Potent Noncovalent Thrombin Inhibitors That Utilize the Unique Amino Acid d-Dicyclohexylalanine in the P3 Position. Implications on Oral Bioavailability and Antithrombotic Efficacy-Reference-Cited by-同舟云学术

Potent Noncovalent Thrombin Inhibitors That Utilize the Unique Amino Acid d-Dicyclohexylalanine in the P3 Position. Implications on Oral Bioavailability and Antithrombotic Efficacy

Published:1997-05-01 Issue:11 Volume:40 Page:1565-1569
ISSN:0022-2623
Container-title:Journal of Medicinal Chemistry
language:en
Short-container-title:J. Med. Chem.

Author:

Tucker Thomas J.¹,Lumma William C.¹,Lewis S. Dale¹,Gardell Stephen J.¹,Lucas Bobby J.¹,Baskin Elizabeth P.¹,Woltmann Richard¹,Lynch Joseph J.¹,Lyle Elizabeth A.¹,Appleby Sandra D.¹,Chen I-Wu¹,Dancheck Kimberley B.¹,Vacca Joseph P.¹

Affiliation:

1. Departments of Medicinal Chemistry, Biological Chemistry, General Pharmacology, and Drug Metabolism, Merck Research Laboratories, West Point, Pennsylvania 19486

Publisher

American Chemical Society (ACS)

Subject

Drug Discovery,Molecular Medicine

Link

https://pubs.acs.org/doi/pdf/10.1021/jm970140s

Reference5 articles.

1. There is a previous patent that generically describes the use of this amino acid as a P3 ligand in thrombin inhibitors: Teger-Nilsson, A. C. E.; Bylund, R. E. WO9311152-A1, 1995.

2. Boc and Fmoc-d-diphenylalanine are commercially available from Synthetech, Inc., Albany, OR. Prior to this material becoming commercially available, racemic diphenylalanine was prepared according to Cheng et al.; Synthesis and Biological Activity of Ketomethylene Pseudopeotide Analogs as Thrombin Inhibitors.J. Med. Chem.1992,35, 3364−3370 and references cited therein.

3. Full experimental details for the preparation of CBZ-protectedtrans-4- (aminomethyl)cyclohexylamine are provided in the patent claiming this series of compounds: Brady, S. F.; Feng, D. M.; Freidinger, R. M.; Lumma, W. C.; Lyle, T. A.; Sanderson, P. E. J.; Stauffer, K. J.; Tucker, T. J.; Vacca, J. P. US 5, 510, 369, 1996.

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