Patents by Inventor Wanren Li
Wanren Li has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20150011484Abstract: The present invention provides pro-drugs of D-gamma-glutamyl-[D/L]-tryptophan, said pro-drugs are compounds of Formula I or pharmaceutically acceptable salts thereof, wherein G is C1-C8 alkyl or benzyl, T is C1-C8 alkyl or benzyl, and * is a chiral carbon in a (R) or (S) configuration, provided that when * is in the (R) configuration, at least one of G and T is C5-C8 alkyl; and use of compounds of Formula I in a pharmaceutical composition.Type: ApplicationFiled: March 30, 2012Publication date: January 8, 2015Applicant: APTOEX TECHNOLOGIES, INC.Inventors: Tim Fat Tam, Regis Leung-Toung, Yinsheng Wang, Yanqing Zhao, Tao Xin, Wanren Li, Jolanta Maria Wodzinska, Vrajlal S. Rabadia, Birenkumar Shah, Christopher John Feeney
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Publication number: 20140343050Abstract: Provided are carboxylic ester derivatives of formula (I), methods of preparing them, and methods for using them. These compounds are prodrugs of D-isoglutamyl-[D/L]-tryptophan. The in vitro bioconversion of some of the prodrugs to the parent drug D-isoglutamyl-D-tryptophan (or thymodepressin) was tested in human hepatocytes and in human blood. In vivo pharmacokinetic studies following oral administration of some of the prodrugs to rats are also reported.Type: ApplicationFiled: March 30, 2012Publication date: November 20, 2014Applicant: APTOEX TECHNOLOGIES, INC.Inventors: Tim Fat Tam, Regis Leung-Toung, Yingsheng Wang, Yanqing Zhao, Tao Xin, Wanren Li, Jolanta Maria Wodzinska, Vrajlal S. Rabadia, Christopher John Feeney
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Publication number: 20120157387Abstract: Provided are compounds which are prodrugs of D-gamma-glutamyl-D-tryptophan, methods of making the compounds and methods for using the compounds.Type: ApplicationFiled: February 20, 2012Publication date: June 21, 2012Applicant: APOTEX TECHNOLOGIES INC.Inventors: Tim Fat TAM, Regis Leung-Toung, Yingsheng Wang, Yanqing Zhao, Tao Xin, Wanren Li, Jolanta Maria Wodzinska, Vrajlal S. Rabadia, Birenkumar Shah, Christopher John Feeney
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Patent number: 8097624Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula I wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2R5N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: GrantFiled: May 9, 2008Date of Patent: January 17, 2012Assignee: Apotex Inc.Inventors: Tim Fat Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanqing Zhao, Birenkumar Hasmukhbhai Shah
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Patent number: 7893269Abstract: The present invention relates to a novel process for the preparation of 1-alkyl or 1-cycloalkyl derivatives of 3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxamide of formula (I). The process includes reacting an amine R2NH2 with a compound of formula (II) in a solution of metal hydroxide in water to give a compound of formula (III). Subsequent reaction of the compound of formula (III) with an acid chloride formation reagent in an inert solvent gives compounds of formula (I). The acid chloride formation reagent is selected from oxalyl chloride and dimethylformamide, dimethylchloromethylene-ammonium chloride and thionyl chloride and dimethylformamide. If desired, a compound of formula (I) where R5 is hydrogen may be formed when an intermediate substituent is used wherein R5 is an alcohol protective group removable by catalytic hydrogenation.Type: GrantFiled: November 17, 2005Date of Patent: February 22, 2011Assignee: Apotex IncInventors: Tim Fat Tam, Regis Leung-Toung, Yanqing Zhao, Wanren Li, Yingsheng Wang, Sandra Vittoria Agostino, Birenkumar Hasmukhbhai Shah
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Publication number: 20090170850Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula I wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2R5N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: ApplicationFiled: May 9, 2008Publication date: July 2, 2009Inventors: Tim Fat Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanqing Zhao, Birenkumar Hasmukhbhai Shah
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Patent number: 7410985Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula (I); wherein R1 is X with the proviso that R2 is Y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2 R5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: GrantFiled: November 18, 2004Date of Patent: August 12, 2008Assignee: Apotex Inc.Inventors: Tim Fat Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanqing Zhao, Birenkumar Hasmukhbhai Shah
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Publication number: 20080096886Abstract: The present invention relates to a novel process for the preparation of 1-alkyl or 1-cycloalkyl derivatives of 3-hydroxy-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I. The process includes reacting an amine R2NH2 with a compound of formula II in a solution of metal hydroxide in water to give a compound of formula III. Subsequent reaction of the compound of formula III with an acid chloride formation reagent in an inert solvent gives compounds of formula I. The acid chloride formation reagent is selected from oxalyl chloride and dimethylformamide, dimethylchloromethylene-ammonium chloride and thionyl chloride and dimethylformamide. If desired, a compound of formula I where R5 is hydrogen may be formed when an intermediate substituent is used wherein R5 is an alcohol protective group removable by catalytic hydrogenation.Type: ApplicationFiled: November 17, 2005Publication date: April 24, 2008Applicant: APOTEX INC.Inventors: Tim Tam, Regis Leung-Toung, Yanqing Zhao, Wanren Li, Yingsheng Wang, Sandra Agostino, Birenkumar Shah
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Publication number: 20070082904Abstract: The present invention provides an cycloalkyl derivative of 3-hydroxy-4-pyridinone which is useful for the chelation of metal ions such as iron. Its preparation and use is described. In particular, the invention concerns the removal of iron in chemical and biological systems including chelating agents having the formula (I); wherein R1 is X with the proviso that R2 is y; or R1 is T with the proviso that R2 is W; or R1 is X with the proviso that R2R5 N when taken together form a heterocyclic ring selected from piperidinyl, morpholinyl, pyrrolidinyl or piperazinyl, wherein the group piperidinyl, morphoninyl, pyrrolidinyl or piperazinyl is either unsubstituted or substituted with one to three C1 to C6 alkyl groups.Type: ApplicationFiled: November 18, 2004Publication date: April 12, 2007Inventors: Tim Tam, Michael Spino, Wanren Li, Yingsheng Wang, Yanging Zhao, Birenkumar Shah
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Publication number: 20030225007Abstract: A method of inhibiting the activity of transglutaminases containing a cysteine residue comprising administering to a mammal an effective amount of a sulfonamide derivative of imidazo[1,2-d]-1,2,4-thiadiazoles sufficient to inhibit the activity.Type: ApplicationFiled: March 27, 2003Publication date: December 4, 2003Applicant: Apotex Inc.Inventors: Tim Fat Tam, Khashayar Karimian, Regis C.S.H. Leung-Toung, Yanqing Zhao, Jolanta Maria Wodzinska, Wanren Li, Jayme Nicole Lowrie
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Patent number: 6476229Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: March 19, 2002Date of Patent: November 5, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6472532Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-4-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyidiimidazole in an inert solvent affords 3-O-protected-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: March 19, 2002Date of Patent: October 29, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6468977Abstract: Novel 1,2,4-thiadiazole compounds are provided, which are effective as inhibitors of cysteine activity-dependent enzymes and in particular of cysteine proteases. The compounds are useful in treating acne by inhibition of transglutaminase, common cold by inhibition of human rhinovirus 3C protease and inflammatory joint disease by inhibition of cathepsins. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadazole of the general formula (I): where Z is a nitrogen containing group with recognition sequence for the enzyme and Y is a substituent that tunes the reactivity of the inhibitor towards the thiol group of the cysteine activity-dependent enzyme. The Y group may also serve in recognition.Type: GrantFiled: May 23, 2000Date of Patent: October 22, 2002Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li, Steve Patrick Bryson, Jolanta Maria Wodzinska
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Patent number: 6426418Abstract: The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.Type: GrantFiled: November 2, 2001Date of Patent: July 30, 2002Assignee: Apotex, Inc.Inventors: Tim F. Tam, Wanren Li
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Patent number: 6162791Abstract: Novel 1,2,4-thiadiazole compounds are provided, which are effective as inhibitors of cysteine activity-dependent enzymes and in particular of cysteine proteases. The compounds are useful in treating acne by inhibition of transglutaminase, common cold by inhibition of human rhinovirus 3C protease and inflammatory joint disease by inhibition of cathepsins. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadazole of the general formula (I): ##STR1## where Z is a nitrogen containing group with recognition sequence for the enzyme and Y is a substituent that tunes the reactivity of the inhibitor towards the thiol group of the cysteine activity-dependent enzyme. The Y group may also serve in recognition.Type: GrantFiled: March 2, 1998Date of Patent: December 19, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li
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Patent number: 6114537Abstract: Thiols are trapped, and converted to disulfide compounds, by a process of reacting them with compounds containing a 1,2,4-thiadiazole ring structure carrying a substituent at position 3 of the thiadiazole ring, and being unsubstituted at position N-2. The process is useful pharmacologically, in inhibiting certain thiol-containing enzymes such as H.sup.+ /K.sup.+ -ATPase (the proton pump), and industrially, in selective removal of thiol compounds from gas or liquid mixtures.Type: GrantFiled: February 21, 1997Date of Patent: September 5, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim F. Tam, Denis Desilets, Sue Lee, Tullio Cappelletto, Wanren Li
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Patent number: 6093738Abstract: Novel thiadiazole compounds are provided, which are effective as proton pumps inhibitors, useful in treating peptic ulcers by inhibition of the proton pump enzyme H.sup.+ /K.sup.+ -ATPase. The compounds are 3-substituted 1,2,4-thiadiazolo [4,5-.alpha.]benzimidazole and 3-substituted imidazo[1,2-d]-1,2,4-thiadiazoles corresponding to the general formula: ##STR1## where X and Z either represent an optionally substituted benzene ring fused to the diazole nucleus, or represent a variety of independent chemical groupings (hydrogen, lower alkyl, halo, etc.) and Y is selected from a wide range, e.g. heterocyclics and carbonyl groups.Type: GrantFiled: February 21, 1997Date of Patent: July 25, 2000Inventors: Khashayar Karimian, Tim F. Tam, Denis Desilets, Sue Lee, Tullio Cappelletto, Wanren Li
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Patent number: 6060472Abstract: Novel 3,5-disubstituted 1,2,4-thiadiazole compounds are provided, which are effective in treating peptic ulcers by the inhibition of H.sup.+ /K.sup.+ -ATPase. The compounds of the present invention are 3,5-disubstituted 1,2,4-thiadiazole corresponding to the general formula (I): ##STR1## where R.sup.1 is a group with cell penetration properties for the inhibition of the enzyme in-vitro and in-vivo, and Y is a substituent that tunes the reactivity of the inhibitor towards the cysteine residue of H.sup.+ /K.sup.+ -ATPase. The Y group may also serve in recognition.Type: GrantFiled: April 6, 1998Date of Patent: May 9, 2000Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim Fat Tam, Regis C. S. H. Leung-Toung, Wanren Li
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Patent number: 5677302Abstract: Novel thiadiazole compounds are provided, which are effective as proton pumps inhibitors, useful in treating peptic ulcers by inhibition of the proton pump enzyme H.sup.+ /K.sup.+ -ATPase. The compounds are 3-substituted 1,2,4-thiadiazolo ?4,5-.alpha.!benzimidazole and 3-substituted imidazo?1,2-d!-1,2,4-thiadiazoles corresponding to the general formula: ##STR1## where X and Z either represent an optionally substituted benzene ring fused to the diazole nucleus, or represent a variety of independent chemical groupings (hydrogen, lower alkyl, halo, etc.) and Y is an electronegative group.Type: GrantFiled: February 26, 1996Date of Patent: October 14, 1997Assignee: Apotex Inc.Inventors: Khashayar Karimian, Tim F. Tam, Denis Desilets, Sue Lee, Tullio Cappelletto, Wanren Li