Patent SG-11201408387Y-A (SG)
Title: Compounds with (1e, 6e)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disstituted-hepa-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof
Inventor: SHIH CHARLES
IPC: A61P17/02
Filed: 2013-06-17
Abstract: (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 27 December 2013 (27.12.2013) WIPOIPCT (10) International Publication Number WO 2013/192091 Al (51) International Patent Classification: A61K31/121 (2006.01) A01N35/02 (2006.01) A61P17/02 (2006.01) (21) International Application Number: PCT/US2013/046138 (22) International Filing Date: 17 June 2013 (17.06.2013) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 13/525,941 18 June 2012 (18.06.2012) US (71) Applicant: ANDROSCIENCE CORPORATION [US/US]; 11175 Flintoke Ave., Suite F, San Diego, Cali­ fornia 92121 (US). (72) Inventors: SHIH, Charles; AndroScience Corporation, 11175 Flintkote Ave., San Diego, California 92121 (US). SHI, Qian; AndroScience Corporation, 11175 Flintkote Ave., Suite F, San Diego, California 92121 (US). WANG, Hui-Kang; AndroScience Corporation, 11175 Flintkote Ave., Suite San Diego, California F, 92121. (US). (74) Agent: PRESTON, David; David R. Preston & Associ­ ates, 10765 Wallingford Road, San Diego, California 92126 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available)'. AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, 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, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available)'. ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, 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, 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, GW, KM, ML, MR, NE, SN, TD, TG). [Continued on next page] (54) Title: COMPOUNDS WITH (IE, 6E)-l,7-BIS-(3,4-DIMETHOXYPHENYL)-4,4-DISSTITUTED-HEPA-l,6-DIENE-3,5-DI- ONE STRUCTURAL SCAFFOLD, THEIR BIOLOGICAL ACTIVITY, AND USES THEREOF 0\ © CJ 0\ i-H cn i-H o CJ o & FKi. 1 OA. Summary of representative compounds including 4,4-disubsrituted 1,7-bis- (3,4-dimc;ihoxyphenyl)-hcpta-I,6-dii?neo5-dionc : and 6,6-disubstituted 1,11- bisfsubsti tuted phenylj-undcca-1.3.8.10-ielniene-5,7-diore scaffolds. 0 o Compound 1 ID Ri R> R3 R 4 n formula 1 3'4'-OCH 3 3'4'-OCH 3 CH <] ? CH 3 1 C. H O s 32 b 464.S5 2 3'4'-OCH 3 3'4'-OCH 3 C H ,<> CH 3 1 C,H O ; 34 6 478.5767 3 3'4'-OCH 3 3'4'-OCHJ C H 2 <; H 1 C gH 0 2 3i 5 478.58 4 3'4'-OCH 3 3'4-CCH, CHJ-/\" ] CH; 1 C H O 30 3b t 49'.60 5 3'4'-OCH 3 3'4'-OCHj CHK 2 } CH 3 C31H3JO6 506.63 6 3'4'-OCH 3 3'4'-OCH 3 CH, Y 0 CH 3 C50H37NO7 523.62 7 3'4'-OCH 3 3'4'-OCH 3 0 CH 3 C H N!0, 28 33 495.56 8 3'4'-OCH 3 3'4'-OCH 3 (CH } CHJ 2 3 CH 3 C,H,O 8 3 6 466.57 3 3'4'-OCH 3 3'4'-OCH 3 1 C; H NO 5 33 & 523.57 10 3'4'~OCH 3 S'i'-OCHj 0 H 536.60 11 3'4'-CH 3 3V.'-CHs C \"'Y CH 3 1 C OH NOS 3 35 537.60 VI B'4'-0CH-i 3'4'-OCH 3 CH,. .NH-f |] T »- JI CH 3 : C29H30N2O7S 550.62 13 3'4'-OCH, SM'-OCHi CH,<] F 1 C27H FO 29 b 4S8.S1 14 3'4'-OOCH= 3'4'-GCH; F 1 C H FO 2S 3I 5 482.54 \" 3'4'-OCH 3 3'4'-OCH 3 F 1 C: H.v.FOc 9 496.57 (57) Abstract: The present invention includes compounds, pharmaceuticals and cosmetics having at least one (substituted phenyl)-propenal moiety. The compounds and compositions of the present invention are useful in the treat­ ment or prevention of medical conditions including androgen associated conditions, androgen associated inflammation, a wound (the compounds as­ sist with wound healing), acne, rheumatoid arthritis, psoriasis, rosacea, and alopecia; Kennedy's disease (spinal and bulbar muscular atrophy, or SBMA), polyglutamine-mediated motor neuron degeneration; cancers such as pro­ state cancer, bladder cancer, breast cancer, ovarian cancer, hepatocellular (liver) cancer, and pancreatic cancer; and other medical conditions described herein. Treatment of such medical conditions includes administering to an individual suffering from medical condition describe herein, a a therapeutic - ally effective amount of any of the disclosed compounds, their derivatives, or pharmaceutical compositions thereof. WO 2013/192091 A11 lllll llllllll II llllll III lllll lllll III III III lllll lllll lllll llll llll lllll lllll lllllll llll llll u ls e ' — before the expiration of the time limit for amending the — with international search report (Art. 21(3)) claims and to be republished in the event of receipt of amendments (Rule 48.2(h))