Claims
- 1. 2"-Amino-2"-deoxyarbekacin having the formula ##STR45## or a pharmaceutically acceptable acid addition salt thereof.
- 2. 2"-Amino-2"-deoxydibekacin having the formula ##STR46## or a pharmaceutically acceptable acid addition salt thereof.
- 3. 2"-Amino-5,2"-dideoxy-5-epi-fluoroarbekacin having the formula ##STR47## or a pharmaceutically acceptable acid addition salt thereof.
- 4. An antibacterial composition comprising an antibacterially effective amount of 2"-amino-2"-deoxyarbekacin according to claim 1 or a pharmaceutically acid addition salt thereof as active ingredient, in combination with a pharmaceutically acceptable carrier for the active ingredient.
- 5. An antibacterial composition comprising an antibacterially effective amount of 2"-amino-2"-deoxydibekacin according to claim 2 or a pharmaceutically acid addition salt thereof as active ingredient, in combination with a pharmaceutically acceptable carrier for the active ingredient.
- 6. An antibacterial composition comprising an antibacterially effective amount of 2"-amino-5,2"-dideoxy-5-epi-fluoroarbekacin according to claim 3 or a pharmaceutically acid addition salt thereof as active ingredient, in combination with a pharmaceutically acceptable carrier for the active ingredient.
- 7. A process for the-preparation of 2"-amino-2"-deoxyarbekacin of the following formula (Ia) ##STR48## which comprises the steps of: protecting each of the 1- and 3"-amino groups of 3,2',6'-N-tris(alkoxycarbonyl)-dibekacin represented by general formula (III) ##STR49## wherein A means an alkoxycarbonyl group serving as an amino-protecting group removable by hydrolysis, with an aralkyloxycarbonyl group which is an amino-protecting group removable by hydrogenolysis, to form a 1,3"-N-bis(aralkyloxycarbonyl)-3,2',6'-N-tris (alkoxycarbonyl)-dibekacin represented by general formula (IV) ##STR50## wherein A has the meaning as defined above and B means an aralkyloxycarbonyl group;
- protecting both of the two hydroxyl groups at the 4"- and 6"-positions of the compound of general formula (IV) with an aralkylidene or alkylidene group as a hydroxyl-protecting group, to form a 4",6"-O-aralkylidene or alkylidene-1,3"-N-bis(aralkyloxycarbonyl)-3,2',6'-N-tris-(alkoxycarbonyl)-dibekacin represented by the following formula (V) ##STR51## wherein A and B have the meanings as defined above and Y means an aralkylidene or alkylidene group;
- oxidizing the 2"-hydroxyl group of the compound of formula (V) with an oxidizing agent to form a 4",6"-O-aralkylidene or alkylidene-1,3"-N-bis(aralkyloxycarbonyl)-3,2'-6'-N-tris (alkoxycarbonyl)-2"-deoxy-2"-oxodibekacin represented by the following formula (VI) ##STR52## wherein A, B and Y have the meanings as defined above; converting the 2"-oxo group of the compound of formula (VI) into 2"-amino group by reducing the same with a hydride in the presence of ammonium acetate, thereby to form a 2"-amino-4",6"-O-aralkylidene or alkylidene-1,3"-N-bis(aralkyloxycarbonyl)-3,2',6'-N-tris(alkoxycarbonyl)-2-deoxydibekacin represented by the following formula (VII) ##STR53## wherein A, B and Y have the meanings as defined above; protecting the 2"-amino group of the compound of formula (VII) with an alkoxycarbonyl group (A) to form a 2"-amino-4",6"-O-aralkylidene or alkylidene-1,3"-N-bis(aralkyloxycarbonyl)-3,2',6',2"-N-tetrakis (alkoxycarbonyl)-2"-deoxydibekacin represented by the following formula (VIII) ##STR54## wherein A, B and Y have the meanings as defined above; eliminating the aralkyloxycarbonyl groups (B) from the 1- and 3"-amino groups by hydrogenolysis to form a 2"-amino-4",6"-O-aralkylidene or alkylidene-3,2',6',2"-N-tetrakis(alkoxycarbonyl)-2"-deoxydibekacin represented by the following formula (IX) ##STR55## wherein A and Y have the meanings as defined above; acylating the 1- amino group of the compound of formula (IX) with an active ester or acid halide of (S)-4-(p-alkoxy-substituted-benzyloxycarbonyl- or alkoxycarbonylamino)-2-hydroxybutyric acid represented by the following formula (X) ##STR56## wherein A' means a p-alkoxy-substituted-benzyloxycarbonyl or alkoxycarbonyl group as an amino-protecting group removable by hydrolysis, to form a 1-N-[(S)-4-(p-alkoxy-substituted-benzyloxycarbonyl- or alkoxycarbonyl-amino)-2-hydroxybutyryl]-2"-amino-4",6"-O-aralkylidene or alkylidene-3,2',6',2"-N-tetrakis (alkoxycarbonyl)-2"-deoxydibekacin represented by the following formula (XI) ##STR57## wherein A, Y and A' have the meanings as defined above; and hydrolyzing the compound of formula (XI) to remove therefrom the alkoxycarbonyl group (A), the p-alkoxy-substituted-benzyloxycarbonyl or alkoxycarbonyl group (A'), and the aralkylidene or alkylidene group (Y) and to produce the compound of formula (Ia).
- 8. A process for the preparation of 2"-amino-5,2"-dideoxyarbekacin of the following formula (Ib) ##STR58## which comprises the steps of: eliminating by a known deoxygenation method the 5-hydroxyl group of a 2"-amino-4",6"-O-aralkylidene or alkylidene 1,3"-N-bis(aralkyloxycarbonyl)-3,2',6',2"-N-tetrakis(alkoxycarbonyl)-2"-deoxyydibekacin represented by general formula (VIII) ##STR59## wherein A means an alkoxycarbonyl group, B means an aralkyloxycarbonyl group and Y means an aralkylidene or alkylidene group, to form a 2"-amino-4",6"-O-aralkylidene or alkylidene-1,3"-N-bis(aralkyloxycarbonyl)-3,2',6',2"-N-tetrakis (alkoxycarbonyl)-5,2"-dideoxydibekacin represented by the following formula (XII) ##STR60## wherein A, B and Y have the meanings as defined above; eliminating the aralkyloxycarbonyl groups (B) from the 1- and 3"-amino groups of the compound of formula (XII) to form a 2"-amino-4",6"-O-aralkylidene or alkylidene-3,2',2"-N-tetrakis(alkoxycarbonyl)-5,2"-dideoxydibekacin represented by the following formula (XIII) ##STR61## wherein A and Y have the meanings as defined above; acylating the 1- amino group of the compound of formula (XIII) with an active ester or acid halide of (S)-4-(p-alkoxy-substituted-benzyloxycarbonyl- or alkoxycarbonylamino)-2-hydroxybutyric acid represented by the following formula (X): ##STR62## wherein A' means a p-alkoxy-substituted-benzyloxycarbonyl or alkoxycarbonyl group as an amino-protecting group removable by hydrolysis, to form a 1-N-[(S)-4-(p-alkoxy-substituted-benzyloxycarbonyl- or alkoxycarbonyl-amino)-2-hydroxybutyryl]-2"-amino-4",6"-O-aralkylidene or alkylidene-3,2',6',2"-N-tetrakis(alkoxycarbonyl)-5,2"-dideoxydibekacin represented by the following formula (XIV) ##STR63## wherein A, Y and A' have the meanings as defined above; and hydrolyzing the compound of formula (XIV) to remove therefrom the alkoxycarbonyl group (A), the p-alkoxy-substituted-benzyloxycarbonyl or alkoxycarbonyl group (A'), and the aralkylidene or alkylidene group (Y) and to produce the compound of formula (Ib).
- 9. A process for the preparation of 2"-amino-2"-deoxydibekacin of formula (IIa) ##STR64## which comprises removing9 the aralkylidene or alkalidens group (Y) and alkoxycarbonyl group (A) of a 2"-amino-4", 6"-O-aralkylidene-or alkylidene-3,2',6',2"-N-tetrakis(alkoxycarbonyl)-2"-deoxydibekacin represented by general formula (IX): ##STR65## wherein A means an alkoxycarbonyl group and Y means an aralkylidene or alkylidene group, from the compound of formula (IX) to produce the compound of formula (IIa).
Priority Claims (2)
Number |
Date |
Country |
Kind |
4-341314 |
Nov 1992 |
JPX |
|
5-247327 |
Sep 1993 |
JPX |
|
Parent Case Info
This is a division of application Ser. No. 08/154,002 filed Nov. 18, 1993 now U.S. Pat. No. 5,988,038.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
4107424 |
Umezawa et al. |
Aug 1978 |
|
4156078 |
Umezawa et al. |
May 1979 |
|
4187372 |
Carney et al. |
Feb 1980 |
|
4873225 |
Umezawa et al. |
Oct 1989 |
|
Divisions (1)
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Number |
Date |
Country |
Parent |
154002 |
Nov 1993 |
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