CA2382405C - Nouveaux procedes de synthese de la (3as)-5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine - Google Patents
Nouveaux procedes de synthese de la (3as)-5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine Download PDFInfo
- Publication number
- CA2382405C CA2382405C CA002382405A CA2382405A CA2382405C CA 2382405 C CA2382405 C CA 2382405C CA 002382405 A CA002382405 A CA 002382405A CA 2382405 A CA2382405 A CA 2382405A CA 2382405 C CA2382405 C CA 2382405C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- pyrrolo
- benzothiadiazine
- dioxo
- 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
- 238000000034 method Methods 0.000 title claims abstract description 18
- MNTIJYGEITVWHU-SNVBAGLBSA-N (3as)-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound C12=CC=CC=C2S(=O)(=O)N[C@@H]2N1CCC2 MNTIJYGEITVWHU-SNVBAGLBSA-N 0.000 title claims description 3
- 230000002194 synthesizing effect Effects 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- HWOJZNGWXRYGBY-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide Chemical compound C12=CC=CC=C2S(=O)(=O)N=C2N1CCC2 HWOJZNGWXRYGBY-UHFFFAOYSA-N 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 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 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 2
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- 102000003678 AMPA Receptors Human genes 0.000 description 1
- 108090000078 AMPA Receptors Proteins 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- PZTVCDSGEXHVBL-ODQAEMFESA-L dichlororuthenium;(1r,2r)-1,2-diphenylethane-1,2-diamine;[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane Chemical compound [Cl-].[Cl-].[Ru+2].C1([C@@H](N)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1.C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 PZTVCDSGEXHVBL-ODQAEMFESA-L 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR01.05226 | 2001-04-18 | ||
| FR0105226A FR2823753B1 (fr) | 2001-04-18 | 2001-04-18 | Nouveau procede de synthese de la (3as)-5,5-dioxo-2,3,3a, 4-tetrahydro-1h-pyrrolo [2,1-c] [1,2,4] benzothiadiazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2382405A1 CA2382405A1 (fr) | 2002-10-18 |
| CA2382405C true CA2382405C (fr) | 2007-03-06 |
Family
ID=8862416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002382405A Expired - Fee Related CA2382405C (fr) | 2001-04-18 | 2002-04-18 | Nouveaux procedes de synthese de la (3as)-5,5-dioxo-2,3,3a,4-tetrahydro-1h-pyrrolo[2,1-c][1,2,4]benzothiadiazine |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6518422B2 (enExample) |
| EP (1) | EP1251132B1 (enExample) |
| JP (1) | JP4011956B2 (enExample) |
| KR (1) | KR100468066B1 (enExample) |
| CN (1) | CN1169811C (enExample) |
| AR (1) | AR036871A1 (enExample) |
| AT (1) | ATE269339T1 (enExample) |
| AU (1) | AU782080B2 (enExample) |
| BR (1) | BR0201307A (enExample) |
| CA (1) | CA2382405C (enExample) |
| DE (1) | DE60200627T2 (enExample) |
| DK (1) | DK1251132T3 (enExample) |
| EA (1) | EA004927B1 (enExample) |
| ES (1) | ES2223031T3 (enExample) |
| FR (1) | FR2823753B1 (enExample) |
| HU (1) | HUP0201256A3 (enExample) |
| MX (1) | MXPA02003639A (enExample) |
| NO (1) | NO20021768L (enExample) |
| NZ (1) | NZ518422A (enExample) |
| PL (1) | PL353512A1 (enExample) |
| PT (1) | PT1251132E (enExample) |
| SI (1) | SI1251132T1 (enExample) |
| ZA (1) | ZA200203085B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US20060014887A1 (en) * | 2004-07-19 | 2006-01-19 | 3M Innovative Properties Company | Method of hydrolyzing a dispersion of ionic fluoropolymer |
| FR2879201B1 (fr) * | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP2230094B1 (de) | 2009-03-20 | 2013-12-11 | Kremstal Türenwerk GmbH | Verfahren für das Beschichten von Plattenwerkstoffen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294791A (en) * | 1966-03-14 | 1966-12-27 | American Home Prod | Tetrahydro-2, 5-methano-1, 2, 5-benzothiadiazepine 1, 1-dioxide |
| US3471483A (en) * | 1967-11-09 | 1969-10-07 | American Home Prod | 1 - substituted - 2,3,3a - 4 - tetrahydro - 1h-pyrrolo(2,1 - c)(1,2,4)benzothiadiazine,5,5-dioxide |
| JPH06192272A (ja) * | 1992-12-24 | 1994-07-12 | Japan Tobacco Inc | 新規なトリアゾロベンゾチアジアジン及びトリアゾロベンゾチアジアゼピン誘導体 |
| FR2722502B1 (fr) * | 1994-07-12 | 1996-08-23 | Adir | Nouveau derive de benzothiadiazine, son procede depreparation et les compositions pharmaceutiques qui le contiennent |
| FR2812291B1 (fr) * | 2000-07-28 | 2002-12-13 | Adir | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-04-18 FR FR0105226A patent/FR2823753B1/fr not_active Expired - Fee Related
-
2002
- 2002-04-10 MX MXPA02003639A patent/MXPA02003639A/es active IP Right Grant
- 2002-04-15 NO NO20021768A patent/NO20021768L/no not_active Application Discontinuation
- 2002-04-16 DK DK02290946T patent/DK1251132T3/da active
- 2002-04-16 PT PT02290946T patent/PT1251132E/pt unknown
- 2002-04-16 ES ES02290946T patent/ES2223031T3/es not_active Expired - Lifetime
- 2002-04-16 AT AT02290946T patent/ATE269339T1/de not_active IP Right Cessation
- 2002-04-16 SI SI200230015T patent/SI1251132T1/xx unknown
- 2002-04-16 DE DE60200627T patent/DE60200627T2/de not_active Expired - Fee Related
- 2002-04-16 EP EP02290946A patent/EP1251132B1/fr not_active Expired - Lifetime
- 2002-04-16 JP JP2002113278A patent/JP4011956B2/ja not_active Expired - Fee Related
- 2002-04-17 EA EA200200378A patent/EA004927B1/ru not_active IP Right Cessation
- 2002-04-17 NZ NZ518422A patent/NZ518422A/xx unknown
- 2002-04-17 BR BR0201307-0A patent/BR0201307A/pt not_active IP Right Cessation
- 2002-04-17 HU HU0201256A patent/HUP0201256A3/hu unknown
- 2002-04-17 AR ARP020101386A patent/AR036871A1/es not_active Application Discontinuation
- 2002-04-18 KR KR10-2002-0021237A patent/KR100468066B1/ko not_active Expired - Fee Related
- 2002-04-18 PL PL02353512A patent/PL353512A1/xx unknown
- 2002-04-18 US US10/125,192 patent/US6518422B2/en not_active Expired - Fee Related
- 2002-04-18 CA CA002382405A patent/CA2382405C/fr not_active Expired - Fee Related
- 2002-04-18 AU AU34405/02A patent/AU782080B2/en not_active Ceased
- 2002-04-18 CN CNB021057907A patent/CN1169811C/zh not_active Expired - Fee Related
- 2002-04-18 ZA ZA200203085A patent/ZA200203085B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |