RU2003122192A

RU2003122192A - METHOD FOR PRODUCING SULFAMID-SUBSTITUTED IMIDAZOTRIAZINES

Info

Publication number: RU2003122192A
Application number: RU2003122192/04A
Authority: RU
Inventors: Марк НОВАКОВСКИ; Райнхольд Геринг; Вернер ХАЙЛЬМАНН; Карл-Хайнц ВАЛЬ
Original assignee: Байер ХельсКер АГ
Priority date: 2000-12-18
Filing date: 2001-12-05
Publication date: 2004-12-27

Claims

1. The method of obtaining compounds of formula (I)

wherein

R ¹ means hydrogen or straight or branched alkyl containing up to 4 carbon atoms,

R ² means direct alkyl containing up to 4 carbon atoms,

R ³ and R ⁴ may be the same or different and mean a straight or branched alkyl chain which contains up to 5 carbon atoms and which, if necessary, may contain up to two identical or different substituents hydroxy or methoxy, or

R ³ and R ⁴ together with the nitrogen atom form a piperidinyl, morpholinyl, thymorpholinyl ring or a residue of the formula

where R ⁷ means hydrogen, formyl; straight or branched acyl or alkoxycarbonyl containing, respectively, up to 6 carbon atoms; or straight or branched alkyl containing up to 6 carbon atoms and which, if necessary, may be substituted once or twice by the same or different substituents from the group of hydroxy, carboxyl, straight or branched alkoxy or alkoxycarbonyl containing, respectively, up to 6 carbon atoms; or cycloalkyl with 3-8 carbon atoms,

and the above for R ³ and R ⁴ formed together with a nitrogen atom, the heterocycle, if necessary, can be substituted once or twice by the same or different, if necessary, geminal, hydroxy, formyl, carbonyl, straight or branched acyl or alkoxycarbonyl groups, containing, respectively up to 6 carbon atoms,

and / or the above for R ³ and R ⁴ formed together with a nitrogen atom, the heterocycle, if necessary, may be substituted by straight or branched alkyl containing up to 6 carbon atoms and, if necessary,

once or twice substituted by the same or different hydroxyl, carboxyl groups,

and / or the above for R ³ and R ⁴ formed together with a nitrogen atom, the heterocycle, if necessary, may be substituted by piperidinyl or pyrrolidinyl bound via nitrogen,

R ⁵ and R ⁶ may be the same or different and mean hydrogen, straight or branched alkyl containing up to 6 carbon atoms, hydroxy or straight or branched alkoxy containing up to 6 carbon atoms,

characterized in that the compound of formula (II)

where R ¹ , R ² , R ⁵ and R ⁶ have the above meanings,

reacted with sulfuric acid to form compounds of formula (III)

where R ¹ , R ² , R ⁵ and R ⁶ have the above meanings,

followed by its interaction with thionyl chloride, and the product thus obtained without isolation in an inert solvent is reacted with an amine of the formula (IV)

where R ³ and R ⁴ have the above meanings,

and, if necessary, are converted to the corresponding salts, hydrates or N-oxides.

2. The method according to claim 1, characterized in that

R ² means direct alkyl containing up to 4 carbon atoms,

R ³ and R ⁴ together with the nitrogen atom form a piperidinyl, morpholinyl ring or a residue of the formula

where R ⁷ means hydrogen; straight or branched alkyl containing up to 4 carbon atoms, and which, if necessary, may be substituted once or twice by the same or different substituents from the hydroxy group, straight or branched alkoxy containing up to 4 carbon atoms, respectively; or cycloalkyl with 3-8 carbon atoms, and

and the above for R ³ and R ⁴ , the heterocycle formed together with the nitrogen atom, if necessary, can be substituted once or twice by the same or different, if necessary, geminal, hydroxy groups, a straight or branched acyl or alkoxycarbonyl containing, respectively, up to 4 atoms carbon

and / or the above for R ³ and R ⁴ formed together with a nitrogen atom, the heterocycle, if necessary, may be substituted by straight or branched alkyl containing up to 4 carbon atoms and, if necessary, once or twice substituted by the same or different hydroxyl groups,

R ⁵ and R ⁶ may be the same or different and mean hydrogen, straight or branched alkyl containing up to 6 carbon atoms, hydroxy or straight or branched alkoxy containing up to 6 carbon atoms.

3. The method according to claim 1, characterized in that

R ² means direct alkyl containing up to 4 carbon atoms,

R ³ and R ⁴ may be the same or different and mean methyl or ethyl, which, if necessary, may contain up to two identical or different hydroxyl substituents, or

R ³ and R ⁴ together with the nitrogen atom form a piperidinyl, morpholinyl ring or residue of the formula

where R ⁷ means hydrogen; methyl or ethyl, which, if necessary, may be substituted once or twice by the same or different substituents from the group of hydroxy, methoxy or ethoxy;

or cyclopentyl or cyclohexyl, and

and the above for R ³ and R ⁴ formed together with a nitrogen atom, the heterocycle, if necessary, can be substituted once or twice by the same or different, if necessary, geminal, hydroxy, methyl or ethyl groups,

4. The method according to claim 1, characterized in that

R ¹ means methyl or ethyl,

R ² means n-propyl,

or cyclopentyl or cyclohexyl, and

R ⁵ means hydrogen,

R ⁶ means ethoxy.

5. The method according to claim 1, characterized in that the compounds of formula (II) are obtained by reacting compounds of the formula (V)

wherein

R ¹ and R ² have the above meaning and

L means straight or branched alkyl containing up to 4 carbon atoms,

with a compound of general formula (VI)

wherein

R ⁵ and R ⁶ have the above meaning,

in 2 stages in the systems methanol and phosphorus oxytrichloride / acetic acid or methanol and acetyl chloride / acetic acid.