DE2109855C3 - l,6-Di-O-alkylsulfonyl-2,3-4,5dianhydro-idit-derivate und diese enthaltende Mittel - Google Patents
l,6-Di-O-alkylsulfonyl-2,3-4,5dianhydro-idit-derivate und diese enthaltende MittelInfo
- Publication number
- DE2109855C3 DE2109855C3 DE19712109855 DE2109855A DE2109855C3 DE 2109855 C3 DE2109855 C3 DE 2109855C3 DE 19712109855 DE19712109855 DE 19712109855 DE 2109855 A DE2109855 A DE 2109855A DE 2109855 C3 DE2109855 C3 DE 2109855C3
- Authority
- DE
- Germany
- Prior art keywords
- dideoxy
- dibromo
- acetone
- anhydrous
- melting point
- 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.)
- Expired
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- KEOBBYNROASRIK-UHFFFAOYSA-N 1,2-bis(2-bromo-1-hydroxyethyl)-3,3-dimethylcyclopropane-1,2-diol Chemical compound CC1(C)C(O)(C(O)CBr)C1(O)C(O)CBr KEOBBYNROASRIK-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- NGDDCFINDCHPTF-UHFFFAOYSA-N [Br].[Ag] Chemical compound [Br].[Ag] NGDDCFINDCHPTF-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 231100000053 low toxicity Toxicity 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- LJDVQYVDNYHZAV-UHFFFAOYSA-N ethanesulfonic acid;silver Chemical compound [Ag].CCS(O)(=O)=O LJDVQYVDNYHZAV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001128 | 1970-03-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2109855A1 DE2109855A1 (de) | 1971-12-09 |
| DE2109855B2 DE2109855B2 (de) | 1973-03-22 |
| DE2109855C3 true DE2109855C3 (de) | 1973-10-18 |
Family
ID=10996679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712109855 Expired DE2109855C3 (de) | 1970-03-02 | 1971-03-02 | l,6-Di-O-alkylsulfonyl-2,3-4,5dianhydro-idit-derivate und diese enthaltende Mittel |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS549176B1 (Direct) |
| AT (1) | AT304581B (Direct) |
| CH (1) | CH557343A (Direct) |
| DE (1) | DE2109855C3 (Direct) |
| DK (1) | DK132949C (Direct) |
| NL (1) | NL7102507A (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012067248A1 (ja) * | 2010-11-19 | 2012-05-24 | 三菱化学株式会社 | ４－アルキニル－１，３－ジオキソラン－２－オン誘導体の製造法 |
-
1971
- 1971-02-23 AT AT155671A patent/AT304581B/de not_active IP Right Cessation
- 1971-02-25 NL NL7102507A patent/NL7102507A/xx unknown
- 1971-02-26 CH CH281571A patent/CH557343A/xx not_active IP Right Cessation
- 1971-03-01 DK DK93771A patent/DK132949C/da active
- 1971-03-02 DE DE19712109855 patent/DE2109855C3/de not_active Expired
- 1971-03-02 JP JP1091371A patent/JPS549176B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK132949C (da) | 1976-07-26 |
| CH557343A (de) | 1974-12-31 |
| NL7102507A (Direct) | 1971-09-06 |
| AT304581B (de) | 1973-01-10 |
| DE2109855B2 (de) | 1973-03-22 |
| DK132949B (da) | 1976-03-01 |
| DE2109855A1 (de) | 1971-12-09 |
| JPS549176B1 (Direct) | 1979-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |