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Claims for Patent: 8,697,686

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Claims for Patent: 8,697,686

Title:Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-thtrahydro-1H-3-benzazepine hydrochloride
Abstract: The present invention is directed to crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, compositions containing the same and uses thereof.
Inventor(s): Agarwal; Rajesh K. (San Diego, CA), Betts, III; William L. (San Diego, CA), Henshilwood; James A. (Carlsbad, CA), Kiang; Yuan-Hon (Newbury Park, CA), Post; Noah (San Diego, CA)
Assignee: Arena Pharmaceuticals, Inc. (San Diego, CA)
Application Number:13/425,669
Patent Claims: 1. A method for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate comprising the step of: exposing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride to water to form (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate.

2. A method according to claim 1, wherein said (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride is hygroscopic.

3. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate prepared by the method of claim 1.

4. A method of preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate comprising mixing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride with a crystallizing solvent containing water, and inducing precipitation of the hemihydrate from the crystallizing solvent.

5. A method according to claim 4, wherein the crystallizing solvent contains an alcohol, water, and a hydrocarbon.

6. A method according to claim 5, wherein the alcohol is methanol, ethanol, 2-nitroethanol, 2-fluoroethanol, 2,2,2-trifluoroethanol, ethylene glycol, 1-propanol, 2-propanol, 2-methoxyethanol, 1-butanol, 2-butanol, i-butyl alcohol, t-butyl alcohol, 2-ethoxyethanol, diethylene glycol, 1-, 2-, or 3-pentanol, neo-pentyl alcohol, t-pentyl alcohol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, cyclohexanol, benzyl alcohol, phenol, or glycerol.

7. A method according to claim 6, wherein the alcohol is 2-propanol.

8. A method according to claim 5, wherein the hydrocarbon is benzene, cyclohexane, pentane, hexane, toluene, cycloheptane, methylcyclohexane, heptane, ethylbenzene, m-xylene, o-xylene, p-xylene, octane, indane, nonane, or naphthalene.

9. A method according to claim 8, wherein the hydrocarbon is cyclohexane.

10. A method according to claim 5, wherein the weight ratio of alcohol to water in the crystallizing solvent is 35:1 to 25:1.

11. A method according to claim 10, wherein the weight ratio of alcohol to water in the crystallizing solvent is 32:1 to 27:1.

12. A method according to claim 11, wherein the weight ratio of alcohol to water in the crystallizing solvent is 30:1 to 28:1.

13. A method according to claim 12, wherein the weight ratio of alcohol to water is about 29:1.

14. A method according to claim 5, wherein the weight ratio of alcohol plus water to hydrocarbon in the crystallizing solvent is 5:1 to 2:1.

15. A method according to claim 14, wherein the weight ratio of alcohol plus water to hydrocarbon in the crystallizing solvent is 3:1 to 2:1.

16. A method according to claim 15, wherein the weight ratio of alcohol plus water to hydrocarbon in the crystallizing solvent is or about 2.5:1.

17. A method according to claim 4, wherein the weight ratio of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride to crystallizing solvent is 1:2 to 1:15.

18. A method according to claim 17, wherein the weight ratio of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride to crystallizing solvent is 1:6 to 1:10.

19. A method according to claim 18, wherein the weight ratio of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride to crystallizing solvent is about 1:8.

20. A method according to claim 4, wherein the mixture containing the crystallizing solvent and (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride is maintained at and/or heated to a temperature of 40 to 80.degree. C. prior to inducing precipitation.

21. A method according to claim 20, wherein the mixture containing the crystallizing solvent and (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride is maintained at and/or heated to a temperature of 50 to 70.degree. C. prior to inducing precipitation.

22. A method according to claim 21, wherein the mixture containing the crystallizing solvent and (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride is maintained at and/or heated to a temperature of about 60.degree. C.

23. A method according to claim 4, wherein (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride is dissolved in the crystallizing solvent prior to inducing precipitation.

24. A method according to claim 23, wherein the dissolution is achieved by heating the mixture to a temperature between 40 and 80.degree. C.

25. A method according to claim 24, wherein the dissolution is achieved by heating the mixture to a temperature of about 60.degree. C.

26. A method according to claim 4, wherein precipitation of the hemihydrate is induced by cooling the mixture containing the crystallizing solvent and (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride.

27. A method according to claim 26, wherein precipitation of the hemihydrate is induced by cooling the mixture to a temperature of -15 to 15.degree. C.

28. A method according to claim 27, wherein precipitation of the hemihydrate is induced by cooling the mixture to a temperature of -5 to 10.degree. C.

29. A method according to claim 28, wherein precipitation of the hemihydrate is induced by cooling the mixture to a temperature of 0 to 5.degree. C.

30. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate obtained by a method according to claim 4.

31. A method of preparing a pharmaceutical composition comprising mixing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate with a pharmaceutically acceptable carrier.

32. The method of claim 31, wherein the (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate is prepared by a method of claim 1.

33. The method of claim 31, wherein the (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate is prepared by a method of claim 4.

34. A method according to claim 31, further comprising forming the pharmaceutical composition into a tablet, a pill, a powder, a lozenge, a sachet, a cachet, an elixir, a suspension, emulsions, a solution, a syrup, soft or hard gelatin capsule, a suppository, a sterile injectable solution, or a sterile packaged powder.

35. A pharmaceutical composition prepared by the method of claim 31.

36. A pharmaceutical composition prepared by the method of claim 34.
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