cas 154361-50-9, Capecitabine | Articles data

Articles about 154361-50-9Total 31 be found

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Synthesis of the antitumoral nucleoside capecitabine through a chemo-enzymatic approach
Capecitabine is a 5′-deoxynucleoside endowed with antitumoral activity. We planned a new approach to its synthesis: a cross linked enzyme aggregate subtilisin (Alcalase CLEA)-catalyzed alcoholysis allowed the selective deprotection of primary acetyl ester of the N1-(2′,3′,5′-tri-O-acetyl-β-d-ribofuranosyl)-5-fluoro-N4-(n-pentyloxycarbonyl)cytosine affording the corresponding 5′-hydroxyderivative; the 5′-alcohol was transformed into the methyl group of capecitabine after a careful investigation about the best reducing agent and reaction conditions.
Ciceri, Samuele,Ciuffreda, Pierangela,Grisenti, Paride,Ferraboschi, Patrizia
p. 5909 - 5913
(2015)
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Continuous-Flow Sequential Schotten-Baumann Carbamoylation and Acetate Hydrolysis in the Synthesis of Capecitabine
Capecitabine is an important anticancer drug whose synthesis comprises late-stage carbamoylation and ester hydrolysis. Herein we report the use of the Schotten-Baumann reaction in order to perform these transformation in one pot both in batch and under continuous flow. In batch, capecitabine was obtained in 82% yield in 5 h, while under continuous flow it was obtained in 81% yield in 30 min. This one-pot reaction reduces the chemical waste produced, labor, time, and cost and additionally comprises the use of environmentally friendly solvents and reagents as well as energy-efficient and safe methods, all of which fulfill the requirements of a green process.
Miranda, Leandro S. De M.,De Souza, Rodrigo O. M. A.,Lea?, Raquel A. C.,Carneiro, Paula F.,Pedraza, Sergio F.,De Carvalho, Otavio V.,De Souza, Stefania P.,Neves, Rebeca V.
p. 2516 - 2520
(2019)
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Preparation of capecitabine intermediate
The invention belongs to the field of medicine synthesis, and provides a preparation method of capecitabine intermediate, in particular to a compound of the formula I II in the presence of a ketone solvent and an organic base.
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Paragraph 0025-0028

(2021/09/01)

Cytidine derivative and method for preparing capecitabine medicines through derivative
The invention discloses a 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as shown in a general formula (I) and a preparation method of the derivative, and a method for preparing a N4-deoxycarbonyl cytidine derivative and antitumor medicines namely capecitabine by using the general formula (I) as a raw material, wherein the structure of the general formula (I) is as shown in the description. The 5-deoxy-D-ribofuranose 1-[2-(1-styyl) benzoate] derivative as the raw material of a reaction is used as a glycosyl donor and can be activated under the condition of Lewis acid trimethylsilyl trifluoromethanesulfonate and N-lodosuccinimide in catalysis quantity, so that Lewis acid in traditional use equivalent or excessive quantity is avoided, and a reaction system is mild, free from occurrence of other side reactions and efficient.
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Paragraph 0065-0069

(2020/05/14)

A capecitabine synthetic method
The invention belongs to the technical field of medicine preparation and relates to a synthetic method of capecitabine. The method comprises the following steps: 1) condensation reaction: reacting 2', 3'-bi-O-acetyl-5'-deoxy-5-fluoro-cytidine with halo n-amyl formate in the presence of an acid applying agent and a dimethylamino-pyridine catalyst to prepare N-pentyloxy carbonyl-2' 3'-bi-O-actyl-5'-deoxy-5-fluoro-cytidine; and 2) hydrolysis reaction: carrying out hydrolysis reaction on N-pentyloxy carbonyl-2' 3'-bi-O-actyl-5'-deoxy-5-fluoro-cytidine in the presence of an inorganic base to prepare the final product capecitabine. Compared with the prior art, the method provided by the invention has the advantages that by taking the inorganic base as the acid applying agent, use of a lot of organic bases is avoided and therefore the yield is improved, the production cost lowered, the environmental pollution is reduced, the physical health of the worker is ensured, and industrial production is facilitated.
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Paragraph 0020; 0023; 0026; 0027; 0029

(2018/06/21)

A capecitabine synthetic method
The invention discloses a synthesis method for capecitabine. The method comprises the following five steps of (1) carrying out reaction on D-ribose and acetic anhydride so as to prepare a compound V; (2) carrying out reaction on the compound V and 5-FC so as to prepare a compound IV; (3) hydrolyzing the compound IV so as to prepare a compound III; (4) hydroxylating the compound III so as to prepare a compound II; and (5) deprotecting so as to prepare the capecitabine (a compound I) finally. The synthesis method has simple operation steps and mild reaction conditions, is easy to extract and separate the product, has high yield, greatly lowers the production cost, and is beneficial to industrial production.
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(2017/07/14)

Method for preparing capecitabine from capecitabine waste water extract
The invention discloses a method for preparing capecitabine from capecitabine waste water extract. The method comprises the following steps: extracting 5'-deoxy-5-gemcitabine from capecitabine waste water, introducing isopropylidene at hydroxy of a saccharide structure part of a compound for protection, further introducing acryl at an amino group, and eliminating the isopropylidene protection from the saccharide structure part to obtain capecitabine. By adopting the method, not only is the waste water harmlessly treated, but also the reutilization of impurities in the waste water is realized, the production cost is decreased, the operation is convenient, raw materials needed for preparation are easy to obtain, and the industrialized production is facilitated (shown in the description).
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Paragraph 0039; 0044; 0045

(2017/07/20)

For a continuously operated synthetic capecitabine method
The invention discloses a method for synthesizing capecitabine by continuous operations. The method comprises the following steps: acylating 5'-deoxy-2', 3'-2-O-acetyl-5-gemcitabine to obtain 5'-deoxy-2',3'-2-O-acetyl-N-[(pentyl acetal) carbonyl]-5-fluorine cytidine methylene chloride solution; then directly adding an alkaline aqueous solution; adding alcohol, and hydrolyzing and synthesizing capecitabine. The method disclosed by the invention is short in reaction time to more than ten minutes, fewer in treatment steps, simple to operate, low in cost and small in pollution.
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Paragraph 0025-0026

(2017/08/31)

Preparation method of 2'-3'-bis-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine
The invention relates to the field of pharmaceutical chemistry, in particular to a preparation method of 2'-3'-bis-O-acetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine; the method comprises: reacting a compound of formula IV as a raw material with n-amyl chloroformate under the action of K3PO4 to obtain the compound of formula V, 2',3'-bis-O-acetyl-5'-deoxy-5-fluorine-N4-[(pentyloxy)carbonyl]cytidine. The invention also provides application of the method in the preparation of capecitabine. The preparation method has the advantages that reaction yield can be significantly increased, product purity is high, reaction conditions are mild, the use of pyridine is avoided, pyridine residue in the product is avoided, and the method is suitable for industrial production of medicine.
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(2017/08/28)

Preparation method of capecitabine
The invention belongs to the field of medicinal chemistry and specifically relates to a preparation method of capecitabine. Firstly, steps of silylanization, glycosylation, acylation, esterification and deprotection are successively carried out. An intermediate doesn't require separation and purification, and a product is synthesized by a one-pot method. The final product capecitabine is separated and purified through extraction and recrystallization. The reaction operation is simple. Secondly, during the glycosylation reaction, BF3.OEt2 is used as a Lewis acid, production cost is low, and reaction materials have little toxicity. Thirdly, during the silylanization reaction, trimethylchlorosilane is used as a silylating reagent, dichloromethane is used as a solvent, potassium carbonate is used as an acid-binding agent, and the agents are easy to remove after the end of the reaction, which is beneficial to the next reaction. In addition, reaction temperatures of the reaction steps of silylanization, glycosylation, acylation and esterification in the preparation method are all 20-30 DEG C, and reaction conditions are mild.
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Paragraph 0036; 0038; 0040; 0042; 0044

(2016/11/21)

Capecitabine and wherein the intermediate preparation method
The invention discloses a preparation method of capecitabine. The method comprises the following steps: based on D-ribose serving as a starting raw material, carrying out hydroxyl protection, 5-site tosylation, iodine substitution, hypophosphorous acid deiodination and acetylation so as to obtain the key intermediate 12,3-tri-O-acetyl-5-deoxy-beta-D-ribofuranose; carrying out glycosylation on the key intermediate and 5-fluorocytosine; and finally, carrying out N-4 site acylation and deprotection so as to obtain the capecitabine. In the method, a metal catalyst dose not need to be used for participating in reaction, the reaction condition is mild, and the yield is high, thus the method is economical and effective as well as suitable for industrial production on a large scale.
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(2017/02/09)

The capecitabine industrial preparation method
The invention optimizes the synthesis process of capecitabine bulk drug, especially improves the purification method of capecitabine. The method involved in the invention is suitable for industrial production, remarkably reduces the quantity and limit of related impurities in the capecitabine bulk drug, and improves the quality of the capecitabine bulk drug.
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(2017/01/23)

Safe and Alternate Process for the Reductions of Methanesulfonates: Application in the Synthesis of 1,2,3-Triacetyl-5-deoxy-d-ribofuranoside
Diethylene glycol dimethyl ether, diglyme, and 1,2-bis(2-methoxyethoxy)ethane, triglyme, are found to be suitable and safe alternate solvents to DMSO for the reduction of methanesulfonate in sodium borohydride. Addition of anhydrous lithium chloride led to the complete reduction of methanesulfonate esters to the corresponding alkanes in the presence of sodium borohydride in these solvents (diglyme and triglyme). This protocol is useful in the preparation of 1,2,3-triacetyl-5-deoxy-d-ribofuranoside, 7, a key intermediate of Capecitabine, 1, on the commercial scale.
Mekala, Nagaraju,Moturu, Murthy V.R.K.,Dammalapati, Rao V.L.N.,Parimi, Atchuta R.
p. 609 - 614
(2016/04/04)

Synthesis and biological activity evaluation of cytidine-5′-deoxy-5- fluoro-N-[(alkoxy/aryloxy)] carbonyl-cyclic 2′,3′-carbonates
Capecitabine, an oral prodrug of 5-FU was developed to improve the tumor selectivity and tolerability. To enhance the efficacy of capacitabine, a series of 5′-deoxy-5-fluorocytidine derivatives 5a-e were synthesized. In the present study, we investigated antitumor activity of 5′-deoxy-5- fluorocytidine derivatives both in vivo and in vitro methods. Title compounds were non-mutagenic to Salmonella typhimurium tester strain in Ames test. Compounds 5d and 5e are potent to inhibit the proliferation of NCI-69, PZ-HPV-7, MCF-7 and HeLa cells in MTT assay. In particular, 5d and 5e showed potent antitumor activities against L1210 leukemia cell line. Collectively, these findings suggest that 5d and 5e are more potent anti-cancer compounds than capecitabine.
Jhansi Rani,Raghavendra,Kishore,Nanda Kumar,Hema Kumar,Jagadeeswarareddy
p. 690 - 696
(2012/09/08)

Rapid continuous synthesis of 5′-deoxyribonucleosides in flow via Br?nsted acid catalyzed glycosylation
A general, green, and efficient Br?nsted acid-catalyzed glycosylation serves as a key step in the one-flow, multistep syntheses of several important 5′-deoxyribonucleoside pharmaceuticals.
Shen, Bo,Jamison, Timothy F.
p. 3348 - 3351
(2012/08/08)

ONE STEP PROCESS FOR THE PREPARATION OF CAPECITABINE
The present invention relates a one step process for the preparation of capecitabine and analogues thereof, such as galocitabine, sapacitabine, 5'-deoxy-5-fiuoro-N- [(cyclohexyloxy)carbonyl]cytidine, and N-[(heptyloxy)carbonyl]cytarabine.
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Page/Page column 18

(2011/09/30)

CYCLIC SULPHINYL ESTERS OF CYTIDINE
The present invention relates to novel intermediates and to an improved process for the preparation of N- functionalised cytidine derivatives such as capecitabine, galocitabine and sapacitabine. Said intermediates are se from a copound of formula (A- 2), (A-3), (A-6), (A-7). wherein: R1 and R3 arc each independendy selected from hydrogen, -F, -CI, -Br, -I, -CN, -NO2, -N3, -O-R7, -S-R7, -N(R7)2, -N(R7)3+ or -0-Si(R7)3; R4 and R5 arc each independendy selected from hydrogen, -F, -CI, -Br and -I; R6 is selected from an alkyl, alkenyl, alkynyl, atyl, aiylalkyl, arylalkenyl, arylalkynyl, alkylaiyl, alkenylaryl or alkynylaryl group, each of which may optionally be substituted, and each of which may optionally include one or more heteroatoms N, O or S in its carbon skeleton; and each R7 is independendy selected from hydrogen, or an alkyl, alkenyl, alkynyl, atyl, aiylalkyl, arylalkenyl, arylalkynyl, alkylaiyl, alkenylaryl or alkynylaryl group, each of which may optionally he substituted, and each of which may optionally include one or more heteroatoms N, O or S in its carbon skeleton, and wherein any two or more R7 groups may, together with rhe atom or atoms to which they are attached, form a cyclic alkyl, alkenyl, alkynyl, aryl, aiylalkyl, arylalkcnyl, arylalkynyl, alkylaiyl, alkenylaryl or alkynylaryl group, each of which may optionally be substituted, and each of which may optionally include one or more heteroatoms N, O or S in its carbon skeleton.
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(2011/06/25)

Process for Producing Fluorocytidine Derivatives
A process for making a capecitabine or its derivative comprising (a) reacting a compound of the formula (II): wherein each of R1 and R2 independently represents a hydroxyl protecting group, with an acylating agent of formula (III): X—C(═O)—R3, wherein X is an acyl activating group in an organic solvent to produce an acylated compound; (b) deprotecting the acylated compound to obtain the compound of formula (I); and (c) purifying the compound of formula (I) with a solvent.
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Page/Page column 3; 7

(2011/02/18)

Therapeutic use of at least one botulinum neurotoxin in the treatment of pain induced by at least one anti-neoplastic agent
The present invention relates to a method of treating or preventing pain or pains induced by an anti-neoplastic agent, comprising the step of administering an effective amount of at least one botulinum neurotoxin to a patient in need thereof.
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(2010/04/23)

METHOD FOR THE PREPARATION OF CAPECITABINE AND INTERMEDIATES USED IN SAID METHOD
A process to obtain capecitabine compound and its pharmaceutically acceptable derivatives is hereby disclosed. Likewise, novel intermediates to be used in the preparation of capecitabine compound and its pharmaceutically acceptable derivatives are also disclosed. The procedure comprises the stage of causing a reaction of N4-(n-pentyloxycarbonyl))-5- fluorocytosine with (1,2,3-tri-O-acetyl-5-deoxy- α,β-D-ribofuranose.
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Page/Page column 10

(2010/11/03)

PREPARATION OF CAPECITABINE
The present invention relates to substantially pure capecitabine and processes for the preparation thereof.
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Page/Page column 9; 24

(2010/06/20)

Process for the preparation of capecitabine
The present application relates to an improved process for the preparation of capecitabine.
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Page/Page column 10

(2009/09/05)

METHODS FOR PREPARING CAPECITABINE AND BETA-ANOMER-RICH TRIALKYL CARBONATE COMPOUND USED THEREIN
The present invention relates to a method for preparing capecitabine and a method for preparing a β-anomer-rich trialkyl carbonate compound used therein, and a highly pure capecitabine can be efficiently prepared with a high yield by the method of the present invention using the β-anomer-rich trialkyl carbonate compound as an intermediate.
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Page/Page column 13

(2009/06/27)

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Described herein are compositions and methods for using these compositions in the treatment of cancer, tumors, and tumor-related disorders in a subject.
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Page/Page column 56

(2009/05/29)

PROCESS FOR PREPARING CAPECITABINE
There is provided processes for the preparation of capecitabine and intermediates thereof.
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Page/Page column 34-35; 36

(2008/12/08)

PROCESSES RELATED TO MAKING CAPECITABINE
An intermediate (2) useful in making capecitabine can be formed without the use, or presence, of a silylation agent.
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Page/Page column 1; 4

(2009/01/20)

Herbal composition PHY906 and its use in chemotherapy
This invention provides herbal compositions useful for increasing the therapeutic index of drugs, including those used in the treatment of disease, especially viral infections and neoplasms of cancer. This invention provides methods useful for improving the quality of life of an individual undergoing chemotherapy. Furthermore, this invention improves the treatment of disease by increasing the therapeutic index of chemotherapy drugs by administering the herbal composition PHY906 to a person undergoing such chemotherapy.
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(2008/06/13)

5'-deoxy-cytidine derivatives
Novel 5'-deoxy-cytidine derivatives represented by the general formula (I) wherein R1 is a hydrogen atom or a group easily hydrolyzable under physiological conditions; R2 is a hydrogen atom, or -CO-OR4 group [wherein R4 is a saturated or unsaturated, straight or branched hydrocarbon group consisting of one to fifteen carbon atoms, or a group of the formula -(CH2)n-Y (in which Y is cyclohexyl or phenyl; n is an integer from 0 to 4)]; R3 is a hydrogen atom, bromo, iodo, cyano, a C1-4 alkyl group [which may be substituted with halogen atom(s)], a vinyl or ethynyl group [which may be substituted with halogen atom(s), C1-4 alkyl, cycloalkyl, aralkyl, or aromatic ring which may have one or more hetero atom(s)], or an aralkyl group which may be substituted for use in medical therapy, especially tumor therapy.
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(2008/06/13)

The design and synthesis of a new tumor-selective fluoropyrimidine carbamate, Capecitabine
To identify an orally available fluoropyrimidine having efficacy and safety profiles greatly improved over those of parenteral 5-fluorouracil (5-FU: 1), we designed a 5-FU prodrug that would pass intact through the intestinal mucisa and be sequentially converted to 5-FU by enzymes that are highly expressed in the human liver and then in tumors. Among various N4-substituted 5'-deoxy-5-fluorocytidine derivatives, a series of N4-alkoxycarbonyl derivatives were hydrolyzed to 5'-deoxy-5-fluorocytidine (5'-DFCR: 8) specifically by carboxylesterase, which exists preferentially in the liver in humans and monkeys. Particularly, derivatives having an N4-alkoxylcarbonyl moiety with a C4-C6 alkyl chain were the most susceptible to the human carboxylesterase. Those were then converted to 5'-deoxy-5-fluorouridine (5'-DFUR: 4) by cytidine deaminase highly expressed in the liver and solid tumors and finally to 5-FU by thymidine phosphorylase (dThdPase) preferentially located in tumors. When administered orally to monkeys, a derivative having the N4-alkoxylcarbonyl moiety with a C5 alkyl chain (capecitabine: 6) The highest AUC and Cmax for plasma 5'-DFUR. In tests with various human cancer xenograft models, capecitabine was more efficacious at wider dose ranges than either 5-FU or 5'-DFUR and was significantly less toxic to the intestinal tract than the others in monkeys. Copyright (C) 2000 Elsevier Science Ltd.
Shimma, Nobuo,Umeda, Isao,Arasaki, Motohiro,Murasaki, Chikako,Masubuchi, Kazunao,Kohchi, Yasunori,Miwa, Masanori,Ura, Masako,Sawada, Noriaki,Tahara, Hitoshi,Kuruma, Isamu,Horii, Ikuo,Ishitsuka, Hideo
p. 1697 - 1706
(2007/10/03)

5'deoxycytidine derivatives
Compounds of the formula (I) STR1 wherein R1 is each independently hydrogen or a group easily hydrolyzable under physiological conditions; R2 is --(CH2)n -cycloalkyl wherein cycloalkyl contains 3 to 5 carbon atoms and n is an integer from 0 to 4, heteroaryl-(lower-alkyl), (lower-alkoxy)-(lower-alkyl), aryloxy-(lower-alkyl), aralkyloxy-(lower-alkyl), (lower-alkylthio)-(lower-alkyl), arylthio-(lower-alkyl), aralkylthio-(lower-alkyl), oxo-(lower-alkyl), acylamino-(lower-alkyl), cyclic amino-(lower-alkyl), (2-oxocyclic amino)-(lower-alkyl) wherein the alkylene chain is unsubstituted or substituted with one or two lower-alkyl group(s); and R3 is iodo, or a vinyl or ethynyl group which group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, C1-4 alkyl, cycloalkyl, aralkyl, carbocyclic aromatic ring and heteorcyclic aromatic ring. The compounds of formula I are useful in the treatment of malignant diseases and can also be administered together with 5-fluorouracil or derivatives thereof to enhance the antitumour activity of the latter.
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(2008/06/13)

N4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine compounds, compositions and methods of using same
The invention relates to N4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine derivatives which are useful as an agent for treating tumors, pharmaceutical compositions including the same, a method of treating tumors and a method of preparing N4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine derivatives for treating tumors. Compounds of formula (I), STR1 wherein R1 is a saturated or unsaturated, straight or branched hydrocarbon radical wherein the number of carbon atoms in the longest straight chain of this hydrocarbon radical ranges from three to seven, or is a radical of the formula --(CH2)n--Y wherein Y is a cyclohexyl radical, a C1 -C4 alkoxy radical or a phenyl radical and wherein when Y is a cyclohexyl radical n is an integer from 0 to 4, and when Y is C1 -C4 alkoxy radical or a phenyl radical n is an integer from 2 to 4, and R2 is a hydrogen atom or a radical easily hydrolyzable under physiological conditions, or a hydrate or solvate thereof. Compounds of formula (I) are useful in the treatment of tumors.
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(2008/06/13)

Chemical Properties

Appearance/Colour :Colourless solid
Melting Point: 110-121 °C
Boiling Point: 437.874oC at 760 mmHg
Flash Point:218.619oC
Density: 1.49 g/cm³
Solubility:H2O: soluble10mg/mL, clear (warmed)
Storage Temp.:-20°C Freezer
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.7
PKA: 5.41±0.40(Predicted)
Merck: 14,1754
PSA: 122.91000
LogP: 0.83320

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Chemical Properties

Appearance/Colour :Colourless solid

Melting Point: 110-121 °C

Boiling Point: 437.874oC at 760 mmHg

Flash Point:218.619oC

Density: 1.49 g/cm³

Solubility:H2O: soluble10mg/mL, clear (warmed)

Storage Temp.:-20°C Freezer

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.7

PKA: 5.41±0.40(Predicted)

Merck: 14,1754

PSA: 122.91000

LogP: 0.83320

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Article Database

154361-50-9

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Chemical Properties

Appearance/Colour :Colourless solid

Melting Point: 110-121 °C

Boiling Point: 437.874oC at 760 mmHg

Flash Point:218.619oC

Density: 1.49 g/cm3

Solubility:H2O: soluble10mg/mL, clear (warmed)

Storage Temp.:-20°C Freezer

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.7

PKA: 5.41±0.40(Predicted)

Merck: 14,1754

PSA: 122.91000

LogP: 0.83320

Global suppliers and manufacturers of 154361-50-9total 362 suppliers on LookChem

Density: 1.49 g/cm³