IP Library › Granted Patent US 10,947,201

Granted Patent B2

US 10,947,201 · App. 15/044,966 · Granted Mar 16, 2021

Certain chemical entities, compositions, and methods

Inventors: Xiangping Qian (Foster City, CA); Yong-Liang Zhu (Fremont, CA)

Assignee: NEUPHARMA, INC.

C07D239/84 A61K31/495 A61P35/00 C07D401/04 C07D401/12 C07D403/12 C07D473/30 C07D473/32

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Quick Facts

Patent No.: US 10,947,201
App. No.: 15/044,966
Granted: Mar 16, 2021
Kind: B2

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Abstract

Chemical entities that are kinase inhibitors, pharmaceutical compositions and methods of treatment of cancer are described.

Claims (141)

1. A compound having the following formula:

or a pharmaceutically acceptable salt thereof, wherein:

X 10 is C—R 35 ;

is aryl or heteroaryl;

each of R 3 , R 4 , R 5 and R 6 is independently hydrogen, cyano, fluoro, or chloro;

R34, R35, R36, R37, and R38 are independently hydrogen, cyano, halo, optionally substituted alkoxy, optionally substituted heterocycloalkyloxy, optionally substituted heterocycloalkyl, optionally substituted amino, or E;

each Q is independently hydrogen, cyano, or halo;

wherein E is

and

m is 0, 1, or 2;

wherein at least one of R 34 , R 35 , R 36 , R 37 , and R 38 is E;

wherein:

each substituted alkoxy is —O-(substituted alkyl);

each substituted amino is —NHR d or —NR d R e ; wherein each R d is independently unsubstituted or substituted alkyl, or unsubstituted or substituted heterocycloalkyl; and each R e is independently unsubstituted or substituted alkyl, or unsubstituted or substituted heterocycloalkyl; and

each substituted alkyl and substituted heterocycloalkyl is substituted with one or more groups independently selected from —R a , —OR b , —NH 2 —NHR d , —NR d R e , and halo; each R a is independently unsubstituted or substituted C 1 -C 6 alkyl; each R b is independently hydrogen or unsubstituted or substituted C 1 -C 6 alkyl; each R d is independently unsubstituted or substituted alkyl; and each R e is independently unsubstituted or substituted alkyl;

wherein when any R a , R b , R d , or R e group is substituted, the R a , R b , R d , or R e group is substituted with one or more substituents independently selected from a group D consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, —OC 1 -C 4 alkyl, halo, —OH, —NH 2 , —N(C 1 -C 4 alkyl)(C 1 -C 4 alkyl), and —NH(C 1 -C 4 alkyl).

2. The compound or pharmaceutically acceptable salt of claim 1 , wherein

is aryl.

3. The compound or pharmaceutically acceptable salt of claim 1 , wherein R 35 or R 37 is E.

4. The compound or pharmaceutically acceptable salt of claim 3 , wherein R 36 is

wherein R 28 is hydrogen or alkyl.

5. The compound or pharmaceutically acceptable salt of claim 1 , wherein

is phenyl or pyridinyl.

6. The compound or pharmaceutically acceptable salt of claim 1 , having the following Formula:

wherein

R 34 , R 36 , R 37 , and R 38 are independently hydrogen, cyano, halo, optionally substituted alkoxy, optionally substituted heterocycloalkyloxy, optionally substituted heterocycloalkyl, or optionally substituted amino.

7. The compound or pharmaceutically acceptable salt of claim 6 , wherein R 3 , R 4 , R 6 and R 5 are each hydrogen.

8. The compound of claim 1 , selected from the group consisting of:

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxyphenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-morpholinophenyl)acrylamide,

N-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(2-(3-(dimethylamino)azetidin-1-yl)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-morpholinophenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)pyrrolidin-1-yl)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)azetidin-1-yl)-4-methoxyphenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-morpholinophenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)pyrrolidin-1-yl)-4-methoxyphenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)azetidin-1-yl)-4-methoxyphenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-morpholinophenyl)acrylamide,

N-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(2-(3-(dimethylamino)azetidin-1-yl)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(2-(2-(dimethylamino)ethoxy)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(2-(dimethylamino)ethoxy)-4-methoxyphenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(2-(dimethylamino)ethoxy)-4-methoxyphenyl)acrylamide,

N-(2-(2-(dimethylamino)ethoxy)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxyphenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-4-methoxy-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylpyrrolidin-3-yl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylpiperidin-4-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(methyl(1-methylazetidin-3-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-morpholinophenyl)acrylamide,

N-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(2-(3-(dimethylamino)azetidin-1-yl)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-morpholinophenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)azetidin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-morpholinophenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(3-(dimethylamino)azetidin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-(4-methylpiperazin-1-yl)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-morpholinophenyl)acrylamide,

N-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(2-(3-(dimethylamino)azetidin-1-yl)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylpyrrolidin-3-yl)oxy)phenyl)acrylamide,

N-(2-(2-(dimethylamino)ethoxy)-5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(2-(dimethylamino)ethoxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-(2-(dimethylamino)ethoxy)phenyl)acrylamide,

N-(2-(2-(dimethylamino)ethoxy)-5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylpiperidin-4-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-fluoropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(5-chloropyridin-3-yl)quinazolin-2-yl)amino)-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(5-((8-(3-fluorophenyl)quinazolin-2-yl)amino)-2-((1-methylazetidin-3-yl)oxy)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-phenylquinazolin-2-yl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(pyridin-4-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(2-chlorophenyl)quinazolin-2-yl)amino)-2-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(2-fluorophenyl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((8-(pyridin-3-yl)quinazolin-2-yl)amino)phenyl)acrylamide,

N-(5-((8-(2-chlorophenyl)quinazolin-2-yl)amino)-2-(2-(dimethylamino)ethoxy)phenyl)acrylamide, and

N-(5-((8-(3-chlorophenyl)quinazolin-2-yl)amino)-2-(2-methoxyethoxy)phenyl)acrylamide,

or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound or pharmaceutically acceptable salt of claim 1 .

10. A packaged pharmaceutical composition comprising the pharmaceutical composition of claim 9 and instructions for using the composition to treat a subject suffering from cancer.

11. A method of treating cancer in a subject which comprises administering to the subject in need thereof a therapeutically effective amount of the compound or pharmaceutically acceptable salt of claim 1 .

12. A method of treating a disorder mediated by EGFR in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound or pharmaceutically acceptable salt of claim 1 .

13. A method of treating a disorder in a subject in need thereof, comprising:

a) determining the presence or absence of an EGFR mutation in a biological sample isolated from the subject; and

b) if the EGFR mutation is determined to be present in the subject, administering to the subject a therapeutically effective amount of the compound or pharmaceutically acceptable salt of claim 1 .

14. The compound or pharmaceutically acceptable salt of claim 1 , wherein at least one of R 34 , R 35 , R 36 , R 37 , and R 38 is cyano, fluoro, chloro, methoxy, 2-methoxyethoxy, 2-(dimethylamino)ethoxy, (1-methylpyrrolidin-3-yl)oxy, (1-methylpiperidin-4-yl)oxy, (1-methylpiperidin-3-yl)oxy, (1-methylazetidin-3-yl)oxy (2-(dimethylamino)ethyl)(methyl)amino, dimethylamino, methyl(1-methylazetidin-3-yl)amino, methyl(1-methylpyrrolidin-3-yl)amino, methyl(1-methylpiperidin-4-yl)amino, morpholinyl, piperazinyl, pyrrolidinyl, piperidinyl, or azetidinyl; wherein each of the morpholinyl, piperazinyl, pyrrolidinyl, piperidinyl, or azetidinyl may be substituted.

15. The compound or pharmaceutically acceptable salt of claim 6 , wherein R 36 is methoxy, 2-methoxyethoxy, 2-(dimethylamino)ethoxy, (1-methylpyrrolidin-3-yl)oxy, (1-methylpiperidin-4-yl)oxy, (1-methylpiperidin-3-yl)oxy, (1-methylazetidin-3-yl)oxy (2-(dimethylamino)ethyl)(methyl)amino, dimethylamino, methyl(1-methylazetidin-3-yl)amino, methyl(1-methylpyrrolidin-3-yl)amino, methyl(1-methylpiperidin-4-yl)amino, morpholinyl, piperazinyl, pyrrolidinyl, piperidinyl, or azetidinyl; wherein each of the morpholinyl, piperazinyl, pyrrolidinyl, piperidinyl, or azetidinyl may be substituted.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 16, 2016

From: QIAN, XIANGPING; ZHU, YONG-LIANG

To: NEUPHARMA, INC.

Reel/Frame 038004/0316 →

Continuity (3)

Provisional Application 62117442 · Feb 17, 2015

Provisional Application 62117773 · Feb 18, 2015

Related Publication 20160304471A1 · Oct 20, 2016

Cited By (2)

US 12,202,844 US 12,403,145