Azepine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

540521, 540522, 540523, 514220, 514221, C07D22316, C07D22332, A61K 3155

Patent

active

057081689

ABSTRACT:
Disclosed are methods of preparing azepines by a multistep synthesis including a Diels-Alder reaction. Also disclosed are methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating or preventing opiate tolerance are disclosed by administering to an animal in need of such treatment an azepine which has high binding to the NMDA glycine site.

REFERENCES:
patent: 5254683 (1993-10-01), Chapdelaine et al.
patent: 5446039 (1995-08-01), Chapdelaine et al.
patent: 5492905 (1996-02-01), Harris et al.
Alberola et al., "Derivados de Ciclopentanohidrofenantreno. La reduccion del cis,sin-1,4,4a,4b,5,6,7,8,10,10a-dodecahidro-2-metoxi-1,4-dioxofenantr eno," Anales de Fisica y Quimica 62:691-698 (1966).
Birchall, G.R., and Rees, A.H., "Some Derivatives of 1-Benzazepine. Part II," Can. J. Chem. 52:610-615 (1974).
Bohlmann, et al., "Uber die Regioselektivitat von Diensynthesen substituierter Chinone," Chem. Ber. 110:2028-2045 (1977).
Boisvert, L., and Brassard, P., "Regiospecific Additions of Some Simple Dienes to Haloquinones," Tetrahedron Letts. 24(24):2453-2456 (1983).
Donaldson, et al., "Model Studies Toward the Synthesis of Leukotrienes: Hetero-Diels-Alder Reactivity of Tricarbonyl(diene)iron Complexes," J. Org. Chem. 56(14):4563-4566 (1991).
Giles, R.G.F., and Roos, G.H.P., "Regiospecific Addition of Methoxycyclohexa-1,3-Dienes to 2-Methoxy-1,4-Benzoquinone. Application to the Synthesis of 3-Methoxy-7-Methyljuglone and .alpha.-Caryopterone," Tetrahedron Letts. 47:4159-4160 (1975).
Giles, R.G.F., and Roos, G.H.P., "Syntheses of the Naturally Occurring Dihydro-.alpha.-caryopterone, and O-Methyldihydro-.alpha.-caryopterone," J. Chem. Soc. Perkin Trans. 1:1632-1635 (1976).
Giles, R.G.F., and Roos, G.H.P., "Syntheses of Substituted 1,4-Naphthoquinones by Diels-Alder Addition of Methoxycyclohexadienes to Substituted 1,4-Benzoquinones," J. Chem. Soc. Perkin Trans. 1:2057-2060 (1976).
Horn, et al., "Orthogonal Connection of Acenes via Two-Fold Diels-Alder Reactions," Tetrahedron Letts. 34(37):5889-5892 (1993).
Hughes, et al., "Azatropolones. Part II. The Schmidt Reaction of 2-Methoxy-5-methylbenzoquinone," Can. J. Chem. 52:3327-3330 (1974).
Kamabuchi, et al., "Synthesis and Cycloaddition of 2-(Dialkoxyboryl)-1,3-butadiene," Tetrahedron Letts. 34(30):4827-4828 (1993).
Mikami et al., "Chiral Titanium Complex-Catalyzed Diels-Alder Reaction: A Practical Route to Anthracycline Intermediates," Tetrahedron: Asymmetry 2(7):643-646 (1991). Reaction of Strained Cage Ketones to Triquinane Skeletons: Kinetic Evidence for a Large Acceleration of the Reaction Owing to Stereoelectronic Requirement," Chem. Pharm. Bull. 32(11):4593-4599 (1984).
Reich, et al., "Synthesis of 2,3-Disubstituted 1,3-Butadienes from Organotin Precursors and Butadienyllithium Reagents. Diels-Alder Reactivity," J. Am. Chem. Soc. 115(15):6625-6635 (1993).
Sha, C.-K., and Yang, J.-F., "Total Syntheses of Ellipticine Alkaloids and Their Amino Analogues," Tetrahedron 48(48):10645-10654 (1992).
Swartz, et al., "Competitive Antagonism of Glutamate Receptor Channels by Substituted Benzazepines in Cultured Cortical Neurons," Molec. Pharmacol. 41:1130-1141 (1992). Heterocyclic Chem. 26:793-795 (May-Jun. 1989).
A copy of the International Search Report for the corresponding PCT Application, International Application No. PCT/US95/14572.

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

Azepine compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

     

Profile ID: LFUS-PAI-O-327969

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