Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2008-03-18
2008-03-18
Maier, Leigh C. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S017200, C536S022100
Reexamination Certificate
active
10625645
ABSTRACT:
Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use,wherein,Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”;each of X and Y is optional; X, when present is either —C(R1)2— or —C(R1)2—; Y, when present, is either —CH2— or —CH2—CH2—;z, R5and R5′are optional, and when present z, R5and R5′together form a lower alkyl or a substituted lower alkyl moiety;N is part of either an amine or an amide linkage;E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof;R1and R4are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl;R2and R3are hydroxyl;R5and R6, when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialkylamino-carbonyl; and,R6and R6′are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carboxyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialylamino-carbonyl,with the proviso that Ring 1 is capable of binding to any of:a dopaminergic receptor selected from the group consisting of a D1 receptor and a D5 receptor; a DAT transporter; a VMAT transporter; and,with the proviso that E is capable of binding to a GLUT transporter selected from the group consisting of a GLUT1 receptor and a GLUT3 receptor.
REFERENCES:
patent: 3929813 (1975-12-01), Bodor
patent: 3962447 (1976-06-01), Bodor
patent: 5380837 (1995-01-01), Nakada et al.
patent: 5639737 (1997-06-01), Rubin
patent: 6339064 (2002-01-01), McDevitt et al.
patent: 6548484 (2003-04-01), Christian
patent: 2006/0189547 (2006-08-01), Christian
patent: WO 97/28174 (1997-08-01), None
patent: WO 01/97244 (2007-10-01), None
Tamai, I. et al “Transporter-mediated permeation of drugs . . . ” J. Pharm. Sci. (2000) vol. 89, No. 11, pp. 1371-1388.
Knoerzer, T. et al “Dopaminergic benzo[a]phenanthridines . . .” J. Med. Chem. (1994) vol. 37, No. 15, pp. 2453-2460.
Meiergerd, S. et al“Striatal transporter for dopamine . . .” J. Neurochem. (1994) vol. 62, No. 3, pp. 998-1008.
Jiang, C. et al“Dopaminergic properties and experimental anti-Parkinsonian effects . . .” Clin. Neuropharmacol. (2004) vol. 27, No. 2, pp. 63-73.
Maher, F. et al “Substrate specificity and kinetic parameters of GLUT3 . . .” Biochem. J. (1996) vol. 315, pp. 827-831.
Caplus abstract of “New Approaches Chromatogr. '93 pp. 243-266. (1993)” Accession No. 1995:473353. Accessed Nov. 10, 2006.□□.
Caplus abstract of “J. Drug Targeting 8(6) pp. 395-401 (2000)” Accession No. 2001:307631. Accessed Nov. 10, 2006.□□.
Caplus abstract of “Int. J. Oncology 11(3) pp. 497-507 (1997)” Accession No. 1997:567722. Accessed Nov. 10, 2006.□□□□.
Ovalle, R. et al “Systematic analysis of oxidative degradation . . .” Carbohyd. Res. (2001) vol. 330, pp. 131-139.
Fernandez, C. et al “Synthesis and biological studies of glycosyl dopamine derivatives . . .” Carbohyd. Res. (2000) vol. 327, pp. 353-365.
Likhosherstov, L. et al “Glycoconjugates of amines: alkylation of primary and secondary amines . . . ” Russ. Chem. Bull. (1998) vol. 47, No. 6, pp. 1214-1217.
Alexander et al., “Role of conjugation and red blood cells for inactivation of ciculating catecholamines,”Am. J. Physiol.247(1):R203-R207 (1984).
Alvarado et al., “Phlorizin as a competitive inhibitor of the active transport of sugars by hamster small intestine, in vitro,”Biochim. Biophys. Acta56:170-172 (1960).
Arita et al., “Studies on uptake of phenyl glycosides as inhibitors of D-glucose uptake by Rhesus monkey kidney cells,”J. Biochem.88:1399-1406 (1980).
Barnett et al., “Structural requirements for binding to the sugar transport system of the human erythrocyte,”Biochem. J.131:211-221 (1973).
Barnett et al., “Highlights of D1 dopamine receptor antagonist research,”Neurochem. Int.20 (Suppl.):119S-122S (1992).
Bencsics et al., “Dopamine, as well as, norepinephrine, is a link between noradrenergic nerve terminals and splenocytes,”Brain Res.761(2):236-243 (1997).
Berger et al., “Synthesis and receptor affinities of some conformationally restricted analogues of the dopamine D1 selective ligand (5R)-8-chloro-2,3,4,5-tetrahydro-3-methyl-5-phenyl- 1 H-3-benzazepin-7-ol,”J. Med.(1989).
Brewster et al., “trans-10,11-dihydroxy-5,6,7,8,12b-hexahydrobenzo[a]phen-anthridine: A highly potent selective dopamine D1 full agonist,”J. Med. Chem.33:1756-1764 (1990).
Bodor et al., “Elimination of a quaternary pyridinium salt delivered as its dihydropyridine,”J. Pharr. Sci., 67(5):685 (1978).
Bodor, “Novel Approaches for the Design of Membrane Transport Properties of Drugs” In: “Design of Biopharmaceutical Properties Through Prodrugs and Analogs”, Ed. E.B. Roche et al. APhA Academy of Pharmaceutical Sciences, Washington, D.C., pp. 98-135 (1976).
Bodor et al., “Site-specific, sustained release of drugs to the brain,”Science214:1370-1372 (1981).
Bodor et al., “Redox delivery systems for brain-specific, sustained release of dopamine,”Science221:65-67 (1983).
Casagrande et al., “Synthesis and chemical properties of Ibopamine and of related esters of N-substituted dopamines:Synthesis of Ibopamine metabolites,”Arzneim.Forsch.36(2a):291-303 (1986).
Chen et al., “Transport-dependent accessibility of a cytoplasmic loop cysteine in human dopamine transporter”J. Biol. Chem.275(3):1608-1614 (2000).
Choi et al., “Novel 3-aminomethyland 4-aminopiperidine analogues of 1[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazines: Synthesis and evaluation as dopamine transporter ligands,”J. Med. Chem.43(2):205-213 (2000).
Clarkson et al., “Immortalized dpamine neurons: A model to study neurotoxicity and neuroprotection,”Proc. Soc. Exp. Biol. Med.222(2):157-163 (1999).
Claustre et al., “Conjugation and deamination of circulating dopamine: Relationship between sulfated and free dopamine in man,”J. Auton, Nerv. Syst.29(2):175-182 (1990).
Coffey et al., “[3H]WIN 35,428 binding to the dopamine uptake carrier. I. Effect of tonicity and buffer composition,”J. Neurosci. Methods51(1):23-30 (1994).
Czarnocki et al. “Enantiselective synthesis of (R)-(-)-Laudanosine and (R)-(-)-Glaucine from L-Ascorbic Acid,” Tetrahedron: Assymetry, 7(9):2711-2720 (1996).
Dandrige et al.J. Med. Chem.27:28 (1984).
Diez-Sampedro et al., “Galactose transport inhibition by cytochalasin E in rat intestine in vitro,”Can. J. Physiol. Pharmacol.77(2):96-101 (1999).
Duport et al., “An in vitro blood-brain barrier model: Cocultures between endothelial cells and organtypic brain slice cultures,”Proc. Natl. Acad. Sci.USA 95(4):1840-1845 (1998).
Earles et al., “Multisubstrate mechanism for the inward transport of dopamine by the human dopamine transporter expressed in HEK cells and its inhibition by cocaine,”Synapse33(3):230-238 (1999).
Figlewicz, “Endocrine regulation of neurotransmitter transporters,”Epilepsy Res.37(3) 203-210 (1999).
Findlay et al., “Inhibition of glycosidases by aldonolactones or corresponding configuration. 2. Inhibitors of b-N-acetylglucosaminidase,”Biochemical J.69:467-476 (1958).
Fischer et al., “5-Hydroxytraptamine stimulates glucose transport in cardiomyocytes via a monoamine oxidase-dependent reaction,”Biochem. J.311(2):575-583 (1995).
Fodor et al.,Acta Chim.
International Medical Innovations, Inc.
Maier Leigh C.
Needle & Rosenberg PC
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