Patent SG-11201811107W-A (SG)
Title: Heteroaromatic modulators of the retinoid-related orphan receptor gamma
Inventor: JESSIMAN ALAN STUART
IPC: C07D417/14
Filed: 2017-07-11
Abstract: INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date 18 January 2018 (18.01.2018) W I PO I PCT omit VIII °nolo III m OH VIII O II oimIE (10) International Publication Number WO 2018/011201 Al (51) International Patent Classification: CO7D 413/14 (2006.01) CO7D 417/14 (2006.01) CO7D 241/04 (2006.01) A61K 31/496 (2006.01) C07D 413/12 (2006.01) A61P 17/06 (2006.01) (21) International Application Number: PCT/EP2017/067390 (22) International Filing Date: (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 16020268.5 13 July 2016 (13.07.2016) EP (71) Applicant: LEO PHARMA A/S [DK/DK]; Industriparken 55, 2750 Ballerup (DK). (72) Inventors: JESSIMAN, Alan Stuart; c/o LEO Pharma A/S, Industriparken 55, 2750 Ballerup (DK). JOHNSON, Patrick Stephen; c/o LEO Pharma A/S, Industriparken 55, 2750 Ballerup (DK). MAANSSON, Kristoffer; c/o LEO Pharma A/S, Industriparken 55, 2750 Ballerup (DK). SORENSEN, Morten Dahl; c/o LEO Pharma A/S, Indus- triparken 55, 2750 Ballerup (DK). (74) Agent: LEO PHARMA A/S; Patent Department, Industri- parken 55, 2750 Ballerup (DK). (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, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, 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, SA, 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, ST, 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). 11 July 2017 (11.07.2017) Published: — with international search report (Art. 21(3)) W O 20 18/0 1120 1 Al (54) Title: HETEROAROMATIC MODULATORS OF THE RETINOID-RELATED ORPHAN RECEPTOR GAMMA (57) : The present invention relates to a compound according to gen- es R3 eral formula (I) wherein X represents N or CH; R1 is -CN, (Ci-C6)alkyl, (C3- C 7 )cycloalkyl, (3-7 membered)heterocycloalkyl, (5-6 membered)heteroaryl, (C 3 - X- N C7)cycloalkyl(Ci-C4)alkyl, (3-7 membered)heterocycloalkyl-(Ci-C4)alkyl or (5-6 membered)heteroaryl- (Ci-C4)alkyl; R2 is halogen, cyano, (Ci-C4)alkyl or (C3- C 7 )cycloalkyl; R3 is halogen, cyano, (Ci-C4)alkyl, (Ci-C4)haloalkyl or (C3- C7)cycloalkyl; R4 is (Ci-C4)alkyl or (Ci-C4)haloalkyl; R5 is (Ci-C6)alkyl, (C3- C7)cycloalkyl, (Ci-C6)alkyl-(C3-C7)cycloalkyl, (C3-C7)cycloalkyl-(Ci-C6)alkyl, (3-7 membered)heterocycloalkyl, phenyl, (5-6 membered)heteroaryl or -0R a . The invention further relates to said compounds for use in therapy, to pharmaceutical compositions comprising said compounds and to intermediates for preparation of said compounds. (I)