SG11201408617PA - Bifluorodioxalane-amino-benzimidazole kinase inhibitors for the treatment of cancer, autoimmuneinflammation and cns disorders - Google Patents

Abstract

(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 3 January 2014 (03.01.2014) WIPOIPCT (10) International Publication Number WO 2014/001464 A1 (51) International Patent Classification: C07D 491/02 (2006.01) A61P 25/00 (2006.01) A61K31/4188 (2006.01) A61P 29/00 (2006.01) A61K35/00 (2006.01) (21) International Application Number: (22) International Filing Date: (25) Filing Language: (26) Publication Language: PCT/EP2013/063537 27 June 2013 (27.06.2013) English (30) Priority Data: 61/664,936 12174669.7 27 June 2012 (27.06.2012) 2 July 2012 (02.07.2012) English US EP (71) Applicant: 4SC DISCOVERY GMBH [DE/DE]; Am Klopferspitz 19a, 82152 Planegg-Martinsried (DE). (72) Inventors: LEBAN, Johann; Pyrkergasse 31, Appartment 10, A-1190 Wien (AT). ZAJA, Mirko; Horwarthstr. 33, 80804 Munchen (DE). (74) Agent: BOEHMERT & BOEHMERT; Hollerallee 32, 28209 Bremen (DE). (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). Published: — with international search report (Art. 21(3)) (54) Title: BIFLUORODIOXALANE-AMINO-BENZIMIDAZOLE KINASE INHIBITORS FOR THE TREATMENT OF CAN­ CER, AUTOIMMUNEINFLAMMATION AND CNS DISORDERS Y L- <*) •t •t i-H o o o CJ O & (57) Abstract: The invention relates to a compound of the general formula (I) or a physiologically functional derivative, solvate or salt thereof, (I) wherein A is a bond, alkyl or alkoxy optionally substituted with one or more R\" as defined herein, *-N(R'\")CO-, *- CON(R'\")-, *-N(R\")CON(R\"')-, , -S-, -SO-, *-N(R'\")-, *-N(R'\")CO-, *-CON(R'\")-, -CO-, *-COO-, *-OOC-, *-S02N(R'\")-, -S0 , 2 or *- N(R'\")-S02-, wherein R'\" is as defined herein and * specifies the point of attachment to X; X is aryl, cycloalkyl, aralkyl, heterocyclyl or heteroaryl, which may be substituted with one or more R x further described herein; L is a bond or *-N(R )CO-, N *-CON(R )-, N *- N(R )-, N *-C=N(R )-, *-N(R )-alkyI-, *-alkyl-N(R )-, *-N(R )CON(R )-, *-CO-, *-S0 -, N N N N N 2 alkyl, *-alkyl-0-alkyl-, *-NCO-CH=CH-, *- CH=CH-CONH-, * -S0 N(R )-, *-N(R )S0 -, 2 N N 2 or heterocyclyl, wherein * specifies the point of attachment to X; Y is H, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl or heteroaryl, which may be substituted with one or more R Y further described herein; and R and R N are further described herein; as well as their use as a medicament, a pharmaceutical composition comprising them, method of a treat - ment or prevention of medical a condition entailing the administration thereof, and the use thereof in the manufacture of medica a - ment for the treatment or prevention of medical condition, particularly autoimmune a inflammatory disorders, CNS disorders, sleep - ing disorders, or proliferative diseases including cancer. The invention further relates to a specific process for the preparation of said compounds.