C-nitroso compounds and use thereof

Details C-nitroso compounds and use thereof C-nitroso compounds and use thereof

2006-05-23

2006-05-23

Berch, Mark L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S231500, C514S230500, C514S250000, C514S252170, C514S645000, C514S214030, C514S356000, C514S396000, C514S411000, C514S415000, C514S471000, C514S166000, C540S552000, C544S133000, C544S091000, C544S295000, C544S350000, C544S366000, C546S329000, C546S124000, C548S444000, C548S503000, C548S530000, C548S452000, C548S337100, C549S494000, C549S457000, C562S434000, C564S300000, C564S301000, C560S066000

Reexamination Certificate

active

07049308

ABSTRACT:
A C-nitroso compound having a molecular weight ranging from 225 to 1,000 (from 225 to 600 for oral administration) on a monomeric basis wherein a nitroso group is attached to a tertiary carbon, which is obtained by nitrosylation of a carbon acid having a pKa less than about 25, is useful as an NO donor. When the compound is obtained from a carbon acid with a pKa less than about 10, it provides vascular relaxing effect when used at micromolar concentrations and this activity is potentiated by glutathione to be obtained at nanomolar concentrations. When the compound is obtained from a carbon acid with a pKa ranging from about 15 to 20, vascular relaxing effect is obtained at nanomolar concentrations without glutathione. In another embodiment, a biocompatible polymer incorporates a C-nitroso moiety.

REFERENCES:
patent: 3714255 (1973-01-01), Olechowski
patent: 6231894 (2001-05-01), Stamler et al.
patent: 6359182 (2002-03-01), Stamler et al.
patent: 6538116 (2003-03-01), Stamler et al.
patent: WO 96/16645 (1996-06-01), None
patent: WO 96/17604 (1996-06-01), None
patent: WO 02/34705 (2002-05-01), None
Ansari et al. Indian Journal of Chemistry, vol. 27B, Apr. 1988, pp. 355-357).
Zbiral et al. (Tetrahedron, 24 (3), 1363-76, 1968).
Aktaev, N.P., et al.Chemical Abstracts 83:27640j (1975).
Ansari, M.H., et al., Indian Journal of Chemistry, 273, 355-357 (Apr. 1998).
Hornback, J.M., Organic Chemistry, Brooks/Coles Publishing Company, New York, New York, pp. 132-133.
Jolibois, H., et al., Helvetica Chimica Acta 38(6), 1801-1804 (1975).
Rehse, K., et al., Arch. Pharm. Pharm. 331, 111-117 (1998).
Shklyaev, B.C. et al., Izv Akad. Nauk SSSR, Ser. Khim 959 (1986).
Bruice, P.Y., Organic Chemistry Second Edition, Prentice Hall, Upper Saddle River, New Jersey, p. 817.
Feelisch, M. and Stamler, J.S., Method in Nitric Oxide Research, John Wiley & Sons, New York, 1996, p. 71-115.
Rehse, K., et al., Arch. Pharm. Pharm. Med. Chem 331, 79-84 (1998), ibid 104-110.
Sklyar, Yu. E., et al, Khimiya Geterotsiklicheskikh Soedinenii 5(1) 70-73 (1969).
Zbiral, E., et al., Tetrahedron 24, 1363-1376 (1968).
Groves, P.H., et al., Cardiovascular Research 26, 615-619 (1992).
Groves, P.H., et al., Circulation 87, 590-597 (1993).
Chou, Sunwen, et al., Oxidation and Mass Spectra of 4,4-Dimethyloxazolidine-N-Oxyl (Doxyl) Derivatives of Ketones, J. Org. Chem., vol. 39, No. 16, 1974, pp. 2356-2361.
Hamann, Herman C., et al., Pseudohalogens. XI. In Situ Addition of Nitrosyl Formate to Olefins1,2, J. Of Amer. Chem. Soc., vol. 90, Nov. 6, 1968, pp. 6481-6486.
Barclay, L.R. C., et al., “Photolysis of 2,4,6-Tri-T-Butylnitrosobenzene”, Tetrahedron Letters, No. 49, 1973, pp. 4901-4904, Pergamon Press.
Banerjee, S., et al., “Synthesis of 2′-(3α-Benzyloxy-24-Norcholan-23-YL)-2′,4′,4′-Trimethyl-4′,5′-Dihydrooxazoline-N-Oxyl...”, Tetrahedron Ltrs, vol. 48, No. 1992, pp. 133-148, Pergamon Press.
Chemical Abstract, CAPLUS, AN:1968-78027.
Chemical Abstract, CAPLUS, AN:63-62543.
Chemical Abstract, CAPLUS, AN:1970:111204.
Chemical Abstract, CAPLUS, AN:87:21741.
Chemical Abstract, CAPLUS, AN:91:71158-11-7.
Chemical Abstract, CAPLUS, AN:1966:18909.
Beilstein Abstract, BRN: 2029838.
Beilstein Abstract, BRN: 3336431.
Beilstein Abstract, BRN: 2397853.
Beilstein Abstract, BRN: 7008799.
Beilstein Abstract, BRN: 7640852,7640863, 7653010.
Beilstein Abstract, BRN: 7591730.
Beilstein Abstract, BRN: 2380111.
Beilstein Abstract, BRN: 922007.
Beilstein Abstract, BRN: 6142353.
Beilstein Abstract, BRN: 3470606.
Beilstein Abstract, BRN: 4828870.
Beilstein Abstract, BRN: 1321867.
Beilstein Abstract, BRN: 1508646.
Beilstein Abstract, BRN: 2151857.
Beilstein Abstract, BRN: 2888112.
Beilstein Abstract, BRN: 6407255.
Beilstein Abstract, BRN: 2978996.
Abakumov et al. (Bull. Acad. Sci. USSR Div. Chem Sci.).
Ryaboi et al. (Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimcheskaya Tekhnologiya (1965), 8(3), 426-31).
Ozola et al. (Chem. Heterocylc. Compds (Eng. Transl.); 7; 1971; 592-595).
Gutteridge et al. (J. Chem. Soc. (C), 1970, 641-645).
Wilcox et al. (J. Chem. Soc. Chem. Commun. 1993, 1377-1379).

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