CA1042877A - Antiviral agents - Google Patents
Antiviral agentsInfo
- Publication number
- CA1042877A CA1042877A CA218,867A CA218867A CA1042877A CA 1042877 A CA1042877 A CA 1042877A CA 218867 A CA218867 A CA 218867A CA 1042877 A CA1042877 A CA 1042877A
- Authority
- CA
- Canada
- Prior art keywords
- double
- ribonucleic acid
- stranded
- stranded ribonucleic
- rna
- 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
Links
- 239000003443 antiviral agent Substances 0.000 title claims description 6
- 229920002477 rna polymer Polymers 0.000 claims abstract description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 13
- 241000700605 Viruses Species 0.000 claims description 9
- 229920000447 polyanionic polymer Polymers 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000003792 electrolyte Substances 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 241000892910 Aspergillus foetidus Species 0.000 claims description 3
- 241000228245 Aspergillus niger Species 0.000 claims description 3
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 3
- 241000228145 Penicillium brevicompactum Species 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 241000228143 Penicillium Species 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 abstract description 8
- 229920000642 polymer Polymers 0.000 abstract description 5
- 150000001768 cations Chemical class 0.000 abstract description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 229920000768 polyamine Polymers 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000007912 intraperitoneal administration Methods 0.000 description 9
- 238000007920 subcutaneous administration Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 241000710188 Encephalomyocarditis virus Species 0.000 description 5
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 5
- 230000009385 viral infection Effects 0.000 description 5
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 229940079322 interferon Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000786363 Rhampholeon spectrum Species 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000001641 gel filtration chromatography Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000145903 Bombyx mori cypovirus 1 Species 0.000 description 1
- 101100298998 Caenorhabditis elegans pbs-3 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001480512 Mammalian orthoreovirus 3 Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 102000006382 Ribonucleases Human genes 0.000 description 1
- 108010083644 Ribonucleases Proteins 0.000 description 1
- 241000710961 Semliki Forest virus Species 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 241001136494 Talaromyces funiculosus Species 0.000 description 1
- 241001342522 Vampyrum spectrum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 150000004695 complexes Chemical class 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001965 increasing effect Effects 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000002845 virion Anatomy 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB420774A GB1458586A (en) | 1974-01-29 | 1974-01-29 | Antiviral complexes of double stranded rna and its derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042877A true CA1042877A (en) | 1978-11-21 |
Family
ID=9772754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,867A Expired CA1042877A (en) | 1974-01-29 | 1975-01-28 | Antiviral agents |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3978043A (en, 2012) |
| JP (1) | JPS50116620A (en, 2012) |
| BE (1) | BE824947A (en, 2012) |
| CA (1) | CA1042877A (en, 2012) |
| CH (1) | CH613118A5 (en, 2012) |
| DE (1) | DE2503442A1 (en, 2012) |
| DK (1) | DK141194B (en, 2012) |
| FR (1) | FR2258862B1 (en, 2012) |
| GB (1) | GB1458586A (en, 2012) |
| IL (1) | IL46524A (en, 2012) |
| NL (1) | NL7500955A (en, 2012) |
| SE (1) | SE400976B (en, 2012) |
| ZA (1) | ZA75540B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5998015A (ja) * | 1982-11-27 | 1984-06-06 | Microbial Chem Res Found | 免疫賦活剤 |
| US5091374A (en) * | 1987-07-17 | 1992-02-25 | Hem Research Inc. | Double-stranded RNA correction of abnormalities in circulating immune complexes and monocyte function |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3484521A (en) * | 1966-06-23 | 1969-12-16 | Int Chem & Nuclear Corp | Enhancement of memory processes in mammals with basic addition salts of ribonucleic acid |
| BR6801650D0 (pt) * | 1968-08-20 | 1973-03-07 | R Maes | Processo para preparacao de complexos geradores de interferon |
| BE790953A (fr) * | 1971-11-05 | 1973-05-03 | Beecham Group Ltd | Matiere biologiquement active |
-
1974
- 1974-01-29 GB GB420774A patent/GB1458586A/en not_active Expired
-
1975
- 1975-01-27 US US05/544,211 patent/US3978043A/en not_active Expired - Lifetime
- 1975-01-27 SE SE7500854A patent/SE400976B/xx unknown
- 1975-01-27 ZA ZA00750540A patent/ZA75540B/xx unknown
- 1975-01-28 CA CA218,867A patent/CA1042877A/en not_active Expired
- 1975-01-28 DE DE19752503442 patent/DE2503442A1/de not_active Withdrawn
- 1975-01-28 NL NL7500955A patent/NL7500955A/xx not_active Application Discontinuation
- 1975-01-29 IL IL46524A patent/IL46524A/xx unknown
- 1975-01-29 JP JP50012299A patent/JPS50116620A/ja active Pending
- 1975-01-29 BE BE152853A patent/BE824947A/xx unknown
- 1975-01-29 FR FR7502721A patent/FR2258862B1/fr not_active Expired
- 1975-01-29 DK DK30375AA patent/DK141194B/da unknown
- 1975-01-29 CH CH102875A patent/CH613118A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK141194B (da) | 1980-02-04 |
| AU7770075A (en) | 1976-07-29 |
| IL46524A (en) | 1978-10-31 |
| BE824947A (fr) | 1975-07-29 |
| SE7500854L (en, 2012) | 1975-07-30 |
| DK30375A (en, 2012) | 1975-09-22 |
| GB1458586A (en) | 1976-12-15 |
| IL46524A0 (en) | 1975-05-22 |
| SE400976B (sv) | 1978-04-17 |
| CH613118A5 (en, 2012) | 1979-09-14 |
| NL7500955A (nl) | 1975-07-31 |
| FR2258862B1 (en, 2012) | 1980-02-08 |
| FR2258862A1 (en, 2012) | 1975-08-22 |
| DK141194C (en, 2012) | 1980-07-21 |
| JPS50116620A (en, 2012) | 1975-09-12 |
| DE2503442A1 (de) | 1975-07-31 |
| US3978043A (en) | 1976-08-31 |
| ZA75540B (en) | 1976-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Perreault et al. | Using guanidinium groups for the recognition of RNA and as catalysts for the hydrolysis of RNA | |
| US4024222A (en) | Nucleic acid complexes | |
| US4123610A (en) | Nucleic acid crosslinking agent and affinity inactivation of nucleic acids therewith | |
| EP0463540B1 (en) | Anti-virus agent | |
| GB2027024A (en) | Doxorubicin derivatives | |
| US3845033A (en) | Complexes of double-stranded ribonucleic acid with polyquaternary amine | |
| KR960034204A (ko) | 항-천식 작용을 지닌 피리도[3,2-e]피라지논 및 이의 제조방법 | |
| US3737524A (en) | Medicaments derived from nucleic acids,processes for their preparation and their use | |
| US3952097A (en) | Nuclease-resistant hydrophilic complex of polyriboinosinic-polyribocytidylic acid | |
| EP0111388B1 (en) | Therapeutic compounds of platinum and palladium and their preparation | |
| US4018916A (en) | Antiviral ionic complexes of double-standard RNA | |
| CA1042877A (en) | Antiviral agents | |
| HU185314B (en) | Process for producing water-soluble immunostimulant glyco-proteins from klebsiella pneumoniae | |
| US7449537B2 (en) | Antineoplastic polyalkoxyalkylsiloxanes and methods of use thereof | |
| AU6394398A (en) | O-sulfated bacterial polysaccharides | |
| CA2439337A1 (en) | Highly sulfated derivatives of k5 polysaccharide and their preparation | |
| GB1436684A (en) | Method for preparing glucoronyl-glucosamino-glycan sulphates exhibiting antilipaemic activity | |
| US3935185A (en) | Polynucleotides of poly(5-hydroxycytidylic acids) | |
| US3843629A (en) | Complexs of polyriboinosinic acid and polyribo-2-thiocytidylic acid | |
| EP0066379A2 (en) | Composition for combating herpes virus | |
| JP2005176830A (ja) | 核酸導入用キャリアー | |
| Kanehisa et al. | Partial specificity of low-molecular-weight RNA that stimulates RNA synthesis in various tissues | |
| US3660564A (en) | Interferon induction | |
| IE42170B1 (en) | Antiviral agentss | |
| DE2359621C2 (de) | Antiviral wirksame Alkalimetall- oder Ammoniumsalze der Polyacrylsäure |