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Claims for Patent: RE39593

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Claims for Patent: RE39593

Title:1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
Abstract:1-phenyl-3-dimethylaminopropane compounds corresponding to the formula I ##STR00001## a method of preparing them, and the use of these substances as analgesic active ingredients in pharmaceutical compositions.
Inventor(s): Buschmann; Helmut (Esplugues de Llobregat, ES), Strassburger; Wolfgang (Wuerselen, DE), Friderichs; Elmar (Stolberg, DE)
Assignee: Gruenenthal GmbH (Aachen, DE)
Application Number:10/462,844
Patent Claims: 1. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia': ##STR00041## X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents H or a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S-C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.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; R.sup.1 represents a C.sub.1-4-alkyl group; R.sup.2 represents H or CH.sub.3; R.sup.3 is different from R.sup.2 and represents H or CH.sub.3, and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3 or para-CF.sub.3, or R.sup.5 represents para-Cl or para-F, and R.sup.4 represents meta-Cl or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..].

.[.3. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein X represents OH, F, Cl or an OCOR.sup.4 group in which R.sup.6 is a C.sub.1-3-alkyl group..].

.[.4. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein R.sup.2 is C.sub.1-4-alkyl..].

.[.5. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 1, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..].

6. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to .[.the.]. formula Ia, ##STR00042## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.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': ##STR00043## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents H or a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.2-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.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 ##STR00044## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents H or a C.sub.1-4-alkyl group and R.sup.3 represents H or a straight chain C.sub.1-4-alkyl group, or R.sup.2 and R.sup.3 together form a C.sub.4-7 cycloalkyl radical, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid.

.Iadd.9. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia' and Ic'; ##STR00045## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.n-alkyl group, wherein n=1-4, R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.m-alkyl group, wherein 0<m<n, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.10. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia': ##STR00046## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.11. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein R.sup.5 is H, and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.12. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein R.sup.5 is H, and R.sup.4 is meta-OH..Iaddend.

.Iadd.13. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein X represents OH, F, Cl, or H; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.3; R.sup.3 is H; and R.sup.5 represents H, and R.sup.4 represents meta-O--C.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.14. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein X represents OH, F, Cl, or an OCOR.sup.6group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.15. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein R.sup.2 is CH.sub.3, and R.sup.3 is H..Iaddend.

.Iadd.16. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.17. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein X represents OH..Iaddend.

.Iadd.18. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.19. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.20. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.21. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein X represents OH, F, Cl, or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.22. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.23. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein X represents OH..Iaddend.

.Iadd.24. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.25. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia' and Ic': ##STR00047## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.26. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein X represents OH, F, Cl, or H; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.3; R.sup.3 is H; and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.27. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.28. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.29. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.30. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein R.sup.2 is CH.sub.3, and R.sup.3 is H..Iaddend.

.Iadd.31. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.32. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein X represents OH..Iaddend.

.Iadd.33. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.34. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to at least one of formulae Ia and Ic: ##STR00048## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--; or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.35. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.36. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.37. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.38. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.39. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein X represents OH..Iaddend.

.Iadd.40. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.41. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic': ##STR00049## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.42. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein X represents OH, F, Cl, or H; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.3; R.sup.8 is H; and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.43. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.44. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.45. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.46. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein R.sup.2 is CH.sub.3, and R.sup.3 is H..Iaddend.

.Iadd.47. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.48. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein X represents OH..Iaddend.

.Iadd.49. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.50. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic: ##STR00050## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--; or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.51. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.52. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.53. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.54. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.55. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein X represents OH..Iaddend.

.Iadd.56. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.61. (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (-21)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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)..Iaddend.

.Iadd.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': ##STR00051## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--; or a salt thereof with a physiologically acceptable acid, and at least one suitable pharmaceutical carrier or adjuvant..Iaddend.

.Iadd.67. An analgesic composition according to claim 66, wherein X represents OH, F, Cl, or H; R.sup.1 represents a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.3; R.sup.3 is H; and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.68. An analgesic composition according to claim 66, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.69. An analgesic composition according to claim 66, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.70. An analgesic composition according to claim 66, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.71. An analgesic composition according to claim 66, wherein R.sup.2 is CH.sub.2, and R.sup.3 is H..Iaddend.

.Iadd.72. An analgesic composition according to claim 66, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.73. An analgesic composition according to claim 66, wherein X represents OH..Iaddend.

.Iadd.74. An analgesic composition according to claim 66, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.75. An analgesic composition according to claim 66, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia'..Iaddend.

.Iadd.76. An analgesic composition according to claim 66, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic'..Iaddend.

.Iadd.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: ##STR00052## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--; or a salt thereof with a physiologically acceptable acid, and at least one suitable pharmaceutical carrier or adjuvant..Iaddend.

.Iadd.78. An analgesic composition according to claim 77, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.79. An analgesic composition according to claim 77, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.80. An analgesic composition according to claim 77, wherein X represents OH, F, Cl or an OCOR.sup.6group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.81. An analgesic composition according to claim 77, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.82. An analgesic composition according to claim 77, wherein X represents OH..Iaddend.

.Iadd.83. An analgesic composition according to claim 77, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.84. An analgesic composition according to claim 77, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia..Iaddend.

.Iadd.85. An analgesic composition according to claim 77, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic..Iaddend.

.Iadd.86. A method according to claim 8, wherein X represents OH, F, Cl, or H; R.sup.1 represents a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.8; R.sup.3 represents H, and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-8-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.87. A method according to claim 8, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.8..Iaddend.

.Iadd.88. An method according to claim 8, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.89. A method according to claim 8, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.90. A method according to claim 8, wherein R.sup.2 is C.sub.1-4-alkyl, and R.sup.3 is different from R.sup.2 and is H or C.sub.1-3 alkyl..Iaddend.

.Iadd.91. A method according to claim 8, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.92. A method according to claim 8, wherein X represents OH..Iaddend.

.Iadd.93. A method according to claim 8, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.94. A method according to claim 8, wherein X represents H..Iaddend.

.Iadd.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': ##STR00053## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, such that X and the dimethylamino group are disposed threo in relation to each other, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--, or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.96. A method according to claim 95, wherein X represents OH, F, Cl, or H; R.sup.1 represents a C.sub.1-4-alkyl group; R.sup.2 represents CH.sub.3; R.sup.3 represents H, and R.sup.5 represents H, and R.sup.4 represents meta-OC.sub.1-3-alkyl, meta-OH, meta-S--C.sub.1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.97. A method according to claim 95, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.98. An method according to claim 95, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.99. A method according to claim 95, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.100. A method according to claim 95, wherein R.sup.2 is CH.sub.3, and R.sup.3 is H..Iaddend.

.Iadd.101. A method according to claim 95, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.102. A method according to claim 95, wherein X represents OH..Iaddend.

.Iadd.103. A method according to claim 95, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.104. A method according to claim 95, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ia'..Iaddend.

.Iadd.105. A method according to claim 95, wherein the 1-phenyl-3-dimethylaminopropane diastereoisomer has a configuration corresponding to formula Ic'..Iaddend.

.Iadd.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: ##STR00054## wherein X represents OH, F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group; R.sup.1 is a C.sub.1-4-alkyl group; R.sup.2 represents a C.sub.1-4-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.1-4-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.CHO--; or a salt thereof with a physiologically acceptable acid..Iaddend.

.Iadd.107. A method according to claim 106, wherein X represents OH, F, Cl or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.108. A method according to claim 106, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.109. A method according to claim 106, wherein X represents OH..Iaddend.

.Iadd.110. A method according to claim 106, wherein X represents F, Cl, H or an OCOR.sup.6 group in which R.sup.6 is a C.sub.1-3-alkyl group..Iaddend.

.Iadd.111. A method according to claim 106, wherein the compound is a 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ia..Iaddend.

.Iadd.112. A method according to claim 106, wherein the compound is a 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula Ic..Iaddend.

.Iadd.113. A method according to claim 106, wherein R.sup.5 is H and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.114. A method according to claim 106, wherein R.sup.5 is H and R.sup.4 is meta-OH..Iaddend.

.Iadd.115. A method according to claim 8, wherein the compound is (+)-(1RS,2RS)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (+21)..Iaddend.

.Iadd.116. A method according to claim 8, wherein the compound is (+)-(1S,2S)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (+21)..Iaddend.

.Iadd.117. A method according to claim 8, wherein the compound is (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride (-21)..Iaddend.

.Iadd.118. A method according to claim 8, wherein the compound is (+)-(2RS,3RS)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine hydrochloride (+23)..Iaddend.

.Iadd.119. A method according to claim 8, wherein the compound is (+)-(2S,3S)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine hydrochloride (+23)..Iaddend.

.Iadd.120. A method according to claim 8, wherein the compound is (-)-(2R,3R)-[3-(3-methoxyphenyl)-2-methylpentyl]-dimethylamine hydrochloride (-23)..Iaddend.

.Iadd.121. A method according to claim 8, wherein the compound is (+)-(2RS, 3RS)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride (+1)..Iaddend.

.Iadd.122. A method according to claim 8, wherein the compound is (+)-(2R, 3R)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride (+1)..Iaddend.

.Iadd.123. A method according to claim 8, wherein the compound is (-)-(2S, 3S)-1-dimethylamino-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride (-1)..Iaddend.

.Iadd.124. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 6, wherein X is H..Iaddend.

.Iadd.125. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 10, wherein X is H..Iaddend.

.Iadd.126. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 25, wherein X is H..Iaddend.

.Iadd.127. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 34, wherein X is H..Iaddend.

.Iadd.128. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 41, wherein X is H..Iaddend.

.Iadd.129. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 50, wherein X is H..Iaddend.

.Iadd.130. An analgesic composition according to claim 66, wherein X is H..Iaddend.

.Iadd.131. An analgesic composition according to claim 75, wherein X is H..Iaddend.

.Iadd.132. An analgesic composition according to claim 76, wherein X is H..Iaddend.

.Iadd.133. An analgesic composition according to claim 77, wherein X is H..Iaddend.

.Iadd.134. An analgesic composition according to claim 84, wherein X is H..Iaddend.

.Iadd.135. An analgesic composition according to claim 85, wherein X is H..Iaddend.

.Iadd.136. A method according to claim 86, wherein X is H..Iaddend.

.Iadd.137. A method according to claim 95, wherein X is H..Iaddend.

.Iadd.138. A method according to claim 106, wherein X is H..Iaddend.

.Iadd.139. A method according to claim 113, wherein X is H..Iaddend.

.Iadd.140. A method according to claim 114, wherein X is H..Iaddend.

.Iadd.141. An isolated 1-phenyl-3-dimethylaminopropane diastereomer having a configuration corresponding to formula I: ##STR00055## wherein X represents H, R.sup.1 is a C.sub.1-4-alkyl group, R.sup.2 represents a C.sub.1-4-alkyl group, R.sup.3 is different from R.sup.2 and represents H or a straight chain C.sub.1-3-alkyl group, and R.sup.5 represents H, and R.sup.4 represents meta-O--Z, where Z is H, C.sub.1-3-alkyl, PO(OC.sub.14-alkyl).sub.2, CO(OC.sub.1-5-alkyl), CONH--C.sub.6H.sub.4--(C.sub.1-3-alkyl) or CO--C.sub.6H.sub.4--R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3-alkyl or meta- or para-CH.sub.2N(R.sup.8).sub.2, where R.sup.8 is C.sub.1-4-alkyl or 4-morpholino, or R.sup.4 represents meta-S--C.sub.1-3-alkyl, meta-Cl, meta-F, meta-CR.sup.9R.sup.10R.sup.11, ortho-OH, ortho-O--C.sub.2-3-alkyl, para-F or para-CR.sup.9R.sup.10R.sup.11, where R.sup.9, R.sup.10 and R.sup.11 independently represent H or F, or R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3-alkyl, and R.sup.4 represents meta-Cl, meta-F, meta-OH or meta-O--C.sub.1-3-alkyl, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH-- or 3,4-OCH.dbd.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..Iaddend.

.Iadd.142. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 141, wherein R.sup.5 is H, and R.sup.4 is meta-OCH.sub.3..Iaddend.

.Iadd.143. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 141, wherein R.sup.5 is H, and R.sup.4 is meta-OH..Iaddend.

.Iadd.144. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 141, wherein R.sup.2 represents CH.sub.3; R.sup.3 is H; and R.sup.5 represents H, and R.sup.4 represents meta-O--C.sub.1-3-alkyl, meta-OH, meta-S--1-3-alkyl, meta-F, meta-Cl, meta-CH.sub.3, meta-CF.sub.2H, meta-CF.sub.3, or para-CF.sub.3, or R.sup.5 represents para-Cl, or para-F, and R.sup.4 represents meta-Cl, or meta-F, or R.sup.4 and R.sup.5 together represent 3,4-OCH.dbd.CH--..Iaddend.

.Iadd.145. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer according to claim 141, wherein R.sup.2 is CH.sub.3, and R.sup.3 is H..Iaddend.

.Iadd.146. An isolated 1-phenyl-3-dimethylaminopropane diastereomer according to claim 141, wherein R.sup.9, R.sup.10 and R.sup.11 represent F..Iaddend.

.Iadd.147. A pharmaceutically acceptable salt of (-)-(1R,2R)-3R-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol..Iaddend.
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