WO1995019974B1 - Composes a base de calixarene presentant une activite antibacterienne, antifongique, anticancereuse et anti-vih - Google Patents
Composes a base de calixarene presentant une activite antibacterienne, antifongique, anticancereuse et anti-vihInfo
- Publication number
- WO1995019974B1 WO1995019974B1 PCT/IE1995/000008 IE9500008W WO9519974B1 WO 1995019974 B1 WO1995019974 B1 WO 1995019974B1 IE 9500008 W IE9500008 W IE 9500008W WO 9519974 B1 WO9519974 B1 WO 9519974B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- halogen
- hydrogen
- formula
- fungal
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- VTJUKNSKBAOEHE-UHFFFAOYSA-N Calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 title claims abstract 4
- 230000000694 effects Effects 0.000 title abstract 3
- 230000000844 anti-bacterial Effects 0.000 title abstract 2
- 230000000843 anti-fungal Effects 0.000 title abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 4
- YECHEDVCXXVLIY-UHFFFAOYSA-N Cyclotriveratrylene Chemical group C1C2=CC(OC)=C(OC)C=C2CC2=CC(OC)=C(OC)C=C2CC2=C1C=C(OC)C(OC)=C2 YECHEDVCXXVLIY-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 5
- 229910052751 metal Inorganic materials 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- 206010017533 Fungal infection Diseases 0.000 claims 4
- 206010047461 Viral infection Diseases 0.000 claims 4
- 208000001756 Virus Disease Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 230000017613 viral reproduction Effects 0.000 claims 4
- 206010060945 Bacterial infection Diseases 0.000 claims 3
- -1 amino acid ester Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- 150000002500 ions Chemical class 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 239000003429 antifungal agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000003115 biocidal Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2H-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N 4H-1,2,4-triazol-3-amine Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- APKFDSVGJQXUKY-INPOYWNPSA-N BRL-49594 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims 1
- 208000005721 HIV Infections Diseases 0.000 claims 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims 1
- 229950008974 SINEFUNGIN Drugs 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229960003942 amphotericin B Drugs 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 230000001580 bacterial Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 150000002960 penicillins Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229920001568 phenolic resin Polymers 0.000 claims 1
- 239000002459 polyene antibiotic agent Substances 0.000 claims 1
- 150000004291 polyenes Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- LMXOHSDXUQEUSF-YECHIGJVSA-N sinefungin Chemical compound O[C@@H]1[C@H](O)[C@@H](C[C@H](CC[C@H](N)C(O)=O)N)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LMXOHSDXUQEUSF-YECHIGJVSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical class OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000036436 anti-hiv Effects 0.000 abstract 1
- 230000000840 anti-viral Effects 0.000 abstract 1
Abstract
Composés à base de calixarène présentant une activité biologique et notamment antibactérienne, antifongique, anticancéreuse et antivirale. Il s'avère que certains composés présentent une activité anti-VIH. Les composés sont des calixarènes ou oxacalixarènes, des oligomères acycliques de phényle-formol, des dérivés de cyclotrivératrylène, des dérivés cycliques tétramères de résorcinol-aldéhyde appelés composés de Hogberg, et des dérivés cycliques tétramères de pyrogallol-aldéhyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU15453/95A AU1545395A (en) | 1994-01-24 | 1995-01-24 | Calixarene-based compounds having antibacterial, antifungal, anticancer-hiv activity |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE940057 | 1994-01-24 | ||
| IES940057 | 1994-01-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1995019974A2 WO1995019974A2 (fr) | 1995-07-27 |
| WO1995019974A3 WO1995019974A3 (fr) | 1995-09-21 |
| WO1995019974B1 true WO1995019974B1 (fr) | 1995-11-16 |
Family
ID=11040267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IE1995/000008 WO1995019974A2 (fr) | 1994-01-24 | 1995-01-24 | Composes a base de calixarene presentant une activite antibacterienne, antifongique, anticancereuse et anti-vih |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU1545395A (fr) |
| WO (1) | WO1995019974A2 (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2147075A1 (fr) * | 1994-04-28 | 1995-10-29 | Genesis Group Inc. | Composes polymeriques chromotropes d'acide-formaldehyde et de 1-naphtol-formaldehyde |
| JP4180238B2 (ja) * | 1997-12-09 | 2008-11-12 | 株式会社コスモ総合研究所 | 環状フェノール硫化物のスルホン酸化合物及びその製造方法 |
| NL1008988C2 (nl) * | 1998-04-24 | 1999-10-26 | Stichting Tech Wetenschapp | Calixareenverbinding en een selectief molecuul voorzien van een dergelijke verbinding. |
| AU4543899A (en) * | 1998-06-08 | 1999-12-30 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| IES20011021A2 (en) * | 2000-12-01 | 2002-12-11 | Aids Care Pharma Ltd | Anti-viral compounds |
| ATE510547T1 (de) | 2001-03-08 | 2011-06-15 | Univ Pennsylvania | Faciale amphiphile polymere als infektionsbekämpfende mittel |
| IE20020449A1 (en) * | 2002-05-31 | 2003-12-10 | Aids Care Pharma Ltd | Anti-viral compounds |
| DE10226099A1 (de) * | 2002-06-12 | 2004-01-08 | Jörg Martin Dipl.-Chem. Dormann | Filtermaterial für Toxine, Bakterien, Viren und andere physiologische Schadstoffe |
| JP2006521355A (ja) | 2003-03-17 | 2006-09-21 | ザ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・ペンシルベニア・センター・フオー・テクノロジー・トランスフアー | 表面的に両親媒性のポリマー及びオリゴマーならびにそれらの使用 |
| AU2003229567A1 (en) * | 2003-03-24 | 2004-10-18 | Centre National De La Recherche Scientifique | New calix arene compounds, their process of preparation and their use, particularly as enzymatic mimes |
| US7338977B2 (en) * | 2003-11-25 | 2008-03-04 | Aids Care Pharma Limited | Anti-viral compounds |
| CN1922133A (zh) | 2004-01-23 | 2007-02-28 | 宾夕法尼亚州大学理事会 | 表面两亲性聚芳基和聚芳基炔基聚合物和低聚物及其用途 |
| PL1802291T3 (pl) | 2004-10-04 | 2012-05-31 | Univ Minnesota | Oparte na kaliksarenie mimetyki konformacji peptydu, sposoby ich stosowania oraz sposoby przygotowania |
| WO2009025335A1 (fr) * | 2007-08-23 | 2009-02-26 | Jsr Corporation | Composition et composé sensibles au rayonnement |
| FR2939666B1 (fr) * | 2008-12-17 | 2012-11-30 | Irsn | Formulations cosmetiques et pharmaceutiques de molecules de calix[6]arenes |
| FR2974012A1 (fr) * | 2011-04-12 | 2012-10-19 | Univ Nancy 1 Henri Poincare | Utilisation de calixarenes dans le traitement des infections bacteriennes |
| FR2974013B1 (fr) * | 2011-04-12 | 2017-02-17 | Univ De Nancy 1 Henri Poincare | Utilisation de calixarenes associes avec un antibiotique dans le traitement des infections bacteriennes |
| TWI596082B (zh) * | 2011-08-12 | 2017-08-21 | 三菱瓦斯化學股份有限公司 | 環狀化合物、其製造方法、組成物及光阻圖型之形成方法 |
| JP6313046B2 (ja) * | 2011-11-18 | 2018-04-18 | 三菱瓦斯化学株式会社 | 環状化合物、その製造方法、感放射線性組成物及びレジストパターン形成方法 |
| EP2781504B1 (fr) * | 2011-11-18 | 2017-01-04 | Mitsubishi Gas Chemical Company, Inc. | Composé cyclique ainsi que son procédé de fabrication, composition sensible aux rayonnements, et procédé de formation de motif de réserve |
| US20150368213A1 (en) * | 2014-06-20 | 2015-12-24 | The University of Montana, Missoula, MT | Novel Inhibitors of System Xc- |
| CN107043364B (zh) * | 2016-02-05 | 2020-04-03 | 徐州医学院 | 氧杂杯[4]芳烃衍生物及其应用 |
| CN107325810A (zh) * | 2017-06-29 | 2017-11-07 | 广东医科大学 | 一种穴状多羟基荧光化合物及其应用 |
| TW202028199A (zh) * | 2018-09-28 | 2020-08-01 | 大陸商重慶複創醫藥研究有限公司 | 作為蛋白激酶抑制劑的萘啶酮和吡啶基嘧啶酮類化合物 |
| FI20185841A1 (fi) * | 2018-10-08 | 2020-04-09 | Aalto Univ Foundation Sr | Makrosykliset yhdisteet ja niiden käytöt |
| CN115252869B (zh) * | 2022-08-18 | 2023-06-06 | 南通大学 | 一种促进血管再生的纳米敷料及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE59509B1 (en) * | 1987-01-21 | 1994-03-09 | Loctite Ireland Ltd | Functionalised oxacalixarenes, their preparation and use in instant adhesive compositions |
| IE68312B1 (en) * | 1989-12-13 | 1996-06-12 | Loctite Ireland Ltd | Calixarene and oxacalixarene derivatives and use thereof for sequestration of metals |
| US5210216A (en) * | 1985-03-28 | 1993-05-11 | Loctite (Ireland) Limited | Calixarene and oxacalixarene derivatives and use thereof of sequestration metals |
| US5043415A (en) * | 1987-09-24 | 1991-08-27 | Loctite (Ireland) Ltd. | Nitrogen-containing oxacalixarene and calixarene derivatives, polymers including groups related to such derivatives, and use of such compounds |
| US4604404A (en) * | 1985-04-03 | 1986-08-05 | A. H. Robins Company, Inc. | Antiviral sulfonated naphthalene formaldehyde condensation polymers |
| EP0259016B1 (fr) * | 1986-08-29 | 1990-07-04 | LOCTITE (IRELAND) Ltd. | Dérivés de la calixarène et leur utilisation comme accélérateurs pour compositions adhésives instantanées |
| IE862567L (en) * | 1986-09-29 | 1988-03-29 | Loctite Ireland Ltd | Encapsulating compositions |
| IE893986A1 (en) * | 1989-12-13 | 1991-06-19 | Loctite Ireland Ltd | Polymerisable calixarene and oxacalixarene derivatives,¹polymers thereof, and use of such derivatives and polymers¹for sequestration of metals |
| IE904444A1 (en) * | 1990-12-10 | 1992-06-17 | Stephen J Harris | Ion-selective electrodes |
| US5312837A (en) * | 1991-01-29 | 1994-05-17 | Genelabs Technologies, Inc. | Method of treating viral infections with aryl macrocyclic compounds |
| FR2672214A1 (fr) * | 1991-01-31 | 1992-08-07 | Rhone Poulenc Rorer Sa | Application de polymeres biologiquement actifs, pour l'obtention d'un medicament pour le traitement d'infections a retrovirus. |
| WO1994003164A1 (fr) * | 1992-08-06 | 1994-02-17 | Genelabs Technologies, Inc. | Inhibition et traitement de l'infection par un virus a enveloppe avec des composes de calix(n) arene |
-
1995
- 1995-01-24 AU AU15453/95A patent/AU1545395A/en not_active Abandoned
- 1995-01-24 WO PCT/IE1995/000008 patent/WO1995019974A2/fr active Application Filing
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