Patent EA-002254-B1 (EA)
Title: 1-amino-alkylcyclohexane nmda receptor antagonists
Inventor: GOLD MARCUS
IPC: A61K31/40
Filed: 1998-06-24
Abstract: 1. A l-aminoalkylcyclohexane compound selected from those of the formula   wherein R* is -(CH2)n-(CR<6>R<7>)m-NR<8>R<9>  wherein n+m =0, 1, or 2; wherein R<1> to R<9> are independently selected from hydrogen and C1-6alkyl, at least R<1>, R<4>, and R<5> being C1-6alkyl, and pharmaceutically acceptable salts thereof, with proviso that said l-aminoalkylcyclohexane compound is not 1-methylamino-1,3,3,5,-tetramethylcyclohexane. 2. A compound of Claim 1 wherein R<1> through R<5> are methyl. 3. A compound of Claim 1 wherein R<1> is ethyl. 4. A compound of Claim 1 wherein R<2> is ethyl. 5. A compound of Claim 1 wherein R<3> is ethyl. 6. A compound of Claim 1 wherein R<4> is ethyl. 7. A compound of Claim 1 wherein R<5> is ethyl. 8. A compound of Claim 1 wherein R<5> is propyl. 9. A compound of Claim 1 wherein R<6> or R<7> is methyl. 10. A compound of Claim 1 wherein R<6> or R<7> is ethyl. 11. A compound of Claim 1 wherein the compound is selected from the group consisting of 1-amino-1,3,3,5,5-pentamethylcyclohexane, 1-amino-1,3,5,5-tetramethyl-3-ethylcyclohexane, 1-amino-1,5,5-trimethyl-3,3-diethylcyclohexane, 1-amino-1,5,5-trimethyl-cis-3-ethylcyclohexane, 1-amino-1,5,5-trimethyl-trans-3-ethylcyclohexane, 1-amino-1-ethyl-3,3,5,5-tetramethylcyclohexane, 1-amino-1-propyl-3,3,5,5-tetramethylcyclohexane, N-methyl-1-amino-1,3,3,5,5-pentamethylcyclohexane, and N-ethyl-1-amino-1,3,3,5,5-pentamethylcyclohexane, and pharmaceutically acceptable salts of any of the foregoing. 12. A method of treating a living animal for alleviation of a condition which is alleviated by an NMDA receptor antagonist, or for its immunomodulatory, antimalarial, anti-Borna virus, or anti-Hepatitis C effect, comprising the step of administering to the said living animal an amount of a 1-aminoalkylcyclohexane compound selected from those of the formula   wherein R* is -(CH2)n-(CR<6>R<7>)m-NR<8>R<9> wherein n+m =0, 1, or 2 wherein R<1> through R<9> are independently selected from hydrogen and C1-6alkyl and pharmaceutically acceptable salts thereof. 13. A method of Claim 12 wherein R<1> through R<5> are methyl. 14. A method of Claim 12 wherein R<1> is ethyl. 15. A method of Claim 12 wherein R<2> is ethyl. 16. A method of Claim 12 wherein R<3> is ethyl. 17. A method of Claim 12 wherein R<4> is ethyl. 18. A method of Claim 12 wherein R<5> is ethyl. 19. A method of Claim 12 wherein R<5> is propyl. 20. A method of Claim 12 wherein R<6> or R<7> is methyl. 21. A method of Claim 12 wherein R<6> or R<7> is ethyl. 22. A method of Claim 12 wherein the compound is selected from the group consisting of 1-amino-l,3,3,5,5-pentamethylcyclohexane, l-amino-1,3,5,5-tetramethyl-3-ethylcyclohexane, l-amino-1,5,5-trimethyl-3,3-diethylcyclohexane, l-amino-1,5,5-trimethyl-cis-3-ethylcyclohexane, 1-amino-1,5,5-trimethyl-trans-3-ethylcyclohexane, l-amino-l-ethyl-3,3,5,5-tetramethylcyclohexane, l-amino-l-propyl-3,3,5,5-tetramethylcyclohexane, N-methyl-l-amino-1,3,3,5,5-pentamethylcyclohexane, and N-ethyl-l-amino-1,3,3,5,5-pentamethylcyclohexane, and pharmaceutically acceptable salts of any of the foregoing. 23. A method of Claim 12 wherein the compound is administered in the form of a pharmaceutical composition thereof comprising the compound in combination with one or more pharmaceutically acceptable diluents, excipients, or carriers. 24. An NMDA-receptor antagonist pharmaceutical composition comprising an effective NMDA-receptor antagonistic amount, or an effective immunomodulatory, antimalarial, anti-Borna virus, or anti-Hepatitis C amount of a l-aminoalkylcyclohexane compound selected from those of the formula   wherein R* is -(CH2)n-(CR<6>R<7>)m-NR<8>R<9>  wherein n+m =0, 1, or 2 wherein R<1> through R<9> are independently selected from hydrogen and C1-6alkyl, at least R<1>, R<4>, and R<5> being C1-6alkyl, pharmaceutically acceptable salts thereof, in combination with one or more pharmaceutically acceptable diluents, excipients, or carriers. 25. A pharmaceutical composition of Claim 24 wherein R<1> through R<5> are methyl. 26. A pharmaceutical composition of Claim 24 wherein R<1> is ethyl. 27. A pharmaceutical composition of Claim 24 wherein R<2> is ethyl. 28. A pharmaceutical composition of Claim 24 wherein R<3> is ethyl. 29. A pharmaceutical composition of Claim 24 wherein R<4> is ethyl. 30. A pharmaceutical composition of Claim 24 wherein R<5> is ethyl. 31. A pharmaceutical composition of Claim 24 wherein R<5> is propyl. 32. A pharmaceutical composition of Claim 24 wherein R<6> or R<7> is methyl. 33. A pharmaceutical composition of Claim 24 wherein R<6> or R<7> is ethyl. 34. A pharmaceutical composition of Claim 24 wherein the compound is selected from the group consisting of l-amino-1,3,3,5,5-pentamethylcyclohexane, l-amino-1,3,5,5-tetramethyl-3-ethylcyclohexane, l-amino-1,5,5-trimethyl-3,3-diethylcyclohexane, l-amino-1,5,5-trimethyl-cis-3-ethylcyclohexane, l-amino-1,5,5-trimethyl-trans-3-ethylcyclohexane, l-amino-l-ethyl-3,3,5,5-tetramethylcyclohexane, l-amino-l-propyl-3,3,5,5-tetramethylcyclohexane, N-methyl-1-amino-1,3,3,5,5-pentamethylcyclohexane, and N-ethyl-1-amino-1,3,3,5,5-pentamethylcyclohexane, and pharmaceutically acceptable salts of any of the foregoing.