IP Library Granted Patent US 9,023,315
Granted Patent B2
US 9,023,315 · App. 13/742,154 · Granted May 5, 2015

Tricarbonyl complexes with tridentate chelators for myocardium imaging

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Quick Facts
Patent No.
US 9,023,315
App. No.
13/742,154
Granted
May 5, 2015
Kind
B2
Abstract

Chelators of the formulae (I), (II) and (III) and tricarbonyl complexes of radioisotopes of Tc and Re bound to them, for use in myocardial imaging.

Claims (52)

1. A method of myocardial imaging, the method comprising,

(a) administering to a subject a radioisotopic tricarbonyl complex with a tridentate chelator chosen from a compound comprising Formula (I), (II), or (III):

wherein,

n is an integer selected from 1 or 2, and

at least one of R 1 , R 2 , R 3 , and R 4 is a linear or macrocyclic ether group of the type —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5), respectively,

and each of the other three R groups is independently hydrogen; a linear or branched, saturated or unsaturated C 1 to C 9 alkyl; a saturated or unsaturated carbocyclic group; a saturated or unsaturated heterocyclic or heteroaliphatic group with one or more atoms selected from O, N and S, wherein said carbocyclics, heterocyclics and heteroaliphatics are optionally substituted by one or more linear or branched, saturated or unsaturated C 1 to C 9 alkyls; an ether group —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5),

wherein R x and R Y are independently linear or branched, saturated or unsaturated C 1 to C 9 alkyl, or saturated or unsaturated carbocyclics, any of which alkyl and/or carbocyclic groups may be substituted or unsubstituted,

provided that when the tridentate chelator is of the type of formula (I), when R 1 is —R x —O—R Y wherein R Y is substituted, and R 2 , R 3 , and R 4 are each hydrogen, R Y is not substituted apically by a further tris(pyrazolyl)methane moiety; and when R 1 is —R x —O—R Y and R 2 , R 3 and R 4 are each hydrogen, R 1 cannot be —CH 2 —O—CH 2 -(p- t Bu-C 6 H 4 ); and

(b) evaluating the biodistribution of the radioisotopic tricarbonyl complex.

2. The method of claim 1 , wherein the biodistribution of the radioisotopic tricarbonyl complex is evaluated by SPECT or planar scintography.

3. The method of claim 1 , wherein administration is intravenous.

4. The method of claim 1 , wherein the radioisotopic tricarbonyl complex is selected from a Tc or Re radioisotopic tricarbonyl complex.

5. A method of myocardial imaging, the method comprising,

(a) administering to a subject a radioisotopic tricarbonyl complex with a tridentate chelator chosen from a compound comprising Formula (I):

wherein,

at least one of R 1 , R 2 , R 3 , and R 4 is a linear or macrocyclic ether group of the type —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5), respectively,

and each of the other three R groups is independently hydrogen; a linear or branched, saturated or unsaturated C 1 to C 9 alkyl; a saturated or unsaturated carbocyclic group; a saturated or unsaturated heterocyclic or heteroaliphatic group with one or more atoms selected from O, N and S, wherein said carbocyclics, heterocyclics and heteroaliphatics are optionally substituted by one or more linear or branched, saturated or unsaturated C 1 to C 9 alkyls; an ether group —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5),

wherein R x and R Y are independently linear or branched, saturated or unsaturated C 1 to C 9 alkyl, or saturated or unsaturated carbocyclics, any of which alkyl and/or carbocyclic groups may be substituted or unsubstituted,

provided that when R 1 is —R x —O—R Y wherein R Y is substituted, and R 2 , R 3 , and R 4 are each H, R Y is not substituted apically by a further tris(pyrazolyl)methane moiety; and when R 1 is —R x —O—R Y and R 2 , R 3 and R 4 are each H, R 1 cannot be —CH 2 —O—CH 2 -(p- t Bu-C 6 H 4 ); and

(b) evaluating the biodistribution of the radioisotopic tricarbonyl complex.

6. The method of claim 5 , wherein the biodistribution of the radioisotopic tricarbonyl complex is evaluated by SPECT or planar scintography.

7. The method of claim 5 , wherein administration is intravenous.

8. The method of claim 5 , wherein the radioisotopic tricarbonyl complex is selected from a Tc or Re radioisotopic tricarbonyl complex.

9. The method of claim 5 , wherein R1 is hydrogen; R2 and R4 are C 1 to C 3 alkyl; and R3 is the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl.

10. The method of claim 5 , wherein R1 and R3 are hydrogen, and R2 and R4 are the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl.

11. The method of claim 5 , wherein R1 is H and R2, R3, and R4 are the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl.

12. The method of claim 5 , wherein R1, R2, and R4 are hydrogen, and R3 is the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl.

13. The method of claim 5 , wherein R1 is the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl, and R2, R3, and R4 are hydrogen.

14. A method of myocardial imaging, the method comprising,

(a) administering to a subject a radioisotopic tricarbonyl complex with a tridentate chelator chosen from a compound comprising Formula (II):

wherein,

n is an integer selected from 1 or 2, and

at least one of R 1 , R 2 , R 3 , and R 4 is a linear or macrocyclic ether group of the type —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z =2-3, y=3-8, z=2-5), respectively,

and each of the other three R groups is independently hydrogen; a linear or branched, saturated or unsaturated C 1 to C 9 alkyl; a saturated or unsaturated carbocyclic group; a saturated or unsaturated heterocyclic or heteroaliphatic group with one or more atoms selected from O, N and S, wherein said carbocyclics, heterocyclics and heteroaliphatics are optionally substituted by one or more linear or branched, saturated or unsaturated C 1 to C 9 alkyls; an ether group —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5),

wherein R x and R Y are independently linear or branched, saturated or unsaturated C 1 to C 9 alkyl, or saturated or unsaturated carbocyclics, any of which alkyl and/or carbocyclic groups may be substituted or unsubstituted; and

(b) evaluating the biodistribution of the radioisotopic tricarbonyl complex.

15. The method of claim 14 , wherein the biodistribution of the radioisotopic tricarbonyl complex is evaluated by SPECT or planar scintography.

16. The method of claim 14 , wherein the radioisotopic tricarbonyl complex is selected from a Tc or Re radioisotopic tricarbonyl complex.

17. The method of claim 14 , wherein administration is intravenous.

18. The method of claim 14 , wherein n is equal to 1; R1 is the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl; and R2, R3, and R4 are hydrogen.

19. A method of myocardial imaging, the method comprising,

(a) administering to a subject a radioisotopic tricarbonyl complex with a tridentate chelator chosen from a compound comprising Formula (III):

wherein,

n is an integer selected from 1 or 2, and

at least one of R 1 , R 2 , R 3 , and R 4 is a linear or macrocyclic ether group of the type —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5), respectively,

and each of the other three R groups is independently hydrogen; a linear or branched, saturated or unsaturated C 1 to C 9 alkyl; a saturated or unsaturated carbocyclic group; a saturated or unsaturated heterocyclic or heteroaliphatic group with one or more atoms selected from O, N and S, wherein said carbocyclics, heterocyclics and heteroaliphatics are optionally substituted by one or more linear or branched, saturated or unsaturated C 1 to C 9 alkyls; an ether group —R x —O—R Y or [(CH 2 ) x O] y (CH 2 ) z (x=2-3, y=3-8, z=2-5),

wherein R x and R Y are independently linear or branched, saturated or unsaturated C 1 to C 9 alkyl, or saturated or unsaturated carbocyclics, any of which alkyl and/or carbocyclic groups may be substituted or unsubstituted, and

(b) evaluating the biodistribution of the radioisotopic tricarbonyl complex.

20. The method of claim 19 , wherein the biodistribution of the radioisotopic tricarbonyl complex is evaluated by SPECT or planar scintography.

21. The method of claim 19 , wherein the radioisotopic tricarbonyl complex is selected from a Tc or Re radioisotopic tricarbonyl complex.

22. The method of claim 19 , wherein administration is intravenous.

23. The method of claim 19 , wherein n is equal to 2; R1, R2, and R4 are the ether group —R x —O—R Y , where R x and R Y are linear C 1 to C 9 alkyl; and R 3 is hydrogen.

Assignments (4)
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 INTEREST Recorded Jan 31, 2017
From: DEUTSCHE BANK AG NEW YORK BRANCH
To: MALLINCKRODT NUCLEAR MEDICINE LLC
Reel/Frame 041131/0213 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2016
From: MALLINCKRODT LLC
To: MALLINCKRODT NUCLEAR MEDICINE LLC
Reel/Frame 039149/0234 →
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 →