Rimonabant - CAS 168273-06-1
Catalog number: 168273-06-1
Category: Inhibitor
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Molecular Formula:
C22H21Cl3N4O
Molecular Weight:
463.79
COA:
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Targets:
Cannabinoid Receptor
Description:
Rimonabant is a selective antagonist of CB1 with IC50 of 13.6 nM and EC50 of 17.3 nM in hCB1 transfected HEK 293 membrane.
Purity:
>98%
Synonyms:
SR141716; SR 141716; SR-141716
MSDS:
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InChIKey:
JZCPYUJPEARBJL-UHFFFAOYSA-N
InChI:
InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
Canonical SMILES:
CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl
1. Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral
Tomas Gustafsson, Fritiof Ponten and Peter H. Seeberger*. Chem. Commun.,2008, 1100–1102
Rimonabant (SR141716,31, Scheme 1) and efaproxiral (RSR13, 36, Scheme 2), two pharmaceutically active substances, were synthesized in a continuous flow microreac-tor to apply the method. Rimonabant is an anti-obesity drug that acts as a central cannabinoid receptor antagonist, and synthetic routes are established. The last step of the synthetic sequence, the union of an acid chloride and 1-aminopiperidine, may be replaced by direct amide formation. The entire sequence to31was per-formed in a microreactor starting with treatment of ketone with LiHMDS at room temperature (1 min retention time), followed by ethyl oxalate at 501C in a second reactor (10 min retention time, 70% yield). While the synthesis of 29 or its lithium salt can be accomplished in batch reactors, the microreactor method avoids cooling that otherwise requires some effort on scale. After work-up and purification,29 was treated with the HCl salt of 4-chlorophenylhydrazine in AcOH at 125℃ for 16 min to provide pyrazole30 in 80% yield. Finally, rimonabant 31 was conveniently synthesized in gram quantities in 49% overall yield, using the amidation reaction.
2. Formation of new polymorphs without any nucleation step. Desolvation of the rimonabant monohydrate: directional crystallisation concomitant to smooth dehydration
Baptiste Fours, Yohann Cartigny, Samuel Petit and G´ erard Coquerel*. Faraday Discuss.,2015,179,475–488
Crystalline samples of rimonabant were provided by the Sanofi-Aventis Company, with a chemical purity higher than 99%. The monohydrated form was produced by dissolving 8 g of rimonabant in 40 g of acetone at room temperature. Then, 10 g of water was added dropwise and the monohydrate crystallized out spontane-ously. Temperature can be dropped to 5℃ to improve the yield (6.5 g afterfiltration) and drying to a fixed composition in water 3.7% w/w. Single crystals with a needle-like shape were obtained by slow evaporation at RT of the same acetone–water solution.
3. The pentafluorosulfanyl group in cannabinoid receptor ligands: synthesis and comparison with trifluoromethyl andtert-butyl analogues
Stefano Altomonte, Gemma L. Baillie, Ruth A. Ross, Jennifer Riley and Matteo Zanda*. RSC Adv.,2014,4,20164–20176
Most of the tabulated logPvalues for the CB1inverse agonist Rimonabant (SR141716) were determinedin silico, and the two experimental values reported in literature, obtained through the flask-shake technique, are quite different (logD7.4 = 4.6±0.8 and logD7.4 =3.8). In order to obtain a new experimental value we decided to test SR141716 using the previously described RP-HPLC method, which provided a logPvalue of 4.73±0.20 for Rimonabant. This confirmed that all the new ligands presented in this article exhibit higher hydrophobicity than SR141716.
4. 4-Cyano-5-(2-thiophenyl)-pyrazoles are high affinity CB1 receptor ligands
Stefano Altomonte,* Gemma L. Baillie, Ruth A. Ross and Matteo Zanda*. RSC Adv.,2015,5, 13692–13701
The cyano pyrazole5ais an analogue of NESS098A (Fig. 1) and is structurally related to the inverse agonist SR141716 (Rimonabant, Fig. 1). Replacement of the methyl in position 4 on the pyrazole ring with the more polar cyano group increased 4-fold the CB1 /CB2 selectivity of 5a relative to NESS098A (Table 3), while maintaining a similar affinity. Furthermore,5a showed a reduced lipophilicity (experimental logP) relative to that displayed by Rimonabant. Slightly lower CB1affinity and significantly lower CB1 /CB2 selectivity were observed for 5b, having R1 =N-Boc-4-piperidyl as carboxamide substituent.
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CAS 168273-06-1 Rimonabant

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