JP2011515441A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011515441A5 JP2011515441A5 JP2011501210A JP2011501210A JP2011515441A5 JP 2011515441 A5 JP2011515441 A5 JP 2011515441A5 JP 2011501210 A JP2011501210 A JP 2011501210A JP 2011501210 A JP2011501210 A JP 2011501210A JP 2011515441 A5 JP2011515441 A5 JP 2011515441A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- hydrogen atom
- branched
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 21
- -1 pentafluorosulfanyl group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- NVJSPQCVDHGYRE-UHFFFAOYSA-N quinoline-5,8-dione Chemical group C1=CC=C2C(=O)C=CC(=O)C2=N1 NVJSPQCVDHGYRE-UHFFFAOYSA-N 0.000 claims 3
- FWWRTYBQQDXLDD-UHFFFAOYSA-N 1,4-dimethoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=C(OC)C2=C1 FWWRTYBQQDXLDD-UHFFFAOYSA-N 0.000 claims 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethoxynaphthalene Natural products C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 claims 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- UCUNHDIRXPEPHS-UHFFFAOYSA-N 5,8-dimethoxyquinoline Chemical compound C1=CC=C2C(OC)=CC=C(OC)C2=N1 UCUNHDIRXPEPHS-UHFFFAOYSA-N 0.000 claims 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims 2
- 229930192627 Naphthoquinone Natural products 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000003430 antimalarial agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- QMNFFXRFOJIOKZ-UHFFFAOYSA-N cycloguanil Chemical group CC1(C)N=C(N)N=C(N)N1C1=CC=C(Cl)C=C1 QMNFFXRFOJIOKZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 150000002791 naphthoquinones Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims 1
- RHHDMTSHWRREPK-UHFFFAOYSA-N 1,2-dimethoxynaphthalene Chemical compound C1=CC=CC2=C(OC)C(OC)=CC=C21 RHHDMTSHWRREPK-UHFFFAOYSA-N 0.000 claims 1
- ZWGGJMFMHQHTFR-UHFFFAOYSA-N 2,3-dihydronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)CCC(=O)C2=C1 ZWGGJMFMHQHTFR-UHFFFAOYSA-N 0.000 claims 1
- QJNRQJGEIYYPRW-UHFFFAOYSA-N 2,3-dimethoxyquinoline Chemical compound C1=CC=C2N=C(OC)C(OC)=CC2=C1 QJNRQJGEIYYPRW-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims 1
- PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229960001444 amodiaquine Drugs 0.000 claims 1
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 claims 1
- 229960004191 artemisinin Drugs 0.000 claims 1
- 229930101531 artemisinin Natural products 0.000 claims 1
- FIHJKUPKCHIPAT-AHIGJZGOSA-N artesunate Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@@H](OC(=O)CCC(O)=O)[C@@H]4C FIHJKUPKCHIPAT-AHIGJZGOSA-N 0.000 claims 1
- 229960004991 artesunate Drugs 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229960003677 chloroquine Drugs 0.000 claims 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims 1
- ISZNZKHCRKXXAU-UHFFFAOYSA-N chlorproguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C(Cl)=C1 ISZNZKHCRKXXAU-UHFFFAOYSA-N 0.000 claims 1
- 229950000764 chlorproguanil Drugs 0.000 claims 1
- 229960000860 dapsone Drugs 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- GJXWDTUCERCKIX-UHFFFAOYSA-N fosmidomycin Chemical compound O=CN(O)CCCP(O)(O)=O GJXWDTUCERCKIX-UHFFFAOYSA-N 0.000 claims 1
- 229950006501 fosmidomycin Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960001962 mefloquine Drugs 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims 1
- 229960000907 methylthioninium chloride Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UCRHFBCYFMIWHC-UHFFFAOYSA-N piperaquine Chemical compound ClC1=CC=C2C(N3CCN(CC3)CCCN3CCN(CC3)C=3C4=CC=C(C=C4N=CC=3)Cl)=CC=NC2=C1 UCRHFBCYFMIWHC-UHFFFAOYSA-N 0.000 claims 1
- 229950006717 piperaquine Drugs 0.000 claims 1
- 229960005179 primaquine Drugs 0.000 claims 1
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims 1
- 229960005385 proguanil Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 claims 1
- 229960000611 pyrimethamine Drugs 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000005750 substituted cyclic group Chemical group 0.000 claims 1
- 229960004673 sulfadoxine Drugs 0.000 claims 1
- 229960005404 sulfamethoxazole Drugs 0.000 claims 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims 1
- 229960001082 trimethoprim Drugs 0.000 claims 1
- 235000012711 vitamin K3 Nutrition 0.000 claims 1
- 239000011652 vitamin K3 Substances 0.000 claims 1
- 229940041603 vitamin k 3 Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08290278.4 | 2008-03-26 | ||
| EP08290278 | 2008-03-26 | ||
| PCT/EP2009/053483 WO2009118327A1 (en) | 2008-03-26 | 2009-03-25 | 1,4-naphthoquinone derivatives and therapeutic use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011515441A JP2011515441A (ja) | 2011-05-19 |
| JP2011515441A5 true JP2011515441A5 (enExample) | 2012-04-12 |
| JP5725299B2 JP5725299B2 (ja) | 2015-05-27 |
Family
ID=39529700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011501210A Active JP5725299B2 (ja) | 2008-03-26 | 2009-03-25 | １，４−ナフトキノン誘導体およびその治療用途 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9090549B2 (enExample) |
| EP (1) | EP2257515B1 (enExample) |
| JP (1) | JP5725299B2 (enExample) |
| CN (2) | CN104193609B (enExample) |
| AP (1) | AP2660A (enExample) |
| ES (1) | ES2637496T3 (enExample) |
| WO (1) | WO2009118327A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2505583A1 (en) | 2011-03-29 | 2012-10-03 | Centre National de la Recherche Scientifique | Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents |
| US20150224066A1 (en) * | 2012-09-25 | 2015-08-13 | University Of Iowa Research Foundation | Antimicrobial compositions and methods of use |
| JP7266304B2 (ja) * | 2017-04-21 | 2023-04-28 | ユニヴァーシティー オブ タスマニア | 治療化合物および方法 |
| EP4053096A1 (en) * | 2021-03-05 | 2022-09-07 | Centre national de la recherche scientifique | Photoredox radical benzylation process |
| CN113264818B (zh) * | 2021-05-25 | 2022-07-05 | 湖北工业大学 | 一种银催化醌类化合物与醇类的碳碳交叉偶联反应的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398418A (en) * | 1943-08-27 | 1946-04-16 | Louis F Fieser | Introduction of organic radicals into quinones |
| EP0301861B1 (en) * | 1987-07-29 | 1992-04-01 | Takeda Chemical Industries, Ltd. | Cell proliferation inhibitors |
| US5244917A (en) * | 1992-06-02 | 1993-09-14 | The Dupont Merck Pharmaceutical Company | Substituted naphthofurans as anti-inflammatory agents |
| CA2290630A1 (en) * | 1998-03-20 | 1999-09-30 | Suntory Limited | Nf-kb inhibitors containing as the active ingredient phenylmethyl benzoquinone |
| US20040022787A1 (en) * | 2000-07-03 | 2004-02-05 | Robert Cohen | Methods for treating an autoimmune disease using a soluble CTLA4 molecule and a DMARD or NSAID |
| JP4780371B2 (ja) | 2003-06-27 | 2011-09-28 | 武田薬品工業株式会社 | 光学活性化合物の製造法 |
| AU2003265967A1 (en) * | 2003-09-05 | 2005-04-21 | Georgia State University Research Foundation, Inc | Novel amidine compounds for treating microbial infections |
| AU2006202040A1 (en) * | 2005-05-20 | 2006-12-07 | Reto Brun | Novel biochalcophenes and their prodrugs as antiprotozoal agents |
-
2009
- 2009-03-25 ES ES09724636.7T patent/ES2637496T3/es active Active
- 2009-03-25 EP EP09724636.7A patent/EP2257515B1/en active Active
- 2009-03-25 CN CN201410321080.0A patent/CN104193609B/zh active Active
- 2009-03-25 WO PCT/EP2009/053483 patent/WO2009118327A1/en not_active Ceased
- 2009-03-25 CN CN2009801150361A patent/CN102015607A/zh active Pending
- 2009-03-25 JP JP2011501210A patent/JP5725299B2/ja active Active
- 2009-03-25 AP AP2010005435A patent/AP2660A/xx active
- 2009-03-25 US US12/934,382 patent/US9090549B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105906617B (zh) | Hec1活性调节剂及其方法 | |
| JP6511430B2 (ja) | がんの治療のための化合物および組成物 | |
| Singh et al. | Antimalarial pyrido [1, 2-a] benzimidazoles: lead optimization, parasite life cycle stage profile, mechanistic evaluation, killing kinetics, and in vivo oral efficacy in a mouse model | |
| JP2008517983A5 (enExample) | ||
| JP2002513793A5 (enExample) | ||
| JP2011515441A5 (enExample) | ||
| Vennerstrom et al. | Bisquinolines. 2. Antimalarial N, N-bis (7-chloroquinolin-4-yl) heteroalkanediamines | |
| HUP0301932A2 (hu) | IL-1béta és TNF-a inhibitor benzofenon származékok, ezeket tartalmazó gyógyszerkészítmények és ezek alkalmazása gyógyszerkészítmények elżállítására | |
| JP2002030084A5 (enExample) | ||
| JP2018525414A (ja) | 癌を処置するための方法 | |
| JP6149129B2 (ja) | 早期老化、特には早老症を治療する為に有用な化合物 | |
| JP2005538974A5 (enExample) | ||
| JP2003513066A5 (enExample) | ||
| JP2006519807A5 (enExample) | ||
| CN101443008A (zh) | 芳基-和杂芳基-取代的四氢异喹啉和其阻止去甲肾上腺素，3-羟酪胺和5-羟色胺的再吸收的用途 | |
| CN114081890B (zh) | 嘧啶酮类衍生物在抗结核杆菌感染中的应用 | |
| RU2010154417A (ru) | Комбинация частичного агониста никотиновых рецепторов и ингибитора ацетилхолинетеразы, содержащая ее фармацетическая композиция, и ее применение в лечении когнитивных расстройств | |
| JP2006524682A5 (enExample) | ||
| JP2009519227A5 (enExample) | ||
| CN114364673A (zh) | 含三环结构的芳香杂环化合物，及其制备方法和应用 | |
| TW200811100A (en) | Compounds and methods for inhibiting the interaction of BCL proteins with binding partners | |
| JP2007529471A5 (enExample) | ||
| EP0785924B1 (fr) | Bis-2-aminopyridines, leur procede de preparation et leurs applications contre les parasitoses | |
| JP2005529079A5 (enExample) | ||
| Dyablo et al. | Methylamino-and dimethylaminoquinolines |