Patents Assigned to Xenova Limited
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Patent number: 7132419Abstract: A compound which is a benzo[a]phenazine-11-carboxamide derivative of formula (I) wherein each of R1 to R4, which are the same or different, is selected from hydrogen, halogen, hydroxyl, C1–C6 alkoxy which is unsubstituted or substituted, heteroaryloxy, C1–C6 alkyl which is unsubstituted or substituted, nitro, cyano, azido, amidoxime, CO2R10, CON(R12)2, OCON(R12), SR10, SOR11, SO2R11, SO2N(R12)2, N(R12)2, NR10SO2R11, N(SO2R11)2 NR10(CH2)nCN, NR10COR11, OCOR11 or COR10; each of R5 to R7, which are the same or different, is selected from hydrogen, halogen, hydroxy, C1–C6 alkoxy, C1–C6 alkyl, SR10 and N(R12)2; Q is C1–C6 alkylene which is unsubstituted or substituted by (i) C1–C6 alkyl which is unsubstituted or substituted, (ii) hydroxy, provided that the hydroxy group is not ? to either of the N atoms adjacent to Q in formula (I), (iii) CO2R10, or (iv) CON(R12); R8 and R9, which are the same or different, are each hydrogen or C1–C6 alkyl, or R8 and R9 together with the nitrogen atom to which they are attachType: GrantFiled: December 30, 2004Date of Patent: November 7, 2006Assignee: Xenova LimitedInventors: John Milton, Nigel Vicker, Adrian Folkes, Shouming Wang, William Alexander Denny
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Publication number: 20050222199Abstract: A hydrate of an acid addition bis-salt of an anthranilic acid derivative is produced by a process which comprises: (a) combining, in any order, the anthranalic acid derivative, a pharmaceutically acceptable organic solvent, an excess of water and a pharmaceutically acceptable strong acid to form a mixture; (b) warming the mixture until a clear solution forms; (c) filtering the solution while it is warm, to yield a filtrate; and (d) recovering the hydrate as defined above from the filtrate. The hydrate has a defined number of moles of water of crystallisation and possesses better storage stability and dissolution characteristics than conventionally produced hydrates of such acid addition his-salts.Type: ApplicationFiled: May 13, 2003Publication date: October 6, 2005Applicant: Xenova LimitedInventors: David Hayman, Michael Wright
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Publication number: 20050143383Abstract: A compound which is a benzo[a]phenazine-11-carboxamide derivative of formula (I) wherein each of R1 to R4, which are the same or different, is selected from hydrogen, halogen, hydroxyl, C1-C6 alkoxy which is unsubstituted or substituted, heteroaryloxy, C1-C6 alkyl which is unsubstituted or substituted, nitro, cyano, azido, amidoxime, CO2R10, CON(R12)2, OCON(R12), SR10, SOR11, SO2R11, SO2N(R12)2, N(R2)2, NR10SO2R11, N(SO2R11)2 NR10(CH2)nCN, NR10COR11, OCOR11 or COR10; each of R5 to R7, which are the same or different, is selected from hydrogen, halogen, hydroxy, C1-C6 alkoxy, C1-C6 alkyl, SR10 and N(R12)2; Q is C1-C6 alkylene which is unsubstituted or substituted by (i) C1-C6 alkyl which is unsubstituted or substituted, (II) hydroxy, provided that the hydroxy group is not ? to either of the N atoms adjacent to Q in formula (I), (iii) CO2R10, or (iv) CON(R12); R8 and R9, which are the same or different, are each hydrogen or C1-C6 alkyl, or R8 and R9 together with the nitrogen atom to which they are attaType: ApplicationFiled: December 30, 2004Publication date: June 30, 2005Applicant: Xenova LimitedInventors: John Milton, Nigel Vicker, Adrian Folkes, Shouming Wang, William Denny
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Patent number: 6552021Abstract: A compound which is a heteroaromatic[a]phenazine carboxamide derivative of formula (I) wherein X is a five- or six-membered heteroaromatic ring which contains one or two nitrogen atoms and which is unsubstituted or substituted by C1-C6 alkyl, hydroxyl or C1-C6 alkoxy; Q is C1-C6 alkylene which is unsubstituted or substituted by C1-C6 alkyl which is unsubstituted or substituted by a hydroxy group; and R1 and R2 which are the same or different are each C1-C6 alkyl; or a pharmaceutically acceptable salt thereof. These compounds are inhibitors of topoisomerase I and II and can be used to treat tumours, including tumours which express MDR.Type: GrantFiled: March 5, 2001Date of Patent: April 22, 2003Assignee: Xenova LimitedInventors: John Milton, Nigel Vicker, William Alexander Denny, Swarnalatha Akuratiya Gamage, Julie Ann Spicer
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Patent number: 6518316Abstract: A compound of formula (I), wherein &agr;X is ═O, ═N—OR6, &bgr;NHR or &bgr;OH wherein R6 is H or C1-C6 alkyl, bond a is oriented &ggr; or &dgr; and R is H, C1-C6 alkyl which is unsubstituted or substituted by C6-C10 aryl, or C3-C6 cycloalkyl; &egr; is a bond when &zgr; and &eegr; are not bonds or, when X is ═O, &zgr; and &eegr; are both bonds and &egr; is not a bond; R1 and R2, which are the same or different, are H or a halogen; R3 and R4, which are the same or different, are H, C1-C6 alkyl, C3-C6 cycloalkyl, a heterocyclic group or an aromatic group; bond e is oriented &ggr; or &dgr;; and R5 is C1-C6 alkyl; or formula (Ib), or formula (II), or formula (III), has activity as a cytokine production inhibitor and an inhibitor and an inhibitor of tyrosine kinase.Type: GrantFiled: March 27, 2001Date of Patent: February 11, 2003Assignee: Xenova LimitedInventors: Roya Mansour Sadeghi Guilani, Stephen Keith Wrigley, Sangeeta Bahl, Steven Michael Martin, David Andrew Kau, Jenny Seugkin Tang, Michael Moore, David James Hardick
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Patent number: 6218393Abstract: Anthranilic acids of formula (I): wherein each of R to R9 is an organic substituent, n is 0 or 1, m is 0 or an integer of 1 to 6, q is 0 or 1, X is a direct bond, O, S, —S—(CH2)p or —O—(CHO2)p— wherein p is from 1 to 6 and Ar is an unsaturated carbocyclic or heterocyclic group, and the pharmaceutically acceptable salts thereof, have activity as inhibitors of P-glycoprotein and may thus be used, inter alia, as modulators of multidrug resistance in the treatment of multidrug resistant cancers, for example to potentiate the cytotoxicity of a cancer drug.Type: GrantFiled: June 9, 1999Date of Patent: April 17, 2001Assignee: Xenova LimitedInventors: Hamish Ryder, Philip Anthony Ashworth, Michael Bryan Roe, Julie Elizabeth Brumwell, Sukhjit Hunjan, Adrian John Folkes, Jason Terry Sanderson, Susannah Williams, Levi Michael Maximen
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Patent number: 6114332Abstract: A compound which is a bis(acridinecarboxamide) or bis(phenazinecarboxamide) derivative of formula (I): ##STR1## wherein each X, which may be the same or different in a given molecule, is --CH.dbd. or --N.dbd. each of R.sub.1 to R.sub.4 which may be the same or different, H, C.sub.1 -C.sub.4 alkyl, OH, SH, NH.sub.2, C.sub.1 -C.sub.4 alkoxy, aryloxy, NHR, N(R).sub.2, SR, SO.sub.2 R wherein R is C.sub.1 -C.sub.4 alkyl, CF.sub.3, NO.sub.2 or halogen, or R.sub.1 and R.sub.2 together form a methylenedioxy group; each of R.sub.5 and R.sub.6, which may be the same or different, is H or C.sub.1 -C.sub.4 alkyl; Z is (CH.sub.2).sub.n, (CH.sub.2).sub.n O(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.n, (CH.sub.2).sub.n N(R.sub.7)(CH.sub.2).sub.m N(R.sub.7)(CH.sub.2).sub.n or (CH.sub.2).sub.n N(CH.sub.2 CH.sub.2).sub.2 N(CH.sub.2).sub.n wherein R.sub.7 is H or C.sub.1 -C.sub.Type: GrantFiled: June 18, 1999Date of Patent: September 5, 2000Assignee: Xenova LimitedInventors: William Alexander Denny, Swarnalatha Akuritaya Gamage, Julie Ann Spicer, Bruce Charles Baguley, Graeme John Finlay
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Patent number: 6111109Abstract: A process for producing an acridine carboxamide of formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.5 and R.sup.6, which may be the same or different, is H or an organic subsituent, x is from 1 to 6 and Y is N(R)2 wherein R is C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 18, 1999Date of Patent: August 29, 2000Assignee: Xenova LimitedInventors: William Alexander Denny, Swarnalatha Akuratiya Gamage, Julie Ann Spicer, Michael Wright, David Frank Hayman
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Patent number: 5935955Abstract: A piperazinedione of general formula (I): ##STR1## wherein R.sup.1 is selected from hydrogen;a group of formula --(NH).sub.t --COR.sup.3 wherein t is 0 or 1 and R.sup.3 is an organic substituent as defined herein;a group of formula (D): ##STR2## and a group of formula (E): ##STR3## and the pharmaceutically acceptable salts thereof are useful as modulators of multi-drug resistance.Type: GrantFiled: August 29, 1997Date of Patent: August 10, 1999Assignee: Xenova LimitedInventors: Philip A. Ashworth, Sukhjit Hunjan, Ian A. Pretswell, Harnish Ryder, Stephen J. Brocchini
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Patent number: 5902812Abstract: Diketopiperazines of formula (A): ##STR1## wherein each of R.sub.1 to R.sub.8 is H or an organic radical as described herein and the pharmaceutically acceptable salts thereof have activity as inhibitors of plasminogen activator inhibitor.Type: GrantFiled: September 24, 1996Date of Patent: May 11, 1999Assignee: Xenova LimitedInventors: Stephen James Brocchini, Justin Stephen Bryans, Adrian John Folkes, Christopher John Latham, Julie Elizabeth Brumwell
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Patent number: 5891886Abstract: A new treatment schedule for administration of N-?2-(dimethylamino)ethyl!acridine-4-carboxamide and other related carboxamide anticancer drugs in which the drug is administered in a divided-dose schedule comprising two or more administrations at frequent intervals, for example every hour. Schedules to produce cyclic peaks/troughs in plasma levels are mentioned. The compounds can be used for circumventing multidrug resistance in cancers and may, for example, be used in combination with other cytotoxic drugs, especially non-topo II inhibitors. Treatment of melanoma and advanced colon cancer is included.Type: GrantFiled: August 29, 1997Date of Patent: April 6, 1999Assignee: Xenova LimitedInventors: Bruce Charles Baguley, Graham John Atwell, William Alexander Denny, Graeme John Finlay, Gordon William Rewcastle
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Patent number: 5891877Abstract: Diketopiperazines of the formula ##STR1## where one or both of R.sub.1 and R.sub.2, which are different, are chosen from X and a phenyl group substituted by X, C(O)X, OC(O)CH.sub.2 X, OCH.sub.2 CH.sub.2 X, CH.sub.2 X, CONH(CH.sub.2).sub.n X, O(CH.sub.2).sub.n CH(OH)(CH.sub.2).sub.n X ##STR2## and, where appropriate, the other of R.sub.1 and R.sub.2 is a phenyl group optionally substituted by one or more groups selected from halogen, nitro, methoxy, NHC(O)R.sub.12, CO.sub.2 H, O(CH.sub.2).sub.n N(R.sub.12 R.sub.13), C.sub.1 -C.sub.4 alkyl and (CH.sub.2).sub.n C(O)OR.sub.12 ; X is a five- or six-membered heterocyclic ring selected from the group consisting of pyridyl, imidazolyl, furyl, pyrrolyl, pyrrolidinyl, thienyl, piperazinyl, piperidinyl, morpholinyl, quinolyl, isoquinotyl and indolyl, the heteroatom(s) of the said heterocyclic ring, when nitrogen, being optionally substituted by hydrogen, methyl, oxygen, tertiary-butyloxycarbonyl, or SO.sub.Type: GrantFiled: September 25, 1996Date of Patent: April 6, 1999Assignee: Xenova LimitedInventors: Stephen James Brocchini, Justin Stephen Bryans, Adrian John Folkes, Christopher John Latham, Julie Elizabeth Brumwell
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Patent number: 5861400Abstract: Piperazine derivatives of the formula ##STR1## their esters and salts are useful as modulators of multiple drug resistance.Type: GrantFiled: November 4, 1996Date of Patent: January 19, 1999Assignee: Xenova LimitedInventors: Stephen James Brocchini, Justin Stephen Bryans, Christopher John Latham, Adrian John Folkes
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Patent number: 5852018Abstract: Piperazine derivatives of formula (A): ##STR1## wherein .sub.-------- denotes an optional bond, provided that either .sub.----.sup.a.sub.---- and .sub.----.sup.c.sub.---- are both bonds and .sub.----.sup.b.sub.---- and .sub.----.sup.d.sub.---- are not bonds, or .sub.----.sup.b.sub.---- and .sub.----.sup.d.sub.---- are both bonds and .sub.----.sup.a.sub.---- and .sub.----.sup.c.sub.---- are not bonds; each of R.sub.14 and R.sub.15 is independently selected from hydrogen and C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by an organic functional group; and each of R.sub.1 to R.sub.10, which may be the same or different, is independently hydrogen or an organic functional group; and the pharmaceutically acceptable salts and esters thereof have utility as modulators of multiple drug resistance (MDR).Type: GrantFiled: November 4, 1996Date of Patent: December 22, 1998Assignee: Xenova LimitedInventors: Justin Stephen Bryans, Christopher John Latham, Stephen James Brocchini
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Patent number: 5750530Abstract: A diketopiperazine of formula (I): ##STR1## wherein each of R.sub.7 and R.sub.8 which may be the same or different; is hydrogen or a nitro group;Y is ##STR2## --O-- or --S--, wherein each of R.sub.9 and R.sub.10 which may be the same or different, is hydrogen or a nitro group;n is 0, 1 or 2;m is an integer of 1 to 6;each R.sub.6, which may be the same or different, is a C.sub.1 -C.sub.6 alkyl group; andX is selected from(i) a phenyl group of the following formula ##STR3## and the salts and esters thereof; have activity as inhibitors of plasminogen activator inhibitor.Type: GrantFiled: December 17, 1996Date of Patent: May 12, 1998Assignee: Xenova LimitedInventors: Justin Stephen Bryans, Adrian John Folkes, Christopher John Latham
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Patent number: 5700804Abstract: Diketopiperazines of the formula: ##STR1## where each of R.sub.1 to R.sub.10, which may be the same or different, is independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by one or more halogen atoms, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, halogen, hydroxy, nitro, phenyl, -cyano, --CH.sub.2 OH, --CH.sub.2 COOH, --CO.sub.2 R.sup.11, --NHCOR.sup.11, --NHSO.sub.2 R.sup.13, --SO.sub.2 R.sup.13, --CON(R.sup.11 R.sup.12), --SOR.sup.13, --SO.sub.2 N(R.sup.11 R.sup.12), --N(R.sup.11 R.sup.12), and --O(CH.sub.2).sub.n N(R.sup.11 R.sup.12), --O(CH.sub.2).sub.n CO.sub.2 R.sup.11, --OCOR.sup.11, --CH.sub.2 OCOR.sup.11, --CH.sub.2 NHCOR.sup.11, --CH.sub.2 NHCOOR.sup.13, --CH.sub.2 SR.sup.11, --CH.sub.2 SCOR.sup.11, --CH.sub.2 S(O).sub.m R.sup.13 wherein m is 1 or 2, --CH.sub.2 NHCO(CH.sub.2).sub.n CO.sub.2 R.sup.11, --N(R.sup.11)COR.sup.12, --NHCOCF.sub.3, --NHCO(CH.sub.2).sub.n CO.sub.2 R.sup.11, --NHCO(CH.sub.2).sub.n OCOR.sup.11 and --NHCO(CH.Type: GrantFiled: April 11, 1995Date of Patent: December 23, 1997Assignee: Xenova LimitedInventors: Mark Anthony David Collins, Maria Ines Chicarelli-Robinson, Justin Stephen Bryans, Stephen James Brocchini, Christopher John Latham, John Richardson Shaw
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Patent number: 5696131Abstract: A new treatment schedule for administration of N-?2-(dimethylamino)ethyl!acridine-4-carboxamide and other related carboxamide anticancer drugs in which the drug is administered in a divided-dose schedule comprising two or more administrations at frequent intervals, for example every hour. Schedules to produce cyclic peaks/troughs in plasma levels are mentioned. The compounds can be used for circumventing multidrug resistance in cancers and may, for example, be used in combination with other cytotoxic drugs, especially non-topo II inhibitors. Treatment of melanoma and advanced colon cancer is included.Type: GrantFiled: February 13, 1995Date of Patent: December 9, 1997Assignee: Xenova LimitedInventors: Bruce Charles Baguley, Graham John Atwell, William Alexander Denny, Graeme John Finlay, Gordon William Rewcastle
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Patent number: 5565486Abstract: Sesquiterpenes obtainable from the fungal strain Acremonium strictum XO6/15/458, and phannaceutically and veterinarily acceptable salts thereof, are inhibitors of the binding of benzodiazepine to the GABA-benzodiazepine-Cl ionophore receptor complex. These compounds are prepared by (i) fermenting, in a source of carbon, nitrogen and inorganic salts, fungal strain XO6/15/458 (IMI 354451) or a mutant thereof which produces the sesquiterpenes, (ii) isolating the sesquiterpenes from the fermentation medium; and (iii) if desired, converting the sesquiterpene into a pharmaceutically or veterinarily acceptable salt.Type: GrantFiled: August 29, 1995Date of Patent: October 15, 1996Assignee: Xenova LimitedInventors: Didier V. Renno, Gerard B. O'Beirne, Brent R. Copp
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Patent number: 5306732Abstract: Vinigrol or a pharmaceutically acceptable salt thereof is useful as a tumour necrosis factor antagonist. Vinigrol may therefore be used to treat endotoxic shock, inflammation, infection or cachexia.Type: GrantFiled: June 24, 1992Date of Patent: April 26, 1994Assignee: Xenova LimitedInventors: David B. Norris, Paul Depledge, Andrew P. Jackson