IE40796B1 - Derivatives of diaminocyclitols and methods for their preparation - Google Patents
Derivatives of diaminocyclitols and methods for their preparationInfo
- Publication number
- IE40796B1 IE40796B1 IE115/75A IE11575A IE40796B1 IE 40796 B1 IE40796 B1 IE 40796B1 IE 115/75 A IE115/75 A IE 115/75A IE 11575 A IE11575 A IE 11575A IE 40796 B1 IE40796 B1 IE 40796B1
- Authority
- IE
- Ireland
- Prior art keywords
- gentamicin
- antibiotic
- amino
- diaminocyclitols
- aminoglycosyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 abstract 3
- DNYGXMICFMACRA-UHFFFAOYSA-N gentamicin C1A Natural products O1C(CNC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N DNYGXMICFMACRA-UHFFFAOYSA-N 0.000 abstract 2
- LKKVGKXCMYHKSL-LLZRLKDCSA-N gentamycin A Chemical compound O[C@H]1[C@H](NC)[C@@H](O)CO[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](N)C[C@H]1N LKKVGKXCMYHKSL-LLZRLKDCSA-N 0.000 abstract 2
- CEAZRRDELHUEMR-CAMVTXANSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-[(1r)-1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1[C@H]([C@@H](C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-CAMVTXANSA-N 0.000 abstract 1
- XUFIWSHGXVLULG-BSBKYKEKSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-[(1s)-1-aminoethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUFIWSHGXVLULG-BSBKYKEKSA-N 0.000 abstract 1
- BRZYSWJRSDMWLG-DJWUNRQOSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-[(1r)-1-hydroxyethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-DJWUNRQOSA-N 0.000 abstract 1
- XUSXOPRDIDWMFO-CTMSJIKGSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[[(2s,3r)-3-amino-6-[(1s)-1-aminoethyl]-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(O2)[C@H](C)N)N)[C@@H](N)C[C@H]1N XUSXOPRDIDWMFO-CTMSJIKGSA-N 0.000 abstract 1
- ABCLPPNEPBAKRL-ROQIPNNMSA-N (2r,3s,4s,5r,6s)-2-[(1r)-1-aminoethyl]-6-[(1r,2r,3s,4r,6s)-4,6-diamino-3-[(2r,3r,4r,5r)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)N)O2)O)[C@@H](N)C[C@H]1N ABCLPPNEPBAKRL-ROQIPNNMSA-N 0.000 abstract 1
- DAKDDLIZULPEFW-UHFFFAOYSA-N 2-[4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-4-(methylamino)oxane-3,5-diol Chemical compound OC1C(NC)C(O)COC1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N DAKDDLIZULPEFW-UHFFFAOYSA-N 0.000 abstract 1
- VIAXDDBFFSKHGA-UHFFFAOYSA-N Antibiotic G52 Natural products CNC1CC(N)C(OC2OCC(C)(O)C(NC)C2O)C(O)C1OC3OC(=CCC3N)CN VIAXDDBFFSKHGA-UHFFFAOYSA-N 0.000 abstract 1
- YQGZDAPJXRYYLX-ZFAMMYHGSA-N Antibiotic JI-20A Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N YQGZDAPJXRYYLX-ZFAMMYHGSA-N 0.000 abstract 1
- WYJSPPYVEJPMJA-DJWUNRQOSA-N Antibiotic JI-20B Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H]([C@@H](C)N)O2)N)[C@@H](N)C[C@H]1N WYJSPPYVEJPMJA-DJWUNRQOSA-N 0.000 abstract 1
- 229930182566 Gentamicin Natural products 0.000 abstract 1
- HFLKNINDVFJPQT-UHFFFAOYSA-N Gentamicin X2 Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(C(O)C(O)C(CO)O2)N)C(N)CC1N HFLKNINDVFJPQT-UHFFFAOYSA-N 0.000 abstract 1
- HFLKNINDVFJPQT-ZFAMMYHGSA-N Gentamicin X2 Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](N)C[C@H]1N HFLKNINDVFJPQT-ZFAMMYHGSA-N 0.000 abstract 1
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 abstract 1
- 229930192786 Sisomicin Natural products 0.000 abstract 1
- XUSXOPRDIDWMFO-UHFFFAOYSA-N Verdamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(O2)C(C)N)N)C(N)CC1N XUSXOPRDIDWMFO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- -1 antibiotic 66-40B Chemical compound 0.000 abstract 1
- ARCVBMPERJRMKB-UHFFFAOYSA-N antibiotic g-52 Chemical compound O1C(CNC)=CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N ARCVBMPERJRMKB-UHFFFAOYSA-N 0.000 abstract 1
- RHRAMPXHWHSKQB-GGEUKFTFSA-N betamicin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)O)[C@@H](N)C[C@H]1N RHRAMPXHWHSKQB-GGEUKFTFSA-N 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- CEAZRRDELHUEMR-UHFFFAOYSA-N gentamicin Chemical class O1C(C(C)NC)CCC(N)C1OC1C(O)C(OC2C(C(NC)C(C)(O)CO2)O)C(N)CC1N CEAZRRDELHUEMR-UHFFFAOYSA-N 0.000 abstract 1
- RHRAMPXHWHSKQB-UHFFFAOYSA-N gentamicin B Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(C(O)C(O)C(CN)O2)O)C(N)CC1N RHRAMPXHWHSKQB-UHFFFAOYSA-N 0.000 abstract 1
- 229930076781 gentamycin C1 Natural products 0.000 abstract 1
- VEGXETMJINRLTH-BOZYPMBZSA-N gentamycin C1a Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-BOZYPMBZSA-N 0.000 abstract 1
- XUFIWSHGXVLULG-JYDJLPLMSA-N gentamycin C2 Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)[C@@H](C)N)N)[C@@H](N)C[C@H]1N XUFIWSHGXVLULG-JYDJLPLMSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229960005456 sisomicin Drugs 0.000 abstract 1
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The 1-N-X-substituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitols gentamicin A, gentamicin B, gentamicin B1, gentamicin C1, gentamicin C1a, gentamicin C2, gentamicin C2a, gentamicin X2, sisomicin, verdamicin, antibiotic G-418, antibiotic 66-40B, antibiotic 66-40D, antibiotic JI-20A, antibiotic JI-20B and antibiotic G-52, in which X is the S-3-amino-2-hydroxypropionyl or S-4-amino-2-hydroxybutyl group, are prepared. (In the case of gentamicins C1, C1a and C2, X is restricted to S-3-amino-2-hydroxypropionyl.) Owing to the presence of the 1-N-substituent, these compounds have greater activity. The process comprises reacting a 1-N-unsubstituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitol, which may be in the form of a partially neutralised acid addition salt, with an appropriate acid in the presence of a carbodiimide or with a functional derivative of this acid. During the process it is possible for amino groups and/or the hydroxyl group, with the exception of the 1-amino group, in the starting materials to undergo intermediate protection.
[GB1494129A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45257174A | 1974-03-19 | 1974-03-19 | |
| US05/452,586 US4029882A (en) | 1974-03-19 | 1974-03-19 | Selective acylation of the C-1 amino group of aminoglycoside antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40796L IE40796L (en) | 1975-09-19 |
| IE40796B1 true IE40796B1 (en) | 1979-08-15 |
Family
ID=27036813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE115/75A IE40796B1 (en) | 1974-03-19 | 1975-01-21 | Derivatives of diaminocyclitols and methods for their preparation |
Country Status (10)
| Country | Link |
|---|---|
| AR (1) | AR207582A1 (en) |
| BG (1) | BG26400A3 (en) |
| CH (1) | CH612946A5 (en) |
| DE (1) | DE2502296C2 (en) |
| FR (1) | FR2264553B1 (en) |
| GB (1) | GB1494129A (en) |
| HK (1) | HK7681A (en) |
| IE (1) | IE40796B1 (en) |
| IL (1) | IL46467A (en) |
| MY (1) | MY8100350A (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136254A (en) * | 1976-06-17 | 1979-01-23 | Schering Corporation | Process of selectively blocking amino functions in aminoglycosides using transition metal salts and intermediates used thereby |
| DE2753769A1 (en) * | 1977-12-02 | 1979-06-13 | Bayer Ag | 1-N-4,6-DI-O- (AMINOGLYCOSYL) -1,3-DIAMINO-CYCLITOL DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE |
| DE2921973A1 (en) * | 1979-05-30 | 1980-12-11 | Bayer Ag | SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DE3101376A1 (en) * | 1981-01-17 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | SISOMICIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS |
| DK2390255T3 (en) | 2006-04-03 | 2016-11-07 | Technion Res & Dev Foundation | Novel aminoglycosides and uses thereof in the treatment of genetic disorders |
| PL2217610T3 (en) | 2007-11-21 | 2017-04-28 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| CN102481307B (en) * | 2009-05-14 | 2016-08-24 | 尔察祯有限公司 | Treatment of Klebsiella pneumoniae infection with antibacterial aminoglycoside compounds |
| WO2010132765A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132768A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of sisomicin |
| WO2010132759A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of dibekacin |
| WO2010132757A2 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010132760A1 (en) | 2009-05-15 | 2010-11-18 | Achaogen, Inc. | Antibacterial derivatives of tobramycin |
-
1975
- 1975-01-01 AR AR257371A patent/AR207582A1/en active
- 1975-01-21 IL IL46467A patent/IL46467A/en unknown
- 1975-01-21 FR FR7501799A patent/FR2264553B1/fr not_active Expired
- 1975-01-21 IE IE115/75A patent/IE40796B1/en unknown
- 1975-01-21 DE DE2502296A patent/DE2502296C2/en not_active Expired
- 1975-01-21 GB GB2653/75A patent/GB1494129A/en not_active Expired
- 1975-01-22 CH CH77275A patent/CH612946A5/en not_active IP Right Cessation
- 1975-01-24 BG BG028804A patent/BG26400A3/en unknown
-
1981
- 1981-03-12 HK HK76/81A patent/HK7681A/en unknown
- 1981-12-30 MY MY350/81A patent/MY8100350A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE40796L (en) | 1975-09-19 |
| AU7747775A (en) | 1976-07-22 |
| IL46467A0 (en) | 1975-04-25 |
| DE2502296A1 (en) | 1975-09-25 |
| DE2502296C2 (en) | 1983-09-22 |
| FR2264553B1 (en) | 1978-12-01 |
| FR2264553A1 (en) | 1975-10-17 |
| GB1494129A (en) | 1977-12-07 |
| AR207582A1 (en) | 1976-10-15 |
| CH612946A5 (en) | 1979-08-31 |
| IL46467A (en) | 1978-10-31 |
| BG26400A3 (en) | 1979-03-15 |
| HK7681A (en) | 1981-03-20 |
| MY8100350A (en) | 1981-12-31 |
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