Acetylene-cumulene porphycene compounds for photodynamic therapy

• US 5,132,101 A
• Filed: 09/06/1990
• Issued: 07/21/1992
• Est. Priority Date: 05/04/1990
• Status: Expired due to Fees

• Current Assignee: Cytopharm, Inc.
• Original Assignee: Cytopharm, Inc.
• Inventors: Boehm, Stefan, Hennig, Wolfgang, Jux, Norbert, Rodriguez-Val, Eduardo, Vogel, Emanuel, Cross, Alexander D.
• Primary Examiner(s): Bond, Robert T.
• Assistant Examiner(s): WARD, EDWARD C
• Application Number:
  US07/578,346
• Time in Patent Office: 684 Days
• Field of Search: 540/472, 514/410, 424/9, 604/20
• US Class Current: 514/410
• CPC Class Codes: A61K 41/0076 PDT with expanded (metallo)porphyrins, i.e. having more than 20 ring atoms, e.g. texaphyrins, sapphyrins, hexaphyrins, pentaphyrins, porphocyanines
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings

Abstract

Dihydro- and tetrahydro-acetylene-cumulene porphycene compounds having the structure shown below ##STR1## are useful as photogynamic therapy agents.

Claims

1. An acetylene-cumulene porphycene compound having the structure shown below:

##STR13## wherein R is C_6-20 aryl, straight-chain or branched C_1-20 alkyl or alkoxyalkyl of the formula R'"'"'--O--(CH₂)_x --, where R'"'"' is C_1-6 alkyl and x is 1-6.

2. The compound of claim 1, wherein R is C_1-10 alkyl.

3. The compound of claim 1, wherein R is C_1-6 alkyl.

4. A compound having the structure shown below:

##STR14## wherein R is a C_6-20 aryl, straight-chain or branched C_1-20 alkyl or alkoxyalkyl of the formula R'"'"'--O--(CH₂)_x --, where R'"'"' is C_1-6 alkyl and x is 1-6.

5. The compound of claim 4, wherein R is C_1-10 alkyl.

6. The compound of claim 5, wherein R is C_1-6 alkyl.

7. A pharmaceutical composition comprising an effective amount of a compound having the structure shown below:

##STR15## wherein R is C_6-20 aryl, straight-chain or branched C_1-20 alkyl or alkoxyalkyl of the formula R'"'"'--O--(CH₂)_x -- where R'"'"' is C_1-6 alkyl, x is 1-6, and a pharmaceutically acceptable carrier.

8. The composition of claim 7, wherein R is C_1-10 alkyl.

9. The composition of claim 8, wherein R is C_1-6 alkyl.

10. The composition of claim 7, wherein said carrier is a penetrating solvent which enhances percutaneous penetration of said compound.

11. A method of photodynamic therapy, comprising the steps of

administering to a mammal in need thereof, an effective amount of a having the formula shown below:

##STR16## wherein R is C_6-20 aryl, straight-chain or branched C_1-20 alkyl, or alkoxyalkyl of the formula R'"'"'--O--(CH₂)_x --, where R'"'"' is C_1-6 alkyl and x is 1-6, and

irradiating said animal with light at a wavelength in the absorption spectrum of said reduced acetylene-cumulene porphycene.

12. The method of claim 11, wherein said administering is topical administration.

13. The method of claim 11, wherein said administering is enteral, parenteral, intramuscular or oral administration.