Substituted-2-imidazoles

Details Substituted-2-imidazoles Substituted-2-imidazoles

2007-10-31

2010-11-16

Shameem, Golam M (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C548S311100, C548S311400, C548S312100, C546S112000, C546S152000, C514S311000, C514S385000, C514S396000

Reexamination Certificate

active

07834044

ABSTRACT:
The present invention relates to compounds of formula IwhereinR1is selected from the group consisting of hydrogen and lower alkyl;each R2is independently selected from the group consisting of hydrogen and lower alkyl;each R3is independently selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, phenyloxy, benzyloxy, halogen and lower alkyl substituted by halogen;X is selected from the group consisting of —CH2—, —CH— and —O—;Y is selected from the group consisting of —CH2—, —CH— and a bond with the proviso that, when X is —O—, Y may not be a bond;Z is selected from the group consisting of —CH2— and —CH—;m is 0, 1 or 2; andn is 0, 1 or 2;and to pharmaceutically-acceptable acid addition salts of such compounds.The invention relates also to processes for preparing such compounds, compositions comprising such a compound or a pharmaceutically-acceptable acid addition salt thereof, and a method of treating a disease or disorder in a patient comprising administering such a compound, or pharmaceutically-acceptable acid addition salt thereof, to a patient in need of such treatment.

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: 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: 7211672 (2007-05-01), Ghosh et al.
patent: 7504508 (2009-03-01), Ghosh 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: 323 985 (1966-12-01), None
patent: 0 024 829 (1981-03-01), 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: 6 551 (1968-12-01), None
patent: 877306 (1961-09-01), None
patent: 1016514 (1966-01-01), 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 02/76950 (2002-10-01), None
patent: WO 03/092374 (2003-11-01), None
patent: WO 2004/014898 (2004-02-01), None
patent: WO 2006/119411 (2006-11-01), None
patent: WO 2007/024944 (2007-03-01), None
patent: WO 2007/024949 (2007-03-01), None
Altenbach et al., Synthesis and Structure-Activity Studies onN-[5-(1H-Imidazol-4-y1)-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-l-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-Htib/Id Serotonin 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-y1)2-methylpropan-lol 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. Pharmacology (1985), 28:254-268.
Ojida et al., Sterocontrolled synthesis of (1S)-1 -(1H-imidazol-4-yl)-1-(6-methoxy-2-napthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor,Tetrahedron: Asymmetry (2004), 15: 1555-1559.
Olmos et al., Imidazolines stimulate release of insulin from Rin-5AH cells independently from imidazoline I1and I2receptors, European Journal of Pharmacology (1994), 262: 41-48.
Prisinzano et al., 2-(aniline)imidazolines and 2-(benzyl)imidazoline derivatives ash5-HT-IDserotonin receptor ligands, Bioorganic & Medicinal Chemistry Letter (2004), 14:4697-4699.
Savola et al., Cardiovascular and Sedative α-Adrenoceptor Effects of Detomidine-like Arylalkyl Imidazoles

Affiliated with

Also associated with

Rating

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4238820