Uses of benzochlorins, verdins and porphyrin derivatives and of compositions containing such benzochlorins, verdins and porphyrin derivatives

Claim 1

A method for detecting diseased tissue which comprises administering intravenously, intramuscularly, subcutaneously or topically to a human or animal patient an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, and, after sufficient time for healthy tissue to reject the benzochlorin or the like, examining the patient under illumination which causes residual benzochlorin or the like to fluoresce, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR1## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R 3 ) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.

Claim 2

A method for detecting diseased tissue which comprises administering intravenously, intramuscularly, subcutaneously or topically to a human or animal patient an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, and, after sufficient time for healthy tissue to reject the benzochlorin or the like, examining the patient under illumination which causes residual benzochlorin or the like to fluoresce, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR1## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R 3 ) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.

Claim 3

A method for treating a human or animal patient who has diseased tissue, which method comprises administering to the patient, intravenously, intramuscularly, subcutaneously or topically, an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, and, after sufficient time for healthy tissue to reject the benzochlorin or the like, irradiating the diseased tissue with light of a wave length which causes a reaction which destroys the diseased tissue, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR2## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R3) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.

Claim 4

A method for treating a human or animal patient who has diseased tissue, which method comprises administering to the patient, intravenously, intramuscularly, subcutaneously or topically, an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, and, after sufficient time for healthy tissue to reject the benzochlorin or the like, irradiating the diseased tissue with light of a wave length which causes a reaction which destroys the diseased tissue, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR2## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R3) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.

Claim 5

A method for treating blood and other body fluids and tissues which comprises in vitro irradiation of the body fluid or tissue and an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, the irradiation being with light of a wavelength at which the benzochlorin, benzochlorin metal complex, verdin, verdin metal complex, porphyrin derivative or porphyrin derivative metal complex has an absorbance peak, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR3## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R 3 ) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.

Claim 6

A method for treating blood and other body fluids and tissues which comprises in vitro irradiation of the body fluid or tissue and an effective amount of a benzochlorin, a benzochlorin metal complex, a verdin, a verdin metal complex, a porphyrin derivative or a porphyrin derivative metal complex, the irradiation being with light of a wavelength at which the benzochlorin, benzochlorin metal complex, verdin, verdin metal complex, porphyrin derivative or porphyrin derivative metal complex has an absorbance peak, wherein the benzochlorin has the structure of FIG. 3, the metal complex of a benzochlorin has the structure of FIG. 1, the verdin has the structure of FIG. 4, the metal complex of a verdin has the structure of FIG. 2, the porphyrin derivative has the structure of FIG. 9, and the metal complex of a porphyrin derivative has the structure of FIG. 10: ##STR3## wherein M is a metal cation that is complexed with two of the nitrogens of the benzochlorin, verdin or porphyrin derivative and is Ag, Al, Ce, Co, Cr, Cu, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, Mo, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, R13 is an alkyl group having from 1 to 4 carbons, and each of R1 through R8, R10 through R12 and R14 is H or CHO, an alkyl group other than t-butyl having from 1 to 4 carbon atoms, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R 3 ) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl radical having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion, and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, or CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' where R' is H, or an alkyl group other than t-butyl having from one to four carbon atoms, with the proviso that R14 can be SO 3 H or a salt thereof and that not more than one of R1 through R8, R10 through R12 and R14 is CHO, a group having the formula R 2 N(R 3 ) 2 or a group having the formula R 2 N(R 4 ) 3 A.