IL27110A - Thienyloxymethyl penicillins and process for preparing them - Google Patents
Thienyloxymethyl penicillins and process for preparing themInfo
- Publication number
- IL27110A IL27110A IL27110A IL2711066A IL27110A IL 27110 A IL27110 A IL 27110A IL 27110 A IL27110 A IL 27110A IL 2711066 A IL2711066 A IL 2711066A IL 27110 A IL27110 A IL 27110A
- Authority
- IL
- Israel
- Prior art keywords
- penicillin
- thienyloxy
- methyl
- salts
- penicillins
- Prior art date
Links
- 229930182555 Penicillin Natural products 0.000 title claims description 41
- 150000002960 penicillins Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940049954 penicillin Drugs 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 35
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 33
- 239000002243 precursor Substances 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 21
- 238000000855 fermentation Methods 0.000 claims description 17
- 230000004151 fermentation Effects 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 19
- 229930195708 Penicillin V Natural products 0.000 description 18
- 229940056367 penicillin v Drugs 0.000 description 18
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 18
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 10
- 235000011056 potassium acetate Nutrition 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- ZJKVAVOAEMCJGI-UHFFFAOYSA-N 2-thiophen-3-yloxyacetic acid Chemical compound OC(=O)COC=1C=CSC=1 ZJKVAVOAEMCJGI-UHFFFAOYSA-N 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 239000010685 fatty oil Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- -1 penicillin G Chemical compound 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000228150 Penicillium chrysogenum Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229960004793 sucrose Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940056360 penicillin g Drugs 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- GQIBGWZPQLUNEH-UHFFFAOYSA-N CC1=CC(=CS1)OCC(=O)O Chemical compound CC1=CC(=CS1)OCC(=O)O GQIBGWZPQLUNEH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003460 beta-lactamyl group Chemical group 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XPTNNRBWASQCHZ-UHFFFAOYSA-N 2-(4,5-dimethylthiophen-3-yl)oxyacetic acid Chemical compound CC=1SC=C(OCC(O)=O)C=1C XPTNNRBWASQCHZ-UHFFFAOYSA-N 0.000 description 1
- HQEROVXUKINLPI-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanylacetic acid Chemical compound OC(=O)CSC1=CC=C(F)C=C1 HQEROVXUKINLPI-UHFFFAOYSA-N 0.000 description 1
- HKONQZIIRBNRRK-UHFFFAOYSA-N 2-(5-methylthiophen-2-yl)oxyacetic acid Chemical compound CC1=CC=C(OCC(O)=O)S1 HKONQZIIRBNRRK-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- WYZSHSYANZLLRM-UHFFFAOYSA-N 2-thiophen-2-yloxyacetic acid Chemical compound OC(=O)COC1=CC=CS1 WYZSHSYANZLLRM-UHFFFAOYSA-N 0.000 description 1
- AAODRFJDILYMSA-UHFFFAOYSA-N 2-thiophen-3-yloxyacetamide Chemical compound S1C=C(C=C1)OCC(=O)N AAODRFJDILYMSA-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GSGPGZWHEBKKAN-UHFFFAOYSA-N CC1=C(OCC(O)=O)C=CS1 Chemical compound CC1=C(OCC(O)=O)C=CS1 GSGPGZWHEBKKAN-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 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 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004107 Penicillin G sodium Substances 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000019369 penicillin G sodium Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical class OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/933—Penicillium
- Y10S435/935—Penicillium chrysogenum
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0048063 | 1965-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27110A true IL27110A (en) | 1971-02-25 |
Family
ID=7102016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27110A IL27110A (en) | 1965-12-31 | 1966-12-21 | Thienyloxymethyl penicillins and process for preparing them |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3502655A (de) |
| AT (1) | AT278240B (de) |
| BE (1) | BE692091A (de) |
| BR (1) | BR6685826D0 (de) |
| CH (1) | CH481216A (de) |
| DE (1) | DE1467903A1 (de) |
| DK (1) | DK123982B (de) |
| ES (1) | ES335036A1 (de) |
| FI (1) | FI44365B (de) |
| FR (1) | FR1508425A (de) |
| GB (1) | GB1168301A (de) |
| IL (1) | IL27110A (de) |
| NL (1) | NL6618343A (de) |
| SE (1) | SE350067B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354971A (en) * | 1981-06-22 | 1982-10-19 | Eli Lilly And Company | Non-extractive penicillin V recovery process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2479297A (en) * | 1946-03-08 | 1949-08-16 | Lilly Co Eli | Process and culture media for producing new penicillins |
| US2479296A (en) * | 1946-03-08 | 1949-08-16 | Lilly Co Eli | Process and culture media for producing new penicillins |
| US2479295A (en) * | 1946-03-08 | 1949-08-16 | Lilly Co Eli | Process and culture media for producing new penicillins |
-
1965
- 1965-12-31 DE DE19651467903 patent/DE1467903A1/de active Pending
-
1966
- 1966-12-15 AT AT1155366A patent/AT278240B/de not_active IP Right Cessation
- 1966-12-19 US US602527A patent/US3502655A/en not_active Expired - Lifetime
- 1966-12-21 IL IL27110A patent/IL27110A/en unknown
- 1966-12-28 CH CH1869766A patent/CH481216A/de not_active IP Right Cessation
- 1966-12-28 ES ES335036A patent/ES335036A1/es not_active Expired
- 1966-12-28 SE SE17793/66A patent/SE350067B/xx unknown
- 1966-12-29 DK DK674866AA patent/DK123982B/da unknown
- 1966-12-29 NL NL6618343A patent/NL6618343A/xx unknown
- 1966-12-29 FI FI3474/66A patent/FI44365B/fi active
- 1966-12-30 BR BR185826/66A patent/BR6685826D0/pt unknown
-
1967
- 1967-01-02 GB GB77/67A patent/GB1168301A/en not_active Expired
- 1967-01-02 FR FR89691A patent/FR1508425A/fr not_active Expired
- 1967-01-03 BE BE692091D patent/BE692091A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH481216A (de) | 1969-11-15 |
| DE1467903A1 (de) | 1969-01-16 |
| FI44365B (de) | 1971-08-02 |
| ES335036A1 (es) | 1968-03-01 |
| US3502655A (en) | 1970-03-24 |
| NL6618343A (de) | 1967-07-03 |
| BE692091A (de) | 1967-07-03 |
| DK123982B (da) | 1972-08-28 |
| SE350067B (de) | 1972-10-16 |
| GB1168301A (en) | 1969-10-22 |
| AT278240B (de) | 1970-01-26 |
| FR1508425A (fr) | 1968-01-05 |
| BR6685826D0 (pt) | 1973-12-27 |
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