Phthalocyanine salt formulations
AssigneeCase Western Reserve University
InventorsMing Guo, Yun Liu, Malcolm E. Kenney
Life of this patent
Estimating the term…
Abstract
Pharmaceutical compositions of phthalocyanine compounds with a structure according to Formula (I) are described. Phthalocyanines are photosensitizer compounds having a phthalocyanine ring system that can be used for photodynamic therapy. Different phthalocyanines and phthalocyanine salts are shown to have useful characteristics such as water solubility, oil solubility, or tunable photostability. Formulations of phthalocyanines and phthalocyanine salts that can be used for topical and systemic administration are described.
Claims14
A phthalocyanine polyunsaturated fatty acid salt, with a structure according to formula (1):
- wherein M is (R′)cX[OSi(CH3)2(CH2)aN+(R″)b(R″′)cY−]d;
- X is selected from Si or AI;
- R′ is selected from OH, CH3, halogen, OCH3, OC(O)CH3, and OC(O)CH2CH3;
- R′ is selected from H, CH3, C2H5, C4H9, C4H8NH, C4H8N, C4H8NCH3, C4H8S, C4H8O, OC(O)CH3, OC(O), CS, CO, OH, C4H8N(CH2)3CH3, (CH2)2N(CH3)2, (CH2)fN((CH2)g(CH3))2, and an alkyl group having from 1 to 12 carbon atoms;
- R″′ is selected from H, CH3, SO2CH3, (CH2)2N(CH3)2, (CH2)11CH3, C(S)NHC6H11O5, (CH2)fN((CH2)g(CH3))2, and an alkyl group having from 1 to 12 carbon atoms;
- Y is a polyunsaturated fatty acid anion;
- a is an integer from 2 to 4;
- b is an integer from 0 to 3;
- c is an integer from 0 to 2;
- d is 1 or 2;
- e is 0 or 1;
- f is an integer from 1 to 12;
- g is an integer from 1 to 11;
- R1, R4, R5, R8, R9, R12, R13, and R16 are each independently selected from hydrogen, halogen, nitro, cyano, hydroxy, thiol, amino, and methyl;
- and
- R2, R3, R6, R7, R10, R11, R14, and R15 are each independently selected from hydrogen, halogen, nitro, cyano, hydroxy, thiol, amino, carboxy, aryl, heteroaryl, carbocyclyl, heterocyclyl, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C1-6alkoxy, C1-6acyl, C1-6alkylcarbonyloxy, C1-6carbocyclylalkyl, C1-6aminoalkyl, C1-6alkylamino, C1-6thioalkyl, C1-6alkylthio, C1-6hydroxyalkyl, C1-6alkyloxycarbonyl, C1-6alkylaminocarbonyl, and C1-6alkylcarbonylamino.
A phthalocyanine polyunsaturated fatty acid ester, with a structure according to formula (1):
- wherein M is (R′)dX(R″)e [OSi(CH3)2(CH2)aN(R″′)b(R″″)c]h;
- X is selected from Si or Al;
- R′ consists of a polyunsaturated fatty acid attached to X through an ester linkage;
- R″ is selected from OH, CH3, halogen, OCH3, OC(O)CH3, and OC(O)CH2CH3;
- R″′ is selected from H, CH3, C2H5, C4H9, C4H8NH, C4H8N, C4H8NCH3, C4H8S, C4H8O, OC(O)CH3, OC(O), CS, CO, OH, C4H8N(CH2)3CH3, (CH2)2N(CH3)2, (CH2)fN((CH2)g(CH3))2, and an alkyl group having from 1 to 12 carbon atoms;
- R″″ is selected from H, CH3, SO2CH3, (CH2)2N(CH3)2, (CH2)11CH3, C(S)NHC6H11O5, (CH2)fN((CH2)g(CH3))2, and an alkyl group having from 1 to 12 carbon atoms;
- a is an integer from 2 to 4;
- b is an integer from 0 to 3;
- c is an integer from 0 to 2;
- d is 1 or 2;
- e is 0 or 1;
- f is an integer from 1 to 12;
- g is an integer from 1 to 11;
- h is [2−(d+e)])
- R1, R4, R5, R8, R9, R12, R13, and R16 are each independently selected from hydrogen, halogen, nitro, cyano, hydroxy, thiol, amino,and methyl;
- and
- R2, R3, R6, R7, R10, R11, R14, and R15 are each independently selected from hydrogen, halogen, nitro, cyano, hydroxy, thiol, amino, carboxy, aryl, heteroaryl, carbocyclyl, heterocyclyl, C1-6alkyl, C1-6alkenyl, C1-6alkynyl, C1-6alkoxy, C1-6acyl, C1-6alkylcarbonyloxy, C1-6carbocyclylalkyl, C1-6aminoalkyl, C1-6alkylamino, C1-6thioalkyl, C1-6alkylthio, C1-6hydroxyalkyl, C1-6alkyloxycarbonyl, C1-6alkylaminocarbonyl, and C1-6alkylcarbonylamino.
Dependencies are inferred from the claim text.