SU580834A3 - Способ получени производных простагландина - Google Patents
Способ получени производных простагландинаInfo
- Publication number
- SU580834A3 SU580834A3 SU7301911353A SU1911353A SU580834A3 SU 580834 A3 SU580834 A3 SU 580834A3 SU 7301911353 A SU7301911353 A SU 7301911353A SU 1911353 A SU1911353 A SU 1911353A SU 580834 A3 SU580834 A3 SU 580834A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- tetrahydropyranyl
- mixture
- ether
- multiplets
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- -1 acetoxycyclopentyl Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000004071 biological effect Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 239000000543 intermediate Substances 0.000 claims 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims 2
- 150000003180 prostaglandins Chemical class 0.000 claims 2
- 238000001228 spectrum Methods 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- MPRWIVBRDAXEAF-UHFFFAOYSA-N acetyloxy ethaneperoxoate Chemical compound CC(=O)OOOC(C)=O MPRWIVBRDAXEAF-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical class CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000008241 heterogeneous mixture Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000012047 saturated solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
Claims (4)
- Изобретение относитс к способу по лучени новых, не описанных в литера туре соединений - производных проста гландина, которые могут быть использованы в качестве промежуточных продуктов при синтезе простагландинов, обладающих биологической активностью В патентной и технической литерату ре широко, описано получение алканов из алкенов каталитическим гидрированием l3 . Использование известной реакции в данном случае приводит к получению новых, не описанных в литературе соединений общей формулы 1 О 0-C-Ra , Хх-х.Х хСООВ 3 в,о снгон где Т,-2-тетрагидропиранилгруппа, R 2 каждый - алкил с 1-4 атомами углерода. Целью изобретени вл етс получение новых промежуточных соединений, которые могут быть использованы в син тезе, простагландинов, облгщающих вы сокой биологической активностью. Предлагаемый способ получени соединений формулы 1 заключаетс в том, что соединение общей формулы П CHjOCHjCgH, гдеТ., Rj 3 имеют указанные значени , подвергают гидрированию в при сутствии паллади на угле в качестве катализатора и уксусной кислоты в среде этанола при комнатной температуре. Пример. Смесь I,i8 г (0,54 ммол ) метилового эфира7- 2-/3-бензилоксиметил-3-оС- (тетрагидропиранил-2гокси ) -5-ос -оксициклопентил- -с43-ЦИС5-гептеновой кислоты, 5 мл пиридина и 0,736 мл (7,78 ммол ) уксусного ангидрида перемешивают в течение ночи при 50°С в атмосфере азота. Смесь затем охлаждают до комнатной температуры, разбавл ют 75 мл эфира. Эфирный раствор один раз промывают водой и три раза - насыщенным раствором сульфата меди, сушат над безводным сульфатрм магни , упаривают и получают i ,6 р ( выход 93,5%) бесцветного масл нистог метилового эфира 7- 2-/i-бенэилоксиметил-З-оС - (тетрагидропиранил-2-окси -S-ok -ацетоксициклопентил-1-oi - -цйс -гептеновой кислоты, Спектры.. ИК(СНС1з) - 1750 скГ эфирные карбонилы ЯМР(С13С1 : 7,30 & синглет5Н ароматические 5.51- 5,235 мультиплет 2Н олефино5 ,22 - 5,23d мультиплет 1Н -СН-О-Ас 4.52в синглет 2Н -СЕ,-О3 ,бЗдсингпет SH-O-CHj ,67 - 3,205 мультиплеты 8Н - О - С и-0-CHt 2,068-сииглет ЗН - ССН 2,55 - 1,22 5мультиплеты 1бН осталь ные протоны. П р и м е р
- 2. Гетерогенную смесь 1,53 (3,14 ммол ) полученного в приме ре 1 ацетоксиэфира, 305 мг 5% паллади на угле, 15,3 мл смеси абсолютный этанол:лед на уксусна кислота перемешивают при комнатной температуре в атмосфере (одной) водорода в течение . 48 ч. Смесь затем отфильтровывают че)еэ цолит 545, фильтрат упаривают , получают 1,10 г (выход 87,5%) бес цветного масл нистого метилового эфира 7- 2- /3 -оксиметил-З-ой. -тетрагидропиранил-2-окси- (-5- ot.r ацетоксициклопентил )-1-ci-J-гептеновой кислоты. Спектры: ; ИК (СНСи : 1750 см эфирные ке.рбоиилы ЯМР(CDClg): 5,23 - 4,92 ij мультиплет 1Н - СН ОЛс 4,83 - 4,46 мультиплеты 1Н - О -СН-О 3,65 в синглет ЗН-О-СН, 4,32 - 3,18д мультиплеты 7Н - О -СН И -О- ,06 - 2, 70 широкий синглет 1Н -ОН 2,04 5синглрт ЗН - 9 2,58 - 1,00 мультиплеты 2ОН ocтaл ные протоны. Пример
- 3.Повтор ют примеры 1 2,-заменив дигидропиран из примера соответствующим количеством димети опропиЛсилила. П р и м е р
- 4. Повтор ют примеры 1 2, заменив дигидропиран из примера дигидрофураном. Формула изобретени Способ получени производных простаандина общей формулы I О-С-Йа ,х-чХ« 0« , HiO CHzOH где Rj- 2-тетрагидропиранилгруппа, Рд и каждый - алкил а 1-4 атомауглерода , отличающийс м, что соединение общей формулы и , i CHjOCBiCgHj где j и - имеют указанные знаени , подвергают гидрированию в приутствии паллади на угле в качестве атализатора и уксусной кислоты в срее этанола при комнатнойчтемпературе. Источники информации, ггоин тые во нимание при экспертизе: 1.Бюлер к, Пирсон д., Органические М,(1970) ч.I.e.19-20, интезы.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US244882A US3887587A (en) | 1972-04-17 | 1972-04-17 | Synthesis of prostaglandins of the one-series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU580834A3 true SU580834A3 (ru) | 1977-11-15 |
Family
ID=22924496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7301911353A SU580834A3 (ru) | 1972-04-17 | 1973-04-16 | Способ получени производных простагландина |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3887587A (ru) |
| JP (1) | JPS5710104B2 (ru) |
| AR (2) | AR197135A1 (ru) |
| AT (1) | AT336809B (ru) |
| AU (1) | AU470252B2 (ru) |
| BE (1) | BE798316A (ru) |
| CA (1) | CA999579A (ru) |
| CH (2) | CH578497A5 (ru) |
| DE (1) | DE2319017C3 (ru) |
| ES (2) | ES413786A1 (ru) |
| FR (3) | FR2183711B1 (ru) |
| GB (4) | GB1424416A (ru) |
| IE (2) | IE37495B1 (ru) |
| NL (1) | NL160250C (ru) |
| PL (2) | PL103097B1 (ru) |
| SE (4) | SE416543B (ru) |
| SU (1) | SU580834A3 (ru) |
| YU (1) | YU36924B (ru) |
| ZA (1) | ZA732385B (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4243595A (en) * | 1972-07-13 | 1981-01-06 | Pfizer Inc. | 15-Substituted-omega-pentanorprostaglandins |
| GB1432950A (en) * | 1972-11-10 | 1976-04-22 | Ici Ltd | Cyclopentane aldehydes as chemical intermediates |
| US4737590A (en) * | 1973-04-27 | 1988-04-12 | American Cyanamid Company | Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones |
| US4012431A (en) * | 1973-05-21 | 1977-03-15 | The Upjohn Company | Process for preparing 5-oxa PGF1.sub.α -type compounds |
| US4060540A (en) * | 1975-09-18 | 1977-11-29 | American Cyanamid Company | Novel 3-triphenylmethoxy-1-alkynes, 3-triphenyl-methoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates |
| US4039574A (en) * | 1975-09-25 | 1977-08-02 | American Cyanamid Company | 13-Hydroxy-15-deoxy-prostaglandins |
| US4219483A (en) * | 1978-09-11 | 1980-08-26 | Pfizer Inc. | 4-Pyrone prostaglandin antagonists |
| JPH0964603A (ja) * | 1995-08-26 | 1997-03-07 | Nec Corp | 温度補償型位相遅延回路 |
| CN103570599B (zh) * | 2013-11-11 | 2015-05-06 | 陕西大生制药科技有限公司 | 前列腺素a1的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA959485A (en) * | 1970-05-04 | 1974-12-17 | Gordon L. Bundy | 15-alkyl prostaglandins |
| US3736335A (en) * | 1970-06-22 | 1973-05-29 | Merck & Co Inc | Prostaglandins and methods of making same |
| DE2166721A1 (de) * | 1970-09-11 | 1975-05-15 | Upjohn Co | Prostansaeurederivate und deren herstellung |
| CA951723A (en) * | 1970-09-19 | 1974-07-23 | Takashi Yusa | Prostaglandin derivatives and process for the preparation thereof |
| GB1356581A (en) * | 1970-10-09 | 1974-06-12 | Ici Ltd | Cyclopentane derivatives |
-
1972
- 1972-04-17 US US244882A patent/US3887587A/en not_active Expired - Lifetime
-
1973
- 1973-04-02 GB GB119575A patent/GB1424416A/en not_active Expired
- 1973-04-02 GB GB119475A patent/GB1424415A/en not_active Expired
- 1973-04-02 SE SE7304635A patent/SE416543B/xx unknown
- 1973-04-02 GB GB1576773A patent/GB1424414A/en not_active Expired
- 1973-04-02 GB GB184675A patent/GB1424417A/en not_active Expired
- 1973-04-04 IE IE530/73A patent/IE37495B1/xx unknown
- 1973-04-04 IE IE850/76A patent/IE37496B1/xx unknown
- 1973-04-04 CA CA167,967A patent/CA999579A/en not_active Expired
- 1973-04-05 ZA ZA732385A patent/ZA732385B/xx unknown
- 1973-04-09 AU AU54282/73A patent/AU470252B2/en not_active Expired
- 1973-04-14 DE DE2319017A patent/DE2319017C3/de not_active Expired
- 1973-04-16 ES ES413786A patent/ES413786A1/es not_active Expired
- 1973-04-16 AR AR247566A patent/AR197135A1/es active
- 1973-04-16 SU SU7301911353A patent/SU580834A3/ru active
- 1973-04-16 NL NL7305292.A patent/NL160250C/xx not_active IP Right Cessation
- 1973-04-17 YU YU1033/73A patent/YU36924B/xx unknown
- 1973-04-17 FR FR7313904A patent/FR2183711B1/fr not_active Expired
- 1973-04-17 AT AT341273A patent/AT336809B/de not_active IP Right Cessation
- 1973-04-17 CH CH770075A patent/CH578497A5/xx not_active IP Right Cessation
- 1973-04-17 JP JP4276473A patent/JPS5710104B2/ja not_active Expired
- 1973-04-17 BE BE1004973A patent/BE798316A/xx not_active IP Right Cessation
- 1973-04-17 PL PL1973196152A patent/PL103097B1/pl not_active IP Right Cessation
- 1973-04-17 PL PL1973161967A patent/PL99374B1/pl unknown
- 1973-04-17 CH CH554573A patent/CH568264A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR252306A patent/AR204713A1/es active
-
1975
- 1975-09-24 FR FR7529281A patent/FR2275473A1/fr active Granted
- 1975-09-24 FR FR7529282A patent/FR2275453A1/fr active Granted
-
1976
- 1976-01-07 ES ES444110A patent/ES444110A1/es not_active Expired
- 1976-08-12 SE SE7609048A patent/SE7609048L/xx unknown
-
1979
- 1979-10-01 SE SE7908126A patent/SE7908126L/sv not_active Application Discontinuation
- 1979-10-01 SE SE7908125A patent/SE7908125L/sv not_active Application Discontinuation
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