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WO 2013/022996 A2 14 February 2013 (14.02.2013) P O P C T

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WO 2013/022996 A2 14 February 2013 (14.02.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2013/022996 A2 14 February 2013 (14.02.2013) P O P C T (51) International Patent Classification: 9 1125 (US). BOYCE THOMPSON INSTITUTE FOR A61K 31/7052 (2006.01) A61K 31/35 (2006.01) PLANT RESEARCH [US/US]; Tower Road, Ithaca, New A61K 31/70 (2006.01) A61P 29/00 (2006.01) York 14853 (US). A61K 31/404 (2006.01) A61P 37/00 (2006.01) (72) Inventors; and (21) International Application Number: (75) Inventors/Applicants (for US only): CHOE, Andrea PCT/US20 12/05003 1 [US/US]; 5471 1/2 Eagle Rock View Drive, Los Angeles, California 90041 (US). STERNBERG, Paul Warren (22) International Filing Date: [US/US]; 1782 Rose Villa Street, Pasadena, California 8 August 2012 (08.08.2012) 9 1106 (US). SCHROEDER, Frank Clemens [DE/US]; (25) Filing Language: English 113 Glen Place, Apartment 2A, Ithaca, New York 14850 (US). VON REUSS, Stephan Heinrich [DE/US]; 400 (26) Publication Language: English Stewart Avenue, Ithaca, New York 14850 (US). (30) Priority Data: (74) Agents: SENN, Sean et al; Nixon Peabody LLP, Gas 61/521,295 8 August 201 1 (08.08.201 1) US Company Tower, 555 West Fifth Street, 46th Floor, Los 61/620,343 4 April 2012 (04.04.2012) US Angeles, California 90013 (US). 61/620,33 1 4 April 2012 (04.04.2012) us 61/620,348 4 April 2012 (04.04.2012) us (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (71) Applicants (for all designated States except US): CALI¬ AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, FORNIA INSTITUTE OF TECHNOLOGY [US/US]; BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 1200 East California Boulevard, Pasadena, California DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, [Continued on nextpage] (54) Title: THE UTILITY OF NEMATODE SMALL MOLECULES (57) Abstract: The present invention relates to methods of Figure 6. treating immune disorders and/or inflammation using certain modulator compounds. In one embodiment, the present in Nematodes G n - a iv fe a vention provides a method of treating an immune and in flammatory disorders disorder by administering a composi tion comprising a therapeutically effective dosage of an as- caroside compound, or a mixture of ascaroside compounds, or a mixture containing at least one ascaroside.. w o 2013/022996 \ 2 llll II II 11III III II I II II 111II III II I II HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, NO, NZ, OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, GW, ML, MR, NE, SN, TD, TG). ZM, ZW. Published: (84) Designated States (unless otherwise indicated, for every — without international search report and to be republished Mnd of regional protection available): ARIPO (BW, GH, upon receipt of that report (Rule 48.2(g)) GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, THE UTILITY OF NEMATODE SMALL MOLECULES GOVERNMENT RIGHTS This invention was made with United States Government support under NIH Agreement No. GM085285. The Government has certain rights in the invention. FIELD OF THE INVENTION The invention relates to the field of biotechnology, specifically to immunomodulation and nematodes. BACKGROUND OF THE INVENTION All publications herein are incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference. The following description includes information that may be useful in understanding the present invention. It is not an admission that any of the information provided herein is prior art or relevant to the presently claimed invention, or that any publication specifically or implicitly referenced is prior art. Nematodes are the most abundant animals in the world, found to inhabit sulfurous sediment, deep-sea trenches, human lymph nodes, pig intestines, plant roots, whale placenta, arctic ice, and many other ecosystems, making them one of the most successful groups of animals on earth. Many nematode species are known to parasitize humans; a relationship that is thought to have existed for thousands of years. The rise of immune disorders in the industrialized world has been concomitant with the decline of endemic parasitisim, lending way to the etiologic theory that humans are creating an inappropriate immune response that had previously been focused on overcoming the suppressive mechanisms of parasites. Nematodes have been in use to treat some immune disorders. There is a need in the art to develop novel compounds and methods of treating, alleviating, and/or preventing an adverse immune response and/or disorder in the place of live organisms. SUMMARY OF THE INVENTION Small molecules produced specifically by nematodes can mimic the presence of nematodes and thus be used to promote health. Various embodiments include a method of alleviating, treating, or preventing a disorder in a subject, comprising the provision of a composition comprising a compound of the formula: (Formula I), or a pharmaceutical equivalent, derivative, analog and/or salt thereof, and administering a therapeutically effective dosage of the composition to the subject. In another embodiment, the disorder is an inflammatory and/or 1 immune disorder. In another embodiment, R is H, -C(R) 3, -OR, -N(R) 2, halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl. In another embodiment, R1 is absent, H, - C(R)3, -OR, -N(R) 2, halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl. In another embodiment, R2 is a moiety of the formula: (Formula II), or a pharmaceutical equivalent, derivative, analog and/or salt thereof. In another embodiment, R is H, -CR R R8, - C(0)R 8, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R5 of another unit of Formula I. In another embodiment, R4 is H, -CR R R8, -C(0)R 8, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R5 of another unit of Formula I. In another embodiment, R5 is H, -OH, - 6 8 8 6 7 OR , -OCR R R , -CR R R , -NH 2, -NHR , -NR R , halogen, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, an arylalkyl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R or R4 of another unit of Formula I. In another embodiment, the disorder is acne vulgaris, asthma, autoimmune diseases, celiac disease, chronic prostatitis, glomerulonephritis, Hypersensitivities, Inflammatory bowel diseases, pelvic inflammatory disease, reperfusion injury, rheumatoid arthritis, sarcoidosis, transplant rejection, vasculitis, Interstitial cystitis, lupus, scleroderma, certain types of hemolytic anemia, type one diabetes, graves disease, multiple sclerosis, Goodpasture's syndrome, pernicious anemia, some types of myopathy, seasonal allergy, mastocytosis, perennial allergy, anaphylaxis, food allergy, allergic rhinitis, atopic dermatitis, and/or autism. In another embodiment, the disorder is asthma. In another embodiment, the subject is a human. In another embodiment, the subject is selected from the group consisting of primates, humans, equines, horses, cattle, cows, swine, sheep, rodents, rats, pets, cats, dogs, and guinea pigs. In another embodiment, the composition comprises one or more compounds selected from the group consisting of ascr#l, ascr#3, ascr#7, ascr#8, ascr#9, and ascr#10. Other embodiments include a method of reducing inflammation in a subject, comprising providing a composition comprising a compound of the formula: (Formula I), or a pharmaceutical equivalent, derivative, analog and/or salt thereof, and administering a therapeutically effective dosage of the 1 composition to the subject. In another embodiment, R is H, -C(R) 3, -OR, -N(R) 2, halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl. In another embodiment, R1 is absent, H, -C(R) 3, -OR, -N(R) 2, halogen, an alkyl, a haloalkyl, an alkenyl, or a haloalkenyl. In another embodiment, R2 is a moiety of the formula: (Formula II), or a pharmaceutical equivalent, derivative, analog and/or salt thereof. In another embodiment, R is H, -CR R R8, - C(0)R 8, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R5 of another unit of Formula I. In another embodiment, R4 is H, -CR R R8, -C(0)R 8, an alkyl, a haloalkyl, an alkenyl, a haloalkenyl, an aryl, a heteroaryl, a heterocyclyl, a cycloalkyl, a cycloalkenyl, an acyl, an amino acid, a nucleoside, a monosaccharide having 5 or 6 carbon atoms, or a bond connecting to R5 of another unit of Formula I.
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