# US 7,078,566 B2 · Salts of guanidine derivatives and pharmaceutical preparations consisting thereof

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- Number: US 7,078,566 B2
- Document ID: US7078566B2
- Status: Granted
- Kind: B2
- Application number: 10/820,121
- Filed: 2004-04-08
- Published: 2004-09-30
- Granted: 2006-07-18
- Earliest claimed: 2001-10-10
- Assignees: Biosphinks Aktiengesellschaft
- Inventors: Eberhard Amtmann
- Web page: https://patentgrep.com/patent/US7078566B2

## CPC

- C07C 281/18: the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/12: Antivirals
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to salts of guanidine derivatives of formula R—X—C(═NH)NH3+Z−, wherein X represents a valence bond, —CH2—NH—, —CH2—NH—NH— or —CH═N—NH—; R represents a linear or branched C1–C30 alkyl, C3–C20 cycloalkyl, adamantyl, norbornyl, tricyclodecyl, benzyl, furyl, pyridyl, anthracyl, naphthyl, phenanthryl, perinaphthyl or quinuclidinyl residue, which can be substituted by one or more hydroxyl groups, C1–C4 alkoxy groups, C1–C4 alkyl groups and/or one or more halogen atoms or one or more amino groups; Z represents O—CO—Y, O—S(O)2—Y, or O—P(O)(OH)—Y; and Y represents a linear or branched C1–C12 alkyl, C3–C8 cycloalkyl, benzyl, furyl or pyridyl residue, which can be substituted by one or more hydroxyl groups, carboxylic acid groups, C1–C4 alkoxy groups, C1–C4 alkyl groups and/or one or more halogen atoms or one or more amino groups. These compounds are useful for treating tumor diseases, autoimmune diseases, cardiovascular diseases, infections, and viral diseases.

## Claims

### Claim 1

A pharmaceutical preparation for the treatment of tumor diseases, autoimmune diseases, cardiovascular diseases, infections, or viral diseases, comprising one or more salts of guanidine derivatives corresponding to the formula
wherein
X represents —CH2—NH—NH— or —CH═N—NH—,
R represents a linear or branched C1–C30 alkyl, C3–C20 cycloalkyl, or tricyclodecyl residue, which can be substituted by one or more hydroxyl groups, C1–C4 alkoxy groups, C1–C4 alkyl groups and/or one or more halogen atoms or one or more amino groups, and
Z represents O—CO—Y, O—S(O)2—Y, or O—P(O)(OH)—Y, wherein Y represents a linear or branched C1–C12 alkyl, C3–C8 cycloalkyl, benzyl, furyl or pyridyl residue, which can be substituted by one or more hydroxyl groups, carboxylic acid groups, C1–C4 alkoxy groups, C1–C4 alkyl groups and/or one or more halogen atoms or one or more amino groups.

### Claim 2 (depends on 1)

The preparation according to claim 1, wherein Z represents O—CO—Y.

### Claim 3 (depends on 1)

The preparation according to claim 1, wherein R represents a pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, cyclododecyl, tricyclo[5,2,1,02,6]-decyl, or bicyclo[2,2,1]-heptyl residue.

### Claim 4 (depends on 1)

The preparation according to claim 1, wherein R represents a decyl residue.

### Claim 5 (depends on 1)

The preparation according to claim 1, wherein Y is methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, hydroxyethyl or 2-hydroxy-2,3-dicarboxylic acid propyl.

### Claim 6 (depends on 5)

The preparation according to claim 5, wherein R represents a decyl residue.

### Claim 7 (depends on 1)

The preparation according to claim 1, said salt being undecylideneaminoguanidine acetate or undecylideneaminoguanidine lactate.

### Claim 8 (depends on 1)

The preparation according to claim 1, said salt being undecylideneaminoguanidine oenanthate or undecylideneaminoguanidine pelargonate.

### Claim 9 (depends on 1)

The preparation according to claim 1, said salt being undecylideneaminoguanidine decanoate.

### Claim 10 (depends on 1)

The preparation according to claim 1, said salt being undecylideneaminoguanidine hexanoate.

### Claim 11 (depends on 1)

The preparation according to claim 1, wherein Z is O—S(O)2—Y (sulfonic acid group), or O—P(O)(OH)—Y (phosphonic acid group).

### Claim 12 (depends on 1)

The preparation according to claim 1, further comprising a parmaceutically acceptable additives and/or excipients.

### Claim 13

Method for the preparation of a pharmaceutical preparation for the treatment of tumor diseases, autoimmune diseases, cardiovascular diseases, infections, or viral diseases, comprising combining one or more salts of guanidine derivatives corresponding to the formula
wherein
X represents —CH2—NH—NH— or —CH═N—NH—,
R represents a linear or branched C1–C30 alkyl, C3–C20 cycloalkyl, or tricyclodecyl residue, which can be substituted by one or more hydroxyl groups, C1–C4 alkoxy groups, C1–C4 alkyl groups and/or one or more halogen atoms or one or more amino groups, and
Z represents O—CO—Y, O—S(O)2—Y, or O—P(O)(OH)—Y, wherein Y represents a linear or branched C1–C12 alkyl, C3–C8 cycloalky, benzyl, furyl or pyridyl residue, which can be substituted by one or more hydroxyl groups, carboxylic acid groups, C1–C4 alkoxy groups, C1–C4alky groups and/or one or more halogen atoms or one or more amino groups, with a pharmaceutically acceptable additives and/or excipients to produce an administrable form.

### Claim 14 (depends on 13)

Method according to claim 13, comprising: providing approximately equimolar amounts of the corresponding base and acid, and combining the base and acid with the pharmaceutically acceptable additives and/or excipients.

### Claim 15 (depends on 1)

Method for the treatment of tumor diseases, autoimmune diseases, cardiovascular diseases, infections, or viral diseases comprising administering to a patient a pharmaceutically effective amount of the pharmaceutical preparation of claim 1.