Patents Assigned to Lilly Industries Limited
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Patent number: 4665189Abstract: 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: July 30, 1984Date of Patent: May 12, 1987Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William B. Jamieson, Alec Todd
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Patent number: 4636165Abstract: 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: GrantFiled: November 7, 1985Date of Patent: January 13, 1987Assignee: Lilly Industries LimitedInventor: William G. Roast
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Patent number: 4596676Abstract: Bifunctional ester derivatives at C-4 carbon of dimeric indole-dihydroindole alkaloids; e.g., VLB 4-hemisuccinate.Type: GrantFiled: March 26, 1984Date of Patent: June 24, 1986Assignee: Lilly Industries LimitedInventor: George J. Cullinan
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Patent number: 4595540Abstract: 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: October 19, 1983Date of Patent: June 17, 1986Assignee: Lilly Industries LimitedInventors: John Goldsworthy, Winston S. Marshall, John P. Verge
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Patent number: 4558124Abstract: 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: GrantFiled: May 26, 1983Date of Patent: December 10, 1985Assignee: Lilly Industries LimitedInventors: John R. Corfield, Andrew S. Miller
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Patent number: 4542131Abstract: 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: GrantFiled: August 6, 1984Date of Patent: September 17, 1985Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten
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Patent number: 4532257Abstract: 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: GrantFiled: November 30, 1983Date of Patent: July 30, 1985Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, Terry D. Lindstrom, William B. Jamieson, William J. Ross
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Patent number: 4513005Abstract: 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: GrantFiled: June 9, 1982Date of Patent: April 23, 1985Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William B. Jamieson, William J. Ross, Alec Todd
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Patent number: 4492699Abstract: 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: GrantFiled: October 13, 1983Date of Patent: January 8, 1985Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten, David J. Steggles
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Patent number: 4486591Abstract: 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: GrantFiled: September 29, 1982Date of Patent: December 4, 1984Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten
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Patent number: 4482484Abstract: 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: GrantFiled: December 5, 1983Date of Patent: November 13, 1984Assignee: Lilly Industries LimitedInventor: Robin G. Simmonds
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Patent number: 4471129Abstract: 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: GrantFiled: May 20, 1983Date of Patent: September 11, 1984Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4448787Abstract: 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: GrantFiled: September 17, 1981Date of Patent: May 15, 1984Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4442032Abstract: 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: GrantFiled: November 27, 1981Date of Patent: April 10, 1984Assignee: Lilly Industries LimitedInventor: Robin G. Simmonds
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Patent number: 4416892Abstract: 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: GrantFiled: April 14, 1982Date of Patent: November 22, 1983Assignee: Lilly Industries LimitedInventor: William Dawson
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Patent number: 4404137Abstract: 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: GrantFiled: October 2, 1980Date of Patent: September 13, 1983Assignee: Lilly Industries LimitedInventors: Jiban K. Chakrabarti, Terrence M. Hotten
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Quinolone derivatives and their use in a method of controlling an immediate hypersensitivity disease
Patent number: 4390541Abstract: 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: GrantFiled: December 3, 1981Date of Patent: June 28, 1983Assignee: Lilly Industries LimitedInventors: John Goldsworthy, William J. Ross, John P. Verge -
Patent number: 4364956Abstract: 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: GrantFiled: September 17, 1981Date of Patent: December 21, 1982Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: RE31194Abstract: 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: GrantFiled: August 17, 1981Date of Patent: March 29, 1983Assignee: Lilly Industries, LimitedInventors: David C. Horwell, David E. Tupper
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Patent number: RE32196Abstract: 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: GrantFiled: May 19, 1982Date of Patent: July 1, 1986Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, William B. Jamieson, William J. Ross