cas 161596-47-0, (S)-(+)-GLYCIDYL PHTHALIMIDE

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Novel series of highly potent non-peptide growth hormone secretagogues with improved bioavailability
The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2-hydroxypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)- carbonylamino]-3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2- ylpropionamide ((2S)-4e) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.
Ishige, Hirohide,Ishiyama, Nobuo,Mimura, Mitsuo,Hayashida, Mitsuo,Okuno, Tadashi,Ukai, Kiyoharu,Kiyofuji, Takeshi,Yoneda, Yasuo,Tauchi, Shinji,Aoyama, Akinori,Inoguchi, Kiyoshi
p. 561 - 566
(2006)
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Preparation method of (S)-glycidyl phthalimide
The invention provides a preparation method of (S)-glycidyl phthalimide (II). Phthalimide (III) and (S)-1-substituted epoxypropane (IV) which are used as raw materials react under the action of a catalyst to generate 2-((S)-3-substituted-2-hydroxypropyl)isoindoline-1,3-dione (V), and the 2-((S)-3-substituted-2-hydroxypropyl)isoindoline-1,3-dione (V) is subjected to a cyclization reaction to obtainthe (S)-glycidyl phthalimide (II). The method has the advantages of cheap and easily available raw materials, easiness in realization of reaction conditions, low cost, short reaction route, simplicity in operation, simplicity in post-treatment, few side reactions, high yield and high purity of the target product, and suitableness for industrial production.
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(2020/03/29)

Preparation method of rivaroxaban intermediate
The invention provides a preparation method of a rivaroxaban intermediate. The preparation method comprises: (1) carrying out a reaction on a compound A and a compound B in an alcohol or an alcohol aqueous solution to obtain a compound C; and (2) reacting the compound C with N,N'-carbonyldiimidazole in a reaction solvent selected from acetonitrile or butyronitrile to obtain a reaction solution containing a compound D, and performing cooling crystallization to obtain a compound D.
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Paragraph 0057-0065

(2020/05/02)

Low-cost and high-purity S-glycidyl phthalimide synthesis method
The invention relates to a low-cost and high-purity S-glycidyl phthalimide synthesis method, which comprises: carrying out a substitution reaction on potassium phthalimide and R-2,2-disubstituted-4-halomethyl-1,3-dioxolane to generate N-(S-2,2-disubstituted-1,3-dioxolane-4-)methylphthalimide, carrying out a ketone (aldehyde) removing ring-opening reaction to produce N-2-S-hydroxy-3-halogenated n-propyl phthalimide, and finally carrying out an elimination reaction to remove hydrogen halide so as to generate S-glycidyl phthalimide, wherein S-glycidyl phthalimide is the key intermediate for the preparation of rivaroxaban. According to the present invention, the synthesis method has advantages of inexpensive and easily-available raw materials, high stability, high reaction selectivity and highproduction efficiency, and the obtained S-glycidyl phthalimide has advantages of low cost and high purity, and is favorable for the industrial production of high-purity rivaroxaban.
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Paragraph 0062; 0063; 0064; 0065; 0066

(2019/03/10)

A novel homochiral metal-organic framework with an expanded open cage based on (: R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl: synthesis, X-ray structure and efficient HPLC enantiomer separation
A new homochiral metal-organic framework (MOF) with an expanded open cage based on the (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl ligand was synthesized and utilized as a novel chiral stationary phase for high-performance liquid chromatography. Twelve racemates including sec-alcohols, sulfoxides, epoxides, lactone, 1,3-dioxolan-2-one, and oxazolidinone were used as analytes for evaluating the separation properties of the chiral-MOF-packed column. Experimentally, the homochiral MOF offered good molecular recognition ability, which suggests good prospects for the application of chiral MOFs as stationary phases for enantioseparation.
Tanaka, Koichi,Kawakita, Tomohiro,Morawiak, Maja,Urbanczyk-Lipkowska, Zofia
p. 487 - 493
(2019/01/21)

Preparation method of S-N-glycidol phthalimide
The invention relates to a preparation method of S-N-glycidol phthalimide. According to the method, recyclable anion exchange resin is used for catalyzing reaction in the preparation process of the S-N-glycidol phthalimide, so that the production cost is reduced; the emission requirements are reduced; the problem that a phase transfer catalyst is difficultly removed and influences the quality of aproduct is solved; the reaction time is further reduced; the special requirements on equipment caused by application of potassium tert-butoxide are avoided; the production cost is reduced; the preparation method is suitable for industrial production.
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Paragraph 0075; 0076; 0077

(2018/09/12)

Preparation method of rivaroxaban intermediate
The invention relates to a preparation method of rivaroxaban intermediate S-N-glycidyl phthalimide. According to the method, catalytic reaction is carried out by using recoverable aluminum oxide in apreparation process of S-N-glycidyl phthalimide, so that the production cost is reduced, the emission requirement is reduced, the problem that the product quality is affected by a phase transfer catalyst difficultly eliminated is solved, the reaction time is further shortened, the special requirement on equipment caused by the use of potassium tert-butanolate is avoided, the production cost is reduced, and therefore, the preparation method is particularly suitable for industrial production.
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Paragraph 0086; 0087; 0088

(2018/09/12)

AN IMPROVED PROCESS FOR THE PREPARATION OF LINEZOLID
The present invention relates to an improved process for the preparation of Linezolid. More specifically, the present invention relates to an improved process for preparing(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl] phthalimide and (S)-glycidyl phthalimide intermediates, which are used in the preparation of Linezolid.
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(2017/11/14)

Process for the preparation of linezolid
The present invention relates to an improved process for the preparation of Linezolid. More specifically, the present invention relates to an improved process for preparing (S)—N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl] phthalimide and (S)-glycidyl phthalimide intermediates, which are used in the preparation of Linezolid.
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Page/Page column 16

(2017/05/31)

Pilot scale process development of SL65.0102-10, an N-diazabicyclo[2.2.2]-octylmethyl Benzamide
The process development and improvements for route selection, adapted to large scale for the pilot-scale preparation of SL65.0102-10, an N-diazabicyclo[2.2.2]-octylmethyl benzamide, a 5-HT3 and 5-HT4 receptor active ligand for the treatment of neurological disorders such as cognition impairment, are described in this article. Notable steps and enhancements are compared to the original route, including the improvement of a chiral epoxide synthesis by shortening the number of chemical steps, the deprotection of a quaternary ammonium salt, and the redesign of the final amidification coupling to avoid chromatography.
Lienard, Philippe,Gradoz, Philippe,Greciet, Hélène,Jegham, Samir,Legroux, Didier
p. 18 - 22
(2017/11/27)

S-epihydric a phthalic acid imide preparation method
The invention relates to a preparation method of S-glycidylphthalimide. The preparation method is characterized in that in a reaction of potassium phthalimide or phthalimide and (S) epichlorohydrin, a phase transfer catalyst and potassium iodide are used so that S-glycidylphthalimide synthesis is realized. Compared with the prior art, the preparation method greatly improves an S-glycidylphthalimide yield, has simple and safe processes, produces high-purity products, has a low cost and is suitable for industrial production of S-glycidylphthalimide.
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Paragraph 0034; 0035

(2017/03/08)

PROCESS FOR THE PREPARATION OF RIVAROXABAN
Disclosed is a process for the preparation of rivaroxaban and purifying rivaroxaban.
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Paragraph 0131

(2016/06/01)

A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols
A highly enantiospecific, azide-free synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)- and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-diones with the diethyl malonate anion and subsequent decarboxylation.
Babu, Meruva Suresh,Raghunadh, Akula,Ramulu, Konda,Dahanukar, Vilas H.,Syam Kumar, Unniaran K.,Dubey, P. Kumar
p. 1507 - 1515
(2015/02/19)

PROCESSES AND INTERMEDIATES FOR PREPARING RIVAROXABAN
The invention discloses processes for the preparation of rivaroxaban and its pharmaceutically acceptable salts, solvates, and hydrates thereof. The invention also relates to novel intermediates for the preparation of rivaroxaban.
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Paragraph 0207; 0208

(2015/01/07)

PROCESSES AND INTERMEDIATES FOR PREPARING RIVAROXABAN
The invention discloses processes for the preparation of rivaroxaban and its pharmaceutically acceptable salts, solvates, and hydrates thereof. The invention also relates to novel intermediates for the preparation of rivaroxaban.
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Page/Page column 41

(2013/07/19)

A METHOD OF MANUFACTURING 2-({(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]- L,3-OXAZOLIDIN-5-YL}METHYL)-LH-ISOINDOL-L,3(2H)-DIONE WITH A HIGH OPTICAL PURITY
Highly optically pure 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-l,3-oxazolidin- 5-yl} methyl)- lH-isoindol- l,3(2H)-dione (I) is obtained by reaction of 2-((2R)-2-hydroxy-3-[4-(3- oxo-4-moφholinyl)phenyl]amino-propyl)- lH-isoindol- l,3(2H)-dione (III), containing the (2S)- isomer (Illb), with N,N-carbonyldiimidazole in tetrahydrofuran, preferably without the presence of the catalyst 4-dimethylaminopyridine, said reaction being carried out in such a manner that it is terminated at a moment when the reaction mixture still contains the unreacted compound of formula III in an amount which is in the range of a 3 to 5 fold the initial amount of the (2S)- isomer in the starting substance of formula III.
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Page/Page column 9-10

(2012/04/17)

2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.
Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
supporting information; experimental part
p. 1380 - 1382
(2010/09/05)

ACYCLIC 1,4-DIAMINES AND USES THEREOF
This invention relates to novel compounds useful in the treatment of diseases associated with TRPV4 channel receptor. More specifically, this invention relates to certain acyclic diamines, which are agonists of TRPV4 channel receptors.
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Page/Page column 37; 98-99

(2008/06/13)

PROCESS FOR THE PREPARATION OF CHIRAL GLYCIDYLPHTHALIMIDE IN HIGHLY OPTICAL PURITY
The present invention relates to a process for the preparation of highly optical pure glycidylphthalimide. More particularly, the present invention relates to a process for the preparation of chiral glycidylphthalimide, which comprises the steps of reacting an optically active 3-susbstituted 1-amino-2-propanol acid addition salt with phthalic anhydride in a presence of a base to obtain N-(3-substituted-2-hydroxypropyl)phthalimide and subjecting the obtained compound to an epoxide cyclization reaction to prepare the targeted glycidylphthalimide. According to the process, the chirality of the starting material is substantially retained throughout overall procedures. Therefore, the process can prepare the targeted glycidylphthalimide in an optically pure form having 99%ee or higher. And, the reactions are carried out under mild conditions through overall procedures and in a single reaction vessel without any special purification. This increases the yield of the target compound.
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Page/Page column 8-10

(2008/06/13)

PROCESS FOR PREPARATION OF PHTALIMIDE
The present invention is directed to a novel process for the synthesis of (S) -glycidyl phthalimide and to novel intermediates in the process. The process comprises, reacting a (R) -3 -Chloro-1,2-propanediol and phtalimide salt. Then reacting the product with trimethylorthoacetate and an essentially water free acid. Then reacting the product with acetyl halogenide and do a basic ester hydrolysis.
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Page/Page column 5

(2008/06/13)

A Mitsunobu diol cyclisation to chiral morpholines and dioxanes
A diol cyclisation under Mitsunobu conditions is presented, which allows access to chiral substituted morpholines and dioxanes. Georg Thieme Verlag Stuttgart.
Wilkinson, Mark C.,Bell, Rebecca,Landon, Robert,Nikiforov, Petar O.,Walker, Andrew J.
p. 2151 - 2153
(2008/02/05)

Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.
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Page/Page column 23

(2008/06/13)

GLYT1 TRANSPORTER INHIBITORS
The invention provides a compound of formula (I): or a salt, solvate or a physiologically functional derivative thereof, wherein R1 to R10 are as defined in the specification and uses of such compounds. The compounds inhibit GlyT1 transporters and are useful in the treatment of certain neurological and neuropsychiatric disorders, including schizophrenia.
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Page/Page column 57-58

(2010/02/12)

Process for preparing glycidylphthalimide
A process for preparing glycidylphtalimide or its optically active compound by reacting a phthalimide alkali metal salt with an epihalohydrin or an optically active epihalohydrin in an alcohol solvent; or by reacting phthalimide with an epihalohydrin or an optically active epihalohydrin in the presence of an alkali metal carbonate, an alkali metal hydrogencarbonate or a quaternary ammonium salt to obtain a N-(3-halogeno-2-hydroxypropyl)phthalimide and then by cyclizing the product with an alkali metal alkoxide.
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Page 6-7

(2008/06/13)

GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
Compounds of formula (I), salts, solvates and physiologically functional derivatives thereof are disclosed. Methods of preparation and uses thereof in medicine, for the treatment of a disorder mediated by GlyT1, such as for example schizophrenia, are also disclosed.
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Page 17-18

(2008/06/13)

GLYT1 TRANSPORTER INHIBITORS AND USES THEREOF IN TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS
Compounds of formula (I), salts, solvates and physiologically functional derivatives thereof are provided: formula (I) wherein R1 and R2 is independently selected from hydrogen, optionally substituted C1-6alkyl, optionally substituted C3-6cycloalkyl, optionally substituted aryl, optionally substituted arylC1-4alkyl and optionally substituted arylC3-6cycloalkyl, wherein R1 and R2 are not both hydrogen, or R1 and R2, together with the nitrogen atom to which they are attached, are linked to form an optionally substituted 4-, 5-, 6- or 7-membered saturated ring, wherein one or more of the carbon atoms is optionally replaced by a heteroatom independently selected from N, O and S; R3 is an optionally substituted group of formula (a): wherein m and n are independently 0, 1, 2 or 3 and m+n is 2, 3 or 4; each Z is independently -CH2-, -NH-, -O- or -S-; and each Y is independently CH or N; R4 and R5 are independently selected from hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C3-C6cycloalkyl, optionally substituted aryl and optionally substituted arylC1-C4 alkyl; and R6, R7, R8 and R9 are independently selected from hydrogen, optionally substituted C1-C6 alkyl and optionally substituted arylC1-C4alkyl, or R6 and R7 together form an optionally substituted C3-C6 cycloalkyl group, or R8 and R9 together form an optionally substituted C3-C6 cycloalkyl group. Methods of preparation and uses of the compounds in medicine for the treatment of a disorder mediated by GlyT1, for example schizophrenia, are also disclosed.
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Page 18

(2008/06/13)

The preparation and alkylation of a butanedione-derived chiral glycine equivalent and its use for the synthesis of α-amino acids and α,α-disubstituted amino acids
A benzyloxycarbonyl protected glycine equivalent 2 has been prepared in enantiopure form and has been used in the synthesis of both α-substituted amino acids and α,α-disubstituted amino acids. The process involved deprotonation to form the corresponding enolates which underwent stereoselective alkylation with various electrophiles and upon hydrolysis gave the corresponding amino acid derivatives as enantiomerically pure products.
Harding, Christopher I.,Dixon, Darren J.,Ley, Steven V.
p. 7679 - 7692
(2007/10/03)

HETEROCYCLIC COMPOUNDS
The invention concerns blood clotting. The invention particularly concerns certain heterocyclic compounds, methods for the production thereof, their use for treating and/or preventing diseases, and their use for producing medicaments for treating and/or preventing diseases.
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Page/Page column 37

(2010/02/09)

A 2,3-butanedione protected chiral glycine equivalent--a new building block for the stereoselective synthesis of enantiopure N-protected alpha-amino acids.
A new chiral glycine equivalent 7 has been synthesised from glycidol using a chiral memory protocol, and its use in the synthesis of N-Z protected alpha-amino acids was demonstrated in a series of diasteroselective lithium enolate alkylation reactions and subsequent acid hydrolyses.
Dixon, Darren J,Harding, Christopher I,Ley, Steven V,Tilbrook, D Matthew G
p. 468 - 469
(2007/10/03)

Heteroatom-bearing ligands and metal complexes thereof
Novel compounds containing a heteroatom-bearing bridge and novel complexes of these compounds with metals. The novel compounds and complexes are useful in diagnostic and therapeutic methods.
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(2008/06/13)

Studies on quinazolines. 6. Asymmetric synthesis of (S)-(+)- and (R)-(-)-3-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-5-methylthio-2,3- dihydroimidazo[1,2-c]quinazolines
The titled compounds have been synthesized in five steps from commercially available (R)-(+) and (S)-(-)-glycidol. The overall yield was about 29% with ee>98.5%. Copyright
Gutcait, Alexander,Wang, Kuang-Chao,Liu, Hsiu-Wen,Chern, Ji-Wang
p. 1641 - 1648
(2007/10/03)