Patents Assigned to Lilly Industries Limited
  • Patent number: 4304728
    Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: December 8, 1981
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4301280
    Abstract: There is described a process for preparing an enamine of formula (IX): ##STR1## where R.sup.2 is a carboxylic acid protecting group and R.sup.3 is the residue of a carboxylic acid derived acyl group and where R.sup.5 and R.sup.6 are the same or different C.sub.1-4 alkyl or C.sub.7-10 aralkyl groups; or taken together with the adjacent nitrogen atom form a heterocyclic ring containing from 4 to 8 carbon atoms and optionally a further heteroatom selected from oxygen and nitrogen; by reacting a compound of formula (XII): ##STR2## with an amine of formula HNR.sup.5 R.sup.6, the reactant of formula (XII) being prepared by reaction of an appropriate enol derivative with a phosphorus reagent. The enamines of formula (IX) are useful in the preparation of 3-hydroxycephalosporins.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: November 17, 1981
    Assignee: Lilly Industries Limited
    Inventors: John R. Corfield, Derek Johnson, Clifford G. Taylor
  • Patent number: 4293563
    Abstract: Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen;or is thiophene optionally substituted by phenyl or by one or two C.sub.1-4 alkyl groups;R.sup.1 and R.sup.2 are independently hydrogen or taken together represent a chemical bond;R.sup.3 is hydrogen, C.sub.1-6 alkyl or C.sub.2-4 alkenyl; andR.sup.4 is C.sub.1-6 alkyl, C.sub.2-4 alkenyl, phenyl or benzyl;provided that R.sup.3 cannot be hydrogen when Ar is unsubstituted phenyl and R.sup.4 is n-butyl. The compounds are useful in the treatment of immediate hypersensitivity diseases including asthma.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: October 6, 1981
    Assignee: Lilly Industries Limited
    Inventors: William B. Jamieson, William J. Ross, Robin G. Simmonds, John P. Verge
  • Patent number: 4281017
    Abstract: Compounds of formula I ##STR1## wherein either R.sup.1 and R.sup.2 are both hydrogen or R.sup.1 and R.sup.2, taken together, represent a group of formula (a): ##STR2## in which R.sup.5 is hydrogen, halogen or C.sub.1-4 alkyl, R.sup.3 is hydrogen or a group of formula (b): ##STR3## in which R.sup.6 is hydrogen or C.sub.1-4 alkyl, and R.sup.4 is hydrogen or a group of formula --CHR.sup.7 COOH, where R.sup.7 is hydrogen or C.sub.1-4 alkyl,provided that:(i) when R.sup.3 is a group of formula (b), then R.sup.1, R.sup.2 and R.sup.4 are all hydrogen,(ii) when R.sup.3 is hydrogen, then R.sub.4 is --CHR.sup.7 COOH, and(iii) when R.sup.1 and R.sup.2, together, represent a group of formula (a), then R.sub.3 is hydrogen;possess pharmacological activity, in particular anti-inflammatory activity and are particularly useful in treatment of rheumatoid arthritis.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: July 28, 1981
    Assignee: Lilly Industries Limited
    Inventor: William R. N. Williamson
  • Patent number: 4277480
    Abstract: Isoquinoline compounds of the following formula are described: ##STR1## wherein the moiety A-B represents a group of formula;--CH.sub.2 --NR.sup.3 -- or --NR.sup.3 --CH.sub.2 --;wherein R.sup.3 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl C.sub.1-4 alkyl, optionally substituted benzyl, C.sub.3-6 alkenyl or C.sub.1-4 alkanoyl;wherein R represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, or optionally substituted benzyl;wherein R.sup.1 and R.sup.2 each represent hydrogen or taken together represent a chemical bond; and wherein X is hydrogen or halogen; or an acid-addition salt thereof.The compounds are pharmaceuticals and especially useful in the treatment of disorders of the central nervous system.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: July 7, 1981
    Assignee: Lilly Industries Limited
    Inventors: David C. Horwell, David E. Tupper
  • Patent number: 4260357
    Abstract: This invention relates to a ring form of a rigid and durable material with a metal insert arranged in its passageway. The ring is employed to strip thin walled gelatin capsules from capsule-forming pins which are slightly tapered along their entire length.
    Type: Grant
    Filed: February 15, 1980
    Date of Patent: April 7, 1981
    Assignee: Lilly Industries Limited
    Inventors: William G. Roast, Geoffrey E. Adnams
  • Patent number: 4259343
    Abstract: A class of novel 2-oxazolyl ureas and carbamates having anti-allergic activity are described together with methods of making such compounds and pharmaceutical compositions containing the active compounds of the invention.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: March 31, 1981
    Assignee: Lilly Industries Limited
    Inventors: William J. Ross, Alec Todd, John P. Verge
  • Patent number: 4259340
    Abstract: Substituted aurones of formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and can each represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.3-8 cycloalkyl, optionally substituted phenyl, C.sub.1-6 haloalkyl, amido, amino, cyano, hydroxy, nitro, C.sub.2-4 alkenyl, carboxyl, tetrazol-5-yl and --CH.dbd.CHCOOH; orwherein R.sup.1 and R.sup.2 taken together can represent a group of formula --CH.dbd.CH--CH.dbd.CH-- provided that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is carboxyl, tetrazol-5-yl or --CH.dbd.CHCOOH;or a pharmaceutically-acceptable salt or ester thereof, are effective in the prophylactic chemotherapy of allergic conditions such as bronchial asthma.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: March 31, 1981
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, William J. Ross
  • Patent number: 4246281
    Abstract: Acenaphthenes of formula (I) ##STR1## where Ph represents an optionally substituted phenyl group and wherein R.sup.1 represents hydrogen or C.sub.1-4 alkyl are useful anti-inflammatory agents.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: January 20, 1981
    Assignee: Lilly Industries Limited
    Inventor: William R. N. Williamson
  • Patent number: 4245095
    Abstract: Isoquinoline compounds of the following formula are described: ##STR1## wherein the moiety A-B represents a group of formula:--CH.sub.2 --NR.sup.3 -- or --NR.sup.3 --CH.sub.2 --;wherein R.sup.3 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl C.sub.3-6 cycloalkyl-C.sub.1-4 alkyl, optionally substituted benzyl, C.sub.3-6 alkenyl or C.sub.1-4 alkanoyl;wherein R represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, or optionally substituted benzyl;wherein R.sup.1 and R.sup.2 each represent hydrogen or taken together represent a chemical bond; and wherein X is hydrogen or halogen; or an acid-addition salt thereof.The compounds are pharmaceuticals and especially useful in the treatment of disorders of the central nervous system.
    Type: Grant
    Filed: February 1, 1980
    Date of Patent: January 13, 1981
    Assignee: Lilly Industries Limited
    Inventors: David C. Horwell, David E. Tupper
  • Patent number: 4241073
    Abstract: Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen;or is thiophene optionally substituted by phenyl or by one or two C.sub.1-4 alkyl groups;R.sup.1 and R.sup.2 are independently hydrogen or taken together represent a chemical bond;R.sup.3 is hydrogen, C.sub.1-6 alkyl or C.sub.2-4 alkenyl; andR.sup.4 is C.sub.1-6 alkyl, C.sub.2-4 alkenyl, phenyl or benzyl;provided that R.sup.3 cannot be hydrogen when Ar is unsubstituted phenyl and R.sup.4 is n-butyl. The compounds are useful in the treatment of immediate hypersensitivity diseases including asthma.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: December 23, 1980
    Assignee: Lilly Industries Limited
    Inventors: William B. Jamieson, William J. Ross, Robin G. Simmonds, John P. Verge
  • Patent number: 4230709
    Abstract: Pharmaceutical formulations are described, which comprise a hydantoin of formula (I): ##STR1## wherein R.sup.1 is C.sub.1-4 alkyl, R.sup.2 is hydrogen or C.sub.1-4 alkyl; or R.sup.1 and R.sup.2 taken together either represent a C.sub.4-6 alkylene group or a group of formula: ##STR2## where R.sup.5 and R.sup.6 independently represent hydrogen or C.sub.1-4 alkyl;R.sup.3 is C.sub.1-6 alkyl or benzyl;R.sup.4 is hydrogen or C.sub.1-6 alkyl;provided that R.sup.2 and R.sup.4 cannot both be hydrogen;or R.sup.1 and R.sup.4 taken together represent a C.sub.2-4 alkylene group;associated with a pharmaceutically-acceptable carrier therefor. The compounds, some of which are novel, are useful in the treatment of immediate hypersensitivity diseases such as asthma.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: October 28, 1980
    Assignee: Lilly Industries Limited
    Inventors: William B. Jamieson, William J. Ross, Robin G. Simmonds, John P. Verge
  • Patent number: 4230716
    Abstract: Hydantoin compounds are described of the formula (I) : ##STR1## wherein R.sup.1 is phenyl, C.sub.1-4 hydroxyalkyl or carboxy C.sub.1-4 alkyl and wherein R.sub.2 is C.sub.1-6 alkyl. The compounds are useful in the prophylactic treatment of immediate hypersensitivity diseases including asthma.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: October 28, 1980
    Assignee: Eli Lilly Industries Limited
    Inventors: William B. Jamieson, William J. Ross, Robin G. Simmonds, John P. Verge
  • Patent number: 4222946
    Abstract: Acylamino heteroaryl compounds in which the heteroaryl nucleus is a 5-membered ring containing a single heteroatom, which may be oxygen, or sulphur, methods of making the compounds and pharmaceutical formulations containing the compounds. The compounds have anti-allergy activity.
    Type: Grant
    Filed: January 12, 1979
    Date of Patent: September 16, 1980
    Assignee: Lilly Industries, Limited
    Inventors: Delme Evans, Michael R. J. Jolley, William J. Ross, Brian P. Swann
  • Patent number: 4216219
    Abstract: Novel compounds are described of the formula ##STR1## where R is C.sub.2-6 alkyl, R.sup.1 and R.sup.2 are hydrogen or C.sub.1-4 alkyl and n is 3 to 6. The compounds are useful in the prophylactic treatment of immediate hypersensitivity diseases including asthma.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: August 5, 1980
    Assignee: Lilly Industries Limited
    Inventors: William J. Ross, Alec Todd
  • Patent number: 4215074
    Abstract: A process for preparing antidepresssant 2-phenylbicyclooctylamines of formula (I): ##STR1## where R.sup.1 and R.sup.2 represent C.sub.1-3 alkyl and Ar represents a phenyl group optionally substituted by up to two halogen atoms, by reduction of a novel enamine intermediate of formula: ##STR2## where R.sup.3 and R.sup.4 are hydrogen or taken together represent a single bond and where X is hydrogen, bromine or chlorine.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: July 29, 1980
    Assignee: Lilly Industries Limited
    Inventors: David C. Horwell, Graham H. Timms
  • Patent number: 4187232
    Abstract: Acylamino heteroaryl compounds in which the heteroaryl nucleus is a 5-membered ring containing a single heteroatom, which may be oxygen, or sulphur, methods of making the compounds and pharmaceutical formulations containing the compounds. The compounds have anti-allergy activity.
    Type: Grant
    Filed: January 19, 1978
    Date of Patent: February 5, 1980
    Assignee: Lilly Industries Limited
    Inventors: Delme Evans, Michael R. J. Jolley, William J. Ross, Brian P. Swann
  • Patent number: 4186204
    Abstract: Acylamino tetrazolyl compounds having anti-allergic activity, methods of making the compounds and pharmaceutical formulations containing the compounds.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: January 29, 1980
    Assignees: Eli Lilly and Company, Lilly Industries Limited
    Inventors: Roger G. Harrison, William B. Jamieson, William J. Ross, John C. Saunders
  • Patent number: 4176231
    Abstract: 3-Exomethylenecepham sulfoxides are prepared by the reaction of 3-methyl-3-halocepham sulfoxides with mercuric or mercurous perchlorate.
    Type: Grant
    Filed: June 1, 1978
    Date of Patent: November 27, 1979
    Assignee: Lilly Industries Limited
    Inventors: John R. Corfield, Clifford G. Taylor
  • Patent number: D267122
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: November 30, 1982
    Assignee: Lilly Industries Limited
    Inventors: Janet B. Scotton, Mark R. Hawes