New Drug Approvals

Home » Uncategorized » VORICONAZOLE SPECTRAL VISIT

VORICONAZOLE SPECTRAL VISIT

DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

PAYPAL DONATIONS

ORGANIC SPECTROSCOPY

Read all about Organic Spectroscopy on ORGANIC SPECTROSCOPY INTERNATIONAL 

Categories

Blog Stats

  • 1,302,568 hits

Enter your email address to follow this blog and receive notifications of new posts by email.

Join 1,773 other followers

add to any

Share

ChemSpider 2D Image | Voriconazole | C16H14F3N5O.
 VORICONAZOLE
CAS  137234-62-9
(aR,bS)-a-(2,4-Difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimideethanol
 2R,3S-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Manufacturers’ Codes: UK-109496
Trademarks: Vfend (Pfizer)
MF: C16H14F3N5O
MW: 349.31
Percent Composition: C 55.01%, H 4.04%, F 16.32%, N 20.05%, O 4.58%
Properties: mp 127°. [a]D25 -62° (c = 1 in methanol).
Melting point: mp 127°
Optical Rotation: [a]D25 -62° (c = 1 in methanol)
Therap-Cat: Antifungal (systemic)
1H NMR DMSO-d6, peak at 3.3 is HOD
NMR PIC FROM THE NET

 

m.p=134
1H-NMR (300 MHz, DMSO-d6) δ
(ppm): 
9.04 (1H), 8.84 (1H), 8.23 (1H), 7.61 (1H), 7.28 (1H), 7.17 (1H), 6.91 (1H), 

5.97 (1H), 

4.80 (1H), 

4.34 (1H), 

3.93 (1H), 

1.1 (3H)………….US8263769

13 C NMR

DMSO-d6

 NMR PIC FROM THE NET
 1H NMR PREDICT
 
 13C NMR PREDICT
COSY PREDICT

 

HMBC PREDICT

 

HPLC

 

………………….

PAPER

J. Org. Chem., 2013, 78 (22), pp 11396–11403
DOI: 10.1021/jo4019528
……………………..
Org. Proc. Res. Dev., 2001, 5 (1), pp 28–36
DOI: 10.1021/op0000879
(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1). ……………to provide the title compound as a white solid (7.6 g, 40% mass yield or 80% of available enantiomer), mp 134 °C
1H NMR (DMSO-d6) δ 1.1 (d, 3H), 3.93 (q, 1H), 4.34 (d, 1H), 4.80 (d, 1H), 5.97 (bs, 1H), 6.91 (ddd, 1H), 7.17 (ddd, 1H), 7.28 (ddd, 1H), 7.61 (s, 1H), 8.23 (s, 1H), 8.84 (s, 1H), 9.04 (s, 1H) ppm.
Cited Patent Filing date Publication date Applicant Title
US6586594 26 Jul 1996 1 Jul 2003 Pfizer, Inc. Preparation of triazoles by organometallic addition to ketones and intermediates therefor
CN1488630A 8 Oct 2002 14 Apr 2004 张文更 Method for preparing triazole antifungal agent
CN1814597A 9 Dec 2005 9 Aug 2006 北京丰德医药科技有限公司 New method for preparing voriconazole
EP0440372A1 24 Jan 1991 7 Aug 1991 Pfizer Limited Triazole antifungal agents
GB2452049A Title not available
WO1993007139A1 1 Oct 1992 15 Apr 1993 Pfizer Ltd Triazole antifungal agents
WO1997006160A1 26 Jul 1996 20 Feb 1997 Michael Butters Preparation of triazoles by organometallic addition to ketones and intermediates therefor
WO2006065726A2 13 Dec 2005 22 Jun 2006 Reddys Lab Ltd Dr Process for preparing voriconazole
WO2007013096A1 26 Jun 2006 1 Feb 2007 Msn Lab Ltd Improved
process for the preparation of 2r,
3s-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)
butan-2-ol (voriconazole)
WO2007132354A2 29 Jan 2007 22 Nov 2007 Medichem Sa Process for preparing voriconazole, new polymorphic form of intermediate thereof, and uses thereof
WO2009024214A1 * 10 Jul 2008 26 Feb 2009 Axellia Pharmaceuticals Aps Process for the production of voriconazole
WO2009084029A2 2 Dec 2008 9 Jul 2009 Venkatesh Bhingolikar Improved
process for the preparation of (2r,3s)-2-(2,4-
difluqrophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)
butan-2-ol
US8575344 * 1 Feb 2011 5 Nov 2013 Dongkook Pharmaceutical Co., Ltd. Process for preparing voriconazole by using new intermediates
US20130005973 * 1 Feb 2011 3 Jan 2013 Dongkook Pharmaceutical Co., Ltd. Process for preparing voriconazole by using new intermediates
WO2011096697A2 * 1 Feb 2011 11 Aug 2011 Dongkook Pharmaceutical Co., Ltd. Process for preparing voriconazole by using new intermediates
US8263769 * 4 Aug 2008 11 Sep 2012 Hanmi Science Process for preparing voriconazole
US8575344 1 Feb 2011 5 Nov 2013 Dongkook Pharmaceutical Co., Ltd. Process for preparing voriconazole by using new intermediates
US20100190983 * 4 Aug 2008 29 Jul 2010 Hanmi Pharm, Co., Ltd. Process for preparing voriconazole

 

WO1997006160A1 * 26 Jul 1996 20 Feb 1997 Michael Butters Preparation of triazoles by organometallic addition to ketones and intermediates therefor
WO2006065726A2 * 13 Dec 2005 22 Jun 2006 Reddys Lab Ltd Dr Process for preparing voriconazole
EP0440372A1 * 24 Jan 1991 7 Aug 1991 Pfizer Limited Triazole antifungal agents

Reference

1 Butters et al., “Process Development of Voriconazole: A Novel Broad-Spectrum Triazole Antifungal Agent,” Organic Process Research & Development, 2001, vol. 5, pp. 28-36.

References:

Ergosterol biosynthesis inhibitor. Prepn: S. J. Ray, K. Richardson, EP 440372; eidem, US 5278175 (1991, 1994 both to Pfizer); R. P. Dickinson et al., Bioorg. Med. Chem. Lett. 6, 2031 (1996).

Mechanism of action: H. Sanati et al.,Antimicrob. Agents Chemother. 41, 2492 (1997). In vitro antifungal spectrum: F. Marco et al., ibid. 42, 161 (1998).

HPLC determn in plasma: R. Gage, D. A. Stopher, J. Pharm. Biomed. Anal. 17, 1449 (1998).

Review of pharmacology and clinical development: P. E. Verweij et al., Curr. Opin. Anti-Infect. Invest. Drugs 1, 361-372 (1999); J. A. Sabo, S. M. Abdel-Rahman, Ann. Pharmacother. 34, 1032-1043 (2000).

Clinical pharmacokinetics: L. Purkins et al., Antimicrob. Agents Chemother. 46, 2546 (2002).

Clinical comparison with amphotericin B: T. J. Walsh et al., N. Engl. J. Med. 346, 225 (2002).

 

 

MOLFILE

COPY ONLY BLUE SECTION

START

64684.mol

ChemDraw07261512442D

26 28  0  0  0  0  0  0  0  0999 V2000

0.5118    1.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-0.2030    0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-0.9179    0.3031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0

-0.6206    1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-0.2030    2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0

-0.6206    2.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-1.4441    2.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0

-1.8559    2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-1.4441    1.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-1.8559    0.7149    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0

0.2088    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

-0.5062   -0.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0

0.9236    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

0.9236    1.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0

1.5928    1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

1.3354    2.5107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0

0.5118    2.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

0.2545    1.7215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0

0.6205   -0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

0.2088   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

0.6205   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

1.4440   -2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

1.8559   -2.8595    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0

1.8559   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

1.4440   -0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0

1.8559    0.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0

1  2  1  0

2  3  1  1

2  4  1  0

2 11  1  0

4  5  1  0

4  9  2  0

5  6  2  0

6  7  1  0

7  8  2  0

8  9  1  0

9 10  1  0

11 12  1  1

11 13  1  0

11 19  1  0

13 14  1  0

14 15  1  0

14 18  1  0

15 16  2  0

16 17  1  0

17 18  2  0

19 20  1  0

19 25  2  0

20 21  2  0

21 22  1  0

22 23  1  0

22 24  2  0

24 25  1  0

25 26  1  0

M  END

END

/////////

सुकून उतना ही देना प्रभू, जितने से जिंदगी चल जाये। औकात बस इतनी देना, कि औरों का भला हो जाये।
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO …..FOR BLOG HOME CLICK HERE

Join me on Linkedin

View Anthony Melvin Crasto Ph.D's profile on LinkedIn

Join me on Facebook FACEBOOK

Join me on twitterFollow amcrasto on Twitter
Join me on google plus Googleplus

 amcrasto@gmail.com

09b37-misc2b027LIONEL MY SON
He was only in first standard in school when I was hit by a deadly one in a million spine stroke called acute transverse mylitis, it made me 90% paralysed and bound to a wheel chair, Now I keep him as my source of inspiration and helping millions, thanks to millions of my readers who keep me going and help me to keep my son happy
सुकून उतना ही देना प्रभू, जितने से
जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s

Paypal Donate

DR ANTHONY CRASTO

Follow New Drug Approvals on WordPress.com

Enter your email address to follow this blog and receive notifications of new posts by email.

Join 1,773 other followers

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

Personal Links

View Full Profile →

TWITTER

bloglovin

Follow my blog with Bloglovin The title of your home page You could put your verification ID in a comment Or, in its own meta tag Or, as one of your keywords Your content is here. The verification ID will NOT be detected if you put it here.
%d bloggers like this: