# US 4,393,051 A · 1-N(Aminopolyhydroxyalkyl)aminoglycoside antibiotics and method of use

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- Number: US 4,393,051 A
- Document ID: US4393051A
- Status: Granted
- Kind: A
- Application number: 06/155,896
- Filed: 1980-06-02
- Granted: 1983-07-12
- Earliest claimed: 1979-06-19
- Assignees: Bayer Aktiengesellschaft
- Inventors: Peter Stadler; Karl G. Metzger; Eckart Voss; Uwe Petersen; Hans-Joachim Zeiler
- Web page: https://patentgrep.com/patent/US4393051A

## CPC

- C07H 15/234: attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- A61P 31/04: Antibacterial agents
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to pseudotrisaccharides of Formula (I) as defined above, methods for preparing them, compositions containing them and methods for the use of said compounds and compositions.

## Claims

### Claim 1

A compound which is a pseudotrisaccharide of the formula ##STR17## or a pharmaceutically acceptable acid addition salt thereof, in which X denotes a radical of the formulae ##STR18## Y denotes a radical of the formula ##STR19## U and V both denote hydrogen atoms, or one denotes a hydrogen atom and one denotes a hydroxyl group and
W and Z both denote hydrogen atoms, or one denotes a hydrogen atom and one denotes a hydroxyl group, or
Z denotes NHR.sub.6 and
W denotes a hydrogen atom, and
R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 independently of one another denote a hydrogen atom or an amino-polyhydroxyalkyl radical derived from an amino sugar which is optionally N-protected and optionally carries C.sub.1 -C.sub.4 -alkyl, carboxylic acid acyl or C.sub.1 -C.sub.6 -alkylidene radicals on one or more OH-groups, at least one of the radicals R.sub.1 to R.sub.5 being other than hydrogen.

### Claim 2 (depends on 1)

A compound according to claim 1 which is derived from one of the antibiotics gentamicin A, gentamicin B, gentamicin B.sub.1, gentamicin C.sub.1, gentamicin C.sub.1a, gentamicin C.sub.2, gentamicin C.sub.2a, gentamicin C.sub.2b, gentamicin X.sub.2, sisomicin, JI-20A, JI-20B, verdamicin G52, G418, 66-40D, mutamicin 1, mutamicin 2, mutamicin 4, mutamicin 5 and mutamicin 6.

### Claim 3 (depends on 1)

A compound according to claim 1, which is a sisomicin derivative of the formula ##STR20## or a pharmaceutically acceptable acid-addition salt thereof in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the same meanings as in claim 1.

### Claim 4 (depends on 1)

A compound according to claim 1 in which R.sub.4 and one of the radicals R.sub.1 and R.sub.2 are other than a hydrogen atom and the radicals R.sub.3, R.sub.5, R.sub.6 and the other one of the radicals R.sub.1 and R.sub.2 denote a hydrogen atom.

### Claim 5 (depends on 1)

A compound according to claim 1, in which R.sub.1, R.sub.2, R.sub.3, R.sub.5 and R.sub.6 denote a hydrogen atom and R.sub.4 is other than hydrogen.

### Claim 6 (depends on 1)

A pharmaceutical composition containing as an active ingredient an antibacterially effective amount of a compound according to claim 1 in admixture with a solid, liquid or liquefied gaseous diluent.

### Claim 7 (depends on 6)

A pharmaceutical composition of claim 6 in the form of a sterile or physiologically isotonic aqueous solution.

### Claim 8 (depends on 6)

A composition according to claim 6 in the form of an ointment, cream or lotion containing from 0.1 to 3.0 g by weight of the said active ingredient per 100 gm of ointment, cream or lotion.

### Claim 9 (depends on 6)

A medicament of claim 6 in the form of tablets, pills, dragees, capsules, ampoules, or suppositories.

### Claim 10 (depends on 1)

A method of combating bacterial diseases in warm-blooded animals which comprises administering to the animals an antibacterially effective amount of an active compound according to claim 1 either alone or in admixture with a diluent or in the form of a medicament.

### Claim 11 (depends on 10)

A method according to claim 10 in which the active compound is administered in an amount of 100 to 500 mg per day.

### Claim 12 (depends on 10)

A method according to claim 10 in which the active compound is administered parenterally in an amount of 1 to 15 mg of active compound per kilogram of body weight.