Compounds

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

Reexamination Certificate

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C514S338000

Reexamination Certificate

active

06875872

ABSTRACT:
The novel optically pure compounds Na+, Mg2+, Li+, K+, Ca2+and N+(R)4salts of (+)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole or (−)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, in particular sodium and magnesium salt form thereof, where R is an alkyl with 1-4 carbon atoms, processes for the preparation thereof and pharmaceutical preparations containing the compounds as active ingredients, as well as the use of the compounds in pharmaceutical preparations and intermediates obtained by preparing the compounds.

REFERENCES:
patent: 4636499 (1987-01-01), Brandstrom et al.
patent: 4738974 (1988-04-01), Brändström
patent: 4786505 (1988-11-01), Lovgren et al.
patent: 4853230 (1989-08-01), Lovgren et al.
patent: 5045321 (1991-09-01), Makino et al.
patent: 5690960 (1997-11-01), Bengtsson et al.
patent: 5714504 (1998-02-01), Lindberg et al.
patent: 5817338 (1998-10-01), Bergstrand et al.
patent: 5877192 (1999-03-01), Lindberg et al.
patent: 5888535 (1999-03-01), Gray
patent: 5900424 (1999-05-01), Källström et al.
patent: 6214464 (2001-04-01), Huston et al.
patent: 4035455 (1990-11-01), None
patent: 4035455 (1992-05-01), None
patent: 40 35 455 (1997-05-01), None
patent: 0005129 (1981-04-01), None
patent: 0 124 495 (1984-11-01), None
patent: 01 662 87 (1986-01-01), None
patent: 0124495 (1987-01-01), None
patent: 6247983 (1987-04-01), None
patent: 0365947 (1990-05-01), None
patent: 0 652 872 (1995-05-01), None
patent: 0 005 129 (1999-10-01), None
patent: WO 8803921 (1988-06-01), None
patent: 9222284 (1992-12-01), None
patent: 9427988 (1994-12-01), None
patent: 9501783 (1995-01-01), None
patent: 9501977 (1995-01-01), None
patent: 9601623 (1996-01-01), None
patent: 9602535 (1996-02-01), None
Brandstrom “Omeprazole salts” CA 102:137795 (1985).*
Erlandsson et al “Resolution of th eenantiomers of omeprazole . . . ” CA 114:74595 (1991).*
Kohl et al. “Enantiomerically pure . . . ” CA 117:90285 (1992).*
Brandstrom “omeprazole salts” CA 102:137795 (1985).*
Kaellstroem et al. “Preparation of magnesium omeprazole in a crystalline form”, CA122:196964 (1995).*
Lindberg et al. “Preparation of optically pure omeprazole salts” CA 128:154082 (1998).*
Seminars on Organic synthesis vol. 18, 1958 by Japanese Chemical Society.*
Deutsche Apothekerzeitung No. 24 pp. 84-85, 1976.*
Written Decision of the Opposition Panel of the European Patent Office, in the matter of EP 0 652 872, dated Feb. 26, 2004.
Tillet, J.G., et al., “Nucleophilic Substitution as Tricoordinate Sulfur”, Chemical Reviews, 1976, vol. 76, No. 6.
J. March, Advanced Organic Chemistry, 4thedition (1992), John Wiley & Sons, pp. 100, 120, 121, 378 and 379.
A. Pilbrant and C. Cederberg, “Development of an oral formulation of omeprazole”, Scandinavian Journal of Gastroenterology, vol. 20, Supplement 108 (1985) , pp. 113-120.
Beyer Walter, Lehrbuch der Organischen Chemie [Textbook of organic chemistry], 22ndedition (1991), S. Hirzel Verlag, Stuttgart, pp. 735-736.
H.J. Federsel, “Chiral Arzneimittel”, Chemie in unserer Zeit (1993)/No. 2, VCH Vertragsgesellschaft mbH, pp. 78-87.
D. Enders and R.W. Hoffmann, “Asymmetrische Synthese”, Chemie in unserer Zeit (1985)/No. 6, VCH Vertragsgesellschaft mbH, pp. 177-190.
Clinical studies A and B by Astra Hässle AB, introduced into the grant proceedings.
Methoden der Organischen Chemie (Houben Weyl) [Methods of organic chemistry, Houben Weyl], vol. I/1, 1958, chapter “Crystallization”, pp. 345-389.
P. Lindberg et al., “Omeprazole: The First Proton Pump Inhibitor”, Medicinal Research Reviews, vol. 10, No. 1, 1-54 (1990).
P. Erlandsson et al., “Resolution of the enantiomers of omeprazole and some of its analogues by liquid chromatography on a trisphenylcarbamoylcellulose-based stationary phase: The effect of the enantiomers of omeprazole on gastric glands”, Journal of Chromatography 532 (1990) 305-319.
W. Forth et al., “Allgemeine und spezielle Pharmakologie und Toxikologie”. [General and special pharmacology and toxicology], Wissenschaftsverlag, 6thedition 1992, pp. 33, 34, 55-57, 70, 472 and 473.
M. Eichelbaum et al., Effects of Verapamil on P-R-Intervals in Relation to Verapamil Plasma Levels Following Single i.v. and Oral Administration and During Chronic Treatment, Klinische Wochenschrift 58, 919-925 (1980).
P. Dayer et al., Interindividual Variation of Beta-Adrenoceptor Blocking Drugs, Plasma Concentration and Effect: Influence of Genetic Status on Behavior of Atenolol, Bopindolol and Metroprolol, Eur. J. Clin. Pharmacol. (1985) 28(2): 149-153.
“The result of a recent study comparing all PPI's currently on the market”.
P. Fresenius, “Organic Chemical Nomenclature, Introduction to the Basic Principles”, Ellis Horwood Limited, p. 127.
S. Yamada and S. Narita, “Synthesis and Isomerization of Optical Active 2[6,7,8,9-tetrahydro-5H-cyclophepta[b]pyridin-9-yl)sulfinyl]-1H-benzimidazole Analogs” Chem. Pharm. Bull 42(8), 1679-1681 (1994).
Jacobus et al., “Racemization and Cleavage of Sulfoxides by Methyllithium”, Journal of the American Chemical Society 89:20; pp. 5228-5234 (1967).
Tanaka, M. et al.., “Direct Determination of Pantoprazole Enantiomers in Human Serum by Reversed-Phase High-Performance Liquid Chromatography Using a Cellulose-Based Chiral Stationary Phase and Column-Switching System as a Sample Cleanup Procedure”, Analytical Chemistry, vol. 68, No. 9, 1513-1516 (1996).
Cass et al., “Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography”, J. Chromatography B, 766 (2001) 153-160.
Comprehensive Medical Chemistry, Pergamon Press (1990), vol. 2, pp. 193-205.
Renberg et al., “Identification of Two Main Urinary Metabolites of [14C]Omeprazole in Humans”, Drug Metabolism and Disposition, vol. 17, (1989) 69-76.
Abstract #35, Synthesis and Biological Activity of Enantiomers of H+K+-ATPase Inhibiting 2-(2-Pyridyl-methyl) sulphinyl-benzimidazoles (PSBs) from Program of the Fourth International Symposium of Chiral Discrimination, Sep. 19-22, 1993, Montreal, Quebec, Canada.
In the matter of EP 0 652 872, Notice of Opposition and Opposition Brief in the name of Ratiopharm GmbH, dated Jul. 18, 2001.
In the matter of EP 0 652 872, Response to the Opposition Brief by AstraZeneca AB, dated Mar. 27, 2002.
In the matter of EP 0 652 872, third party observations, dated May 30, 2002.
In the matter of EP 0 652 872, opponent submission, dated Jan. 22, 2003.
In the matter of EP 0 652 872, summons to oral proceedings, dated Jul. 15, 2003.
In the matter of EP 0 652 872, opponent submission, dated Oct. 21/23, 2003.
In the matter of EP 0 652 872, patentee submission, dated Oct. 24, 2003.
EPO Notice upholding claims 1-15 of EP 0 652 872, dated Nov. 25, 2003.
In the matter of EP 0 652 872, written decision from EPO, “when available”.
CA 117:90292, Palomo et al. (1992).
Erlandson et al. “Resolution of the enatiomers of omeprazole . . . ” J. Chromatography (1990) 532:305-319.
Chang et al. 1995 “Interphenotye differences . . . ” Brit. J. Clinical Pharmacology 39:511-518.
Rost et al. (1994) “Accelerated caffeine metabolism after omeprazole . . . ” 55:402-411.
Rost et al. (1992) “Increase of cytochrane P4501A2 activity . . . ” 52; 170-180.
Marle et al. “Determination of binding affinity of enantiomers . . . ” J>Chromatography (1988) 456:323-33.
Cairns, et al. “Enantioselective HPLC determination . . . ” Journal of Chromatography 8,666 (1995) 323-328.
Yamada et al. “Synthesis and isomerization of optical active . . . ” Chem. Pharm. Bull. 42 (8) (1994) 1679-1681.
K. Miwa et al. Jpn. Pharmacol. Ther. “Proton pump inhibitor in rats, mice and dogs” 18

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