Patents Represented by Attorney William C. Martens, Jr.
  • Patent number: 4323707
    Abstract: Derivatives of 3-phenyl-4-aroyl-1,2-dihydronaphthalenes and 1-aroyl-2-phenylnaphthalenes are useful as antifertility agents.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: April 6, 1982
    Assignee: Eli Lilly and Company
    Inventors: Tulio Suarez, C. David Jones
  • Patent number: 4322340
    Abstract: 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, Thr, and Hse;R.sub.1 is C.sub.1 -C.sub.3 primary alkyl, cyclopropylmethyl, allyl, ethylthiomethyl, 2-fluoroethyl, or propargyl;X is bromo, iodo, chloro, methyl, trifluoromethyl, or methoxy; andZ is --CH.sub.2 OR.sub.2, ##STR2## in which R.sub.2 is hydrogen, acetyl, or acetoxymethyl and R.sub.3 is C.sub.1 -C.sub.3 alkyl; are useful analgesic agents.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: March 30, 1982
    Assignee: Eli Lilly and Company
    Inventors: Robert T. Shuman, Paul D. Gesellchen
  • Patent number: 4283330
    Abstract: 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; andZ is --CH.sub.2 OR.sub.4, ##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: Grant
    Filed: December 17, 1979
    Date of Patent: August 11, 1981
    Assignee: Eli Lilly and Company
    Inventor: Robert T. Shuman
  • Patent number: 4283329
    Abstract: 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 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--, >S--O or ##STR2## 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, ##STR3## 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: Grant
    Filed: December 17, 1979
    Date of Patent: August 11, 1981
    Assignee: Eli Lilly and Company
    Inventors: Paul D. Gesellchen, Robert T. Shuman
  • Patent number: 4265808
    Abstract: 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 hydrogen, C.sub.1 -C.sub.4 primary or secondary alkyl, cyclopropylmethyl, allyl or propargyl; andZ is --CH.sub.2 OR.sub.4, ##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: Grant
    Filed: December 17, 1979
    Date of Patent: May 5, 1981
    Assignee: Eli Lilly and Company
    Inventors: Paul D. Gesellchen, Robert T. Shuman
  • Patent number: 4251439
    Abstract: Compound 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 hydrogen, C.sub.1 --C.sub.4 primary or secondary alkyl, cyclopropylmethyl, or allyl;X is hydrogen, halo, hydroxy, C.sub.1 --C.sub.3 alkoxy, nitro, C.sub.1 --C.sub.3 alkyl, or trifluoromethyl; andZ is --CH.sub.2 OR.sub.4, ##STR2## in which R.sub.4 is hydrogen or C.sub.1 --C.sub.3 alkyl and R.sub.5 is C.sub.1 --C.sub.3 alkyl; are useful analgesic agents.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: February 17, 1981
    Assignee: Eli Lilly and Company
    Inventors: Paul D. Gesellchen, David L. Smiley
  • Patent number: 4230620
    Abstract: A penicillin is treated with a peroxymonosulfate at a temperature of from about 0.degree. C. to about 50.degree. C. in an aqueous medium to produce a penicillin sulfoxide.
    Type: Grant
    Filed: March 26, 1979
    Date of Patent: October 28, 1980
    Assignee: Eli Lilly and Company
    Inventor: Ta S. Chou
  • Patent number: 4230862
    Abstract: Derivatives of 3-phenyl-4-aroyl-1,2-dihydronaphthalenes and 1-aroyl-2-phenylnaphthalenes are useful both as antifertility agents and in suppressing the growth of mammary tumors.
    Type: Grant
    Filed: August 3, 1978
    Date of Patent: October 28, 1980
    Assignee: Eli Lilly and Company
    Inventors: Tulio Suarez, C. David Jones
  • Patent number: 4199499
    Abstract: 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 and R.sub.2 independently are hydrogen or C.sub.1 -C.sub.3 primary alkyl;R.sub.3 is C.sub.1 -C.sub.4 primary or secondary alkyl, C.sub.1 -C.sub.2 hydroxyalkyl, or --CH.sub.2 CH.sub.2 --U--CH.sub.3, in which U is O or S;R.sub.4 is C.sub.1 -C.sub.3 primary alkyl;Y is hydrogen or acetyl;Z is --CH.sub.2 OH or ##STR2## in which R.sub.5 is C.sub.1 -C.sub.3 alkyl or hydrogen; and W is isopropyl, --VR.sub.6, or --CH.sub.2 --X--CH.sub.3, in which V is O or S, R.sub.6 is C.sub.1 -C.sub.4 alkyl or aralkyl, and X is O, S, or CH.sub.2 --; are useful analgesic agents.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: April 22, 1980
    Assignee: Eli Lilly and Company
    Inventors: Edward L. Smithwick, Jr., Robert C. A. Frederickson, Robert T. Shuman
  • Patent number: 4175082
    Abstract: An N-chloroimide is prepared by contacting the corresponding imide with molecular chlorine under substantially non-aqueous conditions and in the presence of an epoxy compound and a tertiary amine.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: November 20, 1979
    Assignee: Eli Lilly and Company
    Inventor: Ta-Sen Chou
  • Patent number: 4171310
    Abstract: N,N'-Dichlorobicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic-2,3,5,6-diimid e is useful as a reagent in reactions which require a source of positive chlorine.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: October 16, 1979
    Assignee: Eli Lilly and Company
    Inventor: Ian G. Wright
  • Patent number: 4165315
    Abstract: A penicillin sulfoxide ester is reacted with an N-chloro halogenating agent at a temperature of from about 75.degree. C. to about 135.degree. C. to produce a novel 2-chlorosulfinylazetidin-4-one intermediate. The intermediate can be treated with stannic chloride to produce a 3-exomethylenecepham sulfoxide.
    Type: Grant
    Filed: November 17, 1977
    Date of Patent: August 21, 1979
    Assignee: Eli Lilly and Company
    Inventor: Stjepan Kukolja
  • Patent number: 4165316
    Abstract: A penicillin sulfoxide ester is reacted with an N-chloro halogenating agent at a temperature of from about 75.degree. C. to about 135.degree. C. and in the presence of an alkylene oxide and calcium oxide to produce a 2-chlorosulfinylazetidin-4-one intermediate. The intermediate, upon separation from the alkylene oxide, calcium oxide, and any conversion products of both the alkylene oxide and calcium oxide, can be treated with stannic chloride to produce a 3-exomethylenecepham sulfoxide.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: August 21, 1979
    Assignee: Eli Lilly and Company
    Inventor: Ta-Sen Chou
  • Patent number: 4159267
    Abstract: A penicillin sulfoxide is heated in the presence of silylating agent to produce a novel silyl ester azetidine-2-sulfenate which, by treatment with acid, is converted to a desacetoxycephalosporin compound.
    Type: Grant
    Filed: February 9, 1977
    Date of Patent: June 26, 1979
    Assignee: Eli Lilly and Company
    Inventor: Ta-Sen Chou
  • Patent number: 4133814
    Abstract: Derivatives of 2-phenyl-3-aroylbenzothiophenes and 2-phenyl-3-aroylbenzothiophene-1-oxides are useful as antifertility agents. Certain of these compounds also are useful in suppressing the growth of mammary tumors.
    Type: Grant
    Filed: September 17, 1976
    Date of Patent: January 9, 1979
    Assignee: Eli Lilly and Company
    Inventors: C. David Jones, Tulio Suarez
  • Patent number: 4131672
    Abstract: Certain halogenated phenylthioacetamido cephalosporanic acids and derivatives thereof, e.g., 7-[2'-(2",5"-dichlorophenylthio)acetamido]cephalosporanic acid, are effective antibiotics against Staphylococcus aureus cultures which show heterogeneous resistance to methicillin.
    Type: Grant
    Filed: June 16, 1977
    Date of Patent: December 26, 1978
    Assignee: Eli Lilly and Company
    Inventor: George W. Huffman
  • Patent number: 4115383
    Abstract: 2-Sulfinyl (or thio)-.alpha.-isopropenyl (or isopropylidene)-3-amido(or imido)-4-oxo-1-azetidineacetic acids and esters are prepared directly or indirectly from the reaction of a penicillin sulfoxide ester with an ester of acrylic acid. These compounds are active antimicrobial agents or are intermediates to active antimicrobial compounds.
    Type: Grant
    Filed: March 24, 1976
    Date of Patent: September 19, 1978
    Assignee: Eli Lilly and Company
    Inventor: Robin D. G. Cooper
  • Patent number: 4100117
    Abstract: The tetradecapeptide ##STR1## is described along with corresponding non-toxic pharmaceutically-acceptable acid addition salts as well as intermediates useful in the synthesis of the tetradecapeptide. This tetradecapeptide as well as its pharmaceutically-acceptable acid addition salts exhibit various activities including inhibition of the release of gastric acid and reduction of gut motility.
    Type: Grant
    Filed: April 21, 1977
    Date of Patent: July 11, 1978
    Assignee: Eli Lilly and Company
    Inventor: James E. Shields
  • Patent number: 4093574
    Abstract: The tetradecapeptides ##STR1## in which Y is L-Asn or L-Ala are described along with corresponding non-toxic pharmaceutically-acceptable acid addition salts as well as intermediates useful in the synthesis of the tetradecapeptides. These tetradecapeptides as well as their pharmaceutically-acceptable acid addition salts exhibit various activities including inhibition of the release of gastric acid.
    Type: Grant
    Filed: February 2, 1977
    Date of Patent: June 6, 1978
    Assignee: Eli Lilly and Company
    Inventor: James E. Shields
  • Patent number: 4093800
    Abstract: A novel 4-(2'-benzothiazolyldithio)-3-imidoazetidin-2-one of the formula ##STR1## in which X is chloro or bromo and R.sub.2 is methylene or oxygen is ring-closed to the corresponding 3-exomethylenecepham or 3-"oxo" cepham by treatment with sodium or potassium iodide at a temperature of from about 40.degree. C. to about 80.degree. C.
    Type: Grant
    Filed: February 14, 1977
    Date of Patent: June 6, 1978
    Assignee: Eli Lilly and Company
    Inventor: Stjepan Kukolja