NO126914B - - Google Patents
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- Publication number
- NO126914B NO126914B NO03004/69A NO300469A NO126914B NO 126914 B NO126914 B NO 126914B NO 03004/69 A NO03004/69 A NO 03004/69A NO 300469 A NO300469 A NO 300469A NO 126914 B NO126914 B NO 126914B
- Authority
- NO
- Norway
- Prior art keywords
- methylcinnamylamine
- liters
- mixture
- compound
- ethanol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- -1 alkali metal derivative of benzhydrol Chemical class 0.000 claims description 9
- VJQMHUJDWBFFNV-UHFFFAOYSA-N 2-(4-phenylbut-3-enylamino)ethanol Chemical compound C(C=CC1=CC=CC=C1)CNCCO VJQMHUJDWBFFNV-UHFFFAOYSA-N 0.000 claims description 6
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 230000001430 anti-depressive effect Effects 0.000 claims description 5
- 239000000935 antidepressant agent Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- QTKQVDXGCWKEHE-UHFFFAOYSA-N n-(2-benzhydryloxyethyl)-n-methyl-3-phenylprop-2-en-1-amine Chemical compound C=1C=CC=CC=1C=CCN(C)CCOC(C=1C=CC=CC=1)C1=CC=CC=C1 QTKQVDXGCWKEHE-UHFFFAOYSA-N 0.000 claims description 4
- FVOVPMIXOSNWOK-UHFFFAOYSA-N n-(2-chloroethyl)-n-methyl-3-phenylprop-2-en-1-amine Chemical compound ClCCN(C)CC=CC1=CC=CC=C1 FVOVPMIXOSNWOK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RHPMSSCVPPONDM-UHFFFAOYSA-N n-methyl-3-phenylprop-2-en-1-amine Chemical compound CNCC=CC1=CC=CC=C1 RHPMSSCVPPONDM-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000916 dilatatory effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- SKTUNMLBMMTJHS-QPJJXVBHSA-N 2-[[(e)-3-phenylprop-2-enyl]amino]ethanol Chemical compound OCCNC\C=C\C1=CC=CC=C1 SKTUNMLBMMTJHS-QPJJXVBHSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZNVASENTCOLNJT-UHFFFAOYSA-N [2-chloroethoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCCCl)C1=CC=CC=C1 ZNVASENTCOLNJT-UHFFFAOYSA-N 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34700/68A GB1219609A (en) | 1968-07-19 | 1968-07-19 | Diphenylmethoxyethylamino derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126914B true NO126914B (da) | 1973-04-09 |
Family
ID=10368878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03004/69A NO126914B (da) | 1968-07-19 | 1969-07-18 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3666811A (da) |
| AT (4) | AT297687B (da) |
| BE (1) | BE735819A (da) |
| CA (1) | CA976980A (da) |
| CH (1) | CH519468A (da) |
| CS (4) | CS166710B2 (da) |
| DE (1) | DE1936206A1 (da) |
| ES (4) | ES369676A1 (da) |
| FR (1) | FR2013283B1 (da) |
| GB (1) | GB1219609A (da) |
| IL (1) | IL32481A (da) |
| NL (1) | NL6911040A (da) |
| NO (1) | NO126914B (da) |
| SE (1) | SE372521B (da) |
| SU (1) | SU499801A3 (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795735A (fr) * | 1972-03-06 | 1973-06-18 | Cerm Cent Europ Rech Mauvernay | Nouvelles ethylenediamines substituees a activite cardiovasculaire |
| GB1363986A (en) * | 1972-03-07 | 1974-08-21 | Gist Brocades Nv | Diphenylmethoxyethylamines |
| US4049825A (en) * | 1972-03-07 | 1977-09-20 | Gist-Brocades N.V. | Aminoalkylethers; composition and method of use |
| GB1527489A (en) * | 1976-08-05 | 1978-10-04 | Andreu Sa Dr | Amine compound |
| GB8824262D0 (en) * | 1988-10-17 | 1988-11-23 | Pfizer Ltd | Therapeutic agents |
| EP0467435A3 (en) * | 1990-07-19 | 1992-04-01 | Akzo N.V. | Benzhydryl derivatives having calmodulin inhibitor properties |
| US6433196B1 (en) * | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
| JP4927735B2 (ja) * | 2004-08-20 | 2012-05-09 | ユニバーシテイ・オブ・バージニア・パテント・フアウンデーシヨン | Ｔ型カルシウムチャネル阻害剤 |
| US9427429B2 (en) | 2010-03-01 | 2016-08-30 | Tau Therapeutics Llc | Cancer diagnosis and imaging |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2499058A (en) * | 1950-02-28 | B-haloxantfflne salts of diarylalkyl | ||
| GB609455A (en) * | 1946-01-11 | 1948-09-30 | Parke Davis & Co | Quaternary ammonium halides and methods for obtaining the same |
| US2499417A (en) * | 1946-07-15 | 1950-03-07 | Parke Davis & Co | Trialkyl ammonium halides of benzhydryl-aminoethyl ether |
-
1968
- 1968-07-19 GB GB34700/68A patent/GB1219609A/en not_active Expired
-
1969
- 1969-06-25 IL IL32481A patent/IL32481A/en unknown
- 1969-07-03 AT AT1070370A patent/AT297687B/de active
- 1969-07-03 AT AT1070270A patent/AT297686B/de not_active IP Right Cessation
- 1969-07-03 AT AT638269A patent/AT295500B/de not_active IP Right Cessation
- 1969-07-03 AT AT1070470A patent/AT298464B/de not_active IP Right Cessation
- 1969-07-08 BE BE735819D patent/BE735819A/xx unknown
- 1969-07-10 SU SU1346525A patent/SU499801A3/ru active
- 1969-07-11 CS CS4951A patent/CS166710B2/cs unknown
- 1969-07-11 CS CS7367*A patent/CS166713B2/cs unknown
- 1969-07-11 CS CS7365*A patent/CS166711B2/cs unknown
- 1969-07-11 CS CS7366*A patent/CS166712B2/cs unknown
- 1969-07-16 DE DE19691936206 patent/DE1936206A1/de active Pending
- 1969-07-17 CA CA057,261A patent/CA976980A/en not_active Expired
- 1969-07-17 CH CH1097969A patent/CH519468A/de not_active IP Right Cessation
- 1969-07-18 US US843170A patent/US3666811A/en not_active Expired - Lifetime
- 1969-07-18 FR FR696924564A patent/FR2013283B1/fr not_active Expired
- 1969-07-18 NO NO03004/69A patent/NO126914B/no unknown
- 1969-07-18 SE SE6910181A patent/SE372521B/xx unknown
- 1969-07-18 NL NL6911040A patent/NL6911040A/xx unknown
- 1969-07-19 ES ES369676A patent/ES369676A1/es not_active Expired
-
1971
- 1971-03-16 ES ES389279A patent/ES389279A1/es not_active Expired
- 1971-03-16 ES ES389280A patent/ES389280A1/es not_active Expired
- 1971-03-16 ES ES389281A patent/ES389281A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES369676A1 (es) | 1971-07-16 |
| CS166713B2 (da) | 1976-03-29 |
| IL32481A (en) | 1973-05-31 |
| CS166712B2 (da) | 1976-03-29 |
| CS166710B2 (da) | 1976-03-29 |
| AT298464B (de) | 1972-05-10 |
| BE735819A (da) | 1970-01-08 |
| DE1936206A1 (de) | 1970-01-22 |
| FR2013283B1 (da) | 1973-06-08 |
| ES389279A1 (es) | 1973-06-16 |
| GB1219609A (en) | 1971-01-20 |
| CH519468A (de) | 1972-02-29 |
| AT297686B (de) | 1972-04-10 |
| US3666811A (en) | 1972-05-30 |
| NL6911040A (da) | 1970-01-21 |
| AT295500B (de) | 1972-01-10 |
| SU499801A3 (ru) | 1976-01-15 |
| ES389280A1 (es) | 1973-06-16 |
| CS166711B2 (da) | 1976-03-29 |
| CA976980A (en) | 1975-10-28 |
| ES389281A1 (es) | 1973-06-16 |
| AT297687B (de) | 1972-04-10 |
| SE372521B (da) | 1974-12-23 |
| FR2013283A1 (da) | 1970-03-27 |
| IL32481A0 (en) | 1969-08-27 |
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