HUT43596A - Process for production of 4-/2-imidasoline-2-il-amino/-5-chlor-2,1,3-benzothiadiazole /thizanidine/ - Google Patents
Process for production of 4-/2-imidasoline-2-il-amino/-5-chlor-2,1,3-benzothiadiazole /thizanidine/Info
- Publication number
- HUT43596A HUT43596A HU861667A HU166786A HUT43596A HU T43596 A HUT43596 A HU T43596A HU 861667 A HU861667 A HU 861667A HU 166786 A HU166786 A HU 166786A HU T43596 A HUT43596 A HU T43596A
- Authority
- HU
- Hungary
- Prior art keywords
- benzothiadiazole
- amino
- chloro
- thizanidine
- imidasoline
- Prior art date
Links
- 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 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003344 environmental pollutant Substances 0.000 abstract 1
- 231100000719 pollutant Toxicity 0.000 abstract 1
- XFYDIVBRZNQMJC-UHFFFAOYSA-N tizanidine Chemical compound ClC=1C=CC2=NSN=C2C=1NC1=NCCN1 XFYDIVBRZNQMJC-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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)
Abstract
The prepn. of 5-chloro-4-(2-imidazolin-2-yl-amino) 2,1,3-benzo thiadiazole (I) comprises reacting 5-chloro-4-cyanamino -2,1,3-benzothiadiazole (II) with ethylene diamine-mono-p-toluene sulphonate in xylene. - Reaction is at 75-140, pref. 80-110 deg.C, esp. 90-100 deg.C. USE/ADVANTAGE - (I) is a centrally effective myotonolytic. Pure crystalline (I) can be obtd. simply and in very good yields. The process can be carried out on an industrial scale in a single pot and uses no pollutants or hard-to-handle solvents. The process is economical, in that yields are high, energy requirements are low and the solvent is cheap, and does not need to be evapd. off.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863610407 DE3610407A1 (en) | 1986-03-27 | 1986-03-27 | Process for the preparation of tizanidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT43596A true HUT43596A (en) | 1987-11-30 |
| HU197005B 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 (en) |
| AT (1) | AT396237B (en) |
| CA (1) | CA1299576C (en) |
| DE (1) | DE3610407A1 (en) |
| HU (1) | HU197005B (en) |
| IT (1) | IT1216800B (en) |
| MX (1) | MX172623B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2234506C1 (en) * | 2003-06-05 | 2004-08-20 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" | Method for preparing 5-chloro-4-[(2-imidazolin-2-yl)amino]-2,1,3-benzothiadiazole hydrochloride |
| CZ301889B6 (en) * | 2008-12-18 | 2010-07-21 | Farmak, A. S. | Process for preparing tizanidine hydrochloride |
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/en not_active Withdrawn
- 1986-04-21 HU HU861667A patent/HU197005B/en unknown
-
1987
- 1987-03-24 IT IT8747764A patent/IT1216800B/en active
- 1987-03-25 MX MX005705A patent/MX172623B/en unknown
- 1987-03-25 CA CA000532965A patent/CA1299576C/en not_active Expired - Lifetime
- 1987-03-26 AT AT0073487A patent/AT396237B/en not_active IP Right Cessation
- 1987-04-18 KR KR1019870003738A patent/KR960001725B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT8747764A0 (en) | 1987-03-24 |
| HU197005B (en) | 1989-02-28 |
| IT1216800B (en) | 1990-03-14 |
| AT396237B (en) | 1993-07-26 |
| DE3610407A1 (en) | 1987-10-01 |
| KR960001725B1 (en) | 1996-02-03 |
| MX172623B (en) | 1994-01-04 |
| ATA73487A (en) | 1992-11-15 |
| CA1299576C (en) | 1992-04-28 |
| KR880012600A (en) | 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 |