CA1112660A - 1,6-dimesyl-3,4-dimethyl-d-mannitol and a process for the preparation thereof - Google Patents
1,6-dimesyl-3,4-dimethyl-d-mannitol and a process for the preparation thereofInfo
- Publication number
- CA1112660A CA1112660A CA326,848A CA326848A CA1112660A CA 1112660 A CA1112660 A CA 1112660A CA 326848 A CA326848 A CA 326848A CA 1112660 A CA1112660 A CA 1112660A
- Authority
- CA
- Canada
- Prior art keywords
- mannitol
- dimethyl
- dimesyl
- iii
- formula
- 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
- OHPIJHNCKQFIGN-YPRZEIDWSA-N (2s,3r,4r,5s)-3,4-dimethyl-1,6-bis(methylsulfonyl)hexane-1,2,3,4,5,6-hexol Chemical compound CS(=O)(=O)C(O)[C@@H](O)[C@](O)(C)[C@](C)(O)[C@H](O)C(O)S(C)(=O)=O OHPIJHNCKQFIGN-YPRZEIDWSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract 3
- 230000010933 acylation Effects 0.000 claims abstract 2
- 238000005917 acylation reaction Methods 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 238000003328 mesylation reaction Methods 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KKOBWNQHGWMYBG-WCTZXXKLSA-N (2r,3r,4r,5r)-3,4-dimethylhexane-1,2,3,4,5,6-hexol Chemical compound OC[C@@H](O)[C@](O)(C)[C@](C)(O)[C@H](O)CO KKOBWNQHGWMYBG-WCTZXXKLSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 11
- 238000007912 intraperitoneal administration Methods 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 5
- VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 3
- 206010039491 Sarcoma Diseases 0.000 description 3
- ODOISJJCWUVNDJ-WCTZXXKLSA-N [(2r,3r,4r,5r)-2,3,4,5-tetrahydroxy-6-methylsulfonyloxyhexyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COS(C)(=O)=O ODOISJJCWUVNDJ-WCTZXXKLSA-N 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- DYUUGILMVYJEHY-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-4,4,5,5-tetramethyl-3-oxido-2-phenylimidazol-3-ium Chemical compound CC1(C)C(C)(C)N([O])C(C=2C=CC=CC=2)=[N+]1[O-] DYUUGILMVYJEHY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001503951 Phoma Species 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- -1 di-O Chemical class 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229960005485 mitobronitol Drugs 0.000 description 1
- 229950010913 mitolactol Drugs 0.000 description 1
- 210000003914 myeloid leukocyte Anatomy 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78GO1402A HU175923B (en) | 1978-05-03 | 1978-05-03 | Process for preparing 1,6-di-o-methanesulphonyl-3,4-di-o-methyl-d-mannitol |
| HUGO-1402 | 1978-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112660A true CA1112660A (en) | 1981-11-17 |
Family
ID=10996856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA326,848A Expired CA1112660A (en) | 1978-05-03 | 1979-05-03 | 1,6-dimesyl-3,4-dimethyl-d-mannitol and a process for the preparation thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4235803A (en, 2012) |
| JP (1) | JPS5522661A (en, 2012) |
| AT (1) | AT361010B (en, 2012) |
| CA (1) | CA1112660A (en, 2012) |
| DE (1) | DE2917890A1 (en, 2012) |
| DK (1) | DK147069C (en, 2012) |
| FR (1) | FR2424928A1 (en, 2012) |
| GB (1) | GB2021570B (en, 2012) |
| HU (1) | HU175923B (en, 2012) |
| IL (1) | IL57196A (en, 2012) |
| IT (1) | IT1163674B (en, 2012) |
| NL (1) | NL7903475A (en, 2012) |
| SE (1) | SE435497B (en, 2012) |
| SU (1) | SU902663A3 (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5713719U (en, 2012) * | 1980-06-30 | 1982-01-23 | ||
| JPS6037582U (ja) * | 1983-08-24 | 1985-03-15 | 鮫島 康斎 | フレ−ム |
| JP3108511B2 (ja) * | 1992-02-27 | 2000-11-13 | 三菱レイヨン株式会社 | 不飽和アルデヒド及び不飽和カルボン酸合成用触媒の製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB891466A (en) * | 1958-04-24 | 1962-03-14 | Nat Res Dev | New methane sulphonic acid esters of polyols |
| CH381666A (de) * | 1958-04-24 | 1964-09-15 | Nat Res Dev | Verfahren zur Herstellung von Derivaten von polyhydrischen Alkoholen |
| GB945990A (en) * | 1962-01-29 | 1964-01-08 | Chinoin Gyogyszer Es Vegyeszet | Hexitol alkylsulphonic acid esters |
-
1978
- 1978-05-03 HU HU78GO1402A patent/HU175923B/hu unknown
-
1979
- 1979-04-26 US US06/033,492 patent/US4235803A/en not_active Expired - Lifetime
- 1979-05-01 IL IL57196A patent/IL57196A/xx unknown
- 1979-05-01 GB GB7915194A patent/GB2021570B/en not_active Expired
- 1979-05-02 SE SE7903828A patent/SE435497B/sv not_active IP Right Cessation
- 1979-05-02 DK DK180679A patent/DK147069C/da not_active IP Right Cessation
- 1979-05-02 FR FR7910985A patent/FR2424928A1/fr active Granted
- 1979-05-03 NL NL7903475A patent/NL7903475A/xx not_active Application Discontinuation
- 1979-05-03 IT IT22320/79A patent/IT1163674B/it active
- 1979-05-03 DE DE19792917890 patent/DE2917890A1/de active Granted
- 1979-05-03 SU SU762764296A patent/SU902663A3/ru active
- 1979-05-03 CA CA326,848A patent/CA1112660A/en not_active Expired
- 1979-05-03 AT AT330579A patent/AT361010B/de not_active IP Right Cessation
- 1979-05-04 JP JP5520079A patent/JPS5522661A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| HU175923B (en) | 1980-11-28 |
| NL7903475A (nl) | 1979-11-06 |
| DE2917890A1 (de) | 1979-11-15 |
| IL57196A0 (en) | 1979-09-30 |
| JPS5522661A (en) | 1980-02-18 |
| GB2021570A (en) | 1979-12-05 |
| GB2021570B (en) | 1982-06-23 |
| FR2424928A1 (fr) | 1979-11-30 |
| IT1163674B (it) | 1987-04-08 |
| FR2424928B1 (en, 2012) | 1982-08-20 |
| SE435497B (sv) | 1984-10-01 |
| US4235803A (en) | 1980-11-25 |
| SU902663A3 (ru) | 1982-01-30 |
| AT361010B (de) | 1981-02-10 |
| ATA330579A (de) | 1980-07-15 |
| DK180679A (da) | 1979-11-04 |
| DK147069B (da) | 1984-04-02 |
| SE7903828L (sv) | 1979-11-04 |
| DK147069C (da) | 1984-09-10 |
| IT7922320A0 (it) | 1979-05-03 |
| JPS576423B2 (en, 2012) | 1982-02-04 |
| DE2917890C2 (en, 2012) | 1987-10-29 |
| IL57196A (en) | 1982-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |