UA79908C2 - Application of polymeric salts 3,5-dimethyl-1-adamantilammonium as immunostimulative and interferonogenous agent - Google Patents
Application of polymeric salts 3,5-dimethyl-1-adamantilammonium as immunostimulative and interferonogenous agent Download PDFInfo
- Publication number
- UA79908C2 UA79908C2 UAA200604494A UAA200604494A UA79908C2 UA 79908 C2 UA79908 C2 UA 79908C2 UA A200604494 A UAA200604494 A UA A200604494A UA A200604494 A UAA200604494 A UA A200604494A UA 79908 C2 UA79908 C2 UA 79908C2
- Authority
- UA
- Ukraine
- Prior art keywords
- acid
- activity
- carboxyl
- dimethyl
- vinylaminosuccinic
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 33
- 230000003308 immunostimulating effect Effects 0.000 title claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 30
- 230000000286 interferogenic effect Effects 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 7
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 26
- 239000013543 active substance Substances 0.000 abstract description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 28
- 229940079593 drug Drugs 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 22
- 102000014150 Interferons Human genes 0.000 description 13
- 108010050904 Interferons Proteins 0.000 description 13
- 229940079322 interferon Drugs 0.000 description 13
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000004071 biological effect Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000712431 Influenza A virus Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000005714 functional activity Effects 0.000 description 4
- 210000000987 immune system Anatomy 0.000 description 4
- 238000003918 potentiometric titration Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 229930027917 kanamycin Natural products 0.000 description 3
- 229960000318 kanamycin Drugs 0.000 description 3
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 3
- 229930182823 kanamycin A Natural products 0.000 description 3
- 229960004640 memantine Drugs 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- FQMLTEAEJZVTAJ-UHFFFAOYSA-M sodium;2-(9-oxoacridin-10-yl)acetate Chemical compound [Na+].C1=CC=C2N(CC(=O)[O-])C3=CC=CC=C3C(=O)C2=C1 FQMLTEAEJZVTAJ-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 208000027089 Parkinsonian disease Diseases 0.000 description 2
- 206010034010 Parkinsonism Diseases 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229960003805 amantadine Drugs 0.000 description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DUCJNKWNTVBRKF-UHFFFAOYSA-N 2-(ethenylamino)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NC=C DUCJNKWNTVBRKF-UHFFFAOYSA-N 0.000 description 1
- 101100028213 Caenorhabditis elegans osm-3 gene Proteins 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- OZBDFBJXRJWNAV-UHFFFAOYSA-N Rimantadine hydrochloride Chemical compound Cl.C1C(C2)CC3CC2CC1(C(N)C)C3 OZBDFBJXRJWNAV-UHFFFAOYSA-N 0.000 description 1
- 208000004006 Tick-borne encephalitis Diseases 0.000 description 1
- 241000711975 Vesicular stomatitis virus Species 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229960000459 cridanimod Drugs 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 210000001167 myeloblast Anatomy 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/RU2004/000242 WO2006011823A1 (fr) | 2004-06-24 | 2004-06-24 | Agent immunostimulateur et interférogène |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79908C2 true UA79908C2 (en) | 2007-07-25 |
Family
ID=35786482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200604494A UA79908C2 (en) | 2004-06-24 | 2004-06-24 | Application of polymeric salts 3,5-dimethyl-1-adamantilammonium as immunostimulative and interferonogenous agent |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1759703A4 (ru) |
| EA (1) | EA200600428A1 (ru) |
| UA (1) | UA79908C2 (ru) |
| WO (1) | WO2006011823A1 (ru) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014672A1 (de) * | 1990-05-08 | 1991-11-14 | Werner E G Prof Dr Mueller | Verwendung von adamantan-derivaten zur zytoprotektion von nicht-infizierten und virus-infizierten lymphozyten als auch anderen zelltypen |
| RU2071323C1 (ru) * | 1994-09-30 | 1997-01-10 | Санкт-Петербургский государственный технологический институт (технический университет) | Противовирусный препарат "полирем" |
| DE19531342B4 (de) * | 1995-08-25 | 2007-11-29 | Merz Pharma Gmbh & Co. Kgaa | Verwendung von Aminoadamantan-Verbindungen als Immunregulatoren |
| US6613507B1 (en) * | 2000-03-21 | 2003-09-02 | Yu-an Chang | Boraadamantane compounds for the treatment of pathogenic viruses and other medical applications |
| RU2185822C2 (ru) * | 2000-08-01 | 2002-07-27 | Общество с ограниченной ответственностью "Фармаген" | Препарат для лечения и профилактики вирусных заболеваний |
| EP1669379B1 (en) * | 2003-09-23 | 2007-11-14 | Akciju Sabiedriba "Olainfarm" | 3,5-dimethyl-1-adamantyl-ammonium polymeric salts and the use thereof in the form of antiviral agents |
-
2004
- 2004-06-24 WO PCT/RU2004/000242 patent/WO2006011823A1/ru active Application Filing
- 2004-06-24 EA EA200600428A patent/EA200600428A1/ru unknown
- 2004-06-24 EP EP04808945A patent/EP1759703A4/en not_active Withdrawn
- 2004-06-24 UA UAA200604494A patent/UA79908C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006011823A1 (fr) | 2006-02-02 |
| EP1759703A1 (en) | 2007-03-07 |
| EA200600428A1 (ru) | 2007-04-27 |
| EP1759703A4 (en) | 2007-08-01 |
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