CH387018A - Verfahren zur Herstellung der Stereoisomeren und des Racemats von Butan-1,2,3,4-tetrol-1,4-di-(methansulfonat) - Google Patents
Verfahren zur Herstellung der Stereoisomeren und des Racemats von Butan-1,2,3,4-tetrol-1,4-di-(methansulfonat)Info
- Publication number
- CH387018A CH387018A CH203261A CH203261A CH387018A CH 387018 A CH387018 A CH 387018A CH 203261 A CH203261 A CH 203261A CH 203261 A CH203261 A CH 203261A CH 387018 A CH387018 A CH 387018A
- Authority
- CH
- Switzerland
- Prior art keywords
- methanesulfonate
- racemate
- stereoisomers
- diol
- tetrol
- Prior art date
Links
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 10
- XOWDQAHYPSENAC-UHFFFAOYSA-N 1,4-dibromobutane-2,3-diol Chemical compound BrCC(O)C(O)CBr XOWDQAHYPSENAC-UHFFFAOYSA-N 0.000 claims description 5
- MRDIDHLFTJNRDW-UHFFFAOYSA-N 1,4-diiodobutane-2,3-diol Chemical compound ICC(O)C(O)CI MRDIDHLFTJNRDW-UHFFFAOYSA-N 0.000 claims description 4
- SAUBRJOIKMVSRU-UHFFFAOYSA-N 1,4-dichlorobutane-2,3-diol Chemical compound ClCC(O)C(O)CCl SAUBRJOIKMVSRU-UHFFFAOYSA-N 0.000 claims description 3
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- YCPOZVAOBBQLRI-PHDIDXHHSA-N [(2r,3r)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)[C@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-PHDIDXHHSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YCPOZVAOBBQLRI-UHFFFAOYSA-N treosulfan Chemical compound CS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O YCPOZVAOBBQLRI-UHFFFAOYSA-N 0.000 description 2
- XOWDQAHYPSENAC-SYPWQXSBSA-N (3S)-1,4-dibromobutane-2,3-diol Chemical compound BrC[C@H](C(CBr)O)O XOWDQAHYPSENAC-SYPWQXSBSA-N 0.000 description 1
- YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 description 1
- NDEIPVVSKGHSTL-UHFFFAOYSA-N butane-1,1,1,2-tetrol Chemical class CCC(O)C(O)(O)O NDEIPVVSKGHSTL-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- ZFIVKAOQEXOYFY-ZXZARUISSA-N meso-diepoxybutane Chemical compound C1O[C@H]1[C@H]1OC1 ZFIVKAOQEXOYFY-ZXZARUISSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6204/60A GB896052A (en) | 1960-02-22 | 1960-02-22 | The stereo-isomers and the racemate of butane-1,2,3,4-tetrol-1,4-di-(methanesulphonate) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH387018A true CH387018A (de) | 1965-01-31 |
Family
ID=9810315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203261A CH387018A (de) | 1960-02-22 | 1961-02-21 | Verfahren zur Herstellung der Stereoisomeren und des Racemats von Butan-1,2,3,4-tetrol-1,4-di-(methansulfonat) |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE600502A (fr) |
| CH (1) | CH387018A (fr) |
| ES (1) | ES264880A1 (fr) |
| FR (1) | FR1135M (fr) |
| GB (1) | GB896052A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7431815B2 (ja) * | 2018-09-26 | 2024-02-15 | メダック ゲゼルシャフト フィア クリニッシェ スペツィアルプレパラーテ ミット ベシュレンクタ ハフトゥンク | トレオスルファンの結晶形 |
| US12178914B2 (en) | 2018-09-26 | 2024-12-31 | Medac Gesellschaft für klinische Spezialpräparate mbH | Lyophilisate of treosulfan |
-
1960
- 1960-02-22 GB GB6204/60A patent/GB896052A/en not_active Expired
-
1961
- 1961-02-14 ES ES264880A patent/ES264880A1/es not_active Expired
- 1961-02-21 CH CH203261A patent/CH387018A/de unknown
- 1961-02-22 BE BE600502A patent/BE600502A/fr unknown
- 1961-05-13 FR FR861694A patent/FR1135M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE600502A (fr) | 1961-06-16 |
| ES264880A1 (es) | 1961-06-16 |
| GB896052A (en) | 1962-05-09 |
| FR1135M (fr) | 1962-02-19 |
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