DE2341062A1 - Neues cyclohexanpentol-derivat und verfahren zu dessen herstellung - Google Patents
Neues cyclohexanpentol-derivat und verfahren zu dessen herstellungInfo
- Publication number
- DE2341062A1 DE2341062A1 DE19732341062 DE2341062A DE2341062A1 DE 2341062 A1 DE2341062 A1 DE 2341062A1 DE 19732341062 DE19732341062 DE 19732341062 DE 2341062 A DE2341062 A DE 2341062A DE 2341062 A1 DE2341062 A1 DE 2341062A1
- Authority
- DE
- Germany
- Prior art keywords
- myo
- inositol
- azido
- deoxy
- derivative
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- RUOFFXZEQYHVHT-UHFFFAOYSA-N cyclohexane-1,1,2,2,3-pentol Chemical class OC1CCCC(O)(O)C1(O)O RUOFFXZEQYHVHT-UHFFFAOYSA-N 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 229960000367 inositol Drugs 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JXAOTICXQLILTC-WWHKVMGRSA-N (1r,2s,4r,5r)-6-aminocyclohexane-1,2,3,4,5-pentol Chemical compound NC1[C@@H](O)[C@H](O)C(O)[C@H](O)[C@@H]1O JXAOTICXQLILTC-WWHKVMGRSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- -1 alkali metal azide Chemical class 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- IMPKVMRTXBRHRB-UHFFFAOYSA-N cyclohexane-1,2,3,4,5-pentol Chemical compound OC1CC(O)C(O)C(O)C1O IMPKVMRTXBRHRB-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000003999 cyclitols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3830072A GB1382469A (en) | 1972-08-16 | 1972-08-16 | Cyclohexanepentol derivatives and process for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2341062A1 true DE2341062A1 (de) | 1974-02-28 |
Family
ID=10402556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732341062 Pending DE2341062A1 (de) | 1972-08-16 | 1973-08-14 | Neues cyclohexanpentol-derivat und verfahren zu dessen herstellung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3887590A (enExample) |
| JP (1) | JPS4985047A (enExample) |
| AR (1) | AR197250A1 (enExample) |
| AU (1) | AU5916873A (enExample) |
| BE (1) | BE803299A (enExample) |
| CH (1) | CH569701A5 (enExample) |
| DE (1) | DE2341062A1 (enExample) |
| FR (1) | FR2196324A1 (enExample) |
| GB (1) | GB1382469A (enExample) |
| NL (1) | NL7311138A (enExample) |
| OA (1) | OA04460A (enExample) |
| SU (1) | SU462331A3 (enExample) |
| ZA (1) | ZA735342B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988682A (en) * | 1989-02-03 | 1991-01-29 | University Of Pittsburgh | Myo-inositol analogs and method for their use |
| US4937390A (en) * | 1989-02-03 | 1990-06-26 | University Of Pittsburgh | Compound useful for the production of 3-deoxy-3-fluoro-myo-inositol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496196A (en) * | 1965-10-02 | 1970-02-17 | Tanabe Pharm Co Ltd | 4,6-diazido-4,6-dideoxy-myo-inositol tetraacylates |
-
1972
- 1972-08-16 GB GB3830072A patent/GB1382469A/en not_active Expired
-
1973
- 1973-07-30 US US383665A patent/US3887590A/en not_active Expired - Lifetime
- 1973-07-30 AR AR249330A patent/AR197250A1/es active
- 1973-08-02 CH CH1123873A patent/CH569701A5/xx not_active IP Right Cessation
- 1973-08-06 ZA ZA735342A patent/ZA735342B/xx unknown
- 1973-08-07 FR FR7328763A patent/FR2196324A1/fr not_active Withdrawn
- 1973-08-07 BE BE134304A patent/BE803299A/xx unknown
- 1973-08-13 AU AU59168/73A patent/AU5916873A/en not_active Expired
- 1973-08-13 NL NL7311138A patent/NL7311138A/xx unknown
- 1973-08-14 DE DE19732341062 patent/DE2341062A1/de active Pending
- 1973-08-15 SU SU1950286A patent/SU462331A3/ru active
- 1973-08-16 OA OA54987A patent/OA04460A/xx unknown
- 1973-08-16 JP JP48092328A patent/JPS4985047A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH569701A5 (enExample) | 1975-11-28 |
| GB1382469A (en) | 1975-01-29 |
| ZA735342B (en) | 1974-07-31 |
| AU5916873A (en) | 1975-02-13 |
| BE803299A (fr) | 1974-02-07 |
| OA04460A (fr) | 1980-03-15 |
| NL7311138A (enExample) | 1974-02-19 |
| AR197250A1 (es) | 1974-03-22 |
| SU462331A3 (ru) | 1975-02-28 |
| US3887590A (en) | 1975-06-03 |
| JPS4985047A (enExample) | 1974-08-15 |
| FR2196324A1 (enExample) | 1974-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2058248A1 (de) | Lacton | |
| DE2735433A1 (de) | Neue phenylnitromethanverbindungen und verfahren zu ihrer herstellung | |
| DE2341062A1 (de) | Neues cyclohexanpentol-derivat und verfahren zu dessen herstellung | |
| DE2404946C3 (de) | Verfahren zur Herstellung von 7alpha-Acylthio-Steroidspirolactonen | |
| DE2452501A1 (de) | Erythrodiolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel | |
| DE936747C (de) | Verfahren zur Herstellung von neuen Pyrimidinderivaten und deren Salzen | |
| DE957123C (de) | Verfahren zur Herstellung von Thioabkoemmlingen der Colchiceine | |
| DE2447053A1 (de) | Verfahren zur herstellung eines schwefelhaltigen pyridinderivats | |
| AT209007B (de) | Verfahren zur Herstellung von 9 α-Halogen-4-pregnen-16 α, 17 α,21-triol-3, 11, 20-trionen und ihren Estern | |
| DE1960130A1 (de) | Neue Verfahren zur Herstellung von N-(Diaethylaminoaethyl)-4-amino-5-chloro-2-methoxybenzamid | |
| DE1618820B2 (de) | Verfahren zur Herstellung von optisch aktiven 13 beta-substituierten Gonapentaenen und das 17- eckige Klammer auf (2R:3R)-Tartramylhydrazon eckige Klammer zu des 3-Methoxy-8-(14)-seco-13 beta-methyl-14,17-dioxo-gona-1,3,5( 10), 9(ll>tetraens | |
| DE1593925C (de) | Nitrosohydroxylaminopropionsäurederivate und Verfahren zu ihrer Herstellung | |
| DE825686C (de) | Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane | |
| DE749146C (de) | Verfahren zur Herstellung von ªŠ-Oxycarbonsaeuren | |
| DE962075C (de) | Verfahren zur teilweisen Entfernung von Ketogruppen aus ª‡-Diketosteroiden | |
| DE977519C (de) | Verfahren zur Herstellung von 1-Phenyl-2-dihalogenacetamino-1, 3-propandiolen | |
| AT160572B (de) | Verfahren zur Darstellung ungesättigter Oxyketone der Cyclopentanopolydrophenanthrenreihe oder deren Derivaten. | |
| DE965327C (de) | Verfahren zur Herstellung von 3-Oxy-11-ketosteroiden und deren Estern | |
| DE883897C (de) | Verfahren zur Herstellung von 17-(ª‡)-Oxy-20-ketopregnanen | |
| CH514567A (de) | Verfahren zur Herstellung von neuen (3,2-c)-Pyrazol-Verbindungen der Pregnanreihe | |
| DE870103C (de) | Verfahren zur Herstellung von Verbindungen mit Nebennierenrindenhormonwirkung | |
| AT224116B (de) | Verfahren zur Herstellung von neuen, 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen | |
| DE2236005C3 (de) | Dibenzo- eckige Klammer auf d,f eckige Klammer zu -dioxepin- eckige Klammer auf 1,3 eckige Klammer zu -derivate und deren pharmakologisch verträgliche Salze, sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE2200259C3 (de) | 1,2,3,4,6,7,12,12b-E-Octahydroindolo eckige Klammer auf 2,3a eckige Klammer zu chinolizyliden-essigsäureäthylester, Verfahren zu seiner Herstellung und seine Verwendung zur Herstellung von (+-)-Ebumamonin | |
| DE1094258B (de) | Verfahren zur Herstellung von fluorierten 16-Methylsteroiden |