Nitrogen Of The Hetero Ring Is Shared By An Additional Cyclo Of The Tricyclo Ring System Patents (Class 540/496)
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Patent number: 8318726Abstract: The present invention provides a compound of formula 5, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of formula 5a-t.Type: GrantFiled: March 15, 2011Date of Patent: November 27, 2012Assignee: Council of Scientific & Industrial ResearchInventors: Ahmed Kamal, Adla Mallareddy, Paidakula Suresh, Rajesh Venkata Chenna Rama Narasimha Chennamshetti
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Publication number: 20120270857Abstract: Novel 5-HT3 receptor modulators are disclosed. These compounds are used in the treatment of various disorders, including chemotherapy-induced nausea and vomiting, post-operative nausea and vomiting, and irritable bowel syndrome. Methods of making these compounds are also described in the present invention.Type: ApplicationFiled: June 30, 2010Publication date: October 25, 2012Applicant: ALBANY MOLECULAR RESEARCH, INC.Inventors: Peter R. Guzzo, David D. Manning, William Earley
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Patent number: 8293731Abstract: Tricyclic compounds of Formula I are inhibitors of HIV integrase and inhibitors of HIV replication: wherein bond a, ring A, R1, R2 and R3 are defined herein. The compounds are useful for the prophylaxis or treatment of infection by HIV and the prophylaxis, treatment, or delay in the onset of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.Type: GrantFiled: May 13, 2011Date of Patent: October 23, 2012Assignee: Merck Sharp + Dohme Corp.Inventors: Joseph P. Vacca, John S. Wai, Linda S. Payne
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Publication number: 20120253034Abstract: The present invention provides a compound of general formula 7, useful as potential antitumour agents against five human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine linked imidazo[1,5-a]pyridine conjugates attached through a piperazine moiety and different alkane spacers of general formula 7 wherein R represents H, OCH3, CF3, CN, F or Cl; n=3, 4, 5 or 6.Type: ApplicationFiled: March 23, 2011Publication date: October 4, 2012Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventors: Ahmed Kamal, Gadupudi Ramakrishna, Paidakula Raju, Ayinampudi Venkata Subba Rao, Arutla Viswanath, Gorre Balakishan
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Publication number: 20120244172Abstract: The present invention relates to pyrrolo[1,4]benzodiazepine (PBD) dimer conjugates, to the compositions comprising them and to their therapeutic application, in particular as anticancer agents. The invention also relates to the process for the preparation of the conjugates, to their application as anticancer agents and to the dimers themselves.Type: ApplicationFiled: February 24, 2012Publication date: September 27, 2012Applicant: SANOFIInventors: Alain Commercon, Laurence Gauzy-Lazo
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Patent number: 8217167Abstract: The present invention provides a compounds of general formula (6), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formula (6).Type: GrantFiled: March 12, 2009Date of Patent: July 10, 2012Assignee: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Sreekanth Kokkonda, Praveen Kumar Pogula, Balakishan Gorre
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Publication number: 20120142913Abstract: The present invention provides a compound of formula 5, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of formula 5a-t.Type: ApplicationFiled: March 15, 2011Publication date: June 7, 2012Inventors: Ahmed KAMAL, Adla MALLAREDDY, Paidakula SURESH, Rajesh Venkata Chenna Rama Narasimha CHENNAMSHETTI
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Publication number: 20120122835Abstract: Disclosed are compounds of the following formula: in which R1, R2, R3, R4, R5, R6, R7, X, and t are defined in the specification. Also disclosed are pharmaceutical compositions, kits, and articles of manufacture, which contain the compounds, methods and intermediates useful for making the compounds, and methods of using the compounds to treat diseases, disorders, and conditions related to PARP activity.Type: ApplicationFiled: January 18, 2012Publication date: May 17, 2012Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITEDInventors: Anthony R. Gangloff, Andrew John Jennings, Benjamin Jones, Andre A. Kiryanov
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Publication number: 20120101270Abstract: The present invention provides synthesis and in vitro anticancer activity of novel pyrrolo[2,1-c][1,4]benzodiazepine derivatives with dithiocarbamate side chains. The present invention also relates to a process for the preparation of new pyrrolo[2,1-c][1,4]benzodiazepine derivatives with dithiocarbamate side chains of general formula (A) and a process for the preparation thereof.Type: ApplicationFiled: March 24, 2009Publication date: April 26, 2012Applicant: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Sreekanth Kokkonda, Praveen K. Pogula, Balakishan Gorre
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Patent number: 8163736Abstract: The present invention is related to new tomaymycin derivatives, their process of preparation and their therapeutic uses.Type: GrantFiled: July 16, 2008Date of Patent: April 24, 2012Assignee: sanofi-aventisInventors: Laurence Gauzy, Herve Bouchard, Ravi V. J. Chari, Alain Commercon, Robert Zhao, Yonghong Deng, Wei Li
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Publication number: 20120095213Abstract: The present invention provides a compound of general formulae (8a-i), (11a-i), (14a-i), and (17a-i), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of Cinnamido-pyrrolo[2,1-c][1,4]benzodiazepines of general formulae (8a-i), (11a-i), (14a-i), and (17a-i).Type: ApplicationFiled: February 27, 2009Publication date: April 19, 2012Inventors: Kamal Ahmed, Balakishan Gorre, Ramakrishna Gadupudi, Sreekanth Kokkonda, N/A Rajender
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Publication number: 20120095214Abstract: The present invention provides a compound of general formulae 5a-r, 9a-i to 13a-i and 17a-i to 22a-i, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formulae 5a-r, 9a-i to 13a-i and 17a-i to 22a-i.Type: ApplicationFiled: July 13, 2009Publication date: April 19, 2012Applicant: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Earla V. Bharathi, Dudekula Dastagiri, Jonnala S. Reddy, Arutla Viswanath
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Patent number: 8153627Abstract: The present invention provides a compound of general formula 5, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formula (5): wherein n=3, 4, 5, 6, 8 and wherein R1 and R2 is selected from the group consisting of R1?H, R2?H or R1?CH3O, R2=CH3O or R1?CH3O and R2?C2H5O.Type: GrantFiled: October 31, 2008Date of Patent: April 10, 2012Assignee: Council of Scientific & Industrial ResearchInventors: Ahmed Kamal, Bandari Rajendra Prasad, Adla Malla Reddy
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Publication number: 20120040961Abstract: The present invention relates to novel pyrimido-diazepinone compounds, methods of modulating protein kinases, including MPS1 (TTK), ERK5 (BMK1, MAPK7), polo kinase 1, 2, 3, or 4, Ack1, Ack2, AbI, DCAMKL1, ABL1, AbI mutants, DCAMKL2, ARK5, BRK, MKNK2, FGFR4, TNK1, PLK1, ULK2, PLK4, PRKD1, PRKD2, PRKD3, ROS 1, RPS6KA6, TAOK1, TAOK3, TNK2, Bcr-Abl, GAK, cSrc, TPR-Met, Tie2, MET, FGFR3, Aurora, AxI, Bmx, BTK, c-kit, CHK2, Flt3, MST2, p70S6K, PDGFR, PKB, PKC, Raf, ROCK-H, Rsk1, SGK, TrkA, TrkB and TrkC, and the use of such compounds in the treatment of various diseases, disorders or conditions.Type: ApplicationFiled: January 6, 2010Publication date: February 16, 2012Applicant: DANA-FARBER CANCER INSTITUTEInventors: Nathanael S. Gray, Xianming Deng, Nicholas Paul Kwiatkowski
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Patent number: 8063204Abstract: The present invention provides a compound of general formula (9), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4][benzodiazepine g hybrids of general formula (9).Type: GrantFiled: December 31, 2007Date of Patent: November 22, 2011Assignee: Council of Scientific & Industrial ResearchInventors: Ahmed Kamal, K. Srinivasa Reddy, Mohammed Naseer Ahmed Khan, Rajesh V. C. R. N. C Shetti
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Publication number: 20110256157Abstract: Conjugates and compounds for making conjugates which are PBD molecules linked via the N10 position are disclosed, along with the use of the conjugates for treating proliferative diseases, including cancer.Type: ApplicationFiled: April 15, 2011Publication date: October 20, 2011Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Luke Masterson, Arnaud Tiberghien, John A. Flygare, Janet L. Gunzner, Paul Polakis, Andrew Polson, Helga E. Raab, Susan D. Spencer
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Publication number: 20110207924Abstract: The present invention provides a compounds of general formula (6), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formula (6).Type: ApplicationFiled: March 12, 2009Publication date: August 25, 2011Applicant: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Sreekanth Kokkonda, Praveen Kumar Pogula, Balakishan Gorre
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Publication number: 20110201803Abstract: The invention relates to certain pyrrolobenzodiazepines (PBDs), and in particular pyrrolobenzodiazepine dimers bearing C2 substitutions, including compounds of formula (T): wherein: R2 is CHR2A, and R2A is independently selected from H, R, CO2R, COR, CHO, CO2H, and halo; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, NO2, Me3Sn and halo; R7 is independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, NO2, Me3Sn and halo; R8 is independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR?, NO2, Me3Sn and halo; R is independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; or the compound is a dimer with each monomer being of formula (M), where the R7 groups or R8 groups of each monomer form together a dimer bridge having the formula āXāR?āXā linking the monomers; wherein R? is a C3-12 alkylene group, which chain may be interrupted by one or more heteroatoms, e.g. O, S, N(H), and/or aromatic rings, e.g.Type: ApplicationFiled: October 16, 2009Publication date: August 18, 2011Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Stephen John Gregson, Zhizhi Chen, Arnaud Charles Tiberghien, Luke Masterson
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Publication number: 20110196148Abstract: Claimed are unsymmetrical Pyrrolobenzodiazepine-dimers (PBD-dimers) of formula (I), that are unsymmetrical due at least to the values that the variables R12 and R2 represent. Formula (I), wherein: R2 is of formula (II), where A is a C5-7 aryl group, X is selected from the group comprising: OH, SH, CO2H, COH, N?C?O, NHRN, wherein RN is selected from the group comprising H and C1-4 alkyl, and (OC2H4)mOCH3, where m is 1 to 3, and either: (i) Q1 is a single bond, and Q2 is selected from a single bond and āZā(CH2)mā, where Z is selected from a single bond, O, S and NH and n is from 1 to 3; or (ii) Q1 is āCH?CHā, and Q2 is a single bond; R12 is a C5-10 aryl group, optionally substituted by one or more substituents selected from the group comprising: halo, nitro, cyano, ether, C1-7 alkyl, C3-7 heterocyclyl and bis-oxy-C1-3 alkylene. The other variables are as defined in the claims. The compounds are useful for the treatment of proliferative diseases.Type: ApplicationFiled: October 16, 2009Publication date: August 11, 2011Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Stephen John Gregson, Luke Masterson
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Publication number: 20110190275Abstract: The present invention provides a compounds of general formula IXa-d, useful as potential antitumour agents and pharmaceutical composition comprising these compounds exhibits binding affinity with calf thymus (CT) DNA at a molar ratio of 1:5 in aqueous sodium phosphate buffer at pH of 7.00. The present invention further provides a process for the preparation of C2-Fluoro substituted piperazine linked pyrrolo[2,1c][1-4], benzodiazepine of formula (IX).Type: ApplicationFiled: October 31, 2008Publication date: August 4, 2011Inventors: Ahmed Kamal, Rajender, Metuku Kashireddy, Gorre Balakishan
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Publication number: 20110162227Abstract: Methods of preparing ZC-423 (I) which result in varying enantiomeric ratios.Type: ApplicationFiled: July 22, 2009Publication date: July 7, 2011Applicant: SPIROGEN LIMITEDInventors: Philip Wilson Howard, Stephen John Gregson, Zhizhi Chen, Arnaud Charles Tiberghien, Luke Masterson
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Publication number: 20110160192Abstract: Compounds of formula (I): Z?-CO-A-BāNH-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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Publication number: 20110130382Abstract: The present application relates to 1,2,3,4,4a,5,6,7-octahydropyrazino[1,2-a][1,4]benzodiazepine, 1,2,3,4,4a,5,6,7-octahydropyrazino[1,2-a][1,5]benzodiazepine, 2,3,4,4a,5,6,7,11b-octahydro-1H-pyrido[3,4-d][2]benzazepine, 1,2,3,4,4a,5,6,7-octahydropyrazino[1,2-a][1]benzazepine, 1,2,3,4,4a,5-hexahydro-7H-pyrazino[1,2-a][4,1]benzoxazepine, and 2,3,4,4a,5,6-hexahydro-1H-pyrazino[2,1-d][1,5]benzoxazepine, and 5,6,7,7a,8,9,10,11-octahydropyrazino[1,2-d]pyrido[3,2-b][1,4]diazepine derivatives of formula (I) wherein R1, R2, R3, R4, R5, R6, X1, X2, X3, X4, Y1, Y2, and Y3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating disease conditions using such compounds and compositions, and methods for identifying such compounds.Type: ApplicationFiled: October 21, 2010Publication date: June 2, 2011Applicant: ABBOTT LABORATORIESInventors: Ying Wang, Jason T. Brewer, Irini Akritopoulou-Zanze, Stevan W. Djuric, Frauke Pohlki, Wilfried Braje, Ana-Lucia Relo
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Publication number: 20100324027Abstract: The invention relates to compounds that are diazahomoadamantane derivatives, compositions comprising such compounds, and methods of using such compounds and compositions.Type: ApplicationFiled: June 18, 2010Publication date: December 23, 2010Applicant: ABBOTT LABORATORIESInventors: Michael R. Schrimpf, Kevin B. Sippy
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Publication number: 20100316656Abstract: The invention relates to novel tomaymicine derivatives comprising a linker. It also relates to the conjugate molecules that comprise one or more of said tomaymicine derivatives covalently linked to a cell binding agent through a linking group that is present on the linker of the tomaymycin derivative. It also relates to the preparation of the tomaymicine derivatives and of the conjugate molecules.Type: ApplicationFiled: January 19, 2010Publication date: December 16, 2010Applicant: sanofi-aventisInventors: HervƩ Bouchard, Ravi V.J. Chari, Alain Commercon, Yonghong Deng, Laurence Gauzy
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Patent number: 7834005Abstract: Disclosed are compounds of Formula I wherein X, Y, R1-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula I and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula I; a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula I; a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula I; and a method of preparing a compound of Formula I as described herein.Type: GrantFiled: February 13, 2009Date of Patent: November 16, 2010Assignees: The United States of America as represented by the Department of Health and Human Services, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip W. Howard, Luke Y. Hsiao, Gregory Turner
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Patent number: 7790712Abstract: The application relates to compounds of formula Ia and analogues thereof wherein R1 to R13 and X are as defined herein. The invention also relates to the use of the compounds of formula Ia as inhibitors of Mitogen-Activated Protein Kinase-Activated Protein kinase-2 (MAPKAP-k2), and also to a method for preventing or treating a disease or disorder that can be treated or prevented by modulating the activity of MAPKAP-K2 in a subject and to pharmaceutical compositions and kits that include these MAPKAP-K2 inhibitors.Type: GrantFiled: March 17, 2006Date of Patent: September 7, 2010Assignee: Boehringer Ingelheim Pharmaceutical, Inc.Inventors: Derek Cogan, Donghong A. Gao, Daniel R. Goldberg, Craig Andrew Miller, Neil Moss, Matthew Russell Netherton, Philip Dean Ramsden, Zhaoming Xiong
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Publication number: 20100203007Abstract: The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepines of formula (I) and (II), in which the diazepine ring (B) is fused with a heterocyclic ring (CD), wherein the heterocyclic ring is bicyclic or a compound of formula (III), in which the diazepine ring (B) is fused with a heterocyclic ring (C), wherein the heterocyclic ring is monocyclic. The invention provides cytotoxic dimers of these compounds. The invention also provides conjugates of the monomers and the dimers. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention. The invention further relates to methods of using the compounds or conjugates for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.Type: ApplicationFiled: February 4, 2010Publication date: August 12, 2010Applicant: Immunogen Inc.Inventors: Wei Li, Nathan Fishkin, Robert Zhao, Michael Miller, Ravi Chari
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Publication number: 20100190775Abstract: The invention provides a pyrimidodiazepinone derivative represented by the general formula (I) [wherein n represents 1 or 2, Z represents a hydrogen atom or the like, R1 and R2 may be the same or different, and each represents a hydrogen atom or the like, A represents a bond, (CH2)m (wherein m represents an integer of 1 to 4), optionally substituted phenylene, optionally substituted pyridinediyl, or C?O, R3 represents a hydrogen atom, optionally substituted lower alkyl, or the like, and R4 represents a hydrogen atom or the like], or a pharmaceutically acceptable salt thereof or the like.Type: ApplicationFiled: June 2, 2008Publication date: July 29, 2010Applicant: Kyowa Hakko Kirin Co., LtdInventors: Nobumasa Otsubo, Yukihito Tsukumo, Kenji Uchida, Yuichi Matsumoto, Kyoichiro Iida, Hidenori Takada, Fumitake Takizawa, Hitoshi Arai, Shuko Okazaki, Takamichi Imaizumi
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Publication number: 20100190763Abstract: Disclosed are compounds of the following formula: in which R1, R2, R3, R4, R5, R6, R7, X, and t are defined in the specification. Also disclosed are pharmaceutical compositions, kits, and articles of manufacture, which contain the compounds, methods and intermediates useful for making the compounds, and methods of using the compounds to treat diseases, disorders, and conditions related to PARP activity.Type: ApplicationFiled: January 21, 2010Publication date: July 29, 2010Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITEDInventors: Anthony R. Gangloff, Andrew John Jennings, Benjamin Jones, Andre A. Kiryanov
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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 OāR11, 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: 20100113771Abstract: The present invention provides a compound of general formula (9), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4][benzodiazepine g hybrids of general formula (9).Type: ApplicationFiled: December 31, 2007Publication date: May 6, 2010Inventors: Ahmed Kamal, Srinivasa K. Reddy, Mohammed Naseer Ahmed Khan, Rajesh V.C.R.N.C. Shetti
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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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Publication number: 20090291938Abstract: Compounds of the following formula are provided for use with kinases: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.Type: ApplicationFiled: November 19, 2008Publication date: November 26, 2009Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITEDInventors: Sheldon X. Cao, Victoria Feher, Takashi Ichikawa, Benjamin Jones, Stephen W. Kaldor, Andre A. Kiryanov, Betty Lam, Yan Liu, Christopher McBride, Srinivasa Reddy Natala, Zhe Nie, Jeffrey A. Stafford
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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: 7608615Abstract: The present invention provides quinazolinone linked pyrrolo[2,1-c][1,4]benzodiazepine hybrid of general formula 5, wherein, R is alkyl or halo group selected from H, Cl, F or CH3 and n=1 to 3 useful for antitumour/anticancer activity. The present invention also provides a process for the preparation of quinazolinone linked pyrrolo[2,1-c][1,4]benzodiazepine hybrid general formula 5.Type: GrantFiled: August 14, 2007Date of Patent: October 27, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Venkata Ramana Adhi, Hari Babu Ankati
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Patent number: 7569561Abstract: The present invention encompasses compounds of general formula (1) wherein R1 to R6, X and Y are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or anomalous cell proliferation, as well as the use thereof for preparing a pharmaceutical composition with the above-mentioned properties.Type: GrantFiled: February 16, 2007Date of Patent: August 4, 2009Assignee: Boehringer Ingelheim International GmbHInventors: Heinz Stadtmueller, Anke Baum, Guido Boehmelt, Harald Engelhardt, Jens Juergen Quant, Flavio Solca, Martin Steegmaier, Stephan Karl Zahn
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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 āH, ?O, ?CH2, āCN, āR, OR, halo, ?CHāR, OāSO2āR, 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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Publication number: 20090149449Abstract: Disclosed are compounds of Formula I wherein X, Y, R1-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula I and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula I; a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula I; a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula I; and a method of preparing a compound of Formula I as described herein.Type: ApplicationFiled: February 13, 2009Publication date: June 11, 2009Applicants: The United States of America, as represented by the Secretary, Dept. of Health and Human Service, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip W. Howard, Luke Y. Hsiao, Gregory Turner
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Patent number: 7528128Abstract: The present invention provides a compound of general formula 5, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formula 5 wherein, X1, X2, X3 is selected from H or Cl or CH3, Y is selected from O or NH, Z is selected from C?O or CH2 and n=1 to 4.Type: GrantFiled: August 13, 2007Date of Patent: May 5, 2009Assignee: Council of Scientific & Industrial ResearchInventors: Kamal Ahmed, Rajendra Prasad Bandari
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Patent number: 7511032Abstract: Disclosed are compounds of Formula (I) wherein X, Y, Ri-R7, T1, T2, Z, and p are as described herein; a pharmaceutical composition comprising a compound of Formula (I) and a carrier; a method of inhibiting growth of a cell, which method comprises administering in an amount effective to inhibit growth a compound of Formula (I); a method of treating cancer in a mammal, which method comprises administering in an amount effective to treat cancer a compound of Formula (I); a method of treating a viral, parasitic, or bacterial infection of a cell, which method comprises administering in an amount effective to treat a viral, parasitic, or bacterial infection a compound of Formula (I); and a method of preparing a compound of Formula (I) as described herein.Type: GrantFiled: October 22, 2004Date of Patent: March 31, 2009Assignees: The United States of America as represented by the Secretary, Department of Health and Human Services, Starks Associates, Inc., Midwest Research Institute, Spirogen, Ltd.Inventors: Paul S Liu, B. Rao Vishnuvajjala, Kenneth M Snader, David E Thurston, Philip W Howard, Luke Y Hsiao, Gregory Turner
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Patent number: 7476664Abstract: The present invention provides a novel bis 2-difluoro pyrrolo[2,1-c][1,4]benzodiazepine of formula VII wherein, n is 3 to 10. novel bis 2-difluoro pyrrolo[2,1-c][1,4]benzodiazepine of formula VII exhibits biding affinity with calf thymus (CT) DNA at a molar ratio of 1:5 in aqueous sodium phosphate buffer at pH of about 7.00. The present invention further provides a process for the preparation of novel bis 2-difluoro pyrrolo[2,1-c][1,4]benzodiazepine of formula VII.Type: GrantFiled: March 7, 2007Date of Patent: January 13, 2009Inventors: Ahmed Kamal, Depatla Rajasekhar Reddy, Rajendar Rajendar
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Patent number: 7465724Abstract: The present invention provides novel bis-pyrrolo[2,1-c][1,4]benzodiazepine-anthraquinone conjugates of general formula V, useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of novel bis-pyrrolo[2,1 -c][1,4]benzodiazepine-anthraquinone conjugates of general formula V. wherein n=3, 4, or 5.Type: GrantFiled: February 12, 2007Date of Patent: December 16, 2008Assignee: Council of Scientific and Industrial ResearchInventors: Ahmed Kamal, Rondla Ramu, Gollapalli Bhasker Ramesh Khanna
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Patent number: 7429658Abstract: A method of synthesis of a N-10 protected PBD compound of formula (I): via an intermediate of formula (II) or formula (V):Type: GrantFiled: September 10, 2004Date of Patent: September 30, 2008Assignee: Spirogen LimitedInventors: Philip Howard, Luke Masterson
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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: 7312210Abstract: The present invention provides novel pyrrolo [2,1-c][1,4]benzodiazepine compounds. This invention also provides a process for the preparation of novel pyrrolo[2,1-c][1,4]benzodiazepine compounds. These novel pyrrolo [2,1-c][1,4]benzodiazepine compounds are useful as antitumor agents. It also provides a process for the preparation of 7-methoxy-8-{n-[4-(2-oxo-2H-4-chromenyl)piperazino]alkyl}-oxy-(11aS)-1,2,3,11a-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one and 7-methoxy-8-{n-[4-(7-alkoxy-8-methyl-2-oxo-2H-4-chromenyl)piperazino]alkyl}-oxy-(11aS)-1,2,3,11a-5H-pyrrolo[2,1-c][1,4]. benzodiazepine-5-one with aliphatic chain length variations for these compounds.Type: GrantFiled: March 3, 2006Date of Patent: December 25, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Ahmed Kamal, Ankati Hari Babu, Adhi Venkata Ramana, Earla Vijaya Bharathi
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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 āOā(CH2)pāOā, 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: 7244724Abstract: A compound of formula I: or solvate thereof, wherein n is 1 to 10, and M and M? are independently selected from monovalent pharmaceutically acceptable cations, or together represent a divalent pharmaceutically acceptable cation.Type: GrantFiled: May 13, 2005Date of Patent: July 17, 2007Assignees: United States of America, Represented by the Secretary, Department of Health and Human Services, Spirogen, Ltd.Inventors: Paul S. Liu, B. Rao Vishnuvajjala, Kenneth M. Snader, David E. Thurston, Philip Howard, Stephen Gregson
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Patent number: 7189710Abstract: The present invention relates to novel 2-fluoro-pyrrolo[2,1-c][1,4]benzodiazepine dimers useful as antitumour agents and to a process for the preparation thereof.Type: GrantFiled: March 30, 2004Date of Patent: March 13, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Ahmed Kamal, Peram Surakattula Murali Mohan Reddy, Depatla Rajashekhar Reddy