Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2003-09-29
2008-08-12
Shameem, Golam M (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S452000
Reexamination Certificate
active
07411074
ABSTRACT:
A process for preparing a compound of formula (I) where R4and R5are as defined in the specification; and R6is hydrogen or a protecting group, which process comprises cyclisation of a compound of formula (II) where R4, R5and R6are as defined in relation to formula (I), and R7is nitrogen-protecting group, and removing the group R7—, and thereafter if desired or necessary, removing any protecting group R6to obtain the corresponding carboxylic acid. Novel intermediates and the use of the products in the preparation of pharmaceutical compounds is also described and claimed.
REFERENCES:
patent: 2004/0048878 (2004-03-01), Cai et al.
patent: 2004/0142938 (2004-07-01), Sher et al.
patent: 2004/0220229 (2004-11-01), Bussolotti et al.
patent: 1088824 (2001-04-01), None
patent: 1136071 (2003-03-01), None
patent: 1 340 500 (2003-09-01), None
patent: 2004196702 (2004-07-01), None
patent: 364613 (1972-12-01), None
patent: WO-1994/18196 (1994-08-01), None
patent: WO-01/28993 (2001-04-01), None
patent: WO-2001/28993 (2001-04-01), None
patent: 01/32622 (2001-05-01), None
patent: WO-2002/06246 (2002-01-01), None
patent: WO-2002/20530 (2002-03-01), None
patent: 03/072570 (2003-09-01), None
patent: WO-2003/074484 (2003-09-01), None
patent: WO-2003/074485 (2003-09-01), None
patent: WO-2003/074513 (2003-09-01), None
patent: WO-2003/074517 (2003-09-01), None
patent: WO-2003/074531 (2003-09-01), None
patent: WO-2003/074532 (2003-09-01), None
patent: WO-2003/091213 (2003-11-01), None
patent: 2004/031193 (2004-04-01), None
patent: WO-2004/041780 (2004-05-01), None
patent: WO-2004/058715 (2004-07-01), None
patent: 2004/092158 (2004-10-01), None
patent: WO-2004/113345 (2004-12-01), None
patent: 2005/013975 (2005-02-01), None
patent: 2005/013981 (2005-02-01), None
patent: 2005/018637 (2005-03-01), None
patent: 2005/019172 (2005-03-01), None
patent: 2005/020985 (2005-03-01), None
patent: 2005/020986 (2005-03-01), None
patent: 2005/020987 (2005-03-01), None
Freeman, S., et al., “Effect of Glucose on Rat and Human Liver Glycogen Phosphorylasea Activity and Potency of a Glycogen Phosphoylase Inhibitor,” Diabetes, 52, Supp., 1470-P, A340 (2003).
Turnbull, A., et al., “Pharmacological Inhibition of Glycogen Phosphorylase (GP) Lowers Plasma Glucose in Rat Models of Type 2 Diabetes,” Diabetes, 52, Supp., 1485-P, A343 (2003).
Birch, A., et al., “Novel Thienopyrrole Glycogen Phosphorylase Inhibitors: In Vitro SAR and Crystallographic Studies,” Poster, Cambridge Med Chem Symposium (Sep. 2003).
Hudson, S., et al., “The effect of a glycogen phosphorylase inhibitor upon muscle fatigue in anaesthetised rats,” J. Physiol., 539:52-53 (2002).
Vertigan, H. et al. “Impact of cell glycogen content on modulation of hepatocyte glucose metabolism by pharmacological agents”, EASD Munich (2004).
Bartlett, J. et al. “In Vitro and In Vivo Profile of Gpi688, a Novel, Potent Inhibitor of Glycogen Phosphorylase”, ADA San Diego (2005).
Simpson, I. et al. “Novel Orally Active Amino-indan Inhibitors of Glycogen Phosphorylase”, Cambridge Med Chem Conference, (Sep. 2005). Poster EOM.
Green, A R. et al. “The Glycogenic Action of Protein Targeting to Glycogen in Hepatocytes Involves Multiple Mechanisms Including Phosphorylase Inactivation and Glycogen Synthase Translocation”, J Biol Chem, 279(45), 46474-46482 (2004).
Roberts, P A. et al. “The temporal relationship between glycogen phosphorylase and activation of the pyruvate dehydrogenase complex during adrenaline infusion in resting canine skeletal muscle”, J Physiology-London 545(1), 297-304 (2002).
PCT/GB2003/004217 Search Report Jun. 8, 2004.
Meth-Cohn et al., “The preparation and formylation of 2-acetamidothiophenes,” Synthesis 2:133-135 (1980).
Nakamura, “Construction of heterocyclic compounds by use of alpha-diazaphosphonates: new one-pot syntheses of indoles and isocoumarines,” Organic Letters 4(14)2317-2320 (2002).
Shvedov et al., “2-Aminothieno ′2,3-blpyridine derivatives,” Database CA 'Online! Chemical Abstracts Service Database accession No. 78:159580 XP002266826 (1972).
Sugiyama et al., “Condensed thienopyridines. IV. Synthesis and gastric antisecretory activity of 2,3-dihydro-5H-oxazolothienopyrimidine derivatives,” Chemical & Pharmaceutical Bulletin 37(10):2171-2722 (1989).
Sugiyama et al., “Condensed thienopyrimidines. 5. Studies on the thermal cyclization of various ortho-formylthiophenecarbamates with ethanolamine,” Heterocycles 29(7):1317-1323 (1989).
Adams et al., “4-Amino-4,5-dihydrothiophene-2-carboxylic acid,” J. Org. Chem. 50:2730-2736 (1985).
Binder et al., “Eine einfache herstellungsmethode fur 2-aminothiophene,” Synthesis Communications 4:255-256 (1977).
Binder et al., “Thiopen als strukturelement physiologisch aktiver substanzen, 8. mitt. 1H5H-imidazo[1,2-a]thieno[3,4-d]pyrimidin-2(3H-one,” Arch Pharm. 314:556-564 (1981).
Bjork et al., “Improved syntheses of thieno[2,3-b]- and [3,2-b]-fused naphthyridines,” J. Heterocyclic Chem. 32:751-754 (1995).
Boger et al., “Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity,” J. Am. Chem. Soc. 122:6382-6394 (2000).
Brugier et al., “α-Substitution of β-thienylcarbamates: alkylation, vinylation and Pd-catalyzed coupling reactions,” Tetrahedron 56:2985-2993 (2000).
Brugier et al., “Studies on the reactivity of N-(3-thienyl)carbamates,” J. Chem. Soc., Perkin Trans. 1:37-43 (2001).
Brugier et al., “Synthesis and reactivity of alkyl (4-aminothien-3-yl)carbamates,” Tetrahedron 53(30):10331-10344 (1997).
Brunnett et al., “Heterocyclic amines. IV. Urethan and urea derivatives of 3-aminothiophene (1),” J. Heterocyclic Chem. 5(3):417-418 (1968).
Carroll et al., “Competitive ortho metalation effects: the kinetic and thermodynamic lithiation of 3-(tert-Butoxycarbonyl)amino-4-caromethoxythiopene,” Tetrahedron Letters 38(15):2637-2640 (1997).
Eras et al., “Reactivity of theinopyrroles. synthesis of isomeric nitro and bromothienopyrroles,” J. Heterocyclic Chem. 21:215-217 (1984).
Galvez et al., “Synthesis of isomeric β-haloethylthienopyrroles,” J. heterocyclic Chem. 21, 393-395 (1984).
Galvez et al., “Synthesis of thiophenedicarbonyldiazides and Di-t-butyl thiophendicarbamates,” J. Heterocyclic Chem. 23:1103-1108 (1986).
Jones et al., “The Vilsmeier reaction of fully conjugated carbocycles and heterocycles,” Organic Reactions 49:1-39 (1997).
Kobayashi et al., “Heterocyclic sulfonyl compounds and activated blood coagulation factor X (FXa) inhibitors containing them,” Chemical Abstracts XP002267904 & JP 2001 294572 (2001).
Linda et al., “The mechanism of the Vilsmeier-Haach reaction. Part III. Structural and solvent effects,” J. Chem. Soc. Perkins Trans II, 1610-1612 (1974).
Marques et al., “Toward an understanding of the chemical etiology for DNA minor-groove recognition by polyamides,” Helvetica Chimica acta 85:4485-4517 (2002).
Martin et al., “Nucelar magnetic resonance investigations of carbonium ion intermediates. Part II. Exchange reactions in chloro-iminium salts (Vilsmeier-Haack reagents),” Journal Chem. Soc., Perkins Trans II 642-646 (1974).
Martin et al., “Recherches sur la reaction de vilsmeier-haack etude du mecanisme de formation du complexe par des mesures cinetiques en resonance magnetique nucleaire,” Tetrahedron Letters 58:5061-5064 (1970).
Meth-Cohn et al., “A versatile new synthesis of quinolines and related fused pyridines. Part II.,” Tetrahedron Letters 33:3111-3114 (1979).
Meth-Cohn et al., &
Murray Paul
Parker Jeremy Stephen
Schofield Paul
Stocker Andrew
AstraZeneca AB
Shameem Golam M
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