CA2286797C - Procede de preparation de 6,7-dichloro-5-nitro-2,3-dihydroquinoxaline-2,3-dione de haute purete - Google Patents
Procede de preparation de 6,7-dichloro-5-nitro-2,3-dihydroquinoxaline-2,3-dione de haute purete Download PDFInfo
- Publication number
- CA2286797C CA2286797C CA002286797A CA2286797A CA2286797C CA 2286797 C CA2286797 C CA 2286797C CA 002286797 A CA002286797 A CA 002286797A CA 2286797 A CA2286797 A CA 2286797A CA 2286797 C CA2286797 C CA 2286797C
- Authority
- CA
- Canada
- Prior art keywords
- water
- dichloro
- dione
- dihydroquinoxaline
- nitro
- 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 - Fee Related
Links
- HFKWRUBZYILVLT-UHFFFAOYSA-N 6,7-dichloro-5-nitroquinoxaline-2,3-dione Chemical compound O=C1C(=O)N=C2C([N+](=O)[O-])=C(Cl)C(Cl)=CC2=N1 HFKWRUBZYILVLT-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 description 13
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 235000010333 potassium nitrate Nutrition 0.000 description 6
- 239000004323 potassium nitrate Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- CHFSOFHQIZKQCR-UHFFFAOYSA-N licostinel Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C(Cl)=C2[N+](=O)[O-] CHFSOFHQIZKQCR-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AOWDOWTZGBQMNB-UHFFFAOYSA-N 5-nitroquinoxaline-2,3-dione Chemical compound O=C1C(=O)N=C2C([N+](=O)[O-])=CC=CC2=N1 AOWDOWTZGBQMNB-UHFFFAOYSA-N 0.000 description 1
- AVBSIKMUAFYZAV-UHFFFAOYSA-N 6,7-dichloro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C(Cl)=C2 AVBSIKMUAFYZAV-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011850 initial investigation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical compound C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne un procédé de préparation de 6,7-dichloro-5-nitro-2,3-dihydroquinoxaline-2,3-dione de haute pureté, qui consiste à recristalliser l2 6,7-dichloro-5-nitro-2,3-dihydroquinoxaline-2,3-dione brut à partir d'une solution d'eau et de solvants fortement polaires.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84447597A | 1997-04-18 | 1997-04-18 | |
| US08/844,475 | 1997-04-18 | ||
| PCT/US1998/007966 WO1998047878A1 (fr) | 1997-04-18 | 1998-04-20 | Procede de preparation de 6,7-dichloro-5- nitro-2,3-dihydroquinoxaline-2,3-dione de haute purete |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2286797A1 CA2286797A1 (fr) | 1998-10-29 |
| CA2286797C true CA2286797C (fr) | 2008-07-15 |
Family
ID=25292811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002286797A Expired - Fee Related CA2286797C (fr) | 1997-04-18 | 1998-04-20 | Procede de preparation de 6,7-dichloro-5-nitro-2,3-dihydroquinoxaline-2,3-dione de haute purete |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0975607A1 (fr) |
| JP (1) | JP2001522358A (fr) |
| CA (1) | CA2286797C (fr) |
| WO (1) | WO1998047878A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2153819T3 (da) | 2000-07-14 | 2012-12-03 | Allergan Inc | Anvendelse af en opløselighedsforbedrende bestanddel i en vandig sammensætning omfattende brimonidintartrat |
| US8858961B2 (en) | 2000-07-14 | 2014-10-14 | Allergan, Inc. | Compositions containing alpha-2-adrenergic agonist components |
| IL151530A0 (en) | 2000-07-14 | 2003-04-10 | Allergan Sales Inc | Compositions containing alpha-2-adrenergic agonist components |
| US9737531B2 (en) | 2012-07-12 | 2017-08-22 | Glytech, Llc | Composition and method for treatment of depression and psychosis in humans |
| MX393950B (es) | 2017-06-12 | 2025-03-24 | Glytech Llc | Composicion y metodo para el tratamiento de la depresion y psicosis en humanos |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0647137B1 (fr) * | 1992-06-22 | 2008-08-13 | The Regents Of The University Of California | Antagonistes des recepteurs de glycine et leur utilisation |
-
1998
- 1998-04-20 CA CA002286797A patent/CA2286797C/fr not_active Expired - Fee Related
- 1998-04-20 EP EP98919820A patent/EP0975607A1/fr not_active Withdrawn
- 1998-04-20 WO PCT/US1998/007966 patent/WO1998047878A1/fr not_active Ceased
- 1998-04-20 JP JP54625298A patent/JP2001522358A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0975607A1 (fr) | 2000-02-02 |
| CA2286797A1 (fr) | 1998-10-29 |
| JP2001522358A (ja) | 2001-11-13 |
| WO1998047878A1 (fr) | 1998-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160420 |