SU507225A3 - Production method - propionyl-4-hydroxyproline or its salts - Google Patents
Production method - propionyl-4-hydroxyproline or its saltsInfo
- Publication number
- SU507225A3 SU507225A3 SU1972265A SU1972265A SU507225A3 SU 507225 A3 SU507225 A3 SU 507225A3 SU 1972265 A SU1972265 A SU 1972265A SU 1972265 A SU1972265 A SU 1972265A SU 507225 A3 SU507225 A3 SU 507225A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydroxyproline
- propionyl
- salts
- production method
- salt
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Description
СПОСОБ ПОЛУЧЕНИЯ L - N -ПРОПИОНИЛ-4-ОКСИПРОЛИНА METHOD OF OBTAINING L - N-PROPIONIL-4-OXIPROLINE
(54) ИЛИ ЕГО СОЛЕЙ(54) OR HIS SALTS
Изобретение относитс к способу по лучени нового ПРОИЗВОДНОГО; пролина, которое может найти применение в фармацевтической проквлиленности. Известен способ получени N-ацильиых производных взаимодействием амина с ангидридном карбоновой кислоты в рас творе той же кислоты. Использу известный способ примени тельно к Ъ -4-оксипролину, получают неописанный ранее L - N -пропионил4-оксипролин , обладающий иённными фар макологическими свойствами. Согласно изобретению предлагаетс способ получени L - N -пропионил-4оксипропилина , заключающийс в том, что L -4-оксипролин подвергают взаимодействию со смесью пропионового аИгидрида и пропионовой кислоты и целевой продукт выдел ют в виде основани металлической соли или соли с азотсосодержащим основанием. Процесс согласно изобретению обычно провод т при 25-80с. Целевой продукт может быть в случае необходимости очищен известными физическими методами, например хроматографией или перекристаллизацией, или химическими методами, например переведением в металлическую соль, которую сначала перекристаллизовывают , а затем при подкислении перевод т в основание. L - ТЧ -пропионил-4-оксипролин может быть превращен известными способАми в металлическую соль или соль азотсодержащего основани в подход щем растворителе, например спирте, эфире кетонах или воде. Образовавша с соль выпадает в осадок, который отфильтровывают или декантируют |п6сле концент-рировани раствора. В качестве оснований используют гидраты окисей щелочных или щелочноземельных металлов, аммиак или амины. Строение L - N -пропионил-4-оксипролина однозначно доказано ИК-и ЯМР спектрами. ll м е р. К смеси 110 г I. -4оксипролина и 400 мл пропионовой кислоты , нагретой до 50с, прибавл ют по капл м раствор 119,5 г пропионозото ангидрида в 100 мл пропионовой кислоты в течение 30 мин. Реакционную массу перемешивают 10 мин при 50с. Доб1авл ют 800 мл диизопропилового эфира , при этом выдел ют кристаллы продукта . Реакционную смесь охлаждают до 15 С Лприбавл ют еще 300 мл диизопропилового эфира. Кристаллический осадок отфильтровывают, промывают 600 мл диизспропилового эфира. Получают 129 г продукта ст. пл. 138 С. После перекристаллизации из 310 ьл ацетанитрила получают 118 rt -N п ропионил-4-оксипролина с т. пл. 139С,This invention relates to a process for producing a new DERIVATIVE; proline, which can be used in pharmaceutical fertility. A known method for producing N-acyl derivatives by reacting an amine with a carboxylic anhydride in a solution of the same acid. Using the known method applicable to b-4-hydroxyproline, L-N-propionyl-4-hydroxyproline, which has not been described previously, is obtained, which possesses macrophilic properties of headlights. According to the invention, a method for producing L-N-propionyl-4-oxypropylin is proposed, namely, L-4-hydroxyproline is reacted with a mixture of propionic aHydride and propionic acid and the target product is isolated as a base metal salt or salt with a nitrogen-containing base. The process according to the invention is usually carried out at 25-80 seconds. The desired product can, if necessary, be purified by known physical methods, for example by chromatography or recrystallization, or by chemical methods, for example by conversion into a metal salt, which is first recrystallized and then transferred to the base upon acidification. L-PM-propionyl-4-hydroxyproline can be converted by known methods to a metal salt or a salt of a nitrogen-containing base in a suitable solvent, for example, alcohol, ketone ester or water. The resulting salt precipitates, which is filtered or decanted | after concentration of the solution. The bases used are alkali or alkaline earth metal oxide hydrates, ammonia or amines. The structure of L - N-propionyl-4-hydroxyproline is unequivocally proven by IR and NMR spectra. ll merid. To a mixture of 110 g of I. -4-oxyproline and 400 ml of propionic acid heated to 50 s, a solution of 119.5 g of propionic acid anhydride in 100 ml of propionic acid is added dropwise over 30 minutes. The reaction mass is stirred for 10 min at 50 s. 800 ml of diisopropyl ether are added, and product crystals are isolated. The reaction mixture is cooled to 15 ° C. Another 300 ml of diisopropyl ether is added. The crystalline precipitate is filtered off, washed with 600 ml of diisopropyl ether. 129 g of product are obtained. square 138 C. After recrystallization from 310 ml of acetanitrile, 118 rt -N p-pionionyl-4-hydroxyproline with m.p. 139С,
io dtl i-U4 t l. 1, вода).io dtl i-U4 t l. 1, water).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7241639A FR2207702B1 (en) | 1972-11-23 | 1972-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU507225A3 true SU507225A3 (en) | 1976-03-15 |
Family
ID=9107588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1972265A SU507225A3 (en) | 1972-11-23 | 1973-11-22 | Production method - propionyl-4-hydroxyproline or its salts |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS504066A (en) |
| AR (1) | AR199319A1 (en) |
| AU (1) | AU473116B2 (en) |
| BE (1) | BE807684A (en) |
| CA (1) | CA1001635A (en) |
| CH (1) | CH576958A5 (en) |
| DD (1) | DD107455A5 (en) |
| DE (1) | DE2358470A1 (en) |
| ES (1) | ES420780A1 (en) |
| FR (1) | FR2207702B1 (en) |
| GB (1) | GB1397675A (en) |
| HU (1) | HU166917B (en) |
| IL (1) | IL43684A (en) |
| LU (1) | LU68846A1 (en) |
| NL (1) | NL7315685A (en) |
| OA (1) | OA04505A (en) |
| SE (1) | SE382453B (en) |
| SU (1) | SU507225A3 (en) |
| ZA (1) | ZA738874B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1281288C (en) * | 1984-11-05 | 1991-03-12 | Wilhelm Hoerrmann | Tumor therapy |
| JPS63218621A (en) * | 1987-03-09 | 1988-09-12 | Kazuoki Tsuchiya | Composition for prevention and remedy of obesity |
| WO2006046690A1 (en) * | 2004-10-28 | 2006-05-04 | Kyowa Hakko Kogyo Co., Ltd. | Composition for oral cavity |
-
1972
- 1972-11-23 FR FR7241639A patent/FR2207702B1/fr not_active Expired
-
1973
- 1973-11-08 OA OA55056A patent/OA04505A/en unknown
- 1973-11-15 NL NL7315685A patent/NL7315685A/xx unknown
- 1973-11-21 DD DD174787*A patent/DD107455A5/xx unknown
- 1973-11-21 AU AU62771/73A patent/AU473116B2/en not_active Expired
- 1973-11-21 AR AR251096A patent/AR199319A1/en active
- 1973-11-21 JP JP48131160A patent/JPS504066A/ja active Pending
- 1973-11-21 ZA ZA738874A patent/ZA738874B/en unknown
- 1973-11-21 HU HURO760A patent/HU166917B/hu unknown
- 1973-11-22 SU SU1972265A patent/SU507225A3/en active
- 1973-11-22 IL IL43684A patent/IL43684A/en unknown
- 1973-11-22 CH CH1648973A patent/CH576958A5/xx not_active IP Right Cessation
- 1973-11-22 LU LU68846A patent/LU68846A1/xx unknown
- 1973-11-22 GB GB5427473A patent/GB1397675A/en not_active Expired
- 1973-11-22 SE SE7315836A patent/SE382453B/en unknown
- 1973-11-22 CA CA186,521A patent/CA1001635A/en not_active Expired
- 1973-11-22 BE BE138064A patent/BE807684A/en unknown
- 1973-11-23 ES ES420780A patent/ES420780A1/en not_active Expired
- 1973-11-23 DE DE2358470A patent/DE2358470A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1001635A (en) | 1976-12-14 |
| CH576958A5 (en) | 1976-06-30 |
| GB1397675A (en) | 1975-06-18 |
| IL43684A (en) | 1976-06-30 |
| AR199319A1 (en) | 1974-08-23 |
| JPS504066A (en) | 1975-01-16 |
| ZA738874B (en) | 1974-10-30 |
| IL43684A0 (en) | 1974-03-14 |
| OA04505A (en) | 1980-03-30 |
| DD107455A5 (en) | 1974-08-05 |
| ES420780A1 (en) | 1976-04-01 |
| AU473116B2 (en) | 1976-06-10 |
| NL7315685A (en) | 1974-05-27 |
| FR2207702B1 (en) | 1975-11-28 |
| AU6277173A (en) | 1975-05-22 |
| FR2207702A1 (en) | 1974-06-21 |
| DE2358470A1 (en) | 1974-05-30 |
| BE807684A (en) | 1974-05-22 |
| LU68846A1 (en) | 1974-06-21 |
| SE382453B (en) | 1976-02-02 |
| HU166917B (en) | 1975-06-28 |
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