Hebei youze Biotechnology Co.,Ltd(expird)
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CAS NO.148553-50-8
High(1-50)KilogramHigh(51-500)Kilogram
Our Advantage
1.Best quality with competitive price.
2.Quick shipping,delivery on time.
3.We have a pharmaceutical raw material production plant and a reagent R&D center
4.Support multiple trading methods and payment.We support wire transfer, , Paypal or escrow payment.
5.One to one business communication.
6.OEM/ODM Avaliable.
7.We offer convenient one-station purchasing service.Our professionaland thoughtful after-sales service eliminates your worries.
8.We has many years exporting experience in active pharmaceutical ingredient products.,Strictly on selecting raw materials.
Quick Details
Classification: Pharmaceutical Intermediates
Cas NO.: 148553-50-8
Name: Pregabalin
Formula: C8H17NO2
Melting Point: 194-196ºC
Boiling Point: 274.0±23.0 °C at 760 mmHg
Refractive index: 1.465
Flash Point: 119.5±22.6 °C
Density: 1.0±0.1 g/cm3
PSA: 63.32000
LogP: 1.12
Adverse effects: Pregabalin can be associated with adverse effects at the level of the nervous system and other systems.
Usage: Pregabalin has an approved indication and is widely used for the treatment of generalized anxiety disorder. Several randomized, double- blind, placebocontrolled trials found that pregabalin is an effective treatment for patients with generalized anxiety disorder and social anxiety disorder. Possible implications in the treatment of mood disorders and benzodiazepines dependence are emerging. Moreover, pregabalin may be a therapeutic agent for the treatment of alcohol abuse, in both withdrawal phase and relapse prevention.
Pregabalin chemically known as 3 - (5 ) - a m i n o m c t h y 1 - 5 - m c t h y 1 hexanoic acid having structure formula (I), is known to treat several central nervous system disorders that include epilepsy, neuropathic pain, anxiety and social phobia
(S)-Pregabalin has been found to activate GAD ( L-Glutamic Acid Decarboxylase) in a dose dependent manner and promote production of GABA (Gamma-Amino Butyric Acid), one of the major inhibitory neurotransmitters of brain. The discovery of anti-seizure activity was first disclosed in US Patent No. 5,563,175.
Pregabalin has been prepared in various ways. One of the common approaches involves synthesis of racemic Pregabalin typically a 50:50 mixture of R and S isomers and subsequent resolution through diastereomeric salt formation. Such an approach was found in PCT patent publications such as WO2009122215, W02009087674, W02009044409, WO 2008138874, WO2009125427 and W02009001372. The major difficulties associated with these approaches involve the loss of //-enantiomer along with a part of 5- isomer as well and this cannot be effectively recycled leading to increase in cost of production. Another approach has utilized resolution in the intermediate stage as a strategy. The scheme 1 outlines the approach described in PCT patent publication WO 9638405. The synthesis involves Knoevenagel condensation followed by Micheal addition and acidic hydrolysis which gives diacid. The diacid was converted to mono amide which was resolved by ( R )- phenylethylamine. After liberation of iCmono acid amide it was converted to (S)-Pregabalin by Hoffmann degradation. The overall yield was 12% and 99.8% enantiomeric excess (ee) over 8 steps. All commercial reagents were used, and the chiral auxiliary can be recovered.
Scheme 1:
Another approach as shown in scheme 2 is described in PCT patent publication WO2008137512, which involved the resolution of amide intermediate followed by Hoffmann degradation. A further modification was described in Org. Process Res. Dev., 2009, 13, 812-13, which involved the recovery of unwanted isomer i.e. racemization using organic base in solvent which lead to racemic acid amide intermediate.
Scheme 2:
The approach described in patent publications W02008062460 and U.S. Patent No. 6,046,353 is shown in scheme 3, which involved the condensation of diethyl malonate with isovaleraldehyde followed by cyanation. The product is selectively decarboxylated to cyano ester which on further hydrolysis gives cyano acid. The cyano acid was hydrogenated to racemic Pregabalin, which was resolved by using (S)-mandclic acid with overall yield of 15.5% and enantiomeric excess >99.5% over 6 steps.
Scheme 3:
Another commonly used scaffold was found to be 3-isobutylglutaric acid anhydride (IBG). In U.S. Patent publication No. 20090143615 and European Patent publication No. EP2067768 disclosed the synthesis of Pregabalin as shown in scheme 4 which involved the ring opening by hydrazine followed by conversion to urethane acid by Curtius rearrangement. This intermediate was resolved by using (S)-PEA (phenylethylamine). The release of chiral auxiliary followed by hydrolysis gave Pregabalin in overall yield of 12% over 4 steps with 99.8% enantiomeric excess. This method also suffers from the loss of unwanted iUisomer which cannot be efficiently recycled.
Scheme 4:
Asymmetric ring opening of 3-isobutylglutaric acid anhydride and subsequent chemical transformation to enantiopure Pregabalin constitute another approach. The PCT patent publication W02008118427 describes the synthesis of (S)-Pregabalin starting from 3- isobutyl-glutaric anhydride as depicted in scheme 5, which involve the stereo selective ring opening with (S)-PEA with good yield and enantiomeric excess. This was converted to amide by mixed anhydride approach. The amide was subjected to Hoffman degradation followed by PEA amide hydrolysis in two different approach to yield Pregabalin in 59.5% and 38.8% respectively with purity >99.5%.
Packaging & Delivery
Packaging Detail: customized
Payment Term: T/T or L/C, D/P, DIA, WU, MG
Delivery Detail: Usually within 3-5 working days after full payment Shipping: EMS, DHL, TNT, UPS, FEDEX, BY AIR, BY SEA
Our Company
Hebei Youze Biological Technology Co., Ltd. has a registered capital of 1 million yuan and is one of the most dynamic foreign trade companies in the Chinese market. We have a pharmaceutical raw material production plant and a reagent R&D center. We now have the most complete product line. In addition, we have developed and produced tens of thousands of reagents. We also have the business of custom synthesis of various organic compounds as a supplement. We can synthesize almost all chemicals. Our goal is to survive by quality and develop by credit.
In the past two years, our products have spread over more than 30 countries in the world, Europe, South America, North America, Southeast Asia and Africa. We work with friends all over the world to develop the best quality products, the most reasonable prices and safe and effective transportation. Product can be ordered from milligrams to tons. Meet the purchase of new and old customers. We will not let you down.