ZA200204872B - Novel process for the preparation of alpha-(2-4-disulfophenyl)-N-tert-butylnitrone and pharmaceutically acceptable salts thereof. - Google Patents
Novel process for the preparation of alpha-(2-4-disulfophenyl)-N-tert-butylnitrone and pharmaceutically acceptable salts thereof. Download PDFInfo
- Publication number
- ZA200204872B ZA200204872B ZA200204872A ZA200204872A ZA200204872B ZA 200204872 B ZA200204872 B ZA 200204872B ZA 200204872 A ZA200204872 A ZA 200204872A ZA 200204872 A ZA200204872 A ZA 200204872A ZA 200204872 B ZA200204872 B ZA 200204872B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- tert
- reaction
- butylnitrone
- disulfophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 150000003839 salts Chemical class 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000002425 crystallisation Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 239000007810 chemical reaction solvent Substances 0.000 claims description 7
- QGYZLVSWEOXOFT-UHFFFAOYSA-N tert-butyl(hydroxy)azanium;acetate Chemical compound CC(O)=O.CC(C)(C)NO QGYZLVSWEOXOFT-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- UUKHCUPMVISNFW-UHFFFAOYSA-L disodium;4-formylbenzene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=C(C=O)C(S([O-])(=O)=O)=C1 UUKHCUPMVISNFW-UHFFFAOYSA-L 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000004684 trihydrates Chemical class 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- MMMVJDFEFZDIIM-UHFFFAOYSA-N 2-$l^{1}-azanyl-2-methylpropane Chemical compound CC(C)(C)[N] MMMVJDFEFZDIIM-UHFFFAOYSA-N 0.000 description 1
- -1 2-Sulfophenyl Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010254 Concussion Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- JDFDZCXWNASUQH-UHFFFAOYSA-N acetic acid;n-butylhydroxylamine Chemical compound CC(O)=O.CCCCNO JDFDZCXWNASUQH-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XWESXZZECGOXDQ-UHFFFAOYSA-N n-tert-butylhydroxylamine Chemical compound CC(C)(C)NO XWESXZZECGOXDQ-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ADPUQRRLAAPXGT-UHFFFAOYSA-M sodium;2-formylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1C=O ADPUQRRLAAPXGT-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/46—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0000055A SE0000055D0 (sv) | 2000-01-10 | 2000-01-10 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200204872B true ZA200204872B (en) | 2003-10-07 |
Family
ID=20278055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204872A ZA200204872B (en) | 2000-01-10 | 2002-06-18 | Novel process for the preparation of alpha-(2-4-disulfophenyl)-N-tert-butylnitrone and pharmaceutically acceptable salts thereof. |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6479697B2 (sv) |
| EP (1) | EP1265856B1 (sv) |
| JP (1) | JP3748821B2 (sv) |
| KR (1) | KR100687167B1 (sv) |
| CN (1) | CN1198798C (sv) |
| AR (1) | AR029431A1 (sv) |
| AT (1) | ATE263753T1 (sv) |
| AU (1) | AU783255B2 (sv) |
| BR (1) | BR0107483A (sv) |
| CA (1) | CA2395971A1 (sv) |
| CO (1) | CO5280203A1 (sv) |
| DE (1) | DE60102679T2 (sv) |
| DK (1) | DK1265856T3 (sv) |
| EE (1) | EE200200385A (sv) |
| ES (1) | ES2217114T3 (sv) |
| HU (1) | HU225298B1 (sv) |
| IL (2) | IL150403A0 (sv) |
| IS (1) | IS6456A (sv) |
| MX (1) | MXPA02006674A (sv) |
| MY (1) | MY122830A (sv) |
| NO (1) | NO20023316L (sv) |
| NZ (1) | NZ519828A (sv) |
| PL (1) | PL357106A1 (sv) |
| PT (1) | PT1265856E (sv) |
| RU (1) | RU2259996C2 (sv) |
| SE (1) | SE0000055D0 (sv) |
| SK (1) | SK9932002A3 (sv) |
| TR (1) | TR200401307T4 (sv) |
| TW (1) | TW572880B (sv) |
| UA (1) | UA71653C2 (sv) |
| WO (1) | WO2001051460A1 (sv) |
| ZA (1) | ZA200204872B (sv) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60320946D1 (de) | 2002-02-14 | 2008-06-26 | Willett Int Ltd | Elektromagnetventil |
| US20050059638A1 (en) * | 2003-08-04 | 2005-03-17 | Kelly Michael G. | Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders |
| US20050182060A1 (en) * | 2004-02-13 | 2005-08-18 | Kelly Michael G. | 2-Substituted and 4-substituted aryl nitrone compounds |
| US20080193783A1 (en) * | 2004-12-01 | 2008-08-14 | Toyo Boseki Kabushiki Kaisha | Polyester Resin Film and Process for Producing the Same |
| WO2006069246A2 (en) * | 2004-12-22 | 2006-06-29 | Ambrx, Inc. | Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides |
| WO2007013844A1 (en) * | 2005-07-26 | 2007-02-01 | Astrazeneca Ab | Use of 4-[(tert-butylimino)benzene-1,3-disulfonate n-oxide against nausea |
| EP2242360B1 (en) * | 2008-02-12 | 2015-04-08 | Tosk, Inc. | Doxorubicin adjuvants to reduce toxicity and methods for using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1437188A (fr) | 1964-06-17 | 1966-04-29 | Du Pont | Procédé de fabrication d'alpha-phényl-nu-méthyl nitrone |
| US5488145A (en) * | 1993-12-23 | 1996-01-30 | Oklahoma Medical Research Foundation | 2,4-disulfonyl phenyl butyl nitrone, its salts, and their use as pharmaceutical free radical traps |
| SE9802507D0 (sv) * | 1998-07-10 | 1998-07-10 | Astra Ab | Novel salts |
-
2000
- 2000-01-10 SE SE0000055A patent/SE0000055D0/sv unknown
-
2001
- 2001-01-04 DE DE60102679T patent/DE60102679T2/de not_active Expired - Fee Related
- 2001-01-04 AT AT01901619T patent/ATE263753T1/de not_active IP Right Cessation
- 2001-01-04 PT PT01901619T patent/PT1265856E/pt unknown
- 2001-01-04 US US09/806,832 patent/US6479697B2/en not_active Expired - Fee Related
- 2001-01-04 EE EEP200200385A patent/EE200200385A/xx unknown
- 2001-01-04 CA CA002395971A patent/CA2395971A1/en not_active Abandoned
- 2001-01-04 TR TR2004/01307T patent/TR200401307T4/xx unknown
- 2001-01-04 JP JP2001551842A patent/JP3748821B2/ja not_active Expired - Fee Related
- 2001-01-04 RU RU2002118320/04A patent/RU2259996C2/ru not_active IP Right Cessation
- 2001-01-04 IL IL15040301A patent/IL150403A0/xx active IP Right Grant
- 2001-01-04 KR KR1020027008862A patent/KR100687167B1/ko not_active IP Right Cessation
- 2001-01-04 DK DK01901619T patent/DK1265856T3/da active
- 2001-01-04 EP EP01901619A patent/EP1265856B1/en not_active Expired - Lifetime
- 2001-01-04 TW TW90100196A patent/TW572880B/zh not_active IP Right Cessation
- 2001-01-04 PL PL01357106A patent/PL357106A1/xx not_active IP Right Cessation
- 2001-01-04 CN CNB018035841A patent/CN1198798C/zh not_active Expired - Fee Related
- 2001-01-04 AU AU27203/01A patent/AU783255B2/en not_active Ceased
- 2001-01-04 WO PCT/SE2001/000007 patent/WO2001051460A1/en active IP Right Grant
- 2001-01-04 HU HU0204111A patent/HU225298B1/hu not_active IP Right Cessation
- 2001-01-04 SK SK993-2002A patent/SK9932002A3/sk unknown
- 2001-01-04 MX MXPA02006674A patent/MXPA02006674A/es active IP Right Grant
- 2001-01-04 NZ NZ519828A patent/NZ519828A/en unknown
- 2001-01-04 BR BR0107483-0A patent/BR0107483A/pt not_active IP Right Cessation
- 2001-01-04 ES ES01901619T patent/ES2217114T3/es not_active Expired - Lifetime
- 2001-01-05 CO CO01000729A patent/CO5280203A1/es not_active Application Discontinuation
- 2001-01-05 AR ARP010100045A patent/AR029431A1/es not_active Application Discontinuation
- 2001-01-08 MY MYPI20010054A patent/MY122830A/en unknown
- 2001-04-01 UA UA2002065094A patent/UA71653C2/uk unknown
-
2002
- 2002-06-18 ZA ZA200204872A patent/ZA200204872B/en unknown
- 2002-06-25 IL IL150403A patent/IL150403A/en not_active IP Right Cessation
- 2002-07-04 IS IS6456A patent/IS6456A/is unknown
- 2002-07-09 NO NO20023316A patent/NO20023316L/no not_active Application Discontinuation
Also Published As
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