Amino alcohol derivatives, process for their production and pharmaceutical preparations and reagents containing these compounds

1. A composition comprising a compound of formula (I)

wherein

A is selected from the group consisting of hydrogen, a group NR 1 R 2 , a group NR 1 (CH 2 ) p NR 3 R 4 , a group (C═NH)NH 2 and a pyridinyl residue;

B and D are each independently selected from the group consisting of a bond, a C 1 –C 6 alkylene residue and a group NR 5 —(C 2 to C 6 alkylene);

J is selected from the group consisting of piperidinediyl and piperazinediyl;

W and X are each independently selected from the group consisting of a bond and a carbonyl group;

Y and Z are each independently a saturated or unsaturated C 7 –C 24 hydrocarbon residue;

R 1 –R 5 are each independently selected from the group consisting of hydrogen and a C 1 –C 6 alkyl residue;

m is 0, 1 or 2, wherein when m is 2, the two residues J are identical to or different from each other;

n and o are each independently 2, 3 or 4; and

p is 2–6,

or a physiologically tolerated salt thereof,

and that m is other than 0 when A is either hydrogen or a group (C═NH)NH 2 and B and D are each independently a bond or an alkylene residue, wherein the composition further comprises a therapeutic agent.

2. The composition of claim 1 , wherein m is 1 or 2.

3. The composition of claim 1 , wherein the compound contains more than two nitrogens, or if A is (C═NH)NH 2 , the compound contains more than three nitrogens.

4. The composition of claim 1 , further comprising a nucleic acid.

5. A compound of formula (I),

wherein

A is selected from the group consisting of a group NR 1 R 2 , a group NR 1 (CH 2 ) p NR 3 R 4 , a group (C═NH)NH 2 and a pyridinyl residue;

B and D are each independently selected from the group consisting of a bond, a C 1 –C 6 alkylene residue, and a group NR 5 —(C 2 to C 6 alkylene);

J is selected from the group consisting of piperidinediyl and piperazinediyl;

W and X are each independently selected from the group consisting of a bond and a carbonyl group;

Y and Z are each independently a saturated or unsaturated C 7 –C 24 hydrocarbon residue;

R 1 –R 5 are each independently selected from the group consisting of hydrogen and a C 1 –C 6 alkyl residue;

m is 1 or 2, wherein when m is 2, the two residues J are identical to or different from each other;

n and o are each independently 2, 3 or 4; and

p is 2–6,

or a physiologically tolerated salt thereof.

6. The compound of claim 5 , wherein A is NH 2 or N(CH3) 2 .

7. The compound of claim 5 , wherein B and D are each independently selected from the group consisting of a bond and a C 1 –C 3 alkylene residue.

8. The compound of claim 5 , wherein J is piperidinediyl.

9. The compound of claim 5 , wherein m is 1.

10. The compound of claim 5 , wherein W and X each are a carbonyl group.

11. The compound of claim 5 , wherein Y is C 13 H 27 or C 17 H 33 .

12. The compound of claim 5 , wherein Z is C 13 H 27 or C 17 H 33 .

13. The compound of claim 5 , wherein n and o are each 2.

14. The compound of claim 5 , wherein

A is NH 2 or N(CH 3 ) 2 ;

B and D are each independently selected from the group consisting of a bond and a C 1 –C 3 alkylene residue;

J is piperidinediyl;

m is 1;

W and X each are a carbonyl group;

Y and Z are each independently C 13 C 17 H 27 or H 33 ; and

n and o are each 2.

15. A composition comprising a compound as claimed in claim 5 and a therapeutic agent.

16. The composition of claim 15 , further comprising a nucleic acid.

17. A compound of formula (II),

wherein

A is selected from the group consisting of a group NR 1 R 2 , a group NR 1 (CH 2 ) p NR 3 R 4 , a group (C═NH)NH 2 and a pyridinyl residue;

B is selected from the group consisting of a bond, a C 1 –C 6 alkylene residue and a group NR 5 —(C 2 to C 6 alkylene);

D is selected from the group consisting of a C 1 –C 6 alkylene residue and a group NR 5 —(C 2 to C 6 alkylene);

J is selected from the group consisting of piperidinediyl and piperazinediyl;

R 1 –R 5 are each independently selected from the group consisting of hydrogen and a C 1 –C 6 alkyl residue;

m is 1 or 2, wherein when m is 2, the two residues J are identical to or different from each other.

n and o are each independently 2, 3 or 4; and

p is 2–6,

or a physiologically tolerated salt thereof.

18. The compound of claim 17 , wherein A is NH 2 or N(CH 3 ) 2 .

19. The compound of claim 17 , wherein B and D are each independently selected from the group consisting of a bond and a C 1 –C 3 alkylene residue.

20. The compound of claim 17 , wherein J is piperidinediyl.

21. The compound of claim 17 , wherein m is 1.

22. The compound of claim 17 , wherein n and o are each 2.

23. The compound of claim 17 , wherein

A is NH 2 or N(CH 3 ) 2 ;

B and D are each independently selected from the group consisting of a bond and a C 1 –C 3 alkylene residue;

J is piperidenediyl;

m is 1; and

n and o are each 2.

24. A method of introducing a biologically active agent into a target cell, comprising combining the biologically active agent with a composition as claimed in claim 1 to produce a biologically active agent composition; and thereafter introducing the biologically active agent composition into the target cell.

25. The method of claim 24 , wherein the target cell is a mammalian cell.

26. The method of claim 24 , wherein the target cell is a human cell.

27. The method of claim 24 , wherein the biologically active agent composition is introduced into the target cell in vitro.

28. The method of claim 24 , wherein the biologically active agent is selected from the group consisting of a protein, a nucleic acid, a polynucleotide, a peptide hormone, a cytostatic agent and an antibiotic.

29. A method of introducing a biologically active agent into a target cell, comprising combining the biologically active agent with a compound as claimed in claim 5 to produce a biologically active agent composition; and thereafter introducing the biologically active agent composition into the target cell.

30. The method of claim 29 , wherein the target cell is a mammalian cell.

31. The method of claim 29 , wherein the target cell is a human cell.

32. The method of claim 29 , wherein the biologically active agent composition is introduced into the target cell in vitro.

33. The method of claim 29 , wherein the biologically active agent is selected from the group consisting of a protein, a nucleic acid, a polynucleotide, a peptide hormone, a cytostatic agent and an antibiotic.