Patents by Inventor Gerald F. Sigler
Gerald F. Sigler 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: 20010044118Abstract: The present invention provides hapten derivatives useful for the preparation of antigens, antibodies and reagents for use in immunoassays for the detection of LSD and 2-oxo-3-hydroxy LSD. In the present invention, the 2-oxy LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. The resulting haptens can then be further modified at this functionalized position for linking to appropriate immunogenic or labeling groups to provide reagents for immunoassays having substantially equal specificity for both LSD and 2-oxo-3-hydroxy-LSD.Type: ApplicationFiled: December 8, 2000Publication date: November 22, 2001Inventors: Mitali Ghoshal, Stephen Vitone, Gerald F. Sigler, Alan J. McNally
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Patent number: 6262265Abstract: Novel chemical analogs are disclosed for the essential heroin metabolite 6-O-acetyl morphine (6MAM). The analogs optionally can be made to contain protein reactive groups, and can be used to form protein conjugates, fluorescently labeled compounds, and solid-phase adsorbants. The proteins conjugates can be used in turn to raise antibodies reactive with 6MAM and having a low cross-reactivity with the closely related opiates, morphine and codeine. The antibodies can be used in combination with labeled analogs in exquisitely sensitive immunoassays suitable for testing for heroin abuse.Type: GrantFiled: June 18, 1999Date of Patent: July 17, 2001Assignee: Microgenics CorporationInventors: Riaz Rouhani, Gerald F. Sigler
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Patent number: 6207396Abstract: To improve the detection of LSD in biological samples, antibodies are raised to LSD conjugated to a protein carrier, preferably through the indole ring. Selected antibodies are matched with an immunoassay reagent in which the LSD is conjugated in the same position to a labeling or separation means. The set of reagents can be used in immunoassays with remarkably little cross-reactivity with potential interfering substances such as chlorpromazine and ergotamine, and a low false-positive rate in a panel of clinical test samples. Also provided is a set of reagents for measuring glucuronide metabolites of LSD by immunoassay, which permits exposure to LSD to be determined over a longer diagnostic window.Type: GrantFiled: February 20, 1998Date of Patent: March 27, 2001Assignee: Microgenics CorporationInventors: Gerald F. Sigler, Riaz Rouhani, David Davoudzadeh, William A. Coty, Jeffrey E. Shindelman, Paul R. Morrill
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Patent number: 6140137Abstract: Novel chemical analogs of the methadone metabolite 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (EDDP) are disclosed. The derivatives can be used for formation of EDDP-protein conjugates. The conjugates can be used in turn to raise antibodies reactive with EDDP and having a low cross-reactivity with methadone. The antibodies and EDDP-enzyme polypeptide conjugates provide the basis for specific immunoassays used in monitoring compliance with methadone treatment.Type: GrantFiled: September 24, 1998Date of Patent: October 31, 2000Assignee: Microgenics CorporationInventors: Gerald F. Sigler, Michael J. Powell, William A. Coty, Anthony J. Sanchez
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Patent number: 5846702Abstract: A new group of Os(II) and Os(III) compounds useful as redox mediators in electrochemical biosensors. These compounds have 1) low oxidation potential, 2) fast reaction kinetics between the electroactive center of an enzyme and the compound, 3) slow oxidation of osmium by oxygen, and 4) excellent solubility in aqueous medium. These mediators are particularly useful as a component of a reagent used in an electrochemical biosensor, wherein the biosensor is useful for measuring analytes from a biological fluid, such as blood.Type: GrantFiled: December 20, 1996Date of Patent: December 8, 1998Assignee: Boehringer Mannheim CorporationInventors: Zhi David Deng, Gerald F. Sigler, Nigel A. Surridge, Christopher D. Wilsey, Robert J. McEnroe, Walter W. Jernigan, Rebecca W. Muddiman
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Patent number: 5843682Abstract: Novel derivatives of LSD having the formula ##STR1## wherein R.sub.1 is an alkyl, cycloalkyl or aryl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 carbon atom;R.sub.2 is a bond or ##STR2## wherein R.sub.3 is alkyl, cycloalkyl or aryl group having 2 to 10 carbon atoms, preferably an alkyl group having 2 or 5 carbon atoms; Z is an immunogenic carrier substance, an enzyme donor polypeptide or a label selected from the group consisting of an enzyme, a substance having fluorescent or luminescent properties and a radioactive substance; and n is 1 to p where p equals MW of Z/1000. The derivatives include maleimide conjugates of an immunogenic poly(amino acid), an enzyme donor polypeptide or a labeling substance such as an enzyme, a fluorescent substance or a radioactive substance. Novel activated hapten intermediates useful in the preparation of the conjugates and methods for synthesis of the hapten intermediates and their conjugate derivatives are also disclosed.Type: GrantFiled: November 20, 1995Date of Patent: December 1, 1998Assignee: Boehringer Mannheim CorporationInventors: Gerald F. Sigler, Riaz Rouhani, David Davoudzaheh
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Patent number: 5589326Abstract: A new group of Os(II) and Os(III) compounds useful as redox mediators in electrochemical biosensors. These compounds have 1) low oxidation potential, 2) fast reaction kinetics between the electroactive center of an enzyme and the compound, 3) slow oxidation of osmium by oxygen, and 4) excellent solubility in aqueous medium. These mediators are particularly useful as a component of a reagent used in an electrochemical biosensor, wherein the biosensor is useful for measuring analytes from a biological fluid, such as blood.Type: GrantFiled: December 30, 1993Date of Patent: December 31, 1996Assignee: Boehringer Mannheim CorporationInventors: Zhi D. Deng, Gerald F. Sigler, Nigel A. Surridge, Christopher D. Wilsey, Robert J. McEnroe, Walter W. Jernigan, Rebecca W. Muddiman
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Patent number: 5525474Abstract: Novel derivatives of procainamide and N-acetylprocainamide (NAPA) are disclosed having the following formula: ##STR1## wherein: X=hydrogen or acetyl;n=1 to p where p=MW of Z/1000;Z=a poly(amino acid) or polysaccharide; andR3=a bond or ##STR2## wherein R2=an alkyl, cycloalkyl or aryl group having 2 to 10 carbon atoms. The derivatives include maleimide conjugates of proteins or poly(amino acids), enzymes, enzyme donor polypeptides and labeling substances. Novel activated hapten intermediates useful in the preparation of the conjugates and methods for synthesis of the hapten intermediates and derivatives are also disclosed.Type: GrantFiled: January 31, 1994Date of Patent: June 11, 1996Assignee: Boehringer Mannheim CorporationInventors: Gerald F. Sigler, Charles F. Walter, Todd Glancy, Erasmus Huber, Frank E. Klein
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Patent number: 5439798Abstract: Novel derivatives of procainamide and N-acetylprocainamide (NAPA) are disclosed having the following formula: ##STR1## wherein: X=hydrogen or acetyl;R.sub.1 =an alkyl group having 1 to 3 carbon atoms;m=an integer from 2 to 10;R.sub.2 =an alkyl, cycloalkyl or aryl group having 2 to 10 carbon atoms;Z=a poly(amino acid); andn=1 to p where p=MW of Z/1000.The derivatives include maleimide conjugates of proteins or poly(amino acids), enzymes, enzyme donor polypeptides and labeling substances. Novel activated hapten intermediates useful in the preparation of the conjugates and methods for synthesis of the hapten intermediates and derivatives are also disclosed.Type: GrantFiled: December 17, 1993Date of Patent: August 8, 1995Assignee: Boehringer Mannheim CorporationInventors: Gerald F. Sigler, Charles F. Walter, Charles E. Durant, Todd Glancy, Frank E. Klein, Allan R. Dorn
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Patent number: 5336621Abstract: Divalent hapten derivatives wherein two hapten moieties are connected by means of a bifunctional spacer wherein the derivative has the formulaA--X--Awhere A is a bonded hapten moiety and X is a bifunctional spacer having the formula(B).sub.m --Y--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.n --Y--(B).sub.mwhere m is independently 0 or 1, B is (CH.sub.2).sub.n', wherein n' is an integer from 1 to 4, or CO(CH.sub.2).sub.n", wherein n" is an integer from 2 or 4; Y is independently --CONH--, --NHCO--, --OOC, --COO--, --O--, --S--, or --NR--, wherein R is hydrogen or alkyl; n is an integer from 1 to 10; and Z is an organic moiety containing at least one hydrophilic atom, useful for the determination of haptens by immunochemical techniques are disclosed.Type: GrantFiled: June 27, 1988Date of Patent: August 9, 1994Assignee: Hoechst Celanese CorporationInventors: Kathleen J. Primes, Gerald F. Sigler, Gerd Grenner, Wolfgang Kapmeyer
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Patent number: 5320954Abstract: An aromatic substituted glycoside is disclosed of the formula ##STR1## wherein the configuration of the substituted --OR on the anomeric carbon is alpha, n is an integer of 0 or 1, and R is a substituted aromatic radical selected from the group ##STR2## where R.sub.1 through R.sub.6 are independently halogen, NO.sub.2, SO.sub.3 H, COR.sub.7, ##STR3## where R.sub.7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.Type: GrantFiled: September 3, 1992Date of Patent: June 14, 1994Assignee: Hoechst Celanese CorporationInventors: Rodrigo G. Chavez, Harold David, Ernest K. Metzner, Gerald F. Sigler, Emily S. Winn-Deen
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Patent number: 5158872Abstract: An aromatic substituted glycoside is disclosed of the formula ##STR1## wherein the configuration of the substituted --OR on the anomeric carbon is alpha, n is an integer of 0 or 1, and R is a substituted aromatic radical selected from the group ##STR2## where R.sub.1 through R.sub.6 are independently halogen, NO.sub.2, SO.sub.3 H, ##STR3## where R.sub.7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.Type: GrantFiled: August 10, 1990Date of Patent: October 27, 1992Assignee: Hoechst Celanese CorporationInventors: Rodrigo G. Chavez, Harold David, Ernest K. Metzner, Gerald F. Sigler, Emily S. Winn-Deen
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Patent number: 4963479Abstract: An aromatic substituted glycoside is disclosed of the formula ##STR1## wherein the configuration of the substituted --OR on the anomeric carbon is alpha, n is an integer of 0 to 1, and R is a substituted aromatic radical selected from the group ##STR2## where R.sub.1 through R.sub.6 are independently halogen, NO.sub.2, SO.sub.3 H, ##STR3## where R.sub.7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.Type: GrantFiled: September 4, 1987Date of Patent: October 16, 1990Assignee: Hoechst Celanese CorporationInventors: Rodrigo G. Chavez, Harold David, Ernest K. Metzner, Gerald F. Sigler, Emily S. Winn-Deen
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Patent number: 4798795Abstract: Compounds having a dithiopyridyl moiety linked to a biotin moiety are useful as thiol specific biotinylating agents. The biotin label can be cleaved in a reducing environment to yield the native thiol.Type: GrantFiled: September 3, 1987Date of Patent: January 17, 1989Assignee: Hoechst Celanese CorporationInventor: Gerald F. Sigler
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Patent number: 4794082Abstract: Compounds having a dithiopyridyl moiety linked to a biotin moiety are useful as thiol specific biotinylating agents. The biotin label can be cleaved in a reducing environment to yield the native thiol.Type: GrantFiled: September 3, 1987Date of Patent: December 27, 1988Assignee: Hoechst Celanese CorporationInventor: Gerald F. Sigler
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Patent number: 4760142Abstract: Divalent hapten derivatives wherein two hapten moieties are connected by means of a bifunctional spacer wherein the derivative has the formulaA--X--Awhere A is a bonded hapten moiety and X is a bifunctional spacer having the formula(B).sub.m --Y--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.n --Y--(B).sub.mwhere m is independently 0 or 1, B is (CH.sub.2).sub.n', wherein n' is an integer from 1 to 4, or CO(CH.sub.2).sub.n", wherein n" is an integer from 2 to 4; Y is independently --CONH--, NHCO--, OOC--, --COO--, --O--, --S--, or --NR--, wherein R is hydrogen or alkyl; n is an integer from 1 to 10; and Z is an organic moiety containing at least one hydrophilic atom are disclosed.Type: GrantFiled: July 6, 1987Date of Patent: July 26, 1988Assignee: Hoechst Celanese CorporationInventors: Kathleen J. Primes, Gerald F. Sigler, Gerd Grenner, Wolfgang Kapmeyer
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Patent number: 4709037Abstract: Compounds having a dithiopyridyl moiety linked to a biotin moiety are useful as thiol specific biotinylating agents. The biotin label can be cleaved in a reducing environment to yield the native thiol.Type: GrantFiled: February 17, 1987Date of Patent: November 24, 1987Assignee: Hoechst Celanese CorporationInventor: Gerald F. Sigler