DE2262411A1 - Antiviraler komplex, verfahren zu seiner herstellung und diesen komplex enthaltende arzneipraeparate - Google Patents
Antiviraler komplex, verfahren zu seiner herstellung und diesen komplex enthaltende arzneipraeparateInfo
- Publication number
- DE2262411A1 DE2262411A1 DE2262411A DE2262411A DE2262411A1 DE 2262411 A1 DE2262411 A1 DE 2262411A1 DE 2262411 A DE2262411 A DE 2262411A DE 2262411 A DE2262411 A DE 2262411A DE 2262411 A1 DE2262411 A1 DE 2262411A1
- Authority
- DE
- Germany
- Prior art keywords
- complex
- acid
- poly
- antiviral
- aqueous
- 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
- 230000000840 anti-viral effect Effects 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 55
- 239000000243 solution Substances 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 34
- 239000011780 sodium chloride Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229920000447 polyanionic polymer Polymers 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- 229920000620 organic polymer Polymers 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000008151 electrolyte solution Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- AUHDWARTFSKSAC-HEIFUQTGSA-N (2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(6-oxo-1H-purin-9-yl)oxolane-2-carboxylic acid Chemical compound [C@]1([C@H](O)[C@H](O)[C@@H](CO)O1)(N1C=NC=2C(O)=NC=NC12)C(=O)O AUHDWARTFSKSAC-HEIFUQTGSA-N 0.000 claims 1
- GRSZFWQUAKGDAV-UHFFFAOYSA-N Inosinic acid Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-UHFFFAOYSA-N 0.000 claims 1
- 229940028843 inosinic acid Drugs 0.000 claims 1
- 235000013902 inosinic acid Nutrition 0.000 claims 1
- 239000004245 inosinic acid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 13
- 229920002477 rna polymer Polymers 0.000 description 11
- 241000700605 Viruses Species 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KZKAYEGOIJEWQB-UHFFFAOYSA-N 1,3-dibromopropane;n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound BrCCCBr.CN(C)CCCCCCN(C)C KZKAYEGOIJEWQB-UHFFFAOYSA-N 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 229920000209 Hexadimethrine bromide Polymers 0.000 description 4
- 102000006382 Ribonucleases Human genes 0.000 description 4
- 108010083644 Ribonucleases Proteins 0.000 description 4
- 150000003868 ammonium compounds Chemical group 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229950007870 hexadimethrine bromide Drugs 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 241000710188 Encephalomyocarditis virus Species 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 238000007269 dehydrobromination reaction Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010414 supernatant solution Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- 229930183912 Cytidylic acid Natural products 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 108020002230 Pancreatic Ribonuclease Proteins 0.000 description 1
- 102000005891 Pancreatic ribonuclease Human genes 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 108091034057 RNA (poly(A)) Proteins 0.000 description 1
- 241000710961 Semliki Forest virus Species 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- IERHLVCPSMICTF-XVFCMESISA-N cytidine 5'-monophosphate Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O1 IERHLVCPSMICTF-XVFCMESISA-N 0.000 description 1
- IERHLVCPSMICTF-UHFFFAOYSA-N cytidine monophosphate Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(COP(O)(O)=O)O1 IERHLVCPSMICTF-UHFFFAOYSA-N 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- -1 diethylaminoethyl alcohol Chemical compound 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002799 interferon inducing agent Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5946071 | 1971-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2262411A1 true DE2262411A1 (de) | 1973-07-05 |
Family
ID=10483802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2262411A Pending DE2262411A1 (de) | 1971-12-21 | 1972-12-20 | Antiviraler komplex, verfahren zu seiner herstellung und diesen komplex enthaltende arzneipraeparate |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4868728A (enExample) |
| AU (1) | AU5033572A (enExample) |
| BE (1) | BE793157A (enExample) |
| DE (1) | DE2262411A1 (enExample) |
| FR (1) | FR2164724A1 (enExample) |
| IL (1) | IL41098A0 (enExample) |
| NL (1) | NL7217425A (enExample) |
| ZA (1) | ZA728858B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303516A3 (en) * | 1987-08-12 | 1989-12-06 | Hem Research, Inc. | Topically active compositions of double-stranded rnas |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112017000258A2 (pt) * | 2014-07-11 | 2017-10-31 | Genzyme Corp | poliaminas de cadeia principal |
-
0
- BE BE793157D patent/BE793157A/xx unknown
-
1972
- 1972-12-14 ZA ZA728858A patent/ZA728858B/xx unknown
- 1972-12-15 IL IL41098A patent/IL41098A0/xx unknown
- 1972-12-19 JP JP47127615A patent/JPS4868728A/ja active Pending
- 1972-12-20 FR FR7245383A patent/FR2164724A1/fr not_active Withdrawn
- 1972-12-20 AU AU50335/72A patent/AU5033572A/en not_active Expired
- 1972-12-20 NL NL7217425A patent/NL7217425A/xx unknown
- 1972-12-20 DE DE2262411A patent/DE2262411A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0303516A3 (en) * | 1987-08-12 | 1989-12-06 | Hem Research, Inc. | Topically active compositions of double-stranded rnas |
Also Published As
| Publication number | Publication date |
|---|---|
| IL41098A0 (en) | 1973-02-28 |
| NL7217425A (enExample) | 1973-06-25 |
| FR2164724A1 (en) | 1973-08-03 |
| JPS4868728A (enExample) | 1973-09-19 |
| ZA728858B (en) | 1973-10-31 |
| AU5033572A (en) | 1974-06-20 |
| BE793157A (fr) | 1973-06-21 |
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