IP Library › Patent Application 16798226
Patent Application
App. No. 16/798,226

Novel Compounds for Imaging Tau Proteins That Accumulate in the Brain

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Quick Facts
Patent No.
US None
App. No.
16/798,226
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 (62)

1 . 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: