IP Library Granted Patent US 10,059,689
Granted Patent B2
US 10,059,689 · App. 14/880,199 · Granted Aug 28, 2018

Substituted heteroaryl compounds and methods of use

Inventors: Ning Xi (Newbury Park, CA); Minxiong Li (Guangdong, CN); Xiaobo Li (Guangdong, CN); Weilong Dai (Guangdong, CN); Haiyang Hu (Guangdong, CN); Tao Zhang (Guangdong, CN); Wuhong Chen (Guangdong, CN)
Assignees: CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.
C07D401/14A61K31/506A61K45/06
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,059,689
App. No.
14/880,199
Granted
Aug 28, 2018
Kind
B2
Abstract

The present invention provides novel heteroaryl compounds, pharmaceutical acceptable salts and formulations thereof useful in preventing, managing, treating or lessening the severity of a protein kinase-mediated disease. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of protein kinase-mediated disease.

Claims (21)

1. A compound having Formula (I):

or a stereoisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof,

wherein:

W is

wherein W is optionally substituted by 1, 2, or 3 R 2 groups;

Ar is phenyl or 5-6 membered heteroaryl, wherein Ar is optionally substituted by 1, 2, 3, 4 or 5 R 8 groups;

Z is H or C1-C6 alkyl;

B is pyrazolyl, imidazolyl or indazolyl, wherein B is optionally substituted by 1, 2, 3, 4 or 5 R 4 groups;

R 1 is H, F, Cl, Br, I, NO 2 , N 3 , CN or C 1 -C 6 alkyl; and

each R 2 , R 4 and R 8 is independently F, Cl, Br, I, NO 2 , N 3 , CN, C 1 -C 12 alkyl, or C 1 -C 12 , hydroxyalkyl.

2. The compound according to claim 1 , wherein Ar is phenyl, furanyl, imidazolyl, isoxazolyl, oxazolyl, pyrrolyl, pyridyl, pyridonyl, pyrimidinyl, pyrimidonyl, pyridazinyl, thiazolyl, isothiazolyl, tetrazolyl, triazolyl, thienyl, pyrazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl or triazinyl, wherein Ar is optionally substituted by 1, 2 or 3 R 8 groups.

3. The compound according to claim 1 , wherein Z is H, methyl, ethyl, n-propyl, or i-propyl.

4. The compound according to claim 1 , wherein IV is H, F, Cl, Br, CN, methyl, ethyl, n-propyl, or i-propyl.

5. The compound according to claim 1 , wherein each R 2 , R 4 and R 8 is independently F, Cl, Br, CN, N 3 , NO 2 , C 1 -C 6 alkyl or C 1 -C 6 hydroxyalkyl.

6. The compound according to claim 1 , wherein each R 2 , R 4 and R 8 is independently F, Cl, CN, methyl, ethyl, n-propyl, i-propyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 2-hydroxy-2-methylpropyl, or 2-hydroxypropan 2 yl.

7. The compound according to claim 1 , wherein B is:

and wherein B is optionally substituted by 1, 2 or 3 R 4 groups.

8. The compound according to claim 1 having one of the following structures:

or a stereoisomer, a tautomer, an N-oxide, a solvate, or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition comprising the compound of claim 1 , and a pharmaceutically acceptable excipient, carrier, adjuvant, vehicle or a combination thereof.

10. The pharmaceutical composition of claim 9 further comprising a therapeutic agent selected from the group consisting of chemotherapeutic agents, anti-proliferative agents, phosphodiesterase 4 (PDE4) inhibitors, β 2 -adrenoreceptor agonists, corticosteroids, non-steroidal GR agonists, anticholinergic agents, antihistamines, anti-inflammatory agents, immunosuppressants, immunomodulators, agents for treating atherosclerosis, agents for treating pulmonary fibrosis and combinations thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2021
From: CALITOR SCIENCES, LLC.
To: SUNSHINE LAKE PHARMA CO., LTD.
Reel/Frame 056177/0572 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 15/961,688 PREVIOUSLY RECORDED ON REEL 052922 FRAME 0077. ASSIGNOR(S) HEREBY CONFIRMS THE THE ASSIGNMENT. Recorded Sep 29, 2020
From: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
To: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES LLC
Reel/Frame 053921/0538 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2020
From: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
To: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES LLC
Reel/Frame 052922/0077 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2019
From: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC
To: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
Reel/Frame 050776/0657 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2015
From: XI, NING; LI, MINXIONG; LI, XIAOBO; DAI, WEILONG; HU, HAIYANG; ZHANG, TAO; CHEN, WUHONG
To: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC
Reel/Frame 036769/0602 →
Continuity (2)
Provisional Application 62063460 · Oct 14, 2014
Related Publication 20160229837A1 · Aug 11, 2016