RU2005111751A - Способ получения высокочистого 3,5-диамино-6-(2,3-дихлорфенил)-1,2,4-триазина - Google Patents
Способ получения высокочистого 3,5-диамино-6-(2,3-дихлорфенил)-1,2,4-триазина Download PDFInfo
- Publication number
- RU2005111751A RU2005111751A RU2005111751/04A RU2005111751A RU2005111751A RU 2005111751 A RU2005111751 A RU 2005111751A RU 2005111751/04 A RU2005111751/04 A RU 2005111751/04A RU 2005111751 A RU2005111751 A RU 2005111751A RU 2005111751 A RU2005111751 A RU 2005111751A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- aminoguanidine
- molar equivalents
- dichlorophenyl
- diamino
- Prior art date
Links
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract 6
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims abstract 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000000395 magnesium oxide Substances 0.000 claims abstract 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract 4
- FIBBFBXFASKAON-UHFFFAOYSA-N 2,3-dichlorobenzoyl cyanide Chemical compound ClC1=CC=CC(C(=O)C#N)=C1Cl FIBBFBXFASKAON-UHFFFAOYSA-N 0.000 claims abstract 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract 3
- 238000002955 isolation Methods 0.000 claims abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract 2
- 239000007858 starting material Substances 0.000 claims abstract 2
- DLXDQVQGODOEFS-UHFFFAOYSA-N 2-aminoguanidine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NNC(N)=N DLXDQVQGODOEFS-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (8)
1. Способ получения 3,5-диамино-6-(2,3-дихлорфенил)-1,2,4-триазина формулы (I) с использованием 2,3-дихлорбензоилцианида и соли аминогуанидина в качестве исходных продуктов, характеризующийся тем, что 2,3-бензоилцианид формулы (II) реагирует с 1-2 мольными эквивалентами соли аминогуанидина в 3-6 мольных эквивалентах метансульфокислоты с последующим преобразованием полученного аддукта формулы (IV) без его выделения в продукт с помощью оксида магния, после чего полученный таким образом продукт подвергают перекристаллизации из подходящего органического растворителя.
2. Способ по п.1, характеризующийся тем, что используют димезилатную соль аминогуанидина формулы (III) в качестве аминогуанидиновой соли.
3. Способ по п.2, характеризующийся тем, что используют 1,3 мольных эквивалентов димезилата аминогуанидина формулы (III).
4. Способ по п.1, характеризующийся тем, что используют 4,2 мольных эквивалентов метансульфокислоты.
5. Способ по п.1, характеризующийся тем, что реакцию циклизации проводят в присутствии 2-4 мольных эквивалентов оксида магния.
6. Способ по п.5, характеризующийся тем, что используют 3,75 мольных эквивалентов оксида магния в реакции циклизации.
7. Способ по п.1, характеризующийся тем, что используют ацетон для перекристаллизации.
8. Димезилат аминогуанидина формулы (III).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP0203114 | 2002-09-20 | ||
| HU0203114A HU225667B1 (en) | 2002-09-20 | 2002-09-20 | Method for producing high-purity 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005111751A true RU2005111751A (ru) | 2006-10-27 |
| RU2335497C2 RU2335497C2 (ru) | 2008-10-10 |
Family
ID=89980802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005111751/04A RU2335497C2 (ru) | 2002-09-20 | 2003-09-18 | Способ получения высокочистого 3,5-диамино-6-(2,3-дихлорфенил)-1,2,4-триазина |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7390899B2 (ru) |
| EP (1) | EP1539720B8 (ru) |
| AT (1) | ATE346051T1 (ru) |
| AU (1) | AU2003267676A1 (ru) |
| CA (1) | CA2498761A1 (ru) |
| DE (1) | DE60309899T2 (ru) |
| ES (1) | ES2277104T3 (ru) |
| HU (1) | HU225667B1 (ru) |
| IL (1) | IL166953A (ru) |
| PL (1) | PL374724A1 (ru) |
| RU (1) | RU2335497C2 (ru) |
| WO (1) | WO2004026845A1 (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2209639B1 (es) * | 2002-10-31 | 2005-08-01 | Vita Cientifica, S.L. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y obtencion de su intermedio. |
| WO2007138075A1 (en) * | 2006-05-31 | 2007-12-06 | Calaire Chimie Sas | Method for preparing lamotrigine and its intermediate 2,3-dichlorobenzoyl chloride |
| CA2659290A1 (en) * | 2006-08-14 | 2008-02-21 | Jean-Paul Roduit | A process for the preparation of lamotrigine |
| GB0800741D0 (en) | 2008-01-16 | 2008-02-20 | Univ Greenwich | Cyclic triazo and diazo sodium channel blockers |
| GB2471729A (en) | 2009-07-08 | 2011-01-12 | Univ Greenwich | 1,2,4-triazine derivatives and their use as sodium channel blockers |
| WO2018229517A1 (en) | 2017-06-15 | 2018-12-20 | GYURCSÁNSZKY, László György | Pallet for supporting and suspending loads |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR68380B (ru) | 1979-06-01 | 1981-12-28 | Wellcome Found | |
| GB8613183D0 (en) | 1986-05-30 | 1986-07-02 | Wellcome Found | Triazine salt |
| WO1996020934A1 (en) | 1994-12-30 | 1996-07-11 | The Wellcome Foundation Limited | Process for the preparation of lamotrigine |
| GB9426448D0 (en) | 1994-12-30 | 1995-03-01 | Wellcome Found | Process |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| US6639072B1 (en) | 2000-01-03 | 2003-10-28 | Rpg Life Sciences Limited | Process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine |
| CA2366521C (en) * | 2001-12-24 | 2007-03-06 | Brantford Chemicals Inc. | A new and efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines |
-
2002
- 2002-09-20 HU HU0203114A patent/HU225667B1/hu not_active IP Right Cessation
-
2003
- 2003-09-18 AU AU2003267676A patent/AU2003267676A1/en not_active Abandoned
- 2003-09-18 ES ES03748368T patent/ES2277104T3/es not_active Expired - Lifetime
- 2003-09-18 CA CA002498761A patent/CA2498761A1/en not_active Abandoned
- 2003-09-18 RU RU2005111751/04A patent/RU2335497C2/ru not_active IP Right Cessation
- 2003-09-18 PL PL03374724A patent/PL374724A1/xx not_active IP Right Cessation
- 2003-09-18 US US10/528,379 patent/US7390899B2/en not_active Expired - Fee Related
- 2003-09-18 DE DE60309899T patent/DE60309899T2/de not_active Expired - Lifetime
- 2003-09-18 AT AT03748368T patent/ATE346051T1/de not_active IP Right Cessation
- 2003-09-18 EP EP03748368A patent/EP1539720B8/en not_active Expired - Lifetime
- 2003-09-18 WO PCT/HU2003/000072 patent/WO2004026845A1/en active IP Right Grant
-
2005
- 2005-02-17 IL IL166953A patent/IL166953A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2277104T3 (es) | 2007-07-01 |
| HU0203114D0 (ru) | 2002-11-28 |
| HUP0203114A2 (hu) | 2004-05-28 |
| IL166953A (en) | 2009-09-01 |
| AU2003267676A1 (en) | 2004-04-08 |
| WO2004026845A1 (en) | 2004-04-01 |
| EP1539720B8 (en) | 2007-01-03 |
| CA2498761A1 (en) | 2004-04-01 |
| EP1539720A1 (en) | 2005-06-15 |
| HU225667B1 (en) | 2007-05-29 |
| RU2335497C2 (ru) | 2008-10-10 |
| EP1539720B1 (en) | 2006-11-22 |
| DE60309899T2 (de) | 2007-10-18 |
| DE60309899D1 (de) | 2007-01-04 |
| US7390899B2 (en) | 2008-06-24 |
| PL374724A1 (en) | 2005-10-31 |
| ATE346051T1 (de) | 2006-12-15 |
| US20060178511A1 (en) | 2006-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110919 |