Substituted 1,3-diphenylpropane derivatives, preparations and uses thereof

• US 8,258,182 B2
• Filed: 06/21/2007
• Issued: 09/04/2012
• Est. Priority Date: 06/21/2006
• Status: Active Grant

• Current Assignee: Genfit SA
• Original Assignee: Genfit SA
• Inventors: Delhomel, Jean-François, Hanf, Rémy, Caumont-Bertrand, Karine
• Primary Examiner(s): Jean-Louis, Samira
• Application Number:
  US12/308,580
• Publication Number:
  US 20110136888A1
• Time in Patent Office: 1,902 Days
• Field of Search: 514/543, 514/571, 562/405, 562/464, 560/17
• US Class Current: 514/543
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 Antihyperlipidemics
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 39/06 Free radical scavengers or antioxidants
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 5/50 for increasing or potentiating the activity of insulin
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/04 Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 Antihypertensives
• CPC Class Codes: A61P 9/14 Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
• CPC Class Codes: C07C 323/18 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 323/22 : containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
• CPC Class Codes: C07C 323/45 : having at least one of the nitrogen atoms doubly-bound to the carbon skeleton
• CPC Class Codes: C07C 323/52 : the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 59/88 : containing halogen
• CPC Class Codes: C07C 59/90 : containing singly bound oxygen-containing groups
• CPC Class Codes: C07D 335/06 : Benzothiopyrans; Hydrogenated benzothiopyrans

Abstract

The present invention involves substituted 1,3-diphenylpropane derivatives, pharmaceutical compositions comprising them and the therapeutic uses thereof, in particular in the fields of human and animal health.

Claims

1. A compound, derived from substituted 1,3-diphenylpropane, having general formula (I):

2. The compound according to claim 1, wherein A represents a carbonyl group (CO).

3. The compound according to claim 1, wherein represents a G4R4 group, wherein

R4 represents an alkyl group comprising from 1 to 10 carbon atoms, substituent by a —

COOR9, as defined in claim 1.

4. The compound according to claim 1, wherein G4 represents an oxygen atom.

5. The compound according to claim 1, wherein the X4 group corresponds to the formula —

OC(CH₃)₂COOR9, R9 being such as defined in claim 1.

6. The compound according to claim 1, wherein X3 and X5, identical or different, represent respectively a R3 and R5 group, R3 and R5 representing an unsubstituted alkyl group comprising from 1 to 4 carbon atoms.

7. The compound according to claim 1, wherein X1 represents a G1R1 group, G1 being such as defined in claim 1 and R1 representing a non-halogenated alkyl group comprising from 1 to 3 carbon atoms.

8. The compound according to claim 1, wherein said compound is selected from:

2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-oxo-propyl]phenoxy]-ethanoic acid

2-[2,6-dimethyl-4-[3-[4-(propyloxy)phenyl]-3-oxo-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-oxo-propyl]phenoxy]-2-methyl-isopropyl propanoate;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3- hydroxyimino-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(propyloxy)phenyl]-3- hydroxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-cyclohexylmethoxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-butyloxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-isopropyloxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-cyclohexylethyloxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-benzyloxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-hydroxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-ethyloxy-propyl]phenoxy]-2-methyl-propanoic acid;

2-[2,6-dimethyl-4-[3-[4-(methylthio)phenyl]-3-methoxy-propyl]phenoxy]-2-methyl-propanoic acid;

9. A pharmaceutical composition comprising, in a pharmaceutically acceptable support, at least one compound as defined in claim 1.