JPS55149257A - Novel preparation of isoindoline derivative - Google Patents
Novel preparation of isoindoline derivativeInfo
- Publication number
- JPS55149257A JPS55149257A JP4922379A JP4922379A JPS55149257A JP S55149257 A JPS55149257 A JP S55149257A JP 4922379 A JP4922379 A JP 4922379A JP 4922379 A JP4922379 A JP 4922379A JP S55149257 A JPS55149257 A JP S55149257A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- derivative
- isoindoline
- methanol
- solvent
- 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.)
- Granted
Links
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- -1 e.g. Substances 0.000 abstract 2
- JKNKNWJNCOJPLI-UHFFFAOYSA-N o-phthalaldehydic acid Chemical compound C1=CC=C2C(O)OC(=O)C2=C1 JKNKNWJNCOJPLI-UHFFFAOYSA-N 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000009434 installation Methods 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
Abstract
PURPOSE: To obtain the titled compound useful as anti-inflammatory drugs, analgesics, etc. economically in high yields, by reacting an o-phthalaldehydic acid with an aniline derivative in a solvent, e.g., methanol, followed by only subjecting the resulted benzylidene derivative to ring formation in the presence of a reducing agent.
CONSTITUTION: o-Phthalaldehydic acid shown by the formula I is reacted with an aniline derivative shown by the formula II (R is H or 1W2C alkyl; X is carboxy, carboalkoxy, amido, or cyano) in a solvent, e.g., low priced methanol, to give a benzylidene derivative shown by the formula III, which is not isolated and subjected to ring formation in the presence of a reducing agent to prepare an isoindoline derivative shown by the formula IV, e.g., 1-oxo-2-[p-[(α-methyl)carboxymethyl] phnyl]-isoindoline, etc.
EFFECT: Since the reactions is carried out in one bath, the installation and operation for the reaction are simple.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4922379A JPS603381B2 (en) | 1979-04-20 | 1979-04-20 | Novel production method for isoindoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4922379A JPS603381B2 (en) | 1979-04-20 | 1979-04-20 | Novel production method for isoindoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55149257A true JPS55149257A (en) | 1980-11-20 |
| JPS603381B2 JPS603381B2 (en) | 1985-01-28 |
Family
ID=12824927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4922379A Expired JPS603381B2 (en) | 1979-04-20 | 1979-04-20 | Novel production method for isoindoline derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS603381B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5750961A (en) * | 1980-09-10 | 1982-03-25 | Hisamitsu Pharmaceut Co Inc | Novel preparation of isoindoline derivative |
| CN106397298A (en) * | 2016-08-11 | 2017-02-15 | 杭州中美华东制药有限公司 | A pharmaceutical composition containing indobufen and uses thereof |
| CN115850154A (en) * | 2022-12-29 | 2023-03-28 | 山东京卫制药有限公司 | Preparation method of indobufen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62176579U (en) * | 1986-04-30 | 1987-11-10 |
-
1979
- 1979-04-20 JP JP4922379A patent/JPS603381B2/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5750961A (en) * | 1980-09-10 | 1982-03-25 | Hisamitsu Pharmaceut Co Inc | Novel preparation of isoindoline derivative |
| CN106397298A (en) * | 2016-08-11 | 2017-02-15 | 杭州中美华东制药有限公司 | A pharmaceutical composition containing indobufen and uses thereof |
| CN115850154A (en) * | 2022-12-29 | 2023-03-28 | 山东京卫制药有限公司 | Preparation method of indobufen |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS603381B2 (en) | 1985-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS55149257A (en) | Novel preparation of isoindoline derivative | |
| Nitta et al. | Nonacarbonyldiiron-, pentacarbonyliron-, or hexacarbonylmolybdenum-induced reacions of 4, 5-polymethylene-substituted 2-isoxazolines. | |
| JPS55149256A (en) | Novel preparation of isoindoline derivative | |
| JPS5695142A (en) | Preparation of aliphatic aldehyde | |
| JPS5750962A (en) | Novel preparation of isoindoline derivative | |
| JPS5622753A (en) | Preparation of alpha-halogeno-beta-alanine or its salt of mineral acid | |
| JPS5576881A (en) | Preparation of high-purity coproporphyrin 3 alkali salt | |
| JPS57156456A (en) | Preparation of 1,5,5-trimethyl-3-amino-4-cyanocyclohexa-1,3- diene and its derivative | |
| JPS5679661A (en) | Preparation of alpha-chlorohydrocinnamnitrile | |
| JPS5587734A (en) | Preparation of orthoester | |
| JPS55111468A (en) | Preparation of n-benzyl-tetrahydro isoquinoline derivative | |
| JPS5718683A (en) | 3,8-epoxy-7-keto-6-oxabicyclo 3,2,1 octane derivative and its preparation | |
| JPS5718667A (en) | Preparation of aporphine compound | |
| JPS54148773A (en) | Preparation of phthalide | |
| JPS55143963A (en) | Novel nitro compound and its preparation | |
| JPS56158738A (en) | Preparation of 2-substituted-3-oxo-cyclopentylacetic ester | |
| JPS549225A (en) | Preparation of hydrazinoalkanesulfonic acid derivatives | |
| JPS5731685A (en) | Preparation of 2',3',5'-triacetoxy-5-fluorouridine | |
| JPS5551079A (en) | Preparation of benzoxazole derivative | |
| JPS5262291A (en) | Preparation of 7-aamino-deacetoxycephalosporanic acid derivatives | |
| JPS5668668A (en) | Preparation of 2-indolinones | |
| JPS54119485A (en) | Novel optically active pyridoxamine derivative and their preparation | |
| JPS5772965A (en) | Preparation of substituted acetaldoxime | |
| JPS5620556A (en) | Production of alpha-halogeno-beta-alanine | |
| JPS56158754A (en) | Preparation of p-ethoxycarbonylphenyl epsilon-guanidinocaproate |