IL49285A - The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one - Google Patents

The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one

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Publication number
IL49285A
IL49285A IL49285A IL4928573A IL49285A IL 49285 A IL49285 A IL 49285A IL 49285 A IL49285 A IL 49285A IL 4928573 A IL4928573 A IL 4928573A IL 49285 A IL49285 A IL 49285A
Authority
IL
Israel
Prior art keywords
trans
iodo
cyclopentene
och
cyclohexyl
Prior art date
Application number
IL49285A
Original Assignee
Wisconsin Alumni Res Found
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/221,058 external-priority patent/US4031129A/en
Application filed by Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found
Publication of IL49285A publication Critical patent/IL49285A/en

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    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/02—Lithium compounds
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • 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
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Materials Engineering (AREA)
  • Toxicology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1419181 Prostaglandins; organolithium compounds WISCONSIN ALUMNI RESEARCH FOUNDATION 24 Jan 1973 [26 Jan 1972 22 May 1972 29 Sept 1972] 3660/73 Headings C2C and C2J The invention comprises a process for preparing prostaglandins of the Formula I wherein R is H, CH 3 or CH 3 CH 2 ; R<SP>1</SP> is H, C 1 -C 9 saturated hydrocarbyl, pentenyl, hexenyl or benzyl; X is H, OH, 2-tetrahydropyranyloxy, OR<SP>11</SP>, wherein R<SP>11</SP> is C 1 -C 5 hydrocarbyl or benzyl, OCOR<SP>111</SP>, wherein R<SP>111</SP> is C 1 -C 8 hydrocarbyl or benzyl, or OCH(R 1 )OR 2 , wherein R 1 and R 2 each are C 1 -C 5 hydrocarbyl; n is 0 to 5; B is -CH 2 CH 2 - or -CH=CH-; Q is OH, OCH 3 or OCH 2 CH 3 ; and the ring A is by reacting compounds of the Formula II wherein B and ring A are as defined above with the proviso that any free hydroxy groups in ring A are protected, and Q is OCH 3 or OCH 2 CH 3 with compounds of the Formula III trans-Li-CH = CH-C(R)(X<SP>1</SP>)(CH 2 ) n R<SP>1</SP> wherein X<SP>1</SP> is H or protected hydroxy as defined above, and if desired removing any protecting groups and/or ester groups, and if desired converting in known manner one ring A to another ring A, and the novel compound of the formula which are obtained by the above process. The following intermediates and starting materials are also prepared: ethyl 1,3-cyclopentadieneheptanoate, ethyl 3-hydroxy-5-oxo- 1 - cyclopentene - 1 - heptanoate ethyl 5- hydroxy - 3 - oxo - 1 - cyclopentene - 1 - heptenoate ethyl 5 - oxo - 3 - (2 - tetrahydropyranyloxy) - 1 - cyclopentene - 1 - heptanoate, ethyl 3,5 - dioxo - 1 - cyclopentene - 1 - heptanoate, isopropyl 3 - hydroxy - 5 - oxo - 1- cyclopentene - 1 - heptanoate, 1 - iodo - 4 - cyclohexyl - 1 - trans - butene, 1 - iodo - 5- cyclohexyl - 1 - trans - pentene, 1 - iodo - 6- cyclohexyl - 1 - trans - hexene, 1 - iodo - 7- cyclohexyl - 1 - trans - heptene, 1 - iodo - 8- cyclohexyl - 1 - trans - octene, 1 - iodo - 5- phenyl - 1 - trans - pentene, 1 - iodo - 6 - phenyl- 1 - trans - hexene, 1 - iodo - 7 - phenyl - 1- trans - heptene, 1 - iodo 8 - phenyl - 1 - transoctene and 1 - iodo - 9 - phenyl - 1 - transnonene. 1 - Lithio - 1 - trans - octene and 1 - lithio- 3 - (1 - ethoxyethoxy) - trans - 1 - octene are obtained by reacting lithium powder in diethyl ether with solutions of 1-iodo-1-trans-octene and the 3 -(1 - ethoxyethoxy) - 1 - iodo - 1- trans-octene respectively. Pharmaceutical compositions contain the above novel compounds and pharmaceutically acceptable carriers or diluents. The compounds possess prostaglandin-like activities. Reference has been directed by the Comptroller to Specification 1,377,258 also Reference has been directed by the Comptroller to Specifications 1,314,292, 1,314,291, 1,282,661 1,198,071, 1,097,533, 1,097,157 and 1,040,544. [GB1419181A]

Description

The preparation of WISCONSBT RSSBARCH THIS INVENTION relates to a process for preparing a useful in the preparation of certain prostaglandins The process for preparing a comprises reacting a with magnesium dehydrating the reaction product to give epoxidising said octenylcy pentenone to give cleaving the epoxide to give oxidising the aldehyde to give and esterifying the The processes for converting the into and are the subject of Patent Application 41305 The invention is illustrated by the following of which Examples 2 and 3 illustrate the preparation of the prostaglandins 1 Into a dry flask equipped with a j septum thermometer well pressure j equalising dropping and magnetic were j placed dry tetrahydrofuran of and molar equivalent of octadiene distilled over calcium hydride A blanket of nitrogen was j i maintained at all The flask was placed in a water bath at Conversion to the trialkylborane was achieved by the dropwise addition of a solution of The of the solution was at by the addition of ice to the water The solution was stirred at for 1 then methanol of wa3 added to destory Molar equivalents of iodine were added all at followed by molar equivalents of solution of sodium hydroxide in methanol over 5 The reaction mixture was allowed to warm up and stirred for a further The reaction mixture was poured intowater containing sodium thiosulphate of to remove excess iodinef and the aqueous layer wa3 three times with The combined pentane extract dried over magnesium The pentane and most of the excess octadiene was removed on a rotary evaporator and the remaining material was distilled over calcium hydride under reduced pressure to give Mole of the in 50 of tetrahydrofuran was added dropwisa to a mixture of g of turnings in 20 of dry tetrahydrofuran with mechanical stirring a blanket of After completion of the addition 1 hr the mixture was boiled under gentle reflux for an additional 30 To thi3 cooled Grignard was added dropwise mole of followed stirring at room temperature for 30 The resulting was poured onto 200 of chipped ice and 30 of One hundred of 2 IT was then After shaking for 30 the product was extracted with several portions of The with portions of saturated then with of saturated and dried over Evaporation of solvent gave of the crude To g of dissolved in 70 of methanol were added 2 of concentrated the mixture was refluxed for The cooled mixture w neutralized by tho addition of solid After of the 200 of water was added and the resulting mixture was exhaustively with of 600 The extracts were with 150 of saturated HaCl and dried over After the solvent by rotary evaporation and the residual oil was distilled under reduced The fraction boiling was collected as pure g of the olefin was dissolved in 8 of methylene chloride and treated a solution of acid in 20 of methylene was to stand at for two After the usual crude mixture was chrcmatographed on a silicic The was with a gradient benzene and acetate to give of pure epoxide and g of starting material which can be The epoxide was dissolved in iO of and treated with a freshl re ared solution of periodic acid 0 rsg 2k of this solution The then diluted with and the organic layer was washed with dried over sulphate and evaporated to dryness to yield the dc3ired aldehyde The aldehyde dissolved in diethyl ether and the solution added dropwise to a suspension of at e ure was stirred for 1 the silver oxide at this point turned black precipitate was filtered off and the filtrate was extracted with methylene chloride three tinea to unreacted aldehyde The aqueous layer acidified pH 2 and exhaustively extracted with ethyl The ethyl acetate layers dried over sodiura sulphate and evaporated to yield 139 of pure Esterification of the acid was achieved by treating the acid with in accordance with to yield 2 326 of in o other was treated GO of lithium in 5 other at The resulting vinyl lithium solution was siphoned through a filte into 123 of iodide complex in 2 dry diethyl ether at This solution was stirred at for 20 whereupon 107 of in 2 of ether were The reaction solution was allowed to warm to and stirred at to for 1 Stirring was continued at for a further 3 of aqueous solution was added and the solution stirred until 2 clear layers were The upper yellow organic layer from the blus layer9 which a further 3 times with The combined ethereal extract was washed with a saturated sodium chloride solution and Evaporation gave a dark red The oil was over a silicic column x The column was eluted with of benzene in the chamber and of acetate in the reservoir fractions were Fractions were combined and treated with hydrocliloric acid to remove the protecting group to upon of a 332 nnr proton at vinyiic protons at and and was identifie 3 solution of copper in dry ether n treated with a solution of in via a at under a blanket of After stirring at for 30 2 was added via a syringe and solution warned to and stirred for an additional 2 at the allowed to to whereupon the yellow solution began darkening after about 30 minutes 20 of saturated with were added until 9 The resulting was filtered with The residue was washed well with ether and filtrate and washings shaken in a The phases were and the aqueous phase was urther extracted with other The combined ethereal extract was washed with a saturated aqueous sodium chloride solution and dried After evaporation of the crude oily residue was chro atographed on 150 silica gel using a gradient starting with pure and 2 litres of chloroform were After this elution continued with pure Approximately 500 of crude methyl ester were treated with of in 5 of water and 15 of The mixture was stirred magnetically for 15 hours and the methanol was then removed by The aqueous phase was diluted with 5 of water and the resulting mixture was extracted with The aqueous phase was then acidi with hydrochloric acid and extracted with The combined ether layers were dried over magnesium sulphate and the solvent was to yield 255 of a material having the following molecular io at for at and and which was identified as The can be readily converted by known procedures to which via brcanlnation and known bo converted to and which can in turn be by known procedures to and For the synthesis of and optically active can bo used to prepare the ether in insufficientOCRQuality

Claims (4)

1. A process for preparing a 2- (6 ' -alkoxy-carbonylhexyl) -2-cyclopenten-l-one , the process comprising reacting a 2-alkoxy-2-cyclopenten-1-one with l-octen-8-yl magnesium iodide, dehydrating the reaction product to give 2- (1 ' -octen-8 *-yl) -2-cyclopenten-l-one, epoxidising said octenylcyclopentehone give 2-(7' , 81 -epoxyoctyl) -2-cyclopenten-l-one , cleaving the epoxide to give (6 ' -formylhexyl ) -2-cyclopenten-l-one, oxidising the aldehyde to give 2- ( 6 * -carboxyhexyl) -2-cyclopenten-l-one and esterifying the acid.
2. A process according to Claim 1 wherein the alkoxy group is a methoxy group.
3. A process according to Claim 1 substantially as described in Example 1.
4. A 2- ( 6 ' -alkoxycarbonylhexy1 ) -2-cyclopenten-l-one prepared by a process according to any one of the preceding claims.
IL49285A 1972-01-26 1973-01-17 The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one IL49285A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US05/221,058 US4031129A (en) 1972-01-26 1972-01-26 15-Deoxy-PGE1 and method for preparing same
US25572872A 1972-05-22 1972-05-22
US29344272A 1972-09-29 1972-09-29

Publications (1)

Publication Number Publication Date
IL49285A true IL49285A (en) 1977-10-31

Family

ID=27396893

Family Applications (5)

Application Number Title Priority Date Filing Date
IL49285A IL49285A (en) 1972-01-26 1973-01-17 The preparation of 2-(6-alkoxy-carbonylhexyl)-2-cyclopenten-1-one
IL49286A IL49286A (en) 1972-01-26 1973-01-17 1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing them
IL41305A IL41305A (en) 1972-01-26 1973-01-17 Method for preparing prosta-glandins of the a,e,f and 11-deoxy-e series and certain novel 15-deoxoprostaglandins
IL49285A IL49285A0 (en) 1972-01-26 1976-03-25 The preparation of 2'-(6-alkoxycarbonylhexyl)-2-cyclopenten-1-one
IL49286A IL49286A0 (en) 1972-01-26 1976-03-25 Novel 1-iodo-1-trans-alkenes,their preparation and pharmaceutical compositions containing them

Family Applications After (4)

Application Number Title Priority Date Filing Date
IL49286A IL49286A (en) 1972-01-26 1973-01-17 1-iodo-1-trans-alkenes their preparation and pharmaceutical compositions containing them
IL41305A IL41305A (en) 1972-01-26 1973-01-17 Method for preparing prosta-glandins of the a,e,f and 11-deoxy-e series and certain novel 15-deoxoprostaglandins
IL49285A IL49285A0 (en) 1972-01-26 1976-03-25 The preparation of 2'-(6-alkoxycarbonylhexyl)-2-cyclopenten-1-one
IL49286A IL49286A0 (en) 1972-01-26 1976-03-25 Novel 1-iodo-1-trans-alkenes,their preparation and pharmaceutical compositions containing them

Country Status (17)

Country Link
JP (3) JPS5333583B2 (en)
AR (2) AR199893A1 (en)
AU (1) AU452896B2 (en)
BE (1) BE794516A (en)
BG (3) BG25207A3 (en)
CA (1) CA1014092A (en)
CH (3) CH590834A5 (en)
DD (3) DD112750A5 (en)
DE (2) DE2365927A1 (en)
ES (3) ES410962A1 (en)
FR (3) FR2181693B1 (en)
GB (3) GB1419183A (en)
IE (2) IE37106B1 (en)
IL (5) IL49285A (en)
NL (2) NL153514B (en)
RO (1) RO71588A (en)
SE (3) SE7600888L (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1018970A (en) * 1972-10-27 1977-10-11 American Home Products Corporation 15-substituted prostanoic acids
JPS5720305B2 (en) * 1973-02-28 1982-04-27
US4029693A (en) * 1975-01-20 1977-06-14 The Upjohn Company 2A,2B-Dihomo-11-deoxy-17(substituted phenyl)-18,19,20-trinor-PGE2 compounds and their corresponding esters
US4032561A (en) * 1975-05-27 1977-06-28 The Upjohn Company 17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGF1.sub.α compounds
US4016184A (en) * 1975-09-17 1977-04-05 The Upjohn Company 9-Deoxy-9,10-didehydro-PGD1 compounds
US4365075A (en) * 1975-09-17 1982-12-21 The Upjohn Company ω-Aryl-PGD compounds
US4029814A (en) * 1975-12-29 1977-06-14 The Upjohn Company Phenyl-substituted prostaglandin-e type analogs
US4219662A (en) * 1977-02-28 1980-08-26 The Upjohn Company 11-Deoxy-17-phenyl-PGE1 analogs
AU529883B2 (en) * 1978-09-04 1983-06-23 Australian National University, The Substituted cyclopentenones

Also Published As

Publication number Publication date
DE2365513B2 (en) 1978-11-16
BG25208A3 (en) 1978-08-10
NL7708070A (en) 1977-10-31
IL41305A0 (en) 1973-03-30
DE2303612A1 (en) 1973-10-25
IE37108B1 (en) 1977-05-11
ES438594A1 (en) 1977-10-16
IE37106B1 (en) 1977-05-11
DD113214A5 (en) 1975-05-20
CH590834A5 (en) 1977-08-31
CH578502A5 (en) 1976-08-13
FR2257567A1 (en) 1975-08-08
DE2365513A1 (en) 1975-06-26
BG25207A3 (en) 1978-08-10
DD112750A5 (en) 1975-05-05
BE794516A (en) 1973-05-16
ES438595A1 (en) 1977-06-16
IE37106L (en) 1973-07-26
IE37108L (en) 1973-07-26
DD108069A5 (en) 1974-09-05
FR2272642A1 (en) 1975-12-26
FR2257567B1 (en) 1978-02-03
AU5108173A (en) 1974-07-18
BG25206A3 (en) 1978-08-10
IL49286A0 (en) 1976-05-31
GB1419182A (en) 1975-12-24
NL153514B (en) 1977-06-15
SE7600890L (en) 1976-01-28
IL49285A0 (en) 1976-05-31
JPS5253801A (en) 1977-04-30
FR2181693B1 (en) 1979-01-12
RO71588A (en) 1982-02-26
IL49286A (en) 1977-10-31
GB1419183A (en) 1975-12-24
NL7301094A (en) 1973-07-30
CA1014092A (en) 1977-07-19
DE2365513C3 (en) 1979-07-19
CH580046A5 (en) 1976-09-30
JPS5253840A (en) 1977-04-30
SE7600888L (en) 1976-01-28
IL41305A (en) 1977-10-31
JPS4881836A (en) 1973-11-01
GB1419181A (en) 1975-12-24
DE2365927A1 (en) 1976-12-09
AU452896B2 (en) 1974-08-30
FR2272642B1 (en) 1981-08-07
SE7600889L (en) 1976-01-28
FR2181693A1 (en) 1973-12-07
AR200537A1 (en) 1974-11-15
JPS5333583B2 (en) 1978-09-14
DE2303612B2 (en) 1977-04-07
AR199893A1 (en) 1974-10-08
ES410962A1 (en) 1977-04-01

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