RU96105419A - NEW BISNAFTALIMIDES FOR CANCER TREATMENT - Google Patents

NEW BISNAFTALIMIDES FOR CANCER TREATMENT

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Publication number
RU96105419A
RU96105419A RU96105419/04A RU96105419A RU96105419A RU 96105419 A RU96105419 A RU 96105419A RU 96105419/04 A RU96105419/04 A RU 96105419/04A RU 96105419 A RU96105419 A RU 96105419A RU 96105419 A RU96105419 A RU 96105419A
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RU
Russia
Prior art keywords
carbon atoms
group
compound according
alkyl
formula
Prior art date
Application number
RU96105419/04A
Other languages
Russian (ru)
Other versions
RU2138484C1 (en
Inventor
Кайльхауер Герхард
Ромердаль Киндзиа
Фернандез Бранья Мигель
Квиан Ксиао-Донг
Бускет Питер
Мария Кастеллано Берланга Хосе
Моран Мосет Марина
Хесус Перез Дэ Вега Мария
Original Assignee
Басф Аг
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Басф Аг filed Critical Басф Аг
Priority claimed from PCT/EP1994/002621 external-priority patent/WO1995005365A1/en
Publication of RU96105419A publication Critical patent/RU96105419A/en
Application granted granted Critical
Publication of RU2138484C1 publication Critical patent/RU2138484C1/en

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Claims (10)

1. Соединение формулы
Figure 00000001

где X, X', X'' и X''' - одинаковые или различные и выбраны из группы, включающей водород, нитро, амино, NH-низший алкил, алкиламино с 1 - 6 атомами углерода, диалкиламино с 1 - 6 атомами углерода в каждой алкильной группе, гидроксил, алкокси с 1 - 6 атомами углерода, галоген, тригалоидметил, алкил с 1 - 6 атомами углерода, формил, алкилкарбонил с 1 - 6 атомами углерода в алкильной группе, уреил и алкилуреил с 1 - 6 атомами углерода; или X и X' или X'' и X''' могут образовать этиленовый мостик, связанный с атомами углерода в положениях 4 и 5 циклической системы;
R и R' - H, алкил с 1 - 4 атомами углерода, арил или бензил;
A и D - одинаковые или различные и означают группу -CH2-CH2-, которая может быть замещена алкилом с 1 - 4 атомами углерода;
B - -(CH2)n-, где n - 3 или 4 и где один атом водорода может быть заменен алкильной группой с 1 - 4 атомами углерода,
и его фармацевтически приемлемые кислотно-аддитивные соли.1. The compound of the formula
Figure 00000001

where X, X ', X''andX''' are the same or different and are selected from the group consisting of hydrogen, nitro, amino, NH-lower alkyl, alkylamino with 1 to 6 carbon atoms, dialkylamino with 1 to 6 carbon atoms in each alkyl group, hydroxyl, alkoxy with 1 to 6 carbon atoms, halogen, trihalomethyl, alkyl with 1 to 6 carbon atoms, formyl, alkylcarbonyl with 1 to 6 carbon atoms in the alkyl group, ureyl and alkylureyl with 1 to 6 carbon atoms; or X and X 'or X''andX''' may form an ethylene bridge bonded to carbon atoms at positions 4 and 5 of the cyclic system;
R and R 'are H, alkyl with 1 to 4 carbon atoms, aryl or benzyl;
A and D are the same or different and mean the group —CH 2 —CH 2 -, which may be substituted with alkyl of 1 to 4 carbon atoms;
B - - (CH 2 ) n -, where n is 3 or 4 and where one hydrogen atom can be replaced by an alkyl group with 1 to 4 carbon atoms,
and its pharmaceutically acceptable acid addition salts. 2. Соединение по п.1, где X, X', X'' и X''' - одинаковые или различные и выбраны из группы, включающей нитро, амино, NH-низший ацил, галоген. 2. The compound according to claim 1, where X, X ′, X ″ and X ″ are the same or different and are selected from the group consisting of nitro, amino, NH-lower acyl, halogen. 3. Соединение по п.1, где по крайней мере один из X, X', X'' и X''' - амино или NH-низший ацил. 3. The compound according to claim 1, where at least one of X, X ′, X ″ and X ″ is amino or NH-lower acyl. 4. Соединение по п.3, где X и X'' - водород, X' и X''' - группа NHCOCH3 и -A-NR-B-NR-D - группа -CH(CH3)-CH2-NH-CH2-CH2-NH-CH2-CH(CH3)-.4. The compound according to claim 3, where X and X ″ is hydrogen, X ′ and X ″ ″ is an NHCOCH 3 group and —A-NR-B-NR-D is an —CH (CH 3 ) —CH 2 group -NH-CH 2 -CH 2 -NH-CH 2 -CH (CH 3 ) -. 5. Соединение по п.1, где X, X', X'' и X''' - водород, a A-NR-B-NR'-D- - группа -CH2-CH2-NH-CH2-CH2-CH2-NH-CH2- -CH2-.5. The compound according to claim 1, where X, X ', X "and X" are hydrogen, and A-NR-B-NR'-D- is a group -CH 2 -CH 2 -NH-CH 2 -CH 2 -CH 2 -NH-CH 2- -CH 2 -. 6. Фармацевтическая композиция, отличающаяся тем, что она содержит соединение по п.1 и фармацевтически приемлемый носитель. 6. A pharmaceutical composition, characterized in that it contains a compound according to claim 1 and a pharmaceutically acceptable carrier. 7. Способ лечения опухоли у млекопитающего, отличающийся тем, что млекопитающему дают соединение по п.1 в количестве, ингибирующего опухоль. 7. A method of treating a tumor in a mammal, characterized in that the mammal is given the compound according to claim 1 in an amount that inhibits the tumor. 8. Соединение по п.1 для лечения заболеваний. 8. The compound according to claim 1 for the treatment of diseases. 9. Способ получения соединений по п.1, отличающийся тем, что нафталевый ангидрид формулы II
Figure 00000002

где X и X' имеют указанные значения,
подвергают взаимодействию с полиамином формулы III
H2N-A-NR-B-NR'-D-NH2,
где A и B имеют указанные значения,
и нафталевым ангидридом формулы IV
Figure 00000003

где X'' и X''' имеют указанные значения.9. The method of producing compounds according to claim 1, characterized in that the naphthalic anhydride of the formula II
Figure 00000002

where X and X 'have the indicated meanings,
react with a polyamine of formula III
H 2 NA-NR-B-NR'-D-NH 2 ,
where A and B have the indicated meanings,
and naphthalic anhydride of formula IV
Figure 00000003

where X '' and X '''have the indicated meanings. 10. Способ по п. 9, отличающийся тем, что на первой конденсационной стадии концевая аминогруппа полиамина формулы III защищена. 10. The method according to p. 9, characterized in that in the first condensation stage, the terminal amino group of the polyamine of formula III is protected.
RU96105419A 1993-08-18 1994-08-08 Derivatives of bis-naphthalimide and their pharmaceutically acceptable acid-additive salts, pharmaceutical composition showing cytotoxic activity containing thereof RU2138484C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10894993A 1993-08-18 1993-08-18
US08/108949 1993-08-18
PCT/EP1994/002621 WO1995005365A1 (en) 1993-08-18 1994-08-08 New bis-naphthalimides for the treatment of cancer

Publications (2)

Publication Number Publication Date
RU96105419A true RU96105419A (en) 1998-06-10
RU2138484C1 RU2138484C1 (en) 1999-09-27

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Country Status (28)

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US (3) US5616589A (en)
EP (1) EP0714387B1 (en)
JP (1) JPH09501662A (en)
KR (1) KR960703863A (en)
CN (1) CN1039414C (en)
AT (1) ATE166647T1 (en)
AU (1) AU677696B2 (en)
BR (2) BR9407257A (en)
CA (1) CA2169059A1 (en)
CZ (1) CZ34296A3 (en)
DE (1) DE69410614T2 (en)
DK (1) DK0714387T3 (en)
ES (1) ES2116612T3 (en)
FI (1) FI960658A0 (en)
HR (1) HRP940458B1 (en)
HU (1) HU219232B (en)
IL (1) IL110460A (en)
NO (1) NO305554B1 (en)
NZ (1) NZ271374A (en)
PH (1) PH31395A (en)
PL (1) PL313078A1 (en)
RU (1) RU2138484C1 (en)
SG (1) SG64906A1 (en)
SI (1) SI9420053A (en)
TW (1) TW408112B (en)
UA (1) UA42733C2 (en)
WO (1) WO1995005365A1 (en)
ZA (1) ZA946196B (en)

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US5703089A (en) * 1994-04-28 1997-12-30 Knoll Aktiengesellschaft Dihydrodibenzisoquinolinediones
CA2268450C (en) * 1996-10-21 2008-08-05 Allelix Biopharmaceuticals, Inc. Neurotrophin antagonist compositions
AU3883600A (en) 1999-03-16 2000-10-04 Regents Of The University Of California, The Glycosylated polyamines
US6531454B1 (en) 1999-03-16 2003-03-11 The Regents Of The University Of California Glycosylated polyamines and methods of use therefor
US6492380B1 (en) * 1999-05-17 2002-12-10 Queen's University At Kingston Method of inhibiting neurotrophin-receptor binding
US6468990B1 (en) 1999-05-17 2002-10-22 Queen's University At Kingston Method of inhibiting binding of nerve growth factor to p75 NTR receptor
EP1265898B1 (en) * 2000-03-07 2003-09-24 THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES 1,8-NAPHTHALIMIDE IMIDAZO 4,5,1- i de /i ]ACRIDONES WITH ANTI-TUMOR ACTIVITY
EP1689441A1 (en) 2003-11-05 2006-08-16 PhotoBioMed Corporation Bonding tissues and cross-linking proteins with naphthalimide compounds
AU2005238096A1 (en) * 2004-05-05 2005-11-10 Unibioscreen S.A. Naphthalimide derivatives, methods for their production and pharmaceutical compositions therefrom
US20070134243A1 (en) * 2004-12-01 2007-06-14 Gazzard Lewis J Antibody drug conjugates and methods
US7947839B2 (en) 2004-12-01 2011-05-24 Genentech, Inc. Heterocyclic-substituted bis-1,8 naphthalimide compounds, antibody drug conjugates, and methods of use
JP4993645B2 (en) 2004-12-01 2012-08-08 ジェネンテック， インコーポレイテッド Antibody drug conjugates and methods
KR20080058403A (en) 2005-09-15 2008-06-25 페인셉터 파마 코포레이션 Methods of modulating neurotrophin-mediated activity
WO2009089537A2 (en) 2008-01-11 2009-07-16 Northwestern University Anti-cancer compounds

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DE3535496A1 (en) * 1985-10-04 1987-04-16 Bayer Ag METHOD FOR FLUORESCENT EXTINGUISHING AND NEW CATIONIC NAPHTHALINE PERI DICARBONIC ACID IMID DERIVATIVES
DE3707651A1 (en) * 1987-03-10 1988-09-22 Knoll Ag BIS-NAPHTHALIMIDES, THEIR PRODUCTION AND USE
US5086052A (en) * 1987-07-17 1992-02-04 Abbott Laboratories Substituted 1,4,5,6-tetrahydro-2H-pyridazin-3-one and -3-thione compounds having lipoxygenase inhibitory activity
US5086059A (en) * 1990-06-07 1992-02-04 Du Pont Merck Pharmaceutical Company Bis-naphthalimides as anticancer agents
US5206249A (en) * 1991-03-27 1993-04-27 Du Pont Merck Pharmaceutical Company Bis-naphthalimides containing amino-acid derived linkers as anticancer agents
JPH07501822A (en) * 1991-12-11 1995-02-23 デュポン・ファーマシュウティカルズ・カンパニー Highly water-soluble bis-naphthalimide useful as an anticancer agent
DE4232739A1 (en) * 1992-09-30 1994-03-31 Knoll Ag New asymmetrically substituted bis-naphthalimides

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