Patents Assigned to BioNumerik Pharmaceuticals, Inc.
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Patent number: 7687496Abstract: The novel C7-modified camptothecin analogs, and pharmaceutically-acceptable salts thereof, of the present invention: (i) possess potent antitumor activity (i.e., in nanomolar or subnanomolar concentrations) for inhibiting the growth of human and animal tumor cells in vitro; (ii) are potent inhibition of Topoisomerase I; (iii) lack of susceptibility to MDR/MRP drug resistance; (iv) require no metabolic drug activation: (v) lack glucuronidation of the A-ring or B-ring; (vi) reduce drug-binding affinity to plasma proteins; (vii) maintain lactone stability; (viii) maintain drug potency; and (ix) possess a low molecular weight (e.g., MW<600).Type: GrantFiled: October 16, 2007Date of Patent: March 30, 2010Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Kesavaram Narkunan, Xinghai Chen, Harry Kochat, Frederick Hausheer
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Patent number: 7687487Abstract: The present invention discloses: (i) a novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (ii) methods of synthesis of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof; (iii) pharmaceutically-acceptable formulations comprising said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents; (iv) methods of administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more additional chemotherapeutic agents, to subjects in need thereof; and (v) devices for the administration of said novel, lactone-stable, “flipped” E-ring camptothecin, pharmaceutically-acceptable salts, and/or analogs thereof, and, optionally, one or more chemotherapeutic agents, to subjects in need therType: GrantFiled: April 19, 2007Date of Patent: March 30, 2010Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Frederick H. Hausheer
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Patent number: 7569606Abstract: Disclosed herein are novel platinum-based complexes possessing one nitrile substituent group (mononitrile) covalently-bonded to the platinum, one or more nitrogen donor ligands capable of forming hydrogen bonds with the bases in DNA or RNA and leaving groups (i.e., L1 and L2 )which can be hydrolyzed iii vivo to active species, which can then form coordinate adducts with DNA or RNA at the Guanine or Adenine bases thereof. Also disclosed herein are the reaction schemes for the synthesis of said platinum complexes, as well as methods of treatment of various types of cancer by the administration of a pharmaceutically-effective dose of said novel platinum complexes.Type: GrantFiled: April 17, 2006Date of Patent: August 4, 2009Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Zejun Xiao, Frederick H. Hausheer, Pavankumar Petluru
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Patent number: 7282602Abstract: This invention relates to novel salts of medicinal disulfides. The compounds include a terminal sulfonate or phosphonate moiety, and have many uses, such as toxicity reducing agents when administered with many antineoplastic agents.Type: GrantFiled: September 21, 2004Date of Patent: October 16, 2007Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Qiuli Huang, Harry Kochat, Xinghai Chen
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Patent number: 7268244Abstract: Disclosed herein are novel platinum-based analogs with a single substituted imine ligand: R7RC?NR8, wherein the R7RC?NR8 functional group is covalently bonded to the platinum through nitrogen. The analogs also have nitrogen donor ligands capable of forming hydrogen bonds with the bases in DNA or RNA, and one or more leaving groups which can be displaced by water, hydroxide ions or other nucleophiles, which is thought to form active species in vivo, and then, form cross-linked complexes between nucleic acid strands, principally between purines in DNA (or RNA), i.e., at the Guanine or Adenine bases, thereof.Type: GrantFiled: January 26, 2006Date of Patent: September 11, 2007Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Frederick H. Hausheer, Zejun Xiao, Harry Kochat
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Patent number: 7238823Abstract: Disclosed herein are novel platinum-based complexes possessing one nitrile substituent group (mononitrile) covalently-bonded to the platinum, one or more nitrogen donor ligands capable of forming hydrogen bonds with the bases in DNA or RNA and leaving groups (i.e., L1 and L2) which can be hydrolyzed in vivo to active species, which can then form coordinate adducts with DNA or RNA at the Guanine or Adenine bases thereof. Also disclosed herein are the reaction schemes for the synthesis of said platinum complexes, as well as methods of treatment of various types of cancer by the administration of a pharmaceutically-effective dose of said novel platinum complexes.Type: GrantFiled: January 26, 2006Date of Patent: July 3, 2007Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Zejun Xiao, Frederick H. Hausheer, Pavankumar Petluru
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Patent number: 7176192Abstract: This invention relates to a method of treating a patient suffering from ionizing radiation exposure, or of treating a patient about to undergo ionizing radiation therapy. The method includes administering to a patient in need of treatment an effective amount of a thiol or reducible disulfide compound according to the formula set forth in the specification.Type: GrantFiled: October 26, 2001Date of Patent: February 13, 2007Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Frederick H. Hausheer
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Patent number: 7060825Abstract: The invention claimed herein relates to an improvement in a process for synthesizing a compound of formula Ib: wherein R1 and R2 are each individually amino or N-alkyl substituted amino; hydroxy; alkoxy; keto; lower alkyl; or a nitrogen or oxygen protecting group; R3 is hydrogen; hydroxy; alkoxy; trifluoromethyl alkoxy; halo; sulfhydryl or alkylthio; R4 is —C(O)—X; X is hydroxy; alkoxy; or an amino acid residue; in which process a 2-amino-5-nitro-benzonitrile starting reagent is cyclized to form 2,4-diamino-6-nitro-quinazoline, which is converted to 2,4,6-triamino-quinazoline, which is converted to 2,4-diamino-6-cyano-quinazoline, which is converted to 2,4-diamino-6-formyl-quinazoline; in which the improvement includes: reacting an R4-p-benzoic acid alkylene moiety with triethyl phosphite to form a 4-R4-carbonyloxyalkyl-phenyl-alkyldiethylphosphite; and reacting the 2,4-diamino-6-formyl-quinazoline with the 4-R4-carbonyloxyalkyl-phenyl-alkyldiethylphosphite to form the compound of formula Ib.Type: GrantFiled: July 25, 2003Date of Patent: June 13, 2006Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Ye Wu, Harry Kochat
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Patent number: 7053240Abstract: This invention relates to a process for producing a substantially pure disulfide compound of Formula II as disclosed herein, such as disodium 2,2?-dithiobis ethane sulfonate, by an efficient procedure from available, relatively inexpensive raw materials.Type: GrantFiled: December 17, 2004Date of Patent: May 30, 2006Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Koh Kawami, Osamu Tokuda, Yoshihide Niimoto
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Patent number: 7030243Abstract: A process for synthesizing highly lipophilic derivatives of camptothecin. The process includes reacting dissolved, underivatized camptothecin with a silylated heterocyclic compound in a modified Minisci-type alkylation reaction to produce 7-substituted derivatives of camptothecin.Type: GrantFiled: October 28, 2004Date of Patent: April 18, 2006Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Ye Wu, Kesavaram Narkunan, Jianyan Wang, Harry Kochat
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Patent number: 6977311Abstract: A process for synthesizing substantially enantiomerically pure L-amino acids, particularly L-?-methylene glutamic acid, and esters and salts thereof. The process includes the derivatization of (2S)-pyroglutamic acid, and the decyclization of the resulting derivative to form the desired end product.Type: GrantFiled: July 25, 2003Date of Patent: December 20, 2005Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Harry Kochat, Xinghai Chen, Ye Wu, Qiuli Huang, Jianyan Wang, Vincent Gerusz
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Patent number: 6936733Abstract: The invention concerns a novel method for industrial preparation of disodium 2,2?-dithiobis(alkylsulphonates), and in particular disodium 2,2?-dithiobis(ethanesulphate) (dimesna). Said novel method is summarized by the reaction diagram (A). In diagram (A), Hal represents a halogen atom, and preferably a bromine atom; M represents a sodium or potassium atom; and n represents an integer ranging between 0 and 2.Type: GrantFiled: July 17, 2001Date of Patent: August 30, 2005Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Jean-Bernard Cazaux, Eric Manginot, Marc Veyrat
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Patent number: 6723849Abstract: A process for synthesizing highly lipophilic derivatives of camptothecin. The process includes reacting dissolved, underivatized camptothecin with an aldehyde in a modified Minisci-type alkylation reaction to produce 7-substituted derivatives of camptothecin.Type: GrantFiled: July 25, 2003Date of Patent: April 20, 2004Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Kesavaram Narkunan, Harry Kochat, Xinghai Chen
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Patent number: 6596320Abstract: A method of treating patients with cancer that involves administration of a combination regimen of a platinum agent, a taxane agent, and a formula I toxicity-reducing agent. The preferred order of administration is the formula I compound, followed by the platinum complex, followed by the taxane agent.Type: GrantFiled: January 11, 2002Date of Patent: July 22, 2003Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Frederick H. Hausheer
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Patent number: 6525037Abstract: This invention relates to a method of treating patients afflicted with atherosclerosis or to prevent the development of atherosclerosis in patients assessed to be high risk of developing the disease. The method includes administering to a patient in need of treatment an effective amount of a thiol or reducible disulfide compound according to the formula set forth in the specification.Type: GrantFiled: February 25, 2000Date of Patent: February 25, 2003Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Frederick H. Hausheer, Seetharamulu Peddaiahgari
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Patent number: 6504049Abstract: A process for synthesizing pharmaceutically active disulfides, particularly Dimesna and certain derivatives thereof. The process includes reacting an alkylene salt with a sulfurating reagent, then alkalizing the intermediate and flowing oxygen through the mixture to produce the final compound in high yield.Type: GrantFiled: April 30, 2002Date of Patent: January 7, 2003Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Harry Kochat
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Patent number: 6468963Abstract: Formulations and methods for reducing the unwanted toxicity and complications associated with treatments for diabetes mellitus. The formulations include co-formulations of an anti-diabetic agent and a toxicity reducing agent of the formula described in the specification. The methods include administration of effective amounts of the anti-diabetic agent and the toxicity reducing agent to safely treat the diabetic patient.Type: GrantFiled: May 1, 2000Date of Patent: October 22, 2002Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Frederick H. Hausheer, Aulma Parker, Susan E. Hamilton
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Patent number: 6468993Abstract: This invention relates to a method of treating patients afflicted with osteoporosis. The method includes administering to a patient in need of treatment an effective amount of a thiol or reducible disulfide compound according to the formula set forth in the specification.Type: GrantFiled: October 4, 1999Date of Patent: October 22, 2002Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Frederick H. Hausheer
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Patent number: 6245815Abstract: This invention relates to a method of treating patients afflicted with alcoholism. The method includes administering to a patient in need of treatment an effective amount of a thiol or reducible disulfide compound according to the formula set forth in the specification.Type: GrantFiled: April 15, 2000Date of Patent: June 12, 2001Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Seetharamulu Peddaiahgari
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Patent number: 6218540Abstract: A process for preparing the anti-cancer drug camptothecin (CPT) and certain derivatives thereof. The process includes the reacting of three base reagents and a five-step process for synthesizing optically pure CPT in high overall yield from inexpensive starting materials.Type: GrantFiled: May 4, 1999Date of Patent: April 17, 2001Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Marco Ciufolini, Frank Roschangar