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Details for Patent: 6,344,558

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Details for Patent: 6,344,558

Title: 1-phenyl-3-dimethylaminopropane compounds with a pharmacological effect
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: Gruenthal GmbH (Aachen, DE)
Filing Date:Apr 20, 2001
Application Number:09/838,192
Claims:1. A method of preparing a 1-phenyl-3-dimethylaminopropane compound corresponding to formula ##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 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;

when R.sup.5 represents H, R.sup.4 represents:

(A) meta-O--Z, wherein 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

(B) 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;

when R.sup.5 represents para-Cl, para-F, para-OH or para-O--C.sub.1-3 -alkyl, 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--,

as diastereoisomers or enantiomers in the form of free bases;

said method comprising:

(1) reacting a compound of formula I in which X represents Cl with at least one substance selected from the group consisting of zinc borohydride, zinc cyanoborohydride and tin cyanoborohydride to form a final compound in which X represents H;

(2) reacting a compound of formula I in which X represents OH with dimethylaminosulfur trifluoride in a solvent to form a final compound in which X represents F;

(3) reacting a compound of formula I in which X represents OH with thionyl chloride to form a final product in which X represent Cl;

(4) reacting a compound of formula I in which X represents OH or with an acid chloride Cl--COOR.sup.6 to form a final compound in which X represents OCOR.sup.6 ; or

(5) reacting a .beta.-dimethylaminoketone of formula II ##STR42##

with an organometallic compound of formula III ##STR43##

in which Z represents MgCl, MgBr, MgI or Li to form a final compound in which X represent OH; and

optionally converting a free base into a salt with a physiologically acceptable acid.

2. A method 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 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. A method according to claim 1, wherein R.sup.2 and R.sup.3 have different meanings, and wherein said compound is a diastereoisomer having the configuration Ia ##STR44##

4. A method according to claim 1, in which X represents OH, said method comprising reacting a .beta.-dimethylaminoketone of formula II ##STR45##

with an organometallic compound of formula III ##STR46##

in which Z represents MgCl, MgBr, MgI or Li.

5. A method according to claim 1, in which X represents H, said method comprising reacting a compound of formula I in which X represents Cl with at least one substance selected from the group consisting of zinc borohydride, zinc cyanoborohydride and tin cyanoborohydride.

6. A method according to claim 1, in which X represents F, said method comprising reacting a compound of formula I in which X represents OH with dimethylaminosulfur trifluoride in a solvent.

7. A method according to claim 1, in which X represents Cl, said method comprising reacting a compound of formula I in which X represents OH with thionyl chloride.

8. A method according to claim 1, in which X represents an OCOR.sup.6 group in which R.sup.6 is C.sub.1-3 -alkyl group, said method comprising reacting a compound of formula I in which X represents OH with an acid chloride Cl--COOR.sup.6.
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