Patents by Inventor Philip Wilson Howard
Philip Wilson Howard has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20110160192Abstract: Compounds of formula (I): Z?-CO-A-B—NH-Z (I) wherein: Z is H or an amino protecting group; Z? is OH, a protected or activated hydroxyl group or Cl; A is an optionally substituted C5-6 arylene group; and B is an optionally substituted C5-6 arylene group.Type: ApplicationFiled: March 7, 2011Publication date: June 30, 2011Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Geoffrey Wells
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Patent number: 7741319Abstract: The present inventors have developed a key intermediate for the production of C2 substituted PBDs, which has a leaving group at the C2 position, a carbamate protecting group at the N10 position and a protected hydroxy group at the C11 position. In a first aspect, the present invention comprises a compound with a the formula (I), wherein: R10 is a carbamate-based nitrogen protecting group; R11 is an oxygen protecting group; and R2 is a labile leaving group. In a further aspect, the present invention comprises a method of synthesising a compound of formula (III), or a solvate thereof, from a compound of formula (I) as defined in the first aspect, R16 is either O—R11, wherein R11 is as defined in the first aspect, or OH, or R10 and R16 together form a double bond between N10 and C11; and R15 is R. The other substituents are defined in the claims.Type: GrantFiled: March 1, 2005Date of Patent: June 22, 2010Assignee: Spirogen LimitedInventors: Philip Wilson Howard, Stephen John Gregson
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Publication number: 20100113425Abstract: Compounds of the formula I: or solvate thereof, wherein: R2 is an optionally substituted C5-20 aryl group; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, nitro, Me3Sn and halo; where R and R? are independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR?, nitro, Me3Sn and halo; R? is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings; X is selected from O, S, or NH; z is 2 or 3; M is a monovalent pharmaceutically acceptable cation; R2?, R6?, R7?, R9?, X? and M? are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M? may together represent a divalent pharmaceutically acceptable cation.Type: ApplicationFiled: November 2, 2009Publication date: May 6, 2010Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Zhizhi Chen, Stephen John Gregson
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Patent number: 7704924Abstract: A compound of formula (IV): O is a solid support; L is a linking group or a single bond; X? is selected from CO, NH, S, or O; A is O, S, NH, or a single bond; R2 and R3 are independently selected from: H, R, OH, OR, ?O, ?CH—R, ?CH2, CH2—CO2R, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR, CN and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, and R9 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11 is either H or R; Q is S, O or NH; R10 is a nitrogen protecting group; and Y is a divalent group such that HY?R, and other related compounds and collections of compounds.Type: GrantFiled: June 24, 2003Date of Patent: April 27, 2010Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 7612062Abstract: Compounds of the formula: (I) or solvate thereof, wherein: R2 is an optionally substituted C5-20 aryl group; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, nitro, Me3Sn and halo; where R and R? are independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR?, nitro, Me3Sn and halo; R? is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings; X is selected from O, S, or NH; z is 2 or 3; M is a monovalent pharmaceutically acceptable cation; R2?, R6?, R7?, R9?, X? and M? are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M? may together represent a divalent pharmaceutically acceptable cation.Type: GrantFiled: April 21, 2006Date of Patent: November 3, 2009Assignee: Spirogen LimitedInventors: Stephen John Gregson, Philip Wilson Howard, Zhizhi Chen
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Patent number: 7557099Abstract: Compounds and a method of synthesis of compounds of formula (Ia) or (Ib): and salts, solvates, and chemically protected forms thereof, wherein the dotted lines indicate the optional presence of a double bond between C1 and C2 or C2 and C3; R2 and R3 are independently selected from —H, ?O, ?CH2, —CN, —R, OR, halo, ?CH—R, O—SO2—R, CO2R and COR; R10 is a carbamate-based nitrogen protecting group; and R11 is an oxygen protecting group.Type: GrantFiled: March 1, 2005Date of Patent: July 7, 2009Assignee: Spirogen LimitedInventors: Philip Wilson Howard, Gyoung-Dong Kang
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Patent number: 7528126Abstract: A compound of formula (I) and salts and solvates thereof, wherein: R10 is a nitrogen protecting group and R11 is either OH or O—R12, wherein R12 is an oxygen protecting group, or R10 and R11 together form a double bond between N10 and C11; and R10? and R11? are selected from the same options as R10 and R11 respectively.Type: GrantFiled: March 9, 2005Date of Patent: May 5, 2009Assignee: Spirogen LimitedInventors: Philip Wilson Howard, Stephen John Gregson, Peter William Taylor, David Edwin Thurston, Tsveta Stefanova Hadjivassileva
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Publication number: 20080214525Abstract: A compound of formula (I); or a salt or solvate thereof, wherein: the dotted line indicates the optional presence of a double bond between C2 and C3; R2 is selected from —H, —OH, =0, ?CH2, —CN, —R, OR, halo, ?CH—R, O—SO2—R, CO2R and COR; R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, nitro, Me3Sn and halo, where R and R? are independently selected from optionally substituted C1-7 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; R10 and R11 either together form a double bond, or are selected from H and YRY, where Y is selected from O, S and NH and R is H or C1-7 alkyl or H and SOxM, where x is 2 or 3 and M is a monovalent pharmaceutically acceptable cation; each X is independently a heteroarylene group; n is from 1 to 6; and RE is C1-4 alkyl. The compound is useful for the treatment of proliferative diseases.Type: ApplicationFiled: October 5, 2006Publication date: September 4, 2008Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, David Edwin Thurston, Geoffrey Wells
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Patent number: 7407951Abstract: Compounds of formula (I): formula (I) and salts, solvates, chemically protected forms, and prodrugs thereof, are disclosed wherein R2 is selected from: an optionally substituted napthyl group; an optionally substituted thiophenyl or furanyl group; and a phenyl group substituted by: one or more chloro or fluoro groups; an ethyl or propyl group; a 4-t-butyl group; a 2-methyl group; or two methyl groups in the 2- and 6-positions.Type: GrantFiled: November 14, 2003Date of Patent: August 5, 2008Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Publication number: 20080167293Abstract: Compounds of the formula: (I) or solvate thereof, wherein: R2 is an optionally substituted C5-20 aryl group; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, nitro, Me3Sn and halo; where R and R? are independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; R7 is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR?, nitro, Me3Sn and halo; R? is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings; X is selected from O, S, or NH; z is 2 or 3; M is a monovalent pharmaceutically acceptable cation; R2?, R6?, R7?, R9?, X? and M? are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M? may together represent a divalent pharmaceutically acceptable cation.Type: ApplicationFiled: April 21, 2006Publication date: July 10, 2008Applicant: Spirogen LimitedInventors: Philip Wilson Howard, Zhizhi Chen, Stephen John Gregson
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Patent number: 7265105Abstract: A compound of the formula II: wherein: R?2 is CHR?2, where R?2 is H. R6 and R9 are H and R7 is OMe and the compound is a dimer with each monomer being the same and being of formula II, where the R8 groups of the monomers form together a bridge having the formula —O—(CH2)p—O—, where p is 5, linking the monomers.Type: GrantFiled: March 2, 2006Date of Patent: September 4, 2007Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 7067511Abstract: Compounds of the formulae Ia and Ib: wherein: A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula —X—R?—X— linking the monomers, where R? is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH?CH(CONH2) or CH?CH(CONMe2). Other related compounds are also disclosed.Type: GrantFiled: December 12, 2001Date of Patent: June 27, 2006Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 7049311Abstract: Compounds of formula (Ia) and (Ib) wherein A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula (Ia) or (Ib), where the R8 groups of the monomers form together a bridge having the formula —X—R?—X— linking the monomers, where R? is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon—carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula (Ia) when A is a single bond, then R2 is not CH?CH(CONH2) or CH?CH(CONMe2).Type: GrantFiled: August 27, 1999Date of Patent: May 23, 2006Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 6909006Abstract: Compounds of formula (III) or (V), wherein is a solid support; L is a linking group or a single bond; T is a combinatorial unit; n is a positive integer, where if n is greater than 1, each T may be different: X is an electrophilic leaving group; Y is selected from NH-Prot, O-Prot, S-Prot, NO2, —NHOH. N3, NHR, NRR, N?NR, N(O)RR, NHSO2R, N?N?PhR, SR or SSR, where Prot represents a protecting group; A and B collectively represent a fused benzene or pyrrole ring (in either orientation), which is optionally substituted by up to respectively 4 or 2 groups independently selected from R, OH, OR, halo, nitro, amino, Me3Sn, CO2H, CO2R, R1 is a nitrogen protecting group, where if Y includes a protecting group, these protecting groups are orthogonal and R2 and R7 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn, and other related compounds and collections of compounds.Type: GrantFiled: February 22, 2000Date of Patent: June 21, 2005Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Publication number: 20040198722Abstract: A compound of formula (I), wherein: R2 and R3 are independently selected from H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR and CN, and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, R8 and R9 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11 is either H or R; Q is S, O or NH; L is a linking group, or a single bond; O is a solid support; or where one or more of R2, R3, R6, R7 and R8 are independently: H—(T)n—X—Y—A— where: X is CO, NH, S or O; T is a combinatorial unit; Y is a divalent group such that HY═R; A is O, S, NH, or a single bond and n is a positive integer.Type: ApplicationFiled: April 15, 2004Publication date: October 7, 2004Applicant: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 6747144Abstract: A compound of formula (I), wherein: R2 and R3 are independently selected from H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR and CN, and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, R8 and R9 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11 is either H or R; Q is S, O or NH; L is a linking group, or a single bond; O is a solid support; or where one or more of R2, R3, R6, R7 and R8 are independently: H—(T)n—X—Y—A— where: X is CO, NH, S or O; T is a combinatorial unit; Y is a divalent group such that HY=R; A is O, S, NH, or a single bond and n is a positive integerType: GrantFiled: February 26, 2001Date of Patent: June 8, 2004Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Publication number: 20040092736Abstract: A compound of formula (IV): O is a solid support; L is a linking group or a single bond; X′ is selected from CO, NH, S, or O; A is O, S, NH, or a single bond; R2 and R3 are independently selected from: H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR, CN and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, and R9 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11 is either H or R; Q is S, O or NH; R10 is a nitrogen protecting group; and Y is a divalent group such that HY═R, and other related compounds and collections of compounds.Type: ApplicationFiled: June 24, 2003Publication date: May 13, 2004Applicant: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Publication number: 20030195196Abstract: A compound with formula (I) 1Type: ApplicationFiled: March 4, 2003Publication date: October 16, 2003Applicant: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Patent number: 6608192Abstract: A compound of formula (IV): O is a solid support; L is a linking group or a single bond; X′ is selected from CO, NH, S, or O; A is O, S, NH, or a single bond; R2 and R3 are independently selected from: H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R′, CH2—CO2H, CH2—SO2R, O—SO2R, CO2R, COR, CN and there is optionally a double bond between C1 and C2 or C2 and C3; R6, R7, and R9 are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn; R11 is either H or R; Q is S, O or NH; R10 is a nitrogen protecting group; and Y is a divalent group such that HY=R, and other related compounds and collections of compounds.Type: GrantFiled: February 26, 2001Date of Patent: August 19, 2003Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard
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Publication number: 20030120069Abstract: Compounds of the formulae Ia and Ib: 1Type: ApplicationFiled: December 12, 2001Publication date: June 26, 2003Applicant: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard