US2020262829A1PendingUtilityA1
Novel Compounds for Imaging Tau Proteins That Accumulate in the Brain
Assignee: NATIONAL INSTITUTES FOR QUANTUM AND RADIOLOGICAL SCIENCE AND TECHPriority: Dec 21, 2012Filed: Feb 21, 2020Published: Aug 20, 2020
Est. expiryDec 21, 2032(~6.4 yrs left)· nominal 20-yr term from priority
A61K 49/0021C07D 277/64C07D 417/06C07F 7/1804C07D 401/06C07D 405/06A61K 51/00C07D 401/14A61P 25/28A61K 49/10C07D 417/14A61K 49/0017C07D 405/14C07B 2200/05
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Claims
Abstract
The present invention provides a compound represented by the following formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof. wherein: R 1 and R 2 are each separately selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl; R 3 is hydrogen or halogen; ring A is a benzene ring or a pyridine ring; ring B is selected from the group consisting of the following formulas (i), (ii), (iii), and (iv): in the formula (ii), R a is alkyl; R 4 and R 5 are each separately selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl; and [Formula 3] represents a double bond or a triple bond. The above compound can be used as a molecular probe for imaging tau proteins that accumulate in the brain.
Claims
exact text as granted — not AI-modified1 . A compound of Formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof:
wherein:
R 1 and R 2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl;
R 3 is hydrogen or halogen;
ring A is a benzene ring or a pyridine ring;
ring B is selected from the group consisting of the following formulas (i), (ii), (iii), and (iv):
in the formula (ii), R a is alkyl;
R 4 and R 5 are each separately selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl, wherein R 4 and R 5 are not simultaneously hydrogen if ring B is formula (i) or (ii);
and represents a double bond or a triple bond.
2 . The compound according to claim 1 , wherein ring B is formula (i) or (ii).
3 . The compound according to claim 1 , wherein ring A is a pyridine ring.
4 . The compound according to claim 3 , represented by the following formula (II):
wherein R 1 to R 5 and are defined in claim 1 .
5 . The compound according to claim 4 , wherein represents a double bond.
6 . The compound according to claim 4 , wherein represents a triple bond.
7 . The compound according to claim 1 , wherein ring A is a benzene ring.
8 . The compound according to claim 7 , represented by the following formula (III):
wherein R 1 to R 5 and are defined in claim 1 .
9 . The compound according to claim 8 , wherein represents a double bond.
10 . The compound according to claim 8 , wherein represents a triple bond.
11 . The compound according to claim 7 , represented by the following formula (IV):
wherein R 1 to R 5 , R a and are defined in claim 1 .
12 . The compound according to claim 11 , wherein represents a double bond.
13 . The compound according to claim 11 , wherein represents a triple bond.
14 . The compound according to claim 1 , wherein ring B is formula (iii).
15 . The compound according to claim 14 , represented by the following formula (V):
wherein R 1 to R 5 and are defined in claim 1 .
16 . The compound according to claim 15 , wherein represents a double bond.
17 . The compound according to claim 15 , wherein represents a triple bond.
18 . The compound according to claim 1 , wherein ring B is formula (iv).
19 . The compound according to claim 14 , represented by the following formula (VI):
wherein R 1 to R 5 and are defined in claim 1 .
20 . The compound according to claim 19 , wherein represents a double bond.
21 . The compound according to claim 19 , wherein represents a triple bond.
22 . A compound, a pharmaceutically acceptable salt thereof, or a solvate thereof, selected from the following group:
23 . The compound according to claim 1 , wherein one or more atoms are a radioisotope of the atom or atoms.
24 . A composition comprising a compound according to claim 1 , and a pharmaceutically acceptable carrier.
25 . A composition for tau imaging, comprising a compound of represented formula (I),
wherein:
R 1 and R 2 are each separately selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl;
R 3 is hydrogen or halogen;
ring A is a benzene ring or a pyridine ring;
ring B is selected from the group consisting of the following formulas (i), (ii), (iii), and (iv):
in the formula (ii), R a is alkyl;
R 4 and R 5 are each separately selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl; and represents a double bond or a triple bond;
or a pharmaceutically acceptable salt thereof, or a solvate thereof; and a pharmaceutically acceptable carrier.
26 . The composition for tau imaging according to claim 25 , wherein, in the compound, one or more atoms are a radioisotope of the atom or atoms.
27 . An intermediate for synthesizing the compound according to the formula (I), represented by one of the following formula (I-i), (I-ii), (I-i) protector 1, (I-i) protector 2, (a6) protector, (a7), (a8-1), or (a8-2):
wherein R 3 , R 4 , R 5 and are defined in claim 1 .
28 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (I-ii):
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and are defined in claim 1 .
29 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (I-i) protector 1:
wherein R 3 , R 5 and are defined in claim 1 .
30 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (I-i) protector 2:
wherein R 3 , R 5 , and are defined in claim 1 .
31 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (a6) protector:
wherein R 1 , R 5 , and are defined in claim 1 .
32 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (a7):
wherein R 1 to R 3 , R 5 , and are defined in claim 1 .
33 . The intermediate of claim 27 for synthesizing the compound according to the formula (I), represented by the following formula (a8-1) or (a8-2):
wherein R 1 to R 3 , R 5 , and are defined in claim 1 , and Alk is alkyl.
34 . The intermediate of claim 27 for synthesizing the compound according to claim 1 , selected from the following group:Join the waitlist — get patent alerts
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