Abstract: The invention is a process for preparing a compound of formula Ia
comprising reducing the compound of formula IIId
wherein R3 is 1-piperidinyl, 1-pyrrolidinyl, dimethylamino, diethylamino or 1-hexamethyleneimino, R1a, R1b, R2a, R2b, and n are as defined in the specification, with a reducing agent in the presence of a solvent, heating to reflux.
Type:
Grant
Filed:
April 21, 1995
Date of Patent:
August 20, 2002
Assignee:
Eli Lilly and Company
Inventors:
Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
Abstract: The present invention provides a compound of formula I
wherein
R1 is —H, —OH, —O(C1-C4 alkyl) , —OCOC6H5, —OCO(C1-C6 alkyl), or —OSO2 (C4-C6 alkyl);
R2 is —H, —OH, —O(C1-C4 alkyl), —OCOC6H5, —OCO(C1-C6 alkyl) or —OSO2 (C4-C6 alkyl);
n is 2 or 3; and
R3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof. Compounds of formula I are useful in treating osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.
Type:
Grant
Filed:
April 21, 1995
Date of Patent:
June 25, 2002
Assignee:
Eli Lilly and Company
Inventors:
Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
Abstract: The present invention provides novel compound of the formula:
wherein
Ra is —OH or
—O—(C1-C4 alkyl);
R1a is —OH or
—O—(C1-C4 alkyl);
n is 2 or 3;
R2 and R3 are each independently:
—C1-C4 alkyl, or
combine to form
1-piperidinyl,
1-pyrrolidinyl,
1-pyrrolidinyl substituted with one or two methyl groups,
4-morpholino or
1-hexamethyleneimino;
or a pharmaceutically acceptable salt thereof.
Type:
Grant
Filed:
May 10, 1995
Date of Patent:
June 18, 2002
Assignee:
Eli Lilly and Company
Inventors:
Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
Abstract: Polymorphs Form B, Form C, and amorphous of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone, commonly known as cilostazol, have been identified. These polymorphs may be formed in pure form, in combination with each other, in combination with other polymorphs of cilostazol, or together with other pharmaceutical agents. Processes for preparing these polymorphs, and combinations of these polymorphs, as well as methods of use and unit dosages of these polymorphic forms, and their combinations, are described.
Type:
Grant
Filed:
June 29, 2001
Date of Patent:
May 14, 2002
Inventors:
Grayson Walker Stowell, Robert R. Whittle
Abstract: Compounds represented by formula (Ia) are disclosed by the invention, along with compositions and complexes thereof, optionally in combination with compounds of formula (Ib). Pharmaceutical formulations and methods of making and using such compounds are also disclosed.
Type:
Grant
Filed:
August 24, 2000
Date of Patent:
April 9, 2002
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall
Abstract: The present invention relates to novel, liquid and semi-solid pharmaceutical compositions which can be administered in liquid form or can be used for preparing capsules containing such pharmaceutical compositions. Also provided are methods of using and processes for preparing the pharmaceutical compositions of the present invention.
Type:
Grant
Filed:
July 16, 1999
Date of Patent:
April 2, 2002
Inventors:
Glenn A. Meyer, Laura A. Trespidi, Edward S. Wilson, Christy M. Clark, Ashok J. Desai, Frederick D. Sancilio
Abstract: The present invention provides dry blend pharmaceutical formulations in unit dosage forms comprising per dosage unit one or more active pharmaceutical ingredients or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof wherein the ratio of said one or more active pharmaceutical ingredients in said formulations is essentially the same as the ratio of said active pharmaceutical ingredients in the corresponding, non-formulated drug substance and, wherein said formulations in unit dosage form are adapted for oral administration.
Type:
Grant
Filed:
August 24, 2000
Date of Patent:
December 4, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall
Abstract: Pharmaceutical compositions and formulations comprised of one or more active ingredients or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof combined with at least one cyclodextrin.
Type:
Grant
Filed:
July 31, 2000
Date of Patent:
November 13, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall, Glenn Alan Meyer
Abstract: Pharmaceutical formulations, in oral unit dosage forms, have one or more active ingredients or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof combined with at least one cyclodextrin.
Type:
Grant
Filed:
July 31, 2000
Date of Patent:
November 6, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall, Glenn Alan Meyer, Steven A. Fontana
Abstract: Improved bioavailability method of one or more of certain pharmaceutically active compounds or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof that include administering a non-toxic, therapeutically effective amount of the compounds combined with at least one cyclodextrin to a mammal in need of treatment of gastric acid related diseases.
Type:
Grant
Filed:
July 31, 2000
Date of Patent:
November 6, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall, Glenn Alan Meyer
Abstract: The present invention provides novel amorphous fluoxetine hydrochloride as a useful intermediate for the preparation of Form A of fluoxetine hydrochloride.
Type:
Grant
Filed:
January 31, 2001
Date of Patent:
October 30, 2001
Inventors:
Grayson Walker Stowell, Robert R. Whittle
Abstract: The present invention relates to novel, liquid and semi-solid pharmaceutical compositions which can be administered in liquid form or can be used for preparing capsules containing such pharmaceutical compositions. Also provided are methods of using and processes for preparing the pharmaceutical compositions of the present invention.
Type:
Grant
Filed:
January 15, 1999
Date of Patent:
September 11, 2001
Inventors:
Edward S. Wilson, Laura A. Trespidi, Christy M. Clark, Ashok J. Desai, Glenn A. Meyer
Abstract: The present invention provides pharmaceutical formulations comprising compositions one or more of certain active pharmaceutical ingredients or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof wherein the ratio of said one or more active pharmaceutical ingredients in said formulations is essentially the same as the ratio of said active pharmaceutical ingredients in the corresponding, non-formulated drug substance. Methods for using the same are included.
Type:
Grant
Filed:
August 24, 2000
Date of Patent:
July 31, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall, Steven A. Fontana
Abstract: Compounds of the formula (Ia) are disclosed by the invention, along with compositions thereof optionally in combination with compounds of formulae (Ib). Methods of making and using the same are also disclosed.
Type:
Grant
Filed:
March 7, 2000
Date of Patent:
July 17, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall
Abstract: Pharmaceutical oral unit dosage forms are comprised of, per dosage unit, one or more active ingredients or pharmaceutically acceptable salts, solvates, hydrates, or combinations thereof.
Type:
Grant
Filed:
July 31, 2000
Date of Patent:
July 17, 2001
Inventors:
Robert R. Whittle, Frederick D. Sancilio, Grayson Walker Stowell, Douglas John Jenkins, Linda B. Whittall, Steven A. Fontana
Abstract: The present invention provides processes for preparing compounds comprising flutamide API having a specific surface area of at least 0.35 m2/cm3 which comprise blending pharmaceutically acceptable diluents with unmilled flutamide API and milling the blended material until the specific surface area is at least 0.35 m2/cm3. The present invention also provides compounds prepared by such processes.
Type:
Grant
Filed:
October 11, 2000
Date of Patent:
May 8, 2001
Inventors:
Jack Lawrence James, Louis Frank Molnar, Jr., Tania E. Toney-Parker