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RU99127343A - PROTOCOLAL FORMS OF RIBONUCLEOTIDREDUCTASE INHIBITORS 3-AP AND 3-AMP - Google Patents

PROTOCOLAL FORMS OF RIBONUCLEOTIDREDUCTASE INHIBITORS 3-AP AND 3-AMP

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Publication number
RU99127343A
RU99127343A RU99127343/04A RU99127343A RU99127343A RU 99127343 A RU99127343 A RU 99127343A RU 99127343/04 A RU99127343/04 A RU 99127343/04A RU 99127343 A RU99127343 A RU 99127343A RU 99127343 A RU99127343 A RU 99127343A
Authority
RU
Russia
Prior art keywords
substituted
benzyl
ortho
para
composition
Prior art date
Application number
RU99127343/04A
Other languages
Russian (ru)
Other versions
RU2199531C2 (en
Inventor
Юн Ли
Чуан-Сенг НИУ
Ксиюйан ЛИ
Терренс В. ДОЙЛ
Су-Хюи ЧЕН
Original Assignee
Вион Фармасьютикалз, Инк.
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
Priority claimed from US08/856,568 external-priority patent/US5767134A/en
Application filed by Вион Фармасьютикалз, Инк. filed Critical Вион Фармасьютикалз, Инк.
Publication of RU99127343A publication Critical patent/RU99127343A/en
Application granted granted Critical
Publication of RU2199531C2 publication Critical patent/RU2199531C2/en

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Claims (1)

1. Соединение, соответствующее формуле:
Figure 00000001

где R4 представляет собой Н или CH3, и
R5 представляет собой СНR, бензил или орто- или пара-замещенный бензил;
R представляет собой Н, CH3, CH2CH3, CH2CH2CH3 или
Figure 00000002

R' представляет собой остаток фосфорной кислоты, соль фосфорной кислоты или -S-S-R'' группу;
R'' представляет собой CH2CH2NHR6, CH2CH2ОН, CH2СООR7, орто- или пара-замещенный C1-C3 алкилфенил или орто- или пара-замещенный нитрофенил;
R6 представляет собой Н, C1-C4 ацильную группу, трифторацетильную, бензоильную или замещенную бензоильную группу, и
R7 представляет собой Н, C1-C4 алкил, фенил, замещенный фенил или бензил, или замещенный бензил.1. The compound corresponding to the formula:
Figure 00000001

where R 4 represents H or CH 3 , and
R 5 is CHR, benzyl, or ortho or para-substituted benzyl;
R is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 or
Figure 00000002

R 'is a phosphoric acid residue, a salt of phosphoric acid or a -SS-R "group;
R "represents CH 2 CH 2 NHR 6 , CH 2 CH 2 OH, CH 2 COOR 7 , ortho or para-substituted C 1 -C 3 alkylphenyl or ortho or para-substituted nitrophenyl;
R 6 represents H, C 1 -C 4 acyl group, trifluoroacetyl, benzoyl or substituted benzoyl group, and
R 7 is H, C 1 -C 4 alkyl, phenyl, substituted phenyl or benzyl, or substituted benzyl. 2. Соединение по п.1, где R5 представляет собой CH2.2. The compound according to claim 1, where R 5 represents CH 2 . 3. Соединение по п.1, где R5 представляет собой
Figure 00000003

4. Соединение по п.3, где R представляет собой CH3.3. The compound according to claim 1, where R 5 represents
Figure 00000003

4. The compound according to claim 3, wherein R is CH 3 . 5. Соединение по п.1, где R4 представляет собой Н.5. The compound according to claim 1, where R 4 represents N. 6. Соединение по п.1, где R4 представляет собой CH3.6. The compound according to claim 1, where R 4 represents CH 3 . 7. Соединение по п.1, которое представляет собой соединение формулы:
Figure 00000004

где R4 представляет собой Н или CH3, R5 представляет собой CH2 или
Figure 00000005

и R8 представляет собой CH2CH2NH2, CH2CH2NНАс, CH2CH2ОН или CH2СО2Н. 8. Соединение по п.7, где R4 представляет собой CH3.7. The compound according to claim 1, which is a compound of the formula:
Figure 00000004

where R 4 is H or CH 3 , R 5 is CH 2 or
Figure 00000005

and R 8 is CH 2 CH 2 NH 2 , CH 2 CH 2 NHАс, CH 2 CH 2 OH or CH 2 CO 2 N. 8. The compound according to claim 7, wherein R 4 is CH 3 . 9. Соединение по п.7, где R4 представляет собой Н.9. The compound according to claim 7, where R 4 represents N. 10. Композиция, используемая при лечении неоплазии у животных, включая человека, включающая терапевтически эффективное количество соединения, соответствующего формуле:
Figure 00000006

где R4 представляет собой Н или CH3, и
R5 представляет собой СНR, бензил или орто- или пара-замещенный бензил;
R представляет собой Н, CH3, CH2CH3, CH2CH2CH3 или
Figure 00000007

R' представляет собой остаток фосфорной кислоты, соль фосфорной кислоты или -S-S-R'' группу;
R'' представляет собой CH2CH2NHR6, CH2CH2ОН, CH2СОOR7, орто- или пара-замещенный C1-C3 алкилфенил или орто- или пара-замещенный нитрофенил;
R6 представляет собой Н, C1-C4 ацильную группу, трифторацетильную, бензоильную или замещенную бензоильную группу, и
R7 представляет собой Н, C1-C4 алкил или бензил, или замещенный бензил.10. The composition used in the treatment of neoplasia in animals, including humans, comprising a therapeutically effective amount of a compound corresponding to the formula:
Figure 00000006

where R 4 represents H or CH 3 , and
R 5 is CHR, benzyl, or ortho or para-substituted benzyl;
R is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 or
Figure 00000007

R 'is a phosphoric acid residue, a salt of phosphoric acid or a -SS-R "group;
R ″ is CH 2 CH 2 NHR 6 , CH 2 CH 2 OH, CH 2 COOR 7 , ortho or para-substituted C 1 -C 3 alkylphenyl, or ortho or para-substituted nitrophenyl;
R 6 represents H, C 1 -C 4 acyl group, trifluoroacetyl, benzoyl or substituted benzoyl group, and
R 7 is H, C 1 -C 4 alkyl or benzyl, or substituted benzyl. 11. Композиция по п. 10, где R4 представляет собой Н или CH3, и R6 представляет собой CH2CH2NH2, CH2CH2NНАс, CH2CH2ОН или CH2СО2Н.11. The composition according to claim 10, wherein R 4 is H or CH 3 , and R 6 is CH 2 CH 2 NH 2 , CH 2 CH 2 NHАс, CH 2 CH 2 OH or CH 2 CO 2 N. 12. Композиция по п.10, где R4 представляет собой Н.12. The composition according to claim 10, where R 4 represents N. 13. Композиция по п.10, где R4 представляет собой CH3.13. The composition of claim 10, where R 4 is CH 3 . 14. Композиция по п.10, где R4 представляет собой Н или CH3, R5 представляет собой CH2 или
Figure 00000008
и R'' представляет собой пара- или ортозамещенный нитрофенил.14. The composition of claim 10, where R 4 is H or CH 3 , R 5 is CH 2 or
Figure 00000008
and R "represents para- or ortho-substituted nitrophenyl. 15. Композиция по п.14, где R4 представляет собой Н.15. The composition according to p. 14, where R 4 represents N. 16. Композиция по п.14, где R4 представляет собой CH3.16. The composition according to p. 14, where R 4 represents CH 3 . 17. Композиция по п.14, где R5 представляет собой
Figure 00000009

18. Композиция по п.14, где R5 представляет собой CH2.17. The composition according to p. 14, where R 5 represents
Figure 00000009

18. The composition according to p. 14, where R 5 represents CH 2 . 19. Композиция, используемая при лечении неоплазии у больных животных или людей, по п.10, включающая терапевтически эффективное количество соединения, соответствующего формуле:
Figure 00000010

где R4 представляет собой Н или CH3, R5 представляет собой CH2 или
Figure 00000011

и R8 представляет собой CH2CH2NH2, CH2CH2NНАс, CH2CH2ОН или CH2CO2Н. 20. Композиция по п.19, где R4 представляет собой CH3.19. The composition used in the treatment of neoplasia in sick animals or people, according to claim 10, comprising a therapeutically effective amount of a compound corresponding to the formula:
Figure 00000010

where R 4 is H or CH 3 , R 5 is CH 2 or
Figure 00000011

and R 8 is CH 2 CH 2 NH 2 , CH 2 CH 2 NHАс, CH 2 CH 2 ОН or CH 2 CO 2 N. 20. The composition according to claim 19, where R 4 is CH 3 . 21. Композиция по п.19, где R4 представляет собой Н.21. The composition according to claim 19, where R 4 represents N. 22. Соединение по любому из пп.1-9 используемое для получения лекарственного средства для лечения неоплазии. 22. The compound according to any one of claims 1 to 9 used to obtain drugs for the treatment of neoplasia.
RU99127343/04A 1997-05-15 1998-05-14 Pyridine-2-carboxaldehyde thiosemicarbazones and pharmaceutical composition based on thereof RU2199531C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/856,568 1997-05-15
US08/856,568 US5767134A (en) 1997-05-15 1997-05-15 Prodrug forms of ribonucleotide reductase inhibitors 3-AP and 3-AMP

Publications (2)

Publication Number Publication Date
RU99127343A true RU99127343A (en) 2001-10-20
RU2199531C2 RU2199531C2 (en) 2003-02-27

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Country Status (12)

Country Link
US (1) US5767134A (en)
EP (1) EP0988285B1 (en)
JP (1) JP2001526664A (en)
KR (1) KR20010012606A (en)
CN (2) CN101302192B (en)
AT (1) ATE309217T1 (en)
AU (1) AU727848B2 (en)
BR (1) BR9809633A (en)
CA (1) CA2290617C (en)
DE (1) DE69832276T2 (en)
RU (1) RU2199531C2 (en)
WO (1) WO1998051669A1 (en)

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AU6060499A (en) * 1998-09-24 2000-04-10 Trustees Of Columbia University In The City Of New York, The A small protein that interacts with a ribonucleotide reductase subunit and uses thereof
AU776511B2 (en) * 1999-02-18 2004-09-09 Baylor University Compositions and methods for use in targeting vascular destruction
BR0114598A (en) * 2000-10-13 2003-07-01 Vion Pharmaceuticals Inc Modified ap / amp forms prodrug
US6911460B2 (en) * 2001-04-20 2005-06-28 Vion Pharmaceuticals, Inc. Antiviral agents and methods of treating viral infections
US6855695B2 (en) * 2003-06-13 2005-02-15 Vion Pharmaceuticals, Inc. Water-soluble SHPs as novel alkylating agents
EP1691801A4 (en) * 2003-12-08 2009-12-09 Univ Arizona State SYNERGISTIC ANTICANCER COMPOSITIONS
US7605137B2 (en) * 2004-03-26 2009-10-20 Vion Pharmaceuticals, Inc. Combination therapy comprising cloretazine
CA2564868C (en) * 2004-04-28 2013-11-26 Molecules For Health, Inc. Methods for treating or preventing restenosis and other vascular proliferative disorders
BRPI0515218A (en) 2004-08-26 2008-07-08 Nicholas Piramal India Ltd compound, pharmaceutical composition, method for the treatment of a mammal or human, method of using the compound, new intermediates, use of the new intermediates, process for the preparation of a compound
TW200616604A (en) 2004-08-26 2006-06-01 Nicholas Piramal India Ltd Nitric oxide releasing prodrugs containing bio-cleavable linker
WO2006034266A2 (en) * 2004-09-21 2006-03-30 Vion Pharmaceuticals, Inc. Sulfonyl hydrazines as hypoxia-selective antineoplastic agents
US20090298891A1 (en) * 2005-09-16 2009-12-03 Government Of The Us, As Represented By The Secretady Of Health And Human Services Methods of Treating or Preventing Cancer Using Pyridine Carboxaldehyde Pyridine Thiosemicarbazone Radiosensitizing Agents
US9526707B2 (en) * 2007-08-13 2016-12-27 Howard L. Elford Methods for treating or preventing neuroinflammation or autoimmune diseases
MD3995C2 (en) * 2009-05-11 2010-07-31 Государственный Университет Молд0 Use of di(m-Ophenoxy)-di{[2-(4-aminobenzenesulfamido)-5-ethyl-1,3,4-thiadiazole]-3,5-dibromosalicylidenethiosemicarbazonato(-1)-copper} as inhibitor of mammary cancer T-47D cell proliferation
MD4126C1 (en) * 2010-11-15 2012-04-30 Государственный Университет Молд0 N,N'-[4,4'-(perfluoro-1,4-phenylenedioxy)-bis(4,1-phenylene)]-bis[2-(pyridine-2-ilmethylene)hydrazinecarbothioamide] and use thereof as prostate cancer LNCaP cell proliferation inhibitor
AR088728A1 (en) * 2011-03-25 2014-07-02 Bristol Myers Squibb Co LXR MODULATORS AS IMIDAZOL PRODROGA
US20140271812A1 (en) 2013-03-14 2014-09-18 Panacea Pharmaceuticals Treatment for chemotherapy-induced cognitive impairment
US20140287021A1 (en) 2013-03-21 2014-09-25 Panacea Pharmaceuticals Treatment of chemotherapy-induced peripheral neuropathy
GB2589912A (en) * 2019-12-12 2021-06-16 Chemestmed Ltd Method of suppressing cancer by RNA m6A methyltransferase mettl16 inhibitors

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US4447427A (en) * 1979-01-04 1984-05-08 The United States Of America As Represented By The Secretary Of The Army Method for treating bacterial infections with 2-acetyl- and 2-propionylpyridine thiosemicarbazones
US4385055A (en) * 1979-01-04 1983-05-24 The United States Of America As Represented By The Secretary Of The Army 2-Acetyl-and 2-propionylpyridine thiosemicarbazones as antimalarials
US4696938A (en) * 1986-04-25 1987-09-29 Rohm And Haas Company Insecticidal 6-aryl-pyridine thiosemicarbazones
US5281715A (en) * 1992-05-13 1994-01-25 Yale University 2-formylpyridine thiosemicarbazone compounds

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