Cytotoxic agents

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C514S063000, C514S081000, C544S363000, C546S085000, C546S135000, C546S146000, C546S187000, C548S421000, C548S433000

Reexamination Certificate

active

07129261

ABSTRACT:
The present invention provides analogues of duocarmycins that are potent cytotoxins. Also provided are peptidyl and disulfide linkers that are cleaved in vivo. The linkers are of use in forming prodrugs and conjugates of the cytotoxins of the invention as well as other diagnostic and therapeutic moieties. The invention provides prodrugs and conjugates of the duocarmycin analogues with the linker arms of the invention.

REFERENCES:
patent: 4169888 (1979-10-01), Hanka et al.
patent: 4671958 (1987-06-01), Rodwell et al.
patent: 4912227 (1990-03-01), Kelly et al.
patent: 4923990 (1990-05-01), Nakano et al.
patent: 4952394 (1990-08-01), Senter
patent: 4975278 (1990-12-01), Senter et al.
patent: 4978757 (1990-12-01), Kelly et al.
patent: 4994578 (1991-02-01), Ohba et al.
patent: 5037993 (1991-08-01), Ohba et al.
patent: 5070092 (1991-12-01), Kanda et al.
patent: 5084468 (1992-01-01), Saito et al.
patent: 5101038 (1992-03-01), Nakano et al.
patent: 5117006 (1992-05-01), Saito et al.
patent: 5137877 (1992-08-01), Kaneko et al.
patent: 5138059 (1992-08-01), Takahashi et al.
patent: 5187186 (1993-02-01), Kanda et al.
patent: 5332740 (1994-07-01), Saito et al.
patent: 5332837 (1994-07-01), Kelly et al.
patent: 5475092 (1995-12-01), Chari et al.
patent: 5547667 (1996-08-01), Angelucci et al.
patent: 5585499 (1996-12-01), Chari et al.
patent: 5587161 (1996-12-01), Burke et al.
patent: 5606017 (1997-02-01), Willner et al.
patent: 5622929 (1997-04-01), Willner et al.
patent: 5629430 (1997-05-01), Terashima et al.
patent: 5641780 (1997-06-01), Amishiro et al.
patent: 5660829 (1997-08-01), Burke et al.
patent: 5703080 (1997-12-01), Nakakura et al.
patent: 5712374 (1998-01-01), Kuntsmann et al.
patent: 5714586 (1998-02-01), Kunstmann et al.
patent: 5739350 (1998-04-01), Kelly et al.
patent: 5773001 (1998-06-01), Hamann et al.
patent: 5773435 (1998-06-01), Kadow et al.
patent: 5786377 (1998-07-01), Garcia et al.
patent: 5786486 (1998-07-01), Fukuda et al.
patent: 5846545 (1998-12-01), Chari et al.
patent: 5877296 (1999-03-01), Hamann et al.
patent: 5962216 (1999-10-01), Trouet et al.
patent: 5985908 (1999-11-01), Boger
patent: 6060608 (2000-05-01), Boger
patent: 6066742 (2000-05-01), Fukuda
patent: 6103236 (2000-08-01), Suzawa et al.
patent: 6132722 (2000-10-01), Siemers et al.
patent: 6143901 (2000-11-01), Dervan
patent: 6194612 (2001-02-01), Boger et al.
patent: 6214345 (2001-04-01), Firestone et al.
patent: 6262271 (2001-07-01), Boger
patent: 6281354 (2001-08-01), Boger
patent: 6310209 (2001-10-01), Boger
patent: 6329497 (2001-12-01), Boger
patent: 6342480 (2002-01-01), Trouet et al.
patent: 6486326 (2002-11-01), Boger
patent: 6512101 (2003-01-01), King et al.
patent: 6534660 (2003-03-01), Yongxin et al.
patent: 6548530 (2003-04-01), Boger
patent: 6555693 (2003-04-01), Ge et al.
patent: 6566336 (2003-05-01), Sugiyama et al.
patent: 6586618 (2003-07-01), Zhao et al.
patent: 2003/0096743 (2003-05-01), Senter et al.
patent: 2003/0130189 (2003-07-01), Senter et al.
patent: 10008089 (2001-10-01), None
patent: 0154445 (1985-02-01), None
patent: 0537575 (1992-10-01), None
patent: 0689845 (2002-09-01), None
patent: WO 88/04659 (1988-06-01), None
patent: WO96/10405 (1996-04-01), None
patent: WO97/12862 (1997-04-01), None
patent: WO97/32850 (1997-09-01), None
patent: WO97/45411 (1997-12-01), None
patent: WO98/25900 (1998-06-01), None
patent: WO 98/52925 (1998-11-01), None
patent: WO 99/19298 (1999-04-01), None
patent: WO 99/29642 (1999-06-01), None
patent: WO 00/33888 (2000-06-01), None
patent: WO 01/16324 (2001-03-01), None
patent: WO 01/49698 (2001-07-01), None
patent: WO 01/74898 (2001-10-01), None
patent: WO 01/83482 (2001-11-01), None
patent: WO 01/85733 (2001-11-01), None
patent: WO 01/95943 (2001-12-01), None
patent: WO 0195945 (2001-12-01), None
patent: WO 02/00263 (2002-01-01), None
patent: WO 02/15700 (2002-02-01), None
patent: WO 02/083180 (2002-10-01), None
patent: WO 02/088172 (2002-11-01), None
patent: WO 03/022806 (2003-03-01), None
International Search Report, issued in International Application No. PCT/US02/17210.
Synthesis and Biochemical Evaluation of the CBI-PDE-I-dimer, a Benzannelated Analog of (+)-CC-1065 That Also Produces Delayed Toxicity in Mice, Paul A. Aristoff,J. Med. Chem.1993, 36, 1956-1963.
CC-1065 and the Duocarmycins: Synthetic Studies, Dale L. Boger,Chemical Review, vol. 97, No. 3, pp. 787-828.
Synthesis, Chemical Properties, and Preliminary Evaluation of Substituted CBI Analogs of CC-1065 and the Duocarmycins . . . , Dale L. Boger,J. Org. Chem.1996, 61, 4894-4912.
Duocarmycin SA Shortened, Simplified, and Extended Agents: A Systematic Examination of the Role of the DNA Binding Subunit, Dale L. Boger,J. Am. Chem. Soc.,vol. 119, No. 21, 1997 4979.
Synthesis and Preliminary Evaluation of (+)-CBI-Indole2: An Enhanced Functional Analog (+)-CC-1065, Dale L. Boger,Inorganic&Medicinal Chemistry Letters,vol. 1, No. 2, pp. 115-120, 1991.
Synthesis of N-(tert-Butyloxycarbonyl)-CBI, CBI, CBI—CDPI and CBI-CDPI2: Enhanced Functional Analogues of CC-1065 Incorporating the 1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indo-4-one (CBI) Left-Hand Subunit, Dale L. Boger,J. Org. Chem,1990, 55, 5823-5832.
CC-1065 and the Duocarmycins: Understanding their Biological Function through Mechanistic Studies, Dale L. Boger,Angew. Chem. Int. Ed. Engl. 1996, 35, 1438-1474.
1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) Analogs of CC-1065 and the Duocarmycins: Synthesis and Evaluation, Dale L. Boger,Biorganic&Medicinal Chemistry,vol. 3, No. 11, pp. 1429-1453, 1995.
Enhancement of the Selectivity and Antitumor Efficacy of a CC-1065 Analogue through Immunoconjugate Formation, Ravi V. J. Chari,Cancer Research,55, 4079-4084, Sep. 15, 1995.
Snythesis and Biological Evaluation of 2′-Carbamate-Linked and 2′-Carbonate-Linked Prodrugs of Paclitaxel: Selective Activation by the Tumor-Associated Protease Plasmin, Franciscus M.H. de Groot,J. Med. Chem. 2000, 43, 3093-3102.
Novel Synthesis of Optically Active CC-1065; U-73,975 (Adozelesin), U-80,244 (Carzelesin), U-77,779 (Bizelesin), KW-2189 and DU-861, Yasumichi Fukuda,Heterocycles,vol. 45, No. 12, 1997.
Cytotoxicity and Antitumor Activity of Carzelesin, a Prodrug Cyclopropylpyrroloindole Analogue1, L.H. Li,Cancer Research 52, 4904-4913, Sep. 15, 1992.
Snythesis and Antitumor Activity of Duocarmycin Derivatives: Modification of Segment A of Duocarmycin B2, Satoru Nagamura, (1996) Chem. Pharm. Bull 44(9) 1723-1730.
Synthesis and Antitumor Activity of Duocarmycin Derivatives, Satoru Nagamura,Chem. Pharm. Bull,43(9) 1530-1535 (1995).
Antitumor Antibiotics: Duocarmycins, Satoru Nagamura,Chemistry of Heterocyclic Compounds,vol. 34, No. 12, 1998.
Structure-Activity Relationships of (+)-CC-1065 Analogues in the Inhibition of Helicase-Catalyzed Unwinding of Duplex DNA, Daekyu Sun,Journal of Medicinal Chemistry,1992, vol. 35, No. 10.
Preparation andIn VitroCytotoxicity of a Methotrexate-Anti-MM46 Monoclonal Antibody Conjugate Via An Oligopeptide Spacer, Naoji Umemoto,Int. J. Cancer: 43, 677-684 (1989).
Dissecting the Complex Structure of CC-1065, Martha A. Warpehoski,Drugs of the Future 1991, 16(2) 131-141.
Stereoelectronic Factors Influencing the Biological Activity and DNA Interaction of Synthetic Antitumor Agents Modeled on CC-1065, M.A. Warpehoski,J. Med. Chem 1988, 31, 590-603.
Warpehoski, M. et al. (1986) “Regioselective [2,3] Sigmatropic Rearrangement to the Pyrrolo[3,2-e] Indole Ring System of CC-1065,” Tetrahedron Letters, 27(24):2735-2738.
Fukuda, Y. et al. (1998) “The Novel Cycloproparyrroloindole(CPI) Bisalkylators Bearing Methoxycarbonyl and Trifluoromethyl Groups,” Bioorganic & Medicinal Chemistry Letters 8, pp. 1387-1390.
Fukuda, Y. et al. (1998) “The Novel Cyclopropapyrroloindole(CPI) Bisalkylators Bearing 3,3′-(1,4-Phenylene)Diacryloy Group as a Linker,” Bioorganic & Medicinal Chemistry Letters 8, pp. 2003-2004.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Cytotoxic agents does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cytotoxic agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cytotoxic agents will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3637532

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.