Delta.sup.1,6 bicyclo 4,4,0! functional dyes for contrast enhancement in optical imaging
First Claim
1. A diagnostic composition comprising a compound of the formula:
- ##STR6## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--;
R3 and R4 may be the same or different and are selected from the group consisting of C1 -C10 alkyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkyl sulfonate, mercapto alkyl and --(CH2)m N(R6)(R7);
W1 and W2 may be the same or different and are selected from the group consisting of --S--, --O--, --Se--, --Te--, --NR8 and C(R9)(R10); and
m is about 0-10;
R8, R9, and R10 are independently hydrogen, C1 -C10 alkyl, C1 -C10 alkoxy, C1 -C10 mercaptoalkyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkoxycarbonyl, C1 -C10 alkylthio, and --(CH2)m --N(R6)(R7); and
A is selected from the group consisting of --(CH2)--, --O--, --S--, or --NR8.
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Accused Products
Abstract
This invention provides functional dyes of the general formula: ##STR1## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--; R3 and R4 may be the same or different and are selected from the group consisting of C1 -C10 alkyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkyl sulfonate, mercapto alkyl and --(CH2)m N(R6)(R7); W1 and W2 may be the same or different and are selected from the group consisting of --S--, --O--, --Se--, --Te--, --NR8 and C(R9)(R10); and m is about 0-10; R8, R9, and R10 are independently hydrogen, C1 -C10 alkyl, C1 -C10 alkoxy, C1 -C10 mercaptoalkyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkoxycarbonyl, C1 -C10 alkylthio, and --(CH2)m --N(R6)(R7); and A is selected from the group consisting of --(CH2)--, --O--, --S--, or --NR8. Also provided are methods of using dyes of the invention comprising administering a diagnostically effective amount of the dye to a patient and visualizing the dye.
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Citations
10 Claims
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1. A diagnostic composition comprising a compound of the formula:
- ##STR6## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--;
R3 and R4 may be the same or different and are selected from the group consisting of C1 -C10 alkyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkyl sulfonate, mercapto alkyl and --(CH2)m N(R6)(R7);
W1 and W2 may be the same or different and are selected from the group consisting of --S--, --O--, --Se--, --Te--, --NR8 and C(R9)(R10); and
m is about 0-10;
R8, R9, and R10 are independently hydrogen, C1 -C10 alkyl, C1 -C10 alkoxy, C1 -C10 mercaptoalkyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkoxycarbonyl, C1 -C10 alkylthio, and --(CH2)m --N(R6)(R7); and
A is selected from the group consisting of --(CH2)--, --O--, --S--, or --NR8. - View Dependent Claims (2, 3, 4, 5)
- ##STR6## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--;
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6. A method of imaging a patient comprising the administration of a diagnostically effective amount of a compound of the formula:
- ##STR7## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--;
R3 and R4 may be the same or different and are selected from the group consisting of C1 -C10 alkyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkyl sulfonate, mercapto alkyl and --(CH2)m N(R6)(R7);
W1 and W2 may be the same or different and are selected from the group consisting of --S--, --O--, --Se--, --Te--, --NR8 and C(R9)(R10); and
m is about 0-10;
R8, R9, and R10 are independently hydrogen, C1 -C10 alkyl, C1 -C10 alkoxy, C1 -C10 mercaptoalkyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, C1 -C10 carboxylalkyl, C1 -C10 alkoxycarbonyl, C1 -C10 alkylthio, and --(CH2)m --N(R6)(R7); and
A is selected from the group consisting of --(CH2)--, --O--, --S--, or --NR8. - View Dependent Claims (7, 8, 9, 10)
- ##STR7## wherein R1, R2, and R5 may be the same or different and are selected from the group consisting of hydrogen, C1 -C10 alkyl, C1 -C10 alkoxyl, hydroxyl, C1 -C10 hydroxyalkyl, C1 -C10 alkoxyalkyl, C1 -C10 aryl, carboxyl, C1 -C10 carboxylalkyl, halogen, nitro, C1 -C10 alkoxycarbonyl, mercapto, C1 -C10 mercaptoalkyl, C1 -C10 alkylthio, sulfonate, and --(CH2)m --N(R6)(R7) wherein R6 and R7 are independently hydrogen or C1 -C10 alkyl, C1 -C10 acyl, and R6 and R7 are capable of forming 5, 6, or 7 membered rings which may optionally be substituted with --O--, --NR8, or --S--;
Specification
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- Resources
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Current AssigneeMallinckrodt Medical Inc. (Mallinckrodt plc)
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Original AssigneeMallinckrodt Medical Inc. (Mallinckrodt plc)
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InventorsRajagopalan, Raghavan, Fung, Ella Y.
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Primary Examiner(s)Kight, John
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Assistant Examiner(s)JONES, DAMERON LEVEST
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Application NumberUS08/649,850Time in Patent Office505 DaysField of Search424/1.11, 424/1.65, 424/9.1, 424/9.3, 424/9.4, 424/9.6, 424/9.5, 424/9.44, 424/9.361, 546/184, 546/249, 546/152, 548/100, 548/400US Class Current424/9.6CPC Class CodesA61K 49/0021 the fluorescent group being...A61K 49/0032 Methine dyes, e.g. cyanine ...G01N 33/52 Use of compounds or composi...
