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PDE4 inhibitor , Sumitomo Dainippon Pharma Company



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2-[2-Methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-benzimidazol-5-yl]-1,3-benzoxazole Hemifumarate

Sumitomo Dainippon Pharma Company,



CAS FREE FORM 1256966-65-0

Benzoxazole, 2-[2-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-benzimidazol-5-yl]-

MF C20 H19 N3 O2, MW, 333.38 FREE FORM

1H NMR (400 MHz, DMSO-d6)

δ 13.1 (br, 1H), 8.33 (d, J = 1.5 HZ, 1H), 8.06 (dd, J = 5.1, 1.6 Hz, 1H), 7.89 (d, J = 0.8 Hz, 1H), 7.82–7.76 (m, 2H), 7.43–7.38 (m, 2H), 6.64 (s, 1H), 4.71–4.62 (m, 1H), 4.06 (dd, J = 11.4, 4.3 Hz, 2H), 3.58 (dd, J = 11.7, 11.4 Hz, 2H), 2.67 (s, 3H), 2.47–2.36 (m, 2H), 1.90–1.86 (m, 2H).

13C NMR (100 MHz, DMSO-d6)

δ 165.92, 163.26, 153.94, 150.20, 142.94, 141.75, 136.21, 133.93, 124.94, 124.67, 120.89, 119.40, 117.70, 112.44, 110.72, 66.50, 52.67, 30.70, 14.62.
Compound 1 is a PDE4 inhibitor and is expected to improve memory impairment. In addition to the mechanism of action, 1 enhances BDNF signal transduction and induces NXF, a brain specific transcription factor, in the presence of low concentrations of BDNF. NXF induction is expected to lead to nerve regeneration and neuroprotective efficacy.
US88290352014-09-09Agent for treatment or prevention of diseases associated with activity of neurotrophic factors
Example 11
5- (benzoxazol-2-yl) -2-methyl -1-(tetrahydropyran-4-yl) benzimidazole  eggplant flask (100 mL), 2- methyl-1- (tetrahydropyran – 4-yl) reference benzimidazole-5-carboxylic acid (example 4-3) (0.64 g, 2.46 mmol ), 2- amino-phenol (0.32 g, 2.95 mmol), and polyphosphoric acid (about 18 g) put, heated to 160 ℃, and the mixture was stirred for 17 hours. After cooling, ice was added, and the mixture was about pH 9 the liquid with concentrated aqueous ammonia (28%). Extraction with chloroform (about 50 mL X 3 times), dried over anhydrous magnesium sulfate, the crude product obtained by distilling off the solvent (0.08 g) PTLC (CHCl 3 by weight deploy purified), the title compound ( 0.002 g, 0.2% yield) was obtained as a yellow-brown semi-solid. 1H-NMR (CDCl 3 ) Deruta (Ppm): 1.88-1.92 (M, 2 H), 2.58-2.68 (M, 2 H), 2.70 (S, 3 H), 3.57-3.64 (M , 2 H), 4.21-4.25 (m , 2 H), 4.43-4.49 (m, 1 H), 7.29 (d, 1H, J = 9.2 Hz), 7.33-7.35 (m, 2 H ), 7.59-7.62 (m, 1 H ), 7.76-7.78 (m, 1 H), 8.18 (dd, 1 H, J = 8.6, 1.6 Hz), 8.57 (d, 1 H, J = 1.4 Hz).


Abstract Image

A short and practical synthetic route of a PDE4 inhibitor (1) was established by using Pd–Cu-catalyzed C–H/C–Br coupling of benzoxazole with a heteroaryl bromide. The combination of Pd(OAc)2-Cu(OTf)2-PPh3 was found to be effective for this key step. Furthermore, telescoping methods were adopted to improve the yield and manufacturing time, and a two-step synthesis of1 was accomplished in 71% overall yield.

Direct Synthesis of a PDE4 Inhibitor by Using Pd–Cu-Catalyzed C–H/C–Br Coupling of Benzoxazole with a Heteroaryl Bromide

Process Chemistry Research and Development Laboratories, Technology Research & Development Division andDSP Cancer Institute, Sumitomo Dainippon Pharma Company, Ltd., 3-1-98 Kasugade-naka, Konohana-ku, Osaka 554-0022, Japan
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00106

///////////PDE4 inhibitor , Sumitomo Dainippon Pharma Company


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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 GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 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, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, 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 30 year tenure till date Dec 2017, 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 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, 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 19 lakh plus views on New Drug Approvals Blog in 216 countries...... , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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