JPS55344A - 2-nitrosoiminobenzthiazoline derivative - Google Patents
2-nitrosoiminobenzthiazoline derivativeInfo
- Publication number
- JPS55344A JPS55344A JP14486178A JP14486178A JPS55344A JP S55344 A JPS55344 A JP S55344A JP 14486178 A JP14486178 A JP 14486178A JP 14486178 A JP14486178 A JP 14486178A JP S55344 A JPS55344 A JP S55344A
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- hydroxyethyl
- reacted
- formula
- carbonylmethyl
- 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.)
- Pending
Links
- ZGGPYVRPUSNLPB-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)nitrous amide Chemical class C1=CC=C2SC(NN=O)=NC2=C1 ZGGPYVRPUSNLPB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- LSYZRUOXXOTVAV-UHFFFAOYSA-N (3-chlorophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(Cl)=C1 LSYZRUOXXOTVAV-UHFFFAOYSA-N 0.000 abstract 1
- HRTSXEJEERWVJC-UHFFFAOYSA-N 2-(5-chloro-2-imino-1,3-benzothiazol-3-yl)acetic acid Chemical compound ClC1=CC=C2SC(=N)N(CC(=O)O)C2=C1 HRTSXEJEERWVJC-UHFFFAOYSA-N 0.000 abstract 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 abstract 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 abstract 1
- AVVSRALHGMVQQW-UHFFFAOYSA-N 5-chloro-1,3-benzothiazol-2-amine Chemical compound ClC1=CC=C2SC(N)=NC2=C1 AVVSRALHGMVQQW-UHFFFAOYSA-N 0.000 abstract 1
- -1 5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl-2-iminobenzthiazoline Chemical compound 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000003119 painkilling effect Effects 0.000 abstract 1
- 238000007142 ring opening reaction Methods 0.000 abstract 1
- HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Abstract
NEW MATERIAL:5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl- 2-nitrosoiminobenzthiazoline shown by the formula I.
USE: A synthetic intermediate of 5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl-2-benzthiazolinone, a medicine having antiinflammatory and pain-killing effect.
PROCESS: m-Chloroaniline shown by the formula II is reacted with a thiocyanate (e.g., sodium salt) to give (3-chlorophenyl) thiourea, which is subjected to ring opening reaction by bromine to prepare 5-chloro-2-aminobenzthiazole (compound III). The compound III is reacted with a monohalogenated acetate to give 5-chloro- 2-iminobenzthiazoline-3-acetate shown by the formula IV (R is lower alkyl), which is reacted with 1-(2-hydroxyethyl) piperazine to prepare 5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl-2-iminobenzthiazoline. This compound is reacted with a nitrite (e.g., sodium salt) to give the compound shown by the formula I.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14486178A JPS55344A (en) | 1978-11-22 | 1978-11-22 | 2-nitrosoiminobenzthiazoline derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14486178A JPS55344A (en) | 1978-11-22 | 1978-11-22 | 2-nitrosoiminobenzthiazoline derivative |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52101463A Division JPS5811951B2 (en) | 1977-08-24 | 1977-08-24 | Method for producing 2-benzothiazolinone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS55344A true JPS55344A (en) | 1980-01-05 |
Family
ID=15372096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14486178A Pending JPS55344A (en) | 1978-11-22 | 1978-11-22 | 2-nitrosoiminobenzthiazoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55344A (en) |
-
1978
- 1978-11-22 JP JP14486178A patent/JPS55344A/en active Pending
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