EP3759081A1 - Procédé de préparation amélioré de maléate de propiomazine - Google Patents
Procédé de préparation amélioré de maléate de propiomazineInfo
- Publication number
- EP3759081A1 EP3759081A1 EP19760246.9A EP19760246A EP3759081A1 EP 3759081 A1 EP3759081 A1 EP 3759081A1 EP 19760246 A EP19760246 A EP 19760246A EP 3759081 A1 EP3759081 A1 EP 3759081A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- propiomazine
- preparation
- maleate
- base
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Definitions
- the present invention relates to an improved process for the preparation of Propiomazine maleate. More particularly, the invention relates to a cost-effective process, which provides Propiomazine maleate of formula-I with high purity, which is free from isomeric impurity, specifically isopropiomazine.
- Propiomazine maleate of formula-I is a phenothiazine derivative, chemically known as 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one maleate.
- Propiomazine is an antihistamine drug, which acts by blocking H1 receptors. It is used to treat insomnia, and to produce sleepiness or drowsiness and to relieve anxiety before or during surgery or other procedures and in combination with analgesics also during labor. Propiomazine is a derivative of Phenothiazine.
- the main object of the present invention is to provide simple, cost-effective and industrially viable method for the preparation of Propiomazine maleate of formula-I on commercial scale.
- the main aspect of the present invention is to provide an improved process for the preparation of Propiomazine maleate of formula-I.
- the second aspect of the present invention is process for preparation of Propiomazine maleate with high purity which is free from isomeric impurity of formula-III.
- the isomeric impurity produced during the preparation of Propiomazine base of formula II is controlled during the preparation of Propiomazine maleate.
- the Propiomazine base of formula II is dissolved in alcoholic media to get a clear solution. Addition of maleic acid to the above clear solution produces Propiomazine maleate of formula-I which is free from isomeric impurity.
- the present invention relates to an improved process for the preparation of Propiomazine maleate of formula-I and its purification from the undesired isomeric impurity. i.e., isopropiomazine of formula-III.
- the first embodiment of the present invention is an improved process for the preparation of 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one of formula-II, which comprises condensing 2-propionyl phenothiazine of formula –IV
- Further embodiment of the present invention relates to process for preparation of Propiomazine maleate with high purity and free from isopropiomazine impurity of formula-III.
- the isomeric impurity is controlled during the preparation of Propiomazine maleate.
- the crude Propiomazine base obtained in the above condensation step contains isomeric impurity of 20-25%.
- the Propiomazine base of formula II is dissolved in alcoholic media to get a clear solution. Addition of maleic acid to the above clear solution produces Propiomazine maleate of formula-I which is free from isomeric impurity.
- the process is schematically represented as below:
- the base used in condensation step is selected from potassium hydroxide, sodium hydroxide, potassium tertiary butoxide, preferably potassium hydroxide.
- solvent used in condensation step is selected from the group comprising of toluene, xylene, preferably toluene.
- alcoholic media used in purification step is selected from methanol, ethanol, isopropyl alcohol, preferably methanol.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN201841007386 | 2018-02-27 | ||
PCT/IN2019/050128 WO2019167058A1 (fr) | 2018-02-27 | 2019-02-18 | Procédé de préparation amélioré de maléate de propiomazine |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3759081A1 true EP3759081A1 (fr) | 2021-01-06 |
EP3759081A4 EP3759081A4 (fr) | 2022-01-05 |
Family
ID=67804887
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19760246.9A Pending EP3759081A4 (fr) | 2018-02-27 | 2019-02-18 | Procédé de préparation amélioré de maléate de propiomazine |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP3759081A4 (fr) |
WO (1) | WO2019167058A1 (fr) |
-
2019
- 2019-02-18 WO PCT/IN2019/050128 patent/WO2019167058A1/fr unknown
- 2019-02-18 EP EP19760246.9A patent/EP3759081A4/fr active Pending
Also Published As
Publication number | Publication date |
---|---|
EP3759081A4 (fr) | 2022-01-05 |
WO2019167058A1 (fr) | 2019-09-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2753548C1 (ru) | Способ производства никотина | |
JP5632279B2 (ja) | 塩酸イバブラジンの調製方法及びポリモルフ | |
WO2014026657A2 (fr) | Procédé pour la préparation d'un dérivé d'acide 2-méthyl-2'-phénylpropionique utilisant de nouveaux intermédiaires | |
US11352346B2 (en) | Process for the preparation of 2-(5-methoxyisochroman-1-yl)-4,5-dihydro-1H-imidazole and the hydrogensulfate salt thereof | |
KR20110036055A (ko) | 고순도의 수니티닙 및 이의 약학적으로 허용가능한 염의 개선된 제조 방법 | |
WO2012059941A1 (fr) | Procédé pour préparation de malate de sunitinib et sels correspondants | |
JP2005507900A (ja) | シタロプラムの製造方法 | |
US10654803B2 (en) | Transition metal-catalyzed protodecarboxylation of alpha-halo-acrylic acid derivatives | |
KR20170102204A (ko) | 테트라하이드로퀴놀린 유도체 제조용의 합성 중간체를 제조하기 위한 방법 | |
US20090299077A1 (en) | Salts of (R)-5-(2phenylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole, 5-bromo-3-[(R)-1-methyl-pyrrolidin-2-ylmethyl]-1H-indole and of eletriptan | |
TWI291956B (en) | Improved process | |
WO2005046568A2 (fr) | Procede pour produire du metoprolol et des sels de celui-ci | |
WO2012026897A1 (fr) | Procédé pour la préparation d'imatinib base | |
EP3759081A1 (fr) | Procédé de préparation amélioré de maléate de propiomazine | |
US9745264B2 (en) | Method for preparing silodosin and intermediate thereof | |
AU2002236076B2 (en) | Preparation of phthalanes | |
CN107428648B (zh) | 用于制备可用于合成美托咪定的诸如3-芳基丁醛的化合物的方法 | |
US7943784B2 (en) | Process for the preparation of almotriptan | |
KR20060113792A (ko) | 순수한 온단세트론 하이드로클로라이드 이수화물의 개선된제조 방법 | |
EP0489548B1 (fr) | Un procédé pour la préparation de 2(R)-methyl-4,4,4-trifluorobutylamine, des composés intermédiaires et un procédé pour la préparation d'un dérivé | |
US11459291B2 (en) | Method of preparation of (1R,3S)-3-amino-1-cyclopentanol and salt thereof | |
CN109485567B (zh) | 一种4-羟甲基噻唑的清洁制备方法及其中间体 | |
KR100377578B1 (ko) | 온단세트론 및 그의 염의 제조방법 | |
FR2575469A1 (fr) | N-imidazolylmethyl-diphenylazomethines, leur preparation et leur application en therapeutique | |
EP1955998A1 (fr) | Nouveau sel d'addition de N-amino-N'-pentylguanidine, son procédé de préparation et son utilisation pour obtenir du tégasérod |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20200925 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C07C 51/41 20060101ALI20210827BHEP Ipc: C07D 279/28 20060101AFI20210827BHEP |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20211207 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C07C 51/41 20060101ALI20211201BHEP Ipc: C07D 279/28 20060101AFI20211201BHEP |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20221031 |