29110-47-2 Usage
Uses
Used in Pharmaceutical Industry:
Guanfacine is used as an antihypertensive agent for the treatment of high blood pressure. It helps in lowering blood pressure by acting on the central nervous system, specifically targeting α2-adrenergic receptors.
Used in Central Nervous System Applications:
Guanfacine is also used in the management of attention deficit hyperactivity disorder (ADHD) due to its ability to stimulate the central nervous system and improve focus and attention in patients.
Used in Research and Development:
Guanfacine's selective action on α2-receptors makes it a valuable compound for research and development in the field of neuroscience, particularly in the study of adrenergic receptor function and the development of new medications for various conditions related to the central nervous system.
Originator
Estulic,Sandoz,Switz.,1980
Manufacturing Process
2,6-Dichlorophenyl-acetyl-guanidine: A solution of 3.245 g (0.055 mol) of
guanidine in isopropanol is added to a solution of 11.7 g (0.05 mol) of 2,6-
dichlorophenyl-acetic acid ethyl ester (BP 142°C to 143°C/12 mm of Hg) in
20cc of isopropanol. The reaction mixture is allowed to stand overnight and is
subsequently concentrated by evaporation. After recrystallizing the residue
from methanol/ether 2,6-dichlorophenyl-acetyl-guanidine is obtained in the
form of white grains having a MP of 225°C to 227°C.
2,6-Dichlorophenyl-acetyl-guanidine hydrochloride: A solution of 5.6 g (0.025
mol) of 2,-dichlorophenylacetic acid chloride (BP 137°C to 138°C/12 mm of
Hg) in 10 cc of toluene is added dropwise to a mixture of 4.5 g (0.076 mol) of
guanidine and 60 cc of toluene. The reaction mixture is allowed to stand at
room temperature for 20 minutes, is then heated on a steam bath for 2 hours
and is subsequently cooled. The resulting precipitate is filtered off and washed
twice with 25 cc amounts of water in order to separate the guanidine
hydrochloride. The residue (2,6-dichlorophenyl-acetyl-guanidine) is washed
with chloroform for further purification and is then dissolved in 50 cc of
isopropanol. The pH-value of the solution is adjusted to 6 with ethanolic
hydrochloric acid and the solution is cooled. The resulting white needles are
again washed with chloroform. The resulting 2.6-dichlorophenyl-acetylguanidine hydrochloride has a MP of 213°C to 216°C.
Therapeutic Function
Antihypertensive
Synthesis
Guanfacin, N-amidino-2-(2,6-dichlorophenyl)acetamide (22.3.2), is also synthesized
in a very easy synthesis of reacting the acid chloride or ester of 2,6-
dichlorophenylacetic acid with guanidine.
Check Digit Verification of cas no
The CAS Registry Mumber 29110-47-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,1,1 and 0 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 29110-47:
(7*2)+(6*9)+(5*1)+(4*1)+(3*0)+(2*4)+(1*7)=92
92 % 10 = 2
So 29110-47-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H9Cl2N3O.ClH/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13;/h1-3H,4H2,(H4,12,13,14,15);1H
29110-47-2Relevant articles and documents
Solid-phase synthesis of N,N′-substituted acylguanidines
Dodd, Dharmpal S.,Zhao, Yufen
, p. 1259 - 1262 (2001)
An efficient method for the solid-phase synthesis of N,N′-substituted acylguanidines is presented. The key-step involves the N-acylation of resin immobilized S-methylisothiourea with a variety of carboxylic acids using PyAOP as the coupling agent. The resulting resin bound N-acyl-derivatives are reacted with a host of amines and the N-acyl,N′-alkyl(aryl)guanidines liberated from the resin upon exposure to TFA.
The preparation method of the overall tablet sizes hydrochloride (by machine translation)
-
Paragraph 0027; 0028; 0029, (2017/08/29)
The invention discloses a method for preparing the acid salt of the overall tablet sizes. In order to 2, 6 - dichloro acetic acid and methoxy isourea hydrochloride as the starting material, by catalytic condensation, aminolysis, salt, purifying to obtain the hydrochloric acid overall tablet sizes. The preparation method of mild reaction conditions, the operation is simple, compared with the prior art, reduce the operation step, reducing the total reaction time, reduce energy consumption, pollution is smaller, is beneficial to the environment. (by machine translation)
Substituted phenylacetylguanidines: a new class of antihypertensive agents
Bream,Lauener,Picard,Scholtysik,White
, p. 1477 - 1482 (2007/10/05)
The synthesis of a new series of phenylacetylguanidines is described. Several of them exhibited high antihypertensive activity in the rat. The most potent member of the series is N amidino 2 (2,6 dichlorophenyl) acetamide hydrochloride [2,6 dichlorophenylacetylguanidine hydrochloride, compound 19], which is now in clinical study under the clinical code number BS 100-141. The structure activity relationships in this class of compounds are discussed.
