Patents Assigned to Lilly Industries Limited
  • Patent number: 4963578
    Abstract: 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: Grant
    Filed: November 1, 1989
    Date of Patent: October 16, 1990
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, deceased, Alec Todd
  • Patent number: 4963558
    Abstract: 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: Grant
    Filed: December 7, 1989
    Date of Patent: October 16, 1990
    Assignee: Lilly Industries Limited
    Inventors: Terrence M. Hotten, Graham H. Timms, David E. Tupper
  • Patent number: 4904653
    Abstract: 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: Grant
    Filed: January 6, 1989
    Date of Patent: February 27, 1990
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, David E. Tupper
  • Patent number: 4904686
    Abstract: 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: Grant
    Filed: April 11, 1988
    Date of Patent: February 27, 1990
    Assignee: Lilly Industries Limited
    Inventors: Maria I. F. Fernandez, Terrence M. Hotten, David E. Tupper
  • Patent number: 4892766
    Abstract: 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: Grant
    Filed: September 8, 1988
    Date of Patent: January 9, 1990
    Assignee: Lilly Industries Limited
    Inventor: Brian E. Jones
  • Patent number: 4892963
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: January 9, 1990
    Assignee: Lilly Industries Limited
    Inventors: Peter T. Gallagher, Terence A. Hicks, Graham W. Mullier
  • Patent number: 4886885
    Abstract: 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: Grant
    Filed: October 26, 1988
    Date of Patent: December 12, 1989
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, Alec Todd
  • Patent number: 4845200
    Abstract: 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: Grant
    Filed: June 23, 1986
    Date of Patent: July 4, 1989
    Assignee: Lilly Industries Limited
    Inventors: George J. Cullinan, George F. Rowland, Robin G. Simmonds
  • Patent number: 4845110
    Abstract: 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: Grant
    Filed: December 4, 1986
    Date of Patent: July 4, 1989
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, Alec Todd
  • Patent number: 4841056
    Abstract: 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: Grant
    Filed: January 27, 1988
    Date of Patent: June 20, 1989
    Assignee: Lilly Industries Limited
    Inventor: William H. Hunter
  • Patent number: 4822618
    Abstract: A gelatin capsule cap has an annular groove in the region of its open end to reduce ovality.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: April 18, 1989
    Assignee: Lilly Industries Limited
    Inventors: Bernard Schweiger, Alfred Wagner
  • Patent number: 4801735
    Abstract: 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: Grant
    Filed: November 25, 1985
    Date of Patent: January 31, 1989
    Assignee: Lilly Industries Limited
    Inventors: Mark A. W. Finch, John R. Harris
  • Patent number: 4755389
    Abstract: A hard gelatin capsule is filled with a chewable composition containing an ingredient for buccal absorption or having buccal activity.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: July 5, 1988
    Assignee: Lilly Industries Limited
    Inventors: Brian E. Jones, Paula M. Knight, Mark A. Walker
  • Patent number: 4742075
    Abstract: 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: Grant
    Filed: July 22, 1985
    Date of Patent: May 3, 1988
    Assignee: Lilly Industries Limited
    Inventor: William H. Hunter
  • Patent number: 4740514
    Abstract: 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: Grant
    Filed: May 27, 1986
    Date of Patent: April 26, 1988
    Assignee: Lilly Industries Limited
    Inventors: John Goldsworthy, Winston S. Marshall, John P. Verge
  • Patent number: 4720498
    Abstract: 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: Grant
    Filed: October 28, 1985
    Date of Patent: January 19, 1988
    Assignee: Lilly Industries Limited
    Inventors: Graham H. Timms, David E. Tupper
  • Patent number: 4705807
    Abstract: 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: Grant
    Filed: December 10, 1982
    Date of Patent: November 10, 1987
    Assignee: Lilly Industries Limited
    Inventors: David C. Horwell, Graham H. Timms
  • Patent number: 4675335
    Abstract: 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: Grant
    Filed: January 27, 1986
    Date of Patent: June 23, 1987
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William J. Ross
  • Patent number: 4675333
    Abstract: 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: Grant
    Filed: December 5, 1984
    Date of Patent: June 23, 1987
    Assignee: Lilly Industries Limited
    Inventors: David J. Steggles, John P. Verge
  • Patent number: 4675334
    Abstract: 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: Grant
    Filed: July 11, 1984
    Date of Patent: June 23, 1987
    Assignee: Lilly Industries Limited
    Inventors: David J. Steggles, John P. Verge