Patents by Inventor Saul Wolfe
Saul Wolfe 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: 20060069091Abstract: The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.Type: ApplicationFiled: January 6, 2005Publication date: March 30, 2006Inventors: Saul Wolfe, Gennady Shustov
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Publication number: 20050124612Abstract: The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.Type: ApplicationFiled: January 7, 2005Publication date: June 9, 2005Inventors: Saul Wolfe, Gennady Shustov
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Patent number: 6861416Abstract: The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.Type: GrantFiled: April 10, 2003Date of Patent: March 1, 2005Assignee: Chirologix Pharmaceuticals, Inc.Inventors: Saul Wolfe, Gennady Shustov
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Publication number: 20040023956Abstract: The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.Type: ApplicationFiled: April 10, 2003Publication date: February 5, 2004Inventors: Saul Wolfe, Gennady Shustov
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Publication number: 20030232820Abstract: New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.Type: ApplicationFiled: August 29, 2002Publication date: December 18, 2003Inventors: Saul Wolfe, Marie-Claire Wilson, Ming-Huei Cheng
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Patent number: 6660734Abstract: The invention relates to novel oxazinones designed to bind to the penicillin receptor, methods of synthesizing the compounds, and the use of the compounds as antibacterial agents. The compounds have the general formula (I) Preferably the compounds have a carboxyethyl or a substituted carboxymethyl substituent at the 2-position and a hydroxyl group at the 5-position and have a molecular shape suitable for binding to and reacting with the active site of a pencillin-recognizing enzyme. The compounds are synthesized by condensing a carboxyl-protected N-hydroxy amino acid with a 3-hydroxyprotected-4-bromobutanoic acid to form a a doubly protected N-hydroxy N-acylamino acid, which is cyclized with an organic base to yield a: doubly protected 1,2-oxazin-3-one. The protecting groups are then removed to provide an antibacterial agent.Type: GrantFiled: January 22, 2002Date of Patent: December 9, 2003Assignee: Simon Fraser UniversityInventors: Saul Wolfe, Christiana Akuche, Stephen Ro
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Patent number: 6399600Abstract: The invention relates to novel oxazinones designed to bind to the penicillin receptor, methods of synthesizing the compounds, and the use of the compounds as antibacterial agents. The compounds have the general formula (I) Preferably the compounds have a carboxyethyl or a substituted carboxymethyl substituent at the 2-position and a hydroxyl group at the 5-position and have a molecular shape suitable for binding to and reacting with the active site of a pencillin-recognizing enzyme. The compounds are synthesized by condensing a carboxyl-protected N-hydroxy amino acid with a 3-hydroxyprotected-4-bromobutanoic acid to form a a doubly protected N-hydroxy N-acylamino acid, which is cyclized with an organic base to yield a doubly protected 1,2-oxazin-3-one. The protecting groups are then removed to provide an antibacterial agent.Type: GrantFiled: June 22, 1998Date of Patent: June 4, 2002Assignee: Simon Fraser UniversityInventors: Saul Wolfe, Christiana Akuche, Stephen Ro
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Patent number: 5552543Abstract: Novel six-membered hetero "N" compounds having antibiotic activity, represented by the formula: ##STR1## where X.dbd.S, O, CH.sub.2, or SeY.dbd.OH, NH.sub.2, NHCOR.sub.9, or SHR.sub.1,R.sub.2,R.sub.3,R.sub.4,R.sub.5,R.sub.6,R.sub.7 (which may be identical or different).dbd.H, alkyl, or arylR.sub.9 .dbd.a .beta.-lactam active side chain;computer models for evaluating such compounds and processes for preparing them.Type: GrantFiled: November 4, 1993Date of Patent: September 3, 1996Assignee: Simon Fraser UniversityInventors: Saul Wolfe, Stephen Bruder
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Patent number: 4847200Abstract: A process for producing unnatural penicillins and cephalosporin derivatives thereof in which peptide analogs of ACV in which the L-.alpha.-aminodipyl moiety is replaced by L-S-carboxymethyl cysteine or other obvious substituents, are reacted with cyclase, epimerase, ring expansion and hydroxylase enzymes isolated from a cell free extract of a prokaryotic organism such as S. clavuligerus. The product depends upon the presence or absence of co-factors such as ferrous ion, .alpha.-ketoglutarate, and ascorbate. In an alternative embodiment, a penicillin analog having the formula: ##STR1## may be reduced with L-cysteine to produce an analog of isopenicillin N which may be reacted with the enzyme reagent to produce the desired penicillin or cephalosporin.Type: GrantFiled: September 5, 1986Date of Patent: July 11, 1989Assignee: Queen's University at KingstonInventors: Saul Wolfe, Donald Westlake, Susan Jensen
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Patent number: 4693977Abstract: Enzymes extracted from a prokaryotic .beta.-lactam producing microorganism are immobilized on a support for producing desacetoxycephalosporin and analogs thereof from L-.alpha.-aminoadipyl-L-cysteinyl-D-valine and analogs thereof. The enzymes are an epimerase, a cyclase and a ring expansion enzyme extracted preferably from S. clavuligerus, S. cattleya or S. lipmanii. The support is preferably a diethylaminoethyl ion exchange resin.Type: GrantFiled: January 23, 1986Date of Patent: September 15, 1987Assignee: Queen's University at KingstonInventors: Saul Wolfe, Donald Westlake, Susan Jensen
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Patent number: 4579818Abstract: A process is disclosed for converting a peptide precursor of the ACV type, in which the valine moiety may be replaced by any readily available amino acid, to an unnatural cephalosporin of the type ##STR1## where R.sub.1 is H, lower alkyl or functionalized carboxylic group and R.sub.2 is H or lower alkyl, in which the precursor is reacted with cyclase, epimerase and a ring expansion enzyme isolated from a cell-free extract of a prokaryotic organism such as Streptomyces clavuligerus. The three enzymes may be immobilized on a suitable support medium and the conversion may be carried out in a continuous mode.Type: GrantFiled: February 6, 1985Date of Patent: April 1, 1986Assignee: Queen's University at KingstonInventors: Saul Wolfe, Donald Westlake, Susan Jensen
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Patent number: 4536476Abstract: Cyclase, epimerase and a ring expansion enzyme are isolated separately from a cell free extract of a prokaryotic beta-lactam producing organism to provide three separate and stable enzyme reagents for commercial production of cephalosporins from peptide precursors. Isolation is carried out by using ammonium sulfate, gel filtration and ion exchange chromatography. The enzymes may be immobilized on a suitable support and the production of cephalosporins may be carried out continuously.Type: GrantFiled: June 27, 1983Date of Patent: August 20, 1985Assignee: Queen's University at KingstonInventors: Saul Wolfe, Donald Westlake, Susan Jensen
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Patent number: 4514333Abstract: A process for preparing compounds of the formula ##STR1## in which R is hydrogen or methoxy,R.sub.1 is a hydroxyl group,R.sub.2 is chlorine, bromine, OCOCH.sub.3 or SHET,R.sub.3 is hydrogen or a cleavable carboxy-protecting group preferably selected from loweralkyl, benzyl, benzhydryl, loweralkoxyloweralkyl, loweralkoxybenzyl, phenacyl, trimethylsilyl, 2,2,2-trichloroethyl or pivaloyl,R.sub.4 is hydrogen or a cleavable acyl group, or R.sub.4 NH represents phthalimido, andHET is a five membered aromatic heterocycle containing 1-4 heteroatoms and optionally substituted with loweralkyl,and from which the corresponding 1-oxacephem derivtives can be prepared is described. The novel intermediate compounds of the formula 1 are produced from a penicillin derivative of formula 1 wherein R, R.sub.3 and R.sub.4 are as above described and R.sub.1 and R.sub.2 are both the same halogen, by treatment with a formylating agent in a halogenated hydrocarbon solvent to obtain the corresponding compound in which R.sub.1 and R.Type: GrantFiled: February 10, 1983Date of Patent: April 30, 1985Assignee: Queen's University at KingstonInventors: Saul Wolfe, Chia-Cheng Shaw
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Patent number: 4510246Abstract: The enzymes, cyclase, epimerase and a ring expansion enzyme, are isolated separately from a cell-free extract of a prokaryotic beta-lactam producing organism. The isolated enzymes are used to produce unnatural cephalosporins from polypeptide precursors. Isolation is carried out by adding ammonium sulfate to 40% saturation to the cell-free extract to precipitate contaminating proteins, adding ammonium sulfate to 70% saturation to the resultant supernatant to precipitate the enzymes, suspending the precipitated enzymes in a buffer, separating epimerase from the suspension by gel filtration, and separating cyclase and the ring expansion enzyme from each other by ion exchange chromatography.Type: GrantFiled: August 23, 1982Date of Patent: April 9, 1985Assignee: Queen's University at KingstonInventors: Saul Wolfe, Donald Westlake, Susan Jensen
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Patent number: 4391975Abstract: A process for preparing compounds of the formula ##STR1## in which R is hydrogen or methoxy,R.sub.1 is a hydroxyl group,R.sub.2 is chlorine, bromine, OAc or SHET,R.sub.3 is hydrogen or a cleavable carboxy-protecting group preferably selected from loweralkyl, benzyl, benzhydryl, loweralkoxyloweralkyl, loweralkoxybenzyl, phenacyl, trimethylsilyl, 2,2,2-trichloroethyl or pivaloloxy,R.sub.4 is hydrogen or a cleavable amino-protecting acyl group, or R.sub.4 NH represents phthalimido, andHET is a five or six membered aromatic heterocycle containing 1-4 heteroatoms and optionally substituted with loweralkyl,and from which the corresponding 1-oxacephem derivatives can be prepared is described. The novel intermediate compounds of the formula 1 are produced from a penicillin derivative of formula 1 wherein R, R.sub.3 and R.sub.4 are as above described and R.sub.1 and R.sub.Type: GrantFiled: March 8, 1982Date of Patent: July 5, 1983Assignee: Queen's University at KingstonInventors: Saul Wolfe, Chia-Cheng Shaw
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Patent number: 4208325Abstract: The invention provides a novel process for opening the ring of 2-R-6-(1'-R.sup.1 -oxycarbonyl-2'-methyl-prop-1'-enyl)-1-oxa-3,6-diaza-4S,5R-bicyclo[3,2,0]h ept-2-en-7-one by treatment with a sulfonic acid salt thereby forming R.sup.1 2-(2'R-R-oxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate sulfonic acid salts which can provide oxapenicillins by two different routes depending on the substituent desired on the carboxamido group of the 1-oxapenicillins. In the alternate processes, new intermediates are also provided.Type: GrantFiled: November 30, 1977Date of Patent: June 17, 1980Assignee: Queen's University at KingstonInventor: Saul Wolfe
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Patent number: 4200571Abstract: The present invention relates to a novel group of compounds which are broadly referred to as 1-oxacephems and processes for preparing same.Type: GrantFiled: March 7, 1977Date of Patent: April 29, 1980Assignee: Queens University at KingstonInventor: Saul Wolfe
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Patent number: 4071512Abstract: The invention provides a novel process for opening the ring of 2-R-6-(1'-R.sup.1 -oxycarbonyl-2'-methyl-prop-1'-enyl)-1-oxa-3,6-diaza-4S,5R-bicyclo[3,2,0]h ept-2-en-7-one by treatment with a sulfonic acid salt thereby forming R.sup.1 2-(2'R-R-oxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate sulphonic acid salts which can provide oxapenicillins by two different routes depending on the substituent desired on the carboxamido group of the 1-oxapenicillins. In the alternate processes, new intermediates are also provided.Type: GrantFiled: June 17, 1975Date of Patent: January 31, 1978Assignee: Queen's University at KingstonInventor: Saul Wolfe
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Patent number: 4018782Abstract: The title compounds, which can casually be called 1-oxapenicillins, are produced by total synthesis. Thus 1-oxabenzylpenicillin is produced either by phenylacetylation of 2,2-dimethyl-3R-carboxy-6S-amino-1-oxa-4-aza-5R-bicyclo[3,2,0]heptan-7-one or by hydrolysis and rearrangement of 2-benzyl-6-(1'-methoxycarbonyl-2'-methylprop-1'-enyl)-1-oxa-3,6-diaza-4S, 5R-bicyclo[3,2,0]hept-2-en-7-one.Type: GrantFiled: August 26, 1974Date of Patent: April 19, 1977Assignee: Queen's UniversityInventor: Saul Wolfe
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Patent number: 4013653Abstract: The present invention relates to novel 1-oxacephems of the formula ##STR1## wherein R.sup.9 is hydrogen and R.sup.8 is hydrogen orRCO-wherein R is selected from the group consisting of lower alkyl ##STR2## wherein Ar is a monovalent radical selected from the group consisting of ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 are each a member selected from the group consisting of hydrogen, chloro, bromo, iodo, trifluoromethyl, phenyl, lower-alkyl and lower alkoxy, but only one of said R.sub.1, R.sub.2 and R.sub.3 may represent phenyl;R.sup.4 is hydrogen, amino, carbobenzoxyamino, phenyl, fluoro, chloro, bromo, iodo, carboxyl, SO.sub.3 H, azido, hydroxy, loweralkanoyloxy or loweralkoxy;X is oxygen or sulfur;R.sup.5 and R.sup.6 are hydrogen, phenyl, benzyl, phenethyl or loweralkyl;Z.sup.1, z.sup.2 and Z.sup.3 are loweralkyl or the Ar- group;R.sup.12 is 2,2,2-trichloroethyl or benzyl;Provided that when R.sup.8 and R.sup.Type: GrantFiled: July 21, 1975Date of Patent: March 22, 1977Assignee: Queen's University at KingstonInventor: Saul Wolfe