SU1272986A3 - Способ получени гидрохлорида 1-гексаметиленимино-3-/2,6-диметиланилино/-пропанола-2 - Google Patents
Способ получени гидрохлорида 1-гексаметиленимино-3-/2,6-диметиланилино/-пропанола-2 Download PDFInfo
- Publication number
- SU1272986A3 SU1272986A3 SU833651388A SU3651388A SU1272986A3 SU 1272986 A3 SU1272986 A3 SU 1272986A3 SU 833651388 A SU833651388 A SU 833651388A SU 3651388 A SU3651388 A SU 3651388A SU 1272986 A3 SU1272986 A3 SU 1272986A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compounds
- dimethylanilino
- propanol
- preparation
- lower alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 4
- -1 cyclic imines Chemical class 0.000 claims abstract description 6
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 206010061592 cardiac fibrillation Diseases 0.000 description 3
- 230000002600 fibrillogenic effect Effects 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241001585714 Nola Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- GCGYREODZIZPLJ-UHFFFAOYSA-N azepan-1-ium;chloride Chemical compound Cl.C1CCCNCC1 GCGYREODZIZPLJ-UHFFFAOYSA-N 0.000 description 1
- 230000004397 blinking Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Изобретение касаетс замещенных аминоспиртов, в частности гид-рохлори- да 1-гексаметиленимино-3-
Description
сн 12 Изобретение относитс к области получени нового химического соединени , а именно гидрохлорида-1-гексаметиленимино-3- (2,6-диметиланилино)пропанола-2 , обладающего антиаритмичесКИМ действием. Целью изобретени вл етс разработка , ria основе известного метода, способа получени нового соединени , обладающего ценным фармакологическим свойством. Пример 1. Получение 1-гексаметиленимино-3- (2,6-диметиланилино)пропанола-2 . Смесь 21,37 г (0,1 моль) 1-ксилидино-З-хлорпропанола-2 и 19,83 г (0,2 моль) гексаметиленимина медленн нагревают 1 ч при 140 С. Полученный таким образом раствор разбавл ют 40 мл этилацетата и вьшавший гидрохлорид гексаметиленимина отфильтровы . вают.,Из фильтрата осаждают 50 мл этанола, содержащего 15% сол ной кис лоты, гидрохлорид указанного соединени . Получают 24,6 г гидрохлорида. Выкод 89,2%, т.пл. 221-223 С (из эта нола). Вычислено, %: С 58,45 Н 8,66 N 8,0 Cf 20,30. С|7 H28N20-2HCr (мол. вес. 349,36) 86 Найдено; %: С 58,24 Н 8,69 N 7,93 Сг 20,26. Н-ПМР (CDCf,): 1,5-1,83 (m4,. -СН2-(СНг)4-СИ2); 2,5 (s 6, СН,); 2,8-3,7 (m 8, -СН); 4,65 (s 1, ОН), 4,45-4,85 (m 1, -СН-); 6,9 (s 3,АгН). Эффективность полученного соединени доказана, с помощью следующих тестов . Опыт провод т на кошках (вес 2,23 ,5 кг) при наркозе хлоралозеуретаном (50/30 мг/кг i.v.) путем наблюдени изменени минимальной силы тока, необходимой дл того, чтобы вызвать мерцающую фибрилл цию предсерди и желудочка сердца (так называема наполненна фибрилл ци ), по методу Сцекереса. Терапевтический индекс, счита на антиаритмическое действие, рассчитывают на основании отношени LD . LD50 представл ет собой дозу, котора вызывает 50%-ную смерность крыс, ED 50 дозу дл кошек, вызывающую 50%-ное увеличение наполненной фибрилл ции . Значение LDJQ определ ют на мужских особ х крыс (вес 180-220 г) по методу Литхфлида и Вилкоксона. Полученные результаты приведены в табл. 1. Таблица 1
Из антиаритмической активности, определенной с помощью техники наполненой фибрилл ции (ED , мг/кг, i.v.), рассчитывают относительную активность наркотизированных кошек.
Значение LDjp , i. v. и p.о. определ ют на крысах.
Приведенные результаты показывают,
что антиаритмичное действие новых соединений значительно превосходит такое же действие известного хинидина как в предсердии, так и в желудочкесердца .
Индексы, отнесенные к антиаритмической активности у желудочка сердца, меньше, чем у предсерди . Однако частное отношение р. о. .v. ED у соединени до примеру 5 приблизительно в 1,4 раза больше, чем у хинидина .
Соединени по примерам в вьщеленных препаратах сердца кроликов антиаритмического действи по методам сердечно-электро-физиологическим соответственно снижают спонтанную частоту в правом предсердии, они повышают электрический порог раздражени , удлин ют рефлекторное эффективное врем и продолжительность раздражени . Результаты приведены в табл. 2 в виде процентов основного значени .
Предлагаемые соединени у наркоти-О зированных нембуталом (35 мг/кг, i.v.) собак нормализуют артериальное кров ное давление при дозе 0,5-2 мг/ /кг, кроме.того, они снижают коронарную сопротивл емость, улучшают окси- f5 генирование сердечной мышцы, повышают переток крови в артерию.
Таблнца2
Claims (1)
- Формула изобретениСпособ получени гидрохлорида 1-гексаметиленимино-З-(2,6-диметиланилино )пропанола-2, о т л и ч а ющ и и с тем, что 1-ксилидино-З- . -хлорпропанола-2 подвергают взаимодействию с гексаметиленими ном .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU813308A HU183721B (en) | 1981-11-06 | 1981-11-06 | Process for producing new cyclic imine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1272986A3 true SU1272986A3 (ru) | 1986-11-23 |
Family
ID=10963511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833651388A SU1272986A3 (ru) | 1981-11-06 | 1983-10-13 | Способ получени гидрохлорида 1-гексаметиленимино-3-/2,6-диметиланилино/-пропанола-2 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4530923A (ru) |
| JP (1) | JPS5885879A (ru) |
| AT (1) | AT382371B (ru) |
| BE (1) | BE894889A (ru) |
| CA (1) | CA1197241A (ru) |
| CH (1) | CH652399A5 (ru) |
| DD (1) | DD206992A5 (ru) |
| DE (1) | DE3240908A1 (ru) |
| DK (1) | DK494282A (ru) |
| ES (1) | ES8404328A1 (ru) |
| FI (1) | FI77241C (ru) |
| FR (1) | FR2516080B1 (ru) |
| GB (1) | GB2111485B (ru) |
| HU (1) | HU183721B (ru) |
| IT (1) | IT1218328B (ru) |
| NL (1) | NL8204275A (ru) |
| SE (1) | SE8206230L (ru) |
| SU (1) | SU1272986A3 (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES513980A0 (es) * | 1982-07-14 | 1983-04-16 | Medichem Sa | Un procedimiento para la obtencion de la 2-(hexahidroazepin)-n-(2,6-dimetilfenil)acetamida. |
| AU2002323570A1 (en) * | 2001-08-30 | 2003-03-10 | Chemocentryx, Inc. | Bicyclic compounds as inhibitors of chemokine binding to us28 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1552758A (ru) * | 1963-07-01 | 1969-01-10 | ||
| FR6571M (ru) * | 1967-08-03 | 1968-12-23 | ||
| CA956632A (en) * | 1969-05-16 | 1974-10-22 | Yoshitomi Pharmaceutical Industries | Phenoxy-aminopropanol derivatives |
| BE790133A (fr) * | 1971-10-16 | 1973-04-16 | Basf Ag | Nouveaux derives de la trimethylhydroquinone, leur preparation et leursutilisations therapeutiques |
| DE2300543A1 (de) * | 1973-01-08 | 1974-07-11 | Basf Ag 6700 Ludwigshafen | Neue derivate des trimethylphenols und verfahren zu ihrer herstellung |
| JPS50106947A (ru) * | 1974-02-06 | 1975-08-22 | ||
| CS195321B2 (en) * | 1975-12-23 | 1980-01-31 | Ciba Geigy Ag | Plant growth suppressing agents |
| US4191765A (en) * | 1976-05-25 | 1980-03-04 | Hoechst Aktiengesellschaft | 1-Aryloxy-2-hydroxy-3-aminopropanes |
| DE2915250A1 (de) * | 1979-04-14 | 1980-10-30 | Basf Ag | Salze von alpha -aminoacetaniliden |
| DE3004360A1 (de) * | 1980-02-06 | 1981-09-24 | Chem. pharmaz. Fabrik Dr. Hermann Thiemann GmbH, 4670 Lünen | 1,3-dicarbonyl-2-hydroxy- und -alkoxy-5-(amino-acetamido)-benzolverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
-
1981
- 1981-11-06 HU HU813308A patent/HU183721B/hu not_active IP Right Cessation
-
1982
- 1982-10-12 FI FI823470A patent/FI77241C/fi not_active IP Right Cessation
- 1982-10-20 US US06/435,493 patent/US4530923A/en not_active Expired - Fee Related
- 1982-11-02 SE SE8206230A patent/SE8206230L/xx not_active Application Discontinuation
- 1982-11-02 ES ES517049A patent/ES8404328A1/es not_active Expired
- 1982-11-03 BE BE1/10630A patent/BE894889A/fr not_active IP Right Cessation
- 1982-11-04 FR FR8218475A patent/FR2516080B1/fr not_active Expired
- 1982-11-04 NL NL8204275A patent/NL8204275A/nl not_active Application Discontinuation
- 1982-11-05 CH CH6448/82A patent/CH652399A5/de not_active IP Right Cessation
- 1982-11-05 AT AT0403982A patent/AT382371B/de not_active IP Right Cessation
- 1982-11-05 CA CA000415034A patent/CA1197241A/en not_active Expired
- 1982-11-05 GB GB08231604A patent/GB2111485B/en not_active Expired
- 1982-11-05 DE DE19823240908 patent/DE3240908A1/de not_active Withdrawn
- 1982-11-05 IT IT8224085A patent/IT1218328B/it active
- 1982-11-05 DK DK494282A patent/DK494282A/da not_active Application Discontinuation
- 1982-11-05 DD DD82244611A patent/DD206992A5/de unknown
- 1982-11-06 JP JP57193985A patent/JPS5885879A/ja active Pending
-
1983
- 1983-10-13 SU SU833651388A patent/SU1272986A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Вейганд - Хильгетаг. Методы эксперимента в органической химии.- М.: Хими , 1968, с. 413. * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8204275A (nl) | 1983-06-01 |
| US4530923A (en) | 1985-07-23 |
| FI823470A0 (fi) | 1982-10-12 |
| SE8206230D0 (sv) | 1982-11-02 |
| GB2111485B (en) | 1985-07-17 |
| DD206992A5 (de) | 1984-02-15 |
| IT8224085A0 (it) | 1982-11-05 |
| JPS5885879A (ja) | 1983-05-23 |
| ATA403982A (de) | 1986-07-15 |
| CA1197241A (en) | 1985-11-26 |
| IT1218328B (it) | 1990-04-12 |
| GB2111485A (en) | 1983-07-06 |
| SE8206230L (sv) | 1983-05-07 |
| HU183721B (en) | 1984-05-28 |
| AT382371B (de) | 1987-02-25 |
| FR2516080B1 (fr) | 1985-11-22 |
| BE894889A (fr) | 1983-05-03 |
| FI77241B (fi) | 1988-10-31 |
| DK494282A (da) | 1983-05-07 |
| ES517049A0 (es) | 1984-05-01 |
| FR2516080A1 (fr) | 1983-05-13 |
| FI823470L (fi) | 1983-05-07 |
| FI77241C (fi) | 1989-02-10 |
| ES8404328A1 (es) | 1984-05-01 |
| CH652399A5 (de) | 1985-11-15 |
| DE3240908A1 (de) | 1983-05-19 |
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