HU180321B - Process for producing 6- and 9-substituted 2-amino-purine derivatives - Google Patents
Process for producing 6- and 9-substituted 2-amino-purine derivatives Download PDFInfo
- Publication number
- HU180321B HU180321B HU77WE551A HUWE000551A HU180321B HU 180321 B HU180321 B HU 180321B HU 77WE551 A HU77WE551 A HU 77WE551A HU WE000551 A HUWE000551 A HU WE000551A HU 180321 B HU180321 B HU 180321B
- Authority
- HU
- Hungary
- Prior art keywords
- amino
- formula
- preparation
- general formula
- march
- Prior art date
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- -1 9-substituted 2-amino-purine Chemical class 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims description 50
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 51
- 150000005019 2-aminopurines Chemical class 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000007858 starting material Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 150000003212 purines Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
- 102000055025 Adenosine deaminases Human genes 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical class NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims 1
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical class NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 abstract description 13
- 238000009472 formulation Methods 0.000 abstract description 4
- 208000036142 Viral infection Diseases 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 230000009385 viral infection Effects 0.000 abstract description 2
- ZLIPBFMLCYEHAH-UHFFFAOYSA-N 2-[2-[(2,6-diaminopurin-9-yl)methoxy]ethoxy]ethanol Chemical compound NC1=NC(N)=C2N=CN(COCCOCCO)C2=N1 ZLIPBFMLCYEHAH-UHFFFAOYSA-N 0.000 abstract 2
- GEJGZMHTVMGPJC-UHFFFAOYSA-N 2-amino-9-[2-(2-hydroxyethoxy)ethoxymethyl]-3h-purin-6-one Chemical compound O=C1NC(N)=NC2=C1N=CN2COCCOCCO GEJGZMHTVMGPJC-UHFFFAOYSA-N 0.000 abstract 1
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 241000700605 Viruses Species 0.000 description 5
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- ANSICUUJUXUSNX-UHFFFAOYSA-N 2-[2-(chloromethoxy)ethoxy]ethyl benzoate Chemical compound ClCOCCOCCOC(=O)C1=CC=CC=C1 ANSICUUJUXUSNX-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
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- MTVFDWLEPIRODO-UHFFFAOYSA-N 2-(ethoxymethyl)-7H-purine Chemical compound C(C)OCC1=NC=C2NC=NC2=N1 MTVFDWLEPIRODO-UHFFFAOYSA-N 0.000 description 3
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
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- DNUPYEDSAQDUSO-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl benzoate Chemical compound OCCOCCOC(=O)C1=CC=CC=C1 DNUPYEDSAQDUSO-UHFFFAOYSA-N 0.000 description 2
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- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002036 chloroform fraction Substances 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- NDMXSCGMYOVVJE-UHFFFAOYSA-N ethoxymethyl acetate Chemical compound CCOCOC(C)=O NDMXSCGMYOVVJE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 208000011323 eye infectious disease Diseases 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940097789 heavy mineral oil Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- QNXFUWFRTWSSOK-UHFFFAOYSA-N n-acetyl-n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound O=C1NC(N(C(C)=O)C(=O)C)=NC2=C1NC=N2 QNXFUWFRTWSSOK-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940023462 paste product Drugs 0.000 description 1
- 238000002962 plaque-reduction assay Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/662,899 US4060616A (en) | 1976-03-01 | 1976-03-01 | Purine derivatives with repeating unit |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180321B true HU180321B (en) | 1983-02-28 |
Family
ID=24659686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77WE551A HU180321B (en) | 1976-03-01 | 1977-03-01 | Process for producing 6- and 9-substituted 2-amino-purine derivatives |
Country Status (18)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221909A (en) * | 1978-09-15 | 1980-09-09 | Sloan-Kettering Institute For Cancer Research | P-Acetamidobenzoic acid salts of 9-(hydroxyalkyl) purines |
| US5157120A (en) * | 1980-09-16 | 1992-10-20 | Syntex (U.S.A.) Inc. | Guanine derivatives |
| US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
| NL8202626A (nl) * | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| US4462986A (en) * | 1982-11-04 | 1984-07-31 | Ens Bio Logicals, Inc. | Synergistic anti-herpes compositions |
| US4557934A (en) | 1983-06-21 | 1985-12-10 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one |
| EP0190123A1 (en) * | 1984-07-20 | 1986-08-13 | GAUNTT, Charles, O. | Immunoregulatory and anti-viral compound |
| US4829055A (en) * | 1987-01-23 | 1989-05-09 | Naficy Sadeque S | Method of treatment for herpes infections of external tissues |
| US20110059921A1 (en) * | 2008-03-27 | 2011-03-10 | Ektar Therapeutics | Oligomer-Nitrogenous Base Conjugates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
-
1976
- 1976-03-01 US US05/662,899 patent/US4060616A/en not_active Expired - Lifetime
-
1977
- 1977-02-28 AU AU22760/77A patent/AU506227B2/en not_active Expired
- 1977-03-01 CH CH257277A patent/CH629807A5/de not_active IP Right Cessation
- 1977-03-01 ES ES456407A patent/ES456407A1/es not_active Expired
- 1977-03-01 NZ NZ183468A patent/NZ183468A/xx unknown
- 1977-03-01 IL IL51572A patent/IL51572A/xx unknown
- 1977-03-01 SE SE7702231A patent/SE430505B/xx not_active IP Right Cessation
- 1977-03-01 GB GB8475/77A patent/GB1569393A/en not_active Expired
- 1977-03-01 JP JP2211477A patent/JPS52111594A/ja active Granted
- 1977-03-01 BE BE175385A patent/BE851974A/xx not_active IP Right Cessation
- 1977-03-01 NL NL7702176A patent/NL7702176A/xx not_active Application Discontinuation
- 1977-03-01 HU HU77WE551A patent/HU180321B/hu unknown
- 1977-03-01 CA CA272,884A patent/CA1075237A/en not_active Expired
- 1977-03-01 AT AT134777A patent/AT360552B/de not_active IP Right Cessation
- 1977-03-01 DK DK88977AA patent/DK142546B/da not_active IP Right Cessation
- 1977-03-01 FR FR7705922A patent/FR2342971A1/fr active Granted
- 1977-03-01 DE DE19772708828 patent/DE2708828A1/de not_active Withdrawn
- 1977-03-01 ZA ZA00771219A patent/ZA771219B/xx unknown
-
1978
- 1978-03-16 ES ES467943A patent/ES467943A1/es not_active Expired
-
1981
- 1981-11-03 CH CH700281A patent/CH632759A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK88977A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-09-02 |
| NL7702176A (nl) | 1977-09-05 |
| US4060616A (en) | 1977-11-29 |
| IL51572A (en) | 1980-07-31 |
| SE7702231L (sv) | 1977-09-02 |
| DK142546C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-08-03 |
| DK142546B (da) | 1980-11-17 |
| BE851974A (fr) | 1977-09-01 |
| ES456407A1 (es) | 1978-07-01 |
| ZA771219B (en) | 1978-10-25 |
| IL51572A0 (en) | 1977-05-31 |
| CH629807A5 (de) | 1982-05-14 |
| ATA134777A (de) | 1980-06-15 |
| AU2276077A (en) | 1978-09-07 |
| DE2708828A1 (de) | 1977-09-08 |
| AU506227B2 (en) | 1979-12-20 |
| FR2342971A1 (fr) | 1977-09-30 |
| CH632759A5 (de) | 1982-10-29 |
| AT360552B (de) | 1981-01-26 |
| JPS52111594A (en) | 1977-09-19 |
| JPS6222994B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-20 |
| NZ183468A (en) | 1979-04-26 |
| ES467943A1 (es) | 1978-11-01 |
| FR2342971B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-03 |
| SE430505B (sv) | 1983-11-21 |
| CA1075237A (en) | 1980-04-08 |
| GB1569393A (en) | 1980-06-11 |
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