Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-01-04
2011-01-04
Chang, Celia (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07863451
ABSTRACT:
The present invention concerns new processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines which are useful for preventing or treating diseases or conditions related to an abnormally high level or activity of TNFα. The invention provides processes for the commercial production of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines including, but not limited to, the therapeutically active 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione.
REFERENCES:
patent: 5134127 (1992-07-01), Stella et al.
patent: 5463063 (1995-10-01), Muller
patent: 5635517 (1997-06-01), Muller et al.
patent: 5698579 (1997-12-01), Muller
patent: 5798368 (1998-08-01), Muller et al.
patent: 5874448 (1999-02-01), Muller et al.
patent: 5877200 (1999-03-01), Muller
patent: 5929117 (1999-07-01), Muller et al.
patent: 5955476 (1999-09-01), Muller et al.
patent: 6114355 (2000-09-01), Buerger et al.
patent: 6235756 (2001-05-01), D'Amato
patent: 6281230 (2001-08-01), Muller et al.
patent: 6316471 (2001-11-01), Muller et al.
patent: 6335349 (2002-01-01), Muller et al.
patent: 6380239 (2002-04-01), Muller et al.
patent: 6395754 (2002-05-01), Muller et al.
patent: 6403613 (2002-06-01), Man et al.
patent: 6458810 (2002-10-01), Muller et al.
patent: 6476052 (2002-11-01), Muller et al.
patent: 6555554 (2003-04-01), Muller et al.
patent: 7091343 (2006-08-01), Bebbington et al.
patent: 7153867 (2006-12-01), Shah et al.
patent: 7153876 (2006-12-01), Schudok et al.
patent: 2002/0045643 (2002-04-01), Muller et al.
patent: 2003/0045552 (2003-03-01), Robarge et al.
patent: 2003/0096841 (2003-05-01), Robarge et al.
patent: 2004/0029832 (2004-02-01), Zeldis
patent: 2004/0087546 (2004-05-01), Zeldis
patent: 2004/0091455 (2004-05-01), Zeldis
patent: 2004/0147558 (2004-07-01), Treston et al.
patent: 2004/0220144 (2004-11-01), Zeldis
patent: 2007/0004920 (2007-01-01), Ge et al.
patent: 2007/0049618 (2007-03-01), Muller et al.
patent: 2008/0214615 (2008-09-01), Muller et al.
patent: WO 95/01348 (1995-01-01), None
patent: WO 98/03502 (1998-01-01), None
patent: WO 98/54170 (1998-12-01), None
patent: WO 00/55134 (2000-09-01), None
patent: WO 02/059106 (2002-08-01), None
patent: WO 2005/005409 (2005-01-01), None
patent: WO 2009/111948 (2009-09-01), None
patent: WO 2009/114601 (2009-09-01), None
Exahibit I.
Braga et al. “making crystals . . . ” Chem. Commun. p. 3635-3645 (2005).
Katsura et al. “Preparation of . . . ” CA 133:237671 (2000).
Soederberg et al. “Synthesis of . . . ” CA 141:314104 (2003).
Exhibit I.
Morrison &Boyd “Organic Chemistry” p. 680-681 (1073).
Muller et al. “2-(2,6-dioxopiperidin-3-yl . . . ” CA152:37403 (2009).
“acid chloride to amide” Internet p. 1-3 (2010).
Capitosti et al., Facile synthesis of an azido-labeled thalidomide analogue. Org Lett. Aug. 7, 2003;5(16):2865-7.
Chang et al., A synthesis of racemic thalidomide. Synthetic Communications, 2003, 33(8):1375-1382.
Eger et al., Synthesis, Central nervous system activity and teratogenicity of a homothalidomide. Arzneimittelforschung. Oct. 1990;40(10):1073-5.
Gutschow et al., Aza analogues of thalidomide: synthesis and evaluation as inhibitors of tumor necrosis factor-alpha production in vitro. Bioorg Med Chem. Apr. 2001;9(4):1059-65.
He te al., Synthesis of thalidomide analogs and their biological potential for treatment of great-versus-host disease (GVHD). Abstracts of papers of the American Chemical Society 206:216-MEDI, Aug. 22, 1993.
Hess et al., Synthesis and immunological activity of water-soluble thalidomide prodrugs. Bioorg Med Chem. May 2001 ;9(5):1279-91.
Klinsberg, Erwin.Chemistry of Heterocyclic Compounds. New York: Wiley & Sons, 1960 (pp. 295-296).
Lima et al., Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Bioorg Med Chem. Sep. 2002;10(9):3067-73.
Luzzio et al., Synthesis of racemic cis-5-hydroxy-3-phthalimidoglutarimide. A metabolite of thalidomide isolated from human plasma. J Org Chem. Nov. 25, 2005;70(24):10117-20.
Luzzio et al., Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido-2S,3S(3-hydroxy) ornithine. Tetrahedron Lett. 2000, 41:7151-55.
Luzzio et al., Thalidomide metabolites and analogues. 3. Synthesis and antiangiogenic activity of the teratogenic and TNF alpha-modulatory thalidomide analogue 2-(2,6-dioxopiperidine-3-yl)phthalimidine. J Med Chem. Aug. 28, 2003;46(18):3793-9.
Luzzio et al., Thalidomide metabolites. Part 1: Derivatives of (+)-2-(N-phthalimido)-γ-hydroxyglutamic acid. Tetrahedron Letters, 2000, 41:2275-2278.
Luzzio et al., Thalidomide analogues: derivatives of an orphan drug with diverse biological activity. Expert Opin. Ther. Patents, 2004, 14(2):215-229.
Machado et al., Design, synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide. Bioorg Med Chem Lett. Feb. 15, 2005;15(4):1 169-72.
Man et al., Alpha-fluoro-substituted thalidomide analogues. Bioorg Med Chem Lett. Oct. 20, 2003;13(20):3415-7.
Muller et al., A concise two-step synthesis of thalidomide. Organic Process Research & Development. 1999, 3:139-140.
Muller et al., Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity. J Med Chem. Aug. 16, 1996;39(17):3238-40.
Noguchi et al., Angiogenesis inhibitors derived from thalidomide. Bioorg Med Chem Lett. Dec. 15, 2005;15(24):5509-13.
Pablo Mureil M et al., Synthesis and pharmacological evaluation of a thalidomide analog, the 3-phthalimide-3-(3,4- dimethoxypheny1)-propanioc acid in liver cirrhosis induced by bile duct ligation in the rat. Hepatology, 2001, 34(4):pp517A, Abastract#1379.
Park et al., Synthesis and structure-activity relationships of novel compounds for the inhibition of TNF-alpha production. Arch Pharm Res. Aug. 2000;23(4):332-7.
Shah et al., Synthesis and enantiomeric separation of 2-phthalimidino-glutaric acid analogues: potent inhibitors of tumor metastasis. J Med Chem. Aug. 12, 1999;42(16):3014-7.
U.S. Appl. No. 10/693,794, filed Oct. 23, 2003, Zeldis.
U.S. Appl. No. 10/900,270, filed Jul. 28, 2004, Muller et al.
U.S. Appl. No. 10/900,332, filed Jul. 28, 2004, Muller et al.
U.S. Appl. No. 10/934,863, filed Sep. 3, 2004, Jaworsky et al.
U.S. Appl. No. 60/499,723, filed Sep. 4, 2003, Jaworsky.
U.S. Appl. No. 60/518,600, filed Nov. 6, 2003, Zeldis.
U.S. Appl. No. 60/554,923, filed Mar. 22, 2004, Zeldis et al.
Corral et al., 1999, “Immunomodulation by thalidomide and thalidomide analogues,” Ann. Rheum. Dis. 58(Suppl. 1):1107-113.
Dezube et al., 1990, “Pentoxifylline and wellbeing in patients with cancer,” Lancet 335(8690):662.
Glogau, 2000, “The risk of progression to invasive disease,” J. Am. Acad. Dermatol. 42(1 Pt 2):23-24.
Goette, 1981, “Topical chemotherapy with 5-fluorouracil. A review,” J. Am. Acad. Dermatol. 4(6):633-649.
He et al., 1993, “Synthesis of thalidomie analogs and their biological potential for treatment of graft versus host diseases,” 206th American Chemical Society, Chicago, IL, Med. Chem. paper 216.
Hinshaw et al., 1990, “Survival of primates in LD100 septic shock following therapy with antibody to tumor necrosis factor (TNF alpha),” Circ. Shock. 30(3):279-92.
Jonsson et al., 1972, “Chemical structure and teratogenic properties: 3. A review of available data on structure-activity relationships and mechanism of action of thalidomide analogs,” Acta. Pharm. Suecica 9:521-542.
Marks et al., 1988, “Malignant transformation of solar keratoses to squamous cell carcinoma,” Lancet 1(8589):795-797.
Millar et al., 1989, “Tumour necrosis factor in bronchopulmonary secretions of patients with adult respiratory distress syndrome,” Lancet 2(8665):712-4.
Muller et al., 1996, “Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity,” J. Med. Chem. 39(17):3238-324
Chen Roger
Ge Chuansheng
Muller George W.
Saindane Manohar Tukaram
Celgene Corporation
Chang Celia
Jones Day
LandOfFree
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