IL40514A - Sulphamoyl-pyrimidines containing an asymmetric carbon atom and having a blood sugar lowering activity - Google Patents

Claims (9)

1. 40514/2 What we claim Is:- - ^. 1. A racemate or an optical antlpode of a sulphamoyl-pyr m dlne of the general formula I wherei C* represents an asymmetric carbon atom, X and Y each represents a direct bond or a methylene group, A represents a naphthyl group, a pyrldyl group or a phenyl group which may be substituted by one or two substltuents selected from halogen atoms, alkyl groups containing 1 to 6 carbon atoms and alkoxy group* containing 1 to 4 carbon atoms, R3 and R4 are different from each other and each represents a hydrogen atom, a linear or branched alkyl group containing 1 to 4 carbon atoms, a carboxyl group or an alkoxycarbonyl group containing up to 4 carbon atoms, Rg and ^ are Identical or different and each represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, g represents a linear or branched alkyl group containing 1 to 6 carbon atoms and W represents a direct bond or an oxygen atom, or a salt thereof with a physiologically tolerable base, with the proviso that the symbols A, R3 and Rg do not simultaneously have the meanings given for these symbols in Specification No. 36704.

2. R(+)-4-[N- (5* -Isobutyl -2' -pyrlmldlnyl J-sulphanoyl ]-phenyl-acetic add 1"-a-naphthy1ethylam1de.

3. S(-)-4-[N-( 5' -Isobuty1-2' -pyrlmldlnyl )-sulphamoyl ]-phenyl-acetic acid 1 "-a-naphthyl ethylamide.

4. S(-)-4-[N-(5' -Neopenty1-2' -pyrlmldlnyl )-sulphamoyl]-phenyl -acetic add l"-o-naphthy1ethy1am1de.

5. S(-)-4-[N-(5' -Isopropoxy-2' -pyr1m1d1ny1 )-stflphamoyl ] -phenyl -acetic add l"-a-naphthylethylam1de.

6. 4-[N-(5' -Isobutyl -2' -pyrlmldlnyl )-sulphamoyl ] -phenyl acetic add T'-(2,"-pyr1dyl ) -ethyl amide.

7. A process for the manufacture of a sul phamoyl -pyr1m1d1 ne of the general formula I In which i . C* represents an asymmetric carbon atom, X and Y each represents a direct bond or a methylene group, A represents a naphthyl group, a pyrldyl group or a phenyl group which may be substituted by one or two substltuents selected from halogen atoms, alkyi groups containing 1 to 6 carbon atoms and alkoxy groups containing 1 to 4 carbon atoms, R3 and R4 are different from each other and each represents a hydrogen atom, a linear or branched alkyi group containing 1 to 4 carbon atoms, a carboxyl group or an al koxycarbonyl group containing up to 4 carbon atoms, Rg and R7 are Identical or different and each represents a hydrogen atom or an alkyi group containing 1 to 4 carbon atoms, Rg represents a linear or branched alkyi group containing 1 to 6 carbon atoms and W represents a direct bond or an oxygen atom or a salt thereof with a physiologically tolerable base, with the proviso that the symbols A, R3 and Rg do not simultaneously have the meanings given for these symbols 1n Specification Ho.36704, wherein (a) a sulphohallde of the general formula II 1n which C*, X, Y, A, 3, R^, Rg and R^ have the meanings given above and Q represents a halogen atom. Is reacted with guan dlne or a salt thereof and the resulting guan d nesul phony 1 compound of the general formula Is cycllsed by condensation with a substituted malonic d aldehyde of the general formula In which N and g have the meanings given above, and n which the aldehyde groups may be functionally modified, - } - a sulphohallde of the general fopnula II, In which C*, X, Y, A, R3» R^. and R^ have the meanings given above and Q represents a halogen atom, 1s reacted with a 2-amino-5-W-Rg-pyr1m1d1ne, 1n which W and Rg have the meanings given above, or a suphonamlde of the general formula ^3 ^5 ^7* . A-X-C*-Y-N-CO-CH ~ S02-NH2 . in which C*, X, Y, A, R3, R^, Rg and Ry have the meanings given above, or an alkali metal salt thereof 1s reacted with a pyrlmldine derivative of the general formula 1n which W and g have the meanings given above and Q represents a halogen atom, or an acid chloride of the general formula 1n which , R6 and Ry have the meanings given above, 1s reacted with an amine of the general formula A-X-C*-Y-NH , In which C*, X, Y, A, R3, 4 and Rg have the meanings given above, or when the compound of the general formula I, as defined above, 1s 1n the form of an optical antipode, a racemate of a compound of the general formula I, as defined above, which may have been obtained by method (a), (b), (c) or (d) as defined above, is subjected to and, 1f desired, a resulting free compound Is converted Into a salt thereof with a physiologically tolerable Inorganic or organic base and/or, 19. 11 . A pharmaceutical preparation which comprises an optical antipode as claimed in claim 1, in admixture or conjunction with a pharmaceutically 26.1

8. A pharmaceutical preparation as claimed in claim -25, which 1s 1n the form of a tablet, dragee, capsule or pill. 27·.1

9. A pharmaceutical preparation as claimed n claim "25, which Is 1n the form of a powder, suspension or solution. 28-.20. A system which comprises a racemate as claimed In claim 1 and Instructions for Its use 1n lowering the level of blood sugar in a diabetic patient. 29-.21. A system which comprises an optical antlpode as claimed 1n claim 1 and Instructions for its use 1n lowering the level of blood sugar in a diabetic patient. 30-. 22. A system which comprises a salt of a racemate as claimed In claim 1 with a physiologically tolerable base and Instructions for Its use in lowering the level of blood sugar 1n a diabetic patient. 31, 23.A system which comprises a salt of an optical antlpode as claimed in claim 1 with a physiologically tolerable base and Instructions for Its use In lowering the level of blood ;Sugar in a diabetic patient. 32T 24. system which comprises the compound claimed in any one of 2 6 claims 3 to H and Instructions for its use in lowering the level of blood sugar in a diabetic patient. For the Applicants Wolff, Bregman and Goller By: * . JU