Granted Patent B2

US 12,612,412 · App. 17/720,079 · Granted Apr 28, 2026

Inventors: Adam Szymaniak (Boston, MA); Jianming Yu (Plainsboro, NJ); Kevin McGrath (Brighton, MA); Xiben Li (Lexington, MA); Tyler J. Mann (Brighton, MA); Robert Leon (Sharon, MA); In Jong Kim (Lexington, MA); Yat Sun Or (Waltham, MA); Long Nguyen (Boston, MA)

Assignee: Enanta Pharmaceuticals, Inc.

C07D491/048A61K45/06C07D519/00

Abstract

Claims (171)

1 . A compound represented by Formula (XXV):

or a pharmaceutically acceptable salt thereof,

wherein R 14 is cyclopropyl or 1-fluorocyclopropyl; R 24 is hydrogen, Cl, F, or optionally substituted methoxyl; R 3 is hydroxy; R 4 is cyclopropyl or 1-fluorocyclopropyl; R 41 , R 42 , R 43 , R 44 , and R 45 are each independently selected from hydrogen, halogen, optionally substituted methyl, optionally substituted methoxy and —CN; alternatively, R 42 and R 43 , or R 41 and R 42 are taken together with the carbon atoms to which they are attached to form a fused 4- to 7-membered carbocyclic ring or heterocyclic ring.

2 . The compound of claim 1 , wherein R 24 is methoxy.

3 . The compound of claim 2 , wherein R 14 is cyclopropyl.

4 . The compound of claim 1 , represented by Formula (XXIII-9) or Formula (XXIII-10),

or a pharmaceutically acceptable salt thereof, wherein:

each R 21 is independently —F, —Cl, —CN, —CF 3 , —CH 2 F or —CHF 2 ;

W is methyl; and

R 4 , R 14 , and R 24 are as defined in claim 1 .

5 . A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

6 . A method of treating or preventing a respiratory syncytial virus (RSV) infection in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.

7 . The method of claim 6 , further comprising the step of administering to the subject an additional anti-RSV agent.

8 . The method of claim 6 , further comprising administering to the subject a steroid anti-inflammatory compound.

9 . A method of treating an RSV infection and influenza in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a therapeutically effective amount of an anti-influenza agent.

10 . The method of claim 7 , wherein the compound and the additional anti-RSV agent are co-formulated.

11 . The method of claim 7 , wherein the compound and the additional anti-RSV agent are co-administered.

12 . A method of treating or preventing a human metapneumovirus (HMPV) infection in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of claim 1 .

13 . The method of claim 12 , further comprising the step of administering to the subject an additional anti-HMPV agent.

14 . The method of claim 13 , wherein the compound and the additional anti-HMPV agent are co-formulated.

15 . The method of claim 13 , wherein the compound and the additional anti-HMPV agent are co-administered.

16 . The compound of claim 1 , wherein

R 24 is —F, —Cl, or —OCH 3 ; and

 is selected from the groups below:

17 . A compound selected from the compounds set forth below, or a pharmaceutically acceptable salt thereof:

Structure

 302

 533

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 545

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 554

 555

 559

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 575

 651

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 657

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 668

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 705

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 743

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 790

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 815

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 831

 835

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 849

 871

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1085

1087

1088

1089

1095

1096

1099

1100

1101

1122

1123

1145

1147

1148

1155

1157

1158

1163

1165

1166

1167

1177

1179

1180

1212

1217

1230

1237

1238

1273

1274

1275

1276

1277

1278

1279

1280

1281

1282

1283

1285

1286

1289

1290

1294

1296

1297

1298

1299

1300

1301

1303

1304

1305

1307

1319

P91

P100

P139

P141

P149

P153

P159

18 . The compound of claim 17 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

19 . The compound of claim 17 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

20 . The compound of claim 17 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

21 . The compound of claim 17 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

22 . The compound of claim 17 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Assignments (1)

Continuity (6)

References Cited (180)