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).
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Patent number: 5691353Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is H, OH, halo, OCO(C.sub.1 -C.sub.6 alkyl), OCO(aryl), OSO.sub.2 (C.sub.4 -C.sub.6 alkyl), OCOO(C.sub.1 -C.sub.6 alkyl), OCOO(aryl), OCONH (C.sub.1 -C.sub.6 alkyl), or OCON(C.sub.1 -C.sub.6 alkyl).sub.2 ;R.sub.2 is aryl, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or 4-cyclohexanol;R.sub.3 is O(CH.sub.2).sub.2 or O(CH.sub.2).sub.3 ;R.sub.4 and R.sub.5 are optionally CO(CH.sub.2).sub.3,CO(CH.sub.2).sub.4, C.sub.1 -C.sub.6 alkyl, or R.sub.4 and R.sub.5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrollidine, 3-methylpyrollidine, 3,3-dimethylpyrollidine, 3,4-dimethylpyrollidine, azepine, or pipecoline;R.sub.6 is>CH(C.sub.1 -C.sub.5 alkyl), >CH(C.sub.2 -C.sub.5 alkenyl), >C.dbd.CH(C.sub.1 -C.sub.5 alkyl), >CH(aryl), >C(OH)(C.sub.1 -C.sub.5 alkyl), >C(OH)(C.sub.2 -C.sub.5 alkenyl), C(OH)aryl;and phamaceutically acceptable salts thereof.Type: GrantFiled: December 5, 1995Date of Patent: November 25, 1997Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge
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Patent number: 5663184Abstract: A method of inhibiting one or more CNS disorders in a post-menopausal woman comprising administering to a female 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 pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.Type: GrantFiled: April 28, 1995Date of Patent: September 2, 1997Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Andrew L. Glasebrook, Timothy A. Grese, David L. Phillips
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Patent number: 5658931Abstract: The present invention provides a method of inhibiting hormone-dependent breast carcinoma in a mammal comprising administering to said mammal in need of treatment an effective amount of a first component which is 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, and an effective amount of a second component which is a compound of formula II ##STR2## wherein either R.sup.4 is H or a lower alkyl radical and R.sup.5 is a lower alkyl radical, or R.sup.4 and R.sup.Type: GrantFiled: September 20, 1994Date of Patent: August 19, 1997Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Robin S. L. Fuchs-Young
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Patent number: 5624940Abstract: The present invention provides aqueous inclusion complexes of certain known benzothiophene compounds, particularly Raloxifene, and water soluble cyclodextrins. Also provided are pharmaceutical compositions of such inclusion complexes, and methods of using these complexes for inhibiting bone loss and reducing serum cholesterol in mammals.Type: GrantFiled: June 30, 1995Date of Patent: April 29, 1997Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, George J. Cullinan, Paul C. Francis, David E. Magee, Stephanie A. Sweetana, Arvind L. Thakkar
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Patent number: 5605885Abstract: The present invention includes methods and compositions for affecting the immune system in animals and humans. The methods and compositions include the administration of prolactin agonists to an immunosuppressed animal or human thereby stimulating the immune system. In addition, the present invention includes a vaccine adjuvant comprising the administration of a prolactin agonist with the vaccine.Type: GrantFiled: September 29, 1994Date of Patent: February 25, 1997Assignee: EntreMed, Inc.Inventors: Edward W. Bernton, John W. Holaday, Henry U. Bryant
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Patent number: 5605924Abstract: The present invention relates to compounds of the formula ##STR1## where X is a bond or --CH2--;R.sup.2 is pyrrolidino;R is OH, --OSO.sub.2 --(CH.sub.2).sub.n --CH.sub.3 or ##STR2## R.sup.1 is hydrogen, OH, fluoro, chloro, --OSO.sub.2 --(CH.sub.2).sub.n --CH.sub.3 or ##STR3## each R.sup.3 is independently C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl where the substituent is fluoro, chloro, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy;each n is independently 3, 4 or 5; and pharmaceutically acceptable salts and solvates thereof; provided that at least one of R and R.sup.1 is ##STR4## The invention also relates to methods of use of the compounds of formula I and pharmaceutical compositions which comprise compounds of formula I.Type: GrantFiled: January 17, 1996Date of Patent: February 25, 1997Assignee: Eli Lilly and CompanyInventors: Larry J. Black, Henry U. Bryant, George J. Cullinan
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Patent number: 5604248Abstract: The present invention provides a method of minimizing the uterotrophic effect of non-steroidal antiestrogen compounds of formula II ##STR1## wherein either R.sup.4 is H or a lower alkyl radical and R.sup.5 is a lower alkyl radical, or R.sup.4 and R.sup.5 are joined together with the adjacent nitrogen atom to form a heterocyclic radical;R.sup.6 is H or a lower alkyl radical;R.sup.7 is H, halo, OH, a lower alkyl radical, or is a buta-1,3-dienyl radical which together with the adjacent benzene ring forms a naphthyl radical;R.sup.8 is H or OH; andn is 2;or a pharmaceutically acceptable salt thereof wherein said formula II compound is administered to a woman for the treatment or prevention of breast carcinoma.Type: GrantFiled: May 5, 1994Date of Patent: February 18, 1997Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Robin S. Fuchs-Young
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Patent number: 5599833Abstract: The present invention relates to sulfonate and carbamate 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: GrantFiled: January 17, 1996Date of Patent: February 4, 1997Assignee: Eli Lilly and CompanyInventors: Larry J. Black, Henry U. Bryant, George J. Cullinan
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Patent number: 5578614Abstract: A method of inhibiting weight gain or inducing or facilitating weight loss comprising administering to a human 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: GrantFiled: March 15, 1995Date of Patent: November 26, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge
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Patent number: 5578613Abstract: A method of inhibiting weight gain or inducing or facilitating weight loss comprising administering to a human 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: GrantFiled: December 21, 1993Date of Patent: November 26, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge
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Patent number: 5556876Abstract: 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, C.sub.1 -C.sub.6 alkyl optionally substituted with amino, halo, carbonyl, C.sub.1 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.7 alkanoyloxy, carbamoyl and/or aryl; or R.sup.a is C.sub.1 -C.sub.6 alkenyl optionally substituted with aryl; or R.sup.a is a C.sub.3 -C.sub.7 cycloalkyl; or R.sup.a is aryl optionally substituted with hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, and/or halo; or R.sup.a is --O-aryl;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: GrantFiled: August 15, 1995Date of Patent: September 17, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Timothy A. Grese
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Patent number: 5554628Abstract: The present invention provides a method of minimizing the uterotrophic effect of non-steroidal antiestrogen compounds of formula II ##STR1## and wherein the variables are as defined in the specification and wherein said formula II compound is administered to a woman for the treatment or prevention of breast carcinoma, comprising concurrently or sequentially administering to said woman a compound of formula I ##STR2## wherein the variables are as defined in the specification.Type: GrantFiled: September 20, 1994Date of Patent: September 10, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Steven A. Fontana
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Patent number: 5552433Abstract: A method of lowering serum cholesterol levels is disclosed comprising administering to a human in need of treatment an effective amount of a compound having the formula ##STR1## wherein R is 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 amino, or a pharmaceutically acceptable salt or solvate thereof.Type: GrantFiled: August 15, 1995Date of Patent: September 3, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Timothy A. Grese
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Patent number: 5545635Abstract: The present invention provides methods of inhibiting bone loss in humans comprising administering to a patient in need of treatment an effective amount of d-equilenin, 17.beta.-dihydroequilenin, and 17.alpha.-dihydroequilenin, and pharmaceutical formulations thereof.Type: GrantFiled: May 23, 1995Date of Patent: August 13, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge, Masahiko Sato, Na N. Yang
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Patent number: 5523309Abstract: The present invention provides a compound of formula I ##STR1## wherein R.sub.1 is H, OH, halo, OCO(C.sub.1 -C.sub.6 alkyl), OCO(aryl), OSO.sub.2 (C.sub.4 -C.sub.6 alkyl), OCOO(C.sub.1 -C.sub.6 alkyl), OCOO(aryl), OCONH(C.sub.1 -C.sub.6 alkyl), or OCON(C.sub.1 -C.sub.6 alkyl).sub.2 ;R.sub.2 is aryl, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, or 4-cyclohexanol;R.sub.3 is O(CH.sub.2).sub.2 or O(CH.sub.2).sub.3 ;R.sub.4 and R.sub.5 are optionally CO(CH.sub.2).sub.2 CH.sub.3, CO(CH.sub.2).sub.3 CH.sub.3 C.sub.1 -C.sub.6 alkyl, or R.sub.4 and R.sub.5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrrolidine, 3-methylpyrrolidine, 3,3-dimethylpyrrolidine, 3,4-dimethylpyrrolidine, azepine, or pipecoline;R.sub.6 is >CH(C.sub.1 -C.sub.5 alkyl), >CH(C.sub.2 -C.sub.5 alkenyl), >C.dbd.CH(C.sub.1 -C.sub.5 alkyl) >CH(aryl), >C(OH)(C.sub.1 -C.sub.5 alkyl), >C(OH)(C.sub.2 -C.sub.5 alkenyl), >C(OH)aryl;and pharmaceutically acceptable salts thereof.Type: GrantFiled: March 10, 1995Date of Patent: June 4, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge
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Patent number: 5521172Abstract: 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: GrantFiled: August 15, 1995Date of Patent: May 28, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Timothy A. Grese
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Patent number: 5521214Abstract: 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: GrantFiled: January 25, 1995Date of Patent: May 28, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, Jeffrey A. Dodge
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Patent number: 5492921Abstract: 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 -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 aortal smooth muscle proliferation.Type: GrantFiled: April 19, 1995Date of Patent: February 20, 1996Assignee: 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: 5484797Abstract: 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 endometriosis.Type: GrantFiled: April 21, 1995Date of Patent: January 16, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl
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Patent number: 5484795Abstract: 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 treating restenosis.Type: GrantFiled: April 21, 1995Date of Patent: January 16, 1996Assignee: Eli Lilly and CompanyInventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones, Charles W. Lugar, Brian S. Muehl