Patents Assigned to Lilly Industries Limited
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Patent number: 4963578Abstract: There are described compounds of formula ##STR1## in which n is 0, 1 or 2, R.sup.1 is a hydrocarbyl group optionally substituted with an optionally substituted phenyl group and containing from 5 to 30 carbon atoms, R.sup.2 is optionally substituted phenyl or C.sub.1-10 alkyl optionally substituted by one or more substituents selected from optionally protected hydroxyl, optionally protected carboxyl, nitrile, optionally protected tetrazolyl, --COR.sup.6 where R.sup.6 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.7 where each R.sup.7 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.8 where R.sup.8 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.9 where R.sup.9 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and R.sup.3, R.sup.4 and R.sup.5 are each selected from hydrogen, carboxyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkyl, C.sub.Type: GrantFiled: November 1, 1989Date of Patent: October 16, 1990Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William B. Jamieson, deceased, Alec Todd
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Patent number: 4963558Abstract: Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 is hydrogen or C.sub.1-6 alkyl, R.sup.2 is hydrogen, C.sub.1-6 alkyl optionally substituted by C.sub.3-9 cycloalkyl or optionally substituted phenyl, C.sub.3-9 cycloalkyl, optionally substituted phenyl, or --SR.sup.4 where R.sup.4 is C.sub.1-6 alkyl optionally substituted by C.sub.3-9 cycloalkyl or optionally substituted phenyl, or C.sub.3-9 cycloalkyl, R.sup.3 is hydrogen, C.sub.1-6 alkyl optionally substituted by C.sub.3-9 cycloalkyl or optionally substituted phenyl, c.sub.3-9 cycloalkyl, or optionally phenyl, and either X and Y are both hydrogen or together are .dbd.O; and acid addition salts thereof. These compounds show useful effects on the central nervous system.Type: GrantFiled: December 7, 1989Date of Patent: October 16, 1990Assignee: Lilly Industries LimitedInventors: Terrence M. Hotten, Graham H. Timms, David E. Tupper
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Patent number: 4904653Abstract: Compounds of 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 alkylcarbonyl, 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, hydroxy, nitro, cyano, halo, amino, carboxamido, acetamido, hydroxy-C.sub.1-4 alkyl, carboxyaldehydo, C.sub.1-4 alkylcarbonyl, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, oximino or aminomethyl, 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.Type: GrantFiled: January 6, 1989Date of Patent: February 27, 1990Assignee: Lilly Industries LimitedInventors: Barry P. Clark, David E. Tupper
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Patent number: 4904686Abstract: Compounds of the following formula have pharmacutical properties: ##STR1## in which R.sup.1 and R.sup.2 independently are hydrogen, halo, nitro, amino, C.sub.2-5 acylamino, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl, N-substituted heterocyclyl, optionally substituted phenyl, optionally substituted phenylthio, optionally substituted phenylsulphonyl or optionally substituted phenylsulphonamido, or R.sup.1 and R.sup.2 together form a C.sub.3-5 alkylene bridge, 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: April 11, 1988Date of Patent: February 27, 1990Assignee: Lilly Industries LimitedInventors: Maria I. F. Fernandez, Terrence M. Hotten, David E. Tupper
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Patent number: 4892766Abstract: Hard gelatin capsules are made from gelatin containing up to 10% of a preferably hydrophilic fibrous material. They do not split after storage when filled with hygroscopic or deliquescent materials.Type: GrantFiled: September 8, 1988Date of Patent: January 9, 1990Assignee: Lilly Industries LimitedInventor: Brian E. Jones
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Patent number: 4892963Abstract: Compounds of the following formula have pharmaceutical properties: ##STR1## in which X is R.sup.1 (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 and R.sup.5 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 R'"CONH-- where R'" is C.sub.1-4 alkyl, R.sup.6, R.sup.7 and R.sup.8 are each C.sub.1-6 alkyl, halo-substituted C.sub.1-6 alkyl or optionally substituted phenyl, or R.sup.6 and R.sup.7, together with the carbon atom to which they are attached, form a cycloalkyl group containing 3 to 7 carbon atoms, or R.sup.6, R.sup.7 and R.sup.Type: GrantFiled: August 7, 1987Date of Patent: January 9, 1990Assignee: Lilly Industries LimitedInventors: Peter T. Gallagher, Terence A. Hicks, Graham W. Mullier
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Patent number: 4886885Abstract: 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 and the alkenyl and alkynyl groups containing 1 to 3 unsaturated bonds, R.sup.2 is (i) optionally substituted phenyl, (ii) C.sub.1-10 alkyl optionally substituted by one or more substituents selected from optionally protected hydroxyl, optionally protected carboxyl, nitrile, optionally protected tetrazolyl, --COR.sup.4 where R.sup.4 is C.sub.1-14 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.5 where each R.sup.5 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.6 where R.sup.6 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.7 where R.sup.7 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or (iii) C.sub.1-10 alkyl substituted with a group selected from ##STR2## where each R.sup.8 is hydrogen or C.sub.Type: GrantFiled: October 26, 1988Date of Patent: December 12, 1989Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, Alec Todd
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Patent number: 4845200Abstract: A conjugate comprising a vinca moiety convalently linked at the 4-position via a group of the formula --OCOXCO-- where X represents a single chemical bond or an optionally substituted C.sub.1-10 chain, to an immunoglobulin or an immunoglobulin fragment.The conjugates are useful in the treatment of cancer.Type: GrantFiled: June 23, 1986Date of Patent: July 4, 1989Assignee: Lilly Industries LimitedInventors: George J. Cullinan, George F. Rowland, Robin G. Simmonds
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Patent number: 4845110Abstract: There are provided anti-allergic pharmaceutical compounds of formula: ##STR1## in which n is 0, 1 or 2; R.sup.1 is a hydrocarbyl group containing 6 to 30 carbon atoms and optionally substituted with an optionally substituted phenyl group; R.sup.2 is (i) optionally optionally protected tetrazolyl, --COR.sup.6 where R.sup.6 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.7 where each R.sup.7 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.8 where R.sup.8 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.9 where R.sup.9 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or (iii) C.sub.1-10 alkyl substituted with a group selected from ##STR2## where each R.sup.10 is hydrogen or C.sub.1-4 alkyl; and R.sup.3, R.sup.4 and R.sup.5 are each selected from hydrogen, carboxyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkyl, hydroxyl, optionally protected tetrazolyl, halo, trifluoromethyl, nitrile, nitro and --CONR.sub.2.sup.Type: GrantFiled: December 4, 1986Date of Patent: July 4, 1989Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, Alec Todd
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Patent number: 4841056Abstract: There are disclosed intermediates to pharmaceutical compounds of the formula ##STR1## in which R.sup.1 is an aliphatic or aromatic function, and R.sup.2 and R.sup.3 are each hydrogen, C.sub.1-4 alkyl or a protecting group; and salts thereof.Type: GrantFiled: January 27, 1988Date of Patent: June 20, 1989Assignee: Lilly Industries LimitedInventor: William H. Hunter
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Patent number: 4822618Abstract: A gelatin capsule cap has an annular groove in the region of its open end to reduce ovality.Type: GrantFiled: May 13, 1987Date of Patent: April 18, 1989Assignee: Lilly Industries LimitedInventors: Bernard Schweiger, Alfred Wagner
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Patent number: 4801735Abstract: Compounds are described of the following formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-12 alkyl or C.sub.2-12 alkenyl, at least one of R.sup.1 and R.sup.2 being C.sub.1-12 alkyl or C.sub.2-12 alkenyl; X.sup.1 and X.sup.2 are each hydrogen or a protecting group; and Y is(a) --(CH.dbd.CH).sub.n Z in which n is 1, 2 or 3 and Z is --CHO, --CH.sub.2 OH, --COR.sup.3, --(CH.sub.2).sub.m --COR.sup.3 or --(CH.sub.2).sub.p CH.dbd.CH(CH.sub.2).sub.q --COR.sup.3 in which m is an integer of 1 to 12, p is an integer of 1 to 4, q is an integer of 1 to 10 and R.sup.3 is (i) --OH or (ii) --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are each hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholino, pyrrolidinyl or piperidino ring,(b) --CH.dbd.NR.sup.6 in which R.sup.6 is (i) --OH, (ii) C.sub.1-12 alkyl optionally substituted by --OH, --COOH or --NR.sup.7 R.sup.8 where R.sup.7 and R.sup.Type: GrantFiled: November 25, 1985Date of Patent: January 31, 1989Assignee: Lilly Industries LimitedInventors: Mark A. W. Finch, John R. Harris
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Patent number: 4755389Abstract: A hard gelatin capsule is filled with a chewable composition containing an ingredient for buccal absorption or having buccal activity.Type: GrantFiled: September 10, 1986Date of Patent: July 5, 1988Assignee: Lilly Industries LimitedInventors: Brian E. Jones, Paula M. Knight, Mark A. Walker
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Patent number: 4742075Abstract: There are disclosed pharmaceutical compounds of the formula ##STR1## in which R.sup.1 is an aliphatic or aromatic function, and R.sup.2 and R.sup.3 are each hydrogen, C.sub.1-4 alkyl or a protecting group; and salts thereof.Type: GrantFiled: July 22, 1985Date of Patent: May 3, 1988Assignee: Lilly Industries LimitedInventor: William H. Hunter
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Patent number: 4740514Abstract: There are described compounds of the formula ##STR1## in which R.sup.1 is hydrogen or C.sub.1-6 alkyl, R.sup.2 is hydrogen, C.sub.1-6 alkyl or C.sub.3-6 alkenyl, X and Y are each oxygen, sulphur, sulphinyl or sulphonyl, n is 2 to 6 and Z is 1H-tetrazol-5-yl, 1H-tetrazol-5-ylthio, 1H-tetrazol-5-ylsulphinyl, 1H-tetrazol-5-ylsulphonyl, cyano or thiocyano, provided that when both X and Y are oxygen Z is 1H-tetrazol-5-ylthio, 1H-tetrazol-5-ylsulphinyl, 1H-tetrazol-5-ylsulphonyl or thiocyano; and salts thereof. The compounds in which Z is other than cyano or thiocyano have pharmaceutical activity and inhibit leukotriene action or formation.Type: GrantFiled: May 27, 1986Date of Patent: April 26, 1988Assignee: Lilly Industries LimitedInventors: John Goldsworthy, Winston S. Marshall, John P. Verge
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Patent number: 4720498Abstract: There is described a compound of the formula ##STR1## in which R.sup.1 is hydrogen or C.sub.1-4 alkyl, R.sup.2 is hydrogen, C.sub.1-4 alkyl, hydroxy C.sub.1-4 alkyl, C.sub.1-4 alkoxy C.sub.1-4 alkyl, HSC.sub.1-4 alkyl, C.sub.1-4 alkyl-S-C.sub.1-4 alkyl, C.sub.1-4 alkylthio, optionally substituted arylthio or optionally substituted aralkylthio, and R.sup.3 is hydrogen, C.sub.1-4 alkyl, optionally substituted aryl or optionally substituted aralkyl; and salts thereof. The compounds show useful effects on the central nervous system.Type: GrantFiled: October 28, 1985Date of Patent: January 19, 1988Assignee: Lilly Industries LimitedInventors: Graham H. Timms, David E. Tupper
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Patent number: 4705807Abstract: Novel amines of formula:R--(CH.sub.2).sub.n --NR.sup.1 R.sup.2where R is cis-2-phenylbicyclo[2,2,2]octane or 2-phenylbicyclo[2,2,2]oct-2-ene nucleus, n is 1 to 3, R.sup.1 is C.sub.1-3 alkyl and R.sup.2 is hydrogen or C.sub.1-3 alkyl, and acid-addition salts thereof, which are useful for the treatment of disorders of the central nervous system.Type: GrantFiled: December 10, 1982Date of Patent: November 10, 1987Assignee: Lilly Industries LimitedInventors: David C. Horwell, Graham H. Timms
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Patent number: 4675335Abstract: Pharmaceutical compounds are described of the formula ##STR1## in which R.sup.1 is (i) R.sup.4 O(CH.sub.2 CH.sub.2 O).sub.n (CH.sub.2).sub.m --, where R.sup.4 is hydrogen or C.sub.1-5 alkyl, n is 0 or 1 to 5 and m is 1 to 7, or (ii) R.sup.5 --X-- where R.sup.5 is a polar group and X is a C.sub.6-20 alkylene or a C.sub.6-20 alkenylene radical containing from 1 to 3 double bonds, R.sup.2 is a group of the formula A--B-- where A is --COOH or ##STR2## where R.sup.6 is hydrogen or a protecting group, and B is C.sub.1-6 alkylene, and R.sup.3 is --COOH or ##STR3## where R.sup.7 is hydrogen or a protecting group; or a salt or ester thereof.Type: GrantFiled: January 27, 1986Date of Patent: June 23, 1987Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William J. Ross
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Patent number: 4675333Abstract: There are described compounds of the formula ##STR1## in which R.sup.1 is hydrogen or C.sub.1-6 alkyl, R.sup.2 is hydrogen, C.sub.1-6 alkyl or C.sub.3-6 alkenyl, R.sup.3 is hydrogen or C.sub.1-6 alkyl, R.sup.4 is hydrogen or an N-protecting group, n is 2, 3, 4 or 5, and X is oxygen, sulphur or --CH.sub.2 --, provided that when X is --CH.sub.2 -- n is 0; and salts thereof. The compounds in which R.sup.4 is hydrogen have pharmaceutical activity.Type: GrantFiled: December 5, 1984Date of Patent: June 23, 1987Assignee: Lilly Industries LimitedInventors: David J. Steggles, John P. Verge
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Patent number: 4675334Abstract: Compounds of formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently selected from H, OH, C.sub.1 -C.sub.4 alkyl, R.sub.4 --CO and halogen, where R.sub.4 is C.sub.1 -C.sub.4 alkyl; R.sub.5 and R.sub.6 are each independently selected from H, C.sub.1 -C.sub.4 alkyl and optionally-substituted phenyl; R.sub.7 is an alkylene group having from 1 to 4 carbon atoms, optionally containing a substituted or unsubstituted phenyl group; p is 0 or 1; and Z is a 1H-tetrazol-5-yl or a --CN group; and salts thereof, may be prepared by reacting a compound of formula. ##STR2## with a compound of formula ##STR3## wherein R.sub.1 -R.sub.7 are as defined in claim 1, in an organic solvent at a temperature in the range of 40.degree.-120.degree. C.Type: GrantFiled: July 11, 1984Date of Patent: June 23, 1987Assignee: Lilly Industries LimitedInventors: David J. Steggles, John P. Verge