NO133199B - - Google Patents
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- Publication number
- NO133199B NO133199B NO2086/70A NO208670A NO133199B NO 133199 B NO133199 B NO 133199B NO 2086/70 A NO2086/70 A NO 2086/70A NO 208670 A NO208670 A NO 208670A NO 133199 B NO133199 B NO 133199B
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- nitro
- carbon atoms
- oxazolidinone
- Prior art date
Links
- -1 alkanoyl isocyanate Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002826 nitrites Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RHBOVQDOJHSHOB-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl n-methylcarbamate Chemical group O=C1OC(COC(=O)NC)CN1N=CC1=CC=C([N+]([O-])=O)O1 RHBOVQDOJHSHOB-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 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 3
- YPPHQQALPLDHRH-UHFFFAOYSA-N 5-(hydroxymethyl)-3-[(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one Chemical compound O=C1OC(CO)CN1N=CC1=CC=C([N+]([O-])=O)O1 YPPHQQALPLDHRH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RHLWQEFHFQTKNT-UHFFFAOYSA-N (2z)-1-cyclooctyl-2-diazocyclooctane Chemical compound [N-]=[N+]=C1CCCCCCC1C1CCCCCCC1 RHLWQEFHFQTKNT-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- RCEGZZHKSORNTP-UHFFFAOYSA-N 3-(furan-2-ylmethylideneamino)-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound C(C1=CC=CO1)=NN1C(OC(C1)CO)=O RCEGZZHKSORNTP-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000616862 Belliella Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- VJDDQSBNUHLBTD-GGWOSOGESA-N [(e)-but-2-enoyl] (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(=O)\C=C\C VJDDQSBNUHLBTD-GGWOSOGESA-N 0.000 description 1
- PCTOQTZSCFMZDA-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl N-acetyl-N-methylcarbamate Chemical group C(C)(=O)N(C(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-])C PCTOQTZSCFMZDA-UHFFFAOYSA-N 0.000 description 1
- JYGJILGJZYQOQD-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl N-ethylcarbamate Chemical group C(C)NC(=O)OCC1CN(C(O1)=O)N=CC1=CC=C(O1)[N+](=O)[O-] JYGJILGJZYQOQD-UHFFFAOYSA-N 0.000 description 1
- RTTQBWBXZZBILA-UHFFFAOYSA-N [3-[(5-nitrofuran-2-yl)methylideneamino]-2-oxo-1,3-oxazolidin-5-yl]methyl N-propylcarbamate Chemical group [N+](=O)([O-])C1=CC=C(C=NN2C(OC(C2)COC(NCCC)=O)=O)O1 RTTQBWBXZZBILA-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000002192 coccidiostatic effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 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 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- IPFUISOJBWATGQ-UHFFFAOYSA-M sodium;5-(2-methylsulfanylethyl)-5-pentan-2-yl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].CCCC(C)C1(CCSC)C(=O)NC(=S)[N-]C1=O IPFUISOJBWATGQ-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
- A23K20/126—Lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Animal Husbandry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28421/69A GB1280354A (en) | 1969-06-05 | 1969-06-05 | Nitrofuran derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133199B true NO133199B (hr) | 1975-12-15 |
| NO133199C NO133199C (hr) | 1976-03-24 |
Family
ID=10275363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2086/70A NO133199C (hr) | 1969-06-05 | 1970-05-29 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3686170A (hr) |
| AT (4) | AT298504B (hr) |
| BE (1) | BE751452A (hr) |
| BG (5) | BG17612A3 (hr) |
| CA (1) | CA919670A (hr) |
| CH (1) | CH546787A (hr) |
| DE (1) | DE2027557A1 (hr) |
| DK (1) | DK135772B (hr) |
| ES (5) | ES380389A1 (hr) |
| FI (1) | FI50881C (hr) |
| FR (1) | FR2052933B1 (hr) |
| GB (1) | GB1280354A (hr) |
| IE (1) | IE34264B1 (hr) |
| IL (1) | IL34665A (hr) |
| NL (1) | NL7007851A (hr) |
| NO (1) | NO133199C (hr) |
| PL (1) | PL80668B1 (hr) |
| RO (5) | RO62333A (hr) |
| SE (1) | SE356750B (hr) |
| SU (1) | SU468425A3 (hr) |
| YU (1) | YU140970A (hr) |
| ZA (1) | ZA703790B (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002535680A (ja) | 1999-01-27 | 2002-10-22 | ファルマシア・アンド・アップジョン・カンパニー | 延長因子ｐ活性モジュレーターのアッセイ方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1199205A (en) * | 1967-12-19 | 1970-07-15 | Geigy Ag J R | 5-Nitro-2-Furfurylideneamino-Oxazolidines |
-
1969
- 1969-06-05 AT AT05003/70A patent/AT298504B/de not_active IP Right Cessation
- 1969-06-05 GB GB28421/69A patent/GB1280354A/en not_active Expired
-
1970
- 1970-05-22 CH CH757170A patent/CH546787A/xx not_active IP Right Cessation
- 1970-05-29 FI FI701523A patent/FI50881C/fi active
- 1970-05-29 DK DK277170AA patent/DK135772B/da unknown
- 1970-05-29 SE SE07421/70A patent/SE356750B/xx unknown
- 1970-05-29 NO NO2086/70A patent/NO133199C/no unknown
- 1970-05-29 NL NL7007851A patent/NL7007851A/xx unknown
- 1970-06-03 YU YU01409/70A patent/YU140970A/xx unknown
- 1970-06-04 AT AT340371A patent/AT297735B/de not_active IP Right Cessation
- 1970-06-04 ES ES380389A patent/ES380389A1/es not_active Expired
- 1970-06-04 ZA ZA703790A patent/ZA703790B/xx unknown
- 1970-06-04 IE IE726/70A patent/IE34264B1/xx unknown
- 1970-06-04 AT AT340471A patent/AT297736B/de not_active IP Right Cessation
- 1970-06-04 IL IL34665A patent/IL34665A/en unknown
- 1970-06-04 BG BG016316A patent/BG17612A3/xx unknown
- 1970-06-04 AT AT340271A patent/AT297734B/de not_active IP Right Cessation
- 1970-06-04 ES ES380388A patent/ES380388A1/es not_active Expired
- 1970-06-04 FR FR7020532A patent/FR2052933B1/fr not_active Expired
- 1970-06-04 BG BG014856A patent/BG17325A3/xx unknown
- 1970-06-04 BG BG016315A patent/BG17611A3/xx unknown
- 1970-06-04 PL PL1970141093A patent/PL80668B1/pl unknown
- 1970-06-04 US US43586A patent/US3686170A/en not_active Expired - Lifetime
- 1970-06-04 BG BG016317A patent/BG17613A3/xx unknown
- 1970-06-04 ES ES380385A patent/ES380385A1/es not_active Expired
- 1970-06-04 CA CA084657A patent/CA919670A/en not_active Expired
- 1970-06-04 DE DE19702027557 patent/DE2027557A1/de active Pending
- 1970-06-04 ES ES380387A patent/ES380387A1/es not_active Expired
- 1970-06-04 BG BG016314A patent/BG17610A3/xx unknown
- 1970-06-04 ES ES380386A patent/ES380386A1/es not_active Expired
- 1970-06-04 BE BE751452D patent/BE751452A/xx unknown
- 1970-06-04 SU SU1445756A patent/SU468425A3/ru active
- 1970-06-05 RO RO71676A patent/RO62333A/ro unknown
- 1970-06-05 RO RO71675A patent/RO62332A/ro unknown
- 1970-06-05 RO RO63554A patent/RO56799A/ro unknown
- 1970-06-05 RO RO7000071673A patent/RO62446A/ro unknown
- 1970-06-05 RO RO71674A patent/RO62331A/ro unknown
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