R(−)-11-hydroxyaporphine derivatives and uses thereof

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C546S075000

Reexamination Certificate

active

08063060

ABSTRACT:
The invention features derivatives of R(−)-11-hydroxyaporphines and methods of treating Parkinson's disease, sexual dysfunction, and depressive disorders therewith.

REFERENCES:
patent: 4353912 (1982-10-01), Neumeyer
patent: 5258384 (1993-11-01), Cannon et al.
patent: 5744476 (1998-04-01), Locke
patent: 5994363 (1999-11-01), El-Rashidy et al.
patent: 6313134 (2001-11-01), Su
patent: 7057044 (2006-06-01), Su
patent: 7648995 (2010-01-01), Neumeyer et al.
patent: WO 90/12574 (1990-11-01), None
patent: WO-90/12574 (1990-11-01), None
patent: WO 00/35457 (2000-06-01), None
patent: WO 02/14279 (2002-02-01), None
patent: WO 2009/009083 (2009-01-01), None
patent: WO 2010/019856 (2010-02-01), None
Granchelli et al.: Aporphines.23.Normorphothebaine derivatives: synthesis of an aporphine nitrogen mustard. J. Org. Chem. vol. 42, pp. 2014-2017, 1977.
Gao, Y. et al.: Synthesis and dopamine agonist and antagonist effects of ( R )-(−) and (S)-(+)-11-hydroxy-N-n-propylnoraporphine. J. Med. Chem. vol. 31, pp. 1392-1396, 1988.
Bentley, K. et al.: The morphine-the baine group of alkaloids. J. of the Chem. Soc., pp. 3252-3260, 1955.
Arana et al., “Pharmacology of High-Affinity Binding of [3H] (+/−)2-Amino-6,7-Dihydroxy-1,2,3,4-Tetrahydronaphthalne (ADTN) to Bovine Caudate Nucleus Tissue,”Biochem. Pharmacol. 32:2873-2880 (1983).
Atkinson et al. “Derivatives of Apomorphine and of Other N-Substituted Norapomorphines,”J. Pharmacol. Sci. 65:1682-1685 (1976).
Baldessarini et al. “Esters of Apomorphine and N,N-Dimethyldopamine as Agonists of Dopamine Receptors in the Rat Brain In Vivo,”Neuropharmacology14:725-731 (1975).
Baldessarini et al., “Receptor Affinities of Aporphine Enantiomers in Rat Brain Tissue,”Eur. J. Pharmacol. 254:199-203 (1994).
Baldessarini et al., “Prolonged Apomorphine-Like Behavioural Effects of Apomorphine Esters,”Neuropharmacology15:471-478 (1976).
Baldessarini et al., “Prolonged D2 Antidopaminergic Activity of Alkylating and Nonalkylating Derivatives of Spiperone in Rat Brain,” Mol. Pharmacol. 42:856-863 (1992).
Berenyi et al., “Synthesis of NewN-SubstitutedN-Demethylaporphine Derivatives,”Acta Chim. Hung. 120:201-205 (1985).
Berenyi et al., “Preparation of Demethoxyoripavine and Its Conversion intoN-SubstitutedN-Demethylapomorphine Derivatives,” Acta Chim. Hung. 113:51-60 (1983).
Berenyi et al., “A New Efficient Method for the Preparation of 2-Fluoro-N-propylnorapomorphine,”J. Chem. Soc. Perkin Trans. I.:2693-2694 (1992).
Berenyi et al., “Rearrangement of Morphinandienes in Methanesulfonic Acid,”J. Chem. Perkin Trans. I:2137-2139 (1993).
Borgman et al. “Diester Derivatives as Apomorphine Prodrugs,”J. Med. Chem. 19:717-719 (1976).
Campbell et al., “Behavioral Effects of (−)10,11-Methylenedioxy-N-n-propylnoraporphine, An Orally Effective Long-Acting Agent Active at Central Dopamine Receptors, and Analogous Aporphines,”Neuropharmacology21:953-961 (1982).
Campbell et al., “R(−) and S(+) Stereoisomers of 11-Hydroxy- and 11-Methoxy-N-n-Propylnoraporphine: Central Dopaminergic Behavioral Activity in the Rat.”Neuropharmacology. 29(6):527-536. (1990).
Campbell et al., “Selective Antidopaminergic Effects of S(+)N-n-propylnoraporphines in Limbic Versus Extrapyramidal Sites in Rat Brain: Comparisons with Typical and Atypical Antipsychotic Agents”Psychopharmacology(Berl.) 103:323-329 (1991).
Cannon et al., “(R)-(−)-10-Methyl-11-hydroxyaporphine: a Highly Selective Serotonergic Agonist,”J. Med. Chem. 31:313-318 (1988).
Csutoras et al. “Synthesis and Neuropharmacological Evaluation of R(− )-N-alkyl-11-hydroxynoraporphines and Their Esters,”Bioinorg. Med. Chem. 12:3553-3559 (2004).
Gao et al. “Synthesis and Dopamine Agonist and Antagonist Effects of (R)-(−)-and (S)-(+)-11-Hydroxy-N-n-propylnoraporphine,”J. Med. Chem. 31:1392-1396 (1988).
Granchelli et al. “Aporphines. 23. Normorphothebaine Derivatives: Synthesis of an Aporphine Nitrogen Mustard,”J. Org. Chem. 42:2014-2017 (1977).
Granchelli et al., “Aporphines. 27. Mechanistic Aspects of the Rearrangement of Thebaine and Codeine Analogues in Methanesulfonic Acid. Improved Method for Synthesis of N-Alkylated Aporphines,”J. Org. Chem. 45:2275-2282 (1980).
Green et al., “Aporphines. XXVI: GLC and Mass Spectrometric Properties of Trifluoroacetyl Derivatives of N-Methyl-, N-Propyl-, and Noraporphines,”STN Caplus(XP002948161) (1980).
Hedberg et al., “(R)-11-Hydroxy- and (R)-11-Hydroxy-10-methylaporphine: Synthesis, Pharmacology, and Modeling of D2Aand 5-HT1AReceptor Interactions,”.J. Med. Chem. 38:647-658 (1995).
Hosztafi et al., “Process for Preparing N-Substituted N-Demethylated 2-Fluoroapocodeine and Apomorphine Derivatives,”STNDatabase Accession No. 1995:623521 (XP0025897400) (1992).
Joyce, “Multiple Dopamine Receptors and Behavior,”Neurosci. Biobehav. Rev. 7:227-256 (1983).
Kula et al., “[3H]β-CIT: A Radioligand for Dopamine Transporters in Rat Brain Tissue,”Eur. J. Pharmacol. 385:291-294 (1999).
Kula et al., “RBI-257: A Highly Potent Dopamine D4Receptor-Selective Ligand,”Eur. J. Pharmacol331:333-336 (1997).
Lal et al., “Effects of Aporphine and Emetine Alkaloids on Central Dopaminergic Mechanisms in Rats,”Eur. Journ. of Pharmacol. 20:71-79 (1972).
Liu et al., “Synthesis and Pharmacological Investigation of Novel 2-Aminothiazole-Privileged Aporphines,”Bioorganic&Med. Chem. 16:6675-6681 (2008).
Liu et al., “N-Propylnoraporphin-11-O-yl Carboxylic Esters as Potent Dopamine D2and Serotonin 5-HT1AReceptor Dual Ligands,”Bioorganic&Med. Chem. 16:8335-8338 (2008).
Makleit et al., “Conversions of Tosyl and Mesyl Derivatives of the morphine Group, XI,” Acta Chim. Sci. Hung. 74:111-113 (1972).
Martinez et al. “Clinical Experience with Apomorphine Hydrochloride: the First 107 Patients,”J. Urology170:2352-2355 (2003).
Morin et al., “N-Monofluoroalkylnoraporphines: Synthesis and Binding Dopamine Receptor Studies,”Med. Chem. Res. 2:354-360 (1992).
Neumeyer et al., “Aporphines 65: Chemical, Microbial Synthesis and Characterization by Gas Chromatography/Mass Spectrometry of (R)-(−)-10-Hydroxy 11-Methoxy-N-n-Propylnoraporphine, a Potential Metabolite of N-n-Propylnorapomorphine.”Biomed. Environ. Mass Spectrom. 13(5):223-229 (1986).
Neumeyer et al., “Therapeutic and Diagnostic Agents for Parkinson's Disease” Chapter 12, vol. 6, Abraham D (ed): Burger's Medicinal Chemistry and Drug Discovery, 6thEdition. New York, John Wiley & Sons, pp. 711-741 (2003).
Neumeyer and Baldessarini, “Apomorphine: New Uses for an Old Drug,”Pharmaceut. News4:12-16 (1997).
Neumeyer et al. “Aporphines, 36. Dopamine Receptor Interactions of Trihydroxyaporphines. Synthesis, Radioreceptor Binding, and Striatal Adenylate Cyclase Stimulation of 2,10,11-Trihydroxyaporphines in Comparison with Other Hydroxylated Aporphines,”J. Med. Chem24:1440-1445 (1981).
Neumeyer et al., “R and S Enantiomers of 11-Hydroxy- and 10,11-Dihydroxy-N-allylnoraporphine: Synthesis and Affinity for Dopamine Receptors in Rat Brain Tissue,”J. Med. Chem. 34:24-28 (1991).
Neumeyer and Granchelli, “Aporphines. 11. Synthesis and Dopaminergic Activity of Monohydroxyaporphines. Total synthesis of (+,−)-11-Hydroxyaporphine, (+,−)-11-Hydroxynoraporphine, and (+,−)-11-Hydroxy-N-n-propylnoraporphine,”J. Med. Chem. 17:1090-1095 (1974).
Ram and Neumeyer, “Aporphines. 42. Synthesis of (R)-(−)-11-Hydroxyaporphines from Morphine,”J. Org. Chem. 47:4372-4374 (1982).
Ram and Neumeyer, “Synthesis of (R)-1,2,11-Trihydroxy-, (R)-2,11-, and (R)-2,10-Dihydroxyaporphines—Non Naturally Occurring Aporphi

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

R(−)-11-hydroxyaporphine derivatives and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with R(−)-11-hydroxyaporphine derivatives and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and R(−)-11-hydroxyaporphine derivatives and uses thereof will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4309584

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.