Patents Assigned to Lilly Industries Limited
  • Patent number: 4665189
    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: July 30, 1984
    Date of Patent: May 12, 1987
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, Alec Todd
  • Patent number: 4636165
    Abstract: A ring for stripping capsule sections from a tapered capsule-forming pin has an annular outer member 11 with a tapered surface 12 engaging tapered surfaces 13 on four angularly spaced sections 14 forming an inner member and with inner surfaces 15 defining a bore slidable on the pin. A spring plate 60 is held in groove 62 in member 11 and bears on an end face of the sections 14 to hold the sections in engagement with the pin and resist radially outwards movement of the sections 14 when they engage the capsule section. In modified arrangements the plate 60 embraces the member 11 and engages an end face of the sections 14; and the plate 60 is replaced by a spring clip embracing the sections 14 which extend beyond the member 11.
    Type: Grant
    Filed: November 7, 1985
    Date of Patent: January 13, 1987
    Assignee: Lilly Industries Limited
    Inventor: William G. Roast
  • Patent number: 4596676
    Abstract: Bifunctional ester derivatives at C-4 carbon of dimeric indole-dihydroindole alkaloids; e.g., VLB 4-hemisuccinate.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: June 24, 1986
    Assignee: Lilly Industries Limited
    Inventor: George J. Cullinan
  • Patent number: 4595540
    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: October 19, 1983
    Date of Patent: June 17, 1986
    Assignee: Lilly Industries Limited
    Inventors: John Goldsworthy, Winston S. Marshall, John P. Verge
  • Patent number: 4558124
    Abstract: There is described a process for preparing a sulphoxide of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4, taken individually, are alkyl, alkoxy or aryl groups, X is an alkylene group, R.sup.5 is a carboxylic acid protecting group and Y is a linking group through one or two carbon atoms forming a penam or cephem nucleus, which comprises reacting a compound of formula ##STR2## with an oxidizing agent. .alpha.-Sulphoxide compounds of formula (I) are also provided as novel intermediates.
    Type: Grant
    Filed: May 26, 1983
    Date of Patent: December 10, 1985
    Assignee: Lilly Industries Limited
    Inventors: John R. Corfield, Andrew S. Miller
  • Patent number: 4542131
    Abstract: Compounds are described of the formula ##STR1## or an acid addition salt thereof; in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, halogen, C.sub.1-4 haloalkyl, C.sub.1-4 alkanoyl, nitro, amino, C.sub.2-4 acylamino, cyano, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 haloalkoxy or a group of the formula --SO.sub.2 N(R.sup.8).sub.2, --SO.sub.2 R.sup.8 or --SO.sub.3 R.sup.8 where R.sup.8 is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or optionally substituted phenyl; in which R.sup.5 is a group of the formula ##STR2## where R.sup.9 is hydrogen, C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkanoyl, benzyl, cyano or optionally substituted phenyl, where R.sup.10 is hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl and where n is 0 or 1; in which R.sup.6 is hydrogen, C.sub.1-10 alkyl, C.sub.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: September 17, 1985
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten
  • Patent number: 4532257
    Abstract: There are described compounds of the formula ##STR1## in which either R.sup.1 and R.sup.2 are both hydrogen or R.sup.1 is carboxyl and R.sup.2 is hydrogen, C.sub.3-4 alkenyl or C.sub.1-4 alkyl, and R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, nitro, hydroxyl, carboxyl, carboxyC.sub.1-2 alkoxy, C.sub.3-4 alkenyl, C.sub.1-4 alkyl, C.sub.3-4 alkenyloxy, C.sub.1-4 alkoxy or the group ##STR2## where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl; and salts and esters thereof. The compounds are indicated for use in the treatment of immediate sensitivity reactions and inflammatory diseases.
    Type: Grant
    Filed: November 30, 1983
    Date of Patent: July 30, 1985
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, Terry D. Lindstrom, William B. Jamieson, William J. Ross
  • Patent number: 4513005
    Abstract: There are described pharmacologically active compounds, useful in the treatment of allergic/inflammatory disorders involving SRS-A as causal mediator and which, in free acid form, are of formula I, ##STR1## in which R.sub.1 is (i) an aliphatic, saturated or unsaturated hydrocarbyl radical of up to 20 carbon atoms, unsubstituted or substituted by at least one substituent selected from halogen, hydroxy, C.sub.3-6 alkoxy, C.sub.3-6 cycloalkyl, aryl or heteroaryl, the cycloalkyl, aryl or heteroaryl being unsubstituted or substituted by at least one substituent selected from hydroxy, halogen and alkyl, alkenyl or alkynyl of up to 10 carbon atoms,(ii) cycloalkyl of 3 to 8 carbon atoms unsubstituted or substituted by alkyl, alkenyl or alkynyl of up to 16 carbon atoms, or(iii) aryl or heteroaryl, unsubstituted or substituted by hydroxyl, C.sub.1-4 alkoxy, halogen or alkyl, alkenyl or alkynyl of up to 16 carbon atoms; and R.sub.
    Type: Grant
    Filed: June 9, 1982
    Date of Patent: April 23, 1985
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, William J. Ross, Alec Todd
  • Patent number: 4492699
    Abstract: These are described compounds of formula (I) ##STR1## or an acid addition salt thereof; in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent 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 or C.sub.1-6 alkyl, 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; and in which R.sup.6 is attached to the 1, 2 or 3 position of the triazole ring and is hydrogen, C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, phenyl, benzyl or acyl. These compounds are pharmaceutically active and are especially useful in the treatment of disorders of the central nervous system. They are prepared by reacting an amine of formula R.sup.
    Type: Grant
    Filed: October 13, 1983
    Date of Patent: January 8, 1985
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten, David J. Steggles
  • Patent number: 4486591
    Abstract: Compounds are described of the formula ##STR1## or an acid addition salt thereof; in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, halogen, C.sub.1-4 haloalkyl, C.sub.1-4 alkanoyl, nitro, amino, C.sub.2-4 acylamino, cyano, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 haloalkoxy or a group of the formula -SO.sub.2 N(R.sup.8).sub.2, -SO.sub.2 R.sup.8 or -SO.sub.3 R.sup.8 where R.sup.8 is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or optionally substituted phenyl; in which R.sup.5 is a group of the formula ##STR2## where R.sup.9 is hydrogen, C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkanoyl, benzyl, cyano or optionally substituted phenyl, where R.sup.10 is hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl and where n is 0 or 1; in which R.sup.6 is hydrogen, C.sub.1-10 alkyl, C.sub.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: December 4, 1984
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten
  • Patent number: 4482484
    Abstract: Compounds of formula (I) ##STR1## in which n is 1 or 2, R.sup.1 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, amino, halo or hydroxy, m is 0, 1 or 2, R.sup.2 is an immunogenic determinant and x is 1 or 2, provided that when n is 1, x is 1 or 2 and there is one diazo moiety at the 3-position or two diazo moieties at the 3- and 5-positions, with respect to the isothiocyanate group, and the hydroxy group is at the 4-position; and provided that when n is 2, x is 1 and the diazo moiety is at the 4-position and the hydroxy groups are at the 3- and 5-positions, are described. The compounds are useful in the preparation of immunoglobulin conjugates for employment in diagnostic techniques.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: November 13, 1984
    Assignee: Lilly Industries Limited
    Inventor: Robin G. Simmonds
  • Patent number: 4471129
    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: May 20, 1983
    Date of Patent: September 11, 1984
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4448787
    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: September 17, 1981
    Date of Patent: May 15, 1984
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4442032
    Abstract: Compounds of formula (I) ##STR1## in which n is 1 or 2, R.sup.1 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, amino, halo or hydroxy, m is 0, 1 or 2, R.sup.2 is an immunogenic determinant and x is 1 or 2, provided that when n is 1, x is 1 or 2 and there is one diazo moiety at the 3-position or two diazo moieties at the 3- and 5-positions, with respect to the isothiocyanate group, and the hydroxy group is at the 4-position; and provided that when n is 2, x is 1 and the diazo moiety is at the 4-position and the hydroxy groups are at the 3- and 5-positions, are described. The compounds are useful in the preparation of immunoglobulin conjugates for employment in diagnostic techniques.
    Type: Grant
    Filed: November 27, 1981
    Date of Patent: April 10, 1984
    Assignee: Lilly Industries Limited
    Inventor: Robin G. Simmonds
  • Patent number: 4416892
    Abstract: The invention relates to a method for the prophylactic or therapeutic treatment of an immediate hypersensitivity disease, which comprises administering to a mammal, including a human, a compound of the following formula ##STR1## in which the group --CHR.sup.1 R.sup.2 is in the 5- or 6- position of the benzoxazole nucleus, R.sup.1 is hydrogen or C.sub.1-4 alkyl, R.sup.2 is selected from the group --COOH or a salt or ester thereof, the group --CONH.sub.2 and the group --CH.sub.2 OH, and in which R.sup.4 is a phenyl group optionally substituted by one or two groups selected from halogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl and C.sub.1-4 haloalkyl, or optionally substituted in two adjacent positions by methylenedioxy.
    Type: Grant
    Filed: April 14, 1982
    Date of Patent: November 22, 1983
    Assignee: Lilly Industries Limited
    Inventor: William Dawson
  • Patent number: 4404137
    Abstract: Compounds are described of the formula ##STR1## or an acid addition salt thereof; in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, halogen, C.sub.1-4 haloalkyl, C.sub.1-4 alkanoyl, nitro, amino, C.sub.2-4 acylamino, cyano, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 haloalkoxy or a group of the formula --SO.sub.2 N(R.sup.8).sub.2, --SO.sub.2 R.sup.8 or --SO.sub.3 R.sup.8 where R.sup.8 is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl or optionally substituted phenyl; in which R.sup.5 is a group of the formula ##STR2## where R.sup.9 is hydrogen, C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkanoyl, benzyl, cyano or optionally substituted phenyl, where R.sup.10 is hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl and where n is 0 or 1; in which R.sup.6 is hydrogen, C.sub.1-10 alkyl, C.sub.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: September 13, 1983
    Assignee: Lilly Industries Limited
    Inventors: Jiban K. Chakrabarti, Terrence M. Hotten
  • Patent number: 4390541
    Abstract: Compounds of the following formula are described: ##STR1## in which n is 0, 1 or 2, R.sup.1 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl, trifluoromethyl, halo or nitro, and R.sup.2 and R.sup.3 are each independently hydrogen or C.sub.1-4 alkyl, and salts thereof. The compounds are useful in the treatment of immediate hypersensitivity conditions and are prepared by reaction of the appropriate formylquinolone with malonic acid, ylid or phosphonate.
    Type: Grant
    Filed: December 3, 1981
    Date of Patent: June 28, 1983
    Assignee: Lilly Industries Limited
    Inventors: John Goldsworthy, William J. Ross, John P. Verge
  • Patent number: 4364956
    Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or 5-tetrazolylaminocarbonyl, where R.sup.5 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is a group of the formulaR.sup.6 --(Z).sub.m --where m is O or 1, Z is O, S, SO, SO.sub.2 or CO, and R.sup.6 phenyl optionally substituted by one or more group selected from halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkoxy, benzyloxy, hydroxy, nitro, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, amino and NHR.sup.7 where R.sup.7 is C.sub.2-6 acyl; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. These compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
    Type: Grant
    Filed: September 17, 1981
    Date of Patent: December 21, 1982
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: RE31194
    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: August 17, 1981
    Date of Patent: March 29, 1983
    Assignee: Lilly Industries, Limited
    Inventors: David C. Horwell, David E. Tupper
  • Patent number: RE32196
    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: May 19, 1982
    Date of Patent: July 1, 1986
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, William J. Ross