ES8602003A1 - Prepn. of tetra:hydro-pyrano-indole deriv. anti-inflammation drug - Google Patents
Prepn. of tetra:hydro-pyrano-indole deriv. anti-inflammation drugInfo
- Publication number
- ES8602003A1 ES8602003A1 ES540920A ES540920A ES8602003A1 ES 8602003 A1 ES8602003 A1 ES 8602003A1 ES 540920 A ES540920 A ES 540920A ES 540920 A ES540920 A ES 540920A ES 8602003 A1 ES8602003 A1 ES 8602003A1
- Authority
- ES
- Spain
- Prior art keywords
- solvent
- pyrano
- prepn
- hydro
- tetra
- 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
Links
- 206010061218 Inflammation Diseases 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The process comprises reaction of an indole deriv. of formula (II) with a nitrile of formula (III) in a solvent such as toluene, benzene or xylene in the presence of e.g. toluene sulphonic acid. Hydrolysis of the intermediate cpd. using as solvent a mixt. of water and dioxane or tetrahydrofuran at boiling point in the presence of e.g. sulphuric acid gives the prod. of formula (I). This is isolated by distillation of the organic solvent and filtration of the resulting aq. suspension, with purificn. by crystallisation in a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES540920A ES8602003A1 (en) | 1985-03-05 | 1985-03-05 | Prepn. of tetra:hydro-pyrano-indole deriv. anti-inflammation drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES540920A ES8602003A1 (en) | 1985-03-05 | 1985-03-05 | Prepn. of tetra:hydro-pyrano-indole deriv. anti-inflammation drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES540920A0 ES540920A0 (en) | 1985-11-16 |
| ES8602003A1 true ES8602003A1 (en) | 1985-11-16 |
Family
ID=8488790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES540920A Expired ES8602003A1 (en) | 1985-03-05 | 1985-03-05 | Prepn. of tetra:hydro-pyrano-indole deriv. anti-inflammation drug |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES8602003A1 (en) |
-
1985
- 1985-03-05 ES ES540920A patent/ES8602003A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES540920A0 (en) | 1985-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1A | Transfer granted | ||
| FD1A | Patent lapsed |
Effective date: 20050718 |