Patents by Inventor Robert T Shuman
Robert T Shuman 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: 6303610Abstract: This invention relates to a method of treating gout with certain indole compounds and other aromatic compounds.Type: GrantFiled: March 6, 2000Date of Patent: October 16, 2001Assignee: Eli Lilly and CompanyInventors: Douglas W Johnson, John M Morin, Jr., Jason S Sawyer, Robert T Shuman
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Patent number: 5726159Abstract: This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH.sub.2).sub.r --G Iwhere X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.Type: GrantFiled: September 1, 1995Date of Patent: March 10, 1998Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Robert T. Shuman, Gerald F. Smith, Michael R. Wiley
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Patent number: 5646242Abstract: The present invention relates to the acylation of proteins. More particularly, the invention relates to a one-step process for selectively acylating the free .epsilon.-amino group of insulin, insulin analog, or proinsulin in the presence of a free .alpha.-amino group.Type: GrantFiled: November 17, 1994Date of Patent: July 8, 1997Assignee: Eli Lilly and CompanyInventors: Jeffrey C. Baker, Victor J. Chen, Jose M. Hanquier, Aidas Kriauciunas, Brian A. Moser, Robert T. Shuman
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Patent number: 5602101Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: October 5, 1994Date of Patent: February 11, 1997Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Robert T. Shuman, Gerald F. Smith, James H. Wikel, Michael R. Wiley
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Patent number: 5578574Abstract: This invention relates to L-arginine aldehyde derivatives, having the formula I ##STR1## where X and Y have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.Type: GrantFiled: March 2, 1995Date of Patent: November 26, 1996Assignee: Eli Lilly and CompanyInventors: Robert T. Shuman, Robert B. Rothenberger, Kenneth D. Kurz, Daniel J. Sall, Gerald F. Smith, Michael R. Wiley
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Patent number: 5488037Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: March 4, 1994Date of Patent: January 30, 1996Assignee: Eli Lilly and CompanyInventors: Daniel J. Sall, Robert T. Shuman
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Patent number: 5484772Abstract: This invention relates to L-arginine aldehyde derivatives, pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: October 5, 1994Date of Patent: January 16, 1996Assignee: Eli Lilly and CompanyInventors: Daniel J. Sall, Robert T. Shuman, Gerald F. Smith, Michael R. Wiley
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Patent number: 5455229Abstract: The present invention is a method for minimizing and containing injury caused when tissue is subject to ischemia and reperfusion. The method comprises administering certain derivatized tripeptide arginal compounds concurent with, or immediately after, reestablishing blood flow to the ischemic tissue. The method is particularly useful for minimizing and containing damage to the heart during evolving myocardial infarction.Type: GrantFiled: December 23, 1992Date of Patent: October 3, 1995Assignee: Eli Lilly and CompanyInventors: Richard A. Hahn, Brian R. MacDonald, Robert T. Shuman, Gerald F. Smith
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Patent number: 5439888Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compound and methods of their use as thrombin inhibitors.Type: GrantFiled: March 4, 1994Date of Patent: August 8, 1995Assignee: Eli Lilly and CompanyInventors: Robert T. Shuman, Gerald F. Smith
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Patent number: 5436229Abstract: This invention relates to bisulfite adducts of L-Arginine aldehyde derivatives, pharmaceutical formulations containing those adducts and methods of their use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents.Type: GrantFiled: March 4, 1994Date of Patent: July 25, 1995Assignee: Eli Lilly and CompanyInventors: Kenneth J. Ruterbories, Robert T. Shuman
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Patent number: 5430023Abstract: Thrombin inhibitors represented by the formula ##STR1## as provided wherein A(C.dbd.O)-- is, inter alia, phenylglycyl, cyclohexylglycyl, cyclohexenylglycyl, thienylglycyl or naphthylglycyl, wherein the .alpha.-amino group is preferably substituted by alkyl e.g. methyl or an alkoxycarbonyl, cycloalkoxycarbonyl or arylkoxycarbonyl group e.g. t-butyloxycarbonyl. A(C.dbd.O)-- also represents an .alpha.-substituted acetyl group such as .alpha.-methoxyphenylacetyl; or a bicyclic group such as a tetrahydroisoquinolin-1- or 3-carbonyl group; a perhydroisoquinolin -1- or -3-carbonyl group; or a 1-amino or (substituted amino) cycloalkylcarbonyl group such as 1-aminocyclohexylcarbonyl. Also provided are a method for inhibiting the formation of blood clots in man and animals by administering a thrombin inhibitor of the above formula and pharmaceutical formulations useful in the method.Type: GrantFiled: September 14, 1993Date of Patent: July 4, 1995Assignee: Eli Lilly and CompanyInventors: Paul D. Gesellchen, Robert T. Shuman
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Patent number: 5416093Abstract: Thrombin inhibitors represented by the formula ##STR1## as provided wherein A is e.g. phenylglycyl, and phenylalanyl, .alpha.-methylphenylalanine and .alpha.-methylphenylglycine wherein the amino group is preferably substituted with lower alkyl alkanoyl or lower alkoxycarbonyl, or a bicyclo group e.g. 1,2,3,4-tetrahydroisoquinolin-1-yl or -3-yl and perhydroisoquinolin-1-yl or -3-yl. Also provided are a method for inhibiting clot formation in man and animals, pharmaceutical formulations useful in the method and intermediates for the inhibitors.Type: GrantFiled: August 13, 1993Date of Patent: May 16, 1995Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: 5252566Abstract: Thrombin inhibitors represented by the formula ##STR1## as provided wherein A is e.g. phenylglycyl, and phenylalanyl, .alpha.-methylphenylalanine and .alpha.-methylphenylglycine wherein the amino group is preferably substituted with lower alkyl alkanoyl or lower alkoxycarbonyl, or a bicyclo group e.g. 1,2,3,4-tetrahydroisoquinolin-1-yl. Also provided are a method for inhibiting clot formation in man and animals, pharmaceutical formulations useful in the method and intermediates for the inhibitors.Type: GrantFiled: October 16, 1992Date of Patent: October 12, 1993Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: 5250660Abstract: Tripeptides, D-Phe-L-Pro-L-Arg-H, D-Phg-L-Pro-L-Arg-H and related compounds are purified in a process comprising 1) HPLC chromatography over an alkylsilane resin and elution with a gradient comprising an organic phase of between about 2% and about 40% of acetonitrile in an aqueous acidic phase containing an inorganic acid e.g. H.sub.2 SO.sub.4 and HCl, at a pH between about 2 and about 3, and 2) adjusting the pH of the acidic eluate with a water insoluble basic ion-exchange resin to about 4 to about 6.5. The purified peptides are useful antithrombotic agents.Type: GrantFiled: November 12, 1991Date of Patent: October 5, 1993Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: 4510082Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in whichR is hydrogen, methyl, ethyl, cyclopropylmethyl, or allyl;A is a residue of a D-amino acid selected from the goup consisting of Ala, Abu, Nva, Val, Nle, Leu, Ile, Gly(Al), Gly(Cp) Met, Cys(Me), Met(O), Cys(Me) (O), Ser, Ser(Me), Thr, and Hse;R.sub.1 is hydrogen, C.sub.1 -C.sub.3 primary alkyl, cyclopropylmethyl, allyl, ethylthiomethyl, 2-fluoroethyl, or propargyl; andX is hydrogen, fluoro, bromo, iodo, chloro, hydroxy, C.sub.1 -C.sub.3 alkyl, trifluoromethyl, or C.sub.1 -C.sub.2 alkoxy; are useful analgesic agents.Type: GrantFiled: March 7, 1983Date of Patent: April 9, 1985Assignee: Eli Lilly and CompanyInventors: Paul D. Gesellchen, Robert T. Shuman
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Patent number: 4473497Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in whichR is hydrogen, methyl, ethyl, cyclopropylmethyl, or allyl;A is a residue of a D-amino acid selected from the group consisting of Ala, Abu, Nva, Val, Nle, Leu, Ile, Gly(Al), Gly(Cp), Met, Cys(Me), Met(O), Cys(Me)(O), Ser, Ser(Me), Thr, and Hse;R.sub.1 is hydrogen, C.sub.1 -C.sub.3 primary alkyl, cyclopropylmethyl, allyl, ethylthiomethyl, 2-fluoroethyl, or propargyl; andX is hydrogen, fluoro, bromo, iodo, chloro, hydroxy, C.sub.1 -C.sub.3 alkyl, trifluoromethyl, or C.sub.1 -C.sub.2 alkoxy; are useful analgesic agents.Type: GrantFiled: March 7, 1983Date of Patent: September 25, 1984Assignee: Eli Lilly and CompanyInventors: Paul D. Gesellchen, Robert T. Shuman
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Patent number: 4448717Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in whichR is hydrogen, methyl, ethyl, cyclopropylmethyl, or allyl;A is a residue of a D-amino acid selected from the group consisting of Ala, Abu, Nva, Val, Nle, Leu, Ile, Gly(Al), Gly(Cp), Met, Cys(Me), Met(O), Cys(Me) (O), Ser, Ser(Me), Thr, and Hse;R.sub.1 is hydrogen, C.sub.1 -C.sub.3 primary alkyl, cyclopropylmethyl, allyl, ethylthiomethyl, 2-fluoroethyl, or propargyl;X is fluoro, bromo, iodo, chloro, hydroxy, C.sub.1 -C.sub.3 alkyl, trifluoromethyl, or C.sub.1 -C.sub.2 alkoxy; andZ is methyl or ethyl; are useful analgesic agents.Type: GrantFiled: November 12, 1982Date of Patent: May 15, 1984Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: 4351763Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in whichL and D define the chirality;R.sub.1 is hydrogen or C.sub.1 -C.sub.3 primary alkyl;R.sub.2 is C.sub.1 -C.sub.4 primary or secondary alkyl, allyl, cyclopropylmethyl, C.sub.1 -C.sub.2 hydroxyalkyl, or --(CH.sub.2).sub.m -U-CH.sub.3 in which U is --S-- or ##STR2## and m is 1 or 2; R.sub.3 is hydrogen, C.sub.1 -C.sub.4 primary or secondary alkyl, cyclopropylmethyl, or allyl;R.sub.4 is hydrogen, C.sub.1 -C.sub.5 primary or secondary alkyl, --(CH.sub.2).sub.n --X--(CH.sub.2).sub.p --CH.sub.3 in which X is --O--, --S--, ##STR3## n is 1 or 2, and p is 0 or 1, phenyl, or monosubstituted phenyl in which the substituent is halo, hydroxy, C.sub.1 -C.sub.3 alkoxy, nitro, C.sub.1 -C.sub.3 alkyl, or trifluoromethyl;R.sub.5 is hydrogen or C.sub.1 -C.sub.4 primary alkyl; andZ is --CH.sub.2 OR.sub.6, ##STR4## in which R.sub.6 is hydrogen or C.sub.1 -C.sub.3 alkyl and R.sub.7 is C.sub.1 -C.sub.Type: GrantFiled: April 24, 1981Date of Patent: September 28, 1982Assignee: Eli Lilly and CompanyInventors: Paul D. Gesellchen, Robert T. Shuman
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Patent number: 4333873Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, in which L and D define the chirality;R.sub.1 is hydrogen or C.sub.1 -C.sub.3 primary alkyl;R.sub.2 is C.sub.1 -C.sub.4 primary or secondary alkyl, allyl, cyclopropylmethyl, C.sub.1 -C.sub.2 hydroxyalkyl, or --(CH.sub.2).sub.m --U--CH.sub.3 in which U is --S-- or >S--O and m is 1 or 2,R.sub.3 is cyclopropylmethyl or allyl; and ##STR2## in which R.sub.4 is hydrogen, acetyl, or acetoxymethyl and R.sub.5 is C.sub.1 -C.sub.3 alkyl; are useful analgesic agents.Type: GrantFiled: April 24, 1981Date of Patent: June 8, 1982Assignee: Eli Lilly and CompanyInventor: Robert T. Shuman
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Patent number: RE37971Abstract: The present invention relates to the acylation of proteins. More particularly, the invention relates to a one-step process for selectively acylating the free &egr;-amino group of insulin, insulin analog, or proinsulin in the presence of a free &agr;-amino group.Type: GrantFiled: July 8, 1999Date of Patent: January 28, 2003Assignee: Eli Lilly and CompanyInventors: Jeffrey C. Baker, Victor J. Chen, Jose M. Hanquier, Aidas Kriauciunas, Brian A. Moser, Robert T. Shuman