10349. Vicriviroc

Nomenclature

CAS number: 306296-47-9
(4,6-Dimethyl-5-pyrimidinyl)[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methyl-1-piperidinyl]methanone; 1-[(4,6-dimethyl-5-pyrimidinyl)carbonyl]-4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methyl-1-piperazinyl]-4-methylpiperidine; SCH-D.
C28H38F3N5O2; mol wt 533.63.
C 63.02%, H 7.18%, F 10.68%, N 13.12%, O 6.00%.

Description and references

CCR5 chemokine receptor antagonist; HIV viral entry inhibitor. Prepn: B. M. Baroudy et al., WO 0066558; eidem, US 6391865 (2000, 2002 both to Schering Corp.); J. R. Tagat et al., J. Med. Chem. 47, 2405 (2004) DOI PubMed; D.-Z. Feng et al., Org. Biomol. Chem. 5, 2690 (2007) DOI PubMed. Pharmacology: J. M. Strizki et al., Antimicrob. Agents Chemother. 49, 4911 (2005) DOI PubMed. Pharmacokinetics in HIV-infected adults: D. Schürmann et al., AIDS 21, 1293 (2007) DOI PubMed. Clinical evaluation in HIV infection: R. M. Gulick et al., J. Infect. Dis. 196, 304 (2007) DOI PubMed; in treatment-naive patients: R. J. Landovitz et al., ibid. 198, 1113 (2008) DOI PubMed.

Chemical structure

Properties

White foam. [α]D22 +6.6° (c = 0.5 in methanol). Sol in ethyl acetate, isopropyl acetate, isopropanol, methanol.

Derivative

Hydrochloride.

Nomenclature

CAS number: 541503-48-4
C28H38F3N5O2.HCl; mol wt 570.09.
C 58.99%, H 6.90%, F 10.00%, N 12.28%, O 5.61%, Cl 6.22%.

Properties

Off-white solid from ethyl acetate, mp 175°. [α]D25 +13.3° (c = 2.44 in methanol).

Derivative

Maleate.

Nomenclature

CAS number: 599179-03-0
Sch-417690.
C28H38F3N5O2.C4H4O4; mol wt 649.70.
C 59.16%, H 6.52%, F 8.77%, N 10.78%, O 14.78%.

Properties

White crystals.

Therapeutic Category

Antiretroviral.

Keywords

Antiretroviral; Entry Inhibitors