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Synthesis and application of sulfonamide compounds

A technology of sulfonyl carbonamide and sulfonamide carbonamide, which is applied in the field of medicine, can solve the problems of high irritation of products, pain of patients, and low pH value of injections

Active Publication Date: 2015-02-11
北京桦冠医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the strong acidity of the sulfonic acid group, the pH of the injection is low, and the product is very irritating, which brings pain to the patient.
And because of its poor stability, it is easy to remove sulfonate groups during the drug placement process to form tanshinone IIA, which is precipitated in the injection

Method used

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  • Synthesis and application of sulfonamide compounds
  • Synthesis and application of sulfonamide compounds
  • Synthesis and application of sulfonamide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] [Example 1]: N-(1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthrene[1,2-b] Preparation of furan-2-ylsulfonyl)acetamide sodium salt

[0040] Step 1: Preparation of Intermediate-1 Tanshinone IIA Sulfonyl Chloride

[0041] Tanshinone IIA (10 g, 33 mmol) was added dropwise into 150 mL of sulfuryl chloride, and refluxed for 1 hour. The temperature of the reaction system was lowered to room temperature, and the unconsumed sulfuryl chloride was distilled off under reduced pressure. The remaining black oily liquid was dried under reduced pressure with an oil pump for 2 hours under the condition of avoiding light, and the obtained black oily liquid was directly used in the next reaction.

[0042] Step 2: Preparation of Tanshinone IIA Sulfonamide

[0043] The product obtained in Step 1 (1 g, 2.55 mmol) was dissolved in 10 mL of THF, and added dropwise to vigorously stirred 0-degree ammonia water (10 mL). After the dropwise addition was complete, stir at room...

Embodiment 2

[0048] Example [2]: N-(1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthrene [ 1,2-b] preparation of furan-2-ylsulfonyl)propionamide sodium salt

Embodiment 1

[0049] According to the preparation method of Example [1], replace acetyl chloride with propionyl chloride to obtain N-(1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11 - Hexahydrophenanthrene[1,2-b]furan-2-ylsulfonyl)propionamide sodium salt. 1 H NMR (400MHz, D 2 O) δ7.90-7.86(m, 2H), 3.20(m, 2H), 2.52(s, 3H), 2.01(m, 2H), 1.60(m, 2H), 1.53(m, 2H), 1.29( s, 6H), 1.11(t, 3H), LCMS m / z, 428.1(M-1) +

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Abstract

The invention relates to tanshinone IIA derivatives. The structure of the tanshinone IIA derivatives are carbonylated and acylated products of tanshinone IIA furan ring 2-position sulfonamide as show in a formula (I), wherein R is C1-6 alkyl, cycloalkyl, alkenyl, alkynyl, aryl and aromatic heterocycle and M is a metal ion such as a sodium salt. According to the compounds, on the basis that the activity and water solubility of sodium tanshinone IIA sulfonate are maintained, the acidity of the compounds is reduced; when sodium tanshinone IIA sulfonate is injected, the stimulation to patients is reduced and the stability of the compounds is improved.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to tanshinone IIA sulfonyl carbonamide, its pharmaceutically acceptable salt and its hydrate. The present invention also relates to a preparation method of these compounds, a pharmaceutical composition containing these compounds, a compound drug containing these compounds and one or more other pharmaceutically active substances, and the use of these compounds in the preparation of cardiovascular and cerebrovascular system disease treatment and prevention drugs Applications. Background technique [0002] Salvia miltiorrhiza is the dry root and rhizome of Salvia miltiorrhizaBge., a plant of the Labiatae family, which is included in "Shen Nong's Materia Medica" and successive dynasties of herbal medicines. Danshen is a traditional Chinese medicine that promotes blood circulation and removes blood stasis, and is often used to treat cardiovascular and cerebrovascular diseases. The compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61K31/58A61P9/10A61P29/00A61P9/06A61P9/00A61P1/16A61P11/00A61P11/06A61P35/00A61P13/12A61P27/02A61P9/12A61P19/08A61P17/02A61P41/00
CPCA61K9/08A61K9/19C07J73/003
Inventor 付翌秋陈剑
Owner 北京桦冠医药科技有限公司