388082-77-7 Usage
Description
Lapatinib ditosylate, also known as Tykerb, is a reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. It is an antineoplastic agent that was launched for the treatment of advanced or metastatic HER2 (ErbB2) positive breast cancer in women who have received prior therapy. The drug was discovered and developed by GlaxoSmithKline and is also currently being evaluated for several additional cancer indications. Lapatinib ditosylate is a yellow solid.
Uses
Used in Oncology:
Lapatinib ditosylate is used as an antineoplastic agent for the treatment of advanced or metastatic HER2 (ErbB2) positive breast cancer in women who have received prior therapy. It works by inhibiting the ErbB1 and ErbB2 tyrosine kinases, which are involved in the growth and progression of cancer cells.
Used in Cancer Research:
Lapatinib ditosylate is used as a research tool for studying the role of ErbB1 and ErbB2 tyrosine kinases in various types of cancer. It helps researchers understand the molecular mechanisms underlying cancer development and progression, as well as the potential of targeting these kinases for therapeutic intervention.
Used in Drug Development:
Lapatinib ditosylate serves as a starting point for the development of new drugs targeting ErbB1 and ErbB2 tyrosine kinases. Researchers can use its chemical structure and mechanism of action to design and synthesize novel compounds with improved potency, selectivity, and pharmacokinetic properties.
Used in Combination Therapy:
Lapatinib ditosylate is used in combination with other antineoplastic agents to enhance the treatment of various types of cancer. The combination of Lapatinib ditosylate with other drugs can help overcome drug resistance, improve treatment efficacy, and reduce the likelihood of side effects.
Used in Clinical Trials:
Lapatinib ditosylate is used in clinical trials to evaluate its safety, efficacy, and potential for treating various types of cancer beyond HER2 positive breast cancer. These trials help determine the optimal dosing regimens, identify potential side effects, and establish the drug's place in the treatment landscape for different cancer types.
Synthesis
The synthesis started
with Williamson ether synthesis between 2-chloro-4-nitrophenol
(58) and 3-fluorobenzyl bromide to give ether 59 in the following scheme; however, no specific yields were provided.
Reduction of the nitro group of compound 59 by catalytic
hydrogenation over Pt/C and subsequent condensation of the
resulting aniline with 4-chloro-6-iodoquinazoline (61) in
refluxing i-PrOH afforded compound 62. 4-Chloro-6-iodoquinazoline
(61) was prepared by reacting 6-iodoquinazolin-
4(3H)-one (60) with POCl3 in the presence of triethylamine.
Compound 62 was subjected to Stille coupling with 5-
dioxolanyl-2-(tributylstannyl)furan (63) in the presence of
PdCl2(PPh3)2 to give 64. Acidic hydrolysis of acetal 64 using
HCl in THF/H2O provided the corresponding aldehyde which
was further subjected to reductive amination with 2-(methan-esulfonyl)ethylamine in the presence of sodium triacetoxyborohydride
to yield lapatinib. Lapatinib was treated with ptoluenesulfonic
acid solution to give lapatinib ditosylate
(IX).
Check Digit Verification of cas no
The CAS Registry Mumber 388082-77-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,8,8,0,8 and 2 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 388082-77:
(8*3)+(7*8)+(6*8)+(5*0)+(4*8)+(3*2)+(2*7)+(1*7)=187
187 % 10 = 7
So 388082-77-7 is a valid CAS Registry Number.
InChI:InChI=1/C29H26ClFN4O4S.2C6H6O3S.H2O/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19;2*7-10(8,9)6-4-2-1-3-5-6;/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35);2*1-5H,(H,7,8,9);1H2
388082-77-7Relevant articles and documents
An environment friendly process for the preparation of Lapatinib Ditosylate of Formula 1(b)
-
, (2022/02/15)
The present invention relates to a process for the preparation of Lapatinib Ditosylate of formula 1(b). More particularly, the present invention relates to environment friendly process that involves green chemistry in preparation of Lapatinib Ditosylate of formula 1(b). The said process is economically and commercially viable as initial 2 stages of processes use water as solvent avoiding hazardous reagent or solvent during the preparation of Lapatinib Ditosylate of formula 1(b).
A high-purity paratoluene sulfonic acid lapatinib a preparation method of water composition
-
Paragraph 0020, (2019/04/04)
The invention relates to a high-purity paratoluene sulfonic acid lapatinib a water composition of the preparation method, the method comprises the following steps: (1) the compound II with compound III under alkaline conditions, the catalyst under the action of the Suzuki coupling to obtain compound IV; (2) the compound IV with a compound V in weakly alkaline conditions, in the catalyst under the action of the joint, by the three-b acyl sodium borohydride reduction, paratoluene sulfonic acid to form the salt to obtain compound VI; (3) the compound VI with the recrystallization to obtain compound I, is the second-to-toluene sulfonic acid lapatinib a hydrate. The programme provides at least to a certain extent one of the solve the above technical problems or at least provide a useful commercial choice. To avoid the use of toxicity is relatively high, the environmentally harmful solvent or reagent, the reaction route is operating time is short, the reaction system is stable, the purification process is simple, the product purity is higher, it is suitable for industrial production.
Method for synthesizing lapatinib or intermediate 5-(4-hydroxy quinazoline)-furan-2-formaldehyde of lapatinib
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Paragraph 0034; 0051; 0052; 0053, (2017/03/22)
The invention relates to a method for synthesizing lapatinib or intermediate 5-(4-hydroxy quinazoline)-furan-2-formaldehyde of lapatinib. The method for synthesizing the intermediate comprises steps as follows: 4-hydroxy-6-nitro quinazoline reacts with hydrazine hydrate in a solvent in the presence of a catalytic amount of catalyst, and 4-hydroxy-6-amino quinazoline is prepared; 4-hydroxy-6-amino quinazoline reacts with furaldehyde in the solvent in presence of acid, sodium nitrite and a catalytic amount of catalyst, and the intermediate is prepared. The invention further relates to a method for synthesizing lapatinib and/or a lapatinib salt, a lapatinib intermediate and/or a pharmaceutically acceptable salt of the intermediate. The method is performed by using the intermediate synthesized with the method. The method has the advantages that steps are simplified, agents are cheap, available and high in utilization rate, heavy metal pollution is avoided, the reaction condition/operation requirement is lower and/or the yield is high and the like.
