NO791770L - Arylalkyl- og aryloksyalkylfosfonater, og fremgangsmaate til dens fremstilling - Google Patents
Arylalkyl- og aryloksyalkylfosfonater, og fremgangsmaate til dens fremstillingInfo
- Publication number
- NO791770L NO791770L NO791770A NO791770A NO791770L NO 791770 L NO791770 L NO 791770L NO 791770 A NO791770 A NO 791770A NO 791770 A NO791770 A NO 791770A NO 791770 L NO791770 L NO 791770L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- diethyl
- chloro
- methoxyphenoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 alkali metal salt Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UKOSNWUWCKENON-UHFFFAOYSA-N 1-(6-bromohexoxy)-2-chloro-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCCBr)C(Cl)=C1 UKOSNWUWCKENON-UHFFFAOYSA-N 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 241001180873 Saposhnikovia divaricata Species 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- RSAFKRSMGOSHRK-UHFFFAOYSA-N 1-diethoxyphosphorylpropan-2-one Chemical compound CCOP(=O)(CC(C)=O)OCC RSAFKRSMGOSHRK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910000103 lithium hydride Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
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- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
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- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 3
- ZSOUGLKBPPCQTN-UHFFFAOYSA-N 4-(6-iodohexyl)phenol Chemical compound OC1=CC=C(CCCCCCI)C=C1 ZSOUGLKBPPCQTN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HVLCUJYBHMLGOR-UHFFFAOYSA-N 1-iodo-4-(6-iodohexyl)benzene Chemical compound ICCCCCCC1=CC=C(I)C=C1 HVLCUJYBHMLGOR-UHFFFAOYSA-N 0.000 description 2
- QOLSAZPSEJXYSH-UHFFFAOYSA-N 6-bromohexoxybenzene Chemical compound BrCCCCCCOC1=CC=CC=C1 QOLSAZPSEJXYSH-UHFFFAOYSA-N 0.000 description 2
- WDWDITZIWOKNSW-UHFFFAOYSA-N 6-iodohexylbenzene Chemical compound ICCCCCCC1=CC=CC=C1 WDWDITZIWOKNSW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010019973 Herpes virus infection Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- QLQZHOCCTBIRPH-UHFFFAOYSA-N ethyl 4-(6-bromohexoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCCCCCCBr)C=C1 QLQZHOCCTBIRPH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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- GDXQOJQCDWXWKG-UHFFFAOYSA-N 1-(4-iodobutyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCCCI)C=C1 GDXQOJQCDWXWKG-UHFFFAOYSA-N 0.000 description 1
- WGDAXAHMRRWYEO-UHFFFAOYSA-N 1-(6-iodohexoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCCI)C=C1 WGDAXAHMRRWYEO-UHFFFAOYSA-N 0.000 description 1
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- WXRGRXGNGYSIPW-UHFFFAOYSA-N 2-chloro-1-(5-iodopentoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCI)C(Cl)=C1 WXRGRXGNGYSIPW-UHFFFAOYSA-N 0.000 description 1
- SENPRWJKAUOQBP-UHFFFAOYSA-N 2-chloro-1-(6-iodohexoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCCI)C(Cl)=C1 SENPRWJKAUOQBP-UHFFFAOYSA-N 0.000 description 1
- ICYWESMZZMOEGP-UHFFFAOYSA-N 2-chloro-1-(7-iodoheptoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCCCI)C(Cl)=C1 ICYWESMZZMOEGP-UHFFFAOYSA-N 0.000 description 1
- DPQKIWJXCOXIFP-UHFFFAOYSA-N 2-chloro-1-(8-iodooctoxy)-4-methoxybenzene Chemical compound COC1=CC=C(OCCCCCCCCI)C(Cl)=C1 DPQKIWJXCOXIFP-UHFFFAOYSA-N 0.000 description 1
- MBFMCYXCZPBNHI-UHFFFAOYSA-N 3-diethoxyphosphoryl-9-phenylnonan-2-one Chemical compound CCOP(=O)(OCC)C(C(C)=O)CCCCCCC1=CC=CC=C1 MBFMCYXCZPBNHI-UHFFFAOYSA-N 0.000 description 1
- ABDLJYZPOSEWDB-UHFFFAOYSA-N 4-(6-bromohexoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCCCCCCBr)C=C1 ABDLJYZPOSEWDB-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
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- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
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- KXIMOCKAXPRGAL-UHFFFAOYSA-N [4-(6-iodohexyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(CCCCCCI)C=C1 KXIMOCKAXPRGAL-UHFFFAOYSA-N 0.000 description 1
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- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
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- GLMAUUCGSVRVNZ-UHFFFAOYSA-N ethyl 8-(2-chloro-4-methoxyphenoxy)-2-diethoxyphosphoryloctanoate Chemical compound CCOC(=O)C(P(=O)(OCC)OCC)CCCCCCOC1=CC=C(OC)C=C1Cl GLMAUUCGSVRVNZ-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
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- KNBQMQYQYHZXSX-UHFFFAOYSA-M sodium;2-phosphonoacetate Chemical compound [Na+].OP(O)(=O)CC([O-])=O KNBQMQYQYHZXSX-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/912,502 US4182759A (en) | 1978-06-05 | 1978-06-05 | Arylalkyl and aryloxyalkyl phosphonates and use as antiviral agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791770L true NO791770L (no) | 1979-12-06 |
Family
ID=25432033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791770A NO791770L (no) | 1978-06-05 | 1979-05-29 | Arylalkyl- og aryloksyalkylfosfonater, og fremgangsmaate til dens fremstilling |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4182759A (fr) |
| JP (1) | JPS54160348A (fr) |
| KR (1) | KR840002462B1 (fr) |
| AR (1) | AR223343A1 (fr) |
| AT (1) | AT373897B (fr) |
| AU (1) | AU528266B2 (fr) |
| BE (1) | BE876680A (fr) |
| CA (1) | CA1108176A (fr) |
| CH (1) | CH641188A5 (fr) |
| DE (1) | DE2922054A1 (fr) |
| DK (1) | DK223579A (fr) |
| ES (2) | ES481227A1 (fr) |
| FI (1) | FI66009C (fr) |
| FR (1) | FR2428047A1 (fr) |
| GB (1) | GB2022589B (fr) |
| IE (1) | IE48334B1 (fr) |
| IL (1) | IL57300A (fr) |
| IT (1) | IT1203687B (fr) |
| LU (1) | LU81350A1 (fr) |
| MX (1) | MX6013E (fr) |
| NL (1) | NL7904265A (fr) |
| NO (1) | NO791770L (fr) |
| NZ (1) | NZ190460A (fr) |
| PH (2) | PH14734A (fr) |
| PT (1) | PT69693A (fr) |
| SE (1) | SE7904687L (fr) |
| ZA (1) | ZA792447B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2043073B (en) * | 1979-02-13 | 1983-05-11 | Symphar Sa | Mono-and diphosphonate compounds |
| US4556520A (en) * | 1982-10-08 | 1985-12-03 | Zoecon Corporation | 2-Nitro(cyano)phenyloxy(thio)alkyl phosphinates or phosphonates |
| DE4003054A1 (de) * | 1990-02-02 | 1991-08-08 | Hoechst Ag | Verwendung von benzylphosphonsaeurederivaten zur behandlung von durch viren verursachte krankheiten |
| CA2772261A1 (fr) * | 2009-08-27 | 2011-03-17 | Epiphany Biosciences, Inc. | Nouveaux nucleosides phosphonates et analogues |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2934507A (en) * | 1954-06-18 | 1960-04-26 | Monsanto Chemicals | Polyvinyl chloride resins stabilized with mixtures of phosphonate esters, epoxy compounds and metallic salts of fatty acids |
| US3917718A (en) * | 1972-06-22 | 1975-11-04 | Sterling Drug Inc | Cyclopropyl carbinol derivatives |
| US4031246A (en) * | 1973-07-23 | 1977-06-21 | Sterling Drug Inc. | Aryloxyalkyl diketones |
-
1978
- 1978-06-05 US US05/912,502 patent/US4182759A/en not_active Expired - Lifetime
-
1979
- 1979-05-14 CA CA327,532A patent/CA1108176A/fr not_active Expired
- 1979-05-15 NZ NZ190460A patent/NZ190460A/xx unknown
- 1979-05-16 IL IL57300A patent/IL57300A/xx unknown
- 1979-05-21 AU AU47249/79A patent/AU528266B2/en not_active Ceased
- 1979-05-21 ZA ZA792447A patent/ZA792447B/xx unknown
- 1979-05-22 GB GB7917778A patent/GB2022589B/en not_active Expired
- 1979-05-23 PH PH22550A patent/PH14734A/en unknown
- 1979-05-25 IT IT23000/79A patent/IT1203687B/it active
- 1979-05-29 NO NO791770A patent/NO791770L/no unknown
- 1979-05-29 SE SE7904687A patent/SE7904687L/xx not_active Application Discontinuation
- 1979-05-29 FR FR7913632A patent/FR2428047A1/fr active Granted
- 1979-05-29 FI FI791718A patent/FI66009C/fi not_active IP Right Cessation
- 1979-05-29 PT PT69693A patent/PT69693A/pt unknown
- 1979-05-30 MX MX798035U patent/MX6013E/es unknown
- 1979-05-30 DE DE19792922054 patent/DE2922054A1/de not_active Withdrawn
- 1979-05-30 NL NL7904265A patent/NL7904265A/xx not_active Application Discontinuation
- 1979-05-30 JP JP6738479A patent/JPS54160348A/ja active Pending
- 1979-05-30 DK DK223579A patent/DK223579A/da not_active Application Discontinuation
- 1979-05-31 BE BE1/9408A patent/BE876680A/fr not_active IP Right Cessation
- 1979-05-31 LU LU81350A patent/LU81350A1/fr unknown
- 1979-06-01 AT AT0401779A patent/AT373897B/de not_active IP Right Cessation
- 1979-06-01 CH CH515879A patent/CH641188A5/fr not_active IP Right Cessation
- 1979-06-02 ES ES481227A patent/ES481227A1/es not_active Expired
- 1979-06-04 KR KR7901821A patent/KR840002462B1/ko active
- 1979-06-04 AR AR276794A patent/AR223343A1/es active
- 1979-08-08 IE IE945/79A patent/IE48334B1/en unknown
-
1980
- 1980-03-14 ES ES489590A patent/ES489590A0/es active Granted
-
1981
- 1981-08-21 PH PH24473A patent/PH15469A/en unknown
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