NZ500789A - Analogs of duocarmycin and CC-1065 - Google Patents
Analogs of duocarmycin and CC-1065Info
- Publication number
- NZ500789A NZ500789A NZ500789A NZ50078998A NZ500789A NZ 500789 A NZ500789 A NZ 500789A NZ 500789 A NZ500789 A NZ 500789A NZ 50078998 A NZ50078998 A NZ 50078998A NZ 500789 A NZ500789 A NZ 500789A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkylation
- dna
- equiv
- dsa
- etoac
- Prior art date
Links
- VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 title abstract description 46
- 229960005532 CC-1065 Drugs 0.000 title abstract description 17
- UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical compound C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 title abstract description 17
- 229960005501 duocarmycin Drugs 0.000 title description 8
- 229930184221 duocarmycin Natural products 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 230000002152 alkylating effect Effects 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 23
- 238000000338 in vitro Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 description 191
- 230000029936 alkylation Effects 0.000 description 160
- 239000003795 chemical substances by application Substances 0.000 description 157
- 230000007118 DNA alkylation Effects 0.000 description 131
- 238000005481 NMR spectroscopy Methods 0.000 description 90
- 235000011468 Albizia julibrissin Nutrition 0.000 description 80
- 241001070944 Mimosa Species 0.000 description 80
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 75
- 150000001408 amides Chemical class 0.000 description 75
- 239000007787 solid Substances 0.000 description 73
- 239000000243 solution Substances 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 230000027455 binding Effects 0.000 description 68
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 65
- 230000009257 reactivity Effects 0.000 description 60
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 58
- 108020004414 DNA Proteins 0.000 description 56
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- 238000003797 solvolysis reaction Methods 0.000 description 51
- 238000004587 chromatography analysis Methods 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 238000007792 addition Methods 0.000 description 45
- 238000006555 catalytic reaction Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 41
- 229930024421 Adenine Natural products 0.000 description 39
- 229960000643 adenine Drugs 0.000 description 39
- 230000021615 conjugation Effects 0.000 description 38
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- -1 palladium hydride Chemical class 0.000 description 25
- 230000004568 DNA-binding Effects 0.000 description 24
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- 101150041968 CDC13 gene Proteins 0.000 description 23
- VQNATVDKACXKTF-UHFFFAOYSA-N Duocarmycin SA Natural products COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C(C64CC6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-UHFFFAOYSA-N 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
- 229960005510 duocarmycin SA Drugs 0.000 description 23
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 21
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- 230000001472 cytotoxic effect Effects 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 20
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 15
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- 230000004913 activation Effects 0.000 description 15
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- 229910052799 carbon Inorganic materials 0.000 description 15
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 15
- 238000006265 spirocyclization reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
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- 238000003818 flash chromatography Methods 0.000 description 13
- AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 238000005119 centrifugation Methods 0.000 description 11
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- 230000036515 potency Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
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- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 10
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
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- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- SNLLCSDUARMKPB-UHFFFAOYSA-M oxan-2-yloxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)COC1CCCCO1 SNLLCSDUARMKPB-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- OFTHSKYOGOJVQF-UHFFFAOYSA-N pent-4-enyl methanesulfonate Chemical compound CS(=O)(=O)OCCCC=C OFTHSKYOGOJVQF-UHFFFAOYSA-N 0.000 description 1
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- YLZWEPNHBVOIBC-UHFFFAOYSA-N pyrrolo[3,2-e]indole Chemical compound C1=CC2=NC=CC2=C2C=CN=C21 YLZWEPNHBVOIBC-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/32—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4850597P | 1997-05-22 | 1997-05-22 | |
| PCT/US1998/010535 WO1998052925A1 (en) | 1997-05-22 | 1998-05-22 | Analogs of duocarmycin and cc-1065 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ500789A true NZ500789A (en) | 2002-05-31 |
Family
ID=21954939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ500789A NZ500789A (en) | 1997-05-22 | 1998-05-22 | Analogs of duocarmycin and CC-1065 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6281354B1 (https=) |
| EP (1) | EP0983248B1 (https=) |
| JP (1) | JP2002503228A (https=) |
| AT (1) | ATE271041T1 (https=) |
| AU (1) | AU754083B2 (https=) |
| CA (1) | CA2290789A1 (https=) |
| DE (1) | DE69825048D1 (https=) |
| NZ (1) | NZ500789A (https=) |
| WO (1) | WO1998052925A1 (https=) |
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| ES2299560T3 (es) | 2001-02-22 | 2008-06-01 | University Of Bradford | Derivados de pirrolindol y de pirroloquinolina como profarmacos para el tratamiento de tumores. |
| AU2002311919B8 (en) | 2001-05-11 | 2007-03-22 | Ludwig Institute For Cancer Research Ltd | Specific binding proteins and uses thereof |
| US20100056762A1 (en) | 2001-05-11 | 2010-03-04 | Old Lloyd J | Specific binding proteins and uses thereof |
| US6989452B2 (en) * | 2001-05-31 | 2006-01-24 | Medarex, Inc. | Disulfide prodrugs and linkers and stabilizers useful therefor |
| DE10147672A1 (de) | 2001-09-27 | 2003-04-10 | Bayer Ag | Substituierte 2,5-Diamidoindole und ihre Verwendung |
| WO2004035571A1 (en) * | 2002-10-15 | 2004-04-29 | Rigel Pharmaceuticals, Inc. | Substituted indoles and their use as hcv inhibitors |
| WO2004043350A2 (en) * | 2002-11-14 | 2004-05-27 | The Scripps Research Institute | PURIFIED COMPOUNDS THAT INHIBIT INTRACELLULAR α4/PAXILLIN BINDING |
| CN100519555C (zh) * | 2004-03-13 | 2009-07-29 | Tmrc株式会社 | 将dna的特定碱基序列烷基化的新吲哚衍生物和使用其的烷基化剂以及药剂 |
| US7691962B2 (en) * | 2004-05-19 | 2010-04-06 | Medarex, Inc. | Chemical linkers and conjugates thereof |
| JP4806680B2 (ja) | 2004-05-19 | 2011-11-02 | メダレックス インコーポレイテッド | 自己犠牲リンカー及び薬剤複合体 |
| US7714016B2 (en) * | 2005-04-08 | 2010-05-11 | Medarex, Inc. | Cytotoxic compounds and conjugates with cleavable substrates |
| NZ566395A (en) | 2005-09-26 | 2012-03-30 | Medarex Inc | Human monoclonal antibodies to CD70 |
| EP2354163A3 (en) * | 2005-09-26 | 2013-04-24 | Medarex, Inc. | Conjugates of duocarmycin and anti-CD70 or anti-PSMA antibodies |
| RS52100B (sr) | 2005-10-26 | 2012-06-30 | Medarex, Inc. | Postupci i jedinjenja za pripremu analoga cc-1065 |
| WO2007059404A2 (en) | 2005-11-10 | 2007-05-24 | Medarex, Inc. | Duocarmycin derivatives as novel cytotoxic compounds and conjugates |
| US8383118B2 (en) | 2005-12-08 | 2013-02-26 | Medarex, Inc. | Human monoclonal antibodies to fucosyl-GM1 and methods for using anti-fucosyl-GM1 |
| EA017812B1 (ru) | 2005-12-08 | 2013-03-29 | Медарекс, Инк. | Выделенное моноклональное антитело или его антигенсвязывающий участок, которые связываются с протеинтирозинкиназой 7 ( ptk7) человека, и их применение |
| US20090175886A1 (en) | 2006-01-17 | 2009-07-09 | Medarex, Inc. | Monoclonal antibodies against cd30 lacking in fucosyl and xylosyl residues |
| CA2662350A1 (en) | 2006-09-05 | 2008-03-13 | Medarex, Inc. | Antibodies to bone morphogenic proteins and receptors therefor and methods for their use |
| US8481683B2 (en) | 2006-12-01 | 2013-07-09 | Medarex, Inc. | Human antibodies that bind CD22 and uses thereof |
| CL2007003622A1 (es) | 2006-12-13 | 2009-08-07 | Medarex Inc | Anticuerpo monoclonal humano anti-cd19; composicion que lo comprende; y metodo de inhibicion del crecimiento de celulas tumorales. |
| MX2009006277A (es) | 2006-12-14 | 2009-07-24 | Medarex Inc | Anticuerpos humanos que se enlazan a cd70 y usos de los mismos. |
| TWI412367B (zh) | 2006-12-28 | 2013-10-21 | 梅達雷克斯有限責任公司 | 化學鏈接劑與可裂解基質以及其之綴合物 |
| US9090693B2 (en) | 2007-01-25 | 2015-07-28 | Dana-Farber Cancer Institute | Use of anti-EGFR antibodies in treatment of EGFR mutant mediated disease |
| AR065404A1 (es) | 2007-02-21 | 2009-06-03 | Medarex Inc | Conjugados farmaco-ligando, los que se unen a citotoxinas potentes, composicion farmaceutica que los contienen y su uso para retardar o detener el crecimiento de un tumor en un mamifero |
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| RU2680404C2 (ru) | 2014-01-10 | 2019-02-21 | Синтон Байофармасьютикалс Б. В. | Способ очистки cys-связанных конъюгатов антитело-лекарственное средство |
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| WO2018064094A1 (en) | 2016-09-28 | 2018-04-05 | Bristol-Myers Squibb Company | Enantioselective synthesis of pyrroloindole compounds |
| KR20220150408A (ko) | 2016-11-14 | 2022-11-10 | 항저우 디에이씨 바이오테크 씨오, 엘티디 | 결합 링커, 그러한 결합 링커를 함유하는 세포 결합 분자-약물 결합체, 링커를 갖는 그러한 결합체의 제조 및 사용 |
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Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1238907A (en) * | 1984-02-21 | 1988-07-05 | Robert C. Kelly | 1,2,8,8a-tetrahydrocyclopropa¬c|pyrrolo(3,2-e)- indol-4(5h)-ones and related compounds |
| US5084468A (en) * | 1988-08-11 | 1992-01-28 | Kyowa Hakko Kogyo Co., Ltd. | Dc-88a derivatives |
| US5008271A (en) * | 1988-10-21 | 1991-04-16 | Kyowa Hakko Kogyo Co., Ltd. | DC-88A derivatives |
| US5214065A (en) * | 1990-06-11 | 1993-05-25 | Kyowa Hakko Kogyo Co., Ltd. | Dc-89 derivatives |
| EP0934269A4 (en) * | 1996-05-31 | 2000-01-12 | Scripps Research Inst | ANALOGS OF CC-1065 AND DUOCARMYCINE |
-
1998
- 1998-05-22 NZ NZ500789A patent/NZ500789A/en unknown
- 1998-05-22 EP EP98924851A patent/EP0983248B1/en not_active Expired - Lifetime
- 1998-05-22 AT AT98924851T patent/ATE271041T1/de not_active IP Right Cessation
- 1998-05-22 CA CA002290789A patent/CA2290789A1/en not_active Abandoned
- 1998-05-22 AU AU76927/98A patent/AU754083B2/en not_active Ceased
- 1998-05-22 DE DE69825048T patent/DE69825048D1/de not_active Expired - Lifetime
- 1998-05-22 JP JP55069798A patent/JP2002503228A/ja not_active Ceased
- 1998-05-22 WO PCT/US1998/010535 patent/WO1998052925A1/en not_active Ceased
-
1999
- 1999-11-09 US US09/423,576 patent/US6281354B1/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| EP0983248B1 (en) | 2004-07-14 |
| CA2290789A1 (en) | 1998-11-26 |
| EP0983248A1 (en) | 2000-03-08 |
| AU7692798A (en) | 1998-12-11 |
| EP0983248A4 (en) | 2000-09-13 |
| ATE271041T1 (de) | 2004-07-15 |
| DE69825048D1 (de) | 2004-08-19 |
| WO1998052925A1 (en) | 1998-11-26 |
| AU754083B2 (en) | 2002-11-07 |
| JP2002503228A (ja) | 2002-01-29 |
| US6281354B1 (en) | 2001-08-28 |
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