SU538659A3 - Способ получени соединений р да простагландинов - Google Patents
Способ получени соединений р да простагландиновInfo
- Publication number
- SU538659A3 SU538659A3 SU1971421A SU1971421A SU538659A3 SU 538659 A3 SU538659 A3 SU 538659A3 SU 1971421 A SU1971421 A SU 1971421A SU 1971421 A SU1971421 A SU 1971421A SU 538659 A3 SU538659 A3 SU 538659A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- phenylphenol
- tetranor
- methylene chloride
- biphenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 5
- 150000003180 prostaglandins Chemical class 0.000 title claims 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 239000000741 silica gel Substances 0.000 claims 4
- 229910002027 silica gel Inorganic materials 0.000 claims 4
- -1 tetrahydropyran-2-yloxy Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000002474 experimental method Methods 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 235000014676 Phragmites communis Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 239000013076 target substance Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
Claims (2)
- гываюг 4енилфенолом в присутствии водо отнимающего агента, преимущественно дициклогексилкарбодиимида (ДЦГКД), с после дующим удалением тетрагидропиранильного остатка. Полученные соединени очищают методом хроматографии на нейтральной окиси алюмини или силикагеле, предпочтительно на с№ ликагеле с размером частиц 60-200 меш, использу в качестве элюента эфир, эти; адетат , бензол, хлороформ, метиленхлорид, 1щклогексан и -гексан. Пример 1. гр-Бифенил -9-оксо-11 dt, 15 А -био-(тетрагидропиран-2-илокси}-16-фениль-дио-5-трано- СО-тетра норпростадиеноат. Раствор 9-oKco-lldv, 15 с1с-бис-{тетра гидропиран-2-илокси )-16-фенил-цио-5-тран 1-13 Ct -тетранорпростадиеновой кислоты (10а) (1 экв), п-фенилфенола (Ю экв) и дициклогексилкарбодиимида (1,25 экв) в метиленхлориде перемешивают в течение но чи, концентрируют в вакууме, хроматографи руют и получают целевой продукт. Приме р2, п-Бифени; -9с1-окси-llck , 15 с -бис-(тетрагидропира№-2-илокси )-16-фенил-цио-5-трано-13 U -тетранорПростадиеноата , Из раствора п-бифенил-9сК.-окси-11(А., 15 о -био- (тетрагидропиран-2-илокси )-16-фeниJ -циo-5-тpaнc -l 3 и -тетранорпростадиеновой кислоты (9а) (1 экв), п-фенилфенола (10 экв) и дидиклогексилкарбодии- МИДа (1,25 экв) в метиленхлориде аналогично примеру 1 получают целевой продукт. Пример 3. п-Фенилфенольный сложный эфир 16-Л-тиенил-teP -тетранор PQE ,j. Раствор 246 мг (0,65 моль) 16с -тиенил-ce -TeTpaHofH-PQEg , 68Омг (4ммоль) п-фенилфенола и 412 мг (1 ммоль) дицик- логексилкарбодиимида в метиленхлориде и 15 мл метиленхлорида перемещивают в течение ночи при комнатной температуре, ко№ центрируют в вакууме, хроматографируюг на силикагеле (фирма Бeйкepf 60-200 меш) и подучают 60 мг целевого эфира, т.цл. 115-117°С (эфир-пентан). Аналогично получают п-фенилфенольный сложный эфир 16- ,Р -тиени№- ttP -тетранорпростагландина Е„, т.пл. 126-128 С. 659 Примеры 4-2О, Провод т опыт, как в примере 3, и получают п-фенилфенол ные сложные эфиры соединений р да проотагландина . Услови опыта и свойства полученных эфиров приведены в таблице. Во всех опытах, кроме специально оговоренных случаев, целевые продукты перекристаллизовьтают из смеси эфир-пентан. Пример 21, п-Бифенильный сло.жный эфир 9-оксо-11(К, 15 с(ч.-диокср -16-фенил-цис -5-трансн-13 t -тетранорпростаг ландина . Раствор 200 мг (О,535 ммоль) 9-оксо -11 сК., 15 (.-диокси-16-фeниJ -циo-5-транс-13- оО -тетранорпростагландина (На), 90О мг (5,3 ммоль) п-фенилфенола, 7 мл 0,О97 М раствора ДЦГКД в метиленхлоридб и 20 мл метиленхлорида перемешивают в течение ночи при комнатной температуре, концентрируют в вакууме, очищают на колонке , заполненной силикагежм (фирмы Бейкер , 6 0-2 О О меш), элюиру хлороформом, а затем этилацетатом, и получают целевое вещество, т.пл, 120-121 С (эфир-пентан). Подобным образом получают п-бифенилыные сложные эфиры: 13, 14-Дигидро-16-фенил-с«3 -тетранор -PQEji , т.пл, 1О8°С 16-Фенил- А)-тетранор-Р(ЗЕ, ТсПЛ, 96-100 :: 17 -Фенил-сО-тетранор-РЭДз.. т.пл. 114,5115 ,5°С 16 р -Нафтиле-из-тетранор-Р Е, т,пл, 79-62°С 1бЛ-Тиенил-U)-тетранор-РОЕ, т,пл, 115-.117°С 20-Окса- ч -roMo-PQEj, т.пл. 72-73°С 17-OKca-PQF5 т,пл, 93-94, 13, 14-Дигидро-15-эпр -16-фенил- i -тетpaHop-PQFj т.пл. 111,5-113,5 С 13, 14-Дигидро-16-фенил-(JO-тетранор-PGF , ,т,пл. 129-131°С 16-п-Бифени; -cO-TeTpaHOp-PQE, т.лл. 1О7-1О9°С т,пл, 104 2 0-Окса- 00 -roMO-PQR 105°С 16dv -Тиенил-сО -тетранор-PQE, т.пл, 120-121°С 16-Фенил- оО -тетранор-PGF , т. пл, 117-119°С 9 Формула изобретени 1. Способ получени соединений р да простагландинов общей формулы Лл7 COORi Eg где R - водород или низший алкил; R( - П бифенил; ffg группа общей формулы АгССН,,,) - или -(CH2)rv. R, - кегогруппа , и I, д образуют одинарную св зь или RI. водород , если R - dc-гидроксил, причем R , R и Кг выбирают таким образом, чтобы была завершена структура простагландина р да А, Е или F; W - одинарна или цио-двойна св зь; Т. - одинарна или тра -двойна св зь; А г- d. - или Ji -фурил, d. или -тиенил, ck. - или -нафтид, 3,4 -диметоксифенил, 3,4-метилендиоксифенил, 3,4,5-триметоксифенил или фени , моноаам щенный на галоид, трифгорметил, фени№-низ 59 п - 0-5, ий алкил или низший алкоксил; П - 1-5, огда Z. - одинарна св зь; или m - 2 огда L. - трано-двойна св зь; о т л и ч а юли 3; Rg- низший алкил, тем, что соединение общей фори и с улы N/ и Z. имеют знагде R , I 5 I ц R -J имеет те же значени , указанные выше; чени , что и Rg, или О-тетрагидропиранил; Rg - гидроксил или О-тетрагидропиранил, подвергают взаимодействию с п-фенилфенолом в присутствии водоотнимающего средсгва с последующим удалением тетрагидропиранильной группы.
- 2. Способ по п. 1, отличающийс тем, что в качестве водоотнимающего средства примен ют дициклогекси№карбодиимид .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481572A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU538659A3 true SU538659A3 (ru) | 1976-12-05 |
Family
ID=23178143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1971421A SU538659A3 (ru) | 1972-11-08 | 1973-11-11 | Способ получени соединений р да простагландинов |
| SU752115232A SU1021340A3 (ru) | 1972-11-08 | 1975-03-20 | Способ получени простагландинов |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752115232A SU1021340A3 (ru) | 1972-11-08 | 1975-03-20 | Способ получени простагландинов |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5644068B2 (ru) |
| AR (2) | AR204816A1 (ru) |
| AT (1) | AT347607B (ru) |
| BE (1) | BE807047A (ru) |
| CA (1) | CA1027559A (ru) |
| CH (1) | CH601222A5 (ru) |
| CS (1) | CS188175B2 (ru) |
| DD (2) | DD111370A5 (ru) |
| DE (2) | DE2365999A1 (ru) |
| ES (2) | ES420326A1 (ru) |
| FI (1) | FI58116C (ru) |
| FR (2) | FR2205339B1 (ru) |
| GB (1) | GB1456511A (ru) |
| HU (2) | HU171818B (ru) |
| IE (1) | IE39686B1 (ru) |
| IL (1) | IL43553A (ru) |
| IN (1) | IN139905B (ru) |
| NL (1) | NL7315240A (ru) |
| NO (2) | NO145437C (ru) |
| PH (2) | PH15504A (ru) |
| SE (2) | SE420198B (ru) |
| SU (2) | SU538659A3 (ru) |
| YU (2) | YU287973A (ru) |
| ZA (1) | ZA738593B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361381A1 (fr) * | 1972-07-13 | 1978-03-10 | Pfizer | Ethers tetrahydropyranyliques, utiles comme intermediaires de synthese de prostaglandines |
| US3929862A (en) * | 1974-01-08 | 1975-12-30 | Upjohn Co | Substituted tolylesters of PGF{HD 2{B {60 |
| US3998869A (en) * | 1974-11-14 | 1976-12-21 | The Upjohn Company | Substituted anilide esters of 16-substituted PGE2 |
| DE2737807A1 (de) * | 1976-08-27 | 1978-03-09 | Pfizer | C tief 1 -p-biphenylester von omega-pentanorprostaglandinen |
| US6531504B2 (en) * | 2001-05-17 | 2003-03-11 | Allergan, Inc. | Prostanoic acid derivatives as agents for lowering intraocular pressure |
-
1973
- 1973-01-01 AR AR250900A patent/AR204816A1/es active
- 1973-11-01 SE SE7314885A patent/SE420198B/xx unknown
- 1973-11-01 GB GB5088973A patent/GB1456511A/en not_active Expired
- 1973-11-02 IL IL43553A patent/IL43553A/xx unknown
- 1973-11-03 DE DE2365999A patent/DE2365999A1/de not_active Withdrawn
- 1973-11-03 DE DE19732355042 patent/DE2355042A1/de not_active Withdrawn
- 1973-11-06 IN IN2443/CAL/73A patent/IN139905B/en unknown
- 1973-11-07 YU YU02879/73A patent/YU287973A/xx unknown
- 1973-11-07 CA CA185,201A patent/CA1027559A/en not_active Expired
- 1973-11-07 FI FI3444/73A patent/FI58116C/fi active
- 1973-11-07 NO NO4290/73A patent/NO145437C/no unknown
- 1973-11-07 NL NL7315240A patent/NL7315240A/xx not_active Application Discontinuation
- 1973-11-07 AT AT937173A patent/AT347607B/de not_active IP Right Cessation
- 1973-11-07 ES ES420326A patent/ES420326A1/es not_active Expired
- 1973-11-08 CS CS737670A patent/CS188175B2/cs unknown
- 1973-11-08 HU HU73PI00000400A patent/HU171818B/hu unknown
- 1973-11-08 PH PH15198A patent/PH15504A/en unknown
- 1973-11-08 JP JP12501173A patent/JPS5644068B2/ja not_active Expired
- 1973-11-08 HU HU73PI00000453A patent/HU171945B/hu unknown
- 1973-11-08 IE IE2013/73A patent/IE39686B1/xx unknown
- 1973-11-08 ZA ZA738593A patent/ZA738593B/xx unknown
- 1973-11-08 DD DD174537A patent/DD111370A5/xx unknown
- 1973-11-08 CH CH1570273A patent/CH601222A5/xx not_active IP Right Cessation
- 1973-11-08 DD DD180196*A patent/DD113211A5/xx unknown
- 1973-11-08 FR FR7339759A patent/FR2205339B1/fr not_active Expired
- 1973-11-08 BE BE1005489A patent/BE807047A/xx unknown
- 1973-11-11 SU SU1971421A patent/SU538659A3/ru active
-
1974
- 1974-07-31 AR AR254983A patent/AR202311A1/es active
- 1974-10-03 NO NO743588A patent/NO146280C/no unknown
-
1975
- 1975-02-13 ES ES434687A patent/ES434687A1/es not_active Expired
- 1975-03-20 SU SU752115232A patent/SU1021340A3/ru active
- 1975-08-18 FR FR7525565A patent/FR2275452A1/fr active Granted
-
1976
- 1976-03-12 PH PH18199A patent/PH13794A/en unknown
-
1977
- 1977-04-15 SE SE7704369A patent/SE7704369L/xx not_active Application Discontinuation
-
1980
- 1980-10-15 YU YU02644/80A patent/YU264480A/xx unknown
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