DE69522585T2 - In 4-position substituierte 2,6-di-tert-butylphenole, diese enthaltende pharmazeutische compositionen und ihre herstellungsverfahren - Google Patents
In 4-position substituierte 2,6-di-tert-butylphenole, diese enthaltende pharmazeutische compositionen und ihre herstellungsverfahrenInfo
- Publication number
- DE69522585T2 DE69522585T2 DE69522585T DE69522585T DE69522585T2 DE 69522585 T2 DE69522585 T2 DE 69522585T2 DE 69522585 T DE69522585 T DE 69522585T DE 69522585 T DE69522585 T DE 69522585T DE 69522585 T2 DE69522585 T2 DE 69522585T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- radical
- compounds
- butyl
- 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.)
- Expired - Lifetime
Links
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- 239000012470 diluted sample Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N gallic acid propyl ester Natural products CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229940078545 isocetyl stearate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002979 macrophagic effect Effects 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 238000004172 nitrogen cycle Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000012809 post-inoculation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 229940069949 propolis Drugs 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (19)
1. Verbindungen der Formel:
in welcher der Rest R aus den drei Gruppen mit den folgenden Formeln gewählt wird:
-(OCH&sub2;CH&sub2;)n-Y (II)
-O(CH&sub2;CH&sub2;NH)n-Y (III)
in denen:
- n eine ganze Zahl zwischen 1 und 20 ist, aber auch ein Maximalwert von 80 durchaus
möglich ist;
- R1 gewählt wird unter den folgenden Gruppen:
-(CH&sub2;CH&sub2;O)n-Y, -(CH&sub2;CH&sub2;NH)n-Y;
- R2 ein Wasserstoffatom ist oder dieselbe Bedeutung hat wie R1; und
- Y unter den folgenden Gruppen ausgewählt wird: ein Wasserstoffatom, eine OH-
Gruppe, eine NH&sub2;-Gruppe, eine COOH-Gruppe, eine 3,5-Di-t-butyl-4-
hydroxybenzoat-Gruppe, eine primäre, sekundäre oder tertiäre Amino- oder
Hydroxyaminogruppe, eine aliphatische oder aromatische Amid-, Diamid-,
Hydroxyamid- oder Halogenamidgruppe, eine C&sub1;-C&sub1;&sub2;Alkoholgruppe, eine Glykolgruppe, eine
mono-, di- oder trisubstituierte Glyceringruppe, eine heterocyklische Gruppe, eine aliphatische
oder aromatische Thioestergruppe, eine Gruppe der Formel -COOZ, wobei
Z ein C&sub1;-C&sub1;&sub2; Alkylrest, ein C&sub1;-C&sub1;&sub2;Alkenrest, ein C&sub1;-C&sub1;&sub2;Alkinrest, ein C&sub1;-C&sub1;&sub2;
Hydroxyalkylrest, ein C&sub1;-C&sub1;&sub2;Hydroxyalkenrest, ein C&sub1;-C&sub1;&sub2;Hydroxyalkinrest, ein C&sub1;-C&sub1;&sub2;
Aminoalkylrest, ein C&sub1;-C&sub1;&sub2;Aminoalkenrest, ein Arylrest, ein heterocyklischer Rest ist.
2. Die Verbindungen der Formei (Ib), in denen der Rest R eine Gruppe der Formel
-(OCH&sub2;CH&sub2;)n-Y (II)
-O(CH&sub2;CH&sub2;NH)n-Y (III)
darstellt, wobei Y und n die gleiche Bedeutung haben wie in Anspruch 1.
3. Die Verbindungen der Formel (Ib), in denen der Rest R eine Gruppe der Formel
darstellt, wobei R&sub1; und R&sub2; die gleiche Bedeutung haben wie in Anspruch 1.
4. Octaoxyethylenglycol-3,5-di-t-butyl-4-hydroxybenzoat mit der Formel:
5. Verbindungen nach irgendeinem der Ansprüche 1 bis 3, dadurch gekennzeichnet,
daß in den Formeln (II), (III) und (IV), Y eine Gruppe der folgenden Formel ist:
6. Pharmazeutische Zubereitung, dadurch gekennzeichnet, daß sie als Wirkstoff
mindestens eine Verbindung nach irgendeinem der Ansprüche 1 bis 5 enthält, eventuell in
Verbindung mit einem pharmazeutisch akzeptablen Arzneistoffträger.
7. Pharmazeutische Zubereitung nach Anspruch 6, dadurch gekennzeichnet, daß sie
als Wirkstoff mindestens eine Verbindung der Formel (I):
enthält, in der:
A eine -CH&sub2;-Gruppe ist,
m eine ganze Zahl zwischen 0 und 12 ist,
der Rest R aus den drei Gruppen mit den folgenden Formeln gewählt wird:
-(OCH&sub2;CH&sub2;)n-Y (II)
-O(CH&sub2;CH&sub2;NH)n-Y (III)
in denen n, R&sub1;, R&sub2; und Y die gleiche Bedeutung haben wie in Anspruch 1.
8. Pharmazeutische Zubereitung nach Anspruch 7, dadurch gekennzeichnet, daß sie
als Wirkstoff Octaoxyethylenglycol-3,5-di-t-butyl-4-hydroxybenzoat enthält.
9. Pharmazeutische Zubereitung nach einen der Ansprüche 6 bis 8, dadurch
gekennzeichnet, daß sie zusätzlich einen induktiblen NO-Synthase-Inhibitor wie L-NMMA
enthält.
10. Anwendung der Verbindungen der Formel (I) wie in Anspruch 7 definiert, um ein
Medikament zu erhalten, das zur Behandlung und Vorbeugung von Vireninfektionen von
Menschen und Tieren dient.
11. Anwendung nach Anspruch 10, dadurch gekennzeichnet, daß das Medikament zur
Behandlung und Vorbeugung einer Infektion mit Viren mit Lipidhülle dient.
12. Anwendung nach Anspruch 10, dadurch gekennzeichnet, daß das Medikament zur
Behandlung und Vorbeugung einer Infektion mit Herpes- und HIV-Viren dient.
13. Anwendung nach Anspruch 10, dadurch gekennzeichnet, daß das Medikament zur
Behandlung und Vorbeugung einer Infektion mit Papilloma-Viron dient.
14. Anwendung nach Anspruch 10, dadurch gekennzeichnet, daß das Medikament zur
Behandlung von - insbesondere anogenitalen - Condylomen dient, die durch menschliche
Papillomaviren hervorgerufen werden.
15. Anwendung der Verbindungen der Formel (I) wie in Anspruch 7 definiert in Verbindung
mit einem induktiblen NO-Synthase-inhibitor wie L-NMMA, um ein Medikament zu
erhalten, das der Behandlung von Krankheiten dient, bei denen das Stickstof Monoxyd
eine pathologische Wirkung hat.
16. Anwendung der Verbindungen der Formel (I) wie in Anspruch 7 definiert, zur
Verstärkung der antiseptischen, antiviralen, antibakteriellen und antimykotischen Eigenschaften
von pharmazeutischen Geweben wie Pflastern, Verbänden oder Kompressen oder
Implantaten.
17. Anwendung nach Anspruch 16, dadurch gekennzeichnet, daß zumindest ein Teil
der Fasern des erwähnten pharmazeutischen Gewebes oder Implantats mit mindestens
einer Verbindung der Formel (I) wie in Anspruch 7 definiert behandelt wird.
18. Pharmazeutisches Gewebe wie Pflaster, Verband oder Kompresse Implantat, dadurch
gekennzeichnet, daß mindestens eine Verbindung der Formel (I) wie in Anspruch
7 definiert auf alle oder einen Teil der Fasern des erwähnten Gewebes aufgepropft ist.
19. Pharmazeutisches Gewebe oder Implantat nach Anspruch 18, dadurch
gekennzeichnet, daß mindestens ein Teil der Fasern, aus dem es hergestellt ist, die
Verbindung des Anspruchs 4 enthält.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9408061A FR2721924B1 (fr) | 1994-06-30 | 1994-06-30 | Nouveaux composes 2,6-di-tert-butylphenols substitues en position 4, les compositions pharmaceutiques les contenant et leur procede de preparation |
| PCT/FR1995/000882 WO1996000713A1 (fr) | 1994-06-30 | 1995-06-30 | Nouveaux composes 2,6-di-tert-butylphenols substitues en position 4, les compositions pharmaceutiques les contenant et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69522585D1 DE69522585D1 (de) | 2001-10-11 |
| DE69522585T2 true DE69522585T2 (de) | 2002-06-27 |
Family
ID=9464836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69522585T Expired - Lifetime DE69522585T2 (de) | 1994-06-30 | 1995-06-30 | In 4-position substituierte 2,6-di-tert-butylphenole, diese enthaltende pharmazeutische compositionen und ihre herstellungsverfahren |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0804408B1 (de) |
| AT (1) | ATE205180T1 (de) |
| AU (1) | AU2891195A (de) |
| DE (1) | DE69522585T2 (de) |
| ES (1) | ES2165917T3 (de) |
| FR (1) | FR2721924B1 (de) |
| WO (1) | WO1996000713A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2887249B1 (fr) * | 2005-06-21 | 2007-09-28 | Rdw Pharma Soc Par Actions Sim | Compose d-glucopyranose 1-[3,5-bis(1,1-dimenthylethyl)-4- hydroxybenzoate] et ses derives, leur preparation et leurs utilisations |
| US20100016244A1 (en) | 2006-06-23 | 2010-01-21 | Robert Vachy | D-glucopyranose 1-[3,5-bis (1,1-dimethylethy)-4-hydroxybenzoate] and its derivatives, preparation and use thereof |
| FR3058640B1 (fr) * | 2016-11-14 | 2020-06-19 | Robert Vachy | Composes pour leur utilisation dans le traitement de la grippe |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH549407A (de) * | 1970-07-06 | 1974-05-31 | Ciba Geigy Ag | Verwendung sterisch gehinderter phenolestern von glykolen als stabilisatoren. |
| US4032562A (en) * | 1974-11-05 | 1977-06-28 | Ciba-Geigy Corporation | 3,5-dialkyl-4-hydroxyphenylalkanoic acid esters of polyalkylene glycols |
| US3972927A (en) * | 1974-12-30 | 1976-08-03 | American Cyanamid Company | Alkylamides of hindered 3,5-dialkyl-4-hydroxybenzoic acids and use as light stabilizers in polyolefins |
| US4716244A (en) * | 1985-05-02 | 1987-12-29 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
| EP0557404B1 (de) * | 1990-11-12 | 1996-05-15 | Fileco | Antivirale verwendung einer in position-4 substituierten 2,6-di-t-butylphenolverbindung, besonders gegen herpes- und papillomaviren |
-
1994
- 1994-06-30 FR FR9408061A patent/FR2721924B1/fr not_active Expired - Fee Related
-
1995
- 1995-06-30 EP EP95924395A patent/EP0804408B1/de not_active Expired - Lifetime
- 1995-06-30 AU AU28911/95A patent/AU2891195A/en not_active Abandoned
- 1995-06-30 WO PCT/FR1995/000882 patent/WO1996000713A1/fr active IP Right Grant
- 1995-06-30 DE DE69522585T patent/DE69522585T2/de not_active Expired - Lifetime
- 1995-06-30 ES ES95924395T patent/ES2165917T3/es not_active Expired - Lifetime
- 1995-06-30 AT AT95924395T patent/ATE205180T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2165917T3 (es) | 2002-04-01 |
| ATE205180T1 (de) | 2001-09-15 |
| EP0804408A1 (de) | 1997-11-05 |
| AU2891195A (en) | 1996-01-25 |
| FR2721924A1 (fr) | 1996-01-05 |
| EP0804408B1 (de) | 2001-09-05 |
| WO1996000713A1 (fr) | 1996-01-11 |
| FR2721924B1 (fr) | 1996-10-31 |
| DE69522585D1 (de) | 2001-10-11 |
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