Claims
- 1. A compound corresponding to a formula selected from the group consisting of: whereinR14 and R15 may be the same or different and are each independently selected from the group consisting of C1-6-alkyl, aryl and C3-7-cycloalkyl; and R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1, wherein R14 and R15 are each independently selected from the group consisting of C1-6-alkyl.
- 3. A compound according to claim 1, wherein R14 and R15 are both CH3.
- 4. A compound according to claim 1, wherein R21 is selected from the group consisting of C1-6-alkoxy.
- 5. A compound according to claim 4, wherein R21 is a methoxy group.
- 6. A compound according to claim 1, selected from the group consisting of [4-dimethylaminomethyl-3-(3-methoxyphenyl)]-cyclohexanone and [4-dimethylaminomethyl-3-(3-methoxyphenyl)]-cyclohex-2-en-one.
- 7. A method of preparing a compound corresponding to the formula IVa whereinR14 and R15 may be the same or different and are each independently selected from the group consisting of C2-6-alkyl, aryl and C3-7-cycloalkyl; and R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, said method comprising: reacting 3,3-dimethyl-1,5-dioxa-spiro[5.5]-undecan-8-one corresponding to the formula: with an immonium salt corresponding to the formula V: wherein R14 and R15 have the meanings given above, to obtain a Mannich base corresponding to the formula VII: wherein R14 and R15 have the meanings given above,thereafter reacting the Mannich base of formula VII with an organometallic compound corresponding to formula VI: whereinZ represents MgCl, MgBr MgI or lithium, and R22 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, to obtain a compound corresponding to formula III: whereinR14 and R15 have the meanings given above, and R20 has the meaning given above for R21, and then reacting the compound corresponding to formula III with an acid to obtain the compound corresponding to formula IVa.
- 8. A method according to claim 7, wherein the acid with which the compound corresponding to formula III is reacted is selected from the group consisting of hydrochloric acid, formic acid and acetic acid.
- 9. A method according to claim 7, wherein the reaction of the Mannich base corresponding to formula VII with the organometallic compound corresponding to formula VI is carried out in an aliphatic ether.
- 10. A method according to claim 9, wherein said ether is selected from the group consisting of diethyl ether and tetrahydrofuran.
- 11. A method according to claim 7, wherein the reaction of the Mannich base corresponding to formula VII with the organometallic compound corresponding to formula VI is carried out at a temperature in the range from −70° C. to 60° C.
- 12. A method according to claim 7, wherein the reaction of the Mannich base corresponding to formula VII with the organometallic compound corresponding to formula VI is carried out with the addition of an entraining agent.
- 13. A method according to claim 12, wherein said entraining agent is 1,2-dibromoethane.
- 14. A method of preparing a compound corresponding to the formula IV: whereinR14 and R15 may be the same or different and are each independently selected from the group consisting of C2-6-alkyl, aryl and C3-7-cycloalkyl; and R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, said method comprising preparing a compound corresponding to formula IVa: wherein R14, R15 and R21 have the meanings given above, by the method according to claim 7, andthereafter catalytically hydrogenating the compound corresponding to formula IVa to obtain the compound corresponding to formula IV.
- 15. A method according to claim 14, wherein said hydrogenating is carried out in a solvent.
- 16. A method according to claim 15, wherein said solvent is ethyl acetate or a C1-4-alkyl alcohol.
- 17. A method according to claim 14, wherein said hydrogenating is carried out at a hydrogen pressure in the range from 0.1 to 10 bar and a temperature in the range from 20° C. to 80° C.
- 18. A method according to claim 14, wherein said hydrogenating is carried out using a platinum or palladium catalyst absorbed on a support material.
- 19. A method according to claim 18, wherein said support material is activated carbon.
- 20. A cyclohexenone compound corresponding to the formula: whereinR14 and R15 may be the same or different and are each independently selected from the group consisting of C2-6-alkyl, aryl and C3-7-cycloalkyl; and R21 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, said compound being produced by the process of treating a dioxa-spiro compound containing a tertiary OH group corresponding to formula III whereinR14 and R15 have the meanings given above; and R20 is selected from the group consisting of H, C1-6-alkoxy, O-C3-7-cycloalkyl, O-aryl and O-heterocyclyl, with an acid under conditions to effect elimination of the tertiary OH group with formation of a double bond and conversion of the dioxa-spiro linkage to a keto group.
Priority Claims (1)
Number |
Date |
Country |
Kind |
198 30 105 |
Jul 1998 |
DE |
|
CROSS REFERENCE TO RELATED APPLICATION
This application is a division of U.S. Pat. application Ser. No. 09/340,729, filed Jun. 29, 1999, now U.S. Pat. No. 6,077,845.
US Referenced Citations (5)
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EP |
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EP |
Non-Patent Literature Citations (2)
Entry |
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