SU633473A3 - Способ получени производных пиперидина или их солей - Google Patents
Способ получени производных пиперидина или их солейInfo
- Publication number
- SU633473A3 SU633473A3 SU762415648A SU2415648A SU633473A3 SU 633473 A3 SU633473 A3 SU 633473A3 SU 762415648 A SU762415648 A SU 762415648A SU 2415648 A SU2415648 A SU 2415648A SU 633473 A3 SU633473 A3 SU 633473A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- piperidine
- salts
- piperidine derivatives
- salt
- general formula
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
63 те, содержащем гапоидоводород, предпочтительно в метанольном растворе хлористого водорода, или а уксуснокислом растворе в присутствии катализатора из благородного металла, например платинового катализатора, предпочтительно окиси платины , при 1О-5О С, п1редпочтительно при комнатной температуре, и давлени х водорода О S-S атм, предпочтительно при атмосферном давлении. П р и мер. Получение Ф-Феноксиметилнипервдина . Смесь, состо щую из 18,5 г (0,1 мол ) 4-феноксимётилпириднна, 250 мл метанола , 26О мл 3 и, метанольного раствора хлористого водорода и 2 г окиси платины встр хивают при комнатной температуре под давлением водорода 1 атм. После добавлени рассчитанного количества водорода катализатор отфильтровывают, фильт рат упаривают в вакууме и остаток перекристаппизовывают из этанола. Получают 12,Ог гидрохлорида 4-феноксиметнлпипери лина (53% от теории) с т.пл. 218-219 С, Свободное основание Получают обработкой вооным раствором гидроокиси натри . Используемый в качестве исходного соединени 4-феноксиметилпиридин получают следующим образом. 3I Смесь, состо щую из 37,0 г (0,25 мол ) гидрох-лорида .4-оксиметилпиридина и 15О мл тионилхлорида, кип т т 2 ч с обратным холодильником После охлаждени добавл ют 250 мл бензола, фильтруют и промывают осадок бензолом. Получают 32,0 г 4-хлорметилпир1Щина-гидрохлорида (76/о от теории) с ТоПЛ. 171-172°С, К раствору 3,5 г (0,15 мол ) натри в 1ОО мл метанола добавл ют 14,1 г (0,15 мол ) фенола, упаривают, смешивают с 50 мл N , N-диметилформамида и 8,2 г (0,05 мол ) гидрохлорида 4-хлорметилпиридина и нагревают 2О ч при . После охлаждени разбавл ют эфиром , промывают разбавленной гидроокисью натри и водой, высушивают над сульфатом натри , упаривают и перегонжот в вакууме. Получают 8,2 г 4 -феноксиметилпиридина (88% от теории) с т. пло 115-177 С. Аналогичным образом получают 4-(2-нитрофеноксиметил )-пиперидин с т. пл. при 0,О1 мм jfxr. ст. 13О-132 С. В таблице приведен р д производных пиперидина, полученных предлагаемым способом .
4-(2-Бромфеноксиметил)-пиперидин 4-( 2-Хлорфеноксиметил)-пиперидин 4-( 3-Хлорфеноксиметил)-пиперидин 4-(4-Хлорфеноксиметил)-пиперидин 4-( 2-Фторфеноксиметил)-пиперидин 4-(4-Фторфеноксиметил)-пиперидин 4-( 2-Метоксифеноксиметил)-пиперидин 4-( З-Метоксифеноксиметил)-пиперидин 4-(4-Метоксифеиоксиметил)пиперидин 4-( 2-Бутоксифеноксиметил)-пиперидин 4-( 2-Метнлфеноксиметил)-пиперидин 4-(3-Метипфеноксиметил)-пиперидин 4-(4-Метилфеноксиметил)-пиперидин
48-5О
35-37
Claims (1)
- 42-44 Формула изобретени Способ получени производных пиперидина обшей формулы ,-- О где К - водород, галоген, низша алкил на группа, низша алкоксигруппа, или ни рогруппа, или их солей, отличающийс тем, что феноксиметильное производное пиридина обшей формулы Ц 6н« - о где R имеет вышеуказанное значение, или его соль, образованную присоединением кислоты, подвергают каталитическому гидрированию и целевой продукт выдел ют а виде основани или соли или перевод т соответственно в соль нли в основание . Источники информации, прин тые во вниманне при экспертизе: 1. Эльдерфилд, Гетероциклические соединени , М., 1953, т. 1, с. 49О.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752549999 DE2549999A1 (de) | 1975-11-07 | 1975-11-07 | Piperidin-derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU633473A3 true SU633473A3 (ru) | 1978-11-15 |
Family
ID=5961166
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415648A SU633473A3 (ru) | 1975-11-07 | 1976-11-02 | Способ получени производных пиперидина или их солей |
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772534004A SU867298A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
| SU772534003A SU662009A3 (ru) | 1975-11-07 | 1977-10-21 | Способ получени производных пиперидина или их солей |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4243807A (ru) |
| JP (1) | JPS6055509B2 (ru) |
| AT (1) | AT352726B (ru) |
| BE (1) | BE847973A (ru) |
| CA (1) | CA1077942A (ru) |
| CH (3) | CH624102A5 (ru) |
| DD (1) | DD126942A5 (ru) |
| DE (1) | DE2549999A1 (ru) |
| DK (1) | DK494876A (ru) |
| FI (1) | FI763148A (ru) |
| FR (1) | FR2330678A1 (ru) |
| GB (1) | GB1502050A (ru) |
| HU (1) | HU171237B (ru) |
| IE (1) | IE43866B1 (ru) |
| IT (1) | IT1063618B (ru) |
| LU (1) | LU76141A1 (ru) |
| NL (1) | NL7612286A (ru) |
| SE (1) | SE7612234L (ru) |
| SU (3) | SU633473A3 (ru) |
| ZA (1) | ZA766381B (ru) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA848275B (en) * | 1983-12-28 | 1985-08-28 | Degussa | New piridine-2-ethers or pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring |
| US4556664A (en) * | 1984-03-13 | 1985-12-03 | Gunnar A. K. Aberg | Method and composition for the treatment of cardiac arrhythmias |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| US5231184A (en) * | 1987-11-23 | 1993-07-27 | Janssen Pharmaceutica N.V. | Pridazinamine derivatives |
| US4822778A (en) * | 1988-01-19 | 1989-04-18 | Gunnar Aberg | Membrane stabilizing phenoxy-piperidine compounds and pharmaceutical compositions employing such compounds |
| US5109002A (en) * | 1989-09-08 | 1992-04-28 | Du Pont Merck Pharmaceutical Company | Antipsychotic 1-cycloalkylpiperidines |
| NZ239846A (en) * | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| US5264420A (en) * | 1990-09-27 | 1993-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| IL99537A (en) * | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical preparations containing them |
| FR2667317B1 (fr) * | 1990-10-02 | 1992-12-04 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| HUT68769A (en) * | 1991-05-07 | 1995-07-28 | Merck & Co Inc | FIBRINOGéN RECEPTOR ANTAGONIST COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM AS EFFECTIVE SUBSTANCE |
| US5321034A (en) * | 1991-05-07 | 1994-06-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5389631A (en) * | 1991-10-29 | 1995-02-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5272158A (en) * | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5416099A (en) * | 1991-10-29 | 1995-05-16 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5559127A (en) * | 1992-10-14 | 1996-09-24 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5358956A (en) * | 1992-10-14 | 1994-10-25 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| EP0673247A4 (en) * | 1992-12-01 | 1996-05-01 | Merck & Co Inc | FIBRINOGEN RECEPTOR ANTAGONISTS. |
| US5441952A (en) * | 1993-04-05 | 1995-08-15 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5397791A (en) * | 1993-08-09 | 1995-03-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5719144A (en) * | 1995-02-22 | 1998-02-17 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| WO1997011939A1 (fr) * | 1995-09-28 | 1997-04-03 | Kaken Pharmaceutical Co., Ltd. | Procede d'elaboration de 4-methylenepiperidines |
| US5789421A (en) * | 1995-10-26 | 1998-08-04 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5780480A (en) * | 1996-02-28 | 1998-07-14 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5889023A (en) * | 1996-05-10 | 1999-03-30 | Merck & Co., Inc. | Fibrinogen receptor antagonist |
| US5981584A (en) * | 1997-02-06 | 1999-11-09 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| US7888386B2 (en) * | 2008-07-24 | 2011-02-15 | Theravance, Inc. | 3-(phenoxyphenylmethyl)pyrrolidine compounds |
| DK2358674T3 (da) | 2008-11-14 | 2013-04-08 | Theravance Inc | Fremgangsmåde til fremstilling af 4-[2-(2-fluorphenoxymethyl)phenyl]piperidinforbindelser |
| WO2010120910A1 (en) * | 2009-04-15 | 2010-10-21 | Theravance, Inc. | 3-(phenoxypyrrolidin-3-yl-methyl)heteroaryl, 3-(phenylpyrrolidin-3-ylmethoxy)heteroaryl, and 3-(heteroarylpyrrolidin-3-ylmethoxy)heteroaryl compounds |
| MX2012000685A (es) * | 2009-07-13 | 2012-02-28 | Theravance Inc | Compuesto de 3-fenoximetilpirrolidina. |
| ES2495366T3 (es) | 2009-07-21 | 2014-09-17 | Theravance, Inc. | Compuestos de 3-fenoximetilpirrolidina |
| EP2523945A1 (en) * | 2010-01-11 | 2012-11-21 | Theravance, Inc. | 1 - (2 - phenoxymethylphenyl) piperazine compounds as serotonin and norepinephrine reuptake inhibitors |
| ES2543064T3 (es) * | 2010-03-22 | 2015-08-14 | Theravance Biopharma R&D Ip, Llc | Compuestos de 1-(2-fenoximetilheteroaril)piperidina y piperazina |
| WO2012051103A1 (en) | 2010-10-11 | 2012-04-19 | Theravance, Inc. | Serotonin reuptake inhibitors |
| WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
| DE2245061A1 (de) * | 1972-09-14 | 1974-03-28 | Boehringer Mannheim Gmbh | Derivate des adenins |
| DE2401254A1 (de) * | 1974-01-11 | 1975-11-27 | Boehringer Mannheim Gmbh | Neue derivate von n hoch 6-substituierten adeninen |
| DE2550000A1 (de) * | 1975-11-07 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue purin-derivate und verfahren zu ihrer herstellung |
-
1975
- 1975-11-07 DE DE19752549999 patent/DE2549999A1/de active Granted
-
1976
- 1976-10-25 ZA ZA766381A patent/ZA766381B/xx unknown
- 1976-10-28 CA CA264,608A patent/CA1077942A/en not_active Expired
- 1976-10-29 IE IE2394/76A patent/IE43866B1/en unknown
- 1976-11-01 HU HU76BO00001639A patent/HU171237B/hu not_active IP Right Cessation
- 1976-11-01 US US05/737,518 patent/US4243807A/en not_active Expired - Lifetime
- 1976-11-02 DK DK494876A patent/DK494876A/da not_active Application Discontinuation
- 1976-11-02 SU SU762415648A patent/SU633473A3/ru active
- 1976-11-03 CH CH1385576A patent/CH624102A5/de not_active IP Right Cessation
- 1976-11-03 SE SE7612234A patent/SE7612234L/xx not_active Application Discontinuation
- 1976-11-03 FI FI763148A patent/FI763148A/fi not_active Application Discontinuation
- 1976-11-04 DD DD195610A patent/DD126942A5/xx unknown
- 1976-11-04 BE BE172068A patent/BE847973A/xx not_active IP Right Cessation
- 1976-11-04 GB GB45916/76A patent/GB1502050A/en not_active Expired
- 1976-11-05 LU LU76141A patent/LU76141A1/xx unknown
- 1976-11-05 NL NL7612286A patent/NL7612286A/xx not_active Application Discontinuation
- 1976-11-05 JP JP51133139A patent/JPS6055509B2/ja not_active Expired
- 1976-11-05 IT IT29083/76A patent/IT1063618B/it active
- 1976-11-05 AT AT823776A patent/AT352726B/de not_active IP Right Cessation
- 1976-11-05 FR FR7633389A patent/FR2330678A1/fr active Granted
-
1977
- 1977-10-21 SU SU772534004A patent/SU867298A3/ru active
- 1977-10-21 SU SU772534003A patent/SU662009A3/ru active
-
1980
- 1980-10-03 CH CH742480A patent/CH627166A5/de not_active IP Right Cessation
- 1980-10-03 CH CH742380A patent/CH625788A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2549999A1 (de) | 1977-05-12 |
| DE2549999C2 (ru) | 1989-01-26 |
| AT352726B (de) | 1979-10-10 |
| ZA766381B (en) | 1977-10-26 |
| SU662009A3 (ru) | 1979-05-05 |
| CH627166A5 (ru) | 1981-12-31 |
| HU171237B (hu) | 1977-12-28 |
| ATA823776A (de) | 1979-03-15 |
| DK494876A (da) | 1977-05-08 |
| DD126942A5 (ru) | 1977-08-24 |
| IE43866L (en) | 1977-05-07 |
| CH624102A5 (ru) | 1981-07-15 |
| CA1077942A (en) | 1980-05-20 |
| SU867298A3 (ru) | 1981-09-23 |
| FI763148A (ru) | 1977-05-08 |
| NL7612286A (nl) | 1977-05-10 |
| LU76141A1 (ru) | 1977-05-18 |
| SE7612234L (sv) | 1977-05-07 |
| CH625788A5 (ru) | 1981-10-15 |
| BE847973A (fr) | 1977-05-04 |
| JPS5259163A (en) | 1977-05-16 |
| FR2330678B1 (ru) | 1980-11-07 |
| JPS6055509B2 (ja) | 1985-12-05 |
| IT1063618B (it) | 1985-02-11 |
| FR2330678A1 (fr) | 1977-06-03 |
| GB1502050A (en) | 1978-02-22 |
| IE43866B1 (en) | 1981-06-17 |
| US4243807A (en) | 1981-01-06 |
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