Patents Represented by Attorney, Agent or Law Firm James J. Sales
  • Process for preparing 3-(4-aminoethoxy-benzoyl) benzo (B)-thiophenes
    Patent number: 5523416
    Abstract: The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo[B]thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)benzoyl]benzo[B]thiophen es via acylation of a dialkoxy benzo[B]thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo[B]thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: June 4, 1996
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Alt
  • Methods and compounds for the preparation of carbacephems
    Patent number: 5521307
    Abstract: A chiral process for preparing compounds of the formula: ##STR1## from a compound of the formula: ##STR2## in which the compound formula (IV) is reacted with trimethylsilyl iodide to remove the chiral auxiliary at the 7-position and the carboxy protecting group. The process allows for the retention of the amino and carboxy protecting groups throughout the preparation of Compound IV. Also disclosed are novel intermediates.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 28, 1996
    Assignee: Eli Lilly and Company
    Inventors: Jack W. Fisher, Lowell D. Hatfield, Richard C. Hoying, James E. Ray
  • Methods for lowering serum cholesterol
    Patent number: 5521172
    Abstract: A method of lowering serum cholesterol levels comprising administering to a human in need of treatment an effective amount of a compound having the formula ##STR1## wherein R is as herein defined;R.sup.1 is halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.7 alkyl substituted with C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 cycloalkyl, or substituted or unsubstituted C.sub.3 -C.sub.7 cycloalkenyl;R.sup.2 is O or CH.sub.2 ;R.sup.3 is CH.sub.2 or (CH.sub.2).sub.2 ;R.sup.4 is ##STR2## CH.sub.2, or a bond; and R.sup.5 is an N-heterocyclic ring, other than pyrrolidin or piperidino, which optionally has another hetero atom selected from N, O, or S in said ring; or a pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: August 15, 1995
    Date of Patent: May 28, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Methods of inhibiting environmental estrogens
    Patent number: 5521214
    Abstract: A method of inhibiting effects of environmental estrogens comprising administering to a human or other animal in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, -CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: May 28, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Methods of inhibiting autoimmune diseases
    Patent number: 5521198
    Abstract: A method of inhibiting autoimmune diseases comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: December 21, 1993
    Date of Patent: May 28, 1996
    Assignee: Eli Lilly and Company
    Inventor: Steven H. Zuckerman
  • Benzothiophene compounds useful for inhibiting lipoxygenase
    Patent number: 5514703
    Abstract: A method of inhibiting 5-lipoxygenase comprising administering to a mammal in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.3 is hydrogen, or a group of the formula ##STR2## wherein R.sub.4 phenyl, substituted phenyl, naphthyl or substituted naphthyl, with the proviso that when R.sub.1 and R.sub.2 are both C.sub.1 -C.sub.6 alkyl, R.sub.3 is not hydrogen; and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: May 7, 1996
    Assignee: Eli Lilly and Company
    Inventors: Donald G. Carlson, George J. Cullinan, Kennan J. Fahey, William T. Jackson, Neal W. Roehm, Stephen M. Spaethe
  • Benzothiophenes to inhibit leukotrienes
    Patent number: 5514704
    Abstract: A method of inhibiting leukotrienes comprising administering to a mammal in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.3 is hydrogen, or a group of the formula ##STR2## wherein R.sub.4 is phenyl, substituted phenyl, naphthyl or substituted naphthyl, with the proviso that when R.sub.1 and R.sub.2 are both C.sub.1 -C.sub.6 alkyl, R.sub.3 is not hydrogen; and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 13, 1995
    Date of Patent: May 7, 1996
    Assignee: Eli Lilly and Company
    Inventors: Donald G. Carlson, George J. Cullinan, Kennan J. Fahey, William T. Jackson, Neal W. Roehm, Stephen M. Spaethe
  • Process for preparing 3-(4-aminoethoxy-benzoyl) benzo B!-thiophenes
    Patent number: 5512684
    Abstract: The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo B!thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3- 4-(2-aminoethoxy)benzoyl!benzo B!thiophen es via acylation of a dialkoxy benzo B!thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo B!thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: April 30, 1996
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Alt
  • Methods of decreasing serum calcium levels
    Patent number: 5512583
    Abstract: A method of lowering serum calcium levels comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.l and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: April 30, 1996
    Assignee: Eli Lilly and Company
    Inventors: Susan M. Boss, Willard H. Dere
  • Methods for inhibiting neuronal damage
    Patent number: 5512296
    Abstract: A method for inhibiting neuronal damage due to hypoglycemia comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: April 30, 1996
    Assignee: Eli Lilly and Company
    Inventor: George J. Cullinan
  • Parathyroid hormone and raloxifene for increasing bone mass
    Patent number: 5510370
    Abstract: The present invention includes a method for increasing bone mass in a subject by administration of PTH and raloxifene. Another aspect of the invention is a method for treating bone loss in a subject by administration of PTH and raloxifene. The invention further provides for a composition of PTH and raloxifene for increasing bone mass in a subject. Another aspect of the invention is a composition of PTH and raloxifene for treatment of bone loss in a subject.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Janet M. Hock
  • Benzothiophene compounds as anti-estrogenic agents
    Patent number: 5510357
    Abstract: The present invention provides pharmaceutically active compounds of formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO (C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl), or halo, providing when Z is --S--, R.sup.2 is not halo;R.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino;n is 2 or 3; andz is --O-- or --S--;or a pharmaceutically acceptable salt thereof for, inter alia, alleviating the symptoms of post menopausal syndrome and hormonally-dependent cancer, particularly breast cancer.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Methods of inhibiting thrombin
    Patent number: 5508292
    Abstract: A method of inhibiting thrombin and its attending diseases and conditions comprising administering to a human in need of treatment an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidino, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: April 16, 1996
    Assignee: Eli Lilly and Company
    Inventors: Daniel J. Sall, Gerald F. Smith
  • Use of bengothiophenls to treat pain due to an excess of neuropeptide y
    Patent number: 5504094
    Abstract: A method of inhibiting a physiological disorder associated with an excess of neuropeptide Y or its symptoms comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: August 21, 1995
    Date of Patent: April 2, 1996
    Assignee: Eli Lilly and Company
    Inventors: Robert F. Bruns, Jr., Donald R. Gehlert, J. Jeffry Howbert, William H. W. Lunn
  • Benzothiophenes for bone healing and fracture repair
    Patent number: 5502074
    Abstract: A method of facilitating bone healing and fracture repair comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: March 26, 1996
    Assignee: Eli Lilly and Company
    Inventors: George J. Cullinan, Masahiko Sato
  • Methods of inhibiting ulcerative mucositis
    Patent number: 5496828
    Abstract: A method of inhibiting ulcerative mucositis comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: March 5, 1996
    Assignee: Eli Lilly and Company
    Inventor: George J. Cullinan
  • Methods of inhibiting cell-cell adhesion
    Patent number: 5496851
    Abstract: A method of inhibiting cell-cell adhesion comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: March 5, 1996
    Assignee: Eli Lilly and Company
    Inventor: Brian W. Grinnell
  • Methods of inhibiting viral replication
    Patent number: 5494920
    Abstract: A method of inhibiting viral replication comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: February 27, 1996
    Assignee: Eli Lilly and Company
    Inventors: Andrew L. Glasebrook, David L. Phillips
  • Methods of inhibiting growth hormone effects
    Patent number: 5494929
    Abstract: A method of inhibiting effects of growth hormone comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically accepatable salt of solvate thereof.
    Type: Grant
    Filed: January 12, 1995
    Date of Patent: February 27, 1996
    Assignee: Eli Lilly and Company
    Inventor: Timothy A. Grese
  • Methods for inhibiting vascular smooth muscle cell proliferation and restinosis
    Patent number: 5492926
    Abstract: Methods of inhibiting vascular smooth muscle cell proliferation and vascular restinosis comprising administering to a human or other mammal in need of treatment an effective amount of a compound having the formula ##STR1## wherein R.sub.1 and R.sub.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sub.2 is ##STR3## R.sub.4 is hydrogen or --OR.sub.1, and pharmaceutically acceptable salts and solvates thereof.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: February 20, 1996
    Assignee: Eli Lilly and Company
    Inventors: George J. Cullinan, Jai P. Singh, Dan L. Wood