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Indoline-3-acetic acid derivative and preparation method thereof as well as application of derivative in medicine

A technology of indoline and derivatives is applied in the application field of indoline-3-acetic acid derivatives in the preparation of anti-type 2 diabetes drugs, and can solve problems such as weight gain, cardiovascular disease and the like

Active Publication Date: 2013-04-17
贵州中森医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the long-term and extensive clinical use of thiazolidinedione insulin sensitizers, their clinical status is controversial due to their side effects of weight gain, fat accumulation, water and sodium retention, osteoporosis and cardiovascular diseases

Method used

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  • Indoline-3-acetic acid derivative and preparation method thereof as well as application of derivative in medicine
  • Indoline-3-acetic acid derivative and preparation method thereof as well as application of derivative in medicine
  • Indoline-3-acetic acid derivative and preparation method thereof as well as application of derivative in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The preparation method of 2-methyl-1-(4-chlorobenzoyl)-5-benzyloxy-2,3-dihydro-indole-3-acetic acid (compound 1), comprising the following steps:

[0085]

[0086] Compound 1 synthetic route

[0087] (1): Methyl 2-methyl-1-(4-chlorobenzoyl)-5-benzyloxy-2,3-dihydro-indole-3-acetate (1-1)

[0088] 2-Methyl-5-benzyloxy-2,3-dihydro-indole-3-acetic acid methyl ester (0.205g, 0.66mmol) was dissolved in ethyl acetate 5ml and acetonitrile 10ml, and p-chlorobenzene was added to the solution Formic acid (0.207g, 1.32mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.278g, 1.45mmol) N-methylmorpholine (0.16ml, 1.45mmol ) and stirred at room temperature for 12h. After the reaction, the reaction solution was washed with 1N hydrochloric acid (20ml×3), saturated sodium bicarbonate (20ml×3), distilled water 20ml, saturated sodium chloride 20ml, dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was passed through a silica gel column...

Embodiment 2

[0092] The preparation method of 2-methyl-1-(4-fluorobenzoyl)-5-benzyloxy-2,3-dihydro-indole-3-acetic acid (compound 2), comprising:

[0093]

[0094] Substituting p-fluorobenzoic acid for p-chlorobenzoic acid, the title compound was prepared according to the method of Example 1 with a yield of 39.2%. 1 H NMR (CDCl 3 ): δ=1.34 (d, 3H); 2.71 (d, 2H); 3.06 (m, 1H); 4.18 (m, 1H); 5.01 (s, 2H); 6.80 (dd, 1H); 1H); 7.36-7.40 (m, 5H); 7.40 (d, 2H); 7.60 (d, 1H); 8.10 (d, 2H). Elemental Analysis, C 25 h 22 FNO 4 , found (calculated), %: C 71.54 (71.59); H 5.23 (5.29); N 3.30 (3.34).

Embodiment 3

[0096] The preparation method of 2-methyl-1-(4-trifluoromethylbenzoyl)-5-benzyloxy-2,3-dihydro-indole-3-acetic acid (compound 3), comprising:

[0097]

[0098] Substituting 4-trifluoromethylbenzoic acid for p-chlorobenzoic acid, the title compound was prepared according to the method of Example 1 with a yield of 32.3%. 1 H NMR (CDCl 3): δ=1.26 (d, 3H); 2.65 (d, 2H); 3.19 (m, 1H); 4.15 (m, 1H); 5.01 (s, 2H); 6.91 (d, 2H); 7.33-7.40 ( m, 6H); 7.60 (d, 2H); 7.70 (d, 2H). Elemental Analysis, C 26 h 22 f 3 NO 4 , found (calculated), %: C 66.50 (66.52); H 4.69 (4.72); N 2.97 (2.98).

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Abstract

The invention discloses an indoline-3-acetic acid derivative and a preparation method thereof. The indoline-3-acetic acid derivative is shown by the following general formula (I), wherein R1 represents one of the following groups as shown in the specification, and R2 represents one of the following groups as shown in the specification. The invention also discloses the application of the indoline-3-acetic acid derivative in medicine used for resisting II-type diabetes mellitus.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to indoline-3-acetic acid derivatives, a preparation method of the indoline-3-acetic acid derivatives, and the preparation of indoline-3-acetic acid derivatives Application of anti-type 2 diabetes drugs. [0002] Background technique [0003] Diabetes mellitus (DM) is a systemic chronic secretory and metabolic disease associated with genetic factors. It is a metabolic disorder of sugar, fat, and protein caused by absolute or relative insufficiency of insulin secretion in the body. Its main features are hyperglycemia and urine sugar, often accompanied by atherosclerotic cardiovascular and cerebrovascular diseases, diabetic nephropathy, nervous system lesions and eye lesions such as cataracts, retinopathy and other complications in clinical practice. With the improvement of living standards and changes in living habits, the incidence of type 2 diabetes is increasing year b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/28C07D209/26C07D401/06C07D401/12C07D401/14C07D209/22A61P3/10A61P5/50
Inventor 汤磊李志艳钟刚王建塔崔杏
Owner 贵州中森医药有限公司
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