Methods of syntheses of phthalocyanine compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

514 63, C09B 4704, C09B 4708, C07F 718

Patent

active

057636028

ABSTRACT:
The present invention provides improved methods for synthesizing phthalocyanines, particularly HOSiPcOSi(CH.sub.3).sub.2 (CH.sub.2).sub.3 N(CH.sub.3).sub.2, which do not involve photolysis, and which produces purity of at least about 95%, and in the preferred embodiment of the first method of synthesis provide a yield of greater than about 70% and typically greater than 80%. The first method involves a method for synthesizing a phthalocyanine compound comprising the following steps: providing a phthalocyanine precursor having a central silicon; adding a first aminosiloxy ligand to the central silicon of the phthalocyanine precursor; adding a second aminosiloxy ligand to the central silicon of the phthalocyanine precursor; displacing the second aminosiloxy ligand by an organic acid ligand, preferably Cl.sub.3 CCOO ligand; then displacing the Cl.sub.3 CCOO ligand with an HO ligand. The second method for making Pc4 is a method for synthesizing a phthalocyanine compound comprising the following steps: providing a phthalocyanine precursor having a central silicon; providing a siloxy ligand with an iodo group; adding a first and second siloxyiodo ligand to the central silicon of the phthalocyanine precursor; displacing the second siloxyiodo ligand by an organic acid, preferably a Cl.sub.3 CCOO ligand; then displacing the a Cl.sub.3 CCOO ligand with an HO ligand; and then displacing the iodo group with a dimethylamino group.

REFERENCES:
patent: 4927735 (1990-05-01), Era et al.
patent: 5166197 (1992-11-01), Kenney et al.
patent: 5358940 (1994-10-01), Capraro et al.
patent: 5484778 (1996-01-01), Kenney et al.
"Silicon Phthalocyanine/Methyl Methacrylate Copolymer Slab Directional Couplers for All-Optical Switching" by Sounik, et al., Journal of Applied Polymer Science, vol. 53, pp. 677-685, (1994).
"Synthesis of Ampjiphilic Phthalocyanines and Langmuir-Blodgett Film Balance Studies of These Compounds" by Batzel, submitted in partial fulfillment of requirements for degree of Doctor of Philosophy, Dept. of Chemistry, Case Western Reserve University, Mar. 26, 1990. (Entered in OCLC/Cataloged 21265660).
"The Synthesis, Photophysical and Photobiological Properties, and In Vitro Structure-Activity Relationships of a Set of Silicon Phthalocyanine PDT Photosensitizers" by He, et al., Photochem. Photobiol.*, vol. 65, No. 3, Mar. 1997, pp. 581-586.
Abstract 126:239641s "Organosilicon (na)phthalocyanine photoactivators and cleaning compositions containing them" by A.D. Wiley, CA Selects Plus: Organosilicon Chemistry, Issue 9, 1997, p. 43.
Abstract 126:239642t "Low-hue photodisinfectants", by A.D. Wiley, CA Selects Plus: Organosilicon Chemistry, Issue 9, 1997, p. 43.
U.S. application Ser. No. 08/829,527, filed Mar. 28, 1997.
"New Phthalocyanine Photosensitizers for Photodynamic Therapy," by Oleinick et al., Photochemistry and Photobiology, vol. 57, No. 2, pp. 242-247, Feb. 1993.
"DNA Lesions and DNA Degradation in Mouse Lymphoma L5178Y Cells After Photodynamic Treatment Sensitized by Chloraluminum Phthalocyanine," by Ramakrishnan et al., Photochemistry and Photobiology, vol. 50, No. 3, pp. 373-378, Sep. 1989.
"Photodynamic Therapy Induces Rapid Cell Death by Apoptosis in L5178Y Mouse Lymphoma Cells," by Agarwal et al., Cancer Research, vol. 51, No. 51, pp. 5993-5996, Nov. 1, 1991.
"The Phthalocyanines: A New Class of Mammalian Cell Photosensitizers With a Potential for Cancer Phototherapy," by Ben-Hur et al., Int. J. Radiat. Biol., vol. 47, No. 2, pp. 145-147, Feb. 1985.
"Activity of Phthalocyanine Photosensitizers Against Human Glioblastoma in Vitro," by Abernathy et al., Neurosurgery, 21, No. 4, pp. 468-473, Oct. 1987.
"The Role of Singlet Oxygen in the Photoemolysis of Red Blood Cells Sensitized by Phthalocyanine Sulfonates," by Sonoda et al., Photochem. Photobiol., vol. 46, No. 5, pp. 625-631, Nov. 1987.
"Evaluation of Sulfonated Aluminum Phthalocyanines for Use in Photochemotherapy," by Berg et al., Cancer Letters, vol. 44, pp. 7-15, 1989.
"The Effect of Substitutents on Phthalocyanine Phototoxicity," by Rosenthal et al., Photochem. Photobiol., vol. 46, No. 6, pp. 959-963, Dec. 1987.
"Synthesis and Photocytotoxicity of Some New Substituted Phthalocyanines," by Leznoff et al., Photochem. Photobiol., vol. 49, pp. 279-284, Mar. 1989.
The Merck Manual, 15th Edition, Robert Berkow, ed., pp. 1219-1220, 1227.
"The Nuclear Magnetic Resonance Spectra and the Electronic Spectra of Some Silicon and Germanium Phthalocyanines," Kane et al., Inorganic Chemistry, vol. 9, pp. 1445-1448.
"Photodynamic Therapy With Phthalocyanine Photosensitisation: Quantitative Studies in a Transplantable Rat Fibrosarcoma," by Tralau et al., Br. J. Cancer, vol. 55, No. 4, pp. 389-395, Apr. 1987.
"Biological Activities of Phthalocyanines--IX. Photosensitization of V-79 Chinese Hamster Cells and EMT-6 Mouse MAmmary Tumor by Selectively Sulfonated Zine Phthalocyanines," by Brasseur et al., Photochem. Photobiol., vol. 47, No. 5, pp. 705-711, May 1988.
"Tissue Uptake, Distribution and Potency of the Photoactivable Dye Chloraluminum Sulfonated Phthalocyanine in Mice Bearing Transplantable Tumors," by Chan et al., Cancer Res., vol. 48, No. 11, pp. 3040-3044, Jun. 1, 1988.
"Photodynamic Therapy for Experimental Intraocular Melanoma Using Chloroaluminum Sulfonated Phthalocyanine," Arch. Ophthalmol., vol. 107, pp. 886-890, Jun. 1989.
"Synthesis of Positively Charged Phthalocyanines and Their Activity in the Photodynamic Therapy of Cancer Cells," by Wohrle et al., Photochem. Photobiol., vol. 51, No. 3, pp. 351-356, Mar. 1990.
"Laser-Induced Photodynamic Therapy With Aluminum Phthalocyanine Tetrasulfonate as the Photosensitizer: Differential Phototoxicity in Normal and Malignant Human Cells in Vitro," by Glassberg et al., J. Inv. Dermatol., vol. 94, No. 5, pp. 604-610, May 1990.
"Photodynamic Therapy of Spontaneous Cancers in Felines, Canines, and Snakes With Chloro-Aluminum Sulfonated Phthalocyanine," by Roberts et al., J. Natl. Cancer Inst., vol. 83, No. 1, p. 1823, Jan. 2, 1991.
"Inactivation of Viruses in Red Cell and Platelet Concentrates With Aluminum Phthalocyanine (AlPc) Sulfonates," by Horowitz et al., Blood Cells, vol. 18, No. 1, pp. 141-150, Jan. 1992.
"Photodynamic Therapy of Chemically-and Ultraviolet B Radiation-Induced Murine Skin Papillomas by Chloroaluminum Phthalocyanine Tetrasulfonate," by Agarwal et al., Photochem. Photobiol., vol. 56, No. 1, pp. 43-50, Jul. 1992.
"Biological Activities of Phthalocyanines--XVI. Tetrahydroxy-and Tetraalkylhydroxy Zinc Phthalocyanines. Effect of Alkyl Chain Length on In Vitro and In Vivo Photodynamic Activities," by Boyle et al., Br. J. Cancer, vol. 67, No. 6, pp. 1177-1181, Jun. 1993.
"Phthalocyanines in Photobiology," by I. Rosenthal and E. Ben-Hur, in Phthalocyanines: Properties and Applications, ed. by C.C. Leznoff and A.B.P. Lever, VCH Publishers, Inc., New York, pp. 397-425, 1989.
"Preclinical Examination of First and Second Generation Photosensitizers Used in Photodynamic Therapy," by C.J. Gomer, Photochem. Photobiol., vol. 54, No. 6, pp. 1093-1107, Dec. 1991.
"Photodynamic Therapy in Oncology: Mechanisms and Clinical Use," H.I. Pass, J. Natl. Can. Inst., vol. 85, No. 6, pp. 443-456, Mar. 17, 1993.
"Phthalocyanines as Photodynamic Sensitizers," by I. Rosenthal, Photochem. Photobiol., vol. 53, No. 6, pp. 859-870, Jun. 1991.
"Photodynamic effects of silicon phthalocyanines in model cells and tumors," by Oleinick, et al., SPIE vol. 1645, Optical Methods for Tumor Treatment and Detection, 1992, pp. 242-250.
Abstract 108:178915p ".pi.-.pi. Interaction, architecture, and bandwidths in molecular metals," by Doris, et al., Is. J. Chem., 1986.
Abstract 102:78944e "The .pi.-.pi. Interactions and bandwidths in molecular metals", Ciliberto, et al., J. Am. Chem. Soc. 1984.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Methods of syntheses of phthalocyanine compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Methods of syntheses of phthalocyanine compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods of syntheses of phthalocyanine compounds will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2200751

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.