Patents Represented by Attorney Gary M. Birch
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Patent number: 8030330Abstract: This invention provides compounds of formula I and pharmaceutically acceptable salts and solvates thereof, characterized that the compound is in particulate form and having a specific size range. The present invention further provides pharmaceutical compositions containing or formulated using compounds of formula I, and the use of such compounds for alleviating human pathologies, including osteoporosis, serum lipid lowering, and breast cancer.Type: GrantFiled: April 9, 2010Date of Patent: October 4, 2011Assignee: Eli Lilly and CompanyInventors: Gordon Nelson Arbuthnot, Brian Weston Dalder, Kerry John Hartauer, Wayne Douglas Luke, Robert Eugene Stratford, Jr.
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Patent number: 7045628Abstract: The present invention relates to a one-pot process for preparing a compound of formula I: I; by reacting a compound of formula II with a compound of formula III: in the presence of a suitable solvent, a suitable base, a palladium catalyst and a suitable ligand.Type: GrantFiled: November 15, 2001Date of Patent: May 16, 2006Assignee: Eli Lilly and CompanyInventors: Scott Allan May, Thomas Michael Wilson, Tony Yantao Zhang
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Patent number: 7012153Abstract: An improved process for the preparation of 4[(2-piperidin-1-yl)ethoxy]benzoic acid derivatives, comprising reacting a haloalkyl amine of formula (III) with a compound of formula (IV) in the presence of a hydrated inorganic base in an appropriate solvent.Type: GrantFiled: December 22, 2003Date of Patent: March 14, 2006Assignee: Eli Lilly and CompanyInventor: Wayne Douglas Luke
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Patent number: 6921827Abstract: The present invention relates to a process for preparing a compound of formula (I): which includes cyclodehydrating a compound of formula (II): in the presence of an acid activated clay or acid activated zeolite catalyst and in the presence of a suitable solventType: GrantFiled: November 14, 2001Date of Patent: July 26, 2005Assignee: Eli Lilly and CompanyInventors: Wayne Douglas Luke, Heidi Ann Sanderson, Hua Zheng
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Patent number: 6812244Abstract: The instant invention provides novel substituted naphthyl compounds, intermediates, compositions, pharmaceutical formulations, and methods of use.Type: GrantFiled: May 27, 2003Date of Patent: November 2, 2004Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones, Alan David Palkowitz
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Patent number: 6713494Abstract: The instant invention provides an amorphous form of a compound of formula I Methods of preparing an amorphous form of a compound of formula I, pharmaceutical formulations containing same, and methods of using same are also provided.Type: GrantFiled: August 25, 1997Date of Patent: March 30, 2004Assignee: Eli Lilly and CompanyInventors: George William Cuff, Arvind Lavji Thakkar
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Patent number: 6703407Abstract: The present invention provides novel, reduced benzothiophenes of formula I wherein R is —H, —OH, —O(C1-C4 alkyl), —O—CO—(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, or —O—SO2—(C4-C6 alkyl); R1 is —H, —OH, —O(C1-C4 alkyl), —O—CO—(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, —O—SO2—(C4-C6 alkyl) chloro or bromo; n is 2 or 3; and R2 and R3 each are independently C1-C4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidino, dimethyl-1-pyrrolidino, 4-morpholino or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof. Further provided are methods for alleviating the symptoms of post-menopausal syndrome, and inhibiting endometriosis, uterine fibrosis, and aortal smooth muscle cell proliferation.Type: GrantFiled: September 20, 1994Date of Patent: March 9, 2004Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
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Patent number: 6653328Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel 3-benzyl-benzothiophenes which are &agr;-substituted with ether, thioether amino, cyano or halo that are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.Type: GrantFiled: March 10, 1995Date of Patent: November 25, 2003Assignee: Eli Lilly and CompanyInventor: Brian S. Muehl
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Patent number: 6599920Abstract: This invention relates to the field of pharmaceutical and organic chemistry and provides naphthalene compounds, intermediates, formulations, and methods.Type: GrantFiled: August 26, 1997Date of Patent: July 29, 2003Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones
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Patent number: 6593345Abstract: The instant invention provides novel substituted naphthyl compounds, intermediates, compositions, pharmaceutical formulations, and methods of use.Type: GrantFiled: August 27, 1997Date of Patent: July 15, 2003Assignee: Eli Lilly and CompanyInventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones, Alan David Palkowitz
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Patent number: 6509356Abstract: A class of substituted benzylnaphthylene compounds of the structure where R1 and R2 are independently hydrogen, alkyl of one to six carbon atoms, acyl of two to six carbon atoms, or phenacyl; X is —(CH2)1-6; Y is absent or is selected from 1,4-piperazinylene; ureido; N-(lower alkyl)ureido; N′-(lower alkyl)ureido; or N, N′-(di-lower alkyl ureido; and Z is 1-, 2- or 3-pyrrolidinyl; 1-, 2-, or 3-[1-(lower alkyl) pyrrolidinyl]; 1- 2-, 3- or 4-piperidinyl; 1-, 2-, 3- or 4-[1-lower alkyl)piperidinyl]; N,N-dialkyl; 1-azepinyl; 1- or 2-naphthylamino, 4-morpholinyl, dimethyl-4-morpholinyl, 3-azaspiro[5.Type: GrantFiled: August 4, 1998Date of Patent: January 21, 2003Assignee: Eli Lilly and CompanyInventors: Jeffrey Alan Dodge, Andrew Lawrence Glasebrook, Charles Willis Lugar, III
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Patent number: 6479517Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel phosphorous-containing benzothiophene compounds which are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.Type: GrantFiled: February 28, 1995Date of Patent: November 12, 2002Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge, Jeffrey S. Nissen
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Patent number: 6451817Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel 1-benzyl-naphthyls which are &agr;-substituted with ether, thioether, amino, hydrazino, cyano or halo that are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.Type: GrantFiled: September 29, 1995Date of Patent: September 17, 2002Assignee: Eli Lilly and CompanyInventor: Brian S. Muehl
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Patent number: 6444688Abstract: The instant invention provides compounds of formula I wherein R1 is OH, O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, or O—C(O)—O—Ar; R2 is H, OH, O(C1-C6 alkyl), O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, O—C(O)—O—Ar, O—SO2—(C4-C6 alkyl), chloro, fluoro, or bromo; V is S, O, or CH2CH2; W is CHOH, C(O), or CH2; X is (CH2)n; R3 and R4 each, independently, are H, C1-C6 alkyl, C(O)—(C1-C6 alkyl), C(O)—NH—(C1-C6 alkyl), C(O)—Ar, or together with the nitrogen to which they are attached form a 5- or 6-membered imide or cyclic amide; n is 1, 2, or 3; and Ar is optionally substituted phenyl; povided that at least one of R3 and R4 contains a carbonyl functional group, and their use in the treatment of estrogen deficiency pathologies.Type: GrantFiled: June 7, 1995Date of Patent: September 3, 2002Assignee: Eli Lilly and CompanyInventors: Jeffrey A. Dodge, Charles D. Jones, Kristin Marron, James P. Sluka, Mark G. Stocksdale
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Patent number: 6440958Abstract: This invention is directed to a class of acrylic and propionic acid compounds and their use in the treatment of post-menopausal symptoms and restenosis. In other embodiments, the invention is directed to intermediates and to processes for the preparation of the acrylic and propionic acid compounds.Type: GrantFiled: June 25, 1996Date of Patent: August 27, 2002Assignee: Eli Lilly and CompanyInventors: Charles David Jones, Alan David Palkowitz, Kenneth Jeff Thrasher
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Patent number: 6432982Abstract: The invention provides novel benzothiophenes of the formula: wherein R1 is —H, —OH, —O(C1-C4 alkyl), —O—CO(C1-C6 alkyl), —OSO2(C4-C6 alkyl, or —OCOAr where Ar is optionally substituted phenyl; R2 is —H, —OH, —Cl, —Br, —O(C1-C4 alkyl), —OCO(C1-C6 alkyl), —OSO2(C4-C6 alkyl, or —OCOAr where Ar is optionally substituted phenyl; R3 is —H, —F, —Cl, —(C1-C4 alkyl), —CN, or —O(C1-C3 alkyl); R4 is —H, —F, —Cl, —(C1-C4 alkyl), —CN or —O(C1-C3 alkyl); R5 is —H, —F, —Cl, —(C1-C4 alkyl), or —O(C1-C3 alkyl); and R6 is —H, —F, —Cl, —(C1-C4 alkyl), or —O(C1-C3 alkyl); with the provisos that R3, R4, R5 and R6 can not all be hydrogen, and that when one of R3, R4, R5 or R6 is C1-C4 alkyl, no more than two of R3, R4, R5 and R6 can be hydrogen; Y is —CO—, —CHOH—, or &mdaType: GrantFiled: January 14, 1997Date of Patent: August 13, 2002Assignee: Eli Lilly and CompanyInventors: George Joseph Cullinan, Kennan Joseph Fahey
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Patent number: 6432983Abstract: The instant invention provides compound of formula I wherein: R1 is —H, —OH, —O(C1-C4 alkyl), —O—CO—(C1-C6 alkyl), —O—CO—O(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, or —O—SO2—(C4-C6 alkyl); R2 is —H, —OH, —O(C1-C4 alkyl), —O—CO—(C1-C6 alkyl), —O—CO—O(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, —O—SO2—(C4-C6 alkyl), —F, —Cl, or —Br; n is an integer from 5 to 8; R3 and R4 each are independently C1-C4 alkyl, or combine to form, with the nitrogen to which they are attached, piperidinyl, pyrrolidinyl, methylpyrrolidinyl, dimethylpyrrolidinyl, or hexamethyleneimino; or a pharmaceutically acceptable salt or solvate thereof, intermediates, pharmaceutical formulations, processes, and methods of use.Type: GrantFiled: June 30, 1997Date of Patent: August 13, 2002Assignee: Eli Lilly and CompanyInventors: George Joseph Cullinan, Kennan Joseph Fahey
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Patent number: 6417199Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel 3-benzyl-benzothiophenes which are a-substituted with ether, thioether amino, hydrazino, cyano or halo that are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.Type: GrantFiled: September 29, 1995Date of Patent: July 9, 2002Assignee: Eli Lilly and CompanyInventor: Brian S. Muehl
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Patent number: 6407243Abstract: 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: GrantFiled: May 10, 1995Date of Patent: June 18, 2002Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
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Patent number: 6403614Abstract: This invention provides novel benzothiophene compounds of formula I: which are useful for the inhibition of the various medical conditions associated with postmenopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus, and cervix. The present invention further. relates to pharmaceutical formulations of compounds of formula I.Type: GrantFiled: September 30, 1998Date of Patent: June 11, 2002Assignee: Eli Lilly and CompanyInventors: Jeffrey Alan Dodge, Mark Gregory Stocksdale