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US4497790A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for forming cationic technetium complexes useful as radiodiagnostic agents

Assignee: Bristol Myers Squibb Pharma Co
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Filing: 1982-09-03
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Granted: 1985-02-05
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Expires: 2002-09-03
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Abstract

Abstract The present invention relates to methods for making cationic radiodiagnostic agents and, in particular, to methods for preparing 99mTc-labelled cationic radiodiagnostic agents.

Inventors

  • 👤 Manuel S. Rodriguez

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 07:20
CPC Classifications
A; A61; A61K; A61K51/00; A61K51/02; A61K51/04; A61K2123/00

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 424 words
A method for preparing cationic lipophilic technetium complexes for radiodagnostic imaging, said method comprising (1) admising 99m Tc-pertechnetate with a target-seeking ligand or aqueous salt thereof, said ligand having the following structure: ##STR9## wherein: i is an integer from 1 to 6; R, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups, and R plus R i may be taken together to form a cyclic compound or separately to form a linear compound; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; A 1 , A 2 , A 3 , A 4 , A 5 and A 6 are each, independently, a donor atom having a free-electron pair available for complexing with Tc-99m or Tc-99 to form a cationic complex; and k 1 , k 2 , k 3 , k 4 , k 5 and k 6 are each independently zero or one; or ##STR10## wherein: R, R' and R" are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocylcloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; X and X' are saturated or unsaturated alkyl groups; A, A' and A" are independently selected from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99 to form a cationic complex; t and t' are independently 0 or 1; n is 0, 1 or 2; and n' and n" are independently the integer 1 or 2; or ##STR11## wherein R, R', R" and R'" are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; A', A" and A'" are independently selected from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99 to form a cationic complex; B is an atom from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99, boron, or from the elements of Group IV A of the periodic table; m is 0 or 1; and n, n', n" and n'" are independently the integer 1 or 2; and (2) heating the admixture to a temperature greater than 100° C. for a suitable length of time to complete the labelling reaction.
Claim 2
Independent Claim 424 words
A method for preparing cationic lipophilic technetium complexes for radiodagnostic imaging, said method comprising (1) admising 99m Tc-pertechnetate with a target-seeking ligand or aqueous salt thereof, said ligand having the following structure: ##STR9## wherein: i is an integer from 1 to 6; R, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups, and R plus R i may be taken together to form a cyclic compound or separately to form a linear compound; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; A 1 , A 2 , A 3 , A 4 , A 5 and A 6 are each, independently, a donor atom having a free-electron pair available for complexing with Tc-99m or Tc-99 to form a cationic complex; and k 1 , k 2 , k 3 , k 4 , k 5 and k 6 are each independently zero or one; or ##STR10## wherein: R, R' and R" are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocylcloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; X and X' are saturated or unsaturated alkyl groups; A, A' and A" are independently selected from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99 to form a cationic complex; t and t' are independently 0 or 1; n is 0, 1 or 2; and n' and n" are independently the integer 1 or 2; or ##STR11## wherein R, R', R" and R'" are independently selected from hydrogen or substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl, monocycloalkyl, polycycloalkyl, heterocyclic and carbocyclic groups; A', A" and A'" are independently selected from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99 to form a cationic complex; B is an atom from the group of donor atoms having a pair of electrons available for complexing with Tc-99m or Tc-99, boron, or from the elements of Group IV A of the periodic table; m is 0 or 1; and n, n', n" and n'" are independently the integer 1 or 2; and (2) heating the admixture to a temperature greater than 100° C. for a suitable length of time to complete the labelling reaction.
Claim 3
Dependent Claim 30 words
The method of claim 1 wherein each A is selected from the group consisting of P, As, N, O, S, Sb, Se and Te, thus obtaining a technetium-labelled radiodiagnostic agent.
Claim 4
Dependent Claim 20 words
The method of claim 1 wherein said temperature is in the range of about 130° C. to about 150° C.
Claim 5
Dependent Claim 67 words
The method of claim 1 wherein said target-seeking ligand has the formula: ##STR12## wherein M and M' are arsenic, phosphorus, nitrogen, sulfur, oxygen, selenium, tellurium, or any combination of them, n and n' are independently 1 or 2 depending upon the particular M and M', and R and R' are independently hydrogen, an alkyl group having from 1 to about 5 carbon atoms, or an aryl group.
Claim 6
Dependent Claim 69 words
The method of claim 1 wherein said target-seeking ligand has the formula: R'.sub.n' M'--CX'.sub.2 CX.sub.2 --MR.sub.n wherein M and M' are arsenic, phosphorus, nitrogen, sulfur, oxygen, selenium, tellurium, or any combination of them, n and n' are independently 1 or 2 depending on the particular M and M', R and R' are independently hydrogen, halide, an alkyl group having 1 to about 6 carbon atoms, or an aryl group.
Claim 7
Dependent Claim 78 words
The method of claim 1 wherein said target-seeking ligand has the formula: ##STR13## wherein M, M' and M" are independently selected from arsenic, phosphorous, nitrogen, sulfur, oxygen, selenium, and tellurium, n is 0 or 1 and n' and n" are independently 1 or 2 depending upon the particular M, M' and M" used, and R, R' and R" are independently selected from hydrogen, halide, an alkyl group having 1 to about 6 carbon atoms, or an aryl group.
Claim 8
Dependent Claim 39 words
The method of claim 1 wherein said target-seeking ligand has the formula: ##STR14## wherein A is P or As; and each R is independently H, a lower alkyl group having from 1 to about 6 carbon atoms, or phenyl.
Claim 9
Dependent Claim 13 words
The method of claim 1 wherein said target-seeking ligand has the formula: ##STR15##
Claim 10
Dependent Claim 29 words
The method of claim 1 wherein said target-seeking ligand has the formula: ##STR16## wherein R is H or a lower alkyl group having 1 to about 6 carbon atoms.
Claim 11
Dependent Claim 21 words
The method of claim 1 wherein said admixture is heated for a period of from about 5 to about 30 minutes.
Claim 12
Dependent Claim 17 words
The method of claim 1 wherein said admixture is heated to a temperature of about 150° C.
Claim 13
Dependent Claim 21 words
The method of claim 11 wherein said admixture is heated for a period of from about 5 to about 10 minutes.
Claim 14
Dependent Claim 18 words
The method of claim 1 wherein said admixture is heated to a temperature of at least 130° C.
Claim 15
Dependent Claim 20 words
The method of claim 1 wherein said target-seeking ligand is selected from the group consisting of dimethylphosphinoethane, diethylphosphinoethane, and dimethylphosphinopropane.

References Cited (Backward Citations)

US2587805A Cited
US4338248A Cited
US4363793A Cited
EP0038756A2 Cited
US4387087A Cited
US4451450A Cited
US4374821A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-02-05 1988-08-06 1989-02-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-02-05 1992-08-06 1993-02-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-02-05 1996-08-06 1997-02-05 $7700.00 Window Closed / Lapsed

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