Claims for Patent: RE39593

Summary for Patent: RE39593

Title:	1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
Abstract:	1-phenyl-3-dimethylaminopropane compounds corresponding to the formula I a method of preparing them, and the use of these substances as analgesic active ingredients in pharmaceutical compositions.
Inventor(s):	Helmut Buschmann, Wolfgang Strassburger, Elmar Friderichs
Assignee:	Gruenenthal GmbH
Application Number:	US10/462,844
Patent Claims:	1. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia′: X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group; R1 is a C1-4-alkyl group; R2 represents H or a C1-4-alkyl group, and R3 is different from R2 and represents H or a straight chain C1-4-alkyl group, and R5 represents H, and R4 represents meta-O—Z, where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino, or R4 represents meta-S-C1-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—; or a salt thereof with a physiologically acceptable acid. 2. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein X represents OH, F, Cl or H; R1 represents a C1-4-alkyl group; R2 represents H or CH3; R3 is different from R2 and represents H or CH3, and R5 represents H, and R4 represents meta-OC1-3-alkyl, meta-OH, meta-S—C1-3-alkyl, meta-F, meta-Cl, meta-CH3, meta-CF2H, meta-CF3 or para-CF3, or R5 represents para-Cl or para-F, and R4 represents meta-Cl or meta-F, or R4 and R5 together represent 3,4-OCH═CH—. 3. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein X represents OH, F, Cl or an OCOR4 group in which R6 is a C1-3-alkyl group. 4. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein R2 is C1-4-alkyl. 5. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein R9, R10 and R11 represent F. 6. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to the formula Ia, wherein X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group; R1 is a C1-4-alkyl group; R2 represents a C1-4-alkyl group, and R5 represents H, and R4 represents meta-O—Z, where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino, or R4 represents meta-S—C1-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—; or a salt thereof with a physiologically acceptable acid. 7. An analgesic composition comprising at least one 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia′: wherein X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group; R1 is a C1-4-alkyl group; R2 represents H or a C1-4-alkyl group, and R3 is different from R2 and represents H or a straight chain C1-4-alkyl group, and R5 represents H, and R4 represents meta-O—Z, where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino, or R4 represents meta-S—C2-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—; or a salt thereof with a physiologically acceptable acid, and at least one conventional pharmaceutical carrier or adjuvant. 8. A method of treating a mammal suffering from pain, said method comprising administering to said mammal an effective analgesic amount of a 1-phenyl-3-dimethylaminopropane compound corresponding to formula I wherein X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group; R1 is a C1-4-alkyl group; R2 represents H or a C1-4-alkyl group and R3 represents H or a straight chain C1-4-alkyl group, or R2 and R3 together form a C4-7 cycloalkyl radical, and R5 represents H, and R4 represents meta-O—Z, where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino, or R4 represents meta-S—C1-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—, or a salt thereof with a physiologically acceptable acid. 9. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia′ and Ic′; wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group, R 1 is a C 1-4-alkyl group, R 2 represents a C n-alkyl group, wherein n=1-4, R 3 is different from R 2 and represents H or a straight chain C m-alkyl group, wherein 0 10. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia′: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group, R 1 is a C 1-4-alkyl group, R 2 represents a C 1-4-alkyl group, and R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—, or a salt thereof with a physiologically acceptable acid. 11. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein R 5 is H, and R 4 is meta-OCH 3 . 12. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein R 5 is H, and R 4 is meta-OH. 13. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein X represents OH, F, Cl, or H; R 1 is a C 1-4-alkyl group; R 2 represents CH 3 ; R 3 is H; and R 5 represents H, and R 4 represents meta-O—C 1-3-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 14. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein X represents OH, F, Cl, or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 15. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein R 2 is CH 3 , and R 3 is H. 16. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein R 9 , R 10 and R 11 represent F. 17. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein X represents OH. 18. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 19. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein R 5 is H and R 4 is meta-OCH 3 . 20. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein R 5 is H and R 4 is meta-OH. 21. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein X represents OH, F, Cl, or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 22. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein R 9 , R 10 and R 11 represent F. 23. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein X represents OH. 24. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 25. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia′ and Ic′: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group, R 1 is a C 1-4-alkyl group, R 2 represents a C 1-4-alkyl group, and R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—, or a salt thereof with a physiologically acceptable acid. 26. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein X represents OH, F, Cl, or H; R 1 is a C 1-4-alkyl group; R 2 represents CH 3 ; R 3 is H; and R 5 represents H, and R 4 represents meta-OC 1-3-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 27. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein R 5 is H and R 4 is meta-OCH 3 . 28. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein R 5 is H and R 4 is meta-OH. 29. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein X represents OH, F, Cl or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 30. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein R 2 is CH 3 , and R 3 is H. 31. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein R 9 , R 10 and R 11 represent F. 32. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein X represents OH. 33. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 34. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia and Ic: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group; R 1 is a C 1-4-alkyl group; R 2 represents a C 1-4-alkyl group, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—; or a salt thereof with a physiologically acceptable acid. 35. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein R 5 is H and R 4 is meta-OCH 3 . 36. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein R 5 is H and R 4 is meta-OH. 37. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein X represents OH, F, Cl or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 38. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein R 9 , R 10 and R 11 represent F. 39. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein X represents OH. 40. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 41. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic′: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group, R 1 is a C 1-4-alkyl group, R 2 represents a C 1-4-alkyl group, and R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—, or a salt thereof with a physiologically acceptable acid. 42. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein X represents OH, F, Cl, or H; R 1 is a C 1-4-alkyl group; R 2 represents CH 3 ; R 8 is H; and R 5 represents H, and R 4 represents meta-OC 1-3-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 43. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein R 5 is H and R 4 is meta-OCH 3 . 44. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein R 5 is H and R 4 is meta-OH. 45. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein X represents OH, F, Cl or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 46. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein R 2 is CH 3 , and R 3 is H. 47. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein R 9 , R 10 and R 11 represent F. 48. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein X represents OH. 49. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 50. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group; R 1 is a C 1-4-alkyl group; R 2 represents a C 1-4-alkyl group, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 1-4-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—; or a salt thereof with a physiologically acceptable acid. 51. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein R 5 is H and R 4 is meta-OCH 3 . 52. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein R 5 is H and R 4 is meta-OH. 53. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein X represents OH, F, Cl or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 54. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein R 9 , R 10 and R 11 represent F. 55. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein X represents OH. 56. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein X represents F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group. 57. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is ( 2S, 3S)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan- 3 -ol hydrochloride (− 1 ). 58. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 2R, 3R)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan- 3 -ol hydrochloride (+ 1 ). 59. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 2R, 3R)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan- 3 -ol hydrochloride (+ 1 ). 60. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 1S,2S)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (+ 21 ). 61. (−)-( 1R,2R)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (− 21 ). 62. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 1RS,2RS)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (+ 21 ). 63. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 2S,3S)-[ 3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (+ 23 ). 64. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (−)-( 2R,3R)-[ 3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (− 23 ). 65. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein the compound is (+)-( 2RS, 3RS)-[3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (+23). 66. An analgesic composition comprising at least one 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia′ and Ic′: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group; R 1 is a C 1-4-alkyl group; R 2 represents a C 1-4-alkyl group, and R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R 5 represents H, and R 4 represents meta-O—Z, C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—; or a salt thereof with a physiologically acceptable acid, and at least one suitable pharmaceutical carrier or adjuvant. 67. An analgesic composition according to claim 66, wherein X represents OH, F, Cl, or H; R 1 represents a C 1-4-alkyl group; R 2 represents CH 3 ; R 3 is H; and R 5 represents H, and R 4 represents meta-OC 1-3-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 68. An analgesic composition according to claim 66, wherein R5 is H and R 4 is meta-OCH 3 . 69. An analgesic composition according to claim 66, wherein R5 is H and R 4 is meta-OH. 70. An analgesic composition according to claim 66, wherein X represents OH, F, Cl or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 71. An analgesic composition according to claim 66, wherein R2 is CH 2 , and R 3 is H. 72. An analgesic composition according to claim 66, wherein R9 , R 10 and R 11 represent F. 73. An analgesic composition according to claim 66, wherein X represents OH. 74. An analgesic composition according to claim 66, wherein X represents F, Cl, H or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 75. An analgesic composition according to claim 66, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia′. 76. An analgesic composition according to claim 66, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic′. 77. An analgesic composition comprising at least one 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia and Ic: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group; R 1 is a C 1-4-alkyl group; R 2 represents a C 1-4-alkyl group, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 1-4-alkyl)2 , CO(OC1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—; or a salt thereof with a physiologically acceptable acid, and at least one suitable pharmaceutical carrier or adjuvant. 78. An analgesic composition according to claim 77, wherein R5 is H and R 4 is meta-OCH 3 . 79. An analgesic composition according to claim 77, wherein R5 is H and R 4 is meta-OH. 80. An analgesic composition according to claim 77, wherein X represents OH, F, Cl or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 81. An analgesic composition according to claim 77, wherein R9 , R 10 and R 11 represent F. 82. An analgesic composition according to claim 77, wherein X represents OH. 83. An analgesic composition according to claim 77, wherein X represents F, Cl, H or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 84. An analgesic composition according to claim 77, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia. 85. An analgesic composition according to claim 77, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic. 86. A method according to claim 8, wherein X represents OH, F, Cl, or H; R 1 represents a C 1-4-alkyl group; R 2 represents CH 8 ; R 3 represents H, and R 5 represents H, and R 4 represents meta-OC 1-8-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 87. A method according to claim 8, wherein R5 is H and R 4 is meta-OCH 8 . 88. An method according to claim 8, wherein R5 is H and R 4 is meta-OH. 89. A method according to claim 8, wherein X represents OH, F, Cl or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 90. A method according to claim 8, wherein R2 is C 1-4-alkyl, and R 3 is different from R 2 and is H or C 1-3 alkyl. 91. A method according to claim 8, wherein R9 , R 10 and R 11 represent F. 92. A method according to claim 8, wherein X represents OH. 93. A method according to claim 8, wherein X represents F, Cl, H or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 94. A method according to claim 8, wherein X represents H. 95. A method according to claim 8, wherein the compound of formula I has a configuration corresponding to at least one of formulae Ia′ and Ic′: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group, R 1 is a C 1-4-alkyl group, R 2 represents a C 1-4-alkyl group, and R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—, or a salt thereof with a physiologically acceptable acid. 96. A method according to claim 95, wherein X represents OH, F, Cl, or H; R 1 represents a C 1-4-alkyl group; R 2 represents CH 3 ; R 3 represents H, and R 5 represents H, and R 4 represents meta-OC 1-3-alkyl, meta-OH, meta-S—C 1-3-alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 97. A method according to claim 95, wherein R5 is H and R 4 is meta-OCH 3 . 98. An method according to claim 95, wherein R5 is H and R 4 is meta-OH. 99. A method according to claim 95, wherein X represents OH, F, Cl or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 100. A method according to claim 95, wherein R2 is CH 3 , and R 3 is H. 101. A method according to claim 95, wherein R9 , R 10 and R 11 represent F. 102. A method according to claim 95, wherein X represents OH. 103. A method according to claim 95, wherein X represents F, Cl, H or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 104. A method according to claim 95, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia′. 105. A method according to claim 95, wherein the 1-phenyl- 3 -dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic′. 106. A method according to claim 8, wherein the compound of formula I has a configuration corresponding to at least one of formulae Ia and Ic: wherein X represents OH, F, Cl, H or an OCOR 6 group in which R 6 is a C 1-3-alkyl group; R 1 is a C 1-4-alkyl group; R 2 represents a C 1-4-alkyl group, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 1-4-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—; or a salt thereof with a physiologically acceptable acid. 107. A method according to claim 106, wherein X represents OH, F, Cl or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 108. A method according to claim 106, wherein R9 , R 10 and R 11 represent F. 109. A method according to claim 106, wherein X represents OH. 110. A method according to claim 106, wherein X represents F, Cl, H or an OCOR6 group in which R 6 is a C 1-3-alkyl group. 111. A method according to claim 106, wherein the compound is a 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia. 112. A method according to claim 106, wherein the compound is a 1-phenyl- 3 -dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic. 113. A method according to claim 106, wherein R5 is H and R 4 is meta-OCH 3 . 114. A method according to claim 106, wherein R5 is H and R 4 is meta-OH. 115. A method according to claim 8, wherein the compound is (+)-( 1RS,2RS)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (+ 21 ). 116. A method according to claim 8, wherein the compound is (+)-( 1S,2S)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (+ 21 ). 117. A method according to claim 8, wherein the compound is (−)-( 1R,2R)- 3 -( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol hydrochloride (− 21 ). 118. A method according to claim 8, wherein the compound is (+)-( 2RS,3RS)-[ 3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (+23 ). 119. A method according to claim 8, wherein the compound is (+)-( 2S,3S)-[ 3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (+ 23 ). 120. A method according to claim 8, wherein the compound is (−)-( 2R,3R)-[ 3 -( 3 -methoxyphenyl)- 2 -methylpentyl]-dimethylamine hydrochloride (− 23 ). 121. A method according to claim 8, wherein the compound is (+)-( 2RS, 3RS)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan-3-ol hydrochloride (+ 1 ). 122. A method according to claim 8, wherein the compound is (+)-( 2R, 3R)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan-3-ol hydrochloride (+ 1 ). 123. A method according to claim 8, wherein the compound is (−)-( 2S, 3S)- 1 -dimethylamino- 3 -( 3 -methoxyphenyl)- 2 -methylpentan-3-ol hydrochloride (− 1 ). 124. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 6 , wherein X is H. 125. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 10 , wherein X is H. 126. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 25 , wherein X is H. 127. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 34 , wherein X is H. 128. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 41 , wherein X is H. 129. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 50 , wherein X is H. 130. An analgesic composition according to claim 66, wherein X is H. 131. An analgesic composition according to claim 75, wherein X is H. 132. An analgesic composition according to claim 76, wherein X is H. 133. An analgesic composition according to claim 77, wherein X is H. 134. An analgesic composition according to claim 84, wherein X is H. 135. An analgesic composition according to claim 85, wherein X is H. 136. A method according to claim 86, wherein X is H. 137. A method according to claim 95, wherein X is H. 138. A method according to claim 106, wherein X is H. 139. A method according to claim 113, wherein X is H. 140. A method according to claim 114, wherein X is H. 141. An isolated 1-phenyl- 3 -dimethylaminopropane diastereomer having a configuration corresponding to formula I: wherein X represents H, R 1 is a C 1-4-alkyl group, R 2 represents a C 1-4-alkyl group, R 3 is different from R 2 and represents H or a straight chain C 1-3-alkyl group, and R 5 represents H, and R 4 represents meta-O—Z, where Z is H, C 1-3-alkyl, PO(OC 14-alkyl)2 , CO(OC 1-5-alkyl), CONH—C 6 H 4—(C 1-3-alkyl) or CO—C 6 H 4 —R 7 , in which R 7 is ortho-OCOC 1-3-alkyl or meta- or para-CH 2 N(R 8)2 , where R 8 is C 1-4-alkyl or 4 -morpholino, or R 4 represents meta-S—C 1-3-alkyl, meta-Cl, meta-F, meta-CR 9 R 10 R 11 , ortho-OH, ortho-O—C 2-3-alkyl, para-F or para-CR 9 R 10 R 11 , where R 9 , R 10 and R 11 independently represent H or F, or R 5 represents para-Cl, para-F, para-OH or para-O—C 1-3-alkyl, and R 4 represents meta-Cl, meta-F, meta-OH or meta-O—C 1-3-alkyl, or R 4 and R 5 together represent 3,4 -OCH═CH— or 3,4 -OCH═CHO—, and wherein carbon atoms at positions 1 and 2 are both asymmetric carbons and the diastereomer has a ( 1R, 2R) or ( 1S, 2S) configuration, or a salt thereof with a physiologically acceptable acid. 142. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 141 , wherein R 5 is H, and R 4 is meta-OCH 3 . 143. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 141 , wherein R 5 is H, and R 4 is meta-OH. 144. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 141 , wherein R 2 represents CH 3 ; R 3 is H; and R 5 represents H, and R 4 represents meta-O—C 1-3-alkyl, meta-OH, meta-S—1-3 -alkyl, meta-F, meta-Cl, meta-CH 3 , meta-CF 2 H, meta-CF 3 , or para-CF 3 , or R 5 represents para-Cl, or para-F, and R 4 represents meta-Cl, or meta-F, or R 4 and R 5 together represent 3,4 -OCH═CH—. 145. An isolated 1-phenyl- 3 -dimethylaminopropane diastereoisomer according to claim 141 , wherein R 2 is CH 3 , and R 3 is H. 146. An isolated 1-phenyl- 3 -dimethylaminopropane diastereomer according to claim 141 , wherein R 9 , R 10 and R 11 represent F. 147. A pharmaceutically acceptable salt of (−)-( 1R,2R)- 3R-( 3 -dimethylamino- 1 -ethyl- 2 -methylpropyl)-phenol.