Biologically active methylene blue derivatives

Details Biologically active methylene blue derivatives Biologically active methylene blue derivatives

2008-06-18

2010-12-21

Royds, Leslie A. (Department: 1614)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07855197

ABSTRACT:
A phenothiazinium compound of Formula (I)wherein:A and B each independently isin which R′ and R″ each independently is a linear, branched or cyclic hydrocarbon group, or R′ and R″ together with the N atom to which they are attached form an optionally substituted 5-, 6- or 7-membered ring;and where XP−is a counteranion and P is 1, 2 or 3;except for the compounds in which A and B are both either —N(CH3)2or —N(CH2CH3)2for use in a treatment that requires removal, deactivation or killing of unwanted tissues or cells.

REFERENCES:
patent: 3579339 (1971-05-01), Chang et al.
patent: 4622395 (1986-11-01), Bellus et al.
patent: 4880769 (1989-11-01), Dix et al.
patent: 5085947 (1992-02-01), Saito et al.
patent: 5085974 (1992-02-01), Frass et al.
patent: 5239405 (1993-08-01), Varaprasad et al.
patent: 5344928 (1994-09-01), Masuya et al.
patent: 5358876 (1994-10-01), Inoue et al.
patent: 5532171 (1996-07-01), Motsenbocker
patent: 5545516 (1996-08-01), Wagner
patent: 5611793 (1997-03-01), Wilson et al.
patent: 5685994 (1997-11-01), Johnson
patent: 5882627 (1999-03-01), Pomerantz
patent: 6183764 (2001-02-01), Shanbrom
patent: 6251127 (2001-06-01), Biel
patent: 6551346 (2003-04-01), Crossley
patent: 6562295 (2003-05-01), Neuberger
patent: 6623513 (2003-09-01), Biel
patent: 6952392 (2005-10-01), Vig et al.
patent: 7101977 (2006-09-01), Rosenblum et al.
patent: 7176308 (2007-02-01), Vig et al.
patent: 7220879 (2007-05-01), Bass et al.
patent: 7229447 (2007-06-01), Biel
patent: 7371744 (2008-05-01), Brown et al.
patent: 2002/0061330 (2002-05-01), Chowdhary et al.
patent: 2002/0183808 (2002-12-01), Biel
patent: 2003/0158204 (2003-08-01), Galey
patent: 2004/0055965 (2004-03-01), Hubig et al.
patent: 2004/0147508 (2004-07-01), Brown et al.
patent: 2004/0213736 (2004-10-01), Wischik et al.
patent: 2007/0161625 (2007-07-01), Brown et al.
patent: 19640758 (1999-11-01), None
patent: 0128414 (1984-12-01), None
patent: 2373787 (2002-02-01), None
patent: 63187154 (1988-08-01), None
patent: 2001124699 (2001-05-01), None
patent: WO 91/16911 (1991-11-01), None
patent: WO 96/30766 (1996-10-01), None
patent: WO 99/25314 (1999-05-01), None
patent: WO 01/62289 (2001-08-01), None
patent: WO 01/70699 (2001-09-01), None
patent: WO 02/096896 (2002-12-01), None
Merriam-Webster Dictionary [Online]. “Deactivate”. [Retrieved Jun. 10, 2009]. Retrieved from the Internet: <URL: http://www.m-w-com/dictionary/deactivate>.
Corriere et al. “MRSA: An Evolving Pathogen”. Disease-A-Month. Dec. 2008; 54(12):751-755.
www.sigma-aldrich.com, M9140 Methylene Blue, (2006).
www.sigma-aldrich.com, T3260 Toluidine Blue O, (2006).
www.sigma-aldrich.com, T7029 Thionin acetate, (2006).
www.sigma-aldrich.com, A6270 Azure A chloride, (2006).
www.sigma-aldrich.com, A4043 Azure B, (2006).
www.sigma-aldrich.com, 11667 Azure C, (2006).
www.sigma-aldrich.com, 302643 Trypan Blue, (2006).
www.sigma-aldrich.com, 211109 Methylene Green zinc chloride double salt, (2006).
www.sigma-aldrich.com, N3013 Nile Red, (2006).
“Methylene Blue” (Monograph No. 5979). The Merck Index (Eleventh Edition), Merck & Co., Inc., p. 954 (1989).
Poster titled “In Vitro Photodynamic Activity of a Series of novel Methylene Blue Analogues” by Mellish et al, Centre for Photobiology and Photodynamic Therapy, 1 page, Jul. 2000.
Wainwright et al, “Photobactericidal Activity of Phenothiazinium Dyes Against Methicillin-Resistant Strans ofStaphylococcus aureus”, FEMS Microbiology Letters, 160:177-181 (1998).
Valduga et al, “Effect of extracellularly generated singlet oxygen on Gram-positive and Gram-negative bacteria”, J. Photochem. Photobiol. B: Biol. 21:81-86 (1993).
Weng et al, “Adsorption of a cationic dye (methylene blue) onto spent activated clay”, Journal of Hazardous Materials 144:355-362 (2007).
Gürses et al, “The adsorption kinetics of the cationic dye, methylene blue, onto clay”, Journal of Hazardous Materials B131:217-228 (2006).
Methylene blue clay test kit, Website accessed Aug. 9, 2007, http://www.ofite.com/products/Drilling/Kits/168-00,htm.
Fujii et al, “Synthesis of 2-(D-Arabino-tetra-hydroxybutyl)pyrazine-5-sulfonic Acid”, Agric. Biol. Chem. 46(8):2169-2172 (1982).
Wainwright et al, “Increased cytotoxicity and phototoxicity in the methylene blue series via chromophore methylation”, Journal of Photochemistry and Photobiology B: Biology 40:233-239 (1997).
Wainwright, “Photodynamic therapy—from dyestuffs to high-tech clinical practice”, Rev. Prog. Color. 34:95-109 (2004).
Wainwright, “Photodynamic antimicrobial chemotherapy (PACT)”, Journal of Antimicrobial Chemotherapy 42:13-28 (1998).
Kiernan, Dyes and other colorants in microtechnique and biomedical research Color. Technol. 122:1-21 (2006).
Wainwright, “Non-porphyrin Photosensitizers in Biomedicine”, Chemical Society Reviews, pp. 351-359 (1996).
Colour Index, Third Edition, vol. 4 (1971), (The Society of Dyers and Colourists/American Association of Textile Chemists and Colorists), http://www.colour-index.org.
The Sigma-Aldrich Handbook of Stains, Dyes and Indicators, Floyd J. Green (Aldrich Chemical Company Inc., Milwaukee, Wisconsin (1990).
Stains and Dyes—Certified and Non-Certified, http://www.sigmaaldrich.com [http://www.sigmaaldrich.com/Area—of—Interest/Research—Essentials/Hematology—and—Histology/Product—Lines/Stains—and—Dyes.htmI.].
Bernthsen, “Studien in der Methylenblaugruppe”, Justus Liebig's Annalen Der Chemie 251, Abschnitt 6, Homologe Indamine und Thioninfarbstoffe, pp. 83-97 (1888) and English Translation.
Moura et al, “Synthetic routes to 3,7-bis(dialkylamino)phenothiazin-5-ium compounds”, Current Drug Targets 4(2):133-142 (2003).
http://photopharmica.com
ews/01—07—07.htm “Photopharmica . . . Phase II Data”(2007).
Mellish et al, “In Vitro Photodynamic Activity of a Series of Methylene Blue Analogues”, Photochemistry and Photobiology 75(4):392-397 (2002).
Merriam-Webster Dictinary [Online], “Remove”. [Retrived Mar. 16, 2007]. Retrieved from the Internet: <URL: http://www.m-w.com/dictinoary/remove.>.
Mutschler et al, “Drug Actions” Basic Principles and Therapeutic Aspects, Medpharm Scientific Publishers, pp. 515-580 (1995).
U.S. Appl. No. 12/078,805, filed Apr. 4, 2008.
U.S. Appl. No. 12/149,996, filed May 12, 2008.
U.S. Appl. No. 12/171,121, filed Jul. 10, 2008.
Stains File, internet resource for histotechnologists, http://stainsfile.info/StainsFile/theory/solvent.htm, May 2005.
Office Action dated Jun. 16, 2009 from U.S. Appl. No. 12/078,805.
Office Action dated May 29, 2009 from U.S. Appl. No. 12/171,121.
STN Registry No. 61-73-4, “Methylene Blue”, STn Registry Database p. 1-2. Retrieved May 21, 2009.
Office Action dated Jul. 8, 2010 from U.S. Appl. No. 12/078,805.
Moura et al; “Synthesis and Evaluation of Phenothiazine Singlet Oxygen Sensitizing Dyes for Application in Cancer Phototherapy”. Phosphorus, Sulfur and Silicon, 1997; 120&121:459-460.
Office Action dated Jan. 12, 2010 in U.S. Appl. No. 12/149,996.
Office Action dated Jun. 14, 2010 in U.S. Appl. No. 12/149,996.
Merriam-Webster Dictionary [Online]. “Moiety”. [Retrieved Jun. 9, 2010]. Retrieved from the internet: <URL: http://www.m-w.com/dictionary/moiety>.

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