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Doxercalciferol, доксэркальциферол , دوكساركالسيفيرول , 度骨化醇

November 22, 2016 10:32 am / Leave a comment

ChemSpider 2D Image | doxercalciferol | C28H44O2

Doxercalciferol

Molecular FormulaC₂₈H₄₄O₂
Average mass412.648

доксэркальциферол [Russian]

دوكساركالسيفيرول [Arabic]

度骨化醇 [Chinese]

1,3-Cyclohexanediol, 4-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-4H-inden-4-ylidene]ethylidene]-, (1R,3S,5Z)-

54573-75-0

Title: Doxercalciferol

CAS Registry Number: 54573-75-0

CAS Name: (1a,3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3-diol

Additional Names: 1a-hydroxyvitamin D2; 1-hydroxyergocalciferol

Trademarks: Hectorol (Bone Care)

Molecular Formula: C28H44O2

Molecular Weight: 412.65

Percent Composition: C 81.50%, H 10.75%, O 7.75%

Literature References: Synthetic vitamin D prohormone. Prepn: H.-Y. P. Lam et al., Science 186, 1038 (1974); eidem, Steroids30, 671 (1977); H. E. Paaren et al., J. Org. Chem. 45, 3253 (1980). Comparative activity and toxicity: G. Sjöden et al., Proc. Soc. Exp. Biol. Med. 178, 432 (1985). Metabolism to bioactive form: J. C. Knutson et al., Endocrinology 136, 4749 (1995). Pharmacology: J. W. Coburn et al., Nephrol. Dial. Transplant. 11, Suppl. 3, 153 (1996). Clinical trial for suppression of secondary hyperparathyroidism in hemodialysis: J. M. Frazao et al., ibid. 13, Suppl. 3, 68 (1998).

Properties: Crystals, mp 138-140°. uv max (ethanol): 265 nm (e 18300). LD50 orally in rats: 3.5-6.5 mg/kg (Sjöden).

Melting point: mp 138-140°

Absorption maximum: uv max (ethanol): 265 nm (e 18300)

Toxicity data: LD50 orally in rats: 3.5-6.5 mg/kg (Sjöden)

Therap-Cat: Antihyperparathyroid.

Keywords: Antihyperparathyroid.

Image result for Doxercalciferol

CLIP

Abstract Image

Doxercalciferol (1α-hydroxyvitamin D2) is a commercially approved vitamin D derivative used to treat chronic kidney disease (CKD) patients whose kidneys cannot metabolically introduce a hydroxyl group at C1. A new process for the production of doxercalciferol from ergocalciferol was developed using a continuous photoisomerization of a known vitamin D intermediate as the key step, thus circumventing the limitations of batch photoisomerization processes. Doxercalciferol is produced in an overall yield of about 10% from ergocalciferol.

Doxercalciferol

1H NMR (CDCl3) δ 6.40 (d, 1H, J = 11.2), 6.04 (d, 1H, J = 11.2), 5.35 (s, 1H), 5.15–5.29 (m, 2H), 5.03 (s, 1H), 4.45 (dd, 1H, J = 7.3, 4.0), 4.21–4.31 (m, 1H), 2.81–2.90 (m, 1H), 2.62 (d, 1H, J = 13.3), 2.34 (dd, 1H, J = 13.3, 6.5), 1.83–2.11(m, 6H), 1.42–1.79 (m, 7H), 1.21–1.40 (m, 3H), 1.04 (d, 3H, J = 6.6), 0.94 (d, 3H, J = 6.8), 0.86 (t, 6H, J = 7.3), 0.58 (s, 3H) ppm.

Doxercalciferol (trade name Hectorol) is drug for secondary hyperparathyroidism and metabolic bone disease.^[1] It is a synthetic analog of ergocalciferol (vitamin D₂). It suppresses parathyroid synthesis and secretion.^[2]

PATENT

https://www.google.com/patents/US20130023681

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CLIP

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References

Jump up^ Sprague S M; Ho L T (2002). “Oral doxercalciferol therapy for secondary hyperparathyroidism in a peritoneal dialysis patient”.Clinical nephrology. 58 (2): 155–160. PMID 12227689.

Doxercalciferol
Names

IUPAC name (1S,3R,5Z,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraene-1,3-diol
Other names 1-Hydroxyergocalciferol; 1-Hydroxyvitamin D2; 1α-Hydroxyergocalciferol; 1α-Hydroxyvitamin D2; Hectorol; TSA 840
Identifiers
CAS Number	54573-75-0
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1200810
ChemSpider	4444554
DrugBank	DB06410
ECHA InfoCard	100.170.997
IUPHAR/BPS	2790
PubChem	5281107
UNII	3DIZ9LF5Y9
InChI [show]
SMILES [show]
Properties
Chemical formula	C₂₈H₄₄O₂
Molar mass	412.66 g·mol⁻¹
Pharmacology
ATC code	H05BX03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Now online – Stimuli article on the proposed USP General Chapter “The Analytical Procedure Lifecycle “

November 22, 2016 9:54 am / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

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Now online – Stimuli article on the proposed USP General Chapter “The Analytical Procedure Lifecycle <1220>”

A Stimuli Article to the Revision Process regarding the proposed New USP General Chapter “The Analytical Procedure Lifecycle <1220>” has been published. Read more about the new concept for the lifecycle managment of analytical methods.

http://www.gmp-compliance.org/enews_05629_Now-online—Stimuli-article-on-the-proposed-USP-General-Chapter-%22The-Analytical-Procedure-Lifecycle–1220-%22_15438,Z-PDM_n.html

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The General Chapters—Chemical Analysis Expert Committee is currently developing a new general chapter <1220> The Analytical Procedure Lifecycle. The purpose of this new chapter will be to more fully address the entire procedure lifecycle and define concepts that may be useful.

A Stimuli article on the proposed General Chapter <1220> has been approved for publication in Pharmacopeial Forum 43(1) [Jan.-Feb. 2017]. USP is providing this Stimuli article in advance of its publication to provide additional time for comments.

In addition to offering a preview of the proposed general chapter, the General Chapters—Chemical Analysis Expert Committee and the Validation and…

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New EDQM’s Public Document informs about the Details required in a New CEP Application for already Referenced Substances

November 22, 2016 9:54 am / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

A Policy Document recently published by the EDQM describes regulations for referencing already existing CEPs in an application for a new CEP. Read more about how the certificates of an intermediate or starting material have to be used in new applications for a CEP.

http://www.gmp-compliance.org/enews_05624_New-EDQM-s-Public-Document-informs-about-the-Details-required-in-a-New-CEP-Application-for-already-Referenced-Substances_15429,15332,15982,15721,S-WKS_n.html

When applying for a Certificate of Suitability (CEP) for an API, detailed information has to be provided regarding the synthesis stages, the starting material and the intermediates. In the event that the starting materials or the intermediates are already covered by a CEP, the EDQM has recently published a “Public Document” entitled “Use of a CEP to describe a material used in an application for another CEP”. The document contains regulations on how to reference the “CEP X” of a starting material or an intermediate in the application for the “CEP Y” of an API. The requirements for both scenarios are described as follows:

CEP…

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Opportunities for Reducing Sampling and Testing of Starting Materials

November 22, 2016 9:53 am / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

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Chapter 5 of the EC GMP Guide for the area of production was updated last year. This chapter contains concrete information about the conditions when testing and sampling of APIs and excipients can be reduced. Read more here about the sections 5.35 and 5.36 of the EU GMP Guide.

http://www.gmp-compliance.org/enews_05655_Opportunities-for-Reducing-Sampling-and-Testing-of-Starting-Materials_15461,15911,15462,Z-QCM_n.html

Chapter 5 of the EC GMP Guide for the area of production was already updated last year. However, not everybody really knows that it contains concrete information about the conditions when testing and sampling of APIs and excipients can be reduced. Particularly sections 5.35 and 5.36 include requirements and thus show possibilities for a reduction.

Basically, the manufacturers of finished products are responsible for every testing of starting materials as described in the marketing authorisation dossier. Yet, part of or complete test results from the approved starting material manufacturer can be used, but at least their identity has to be tested…

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EMA/ FDA Mutual Recognition Agreement on drug facility inspections moving forward

November 22, 2016 9:52 am / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

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EMA/ FDA Mutual Recognition Agreement moving forward

A possible agreement between the EMA and the US FDA on mutual recognition agreement on drug facility inspections could already be signed in January 2017.

http://www.gmp-compliance.org/enews_05650_EMA–FDA-Mutual-Recognition-Agreement-moving-forward_15642,15660,15656,Z-QAMPP_n.html

A possible agreement between the European Medicines Agency EMA and the US Food and Drug Administration FDA on mutual recognition of drug facility inspections could already be signed in January 2017. This is noted in a report of the EU Commission: “The state-of-play and the organisation of the evaluation of the US and the EU GMP inspectorates were discussed. In light of the progress achieved, the conclusion of a mutual recognition agreement of Good Manufacturing Practices (GMPs) inspections by January 2017 is under consideration.”

But, according to the Commission, some issues are still not resolved – like, for example, the exchange of confidential information and the inclusion of veterinary products in the scope of the text.

The “Report of the…

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New EDQM’s Public Document informs about the Details required in a New CEP Application for already Referenced Substances

November 10, 2016 1:00 am / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

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click

http://www.gmp-compliance.org/enews_05624_New-EDQM-s-Public-Document-informs-about-the-Details-required-in-a-New-CEP-Application-for-already-Referenced-Substances_15429,15332,15982,15721,S-WKS_n.html

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Acetylcholine Chloride

November 9, 2016 11:57 am / 1 Comment on Acetylcholine Chloride

Acetylcholine Chloride

2-acetyloxyethyl(trimethyl)azanium;chloride

60-31-1

Molecular Formula:	C7H16ClNO2
Molecular Weight:	181.66 g/mol

Acetylcholine chloride is obtained as white or off-white hygroscopic crystals, or as a crystalline powder. The salt is odorless, or nearly odorless, and is a very deliquescent powder. Acetylcholine bromide is obtained as deliquescent crystals, or as a white crystalline powder. The substance is hydrolyzed by hot water and alkali

Image result for acetylcholine chloride

Acetylcholine is an organic chemical that functions in the brain and body of many types of animals, including humans, as a neurotransmitter—a chemical released by nerve cells to send signals to other cells. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic. Substances that interfere with acetylcholine activity are called anticholinergics.

Acetylcholine is the neurotransmitter used at the neuromuscular junction—in other words, it is the chemical that motor neurons of the nervous system release in order to activate muscles. This property means that drugs that affect cholinergic systems can have very dangerous effects ranging from paralysis to convulsions. Acetylcholine is also used as a neurotransmitter in the autonomic nervous system, both as an internal transmitter for the sympathetic nervous system and as the final product released by the parasympathetic nervous system.

Inside the brain, acetylcholine functions as a neuromodulator—a chemical that alters the way other brain structures process information rather than a chemical used to transmit information from point to point. The brain contains a number of cholinergic areas, each with distinct functions. They play an important role in arousal, attention, and motivation.

Partly because of its muscle-activating function, but also because of its functions in the autonomic nervous system and brain, a large number of important drugs exert their effects by altering cholinergic transmission. Numerous venoms and toxins produced by plants, animals, and bacteria, as well as chemical nerve agents such as Sarin, cause harm by inactivating or hyperactivating muscles via their influences on the neuromuscular junction. Drugs that act on muscarinic acetylcholine receptors, such as atropine, can be poisonous in large quantities, but in smaller doses they are commonly used to treat certain heart conditions and eye problems. Scopolamine, which acts mainly on muscarinic receptors in the brain, can cause delirium and amnesia. The addictive qualities of nicotine derive from its effects on nicotinic acetylcholine receptors in the brain.

Chemistry

Acetylcholine is a choline molecule that has been acetylated at the oxygen atom. Because of the presence of a highly polar, charged ammonium group, acetylcholine does not penetrate lipid membranes. Because of this, when the drug is introduced externally, it remains in the extracellular space and does not pass through the blood–brain barrier. A synonym of this drug is miochol.

History

Acetylcholine (ACh) was first identified in 1915 by Henry Hallett Dale for its actions on heart tissue. It was confirmed as a neurotransmitter by Otto Loewi, who initially gave it the name Vagusstoff because it was released from the vagus nerve. Both received the 1936 Nobel Prize in Physiology or Medicine for their work. Acetylcholine was also the first neurotransmitter to be identified.

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CLIP

http://drugsynthesis.blogspot.in/2011/11/laboratory-synthesis-of-acetylcholine.html

Laboratory Synthesis Of Acetylcholine chloride

Acetylcholine chloride Chemical Name: 2- (acetyl oxy)- N ,N ,N- tri methyl ethan aminium chloride

Acetylcholine chloride Use: parasympathomimetic, miotic, vasodilator (peripheral)

Acetylcholine chloride MW: 181.66

Acetylcholine chloride MF: C7H16ClNO2

Acetylcholine chloride LD50: 10 mg/kg (M, i.v.); 3 g/kg (M, p.o.);

22 mg/kg (R, i.v.); 2500 mg/kg (R, p.o.)

Reference(s):

Baeyer, A. v.: Justus Liebigs Ann. Chem. (JLACBF) 142, 235 (1867).
Nothnagel: Arch. Pharm. (Weinheim, Ger.) (ARPMAS) 232, 265 (1894).
Fourneau, E.; Page, H.J.: Bull. Soc. Chim. Fr. (BSCFAS) [4] 15, 544 (1914).
DE 801 210 (BASF; appl. 1948).
US 1 957 443 (Merck & Co.; 1934; appl. 1931).
US 2 012 268 (Merck & Co.; 1935; appl. 1931).
US 2 013 536 (Merck & Co.; 1935; appl. 1931).

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Acetylcholine

IUPAC name	2-Acetoxy-N,N,N-trimethylethanaminium
Abbreviation	ACh
Sources	motor neurons, parasympathetic nervous system, brain
Targets	skeletal muscles, brain, many other organs
Receptors	nicotinic, muscarinic
Agonists	nicotine, muscarine, cholinesterase inhibitors
Antagonists	tubocurarine, atropine
Precursor	choline, acetyl-CoA
Synthesizing enzyme	choline acetyltransferase
Metabolizing enzyme	acetylcholinesterase
Database links
CAS Number	51-84-3
PubChem	CID: 187
IUPHAR/BPS	294
DrugBank	EXPT00412
ChemSpider	182
KEGG	C01996

Image result for acetylcholine chloride

1H NMR PREDICT

13 C NMR PREDICT

/////////CC(=O)OCC[N+](C)(C)C.[Cl-]

Valdetamide

November 7, 2016 3:01 am / Leave a comment

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CAS Registry Number: 512-48-1

CAS Name: 2,2-Diethyl-4-pentenamide

Additional Names: diethylallylacetamide

Trademarks: Novonal (Hoechst)

Molecular Formula: C9H17NO

Molecular Weight: 155.24

Percent Composition: C 69.63%, H 11.04%, N 9.02%, O 10.31%

Literature References: Description: Bockmühl, Schaumann, Dtsch. Med. Wochenschr. 54, 270 (1928). Pharmacokinetics and metabolism: H. Uehleke, M. Brinkschulte-Freitas, Arch. Pharmacol. 302, 11 (1978). TLC determn in urine: E. Klug, P. Toffel, Arzneim.-Forsch. 29, 1651 (1979).

Properties: White powder, mp 75-76°. Sol in 120 parts water; freely sol in alcohol, ether.

Melting point: mp 75-76°

Therap-Cat: Sedative, hypnotic.

Keywords: Sedative/Hypnotic; Amides.

Valdetamid (Valdetamide)

Structural formula

UV – spectrum

The solvent designation schedule	methanol	Water	0.1 M HCl	0.1M NaOH

Conditions : Concentration – 50 mg / 100 ml
maximum absorption	–	–	–	–
	–	–	–	–
ε	–	–	–	–

IR – spectrum

Wavelength (μm)

Wave number (cm ^-1 )

Range

10 largest peaks:
Peak	53	55	57	67	69	81	112	126	127	140
Value	152	848	115	141	929	156	286	999	338	238

References

UV and IR Spectra. H.-W. Dibbern, RM Muller, E. Wirbitzki, 2002 ECV
NIST / EPA / NIH Mass Spectral Library 2008
Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman.Academic Press, 2000.
Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Brief background information

Salt	ATC	Formula	MM	CAS
–	N05C	C ₉ H ₁₇ NO	155.24 g / mol	512-48-1

Using

hypnotic

Classes substance

Amides

Synthesis Way

Synthesis of a)

Trade names

A country	Tradename	Manufacturer
Germany	Arantxa	Hoechst
	Betadorm-H	Woelm
	insomnia	ICN
	Nokturetten	Starke
	New Dolestan	Much
Ukraine	no	no

Formulations

dragees 50 mg;
300 mg Tablets

References

DRP 473 329 (IG Farben; appl 1925.).
DRP 616 876 (IG Farben; appl 1930.).
DRP 622 875 (IG Farben; appl 1931.).
GB 253,950 (IG Farben; appl 1926;.. D-prior 1925).

1H NMR PREDICT

13C NMR PREDICT

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ENHANCED ANALYTICAL METHOD CONTROL STRATEGY CONCEPT

November 6, 2016 12:34 pm / Leave a comment

DRUG REGULATORY AFFAIRS INTERNATIONAL

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ENHANCED ANALYTICAL METHOD CONTROL STRATEGY CONCEPT

The benefits of quality by design (QbD) concepts related to both product (ICH Q8)1 and drug substance (ICH Q11)2 are well-established, particularly in regards to the potential to use knowledge to affect process changes without major regulatory hurdles, i.e., revalidation/regulatory filing, etc. Less wellestablished, but potentially of significant value, is the application of the same concepts to analytical methods.

Analytical methods play an obvious key role in establishing the quality of final product as they establish conformance with product acceptance criteria (i.e., specifications) and indicate the integrity of the product through indication of product stability. Analytical methods are validated, like manufacturing processes, but what if the operational ranges could be established during method validation when demonstrating fitness for purpose?

Would it be possible to drive method improvement, especially post validation in the same way that the concept of continuous improvement is a key driver for…

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Discovery of Pyrazolopyrimidine Derivatives as Novel Dual Inhibitors of BTK and PI3Kδ

November 6, 2016 5:07 am / Leave a comment

(-)-32 as an off-white solid.
Analytical data
LCMS 418 [M+H]+1
H NMR (400 MHz, DMSO-d6) δ 8.23 (s, 1H), 6.88 (d, J = 8.0 Hz, 1H), 6.68 (s, 1H), 6.61 (dd,J = 11.2, 2.0 Hz, 1H), 6.49-6.38 (m, 2H), 6.33 (s, 1H), 5.61 (m, 1H), 4.88 (s, 2H), 4.20(t, J = 4.3 Hz, 2H), 3.35-3.18 (m, 6H).
Optical rotation [α]D20 -38.5° (c = 0.107, DMSO)

PAPER

Discovery of Pyrazolopyrimidine Derivatives as Novel Dual Inhibitors of BTK and PI3Kδ

Brahmam Pujala^‡, Anil K. Agarwal^‡, Sandip Middya^§, Monali Banerjee^§, Arjun Surya^§, Anjan K. Nayak^‡, Ashu Gupta^‡, Sweta Khare^‡, Rambabu Guguloth^‡, Nitin A. Randive^‡, Bharat U. Shinde^‡, Anamika Thakur^‡, Dhananjay I. Patel^‡, Mohd. Raja^‡, Michael J. Green^†, Jennifer Alfaro^∥, Patricio Avila^∥, Felipe Pérez de Arce^∥^⊥, Ramona G. Almirez^†, Stacy Kanno^†, Sebastián Bernales^†, David T. Hung^†, Sarvajit Chakravarty^†, Emma McCullagh^†, Kevin P. Quinn^†, Roopa Rai^†, and Son M. Pham ^*^†

^† Medivation, Inc., 525 Market Street, 36th Floor, San Francisco, California 94105, United States

^‡ Integral BioSciences, Pvt. Ltd., C-64, Hosiery Complex Phase II Extension, Noida, Uttar Pradesh 201306, India

^§ Curadev, Pvt. Ltd., B-87, Sector 83, Noida, Uttar Pradesh 201305, India

^∥ Fundación Ciencia y Vida, Avenida Zañartu 1482, Ñuñoa, Santiago 7780272, Chile

^⊥ Departamento de Ciencias Biológicas, Facultad de Ciencias Biológicas, Universidad Andrés Bello, Santiago 8370146, Chile

ACS Med. Chem. Lett., Article ASAP

DOI: 10.1021/acsmedchemlett.6b00356

*E-mail: son.pham@medivation.com.

Son Pham

Associate Director, Medicinal Chemistry at Medivation

Roopa Rai

Sr. Director, Medicinal Chemistry at Medivation

Brahmam Pujala

Senior Research Scientist at Integral Biosciences

Ashu Gupta

Research Scientist at Integral Biosciences

rambabu guguloth

Rambabu guguloth

Abstract

The aberrant activation of B-cells has been implicated in several types of cancers and hematological disorders. BTK and PI3Kδ are kinases responsible for B-cell signal transduction, and inhibitors of these enzymes have demonstrated clinical benefit in certain types of lymphoma. Simultaneous inhibition of these pathways could result in more robust responses or overcome resistance as observed in single agent use. We report a series of novel compounds that have low nanomolar potency against both BTK and PI3Kδ as well as acceptable PK properties that could be useful in the development of treatments against B-cell related diseases.

Monali Banerjee

Director, R&D

Ms. Banerjee has more than 10 years of research experience, during which she has held positions of increasing responsibility. Her past organizations include TCG Lifesciences (Chembiotek) and Sphaera Pharma. Ms. Banerjee is a versatile scientist with a deep understanding of the fundamental issues that underlie various aspects of drug discovery. At Curadev, she has been responsible for target selection, patent analysis, pharmacophore design, assay development, ADME/PK and in vivo and in vitro pharmacology. Ms. Banerjee holds a Masters in Biochemistry and a Bachelors in Chemistry both from Kolkata University.

Nidhi Adlaka & Neha Munjal are developing a bioprocess for butanediol. Over the next few decades, chemical routes of manufacture will gradually be replaced by more environment friendly biological methods.

Dr. Arjun Surya, CSO, Curadev enthralling participants with anecdotes of his entrepreneurial jrney in drugdiscovery

Manish Tandon

Co-founder Curadev Pharma Pvt Ltd

//////////////B-cell, BCR, BTK, inhibitor, p110δ, PI3K, pyrazolopyrimidine, Novel Dual Inhibitors, BTK , PI3Kδ, Medivation, Integral BioSciences, Curadev, Fundación Ciencia y Vida, Departamento de Ciencias Biológicas,

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Doxercalciferol

Doxercalciferol

References

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Chemistry

History

Laboratory Synthesis Of Acetylcholine chloride

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Discovery of Pyrazolopyrimidine Derivatives as Novel Dual Inhibitors of BTK and PI3Kδ

Son Pham

Roopa Rai

Brahmam Pujala

Ashu Gupta

Rambabu guguloth

Abstract

Monali Banerjee

Director, R&D

Dr. Arjun Surya, CSO, Curadev enthralling participants with anecdotes of his entrepreneurial jrney in drugdiscovery

Manish Tandon

//////////////B-cell, BCR, BTK, inhibitor, p110δ, PI3K, pyrazolopyrimidine, Novel Dual Inhibitors, BTK , PI3Kδ, Medivation, Integral BioSciences, Curadev, Fundación Ciencia y Vida, Departamento de Ciencias Biológicas,

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