Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same

A process for preparing a compound of formula I

• wherein R1 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, F, Cl, Br, I, —CN, NR5R6, —Op—(CH2)n—(CF2)o—CF3 or —(SOm)q—(CH2)r(CF2)s—CF3;
• R5 and R6 are, independently of one another, hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or —CH2—CF3;
• m is zero, 1 or 2;
• n, o, p, q, r and s are, independently of one another, zero or 1;
• R2 is hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, alkoxy having 1, 2, 3 or 4 carbon atoms, F, Cl, Br, I, —CN, NR7R8, —Ot—(CH2)u—(CF2)v—CF3 or —(SOw)x—(CH2)y—(CF2)z—CF3;
• R7 and R8 are, independently of one another, hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, or —CH2—CF3;
• w is zero, 1 or 2;
• t, u, v, x, y and z are, independently of one another, zero or 1;
• R3 is Cl, Br, I, —CN, —SO2CH3, alkoxy having 1, 2, 3 or 4 carbon atoms, NR9R10, —Oa—(CH2)b—(CF2)c—CF3, —(SOd)e—(CH2)f—(CF2)g—CF3, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms or cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, wherein 1, 2, 3 or 4 hydrogen atoms may be replaced by fluorine atoms;
• R9 and R10 are, independently of one another, hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms, or —CH2—CF3;
• a, b and c are, independently of one another, zero or 1;
• d is zero, 1 or 2;
• e is zero or 1;
• f is zero, 1, 2, 3 or 4;
• g is zero or 1;
• or R3 is —(CH2)h-phenyl or —O-phenyl, in which the phenyl radicals are unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of F, Cl, Br, I, —Oj—(CH2)k—CF3, alkoxy having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms, and —SO2CH3;
• j is zero or 1;
• k is zero, 1, 2 or 3;
• h is zero, 1, 2, 3 or 4;
• or R3 is —(CH2)aa-heteroaryl, which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of F, Cl, Br, I, —Obb—(CH2)cc—CF3, alkoxy having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms, and —SO2CH3;
• bb is zero or 1;
• cc is zero or 1, 2 or 3;
• aa is zero, 1, 2, 3 or 4;
• R4 is hydrogen, F, Cl, Br, I, —CN, —SO2CH3, alkoxy having 1, 2, 3 or 4 carbon atoms, NR11R12, —Odd—(CH2)ee—(CF2)ff—CF3;
• —(SOgg)hh—(CH2)jj—(CF2)kk—CF3, alkyl having 1, 2, 3, 4, 5 or 6 carbon atoms or cycloalkyl having 3, 4, 5, 6, 7 or 8 carbon atoms, wherein 1, 2, 3 or 4 hydrogen atoms may be substituted by fluorine atoms;
• R11 and R12 are, independently of one another, hydrogen, alkyl having 1, 2, 3 or 4 carbon atoms or —CH2—CF3;
• dd, ee and ff are, independently of one another, zero or 1;
• gg is zero, 1 or 2;
• hh is zero or 1;
• jj is zero, 1, 2, 3 or 4;
• kk is zero or 1;
• or R4 is —(CH2)ll-phenyl or —O-phenyl, wherein the phenyl radicals are unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of F, Cl, Br, I, —Omm—(CH2)nn—CF3, alkoxy having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms, and —SO2CH3;
• mm is zero or 1;
• nn is zero, 1, 2 or 3;
• ll is zero, 1, 2, 3 or 4;
• or R4 is —(CH2)oo-heteroaryl, which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of F, Cl, Br, I, —Opp—(CH2)n—CF3, alkoxy having 1, 2, 3 or 4 carbon atoms, alkyl having 1, 2, 3 or 4 carbon atoms, and —SO2CH3;
• pp is zero or 1;
• rr is zero, 1, 2 or 3;
• and
• oo is zero, 1, 2, 3 or 4,
• said process comprising the step of:
• reacting a compound of formula II,
• wherein R1 to R4 are as previously defined, and L is a leaving group which can undergo nucleophilic substitution, with guanidine.