FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to new substituted cycloheptenes eliciting with analgetic effect of the general formula (I):
wherein R1 means hydroxyl (OH), (O-C1-C6)-alkyl; R2 means (C1-C6)-alkyl, (CH2)(1-2)aryl; R3 means (CH2)(0-1)-(C5-C7)-cycloalkyl, (CH2)(0-2)-aryl wherein aryl residue can be substituted once or multiple with hydroxyl (OH), fluorine (F), chlorine (Cl) atom, CF3, (C1-C6)-alkyl as their racemate or enantiomers being as bases or as salts of physiologically acceptable acids. Method for preparing compound of the formula (I) involves interaction of tertiary alcohol of the general formula (II):
wherein R1-R3 have the same values as in the formula (I) with acid in the range of temperature 20-100 C. Used tertiary alcohol of the general formula (II) is prepared by interaction of aminoketone of the general formula (III)
wherein R2 has values as in the formula (I); R4 is similar with R3; if R has hydroxyl group (with exception for cases when presenting hydroxyl group is represented in the protected form as benzyloxy- or silanyloxy-group) with metalloorganic compound of the formula (IV)
wherein X means MgCl2, MgBr2, MgJ2 or corresponding Li salts; R5 has values that are similar with R1 (with exception of cases when presenting hydroxyl group is represented in the protected form as benzyloxy or silanyloxy-group). The prepared intermediate compound of the formula (IIa)
wherein R4 and R5 have above indicated values is converted to compound of the formula (II).
EFFECT: improved preparing method.
5 cl, 2 tbl, 4 ex
| Title | Year | Author | Number |
|---|---|---|---|
| DERIVATIVES OF HETEROCYCLIC BENZOCYCLOALKENES AND METHOD OF THEIR SYNTHESIS | 1998 |
|
RU2197484C2 |
| DERIVATIVES OF ACRIDINE AND METHOD FOR THEIR PREPARING | 1999 |
|
RU2225399C2 |
| SUBSTITUTED AMINO-COMPOUNDS AND METHOD OF THEIR SYNTHESIS | 1998 |
|
RU2197474C2 |
| 6-DIMETHYLAMINOMETHYL-1-PHENYLCYCLOHEXANE COMPOUNDS AS PHARMACEUTICALLY ACTIVE SUBSTANCES AND METHOD OF THEIR SYNTHESIS (VARIANTS) | 1996 |
|
RU2178409C2 |
| DIMETHYL-(3-ARYLBUT-3-ENYL)-AMINO-COMPOUNDS AND METHODS OF THEIR SYNTHESIS | 1997 |
|
RU2167146C2 |
| ARYLPYRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITION | 1997 |
|
RU2189976C2 |
| SULFATED AMINO ACID DERIVATIVES AND METALLOPROTEINASE INHIBITORS COMPRISING THEREOF | 1997 |
|
RU2198656C2 |
| 1-PHENYL-2-DIMETHYLAMINOMETHYLCYCLOHEXANE-1-OL COMPOUNDS, METHODS OF THEIR SYNTHESIS AND DRUG BASED ON THEREOF | 1996 |
|
RU2167148C2 |
| NEW DERIVATIVES OF PROPARGYL ETHER | 2000 |
|
RU2237058C2 |
| SUBSTITUTED OXAZOLE DERIVATIVES WITH ANALGETIC ACTION | 2006 |
|
RU2424236C2 |
