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Last Updated: March 28, 2024

Details for Patent: 6,248,737


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Title: 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects
Abstract:1-phenyl-3 -dimethylaminopropane compounds corresponding to the formula I ##STR1## a method of preparing them, and the use of these substances as analgesic active ingredients in pharmaceutical compositions.
Inventor(s): Buschmann; Helmut (Aachen, DE), Strassburger; Wolfgang (Wuerselen, DE), Friderichs; Elmar (Stolberg, DE)
Assignee: Gruenenthal GmbH (Aachen, DE)
Filing Date:Jun 06, 1995
Application Number:08/466,911
Claims:1. An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula I ##STR41##

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.1-4 alkyl).sub.2, CO(OC.sub.1-5 -alkyl), CONH--C.sub.6 H.sub.4 --(C.sub.1-3 -alkyl) or CO--C.sub.6 H.sub.4 --R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3 -alkyl or meta- or para-CH.sub.2 N(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.9 R.sup.10 R.sup.11, ortho-OH, ortho-O--C.sub.2-3 -alkyl, para-F or para-CR.sup.9 R.sup.10 R.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.2 H, 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.6 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 ##STR42##

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.6 H.sub.4 --(C.sub.1-3 -alkyl) or CO--C.sub.6 H.sub.4 --R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3 -alkyl or meta- or para-CH.sub.2 N(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.9 R.sup.10 R.sup.11, ortho-OH, ortho-O--C.sub.2-3 -alkyl, para-F or para-CR.sup.9 R.sup.10 R.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 I ##STR43##

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.1-4 alkyl).sub.2, CO(OC.sub.1-5 -alkyl), CONH--C.sub.6 H.sub.4 --(C.sub.1-3 -alkyl) or CO--C.sub.6 H.sub.4 --R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3 -alkyl or meta- or para-CH.sub.2 N(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.9 R.sup.10 R.sup.11, ortho-OH, ortho-O--C.sub.2-3 -alkyl, para-F or para-CR.sup.9 R.sup.10 R.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 ##STR44##

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.1-4 alkyl),.sub.2 CO(OC.sub.1-5 -alkyl), CONH--C.sub.6 H.sub.4 --(C.sub.1-3 -alkyl) or CO--C.sub.6 H.sub.4 --R.sup.7, in which R.sup.7 is ortho-OCOC.sub.1-3 -alkyl or meta- or para-CH.sub.2 N(R.sup.8).sub.2, where R.sup.6 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.9 R.sup.10 R.sup.11, ortho-OH, ortho-O--C.sub.2-3- alkyl, para-F or para-CR.sup.9 R.sup.10 R.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.

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