CA2514105A1 - Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique - Google Patents
Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique Download PDFInfo
- Publication number
- CA2514105A1 CA2514105A1 CA002514105A CA2514105A CA2514105A1 CA 2514105 A1 CA2514105 A1 CA 2514105A1 CA 002514105 A CA002514105 A CA 002514105A CA 2514105 A CA2514105 A CA 2514105A CA 2514105 A1 CA2514105 A1 CA 2514105A1
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- Prior art keywords
- amide
- methyl
- formula
- products
- pyridine
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 108091081406 G-quadruplex Proteins 0.000 title claims abstract description 24
- 239000002246 antineoplastic agent Substances 0.000 title abstract description 4
- 239000000126 substance Substances 0.000 title description 3
- -1 heterocyclic diamides Chemical class 0.000 claims abstract description 189
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 45
- 238000002360 preparation method Methods 0.000 claims abstract description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 24
- 108020004414 DNA Proteins 0.000 claims abstract description 19
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- 125000003118 aryl group Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 42
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- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 30
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 27
- 239000011707 mineral Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
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- 239000003814 drug Substances 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 22
- RTQPKEOYPPMVGQ-UHFFFAOYSA-N 1-methylquinolin-1-ium Chemical compound C1=CC=C2[N+](C)=CC=CC2=C1 RTQPKEOYPPMVGQ-UHFFFAOYSA-N 0.000 claims description 20
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
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- 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 claims description 8
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- KEOLYURDXNRJEY-UHFFFAOYSA-N 1,2-dimethylquinolin-1-ium Chemical compound C1=CC=CC2=[N+](C)C(C)=CC=C21 KEOLYURDXNRJEY-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
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- MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-N 0.000 claims description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 4
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0301478A FR2850970B1 (fr) | 2003-02-07 | 2003-02-07 | Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique |
| FR03/01478 | 2003-02-07 | ||
| PCT/FR2004/000260 WO2004072027A2 (fr) | 2003-02-07 | 2004-02-05 | Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2514105A1 true CA2514105A1 (fr) | 2004-08-26 |
Family
ID=32731875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002514105A Abandoned CA2514105A1 (fr) | 2003-02-07 | 2004-02-05 | Derives chimiques se liant de maniere tres specifique aux structures d'adn en g-quadruplexe et leur application comme agent anticancereux specifique |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1603898A2 (enExample) |
| JP (1) | JP2006518726A (enExample) |
| AU (1) | AU2004210753A1 (enExample) |
| BR (1) | BRPI0407320A (enExample) |
| CA (1) | CA2514105A1 (enExample) |
| FR (1) | FR2850970B1 (enExample) |
| MX (1) | MXPA05007648A (enExample) |
| WO (1) | WO2004072027A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887873B2 (en) | 2001-03-23 | 2005-05-03 | Aventis Pharma S.A. | Triazine derivatives and their application as antitelomerase agents |
| US8293716B2 (en) | 2005-05-26 | 2012-10-23 | Ramot At Tel Aviv University Ltd. | Method of treating cancer by modulation of mortalin |
| WO2008032324A2 (en) * | 2006-09-14 | 2008-03-20 | Ramot At Tel Aviv University Ltd. | Combination therapy for tumoral disease treatment |
| GB0706932D0 (en) * | 2007-04-10 | 2007-05-16 | Univ London Pharmacy | Ureylene derivatives |
| US8470793B2 (en) | 2007-09-25 | 2013-06-25 | Ramot At Tel-Aviv University Ltd. | Down-regulation of mortalin by siRNA |
| WO2009144914A1 (ja) | 2008-05-27 | 2009-12-03 | パナソニック株式会社 | Ｇ－ｑｕａｄｒｕｐｌｅｘ検出方法、Ｇ－ｑｕａｄｒｕｐｌｅｘ形成ＤＮＡ検出方法およびテロメラーゼ活性測定方法 |
| JP4510929B1 (ja) | 2009-04-09 | 2010-07-28 | パナソニック株式会社 | テロメラーゼ反応阻害方法およびそれに用いられるテロメラーゼ反応阻害剤 |
| CN108066340B (zh) * | 2016-11-10 | 2020-10-27 | 中国科学院化学研究所 | 药物组合物 |
| CN108066341B (zh) * | 2016-11-10 | 2020-10-30 | 中国科学院化学研究所 | 化合物在制备抗癌药物中的用途 |
| WO2018211148A1 (en) * | 2017-05-19 | 2018-11-22 | Universite De Bretagne Occidentale | Bisquinolium derivatives for preventing or treating ebv-related cancers |
| CN113272294A (zh) * | 2018-08-24 | 2021-08-17 | 雅典学院生物医学研究基金会 | 2,6-双(((1h-苯并[d]咪唑-2-基)硫)甲基)吡啶和n2,n6-二苄基吡啶-2,6-二甲酰胺衍生物以及相关化合物作为磷酸肌醇3-激酶(pi3k)抑制剂用于治疗癌症 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003515604A (ja) * | 1999-11-29 | 2003-05-07 | アベンテイス・フアルマ・ソシエテ・アノニム | アリールアミン誘導体およびそれらの抗−テロメラーゼ剤としての使用 |
| FR2819255B1 (fr) * | 2001-01-09 | 2003-02-28 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| FR2821355A1 (fr) * | 2001-02-23 | 2002-08-30 | Aventis Pharma Sa | Derives chimiques et leur application comme agent antitelomerase |
| CO5380035A1 (es) * | 2001-03-23 | 2004-03-31 | Aventis Pharma Sa | Derivados quimicos y su aplicacion como agente antitelomerasa |
| JP2004534046A (ja) * | 2001-05-28 | 2004-11-11 | アベンティス・ファーマ・ソシエテ・アノニム | 化学誘導体および抗テロメラーゼ剤としてのその使用 |
-
2003
- 2003-02-07 FR FR0301478A patent/FR2850970B1/fr not_active Expired - Fee Related
-
2004
- 2004-02-05 CA CA002514105A patent/CA2514105A1/fr not_active Abandoned
- 2004-02-05 WO PCT/FR2004/000260 patent/WO2004072027A2/fr not_active Ceased
- 2004-02-05 EP EP04708378A patent/EP1603898A2/fr not_active Withdrawn
- 2004-02-05 AU AU2004210753A patent/AU2004210753A1/en not_active Abandoned
- 2004-02-05 BR BRPI0407320-7A patent/BRPI0407320A/pt not_active IP Right Cessation
- 2004-02-05 JP JP2006502131A patent/JP2006518726A/ja active Pending
- 2004-02-05 MX MXPA05007648A patent/MXPA05007648A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2850970A1 (fr) | 2004-08-13 |
| MXPA05007648A (es) | 2006-12-15 |
| EP1603898A2 (fr) | 2005-12-14 |
| WO2004072027A2 (fr) | 2004-08-26 |
| WO2004072027A3 (fr) | 2004-09-23 |
| BRPI0407320A (pt) | 2006-02-21 |
| JP2006518726A (ja) | 2006-08-17 |
| FR2850970B1 (fr) | 2006-07-07 |
| AU2004210753A1 (en) | 2004-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |