cas 150683-30-0, Tolvaptan | Articles data

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INTERMEDIATES AND METHODS FOR THE PREPARATION OF TOLVAPTAN AND ITS DERIVATIVES
The present invention relates to new intermediates for the synthesis of tolvaptan and its derivatives, as well as a method for its preparation involving said intermediates.
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(2021/12/31)

Preparation method of high-purity tolvaptan
The invention provides a preparation method of high-purity tolvaptan. Specifically, the quality of an intermediate N-(4-(7-chloro-5-oxo-2, 3, 4, 5-tetrahydro-1H-benzo[b]aza-1-ylcarbonyl)-3-methylphenyl)-2-methylbenzamide is controlled through crystallization and purification, so that the high-purity intermediate is obtained, and the high-purity tolvaptan is obtained by controlling the process conditions of reducing the intermediate to obtain the tolvaptan and subsequently purifying the tolvaptan. The method is low in cost, simple in preparation process and mild in reaction condition, the purity of the prepared tolvaptan reaches 99.9% or above, the yield reaches 80% or above, and industrial production is facilitated.
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(2021/06/23)

MANUFACTURING METHOD OF TOLVAPTAN, SALT THEREOF AND SOLVATE
PROBLEM TO BE SOLVED: To provide a manufacturing method of high purity and high yield tolvaptan, a salt thereof, or a solvate thereof without using a solvent with large environmental load, and having enhanced operability of a reaction. SOLUTION: There is provided a manufacturing method of tolvaptan, a salt thereof, or a solvate thereof, including a process for reacting following a described carboxylic acid derivative (I) with a chlorination agent such as thionyl chloride to convert it to a corresponding acid chloride (I), in which the reaction process is conducted in a presence of a solvent having relative dielectric constant of 10 or more and donor number of 20 or more, and represented by N,N-dimethyl acetamide, N-methyl-2-pyrrolidone, N.N'-dimethyl propylene urea or N,N,N',N'-tetramethyl urea. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
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(2020/04/18)

IMPROVED METHODS OF PRODUCING SYNTHETIC INTERMEDIATES OF TOLVAPTAN
PROBLEM TO BE SOLVED: To provide improved methods of producing 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine. SOLUTION: The present invention provides methods of producing 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine and 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine, which are synthetic intermediates of tolvaptan, by condensing an amino group and a carboxyl group in the presence of magnesium hydroxide. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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(2018/04/07)

Preparation method of high-purity tolvaptan
The invention discloses a preparation method of high-purity tolvaptan. The preparation method comprises the step of reducing N-[4-[(5R)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1-benazepine-1-formyl]-3-methyl phenyl]-2-methyl benzamide with sodium bis(2-methoxyethoxy) aluminumhydride, thereby obtaining the high-purity tolvaptan with the purity higher than or equal to 99.95%. The preparation method disclosed by the invention has the advantages that sodium bis(2-methoxyethoxy) aluminumhydride is adopted as a reducing agent for preparing tolvaptan by reducing N-[4-[(5R)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1-benazepine-1-formyl]-3-methyl phenyl]-2-methyl benzamide, the production of a dechlorination impurity IV can be extremely effectively inhibited, and finally the high-purity tolvaptan with the purity higher than or equal to 99.95% can be obtained, and high yield being 90% or above can be obtained while tetrahydrofuran or methyltetrahydrofuran is adopted as a reaction solvent.
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Paragraph 0023; 0024; 0025; 0026; 0027; 0028

(2018/03/01)

Preparation method of tolvaptan
The invention discloses a preparation method of tolvaptan. According to the preparation method, 7-chloro-1,2,3,4-tetrahydrobenzo[b]azepine-5-one and 4-nitro-2-methyl bromobenzene are taken as the primary raw materials; high purity tolvaptan is obtained after steps of carbonyl inserting reactions, reduction reactions, and acylation reactions, and the yield is high. The preparation method has the advantages that no bromine or tin dichloride is used; the preparation method does not generate a large amount of industrial waste water, and the environment is protected. At the same time, the generation of impurities namely a compound V and a compound VIII is avoided, and the purification becomes easier. No explosive, flammable, and toxic solvent such as chloroform, ether, and the like, is used, the requirements on the protection of workers are lowered, and the safe production is guaranteed. Moreover, the route design is novel, the raw materials are easily available, the operation of the technology is simple and feasible, and a simple and feasible method is provided for the massive industrial production of tolvaptan.
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(2017/07/22)

Preparation method for cardiovascular disease treatment drug
The invention provides a preparation method for a cardiovascular disease treatment drug. Specifically, the invention provides a compound represented by a formula (IV) shown in the description and a method for preparing Tolvaptan from the compound represented by the formula (IV). The method provided by the invention has the advantages of being environment-friendly, being easy in raw material obtaining and high in total yield, and the like, thereby being applicable to the industrialized preparation of Tolvaptan.
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(2016/10/08)

Preparation method of high-efficiency low-toxicity pitressin antagonist
The invention provides a preparation method of a high-efficiency low-toxicity pitressin antagonist. Specifically, the invention provides a compound having the formula A shown in the description, and a method for preparing tolvaptan through the compound having the formula A. All groups in the formula are defined in the description. The method has advantages of environmental protection, available raw materials, and high overall yield, and is suitable for industrial preparation of tolvaptan.
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(2016/10/17)

PROCESS FOR THE PREPARATION OF A BENZAZEPINE DERIVATIVE
Provided is an industrially scalable process for the preparation of a benzazepine derivative, namely, 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methyl benzoyl amino) benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (generically referred as Tolvaptan).
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Paragraph 0027

(2015/04/28)

PROCESS FOR PREPARING TOLVAPTAN INTERMEDIATES
The present invention provides a novel process for the preparation of 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one. The present invention also provides an improved process for the preparation of 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine. The present invention further provides an improved process for the preparation of 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine.
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(2013/07/31)

PROCESS FOR PREPARING TOLVAPTAN INTERMEDIATES
The present invention provides a novel process for the preparation of 7-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one. The present invention also provides an improved process for the preparation of 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine. The present invention further provides an improved process for the preparation of 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine.
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(2012/04/23)

PHARMACEUTICAL SOLID PREPARATION
An object of the present invention is to provide a gradual disintegration-type, sustained-release pharmaceutical solid preparation whose pharmacologically active substance release behavior is controlled. The solid pharmaceutical preparation of the present invention is a matrix-type preparation containing: (a) a pharmacologically active substance; (b) calcium polycarbophil; and (c) a specific sugar and/or sugar alcohol.
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(2011/07/29)

MATRIX-TYPE PHARMACEUTICAL SOLID PREPARATION
The present invention aims to provide a matrix-type solid preparation that has high-level release controllability for suppressing drug release in the upper gastrointestinal tract and accelerating drug release in the lower gastrointestinal tract, and that solves of all the above drawbacks caused by combining a plasticizer. The present invention provides a matrix-type pharmaceutical solid preparation that contains: (a) a methacrylic acid-based enteric polymer; and (b) a sugar and/or a sugar alcohol, wherein 1 g of the sugar and/or the sugar alcohol can be dissolved in not more than 4 g of water at a water temperature of 20 to 25° C.
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(2010/09/18)

PROCESS FOR PREPARING BENZAZEPINE COMPOUNDS OR SALTS THEREOF
This invention provides a process for preparing benzazepine compounds of the formula (1): wherein X1is a halogen atom, R1and R2are a lower alkyl group, or salts thereof as well as intermediate benzoic acid compounds in high yield and high purity on industrial scale, which are useful as an intermediate for preparing a pharmaceutically active 2,3,4,5-tetrahydro-1H-1-benzazepine compound having vasopressin antagonistic activity.
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Page/Page column 33-36

(2008/06/13)

Method of preparing benzazepines and derivatives thereof
The invention relates to a method of preparing benzazepine compounds having general formula (IA) consisting in reacting at least one compound having general formula (IIA) with an olefin, the compound thus obtained then being cyclised such as to produce tetralone, followed by the oxime derivative of same, which, by transformation by a Beckmann rearrangement, gives rise to the desired compounds.
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Page/Page column 13

(2008/06/13)

Aminocarbonylation route to tolvaptan
Pd-catalyzed aminocarbonylation between aryl bromide and NH-benzazepinone was effectively carried out to furnish the key intermediate for tolvaptan (up to 85%) in one step.
Torisawa, Yasuhiro,Furuta, Takuya,Nishi, Takao,Aki, Shinji,Minamikawa, Jun-ichi
p. 6455 - 6458
(2008/03/14)

A flexible approach for the preparation of substituted benzazepines: Application to the synthesis of tolvaptan
A practical preparation of benzazepine derivatives using a series of radical and ionic reactions is reported. This approach was applied to the synthesis of tolvaptan, a very promising vasopressin V2 receptor antagonist currently in clinical trials.
Cordero-Vargas, Alejandro,Quiclet-Sire, Beatrice,Zard, Samir Z.
p. 6165 - 6173
(2007/10/03)

7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5- tetrahydro-1H-1-benzazepine (OPC-41061): A potent, orally active nonpeptide arginine vasopressin V2 receptor antagonist
We previously reported a series of benzazepine derivatives as orally active nonpeptide arginine vasopressin (AVP) V2 receptor antagonists. After the lead structure OPC-31260 was structurally evaluated and optimized, the introduction of the 7-Cl moiety on the benzazepine and 2-CH3 on the aminobenzoyl moiety enhanced its oral activity. The new AVP-V2 selective antagonist OPC-41061 was determined to be a potent and orally active agent. Copyright (C) 1999 Elsevier Science Ltd.
Kondo, Kazumi,Ogawa, Hidenori,Yamashita, Hiroshi,Miyamoto, Hisashi,Tanaka, Michinori,Nakaya, Kenji,Kitano, Kazuyoshi,Yamamura, Yoshitaka,Nakamura, Shigeki,Onogawa, Toshiyuki,Mori, Toyoki,Tominaga, Michiaki
p. 1743 - 1754
(2007/10/03)