IL32481A - Diphenylmethoxyethylamino derivatives,their preparation and pharmaceutical compositions containing them - Google Patents
Diphenylmethoxyethylamino derivatives,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL32481A IL32481A IL32481A IL3248169A IL32481A IL 32481 A IL32481 A IL 32481A IL 32481 A IL32481 A IL 32481A IL 3248169 A IL3248169 A IL 3248169A IL 32481 A IL32481 A IL 32481A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- derivatives
- preparation
- acid addition
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- -1 Diphenylmethoxyethylamino Chemical class 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- RDAFNSMYPSHCBK-QPJJXVBHSA-N (e)-3-phenylprop-2-en-1-amine Chemical compound NC\C=C\C1=CC=CC=C1 RDAFNSMYPSHCBK-QPJJXVBHSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000243 solution Substances 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
- 230000000916 dilatatory effect Effects 0.000 description 4
- 239000013543 active substance Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 235000019890 Amylum Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VFYFMNCKPJDAPV-UHFFFAOYSA-N 2,2'-(5-oxo-1,3-dioxolan-4,4-diyl)diessigs Chemical compound C1N(C2)CN3CN1CN2C3.OC(=O)CC1(CC(O)=O)OCOC1=O VFYFMNCKPJDAPV-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
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 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 1
- 101100459301 Mus musculus Myl4 gene Proteins 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-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
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010932 ethanolysis reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 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
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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 (2)
| Publication Number | Publication Date |
|---|---|
| IL32481A0 IL32481A0 (en) | 1969-08-27 |
| IL32481A true IL32481A (en) | 1973-05-31 |
Family
ID=10368878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32481A IL32481A (en) | 1968-07-19 | 1969-06-25 | Diphenylmethoxyethylamino derivatives,their preparation and pharmaceutical compositions containing them |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3666811A (en, 2012) |
| AT (4) | AT295500B (en, 2012) |
| BE (1) | BE735819A (en, 2012) |
| CA (1) | CA976980A (en, 2012) |
| CH (1) | CH519468A (en, 2012) |
| CS (4) | CS166712B2 (en, 2012) |
| DE (1) | DE1936206A1 (en, 2012) |
| ES (4) | ES369676A1 (en, 2012) |
| FR (1) | FR2013283B1 (en, 2012) |
| GB (1) | GB1219609A (en, 2012) |
| IL (1) | IL32481A (en, 2012) |
| NL (1) | NL6911040A (en, 2012) |
| NO (1) | NO126914B (en, 2012) |
| SE (1) | SE372521B (en, 2012) |
| SU (1) | SU499801A3 (en, 2012) |
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 |
| US4049825A (en) * | 1972-03-07 | 1977-09-20 | Gist-Brocades N.V. | Aminoalkylethers; composition and method of use |
| GB1363986A (en) * | 1972-03-07 | 1974-08-21 | Gist Brocades Nv | Diphenylmethoxyethylamines |
| 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 |
| CA2576191C (en) | 2004-08-20 | 2013-03-19 | University Of Virginia Patent Foundation | T type calcium channel inhibitors |
| SG183114A1 (en) | 2010-03-01 | 2012-09-27 | 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 AT638269A patent/AT295500B/de not_active IP Right Cessation
- 1969-07-03 AT AT1070470A patent/AT298464B/de not_active IP Right Cessation
- 1969-07-03 AT AT1070370A patent/AT297687B/de active
- 1969-07-03 AT AT1070270A patent/AT297686B/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 CS7366*A patent/CS166712B2/cs unknown
- 1969-07-11 CS CS7365*A patent/CS166711B2/cs unknown
- 1969-07-11 CS CS7367*A patent/CS166713B2/cs unknown
- 1969-07-11 CS CS4951A patent/CS166710B2/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 FR FR696924564A patent/FR2013283B1/fr not_active Expired
- 1969-07-18 NL NL6911040A patent/NL6911040A/xx unknown
- 1969-07-18 US US843170A patent/US3666811A/en not_active Expired - Lifetime
- 1969-07-18 NO NO03004/69A patent/NO126914B/no unknown
- 1969-07-18 SE SE6910181A patent/SE372521B/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 |
|---|---|
| GB1219609A (en) | 1971-01-20 |
| NL6911040A (en, 2012) | 1970-01-21 |
| ES389279A1 (es) | 1973-06-16 |
| NO126914B (en, 2012) | 1973-04-09 |
| BE735819A (en, 2012) | 1970-01-08 |
| IL32481A0 (en) | 1969-08-27 |
| ES369676A1 (es) | 1971-07-16 |
| CS166710B2 (en, 2012) | 1976-03-29 |
| US3666811A (en) | 1972-05-30 |
| CS166712B2 (en, 2012) | 1976-03-29 |
| AT295500B (de) | 1972-01-10 |
| ES389280A1 (es) | 1973-06-16 |
| DE1936206A1 (de) | 1970-01-22 |
| AT298464B (de) | 1972-05-10 |
| AT297687B (de) | 1972-04-10 |
| SE372521B (en, 2012) | 1974-12-23 |
| FR2013283B1 (en, 2012) | 1973-06-08 |
| FR2013283A1 (en, 2012) | 1970-03-27 |
| ES389281A1 (es) | 1973-06-16 |
| CS166713B2 (en, 2012) | 1976-03-29 |
| AT297686B (de) | 1972-04-10 |
| SU499801A3 (ru) | 1976-01-15 |
| CS166711B2 (en, 2012) | 1976-03-29 |
| CH519468A (de) | 1972-02-29 |
| CA976980A (en) | 1975-10-28 |
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