IP Library › Granted Patent US 12,612,385

Granted Patent B2

US 12,612,385 · App. 18/519,938 · Granted Apr 28, 2026

Compounds and methods for targeting pathogenic blood vessels

Inventors: Hui Sun (Culver City, CA); Pu Sun (San Jose, CA); Guo Cheng (Los Angeles, CA); Adrian Chichuen Au (Los Angeles, CA); Ming Zhong (Nanjing, CN)

Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

C07D401/14 A61P35/00 C07D215/42 C07D215/44 C07D215/46 C07D401/04 C07D401/12 C07D405/12 C07D405/14 C07D409/12 C07D417/12 C07D487/08 C07D491/113 C07D498/04 C07H15/26

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Quick Facts

Patent No.: US 12,612,385
App. No.: 18/519,938
Granted: Apr 28, 2026
Kind: B2

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Abstract

The disclosure provides compounds, and compositions, including pharmaceutical compositions, kits that include the compounds, and methods of using (or administering) and making the compounds. The disclosure further provides compounds or compositions thereof for use in a method of modulating PLXDC1 (TEM7) and/or PLXDC2 or killing pathogenic blood vessels. The disclosure further provides compounds or compositions thereof for use in a method of treating a disease, disorder, or condition that is mediated, at least in part, by PEDF receptors or by angiogenesis.

Claims (431)

1 . A compound of Formula (I):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof;

wherein

n is 0, 1, 2, 3 or 4;

R 1 is

each of s, t, u, v, p and q is independently 0, 1, 2, or 3, provided that the sum of s and t is 1, 2, 3 or 4, the sum of u and vis 1 , 2 , 3 or 4 , and the sum of p and q is 1, 2, 3 or 4;

y is 1;

z is 0 or 1;

Z 1 is CH or N;

Z 2 is CH or N;

Z 3 is CH or N;

Z 4 is CH or N;

Z 5 is CH 2 , CHR 25 , CR 25 R 25 , C(═O), NR 25 , O, or S(O) 0-2 ;

each R 25 is independently H, halo, alkyl or hydroxyalkyl;

n is 0, 1, 2, 3, or 4;

R 2 is C 2-40 alkoxy,

R 5 , R 7 , and R 8 are each independently hydrogen;

R 6 is haloalkoxy, sulfoxido, or sulfonyl; and

each R 9 is independently selected from halo, alkyl, —OH, alkoxy, —CN, and amino.

2 . The compound of claim 1 , wherein R 9 is H or fluoro.

3 . A compound of Formula (XII):

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof;

wherein:

R 1 is

each of s, t, u, v, p and q is independently 0, 1, 2, or 3, provided that the sum of s and tis 1, 2, 3 or 4, the sum of u and v is 1, 2, 3 or 4, and the sum of p and q is 1, 2, 3 or 4;

y is 1;

z is 0 or 1;

Z 1 is CH or N;

Z 2 is CH or N;

Z 3 is CH or N;

Z 4 is CH or N;

Z 5 is CH 2 , CHR 25 , CR 25 R 25 , C(═O), NR 25 , O, or S(O) 0-2 ;

each R 25 is independently H, halo, alkyl or hydroxyalkyl;

R 211 is C 2-40 alkyl, C 2-40 alkenyl, or C 2-40 alkynyl;

R 6 is haloalkoxy, sulfoxido, or sulfonyl; and

R 91 and R 92 are independently selected from H and halo.

4 . The compound of claim 1 or 3 , wherein z is 1.

5 . The compound of claim 1 or 3 , wherein s, t, u, v, p and q are 1.

6 . The compound of claim 1 or 3 , wherein Z 1 and Z 3 are CH.

7 . The compound of claim 1 or 3 , wherein Z 2 and Z 4 are N.

8 . The compound of claim 3 , wherein R 91 and R 92 are independently selected from H and F.

9 . A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

10 . The compound of claim 1 , wherein the compound is selected from the group consisting of:

TABLE 1

Ex.

Structure

Name

119

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

167

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinoline

169

4-([1,4′-bipiperidin]-1′-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfonyl)quinoline

221

4-([1,4′-bipiperidin]-1′-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

235

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)morpholine

236

2-(4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

237

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinoline

240

(1′-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)methanol

241

3-((4-butoxyphenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

245

4-(1-(3-((4-butoxyphenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)thiomorpholine

253

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

256

3-((4-(heptyloxy)phenyl)sulfonyl)-4-(4- (4-methyl-1,4-diazepan-1-yl)piperidin-1- yl)-6-(methylsulfinyl)quinoline

257

2-(4-(1-(3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

258

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

264

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

267

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)piperidin-1-yl)- 6-(methylsulfinyl)quinoline

268

2-(4-(1-(3-((4- (decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

269

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

277

4-(4-(1-ethylpiperidin-4-yl)piperazin-1- yl)-3-((4-(heptyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

283

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(1- ethylpiperidin-4-yl)piperazin-1-yl)-6- (methylsulfinyl)quinoline

284

2-(4-(1-(3-((4-((3,7- dimethyloctyl)oxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

285

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

286

4-(1′-(3-((4-(decyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)morpholine

287

3-((4-(decyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

289

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- ((3,7- dimethyloctyl)oxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

290

([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (decyloxy)-3-fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinoline

291

2-(4-(1-(3-((4-(decyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

292

2-(4-(1′-(3-((4- (decyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethan-1- ol

339

2-(4-(1-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethan-1-ol

340

2-(4-(1′-(3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethan-1- ol

341

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

342

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

344

2-(4-(1-(6-(methylsulfinyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)piperidin-4-yl)piperazin-1-yl)ethan- 1-ol

345

2-(4-(1′-(6-(methylsulfinyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinolin- 4-yl)-[1,4′-bipiperidin]-4-yl)piperazin-1- yl)ethan-1-ol

346

4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

347

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methyl(λ 1 -oxidanyl)-λ 3 -sulfanyl)-3-((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

362

2-(4-(1-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

363

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)-3-fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinoline

365

2-(4-(1-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

366

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((3- fluoro-4-(tetradecyloxy)phenyl)sulfonyl)- 6-(methylsulfinyl)quinoline

368

2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

369

2-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

370

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

371

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

376

2-(4-(1-(3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)piperidin-4- yl)piperazin-1-yl)ethanol

377

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

380

2-(4-(1-(6-(methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinolin-4- yl)piperidin-4-yl)piperazin-1-yl)ethanol

381

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methylsulfinyl)-3-((4- (undecyloxy)phenyl)sulfonyl)quinoline

384

2-(4-((4-([1,4′:1′,4″-terpiperidin]-1″-yl)-6- (methylsulfinyl)quinolin-3- yl)sulfonyl)phenoxy)-N,N- diethylethanamine

385

2-(4-(1′-(3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

386

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

387

2-(4-(1′-(3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

388

3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

390

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

391

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

392

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methyl-1,4-diazepan-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

393

4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)morpholine

394

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

395

3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

396

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

397

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

398

4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

399

3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

400

4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)thiomorpholine

402

3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfonyl)quinoline

407

(R)-2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

408

(S)-2-(4-(1′-(3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

409

(R)-2-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

410

(S)-2-(4-(1′-(3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinolin-4-yl)-[1,4′- bipiperidin]-4-yl)piperazin-1-yl)ethanol

411

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

412

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

413

3-((4-(dodecyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

414

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

415

3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

416

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

417

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

418

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

419

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

420

3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

421

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

422

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

423

3-((2,3-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

424

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

425

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

426

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

427

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

428

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

429

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

430

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

431

3-((4-(dodecyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

432

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

433

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

434

3-((3,5-difluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

435

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

436

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

437

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

438

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

439

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

440

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

441

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

442

3-((4-(dodecyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

443

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

444

3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

445

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

446

3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

447

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

448

3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

449

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

450

4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3-((4- (dodecyloxy)-2,3- difluorophenyl)sulfonyl)-6- (methylsulfinyl)quinoline

451

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-ethylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

452

3-((4-(dodecyloxy)phenyl)sulfonyl)-4-(4- (4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

453

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

454

4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetradecyloxy)phenyl)sulfonyl)quinoline

455

(R)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

456

(S)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

457

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

458

(S)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

461

3-((4-(icosyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

462

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

463

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

464

(S)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

465

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

466

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-ethylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

467

(R)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

468

(S)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

469

(R)-3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

470

(S)-3-((4-(dodecyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4- ethylpiperazin-1-yl)-[1,4′-bipiperidin]-1′- yl)-6-(methylsulfinyl)quinoline

471

(R)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

472

(S)-4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((3-fluoro-4- (tetradecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

473

(R)-3-((4-(dodecyloxy)phenyl)sulfonyl)- 4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

474

(S)-3-((4-(dodecyloxy)phenyl)sulfonyl)- 4-(4-(4-isopropylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfinyl)quinoline

475

(R)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

476

(S)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- methylpiperazin-1-yl)-[1,4′-bipiperidin]- 1′-yl)-6-(methylsulfinyl)quinoline

477

(R)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

478

(S)-4-(4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

479

(R)-4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3- ((4-(dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

480

(S)-4-([1,4′:1′,4″-terpiperidin]-1″-yl)-3- ((4-(dodecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

482

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfonyl)quinoline

483

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

484

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

485

(R)-4-(4-(4-(1-ethylpiperidin-4- yl)piperazin-1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

486

(S)-4-(4-(4-(1-ethylpiperidin-4- yl)piperazin-1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

487

(R)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

488

(S)-3-((4-(docosyloxy)phenyl)sulfonyl)- 4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

489

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6-(methylsulfinyl)-3- ((4- (tetracosyloxy)phenyl)sulfonyl)quinoline

490

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-(methylsulfinyl)-3- ((4- (tetracosyloxy)phenyl)sulfonyl)quinoline

491

4-(4-(4-ethylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (hexacosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

492

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexacosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

493

3-((4-(icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(4-propylpiperazin- 1-yl)-[1,4′-bipiperidin]-1′-yl)quinoline

494

4-(4-(4-butylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

495

3-((4-(docosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)-4-(4-(4-propylpiperazin- 1-yl)-[1,4′-bipiperidin]-1′-yl)quinoline

496

4-(4-(4-butylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-3-((4- (docosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

497

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylthio)quinoline

498

3-((4-(hexadecyloxy)phenyl)sulfonyl)-4- (4-(4-methylpiperazin-1-yl)-[1,4′- bipiperidin]-1′-yl)-6- (methylsulfonyl)quinoline

499

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylthio)quinoline

500

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

502

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

504

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

506

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

508

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-6-(methylsulfinyl)-3- ((4- (octadecyloxy)phenyl)sulfonyl)quinoline

510

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (octadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

512

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

514

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- methoxyquinoline

516

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

518

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

520

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (methylsulfinyl)quinoline

522

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((3-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

524

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

526

3-((4-(docosyloxy)phenyl)sulfonyl)-4-(4- (4-(1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

528

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (methylsulfinyl)quinoline

530

3-((4-(docosyloxy)-3- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

531

3-((4-(docosyloxy)-3,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

532

3-((4-(docosyloxy)-2,3- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

533

3-((4-(docosyloxy)-2- fluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

534

3-((3,5-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

535

3-((2,3-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

536

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (icosyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

537

3-((3,5-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

538

3-((2,3-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

539

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (octadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

540

3-((3,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

541

3-((2,3-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

542

4-(4-(4-(1-ethylpiperidin-4-yl)piperazin- 1-yl)piperidin-1-yl)-3-((2-fluoro-4- (hexadecyloxy)phenyl)sulfonyl)-6- (trifluoromethoxy)quinoline

543

3-((2,6-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

544

3-((2,6-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

545

3-((2,6-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

546

3-((4-(docosyloxy)-2,6- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

547

3-((2,5-difluoro-4- (hexadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

548

3-((2,5-difluoro-4- (octadecyloxy)phenyl)sulfonyl)-4-(4-(4- (1-ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

549

3-((2,5-difluoro-4- (icosyloxy)phenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline and

550

3-((4-(docosyloxy)-2,5- difluorophenyl)sulfonyl)-4-(4-(4-(1- ethylpiperidin-4-yl)piperazin-1- yl)piperidin-1-yl)-6- (trifluoromethoxy)quinoline

or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

11 . A pharmaceutical composition comprising a compound of claim 10 , or a pharmaceutically acceptable salt, isotopically enriched analog, stereoisomer, mixture of stereoisomers, or tautomer thereof.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2025

From: SUN, PU

To: ATENGEN, INC.

Reel/Frame 071987/0109 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2025

From: SUN, HUI; AU, ADRIAN CHICHUEN; CHENG, GUO; ZHONG, MING

To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

Reel/Frame 071987/0212 →

Continuity (3)

Continuation 17072844 · Oct 16, 2020

Provisional Application 62916983 · Oct 18, 2019

Related Publication 20240270717A1 · Aug 15, 2024

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Bagley et al., “Tumor endothelial marker 7 (TEM-7): a novel target for antiangiogenic therapy”, [cited by applicant]

Beaty et al., “PLXDC1 (TEM7) is identified in a genome-wide expression screen of glioblastoma endothelium.” [cited by applicant]

Cheng et al., “Identification of PLXDC1 and PLXDC2 as the transmembrane receptors for the multifunctional factor PEDF”, [cited by applicant]

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Galambos et al., “4-Aryl-3-arylsulfonyl-quinolines as negative allosteric modulators of metabotropic GluR5 receptors: From HTS hit to development candidate”, [cited by applicant]

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International Search Report and Written Opinion issued in International Application No. PCT/US2020/055979, mailed Dec. 22, 2020. [cited by applicant]

International Search Report and Written Opinion issued in International Application No. PCT/US2020/056003, mailed Feb. 17, 2021. [cited by applicant]

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Ivachtchenko et al., “Antagonists of Serotonin 5-HT6 Receptors. VI. Substituted 3-(Phenylsulfonyl)Quinolines, Synthesis and Structure-Activity Relationships”, [cited by applicant]

Jiang, et al., “A novel peptide isolated from a phage display peptide library with trastuzumab can mimic antigen epitope of HER-2”, [cited by applicant]

Kang et al., “One-pot Synthesis of Highly Functionalizable 3-(Phenylsulfonyl)-2,3-dihydro-4(1H)quinolinones via a Cu-catalyzed Aza-Michael Addition/Cyclization Reaction”, [cited by applicant]

Lee et al., “Identification of the basement membrane protein nidogen as a candidate ligand for tumor endothelial marker 7 in vitro and in vivo.” [cited by applicant]

Li et al., “Copper-Catalyzed Electrophilic Cyclization of N-Propargylamines with Sodium Sulfinate for the synthesis of 3-Sulfonated Quinolines”, [cited by applicant]

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Office Action issued in corresponding U.S. Appl. No. 17/072,952, dated Dec. 16, 2022. [cited by applicant]

Shao et al., “Choroid sprouting assay: an ex vivo model of microvascular angiogenesis”, [cited by applicant]

Smusz et al., “Fingerprint-based consensus virtual screening towards structurally new 5-HT(6)R ligands”, [cited by applicant]

Sun et al., “Visible-light-induced multicomponent cascase cycloaddition involving N-Propargyl aromatic amines, diaryliodonium salts and sulfur dioxide: rapid access to 3-arylsulfonylquinolines”, [cited by applicant]

Yamaji et al., “TEM7 (PLXDC1) in neovascular endothelial cells of fibrovascular membranes from patients with proliferative diabetic retinopathy”, [cited by applicant]

Yang et al., “An iron delivery pathway mediated by a lipocalin.” [cited by applicant]

Yang et al., “Discovery of Orally Bioavailable Quinoline-Based Aldehyde Dehydrogenase 1A1 (ALDH1A1) Inhibitors with Potent Cellular Activity”, [cited by applicant]

Zhang et al., “Antiproliferative activities of the second-generation antipsychotic drug sertindole against breast cancers with a potential application for treatment of breast-to-brain metastases”, [cited by applicant]

Zhang et al., “tert-Butyl Hydroperoxide Mediated Cascade Synthesis of 3-Arylsulfonylquinolines”, [cited by applicant]

Stancovski, et al. “Mechanistic aspects of the opposing effects of monoclonal antibodies to the ERBB2 receptor on tumor growth”, [cited by applicant]

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Office Action issued in corresponding Korean Application No. 10-2022-7016790, dated Sep. 8, 2025. [cited by applicant]