Enantiomerically pure phosphoindoles as HIV inhibitors

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C514S415000, C548S492000

Reexamination Certificate

active

07960428

ABSTRACT:
3-phosphoindole compounds substantially in the form of a single enantiomer useful for the treatment of Flaviviridae virus infections, and particularly for HIV infections are provided. Also provided are pharmaceutical compositions comprising the 3-phosphoindole compounds alone or in combination with one or more other anti-viral agents, processes for their preparation, and methods of manufacturing a medicament incorporating these compounds.

REFERENCES:
patent: 4866084 (1989-09-01), Gunasekera et al.
patent: 5124327 (1992-06-01), Greenlee et al.
patent: 5424329 (1995-06-01), Boschelli et al.
patent: 5489685 (1996-02-01), Houpis et al.
patent: 5527819 (1996-06-01), Williams et al.
patent: 5565446 (1996-10-01), Boschelli et al.
patent: 5703069 (1997-12-01), Connor et al.
patent: 5830894 (1998-11-01), Pevear et al.
patent: 5852011 (1998-12-01), Matsunaga et al.
patent: 5929114 (1999-07-01), Domagala et al.
patent: 5935982 (1999-08-01), Dykstra et al.
patent: 5945440 (1999-08-01), Kleinschroth et al.
patent: 5981525 (1999-11-01), Farina et al.
patent: 6017903 (2000-01-01), Slusher et al.
patent: 6025345 (2000-02-01), Jackson et al.
patent: 6025390 (2000-02-01), Farina et al.
patent: 6297270 (2001-10-01), Beller et al.
patent: 6506787 (2003-01-01), Fujishita et al.
patent: 6710068 (2004-03-01), La Colla et al.
patent: 6716605 (2004-04-01), Fujishita et al.
patent: 6825201 (2004-11-01), Wang et al.
patent: 6900206 (2005-05-01), Kadow et al.
patent: 7534809 (2009-05-01), Storer et al.
patent: 2002/0019434 (2002-02-01), Fujishita et al.
patent: 2003/0096825 (2003-05-01), Wang et al.
patent: 2003/0236277 (2003-12-01), Kadow et al.
patent: 2004/0006090 (2004-01-01), Kadow et al.
patent: 2004/0063746 (2004-04-01), Regueiro-Ren et al.
patent: 2006/0074054 (2006-04-01), Storer et al.
patent: 2009/0163444 (2009-06-01), Storer et al.
patent: 1799696 (2008-11-01), None
patent: WO 94/19321 (1994-09-01), None
patent: WO 96/29077 (1996-09-01), None
patent: WO 97/48399 (1997-12-01), None
patent: WO 97/48400 (1997-12-01), None
patent: WO 97/48409 (1997-12-01), None
patent: WO 98/13046 (1998-04-01), None
patent: WO 98/38332 (1998-09-01), None
patent: WO 98/53812 (1998-12-01), None
patent: WO 99/52915 (1999-10-01), None
patent: WO 01/02388 (2001-01-01), None
patent: WO 03/068221 (2003-08-01), None
patent: WO 03/090690 (2003-11-01), None
patent: WO 03/090691 (2003-11-01), None
patent: WO 03/091264 (2003-11-01), None
patent: WO 2004/014364 (2004-02-01), None
patent: WO 2006/054182 (2006-05-01), None
patent: WO 2008/042240 (2008-04-01), None
Alexandre et al., “Synthesis and Antiviral Activity of Phospho-Indoles as Novel NNRTI with Potent Anti-HIV Activity and Enhanced Barrier to Resistance,” Poster presented at ASMC07, St. Petersburg, Russia (Aug. 28-31, 2007).
Alexandre et al., “IDX 12899; A Novel and Highly Potent anti-HIV Non-Nucleosidic-Reverse-Transcriptase-Inhibitor with Enhanced Barrier to Resistance Profile,” Poster 21 presented at 14thSCI-RSC Medicinal Chemistry Symposium, Cambridge, UK (Sep. 23-26, 2007).
Aoyagi et al., “Studies on Chromogenic and Fluorogenic Substrates for Detection of Enzymatic Activities,” J. Fac. Eng. Chiba Univ., 26(49):185-191 (1974).
Artico et al., “2-Sulfonyl-4-Chloroanilino Moiety: A Potent Pharmacophore for the Anti-Human Immunodeficiency Virus Type 1 Activity of Pyrrolyl Aryl Sulfones,” J. Med. Che., 39:522-530 (1996).
Artico et al., “1-Arylsulfonyl-3-(α-hydroxybenzyl)-1H-Pyrroles, a Novel Class of Anti-HIV-1 Reverse Transcriptase Inhibitors,” Bioorganic & Med. Chem. Letters 7:1931-1936 (1997).
Artico et al., “Strucure-Based Design, Synthesis, and Biological Evaluation of Novel Pyrrolyl Aryl Sulfones: HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors Active at Nanomolar Concentrations,” J. Med. Chem., 43:1886-1891 (2000).
Baba et al., “Highly Potent and Selective Inhibition of HIV-1 Replication by 6-Phenylthiouracil Derivatives,” Antiviral Res., 17:245-264 (1992).
Balzarini et al., “2′5′-Bis-O-(tert-Butyldimethylsilyl)-3′-Spiro5″-(4″-Amino-1″,2″-Oxathiole-2″,2″-Dioxide) Pyrimidine (TSAO) Nucleoside Analogues: Highly Selective Inhibitors of Human Immunodeficiency Virus Type 1 that are Targeted at the Viral Reverse Transcriptase,” PNAS, 89:4392-4396 (1992).
Beilstein Registry No. 284968, Chemical Name “di-indol-3-yl-phosphinic acid,” Beilstein Entry Date: Jun. 27, 1988.
Bell et al., “Phenethylthiazolethiourea (PETT) Compounds, a New Class of HIV-1 Reverse Transcriptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies of PETT Analogs,” J. Med. Chem., 38:4929-4936 (1995).
Cantrell et al., “Phenethylthiazolylthiourea (PETT) Compounds as a New Class of HIV-1 Reverse Transcriptase Inhibitors. 2. Synthesis and Further Structure-Activity Relationship Studies of PETT Analogs,” J. Med. Chem., 39:4261-4274 (1996).
Chen et al., “Synthesis of Indoles via a Palladium-Catalyzed Annulation between Iodoanilines and Ketones,” J. Org. Chem., 62(9):2676-2677 (1997).
Danel et al., “Synthesis of Potent Anti-HIV-1 Activity of Novel 6-Benzyluracil Analogues of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine,” J. Med. Chem., 39:2427-2431 (1996).
Danel et al., “Anti-HIV Active Naphthyl Analogues of HEPT and DABO,” Acta Chemica Scandinavica, 51:426-430 (1997).
DeClercq, “HIV Inhibitors Targeted at the Reverse Transcriptase,” Aids Research and Human Retroviruses, 8(2):119-134 (1992).
Greene, “The Molecular Biology of Human Immunodeficiency Virus Type 1 Infection,” New England Journal of Medicine, 324:308-317 (1991).
Gurevich et al., “Phosphorylation of Indoles with Phosphorus (III) Acid Chlorides,” J. Gen. Chem. USSR (Engl. Transl.), 55(5):1121-1125 (1985).
Haikal, “Synthesis of Guanosine-3′-(5-Bromo-4-Chloroindol-3-YL)-Phosphate (G-3′-BCIP),” Collection of Czechoslovak Chemical Communications, 61(3):427-431 (1996).
Horwitz et al., “Substrates for Cytochemical Demonstration of Enzyme Activity II. Some Dihalo-3-Indolyl Phosphates and Sulfates,” Journal of Medicinal Chemistry, 447 (May 1966).
Horwitz et al., “Substrates for Cytochemical Demonstration of Enzyme Activity V. Thymidine 3′-and 5′-(5-Bromo-4-Chloro-3-Indolyl) Phosphates,” Journal of Medicinal Chemistry, 13(5):1024-1025 (1970).
Jakubik et al., “IDX 12899 anti-HIV-1 Activity and Resistance Profile is Superior to Efavirenz,” Poster 1657 presented at the XVI International HIV Drug Resistance Workshop, Barbados, West Indies (Jun. 12-16, 2007).
Kohlstaedt et al., “Crystal Structure at 3.5 \Anstrom Resolution of HIV-1 Reverse Transcriptase Complexed with an Inhibitor,” Science, 256(5065):1783-1790 (1992).
Mai et al., “Dihydro(alkylthio)(naphthylmethyl)oxopyrimidines: Novel Non-Nucleoside Reverse Transcriptase Inhibitors of the S-DABO Series,” J. Med. Chem., 40:1447-1454 (1997).
March et al., “The Synthesis of Ribonucleotide-5′-(5-Iodoindol-3-ol) and (4-Methylcoumarin-7-ol) Esters for the Histochemical Demonstration of Nucleases (1A),” Journal of Heterocyclic Chemistry, 7(4):885-889 (1970).
Mitsuya et al., “Molecular Targets for AIDS Therapy,” Science, 249(4976):1533-1544 (1990).
Pauwels et al., “Potent and Selective Inhibition of HIV-1 Replication in vitro by a Novel Series of TIBO Derivatives,” Nature, 343:470-474 (1990).
Pauwels et al., “Potent and Highly Selective Human Immunodeficiency Virus Type 1 (HIV-1) Inhibition by a Series of α-anilinophenylacetamide Derivates Targeted at HIV-1 Reverse Transcriptase,” PNAS, 90:1711-1715 (1993).
Pontikis et al., “Synthesis and Anti-HIV Activity of Novel N-1 Side Chain-Modified Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT),” J. Med. Chem., 40:1845-1854

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