CH627156A5 - - Google Patents
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- Publication number
- CH627156A5 CH627156A5 CH44281A CH44281A CH627156A5 CH 627156 A5 CH627156 A5 CH 627156A5 CH 44281 A CH44281 A CH 44281A CH 44281 A CH44281 A CH 44281A CH 627156 A5 CH627156 A5 CH 627156A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- acid
- temperature
- water
- oxime
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004280 Sodium formate Substances 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 3
- 235000019254 sodium formate Nutrition 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- -1 4 "nitro-4 Chemical class 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- XWMRMJOORZIBKJ-UHFFFAOYSA-N 2-hydroxy-3-methylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O.CC1=CC=CC(C(O)=O)=C1O XWMRMJOORZIBKJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000001307 Myosotis scorpioides Species 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/30—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing —CHO groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52999/75A GB1560880A (en) | 1975-12-29 | 1975-12-29 | Diphenylmethane derivatives and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627156A5 true CH627156A5 (fr) | 1981-12-31 |
Family
ID=10466224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1643576A CH624378A5 (fr) | 1975-12-29 | 1976-12-29 | |
| CH44281A CH627156A5 (fr) | 1975-12-29 | 1981-01-22 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1643576A CH624378A5 (fr) | 1975-12-29 | 1976-12-29 |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US4113879A (fr) |
| JP (1) | JPS5283356A (fr) |
| AU (1) | AU512090B2 (fr) |
| BE (1) | BE849872A (fr) |
| CA (1) | CA1086743A (fr) |
| CH (2) | CH624378A5 (fr) |
| CS (1) | CS191326B2 (fr) |
| CY (1) | CY1147A (fr) |
| DD (1) | DD128671A5 (fr) |
| DE (1) | DE2658840A1 (fr) |
| DK (1) | DK147105C (fr) |
| ES (1) | ES454657A1 (fr) |
| FI (1) | FI763735A (fr) |
| FR (1) | FR2336921A1 (fr) |
| GB (1) | GB1560880A (fr) |
| HK (1) | HK61881A (fr) |
| HU (1) | HU176679B (fr) |
| IE (1) | IE43994B1 (fr) |
| IL (1) | IL51065A (fr) |
| IN (1) | IN145508B (fr) |
| KE (1) | KE3169A (fr) |
| LU (1) | LU76483A1 (fr) |
| MX (1) | MX4655E (fr) |
| NL (1) | NL7614015A (fr) |
| NO (1) | NO146138C (fr) |
| NZ (1) | NZ182807A (fr) |
| PH (1) | PH13545A (fr) |
| PL (1) | PL104291B1 (fr) |
| SE (1) | SE428468B (fr) |
| ZA (1) | ZA767215B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434185A (en) * | 1993-05-17 | 1995-07-18 | The University Of Kentucky Research Foundation | Method for inhibiting angiogenesis with aurintricarboxylic acid, its analogues or salts |
| US5312988A (en) * | 1993-05-28 | 1994-05-17 | Hoechst Celanese Corporation | Amines derived from THPE |
| US5756781A (en) * | 1995-09-29 | 1998-05-26 | General Electric Company | Method for making tris(hydroxyphenyl) compounds using ion exchange |
| US9751824B2 (en) | 2013-11-18 | 2017-09-05 | Aurin Biotech Inc. | Acetyl salicyclic acid dimers, synthesis thereof, and uses thereof to prevent and treat complement-mediated disorders |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1004609A (en) * | 1911-02-07 | 1911-10-03 | Farbenfab Vorm Bayer F & Co | Triphenylmethane dye. |
| US998139A (en) * | 1911-04-11 | 1911-07-18 | Farbenfab Vorm Bayer F & Co | Greenish-blue triphenylmethane dye. |
| US1034173A (en) * | 1911-09-07 | 1912-07-30 | Farbenfab Vorm Bayer F & Co | Red-violet triphenylmethane dye. |
| US2506486A (en) * | 1948-04-21 | 1950-05-02 | Union Carbide & Carbon Corp | Thermosetting resin from a diphenol and a diglycidyl ether of a diphenol |
| US2764590A (en) * | 1952-03-17 | 1956-09-25 | Thomae Gmbh Dr K | Certain 4, 4'-disubstituted-diphenylpyridyl methanes and process |
| US3558641A (en) * | 1967-10-06 | 1971-01-26 | Merck & Co Inc | Certain pyridyl salicylic acid derivatives |
| US3549656A (en) * | 1967-12-28 | 1970-12-22 | Kefalas As | Antidepressant 1 - aminoalkyl - thiophthalanes and acid addition salts thereof |
| US3579542A (en) * | 1968-06-26 | 1971-05-18 | Hoechst Co American | 4,4',4''-trihydroxytriphenylmethyl-methane |
| US3714226A (en) * | 1970-06-09 | 1973-01-30 | Merck & Co Inc | Phenyl benzoic acid compounds |
| US3794642A (en) * | 1973-01-15 | 1974-02-26 | Lilly Co Eli | Oxidation of substituted methanes to the corresponding substituted methanols |
-
1975
- 1975-12-29 GB GB52999/75A patent/GB1560880A/en not_active Expired
-
1976
- 1976-11-29 CY CY1147A patent/CY1147A/xx unknown
- 1976-12-01 IE IE2633/76A patent/IE43994B1/en not_active IP Right Cessation
- 1976-12-03 ZA ZA767215A patent/ZA767215B/xx unknown
- 1976-12-04 IN IN2159/CAL/76A patent/IN145508B/en unknown
- 1976-12-06 US US05/747,995 patent/US4113879A/en not_active Expired - Lifetime
- 1976-12-06 NZ NZ182807A patent/NZ182807A/xx unknown
- 1976-12-06 CA CA267,212A patent/CA1086743A/fr not_active Expired
- 1976-12-07 IL IL51065A patent/IL51065A/xx unknown
- 1976-12-10 MX MX765211U patent/MX4655E/es unknown
- 1976-12-14 PH PH19243A patent/PH13545A/en unknown
- 1976-12-16 AU AU20605/76A patent/AU512090B2/en not_active Expired
- 1976-12-17 NL NL7614015A patent/NL7614015A/xx not_active Application Discontinuation
- 1976-12-20 HU HU76IE770A patent/HU176679B/hu unknown
- 1976-12-20 SE SE7614304A patent/SE428468B/xx not_active IP Right Cessation
- 1976-12-21 PL PL1976194591A patent/PL104291B1/pl unknown
- 1976-12-23 FR FR7638911A patent/FR2336921A1/fr active Granted
- 1976-12-24 DE DE19762658840 patent/DE2658840A1/de not_active Ceased
- 1976-12-24 BE BE173648A patent/BE849872A/fr not_active IP Right Cessation
- 1976-12-28 DD DD7600196658A patent/DD128671A5/xx unknown
- 1976-12-28 NO NO764371A patent/NO146138C/no unknown
- 1976-12-28 JP JP16078376A patent/JPS5283356A/ja active Granted
- 1976-12-28 LU LU76483A patent/LU76483A1/xx unknown
- 1976-12-29 DK DK586576A patent/DK147105C/da not_active IP Right Cessation
- 1976-12-29 CH CH1643576A patent/CH624378A5/de not_active IP Right Cessation
- 1976-12-29 ES ES454657A patent/ES454657A1/es not_active Expired
- 1976-12-29 FI FI763735A patent/FI763735A/fi not_active Application Discontinuation
- 1976-12-29 CS CS768759A patent/CS191326B2/cs unknown
-
1980
- 1980-03-04 US US06/127,135 patent/USRE31467E/en not_active Expired - Lifetime
-
1981
- 1981-01-22 CH CH44281A patent/CH627156A5/de not_active IP Right Cessation
- 1981-10-19 KE KE3169A patent/KE3169A/xx unknown
- 1981-12-10 HK HK618/81A patent/HK61881A/xx unknown
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