FIELD: organic chemistry, chemical technology.
SUBSTANCE: invention relates to a new improved method for preparing derivatives of 3,3-diarylpropylamines of the general formula (I) 
and sterically highly pure stable intermediate substances and their using for preparing pharmaceutical compositions. Method for preparing 3,3-diarylpropylamines of the general formula (I) wherein R means hydrogen atom, linear or branched (C1-C6)-alkyl but preferably methyl or isopropyl; R' and R'' can be similar or different and mean linear or branched (C1-C6)-alkyl but preferably methyl or isopropyl. Method involves condensation of cinnamic acid with compound of the general formula (1) 
to form compound of the general formula (2a) 
and the following reaction of the latter with chiral tertiary amine - cinchonidine to yield the corresponding salt of compound of the general formula (2b): 
and then from this compound the crystalline form of compound of the formula (3): 
is isolated followed by its either direct reduction with equivalent excess of hydride to yield lactol of the formula (5a) 
or via intermediate step by formation of corresponding acid chloroanhydride to form ester with alcohols of type R-OH wherein R is given above and the following conversion to compound of the formula (4): 
and the latter is hydrogenated with diisobutylaluminum-hydride or tri-tert.-butoxyaluminum-hydride to yield lactol of the formula (5) 
. Prepared lactols of the formula (5a) or (5) after reductive amination with secondary amine form compounds of the formula (I).
EFFECT: improved preparing method.
10 cl, 1 sch, 1 tbl, 13 ex
| Title | Year | Author | Number |
|---|---|---|---|
| METHOD FOR PREPARING BENZOPYRAN-2-OL DERIVATIVES | 2007 |
|
RU2397163C2 |
| SYNTHESIS OF ATORVASTATINE AND INTERMEDIATE PHENYLBORONATE (VARIANTS) | 2001 |
|
RU2269515C2 |
| DERIVATIVES OF CHROMAN OR THIOCHROMAN AND METHODS OF THEIR SYNTHESIS (VARIANTS) | 1990 |
|
RU2092483C1 |
| NEW METHOD FOR PREPARING 5-(4-FLUOROPHENYL)-1-[2-(2R,4R)-4-HYDROXY-6-OXOTETRAHYDROPYRAN-2-YL)ETHYL]-2-ISOPROPYL-4-PHENYL-1H-PYRROL-3-CARBOXYLI9C ACID PHENYLAMIDE | 2001 |
|
RU2244714C1 |
| 2-THIOSUBSTITUTED CARBAPENEMS, INTERMEDIATE COMPOUNDS FOR SYNTHESIS, METHODS OF SYNTHESIS (VARIANTS), PHARMACEUTICAL COMPOSITION | 1994 |
|
RU2130457C1 |
| HETEROCYCLIC NITROGEN-CONTAINING DERIVATIVES OF CARBOXYLIC ACID, METHOD OF THEIR SYNTHESIS, PHARMACEUTICAL COMPOSITION | 1993 |
|
RU2124503C1 |
| DERIVATIVES OF INDOLE | 1992 |
|
RU2061694C1 |
| 4-HYDROXYBENZOPYRAN-2-ONE OR 4-HYDROXYCYCLOALKYL[B]BENZOPYRAN- -2-ONE AND, METHOD OF SYNTHESIS OF N-[3-[CYCLOPROPYL- -(5,6,7,8,9,10-HEXAHYDRO-4-HYDROXY-2-OXO-2H-CYCLOOCTA[B]- -PYRAN-3-YL)METHYL]PHENYL]-BENZENESULFONE | 1994 |
|
RU2125999C1 |
| METHOD OF PRODUCING CARBOPROST AND ITS TROMETHAMINE SALT | 2016 |
|
RU2729626C2 |
| RENNIN INHIBITOR SYNTHESIS WITH USING CYCLOADDITION REACTION | 2006 |
|
RU2423348C2 |
