2-imidazoles

Details 2-imidazoles 2-imidazoles

2007-12-05

2010-12-28

Saeed, Kamal A (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S331500

Reexamination Certificate

active

07858653

ABSTRACT:
The present invention relates to compounds of formula I,whereinX is —CH2— or —NH—;Y is —CH(lower alkoxy)-, —CH(lower alkyl)-, —O—, —S—, —S(O)—, —S(O)2— or —CH2—; andAr is phenyl or naphthyl, which rings are optionally substituted by one or two substituents selected from the group consisting of halogen, lower alkoxy, lower alkyl and lower alkyl substituted by halogen;or a pharmaceutically-acceptable acid-addition salt thereof;with the proviso that, when X is —NH—, Y is —CH(lower alkyl)- or —CH2—;and the further proviso that the compound is not2-phenethyl-1H-imidazole hydrochloride,2-(3,4-dichloro-phenoxymethyl)-1H-imidazole hydrochloride,2-(2-chloro-phenoxymethyl)-1H-imidazole hydrochloride,2-(2,3-dichloro-phenoxymethyl)-1H-imidazole,benzyl-(1H-imidazol-2-yl)-amine,(4-chloro-benzyl)-(1H-imidazol-2-yl)-amine, or(2-chloro-benzyl)-(1H-imidazol-2-yl)-amine.The invention relates also to a pharmaceutically-acceptable acid-addition salt of such a compound, processes for making the compound, and a composition comprising such a compound.

REFERENCES:
patent: 2161938 (1939-06-01), Sonn
patent: 2457047 (1948-12-01), Kyrides
patent: 2731471 (1956-01-01), Synerholm et al.
patent: 2744909 (1956-05-01), Speeter
patent: 2744910 (1956-05-01), Speeter
patent: 2778836 (1957-01-01), Morren
patent: 2919274 (1959-12-01), Faust et al.
patent: 3161653 (1964-12-01), Fruhstorfer et al.
patent: 3354175 (1967-11-01), Fruhstorfer et al.
patent: 3377247 (1968-04-01), Elbe
patent: 3459763 (1969-08-01), Gruenfeld
patent: 3586695 (1971-06-01), Wysong et al.
patent: 3622579 (1971-11-01), Stahle et al.
patent: 3660423 (1972-05-01), Wysong et al.
patent: 3758476 (1973-09-01), Rippel et al.
patent: 3818035 (1974-06-01), Binon et al.
patent: 3818094 (1974-06-01), Stahle et al.
patent: 3992403 (1976-11-01), Roebke
patent: 4125620 (1978-11-01), Stahle et al.
patent: 4146647 (1979-03-01), Lafon
patent: 4323570 (1982-04-01), Stenzel et al.
patent: 4665095 (1987-05-01), Winn et al.
patent: 5610174 (1997-03-01), Craig et al.
patent: 5658938 (1997-08-01), Geerts et al.
patent: 2002/0019390 (2002-02-01), Wong et al.
patent: 2003/0181354 (2003-09-01), Abdulrazik
patent: 2003/0236274 (2003-12-01), Tasaka et al.
patent: 2246027 (2000-02-01), None
patent: 16 95 005 (1971-02-01), None
patent: 0 024 829 (1981-03-01), None
patent: 0 086 043 (1983-08-01), None
patent: 0 125 410 (1984-11-01), None
patent: 0 166 937 (1986-01-01), None
patent: 0 331 374 (1989-09-01), None
patent: 0 424 059 (1991-04-01), None
patent: 0 857 483 (1998-08-01), None
patent: 0 924 209 (1999-06-01), None
patent: 1 103 243 (2001-05-01), None
patent: 1 413 576 (2004-04-01), None
patent: 323 985 (1966-12-01), None
patent: 6 551 (1968-12-01), None
patent: 877306 (1961-09-01), None
patent: 1016514 (1966-01-01), None
patent: 1131191 (1968-10-01), None
patent: WO 96/22768 (1996-08-01), None
patent: WO 97/12874 (1997-04-01), None
patent: WO 98/12183 (1998-03-01), None
patent: WO 01/30762 (2001-05-01), None
patent: WO 01/81334 (2001-11-01), None
patent: WO 02/22801 (2002-03-01), None
patent: WO 02/40453 (2002-05-01), None
patent: WO 02/076950 (2002-10-01), None
patent: WO 03/092374 (2003-11-01), None
patent: WO 2004/014898 (2004-02-01), None
patent: WO 2006/107923 (2006-10-01), None
patent: WO 2006/119411 (2006-11-01), None
patent: WO 2007/024944 (2007-03-01), None
Gruenfeld et al, caplus an 1969:47457.
Freiter, E.R., et al., J. Heterocyclic Chem., vol. 10, No. 3, pp. 391-394 (1973), XP008087527.
Tarnchompoo, B., et al., vol. 31, No. 40, pp. 5779-5780 (1990), XP002118267.
Wilkinson, C.F., et al., Biochem. Pharmacol., vol. 21, pp. 3187-3192 (1972), XP :008087536.
Raddatz, Rita , et al., J. Pharmacol. Exp. Therap., vol. 292, No. 3, pp. 1135-1145 (2000), XP008087488.
Shafiee, A., et al., Journal of Heterocyclic Chemistry, pp. 607-610 (1998), XP001069546.
Robertson, David W., J. Med. Chem., vol. 29, pp. 1577-1586 (1986), XP008087539.
Database CA, Chemical Abstracts, Yamaguchi, Hideaki, XP002465006 & JP 06 268356 (1994).
Altenbach et al., Synthesis and Structure-Activity Studies onN-[5-(1H-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidasole-Containing α1A-Adrenoceptor Agonist, J. Med. Chem. (2004), 47: 3220-3235.
Amemiya et al., Synthesis and α-Adrenergic Activities of 2-and 4-Substituted Imidazoline and Imidazoline Analogues, J. Med. Chem. (1992), 35:750-755.
Bagley et al., Synthesis and α2-Adrenegeric Activities of Imidazole and Imidazolidine Analogues: In Vitro and In Vivo Selectivity, Medicinal Chemistry Research (1994), 4:346-364.
Branchek et al., Trace amine receptors as targets for novel therapeutics: legend, myth and fact, Curr. Opin. Phamacol. (2003), 3:90-97.
Bunzow et al., Amphetamine, 3,4-Methylenedioxymethamphetamine, Lysergic Acid Diethylamide, and Metabolites of the catecholamine Neurotransmitters Are Agonists of a Rat Trace Amine Receptor, Molecular Pharmacology (2001), 60: 1181-1188.
Carroll et al., In Vitro and In Vivo Characterization of Alpha-1A Selective Agonists and Their Utility For Stress Incontinence, Med. Chem. Res. (2004), 13:134-148.
De Bernardis et al., Conformationally Defined Adrenergic Agents. 3. Modifications to the Carbocyclic Ring of 5,6-Dihydroxy-1-(2-imidazolinyl)tetralin: Improved Separation of α1and α2Adrenergic Activities, J. Med. Chem. (1986), 29:1413-1417.
De Bernardis et al., Conformationally Defined Adregernic Agents. 5. Resolution, Absolute Configuration, and Pharmacological Characterization of the Enantiomers of 2-(5,6-Dihydroxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline: A Potent Agonist at α—Adrenoceptors, J. Med. Chem. (1987), 30:1011-1017.
Faust et al., Antihypertensive Agents: Derivatives of 2-Imidazoline and 1,4,5,6-Tetrahydropyrimidine, J. Org. Chem. (1961), 26: 4044-4047.
Hirashima et al., Three-Dimensional Common-Feature Hypotheses for Octopamine Agonist 2-(Arylimino)imidazolidines, Bioorganic & Medicinal Chemistry (2002), 10:117-123.
Holt, A., Imidazoline binding sites on receptors and enzymes:Emerging targets for novel antidepressant drugs?, Journal of Psychiatry & Neuroscience (2003), 28:409-414.
Jetter et al., Synthesis of 4-Substituted Imidazoles via Palladium-Catalyzed Cross-Coupling Reactions, Synthesis (1998), 829-831.
Law et al., Benzylimidazolines as h5-HT1B/1DSerotonin Receptor Ligands: A Structure-Affinity Investigation, J. Med. Chem. (1998), 41:2243-2251.
Lee et al., 4-[(N-Imidazol-2-ylmethyl)aniline]pyranopyridine Analogs as Novel Anti-Angiogenic Agents, Bull. Korean Chem. Soc. (2005), 25: 619-628.
Lindemann et al., A renaissance in trace amines inspired by a novel GPCR family, Trends in Pharmacol. Sci. (2005), 26:274-281.
Lindemann et al., Trace amine-associated receptors form structurally and functionally distinct subfamilies of novel G protein-coupled receptors, Genomics (2005), 85: 372-385.
Matsunaga et al., C17,20inhibitors. Part 2: Design, synthesis and structure-activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors, Bioorganic & Medicinal Chemistry (2004), 4314.
Matsunaga et al., Synthetic studies on (1S)-6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)2-methylpropan-1-ol as a selective C17,20-lyase inhibitor, Tetrahedron: Asymmetry (2004), 15: 2021-2028.
McCormack et al., Autoradiographic Localization of Tryptamine Binding Sites in the Rat and Dog Central Nervous System, J. Neurosci. (1986), 6:94-101.
McLennan, P;L., The Hypothermic Effect of Clonidine and Other Imidazolidines in Relation to their Ability to Enter the Central Nervous System in Mice, European Journal of Pharmacology (1981), 69:477-482.
Mosseau et al., A high-affinity [3H]tryptamine binding site in human brain, Prog. Brain Res. (1995), 106:285-291.
Nathanson, J.A.,Phenyliminoimidazolines: Characterization of a Class of Potent Agonists of Octopamine-Sensitive Adenylate Cylcase and Their Use in Understanding the Pharmacology of Octopamine Receptors, Amer. Soc. Ph

Affiliated with

Also associated with

Rating

2-imidazoles does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-imidazoles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-imidazoles will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4222885