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US4396609A
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Aminocyclitol antibiotics, pharmaceutical compositions and method of using same
Assignee: Sanofi SA
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Filing: 1977-09-06
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Granted: 1983-08-02
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Expires: 1997-09-06
Abstract
Abstract Aminocyclitol analogs of gentamicin C1, C2 and C1a and the corresponding compounds acylated on the 1-, 3- and 2'-amino groups with an omega -amino- alpha -hydroxy-lower-alkanoyl group are prepared by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and an added aminocyclitol with a mutant of Micromonospora purpurea and acylating the product with an ester of an omega -(N-benzyloxycarbonyl)amino- alpha -hydroxy-lower-alkanoic acid followed by catalytic hydrogenolysis of the benzyloxycarbonyl group.
Inventors
- 👤 Sol J. Daum
- 👤 Robert L. Clarke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 06:56
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/226; C07H15/234; C07H15/236; C07D; C07D231/00; C07D231/54; C07D303/00; C07D303/02; C07D303/12; C07D303/14
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
95 words
A compound having the formula: ##STR6## where R 1 , R 3 and R 5 each represent hydrogen, or one of R 1 , R 3 and R 5 represents an ω-amino-α-hydroxy-lower-alkanoyl group having the formula: H.sub.2 NCH.sub.2 (CH.sub.2).sub.n CHOHCO-- where n is zero or 1, the other of R 1 , R 3 and R 5 being hydrogen; R 2 represents hydrogen or hydroxy; R 4 represents hydrogen, hydroxy or halogen, except that when R 2 is hydrogen, R 4 is not hydroxy; and R 6 and R 7 each represent hydrogen or methyl.
Claim 2
Dependent Claim
95 words
A compound having the formula: ##STR6## where R 1 , R 3 and R 5 each represent hydrogen, or one of R 1 , R 3 and R 5 represents an ω-amino-α-hydroxy-lower-alkanoyl group having the formula: H.sub.2 NCH.sub.2 (CH.sub.2).sub.n CHOHCO-- where n is zero or 1, the other of R 1 , R 3 and R 5 being hydrogen; R 2 represents hydrogen or hydroxy; R 4 represents hydrogen, hydroxy or halogen, except that when R 2 is hydrogen, R 4 is not hydroxy; and R 6 and R 7 each represent hydrogen or methyl.
Claim 3
Dependent Claim
18 words
A compound according to claim 1 where R 1 , R 3 and R 5 each represent hydrogen.
Claim 4
Dependent Claim
47 words
A compound according to claim 1 where one of R 1 , R 3 and R 5 represents an ω-amino-α-hydroxy-lower-alkanoyl group having the formula: H.sub.2 NCH.sub.2 (CH.sub.2).sub.n CHOHCO-- where n is zero or 1, the other of R 1 , R 3 and R 5 being hydrogen.
Claim 5
Dependent Claim
15 words
A compound according to claim 3 where R 2 and R 4 each represent hydroxy.
Claim 6
Dependent Claim
5 words
O-[3-Deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)]-O-[2-amino-6-methylamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-D-streptamine according to claim 2.
Claim 7
Dependent Claim
5 words
O-3-Deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-D-streptamine according to claim 2.
Claim 8
Dependent Claim
5 words
O-3-Deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1.fwdarw.4)]-D-streptamine according to claim 2.
Claim 9
Dependent Claim
5 words
O-3-Deoxy-4-C-methyl-3-methylamino-.beta.-L-arabinopyranosyl-(1→6)-O-[2-amino-6-methylamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-2,5-dideoxystreptamine according to claim 2.
Claim 10
Dependent Claim
5 words
O-3-Deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-2,5-dideoxystreptamine according to claim 2.
Claim 11
Dependent Claim
5 words
O-3-Deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-2,5-dideoxystreptamine according to claim 2.
Claim 12
Dependent Claim
5 words
2'-[S-(-)-γ-Amino-α-hydroxybutyryl]-O-[3-deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)]-O-[2-amino-6-methylamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-D-streptamine according to claim 4.
Claim 13
Dependent Claim
5 words
1-[S-(-)-γ-Amino-α-hydroxybutyryl]-O-[3-deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)]-O-[2-amino-6-methylamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-D-streptamine according to claim 4.
Claim 14
Dependent Claim
5 words
3-[S-(-)-γ-Amino-α-hydroxybutyryl]-O-[3-deoxy-4-C-methyl-3-methylamino-β-L-arabinopyranosyl-(1→6)]-O-[2-amino-6-methylamino-6-C-methyl-2,3,4,6-tetradeoxy-α-D-erythro-glucopyranosyl-(1→4)]-D-streptamine according to claim 4.
Claim 15
Dependent Claim
59 words
A 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1-N-X derivatives thereof wherein X is ##STR7## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
59 words
A 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1-N-X derivatives thereof wherein X is ##STR7## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof.
Claim 17
Dependent Claim
9 words
A compound of claim 14 which is a 4-O-aminoglycosyl-6-O-garosaminyl-2,5-dideoxystreptamine.
Claim 18
Dependent Claim
11 words
A compound of claim 15 which is 5-deoxygentamicin C 2 .
Claim 19
Dependent Claim
12 words
A compound of claim 14 which is 1-N-X-4-O-aminoglycosyl-6-O-garosaminyl-2,5-dideoxystreptamine wherein X is 4-amino-2-hydroxybutyryl.
Claim 20
Independent Claim
103 words
The method of eliciting an antibacterial response in a warm-blooded animal having a susceptible bacterial infection which comprises administering to said animal a non-toxic, antibacterially effective amount of a member selected from the group consisting of a 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1N-X derivatives thereof wherein X is a substituent selected from the group consisting of ##STR8## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof.
Claim 21
Independent Claim
103 words
The method of eliciting an antibacterial response in a warm-blooded animal having a susceptible bacterial infection which comprises administering to said animal a non-toxic, antibacterially effective amount of a member selected from the group consisting of a 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1N-X derivatives thereof wherein X is a substituent selected from the group consisting of ##STR8## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof.
Claim 22
Dependent Claim
91 words
A pharmaceutical composition comprising an antibacterially effective amount of a member selected from the group consisting of a 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1-N-X derivatives thereof wherein X is a substituent selected from the group consisting of ##STR9## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof; together with a non-toxic pharmaceutically acceptable carrier.
Claim 23
Dependent Claim
91 words
A pharmaceutical composition comprising an antibacterially effective amount of a member selected from the group consisting of a 5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol selected from the group consisting of 5-deoxygentamicin C 1a , 5-deoxygentamicin C 2 , the 1-N-X derivatives thereof wherein X is a substituent selected from the group consisting of ##STR9## wherein Z is aminohydroxyalkyl, said substituent Z having up to 3 carbon atoms and, when substituted by amino and hydroxy, bearing the substituents on different carbon atoms; and the pharmaceutically acceptable acid addition salts thereof; together with a non-toxic pharmaceutically acceptable carrier.
Claim 24
Dependent Claim
15 words
A compound of claim 14 which is a 1-N-X-4-O-aminoglycosyl-6-O-garosaminyl-2,5-dideoxystreptamine wherein X is 3-amino-2-hydroxypropionyl or 4-amino-2-hydroxybutyryl.
Claim 25
Dependent Claim
24 words
A compound according to claim 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 each represent hydrogen.
Claim 26
Dependent Claim
35 words
A compound according to claim 1 where R 3 and R 5 each represent hydrogen and R 1 represents an ω-amino-α-hydroxy-lower-alkanoyl group having the formula: H.sub.2 NCH.sub.2 (CH.sub.2).sub.n CHOHCO-- where n is 0 or 1.
Claim 27
Dependent Claim
33 words
The method of eliciting an antibacterial response in a warm-blooded animal having a susceptible bacterial infection which comprises administering to said animal a non-toxic antibacterially effective amount of a compound of claim 1.
Claim 28
Dependent Claim
21 words
A pharmaceutical composition comprising an antibacterially effective amount of a compound of claim 1, together with a non-toxic pharmaceutically acceptable carrier.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-08-01 | 1987-01-31 | 1987-08-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-01 | 1991-01-31 | 1991-08-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-01 | 1995-01-31 | 1995-08-02 | $7700.00 | Window Closed / Lapsed |