Patents Assigned to Lilly Industries Limited
  • Patent number: 5378699
    Abstract: Methods of treating an immune disease, cell proliferation, restenosis and vascular smooth muscle cells using the pharmaceutical compounds of the formula ##STR1## in which R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; and salts thereof.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 3, 1995
    Assignees: Lilly Industries Limited, Eli Lilly and Company
    Inventors: Michael Brunavs, Colin P. Dell, Peter T. Gallagher, William M. Owton, Jai P. Singh, Colin W. Smith
  • Patent number: 5338735
    Abstract: Compounds of the formula: ##STR1## in which each R.sup.1 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or nitro, and n is 0, 1, 2 or 3, R.sup.2 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1-4 alkyl, optionally substituted phenyl or C.sub.6-9 cycloalkyl optionally substituted by 1 to 4 C.sub.1-4 alkyl groups, R.sup.5 is optionally substituted phenyl, tetrahydronaphthyl, phthalimido, saccharinyl, glutaramido, C.sub.6-10 cycloalkyl optionally substituted with 1 to 4 C.sub.1-4 alkyl groups or a phenyl group, or C.sub.4-9 heterosubstituted cycloalkyl optionally substituted with 1 to 4 alkyl groups, x is 1, 2 or 3, y is 0 or 1 and z is 0, 1, 2 or 3; and salts thereof.The compounds are indicated for use in the treatment of disorders of the central nervous system.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: August 16, 1994
    Assignee: Lilly Industries Limited
    Inventors: John Fairhurst, David E. Tupper
  • Patent number: 5284868
    Abstract: A pharmaceutical compound of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R.sup.1 is halo, trifluoromethyl, C.sub.1-4 alkoxy, hydroxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, trifluoromethoxy, carboxy, --COOR.sup.5 where R.sup.5 is an ester group, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl; R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; R.sup.3 is nitrile, carboxy, --COOR.sup.8 where R.sup.8 is an ester group, --CONR.sup.9 R.sup.10 where R.sup.9 and R.sup.10 are each hydrogen or C.sub.1-4 alkyl, or R.sup.11 SO.sub.2 -- where R.sup.11 is C.sub.1-4 alkyl or optionally substituted phenyl; and R.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: February 8, 1994
    Assignees: Eli Lilly and Company, Lilly Industries Limited
    Inventors: Colin P. Dell, Jai P. Singh, Colin W. Smith
  • Patent number: 5281593
    Abstract: A compound of the formula ##STR1## in which R.sup.1 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C.sub.1-4 alkyl, aldehydo, --CH.sub.2 Z, --CH.dbd.CH--Z or --CH.sub.2 CH.sub.2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R.sup.2 is halo, nitrile, an optionally protected acid group or --CONR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-4 alkyl; R.sup.3 and R.sup.4 are each hydrogen, C.sub.1-4 alkyl, optionally substituted phenyl, or C.sub.1-4 alkyl substituted by --CONR.sup.7 R.sup.8 or an optionally protected acid group; R.sup.5 is ##STR2## where W is --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --O-- or --S--, R.sup.9 is hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or trihalomethyl, and R.sup.10 is hydrogen, C.sub.1-4 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.1-4 alkyl-C.sub.3-6 cycloalkyl; R.sup.6 is hydrogen or C.sub.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: January 25, 1994
    Assignee: Lilly Industries Limited
    Inventors: Jeremy Gilmore, Alec Todd
  • Patent number: 5258378
    Abstract: The invention relates to a compound of formula (I) ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, halo, hydroxy, nitro, C.sub.1-4 alkylcarbonyl, hydroxy-C.sub.1-4 alkyl, R.sup.3 is hydrogen or optionally substituted phenylsulphonyl, R.sup.4 is optionally substituted phenyl, benzofuranyl or dihydrobenzofuranyl, and R.sup.5 is hydrogen or C.sub.1-4 alkyl; and salts thereof. These compounds are useful dopaminergic agents.
    Type: Grant
    Filed: November 19, 1991
    Date of Patent: November 2, 1993
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, Graham H. Timms, David E. Tupper
  • Patent number: 5229382
    Abstract: 2-Methyl-10-(4-methyl-1-piperazinyl)-4H-thieno-[2,3-b][1,5]benzodiazepine, or an acid salt thereof, has pharmaceutical properties, and is of particular use in the treatment of disorders of the central nervous system.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: July 20, 1993
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten, David E. Tupper
  • Patent number: 5185361
    Abstract: A pharmaceutical compound of the formula ##STR1## in which A is selected from --NHCOR.sup.1, --NHCOOR.sup.1, --NHCONHR.sup.1, --NHCSNHR.sup.1, --CONHR.sup.1, where R.sup.1 is optionally halo-substituted C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.3-7 cycloalkyl-C.sub.1-4 alkyl or phenyl-C.sub.1-4 alkyl B is optionally substituted phenyl, and --X--Y-- is --CH=CH-- or --CH.sub.2 --CH.sub.2 --; and salts thereof. The compounds are leukotriene antagonists.
    Type: Grant
    Filed: September 18, 1991
    Date of Patent: February 9, 1993
    Assignee: Lilly Industries Limited
    Inventor: Jeremy Gilmore
  • Patent number: 5158971
    Abstract: A pharmaceutical compound of the formula ##STR1## in which R.sup.1 is halo-C.sub.1-10 alkyl, C.sub.1-10 alkylthio, halo-C.sub.1-10 alkylthio or optionally substituted phenylthio, R.sup.2 is hydrogen or C.sub.1-4 alkyl, R.sup.3 and R.sup.4 are each hydrogen or C.sub.1-4 alkyl, and X is oxygen or sulphur; and salts thereof.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: October 27, 1992
    Assignee: Lilly Industries limited
    Inventors: Trafford Clarke, David J. Steggles
  • Patent number: 5066797
    Abstract: There is described a process for producing exomethylene cepham intermediates useful in cephalosporin chemistry. The process comprises the preparation of a compound of the formula ##STR1## in which R.sup.1 is an amino group, a protected amino group, an acylamino group or a diacylamino group,R.sup.2 is hydrogen, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio,R.sup.3 is hydrogen, a salt ion or an ester-forming group, andR.sup.4 is hydrogen or C.sub.1-3 alkyl,by reacting a compound of the formula ##STR2## in which Y is a bridging group of the formula ##STR3## Z is chloro, bromo or iodo, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the above defined values, with a reagent providing cobalt I, under reducing conditions.
    Type: Grant
    Filed: July 10, 1989
    Date of Patent: November 19, 1991
    Assignee: Lilly Industries Limited
    Inventor: Jack E. Baldwin
  • Patent number: 5051516
    Abstract: Pharmaceutical thiazolo-[1,5]benzodiazepines of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halogen, C.sub.1-4 haloalkyl, nitro, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylthio or phenylsulphonyl; in which R.sup.5 is a group of the formula formula ##STR2## where R.sup.7 is hydrogen, C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, benzyl or ZO--C.sub.2-6 alkyl where Z is hydrogen or an acyl group, R.sup.8 is hydrogen or C.sub.1-4 alkyl and n is 0 or 1, provided that when R.sup.7 is hydrogen n is 0; in which R.sup.6 is hydrogen, C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio; and in which ##STR3## represents a thiazole ring selected from ##STR4## and acid addition salts thereof. The compounds have central nervous system activity.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: September 24, 1991
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten
  • Patent number: 5041461
    Abstract: A pharmaceutically-active compound of the formula ##STR1## in which R.sup.1 is C.sub.1-4 alkythio, C.sub.1-4 alkylsulphinyl or C.sub.1-4 alkylsulphonyl, R.sup.2 is C.sub.1-4 alkyl, R.sup.3 is C.sub.1-4 alkyl or C.sub.2-4 alkenyl, and X is (i) --(CH.sub.2).sub.n N(R.sup.4).sub.2 where each R.sup.4 independently is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or optionally substituted C.sub.6 H.sub.5 CH.sub.2 --, and n is 1, 2 or 3, or (ii) a 5- to 8-membered alicyclic group containing one or two nitrogen atoms and directly attached to the amido nitrogen or attached by a C.sub.1-3 alkylene chain; and salts thereof.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: August 20, 1991
    Assignee: Lilly Industries Limited
    Inventors: Maria I. Fernandez Fernandez, Terrence M. Hotten, David E. Tupper
  • Patent number: 5037698
    Abstract: Capsules containing a hygroscopic or deliquescent component are stabilized by a) forming a mixture of the hydrogscopic or deliquescent compound with a sufficient quantity of water to achieve an equilibrium, b) adding a thickening agent and c) heating the solution or suspension; and introducing the heated composition so formed into the capsule. Preferably an equilibrium-protecting agent, such as glycerin, is also added.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: August 6, 1991
    Assignee: Lilly Industries Limited
    Inventor: Francois Brunel
  • Patent number: 5028602
    Abstract: Pharmaceutical compounds having the formula ##STR1## in which R.sup.1 is hydrogen, hydroxy, nitro, cyano, halo, amino, acetamido, hydroxy-C.sub.1-4 alkyl, carboxaldehydo, C.sub.1-4 alkyl-carbonyl, carboxy, C.sub.1-4 alkoxy-carbonyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl or C.sub.1-4 alkoxy-C.sub.1-4 alkyl, R.sup.2 is hydrogen or halo, R.sup.3 is optionally substituted phenyl or optionally substituted phenyl ortho condensed with an optionally substituted ring selected from benzene, cyclohexane, cyclohexene, cyclopentane or cyclopentene, in which ring one of the carbon atoms may be replaced by oxygen, sulphur or nitrogen, and R.sup.4 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or optionally substituted benzyl; and salts thereof.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: July 2, 1991
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, David E. Tupper
  • Patent number: 5021449
    Abstract: A pharmaceutical compound of the formula ##STR1## in which R.sup.1 is --CHO, CH.sub.2 OH, --CH.sub.2 OC.sub.1-4 alkyl, --COC.sub.1-3 alkyl, --CH(OH)C.sub.1-3 alkyl or --COOH, R.sup.2 is C.sub.1-4 alkyl, --CHO, --CH.sub.2 OH, --CH.sub.2 OC.sub.1-4 alkyl, --COC.sub.1-3 alkyl, --CH(OH)C.sub.1-3 alkyl or --COOH, R.sup.3 is C.sub.1-4 alkyl and X is pyrrolidinyl or pyrrolidinylmethyl; and salts and esters thereof.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: June 4, 1991
    Assignees: Lilly S.A., Lilly Industries Limited
    Inventors: Maria I. Fernandez Fernandez, Terrence M. Hotten, David E. Tupper
  • Patent number: 5021441
    Abstract: There are disclosed pharmaceutical compounds of the formula: ##STR1## in which R.sup.1 is halo-substituted alkyl;X is alkenylene; and R.sup.1 --X-- contains 6 to 34 carbon atoms;R.sup.2 is C.sub.1-5 alkyl substituted by(i) optionally protected carboxyl, nitrile, optionally protected tetrazolyl or --CONR'R", in which R' and R" are each hydrogen or C.sub.1-4 alkyl, ##STR2## (ii) in which R' and R" are each hydrogen or C.sub.1-4 alkyl, or ##STR3## (iii) in which R', R" and R'" are each hydrogen or C.sub.1-4 alkyl, or R.sup.2 is a group of the formula ##STR4## in which R' is hydrogen or an optionally protected amino acid residue, and R" is --OH or an optionally protected amino acid residue; andR.sup.3, R.sup.4 and R.sup.5 are each hydrogen, optionally protected carboxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxyl, optionally protected tetrazolyl, halo, trifluoromethyl, nitrile, nitro or --CONR'R" where R' and R" are each hydrogen or C.sub.1-4 alkyl; and salts thereof.
    Type: Grant
    Filed: March 22, 1989
    Date of Patent: June 4, 1991
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, Alec Todd
  • Patent number: 5015656
    Abstract: A pharmaceutical compound of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen, hydroxy, halo, nitro, amino, C.sub.2-5 acylamino, C.sub.1-4 alkyl, --CHO, --CH.sub.2 OH, --CH.sub.2 OC.sub.1-4 alkyl, --COOH, --COC.sub.1-3 alkyl, --CH(OH)C.sub.1-3 alkyl, C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N-substituted heterocyclyl, optionally substituted phenyl, optionally substituted phenylthio, optionally substituted phenylsulphinyl, optionally substituted phenylsulphonyl or optionally substituted phenylsulphonamido, or R.sup.1 and R.sup.2 together form a C.sub.3-5 alkylene bridge; provided that at least one of R.sup.2 and R.sup.3 is C.sub.1-4 alkoxy or C.sub.2-4 alkenyloxy; and X is (i) --(CH.sub.2).sub.n N(R.sup.4).sub.2 where each R.sup.4 independently is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or optionally substituted C.sub.6 H.sub.5 CH.sub.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: May 14, 1991
    Assignees: Lilly S.A., Lilly Industries Limited
    Inventors: Maria I. F. Fernandez, Terrence M. Hotten, David E. Tupper
  • Patent number: 4992471
    Abstract: A method and composition for controlling molluscs employs fluorinated carboxanilides.
    Type: Grant
    Filed: March 18, 1987
    Date of Patent: February 12, 1991
    Assignee: Lilly Industries Limited
    Inventor: Christopher Longhurst
  • Patent number: 4983619
    Abstract: Compounds of the following formula have pharmaceutical properties: ##STR1## in which X is R'(HO)C.dbd.C(CN)--, R.sup.1 (CO)--CH(CN)-- or ##STR2## R.sup.1 and R.sup.2 are each hydrogen or C.sub.1-6 alkyl, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each hydrogen, hydroxy, halogen, nitro, cyano, carboxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halo-substituted C.sub.1-4 alkyl, halo-substituted C.sub.1-4 alkoxy, halo-substituted C.sub.1-4 alkylthio, C.sub.2-5 alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, R'R"N-- where R' and R" are each hydrogen or C.sub.1-4 alkyl or R'"CONH-- where R'" is C.sub.1-4 alkyl, or a group of the formula --CR.sup.7 R.sup.8 R.sup.9 in which R.sup.7, R.sup.8 and R.sup.9 are each C.sub.1-6 alkyl, halo-substituted C.sub.1-6 alkyl or optionally substituted phenyl, or R.sup.7 and R.sup.8, together with the carbon atom to which they are attached, form a cycloalkyl group containing 3 to 7 carbon atoms, or R.sup.7, R.sup.8 and R.sup.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: January 8, 1991
    Assignee: Lilly Industries Limited
    Inventors: Peter T. Gallagher, Terence A. Hicks
  • Patent number: 4977150
    Abstract: Pharmaceutical thiazolo-[1,5]benzodiazepines of the formula ##STR1## in which R.sup.1, R.sup.2 , R.sup.3 and R.sup.4 are independently hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halogen, C.sub.1-4 haloalkyl, nitro, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylthio or phenylsulphonyl; in which R.sup.5 is a group of the formula ##STR2## where R.sup.7 is hydrogen, C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, benzyl or ZO-C.sub.2-6 alkyl wherein Z is hydrogen or an acyl group, R.sup.8 is hydrogen or C.sub.1-4 alkyl and n is 0 or 1, provided that when R.sup.7 is hydrogen n is 0; in which R.sup.6 is hydrogen, C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio; and in which ##STR3## represents a thiazole ring selected from ##STR4## and acid addition salts thereof. The compounds have cental nervous system activity.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: December 11, 1990
    Assignee: Lilly Industries Limited
    Inventors: Jiban Kumar Chakrabarti, Terrence M. Hotten
  • Patent number: 4968711
    Abstract: There is disclosed a pharmaceutical compound of the formula ##STR1## in which R.sup.1 is C.sub.7-20 alkyl, C.sub.7-20 alkenyl, or C.sub.7-20 alkynyl, the alkyl, alkenyl or alkynyl group being optionally substituted by phenyl or substituted phenyl, R.sup.2 is --CN, --COOR.sup.3 or ##STR2## wherein R.sup.3 is hydrogen or a protecting group, X is alkylene containing 1 to 6 carbon atoms and Y is a nitrogen-containing group selected from ##STR3## where each R.sup.4 independently is hydrogen or C.sub.1-4 alkyl; and salts thereof.
    Type: Grant
    Filed: April 18, 1988
    Date of Patent: November 6, 1990
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, John Goldsworthy, William J. Ross