DE2256781A1 - Formaldehyd-modifizierte ribonucleinsaeure natuerlichen ursprungs mit interferoninduzierender wirkung, verfahren zu ihrer herstellung und eine solche ribonucleinsaeure enthaltende arzneipraeparate - Google Patents
Formaldehyd-modifizierte ribonucleinsaeure natuerlichen ursprungs mit interferoninduzierender wirkung, verfahren zu ihrer herstellung und eine solche ribonucleinsaeure enthaltende arzneipraeparateInfo
- Publication number
- DE2256781A1 DE2256781A1 DE19722256781 DE2256781A DE2256781A1 DE 2256781 A1 DE2256781 A1 DE 2256781A1 DE 19722256781 DE19722256781 DE 19722256781 DE 2256781 A DE2256781 A DE 2256781A DE 2256781 A1 DE2256781 A1 DE 2256781A1
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- double
- ribonucleic acid
- stranded
- 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.)
- Pending
Links
- 229920002477 rna polymer Polymers 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 230000000694 effects Effects 0.000 title description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 141
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 241000700605 Viruses Species 0.000 claims description 26
- 241000699670 Mus sp. Species 0.000 claims description 25
- 102000040650 (ribonucleotides)n+m Human genes 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- 239000002773 nucleotide Substances 0.000 claims description 13
- 125000003729 nucleotide group Chemical group 0.000 claims description 13
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 238000010790 dilution Methods 0.000 claims description 8
- 239000012895 dilution Substances 0.000 claims description 8
- 102000014150 Interferons Human genes 0.000 claims description 7
- 108010050904 Interferons Proteins 0.000 claims description 7
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 7
- 230000000295 complement effect Effects 0.000 claims description 7
- 229940079322 interferon Drugs 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
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- 230000004083 survival effect Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 2
- 208000009525 Myocarditis Diseases 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 230000000840 anti-viral effect Effects 0.000 description 20
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 238000012360 testing method Methods 0.000 description 12
- 231100000419 toxicity Toxicity 0.000 description 11
- 230000001988 toxicity Effects 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- 235000011056 potassium acetate Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229920002684 Sepharose Polymers 0.000 description 7
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- 125000003277 amino group Chemical group 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 238000004062 sedimentation Methods 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000003362 replicative effect Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 102000053602 DNA Human genes 0.000 description 3
- 108020004414 DNA Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 238000012869 ethanol precipitation Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 241000710188 Encephalomyocarditis virus Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000001502 gel electrophoresis Methods 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 206010022000 influenza Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 102000040430 polynucleotide Human genes 0.000 description 2
- 108091033319 polynucleotide Proteins 0.000 description 2
- 239000002157 polynucleotide Substances 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- 101150071434 BAR1 gene Proteins 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 244000237786 Lathyrus tuberosus Species 0.000 description 1
- 208000004852 Lung Injury Diseases 0.000 description 1
- 241001480512 Mammalian orthoreovirus 3 Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000228145 Penicillium brevicompactum Species 0.000 description 1
- 241000045615 Penicillium chrysogenum virus Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 239000013614 RNA sample Substances 0.000 description 1
- 241000702632 Rice dwarf virus Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 241001136494 Talaromyces funiculosus Species 0.000 description 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 229940121357 antivirals Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
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- 238000002264 polyacrylamide gel electrophoresis Methods 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
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- 150000003212 purines Chemical class 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/30—Nucleotides
- C12P19/34—Polynucleotides, e.g. nucleic acids, oligoribonucleotides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5402171A GB1411748A (en) | 1971-11-20 | 1971-11-20 | Derivatives of double-stranded rna |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2256781A1 true DE2256781A1 (de) | 1973-05-24 |
Family
ID=10469702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722256781 Pending DE2256781A1 (de) | 1971-11-20 | 1972-11-20 | Formaldehyd-modifizierte ribonucleinsaeure natuerlichen ursprungs mit interferoninduzierender wirkung, verfahren zu ihrer herstellung und eine solche ribonucleinsaeure enthaltende arzneipraeparate |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4862878A (enExample) |
| AU (1) | AU474927B2 (enExample) |
| BE (1) | BE791654A (enExample) |
| CH (1) | CH571016A5 (enExample) |
| DE (1) | DE2256781A1 (enExample) |
| DK (1) | DK129793B (enExample) |
| ES (1) | ES408778A1 (enExample) |
| FR (1) | FR2160424A1 (enExample) |
| GB (1) | GB1411748A (enExample) |
| NL (1) | NL7215648A (enExample) |
-
0
- BE BE791654D patent/BE791654A/xx unknown
-
1971
- 1971-11-20 GB GB5402171A patent/GB1411748A/en not_active Expired
-
1972
- 1972-11-13 FR FR7240148A patent/FR2160424A1/fr not_active Withdrawn
- 1972-11-16 DK DK570472A patent/DK129793B/da unknown
- 1972-11-17 NL NL7215648A patent/NL7215648A/xx not_active Application Discontinuation
- 1972-11-18 ES ES408778A patent/ES408778A1/es not_active Expired
- 1972-11-20 DE DE19722256781 patent/DE2256781A1/de active Pending
- 1972-11-20 AU AU49067/72A patent/AU474927B2/en not_active Expired
- 1972-11-20 CH CH1686872A patent/CH571016A5/xx not_active IP Right Cessation
- 1972-11-20 JP JP11706572A patent/JPS4862878A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES408778A1 (es) | 1975-12-01 |
| BE791654A (fr) | 1973-05-21 |
| FR2160424A1 (enExample) | 1973-06-29 |
| NL7215648A (enExample) | 1973-05-22 |
| JPS4862878A (enExample) | 1973-09-01 |
| AU4906772A (en) | 1974-05-23 |
| DK129793B (da) | 1974-11-18 |
| DK129793C (enExample) | 1975-04-28 |
| CH571016A5 (enExample) | 1975-12-31 |
| GB1411748A (en) | 1975-10-29 |
| AU474927B2 (en) | 1976-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |