Patents Assigned to Spirogen Limited
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Publication number: 20070185073Abstract: 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: ApplicationFiled: March 9, 2005Publication date: August 9, 2007Applicant: Spirogen LimitedInventors: Philip Howard, Stephen Gregson, Peter Taylor, David Thurston, Tsveta Hadjivassileva
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Publication number: 20070173497Abstract: 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: ApplicationFiled: March 1, 2005Publication date: July 26, 2007Applicant: Spirogen LimitedInventors: Philip Howard, Stephen Gregson
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Publication number: 20060264622Abstract: A method of synthesis of a N-10 protected PBD compound of formula (I): via an intermediate of formula (II) or formula (V):Type: ApplicationFiled: September 10, 2004Publication date: November 23, 2006Applicant: Spirogen LimitedInventors: Philip Howard, Luke Masterson
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Publication number: 20060148788Abstract: 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: ApplicationFiled: March 2, 2006Publication date: July 6, 2006Applicant: Spirogen LimitedInventors: David Thurston, Philip 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
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Patent number: 6562806Abstract: A compound with formula (I) where R10 is a therapeutically removable nitrogen protecting group; R2 and R3 are independently selected from: H, R, OH, OR, ═O, ═CH—R, ═CH2, CH2—CO2R, CH2—CO2H, CH2—SO2R, O—SO2—R, CO2R, COR and CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, nitro, Me3Sn; X is S, O or NH; R11 is either H or R; and where there is optionally a double bond between C1 and C2 or C2 and C3; and R8 is selected from H, R, OH, OR, halo, amino, nitro, Me3Sn, or R7 and R8 together form a group —O—(CH2)p—O—, where p is 1 or 2. Such compounds may be used in methods of ADEPT, GDEPT, NPEPT or PDT.Type: GrantFiled: February 26, 2001Date of Patent: May 13, 2003Assignee: Spirogen LimitedInventors: David Edwin Thurston, Philip Wilson Howard