New developments in Non-Nucleoside Reverse Transcriptase Inhibitors(NNRTIs); from TIBO to Rilpivirine (TMC278)
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1 ew developments in on-ucleoside Reverse Transcriptase Inhibitors(RTIs); from TIBO to Rilpivirine (TMC278) Jan Heeres and Paul J. Lewi Formerly Center for Molecular Design, Janssen Pharmaceutica V, Vosselaar (Belgium)
2 HIV/AIDS, a Worldwide Epidemic HIV-infected people in 2007 => 33.2 million ( million) orth America 1.2 million The Caribbean West & Central Europe orth Africa & Middle East East Europe & Central Asia 1,6 million East Asia South & South-East Asia 7,4 millions South America 1,8 million Sub-Saharan Africa 25.8 millions South Sea Islands ewly infected patients in 2007 => 2.5 million ( million) umber of deaths due to HIV in 2006 => 2.1 million ( million) UAIDS Dec including 380, 000 children
3 HIV/AIDS, a Worldwide Epidemic HIV-infected people in 2013 => 35.0 million Estimated newly infected 2.1 million in million died of AIDS related cause in 2013 UAIDS Dec. 2013
4 Molecular Modeling of R (TMC278) Hydrophobic Steric Dipole- Dipole Hydrogen Bridges C C H H Vinkers H. M., Koymans L., Daeyaert F., de Jonge M., Heeres J., Arnold E., Das K., Lewi P. and Janssen P., 2001
5 TMC278, Molecular Modeling In 2008, resolution of the structure of the wild type HIV-1 RT complexed with TMC278 at 1.8A Interactions in the RTI-binding pocket: => H-bond between linker of the right wing & the C=O of K101. => of the left wing is involved in a H 2 O mediated H-bond with C=O of E138 of the p51 subunit. => Trisubstituted phenyl ring interacts with the hydrophobic core of the binding pocket. => -CH=CH-C fits into hydrophobic tunnel. PDB ID: 2ZD1 Extensive interactions of -CH=CH-C with the hydrophobic tunnel explains high potency of TMC278 as RTI PAS, 2008, 105,
6 TMC278, Physico Chemical Properties C Crystalline structure ot hygroscopic C 22 H 18 6, H= ( ) mp = 250 C logp (ph=8)= 4.8 pka = 5.6 Stereochemistry => no stereogenic center C Solubility => H 2 O ~20ng/ml at ph7.0 H H PEG400 (40 mg/ml)
7 SAR- 2,6 disubstitution C C R1 R2 H H * IIIB K103 Y181C L100I Y188L F227C L100I+ K103 K103+ Y181C F227C+ V106A Entry R 1 R 2 pec 50 1 H H 7.4 T T T T T T T T 2 H Me T 3 H OMe 8.8 T T T 4 Me Me Me * SI (Selectivity Index) > 1000 / T= not tested Eur. J. Med. Chem. 2007, 42(5),
8 TMC278, Synthesis Pathway C C X = Br, I X CH 2 =CHC, Pd(OAc) 2, P(o-Tol) 3, Et 3, CH 3 C, 150 C, 12h Y = 60% H/EtOH, Et 2 O, 60 C, 30 min Y = 77% E/Z= 98/2 H 2 H 2 H 2.H C C C C + H CH 3 C reflux Y = 69% H H H 2.H 1- aoh, ICH 3, Y=90% 2- p-cyanoaniline, dyglime, Y=80% H S 3- PO 3, CH 3 C, reflux, Y=90% H O Organic Process Research & Dev. 2008,12,
9 pec 50 (IIIB) = H O H S H O H 2 H 2 S TIBO tivirapine R APA R ITU R Br H O H S H evirapine - Viramune Boehringer Ingelheim 1990 PETT - Trovirdine Medivir, Lilly 1993
10 H H H 2 ITU R C-imino analog of ITU H 2 DATA R H H 2 Pyrimidine analog of DATA R
11 H H H 2 R DATA R F F C F O H H O Efavirenz -Sustiva Dupont, Merck, BMS HO H R
12 H H H H R Dapivirine TMC120 - R R
13 O H Br H Etravirine TMC125, R R H H Rilpivirine TMC278 - R
14 pec 50 (IIIB) = TIBO 1990 S H 8.3 H H 2 S H H H H H O ITU 1993 DATA 1994 Dapivirine TMC120 - R O H 2 DAPY -APA O H Br H H H 2 Etravirine TMC125, R Rilpivirine TMC278 - R
15 TMC125, a novel RTI HIV activity (EC 50 ) O Br C H 2 C H Wild-type nm L100I 3.3 nm K nm Y181C 6.9 nm Y188L 5.0 nm Cytotoxicity (MT4 cells) CC 50 > 100 μm Selectivity ITELECE (TMC125) > 70,000 index Approved in 2008 TMC125 is the first RTI to show significant activity in patients with prior RTI failure Antimicrob. Agents Chemother. 2004, 48(12), / Lancet (2007), 370(9581), & 370(9581),
16 Torsional FlexibilityTo Daeyaert F., de Jonge M., Vinkers H. M., Koymans L., Heeres J. and Lewi P.J., 2003
17
18 Aggregate Formation 200 nm R R Electron Microscopy Atomic Force Microscopy Wang Y-H, Volovik Frenkel Y. and Arnold E., 2003 Ivanov Y., Lisitsa A., Karuzina I. and Archakov A. I., 2004
19
20
21 TMC278, Virology Profile Activity against >1500 RTI resistant clinical isolates in the absence of human serum protein EC 50 > 100 nm 10 nm < EC 50 < 100 nm 1 nm < EC 50 < 10 nm EC 50 < 1 nm VP EFV TMC125 TMC278
22 TMC278, Conclusion Highly potent against wild-type and resistant HIV-1 High genetic barrier to development of resistance in vitro Favorable PK profile Safe and well tolerated C C H H TMC278 is now in phase III development. Two global clinical trials (ECHO & THRIVE) are ongoing with 25mg of TMC278 given orally once daily.
23 Drawing by Jeanne Goodman, 2001a
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