JP2006518726A5 - - Google Patents
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- Publication number
- JP2006518726A5 JP2006518726A5 JP2006502131A JP2006502131A JP2006518726A5 JP 2006518726 A5 JP2006518726 A5 JP 2006518726A5 JP 2006502131 A JP2006502131 A JP 2006502131A JP 2006502131 A JP2006502131 A JP 2006502131A JP 2006518726 A5 JP2006518726 A5 JP 2006518726A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- formula
- methylquinolinio
- amido
- 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.)
- Pending
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- -1 1-methylquinolinio-6-yl Chemical group 0.000 claims description 39
- 125000003368 amide group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 58
- 150000003839 salts Chemical class 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 150000001408 amides Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 201000011510 cancer Diseases 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 150000007522 mineralic acids Chemical class 0.000 claims 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 6
- 150000007524 organic acids Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 150000007529 inorganic bases Chemical class 0.000 claims 5
- 238000000638 solvent extraction Methods 0.000 claims 5
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 238000002512 chemotherapy Methods 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 150000007530 organic bases Chemical class 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 108091081406 G-quadruplex Proteins 0.000 claims 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 235000005985 organic acids Nutrition 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- RTQPKEOYPPMVGQ-UHFFFAOYSA-N 1-methylquinolin-1-ium Chemical group C1=CC=C2[N+](C)=CC=CC2=C1 RTQPKEOYPPMVGQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 206010020112 Hirsutism Diseases 0.000 claims 2
- 208000026350 Inborn Genetic disease Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005237 alkyleneamino group Chemical group 0.000 claims 2
- 230000001093 anti-cancer Effects 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims 2
- 208000016361 genetic disease Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 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 1
- 102000015790 Asparaginase Human genes 0.000 claims 1
- 108010024976 Asparaginase Proteins 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 208000005692 Bloom Syndrome Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010052465 Congenital poikiloderma Diseases 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010023825 Laryngeal cancer Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000000791 Rothmund-Thomson syndrome Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 101710183280 Topoisomerase Proteins 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 201000011032 Werner Syndrome Diseases 0.000 claims 1
- 150000003838 adenosines Chemical class 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 1
- JKOQGQFVAUAYPM-UHFFFAOYSA-N amifostine Chemical compound NCCCNCCSP(O)(O)=O JKOQGQFVAUAYPM-UHFFFAOYSA-N 0.000 claims 1
- 229960001097 amifostine Drugs 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000001772 anti-angiogenic effect Effects 0.000 claims 1
- 229940044684 anti-microtubule agent Drugs 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229960003272 asparaginase Drugs 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical group [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 claims 1
- 230000001977 ataxic effect Effects 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims 1
- 229960000605 dexrazoxane Drugs 0.000 claims 1
- 150000004891 diazines Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 150000005699 fluoropyrimidines Chemical class 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 229940022353 herceptin Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 1
- 229960004768 irinotecan Drugs 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000810 peripheral vasodilating agent Substances 0.000 claims 1
- 229960002116 peripheral vasodilator Drugs 0.000 claims 1
- 150000003057 platinum Chemical class 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229960005314 suramin Drugs 0.000 claims 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- 229960001727 tretinoin Drugs 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (2)
| 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 |
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2006518726A JP2006518726A (ja) | 2006-08-17 |
| JP2006518726A5 true JP2006518726A5 (enrdf_load_stackoverflow) | 2007-04-05 |
Family
ID=32731875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006502131A Pending JP2006518726A (ja) | 2003-02-07 | 2004-02-05 | Ｇ四重鎖ｄｎａ構造に極めて特異的に結合する化学誘導体、および、特異的な抗ガン剤としてのそれらの使用 |
Country Status (8)
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 |
| US20110059070A1 (en) * | 2006-09-14 | 2011-03-10 | Ramot At Tel Aviv University Ltd. | Combination therapy for tumoral desease treatment |
| GB0706932D0 (en) * | 2007-04-10 | 2007-05-16 | Univ London Pharmacy | Ureylene derivatives |
| WO2009040819A2 (en) | 2007-09-25 | 2009-04-02 | Ramot At Tel Aviv University Ltd. | DOWN-REGULATION OF MORTALIN BY siRNA |
| CN101889210B (zh) | 2008-05-27 | 2014-12-10 | 松下电器产业株式会社 | G-quadruplex检测方法、形成G-quadruplex的DNA的检测方法以及端粒酶活性测定方法 |
| 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 |
| US20210246120A1 (en) * | 2018-08-24 | 2021-08-12 | Biomedical Research Foundation Of The Academy Of Athens (Brfaa) | Method of preparation and use of phosphoinositide 3-kinase inhibitors in treating cancer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020058043A (ko) * | 1999-11-29 | 2002-07-12 | 추후제출 | 아릴아민 유도체 및 안티-텔로머라제로서 이의 용도 |
| 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 |
| WO2002096903A2 (fr) * | 2001-05-28 | 2002-12-05 | Aventis Pharma S.A. | Derives chimiques et leur application comme agent antitelomerase |
-
2003
- 2003-02-07 FR FR0301478A patent/FR2850970B1/fr not_active Expired - Fee Related
-
2004
- 2004-02-05 BR BRPI0407320-7A patent/BRPI0407320A/pt not_active IP Right Cessation
- 2004-02-05 AU AU2004210753A patent/AU2004210753A1/en not_active Abandoned
- 2004-02-05 MX MXPA05007648A patent/MXPA05007648A/es not_active Application Discontinuation
- 2004-02-05 EP EP04708378A patent/EP1603898A2/fr not_active Withdrawn
- 2004-02-05 CA CA002514105A patent/CA2514105A1/fr not_active Abandoned
- 2004-02-05 JP JP2006502131A patent/JP2006518726A/ja active Pending
- 2004-02-05 WO PCT/FR2004/000260 patent/WO2004072027A2/fr not_active Ceased
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