Synthesis of benzonitriles from substituted benzoic acid

Details Synthesis of benzonitriles from substituted benzoic acid Synthesis of benzonitriles from substituted benzoic acid

2005-04-05

2005-04-05

Dentz, Bernard (Department: 1625)

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

Organic compounds

Nitriles

C558S423000, C548S237000

Reexamination Certificate

active

06875882

ABSTRACT:
There is a significant demand for organic nitriles, based on their versatility in reactions. Compounds prepared from nitriles have properties including superoxide inhibition, ferrielectric liquid crystal dopant, antipicornaviral agents, anti-inflammatory agents, anti-asthma agents, and fibringoen antagonists. The present invention discloses a facile synthesis for 2,4-dihydroxybenzonitrile, and ethers and diethers thereof, from 2,4-dihydroxybenzoic acid. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, 2,4-dihydroxybenzonitrile is condensed with (S)-2-methylcysteine.

REFERENCES:
patent: 4406905 (1983-09-01), Zähner et al.
patent: 5554753 (1996-09-01), O'Donnell et al.
patent: 5840739 (1998-11-01), Bergeron, Jr.
patent: 5872259 (1999-02-01), Reuter
patent: 5929232 (1999-07-01), Jacobsen et al.
patent: 6083966 (2000-07-01), Bergeron, Jr.
patent: 6159983 (2000-12-01), Bergeron, Jr.
patent: 6383233 (2002-05-01), Reuter
patent: 6428583 (2002-08-01), Reuter
patent: 6521652 (2003-02-01), Bergeron
patent: 6525080 (2003-02-01), Bergeron
patent: 6559315 (2003-05-01), Bergeron
patent: 20030088105 (2003-05-01), Krich et al.
patent: 20030220504 (2003-11-01), Chorghade et al.
patent: 20030225287 (2003-12-01), Chorghade et al.
patent: 20030229231 (2003-12-01), Chorghade et al.
patent: 20030236404 (2003-12-01), Gimi et al.
patent: 20030236426 (2003-12-01), Chorghade et al.
patent: 20030236434 (2003-12-01), Gimi et al.
patent: 20030236435 (2003-12-01), Gimi et al.
patent: 20040006224 (2004-01-01), Chorghade et al.
patent: 20040024224 (2004-02-01), Chorghade et al.
patent: 20040082796 (2004-04-01), Chorghade et al.
patent: 2020866 (1971-11-01), None
patent: 30 02 989 (1981-07-01), None
patent: 1 302 467 (2003-04-01), None
patent: 1 292 170 (1972-10-01), None
patent: WO 9411367 (1994-05-01), None
patent: WO 9736885 (1997-10-01), None
patent: WO 0001670 (2000-01-01), None
patent: WO 0012493 (2000-03-01), None
patent: WO 0016763 (2000-03-01), None
patent: WO 0151477 (2001-07-01), None
Bergeron, R., et al., “Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators,”J. Med. Chem., 42:95-108 (1999).
Bergeron, R. et al., “Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators,”J. Med. Chem., 39:1575-1581 (1996).
Bergeron, R. et al., “Evaluation of Desferrithiocin and Its Synthetic Analogues as Orally Effective Iron Chelators,”J. Med. Chem., 34:2072-2078 (1991).
Bergeron, R. et al., “Evaluation of the Desferrithiocin Pharmacophore as a Vector for Hydroxamates,”J. Med. Chem., 42:2881-2886 (1999).
Bergeron, R. et al., “An Investigation of Desferrithiocin Metabolism,”J. Med. Chem., 37:2889-2895 (1994).
Bergeron, R. et al., “A Comparative Study of the Iron-Clearing Properties of Desferrithiocin Analogues with Desferrioxamine B in aCebusMonkey Model,”Blood, 81(8):2166-2173 (1993).
Bergeron, R. et al., “Pharmacokinetics of Orally Administered Desferrithiocin Analogs inCebus ApellaPrimates,”Drug Metabolism and Disposition, 27(12):1496-1498 (1999).
“Aliphatic Nucleophilic Substitution,” InAdvanced Organic Chemistry, by Jerry March (Wiley Interscience), Ch. 10, pp. 433-434 (1992).
“Eliminations,” InAdvanced Organic Chemistry, by Jerry March (Wiley Interscience), Ch. 17, pp. 1012-1014 (1992).
Mulqueen, G. C., et al., “Synthesis of the Thiazoline-based Siderophore (S)-Desferrithiocin,”Tetrahedron, 49(24):5359-5364 (1993).
O'Donnell, M.J., et al., “α-Methyl Amino Acids by Catalytic Phase-Transfer Aklylations,”Tetrahedron Letters, 23(41):4259-4262 (1982).
House, Herbert O., “Modern Synthetic Reactions,” 2ndedition, W. A. Benjamin, Inc., London, pp. 546-547 (1972).
Bergeron, R.J., et al., “The Desferrithiocin Pharmacophore,”J. Med. Chem., 37: 1411-1417 (1994).
Bergeron, R.J., et al., “Effects of C-4 Stereochemistry and C-4′ Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues,”J. Med. Chem., 42: 2432-2440 (1999).

Affiliated with

Also associated with

Rating

Synthesis of benzonitriles from substituted benzoic acid does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of benzonitriles from substituted benzoic acid, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of benzonitriles from substituted benzoic acid will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3402490