Zoektocht naar innovatieve geneesmiddelen voor de toekomst - Verslaving en ander gedrag in moleculair perspectief
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1 Zoektocht naar innovatieve geneesmiddelen voor de toekomst - Verslaving en ander gedrag in moleculair perspectief Prof. dr. Chris Kruse Swammerdam Institute, UvA Solvay Pharmaceuticals
2 Drug Discovery Assets Successful drug research relies on: innovative high quality compounds acting on disease relevant targets
3 Targets and Compounds What is a target? a (big) molecular entity inside the body interacting with a compound What is a compound? a (small) molecule interacting with a target
4
5 How to find Compounds? screening of hundreds of thousands of compounds design based upon: structures of known ligands structure of target protein (if available)
6
7 Discovery of ovel asses of Selective CB 1 Receptor Antagonists Chris Kruse Jos Lange Hein Coolen Arnoud Herremans
8 Chronology Use of Cannabis sativa for ~ 40 centuries medicinal/recreational purposes Discovery of active ingredient 9-THC 1964, Mechoulam et al. oning of CB 1 receptor 1990, Matsuda et al. Discovery of anandamide 1992, Mechoulam et al.
9 Locations of CB 1 -Receptors Substantia igra Globus Pallidus Caudate ucleus Putamen Basal Ganglia Amygdala Hippocampus Limbic System Hypothalamus Cerebral Cortex
10 Endocannabinoids Endogenous cannabinoid ligands: Fatty acid derivatives? Anandamide (AEA) 2-Arachidonyl glycerol oladin ether (porcine) Virodhamine ADA H H H H H H H 2 H H H Anandamide (1992) 2-Arachidonylglycerol (1995) oladin ether (2001) Virodhamine (2002) ADA (2002) Endocannabinoid signaling is altered in neurological, psychiatric, cardiovascular, gastrointestinal, reproductive and eating disorders and cancer Vandevoorde and Lambert, Curr. Pharm. Des. 2005, 11, DiMarzo et al., BJP 141, 765 (2004) Lambert and Fowler, J. Med. Chem. 2005, 48, Piomelli, at. Med. 10, 19 (2004) Di Marzo et al., at Rev. Drug Discov. 3, , 2004 Rodriguez de Fonseca, Alcohol Alcoholism 2005, 40, 2-14
11 CB1 antagonists: Potential Therapeutic Applications besity Addiction / smoking cessation Cognitive and memory disorders
12 Cannabinoids and feeding Endogenous cannabinoids Play a role in the natural reward pathways of the brain Modulation of the appetitive value of food: Mediation of behavioral, food searching effects Affect energy homeostasis Central: Leptin, CRH, MC 4, PY, others? Peripheral: lipogenic mechanisms, involved in FA oxidation? H! 9 -THC (Tetrahydrocannabinol) Consequently CB 1 agonists are useful for appetite stimulation Whereas The CB 1 antagonist rimonabant showed clinical efficacy in obesity / metabolic syndrome H Boyd and Fremming, Ann. Pharmacother. 2005, 39, Fernandez and Allison, Curr. pin. Investig. Drugs 2004, 5, Carai, Life Sc. 2005, 77, Cox, Drugs Today 2005, Rimonabant
13
14 CB 1 antagonists: Level of competitive R&D umber of patent applications The yearly number of patents wherein CB 1 receptor antagonists have been claimed is increasing Year Lange and Kruse, Drug Discov. Today 10, (2005)
15 Examples of CB 1 receptor antagonists H Rimonabant (SR141716A) C C CP Review: Lange and Kruse, Curr. pin. Drug Discovery Dev. 2004, 7(4), H LY
16 Rimonabant blocks relapse Extinction of lever pressing for cocaine reward Reinstatement by reward associated stimuli Attenuated by Rimonabant (De Vries et al, 2001, nature med, 7, )
17 Rimonabant improves memory retention social recognition Rimonabant investigation time (sec) * * recognition index First contact Second contact Recognition index (second/first) Rimonabant (mg/kg po)
18 Lead Finding Strategies I. Conformationally Constrained Analogues of Rimonabant Lange et al. Chem. Pharm. Bull. 50, 1109 (2002) II. Bioisosteric Scaffolds. Analogues of Rimonabant Lange et al. J. Med. Chem. 48, 1823 (2005) III. Screening Lange et al., J. Med. Chem. 47, 627 (2004) Start research program in 1996
19 I. Conformationally Constrained Analogues H H Rimonabant (SR A) = or Stoit et al., Chem. Pharm. Bull. 50, 1109 (2002); Ruiu et al., J. Pharmacol. Exp. Ther. 306, 363 (2003); ibid., Bioorg. Med. Chem. 13, 3309 (2005) Adam et al., Progress Med. Chem. 44, 2006, , Eds. King and Lawton.
20 II. Bioisosteric Scaffolds Replace central pyrazole moiety in rimonabant by other fivemembered ring heterocycles S H Thiazole bioisostere H H Rimonabant Imidazole bioisostere H Triazole bioisostere
21 Key compounds / In vivo results R BP TEMP H R (mg/kg/po) ED 50 (mg/kg, po) LED H 12 >30 H CH C 2 H Rimonabant Rimonabant 5.5 3
22 III. Screening Limited set of compounds initially screened (~6000) ne relevant hit found: DU Source: Diversity library from stock (CADD) H 2 S Pharmacological activity DU : DU Moderately active in vitro as CB 1 antagonist But: completely inactive in vivo
23 Screening (2) bjectives Lead ptimization Improve pharmacodynamics * low nm range Improve pharmacokinetics * assure oral bioavailability
24 Lead optimisation program Ar 1 Ar 2 R4 S R3 R5 R1 R2 Ca. 950 compounds synthesized ~50/50 singles/libraries Result: Several compounds with CC potential
25 SLV326 and Rimonabant HCH 3 S H R R= CF 3 SLV326 Rimonabant
26 Pharmacological key results SLV 326 is also active in relapse models for cocaine, nicotine and alcohol
27 Receptor-docking alignment rimonabant
28 Protein model of CB1 receptor with antagonist
29 Conclusions Three independent approaches led to in vitro potent and selective CB 1 receptor antagonists Conformationally constrained rimonabant analogues showed poor Pharmacokinetic properties Scaffold exchange in rimonabant (1,5-pyrazole 1,2- imidazole) resulted in a bioisosteric analogue, both in Pharmacodinamic as in Pharmacokinetic Limited screening resulted in a lead from company stock; lead optimization offered several clinical candidates
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