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WO 2008/084303 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 17 July 2008 (17.07.2008) WO 2008/084303 Al (51) International Patent Classification: (US). SCHAUM, Robert, Philip [CA/US]; Pfizer Global C07D 471/04 (2006.01) A61P 3/10 (2006.01) Research and Development, 50 Pequot Avenue, New A61K 31/437 (2006.01) London, CT 06320 (US). (21) International Application Number: (74) Agent: FULLER, Grover, E ; c/o GEORGE, Nancy Mc- PCT/IB2007/003844 Graw, Pfizer Inc. MS8260-1615, Eastern point Road, Gro ton, CT 06340 (US). (22) International Filing Date: 3 December 2007 (03.12.2007) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (25) Filing Language: English AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, (26) Publication Language: English ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, (30) Priority Data: LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, 60/876,334 2 1 December 2006 (21.12.2006) US MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, 60/970,653 7 September 2007 (07.09.2007) US PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (71) Applicant (for all designated States except US): PFIZER ZM, ZW PRODUCTS INC. [US/US]; Eastern Point Road, Groton, CT 06340 (US). (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (72) Inventors; and GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (75) Inventors/Applicants (for US only): BIGGE, Christo¬ ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), pher, Franklin [US/US]; 4714 Parkside Court, Ann European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, Arbor, MI 48105 (US). CASIMIRO-GARCIA, Agustin FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, [MX/US]; Pfizer Global Research & Development, East PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, ern Point Road, Groton, CT 06340 (US). LEE, Chitase GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). [US/US]; 695 Skynob, Ann Arbor, MI 48105 (US). RIS- LEY, Hud, Lawrence [US/US]; Pfizer Global Research Published: & Development, Eastern Point Road, Groton, CT 06340 — with international search report (54) Title: COMPOUNDS HAVING BOTH ANGIOTENSIN II RECEPTOR ANTAGONISM AND PPARY ACTIVATING AC- TIVITIES (57) Abstract: Compounds of following formula (I) are provided that have both angiotensin Il receptor antagonist activity and PPARy agonist activity. Also provided are pharmaceutical compositions comprising the compounds and methods of treatment of diseases with the compounds including type 2 diabetes, insulin resistance, hyperinsulinemia, hyperlipidemia, hypertriglyceridemia, metabolic syndrome, congestive heart failure, and hypertension. COMPOUNDS HAVING BQTH ANGIOTENSIN Il RECEPTOR ANTAGONISM AND PPARy ACTIVATING ACTIVITIES BACKGROUND OF THE INVENTION This invention relates to compounds that have both angiotensin Il receptor antagonism and PPARY activating activities. US Patent 5,338,740 and Carpino et al., Bioorganic & Medicinal Chemistry Letters, (1994). Vol. 4 , No. 1, 93-8 disclose that certain substituted [2-(1 H-tetrazol-5-yl)- phenyl]-indan-1-yl}-3H-imidazo[4,5-b]pyridines are angiotensin Il receptor antagonists (ARB). The compounds are useful in the treatment of hypertension, glaucoma, renal disease, congestive heart failure, cognitive dysfunction, and other conditions in which the action of angiotensin Il is implicated. US Publication 2003/01 58090 discloses a method of treating diabetes, which comprises administration of an inhibitor of the angiotensin Il system and an anti-diabetic agent. WO 2004/017896 discloses a method of treating hypertension and type-2 diabetes mellitus, metabolic syndrome or pre-diabetic condition comprising administering a combination of a dual PPARα/γ (peroxisome proliferator-activated receptor α/γ ) agonist and an angiotensin Il type I receptor antagonist. A dual PPARα/γ agonist has both PPARα and PPARy activity in comparison to the glitazones that have only PPARY activity. WO 2004/014308 and US Publication 2004/0127443 disclose a method of treatment and compounds that are angiotensin Il type I receptor antagonists (ARB) and can also increase the activity of PPAR's. The diseases that these molecules are used to treat are type-2 diabetes, metabolic syndrome, insulin resistance, and inflammatory disorders. Peroxisome proliferator-activated receptors (PPARs) are members of the nuclear receptor superfamily of ligand-activated transcription factors. Three subtypes of PPARs have been cloned from the mouse and human: i.e., PPARα, PPARy, and PPARδ . The PPARs are important regulators of carbohydrate and lipid metabolism, cell growth and differentiation, phenotype transition, apoptosis, neovascularization, immunoregulation and the inflammatory response. Compounds that activate PPARs are useful for the treatment and prevention of a variety of clinical disorders such as type 2 diabetes, insulin resistance, hyperinsulinemia, hyperlipidemia, hypertriglyceridemia, and metabolic syndrome. Type 2 diabetes is associated with a wide variety of conditions such as hyperglycemia, insulin resistance, hyperinsulinemia, excess weight, high blood pressure, and dyslipidemia (hypertriglyceridemia and low levels of high density lipoproteins), which can lead to the deposition of plaque in the arteries. This cluster of associated conditions has often been referred to as metabolic syndrome, and is strongly associated with an elevated risk for heart disease. Examples of known compounds that can activate PPARs include thiazolidinediones (e.g. rosiglitazone, pioglitazone, MK 767 (KRP-297), MCC-555, netoglitazone, balaglitazone, rivoglitazone) that primarily activate PPARy, or PPARy and PPARα, and non-thiazolidinediones that can activate any combination of PPARα, PPARY, and PPARδ are JTT-501 , LSN862, DRF 4832, LM 4 156, LY 510929, LY 51981 8, TY 5 1501 , X 334, certain tyrosine-based derivatives such as GW1929, and GW7845, phenylacetic acid-based derivatives, phenoxazine phenyl propanoic acid derivatives such as DRF 2725, DRF 2189, cinammic and dihydrocinammic acid-based derivatives such as tesaglitazar (AZ 242)), and 3-Phenyl-7-propylbenzisoxazoles (Adams A D, et al. Bioorg Med Chem Lett. (2003) 13:931-5), that can activate PPARy in combination with PPARα or PPARδ or both PPARα and PPARδ. Molecules with PPARy agonist activity are used to treat type 2 diabetes and are known to decrease insulin resistance, hyperglycemia, hyperinsulinemia, and hypertriglyceridemia. PPARy agonists, however, are not used for the treatment of high blood pressure. Molecules with angiontensin Il receptor antagonist activity are useful in the treatment of high blood pressure. There is a need for a molecule that has both angiontensin Il receptor antagonist and PPARy agonist activities that can be used to treat conditions such as type 2 diabetes, insulin resistance, hyperinsulinemia, hyperlipidemia, hypertriglyceridemia, metabolic syndrome, congestive heart failure, or hypertension. There remains a need for pharmaceutical agents that have both angiotensin Il receptor antagonism and PPARy activating activities and are useful in the treatment, prevention or diminution of the manifestations of the maladies described herein. SUMMARY OF THE INVENTION The present invention is directed to a compound of the Formula I Formula I wherein: 1 R is (Ci - C4)alkyl or ethoxy; 2 R is (Ci - C8)alkyl, (C2 - C8)alkenyl or (C2 - C8)alkynyl, said (Ci - C8)alkyl, (C2 - C8)alkenyl or (C2 - C8)alkynyl mono-, di- or tri- substituted independently with hydroxyl, (CrC 5)alkylcarbonyloxy, benzylcarbonyloxy, (CrC 3)alkoxy, halo, trifluoromethyl, nitrile, oxo or a 3 to 8 membered partially saturated, fully saturated or fully unsaturated ring optionally having one to three heteroatoms selected independently from one, two or three N, one O or one S and said 3 to 8 membered ring optionally mono-, di- or tri- substituted independently with halo, (C2-C6)alkenyl, (CrC 6)alkyl, hydroxyl, (Cr C jalkoxy, (CrC 4)alkylthio, amino, nitro, cyano, oxo, carboxy, (CrC 6)alkyloxycarbonyl or mono-N- or di-N,N-(Ci-C 6)alkylamino wherein said (Ci-C 6)alkyl substituent is optionally mono-, di- or tri-substituted independently with halo, hydroxyl, (Ci-C 6)alkoxy, (Cr C )alkylthio, amino, nitro, cyano, oxo, carboxy, (CrC 6)alkyloxycarbonyl or mono-N- or di-N,N-(CrC 6)alkylamino and wherein said (d-C 6)alkyl substituent is also optionally substituted with from one to nine fluorines; and 3 R is CH3, or a pharmaceutically acceptable salt thereof. Another aspect of this invention is directed to methods of treating hypertension, obesity, overweight condition, hypertriglyceridemia, hyperlipidemia, hypoalphalipoproteinemia, Syndrome X (Metabolic Syndrome), diabetes mellitus (especially Type II), hyperinsulinemia, impaired glucose tolerance, insulin resistance, a diabetic complication, atherosclerosis, coronary heart disease, hypercholesterolemia, inflammation, thrombosis or congestive heart failure in a mammal (including a human being) which comprise administering to said mammal a therapeutically effective amount of a compound of Formula I a prodrug of said compound, or a pharmaceutically acceptable salt of said compound or prodrug. Also provided herein are compositions
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