BR9809633A - Formas de pró-drogas de inibidores de ribonucleotìdeo redutase 3-ap e 3-amp - Google Patents
Formas de pró-drogas de inibidores de ribonucleotìdeo redutase 3-ap e 3-ampInfo
- Publication number
- BR9809633A BR9809633A BR9809633-8A BR9809633A BR9809633A BR 9809633 A BR9809633 A BR 9809633A BR 9809633 A BR9809633 A BR 9809633A BR 9809633 A BR9809633 A BR 9809633A
- Authority
- BR
- Brazil
- Prior art keywords
- benzyl
- ortho
- substituted
- reductase inhibitors
- pro
- Prior art date
Links
- 229940002612 prodrug Drugs 0.000 title abstract 2
- 239000000651 prodrug Substances 0.000 title abstract 2
- 229940127395 Ribonucleotide Reductase Inhibitors Drugs 0.000 title 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- FYAKAEANAJIHHV-UUILKARUSA-N [(e)-(3-amino-4-methylpyridin-2-yl)methylideneamino]thiourea Chemical compound CC1=CC=NC(\C=N\NC(N)=S)=C1N FYAKAEANAJIHHV-UUILKARUSA-N 0.000 abstract 2
- XMYKNCNAZKMVQN-NYYWCZLTSA-N [(e)-(3-aminopyridin-2-yl)methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=NC=CC=C1N XMYKNCNAZKMVQN-NYYWCZLTSA-N 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 229960005526 triapine Drugs 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 102000028649 Ribonucleoside-diphosphate reductase Human genes 0.000 abstract 1
- 108010038105 Ribonucleoside-diphosphate reductase Proteins 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- -1 and R7 is H Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Patente de Invenção: <B>"FORMAS DE PRó-DROGAS DE INIBIDORES DE RIBONUCLEOTìDEO REDUTASE 3-AP E 3-AMP"<D>. A presente invenção refere-se a novas formas de pró-drogas de inibidores de ribonucleosídeo difosfato redutase 3-aminopiridina-2-carbocaldeído tiosemicarbanoza (3-AP) e 3-amino-4-metilpiridina-2-carboxaldeíddo tioesemcarbazona (3-AMP) as quais têm aumentada solubilidade em água, biodisponibilidade e resistência a acetilação in vivo de suas funções amino. Novos compostos de acordo com a presente invenção referem-se aos de fórmula (1), em que R^ 4^ é H ou CH~ 3~ e R^ 5^ é CHR, benzila ou benzil orto ou para substituído; R é H, CH~ 3~, CH~ 2~CH~ 3~, CH~ 2~CH~ 2~CH~ 3~ ou (a); R' é um fosfato ácido livre, sal de fosfato ou um grupo -S-S-R"; R" é CH~ 2~CH~ 2~NHR^ 6^, CH~ 2~CH~ 2~OH, CH~ 2~COOR^ 7^, alquilfenila orto ou para substituído e um nitrofenila orto ou para substituído; R^ 6^ é H, grupo C~ 1~ - C~ 4~ acila, grupo trifluoroacetila, grupo benzoíla ou benzoíla substituída, e R^ 7^ é H, C~ 1~ - C~ 4~ alquila ou um benzila ou benzila substituída.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/856,568 US5767134A (en) | 1997-05-15 | 1997-05-15 | Prodrug forms of ribonucleotide reductase inhibitors 3-AP and 3-AMP |
| PCT/US1998/009705 WO1998054695A1 (en) | 1997-05-27 | 1998-05-14 | Method of accessing a dial-up service |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR9809633A true BR9809633A (pt) | 2000-07-11 |
Family
ID=25323971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9809633-8A BR9809633A (pt) | 1997-05-15 | 1998-05-14 | Formas de pró-drogas de inibidores de ribonucleotìdeo redutase 3-ap e 3-amp |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5767134A (pt) |
| EP (1) | EP0988285B1 (pt) |
| JP (1) | JP2001526664A (pt) |
| KR (1) | KR20010012606A (pt) |
| CN (2) | CN101302192B (pt) |
| AT (1) | ATE309217T1 (pt) |
| AU (1) | AU727848B2 (pt) |
| BR (1) | BR9809633A (pt) |
| CA (1) | CA2290617C (pt) |
| DE (1) | DE69832276T2 (pt) |
| RU (1) | RU2199531C2 (pt) |
| WO (1) | WO1998051669A1 (pt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2002537262A (ja) * | 1999-02-18 | 2002-11-05 | オキシジェン，インコーポレイティド | 血管破壊のターゲッティングに使用するための組成物および方法 |
| KR20030063360A (ko) * | 2000-10-13 | 2003-07-28 | 비온 퍼마슈티컬즈 인코포레이티드 | 에이피/에이엠피 유도 전구약물 형태 |
| WO2002085358A2 (en) * | 2001-04-20 | 2002-10-31 | 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 |
| WO2005055952A2 (en) * | 2003-12-08 | 2005-06-23 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Synergistic anti-cancer compositions |
| WO2005094282A2 (en) * | 2004-03-26 | 2005-10-13 | Vion Pharmaceuticals, Inc. | Combination therapy comprising cloretazinetm |
| WO2005115405A1 (en) * | 2004-04-28 | 2005-12-08 | Molecules For Health, Inc. | Methods for treating or preventing restenosis and other vascular proliferative disorders |
| TW200616604A (en) | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| KR20070053214A (ko) | 2004-08-26 | 2007-05-23 | 니콜라스 피라말 인디아 리미티드 | 신규 생분해성 링커를 함유하는 프로드럭 |
| EP1793823B1 (en) * | 2004-09-21 | 2012-08-08 | Vion Pharmaceuticals, Inc. | Phosphate containing prodrugs of sulfonyl hydrazines as hypoxia-selective antineoplastic agents |
| WO2007035489A2 (en) * | 2005-09-16 | 2007-03-29 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of treating or preventing cancer using pyridine carboxaldehyde pyridine thiosemicarbazone radiosensitizing agents |
| EP2030615A3 (en) * | 2007-08-13 | 2009-12-02 | ELFORD, Howard L. | Ribonucleotide reductase inhibitors for use in the treatment or prevention of neuroinflammatory or autoimmune diseases |
| MD3995C2 (ro) * | 2009-05-11 | 2010-07-31 | Государственный Университет Молд0 | Utilizare a di(µ-Ofenoxi)-di{[2-(4-aminobenzensulfamido)-5-etil-1,3,4-tiadiazol]-3,5-dibromosalicilidentiosemicarbazonato(-1)-cupru} în calitate de inhibitor al proliferării celulelor T-47D ale cancerului mamar |
| MD4126C1 (ro) * | 2010-11-15 | 2012-04-30 | Государственный Университет Молд0 | N,N'-[4,4'-(perfluoro-1,4-fenilendioxi)-bis(4,1-fenilen)]-bis[2-(piridin-2-ilmetilen)hidrazincarbotioamidă] şi utilizarea ei în calitate de inhibitor al proliferării celulelor LNCaP ale cancerului prostatei |
| TW201242953A (en) * | 2011-03-25 | 2012-11-01 | Bristol Myers Squibb Co | Imidazole prodrug LXR modulators |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1997
- 1997-05-15 US US08/856,568 patent/US5767134A/en not_active Expired - Lifetime
-
1998
- 1998-05-14 EP EP98922247A patent/EP0988285B1/en not_active Expired - Lifetime
- 1998-05-14 AU AU74840/98A patent/AU727848B2/en not_active Ceased
- 1998-05-14 WO PCT/US1998/009750 patent/WO1998051669A1/en active IP Right Grant
- 1998-05-14 CA CA002290617A patent/CA2290617C/en not_active Expired - Fee Related
- 1998-05-14 CN CN200810095427.9A patent/CN101302192B/zh not_active Expired - Lifetime
- 1998-05-14 RU RU99127343/04A patent/RU2199531C2/ru not_active IP Right Cessation
- 1998-05-14 AT AT98922247T patent/ATE309217T1/de not_active IP Right Cessation
- 1998-05-14 JP JP54948498A patent/JP2001526664A/ja not_active Ceased
- 1998-05-14 CN CN98805148A patent/CN1256687A/zh active Pending
- 1998-05-14 DE DE69832276T patent/DE69832276T2/de not_active Expired - Fee Related
- 1998-05-14 KR KR1019997010565A patent/KR20010012606A/ko not_active Application Discontinuation
- 1998-05-14 BR BR9809633-8A patent/BR9809633A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2290617A1 (en) | 1998-11-19 |
| EP0988285A4 (en) | 2000-08-16 |
| AU727848B2 (en) | 2001-01-04 |
| WO1998051669A1 (en) | 1998-11-19 |
| DE69832276T2 (de) | 2006-08-03 |
| RU2199531C2 (ru) | 2003-02-27 |
| CN101302192B (zh) | 2014-01-22 |
| EP0988285B1 (en) | 2005-11-09 |
| EP0988285A1 (en) | 2000-03-29 |
| US5767134A (en) | 1998-06-16 |
| CN101302192A (zh) | 2008-11-12 |
| CN1256687A (zh) | 2000-06-14 |
| ATE309217T1 (de) | 2005-11-15 |
| JP2001526664A (ja) | 2001-12-18 |
| KR20010012606A (ko) | 2001-02-15 |
| DE69832276D1 (de) | 2005-12-15 |
| AU7484098A (en) | 1998-12-08 |
| CA2290617C (en) | 2008-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B11B | Dismissal acc. art. 36, par 1 of ipl - no reply within 90 days to fullfil the necessary requirements |