Compounds useful as kinase inhibitors
US-2019000806-A1 · Jan 3, 2019 · US
Pyrazolopyrimidine derivatives useful as inhibitors of Bruton's tyrosine kinase
US10538524B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10538524-B2 |
| Application number | US-201815977470-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 11, 2018 |
| Priority date | Jun 11, 2014 |
| Publication date | Jan 21, 2020 |
| Grant date | Jan 21, 2020 |
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Abstract
Official abstract text for this publication.
This invention relates to compounds of formula (I). The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK). The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia and immunological diseases.
First claim
Opening claim text (preview).
The invention claimed is: 1. A compound selected from the group consisting of: N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide; N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide; and N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide; or a pharmaceutically acceptable salt thereof. 2. The compound of claim 1 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 3. The compound of claim 1 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide, or a pharmaceutically acceptable salt thereof. 4. The compound of claim 1 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 5. The compound of claim 1 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 6. The compound of claim 1 , wherein the compound is N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide, or a pharmaceutically acceptable salt thereof. 7. The compound of claim 1 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 8. The compound of claim 1 , wherein the compound is selected from the group consisting of: N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide; N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide; and N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide. 9. The compound of claim 1 , wherein the compound is in the form of a pharmaceutically acceptable salt. 10. A pharmaceutical composition comprising a compound selected from the group consisting of: N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide; N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide; and N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide; or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable diluent or carrier. 11. The pharmaceutical composition of claim 10 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 12. The pharmaceutical composition of claim 10 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide, or a pharmaceutically acceptable salt thereof. 13. The pharmaceutical composition of claim 10 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 14. The pharmaceutical composition of claim 10 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 15. The pharmaceutical composition of claim 10 , wherein the compound is N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide, or a pharmaceutically acceptable salt thereof. 16. The pharmaceutical composition of claim 10 , wherein the compound is N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide, or a pharmaceutically acceptable salt thereof. 17. The pharmaceutical composition of claim 10 , wherein the compound is selected from the group consisting of: N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-5-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-methyl-benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-methoxy-4-(trifluoromethyl)benzamide; N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo-[3,4-d]pyrimidin-3-yl]phenyl]methyl]-2-fluoro-3-(trifluoromethyl)benzamide; N-[[3-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-fluoro-2-methoxy-benzamide; and N-[[4-[4-amino-1-[(3R)-1-prop-2-enoyl-3-piperidyl]pyrazolo[3,4-d]pyrimidin-3-yl]phenyl]methyl]-4-(trifluoromethyl)benzamide. 18. The composition of claim 10 , wherein the compound is in the form of a pharmaceutically acceptable salt.
Assignees
Inventors
Classifications
Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title
Immunosuppressants, e.g. drugs for graft rejection · CPC title
Immunomodulators · CPC title
Drugs for immunological or allergic disorders · CPC title
specific for metastasis · CPC title
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- What does patent US10538524B2 cover?
- This invention relates to compounds of formula (I). The compounds of the invention are tyrosine kinase inhibitors. Specifically, the compounds of the invention are useful as inhibitors of Bruton's tyrosine kinase (BTK). The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of Bruton's tyrosine kinase, for example cancer, lymphoma, leukemia …
- Who is the assignee on this patent?
- Loxo Oncology Inc
- What technology area does this patent fall under?
- Primary CPC classification C07D487/04. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Jan 21 2020 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 6 related publications on this page (citations in our corpus or others sharing the same primary CPC).