaceutically acceptable salt, solvate, or prodrug thereof; and (b) instructions for administering the compound to a subject. [0011] The general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as defined in the appended claims. Other aspects of the present invention will be apparent to those skilled in the art in view of the detailed description of the invention as provided herein. BRIEF DESCRIPTION OF THE DRAWINGS [0012] The summary, as well as the following detailed description, is further understood when read in conjunction with the appended drawings. For the purpose of illustrating the invention, there are shown in the drawings exemplary embodiments of the invention; however, the invention is not limited to the specific methods, compositions, and devices disclosed. In addition, the drawings are not necessarily drawn to scale. In the drawings: [0013] FIG. 1 is a bar graph illustrating the effects of control vehicle C57BL/6N (■ bar), G6C3F1 (□ bar), acetaminophen ( bar) at concentrations of 400, 800, and 1600 mg/kg and 5- hydroxyindole (5-HI; bar) at concentrations of 75, 150, and 500 mg/kg in B6C3F1 Mice. ***P<0.001; ANOVA with Dunnett's post hoc compared to Vehicle control B6C3F1/Tac. [0014] FIG. 2 is a bar graph illustrating the effect of acetaminophen alone at 0, 30, 100, and 300 mg/kg as a factor of the number of writhing responses. *p < 0.05; **p < 0.01 compared to vehicle control (dose = 0) by one-way ANOVA. [0015] FIG. 3 is a bar graph illustrating the effect of 5-hydroxy-7-methyloxindole as a factor of the number of writhing responses. *p < 0.05 and **p < 0.01 compared to vehicle control (dose = 0) by one-way ANOVA. [0016] FIG. 4 is a dose-response curve for 0, 30, 100, and 300 mg/kg concentrations of 5- hydroxy-7-methyloxindole vs. the number of writhing responses. [0017] FIG. 5 is a bar graph illustrating the effect of acetaminophen in 6% Tween® 20 reagent for concentrations 0, 100, and 300 mg/kg concentrations on the number of writhing responses. *p < 0.05 compared to vehicle control (dose = 0) by one-way ANOVA. [0018] FIG. 6 is a dose-response for 0, 100, and 300 mg/kg concentrations of 5-hydroxy-7- methyloxindole in 6% Tween® 20 reagent on the number of writhing responses. **p < 0.01 compared to vehicle control (dose = 0) by one-way ANOVA. DETAILED DESCRIPTION [0019] The present invention may be understood more readily by reference to the following detailed description taken in connection with the accompanying figures and examples, which form a part of this disclosure. It is to be understood that this invention is not limited to the specific devices, methods, applications, conditions or parameters described and/or shown herein, and that the terminology used herein is for the purpose of describing particular embodiments by way of example only and is not intended to be limiting of the claimed invention. Also, as used in the specification including the appended claims, the singular forms "a," "an," and "the" include the plural, and reference to a particular numerical value includes at least that particular value, unless the context clearly dictates otherwise.
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