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Indane Acetic Acid Derivatives and Their Use As Pharmaceutical Agents, Intermediates, and Method of Preparation

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Indane Acetic Acid Derivatives and Their Use As Pharmaceutical Agents, Intermediates, and Method of Preparation (19) TZZ___T (11) EP 1 578 715 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 57/62 (2006.01) C07C 69/612 (2006.01) 02.03.2011 Bulletin 2011/09 C07C 211/48 (2006.01) C07C 327/48 (2006.01) C07D 261/20 (2006.01) C07D 209/08 (2006.01) (2006.01) (2006.01) (21) Application number: 03800063.4 C07D 307/79 C07D 277/64 C07D 215/06 (2006.01) C07D 333/10 (2006.01) C07D 239/30 (2006.01) C07D 239/26 (2006.01) (22) Date of filing: 19.12.2003 C07D 401/04 (2006.01) A61K 31/33 (2006.01) A61K 31/185 (2006.01) (86) International application number: PCT/US2003/040842 (87) International publication number: WO 2004/058174 (15.07.2004 Gazette 2004/29) (54) INDANE ACETIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICAL AGENTS, INTERMEDIATES, AND METHOD OF PREPARATION INDANESSIGSÄURE-DERIVATE UND IHRE VERWENDUNG ALS PHARMAZEUTISCHE MITTEL SOWIE ZWISCHENPRODUKTE UND METHODEN ZU IHRER HERSTELLUNG DERIVES D’ACIDE ACETIQUE D’INDANE ET LEUR UTILISATION EN TANT QU’AGENTS PHARMACEUTIQUES ET INTERMEDIAIRES, ET PROCEDE DE PREPARATION CORRESPONDANT (84) Designated Contracting States: • LIANG, Sidney, X. DE ES FR GB IT Bethany, CT 06524 (US) • AKUCHE, Christiana (30) Priority: 20.12.2002 US 435310 P Hamden, CT 06514 (US) • LAVOIE, Rico, C. (43) Date of publication of application: Hamden, CT 06517 (US) 28.09.2005 Bulletin 2005/39 • CHEN, Libing Milford, CT 06460 (US) (73) Proprietor: Bayer Pharmaceuticals Corporation • MAJUMDAR, Dyuti West Haven, CT 06516 (US) Milford, CT 06460 (US) • WICKENS, Philip, L. (72) Inventors: Wallingford, CT 06492 (US) • CANTIN, Louis-David Hamden, CT 06514 (US) (74) Representative: Wilson, Gary • CHOI, Soongyu Harrison Goddard Foote Skiooman, NJ 08558 (US) 106 Hope Street • CLARK, Roger, B. Glasgow Middletown, CT 06457 (US) G2 6PH (GB) • HENTEMANN, Martin, F. Hamden, CT 06517 (US) (56) References cited: • MA, Xin EP-A- 0 298 465 WO-A-03/011842 Bethany, CT 06524 (US) WO-A-03/089418 • RUDOLPH, Joachim Guilford, CT 06437 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 578 715 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 578 715 B1 Description FIELD OF THE INVENTION 5 [0001] This invention is directed to indane acetic acid derivatives and their use In pharmaceutical compositions for the treatment of diseases such as diabetes, obesity, hyperlipidemia, and atherosclerotic disease. The invention is also directed to intermediates useful in preparation of indane acetic derivatives and to methods of preparation. BACKGROUND OF THE INVENTION 10 [0002] Type 2 diabetes Is the more common form of diabetes, with 90-95% of hyperglycemic patients experlencing this form of the disease. In type 2 diabetes, there appears to be a reduction in the pancreatic β-cell mass, several distinct defects in insulin secretion, and a decrease in tissue sensitivity to insulin. The symptoms and consequences of this form of diabetes include fatigue, frequent urination, thirst, blurred vision, frequent infections and slow healing of sores, diabetic 15 nerve damage, retinopathy, micro and macro blood vessel damage, and heart and renal disease. [0003] Resistance to the metabolic actions of insulin is one of the key features of type 2 diabetes. Insulin resistance is characterized by impaired uptake and utilization of glucose in insulin-sensitive target organs, for example, adipocytes and skeletal muscle, and by impaired inhibition of hepatic glucose output, Functional insulin deficiency, insulin resistance in the periphery, and the failure of insulin to suppress hepatic glucose output results in fasting hyperglycemia. Pancreatic 20 β-cells compensate for the insulin resistance by secreting increased levels of insulin. However, the β-cells are unable to maintain this high output of insulin, and eventually, the glucose-induced insulin secretion falls, leading to the deteri- oration of glucose homeostasis and to the subsequent development of overt diabetes. Hyperinsullnemia Is also linked to insulin resistance, hypertriglyceridemia, low high-density Ilpoprotein (HDL) cholesterol, and increased plasma con- centration of low-density lipoproteins (LDL). The association of insulin resistance and hyperinsullnemia with these met- 25 abolic disorders has been termed "Syndrome X," and has been strongly linked to an increased risk of hypertension and coronary artery disease. [0004] Obesity is an excessive accumulation of adipose tissue. Excess adipose tissue is associated with the devel- opment of serious medical conditions, for example, type 2 diabetes, hypertension, coronary artery disease, hyperlipi- demia, obesity, and certain malignancies. The adipocyte may also influence glucose homeostasis through the production 30 of tumor necrosis factor α (TNFα) and other molecules. [0005] Atherosclerotic disease Is known to be caused by a number of factors, for example, hypertension, diabetes, low levels of HDL, and high levels of LDL. Atherosclerotic-related diseases include cardiovascular disease, coronary heart disease (CHD), cerebrovascular disease, and peripheral vessel disease. Coronary heart disease includes CHD death, myocardial infarction, and coronary revascularization. Cerebrovascular disease includes ischemic or hemorrhagic 35 stroke, and transient ischemic attacks. [0006] Accordingly, despite the presence of some pharmaceuticals that are used to treat these diseases, there remains a need for new pharmaceuticals that are both safe and effective agents for the treatment of the disease, and for useful methods to prepare them. 40 DESCRIPTION OF THE INVENTION [0007] The invention relates to the group of compounds as defined in claim 1. DEFINITIONS 45 [0008] The terms Identified in the present application have the following meaning throughout: The term "halo" means F, Cl, Br, or I. [0009] The term "C1-C6 alkyl" means a straight or branched saturated hydrocarbon carbon chain of from 1 to about 6 carbon atoms, respectively. Examples of such groups include methyl, ethyl, isopropyl, sec-butyl, 2-methylpentyl and 50 n-hexyl. [0010] The term "C2-C6 alkenyl" means a straight or branched unsaturated hydrocarbon carbon chain of from 2 to about 6 carbon atoms. Examples of such groups include vinyl, allyl, Isopropenyl, 2-butenyl, 3-ethyl-2-butenyl, and 4- hexenyl. [0011] The term "C1-C6 haloalkyl" means a C1-C6 alkyl group substituted by 1 to 3 halogen atoms or fluorine up to 55 the perfluoro level. Examples of such groups include trifluoromethyl, tetrafluoroethyl, 1,2-dichloropropyl, 5-bromopentyl, 6-iodohexyl. [0012] The terms "C3-C6 cycloalkyl" and "C3-C8 cycloalkyl" mean a saturated carbocyclic ring system of from 3 to about 6 carbon atoms or from 3 to about 8 carbon atoms, respectively. Examples of such groups include cyclopropyl, 2 EP 1 578 715 B1 cyclobutyl, cyclopentyl, cyclohexyl. [0013] The term "C1-C6 acyl" means a C1-C6 alkyl group attached at the carbonyl carbon atom. The radical is attached to the rest of the molecule at the carbonyl bearing carbon atom. Examples of such groups include acetyl, propionyl, n- butanoyl, 2-methylpentantoyl. 5 [0014] The term "C1-C6 alkoxy" means a linear or branched saturated carbon group having from 1 to about 6 C atoms, said carbon group being attached to an O atom. The O atom is the point of attachment of the alkoxy substituent to the rest of the molecule. Such groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy. [0015] The term "C1-C6 thioalkyl" means a linear or branched saturated carbon group having from 1 to about 6 C atoms, said carbon group being attached to an S atom. The S atom is the point of attachment of the thioalkyl substituent 10 to the rest of the molecule. Such groups include, for example, methylthio, propylthio, hexylthio. [0016] The term "C1-C6 haloalkoxy" means a C1-C6 alkoxy group further substituted on C with 1 to 3 halogen atoms or fluorine up to the perfluoro level. [0017] The term "C3-C8 cycloalkoxy" means a C3-C8 cycloalkyl group attached to an O atom. The O atom is the point of attachment of the cycloalkoxy group with the rest of the molecule. 15 [0018] The term "phenoxy" means a phenyl group attached to an O atom. The O atom is the point of attachment of the phenoxy group to the rest of the molecule. [0019] The term "6-membered heteroaryl ring" means a 6-membered monocyclic heteroaromatic ring radical containing 1-5 carbon atoms and up to the indicated number of N atoms. Examples of 6-membered heteroaryl rings are pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl. 20 [0020] The term "5- or 6-membered heterocyclic ring" means a 5 or 6-membered ring containing 1-5 C atoms and up to the indicated number of N, O, and S atoms, and may be aromatic, partially saturated, or fully saturated. [0021] The term "optionally substituted" means that, unless indicated otherwise, the moiety so modified may have from one to up to the number of the substituents indicated, provided the resulting substitution is chemically feasible as recogized in the art. Each substituent may replace any H atom on the moiety so modified as long as the replacement 25 is chemically possible and chemically stable. For example, a chemically unstable compound would be one where each of two substituents is bonded to a single C atom through each substituents heteroatom. Another example of a chemically unstable compound would be one where an alkoxy group is bonded to the unsaturated carbon of an alkene to form an enol ether. When there are two or more substituents on any moiety, each substituent is chosen independently of the other substituent so that, accordingly, the substituents can be the same or different.
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