Abstract A group of hydro-dibenzoporphyrins prepared by di-Diels-Alder additions at the A and C rings of the appropriate divinyl porphyrins have absorption maxima in the range of 700-820 nanometers and are photosensitizing agents. These compounds are useful in treating disorders or conditions which are subject to hematoporphyrin derivative (HPD) treatment in the presence of light, or in treating biological materials generally to destroy unwanted targets such as viruses, cells and tissues. The use of the compounds of the invention permits irradiation with wavelengths other than those absorbed by blood. The compounds of the invention may also be conjugated to ligands specific for receptors or to specific immunoglobulins or fragments thereof to home to target tissues or cells for the radiation treatment. Use of these materials permits lower levels of photosensitizer to be used, thus preventing side reactions which might destroy normal tissues.
A compound of the formulas 1-1 through 1-6 ##STR9## which compound is fluorescent and photosensitizing, wherein at least one of R 1 and R 2 is selected from the group consisting of carbalkoxy (2-6C); aryl (6-10C); alkyl (1-6C) or aryl (6-10C) sulfonyl; cyano; and --CONR 5 CO--, wherein R 5 is aryl (6-10C) or alkyl (1-6C); and the other R 1 and R 2 is selected from the group consisting of the aforesaid substituents and H; and wherein each R 3 and R 4 is independently selected from the group consisting of substituted or unsubstituted alkyl (1-6C); and substituted and unsubstituted omega-carboxyalkyl (2-6C) and the esters, amides, and salts thereof.
Claim 2
Dependent Claim
110 words
A compound of the formulas 1-1 through 1-6 ##STR9## which compound is fluorescent and photosensitizing, wherein at least one of R 1 and R 2 is selected from the group consisting of carbalkoxy (2-6C); aryl (6-10C); alkyl (1-6C) or aryl (6-10C) sulfonyl; cyano; and --CONR 5 CO--, wherein R 5 is aryl (6-10C) or alkyl (1-6C); and the other R 1 and R 2 is selected from the group consisting of the aforesaid substituents and H; and wherein each R 3 and R 4 is independently selected from the group consisting of substituted or unsubstituted alkyl (1-6C); and substituted and unsubstituted omega-carboxyalkyl (2-6C) and the esters, amides, and salts thereof.
Claim 3
Dependent Claim
16 words
The compound of claim 1 which is has the formula shown as 1-1, 1-3 or 1-5.
Claim 4
Dependent Claim
11 words
The compound of claim 1 wherein all R 4 are methyl.
Claim 5
Dependent Claim
22 words
The compound of claim 1 wherein each R 3 is unsubstituted alkyl or unsubstituted 1-carboxyalkyl or the ester, amide or salt thereof.
Claim 6
Dependent Claim
18 words
The compound of claim 4 wherein each R 3 is 1-carboxyalkyl or the ester, amide or salt thereof.
Claim 7
Dependent Claim
32 words
A pharmaceutical composition which is useful in targeting specific biological material which composition comprises an effective amount of the compound of claim 1 in admixture with at least one pharmaceutically acceptable excipient.