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DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO
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Novartis First-Generation Lung Cancer Drug Tweaked To Reduce Potential Side Effects
Sponge molecules isolated and synthesized for drug trials
By scouring the oceans for disease-fighting molecules, researchers have identified two new anticancer compounds. Isolated from a sea sponge, the compounds represent a new class of the natural products called polyketides, many of which have biological activity. Because it’s not possible to extract sufficient amounts of the molecules from the sponges, the researchers also devised chemical syntheses that allowed them to make enough material to initiate clinical trials on one of the substances,
Cancer Fighters From The Sea
Natural Products: Sponge molecules isolated and synthesized for drug trials.
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BENAZEPRIL SYNTHESIS
CAS NO AS HCl SALT
| 86541-75-5 |
The reaction of 3-bromo-1-phenylpropane (I) with KCN gives 4-phenylbutyronitrile (II), which is hydrolyzed to the corresponding butyric acid (III). The cyclization of (III) with polyphosphoric acid affords 1-tetralone (IV), which is brominated to 2-bromo-1-tetralone (V) and treated with hydroxylamine to give the oxime (VI). The Beckman rearrangement of (VI) yields 3-bromo-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (VII), which is treated with sodium azide to afford the azide derivative (VIII). The N-alkylation of (VIII) with ethyl bromoacetate (IX) by means of KOH and tetrabutylammonium bromide in THF gives the N-alkylated azide (X), which is reduced by catalytic hydrogenation to the corresponding amine (XI). The hydrolysis of the ester group of (XI) with NaOH yields the free acetic acid derivative (XII), which is finally reductocondensed with ethyl 2-oxo-4-phenylbutyrate (XIII) by means of sodium cyanoborohydride
WO 2003092698 A1
Pilot Plant PAT Approach for the Diastereoselective Diimide Reduction of Artemisinic Acid
Pilot Plant PAT Approach for the Diastereoselective Diimide Reduction of Artemisinic Acid
In this study, an attractive route for the diastereoselective synthesis of dihydroartemisinic acid (DHAA) starting from artemisinic acid (AA) is presented. Diimide was used as a reducing agent, which was generated by two different methods: (1) by the reaction of hydrazine monohydrate and hydrogen peroxide and (2) by the reaction of hydrazine monohydrate and oxygen. Both methods were found to be suitable for the diimide reduction of AA showing full conversion and a high diastereoselectivity. Due to advantages in the crystallization step of DHAA, the second option for generation of diimide was chosen for the pilot plant scale-up. The reaction and the crystallization process development as well as the batch production in the pilot plant were monitored and controlled using dispersive Raman spectroscopy as PAT tool. Three DHAA batches in kilogram scale were successfully produced by the reaction of artemisininic acid, hydrazine monohydrate, and a gas mixture of nitrogen and oxygen (containing 5% v/v oxygen) in 2-propanol at 40 °C. Excellent yields of >90% (including the crystallization, isolation, and drying step) as well as high diastereoselectivities (≥97:3) of the products were achieved by the elaborated pilot plant manufacturing processes.
Novartis’ Serelaxin Gets FDA Breakthrough Designation
Recognition by the US Food and Drug Administration (FDA) that RLX030 has the potential to address a serious unmet medical need
If approved, RLX030 has the potential to be the first treatment breakthrough for Acute Heart Failure patients in 20 years
RLX030 is the second Breakthrough Therapy designation by the FDA for Novartis investigational treatments, following LDK378
Basel, June 21, 2013 – Novartis announced today that the US Food and Drug Administration (FDA) has granted Breakthrough Therapy designation status to RLX030 (serelaxin), an investigational treatment for patients with acute heart failure (AHF). The FDA has concluded that RLX030 qualifies for a Breakthrough Therapy designation after considering the available clinical evidence which supports a substantial improvement over currently available therapies for AHF[3], a life-threatening illness…………….
http://www.pharmalive.com/novartis-serelaxin-gets-fda-breakthrough-designation
Serelaxin (RLX030) is an investigational drug targeting the relaxin receptor. Serelaxin is a recombinant form of human relaxin-2, a hormone that (among other functions) is produced during pregnancy and mediates the haemodynamic changes that occur during this time , such as increased blood output of the heart and blood flow in the kidney.
Serelaxin is currently undergoing clinical trials in patients with acute heart failure, and is being developed by Novartis.
structure
L-Serine, L-α-aspartyl-L-seryl-L-tryptophyl-L-methionyl-L-α-glutamyl-L-α-glutamyl-L-valylL-isoleucyl-L-lysyl-L-leucyl-L-cysteinylglycyl-L-arginyl-L-α-glutamyl-L-leucyl-L-valyl-L- arginyl-L-alanyl-L-glutaminyl-L-isoleucyl-L-alanyl-L-isoleucyl-L-cysteinylglycyl-L- methionyl-L-seryl-L-threonyl-L-tryptophyl-, cyclic (11→11′),(23→24′)-bis(disulfide) with 5-oxo-L-prolyl-L-leucyl-L-tyrosyl-L-seryl-L-alanyl-L-leucyl-L-alanyl-L-asparaginyl-L-lysyl-L- cysteinyl-L-cysteinyl-L-histidyl-L-valylglycyl-L-cysteinyl-L-threonyl-L-lysyl-L-arginyl-L- seryl-L-leucyl-L-alanyl-L-arginyl-L-phenylalanyl-L-cysteine cyclic (10’→15′)-disulfide
CHEMICAL NAMES
1. L-Serine, L-α-aspartyl-L-seryl-L-tryptophyl-L-methionyl-L-α-glutamyl-L-α-glutamyl-L-valyl-
L-isoleucyl-L-lysyl-L-leucyl-L-cysteinylglycyl-L-arginyl-L-α-glutamyl-L-leucyl-L-valyl-L-
arginyl-L-alanyl-L-glutaminyl-L-isoleucyl-L-alanyl-L-isoleucyl-L-cysteinylglycyl-L-
methionyl-L-seryl-L-threonyl-L-tryptophyl-, cyclic (11→11′),(23→24′)-bis(disulfide) with
5-oxo-L-prolyl-L-leucyl-L-tyrosyl-L-seryl-L-alanyl-L-leucyl-L-alanyl-L-asparaginyl-L-lysyl-L-
cysteinyl-L-cysteinyl-L-histidyl-L-valylglycyl-L-cysteinyl-L-threonyl-L-lysyl-L-arginyl-L-
seryl-L-leucyl-L-alanyl-L-arginyl-L-phenylalanyl-L-cysteine cyclic (10’→15′)-disulfide
2. Human relaxin 2 (relaxin H2)
MOLECULAR FORMULA C256H408N74O74S8
MOLECULAR WEIGHT 5.96 kDa
SPONSOR Novartis Pharma AG
CODE DESIGNATION RLX030
CAS REGISTRY NUMBER 99489-94-8
Treatment of acute heart failure
Structure
http://www.ama-assn.org/resources/doc/usan/serelaxin.pdf
- H. Spreitzer (4 March 2013). “Neue Wirkstoffe – Serelaxin”. Österreichische Apothekerzeitung (in German) (5/2013): 36.
- Dirk Einecke (23 November 2012). “Schwangerschaftshormon gegen Herzschwäche” [Pregnancy hormone against heart failure]. ÄrzteZeitung.
- Conrad KP (August 2011). “Maternal vasodilation in pregnancy: the emerging role of relaxin”. Am. J. Physiol. Regul. Integr. Comp. Physiol. 301 (2): R267–75. doi:10.1152/ajpregu.00156.2011. PMC 3154715. PMID 21613576.
- Teerlink, John R; Cotter, Gad; Davison, Beth A; Felker, G Michael; Filippatos, Gerasimos; Greenberg, Barry H; Ponikowski, Piotr; Unemori, Elaine; Voors, Adriaan A; Adams, Kirkwood F; Dorobantu, Maria I; Grinfeld, Liliana R; Jondeau, Guillaume; Marmor, Alon; Masip, Josep; Pang, Peter S; Werdan, Karl; Teichman, Sam L; Trapani, Angelo; Bush, Christopher A; Saini, Rajnish; Schumacher, Christoph; Severin, Thomas M; Metra, Marco (1 November 2012). “Serelaxin, recombinant human relaxin-2, for treatment of acute heart failure (RELAX-AHF): a randomised, placebo-controlled trial”. The Lancet.doi:10.1016/S0140-6736(12)61855-8.
Supervision of Chinese-Made Drug Substances by Philippe André
Why source drug substances from China?
Large markets, economies of scale and cheaper labor;An industrial ecosystem supplying raw materials and equipment;Developed infrastructure and industry friendly policies;About 5,000 manufacturers;
Thousands of chemists and students across China looking for novel synthesis routes for generic drug substances and intermediates.
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http://www.allfordrugs.com/2013/06/21/supervision-of-chinese-made-drug-substances-by-philippe-andre/
Pharmaceutical Industry In Global Market: Issues To Be Handled For Better Growth
In the global market, the position of the pharmaceutical industry is not parallel as compared to other information and technology based industries.
Among the Leading industries, the pharmaceutical industry lacks behind in the growth rate as far as innovative research, capital investment and
government regulations are concern. Most of the countries simply depends on bulk production of the generic drugs and not focused on core research. In
comparison with the growth rate of the electronic and IT industry stands first where as the pharmaceutical comes at the 9th position.
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Vivus has presented data on its already-approved but not-yet-marketed erectile dysfunction drug Stendra which shows that the treatment is effective for sexual activity within 15 minutes.
Stendra (avanafil) was given the green light by the US Food and Drug Administration over a year ago, but there has been no launch yet as Vivus has been seeking a partner. The latest data should be attractive to potential suitors and could help Stendra take on other phosphodiesterase type 5 (PDE5) inhibitors, notably Pfizer’s Viagra (sildenafil) but also Eli Lilly’s Cialis (tadalafil) and Bayer’s Levitra (vardenafil).
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http://www.pharmatimes.com/Article/13-06-20/Vivus_ED_drug_gets_to_work_in_less_than_15_mins.aspx
Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:Yamada, K.; Matsuki, K.; Omori, K.; Kikkawa, K.; 2004, U.S. Patent 6,797,709
- A cutting that phenanthrene by a methylthio urea ( a ) and ethoxy methylene malonate ( 2 ) cyclization of 3 , chloride, phosphorus oxychloride get 4 , 4 with benzyl amine 5 occurred SNAr the reaction product after oxidation with mCPBA 6 . In pyrimidine, if the 2 – and 4 – positions are active simultaneously the same leaving group in the case, SNAr reaction occurs preferentially at 4 – position, but does not guarantee the 2 – side reaction does not occur. Here is an activity of the poor leaving group sulfide spans 2 – bit, and a good leaving group active chlorine occupy four – position, thus ensuring a high regioselectivity of the reaction. 4 – position after completion of the reaction, then the 2 – position of the group activation, where sulfide sulfoxide better than the leaving group. Amino alcohols 7 and 6 recurrence SNAr reaction 8 , 8 after alkaline hydrolysis and acid alpha amidation get that phenanthrene.
HPV Vaccine Halves Infection Rate in Teen Girls
A vaccine against a cervical cancer virus has cut infections in teen girls by half, according to a study released.
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A vaccine against a cervical cancer virus has cut infections in teen girls by half, according to a study released. The study confirms research done before the HPV vaccine came on the market in 2006. But this is the first evidence of how well it works now that it is in general use.
New Drug Approvals 