FIELD: organic chemistry, chemical technology, medicine, pharmacy. SUBSTANCE: invention relates to novel substituted amino-compounds of the formula (I) , their pharmaceutically acceptable salts and to method of their synthesis. Indicated compound elicit analgetic activity and can be used for preparing medicinal agent as analgetic drug. In compounds of the formula (I) R1 means H, OH, O-C1-6-alkyl being R1 is not H if R2 and R7 mean H or OCH3-group is substituted at position 7; R2 means H (if R1 is not H), OH, C1-6-alkyl, O-aryl, C2-6-alkenylenearyl, Cl, F, C1-6-alkoxy-group, aryl, C1-6-alkylaryl, 5,6- or 6,7-benzo-group that is unsubstituted, mono- or disubstituted one with Cl, F, CF3, C1-6-alkyl, O-C1-6- alkyl, OH (if R1 and R2 or R7 are H then R2 or R7 can not mean CF3-group and R2 and R7 can not mean OCH3-group at position 7); or R2 and R7 both in common mean -O-C(CH2)(1-2)-O- (at position 5,6 or 6,7); R3 means H; R4 means C1-6/ -alkyl or R3 and R4 both in common mean -(CH2)(1-4)-; R5 means C1-6-alkyl, C3-7- cycloalkyl; R6 means C1-6-alkyl, C1-6- alkylaryl, -CH2-CH=C(R8)2, -CH2-(C3-7)-cycloalkyl, C3-7-cycloalkyl, C1-6-alkylhetero-cyclyl; R7 means H (if R1 is not H), OH, C1-6-alkyl, O-aryl, C2-6-alkenylenearyl, C1-6-alkoxy-group, Cl, F, aryl, C1-6-alkylaryl, 5,6- or 6,7-benzo-group that is unsubstituted, mono- or disubstituted with Cl, F, CF3, C1-6-alkyl, O-C1-6-alkyl, OH (if R1 and R2 or R7 are H then R2 and R7 can not mean CF3-group and R2 and R7 can not mean OCH3-group at position 7); and R8 means H or CH3/ and "heterocyclyl" means 5- or 6- membered unsaturated or saturated heterocyclic system optionally condensed with aryl and containing 1 or 2 heteroatoms among group involving nitrogen, oxygen and/or sulfur atom. Invention relates to method of synthesis of amino-compound of the formula (I) that involves interaction of tertiary alcohol of the formula (II) where R1-R7 have values given in the formula (I) with inorganic or organic acids in the range of temperatures from 0 C to 100 C. Tertiary alcohol of the formula (II) is synthesized by interaction of β- aminoketone of the formula (III) where R3-R6 have the above given values and R9 is similar with R2 and R10 is similar with R7 (with exception of cases when hydroxy- -group is protected and means benzylhydroxy- or silanylhydroxy-groups) with metalloorganic compound of the formula (IV) where Z means MgCl, MgBr, MgJ or Li and R11 means hydrogen atom, O-C1-6-alkyl or protected hydroxyl group as indicated above to yield compound of the formula (IIa) which is converted to compound of the formula (II). EFFECT: improved method of synthesis, valuable medicinal properties of compounds. 8 cl, 1 tbl
Title | Year | Author | Number |
---|---|---|---|
DERIVATIVES OF HETEROCYCLIC BENZOCYCLOALKENES AND METHOD OF THEIR SYNTHESIS | 1998 |
|
RU2197484C2 |
DIMETHYL-(3-ARYLBUT-3-ENYL)-AMINO-COMPOUNDS AND METHODS OF THEIR SYNTHESIS | 1997 |
|
RU2167146C2 |
DERIVATIVES OF ACRIDINE AND METHOD FOR THEIR PREPARING | 1999 |
|
RU2225399C2 |
1-PHENYL-2-DIMETHYLAMINOMETHYLCYCLOHEXANE-1-OL COMPOUNDS, METHODS OF THEIR SYNTHESIS AND DRUG BASED ON THEREOF | 1996 |
|
RU2167148C2 |
6-DIMETHYLAMINOMETHYL-1-PHENYLCYCLOHEXANE COMPOUNDS AS PHARMACEUTICALLY ACTIVE SUBSTANCES AND METHOD OF THEIR SYNTHESIS (VARIANTS) | 1996 |
|
RU2178409C2 |
PHARMACEUTICAL SALTS AND MEDICINAL AGENT | 2002 |
|
RU2309942C2 |
SUBSTITUTED CYCLOHEPTENES AND METHOD FOR THEIR PREPARING | 1999 |
|
RU2233268C2 |
SUBSTITUTED DERIVATIVES OF C-CYCLOHEXYLMETHYLAMINE, MEDICINAL AGENT AND USING | 2001 |
|
RU2295515C2 |
COMBINATION OF SPECIFIC OPIOIDS WITH MUSCARINE ANTAGONISTS FOR INCONTINENCE THERAPY | 2002 |
|
RU2305562C2 |
SUBSTITUTED DERIVATIVES OF CYCLOHEXAN-1,4-DIAMINE, METHOD FOR THEIR PREPARING AND DRUG | 2002 |
|
RU2321579C2 |
Authors
Dates
2003-01-27—Published
1998-03-12—Filed