SU965359A3 - Способ получени 1N-( @ -окси- @ -аминоалканоил)-6N-метил-3,4-дидеоксиканамицина В - Google Patents
Способ получени 1N-( @ -окси- @ -аминоалканоил)-6N-метил-3,4-дидеоксиканамицина В Download PDFInfo
- Publication number
- SU965359A3 SU965359A3 SU752180255A SU2180255A SU965359A3 SU 965359 A3 SU965359 A3 SU 965359A3 SU 752180255 A SU752180255 A SU 752180255A SU 2180255 A SU2180255 A SU 2180255A SU 965359 A3 SU965359 A3 SU 965359A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- amino
- formula
- solution
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 7
- 229930027917 kanamycin Natural products 0.000 abstract description 7
- 229960000318 kanamycin Drugs 0.000 abstract description 7
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound 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 abstract description 7
- 229930182823 kanamycin A Natural products 0.000 abstract description 7
- 238000005917 acylation reaction Methods 0.000 abstract description 6
- 230000010933 acylation Effects 0.000 abstract description 4
- 241000894006 Bacteria Species 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 5
- 125000006239 protecting group Chemical group 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 241000192125 Firmicutes Species 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 14
- -1 L-isoseryl Chemical group 0.000 description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 5
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- SKKLOUVUUNMCJE-FQSMHNGLSA-N kanamycin B Chemical class N[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 SKKLOUVUUNMCJE-FQSMHNGLSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960001192 bekanamycin Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 229930182824 kanamycin B Natural products 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- AKIMZZDYSCXKGF-UHFFFAOYSA-N butan-1-ol;chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl.CCCCO AKIMZZDYSCXKGF-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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
- C07H15/226—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Physical Vapour Deposition (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49115199A JPS5148634A (en) | 1974-10-08 | 1974-10-08 | Taiseikinnyukona 11nn * arufua hidorokishi omega aminoashiru * 6**nn mechiru 3* *hh jideokishikanamaishin b no seizoho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU965359A3 true SU965359A3 (ru) | 1982-10-07 |
Family
ID=14656799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752180255A SU965359A3 (ru) | 1974-10-08 | 1975-10-08 | Способ получени 1N-( @ -окси- @ -аминоалканоил)-6N-метил-3,4-дидеоксиканамицина В |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5148634A (xx) |
| BE (1) | BE834236A (xx) |
| CA (1) | CA1050537A (xx) |
| CH (1) | CH615685A5 (xx) |
| DE (1) | DE2543535C3 (xx) |
| DK (1) | DK148262C (xx) |
| FR (1) | FR2287233A1 (xx) |
| GB (1) | GB1475481A (xx) |
| HU (1) | HU173702B (xx) |
| IE (1) | IE42354B1 (xx) |
| LU (1) | LU73533A1 (xx) |
| NL (1) | NL181503C (xx) |
| SE (1) | SE431216B (xx) |
| SU (1) | SU965359A3 (xx) |
| YU (1) | YU39659B (xx) |
| ZA (1) | ZA756291B (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2458931C2 (ru) * | 2006-06-02 | 2012-08-20 | Мейдзи Сейка Фарма Ко., Лтд. | Новые аминогликозидные антибиотики |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175198A (en) * | 1981-04-20 | 1982-10-28 | Microbial Chem Res Found | 1-n-acyl derivative of 5,3,4-trideoxy-6-n-methylkanamycin b and their preparation |
| JPS60179468U (ja) * | 1984-05-11 | 1985-11-28 | 大成プラス株式会社 | 多色スタンプ |
| DE102006004062A1 (de) | 2006-01-28 | 2007-08-09 | Degussa Gmbh | Kautschukmischungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001208A (en) * | 1972-10-06 | 1977-01-04 | Zaidan Hojin Biseibutsu Kagaku Kenkyo Kai | 1-N-[(S)-α-hydroxy-ω-aminoacyl] |
-
1974
- 1974-10-08 JP JP49115199A patent/JPS5148634A/ja active Granted
-
1975
- 1975-09-16 GB GB3806475A patent/GB1475481A/en not_active Expired
- 1975-09-17 IE IE2043/75A patent/IE42354B1/en unknown
- 1975-09-30 DE DE2543535A patent/DE2543535C3/de not_active Expired
- 1975-10-03 ZA ZA00756291A patent/ZA756291B/xx unknown
- 1975-10-03 NL NLAANVRAGE7511662,A patent/NL181503C/xx not_active IP Right Cessation
- 1975-10-06 LU LU73533A patent/LU73533A1/xx unknown
- 1975-10-06 BE BE160728A patent/BE834236A/xx not_active IP Right Cessation
- 1975-10-07 HU HU75BI525A patent/HU173702B/hu not_active IP Right Cessation
- 1975-10-07 CH CH1303375A patent/CH615685A5/de not_active IP Right Cessation
- 1975-10-07 YU YU2530/75A patent/YU39659B/xx unknown
- 1975-10-07 CA CA237,157A patent/CA1050537A/en not_active Expired
- 1975-10-07 FR FR7531209A patent/FR2287233A1/fr active Granted
- 1975-10-07 SE SE7511229A patent/SE431216B/xx not_active IP Right Cessation
- 1975-10-07 DK DK451475A patent/DK148262C/da not_active IP Right Cessation
- 1975-10-08 SU SU752180255A patent/SU965359A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2458931C2 (ru) * | 2006-06-02 | 2012-08-20 | Мейдзи Сейка Фарма Ко., Лтд. | Новые аминогликозидные антибиотики |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5653558B2 (xx) | 1981-12-19 |
| YU39659B (en) | 1985-03-20 |
| DE2543535C3 (de) | 1978-06-01 |
| DE2543535B2 (de) | 1977-10-13 |
| ZA756291B (en) | 1976-06-30 |
| GB1475481A (en) | 1977-06-01 |
| SE431216B (sv) | 1984-01-23 |
| IE42354B1 (en) | 1980-07-30 |
| NL181503B (nl) | 1987-04-01 |
| NL181503C (nl) | 1987-09-01 |
| FR2287233B1 (xx) | 1978-11-10 |
| HU173702B (hu) | 1979-07-28 |
| IE42354L (en) | 1976-04-08 |
| CA1050537A (en) | 1979-03-13 |
| DK451475A (da) | 1976-04-09 |
| BE834236A (fr) | 1976-04-06 |
| FR2287233A1 (fr) | 1976-05-07 |
| DK148262B (da) | 1985-05-20 |
| AU8518975A (en) | 1977-03-31 |
| DE2543535A1 (de) | 1976-04-22 |
| CH615685A5 (en) | 1980-02-15 |
| DK148262C (da) | 1986-02-10 |
| NL7511662A (nl) | 1976-04-12 |
| SE7511229L (sv) | 1976-04-09 |
| JPS5148634A (en) | 1976-04-26 |
| LU73533A1 (xx) | 1976-08-19 |
| YU253075A (en) | 1982-05-31 |
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