Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1,

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C07D48704

Patent

active

056211147

ABSTRACT:
There are described compounds of the formula ##STR1## where (a) X is O or S;

REFERENCES:
patent: 2678899 (1954-05-01), Miller et al.
patent: 2909530 (1959-10-01), Rudner et al.
patent: 3457268 (1969-07-01), Frey et al.
patent: 3547945 (1970-12-01), Frey et al.
patent: 3547947 (1970-12-01), Frey et al.
patent: 3551450 (1970-12-01), Frey et al.
patent: 3897451 (1975-07-01), Gassman
patent: 4278667 (1981-07-01), Madison et al.
patent: 4680172 (1987-07-01), Leeson
patent: 4760083 (1988-07-01), Myers et al.
patent: 4765985 (1988-08-01), Leeson
patent: 4791107 (1988-12-01), Hamer et al.
patent: 4831155 (1989-05-01), Brufani et al.
patent: 4857648 (1989-08-01), Broger et al.
patent: 4900748 (1990-02-01), Brossi et al.
patent: 4914102 (1990-04-01), Glamkowski et al.
patent: 4937341 (1990-06-01), Glamkowski et al.
patent: 4971992 (1990-11-01), Glamkowski et al.
patent: 4978673 (1990-12-01), Meroni et al.
patent: 4983616 (1991-01-01), O'Malley et al.
patent: 5077289 (1991-12-01), Glamkowski et al.
patent: 5081117 (1992-01-01), Glamkowski et al.
patent: 5091541 (1992-02-01), O'Malley et al.
patent: 5171750 (1992-12-01), Brossi et al.
patent: 5173497 (1992-12-01), Flanagan
patent: 5177101 (1993-01-01), Glamkowski et al.
patent: 5187165 (1993-02-01), Hamer et al.
patent: 5206260 (1993-04-01), Hichens et al.
patent: 5216017 (1993-06-01), Allen et al.
patent: 5260452 (1993-11-01), Glamkowski et al.
Atack et al., Comparative Inhibitory Effects of Various Physostigmine Analogs Against Acetyl- and Butyrylcholinesterases, J. Pharmacol. Exp. Therapeutics, 249(1): 194-202 (1989).
Bartolini et al., Eseroline: A New Antinociceptive Agent Derived from Physostigmine with Opiate Receptor Agonist Properties. Experimental In Vivo and In Vitro Studies on Cats and Rodents, Neurosci. Lett., 25: 179-183 (1981).
Berge et al., Pharmaceutical Salts, J. Pharm. Sci., 66: 1-19 (1977).
Bores et al., HP 290: A Potent, Orally Active Cholinesterase Inhibitor for the Treatment of Alzheimer's Disease, Soc. Neurosci. Abstr. 17(1): 699 (1991).
Brossi et al., Chemical Abstracts 109: 740 (1988), Abstract Nos. 190632x and 190633y.
Brzostowska et al., Phenylcarbamates of (-)-Eseroline, (-)-N.sup.1 -Noreseroline and (-)-Physovenol: Selective Inhibitors of Acetyl and, or Butyrylcholinesterase, Med. Chem. Res., 2: 238-246 (1992).
Brufani et al., Anticholinesterase Activity of a New Carbamate, Heptylphysostigmine, in View of Its Use in Patients with Alzheimer-type Dementia, Eur. J. Biochem., 157:115-120 (1986).
Chemical Abstracts, Section 25, Benzene, Its Derivatives, And Condensed Benzenoid Compounds, 108(25): 535-543 (1988).
Colvin, Silicon in Organic Synthesis, Butterworths Monographs in Chemistry and Chemical Engineering, Chapter 10, Butterworths (London) (1981).
Ellis et al., Studies on Physostigmine and Related Substances.sup.1, III. Breakdown Products of Physostigmine; Their Inhibitory Effect on Cholinesterase and Their Pharmacological Action, J. Pharm. Exp. Ther., 79: 309-319 (1943).
Galli et al., Inhibition of [.sup.3 H]naloxone Binding in Homogenates of Rat Brain by Eseroline, a Drug, with Analgesic Activity, Related to Physostigmine, J. Pharm. Pharmacol. (Communications), 31: 784-786 (1979).
Giacobini et al., Pharmacokinetics and Pharmacodynamics of Physostigmine After Intravenous Administration in Beagle Dogs, Neuropharmacology, 831-836 (1987).
Gorman et al., Comparison of the Cardiovascular Effects of HP 290 and Heptylstigmine (HEP), New Cholinesterase Inhibitors in the Treatment of Alzheimer's Disease, Meeting Abstract No. 7210, FASEB Annual Meeting, Atlanta, GA, Apr., 1991.
Gould, Salt Selection for Basic Drugs, Int. J. Pharmaceutics, 33: 201-217 (1986).
Hamer et al., HP 290: A New, Potent Cholinesterase Inhibitor for the Treatment of Alzheimer's Disease, Meeting Abstract No. 74, American Chemical Society Division of Medicinal Chemistry, Atlanta, GA, Apr., 1991.
Hamer et al., Chemical Abstracts 108: 596 (1988), Abstract No. 221937m.
Howard et al., HP 290: A Potential Alzheimer's Therapeutic Agent with Reduced Cardiovascular Liability, Soc. Neurosci. Abstr., 17(1): 699 (1991).
Isaksson and Kissinger, Metabolism of Physostigmine in Mouse Liver Microsomal Incubations Studied by Liquid Chromatography with Dual-Electrode Amperometric Detection, J. Chromatography, 419: 165-175 (1987).
Julian and Pikl, Studies in the Indole Series. IV. The Synthesis of d,1-Eserethole, J. Am. Chem. Soc., 57: 563-566 (1935).
Julian and Pikl, Studies in the Indole Series, V. The Complete Synthesis of Physostygmine (Eserine), J. Am. Chem. Soc., 57: 755-757 (1935).
King and Robinson, Experiments on the Synthesis of Physostigmine (Eserine). Part XI. The Later Phases of the Synthetical Investigations, J. Chem. Soc., 755-759 (1935).
Merck Index, The, Eleventh Edition (1989), pp. 1172-1173.
New Candidates for Treating Alzheimer's, C & E News, Apr. 29, 1991, p. 28.
Polonovski, Bull. Chem. Soc. France, 19: 47-59 (1916).
Polonovski, Chemical Abstracts, 10: 1329 (1916).
Robinson, Alkaloids of the Calabar Bean, in: The Alkaloids, Manske, ed., Chapter 5, pp. 383-400 (1968).
Robinson, Synthesis of d1-Eseramine.sup.1, Chem. & Ind., Jan. 9, 1985, pp. 87-88.
Robinson and Robinson, The Anti-Acetylcholinesterase Activities of the Alkaloids of Physostigma veneosum Seeds, J. Pharm. Pharmac., 20(Suppl.): 213S-217S (1968).
Roth and Fenner, in: Pharmazeutische Chemie III: Arzneistoffe Struktur-Bioreaktivitat-Wirkungsbezogene Eigenschaften, Verlag (Stuttgart), 1988, pp. 390-395.
Salway, Researches on the Constitution of Physostigmine Part I, J. Chem. Soc., 101: 978-989 (1912).
Schonenberger and Brossi, Fragmentation of Optically Active (1-Phenylethyl)--and (1-Naphthylethyl) ureas in Refluxing Alcohols: Easy Preparation of Optically Active Amines of High Optical Purity, Helvetica Chimica Acta, 69: 1486-1497 (1986).
Schonenberger et al., Comparison of (-)-Eseroline with (+)-Eseroline and Hihydroseco Analogues in Antinociceptive Assays: Confirmation of Rubreserine Structure by X-ray Analysis, J. Med. Chem., 29: 2268-2273 (1986).
Schonenberger et al., Preparation of Optically Active Secondary Amines by Thermal Decomposition of (Methylbenzyl)urea Analogs: Absolute Configuration of (+)-and (-)-Mecamylanime, Helvetica Chimica Acta, 69: 283-287 (1986).
Sibi et al., The Directed Ortho Lithiation of O-Aryl Carbamates. An Anionic Equivalent of the Fries Rearrangement, J. Org. Chem., 48: 1935-1937 (1983).
Somani and Khalique, Pharmacokinetics and Pharmacodynamics of Physostigmine in the Rat After Intravenous Administration, Drug Metabolism and Disposition, 15(5): 627-633 (1987).
Somani, Pharmacokinetics and Pharmacodynamics of Physostigmine in the Rat After Oral Administration, Biopharmaceutics & Drug Disposition, 10: 187-203 (1989).
Stern et al., Effects of Oral Physostigmine in the Alzheimer's Disease, Ann. Neurol., 22: 306-310 (1987).
Sumimoto Pharm. Co., Ltd. (Japan), SM-10888: Agent for Cognition Disorders; Acetylcholinesterase Inhibitor, Drugs of the Future, 16(1): 33-36 (1991).
Trommer et al., Thioeserin, das Thioanalogon des Eserine, Arch. Pharm., 309: 631-638 (1976).
Unni and Somani, Hepatic and Muscle Clearance of Physostigmine in the Rat, Drug Metabolism and Disposition, 14(2): 183-289 (1986).
Unni et al., Kinetics of Cholinesterase Inhibition by Eptastigmine in Man, Eur. J. Clin. Pharmacol., 41:83-84 (1991).
Yu et al., Synthesis and Anticholinesterase Activity of (-)-N.sup.1 -Norphysostigmine, (-)-Eseramine, and Other N(1)-Substituted Analogues of (1)-Physostigmine, J. Med. Chem., 31(12): 2297-2300 (1988).
Yu and Erossi, Practical Synthesis of Unnatural (+)-Physostigmine and Carbamate Analogues, Heterocycles, 27(3): 745-750 (1988).

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

Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1, does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1, , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for preparing 1, 2, 3, 3A, 8, 8A-hexahydro-3A, 8 (and 1, will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-361959

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