Patents Assigned to Lilly Industries Limited
-
Patent number: 5378699Abstract: 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: GrantFiled: February 5, 1993Date of Patent: January 3, 1995Assignees: Lilly Industries Limited, Eli Lilly and CompanyInventors: Michael Brunavs, Colin P. Dell, Peter T. Gallagher, William M. Owton, Jai P. Singh, Colin W. Smith
-
Patent number: 5338735Abstract: 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: GrantFiled: August 12, 1993Date of Patent: August 16, 1994Assignee: Lilly Industries LimitedInventors: John Fairhurst, David E. Tupper
-
Patent number: 5284868Abstract: 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: GrantFiled: September 25, 1992Date of Patent: February 8, 1994Assignees: Eli Lilly and Company, Lilly Industries LimitedInventors: Colin P. Dell, Jai P. Singh, Colin W. Smith
-
Patent number: 5281593Abstract: 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: GrantFiled: April 29, 1993Date of Patent: January 25, 1994Assignee: Lilly Industries LimitedInventors: Jeremy Gilmore, Alec Todd
-
Patent number: 5258378Abstract: 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: GrantFiled: November 19, 1991Date of Patent: November 2, 1993Assignee: Lilly Industries LimitedInventors: Barry P. Clark, Graham H. Timms, David E. Tupper
-
Patent number: 5229382Abstract: 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: GrantFiled: May 22, 1992Date of Patent: July 20, 1993Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten, David E. Tupper
-
Patent number: 5185361Abstract: 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: GrantFiled: September 18, 1991Date of Patent: February 9, 1993Assignee: Lilly Industries LimitedInventor: Jeremy Gilmore
-
Patent number: 5158971Abstract: 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: GrantFiled: May 24, 1991Date of Patent: October 27, 1992Assignee: Lilly Industries limitedInventors: Trafford Clarke, David J. Steggles
-
Patent number: 5066797Abstract: 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: GrantFiled: July 10, 1989Date of Patent: November 19, 1991Assignee: Lilly Industries LimitedInventor: Jack E. Baldwin
-
Patent number: 5051516Abstract: 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: GrantFiled: August 2, 1990Date of Patent: September 24, 1991Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten
-
Patent number: 5041461Abstract: 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: GrantFiled: September 26, 1989Date of Patent: August 20, 1991Assignee: Lilly Industries LimitedInventors: Maria I. Fernandez Fernandez, Terrence M. Hotten, David E. Tupper
-
Patent number: 5037698Abstract: 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: GrantFiled: January 19, 1988Date of Patent: August 6, 1991Assignee: Lilly Industries LimitedInventor: Francois Brunel
-
Patent number: 5028602Abstract: 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: GrantFiled: April 12, 1990Date of Patent: July 2, 1991Assignee: Lilly Industries LimitedInventors: Barry P. Clark, David E. Tupper
-
Patent number: 5021449Abstract: 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: GrantFiled: September 26, 1989Date of Patent: June 4, 1991Assignees: Lilly S.A., Lilly Industries LimitedInventors: Maria I. Fernandez Fernandez, Terrence M. Hotten, David E. Tupper
-
Patent number: 5021441Abstract: 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: GrantFiled: March 22, 1989Date of Patent: June 4, 1991Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, Alec Todd
-
Patent number: 5015656Abstract: 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: GrantFiled: September 26, 1989Date of Patent: May 14, 1991Assignees: Lilly S.A., Lilly Industries LimitedInventors: Maria I. F. Fernandez, Terrence M. Hotten, David E. Tupper
-
Patent number: 4992471Abstract: A method and composition for controlling molluscs employs fluorinated carboxanilides.Type: GrantFiled: March 18, 1987Date of Patent: February 12, 1991Assignee: Lilly Industries LimitedInventor: Christopher Longhurst
-
Patent number: 4983619Abstract: 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: GrantFiled: January 11, 1990Date of Patent: January 8, 1991Assignee: Lilly Industries LimitedInventors: Peter T. Gallagher, Terence A. Hicks
-
Patent number: 4977150Abstract: 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: GrantFiled: August 4, 1989Date of Patent: December 11, 1990Assignee: Lilly Industries LimitedInventors: Jiban Kumar Chakrabarti, Terrence M. Hotten
-
Patent number: 4968711Abstract: 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: GrantFiled: April 18, 1988Date of Patent: November 6, 1990Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, John Goldsworthy, William J. Ross