Claims
- 1. A process for the preparation of a compound of formula (I)
- 2. A process according to claim 1 comprising following method:
a) reacting a compound of formula (II) 28wherein A is as defined above, L is a leaving group selected from hydrogen, halogen or trimethylsilyl, and Q is halogen, with a compound of formula (III), 29wherein X is NR2R3, wherein R2 and R3 are defined above, or a suitable salt thereof, in the presence of a suitable base, to form a compound of formula (IV), 30wherein A and L are as defined above and X is NR2R3; then reacting the compound of formula (IV) with B(OR′)(OR″)(Y), wherein Y is hydrogen or OR′″; R′, R″ and R′″ independently are hydrogen or C1-8-alkyl, or wherein OR′ and OR″ together with the boron atom either form or can be transformed into a 4-12 membered mono- or bicyclic system, to form a compound of formula (V), 31wherein A, R′ and R″ are as defined above and X is NR2R3, and thereupon cyclization of the compound of formula (V), optionally in the presence of a metal specie, to form the compound of formula (I).
- 3. A process according to claim 1 comprising following method:
b) reacting a compound of formula (II) 32wherein A is as defined above, L is a leaving group selected from hydrogen, halogen or trimethylsilyl, and Q is halogen, with a compound of formula (III), 33wherein X is SR1, S(═O)R1 or S(═O)2R1, wherein R1 is defined above, or a suitable salt thereof, in the presence of a suitable base to form a compound of formula (IV), 34wherein A and L are as defined above and X is SR1, S(═O)R1 or S(═O)2R1, then reacting the compound of formula (IV) with B(OR′)(OR″)(Y), wherein Y is hydrogen or OR′″; R′, R″ and R′″ independently are hydrogen or C1-8-alkyl, or wherein OR′ and OR″ together with the boron atom either form or can be transformed into a 4-12 membered mono- or bicyclic system, to form a compound of formula (V), 35wherein A, R′ and R″ are as defined above and X is SR1, S(═O)R1 or S(═O)2R1, and thereupon cyclization of the compound of formula (V), optionally in the presence of a metal specie, to form the compound of formula (I).
- 4. A process according to claim 1 comprising following method:
c) reacting a compound of formula (II) 36wherein A is as defined above, L is a leaving group selected from hydrogen, halogen or trimethylsilyl, and Q is halogen, with a compound of formula (III), 37wherein X is OR′, wherein R1 is defined above, or a suitable salt thereof, in the presence of a suitable base, to form a compound of formula (IV) 38wherein A and L are as defined above and X is OR1, then reacting the compound of formula (IV) with B(OR′)(OR″)(Y), wherein Y is hydrogen or OR′″; R′, R″ and R′″ independently are hydrogen or C1-8-alkyl, or wherein OR′ and OR″ together with the boron atom either form or can be transformed into a 4-12 membered mono- or bicyclic system, to form a compound of formula (V), 39wherein A, R′ and R″ are as defined above and X is OR1, and thereupon cyclization of the compound of formula (V), optionally in the presence of a metal specie, to form the compound of formula (I).
- 5. A process according to claim 1 wherein R2 is hydrogen or C1-6-alkyl, and R3 is hydrogen, C3-6-cycloalkyl, (C3-6-cycloalkyl)C1-6-alkyl or straight or branched C1-18-alkyl.
- 6. A process according to claim 2 wherein R2 is hydrogen or C1-6-alkyl, and R3 is hydrogen, C3-6-cycloalkyl, (C3-6-cycloalkyl)C1-6-alkyl or straight or branched C1-18-alkyl.
- 7. A process according to claim 1 wherein A together with the carbon atoms forming bond e of formula (I) represents a 5 membered heterocyclic system comprising one sulfur atom, the heterocyclic system optionally being substituted with halogen.
- 8. A process according to claim 1 wherein R′ and R″ are hydrogen.
- 9. A process according to claim 1 wherein OR′ and OR″ together with the boron atom form a 1,3,2-dioxaborolan-2-yl, 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, 1,3,2-dioxaborinan-2-yl, 5,5-dimethyl-1,3,2-dioxaborinan-2-yl or a 1,3,2-benzodioxaborol-2-yl group.
- 10. A process according to claim 1 wherein the compounds of formula (I) is selected from the group consisting of:
3-Amino-6-chloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, 6-Chloro-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, 6-Chloro-3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, 6-Chloro-3-ethylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, and 6-Chloro-3-octylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, or a salt thereof with a pharmaceutically acceptable acid or base, or an optical isomer thereof, or a tautomeric form thereof, or metabolites or prodrugs thereof.
- 11. A process according to claim 1 wherein the bases are selected from sodium hydroxide, potassium carbonate, cesium carbonate, potassium hydroxide, pyridine, triethylamine, butyl lithium, hexyl lithium, isopropyl magnesium chloride.
- 12. A process according to claim 1 wherein the metal specie is selected from copper bronze, copper oxide, copper chloride, copper bromide, copper iodide, copper acetate.
Priority Claims (1)
Number |
Date |
Country |
Kind |
PA 2000 01920 |
Dec 2000 |
DK |
|
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of international application no. PCT/DKO1/00836 filed on Dec. 19, 2001, published in English, and claims the benefit of Danish application no. PA 2000 01920 filed on Dec. 21, 2000, and U.S. provisional application No. 60/257,385 filed on Dec. 22, 2000.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60257385 |
Dec 2000 |
US |
Continuations (1)
|
Number |
Date |
Country |
Parent |
PCT/DK01/00836 |
Dec 2001 |
US |
Child |
10464599 |
Jun 2003 |
US |