Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2008-03-04
2008-03-04
Habte, Kahsay (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C544S094000
Reexamination Certificate
active
07339057
ABSTRACT:
A method for preparing a fused oxazinone is disclosed in which (1) a carboxylic acid is contacted with a sulfonyl chloride in the presence of an optionally substituted pyridine compound, the nominal mole ratio of sulfonyl chloride to carboxylic acid being from about 0.75 to 1.5; (2) the mixture prepared in (1) is contacted with an ortho-amino aromatic carboxylic acid in the presence of an optionally substituted pyridine compound, the nominal mole ratio of the ortho-amino aromatic carboxylic acid to carboxylic acid charged in (1) being from about 0.8 to 1.2; and (3) additional sulfonyl chloride is added to the mixture prepared in (2), the nominal mole ratio of additional sulfonyl chloride added in (3) to carboxylic acid charged in (1) being at least about 0.5. Also disclosed is a method for preparing a compound of Formula III, using a compound of Formula 1a that is characterized by preparing the fused oxazinone of Formula 1a by the method above, using a compound of the formula LS(O)2Cl as the sulfonyl chloride, a compound of Formula 2′ as the carboxylic acid, and a compound of Formula 5′ as the ortho-amino aromatic carboxylic acid (FORMULA 1a) (FORMULA III) (FORMULA 2′) (FORMULA 5′) wherein L, X, Y and R1through R9are as defined in the disclosure
REFERENCES:
patent: 2004/0171649 (2004-09-01), Annis et al.
patent: 2004/0198984 (2004-10-01), Lahm et al.
patent: 2004/0198987 (2004-10-01), Freudenberger et al.
patent: 2004/0209923 (2004-10-01), Berger et al.
patent: 2005/0075372 (2005-04-01), Lahm et al.
patent: WO 01/70671 (2001-09-01), None
patent: WO 03/015518 (2003-02-01), None
patent: WO 03/015519 (2003-02-01), None
patent: WO 03/016282 (2003-02-01), None
patent: WO 03/016283 (2003-02-01), None
patent: WO 03/024222 (2003-03-01), None
patent: WO 04/011453 (2004-02-01), None
G.M. Coppola, The Chemistry of 4H-3,1-Benzoxazin-4-Ones, J. Heterocyclic Chemistry, 1999, pp. 563-588, vol. 36.
Jakobsen et. al., Inhibitors of the Tissue Factor/Factor VIIA-Induced Coagulation: Synthesis and In Vitro Evaluation of Novel 2-Aryl Substituted Pyrido[3,4-D]-, Pyrido [2,3-D][1,3], Pyrazino[2,3-D][1,3]-, Pyrimido [4,5-D][1,3]-, Thieno [3,2-D][1,3]-, and Thieno [2,3-D][1,3 ]-Oxazin-4-Ones, Biorganic and Medicinal Chemistry, 2000, pp. 2803-2812, vol. 8.
Jakobsen et al., Inhibitors of the Tissue Factor/Factor VIIA-Induced Coagulation: Synthesis and In Vitro Evaluation of Novel Specific 2-Aryl Substituted 4H-3,1-Benzoxazin-4-Ones, Biorganic and Medicinal Chemistry, pp. 2095-2103, vol. 8, (2000).
D.V. Ramana et. al., Facile Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-Ones, Org. Prep. Proced. Int., 1993, pp. 588-590, 1993, vol. 25.
E.I. Du Pont de Nemours and Company
Habte Kahsay
LandOfFree
Method for preparing fused oxazinones from ortho-amino... 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 fused oxazinones from ortho-amino..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for preparing fused oxazinones from ortho-amino... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2816131