Crystalline salt forms
Disclosed are various crystalline salt forms of D-Arg-Dmt-Lys-Phe-NH 2 .
1. A crystalline form of a salt of Compound I,
wherein said crystalline form has peaks in its XRPD pattern at values of two theta as listed in any one of Tables 1′-20′;
wherein Table 1′ is:
Pos. [°2θ]
4.9500
5.7914
8.5140
9.8145
10.5199
11.9028
12.3400
12.6450
13.1574
16.0665
16.7594
17.0428
19.0804
20.3368
20.7068
21.7397
Table 2′ is:
Pos. [°2θ]
7.4205
9.8832
12.4010
13.0698
13.3833
14.4079
15.0973
15.5537
16.2771
16.8114
17.1732
17.4697
17.7008
19.4681
19.8491
22.8297
29.9651
32.5913
Table 3′ is:
Pos. [°2θ]
6.3236
7.1904
9.0662
11.1993
11.6515
11.8245
12.2481
12.7291
12.9196
13.4259
13.9356
14.0866
14.3102
14.7230
15.3518
15.7767
16.0824
16.6610
16.9655
17.4222
18.1176
18.9399
19.5396
19.7829
34.7854
20.0556
20.2220
21.6820
22.4522
22.7058
23.1326
23.3451
23.7455
24.2204
24.5976
24.7839
25.6635
25.9383
27.0486
27.7138
28.2876
28.5866
28.8350
29.4111
29.7366
30.9351
31.2970
31.8586
34.1666
Table 4′ is:
Pos. [°2θ]
6.5048
7.0412
9.0165
11.5522
11.8465
12.0031
12.4973
13.0115
13.2622
14.2951
14.4394
14.6700
15.0149
15.7182
15.8732
16.0677
17.3224
17.6596
18.0742
19.3625
19.5565
19.6954
20.0052
20.5458
21.1722
21.9749
22.4132
22.7633
23.1157
23.4474
23.7123
24.2578
24.5249
25.0281
25.2220
25.4124
26.1017
26.4002
26.6640
27.2584
27.6862
28.2087
28.4358
28.6690
29.0632
29.7900
30.1856
31.7342
32.5306
34.2641
Table 5′ is:
Pos. [°2θ]
5.6855
6.0206
10.3924
10.9552
11.1560
11.6500
12.0524
13.5772
13.8529
14.7106
14.9409
15.2690
15.7091
15.9920
17.0746
17.5076
17.9935
18.2959
18.5258
18.7728
19.6638
20.4019
20.8566
21.2027
21.3736
21.6173
22.0030
22.1468
22.4678
22.9236
23.4098
24.1636
24.6355
24.8676
25.2453
25.4632
25.9375
26.4465
27.2385
27.8576
28.1594
28.6842
29.1886
30.2331
30.8093
32.2440
32.6305
33.2034
33.6754
34.5344
Table 6′ is:
Pos. [°2θ]
3.2104
4.3126
5.9916
7.4447
9.3645
9.6885
9.9966
10.3209
11.8020
12.0313
12.3878
12.7870
13.6046
14.3857
14.5904
14.9160
15.1627
15.7759
15.9359
16.3636
17.5056
18.0062
18.4116
18.9363
19.4525
19.7728
20.1145
20.6143
21.3512
22.1408
22.7308
23.2392
23.8175
24.0397
24.8469
25.4521
26.0833
26.6795
27.1575
27.8454
28.7187
29.7607
31.1650
32.1555
33.2176
Table 7′ is:
Pos. [°2θ]
4.9532
6.1637
7.2943
7.7207
8.3148
9.8933
10.0378
12.2572
13.1795
13.3769
13.9612
14.5695
14.8668
15.0420
16.1696
16.4614
17.2938
18.0668
18.6224
19.4090
19.6513
20.1142
20.4050
20.6432
21.3207
22.0879
22.5352
22.8692
23.3140
24.0468
24.3692
24.7043
25.7054
26.1300
26.6847
27.4517
28.5093
29.3658
29.8396
30.2682
31.3451
31.6554
33.2878
34.2219
Table 8′ is:
Pos. [°2θ]
3.8204
4.2694
5.6244
6.5112
6.9639
8.1270
9.0666
10.3663
10.7413
11.3178
11.7667
12.3780
13.0244
13.6355
14.4623
14.8263
15.3745
15.7939
16.4008
16.9166
17.3729
17.6682
18.1633
18.3587
19.0634
19.8595
20.3863
20.7089
21.1449
22.3294
22.7660
23.1962
23.5383
23.9992
24.5505
24.9379
25.6244
26.9282
28.5609
29.4356
Table 9′ is:
Pos. [°2θ]
5.4182
5.7226
9.4519
9.7709
10.8340
11.0000
11.7890
13.3227
13.5503
13.9236
14.3536
14.6610
14.7960
15.0602
15.5639
15.7577
16.2767
17.1600
17.4509
17.6937
18.1813
18.8180
18.9824
19.6693
20.5851
21.0850
21.4834
21.7565
22.0457
22.3107
23.1703
23.7448
23.9081
24.4576
24.9599
25.5780
25.9086
26.6417
27.2891
27.5817
28.5785
28.9965
29.5971
30.1716
30.3897
31.0846
Table 10′ is:
Pos. [°2θ]
5.4123
9.6642
9.9532
10.7777
10.9908
11.8302
13.3865
13.9832
14.5130
15.0235
15.6073
15.9886
17.2884
17.7412
18.7012
19.5647
20.0217
21.0255
21.3918
22.0785
22.8159
23.6802
24.0516
25.8493
26.9534
27.7402
28.1612
29.2755
30.5014
Table 11′ is:
Pos. [°2θ]
3.6528
5.3346
6.1921
7.1693
7.2584
7.9555
8.2989
9.2514
10.5913
11.1450
12.0332
12.7127
13.1965
13.5693
13.8163
14.3773
14.6066
15.3422
15.5476
15.9810
16.6013
17.5327
17.8949
18.2706
19.0516
19.3988
19.8836
20.2075
20.3963
20.7842
21.1854
21.8139
22.0119
22.4021
22.6620
22.9995
23.2815
23.5370
23.9934
24.6748
24.8788
25.7236
26.0766
26.8205
27.8212
28.5683
28.9477
29.3638
30.7259
32.1373
Table 12′ is:
Pos. [°2θ]
4.2283
5.2902
5.7064
7.0087
7.2740
8.4471
10.2953
10.4698
11.1043
11.2764
11.6690
12.0243
12.3661
12.6972
13.0211
13.2807
14.8277
15.4615
15.8235
16.0773
16.9930
17.2436
18.1053
19.5434
20.7010
21.1934
21.9721
22.2605
22.6296
23.6035
23.7351
24.0613
24.4738
24.9772
25.5868
26.0270
27.2637
27.9596
28.5769
30.7356
31.2491
Table 13′ is:
Pos. [°2θ]
4.6078
4.7247
5.6369
5.7945
6.9083
7.2036
7.4378
9.2520
9.3801
10.0352
10.3048
11.1685
11.4467
11.7464
12.7059
13.1603
13.3277
13.6611
14.2278
14.6322
14.9188
15.0644
15.7469
15.9535
16.2032
16.3240
16.6769
17.4243
18.2889
18.8043
19.2960
19.5746
19.9329
20.2723
20.5228
21.1443
21.5244
21.7014
22.0764
22.3112
22.3752
22.6648
22.8586
23.1084
23.2825
23.5664
23.9441
24.1708
24.2438
24.5667
24.7979
25.2094
25.5564
26.3596
26.4901
26.8577
27.3567
27.6722
28.0031
28.3434
28.6121
29.0080
29.5671
30.6297
31.2974
31.9650
32.3013
33.4812
33.9277
34.2253
Table 14′ is:
Pos. [°2θ]
4.8468
7.2009
9.2287
9.8752
11.3790
12.3753
13.1003
13.3414
14.0505
14.4103
14.9682
15.5626
16.0210
16.2253
16.5208
16.8847
17.3260
18.0436
18.5063
19.5667
19.8049
20.4746
21.3412
21.6458
21.8878
22.4062
22.9397
23.2065
23.6258
23.8043
24.2839
24.5292
24.9422
25.6526
26.2095
26.5712
26.8039
27.3245
27.9402
28.3452
29.7807
30.4185
32.4348
33.9687
Table 15′ is:
Pos. [°2θ]
5.2173
6.5788
10.4657
11.9526
12.2981
12.9633
13.1469
13.6532
13.9226
14.0801
14.8387
15.2947
15.7415
16.0705
17.0800
17.8037
18.0998
19.2649
19.6536
20.4686
20.9891
21.5138
22.3786
23.1604
24.0181
24.7153
25.0063
25.3823
26.0374
26.3551
27.5053
28.0100
28.7269
31.3366
32.4594
Table 16′ is:
Pos. [°2θ]
6.6183
7.3884
7.6111
8.2981
8.8993
10.0751
11.1019
11.5582
11.8344
12.2224
12.9751
13.4040
13.8874
14.2668
14.4971
15.0582
15.7548
16.3188
17.3388
17.9628
18.5415
18.9064
19.4667
19.7556
20.1836
20.7747
21.5446
22.2369
22.6652
23.0991
23.6074
23.8948
24.1368
24.5986
25.2568
25.9952
26.9499
27.4845
27.8343
28.8828
29.2983
29.6677
30.1333
30.7281
31.5937
32.9662
33.8294
Table 17′ is:
Pos. [°2θ]
5.2074
6.5759
10.4268
11.9087
12.2972
12.8749
13.0948
13.6525
15.2610
15.7084
16.0248
16.4827
17.0200
17.7452
18.0663
19.2467
19.6260
20.4182
20.9504
21.1080
21.4534
22.2977
23.1512
23.9912
24.6413
24.9511
25.3280
25.9830
26.2805
27.4563
28.6746
29.6573
31.2290
32.3846
Table 18′ is:
Pos. [°2θ]
4.7133
7.0625
7.8327
9.4373
10.8320
11.2560
11.5530
12.1400
12.4180
13.2125
13.6676
14.1438
14.5314
14.8391
15.5031
15.6570
15.9242
16.2469
16.7975
18.0638
18.2986
18.6074
18.9236
19.0681
19.8194
20.2669
21.3752
21.6758
21.9446
22.6951
23.2295
23.6142
24.0109
24.4314
25.2281
25.5842
26.1514
26.7925
27.1916
28.1339
28.5109
29.2877
29.7222
30.6360
31.3505
32.6032
32.9347
33.8939
Table 19′ is:
Pos. [°2θ]
5.0941
10.2223
11.8691
13.2023
13.7755
13.9773
14.6467
15.9075
16.7186
20.4020
21.9198
23.0969
23.5325
24.4800
25.2794
and
Table 20′ is:
Pos. [°2θ]
4.1731
5.1086
6.5676
7.9847
9.9321
10.3453
11.9442
13.1111
14.0979
14.5776
14.8894
15.4458
16.0064
17.5761
18.0178
18.5153
18.9551
19.2662
19.9186
20.3646
20.8102
21.1557
22.1676
22.3940
22.8184
23.2383
23.3762
24.1177
25.1899
25.5494
26.0776
27.5686
2. A crystalline form of a salt of Compound I,
wherein said crystalline form has characteristic peaks in its XRPD pattern as described in any one of FIGS. 1-26 .
3. The crystalline form of claim 1 , wherein the crystalline form has peaks in its XRPD pattern at values of two theta as listed in any one of Tables 11′-18′.
4. The crystalline form of claim 1 , wherein the crystalline form has peaks in its XRPD pattern at values of two theta as listed in any one of Tables 5′, 6′, 9′, and 10′.
5. The crystalline form of claim 1 , wherein the crystalline form has peaks in its XRPD pattern at values of two theta as listed in any one of Tables 1′, 2′, 3′, 4′, 7′, 8′, 19′, and 20′.
6. A composition, comprising a crystalline form of claim 1 .
7. A process for making a pharmaceutical composition comprising Compound I,
comprising dissolving a crystalline form of claim 1 .
8. A composition, comprising a crystalline form of claim 2 .
9. A composition, comprising a crystalline form of claim 3 .
10. A composition, comprising a crystalline form of claim 4 .
11. A composition, comprising a crystalline form of claim 5 .
12. A process for making a pharmaceutical composition comprising Compound I,
comprising dissolving a crystalline form of claim 2 .
13. A process for making a pharmaceutical composition comprising Compound I,
comprising dissolving a crystalline form of claim 3 .
14. A process for making a pharmaceutical composition comprising Compound I,
comprising dissolving a crystalline form of claim 4 .
15. A process for making a pharmaceutical composition comprising Compound I,
comprising dissolving a crystalline form of claim 5 .