IP Library › Granted Patent US 10,533,024

Granted Patent B2

US 10,533,024 · App. 16/125,190 · Granted Jan 14, 2020

Methods for synthesizing metal mesoporphyrins

Inventors: Christopher P. Boucher (Newmarket, CA); David Roe (Rockwood, CA)

Assignee: MALLINCKRODT HOSPTIAL PRODUCTS IP LIMITED

C07F7/2284 C07D487/22

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Quick Facts

Patent No.: US 10,533,024
App. No.: 16/125,190
Granted: Jan 14, 2020
Kind: B2

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Abstract

Embodiments describe methods of synthesizing metal mesoporphyrin compounds. In embodiments, a metal mesoporphyrin compound may be formed by hemin transmetallation and subsequent hydrogenation of the tin protoporphyrin IX to form a metal mesoporphyrin. In other embodiments, a method of synthesizing a metal mesoporphyrin compound comprises forming a protoporphyrin methyl ester from hemin and converting the protoporphyrin methyl ester intermediate to a metal mesoporphyrin compound through metal insertion and hydrogenation. In other embodiments, a metal mesoporphyrin compound may be formed from hemin by a hydrogen-free hydrogenation method to form a mesoporphyrin IX intermediate followed by metal insertion and hydrogenation. In embodiments, a method of synthesizing a metal mesoporphyrin compound comprises forming a mesoporphyrin IX dihydrochloride intermediate compound and converting the mesoporphyrin IX intermediate to a metal mesoporphyrin compound through metal insertion. In embodiments, a metal mesoporphyrin compound may be formed directly from hemin without isolation of any intermediates.

Claims (7)

1. A method of synthesizing a metal mesoporphyrin compound comprising:

hydrogenating hemin with ferrous sulfate, palladium on carbon, and poly(methylhydrosiloxane) in formic acid to form a mesoporphyrin formate; converting the mesoporphyrin formate to a mesoporphyrin IX dihydrochloride intermediate compound;

isolating the mesoporphyrin IX dihydrochloride intermediate compound; and inserting a metal into the mesoporphyrin IX dihydrochloride intermediate.

2. The method of claim 1 , wherein the metal may be selected from tin, iron, zinc, chromium, manganese, copper, nickel, magnesium, cobalt, platinum, gold, silver, arsenic, antimony, cadmium, gallium, germanium, and palladium.

3. The method of claim 2 , wherein the metal is tin.

4. The method of claim 3 , wherein the tin is inserted using tin oxide, tin chloride, tin sulfate, tin bromide, tin oxalate, tin pyrophosphate hydrate, tin 2-ethylhexanoate, tin methanesulfonic acid, or tin trifluromethanesulfonate.

5. The method of claim 1 , wherein the metal mesoporphyrin compound is stannsoporfin.

Assignments (15)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2026

From: MALLINCKRODT HOSPITAL PRODUCTS IP UNLIMITED COMPANY

To: MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED

Reel/Frame 075393/0058 →

RELEASE OF SECURITY INTEREST Recorded Aug 14, 2025

From: ACQUIOM AGENCY SERVICES LLC

To: SPECGX LLC; MALLINCKRODT ENTERPRISES LLC; MALLINCKRODT LLC; MALLINCKRODT PHARMA IP TRADING UNLIMITED COMPANY; MALLINCKRODT PHARMACEUTICALS IRELAND LIMITED; OCERA THERAPEUTICS LLC; STRATATECH CORPORATION; SUCAMPO PHARMA AMERICAS LLC; VTESSE LLC

Reel/Frame 072324/0740 →

RELEASE OF PATENT SECURITY INTERESTS RECORDED AT REEL 049822, FRAME 0674 Recorded Nov 16, 2023

From: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT

To: 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; THERAKOS, INC.; IKARIA THERAPEUTICS LLC; INO THERAPEUTICS LLC

Reel/Frame 065609/0454 →

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 →

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

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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

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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 →

SECURITY INTEREST Recorded Jun 17, 2022

To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS SECOND LIEN COLLATERAL AGENT

Reel/Frame 060389/0913 →

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 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 →

NOTICE OF GRANT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jul 22, 2019

From: MALLINCKRODT HOSPITAL PRODUCTS IP LIMITED

To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT

Reel/Frame 049822/0674 →

NUNC PRO TUNC ASSIGNMENT Recorded May 24, 2019

From: INFACARE PHARMACEUTICAL CORPORATION

To: MALLINCKRODT PHARMA IP TRADING D.A.C.

Reel/Frame 049274/0943 →

NUNC PRO TUNC ASSIGNMENT Recorded May 24, 2019

From: MALLINCKRODT IP UNLIMITED COMPANY