DE2253977C2 - Antiviraler Komplex, Verfahren zu seiner Herstellung und diesen Komplex enthaltende Arzneimittel - Google Patents
Antiviraler Komplex, Verfahren zu seiner Herstellung und diesen Komplex enthaltende ArzneimittelInfo
- Publication number
- DE2253977C2 DE2253977C2 DE2253977A DE2253977A DE2253977C2 DE 2253977 C2 DE2253977 C2 DE 2253977C2 DE 2253977 A DE2253977 A DE 2253977A DE 2253977 A DE2253977 A DE 2253977A DE 2253977 C2 DE2253977 C2 DE 2253977C2
- Authority
- DE
- Germany
- Prior art keywords
- complex
- rna
- double
- solution
- complexes
- 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
- 230000000840 anti-viral effect Effects 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 8
- 229940126601 medicinal product Drugs 0.000 title 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 130
- 239000011780 sodium chloride Substances 0.000 claims description 59
- 241000700605 Viruses Species 0.000 claims description 45
- 229920002477 rna polymer Polymers 0.000 claims description 45
- 239000002245 particle Substances 0.000 claims description 18
- 241000228145 Penicillium brevicompactum Species 0.000 claims description 14
- 241000228150 Penicillium chrysogenum Species 0.000 claims description 13
- 229920000447 polyanionic polymer Polymers 0.000 claims description 11
- 229920000620 organic polymer Polymers 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 241000892910 Aspergillus foetidus Species 0.000 claims description 5
- 241000228245 Aspergillus niger Species 0.000 claims description 5
- 241001136494 Talaromyces funiculosus Species 0.000 claims description 5
- 241000228143 Penicillium Species 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 31
- 241001465754 Metazoa Species 0.000 description 26
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- 230000001988 toxicity Effects 0.000 description 22
- 108020004707 nucleic acids Proteins 0.000 description 16
- 102000039446 nucleic acids Human genes 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000007523 nucleic acids Chemical class 0.000 description 15
- 210000002966 serum Anatomy 0.000 description 14
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- 241000699670 Mus sp. Species 0.000 description 13
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- 229920000209 Hexadimethrine bromide Polymers 0.000 description 10
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- 229950007870 hexadimethrine bromide Drugs 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 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 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102000006382 Ribonucleases Human genes 0.000 description 9
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- 229940079322 interferon Drugs 0.000 description 8
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- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 3
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- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
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- 108020002230 Pancreatic Ribonuclease Proteins 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
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- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 230000003362 replicative effect Effects 0.000 description 2
- 239000012146 running buffer Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 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
- 230000004083 survival effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 102000040650 (ribonucleotides)n+m Human genes 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 241000702662 Cypovirus Species 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 229920002491 Diethylaminoethyl-dextran Polymers 0.000 description 1
- 241000710198 Foot-and-mouth disease virus Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000223290 Hypherpes complex Species 0.000 description 1
- 241001480512 Mammalian orthoreovirus 3 Species 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
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- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
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- 229940021013 electrolyte solution Drugs 0.000 description 1
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- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 231100000668 minimum lethal dose Toxicity 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- -1 nucleic acid phosphate Chemical class 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
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 238000002264 polyacrylamide gel electrophoresis Methods 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
- 239000010453 quartz Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 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
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
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Classifications
-
- 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
-
- 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
-
- 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
- A61P31/12—Antivirals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5151471A GB1410013A (en) | 1971-11-05 | 1971-11-05 | Biologically active material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2253977A1 DE2253977A1 (de) | 1973-05-10 |
| DE2253977C2 true DE2253977C2 (de) | 1982-12-16 |
Family
ID=10460317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2253977A Expired DE2253977C2 (de) | 1971-11-05 | 1972-11-03 | Antiviraler Komplex, Verfahren zu seiner Herstellung und diesen Komplex enthaltende Arzneimittel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3845033A (en:Method) |
| JP (1) | JPS5732080B2 (en:Method) |
| AT (1) | AT348138B (en:Method) |
| AU (1) | AU467581B2 (en:Method) |
| BE (1) | BE790953A (en:Method) |
| CA (1) | CA987231A (en:Method) |
| CH (1) | CH581666A5 (en:Method) |
| DE (1) | DE2253977C2 (en:Method) |
| DK (2) | DK135537B (en:Method) |
| FR (1) | FR2158488B1 (en:Method) |
| GB (1) | GB1410013A (en:Method) |
| IL (1) | IL40725A (en:Method) |
| NL (1) | NL7214852A (en:Method) |
| SE (1) | SE400087B (en:Method) |
| ZA (1) | ZA727850B (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4024222A (en) * | 1973-10-30 | 1977-05-17 | The Johns Hopkins University | Nucleic acid complexes |
| GB1458586A (en) * | 1974-01-29 | 1976-12-15 | Beecham Group Ltd | Antiviral complexes of double stranded rna and its derivatives |
| US3952097A (en) * | 1974-09-27 | 1976-04-20 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Nuclease-resistant hydrophilic complex of polyriboinosinic-polyribocytidylic acid |
| US4018916A (en) * | 1975-01-27 | 1977-04-19 | Beecham Group Limited | Antiviral ionic complexes of double-standard RNA |
| FR2353293A1 (fr) * | 1976-06-03 | 1977-12-30 | Beljanski Mirko | Polyribonucleotides ayant une activite dans la genese des leucocytes et des plaquettes sanguines |
| IN150740B (en:Method) * | 1978-11-24 | 1982-12-04 | Hoffmann La Roche | |
| US4503035B1 (en) * | 1978-11-24 | 1996-03-19 | Hoffmann La Roche | Protein purification process and product |
| US4289689A (en) * | 1980-03-14 | 1981-09-15 | Hoffmann-La Roche Inc. | Preparation of homogeneous human fibroblast interferon |
| EP0063657A1 (en) * | 1981-04-29 | 1982-11-03 | Merck & Co. Inc. | Topical application of interferon inducers |
| NZ202454A (en) * | 1981-11-23 | 1985-10-11 | Lilly Co Eli | Pharmaceutical compositions containing double-stranded rna and an aminoglycoside complex |
| US4400375A (en) * | 1981-11-23 | 1983-08-23 | Eli Lilly And Company | Tobramycin-double stranded RNA complex suitable for inducing interferon |
| US5010183A (en) * | 1989-07-07 | 1991-04-23 | Macfarlane Donald E | Process for purifying DNA and RNA using cationic detergents |
| EP1309650A2 (en) * | 2000-08-18 | 2003-05-14 | University Of North Carolina At Chapel Hill | Compositions of nucleic acids that form molten phases and methods of use thereof |
| US20170182087A1 (en) * | 2014-07-11 | 2017-06-29 | Genzyme Corporation | Main chain polyamines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6801650D0 (pt) * | 1968-08-20 | 1973-03-07 | R Maes | Processo para preparacao de complexos geradores de interferon |
-
0
- BE BE790953D patent/BE790953A/xx unknown
-
1971
- 1971-11-05 GB GB5151471A patent/GB1410013A/en not_active Expired
-
1972
- 1972-10-31 SE SE7214089A patent/SE400087B/xx unknown
- 1972-11-02 AT AT931472A patent/AT348138B/de not_active IP Right Cessation
- 1972-11-02 AU AU48475/72A patent/AU467581B2/en not_active Expired
- 1972-11-02 CA CA155,465A patent/CA987231A/en not_active Expired
- 1972-11-02 IL IL40725A patent/IL40725A/xx unknown
- 1972-11-02 NL NL7214852A patent/NL7214852A/xx not_active Application Discontinuation
- 1972-11-03 DK DK548072AA patent/DK135537B/da unknown
- 1972-11-03 DE DE2253977A patent/DE2253977C2/de not_active Expired
- 1972-11-03 FR FR7238942A patent/FR2158488B1/fr not_active Expired
- 1972-11-03 DK DK540872A patent/DK135537C/da active
- 1972-11-06 ZA ZA727850A patent/ZA727850B/xx unknown
- 1972-11-06 US US00303955A patent/US3845033A/en not_active Expired - Lifetime
- 1972-11-06 JP JP11042172A patent/JPS5732080B2/ja not_active Expired
- 1972-11-06 CH CH1615572A patent/CH581666A5/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IL40725A (en) | 1975-08-31 |
| AU467581B2 (en) | 1975-12-04 |
| IL40725A0 (en) | 1973-01-30 |
| US3845033A (en) | 1974-10-29 |
| DK135537B (da) | 1977-05-16 |
| CA987231A (en) | 1976-04-13 |
| FR2158488A1 (en:Method) | 1973-06-15 |
| FR2158488B1 (en:Method) | 1976-04-23 |
| SE400087B (sv) | 1978-03-13 |
| DK135537C (da) | 1977-11-07 |
| NL7214852A (en:Method) | 1973-05-08 |
| ATA931472A (de) | 1978-06-15 |
| AT348138B (de) | 1979-01-25 |
| JPS4856814A (en:Method) | 1973-08-09 |
| GB1410013A (en) | 1975-10-15 |
| BE790953A (fr) | 1973-05-03 |
| CH581666A5 (en:Method) | 1976-11-15 |
| ZA727850B (en) | 1973-08-29 |
| DE2253977A1 (de) | 1973-05-10 |
| JPS5732080B2 (en:Method) | 1982-07-08 |
| AU4847572A (en) | 1974-05-02 |
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| OD | Request for examination | ||
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| 8339 | Ceased/non-payment of the annual fee |