FR2305190A1 - NEW ANTI-BACTERIAL MEDICINAL PRODUCTS BASED ON PSEUDOTRISACCHARIDES AND THEIR PROCESS FOR OBTAINING THEIR - Google Patents
NEW ANTI-BACTERIAL MEDICINAL PRODUCTS BASED ON PSEUDOTRISACCHARIDES AND THEIR PROCESS FOR OBTAINING THEIRInfo
- Publication number
- FR2305190A1 FR2305190A1 FR7613947A FR7613947A FR2305190A1 FR 2305190 A1 FR2305190 A1 FR 2305190A1 FR 7613947 A FR7613947 A FR 7613947A FR 7613947 A FR7613947 A FR 7613947A FR 2305190 A1 FR2305190 A1 FR 2305190A1
- Authority
- FR
- France
- Prior art keywords
- amino
- coz
- alkyl
- pseudotrisaccharides
- bacterial
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 229940088710 antibiotic agent Drugs 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
- 229960000707 tobramycin Drugs 0.000 abstract 2
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 abstract 2
- 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
- 241000282326 Felis catus Species 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
- 206010039438 Salmonella Infections Diseases 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
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000398 anti-amebic effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 229940036589 antiprotozoals Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 208000004396 mastitis Diseases 0.000 abstract 1
- ZBGPYVZLYBDXKO-HILBYHGXSA-N netilmycin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@]([C@H](NC)[C@@H](O)CO1)(C)O)NCC)[C@H]1OC(CN)=CC[C@H]1N ZBGPYVZLYBDXKO-HILBYHGXSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 206010039447 salmonellosis Diseases 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
- 125000003944 tolyl group Chemical group 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
- C07H15/236—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 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
derivs. (I) of gentamicin A, B1, C1, C1a, C2a, C2b, sisomicin; verdamicin; tobramycin; antibiotics G-418, 66-40b, 66-4OD, J1-20A, J1-20B, G-52; mutamicins 1,2,4,5 or 6, substd. on the 1-N atom by CH2X or COZ (where X = H, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkyl aminoalkyl, aminohydroxyalkyl, N-alkyl aminohydroxyalkyl, phenyl, benzyl or tolyl; aliphatic gps. have is not >7C and hydroxy and amino when both present are on separate C atoms; Z = X, provided that COZ is other than 5-3-amino-2-hydroxypropionyl, S-4-amino-2-hydroxybutyryl or (only for tobramycin) S-5-amino-2-hydroxyvaleryl) and their acid addn. salts are broad-spectrum antibacterials active against some strains resistant to the parent 1-amino cpds.; some are also antiprotozoals, antiamoebics and anthelmintics. They are be used therapeutically in human or veterinary medicine (e.g. 1-N-ethylsisomicin and 1-N-ethylverdamicin are useful for controlling mastitis, and Salmonella infections in cats) or as surface disinfectants. (I; COZ) are intermediates for (I; CH2X).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38575173A | 1973-08-06 | 1973-08-06 | |
| US45260074A | 1974-03-19 | 1974-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2305190A1 true FR2305190A1 (en) | 1976-10-22 |
| FR2305190B1 FR2305190B1 (en) | 1980-12-05 |
Family
ID=27011126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7613947A Granted FR2305190A1 (en) | 1973-08-06 | 1976-05-10 | NEW ANTI-BACTERIAL MEDICINAL PRODUCTS BASED ON PSEUDOTRISACCHARIDES AND THEIR PROCESS FOR OBTAINING THEIR |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK150202C (en) |
| FR (1) | FR2305190A1 (en) |
| SE (1) | SE444172B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2391222A1 (en) * | 1977-05-19 | 1978-12-15 | Kyowa Hakko Kogyo Kk | NEW ANTIBIOTICS XK-62-3 AND XK-62-4 AND THEIR MANUFACTURING METHODS BY FERMENTATION OF MICROORGANISMS OF THE GENUS MICROMONOSPORA |
| EP0021215A1 (en) * | 1979-06-19 | 1981-01-07 | Bayer Ag | Pseudotrisaccharides, their preparation and use as medicaments |
-
1976
- 1976-05-10 FR FR7613947A patent/FR2305190A1/en active Granted
-
1978
- 1978-05-17 SE SE7805684A patent/SE444172B/en not_active IP Right Cessation
-
1979
- 1979-02-08 DK DK052779A patent/DK150202C/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2391222A1 (en) * | 1977-05-19 | 1978-12-15 | Kyowa Hakko Kogyo Kk | NEW ANTIBIOTICS XK-62-3 AND XK-62-4 AND THEIR MANUFACTURING METHODS BY FERMENTATION OF MICROORGANISMS OF THE GENUS MICROMONOSPORA |
| EP0021215A1 (en) * | 1979-06-19 | 1981-01-07 | Bayer Ag | Pseudotrisaccharides, their preparation and use as medicaments |
| US4393051A (en) * | 1979-06-19 | 1983-07-12 | Bayer Aktiengesellschaft | 1-N(Aminopolyhydroxyalkyl)aminoglycoside antibiotics and method of use |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7805684L (en) | 1978-05-17 |
| DK150202B (en) | 1987-01-05 |
| DK52779A (en) | 1979-02-08 |
| SE444172B (en) | 1986-03-24 |
| DK150202C (en) | 1987-06-22 |
| FR2305190B1 (en) | 1980-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse | ||
| RC | Opposition against decision of lapse | ||
| DA | Annulment of decision of lapse | ||
| CD | Change of name or company name | ||
| CC | Supplementary protection certificate (spc) laid open to the public (law of 25 june 1990) |
Free format text: 92C0253, 920521 |
|
| CB | Supplementary protection certificate (spc) granted (law of 25 june 1990) |
Free format text: 92C0253, 740801 |
|
| CL | Concession to grant licences |