Guanidinealkyl-1,1-bisphosphonic acid derivatives, process for their preparation and their use

A compound of the tautomeric formula Ia, Ib or Ic ##STR19## a physiologically tolerated salt of the compound of the formula Ia, Ib or Ic;

• R has the following meaning therein:
• I) a radical of the formula V ##STR20## wherein R.sup.11 or R.sup.12 has the following meaning:
• a) R.sup.13 --S(O).sub.n -- or
• b) ##STR21## where R.sup.13 is 1) (C.sub.1 -C.sub.6)-alkyl,
• 2) (C.sub.5 -C.sub.7)-cycloalkyl,
• 3) cyclopentylmethyl,
• 4) cyclohexylmethyl,
• 5) phenyl,
• 6) phenyl substituted once to three times by
• 6.1 fluorine atom,
• 6.2 chlorine atom,
• 6.3 methyl or
• 6.4 methoxy,
• where n is the integer zero, 1 or 2, where R.sup.14 and R.sup.15 are identical or different and have, independently of one another, the following meaning:
• 1) hydrogen atom,
• 2) (C.sub.1 -C.sub.6)-alkyl,
• 3) phenyl,
• 4) phenyl substituted once or twice by
• 4.1 fluorine atom,
• 4.2 chlorine atom,
• 4.3 methyl or
• 4.4 methoxy,
• 5) --(CH.sub.2).sub.m -phenyl where m is an integer from 1 to 4, or
• 6) --(CH.sub.2).sub.m -phenyl where m is an integer from 1 to 4 and the phenyl radical is substituted once or twice by the radicals indicated in 4.1 to 4.4,
• and the other substituent R.sup.11 or R.sup.12 in each case means
• a) hydrogen atom,
• b) halogen atom, selected from the group consisting of fluorine, chlorine, bromine or iodine atom,
• c) (C.sub. -C.sub.4)-alkyl,
• d) (C.sub.2 -C.sub.4)-alkoxy,
• e) phenoxy,
• f) phenoxy substituted once to three times by
• 1) fluorine or chlorine atom,
• 2) methyl or
• 3) methoxy,
• g) R.sup.13 --S(O).sub.n, where n is the integer zero, 1 or 2 and R.sup.13 has the abovementioned meaning, or ##STR22## where R.sup.14 and R.sup.15 have the abovementioned meaning, or II) a radical of the formula VI ##STR23## wherein R.sup.21, R.sup.22, or R.sup.23 has the following meaning:
• a) hydrogen atom,
• b) halogen atom, selected from the group consisting of fluorine, chlorine, bromine and iodine atom, or
• c) (C.sub.1 -C.sub.12)-alkyl, where one of the substituents R.sup.21, R.sup.22 or R.sup.23 may also mean
• 1) N.sub.3,
• 2) CN,
• 3) OH,
• 4) (C.sub.1 -C.sub.10)-alkoxy,
• 5) R.sup.24 --C.sub.n H.sub.2n --O.sub.m,
• where m is the number zero or 1, n is the number zero, 1, 2 or 3,
• R.sup.24 is
• 1) C.sub.p F.sub.2p+1 where
• is the number 1, 2 or 3, as long as
• n is the number zero or 1,
• 2) (C.sub.3 -C.sub.12)-cycloalkyl,
• 3) phenyl,
• where the ring system in the radicals 3) to 6) is unsubstituted or substituted by a radical from the group
• 3. 1 fluorine atom,
• 3.2 chlorine atom,
• 3.3 CF.sub.3,
• 3.4 methyl,
• 3.5 methoxy or
• 3.6 NR.sup.25 R.sup.26
• where R.sup.25 and R.sup.26 are identical or different and have, independently of one another, the meaning
• 3.6.1 hydrogen atom or
• 3.6.2 (C.sub.1 -C.sub.4)-alkyl, or
• R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are identical or different and have, independently of one another, the following meaning
• a) hydrogen atom,
• b) (C.sub.1 -C.sub.5)-alkyl, straight-chain or branched, or
• c) phenyl.