Antiviral azaindole derivatives

Details Antiviral azaindole derivatives Antiviral azaindole derivatives

2005-05-31

2005-05-31

Bernhardt, Emily (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06900323

ABSTRACT:
The invention comprises novel azaindole intermediate compounds useful in the preparation of compounds of the class of azaindole piperazine diamide derivatives, composition thereof and their use as anti-viral agents, and particularly for treating HIV infection.

REFERENCES:
patent: 5023265 (1991-06-01), Scherlock et al.
patent: 5124327 (1992-06-01), Greenlee et al.
patent: 5413999 (1995-05-01), Vacca et al.
patent: 5424329 (1995-06-01), Boschelli et al.
patent: 5681959 (1997-10-01), Bishop et al.
patent: 5811432 (1998-09-01), Marfat et al.
patent: 2003/0069266 (2003-04-01), Wang et al.
patent: 2003/0236277 (2003-12-01), Kadow et al.
patent: 2004/0006090 (2004-01-01), Kadow et al.
patent: 2004/0063744 (2004-04-01), Wang et al.
patent: 2004/0063746 (2004-04-01), Regueiro-Ren et al.
patent: 2004/0110785 (2004-06-01), Wang et al.
patent: 0379314 (1990-07-01), None
patent: 0484071 (1992-05-01), None
patent: 0530907 (1993-03-01), None
patent: WO 93/01181 (1993-01-01), None
patent: WO 95/04742 (1995-02-01), None
patent: WO 96/11929 (1996-04-01), None
patent: WO 00/76521 (2000-12-01), None
H. Hotoda, “Small-Molecule Inhibitors of HIV-1 Entry Via Chemokine Receptors,” Drugs of the Future, 24(12), pp. 1355-1362, 1999.
J. G. Sodroski, “HIV-1 Entry Inhibitors in the Side Pocket,” Cell, 99, pp. 243-246, 1999.
W. S. Blair, et al, “HIV-1 Entry—An Expanding Portal for Drug Discovery,” Drug Discovery Today, 5(5), pp. 183-194, 2000.
B. A. Larder, et al, “Multiple Mutations in HIV-1 Reverse Transcriptase Confer High-Level Resistance to Zidovudine (AZT),” Science, 246, pp. 1155-1158, 1989.
R. M. Gulick, “Curent Antiretroviral Therapy: An Overview,” Quality of Life Research, 6, pp. 471-474, 1997.
D. R. Kuritzkes, “HIV Resistance to Current Therapies,” Antiviral Therapy, 2 (Supplement 3), pp. 61-67, 1997.
S. Morris-Jones, et al, “Antiretroviral Therapies in HIV-1 Infection,” Expert Opinion on Investigational Drugs, 6(8), pp. 1049-1061, 1997.
R. F. Schinazi, et al, “Mutations in Retroviral Genes Associated with Drug resistance,” International Antiviral News, 5(8), pp. 129-142, 1997.
J. P. Vacca, et al, “Clinically Effective HIV-1 Protease Inhibitors,” Drug Discovery Today, 2(7), pp. 261-272, 1997.
D. Flexner, “HIV-Protease Inhibitors,” Drug Therapy, 338(18), pp. 1281-1292, 1998.
B. Berkhout, “HIV-1 Evolution Under Pressure of Protease Inhibitors: Climbing the Stairs of Viral Fitness,” J. Biomed. Sci., 6, pp. 298-305, 1999.
S. Ren, et al, “Development of HIV Protease Inhibitors: A Survey,” Progress in Drug Research, 51, pp. 1-31, 1998.
O. S. Pedersen, et al, “Non-Nucleoside Reverse Transcriptase Inhibitors: the NNRTI Boom,” Antiviral Chemistry & Chemotherapy, 10, pp. 285-314, 1999.
E. De Clercq, “The Role of Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) in the Therapy of HIV-1 Infection,” Antiviral Research, 38, pp. 153-179, 1998.
E. De Clercq, “Perspectives of Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) in the Therapy of HIV-1 Infection,” IL Farmaco, 54, pp. 26-45, 1999.
M. Font, et al, “Indoles and Pyridazino[4,5-b]Indoles as Nonnucleoside Analog Inhibitors of HIV-1 Reverse Transcriptase,” Eur. J. Med. Chem., 30, pp. 963-971, 1995.
D. L. Romero, et al, J. Med. Chem., 36, pp. 1505-1508, 1993.
S. D. Young, et al, “2-Heterocyclic Indole-3-Sulfones as Inhibitors of HIV-1 Reverse Transcriptase,” Bioorganic & Medicinal Chemistry Letters, 5(5), pp. 491-496, 1995.
M. J. Genin, et al, “Synthesis and Bioactivity of Novel Bis(Heteroaryl)Piperazine (BHAP) Reverse Transcriptase Inhibitors: Structure-Activity Relationships and Increased Metabolic Stability of Novel Substituted Pyridine Analogs,” J. Med. Chem., 39, pp. 5267-5275, 1996.
R. Silvestri, et al, Antiviral Chemistry & Chemotherapy, 9, pp. 139-148, 1998.
A. Fredenhagen, et al, “Semicochliodinol A and B: Inhibitors of HIV-1 Protease and EGF-R Protein Tyrosine Kinase Related to Asterriquinones Produced by the FungusChrysosporium merdarium,” Journal of Antibiotics, 50(5), pp. 395-401, 1997.
M. Kato, et al, “New 5-HT3(Serotonin-3) Receptor Antagonists. IV. Synthesis and Structure-Activity Relationships of Azabicycloalkaneacetamide Derivatives,” Chem. Pharm. Bull, 43(8), pp. 1351-1357, 1995.
V. Levacher, et al, “Broadening in the Scope of NADH Models by Using Chiral and Non Chiral Pyrrolo [2,3-b]Pyridine Derivatives,” Tetrahedron, 47(3), pp. 429-440, 1991.
I. Mahadevan, et al, “Synthesis of Pyrrolopyridines (Azaindoles),” J. Heterocyclic Chem., 29, pp. 359-367, 1992.
D. Hands, et al, “Convenient Method for the Preparation of 5-, 6- and 7-Azaindoles and Their Derivatives,” Synthesis, pp. 877-882, 1996.
D. Dobson, et al, “The Synthesis of 7-Alkoxyindoles,” Synthetic Communications, 21(5), pp. 611-617, 1991.
T. Sakamoto, et al, “Condensed Heteroaromatic Ring Systems, XII. Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates,” Chem. Pharm. Bull., 35(5), pp. 1823-1828, 1987.
L. P. Shadrina, et al, “Reactions of Organomagnesium Derivatives of 7-Aza- and Benzoindoles with Diethyl Oxalate and the Reactivity of Ethoxalylindoles,” Khim. Geterotsikl. Soedin., 9, pp. 1206-1209, 1987 (Russian).
T. V. Sycheva, et al, “Some Reactions of 5-Cyano-6-Chloro-7-Azaindoles and Lactam-Lactim Tautomerism in 5-Cyano-6-Hydroxy-7-Azaindolines,” Khim. Geterotsikl. Soedin., 1, pp. 100-106, 1987 (Russian).
H. Li, et al, “3-(Diethoxyphosphoryloxy)-1,2,3-Benzotriazin-4(3H)-one (DEPBT): A New Coupling Reagent with Remarkable Resistance to Racemization,” Organic Letters, 1(1), PP. 91-93, 1999.
M. Desai, et al, “A Convenient Preparation of 1-Aroylpiperazines,” Organic Preparations and Procedures Int., 8(2), pp. 85-86, 1976.
M. Adamczyk, et al, “Synthesis of Procainamide Metabolites N-Acetyl Desethylprocainamide and Desethylprocainamide,” Organic Preparations and Procedures Int., 28(4), pp. 470-474, 1996.
K. Rossen, et al, “Asymmetric Hydrogenation of Tetrahydropyrazines: Synthesis of (S)-Piperazine-2-Tert-Butylcarboxamide, an Intermediate in the Preparation of the HIV Protease Inhibitor Indinavir,” Tetrahedron Letters, 36(36), pp. 6419-6422, 1995.
T. Wang, et al, “Benzoylatin of Dianions: Preparation of Monobenzoylated Derivatives of Symmetrical Secondary Diamines,” J. Org. Chem., 64, pp. 7661-7662, 1999.
T. Wang, et al, “Regioselective Monobenzoylation of Unsymmetrical Piperazines,” J. Org. Chem., 65, pp. 4740-4742, 2000.
N. Harada, et al, “Synthesis and Antitumor Activity of Quaternary Salts of 2-(2′-Oxoalkoxy)-9-Hydroxyellipticines,” Chem. Pharm. Bull., 45(1), pp. 134-137, 1997.
I. Antonini, et al, “Synthesis of 4-Amino-1-β-D-Ribofuranosyl-1H-Pyrrolo[2,3-b]Pyridine (1-Deazatubercidin) as a Potential Antitumor Agent,” J. Med. Chem., 25, pp. 1258-1261, 1982.
S. W. Schneller, et al, J. Org. Chem., 45, pp. 4045-4048, 1980.
M. Wozniak, et al, “Amination of 4-Nitroquinoline with Liquid Methylamine/Potassium Permanganate,” Chemistry of Heterocyclic Compounds, 34(7), pp. 837-840, 1998.
S. Shiotani, et al, J. Heterocyclic. Chem., 34, pp. 901-907, 1997.
S. Minakata, et al, “Regioselective Functionalization of 1H-Pyrrolo[2,3-b]Pyridine Via Its N-Oxide,” Synthesis, pp. 661-663, 1992.
L. H. Klemm, et al, “Chemistry of Theinopyridines, XXIV. Two Transformations of Thieno[2,3-b]Pyridine 7-Oxide (1),” J. Heterocyclic Chem., 13, pp. 1197-1200, 1976.
S. Shiotani, et al, “Furopyridines. XXXIII [1]. Synthesis and Reactions of Chloropyridine Derivatives of Furo[2,3-b]-,-[2,3-c]-and-[3,2-c]Pyridine,” J. Heterocyclic Chem., 34, pp. 925-929, 1997.
M. Hayashida, et al, “Deoxygenative 2-Alkoxylation of Quin

Affiliated with

Also associated with

Rating

Antiviral azaindole derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Antiviral azaindole derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antiviral azaindole derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3386641