Patents by Inventor Arthur L. Campbell
Arthur L. Campbell 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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Patent number: 6127556Abstract: In a method of preparing an aminoepoxide wherein a protected aminoaldehyde is reacted with a halomethyl organometallic reagent in an appropriate solvent at a temperature above -80.degree. C., wherein said halomethyl organometallic reagent is formed by reaction between an organometallic reagent and a dihalomethane, the improvement comprising flowing said protected aminoaldehyde into a mixing zone maintained at a temperature below 0.degree. C., also flowing said halomethyl organometallic reagent in said mixing zone for contacting in said mixing zone with said protected aminoaldehyde and also withdrawing from said mixing zone reaction products of said protected aminoaldehyde and said halomethyl organometallic reagent.Type: GrantFiled: December 16, 1997Date of Patent: October 3, 2000Assignee: G. D. Searle & Co.Inventors: Chin Liu, John S. Ng, James R. Behling, Arthur L. Campbell
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Patent number: 5013864Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.Type: GrantFiled: December 8, 1989Date of Patent: May 7, 1991Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
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Patent number: 5011958Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as epoxide addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes derived from the reaction of a cuprate complex with 1,2-bis-tri-n-butylstannyl ethylene are particularly useful for the addition to epoxides to form vinyl tin intermediates useful for preparing omega side chains of prostaglandins.Type: GrantFiled: October 25, 1989Date of Patent: April 30, 1991Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling, John S. Ng, Kevin A. Babiak
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Patent number: 4952710Abstract: This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula ##STR1## wherein R.sub.1 is hydrogen, --COCH.sub.3, --COCF.sub.3, --CO--phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl;wherein R.sub.2 is --CH.sub.2 OR.sub.1, --COOH, --COOR, --CHO, --CH.sub.2 --OSi(R.sub.12).sub.3, ##STR2## wherein R is lower alkyl and each R.sub.12 is independently lower alkyl or aryl; andwherein Y is ethylene, cis-vinylene, trans-vinylene, or acetylene.Also disclosed is a novel process for preparation of the above-defined cyclopenteneheptenoic acid derivative. This process involves coupling of a higher order cuprate complex with a chiral cyclopentene compound. The resultant product is particularly useful as a starting compound for high yield synthesis of optically active prostaglandins.Type: GrantFiled: October 7, 1988Date of Patent: August 28, 1990Assignee: G. D. Searle & Co.Inventors: Kevin A. Babiak, Arthur L. Campbell
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Patent number: 4952724Abstract: A process for producing aryloxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R-OH wherein R is aryl or substituted aryl with a base in an aprotic organic solvent to give an aryloxide followed by removal of the organic solvent and reaction of the aryloxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding aryloxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the aryloxyacetate salt with an acid.Type: GrantFiled: December 8, 1989Date of Patent: August 28, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A, Partis
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Patent number: 4910310Abstract: Novel intermediates and method for the chemical synthesis of N-substituted 1,5-dideoxy-1,5-imino-L-fucitol derivatives are provided. A preferred intermediate is 1,5-dideoxy-1,5-imino-3, 4-O-isopropylidene-L-fucitol which is used to prepare the HIV inhibitor 1,5-dideoxy-1,5-imino-[N-.omega.-methyl caproate]-L-fucitol. These compounds are prepared in a short synthesis from the known compound 2,3-O-isopropylidene-D-lyxono-1,4-lactone or in a multi-step synthesis from D-galactose.Type: GrantFiled: October 3, 1988Date of Patent: March 20, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling, Kevin A. Babiak, John S. Ng, Richard A. Mueller, George W. J. Fleet
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Patent number: 4904820Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate cmoplex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.Type: GrantFiled: July 14, 1988Date of Patent: February 27, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling
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Patent number: 4812474Abstract: Kojic acid ether-ester derivatives of formula I ##STR1## are useful pharmacological agents for the prevention, management or alleviation of elastase mediated diseases or conditions.Type: GrantFiled: January 12, 1988Date of Patent: March 14, 1989Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Masateru Miyano
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Patent number: 4785124Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as epoxide addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes derived from the reaction of a cuprate complex with 1,2-bis-tri-n-butylstannyl ethylene are particularly useful for the addition to epoxides to form vinyl tin intermediates useful for preparing omega side chains of prostaglandins.Type: GrantFiled: June 8, 1987Date of Patent: November 15, 1988Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling, Sau-hoi N. John, Kevin A. Babiak
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Patent number: 4777275Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.Type: GrantFiled: June 9, 1987Date of Patent: October 11, 1988Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling
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Patent number: 4735964Abstract: Kojic acid ether-ester derivatives of formula I ##STR1## are useful pharmacological agents for the prevention, management or alleviation of elastase mediated diseases or conditions.Type: GrantFiled: May 12, 1986Date of Patent: April 5, 1988Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Masateru Miyano
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Patent number: 4661592Abstract: This invention relates to a class of novel 4H-pyrimido[2,1-a]isoquinoline derivatives. The invention further relates to pharmaceutical compositions containing such 4H-pyrimido[2,1-a]isoquinoline-4-one derivatives and to the use of such compounds and compositions as anorectic agents. In particular, the novel 4H-pyrimido[2,1-a]isoquinoline-4-one derivatives are effective anorectic agents when administered orally.Type: GrantFiled: June 27, 1984Date of Patent: April 28, 1987Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Suzanne Evans Radak, Melanie J. Loots
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Patent number: 4603144Abstract: Kojic acid ether-ester derivatives of formula I ##STR1## are useful pharmacological agents for the prevention, management or alleviation of elastase mediated diseases or conditions.Type: GrantFiled: August 16, 1984Date of Patent: July 29, 1986Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Masateru Miyano