SU488399A3 - The method of obtaining derivatives diphenylaminopropane - Google Patents
The method of obtaining derivatives diphenylaminopropaneInfo
- Publication number
- SU488399A3 SU488399A3 SU1957933A SU1957933A SU488399A3 SU 488399 A3 SU488399 A3 SU 488399A3 SU 1957933 A SU1957933 A SU 1957933A SU 1957933 A SU1957933 A SU 1957933A SU 488399 A3 SU488399 A3 SU 488399A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diphenyl
- salt
- diphenylaminopropane
- hydrogen
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- BCFKYKHGGFAUAF-UHFFFAOYSA-N n-phenyl-n-propylaniline Chemical compound C=1C=CC=CC=1N(CCC)C1=CC=CC=C1 BCFKYKHGGFAUAF-UHFFFAOYSA-N 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- -1 sodium lithium aluminum hydride Chemical compound 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- LVGZJQSCXZRTBW-UHFFFAOYSA-N 3,3-diphenyl-3-propoxypropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN)(OCCC)C1=CC=CC=C1 LVGZJQSCXZRTBW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VXCRRRAZVHYGPA-UHFFFAOYSA-N n-propan-2-ylcyclopropanecarboxamide Chemical compound CC(C)NC(=O)C1CC1 VXCRRRAZVHYGPA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
восстанавливспот комплексными гидридами алюмини в среде инертного растворител и образовавшеес в результате реакции основание (носле удалени избыточного количества восстановител ), выдел ют в свободном виде или в виде соли.The reduction of aluminum complex hydrides in an inert solvent and the base formed by the reaction (removing excess amount of reducing agent) are recovered in free form or in salt form.
В качестве гидрида алюмини в основиом может быть исиользован литийалюминийгидрид и дигидробис- (метоксиэтокси) -алюминат натри . В качестве растворител прежде всего могут быть использованы диэтиловый эфир и тетрагидрофуран. Реакцию восстановлени наиболее целесообразно проводить при нагревании, преимущественно при температуре кипени растворител .As the aluminum hydride, sodium lithium aluminum hydride and sodium dihydrobis (methoxyethoxy) aluminum aluminate can be used as the basis. As the solvent, diethyl ether and tetrahydrofuran can be used primarily. The reduction reaction is most advantageously carried out with heating, preferably at the boiling point of the solvent.
Избыточное количество восстановител разлагают водой, после чего продукт реакции хможет быть получен унариванием в относительно чистой форме. Полученное вещество может быть подвергнуто дальнейшей очистке непосредственно в виде основани или же полученные соединени могут быть переведены в их соли.An excess amount of reducing agent is decomposed with water, after which the reaction product can be obtained by fumigating in a relatively pure form. The resulting material can be further purified directly as a base, or the resulting compounds can be converted to their salts.
Пример 1. 10,6 г 1,1-дифенил-1-нроиокси-3-циклопропилкарбониламиноиропана (т. пл. 144-HS C) загружали в экстрактор Сокслета и затем посредством экстракции прибавл ли к предварительно приготовленной суспепзии 8,0 г литийалюминийгидрида в 300 мл диэтилового эфира. Непосредственно после этого реакционную смесь нагревали при температуре кипени в течение 20 ч. Избыточное количество восстановител разлагали водой, эфирный раствор отдел ли и упаривали. В результате получали 10 г 1,1-дифенил-1-иропокси-3- (циклонронилметил) - аминонропана в виде в зкого маслообразного продукта (88% от теории). Полученна из этого соединени сол нокисла соль после перекристаллизации из этилового эфира уксусной кислоты имела т. пл. 170-174°С.Example 1. 10.6 g of 1,1-diphenyl-1-nroioxy-3-cyclopropylcarbonylaminoiropane (mp. 144-HS C) were loaded into a Soxhlet extractor and then 8.0 g of lithium aluminum hydride were added to the previously prepared suspension in extraction. 300 ml diethyl ether. Immediately thereafter, the reaction mixture was heated at boiling point for 20 hours. The excess amount of reducing agent was decomposed with water, the ether solution was separated and evaporated. As a result, 10 g of 1,1-diphenyl-1-iropoxy-3- (cyclonronylmethyl) - aminonropane was obtained as a viscous oily product (88% of theory). The salt obtained from this soloxide salt after recrystallisation from ethyl acetate was m.p. 170-174 ° C.
Найдено, %: С 73,7; Н 8,4; С1 9,9.Found,%: C 73.7; H 8.4; C1 9.9.
Вычислено, %: С 73,41; Н 8,4; С1 9,85.Calculated,%: C 73.41; H 8.4; C1 9.85.
Примененный в качестве исходного соединени 1,1 -дифенил-1 -пропокси-3-циклонропилкарбониламинопропан получали по следующей методике.The 1,1-diphenyl-1-propoxy-3-cyclonylcarbonylaminopropane used as the starting compound was prepared according to the following procedure.
Смесь, состо щую из 10 г 3,3-дифенил-З-пропоксипропиламина (т. пл. 45-50°С), 7,5 г триэтиламина, 4,7 г хлорангидрида циклопропилкарбоновой кислоты и 160 мл бензола, нагревали в течение 1 ч при 40°С. Затем к реакционной смеси прибавл ли воду и раздел ли образовавщиес слои. Органический слой промывали раствором соды и водой, упаривали и полученный остаток перекристаллизовывали из циклогексана. В результате проведенных операций получали 10,6 г 1,1-дифенил-1-проиокси- 2 -циклопропилкарбониламинопропана, т. пл. 144-148°С.A mixture consisting of 10 g of 3,3-diphenyl-3-propoxypropylamine (mp 45-50 ° C), 7.5 g of triethylamine, 4.7 g of cyclopropylcarboxylic acid chloride and 160 ml of benzene was heated for 1 h at 40 ° C. Water was then added to the reaction mixture and the resulting layers separated. The organic layer was washed with soda solution and water, evaporated and the resulting residue was recrystallized from cyclohexane. As a result of the operations performed, 10.6 g of 1,1-diphenyl-1-pro-2-cyclopropylcarbonylaminopropane were obtained; mp. 144-148 ° C.
Пример 2. 12,1 г N- (3,2-дифенил-2-метоксинропил ) -.|3,р-диметилакриламида восстанавливали литийалюминийгидридом в эфире (растворитель), как в примере 1. Получали 11,0 г 1,1-дифенил-1-метокси-3- (у,у-диметилаллил ) -аминопропана в виде в зкого маслообразного продукта (95% от теории). Полученна из выделенного соединени сол нокисла соль носле перекристаллизации из водыExample 2. 12.1 g of N- (3,2-diphenyl-2-methoxy-propyl) -. | 3, p-dimethylacrylamide was reduced with lithium aluminum hydride in ether (solvent) as in Example 1. 11.0 g of 1.1- was obtained. diphenyl-1-methoxy-3- (y, y-dimethylallyl) -aminopropane as a viscous oily product (95% of theory). The salt obtained from the isolated soloxide salt was carried over to recrystallization from water.
имела т. пл. 85-88°С.had t. pl. 85-88 ° C.
Найдено, %; С 72,8; Н 8,3; N 4,0. Вычислено, %: С 72,92; Н 8,16; N 4,05. Пример 3. 6,0 г амида N- (3,3-дифенил-3-метоксипронил ) -р,р-диметилакриловой кислоты нагревали в течение 60 ч при температуре кипени в 100 мл бензола, причем к реакционной смеси было прибавлено 7,0 мл 70%-ного бензольного раствора дигидробис- (метоксиэтокси ) - алюмината натри . Затем кFound,%; C, 72.8; H 8.3; N 4.0. Calculated,%: C, 72.92; H 8.16; N 4.05. Example 3. 6.0 g of N- (3,3-diphenyl-3-methoxypronyl) -p, p-dimethylacrylic acid amide was heated for 60 hours at boiling point in 100 ml of benzene, and 7.0 were added to the reaction mixture. ml of a 70% benzene solution of dihydrobis- (methoxyethoxy) - sodium aluminate. Then to
реакционной смеси прибавл ли 20 .мл 4 н. раствора гидроокиси натри , раздел ли образовавшиес слои и органическрш слой упаривали . После упаривани оставалось 5,5 г маслообразного вещества (96% от теории, котороеthe reaction mixture was added 20. 4 ml. sodium hydroxide solution, the layers were separated and the organic layer was evaporated. After evaporation, 5.5 g of an oily substance remained (96% of theory, which
раствор ли в диэтиловом эфире и затем пропусканием в раствор хлористого водорода осаждали сол нокислую соль полученного соединени . Полученна сол нокисла соль 1,1-дифенил - 1 - метокси-3 - (у.у-днметплаллил) was dissolved in diethyl ether, and then the hydrochloric acid salt of the obtained compound was precipitated by passing to a solution of hydrogen chloride. The resulting soloxidic salt 1,1-diphenyl-1-methoxy-3- (y.d-dnmetplallyl)
-аминопропана после перекристаллизации из воды имела т. пл. 85-88°С.-minopropane after recrystallization from water had so pl. 85-88 ° C.
Найдено, %; С 72,6; Н 8,0; N4,0. Вычислено, %: С 72,92; Н 8,16; iN 4,05. Нример 4. 0,75 г литийалюминийгидрида суспендировали в 100 мл тетрагидрофурана и к приготовленной суспензии прибавл ли по капл м раствор 3,7 г амида N- (3,3-дифенил-3-метоксинропил ) - коричной кислоты в 40 мл тетрагидрофурана. Затем смесь нагревали при температуре кипени в течение 24 ч, после чего охлаждали и прибавл ли по капл м 4 мл воды. Выделившуюс в осадок соль отдел ли, а образовавшийс раствор упаривали . В результате проведенных операций получали 3,4 г 1,1-дифенил-1-метокси-3-цианамиламинопропана в форме маслообразного вещества (95% от теории). Сол нокисла соль, полученна из этого вещества осаждением хлористым водородом из эфирного раствора,Found,%; C, 72.6; H 8.0; N4.0. Calculated,%: C, 72.92; H 8.16; iN 4.05. Example 4. 0.75 g of lithium aluminum hydride was suspended in 100 ml of tetrahydrofuran, and a solution of 3.7 g of N- (3,3-diphenyl-3-methoxynyl) -cinnamic acid amide in 40 ml of tetrahydrofuran was added dropwise to the prepared suspension. The mixture was then heated at reflux for 24 hours, then cooled and 4 ml of water was added dropwise. The precipitated salt was separated, and the resulting solution was evaporated. As a result of these operations, 3.4 g of 1,1-diphenyl-1-methoxy-3-cyanamylaminopropane was obtained in the form of an oily substance (95% of theory). Soloxide salt obtained from this substance by precipitation with hydrogen chloride from ethereal solution,
имела т. пл. 195-198°С.had t. pl. 195-198 ° C.
Найдено, %; С 76,0; Н 7,2; N 3,4. Вычислено, %: С 76,22; Н 7,16; N 3,56. При м е р 5. Аналогично тому, как описано в примере 1, 10,6 г 1,1-дифенил-1-метокси-2-метил- 3-циклобутилкарбониламипопропана прибавл ли посредством экстрагировани к суспензии, приготовленной из 5,3 г литийалюминийгидрида и смеси 200 мл эфира и 75 мл бензола, затем точно так же обрабатывалиFound,%; C, 76.0; H 7.2; N 3.4. Calculated,%: C, 76.22; H 7.16; N 3.56. Example 5. In a manner similar to that described in Example 1, 10.6 g of 1,1-diphenyl-1-methoxy-2-methyl-3-cyclobutylcarbonylamopropane was added to the suspension prepared from 5.3 g of lithium aluminum hydride by extraction. and mixtures of 200 ml of ether and 75 ml of benzene, then treated in the same way.
реакционную смесь. Получали 10,2 г 1,1-дифенил-1-метокси-2-метил-З - (диклобутилметил)-аминопропана в виде в зкого маслообразного вещества (100% от теории). Сол нокисла соль, полученна из этого вещества, имелаreaction mixture. 10.2 g of 1,1-diphenyl-1-methoxy-2-methyl-3 - (diclobutylmethyl) -aminopropane were obtained as a viscous oily substance (100% of theory). Soloxide salt obtained from this substance had
т. пл. 198-200°С.m.p. 198-200 ° C.
Найдено, %: С 73,4; Н 8,8; N 3,6. Вычислено, %: С 73,41; Н 8,46; N 3,86. Пример 6. 26,7 г 1,1-дифенил-1-метокси-3-циклобутилкарбониламиноироиана восстанавлквали , как описано в примере 1, 13,0 гFound,%: C 73.4; H 8.8; N 3.6. Calculated,%: C 73.41; H 8.46; N 3.86. Example 6. 26.7 g of 1,1-diphenyl-1-methoxy-3-cyclobutylcarbonylamino-ianine were reduced as described in Example 1, 13.0 g
.;u(.uoMniiiiirin;ipii,ua в 400 мл диэтнлового эфирл п 150 1л бензола. Получали 24,7 г (97% от геории) 1Д-д11фен11Л-1-метокси-о- (цнклобутилметил) -аминопропана с т. пл. 60-62°С. Сол нокисла соль, полученна из этого соединени , имела т. нл. 194-196°С..; u (.uoMniiiiirin; ipii, ua in 400 ml of diethylether p 150 1l of benzene. 24.7 g (97% of geography) were obtained. 1D-d11fen11L-1-methoxy-o- (cyclobutylmethyl) -aminopropane with m.p. 60-62 ° C. Soloxyl salt obtained from this compound had 194-196 ° C.
Найдено, %: С 72,2; Н 8,4; N 4,0.Found,%: C 72.2; H 8.4; N 4.0.
Вычислено, %; С 72,92; Н 8,10; N 4,05.Calculated,%; C, 72.92; H 8.10; N 4.05.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT776572A AT320614B (en) | 1972-09-11 | 1972-09-11 | Process for the production of new basic ethers and their acid addition salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU488399A3 true SU488399A3 (en) | 1975-10-15 |
Family
ID=3599260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1957933A SU488399A3 (en) | 1972-09-11 | 1973-07-31 | The method of obtaining derivatives diphenylaminopropane |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5229736B2 (en) |
| AT (1) | AT320614B (en) |
| CA (1) | CA986539A (en) |
| CH (1) | CH580567A5 (en) |
| CS (1) | CS164754B2 (en) |
| DD (1) | DD106032A1 (en) |
| ES (1) | ES416834A1 (en) |
| FI (1) | FI56825C (en) |
| HU (1) | HU165416B (en) |
| LU (1) | LU67864A1 (en) |
| PL (1) | PL84618B1 (en) |
| RO (1) | RO62912A (en) |
| SE (1) | SE398640B (en) |
| SU (1) | SU488399A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5491200A (en) * | 1977-12-28 | 1979-07-19 | Noboru Nakamura | Safety system for house or like |
-
1972
- 1972-09-11 AT AT776572A patent/AT320614B/en not_active IP Right Cessation
-
1973
- 1973-06-21 CS CS4464A patent/CS164754B2/cs unknown
- 1973-06-22 LU LU67864A patent/LU67864A1/xx unknown
- 1973-06-27 FI FI2048/73A patent/FI56825C/en active
- 1973-07-06 HU HUOE201A patent/HU165416B/hu unknown
- 1973-07-12 ES ES416834A patent/ES416834A1/en not_active Expired
- 1973-07-30 RO RO7300075653A patent/RO62912A/en unknown
- 1973-07-30 DD DD172607A patent/DD106032A1/xx unknown
- 1973-07-31 SE SE7310529A patent/SE398640B/en unknown
- 1973-07-31 JP JP48085550A patent/JPS5229736B2/ja not_active Expired
- 1973-07-31 CH CH1117873A patent/CH580567A5/en not_active IP Right Cessation
- 1973-07-31 SU SU1957933A patent/SU488399A3/en active
- 1973-09-06 CA CA180422A patent/CA986539A/en not_active Expired
- 1973-09-11 PL PL1973165149A patent/PL84618B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI56825C (en) | 1980-04-10 |
| PL84618B1 (en) | 1976-04-30 |
| CS164754B2 (en) | 1975-11-28 |
| LU67864A1 (en) | 1973-08-30 |
| SE7310529L (en) | 1974-03-12 |
| HU165416B (en) | 1974-08-28 |
| ES416834A1 (en) | 1976-02-16 |
| DD106032A1 (en) | 1974-05-20 |
| SE398640B (en) | 1978-01-09 |
| FI56825B (en) | 1979-12-31 |
| JPS4980051A (en) | 1974-08-02 |
| RO62912A (en) | 1977-12-15 |
| CH580567A5 (en) | 1976-10-15 |
| AT320614B (en) | 1975-02-25 |
| CA986539A (en) | 1976-03-30 |
| JPS5229736B2 (en) | 1977-08-03 |
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