DE3012131A1 - Verfahren zur herstellung von 3-o-demethylfortimicinen - Google Patents
Verfahren zur herstellung von 3-o-demethylfortimicinenInfo
- Publication number
- DE3012131A1 DE3012131A1 DE19803012131 DE3012131A DE3012131A1 DE 3012131 A1 DE3012131 A1 DE 3012131A1 DE 19803012131 DE19803012131 DE 19803012131 DE 3012131 A DE3012131 A DE 3012131A DE 3012131 A1 DE3012131 A1 DE 3012131A1
- Authority
- DE
- Germany
- Prior art keywords
- boron
- fortimicin
- free base
- antibiotic
- demethylfortimicin
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- BIDUPMYXGFNAEJ-APGVDKLISA-N astromicin Chemical compound O[C@@H]1[C@H](N(C)C(=O)CN)[C@@H](OC)[C@@H](O)[C@H](N)[C@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 BIDUPMYXGFNAEJ-APGVDKLISA-N 0.000 claims description 17
- 229910052796 boron Inorganic materials 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 229930195503 Fortimicin Natural products 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- BIDUPMYXGFNAEJ-UHFFFAOYSA-N Fortimicin A Natural products OC1C(N(C)C(=O)CN)C(OC)C(O)C(N)C1OC1C(N)CCC(C(C)N)O1 BIDUPMYXGFNAEJ-UHFFFAOYSA-N 0.000 claims description 9
- WFMQYKIRAVMXSU-LCVFDZPESA-N Fortimicin B Chemical compound N[C@H]1[C@H](O)[C@H](OC)[C@@H](NC)[C@@H](O)[C@@H]1O[C@@H]1[C@H](N)CC[C@@H]([C@H](C)N)O1 WFMQYKIRAVMXSU-LCVFDZPESA-N 0.000 claims description 7
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 229940088710 antibiotic agent Drugs 0.000 claims description 7
- WFMQYKIRAVMXSU-UHFFFAOYSA-N Fortimicin AE Natural products NC1C(O)C(OC)C(NC)C(O)C1OC1C(N)CCC(C(C)N)O1 WFMQYKIRAVMXSU-UHFFFAOYSA-N 0.000 claims description 6
- 238000010520 demethylation reaction Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 4
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 claims description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- -1 methylene chloride Chemical class 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- KBIFQFMZFNTDKE-KSOXEKJASA-N (1S,2R,3R,4R,5R,6S)-6-amino-5-[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-3-(methylamino)cyclohexane-1,2,4-triol Chemical compound CN[C@@H]1[C@@H](O)[C@@H](O)[C@H](N)[C@@H](O[C@H]2O[C@@H](CC[C@H]2N)C(C)N)[C@@H]1O KBIFQFMZFNTDKE-KSOXEKJASA-N 0.000 description 1
- OWTJVZIKRRJXGS-MAEXYVIMSA-N 2-amino-N-[(1R,2R,3R,4S,5S,6R)-4-amino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]-N-methylacetamide Chemical compound C[C@H](N)[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[C@@H](N)[C@H](O)[C@H](O)[C@H]([C@H]2O)N(C)C(=O)CN)O1 OWTJVZIKRRJXGS-MAEXYVIMSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 102100033070 Histone acetyltransferase KAT6B Human genes 0.000 description 1
- 101100019690 Homo sapiens KAT6B gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000187708 Micromonospora Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical class O[C@@H]1[C@@H](O)[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 SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940041022 streptomycins Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 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
- C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/025,238 US4230848A (en) | 1979-03-29 | 1979-03-29 | Process for producing 3-O-demethylfortimicins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3012131A1 true DE3012131A1 (de) | 1980-10-09 |
Family
ID=21824862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803012131 Withdrawn DE3012131A1 (de) | 1979-03-29 | 1980-03-28 | Verfahren zur herstellung von 3-o-demethylfortimicinen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4230848A (enExample) |
| JP (1) | JPS55167295A (enExample) |
| AR (1) | AR228254A1 (enExample) |
| AU (1) | AU533114B2 (enExample) |
| BE (1) | BE882508A (enExample) |
| CA (1) | CA1134374A (enExample) |
| DE (1) | DE3012131A1 (enExample) |
| ES (1) | ES8104319A1 (enExample) |
| FR (1) | FR2452496A1 (enExample) |
| GB (1) | GB2045247B (enExample) |
| GR (1) | GR67744B (enExample) |
| IT (1) | IT1140788B (enExample) |
| PH (1) | PH16157A (enExample) |
| SE (1) | SE8002295L (enExample) |
| ZA (1) | ZA801397B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427662A (en) * | 1982-04-09 | 1984-01-24 | Abbott Laboratories | 3-Amino-3-demethoxyfortimicins, pharmaceutical compositions thereof and method of use |
| AU1937583A (en) * | 1982-10-08 | 1984-04-12 | Abbott Laboratories | O-demethylation of aminoglycosides |
| US8628434B2 (en) * | 2007-12-19 | 2014-01-14 | Taylor Made Golf Company, Inc. | Golf club face with cover having roughness pattern |
| US9174099B2 (en) | 2007-12-19 | 2015-11-03 | Taylor Made Golf Company, Inc. | Golf club face |
| US20090163289A1 (en) * | 2007-12-19 | 2009-06-25 | Taylor Made Golf Company, Inc. | Method of creating scorelines in club face insert |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124756A (en) * | 1976-12-27 | 1978-11-07 | Abbott Laboratories | 3-DE-O-Methylfortimicins |
-
1979
- 1979-03-29 US US06/025,238 patent/US4230848A/en not_active Expired - Lifetime
-
1980
- 1980-03-03 CA CA000346819A patent/CA1134374A/en not_active Expired
- 1980-03-07 AU AU56281/80A patent/AU533114B2/en not_active Ceased
- 1980-03-10 ZA ZA00801397A patent/ZA801397B/xx unknown
- 1980-03-11 GB GB8008092A patent/GB2045247B/en not_active Expired
- 1980-03-11 PH PH23748A patent/PH16157A/en unknown
- 1980-03-25 SE SE8002295A patent/SE8002295L/xx not_active Application Discontinuation
- 1980-03-26 JP JP3763980A patent/JPS55167295A/ja active Pending
- 1980-03-27 FR FR8006887A patent/FR2452496A1/fr active Granted
- 1980-03-27 ES ES490013A patent/ES8104319A1/es not_active Expired
- 1980-03-27 GR GR61537A patent/GR67744B/el unknown
- 1980-03-28 AR AR280486A patent/AR228254A1/es active
- 1980-03-28 IT IT21036/80A patent/IT1140788B/it active
- 1980-03-28 BE BE0/200014A patent/BE882508A/fr not_active IP Right Cessation
- 1980-03-28 DE DE19803012131 patent/DE3012131A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PH16157A (en) | 1983-07-18 |
| ZA801397B (en) | 1981-03-25 |
| AU5628180A (en) | 1980-10-02 |
| IT1140788B (it) | 1986-10-10 |
| BE882508A (fr) | 1980-09-29 |
| IT8021036A0 (it) | 1980-03-28 |
| GR67744B (enExample) | 1981-09-16 |
| AU533114B2 (en) | 1983-11-03 |
| JPS55167295A (en) | 1980-12-26 |
| US4230848A (en) | 1980-10-28 |
| ES490013A0 (es) | 1981-04-01 |
| FR2452496B1 (enExample) | 1983-04-01 |
| AR228254A1 (es) | 1983-02-15 |
| ES8104319A1 (es) | 1981-04-01 |
| GB2045247A (en) | 1980-10-29 |
| CA1134374A (en) | 1982-10-26 |
| FR2452496A1 (fr) | 1980-10-24 |
| SE8002295L (sv) | 1980-09-30 |
| GB2045247B (en) | 1983-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |