Boron difluoride compounds useful in photodynamic therapy and production of laser light

• US 5,446,157 A
• Filed: 02/19/1993
• Issued: 08/29/1995
• Est. Priority Date: 04/23/1990
• Status: Expired due to Fees

• Current Assignee: BO-DEKK Ventures, Ltd.
• Original Assignee: BO-DEKK Ventures, Ltd.
• Inventors: Boyer, Joseph H., Morgan, Lee R.
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US08/020,293
• Time in Patent Office: 921 Days
• Field of Search: 514/64, 548/405, 548/110, 546/13
• US Class Current: 546/13
• CPC Class Codes: A61K 31/69 Boron compounds
• CPC Class Codes: A61K 41/0057 Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
• CPC Class Codes: C07F 5/022 without C-boron linkages
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09K 11/06 containing organic luminescent materials

Abstract

A new group of fluorescent organic compounds having a variety of uses are described. They are especially useful as dye compounds in dye laser systems, and as photochemical agents in the treatment of diseased tissues using photodynamic therapy techniques. The compounds include a tri-cyclic compound having the following structure: ##STR1## Preferably R₁ -R₅ ═R₉ -R₁₂ ═C; R₇ ═B; R₆ and R₈ ═N; R₁₄ ═lower n-alkyl or an electron withdrawing group such as CN^- ; R₁₆ and R₁₉ are independently selected from the group consisting of lower n-alkyl, a sulfate or an acid or salt thereof, or hydrogen; and R₂₀ ═R₂₁ ═F. Other compounds include compounds of the formula ##STR2##

Claims

1. A compound selected from the group consisting of:

(a) ##STR50## wherein R is H or lower alkyl;

(b) ##STR51## wherein X is CH or N, Y is CH or N, and R is lower alkyl, where at least one of X and Y is N; and

(c) α

,α

'"'"'-dipyridylmethane-BF₂.

2. The compound of claim 1 wherein the compound is

(a) ##STR52## wherein R is H or lower alkyl;

or (b) ##STR53## wherein X is CH, Y is N, and R is lower alkyl, where at least one of X and Y is N.

3. The compound of claim 2 wherein the compound is 2(a).

4. The compound of claim 2 wherein the compound is 2(b).

5. An imidazomethene-BF₂ complex according to the formula ##STR54## wherein R₁ and R₄ are H or lower alkyl and R₂ and R₃ are CH₃ ;

or R₁ -R₄ are lower alkyl.

6. The compound of claim 5 wherein the compound is tetramethyl-2,2'"'"'-biimidazole-BF₂.