IP Library Granted Patent US 8,658,433
Granted Patent B2
US 8,658,433 · App. 11/931,683 · Granted Feb 25, 2014

Dye compounds as photoactive agents

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Quick Facts
Patent No.
US 8,658,433
App. No.
11/931,683
Granted
Feb 25, 2014
Kind
B2
Abstract

Novel azo, azide, and sulfenate photoactive compounds and methods using the compounds for photodiagnostic and/or phototherapeutic procedures. The compounds have the formula E-L-DYE-X—Y, wherein DYE is a photoactive component comprising a photoactive diagnostic agent, a photoactive type 1 agent, a photoactive type 2 agent, or a combination thereof; Y is a photoactive component comprising a photoactive type 1 agent, a photoactive type 2 agent, or a combination thereof; E is a targeting component for targeting the compound to an anatomical and/or physiological site of a patient; L is a linking component for linking E to DYE; and X is a linking component for linking DYE to Y.

Claims (20)

1. A compound of the formula

E-L-DYE-X—Y

for use in a medical phototherapeutic procedure, the compound used to cause at least one of necrosis or apoptosis of a target tissue, wherein:

DYE is a photoactive type 2 photodynamic therapy (PDT) agent that may further comprise a photoactive diagnostic agent, a photoactive type 1 phototherapeutic agent, another photoactive type 2 PDT agent, or a combination thereof wherein said type 2 PDT agent operates through a type 2 mechanism requiring formation of singlet oxygen for causing tissue damage;

Y is a photoactive type 1 phototherapeutic agent that may further comprise another photoactive type 1 phototherapeutic agent, a photoactive type 2 PDT agent, or a combination thereof wherein said type 1 phototherapeutic agent operates through a type 1 mechanism, does not require oxygen for tissue damage and comprises azide or sulfenate moities;

E is a targeting component for targeting the compound to an anatomical and/or physiological site of a patient;

L is a linking component for linking E to DYE where L is selected from the group consisting of —(CH 2 ) a —, —(CH 2 ) b CONR 1 —, —N(R 2 )CO(CH 2 ) c —, —OCO(CH 2 ) d —, —(CH 2 ) e CO 2 —, —OCONH—, —OCO 2 —, —HNCONH—, —HNCSNH—, —HNNHCO—, —OSO 2 —, —NR 3 (CH 2 ) e CONR 4 —, —CONR 5 (CH 2 ) f NR 6 CO—, and —NR 7 CO(CH 2 ) g CONR 8 —; and

X is a linking component for linking DYE to Y where X is selected from the group consisting of —(CH 2 ) h —, —HNCO—, —(CH 2 ) i CO—, and —(CH 2 ) j OCO— where a to j independently range from 0 to 10.

2. A method of using a compound in a medical phototherapeutic procedure, the method comprising:

administering a compound to a patient; and

exposing the administered compound to at least one of visible or infrared light while the compound is at least one of on or in the patient, the compound used to cause at least one of necrosis or apoptosis of a target tissue, wherein the compound is

E-L-DYE-X—Y

wherein:

DYE is a photoactive type 2 photodynamic therapy (PDT) agent that may further comprise a photoactive diagnostic agent, a photoactive type 1 phototherapeutic agent, another photoactive type 2 PDT agent, or a combination thereof wherein said type 2 PDT agent operates through a type 2 mechanism requiring formation of singlet oxygen for causing tissue damage;

Y is a photoactive type 1 phototherapeutic agent that may further comprise another photoactive type 1 phototherapeutic agent, a photoactive type 2 PDT agent, or a combination thereof wherein said type 1 phototherapeutic agent operates through a type 1 mechanism, does not require oxygen for tissue damage and comprises azide or sulfenate moities;

E is a targeting component for targeting the compound to an anatomical and/or physiological site of a patient;

L is a linking component for linking E to DYE where L is selected from the group consisting of —(CH 2 ) a —, —(CH 2 ) b CONR 1 —, —N(R 2 )CO(CH 2 ) c —, —OCO(CH 2 ) d —, —(CH 2 ) e CO 2 —, —OCONH—, —OCO 2 —, —HNCONH—, —HNCSNH—, —HNNHCO—, —OSO 2 —, —NR 3 (CH 2 ) e CONR 4 —, —CONR 5 (CH 2 ) f NR 6 CO—, and —NR 7 CO(CH 2 ) g CONR 8 —; and

X is a linking component for linking DYE to Y where X is selected from the group consisting of —(CH 2 ) h —, —OCO—, —HNCO—, —(CH 2 ) i CO—, and —(CH 2 ) j OCO—,

the method resulting in combined type 1 and type 2 therapy

where a to j independently range from 0 to 10.

Assignments (12)
RELEASE OF SECURITY INTEREST Recorded Aug 14, 2025
From: ACQUIOM AGENCY SERVICES LLC
To: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; OCERA THERAPEUTICS LLC; SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
Reel/Frame 072324/0740 →
RELEASE OF PATENT SECURITY INTERESTS RECORDED AT REEL 060434, FRAME 0536 Recorded Nov 16, 2023
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; VTESSE LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; SUCAMPO PHARMA AMERICAS LLC
Reel/Frame 065601/0347 →
RELEASE OF PATENT SECURITY INTERESTS RECORDED AT REEL 032480, FRAME 0001 Recorded Nov 16, 2023
From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
To: THERAKOS, INC.; MALLINCKRODT INTERNATIONAL FINANCE S.A.; MALLINCKRODT CB LLC; MALLINCKRODT FINANCE GMBH; MALLINCKRODT US HOLDINGS LLC (F/K/A MALLINCKRODT US HOLDINGS INC.); MALLINCKRODT CARRIBEAN, INC.; MALLINCKRODT US POOL LLC; MNK 2011 LLC (F/K/A MALLINCKRODT INC.); LUDLOW LLC (F/K/A LUDLOW CORPORATION); CNS THERAPEUTICS, INC.; MALLINCKRODT ENTERPRISES HOLDINGS LLC (F/K/A MALLINCKRODT ENTERPRISES HOLDINGS, INC.); MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; LAFAYETTE PHARMACEUTICALS LLC; LIEBEL-FLARSHEIM COMPANY LLC; MALLINCKRODT BRAND PHARMACEUTICALS LLC (F/K/A MALLINCKRODT BRAND PHARMACEUTICALS, INC.); MALLINCKRODT VETERINARY, INC.; MALLINCKRODT US HOLDINGS LLC; IMC EXPLORATION COMPANY; MEH, INC.; MALLINCKRODT HOSPITAL PRODUCTS IP UNLIMITED COMPANY (F/K/A MALLINCKRODT HOSPITAL PRODUCTS IP LIMITED); MALLINCKRODT ARD IP UNLIMITED COMPANY (F/K/A MALLINCKRODT ARD IP LIMITED); OCERA THERAPEUTICS LLC (F/K/A OCERA THERAPEUTICS, INC.); SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC (F/K/A VTESSE INC.); MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY (F/K/A MALLINCKRODT PHARMA IP TRADING D.A.C.); INFACARE PHARMACEUTICAL CORPORATION; ST SHARED SERVICES LLC; IKARIA THERAPEUTICS LLC; INO THERAPEUTICS LLC
Reel/Frame 065609/0322 →
RELEASE OF SECURITY INTERESTS IN PATENTS AT REEL 060389/FRAME 0913 Recorded Nov 15, 2023
From: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
To: OCERA THERAPEUTICS LLC (F/K/A OCERA THERAPEUTICS, INC.); MALLINCKRODT LLC; MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 065583/0465 →
SECURITY INTEREST Recorded Nov 15, 2023
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; OCERA THERAPEUTICS LLC; SPECGX LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC
To: ACQUIOM AGENCY SERVICES LLC
Reel/Frame 065595/0376 →
NOTICE OF GRANT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jun 22, 2022
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 060434/0536 →
RELEASE OF SECURITY INTEREST Recorded Jun 17, 2022
From: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
To: OCERA THERAPEUTICS, INC.; MALLINCKRODT LLC; MALLINCKRODT ARD IP UNLIMITED COMPANY (F/K/A MALLINCKRODT ARD IP LIMITED); MALLINCKRODT HOSPITAL PRODUCTS IP UNLIMITED COMPANY (F/K/A MALLINCKRODT HOSPITAL PRODUCTS IP LIMITED); MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY (F/K/A MALLINCKRODT PHARMA IP TRADING DESIGNATED ACTIVITY COMPANY); SPECGX LLC; STRATATECH CORPORATION; VTESSE LLC (F/K/A VTESSE INC.)
Reel/Frame 060389/0839 →
SECURITY INTEREST Recorded Jun 17, 2022
From: MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; SPECGX LLC; OCERA THERAPEUTICS, INC.; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 060389/0913 →
SECURITY INTEREST Recorded Dec 10, 2019
From: MALLINCKRODT ARD IP LIMITED; MALLINCKRODT HOSPITAL PRODUCTS IP LIMITED; SPECGX LLC; OCERA THERAPEUTICS, INC.; MALLINCKRODT PHARMA IP TRADING DESIGNATED ACTIVITY COMPANY; STRATATECH CORPORATION; VTESSE INC.; MALLINCKRODT LLC
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 051256/0829 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 13, 2017
From: MALLINCKRODT LLC
To: SPECGX LLC
Reel/Frame 044891/0376 →
SECURITY INTEREST Recorded Mar 19, 2014
From: MALLINCKRODT INTERNATIONAL FINANCE S.A.; MALLINCKRODT CB LLC; MALLINCKRODT FINANCE GMBH; MALLINCKRODT US HOLDINGS INC.; MALLINCKRODT CARIBBEAN, INC.; MALLINCKRODT US POOL LLC; MALLINCKRODT INC.; LUDLOW CORPORATION; CNS THERAPEUTICS, INC.; ENTERPRISES HOLDINGS, INC.; MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; LAFAYETTE PHARMACEUTICALS LLC; LIEBEL-FLARSHEIM COMPANY LLC; MALLINCKRODT BRAND PHARMACEUTICALS, INC; MALLINCKRODT VETERINARY, INC.; MALLINCKRODT US HOLDINGS LLC; IMC EXPLORATION COMPANY; MEH, INC; MALLINCKRODT ENTERPRISES HOLDINGS, INC.
To: DEUTSCHE BANK AG NEW YORK BRANCH
Reel/Frame 032480/0001 →
CHANGE OF LEGAL ENTITY Recorded Aug 16, 2011
From: MALLINCKRODT INC.
To: MALLINCKRODT LLC
Reel/Frame 026754/0001 →