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Claims for Patent: 5,874,447

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Claims for Patent: 5,874,447

Title: 4-Phenylpiperidine compounds for treating depression
Abstract:The invention relates to a compound, and pharmaceutically acceptable salts, having the formula I: ##STR1## wherein: R represents an alkyl or alkynyl group having 1-4 carbon atoms, or a phenyl group optionally substituted by C.sub.1-4 alkyl, alkylthio, alkoxy, halogen, nitro, acylamino, methylsulfonyl or methylenedioxy, or represents tetrahydronaphthyl, R.sup.1 represents hydrogen, trifluoro (C.sub.1-4) alkyl, alkyl or alkynyl, X represents hydrogen, alkyl having 1-4 carbon atoms, alkoxy, trifluoroalkyl, hydroxy, halogen, methylthio or aralkoxy, R.sup.2 represents: a C1-C10 alkyl group, a phenyl group optionally substituted by one or more of the following groups: a C1-C10 alkyl group, a halogen group, a nitro group, hydroxy group, and/or an alkoxy group.
Inventor(s): Benneker; Franciscus Bernardus Gemma (Nijmegan, NL), Van Dalen; Frans (Neunen, NL), Lemmens; Jacobus Maria (Mook, NL), Peters; Theodorus Hendricus Antonium (Arnhem, NL), Picha; Frantisek (Brno, CS)
Assignee: Synthon B. V. (Nijmegen, NL)
Application Number:08/872,023
Patent Claims: 1. A compound having the formula: ##STR11## wherein R.sup.2 represents C.sub.1 -C.sub.10 alkyl group or a substituted or unsubstituted phenyl group wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.10 alkyl, halogen, nitro, hydroxy, alkoxy, and combinations thereof.

2. The compound according to claim 1, wherein the R.sup.2 group represents a C.sub.1 -C.sub.4 alkyl group.

3. The compound according to claim 1, wherein the R.sup.2 group is a C.sub.1 -C.sub.2 alkyl group.

4. The compound according to claim 1, having a solubility at about 20.degree. C. of at least about 10 mg per ml water.

5. The compound according to claim 4, having a solubility in water of at least 1000 mg per ml at about 20.degree. C.

6. A process, which comprises mixing together a compound, a salt, and/or a base thereof, having the formula: ##STR12## with a sulfonic acid of the general formula R.sup.2 -SO.sub.3 H, wherein R.sup.2 represents C.sub.1 -C.sub.10 alkyl group or a substituted or unsubstituted phenyl group wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.10 alkyl, halogen, nitro, hydroxy, alkoxy, and combinations thereof,

to produce a sulfonate salt compound according to claim 1.

7. The process according to claim 6, which further comprises mixing together said sulfonate salt compound with a reagent selected from the group consisting of hydrochloric acid, hydrobromic acid, hydriodic acid, acetic acid, propionic acid, maleic acid, fumaric acid, oxalic acid, succinic acid, tartaric acid, citric acid, embonic acid/pamoic acid, sulfuric acid, water, methanol, and ethanol, to form a salt or solvate of said reagent.

8. The process according to claim 7, wherein the salt of said reagent is produced and is recovered as a solid having a purity of at least 90 wt %.

9. The process according to claim 7, wherein said reagent is maleic acid; said mixing produces paroxetine maleate; and which further comprises recovering said paroxetine maleate in a purity of at least 98%.

10. The process according to claim 7, wherein said reagent is acetic acid; said mixing produces paroxetine acetate; and which further comprises recovering said paroxetine acetate in a purity of at least 98%.

11. A process according to claim 6, which further comprises mixing together said sulfonate salt compound with at least one of an organic or an inorganic base to form a free base thereof.

12. The process according to claim 11, wherein the base is selected from the group consisting essentially of: sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, sodium carbonate, methylamine, dimethylamine, triethylamine, and pyridine.

13. The process according to claim 11, further comprising isolating said free base in a purity of at least 95%.

14. The process according to claim 13, wherein said isolated free base has a purity of at least 98%.

15. The compound produced by the process according to claim 6.

16. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 and at least one pharmaceutically acceptable carrier or diluent.

17. The pharmaceutical composition according to claim 16, wherein said composition is a solid dosage form.

18. A method for treating depression, obsessive/compulsive disorders, panic disorders, bulimia, anorexia, pain, obesity, senile dementia, migraine, or social phobias, which comprises administering to a patient in need thereof a therapeutically effective amount of the compound as claimed in claim 1.

19. The method according to claim 18, wherein said patient is a human.

20. The method according to claim 18, wherein said method comprises administering an effective antidepressant amount of said compound to a patient suffering from depression.

21. A compound of the following formula: ##STR13##

22. A pharmaceutical composition comprising a therapeutically effective amount of a compound of the following formula: ##STR14## wherein R.sup.2 is methyl, ethyl, benzyl, p-chlorobenzyl, or tolyl; and a pharmaceutically acceptable carrier or diluent.

23. The pharmaceutical composition according to claim 22, wherein said composition is for oral administration.

24. The pharmaceutical composition according to claim 22, wherein R.sup.2 is methyl.

25. The pharmaceutical composition according to claim 24, wherein said composition is a solid dosage form.

26. The pharmaceutical composition according to claim 25, wherein said composition is a tablet.

27. A method of treating depression, obsessive/compulsive disorders or panic disorders which comprises administering to a patient in need thereof an effective amount of a compound of the following formula: ##STR15## wherein R.sup.2 is methyl, ethyl, benzyl, p-chlorobenzyl, or tolyl.

28. The method according to claim 27, wherein R.sup.2 is methyl.

29. The method according to claim 28, wherein an effective antidepressant amount is administered to said patient.
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