Imatinib

ImatinibCAS No:- [152459-95-5]IUPAC Name:- 4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamideM. P.:- 211-213 °CMW: 493.60
4-[(4-methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamideImatinib (originally STI571) is a drug used to treat certain cancers. It is marketed byNovartis as Gleevec (USA) or Glivec (Europe/Australia/Latin America) as its mesylatesalt, imatinib mesilate (INN).Imatinib is the first of a new class of drugs that act by specifically inhibiting a certainenzyme – a receptor tyrosine kinase – that is characteristic of a particular cancer cell, rather than non-specifically inhibiting and killing all rapidly dividing cells. Imatinib was a model for other targeted therapies that inhibited this class of enzymes.It is used in treating chronic myelogenous leukemia (CML), gastrointestinal stromal tumors(GISTs) and some other diseases. By 2011, Gleevec has been FDA approved to treat ten different cancers.In CML, the tyrosine kinase enzyme ABL in white blood cells is locked in its activated form. This causes the excessive proliferation and high white blood cell count which is characteristic of CML. Imatinib binds to the site of tyrosine kinase activity, and prevents its activity, causing tumor cell death (apoptosis).

bcr-abl kinase (green), which causes CML, inhibited by imatinib (red; small molecule).

Chronic myelogenous leukemia

The U.S. Food and Drug Administration (FDA) has approved imatinib as first-line treatment for Philadelphia chromosome (Ph)-positive CML, both in adults and children. The drug is approved in multiple Ph-positive cases CML, including after stem cell transplant, in blast crisis, and newly diagnosed

Legal challenge to generics

In 2007, imatinib became a test case through which Novartis challenged India’s patent laws. A win for Novartis would make it harder for Indian companies to produce generic versions of drugs still manufactured under patent elsewhere in the world. Doctors Without Borders argues a change in law would make it impossible for Indian companies to produce cheap generic antiretrovirals (anti-HIV medication), thus making it impossible for Third World countries to buy these essential medicines.^[43] On 6 August 2007, the Madras High Court dismissed the writ petition filed by Novartis challenging the constitutionality of Section 3(d) of Indian Patent Act, and deferred to the World Trade Organization (WTO) forum to resolve the TRIPS compliance question. As of 2009 India has refused to grant patent exclusivity..

On April 01, 2013 Supreme Court of India dismissed the plea of Novartis for the grant of patent.

in germany

synthesis

i. Cyanamide, nitric acid, ethanol, reflux, 25 h,

ii. 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one, sodium hydroxide, isopropanol, reflux, 12 h,

iii. 10% palladium on carbon, hydrogen gas, ethyl acetate, room temperature, 6.5 h,

iv. 4-(4-methylpiperazinomethyl)-benzoyl chloride, pyridine, room temperature, 23 h

Anticancer drug imatinib mesylate (Imatinib Mesylate). Tradename Gleevec (Gleevec). Manufacturer Novartis. The FDA in May 2001 approved the listing for the treatment of Philadelphia chromosome (Bcr-Abl)-positive chronic myeloid leukemia (Chronic Myelogenous Leukemia, CML) and gastrointestinal stromal tumor (gastrointestinal stromal tumor, GIST) and other illnesses.

Imatinib is a tyrosine kinase inhibitor. In the early high-throughput screening, found two – phenylamino-pyrimidine (2-phenylaminopyrimidine) compounds of the Philadelphia chromosome mutant Bcr-Abl protein have a good inhibition, improvement of its structure obtained after imatinib.

Inverse synthetic analysis will be divided into four imatinib into fragment A has 1,3 – parents electrical, fragment B are 1,3 – parent nuclear, fragments A and B constitute a pyrimidine ring.

Compound 4 can be obtained in two ways, benzyl bromide 1 and secondary amines 2 by SN2 reaction, or the aldehyde 3 with a secondary amine 2 by reductive amination. Sodium cyanoborohydride electron withdrawing effect of the cyano group, thereby reducing the activity of the negative hydrogen, it may be present in acidic solution. Also in the acidic conditions of aldehydes and secondary amines imine positive ions, which is higher than the activity of aldehyde reduction.This is why the reductive amination reagent with inert negative and hydrogen under acidic conditions. 4 hydrolyzed ester with thionyl chloride into the acid chloride 5 . The reaction of aniline and cyanamide dinucleophile guanidine 7 . Compound 8 and DMF-DMA reaction electrophilic reagent parents 9 , 7 , and 9 ring closure under alkaline conditions to generate 10 . Finally, reduction, amidation, and a salt of imatinib mesylate generated.

Medicine for Blood Cancer

‘Imitinef Mercilet’ is a medicine which cures blood cancer.
Its available free of cost at “Adyar Cancer Institute in Chennai”.
Create Awareness. It might help someone.Cancer Institute in Adyar, Chennai

‘Imitinef Mercilet’ is apparently an alternative spelling of the drug Imatinib mesylate which is used in the treatment of some forms of leukemia along with other types of cancer. Imatinib, often referred to a “Gleevec”, has proved to be an effective treatment for some forms of cancers. However, “blood cancer” is a generalized term for cancers that affect the blood, lymphatic system or bone marrow. The three types of blood cancer are listed as leukemia, lymphoma, and multiple myeloma. These three malignancies require quite different kinds of treatments. While drugs (including Imatinib), along with other treatments such as radiation can help to slow or even stop the progress of these cancers, there is currently no single drug treatment that can be said to actually cure all such cancers.

Category: Cancer
Address: East Canal Bank Road , Gandhi Nagar
Adyar, Chennai -600020
Landmark: Near Michael School
Phone: 044-24910754 044-24910754 ,
044-24911526 044-24911526 , 044-22350241

Imatinib is a small molecule selectively inhibiting specific tyrosine kinases that has emerged recently as a valuable treatment for patients with advanced GIST. The use of imatinib as monotherapy for the treatment of GIST has been described in PCT publication WO 02/34727, which is here incorporated by reference. However, it has been reported that primary resistance to imatinib is present in a population of patients, for example 13.7% of patients in one study. In addition, a number of patients acquire resistance to treatment with imatinib. More generally this resistance is partial with progression in some lesions, but continuing disease control in other lesions. Hence, these patients remain on imatinib treatment but with a clear need for additional or alternative therapy.

Imatinib is 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]-benzamide having the formula I

The preparation of imatinib and the use thereof, especially as an anti-tumour agent, are described in Example 21 of European patent application EP-A-0 564 409, which was published on 6 Oct. 1993, and in equivalent applications and patents in numerous other countries, e.g. in U.S. Pat. No. 5,521,184 and in Japanese patent 2706682