US 12,559,494 B2Granted

Functionalized lactams as modulators of the 5-hydroxytryptamine receptor 7 and their method of use

AssigneesTemple University of the Commonwealth System of Higher Education, Praeventix, LLC

InventorsDaniel J. Canney, Benjamin E. Blass, Kevin M. Blattner, Douglas A. Pippin

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Abstract

Pharmaceutical compositions of the invention comprise functionalized lactam derivatives of formula (I) having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity, wherein A is selected from a group consisting of:

Claims19

Dependent claims

A compound having a structure according to Formula (XLIIIb):

or a pharmaceutically acceptable salt thereof, wherein:
R3 is phenyl or substituted phenyl, wherein the substituents are selected from the group consisting of hydroxyl, halo, cyano, C1-6 alkoxy, C1-6 linear alkyl, C3-7 branched alkyl, C1-6 haloalkyl, and heterocyclyl;
R7 is selected from the group consisting of H, COR8, CO2R9, and SO2R10c;
R8 is selected from the group consisting of H, C1-6 linear alkyl, C3-7 branched alkyl, and C3-7 cycloalkyl;
R9 is selected from the group consisting of C1-6 linear alkyl, C3-7 branched alkyl, and C3-7 cycloalkyl;
R10c is C1-6 linear alkyl or C3-7 branched alkyl;
and
n is 1, 2, 3, or 4.

5 more elements

A compound of Formula (XXII), having a structure as described in Table 16:

TABLE 16
Entry
n
R7
R3
1
1
H
Phenyl
2
2
H
Phenyl
3
3
H
Phenyl
4
4
H
Phenyl
13
1
COMe
Phenyl
14
2
COMe
Phenyl
15
3
COMe
Phenyl
16
4
COMe
Phenyl
17
1
CO2Me
Phenyl
18
2
CO2Me
Phenyl
19
3
CO2Me
Phenyl
20
4
CO2Me
Phenyl
21
1
CO2tBu
Phenyl
22
2
CO2tBu
Phenyl
23
3
CO2tBu
Phenyl
24
4
CO2tBu
Phenyl
29
1
SO2Me
Phenyl
30
2
SO2Me
Phenyl
31
3
SO2Me
Phenyl
32
4
SO2Me
Phenyl
37
1
H
3-OH-Phenyl
38
2
H
3-OH-Phenyl
39
3
H
3-OH-Phenyl
40
4
H
3-OH-Phenyl
49
1
COMe
3-OH-Phenyl
50
2
COMe
3-OH-Phenyl
51
3
COMe
3-OH-Phenyl
52
4
COMe
3-OH-Phenyl
53
1
CO2Me
3-OH-Phenyl
54
2
CO2Me
3-OH-Phenyl
55
3
CO2Me
3-OH-Phenyl
56
4
CO2Me
3-OH-Phenyl
57
1
CO2tBu
3-OH-Phenyl
58
2
CO2tBu
3-OH-Phenyl
59
3
CO2tBu
3-OH-Phenyl
60
4
CO2tBu
3-OH-Phenyl
65
1
SO2Me
3-OH-Phenyl
66
2
SO2Me
3-OH-Phenyl
67
3
SO2Me
3-OH-Phenyl
68
4
SO2Me
3-OH-Phenyl
109
1
H
3-OMe-Phenyl
110
2
H
3-OMe-Phenyl
111
3
H
3-OMe-Phenyl
112
4
H
3-OMe-Phenyl
121
1
COMe
3-OMe-Phenyl
122
2
COMe
3-OMe-Phenyl
123
3
COMe
3-OMe-Phenyl
124
4
COMe
3-OMe-Phenyl
125
1
CO2Me
3-OMe-Phenyl
126
2
CO2Me
3-OMe-Phenyl
127
3
CO2Me
3-OMe-Phenyl
128
4
CO2Me
3-OMe-Phenyl
129
1
CO2tBu
3-OMe-Phenyl
130
2
CO2tBu
3-OMe-Phenyl
131
3
CO2tBu
3-OMe-Phenyl
132
4
CO2tBu
3-OMe-Phenyl
137
1
SO2Me
3-OMe-Phenyl
138
2
SO2Me
3-OMe-Phenyl
139
3
SO2Me
3-OMe-Phenyl
140
4
SO2Me
3-OMe-Phenyl
145
1
H
4-CN-Phenyl
146
2
H
4-CN-Phenyl
147
3
H
4-CN-Phenyl
148
4
H
4-CN-Phenyl
157
1
COMe
4-CN-Phenyl
158
2
COMe
4-CN-Phenyl
159
3
COMe
4-CN-Phenyl
160
4
COMe
4-CN-Phenyl
161
1
CO2Me
4-CN-Phenyl
162
2
CO2Me
4-CN-Phenyl
163
3
CO2Me
4-CN-Phenyl
164
4
CO2Me
4-CN-Phenyl
165
1
CO2tBu
4-CN-Phenyl
166
2
CO2tBu
4-CN-Phenyl
167
3
CO2tBu
4-CN-Phenyl
168
4
CO2tBu
4-CN-Phenyl
173
1
SO2Me
4-CN-Phenyl
174
2
SO2Me
4-CN-Phenyl
175
3
SO2Me
4-CN-Phenyl
176
4
SO2Me
4-CN-Phenyl
181
1
H
2-CN-Phenyl
182
2
H
2-CN-Phenyl
183
3
H
2-CN-Phenyl
184
4
H
2-CN-Phenyl
193
1
COMe
2-CN-Phenyl
194
2
COMe
2-CN-Phenyl
195
3
COMe
2-CN-Phenyl
196
4
COMe
2-CN-Phenyl
197
1
CO2Me
2-CN-Phenyl
198
2
CO2Me
2-CN-Phenyl
199
3
CO2Me
2-CN-Phenyl
200
4
CO2Me
2-CN-Phenyl
201
1
CO2tBu
2-CN-Phenyl
202
2
CO2tBu
2-CN-Phenyl
203
3
CO2tBu
2-CN-Phenyl
204
4
CO2tBu
2-CN-Phenyl
209
1
SO2Me
2-CN-Phenyl
210
2
SO2Me
2-CN-Phenyl
211
3
SO2Me
2-CN-Phenyl
212
4
SO2Me
2-CN-Phenyl
217
1
H
3-Me-Phenyl
218
2
H
3-Me-Phenyl
219
3
H
3-Me-Phenyl
220
4
H
3-Me-Phenyl
229
1
COMe
3-Me-Phenyl
230
2
COMe
3-Me-Phenyl
231
3
COMe
3-Me-Phenyl
232
4
COMe
3-Me-Phenyl
233
1
CO2Me
3-Me-Phenyl
234
2
CO2Me
3-Me-Phenyl
235
3
CO2Me
3-Me-Phenyl
236
4
CO2Me
3-Me-Phenyl
237
1
CO2tBu
3-Me-Phenyl
238
2
CO2tBu
3-Me-Phenyl
239
3
CO2tBu
3-Me-Phenyl
240
4
CO2tBu
3-Me-Phenyl
245
1
SO2Me
3-Me-Phenyl
246
2
SO2Me
3-Me-Phenyl
247
3
SO2Me
3-Me-Phenyl
248
4
SO2Me
3-Me-Phenyl
253
1
H
2-F-Phenyl
254
2
H
2-F-Phenyl
255
3
H
2-F-Phenyl
256
4
H
2-F-Phenyl
266
2
COMe
2-F-Phenyl
267
3
COMe
2-F-Phenyl
268
4
COMe
2-F-Phenyl
269
1
CO2Me
2-F-Phenyl
270
2
CO2Me
2-F-Phenyl
271
3
CO2Me
2-F-Phenyl
272
4
CO2Me
2-F-Phenyl
273
1
CO2tBu
2-F-Phenyl
274
2
CO2tBu
2-F-Phenyl
275
3
CO2tBu
2-F-Phenyl
276
4
CO2tBu
2-F-Phenyl
281
1
SO2Me
2-F-Phenyl
282
2
SO2Me
2-F-Phenyl
283
3
SO2Me
2-F-Phenyl
284
4
SO2Me
2-F-Phenyl
289
1
H
4-F-Phenyl
290
2
H
4-F-Phenyl
291
3
H
4-F-Phenyl
292
4
H
4-F-Phenyl
301
1
COMe
4-F-Phenyl
302
2
COMe
4-F-Phenyl
303
3
COMe
4-F-Phenyl
304
4
COMe
4-F-Phenyl
305
1
CO2Me
4-F-Phenyl
306
2
CO2Me
4-F-Phenyl
307
3
CO2Me
4-F-Phenyl
308
4
CO2Me
4-F-Phenyl
309
1
CO2tBu
4-F-Phenyl
310
2
CO2tBu
4-F-Phenyl
311
3
CO2tBu
4-F-Phenyl
312
4
CO2tBu
4-F-Phenyl
317
1
SO2Me
4-F-Phenyl
318
2
SO2Me
4-F-Phenyl
319
3
SO2Me
4-F-Phenyl
320
4
SO2Me
4-F-Phenyl
325
1
H
3-Cl-Phenyl
326
2
H
3-Cl-Phenyl
327
3
H
3-Cl-Phenyl
328
4
H
3-Cl-Phenyl
337
1
COMe
3-Cl-Phenyl
338
2
COMe
3-Cl-Phenyl
339
3
COMe
3-Cl-Phenyl
340
4
COMe
3-Cl-Phenyl
341
1
CO2Me
3-Cl-Phenyl
342
2
CO2Me
3-Cl-Phenyl
343
3
CO2Me
3-Cl-Phenyl
344
4
CO2Me
3-Cl-Phenyl
345
1
CO2tBu
3-Cl-Phenyl
346
2
CO2tBu
3-Cl-Phenyl
347
3
CO2tBu
3-Cl-Phenyl
348
4
CO2tBu
3-Cl-Phenyl
353
1
SO2Me
3-Cl-Phenyl
354
2
SO2Me
3-Cl-Phenyl
355
3
SO2Me
3-Cl-Phenyl
356
4
SO2Me
3-Cl-Phenyl
361
1
H
2-Br-Phenyl
362
2
H
2-Br-Phenyl
363
3
H
2-Br-Phenyl
364
4
H
2-Br-Phenyl
373
1
COMe
2-Br-Phenyl
374
2
COMe
2-Br-Phenyl
375
3
COMe
2-Br-Phenyl
376
4
COMe
2-Br-Phenyl
377
1
CO2Me
2-Br-Phenyl
378
2
CO2Me
2-Br-Phenyl
379
3
CO2Me
2-Br-Phenyl
380
4
CO2Me
2-Br-Phenyl
381
1
CO2tBu
2-Br-Phenyl
382
2
CO2tBu
2-Br-Phenyl
383
3
CO2tBu
2-Br-Phenyl
384
4
CO2tBu
2-Br-Phenyl
389
1
SO2Me
2-Br-Phenyl
390
2
SO2Me
2-Br-Phenyl
391
3
SO2Me
2-Br-Phenyl
392
4
SO2Me
2-Br-Phenyl
397
1
H
4-Br-Phenyl
398
2
H
4-Br-Phenyl
399
3
H
4-Br-Phenyl
400
4
H
4-Br-Phenyl
409
1
COMe
4-Br-Phenyl
410
2
COMe
4-Br-Phenyl
411
3
COMe
4-Br-Phenyl
412
4
COMe
4-Br-Phenyl
413
1
CO2Me
4-Br-Phenyl
414
2
CO2Me
4-Br-Phenyl
415
3
CO2Me
4-Br-Phenyl
416
4
CO2Me
4-Br-Phenyl
417
1
CO2tBu
4-Br-Phenyl
418
2
CO2tBu
4-Br-Phenyl
419
3
CO2tBu
4-Br-Phenyl
420
4
CO2tBu
4-Br-Phenyl
425
1
SO2Me
4-Br-Phenyl
426
2
SO2Me
4-Br-Phenyl
427
3
SO2Me
4-Br-Phenyl
428
4
SO2Me
4-Br-Phenyl
433
1
H
3-CF3-Phenyl
434
2
H
3-CF3-Phenyl
435
3
H
3-CF3-Phenyl
436
4
H
3-CF3-Phenyl
445
1
COMe
3-CF3-Phenyl
446
2
COMe
3-CF3-Phenyl
447
3
COMe
3-CF3-Phenyl
448
4
COMe
3-CF3-Phenyl
449
1
CO2Me
3-CF3-Phenyl
450
2
CO2Me
3-CF3-Phenyl
451
3
CO2Me
3-CF3-Phenyl
452
4
CO2Me
3-CF3-Phenyl
453
1
CO2tBu
3-CF3-Phenyl
454
2
CO2tBu
3-CF3-Phenyl
455
3
CO2tBu
3-CF3-Phenyl
456
4
CO2tBu
3-CF3-Phenyl
461
1
SO2Me
3-CF3-Phenyl
462
2
SO2Me
3-CF3-Phenyl
463
3
SO2Me
3-CF3-Phenyl
464
4
SO2Me
3-CF3-Phenyl
469
1
H
2-iPr-Phenyl
470
2
H
2-iPr-Phenyl
471
3
H
2-iPr-Phenyl
472
4
H
2-iPr-Phenyl
481
1
COMe
2-iPr-Phenyl
482
2
COMe
2-iPr-Phenyl
483
3
COMe
2-iPr-Phenyl
484
4
COMe
2-iPr-Phenyl
485
1
CO2Me
2-iPr-Phenyl
486
2
CO2Me
2-iPr-Phenyl
487
3
CO2Me
2-iPr-Phenyl
488
4
CO2Me
2-iPr-Phenyl
489
1
CO2tBu
2-iPr-Phenyl
490
2
CO2tBu
2-iPr-Phenyl
491
3
CO2tBu
2-iPr-Phenyl
492
4
CO2tBu
2-iPr-Phenyl
497
1
SO2Me
2-iPr-Phenyl
498
2
SO2Me
2-iPr-Phenyl
499
3
SO2Me
2-iPr-Phenyl
500
4
SO2Me
2-iPr-Phenyl
505
1
H
4-iPr-Phenyl
506
2
H
4-iPr-Phenyl
507
3
H
4-iPr-Phenyl
508
4
H
4-iPr-Phenyl
517
1
COMe
4-iPr-Phenyl
518
2
COMe
4-iPr-Phenyl
519
3
COMe
4-iPr-Phenyl
520
4
COMe
4-iPr-Phenyl
521
1
CO2Me
4-iPr-Phenyl
522
2
CO2Me
4-iPr-Phenyl
523
3
CO2Me
4-iPr-Phenyl
524
4
CO2Me
4-iPr-Phenyl
525
1
CO2tBu
4-iPr-Phenyl
526
2
CO2tBu
4-iPr-Phenyl
527
3
CO2tBu
4-iPr-Phenyl
528
4
CO2tBu
4-iPr-Phenyl
533
1
SO2Me
4-iPr-Phenyl
534
2
SO2Me
4-iPr-Phenyl
535
3
SO2Me
4-iPr-Phenyl
536
4
SO2Me
4-iPr-Phenyl
577
1
H
2,4-di-Me-Phenyl
578
2
H
2,4-di-Me-Phenyl
579
3
H
2,4-di-Me-Phenyl
580
4
H
2,4-di-Me-Phenyl
589
1
COMe
2,4-di-Me-Phenyl
590
2
COMe
2,4-di-Me-Phenyl
591
3
COMe
2,4-di-Me-Phenyl
592
4
COMe
2,4-di-Me-Phenyl
593
1
CO2Me
2,4-di-Me-Phenyl
594
2
CO2Me
2,4-di-Me-Phenyl
595
3
CO2Me
2,4-di-Me-Phenyl
596
4
CO2Me
2,4-di-Me-Phenyl
597
1
CO2tBu
2,4-di-Me-Phenyl
598
2
CO2tBu
2,4-di-Me-Phenyl
599
3
CO2tBu
2,4-di-Me-Phenyl
600
4
CO2tBu
2,4-di-Me-Phenyl
605
1
SO2Me
2,4-di-Me-Phenyl
606
2
SO2Me
2,4-di-Me-Phenyl
607
3
SO2Me
2,4-di-Me-Phenyl
608
4
SO2Me
2,4-di-Me-Phenyl
613
1
H
2,6-di-iPr-Phenyl
614
2
H
2,6-di-iPr-Phenyl
615
3
H
2,6-di-iPr-Phenyl
616
4
H
2,6-di-iPr-Phenyl
625
1
COMe
2,6-di-iPr-Phenyl
626
2
COMe
2,6-di-iPr-Phenyl
627
3
COMe
2,6-di-iPr-Phenyl
628
4
COMe
2,6-di-iPr-Phenyl
629
1
CO2Me
2,6-di-iPr-Phenyl
630
2
CO2Me
2,6-di-iPr-Phenyl
631
3
CO2Me
2,6-di-iPr-Phenyl
632
4
CO2Me
2,6-di-iPr-Phenyl
633
1
CO2tBu
2,6-di-iPr-Phenyl
634
2
CO2tBu
2,6-di-iPr-Phenyl
635
3
CO2tBu
2,6-di-iPr-Phenyl
636
4
CO2tBu
2,6-di-iPr-Phenyl
641
1
SO2Me
2,6-di-iPr-Phenyl
642
2
SO2Me
2,6-di-iPr-Phenyl
643
3
SO2Me
2,6-di-iPr-Phenyl
644
4
SO2Me
2,6-di-iPr-Phenyl
685
1
H
2-morpholino-phenyl
686
2
H
2-morpholino-phenyl
687
3
H
2-morpholino-phenyl
688
4
H
2-morpholino-phenyl
697
1
COMe
2-morpholino-phenyl
698
2
COMe
2-morpholino-phenyl
699
3
COMe
2-morpholino-phenyl
700
4
COMe
2-morpholino-phenyl
701
1
CO2Me
2-morpholino-phenyl
702
2
CO2Me
2-morpholino-phenyl
703
3
CO2Me
2-morpholino-phenyl
704
4
CO2Me
2-morpholino-phenyl
705
1
CO2tBu
2-morpholino-phenyl
706
2
CO2tBu
2-morpholino-phenyl
707
3
CO2tBu
2-morpholino-phenyl
708
4
CO2tBu
2-morpholino-phenyl
713
1
SO2Me
2-morpholino-phenyl
714
2
SO2Me
2-morpholino-phenyl
715
3
SO2Me
2-morpholino-phenyl
716
4
SO2Me
2-morpholino-phenyl
721
1
H
4-morpholino-phenyl
722
2
H
4-morpholino-phenyl
723
3
H
4-morpholino-phenyl
724
4
H
4-morpholino-phenyl
729
1
CO2Me
4-morpholino-phenyl
730
2
CO2Me
4-morpholino-phenyl
731
3
CO2Me
4-morpholino-phenyl
732
4
CO2Me
4-morpholino-phenyl
779
1
H
4-OH-Phenyl
780
2
H
4-OH-Phenyl
781
3
H
4-OH-Phenyl
782
4
H
4-OH-Phenyl
791
1
COMe
4-OH-Phenyl
792
2
COMe
4-OH-Phenyl
793
3
COMe
4-OH-Phenyl
794
4
COMe
4-OH-Phenyl
795
1
CO2Me
4-OH-Phenyl
796
2
CO2Me
4-OH-Phenyl
797
3
CO2Me
4-OH-Phenyl
798
4
CO2Me
4-OH-Phenyl
799
1
CO2tBu
4-OH-Phenyl
800
2
CO2tBu
4-OH-Phenyl
801
3
CO2tBu
4-OH-Phenyl
802
4
CO2tBu
4-OH-Phenyl
807
1
SO2Me
4-OH-Phenyl
808
2
SO2Me
4-OH-Phenyl
809
3
SO2Me
4-OH-Phenyl
810
4
SO2Me
4-OH-Phenyl
815
1
H
2-OH-Phenyl
816
2
H
2-OH-Phenyl
817
3
H
2-OH-Phenyl
818
4
H
2-OH-Phenyl
827
1
COMe
2-OH-Phenyl
828
2
COMe
2-OH-Phenyl
829
3
COMe
2-OH-Phenyl
830
4
COMe
2-OH-Phenyl
831
1
CO2Me
2-OH-Phenyl
832
2
CO2Me
2-OH-Phenyl
833
3
CO2Me
2-OH-Phenyl
834
4
CO2Me
2-OH-Phenyl
835
1
CO2tBu
2-OH-Phenyl
836
2
CO2tBu
2-OH-Phenyl
837
3
CO2tBu
2-OH-Phenyl
838
4
CO2tBu
2-OH-Phenyl
843
1
SO2Me
2-OH-Phenyl
844
2
SO2Me
2-OH-Phenyl
845
3
SO2Me
2-OH-Phenyl
846
4
SO2Me
2-OH-Phenyl
863
1
COMe
4-OMe-Phenyl
864
2
COMe
4-OMe-Phenyl
865
3
COMe
4-OMe-Phenyl
866
4
COMe
4-OMe-Phenyl
867
1
CO2Me
4-OMe-Phenyl
868
2
CO2Me
4-OMe-Phenyl
869
3
CO2Me
4-OMe-Phenyl
870
4
CO2Me
4-OMe-Phenyl
871
1
CO2tBu
4-OMe-Phenyl
872
2
CO2tBu
4-OMe-Phenyl
873
3
CO2tBu
4-OMe-Phenyl
874
4
CO2tBu
4-OMe-Phenyl
879
1
SO2Me
4-OMe-Phenyl
880
2
SO2Me
4-OMe-Phenyl
881
3
SO2Me
4-OMe-Phenyl
882
4
SO2Me
4-OMe-Phenyl
887
1
H
2-OMe-Phenyl
888
2
H
2-OMe-Phenyl
889
3
H
2-OMe-Phenyl
890
4
H
2-OMe-Phenyl
899
1
COMe
2-OMe-Phenyl
900
2
COMe
2-OMe-Phenyl
901
3
COMe
2-OMe-Phenyl
902
4
COMe
2-OMe-Phenyl
903
1
CO2Me
2-OMe-Phenyl
904
2
CO2Me
2-OMe-Phenyl
905
3
CO2Me
2-OMe-Phenyl
906
4
CO2Me
2-OMe-Phenyl
907
1
CO2tBu
2-OMe-Phenyl
908
2
CO2tBu
2-OMe-Phenyl
909
3
CO2tBu
2-OMe-Phenyl
910
4
CO2tBu
2-OMe-Phenyl
915
1
SO2Me
2-OMe-Phenyl
916
2
SO2Me
2-OMe-Phenyl
917
3
SO2Me
2-OMe-Phenyl
918
4
SO2Me
2-OMe-Phenyl
923
1
H
3-CN-Phenyl
924
2
H
3-CN-Phenyl
925
3
H
3-CN-Phenyl
926
4
H
3-CN-Phenyl
935
1
COMe
3-CN-Phenyl
936
2
COMe
3-CN-Phenyl
937
3
COMe
3-CN-Phenyl
938
4
COMe
3-CN-Phenyl
939
1
CO2Me
3-CN-Phenyl
940
2
CO2Me
3-CN-Phenyl
941
3
CO2Me
3-CN-Phenyl
942
4
CO2Me
3-CN-Phenyl
943
1
CO2tBu
3-CN-Phenyl
944
2
CO2tBu
3-CN-Phenyl
945
3
CO2tBu
3-CN-Phenyl
946
4
CO2tBu
3-CN-Phenyl
951
1
SO2Me
3-CN-Phenyl
952
2
SO2Me
3-CN-Phenyl
953
3
SO2Me
3-CN-Phenyl
954
4
SO2Me
3-CN-Phenyl
959
1
H
2-Me-Phenyl
960
2
H
2-Me-Phenyl
961
3
H
2-Me-Phenyl
962
4
H
2-Me-Phenyl
971
1
COMe
2-Me-Phenyl
972
2
COMe
2-Me-Phenyl
973
3
COMe
2-Me-Phenyl
974
4
COMe
2-Me-Phenyl
975
1
CO2Me
2-Me-Phenyl
976
2
CO2Me
2-Me-Phenyl
977
3
CO2Me
2-Me-Phenyl
978
4
CO2Me
2-CN-Phenyl
979
1
CO2tBu
2-Me-Phenyl
980
2
CO2tBu
2-Me-Phenyl
981
3
CO2tBu
2-Me-Phenyl
982
4
CO2tBu
2-Me-Phenyl
987
1
SO2Me
2-Me-Phenyl
988
2
SO2Me
2-Me-Phenyl
989
3
SO2Me
2-Me-Phenyl
990
4
SO2Me
2-Me-Phenyl
995
1
H
4-Me-Phenyl
996
2
H
4-Me-Phenyl
997
3
H
4-Me-Phenyl
998
4
H
4-Me-Phenyl
1007
1
COMe
4-Me-Phenyl
1008
2
COMe
4-Me-Phenyl
1009
3
COMe
4-Me-Phenyl
1010
4
COMe
4-Me-Phenyl
1011
1
CO2Me
4-Me-Phenyl
1012
2
CO2Me
4-Me-Phenyl
1013
3
CO2Me
4-Me-Phenyl
1014
4
CO2Me
4-Me-Phenyl
1015
1
CO2tBu
4-Me-Phenyl
1016
2
CO2tBu
4-Me-Phenyl
1017
3
CO2tBu
4-Me-Phenyl
1018
4
CO2tBu
4-Me-Phenyl
1023
1
SO2Me
4-Me-Phenyl
1024
2
SO2Me
4-Me-Phenyl
1025
3
SO2Me
4-Me-Phenyl
1026
4
SO2Me
4-Me-Phenyl
1031
1
H
3-F-Phenyl
1032
2
H
3-F-Phenyl
1033
3
H
3-F-Phenyl
1034
4
H
3-F-Phenyl
1044
2
COMe
3-F-Phenyl
1045
3
COMe
3-F-Phenyl
1046
4
COMe
3-F-Phenyl
1047
1
CO2Me
3-F-Phenyl
1048
2
CO2Me
3-F-Phenyl
1049
3
CO2Me
3-F-Phenyl
1050
4
CO2Me
3-F-Phenyl
1051
1
CO2tBu
3-F-Phenyl
1052
2
CO2tBu
3-F-Phenyl
1053
3
CO2tBu
3-F-Phenyl
1054
4
CO2tBu
3-F-Phenyl
1059
1
SO2Me
3-F-Phenyl
1060
2
SO2Me
3-F-Phenyl
1061
3
SO2Me
3-F-Phenyl
1062
4
SO2Me
3-F-Phenyl
1067
1
H
2-Cl-Phenyl
1068
2
H
2-Cl-Phenyl
1069
3
H
2-Cl-Phenyl
1070
4
H
2-Cl-Phenyl
1079
1
COMe
2-Cl-Phenyl
1080
2
COMe
2-Cl-Phenyl
1081
3
COMe
2-Cl-Phenyl
1082
4
COMe
2-Cl-Phenyl
1083
1
CO2Me
2-Cl-Phenyl
1084
2
CO2Me
2-Cl-Phenyl
1085
3
CO2Me
2-Cl-Phenyl
1086
4
CO2Me
2-Cl-Phenyl
1087
1
CO2tBu
2-Cl-Phenyl
1088
2
CO2tBu
2-Cl-Phenyl
1089
3
CO2tBu
2-Cl-Phenyl
1090
4
CO2tBu
2-Cl-Phenyl
1095
1
SO2Me
2-Cl-Phenyl
1096
2
SO2Me
2-Cl-Phenyl
1097
3
SO2Me
2-Cl-Phenyl
1098
4
SO2Me
2-Cl-Phenyl
1103
1
H
4-Cl-Phenyl
1104
2
H
4-Cl-Phenyl
1105
3
H
4-Cl-Phenyl
1106
4
H
4-Cl-Phenyl
1115
1
COMe
4-Cl-Phenyl
1116
2
COMe
4-Cl-Phenyl
1117
3
COMe
4-Cl-Phenyl
1118
4
COMe
4-Cl-Phenyl
1119
1
CO2Me
4-Cl-Phenyl
1120
2
CO2Me
4-Cl-Phenyl
1121
3
CO2Me
4-Cl-Phenyl
1122
4
CO2Me
4-Cl-Phenyl
1123
1
CO2tBu
4-Cl-Phenyl
1124
2
CO2tBu
4-Cl-Phenyl
1125
3
CO2tBu
4-Cl-Phenyl
1126
4
CO2tBu
4-Cl-Phenyl
1131
1
SO2Me
4-Cl-Phenyl
1132
2
SO2Me
4-Cl-Phenyl
1133
3
SO2Me
4-Cl-Phenyl
1134
4
SO2Me
4-Cl-Phenyl
1139
1
H
3-Br-Phenyl
1140
2
H
3-Br-Phenyl
1141
3
H
3-Br-Phenyl
1142
4
H
3-Br-Phenyl
1151
1
COMe
3-Br-Phenyl
1152
2
COMe
3-Br-Phenyl
1153
3
COMe
3-Br-Phenyl
1154
4
COMe
3-Br-Phenyl
1155
1
CO2Me
3-Br-Phenyl
1156
2
CO2Me
3-Br-Phenyl
1157
3
CO2Me
3-Br-Phenyl
1158
4
CO2Me
3-Br-Phenyl
1159
1
CO2tBu
3-Br-Phenyl
1160
2
CO2tBu
3-Br-Phenyl
1161
3
CO2tBu
3-Br-Phenyl
1162
4
CO2tBu
3-Br-Phenyl
1167
1
SO2Me
3-Br-Phenyl
1168
2
SO2Me
3-Br-Phenyl
1169
3
SO2Me
3-Br-Phenyl
1170
4
SO2Me
3-Br-Phenyl
1175
1
H
3-CF3-Phenyl
1176
2
H
3-CF3-Phenyl
1177
3
H
3-CF3-Phenyl
1178
4
H
3-CF3-Phenyl
1187
1
COMe
3-CF3-Phenyl
1188
2
COMe
3-CF3-Phenyl
1189
3
COMe
3-CF3-Phenyl
1190
4
COMe
3-CF3-Phenyl
1191
1
CO2Me
3-CF3-Phenyl
1192
2
CO2Me
3-CF3-Phenyl
1193
3
CO2Me
3-CF3-Phenyl
1194
4
CO2Me
3-CF3-Phenyl
1195
1
CO2tBu
3-CF3-Phenyl
1196
2
CO2tBu
3-CF3-Phenyl
1197
3
CO2tBu
3-CF3-Phenyl
1198
4
CO2tBu
3-CF3-Phenyl
1203
1
SO2Me
3-CF3-Phenyl
1204
2
SO2Me
3-CF3-Phenyl
1205
3
SO2Me
3-CF3-Phenyl
1206
4
SO2Me
3-CF3-Phenyl
1211
1
H
3-CF3-Phenyl
1212
2
H
3-CF3-Phenyl
1213
3
H
3-CF3-Phenyl
1214
4
H
3-CF3-Phenyl
1223
1
COMe
3-CF3-Phenyl
1224
2
COMe
3-CF3-Phenyl
1225
3
COMe
3-CF3-Phenyl
1226
4
COMe
3-CF3-Phenyl
1227
1
CO2Me
3-CF3-Phenyl
1228
2
CO2Me
3-CF3-Phenyl
1229
3
CO2Me
3-CF3-Phenyl
1230
4
CO2Me
3-CF3-Phenyl
1231
1
CO2tBu
3-CF3-Phenyl
1232
2
CO2tBu
3-CF3-Phenyl
1233
3
CO2tBu
3-CF3-Phenyl
1234
4
CO2tBu
3-CF3-Phenyl
1239
1
SO2Me
3-CF3-Phenyl
1240
2
SO2Me
3-CF3-Phenyl
1241
3
SO2Me
3-CF3-Phenyl
1242
4
SO2Me
3-CF3-Phenyl
1247
1
H
3-iPr-Phenyl
1248
2
H
3-iPr-Phenyl
1249
3
H
3-iPr-Phenyl
1250
4
H
3-iPr-Phenyl
1259
1
COMe
3-iPr-Phenyl
1260
2
COMe
3-iPr-Phenyl
1261
3
COMe
3-iPr-Phenyl
1262
4
COMe
3-iPr-Phenyl
1263
1
CO2Me
3-iPr-Phenyl
1264
2
CO2Me
3-iPr-Phenyl
1265
3
CO2Me
3-iPr-Phenyl
1266
4
CO2Me
3-iPr-Phenyl
1267
1
CO2tBu
3-iPr-Phenyl
1268
2
CO2tBu
3-iPr-Phenyl
1269
3
CO2tBu
3-iPr-Phenyl
1270
4
CO2tBu
3-iPr-Phenyl
1275
1
SO2Me
3-iPr-Phenyl
1276
2
SO2Me
3-iPr-Phenyl
1277
3
SO2Me
3-iPr-Phenyl
1278
4
SO2Me
3-iPr-Phenyl
1355
1
H
2,6-di-Me-Phenyl
1356
2
H
2,6-di-Me-Phenyl
1357
3
H
2,6-di-Me-Phenyl
1358
4
H
2,6-di-Me-Phenyl
1367
1
COMe
2,6-di-Me-Phenyl
1368
2
COMe
2,6-di-Me-Phenyl
1369
3
COMe
2,6-di-Me-Phenyl
1370
4
COMe
2,6-di-Me-Phenyl
1371
1
CO2Me
2,6-di-Me-Phenyl
1372
2
CO2Me
2,6-di-Me-Phenyl
1373
3
CO2Me
2,6-di-Me-Phenyl
1374
4
CO2Me
2,6-di-Me-Phenyl
1375
1
CO2tBu
2,6-di-Me-Phenyl
1376
2
CO2tBu
2,6-di-Me-Phenyl
1377
3
CO2tBu
2,6-di-Me-Phenyl
1378
4
CO2tBu
2,6-di-Me-Phenyl
1383
1
SO2Me
2,6-di-Me-Phenyl
1384
2
SO2Me
2,6-di-Me-Phenyl
1385
3
SO2Me
2,6-di-Me-Phenyl
1386
4
SO2Me
2,6-di-Me-Phenyl
1463
1
H
3-morpholino-phenyl
1464
2
H
3-morpholino-phenyl
1465
3
H
3-morpholino-phenyl
1466
4
H
3-morpholino-phenyl
1475
1
COMe
3-morpholino-phenyl
1476
2
COMe
3-morpholino-phenyl
1477
3
COMe
3-morpholino-phenyl
1478
4
COMe
3-morpholino-phenyl
1479
1
CO2Me
3-morpholino-phenyl
1480
2
CO2Me
3-morpholino-phenyl
1481
3
CO2Me
3-morpholino-phenyl
1482
4
CO2Me
3-morpholino-phenyl
1483
1
CO2tBu
3-morpholino-phenyl
1484
2
CO2tBu
3-morpholino-phenyl
1485
3
CO2tBu
3-morpholino-phenyl
1486
4
CO2tBu
3-morpholino-phenyl
1491
1
SO2Me
3-morpholino-phenyl
1492
2
SO2Me
3-morpholino-phenyl
1493
3
SO2Me
3-morpholino-phenyl
1494
4
SO2Me
3-morpholino-phenyl
1503
1
COMe
4-morpholino-phenyl
1504
2
COMe
4-morpholino-phenyl
1505
3
COMe
4-morpholino-phenyl
1506
4
COMe
4-morpholino-phenyl
1507
1
CO2tBu
4-morpholino-phenyl
1508
2
CO2tBu
4-morpholino-phenyl
1509
3
CO2tBu
4-morpholino-phenyl
1510
4
CO2tBu
4-morpholino-phenyl
1511
1
SO2Me
4-morpholino-phenyl
1512
2
SO2Me
4-morpholino-phenyl
1513
3
SO2Me
4-morpholino-phenyl
1514
4
SO2Me
4-morpholino-phenyl
or a pharmaceutically acceptable salt thereof.

2,699 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/054,468Filed 10 May 2019 · us provisional application
Priority: 11 May 2018
Published: US 2022/0306629 A129 Sep 2022
Granted: 24 Feb 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 471/10
In which the condensed system contains two hetero rings: spiro-condensed systems
A61P 25/00
Drugs for disorders of the nervous system
C07D 207/20
Having one double bond between ring members or between a ring member and a non-ring member: with only hydrogen atoms, hydrocarbon or substituted…
C07D 209/96
Ring systems containing three or more rings: spiro-condensed ring systems

Family

Application62/670,116Us provisional application · filed 11 May 2018
US 2022/0306629 A1Pre-grant publication · published 29 Sep 2022
US 12,559,494 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Citations

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Abstract

Facts

Application

17/054,468Filed 10 May 2019 · us provisional application

Priority

11 May 2018

Published

US 2022/0306629 A129 Sep 2022

Granted

24 Feb 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 471/10
In which the condensed system contains two hetero rings: spiro-condensed systems
A61P 25/00
Drugs for disorders of the nervous system
C07D 207/20
Having one double bond between ring members or between a ring member and a non-ring member: with only hydrogen atoms, hydrocarbon or substituted…
C07D 209/96
Ring systems containing three or more rings: spiro-condensed ring systems