Abstract: Derivatives of 9-deazaguanine are prepared by reacting an aldehyde or ketone with a dialkylaminomalonate to form the corresponding enamine. The enamine is then reacted with a base to form a cyclic pyrrole. The cyclic pyrrole is reacted with an urea compound or a derivative of carbamimidoic acid to provide a protected guanidino compound. The guanidino is converted to the desired 9-deazaguanine derivative by reacting with trifluoracetic acid or with an alkoxide or hydroxide followed by neutralization with an acid.
Type:
Application
Filed:
June 29, 2004
Publication date:
December 16, 2004
Applicant:
BioCryst Pharmaceuticals, Inc.
Inventors:
Arthur J. Elliott, David A. Walsh, Philip E. Morris
Abstract: 4-Oxo-4,5-dihydro-3H-pyrrolo[3,2-d] pyrimidine-7-carboxylic acid methyl ester and process for preparing are provided. The 4-oxo-4,5-dihydro-3H-pyrrole[3,2-d] pyrimidine-7-carboxylic acid methyl ester is useful as a precursor for providing 9-deaza-hypoxanthine, a key intermediate for producing certain PNP inhibitors.
Type:
Application
Filed:
April 23, 2003
Publication date:
October 28, 2004
Applicant:
BIOCRYST PHARMACEUTICALS, INC.
Inventors:
Christopher D. Winslow, Philip E. Morris
Abstract: A method for preparing 1-C-(9-deazaaden-9-yl)-1,4-imino-D-5′-deoxy-5′-methylthiorbitol) and pharmaceutically acceptable salts thereof is provided.
Type:
Grant
Filed:
February 19, 2003
Date of Patent:
August 24, 2004
Assignee:
BioCryst Pharmaceuticals, Inc.
Inventors:
Vivekanand Kamath, Philip E. Morris, Jr.
Abstract: Compounds of formula (I) are useful as inhibitors of trypsin like serine protease enzymes such as thrombin, factor VIIa, factor Xa, TF/FVIIa, and trypsin. These compounds could be useful to treat and/or prevent clotting disorders, and as anticoagulating agents.
Type:
Application
Filed:
December 18, 2003
Publication date:
August 19, 2004
Applicant:
BIOCRYST PHARMACEUTICALS, INC.
Inventors:
Yarlagadda S. Babu, R. Scott Rowland, Pooran Chand, Pravin L. Kotian, Yahya El-Kattan, Shri Niwas
Abstract: Compounds of formula (I) are useful as inhibitors of trypsin like serine protease enzymes such as thrombin, factor VIIa, factor Xa, TF/FVIIa, and trypsin. These compounds could be useful to treat and/or prevent clotting disorders, and as anticoagulating agents.
Type:
Grant
Filed:
April 23, 2002
Date of Patent:
March 2, 2004
Assignee:
BioCryst Pharmaceuticals, Inc.
Inventors:
Yarlagadda S. Babu, R. Scott Rowland, Pooran Chand, Pravin L. Kotian, Yahya El-Kattan, Shri Niwas
Abstract: T-cell inhibition proliferation in a mammalian host by administering effective amounts of 2′-deoxyguanosine and/or prodrugs thereof; and certain PNP inhibitors.
Type:
Grant
Filed:
December 17, 2001
Date of Patent:
December 9, 2003
Assignee:
BioCryst Pharmaceuticals Inc.
Inventors:
Shanta Bantia, John A. Montgomery, Philip E. Morris, Jr.
Abstract: Enhancement of T-cell proliferation in a host inhibition is provided by administering 2′-deoxyguanosine and/or prodrug thereof and a PNP inhibitor. The PNP inhibitor has a Ki value of 50 nanomoles or less.
Type:
Grant
Filed:
July 30, 2002
Date of Patent:
December 2, 2003
Assignee:
Biocryst Pharmaceuticals, Inc.
Inventors:
Shanta Bantia, John A. Montgomery, George A. Omura
Abstract: The present invention is concerned with new compounds, and particularly those having a fused bicyclic ring substituted with an amidine moiety. These compounds are each potent inhibitors of Factor D of the alternate pathway of complement, C1s of the classical pathway of complement, Factors Xa, XIIa, VIIa and thrombin of the coagulation pathway, plasmin in the fibrinolytic pathway, and kallikrein and high molecular weight kininogen in the inflammatory pathways. These proteases, which have serine in their active site, are called serine proteases and they are pivotal to most of the processes of inflammation and coagulation. In fact, these various systems are interactive with one another and it is difficult to activate one pathway without it influencing the others.
Type:
Grant
Filed:
September 27, 2000
Date of Patent:
November 25, 2003
Assignee:
BioCryst Pharmaceuticals, Inc.
Inventors:
Yarlagadda S. Babu, J. Claude Bennett, Shri Niwas, R. Scott Rowland
Abstract: The invention relates to a process for preparing substituted cyclopentane derivatives represented by the formula (I)
wherein R1, R2, R3, R4, X and Y are as described in the specification, and pharmaceutically acceptable salts thereof.
The invention further relates to a process for purifying the compound of formula (Ia)
and novel crystalline forms of the compound of formula (Ia).
Type:
Grant
Filed:
November 26, 2001
Date of Patent:
June 10, 2003
Assignee:
Biocryst Pharmaceuticals Inc.
Inventors:
Ahmed F. Abdel-Magid, Hans-Ulrich Bichsel, Daniel J. Korey, Gunther G. Laufer, Erja A. Lehto, Sebastiano Mattei, Max Rey, Thomas W. Schultz, Cynthia Maryanoff
Abstract:
Compounds I-III wherein U is CH, O, or S; Z is mono- or di-substituted carbon; R is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters; R1 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl; RR1 is O; n is 0-4; R2, R3 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkyl; R4 is (CH2)nOH, (CH2)nNH2, substituted alkyl were prepd. as neuraminidase inhibitors. Thus, (1R,3R,4R,1′S)-(−)-(1′-acetylamino-2 ′-ethyl)butyl-4-(aminoimino)methylaminocyclopentan-1-carboxylic acid was prepd. and tested in vitro as neuraminidase inhibitor (IC50<1.mu.M).
Type:
Grant
Filed:
May 25, 2000
Date of Patent:
May 13, 2003
Assignee:
BioCryst Pharmaceuticals, Inc.
Inventors:
Yarlagadda S. Babu, Pooran Chand, John A. Montgomery
Abstract: Certain substituted pyrrolidine compounds, pharmaceutically acceptable salts thereof, and their method of preparation are disclosed as well as use as influenza virus neuraminidase inhibitors.
Type:
Grant
Filed:
October 20, 2000
Date of Patent:
February 11, 2003
Assignee:
BioCryst Pharmaceuticals, Inc.
Inventors:
Pooran Chand, Pravin L. Kotian, Yarlagadda S. Babu, John A. Montgomery
Abstract: The invention relates to a process for preparing (−)-(1S,4R) N protected 4-amino-2-cylcopentene-1-carboxylate esters represented by the formula (I)
wherein R1 and R2 are as described within the specification.
Type:
Grant
Filed:
December 18, 2001
Date of Patent:
December 17, 2002
Assignee:
BioCryst Pharmaceuticals Inc.
Inventors:
Max Rey, Gregor Welti, Cynthia Maryanoff
Abstract: 1-C-(9-deazaaden-9-yl)-1,4-imino-D-5′-deoxy-5′-methylthioribitol) and pharmaceutically acceptable salts thereof are useful for inhibiting MTAP and treating cancer. A method for preparing the compounds of the present invention is also provided.
Type:
Grant
Filed:
May 4, 2001
Date of Patent:
October 1, 2002
Assignee:
Biocryst Pharmaceuticals, Inc.
Inventors:
John A. Montgomery, Philip E. Morris, Jr.
Abstract: Compounds represented by formula (I), and pharmaceutically acceptacle salts thereof; and their method of preparation are provided. Compounds of the above formula are influenza virus neuraminidase inhibitors and can be used in treating patients infected with influenza virus.
Type:
Grant
Filed:
June 9, 1999
Date of Patent:
June 25, 2002
Assignee:
Biocryst Pharmaceuticals, Inc.
Inventors:
Yarlagadda S. Babu, Pooran Chand, John A. Montgomery