Biologically active methylene blue derivatives

• US 8,188,074 B2
• Filed: 05/12/2008
• Issued: 05/29/2012
• Est. Priority Date: 05/30/2001
• Status: Expired due to Fees

• Current Assignee: Stanley Beames Brown, Stephen John Lyon
• Original Assignee: Photopharmica Limited
• Inventors: Brown, Stanley Beames, O'Grady, Cassandra Claire, Griffiths, John, Mellish, Kirste Joanne, Vernon, David Ian
• Primary Examiner(s): DRAPER, LESLIE A ROYDS
• Application Number:
  US12/149,996
• Publication Number:
  US 20080312219A1
• Time in Patent Office: 1,478 Days
• Field of Search: None
• US Class Current: 514/224.8
• 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: A61K 49/003 Thiazine dyes
• CPC Class Codes: A61K 8/4986 with sulfur as the only hetero atom
• CPC Class Codes: A61L 2/0029 Radiation
• CPC Class Codes: A61L 2/0082 using chemical substances
• CPC Class Codes: A61L 2/08 Radiation
• CPC Class Codes: A61L 2/232 layered or coated
• CPC Class Codes: A61P 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/02 Local antiseptics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61Q 11/00 : Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• CPC Class Codes: C07D 279/18 : [b, e]-condensed with two six-membered rings

Abstract

The present invention relates to a composition which includes a moiety of formula

• • wherein R1, R2, R3 and R4 each represent n-pentyl, and to a method of sterilizing a su fluid using same.

Claims

1. A composition comprising a compound of formula

2. The composition according to claim 1, which includes a delivery vehicle or excipient selected from alcohols, dimethyl sulphoxide, water, saline, solubilisers, isotonising agents, pH regulators, dyes, gelling agents, thickeners, buffers and combinations thereof.

3. The composition according to claim 2, wherein one of said isotonising agents is selected from urea, glycerol, aminoethanol and propylene glycol.

4. The composition according to claim 1, wherein said compound is present at a concentration in the range of 0.0005 to 20 wt %.

5. The composition according to claim 1, wherein said compound is present at a concentration in the range of 100 μ

M to 30 mM.

6. A composition comprising a compound of formula

7. A composition comprising a compound of formula

8. The composition according to claim 7, which includes a delivery vehicle or excipient selected from alcohols, dimethyl sulphoxide, water, saline, solubilisers, isotonising agents, pH regulators, dyes, gelling agents, thickeners, buffers and combinations thereof.

9. The composition according to claim 8, wherein one of said solubilisers is a castor oil derivative.

10. The composition according to claim 8, wherein one of said isotonising agents is selected from urea, glycerol, aminoethanol and propylene glycol.

11. A composition comprising a compound of formula

12. The composition according to claim 11 wherein said counterion is selected from the group consisting of F⁻

, Br⁻

, Cl⁻

, I⁻

, NO₃⁻

, SCN⁻

, ClO₃⁻

, ClO₄⁻

, IO₃⁻

, BF₄⁻

, HSO₄⁻

, H₂PO₄⁻

, CH₃SO₄⁻

, N₃⁻

, SO₄²⁻

, HPO₄²⁻

, PO₄³⁻

, acetate, lactate, citrate, tartrate, glycolate, glycerate, glutamate, β

-hydroxyglutamate, glucouronate, gluconate, malate and aspartate.

13. The composition according to claim 11 wherein said counterion is selected from the group consisting of Cl⁻

, Br⁻

, I⁻

, F⁻

, NO₃⁻

, HSO₄⁻

, CH₃CO₂⁻

, SO₄²⁻

, HPO₄²⁻

and PO₄³⁻

.

14. The composition according to claim 11 wherein said counterion is selected from the group consisting of Cl⁻

, Br⁻

and I⁻

.

15. A composition comprising a compound of formula