Deuterated IRAK degraders and uses thereof
The present invention provides deuterium-enriched compounds, compositions thereof, and methods of using the same.
1 . A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , and R 49 is independently H or D,
provided that at least two of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , and R 49 is D.
2 . The compound of claim 1 , wherein at least one of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 is D.
3 . The compound of claim 1 or 2 , wherein R 6 is D.
4 . The compound of claim 1 or 2 , wherein one or more of R 7 , R 8 , and R 9 is D.
5 . The compound of claim 1 or 2 , wherein R 10 , R 11 , and R 12 is D.
6 . The compound of claim 1 or 2 , wherein R 36 is D.
7 . The compound of claim 1 or 2 , wherein R 39 is D.
8 . The compound of claim 1 or 2 , wherein one or more of R 40 and R 41 is D.
9 . The compound of claim 1 or 2 , wherein at least one of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 has a % deuterium incorporation of about 50% or greater.
10 . The compound of claim 1 or 2 , wherein at least one of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 has a % deuterium incorporation of about 80% or greater.
11 . The compound of claim 1 or 2 , wherein at least one of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 has a % deuterium incorporation of about 90% or greater.
12 . The compound of claim 1 or 2 , wherein each of R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 has a % deuterium incorporation of about 95% or greater.
13 . The compound of claim 1 or 2 , wherein the compound is represented by Formula I-a, I-b, I-c, I-d, I-e, I-f, I-g, I-h, or I-i:
or a pharmaceutically acceptable salt thereof.
14 . The compound of claim 1 or 2 , wherein each of R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 36 , R 39 , R 40 , and R 41 is as defined in an entry set forth below:
Entry
R 6
R 7
R 8
R 9
R 10
R 11
R 12
R 36
R 39
R 40
R 41
i
D
D
D
D
H
H
H
H
H
H
H
ii
D
H
H
H
D
D
D
H
H
H
H
iii
D
H
H
H
H
H
H
D
H
H
H
iv
D
H
H
H
H
H
H
H
D
H
H
v
D
H
H
H
H
H
H
H
H
D
D
vi
H
D
D
D
D
D
D
H
H
H
H
vii
H
D
D
D
H
H
H
D
H
H
H
viii
H
D
D
D
H
H
H
H
D
H
H
ix
H
D
D
D
H
H
H
H
H
D
D
x
H
H
H
H
D
D
D
D
H
H
H
xi
H
H
H
H
D
D
D
H
D
H
H
xii
H
H
H
H
D
D
D
H
H
D
D
xiii
H
H
H
H
H
H
H
D
D
H
H
xiv
H
H
H
H
H
H
H
D
H
D
D
xv
H
H
H
H
H
H
H
H
D
D
D
xvi
H
H
H
H
D
D
H
H
H
H
H
xvii
H
H
H
H
H
D
D
H
H
H
H
xviii
H
H
H
H
D
H
D
H
H
H
H
xix
H
H
H
H
D
D
H
D
H
H
H
xx
H
H
H
H
H
D
D
D
H
H
H
xxi
H
H
H
H
D
H
D
D
H
H
H
xxii
H
H
H
H
D
D
H
H
D
H
H
xxiii
H
H
H
H
H
D
D
H
D
H
H
xxiv
H
H
H
H
D
H
D
H
D
H
H
xxv
H
H
H
H
D
D
H
H
H
D
H
xxvi
H
H
H
H
H
D
D
H
H
D
H
xxvii
H
H
H
H
D
H
D
H
H
D
H
xxviii
H
H
H
H
D
D
H
H
H
H
D
xxix
H
H
H
H
H
D
D
H
H
H
D
xxx
H
H
H
H
D
H
D
H
H
H
D
xxxi
H
H
H
H
D
D
H
H
H
D
D
xxxii
H
H
H
H
H
D
D
H
H
D
D
xxxiii
H
H
H
H
D
H
D
H
H
D
D
or a pharmaceutically acceptable salt thereof.
15 . The compound of claim 13 , wherein each position indicated as “D” has a % deuterium incorporation of about 50% or greater.
16 . The compound of claim 13 , wherein each position indicated as “D” has a % deuterium incorporation of about 80% or greater.
17 . The compound of claim 13 , wherein each position indicated as “D” has a % deuterium incorporation of about 90% or greater.
18 . A compound selected from any one of the following:
or a pharmaceutically acceptable salt thereof.
19 . The compound of claim 18 , wherein each position indicated as “D” has a % deuterium incorporation of about 80% or greater.
20 . The compound of claim 18 , wherein each position indicated as “D” has a % deuterium incorporation of about 90% or greater.
21 . The compound of claim 18 , wherein each position indicated as “D” has a % deuterium incorporation of about 95% or greater.
22 . A composition comprising a compound according to claim 1 or claim 2 and a pharmaceutically acceptable carrier or excipient.
23 . The pharmaceutical composition according to claim 22 , further comprising an additional therapeutic agent.
24 . A method of degrading IRAK1, IRAK2 and/or IRAK4 protein kinase in a patient or biological sample comprising administering to said patient, or contacting said biological sample with a compound according to claim 1 or claim 2 , or a pharmaceutical composition thereof.
25 . A method of treating an IRAK4-mediated disorder, disease, or condition in a patient comprising administering to said patient a compound according to claim 1 or claim 2 , or a pharmaceutical composition thereof,
wherein the IRAK4-mediated disorder, disease or condition is an inflammatory disorder,
wherein the inflammatory disorder is selected from the group consisting of ocular allergy, conjunctivitis, keratoconjunctivitis sicca, vernal conjunctivitis, allergic rhinitis, systemic lupus erythematosus, rheumatoid arthritis, scleroderma, dermatomyositis, ulcerative colitis, Crohn's disease, multiple sclerosis, Sjögren's syndrome, interstitial lung fibrosis, psoriatic arthritis, systemic juvenile idiopathic arthritis, aging, asthma, anaphylaxis, Type 1 diabetes, Type 2 diabetes, atopic dermatitis, allergy, dermatitis, hidradenitis suppurativa, peritonitis, rhinitis, dermatitis herpetiformis, urticaria, acute gout, chronic gout, chronic gouty arthritis, psoriasis, juvenile rheumatoid arthritis, and Cryopyrin Associated Periodic Syndrome (CAPS).
26 . The method according to claim 25 , further comprising administration of an additional therapeutic agent.
27 . The method according to claim 25 , wherein the inflammatory disorder is atopic dermatitis or hidradenitis suppurativa.