CN103923014A - Preparation method of cyclocreatine - Google Patents
Preparation method of cyclocreatine Download PDFInfo
- Publication number
- CN103923014A CN103923014A CN201410185623.0A CN201410185623A CN103923014A CN 103923014 A CN103923014 A CN 103923014A CN 201410185623 A CN201410185623 A CN 201410185623A CN 103923014 A CN103923014 A CN 103923014A
- Authority
- CN
- China
- Prior art keywords
- ethylenediamine
- preparation
- quadrol
- sodium
- acetonitrile
- 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
- 0 *N(CC[N+]1)C1=N Chemical compound *N(CC[N+]1)C1=N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of cyclocreatine. The preparation method comprises the following steps: condensing ethylenediamine and hydroxyl acetonitrile serving as raw materials at 0-20 DEG C to obtain ethylenediamine acetonitrile; then, carrying out catalytic hydrolysis on ethylenediamine acetonitrile and sodium hydroxide at 60-100 DEG C to obtain ethylenediamine sodium acetate; and then, adding and cyclizing ethylenediamine sodium acetate in the environment of a methanol solution through nitrile brominate to obtain cyclocreatine. The preparation method provided by the invention is short in synthetic line, and byproducts can be recycled, so that no solid and gas residues are generated. Ammonia gas produced in the process is absorbed by water to be sold as ammonia water. Solid sodium bromide is obtained in a way of sodium bromide formed by a product mother liquid through decompressed concentration and can be sold as an inorganic chemical material.
Description
technical field:
The present invention relates to a kind of circular muscle acid preparation method.
background technology:
Circular muscle acidifying formal name used at school is called 2-imino--1-imidazolidine acetic acid, and structural formula is:
The current bibliographical information of application of circular muscle acid is few, and it is the nonessential amino acid of human body for just current contents known, is the amino acid that contains imidazolyl heterocycle, and it is known as sports nutrition product, and meanwhile, it has antitumous effect report.Circular muscle acid is expensive, not yet finds at present manufacturer, and the bibliographical information of its synthetic method and synthesis condition has no open.
summary of the invention:
Given this, be necessary to find a kind of circular muscle acid preparation method.
A kind of circular muscle acid preparation method, obtains quadrol base acetonitrile taking quadrol and hydroxyacetonitrile as raw material reacts condensation at 0 ~ 20 DEG C:
,（1）
Then quadrol base acetonitrile is obtained to quadrol guanidine-acetic acid sodium with sodium hydroxide catalytic hydrolysis at 60 ~ 100 DEG C:
， （2）
Again quadrol guanidine-acetic acid sodium is obtained to circular muscle acid through bromination nitrile addition cyclization under methanol solution environment:
， （3）
Preferably, the temperature of reaction of formula (1) is 20 DEG C, and the temperature of reaction of formula (2) is 100 DEG C.
Synthesis path of the present invention is short, and the equal recoverable of byproduct does not have solid, gas residue dirt, the ammonia water producing in technique absorbs to be sold as ammoniacal liquor, the Sodium Bromide that finished mother liquid forms, obtains solid brominated sodium by concentrating under reduced pressure, can be used as Inorganic Chemicals and sells.This technique has all played active effect from environmental protection or cost.
embodiment:
A kind of circular muscle acid preparation method, obtains quadrol base acetonitrile taking quadrol and hydroxyacetonitrile as raw material reacts condensation at 0 ~ 20 DEG C:
，（1）
Then quadrol base acetonitrile is obtained to quadrol guanidine-acetic acid sodium with sodium hydroxide catalytic hydrolysis at 60 ~ 100 DEG C:
， （2）
Again quadrol guanidine-acetic acid sodium is obtained to circular muscle acid through bromination nitrile addition cyclization under methanol solution environment:
， （3）
In the present embodiment, the temperature of reaction of formula (1) is 20 DEG C, and the temperature of reaction of formula (2) is 100 DEG C.
Claims (2)
1. a circular muscle acid preparation method, is characterized in that: obtain quadrol base acetonitrile taking quadrol and hydroxyacetonitrile as raw material reacts condensation at 0 ~ 20 DEG C:
，（1）
Then quadrol base acetonitrile is obtained to quadrol guanidine-acetic acid sodium with sodium hydroxide catalytic hydrolysis at 60 ~ 100 DEG C:
， （2）
Again quadrol guanidine-acetic acid sodium is obtained to circular muscle acid through bromination nitrile addition cyclization under methanol solution environment:
， （3）。
2. circular muscle acid preparation method as claimed in claim 1, is characterized in that: the temperature of reaction of formula (1) is 20 DEG C, and the temperature of reaction of formula (2) is 100 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410185623.0A CN103923014A (en) | 2014-05-05 | 2014-05-05 | Preparation method of cyclocreatine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410185623.0A CN103923014A (en) | 2014-05-05 | 2014-05-05 | Preparation method of cyclocreatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103923014A true CN103923014A (en) | 2014-07-16 |
Family
ID=51141437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410185623.0A Pending CN103923014A (en) | 2014-05-05 | 2014-05-05 | Preparation method of cyclocreatine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103923014A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016036699A1 (en) * | 2014-09-03 | 2016-03-10 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
| JP2018513122A (en) * | 2015-03-11 | 2018-05-24 | ルモス ファーマ， インコーポレイテッド | Synthesis of cyclocreatine and its analogues |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439005A (en) * | 2000-02-15 | 2003-08-27 | 苏根公司 | Pyrrole substituted 2-indolinone protein kinase inhibitors |
| CN1541098A (en) * | 2001-08-15 | 2004-10-27 | �ո��� | Combination therapy for treatment of cancer |
| WO2006073923A2 (en) * | 2004-12-30 | 2006-07-13 | Nour Heart, Inc. | Phosphagen synthesis |
-
2014
- 2014-05-05 CN CN201410185623.0A patent/CN103923014A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439005A (en) * | 2000-02-15 | 2003-08-27 | 苏根公司 | Pyrrole substituted 2-indolinone protein kinase inhibitors |
| CN1541098A (en) * | 2001-08-15 | 2004-10-27 | �ո��� | Combination therapy for treatment of cancer |
| WO2006073923A2 (en) * | 2004-12-30 | 2006-07-13 | Nour Heart, Inc. | Phosphagen synthesis |
Non-Patent Citations (2)
| Title |
|---|
| ROWLEY G. L.等: "On the Specificity of Creatine Kinase. New Glycocyamines and Glycocyamine Analogs Related to Creatine", 《J. AM. CHEM. SOC.》 * |
| 姚方等: "肌氨酸钠的合成研究", 《科技进展》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016036699A1 (en) * | 2014-09-03 | 2016-03-10 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
| CN107001280A (en) * | 2014-09-03 | 2017-08-01 | 卢莫斯制药公司 | The synthesis of circular muscle acid and the like |
| AU2015312159B2 (en) * | 2014-09-03 | 2019-03-07 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
| US10493062B2 (en) | 2014-09-03 | 2019-12-03 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
| JP2018513122A (en) * | 2015-03-11 | 2018-05-24 | ルモス ファーマ， インコーポレイテッド | Synthesis of cyclocreatine and its analogues |
| US10081605B2 (en) | 2015-03-11 | 2018-09-25 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
| US10377721B2 (en) | 2015-03-11 | 2019-08-13 | Lumos Pharma, Inc. | Synthesis of cyclocreatine and analogs thereof |
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| C06 | Publication | ||
| PB01 | Publication | ||
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| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20140716 |