Deuterated compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-10076581-B2
Application number	US-201615006997-A
Country	US
Kind code	B2
Filing date	Jan 26, 2016
Priority date	May 13, 2014
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

The present invention relates to deuterated and optionally detectably labeled compounds of formula (I) and formula (V):

and salts thereof, wherein R 1 , R 2 , A, and X 10 -X 19 have any of the values defined in the specification. Also included are pharmaceutical compositions comprising such compounds and salts, and methods of using such compounds and salts as imaging agents.

First claim

We claim:

1. A deuterated compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof, wherein each carbon marked * has a deuterium isotope enrichment factor of at least 3500.

2. A pharmaceutical composition comprising a deuterated compound as described in claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier.

3. A method for detecting neurofibrillary tangles and/or senile plaques in an animal comprising administering a deuterated compound comprising an imaging isotope as described in claim 1 , or a pharmaceutically acceptable salt thereof, to the animal, and measuring the radioactive signal of the compound.

4. A method of detecting a neurological disorder associated with amyloid plaque and/or tau protein aggregation in an animal comprising administering a deuterated compound comprising an imaging isotope as described in claim 1 , or a pharmaceutically acceptable salt thereof, to the animal, and measuring the radioactive signal of the compound, which is associated with amyloid deposits and/or tau protein aggregates.

5. A method of detecting Alzheimer's disease associated with amyloid plaque and/or tau protein aggregation in an animal comprising administering a deuterated compound comprising an imaging isotope as described in claim 1 , or a pharmaceutically acceptable salt thereof, to the animal, and measuring the radioactive signal of the compound associated with amyloid deposits and/or tau protein aggregates.

6. A method of detecting progressive supranuclear palsy associated with amyloid plaque and/or tau protein aggregation in an animal, comprising administering a deuterated compound comprising an imaging isotope as described in claim 1 , or a pharmaceutically acceptable salt thereof, to the animal, and measuring the radioactive signal of the compound associated with amyloid deposits and/or tau protein aggregates.

7. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

8. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

9. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

10. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

11. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

12. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

13. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

14. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

15. A deuterated compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein the carbon marked * has a deuterium isotope enrichment factor of at least 3500.

Assignees

• Genentech Inc

Inventors

• Marik Jan
• Lyssikatos Joseph P
• Williams Simon

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• A61K51/0459 Primary

  having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title