Abstract: Novel multicyclic erythromycin compounds and pharmaceutically acceptable salts and esters thereof having antibacterial activity having a formula ##STR1## pharmaceutical compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, as well as a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically-effective amount of a compound of formula (I).
Type:
Grant
Filed:
May 29, 1998
Date of Patent:
July 13, 1999
Assignee:
Abbott Laboratories
Inventors:
Yat Sun Or, George Griesgraber, Daniel T. Chu
Abstract: A process for the preparation of N-demethyl-4"-deoxy-erythromycins A and B, having the formula: ##STR1## wherein R.sup.a is H or OH, by stepwise addition of iodine and base to the N-dimethyl-4"-deoxyerythromycin, preferably, accompanied by sparging with an inert gas.
Type:
Grant
Filed:
November 22, 1996
Date of Patent:
July 13, 1999
Assignee:
Abbott Laboratories
Inventors:
Ramiya H. Premchandran, Albert V. Thomas, Juliette K. Busse, John E. Dete
Abstract: The present invention provides a process for the aqueous granulation of a macrolide antibiotic which comprises mixing a macrolide antibiotic and a carbomer; wetting the mixture with water; and blending the mixture to allow formation of a macrolide antibiotic-carbomer granule.
Type:
Grant
Filed:
October 9, 1996
Date of Patent:
July 6, 1999
Assignee:
Abbott Laboratories
Inventors:
Azita Saleki-Gerhardt, Ernest Richard Keske
Abstract: Novel 6-O-alkyl derivatives of erythronolide B are provided. A process for the preparation of 6-O-alkyl derivatives of erythronolide B using erythromycin B is also provided. A process for preparing 6-O-alkyl derivatives of erythromycin C using novel 6-O-alkyl derivatives of erythronolide B is further provided.
Type:
Grant
Filed:
December 1, 1997
Date of Patent:
July 6, 1999
Assignee:
Abbott Laboratories
Inventors:
H. Eugene Gracey, Stephen H. Montgomery, David A. Riley, Jih-Hua Liu
Abstract: The claimed invention provides a novel method of preparing 6-O-methyl erythromycin A. The process comprises the steps of reducing the 9-keto group of erythromycin A to form a 9-hydroxy erythromycin A, protecting the 9-, 2'-, and/or 4"-hydroxyl groups of erythromycin A, selectively methylating the 6-position of the 9-hydroxy erythromycin A derivative, deprotecting the hydroxyl groups and oxidizing the 9-hydroxyl to afford 6-O-methyl erythromycin A.
Type:
Grant
Filed:
December 16, 1997
Date of Patent:
April 6, 1999
Assignee:
Abbott Laboratories
Inventors:
Yi-Yin Ku, David A. Riley, Elaine C. Lee, Jien-Heh Tien
Abstract: Disclosed is an improved and efficient process for N-desmethylating the 3'-amino nitrogen of erythromycins and for converting the 3'-N-desmethylated erythromycins into 3'-N-substituted derivatives of 8,9-anhydro-erythromycin 6,9-hemiketals.
Type:
Grant
Filed:
November 19, 1997
Date of Patent:
March 16, 1999
Assignee:
Abbott Laboratories
Inventors:
John E. Hengeveld, Xiaoxing Dong, Ashok K. Gupta, Richard R. Copp, Jr., Ramiya H. Premchandran
Abstract: A procedure for preparing 6-O-alkyl erythromycin compounds having the formula: ##STR1## wherein R.sup.1 is a loweralkyl group, R.sup.2 and R.sup.3 are independently hydrogen or a hydroxy-protecting group, except that R.sup.2 and R.sup.3 may not both be hydrogen simultaneously; Y is oxygen or a specifically substituted oxime; and Z is hydrogen, hydroxy or protected-hydroxy; by reaction of the compound wherein R.sup.1 is hydrogen with an alkylating reagent, in the presence of a strong alkali metal base and also in the presence of a weak organic amine base, in a suitable stirred or agitated polar aprotic solvent, or a mixture of such polar aprotic solvents maintained at a reaction temperature and for a period of time sufficient to effect alkyation.
Type:
Grant
Filed:
November 21, 1995
Date of Patent:
February 16, 1999
Assignee:
Abbott Laboratories
Inventors:
Jih-Hua Liu, George A. Foster, Jr., Stephen H. Montgomery
Abstract: Antimicrobial compounds having the formula ##STR1## as well as pharmaceutically acceptable salts, esters or prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds.
Type:
Grant
Filed:
July 3, 1997
Date of Patent:
February 2, 1999
Assignee:
Abbott Laboratories
Inventors:
Yat Sun Or, Zhenkun Ma, Richard F. Clark, Daniel T. Chu, Jacob J. Plattner, George Griesgraber
Abstract: Disclosed are novel antifungal agents having the formula: ##STR1## as well as a pharmaceutically acceptable salt, ester of prodrug thereof, whereinR is: ##STR2## --C(O)--R.sub.1 wherein R.sub.1 is alkyl, alkenyl, aryl, arylalkenyl, aryl-aryl-, arylalkoxy-aryl-, aryl-aryl-aryl-, arylkoxy-aryl-aryl-, or ##STR3## wherein R.sub.2 is alkylamino, dialkylamino, (heterocyclic)alkyl, aryl, or arylalkyl; andX is O, NH, or NR.sub.3 wherein R.sub.3 is alkyl or aryl. Also disclosed are pharmaceutical compositions comprising a compound of the invention in combination with a pharmaceutically acceptable carrier; and a process for preparing the compounds of the invention.
Type:
Grant
Filed:
September 30, 1997
Date of Patent:
January 26, 1999
Assignee:
Abbott Laboratories
Inventors:
Geewananda P. Gunawardana, David Frost, Marianna Jackson, James P. Karwowski, Ronald R. Rasmussen
Abstract: The disclosed invention relates to novel 3'-N-O, 9-O-oxime protected, 6-O-alkyl erthyromycin derivatives, a process of preparing the same. The invention also relates to a process of preparing 6-O-alkyl erythromycin A by eliminating the 3'-N-oxide group and 9-O-oxime protecting groups and optionally deprotecting the hydroxy groups at the 2'- and 4"- positions under suitable reaction conditions.
Abstract: The present invention concerns the novel antiobiotic 6-O-methylerythromycin A crystal form I, a process for its preparation, pharmaceutical compositions comprising this compound and a method of use as a therapeutic agent.
Type:
Grant
Filed:
July 29, 1996
Date of Patent:
January 12, 1999
Assignee:
Abbott Laboratories
Inventors:
Jih-Hua Liu, David A. Riley, Steven G. Spanton
Abstract: The present invention provides a uniform dispersion in aqueous medium of droplets comprising: (a) a core comprising water, a non-toxic C.sub.2 -C.sub.5 alkanol, a water-soluble drug, and a surfactant, and (b) a coating surrounding the core comprising one or more pharmaceutically acceptable oils. The compositions of the present invention are particularly useful for the oral delivery of therapeutic agents because of their potential for taste masking, prolonged action, and protection of the drug against the external environment and enzyme entrapment.
Type:
Grant
Filed:
August 7, 1996
Date of Patent:
December 29, 1998
Assignee:
Abbott Laboratories
Inventors:
Mou-Ying Fu Lu, Akwete L. Adjei, Hillard W. Johnson
Abstract: A process of preparing 6-O-alkyl erythromycin A is provided. The process includes the steps of protecting the oxime hydroxyl of 9-oxime erythromycin A with a benzoyl protecting group, protecting the 2'-hydroxyl group and optionally the 4'-hydroxyl group with an O-protecting group, alkylating the 6-hydroxyl, removing the benzoyl and O-protecting groups and deoximating the 9-oxime.
Abstract: The present invention provides a process for the preparation of 6-O-methylerythromycin A Form II comprising converting erythromycin A to 6-O-methylerythromycin A and treating the 6-O-methylerythromycin A with a number of common organic solvents or mixtures of common organic solvents.
Abstract: A process of preparing 6-O-alkylerythromycin A using 9-oximesilyl erythromycin A derivatives is provided. 9-Oximesilyl- and 6-O-alkylerythromycin A derivatives used in the preparation of 6-O-alkylerythromycin A are also provided.
Abstract: A process for the preparation of chiral 3-aminopyrrolidine and analogous bicyclic derivatives from dihydroxy olefins by treatment with titanium isopropoxide, an optically active tartrate ester and tert-butyl hydroperoxide, followed by subsequent alkylation of the intermediate with an alkyl or alkenyl magnesium halide, then pyrrolidine ring formation by condensation with an arylmethylamine, subsequent chiral replacement of a ring hydroxyl group with an amino group with further protection thereof, optional additional substitution closing of the second ring, and hydrogenolysis to remove a ring-nitrogen protecting group.
Type:
Grant
Filed:
November 19, 1997
Date of Patent:
November 17, 1998
Assignee:
Abbott Laboratories
Inventors:
Wei-Bo Wang, Qun Li, Daniel T. Chu, Lisa Anne Hasvold
Abstract: 4"-Deoxy derivatives of erythromycin having the Formula (I) ##STR1## and pharmaceutically acceptable salts thereof, which are enhancers of gastric motility but have minimal antibacterial activity, as well as pharmaceutical compositions containing the same and methods for their use and preparation.
Type:
Grant
Filed:
May 4, 1995
Date of Patent:
November 10, 1998
Assignee:
Abbott Laboratories
Inventors:
Paul A. Lartey, Larry L. Klein, Ramin Faghih, Hugh N. Nellans
Abstract: A process of preparing 9-oxime erythromycin A using a mild acid catalyst such as acetic acid and a mildly polar solvent such as isopropanol is provided. In accordance with that process, erythromycin A is reacted with hydroxylamine in the presence of acetic acid and isopropanol. A process of the present invention can also be used to increase the E to Z isomeric ratio of synthesized 9-oxime erythromycin A.
Abstract: A process for preparing a compound having the formula: ##STR1## wherein R is selected from the group consisting of C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkylmethyl, C.sub.1 -C.sub.6 -alkyl, allyl and 2-methoxyethyl, by reacting: ##STR2## under defined conditions with subsequent stepwise reactions of the respective intermediate compounds with a malonic acid diester, POCl.sub.3, and by heating the final intermediate in a high boiling solvent.
Type:
Grant
Filed:
October 23, 1996
Date of Patent:
August 4, 1998
Assignee:
Abbott Laboratories
Inventors:
Daniel T. Chu, David Allen Degoey, David J. Grampovnik, Larry Lewis Klein, Paul A. Lartey, Christina Louise Leone, Sheela Albert Thomas, Ming Clinton Yeung
Abstract: Novel multicyclic erythromycin compounds and pharmaceutically acceptable salts and esters thereof having antibacterial activity having a formula ##STR1## compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, as well as a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically-effective amount of a compound of the invention.
Type:
Grant
Filed:
September 8, 1997
Date of Patent:
July 14, 1998
Assignee:
Abbott Laboratories
Inventors:
Yat Sun Or, Richard F. Clark, Daniel T. Chu, Jacob J. Plattner