Patents by Inventor Henry U. Bryant

Henry U. Bryant 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).

  • Patent number: 5484798
    Abstract: The present invention provides novel benzothiophene compounds of formula I ##STR1## wherein R is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, or --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl);R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl) chloro or bromo;R.sup.2 is --H or --OH;n is 2 or 3; andR.sup.3 and R.sup.4 each are independently C.sub.1 14 C.sub.4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, or 1-hexamethyleneimino;or a pharmaceutically acceptable salt thereof, for inhibiting restenosis.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: January 16, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
  • Patent number: 5484796
    Abstract: The present invention provides a compound 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.4 -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) or --OSO.sub.2 (C.sub.4 -C.sub.6 alkyl);n is 2 or 3; andR.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof, for inhibiting aortal smooth muscle cell proliferation.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: January 16, 1996
    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
  • Patent number: 5482949
    Abstract: The present invention relates to sulfonate derivatives of 3-aroylbenzo[b]thiophenes, pharmaceutical formulations containing these compounds and methods of using such compounds for inhibiting the loss of bone, lowering serum cholesterol levels and therapeutically treating hormone dependent mammalian breast and uterine carcinoma.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: January 9, 1996
    Assignee: Eli Lilly and Company
    Inventors: Larry J. Black, Henry U. Bryant, George J. Cullinan
  • Patent number: 5482950
    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 hydrogen; hydroxy; C.sub.1 -C.sub.6 alkoxy; a group of the formula --O--C(O)--R.sup.a, wherein R.sup.a is hydrogen, optionally substituted C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl optionally substituted with aryl, C.sub.3 -C.sub.7 cycloalkyl, optionally substituted aryl or R.sup.a is optionally substituted --O--aryl,or R is a group of the formula --O--SO.sub.2 --R.sup.b wherein R.sup.b may be C.sub.1 -C.sub.6 alkyl or optionally substituted aryl;or R is carbamoyloxy wherein the nitrogen may be substituted once or twice with C.sub.1 -C.sub.6 alkyl;or R is a group of the formula --O--C(O)R.sup.c --O--(C.sub.1 -C.sub.6 alkyl) wherein R.sup.c is a bond or C.sub.1 -C.sub.6 alkanediyl;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.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: January 9, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Patent number: 5482958
    Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, orcombine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: April 10, 1995
    Date of Patent: January 9, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5480904
    Abstract: A method of inhibiting uterine fibrosis comprising administering to a human in need of treatment an effective amount of a benzothiophene compound.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: January 2, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Patent number: 5472977
    Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: April 10, 1995
    Date of Patent: December 5, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5464845
    Abstract: A method of lowering serum cholesterol levels comprising administering to a patient a serum cholesterol lowering amount of a compound having the formula ##STR1## wherein n is 0, 1 or 2;R is hydroxyl, methoxy, C.sub.1 -C.sub.7 alkanoyloxy, C.sub.3 -C.sub.7 cycloalkanoyloxy, (C.sub.1 -C.sub.6 alkoxy)-C.sub.1 -C.sub.7 alkanoyloxy, substituted or unsubstituted aroyloxy, or substituted or unsubstituted aryloxycarbonyloxy;R.sup.1 is hydrogen, hydroxyl, chloro, bromo, methoxy, C.sub.1 -C.sub.7 alkanoyloxy, C.sub.3 -C.sub.7 cycloalkanoyloxy, (C.sub.1 -C.sub.6 alkoxy)-C.sub.1 -C.sub.7 alkanoyloxy, substituted or unsubstituted aroyloxy, or substituted or unsubstituted aryloxycarbonyloxy;R.sup.2 is a heterocyclic ring selected from the group consisting of pyrrolidino, piperidino, or hexamethyleneimino; or a pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: November 7, 1995
    Assignee: Eli Lilly and Company
    Inventors: Larry J. Black, Henry U. Bryant, George J. Cullinan, Raymond F. Kauffman
  • Patent number: 5453442
    Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: September 26, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5446061
    Abstract: A method of lowering serum cholesterol levels, comprising administering an effective amount of a compound having the formula ##STR1## wherein: R.sup.1 and R.sup.2 are, independently, --H, --OH, halo, --OC.sub.1 -C.sub.17 alkyl, --OC.sub.3 -C.sub.6 cycloalkyl, --O(CO)C.sub.1 -C.sub.17 alkyl, --O(CO) aryl, --O(CO)O aryl, or --OSO.sub.2 -(n-butyl or n-pentyl);R.sup.3 is ##STR2## and R.sup.4 is --H, methyl, ethyl, propyl, ethenyl or ethynyl; or a pharmaceutically acceptable salt or solvate thereof, to an animal in need of lower cholesterol levels.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: August 29, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Patent number: 5441964
    Abstract: A method of inhibiting bone loss comprising administering to a human in need of treatment an effective amount of a substituted benzothiophene.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: August 15, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Patent number: 5416090
    Abstract: The present invention relates to the use of certain ergoline analogues and BCD tricyclic ergoline part-structure analogues as defined herein as anti-inflammatory agents.
    Type: Grant
    Filed: December 8, 1992
    Date of Patent: May 16, 1995
    Assignee: Eli Lilly and Company
    Inventors: Alison M. Bendele, Henry U. Bryant, John M. Schaus
  • Patent number: 5407955
    Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 allkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: April 18, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Jeffrey A. Dodge
  • Patent number: 5407947
    Abstract: A method of inhibiting bone loss comprising administering to an animal an effective amount of a compound having the formula ##STR1## wherein: R.sup.1 and R.sup.2 are, independently, --H, --OH, halo, --OC.sub.1 -C.sub.17 alkyl, --OC.sub.3 -C.sub.6 cycloalkyl, --O(CO)C.sub.1 -C.sub.17 alkyl, --O(CO) aryl, --O(CO)O aryl, or --OSO.sub.2 -(n-butyl or n-pentyl);R.sup.3 is ##STR2## R.sup.4 is --H, methyl, ethyl, propyl, ethenyl or ethynyl; or a pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: April 18, 1995
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, Timothy A. Grese
  • Patent number: 5063234
    Abstract: A method of inhibiting bone demineralization comprising administration of an effective amount of a compound having the formula ##STR1## where X is CH or N;Y is O or S;R.sup.1 is 2-propenyl, C.sub.1 -C.sub.3 alkyl, benzyl or substituted benzyl where the substitutents are one or two of the same or different and are selected from methyl, ethyl, methoxy, ethoxy, hydroxy, chloro, bromo, or fluoro;R.sup.2 is C.sub.2 -C.sub.3 alkyl, allyl or cyclopropylmethyl;R.sup.3 and R.sup.4 are both hydrogen or combine to form a carbon-carbon bond; and pharmaceutically acceptable acid addition salts thereof to a mammal requiring bone demineralization inhibition.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: November 5, 1991
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, James A. Clemens