Cyclic amino acids and derivatives thereof useful as...

Details Cyclic amino acids and derivatives thereof useful as... Cyclic amino acids and derivatives thereof useful as...

2005-07-26

2005-07-26

Zucker, Paul A. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C562S505000

Reexamination Certificate

active

06921835

ABSTRACT:
The invention is a novel series of cyclic amino acids which are useful in the treatment of epilepsy, faintness attacks, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), and inflammation, especially arthritis. A pharmaceutical composition containing a compound of the invention as well as methods of preparing the compounds and novel intermediates useful in the preparation of the final compounds are included.

REFERENCES:
patent: 4024175 (1977-05-01), Satzinger et al.
patent: 4087544 (1978-05-01), Satzinger et al.
patent: 4152326 (1979-05-01), Hartenstein et al.
patent: 5025035 (1991-06-01), Wallace
patent: 5068413 (1991-11-01), Steiner et al.
patent: 5084479 (1992-01-01), Woodruff
patent: 5132451 (1992-07-01), Jennings et al.
patent: 5210315 (1993-05-01), Saito et al.
patent: 5319135 (1994-06-01), Jennings et al.
patent: 5362883 (1994-11-01), Jennings et al.
patent: 5510381 (1996-04-01), Pande
patent: 5631291 (1997-05-01), Mittendorf et al.
patent: 1085420 (1980-09-01), None
patent: 0458751 (1991-11-01), None
patent: 9307111 (1993-04-01), None
patent: 9519337 (1995-07-01), None
patent: 9603122 (1996-02-01), None
patent: WO 97/33858 (1997-09-01), None
Gee et al., “The Novel Anticonvulsant Drug, Gabapentin (Neurontin), Binds to the alpha2delta Subunit of a Calcium Channel”, The Journal of Biological Chemistry, vol. 271, No. 10, 1996, pp. 5768-5776.
Su et al., “Transport of Gabapentin, a y-Amino Acid Drug, by System L alpha-Amino Acid Transporters: A Comparative Study in Astrocytes, Synaptosomes, and CHO Cells”, Journal of Neurochemistry, vol. 64, 1995, pp. 2125-2131.
James and Fischer, “Transport of Neutral Amino Acids at the Blood-Brain Barrier”, Pharmacology, vol. 22, 1981, pp. 1-7.
Suman-Chauhan et al., “Characterisation of [3H]gabapentin binding to a novel site in rat brain: homogenate binding studies”,Eur. J. Pharmacol., Mol. Pharmacol. Sect., vol. 244, No. 3, 1993, pp 293-301.
Mason et al., “Influence of Bond Angle Distortion and α-æ-Delocalization on the Stability and Chemistry of Allylic Cations”,J. Am. Chem. Soc., vol. 95, No. 6, 1973, pp 1849-1859.
Müller and Pautex, “122. Rh(II)-Catalyzed Isomerizations of Cyclopropenes”,Helv. Chim. Acta. vol. 73, No. 5, 1990, pp 1233-1241.
Piva and Comesse, “Tandem Michaël-Wittig Horner Reaction One-Pot Synthesis of Δ-Substituted αβ Unsaturated Esters”,Tetrahedron Lett., vol. 38, No. 41, 1997, pp 7191-7194.
Müller and Gränicher, “33. Structural Effects on the Rh13-Catalyzed Rearrangement of Cyclopropenes”,Helv. Chim. Acta, vol. 76, No. 1, 1993, pp 521-534.
Bunce and Drumright, “Michael Reaction of Nitromethane with ββ-Disubstituted Acrylate Esters”,Org. Prep. Proced. Int., vol. 19, No. 6, 1987, pp 471-475.
Sircar, “Die Herstellung von substituierten Butyrolactamen”,Chem. Zentralbl., vol. 100, No. 1, 1929, p 741.
Urabe et al., “Intramolecular Cyclization of 2,7- or 2,8-Bis-unsaturated Esters Mediated by (β2-Propene)Ti(O-i-Pr)2. Facile Construction of Mono- and Bicyclic Skeletons with Stereoselective Introduction of a Side Chain. A Synthesis of d-Sabinene”,J. Am. Chem. Soc., vol. 119, No. 42, 1997, pp 10014-10027.
Suzuki et al., “A Novel tandem Cyclization of 2,7- or 2,8-Bis-Unsaturated Esters Mediated by ç2-Propene)TiX2(X=Cl or O-i-Pr). A Facile Construction of Bicyclo[3.3.0]octane, -[4.3.0]nonane, and—[3.1.0]hexane Skeletons”,J. Am. Chem. Soc., vol. 118, No. 36, 1996, pp 8729-8730.
Hiouni and Duhamel, “2,2-Di(ethoxy)vinyllithium: Reactions with Carbonyl Compounds”,Tetrahedron Lett., vol. 37, No. 31, 1996, pp 5507-5510.
de Meijere et al., “Unprecendented Addition of Dialkoxycarbenes to Tetrasubstituted Alkenes: Bicyclopropylidene and 2-Chlorocyclopropylideneacetate”,Liebigs Ann., vol. 4, 1996, pp 601-612.
Müller and Gränicher, “11. Selectivity in Rhodium(II)-Catalyzed Rearangements of Cycloprop-2-ene-1-carboxylates”,Helv. Chim. Acta, vol. 78, No. 1, 1995, pp 129-144.
Gil and Fiaud, “Selectivities in the palladium-catalyzed synthesis of dimethyl [2-(3-substituted cyclobutylidene)ethyl]malonate”,Bull. Soc. Chim. Fr., vol. 131, No. 5, 1994, pp 584-589.
Narasaka et al., “Kinetic Resolution of a-Substituted Ketones by Wittig Reaction using a Chiral Tricyclic Phosphonate”,J. Chem. Soc., Chem. Commun., vol. 2, 1993, pp 102-104.
Fiaud et al., “Kinetic Resolution of 3-tButyl and 3-Phenyl Cyclobutylidenethanols through Lipase-catalyzed Acylation with Succinic Anhydride”,Tetrahedron Lett., vol. 33, No. 46, 1992, pp 6967-6970.
Sugahara et al., “Total Synthesis of (+)-Polyzonimine”,J. Chem. Soc., Chem. Commun., vol. 4, 1984, pp 214-215.
Ibuka and Minakata, “a- and Γ-Substituted reactions of cyclic Γ-acetoxy-a,β-unsaturated esters with a novel reagent BuCu-A1C13”,Synth. Commun, vol. 10, No. 2, 1980, pp 119-125.
Gajewski and Burka, “Alkyl Shifts in Thermolysea. VII. Stereochemistry and Kinetics of the Carbethoxyspiropentane to Carbethoxymethylenecyclobutane Rearrangement. Evidence for Concertion and an Intermediate”,J. Am. Chem. Soc., vol. 94, No. 25, 1972, pp 8865-8875.
Gajewski and Burka, “Alkyl Shifts in Thermolyses. IV. Carbethoxyspiropentane-Carbethoxymethylenecyclobutane Isomerization. Evidence for Orbital Symmetry Control and an Intermediate”,J. Am. Chem. Soc., vol. 94, No. 7, 1972, pp 2554-2556.
Erickson, “Reaction of 1-Bromomethylene-2,2-dimethylcyclobutane with Potassiumtert-Butoxide”,J. Org. Chem., vol. 36, No. 8, 1971, pp 1031-1036.
Jorgenson and Patumtevapibal, “Ring size and conformational effects of photodeconjugation of cycloalkylidene esters”,Tetrahedron Lett., vol. 7, 1970, pp 489-492.
Kon et al., “361. The Chemistry of the Three-carbon System. Part XXIX. Tautomerism of Unsaturated Esters.”,J. Chem. Soc., 1932, pp 2454-2459.
Winternitz et al., “No. 31. Syntheses de substances polycycliques (VI. memoire). Acides phenylcyclopentylacetiques”,Bull. Soc. Chim. Fr., 1953, pp 190-195.
Derwent abstract, DT 2543-821, Godecke AG.
Derwent abstract, DT 2626-467, Godecke AG.
Derwent abstract, EP 414 263 A, Godecke AG.

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