cas 641571-10-0, Nilotinib | Articles data

Articles about 641571-10-0Total 29 be found

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SYNTHESIS OF 6-METHYL-N1-(4-(PYRIDIN-3-YL)PYRIMIDIN-2-YL)BENZENE-1,3-DIAMINE
Processes and useful intermediates for the synthesis of the tyrosine kinase inhibitors Formula (II) nilotinib and Formula (IV) imatinib. Key intermediates, method for their synthesis and their use in a divergent synthesis, making use of a Curtius rearrangement, to nilotinib and imatinib are described.
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Page/Page column 40-41

(2021/04/23)

High-yield synthesis method of nilotinib
The invention discloses a high-yield synthesis method, of nilotinib, and relates to the technical field, of pharmaceutical organic synthesis, and 3 - and, of intermediates 3 - (4 - and) - 5 - are obtained through a closed-loop reaction to obtain the intermediate I, and the intermediate I of the present invention as a starting material II, through an acid addition reaction and a synthesis method for synthesizing meso II intermediate 3 - with the monocyanamide through an acid addition reaction and reducing the cost input) - 2 - and reducing the three-waste generation amount. to obtain the intermediate 70% . The raw material is easy to obtain, through a closed-loop. reaction to obtain a nilotinib, as a starting material by a closed-loop reaction.
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(2020/03/17)

AN IMPROVED PROCESS FOR 3-(4-METHYL-1H-IMIDAZOL-1-YL)-5-(TRIFLUOROMETHYL) ANILINE
The present invention relates to an improved process for the preparation of 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl) aniline of Formula (I).
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(2019/07/17)

Preparation method and intermediate of nilotinib
The invention discloses a nilotinib preparation method and an intermediate of nilotinib. The preparation method comprises: in a solvent, carrying out a reaction defined in the specification on a compound D or a hydrochloride salt thereof, and a compound SM3 under the action of an inorganic base to obtain the compound E nilotinib. According to the present invention, the preparation method has characteristics of simple reaction, easy operation, safe and environmentally friendly reagent, less side reaction and short reaction time. The reaction formula is defined in the specification.
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(2019/05/02)

PROCESS FOR THE PREPARATION OF PURE NILOTINIB AND ITS SALT
Object of the present invention is a process for the preparation of the pharmaceutical active ingredient Nilotinib free base or Nilotinib dihydrochloride dihydrate by means of an improved crystallization procedure.
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Paragraph 0125; 0126

(2018/12/04)

A 3 - (4 - methyl - 1H - imidazole -1 - yl) -5 - trifluoromethyl aniline single hydrochloride crystalline form and application thereof (by machine translation)
The invention relates to a 3 - (4 - methyl - 1 H - imidazole - 1 - yl) - 5 - trifluoromethyl aniline single hydrochloride crystalline form and its application. In particular, the invention discloses 3 - (4 - methyl - 1 H - imidazole - 1 - yl) - 5 - trifluoromethyl aniline single hydrochloride anhydrous crystalline form A, crystalline form A preparation method of synthesizing [...] and this crystalline form in the application. The crystalline form of the present invention A has good stability and purity, can be directly used for the preparation of [...] in production. The invention of the preparation method [...] operation is simple and easy, with comparatively high industrial application value. (by machine translation)
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Paragraph 0101-0102

(2018/10/11)

METHOD FOR PREPARING NILOTINIB
A method for preparing nilotinib includes the following steps: performing an aminocarbonylation reaction on a compound A and 3-(4-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl) aniline to obtain an amination product; and performing deprotection treatment of an R group on the amination product to obtain the nilotinib, wherein the compound A has a structure shown in formula I, and in formula I, an R group is selected from benzyl, —COCF3, —CHO or —CO2R′, where an R′ group is C1?C10 alkyl, C1?C3 alkoxy ethyl or C7?C19 aralkyl.
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Paragraph 0098

(2018/06/09)

The preparation method of the [...]
The invention provides a preparation method for nilotinib. The preparation method comprises the following steps: producing a carbonyl insertion amination reaction of a compound A and 3-(4-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl)phenylamine, and obtaining an amination product; performing R group deprotection treatment on the amination product, and obtaining nilotinib, wherein the compound A has a structure as shown in a formula I, in the formula I, R is selected from benzyl, -COCF3, -CHO or -CO2R', and R' is C1-C10 alkyl, C1-C3 alkoxy ethyl or C7-C19 aralkyl. The preparation method is short in synthetic route and mild in reaction condition, and due to the adoption of special raw materials, the preparation method reduces the process cost while increasing the carbonyl yield.
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Paragraph 0060; 0063; 0064; 0066; 0067; 0069; 0107-00109

(2017/11/16)

Preparation method of high-purity nilotinib
The invention discloses a preparation method of high-purity nilotinib. The method includes two steps of synthesizing and purifying nilotinib. The purification further includes extraction, silica gel column chromatography, secondary extraction, re-crystallization, etc. The nilotinib is more than 99.5% in purity, is less than 0.1% in content of single impurity and is more than 65% in yield. The preparation method is suitable for industrial production in the scale of active pharmaceutical ingredients.
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Paragraph 0019-0027

(2017/08/28)

An optimized approach in the synthesis of imatinib intermediates and analogues
We revisited the classical synthetic procedure for imatinib synthesis providing an improved and optimized approach in the preparation of a series of new imatinib analogues. The proposed methodology effectively overcomes certain problematic steps, saves time and labor, provides a very high yield and purity and has the potential to be used for the synthesis of many analogues. The formation of the desired guanidine salt 4, one of the key steps to the imatinib synthesis, was proceeded almost quantitatively by the reaction of the hydrochloride of the suitable aniline 3 with excess of molten cyanamide, without any solvent. Pure arylamine intermediates 6a-d were obtained quantitatively in a short reaction time after reduction of the nitro group of the intermediate pyrimidines 5a-d with hydrogen over the Adam's catalyst. In addition, the application of this optimized approach can be extended in the synthesis of nilotinib and its analogues intermediates.
Kinigopoulou,Filippidou,Gogou,Giannousi,Fouka,Ntemou,Alivertis,Georgis,Brentas,Polychronidou,Voulgari,Theodorou,Skobridis
p. 61458 - 61467
(2016/07/12)

NOVEL POLYMORPHIC FORM X OF NILOTINIB DIHYDROCHLORIDE HYDRATE
The present invention relates to a novel polymorph of nilotinib hydrochloride(Form X), to processes for its preparation, to pharmaceutical compositions containing the same and to its use in medicine.
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Page/Page column 12

(2016/10/11)

SOLID FORMS OF NILOTINIB HYDROCHLORIDE
A solid form of Nilotinib hydrochloride, which exists as a co-crystal of nilotinib hydrochloride and levulinic acid having a molar ratio of nilotinib hydrochloride to levulinic acid of 1:2, and a process for the preparation of the co-crystal.
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Page/Page column 19

(2016/12/26)

IMIDAZOYL ANILIDE DERIVATIVES AND METHODS OF USE
The present invention provides kinase inhibitor analogs with improved properties, such as improved efficacy, pharmacokinetics, safety, and specificity. In some embodiments, the present invention provides nilotinib analogs that provide therapeutic benefits.
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Paragraph 0118: 0119; 0135

(2016/03/22)

AN IMPROVED PROCESS FOR THE PREPARATION OF NILOTINIB AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF
The present invention relates to an improved process for the preparation of nilotinib and pharmaceutically acceptable salts thereof, with high purity and yields.
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Page/Page column 16

(2015/06/25)

Method for preparing nilotinib
The present invention provides a method for preparing Nilotinib of the following structure: by direct condensation of an ester and an aniline promoted by trialkyl aluminum in an organic solvent.
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Page/Page column 7

(2015/12/04)

Research and development of a novel process for nilotinib: A Bcr-Abl inhibitor
In this study, an efficient, economic and novel process for the production of highly pure nilotinib (1), a Bcr-Abl inhibitor in described. The synthesis comprises the chlorination of 4-methyl-3-nitro benzoic acid (2) to get 4-methyl-3-nitro benzoyl chloride (2A). Condensation of compound (2) with 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzeneamine (11) to obtain 4-methyl-N-[3-(4-methyl-1Himidazol- 1-yl-5-(trifluoromethyl)phenyl]-3-nitro- benzamide hydrochloride (3). Reducing compound (3) with stannous chloride (or) raney nickel to obtain 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl-5- (trifluoromethyl)phenyl]-3-amino-benzamide (4). Reaction of compound (4) with cyanamide to obtain 4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl-5-(trifluoromethyl) phenyl]-3-guanidino-benzamide (5). Condensation of the compound (5) with 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (8) to obtain nilotinib (1).
Amala,Bhujanga Rao,Sreenivas,Dubey
p. 4599 - 4602
(2013/07/04)

PROCESS FOR THE PREPARATION OF NILOTINIB
The present invention relates a process for the preparation of a compound of formula (I): or a pharmaceutically acceptable salt thereof, which process comprises converting a compound of formula (IV): or a pharmaceutically acceptable salt thereof, into the compound of formula (I) or a pharmaceutically acceptable salt thereof.
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Paragraph 0066-0067

(2013/08/28)

Process for the preparation of nilotinib hydrochloride
A process for the preparation of a hydrochloride salt of a compound of formula (I): which process comprises converting a compound of formula (IV): or a pharmaceutically acceptable salt thereof, into the hydrochloride salt of the compound of formula (I).
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Paragraph 0047

(2013/08/28)

INTERMEDIATES FOR A NOVEL PROCESS OF PREPARING IMATINIB AND RELATED TYROSINE KINASE INHIBITORS
4-Oxo-2-phenylaminopyrimidine derivatives as intermediates for synth of tyrosine kinase inhibitors, in particular imatinib and nilotinib.
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(2013/08/28)

An expeditious synthesis of imatinib and analogues utilising flow chemistry methods
A flow-based route to imatinib, the API of Gleevec, was developed and the general procedure then used to generate a number of analogues which were screened for biological activity against Abl1. The flow synthesis required minimal manual intervention and was achieved despite the poor solubility of many of the reaction components.
Hopkin, Mark D.,Baxendale, Ian R.,Ley, Steven V.
p. 1822 - 1839
(2013/04/23)

Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: Application to the synthesis of nilotinib
The completely N1-selective Pd-catalyzed arylation of unsymmetric imidazoles with aryl halides and triflates is described. This study showed that imidazoles have a strong inhibitory effect on the in situ formation of the catalytically active Pd(0)-ligand complex. The efficacy of the N-arylation reaction was improved drastically by the use of a preactivated solution of Pd2(dba)3 and L1. From these findings, it is clear that while imidazoles can prevent binding of L1 to Pd, once the ligand is bound to the metal, these heterocycles do not displace it. The utility of the present catalytic system was demonstrated by the regioselective synthesis of the clinically important tyrosine kinase inhibitor nilotinib.
Ueda, Satoshi,Su, Mingjuan,Buchwald, Stephen L.
supporting information; experimental part
p. 700 - 706
(2012/03/07)

Nilotinib intermediates and preparation thereof
Nilotinib?3HCl and its crystalline forms are described, and processes for the preparation of the same.
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Page/Page column 29

(2011/04/25)

NILOTINIB SALTS AND CRYSTALLINE FORMS THEREOF
Nilotinib salts and crystalline forms thereof have been prepared and characterized.
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Page/Page column 33

(2012/01/14)

NILOTINIB INTERMEDIATES AND PREPARATION THEREOF
Intermediates of Nilotinib were prepared, including, for example, 3-(trifluoromethyl-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine; 3-(4-(pyridin-3-yl)pyrimidin-2-ylamino) -4-methylbenzoyl halogen dihydrochloride; and N-(3-Bromo-5-trifluoromethylphenyl)-4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzamide. Nilotinib.3HCl and its crystalline forms are also described.
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Page/Page column 20

(2010/02/17)

COMBINATIONS COMPRISING BCR-ABL/C-KIT/PDGF-R TK INHIBITORS FOR TREATING CANCER
The invention relates to a combination comprising a Bcr-Abl, c-Kit and PDGF-R tyrosine kinase inhibitor; and one or more pharmaceutically active agents; pharmaceutical compositions comprising said combination; methods of treatment comprising said combination; processes for making said combination; and a commercial package comprising said combination.
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(2009/09/28)

CRYSTALLINE FORMS OF 4-METHYL-N-[3-(4-METHYL-IMIDAZOL-1-YL)-5-TRIFLUOROMETHYL-PHENYL]-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-BENZAMIDE
Crystalline forms of 4-methyl-N-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzamide free base and salts thereof are prepared by various processes.
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Page/Page column 36-37

(2008/06/13)

An efficient synthesis of nilotinib (AMN107)
A concise synthesis of AMN107, a compound currently undergoing several phase II/III clinical trials for chronic myelogenous leukemia is described. The new procedure reduces the number of synthetic steps from eight to four, with an overall yield of 65%. Georg Thieme Verlag Stuttgart.
Huang, Wei-Sheng,Shakespeare, William C.
p. 2121 - 2124
(2008/03/28)

PROCESS FOR THE SYNTHESIS OF ORGANIC COMPOUNDS
The present invention provides a new method of making compounds of formula (I): wherein R1 is mono- or polysubstituted aryl; R2 is hydrogen, lower alkyl or aryl; and R4 is hydrogen, lower alkyl or halogen.
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Page/Page column 6; 8-9

(2008/06/13)

INHIBITORS OF TYROSINE KINASES
The invention relates to compounds of formula (I) Wherein the substituents R1, R2 and R4 have the meaning as set forth and explained in the description of the invention, to processes for the preparation of these compounds, pharmaceutical compositions containing same, the use thereof optionally in combination with one or more other pharmaceutically active compounds for the therapy of a disease which responds to an inhibition of protein kinase activity, especially a neoplastic disease, in particular leukaemia, and a method for the treatment of such disease.
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Page 63

(2008/06/13)