BMS-344577 - CAS 288079-93-6
Catalog number:
288079-93-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C31H37N7O5
Molecular Weight:
587.67
COA:
Inquire
Targets:
Factor Xa
Description:
BMS-344577 is aroylguanidine-based lactam derivative, which is a potent FXa inhibitor (FXa IC(50)=4 nM, EC(2xPT)=7 microM).
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Purity:
≥95%
Appearance:
Solid powder
Synonyms:
N5-[[[(3S)-Hexahydro-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-azepin-3-yl]imino][(2-methyl-5-benzofuranyl)amino]methyl]-N2,N2-dimethyl-2,5-pyridinedicarboxamide; (S,E)-N2,N2-dimethyl-N5-(N'-(2-methylbenzofuran-5-yl)-N-(2-oxo-1-(2-oxo-2-(pyrrolidin-1-yl)ethyl)azepan-3-yl)carbamimidoyl)pyridine-2,5-dicarboxamide;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Aroylguanidine-based factor Xa inhibitor.
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
InChIKey:
YLSKCQOVDOZHTQ-VWLOTQADSA-N
InChI:
1S/C31H37N7O5/c1-20-16-22-17-23(10-12-26(22)43-20)33-31(35-28(40)21-9-11-24(32-18-21)29(41)36(2)3)34-25-8-4-5-15-38(30(25)42)19-27(39)37-13-6-7-14-37/h9-12,16-18,25H,4-8,13-15,19H2,1-3H3,(H2,33,34,35,40)/t25-/m0/s1
Canonical SMILES:
Cc1cc2cc(ccc2o1)N=C(N[C@H]3CCCCN(C3=O)CC(=O)N4CCCC4)NC(=O)c5ccc(nc5)C(=O)N(C)C
Current Developer:
Bristol-Myers Squibb
1.Aroylguanidine-based factor Xa inhibitors: the discovery of BMS-344577.
Shi Y1, Li C, O'Connor SP, Zhang J, Shi M, Bisaha SN, Wang Y, Sitkoff D, Pudzianowski AT, Huang C, Klei HE, Kish K, Yanchunas J Jr, Liu EC, Hartl KS, Seiler SM, Steinbacher TE, Schumacher WA, Atwal KS, Stein PD. Bioorg Med Chem Lett. 2009 Dec 15;19(24):6882-9. doi: 10.1016/j.bmcl.2009.10.084. Epub 2009 Oct 23.
We report the design and synthesis of a novel class of N,N'-disubstituted aroylguanidine-based lactam derivatives as potent and orally active FXa inhibitors. The structure-activity relationships (SAR) investigation led to the discovery of the nicotinoyl guanidine 22 as a potent FXa inhibitor (FXa IC(50)=4 nM, EC(2xPT)=7 microM). However, the potent CYP3A4 inhibition activity (IC(50)=0.3 microM) of 22 precluded its further development. Detailed analysis of the X-ray crystal structure of compound 22 bound to FXa indicated that the substituent at the 6-position of the nicotinoyl group of 22 would be solvent-exposed, suggesting that efforts to attenuate the unwanted CYP activity could focus at this position without affecting FXa potency significantly. Further SAR studies on the 6-substituted nicotinoyl guanidines resulted in the discovery of 6-(dimethylcarbamoyl) nicotinoyl guanidine 36 (BMS-344577, IC(50)=9 nM, EC(2xPT)=2.5 microM), which was found to be a selective, orally efficacious FXa inhibitor with an excellent in vitro liability profile, favorable pharmacokinetics and pharmacodynamics in animal models.
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CAS 288079-93-6 BMS-344577

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