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Fanetizole structure.png


Fanetizole shows immunoregulating activity.
RN: 79069-95-7


Fanetizole mesylate [USAN]

Fanetizole mesylate


Thioureas serve as a convenient starting material for 2-aminothiazoles.

Fanetizole synthesis.

Reaction of β-phenethylamine with ammonium isothiocyanate gives the corresponding thiourea. Treatment of that product with phenacyl bromide thus affords the thiazole product.[1]

  1. Lombardino, J. G.; 1981, U.S. Patent 4,307,106


Systematic (IUPAC) name
Clinical data
Legal status
Pharmacokinetic data
Protein binding %
CAS number 79069-94-6
ATC code ?
PubChem CID 54339
ChemSpider 49083
Chemical data
Formula C17H16N2S 
Mol. mass 280.39 g/mol


Journal of the Chinese Chemical Society, 2009, 56, 455-458

Fanetizole (3j)
mp 114-115 C (Lit.,30 116-117 C). IR (KBr) :3192, 2957, 1562, 1481, 1445, 1332, 698 cm-1;

1H NMR(CDCl3) : 2.81 (t, J = 7.4 Hz, 2H), 3.42 (dd, J = 6.8, 10.8
Hz, 2H), 6.32 (s, 1H), 6.64 (s, 1H), 7.08 (d, J = 6.8 Hz, 2H),
7.15-7.28 (m, 4H), 7.34-7.37 (m, 2H), 7.77-7.80 (m, 2H).

30=. Potewar, T. M.; Ingale, S. A.; Srinivasan, K. V. Tetrahedron
2008, 64, 5019-5022.


A remarkably high-speed solution-phase combinatorial synthesis of 2-substituted-amino-4-aryl thiazoles in polar solvents in the absence of a catalyst under ambient conditions and study of their antimicrobial activities
ISRN Organic Chemistry (2011), 434613, 6 pp. Publisher: (Hindawi Publishing Corp., )








Ley et al  had previously developed a tube-in-tube reactor based on a semipermeable polymer membrane to  enable the transfer of gases into liquid flow streams. and here, we demonstrate the scalability and throughput of this reactor when used with ammonia gas. This was made possible by a the inclusion of a titration method to assess parameters including the liquid and gas configuration, reactor temperatures, flow rates, and solvent polarity. These data were then employed in a scaling-up process affording alkyl thioureas which were ultimately used in a telescoped procedure for the preparation of anti-inflammatory agent fanetizole on a multigram scale.


Researchers at Cambridge have shown how it is possible to calibrate a ‘tube-in-tube’ reactor containing ammonia gas using a simple in-line colourimetric titration technique.

This information was then used to deliver an ammonia solution of stoichiometrically to effect the telescoped 2 stage synthesis of the anti-inflammatory agent Fanetizole.

The automated continuous flow synthesiser was able to produce drug substance at a rate of approximately 10 g per hour, isolating the product by direct precipitation from the outflow reaction stream.

Fanetizole: Scaling-up of continuous flow processes with gases using a tube-in-tube reactor: in-line titrations and fanetizole synthesis with ammonia J. Pastre, D.L. Browne, M. O’Brien and S.V. Ley, Org. Proc. Res. Dev201317, 1183-1191.

N-Phenethyl-4-phenylthiazol-2-amine: fanetizole (4):
IR (cm–1, thin film): 1602, 1585, 1424, 1332, 773, 743, 697;
1H NMR (400 MHz, CDCl3): δ 7.85 (d, J = 7.3 Hz, 2H), 7.49–7.13 (m, 8H), 6.72 (s, 1H), 6.00 (br s, 1H), 3.55 (m, 2H), 2.94 (t, J = 7.1 Hz, 2H);
13C NMR (100 MHz, CDCl3): δ 169.5 (C0), 151.5 (C0), 138.5 (C0), 134.9, 128.7 (CH), 128.6 (CH), 128.5 (CH), 127.6 (CH), 126.5 (CH), 126.0 (CH), 100.6 (CH), 47.2 (CH2), 35.4 (CH2);
HRMS (ESI+) m/z: Calcd for C17H17N2S [M + H+] 281.1107, found 281.1100.


A Hantzsch synthesis of 2-aminothiazoles performed in a heated microreactor system

*Corresponding authors
aGlaxoSmithKline Pharmaceuticals, New Frontiers Science Park (North), Essex, Harlow, UK
Fax: +44 (0)1279 622500 ;
Tel: +44 (0)1279 627993
Lab Chip, 2002,2, 31-33

DOI: 10.1039/B109360F…….!divAbstract

..This paper presents the first example known to the authors of a heated organic reaction performed on a glass microreactor under electro-osmotic flow control. The experiments consisted of the preparation of a series of 2-aminothiazoles by means of a Hantzsch reaction of ring-substituted 2-bromoacetophenones and 1-substituted-2-thioureas carried out in microchannels, with the aim of investigating the generic utility of the reactor in carrying out analogue reactions. The reactions were performed on T-design microchips etched into a thin borosilicate glass plate and sealed over with a thick borosilicate top plate containing reservoirs. The mobility of the reagents and products was achieved using electro-osmotic flow (EOF), with the driving voltages being generated by a computer-controlled power supply. During the experiments the T-shaped chip was heated at 70 °C using a Peltier heater, aligned with the channels and the heat generated by this device was applied to the lower plate. The degree of conversion was quantified by LC-MS using UV detection by comparison with standard calibration curves for starting materials and final products. In all cases, conversions were found to be similar or greater than those found for equivalent macro scale batch syntheses, thus illustrating the potential of this heated microreactor system to generate a series of compounds which contain biologically active molecules.


Bioorganic and Medicinal Chemistry Letters, 1996 ,  vol. 6,   12  pg. 1409 – 1414

Full-size image (1 K)




Heterocycles, 2010 ,  vol. 81,   12  pg. 2849 – 2854

Journal of the Chinese Chemical Society, 2009 ,  vol. 56,  3  pg. 455 – 458

Bioorganic and Medicinal Chemistry Letters, 1996 ,  vol. 6,   12  pg. 1409 – 1414

Pfizer Patent: DD144055DE2922523 , 1979 ;Chem.Abstr.,  vol. 92,  111001

Organic Process Research and Development, 2013 ,  vol. 17,   9  pg. 1183 – 1191

Tetrahedron, 2007 ,  vol. 63,   45  pg. 11066 – 11069

Tetrahedron, 2008 ,  vol. 64,  22  pg. 5019 – 5022

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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 AFRICURE PHARMA, ROW2TECH, NIPER-G, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers, Govt. of India as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 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 Open superstar 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 32 PLUS year tenure till date Feb 2023, Around 35 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 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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