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 5
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract 3
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract 3
- 230000000694 effects Effects 0.000 title abstract 2
- 229940121375 antifungal agent Drugs 0.000 title 1
- 125000004122 cyclic group Chemical group 0.000 claims abstract 3
- 230000000840 anti-viral effect Effects 0.000 claims abstract 2
- 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
- 206010017533 Fungal infection Diseases 0.000 claims 4
- 208000031888 Mycoses Diseases 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- -1 amino acid ester Chemical class 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 230000001580 bacterial effect Effects 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 230000002538 fungal effect Effects 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910021645 metal ion Inorganic materials 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 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
- 239000003429 antifungal agent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 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
- 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 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=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-KKGHZKTASA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000031886 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B 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
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229940079593 drug 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
- 208000015181 infectious disease Diseases 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
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 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
- 229920000642 polymer Polymers 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 229950008974 sinefungin Drugs 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical class OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 abstract 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical class OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000036436 anti-hiv Effects 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- 230000004071 biological effect 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 |
|---|---|---|---|
| IES940057 | 1994-01-24 | ||
| IE940057 | 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 |
| DE69822503T2 (de) * | 1997-12-09 | 2005-01-20 | Cosmo Oil Co. Ltd. | Sulfonierte derivate zyklischer phenolsulfide, verfahren zu ihrer herstellung, mittel zur trennung und gewinnung, die zyklische phenolsulfide enthalten, auf diesen basierende methoden zur trennung ung gewinnung und medikamentzusammensetzungen, die diese sulfide enthalten |
| NL1008988C2 (nl) * | 1998-04-24 | 1999-10-26 | Stichting Tech Wetenschapp | Calixareenverbinding en een selectief molecuul voorzien van een dergelijke verbinding. |
| EP1085846A2 (fr) * | 1998-06-08 | 2001-03-28 | Advanced Medicine, Inc. | Inhibiteurs multiliaison de proteine triglyceride transferase microsomique |
| IES20011021A2 (en) * | 2000-12-01 | 2002-12-11 | Aids Care Pharma Ltd | Anti-viral compounds |
| CA2451117A1 (fr) | 2001-03-08 | 2002-12-19 | The Trustees Of The University Of Pennsylvania | Polymeres amphiphiles faciaux comme agents anti-infectieux |
| 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 |
| US9241917B2 (en) | 2003-03-17 | 2016-01-26 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
| 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 |
| EP1711455A4 (fr) | 2004-01-23 | 2007-11-07 | Univ Pennsylvania | Polymeres et oligomeres de polyaryle et de polyarylalkynyle amphiphiles au niveau facial |
| ATE536177T1 (de) | 2004-10-04 | 2011-12-15 | Univ Minnesota | Calixaren-basierte peptidkonformationsmimetika, verfahren zu ihrer verwendung und verfahren zu ihrer herstellung |
| JP5304648B2 (ja) * | 2007-08-23 | 2013-10-02 | Ｊｓｒ株式会社 | 感放射線性組成物及び化合物 |
| 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 |
| WO2013073583A1 (fr) * | 2011-11-18 | 2013-05-23 | 三菱瓦斯化学株式会社 | Composé cyclique ainsi que son procédé de fabrication, composition sensible aux rayonnements, et procédé de formation de motif de réserve |
| WO2013073582A1 (fr) * | 2011-11-18 | 2013-05-23 | 三菱瓦斯化学株式会社 | Composé cyclique ainsi que son procédé de fabrication, composition sensible aux rayonnements, et procédé de formation de motif de réserve |
| WO2015196086A1 (fr) * | 2014-06-20 | 2015-12-23 | The University of Montana, Missoula, MT | Nouveaux inhibiteurs du système 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 |
| WO2020063860A1 (fr) * | 2018-09-28 | 2020-04-02 | Fochon Pharmaceuticals, Ltd. | Composés de naphthyridinone et de pyridopyrimidinone utiles en tant qu'inhibiteurs de kinases |
| 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 |
|---|---|---|---|---|
| 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 |
| IE68312B1 (en) * | 1989-12-13 | 1996-06-12 | Loctite Ireland Ltd | Calixarene and oxacalixarene derivatives and use thereof for sequestration of metals |
| IE59509B1 (en) * | 1987-01-21 | 1994-03-09 | Loctite Ireland Ltd | Functionalised oxacalixarenes, their preparation and use in instant adhesive compositions |
| 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 |
| US5132345A (en) * | 1990-12-10 | 1992-07-21 | Harris Stephen J | 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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