CA2688694A1 - Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione - Google Patents

Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Download PDF

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CA2688694A1
CA2688694A1 CA 2688694 CA2688694A CA2688694A1 CA 2688694 A1 CA2688694 A1 CA 2688694A1 CA 2688694 CA2688694 CA 2688694 CA 2688694 A CA2688694 A CA 2688694A CA 2688694 A1 CA2688694 A1 CA 2688694A1
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isoindol
piperidine
dihydro
oxo
amino
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CA2688694C (en
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Roger Shen-Chu Chen
George W. Muller
Markian S. Jaworsky
Manohar T. Saindane
Louise M. Cameron
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Celgene Corp
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D51/00—Closures not otherwise provided for
    • B65D51/24—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes
    • B65D51/28—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials
    • B65D51/2807—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container
    • B65D51/2857—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by displacing or removing an element enclosing it
    • B65D51/2864—Closures not otherwise provided for combined or co-operating with auxiliary devices for non-closing purposes with auxiliary containers for additional articles or materials the closure presenting means for placing the additional articles or materials in contact with the main contents by acting on a part of the closure without removing the closure, e.g. by pushing down, pulling up, rotating or turning a part of the closure, or upon initial opening of the container the additional article or materials being released by displacing or removing an element enclosing it the element being a plug or like element closing a passage between the auxiliary container and the main container
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Abstract

Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro- isoindol-2-yl)-piperidine-2,6-dione are disclosed. Compositions comprising the polymorphic forms, methods of making the polymorphic forms and methods of their use are also disclosed.

Claims (88)

1. Crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-
2-yl)-piperidine-2,6-dione which is unsolvated.

2. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to claim 1, which has an X-ray powder diffraction pattern comprising peaks at approximately 8, 14.5 and 16 degrees 2.theta..
3. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to claim 2, wherein the X-ray powder diffraction pattern comprises further peaks at approximately 17.5, 20.5, 24 and 26 degrees 2.theta..
4. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to claim 2 or 3, wherein the X-ray powder diffraction peaks occur at 7.9, 14.4 and 15.8 degrees 2.theta..
5. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to claim 3 or 4, wherein the further X-ray powder diffraction peaks occur at 17.6, 20.6, 24.1 and 26.0 degrees 2.theta..
6. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 5, which has an X-ray powder diffraction pattern corresponding substantially to the representative X-ray powder diffraction pattern as shown in Figure 1.
7. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 6, which has a differential scanning calorimetry thermogram comprising an endotherm at approximately 270°C.
8. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 7, which has a differential scanning calorimetry thermogram corresponding substantially to the representative differential scanning calorimetry thermogram as shown in Figure 4.
9. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 8, which has a thermogravimetric analysis curve indicative of an unsolvated material.
10. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 9, which has a thermogravimetric analysis curve corresponding substantially to the representative thermogravimetric analysis curve as shown in Figure 4.
11. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 10, which has an infrared spectrum corresponding substantially to the representative infrared spectrum as shown in Figure 2.
12. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 11, which has a Raman spectrum corresponding substantially to the representative Raman spectrum as shown in Figure 3.
13. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 12, which does not exhibit a significant weight gain from about 5% to about 95% relative humidity.
14. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 13, which has a moisture sorption/desorption isotherm corresponding substantially to the representative moisture sorption/desorption isotherm as shown in Figure 5.
15. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 14, which has a solubility curve corresponding substantially to the solubility curve as shown in Figure 51.
16. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 15, which has an intrinsic dissolution curve corresponding substantially to the Form A intrinsic dissolution curve as shown in Figure 53 or 54.
17. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 16, obtained by crystallization from a solvent system comprising 1-butanol, butyl acetate, ethanol, methanol, methyl ethyl ketone, or tetrahydrofuran.
18. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 17, obtained by crystallization from a solvent system comprising ethyl acetate.
19. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 2 to 18, wherein the recited X-ray powder diffraction peaks have an intensity at least equal to the median intensity of the other peaks in the X-ray powder diffraction pattern.
20. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 19, which is substantially pure.
21. A composition comprising the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 and amorphous 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
22. The composition of claim 21, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is present in an amount greater than about 50 weight percent.
23. The composition according to claim 21 or 22, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is present in an amount greater than about 80 weight percent.
24. The composition according to claim 21, 22 or 23, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is present in an amount greater than about 90 weight percent.
25. The composition according to claim 21, 22, 23 or 24, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is present in an amount greater than about 95 weight percent.
26. The composition according to claim 21, 22, 23, 24 or 25, wherein the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is present in an amount greater than about 97 weight percent.
27. A pharmaceutical composition comprising the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 and a pharmaceutically acceptable excipient.
28. A pharmaceutical composition comprising the composition as defined in claim 21, 22, 23, 24, 25 or 26 and a pharmaceutically acceptable excipient.
29. The pharmaceutical composition of claim 28, in which greater than about 50 weight percent of the 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is crystalline.
30. The pharmaceutical composition of claim 28 or 29, in which greater than about 75 weight percent of the 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is crystalline.
31. The pharmaceutical composition of claim 28, 29 or 30, in which greater than about 90 weight percent of the 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is crystalline.
32. The pharmaceutical composition according to claim 28, 29, 30 or 31, in which greater than about 95 weight percent of the 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is crystalline.
33. The pharmaceutical composition according to claim 28, 29, 30, 31 or 32, in which greater than about 97 weight percent of the 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione is crystalline.
34. The pharmaceutical composition according to any one of claims 28 to 33, which is a single unit dosage form.
35. The pharmaceutical composition according to any one of claims 28 to 34, which is a transdermal dosage form.
36. The pharmaceutical composition according to any one of claims 28 to 34, which is a mucosal dosage form.
37. The pharmaceutical composition according to any one of claims 28 to 34, which is a nasal dosage form.
38. The pharmaceutical composition according to any one of claims 28 to 34, which is a topical dosage form.
39. The pharmaceutical composition according to any one of claims 28 to 34, which is a parenteral dosage form.
40. The pharmaceutical composition according to any one of claims 28 to 34, which is a sublingual dosage form.
41. The pharmaceutical composition according to any one of claims 28 to 34, which is an oral dosage form.
42. The pharmaceutical composition according to claim 41, which is a tablet dosage form.
43. The pharmaceutical composition according to claim 41, which is a capsule dosage form.
44. The pharmaceutical composition according to claim 43, wherein the capsule contains about 5 mg of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
45. The pharmaceutical composition according to claim 43, wherein the capsule contains about 10 mg of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
46. The pharmaceutical composition according to claim 43, wherein the capsule contains about 25 mg of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
47. The pharmaceutical composition according to claim 43, wherein the capsule contains from about 0.1 mg to about 150 mg of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
48. The crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione according to any one of claims 1 to 20, prepared by a method comprising at least one of the following steps:

(a) crystallization from 1-butanol, butyl acetate, ethanol, ethyl acetate, methanol, methyl ethyl ketone or tetrahydrofuran solvent systems;

(b) conversion of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form B, in a tetrahydrofuran solvent system;

(c) desolvation of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form B;

(d) conversion of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form C in a tetrahydrofuran solvent system;

(e) desolvation of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form C; or (f) desolvation of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form D; or (g) conversion of crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Form H in a tetrahydrofuran solvent system.
49. Use of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the manufacture of a medicament for the treatment of a myelodysplastic syndrome in a patient in need thereof.
50. Use of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the manufacture of a medicament for the treatment of a myelodysplastic syndrome in a patient in need thereof.
51. Use of a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the treatment of a myelodysplastic syndrome in a patient in need thereof.
52. Use of a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the treatment of a myelodysplastic syndrome in a patient in need thereof.
53. The use according to claim 51 or 52, wherein the therapeutically effective amount is 5 mg.
54. The use according to claim 51 or 52, wherein the therapeutically effective amount is 10 mg.
55. The use according to claim 51 or 52, wherein the therapeutically effective amount is 25 mg.
56. The use according to claim 51 or 52, wherein the therapeutically effective amount is from about 0.1 mg to about 150 mg.
57. A pharmaceutical composition for use in the treatment of a myelodysplastic syndrome in a patient in need thereof, comprising:

A) a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; and B) a pharmaceutically acceptable excipient.
58. The pharmaceutical composition according to claim 57, wherein the therapeutically effective amount is 5 mg.
59. The pharmaceutical composition according to claim 57, wherein the therapeutically effective amount is 10 mg.
60. The pharmaceutical composition according to claim 57, wherein the therapeutically effective amount is 25 mg.
61. The pharmaceutical composition according to claim 57, wherein the therapeutically effective amount is from about 0.1 mg to about 150 mg.
62. Use of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the manufacture of a medicament for the treatment of pain.
63. Use of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the manufacture of a medicament for the treatment of macular degeneration.
64. Use of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the manufacture of a medicament for the treatment of a myeloproliferative disease.
65. Use of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the manufacture of a medicament for the treatment of pain.
66. Use of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the manufacture of a medicament for the treatment of macular degeneration.
67. Use of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the manufacture of a medicament for the treatment of a myeloproliferative disease.
68. Use of a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the treatment of pain in a patient in need thereof.
69. Use of a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the treatment of macular degeneration in a patient in need thereof.
70. Use of a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20, in the treatment of a myeloproliferative disease in a patient in need thereof.
71. Use of a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the treatment of pain in a patient in need thereof.
72. Use of a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the treatment of macular degeneration in a patient in need thereof.
73. Use of a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26, in the treatment of a myeloproliferative disease in a patient in need thereof.
74. The use according to any one of claims 68 to 73, wherein the therapeutically effective amount is 5 mg.
75. The use according to any one of claims 68 to 73, wherein the therapeutically effective amount is 10 mg.
76. The use according to any one of claims 68 to 73, wherein the therapeutically effective amount is 25 mg.
77. The use according to any one of claims 68 to 73, wherein the therapeutically effective amount is from about 0.1 mg to about 150 mg.
78. A pharmaceutical composition for use in the treatment of pain in a patient in need thereof, comprising:

A) a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; and B) a pharmaceutically acceptable excipient.
79. A pharmaceutical composition for use in the treatment of macular degeneration in a patient in need thereof, comprising:

A) a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; and B) a pharmaceutically acceptable excipient.
80. A pharmaceutical composition for use in the treatment of a myeloproliferative disease in a patient in need thereof, comprising:

A) a therapeutically effective amount of the crystalline 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione as defined in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20; and B) a pharmaceutically acceptable excipient.
81. A pharmaceutical composition for use in the treatment of pain in a patient in need thereof, comprising:

A) a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26;
and B) a pharmaceutically acceptable excipient.
82. A pharmaceutical composition for use in the treatment of macular degeneration in a patient in need thereof, comprising:

A) a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26;
and B) a pharmaceutically acceptable excipient.
83. A pharmaceutical composition for use in the treatment of a myeloproliferative disease in a patient in need thereof, comprising:

A) a therapeutically effective amount of the composition as defined in claim 21, 22, 23, 24, 25 or 26;
and B) a pharmaceutically acceptable excipient.
84. The pharmaceutical composition according to any one of claims 78 to 80, wherein the therapeutically effective amount is 5 mg.
85. The pharmaceutical composition according to any one of claims 78 to 80, wherein the therapeutically effective amount is 10 mg.
86. The pharmaceutical composition according to any one of claims 78 to 80, wherein the therapeutically effective amount is 25 mg.
87. The pharmaceutical composition according to any one of claims 78 to 80, wherein the therapeutically effective amount is from about 0.1 mg to about 150 mg.
88. The pharmaceutical composition according to any one of claims 57 to 61 or according to any one of claims 78 to 87, further comprising amorphous 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione.
CA 2688694 2003-09-04 2004-09-03 Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione Active CA2688694C (en)

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