HU197005B - Process for producing 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole (tizanidin) - Google Patents
Process for producing 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole (tizanidin) Download PDFInfo
- Publication number
- HU197005B HU197005B HU861667A HU166786A HU197005B HU 197005 B HU197005 B HU 197005B HU 861667 A HU861667 A HU 861667A HU 166786 A HU166786 A HU 166786A HU 197005 B HU197005 B HU 197005B
- Authority
- HU
- Hungary
- Prior art keywords
- benzothiadiazole
- chloro
- amino
- mixture
- liters
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- XFYDIVBRZNQMJC-UHFFFAOYSA-N tizanidine Chemical compound ClC=1C=CC2=NSN=C2C=1NC1=NCCN1 XFYDIVBRZNQMJC-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- BPGDXFFKSUUPBE-UHFFFAOYSA-N (5-chloro-2,1,3-benzothiadiazol-4-yl)cyanamide Chemical compound N#CNC1=C(Cl)C=CC2=NSN=C21 BPGDXFFKSUUPBE-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 claims 1
- 229960000488 tizanidine Drugs 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 2-imidazolin-2-yl--sulfonyl Chemical group 0.000 description 2
- MURNIACGGUSMAP-UHFFFAOYSA-N 5-chloro-2,1,3-benzothiadiazol-4-amine Chemical compound NC1=C(Cl)C=CC2=NSN=C12 MURNIACGGUSMAP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QDPZXGIZWGXDAN-UHFFFAOYSA-N ClC1=C(C=2C(=NSN2)C=C1N)C#N Chemical compound ClC1=C(C=2C(=NSN2)C=C1N)C#N QDPZXGIZWGXDAN-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863610407 DE3610407A1 (de) | 1986-03-27 | 1986-03-27 | Verfahren zur herstellung von tizanidin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT43596A HUT43596A (en) | 1987-11-30 |
| HU197005B true HU197005B (en) | 1989-02-28 |
Family
ID=6297425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU861667A HU197005B (en) | 1986-03-27 | 1986-04-21 | Process for producing 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole (tizanidin) |
Country Status (7)
| Country | Link |
|---|---|
| KR (1) | KR960001725B1 (de) |
| AT (1) | AT396237B (de) |
| CA (1) | CA1299576C (de) |
| DE (1) | DE3610407A1 (de) |
| HU (1) | HU197005B (de) |
| IT (1) | IT1216800B (de) |
| MX (1) | MX172623B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2234506C1 (ru) * | 2003-06-05 | 2004-08-20 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Способ получения 5-хлор-4-/(2-имидазолин-2-ил)амино/-2,1,3-бензотиадиазола хлоргидрата |
| CZ301889B6 (cs) * | 2008-12-18 | 2010-07-21 | Farmak, A. S. | Zpusob prípravy tizanidinu hydrochloridu |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH579565A5 (en) * | 1973-03-15 | 1976-09-15 | Wander Ag Dr A | Imidazolin-2-ylamino-2,1,3-benzothiadiazoles prodn. - by cyclising corresp. beta aminoethyl (thio) ureas, active against muscle tremors and rigor |
| AU505664B2 (en) * | 1977-04-12 | 1979-11-29 | Wander A.G. | 2, 1, 3-benzothiadiazoles |
-
1986
- 1986-03-27 DE DE19863610407 patent/DE3610407A1/de not_active Withdrawn
- 1986-04-21 HU HU861667A patent/HU197005B/hu unknown
-
1987
- 1987-03-24 IT IT8747764A patent/IT1216800B/it active
- 1987-03-25 MX MX005705A patent/MX172623B/es unknown
- 1987-03-25 CA CA000532965A patent/CA1299576C/en not_active Expired - Lifetime
- 1987-03-26 AT AT0073487A patent/AT396237B/de not_active IP Right Cessation
- 1987-04-18 KR KR1019870003738A patent/KR960001725B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT8747764A0 (it) | 1987-03-24 |
| HUT43596A (en) | 1987-11-30 |
| IT1216800B (it) | 1990-03-14 |
| AT396237B (de) | 1993-07-26 |
| DE3610407A1 (de) | 1987-10-01 |
| KR960001725B1 (ko) | 1996-02-03 |
| MX172623B (es) | 1994-01-04 |
| ATA73487A (de) | 1992-11-15 |
| CA1299576C (en) | 1992-04-28 |
| KR880012600A (ko) | 1988-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: NOVARTIS AG (NOVARTIS SA, NOVARTIS INC.), CH |