Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Patent
1992-10-29
1994-04-05
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
C07F 930, A61K 3113, A61K 31185
Patent
active
053006798
ABSTRACT:
Compounds of the formula I ##STR1## wherein R denotes an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic radical having 2 or more carbon atoms, and wherein one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen or, in the case of R.sup.1 and R.sup.2, is hydroxy, and the remaining one of R.sup.1, R.sup.2 and R.sup.3 is hydrogen, or wherein R denotes methyl, R.sub.1 denotes hydrogen or hydroxy, R.sub.2 denotes an aromatic radical and R.sub.3 represents hydrogen, and their salts have GABA.sub.B -antagonistic properties and can be used as GABA.sub.B -antagonists. They are obtained when in a compound of formula II ##STR2## in which R, R.sup.1, R.sup.2 and R.sup.3 have their previous significances, Z represents --NH.sub.2 and R.sup.4 denotes a hydroxy-protective group R.sup.5 or, when R.sup.1 and R.sup.3 denote hydrogen and R.sup.2 denotes hydrogen or alkyl, denotes an alkali metal or ammonium ion R.sup.6, or Z represents a protected or latent amino group Z.sup.o and R.sup.4 denotes hydrogen or a hydroxy-protective group R.sup.5, any group R.sup.5 or R.sup.6 is replaced by hydrogen, and/or any group Z.sup.o is converted into --NH.sub.2.
REFERENCES:
patent: 2535175 (1950-12-01), Tawney
patent: 3184496 (1965-05-01), Baranaucks et al.
patent: 3374288 (1968-03-01), Lange
patent: 3385822 (1968-03-01), Brown
patent: 3493639 (1970-02-01), Tavs
patent: 3637763 (1972-01-01), Firestone
patent: 3784590 (1974-01-01), Firestone
patent: 3812221 (1974-05-01), Braden et al.
patent: 3970586 (1976-07-01), Schliebs et al.
patent: 4064163 (1977-12-01), Drach et al.
patent: 4160779 (1979-07-01), Maier
patent: 4206156 (1980-06-01), Kamiya et al.
patent: 4308147 (1981-12-01), Sommer et al.
patent: 4322375 (1982-03-01), Maier
patent: 4390690 (1983-06-01), DiGiacomo
patent: 4399287 (1983-08-01), Baillie
patent: 4466913 (1984-08-01), Tsuruoka
patent: 4499027 (1985-02-01), Minowa et al.
patent: 4536355 (1985-08-01), Lee et al.
patent: 4618358 (1986-10-01), Maier
patent: 4656298 (1987-04-01), Dingwall et al.
patent: 4657899 (1987-04-01), Rzeszotarski
patent: 4740322 (1988-04-01), Thottathil
patent: 4772738 (1988-09-01), Dingwall
patent: 4908465 (1990-03-01), Dingwall
patent: 5004826 (1991-04-01), Dingwall
patent: 5013863 (1991-05-01), Baylis et al.
patent: 5051524 (1991-09-01), Baylis et al.
Luzzi et al "GABA-Related Activities of Amine Phosphonic Acids on Guinea Pig Ileum Longitudinal Muscle" vol. 105 (1986) Pharmacology, 183873r p. 65-Chemical Abstract.
Gallagher, et al, "Organophosphorus Intermeidates VI The Acid-Catalysed Reaction of Trialkyl Orthoformates with Phosphinic Acid" Aust. J. Chem. 33:287-94 (1980).
Hosford, et al. "The Lethargic Mouse: A Genetic Model of Absence Epilepsy" Soc. Neuroscience, Annual Meeting, New Orleans, Nov. 10-15, (1991) [Abstract].
Cates, et al. "Phosphorus Analogues of .gamma.-Aminobutyric Acid, A New Class of Anticonvulsants" J. Med Chem 27:654-659 (1984).
Liu, et al. "GABA.sub.b -Medicated Mechanisms in Experimental Absence Seizures" Neurology 41:151 (Supp 1) Abs. 131S (1991).
Kreutkamp, et al. "Carbonyl and Cyanophosphonic Acid Esters" Chemical Abstracts 57:5946g (1962).
Dingwall, "New Carboxyphosphonic and Phosphinic Acid Structures of Technical and Biological Interest" Phosphorus and Sulfur, 18:353-356 (1983).
Rupp, et al, "Herbicidal Methylphosphic Acid Derivatives" Chemical Abstracts 97:72585v (1982).
Seabrook, et al. "Electrophysiological Characterization of Potent Antagonists at Pre- and Postsynaptic GABA.sub.b Receptors on Neurones in Rat Brain Slices" Br. J. Pharmacol. 101:949-957 (1990).
Lloyd, et al. "Upregulation of .gamma.-Aminobutyric Acid (GABA).sub.B Binding Sites in Rat Frontal Cortex: A Common Action of Repeated Administration of Different Classes of Antidepressants and Electroshock" J. Pharmacol. Expt. Therapeutics 235(1): 191-199 (1985).
Baylis Eric K.
Bittiger Helmut
Frostl Wolfgang
Hall Roger G.
Maier Ludwig
Ciba-Geigy Corporation
Evans Joseph E.
Fishman Irving M.
Kaiser Karen G.
LandOfFree
Substituted propane-phosphinic acid 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 Substituted propane-phosphinic acid compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted propane-phosphinic acid compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-512653