Aryl boronic acids for treating obesity

Details Aryl boronic acids for treating obesity Aryl boronic acids for treating obesity

2006-01-31

2008-11-25

Gonzalez, P. Nazario (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Boron containing doai

C562S007000

Reexamination Certificate

active

07456156

ABSTRACT:
Disclosed is a phenyl boronic acid compound represented by Structural Formula (I):Ar is a substituted or unsubstituted aryl group.Z and Z′ are independently —O—, —NH— or —S—.X is an electron withdrawing group.R is a substituted or unsubstituted straight chained hydrocarbyl group optionally comprising one or more amine, ammonium, ether, thioether or phenylene linking groups and Y is —H, an amine, —[NH—(CH2)q]r—NH2, halogen, —CF3, thiol, ammonium, alcohol, —COOH, —SO3H, —OSO3H or phosphonium group covalently bonded to the terminal position of R. Each —NH— in —[NH—(CH2)q]r—NH2is optionally N-alkylated or N,N-dialkylated and —NH2in —[NH—CH2)q]r—NH2is optionally N-alkylated, N,N-dialkylated or N,N,N-trialkylated.q is an integer from 2 to about 10 and r is an integer from 1 to about 5.R1and R1′are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group, or, taken together, are a C2-C5 substituted or unsubstituted alkylene group optionally comprising an amine linking group [—N+(R1a)—]. Each R1is Structural Formula (I) is preferably —H.R1ais —H, alkyl, substituted alkyl phenyl or substituted phenyl.Also disclosed is a method of treating obesity in a subject by administering an effective amount of a compound represented by Structural Formula (I) and a pharmaceutical composition comprising the compound and a pharmaceutically acceptable carrier or diluent.

REFERENCES:
patent: 4496722 (1985-01-01), Gallop et al.
patent: 5290817 (1994-03-01), Petraitis
patent: 5356893 (1994-10-01), Bradshaw et al.
patent: 5472628 (1995-12-01), Panandiker et al.
patent: 5631364 (1997-05-01), Sundrehagen et al.
patent: 5631371 (1997-05-01), Bloczynski
patent: 5702952 (1997-12-01), Sundrehagen et al.
patent: 5726343 (1998-03-01), Ziegler et al.
patent: 5739318 (1998-04-01), Frantzen et al.
patent: 5840677 (1998-11-01), Nielsen et al.
patent: 5866568 (1999-02-01), Bradbury et al.
patent: 5972873 (1999-10-01), Nielsen et al.
patent: 6184363 (2001-02-01), Shoichet et al.
patent: 6197967 (2001-03-01), Vollmueller et al.
patent: 6264937 (2001-07-01), Mandeville, III et al.
patent: 6858592 (2005-02-01), Holmes-Farley et al.
patent: 2004/0038940 (2004-02-01), Caron et al.
patent: 3930663 (1990-11-01), None
patent: 4307243 (1993-10-01), None
patent: 0 354 434 (1990-02-01), None
patent: 0 478 050 (1992-04-01), None
patent: 0 495 627 (1992-07-01), None
patent: 0 571 928 (1993-12-01), None
patent: 1 072 597 (2001-01-01), None
patent: 2 276 162 (1994-09-01), None
patent: 07-062023 (1995-03-01), None
patent: 2000336045 (2000-12-01), None
patent: 3257029 (2001-12-01), None
patent: 2002265472 (2002-09-01), None
patent: WO-92/08722 (1992-05-01), None
patent: WO-94/14803 (1994-07-01), None
patent: WO-95/01326 (1995-01-01), None
patent: WO-95/11243 (1995-04-01), None
patent: WO-95/20569 (1995-08-01), None
patent: WO-96/02288 (1996-02-01), None
patent: WO-96/17833 (1996-06-01), None
patent: WO-96/21716 (1996-07-01), None
patent: WO-96/30333 (1996-10-01), None
patent: WO-96/40681 (1996-12-01), None
patent: WO-97/30055 (1997-08-01), None
patent: WO-98/22820 (1998-05-01), None
patent: WO-98/47885 (1998-10-01), None
patent: WO-98/56392 (1998-12-01), None
patent: WO-99/05107 (1999-02-01), None
patent: WO-99/23073 (1999-05-01), None
patent: WO-99/47474 (1999-09-01), None
patent: WO-00/06537 (2000-02-01), None
patent: WO-00/14083 (2000-03-01), None
patent: WO-00/27394 (2000-05-01), None
patent: WO-00/27820 (2000-05-01), None
patent: WO-00/35904 (2000-06-01), None
patent: WO-00/42213 (2000-07-01), None
patent: WO-00/61571 (2000-10-01), None
patent: WO-01/16108 (2001-03-01), None
patent: WO-02/44189 (2002-06-01), None
patent: WO-03/106384 (2003-12-01), None
Liepins et al., Journal of Applied Polymer Science, vol. 17, pp. 2523-2532 (1973).
Barba, V., et al., “Synthesis and molecular structures of dimeric boron compounds”, J. Organometallic Chem., 604:273-282 (2000).
CA:119:139268 abs of EP 533266 Mar. 1993.
CA:120:218155 abs JP 05301880 Nov. 1993.
CA:126:144291 abs of WO 960681 Dec. 1996.
CA:132:331255 abs of Biorganic & Medicinal Chem by DeSantis et al. 8(3) pp. 563-570 2000.
CA:137:249492 abs of JP20022654 Sep. 2002.
CA:137:26190 abs of WO 2002044189 Jun. 2002.
CA:140:59511 abs of WO 2003106384 Dec. 2003.
CA:79:106049 abs of Journal of Applied Polymer Science by Leipins et al. 17 (8) pp. 2523-2532 (1973).
Deantis, G., et al., “Benzophenone boronic acid photoaffinity labeling of subtilisin CMMs to probe altered specificity,” Bioorganic and Medicinal Chemistry, 8(3):563-570 (2000).
Draffin, S.P., et al., “Highly Fructose Selective Transport Promoted by Boronic Acids Based on a Pentaerythritol Core,” American Chemical Society, Organic Letters, 3(6):917-920 (2001).
English patent abstract of JP 2002-265472, Aug. 6, 2004.
English patent abstract of JP 3257029B2, Aug. 9, 2004.
Folch, J., et al., “A Simple Method For The Isolation and Purification of Total Lipides From Animal Tissues”, J. Biol. Chem., 226:497 (1957).
Gravel, M., et al., “Universal Solid-Phase Approach for the Immobilization, Derivatization, and Resin-to-Resin Transfer reactions to Boronic Acids,” J. Org. Chem., 67:3-15 (2002).
Hall, D.G., et al., “N, N-Diethanolaminomethyl Polystyrene: An Efficient Solid Support to Immobilze Boronic Acids,” Angew. Chem. Int. Ed., 38(20):3064-3067 (1998).
Hall, D.G., et al., “N,N-Diethanolaminomethylpolystyrol: ein effizienter fester Träger für die Immobilisierung von Boronsäuren,” Angew. Chem. Int., 111:3250-3253 (1999).
Hall, I., et al., “Hypolipidemic, Anti-obesity, Anti-inflammatory, Anti-osteoporotic, and Anti-neoplastic Properties of Amine Carboxyboranes,” Environ. Health Perspect. Suppl. 102(S3):21-30 (1994).
Hansch, C., et al., “Hammett Sigmas,” Exploring QSAR Hydrophobic, Electronic and Steric Constants, American Chemical Society, 217-232 (1995).
Ishiyama, T., et al., “Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters”, J. Org. Chem., 60(23):7508-7510 (1995).
Kinder, D. H., et al., “Synthesis of 2-Amino-3-Boronopropionic Acid: A Boron-Containing Analogue of Aspartic Acid,” J. Org. Chem., 52(12):2452-2454 (1987).
Kobayashi, Y., et al., “Preparation of Functionalized Zinc Borates an their Coupling Reaction with Allylic Acetates,” Tetrahedron Lett., 39:7537-7540 (1998).
Leipins, R. et al., “Organoboron compounds as durable flame retardants for cotton fabric,” Journal of Applied Polymer Science, 17(8):2523-32 (1973).
Matteson, D. S., et al., “Directed Chiral Synthesis with Pinanediol Boronic Esters”, J. Am. Chem. Soc., 102(25):7590-7591 (1980).
Reuman, M., et al., “Synthesis and Antibacterial Activity of Some Novel 1-Substituted 1,4-Dihydro-4-Oxo-7-pyridinyl-3-quinolinecarboxylic acids. Potent Antistaphylococcal Agents.” J. Med. Chem., 38(14):2531-2540 (1995).
Saito, S., et al., “Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids”, J. Org. Chem. 62:8024-8030 (1997).
Sakai, M., et al., “Rhodium-Catalyzed Addition of Organoboronic Acids to Aldehydes”, Angew. Chem. Int. Ed. 37(23):3279-3281 (1998).
Medilne, abstract No. 11234459, “Obesity: preventing and managing the global epidemic”, Report of a WHO consultation, World Health Organization technical report series, (2000) 894 i-xii, 1-253.

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