IE38390L - 11, 12-secoprostaglandins - Google Patents

11, 12-secoprostaglandins

Info

Publication number
IE38390L
IE38390L IE731863A IE186373A IE38390L IE 38390 L IE38390 L IE 38390L IE 731863 A IE731863 A IE 731863A IE 186373 A IE186373 A IE 186373A IE 38390 L IE38390 L IE 38390L
Authority
IE
Ireland
Prior art keywords
acetoxy
acid
alkyl
methyl
benzyloxyheptadecanoic
Prior art date
Application number
IE731863A
Other versions
IE38390B1 (en
Original Assignee
Merck & Co Inc
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
Application filed by Merck & Co Inc filed Critical Merck & Co Inc
Publication of IE38390L publication Critical patent/IE38390L/en
Publication of IE38390B1 publication Critical patent/IE38390B1/en

Links

Classifications

    • 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
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
    • C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C245/18—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/10—Polyhydroxy carboxylic acids
    • C07C59/105—Polyhydroxy carboxylic acids having five or more carbon atoms, e.g. aldonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/147—Saturated compounds having only one carboxyl group and containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/215—Saturated compounds having only one carboxyl group and containing keto groups containing singly bound oxygen containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/225—Saturated compounds having only one carboxyl group and containing keto groups containing —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/347—Saturated compounds containing more than one carboxyl group containing keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/04—Formic acid esters
    • C07C69/08—Formic acid esters of dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/16—Acetic acid esters of dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • 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 Table
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1431100 11,12-Secoprostaglandins MERCK & CO Inc 22 Oct 1973 [30 Oct 1972 23 Aug 1973] 49040/73 Headings C2C and C2P The invention comprises 11,12-secoprostaglandins of the Formula I in which R is -COOY, CONHNH 2 or where Y is H, C 1-10 alkyl or a pharmaceutically acceptable cation and each of R<SP>6</SP> and R<SP>7</SP> is H, C 1-4 alkyl or C 4-7 dialkylaminoalkyl; A is ethylene trimethylene, α-methylethylene, #- methylethylene, α,α-dimethylene, #,#-dimethylethylene or oxymethylene; R<SP>1</SP> is formyl, acetyl, propionyl or acryloyl and R<SP>3</SP> is H or C 1-6 alkanoyl, or R<SP>1</SP> is 3-hydroxypropionyl, glycoloyl, hydroxymethyl, 1 - hydroxyethyl, 1,2 - dihydroxyethyl, 1,3 - dihydroxypropyl or 1- hydroxy-1-methylethyl and R<SP>3</SP> is H; Z is methylene, ethylene, trimethylene, tetramethylene, vinylene or ethynylene; R<SP>2</SP> is H or (unless Z is vinylene) a methyl radical; each R<SP>4</SP> is independently H or methyl; and R<SP>5</SP> is H, C 1-4 alkyl or CH 2 CF 3 , or (unless Z is vinyl or ethynylene) a vinyl radical, or (unless Z is vinylene) R<SP>5</SP> and R<SP>2</SP> are joined together to form, with the intervening carbon atoms, a C 5-9 carbocyclic ring, and their preparation via actoacetic acid or malonic acid syntheses or Wittig reactions. The following intermediates are also prepared; compounds of the formulµ where R<SP>10</SP> and R<SP>11</SP> are C 1-5 alkyl where X is halogen and Z<SP>1</SP> is (CH 2 ) n where n is 1 to 4, where R<SP>12</SP> is H, C 1-4 alkyl or CH 2 CF 3 ; where R<SP>52</SP> is H, C 1-4 alkyl or CH 2 CF 3 or R<SP>52</SP> and R<SP>3</SP> are joined together to form, with the intervening carbon atoms a C 5-9 carbocyclic ring; 1 - nonen - 4 - ol, 4 - acetoxy - 1 - nonene, 2 - methyl - 2 - hydroxy - 3 - (6 - carboxyhexyl) - 6 - hexyltetrahydropyran; where X<SP>1</SP> is Cl or OH; dimethyl 3-oxosebacoate, 1-chloro 3 -octanol; 3-chloromethoxy-1-chlorooctane; 3-benzyloxy-1-chlorooctane; methyl- 8 - oxo - 9 - methoxycarbonyl - 12 - benzyloxyheptadecanoate; 8-oxo-12-benzyloxyheptadecanoic acid; 3-chloromethoxy-1-bromopropane; 3-benzyloxy-1-bromopropane; 8-(3- benzyloxypropylidenyl) - 12 - benzyloxyheptadecanoic acid; 8-(4-benzyloxynonyl)-8,9-epoxy- 11-benzyloxyundecanoic acid; 8-(3-benzyloxypropionyl) - 12 - benzyloxyheptadecanoic acid; 5-acetoxypentyl chloride; diethyl 2-(5-acetoxypentyl) - 2 - methylmalonate; 7 - bromo - 2- methylheptanoic acid, and its methyl ester; 8- (3 - benzyloxy - 1 - hydroxypropyl) - 12 - benzyloxyheptadecanoic acid; 8-(3-methoxy-1-bydroxypropyl) - 12 - hydroxyheptadecanoic acid; 8,12 - dihydroxyheptadecanoic acid; ethyl ethyl 4-bromobutoxyacetate; N-t-butyl-3-(8- acetyl - 12 - hydroxyheptadecanoyloxy)crotonamide; ethyl 8-diazoacetyl-12-acetoxy-heptadecanoate; 3-acetoxy-1-octyne; 1-diethylamino - 4 - acetoxy - 2 - nonyne; 1-bromo- 4 - acetoxy - 2 - nonyne; diethyl 2 - acetyl- 2 - (4 - acetoxy - 2 - nonynyl)azelate; 8- acetyl - 12 - oxo - heptadecanoic acid; 1- acetoxy - 1 - ethynylcyclohexane, 1 - acetoxy- ] - ethynylcyclooctane; 1 - acetoxy - 1 - (3- diethylamino - 1 - propynyl)cyclohexane; 1- acetoxy - 1 - (3 - diethylamino - 1 - propynyl)-cyclooctane; 1 - acetoxy - 1 - (3- bromo - 1 - propynyl)cyclohexane; and 1- acetoxy - 1 - (3 - bromo - 1 - propynyl)cyclooctane. (3 - Benzyloxypropyl)triphenylphosphonium bromide is obtained by reacting 3-benzyloxy-1- bromopropane with triphenylphosphine. Pharmaceutical compositions suitable for oral, parenteral, rectal or topical administration, contain the above 11,12-secoprostaglandins and pharmaceutically acceptable carriers. The compositions are used to improve renal function, the treatment of hypertension and dwarfism, and prevention of thrombus formation. [GB1431100A]
IE1863/73A 1972-10-30 1973-10-18 11,12-secoprostaglandins IE38390B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30236572A 1972-10-30 1972-10-30
US38990173A 1973-08-23 1973-08-23

Publications (2)

Publication Number Publication Date
IE38390L true IE38390L (en) 1974-04-30
IE38390B1 IE38390B1 (en) 1978-03-01

Family

ID=26972898

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1863/73A IE38390B1 (en) 1972-10-30 1973-10-18 11,12-secoprostaglandins

Country Status (10)

Country Link
JP (1) JPS49100032A (en)
AU (1) AU472337B2 (en)
CA (1) CA1014169A (en)
CH (1) CH605553A5 (en)
ES (1) ES419810A1 (en)
FR (1) FR2204423B1 (en)
GB (1) GB1431100A (en)
IE (1) IE38390B1 (en)
IL (1) IL43436A (en)
NL (1) NL7314109A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5686129A (en) * 1979-12-18 1981-07-13 Teijin Ltd Secoprostaglandin and its preparation
JPS5726640A (en) * 1980-07-24 1982-02-12 Teijin Ltd Novel secoprostaglandin and its preparation

Also Published As

Publication number Publication date
AU6157273A (en) 1975-04-24
GB1431100A (en) 1976-04-07
FR2204423B1 (en) 1977-07-08
NL7314109A (en) 1974-05-02
FR2204423A1 (en) 1974-05-24
AU472337B2 (en) 1976-05-20
CH605553A5 (en) 1978-09-29
CA1014169A (en) 1977-07-19
DE2354085A1 (en) 1974-05-16
JPS49100032A (en) 1974-09-20
IL43436A0 (en) 1974-01-14
IE38390B1 (en) 1978-03-01
IL43436A (en) 1978-12-17
DE2354085B2 (en) 1977-04-07
ES419810A1 (en) 1977-01-01

Similar Documents

Publication Publication Date Title
US4127726A (en) Cis-13-PGE2, 15 methyl ethers
US4120880A (en) 9β-PGD1 Compounds
US4097508A (en) Cis-4,5-didehydro-13,14 dihydro-9, dioxy PGF compounds
US4124620A (en) Cis-4,5-didehydro-9-deoxy-PGD1 compounds
IE38241L (en) Prostanoic acid derivatives
GB1459564A (en) Alkylphenyl benzopyrans
IE38390B1 (en) 11,12-secoprostaglandins
GB1509904A (en) Nitriles derived from indane-1,3-dione and coumarin
GB1506824A (en) Prostaglandins
WO1983004021A1 (en) 2,3,4-trinor-1,5-inter-m-phenylene-prostacycline-i2 analogues, process for the preparation thereof and pharmaceutical compositions containing the same
NZ200633A (en) Carbacyclin derivatives and pharmaceutical compositions
CA1092102A (en) 11-oxo-prostaglandin derivatives and processes for their manufacture
GB1396206A (en) Prostaglandins and the preparation thereof
GB1497011A (en) 2-(omega-haloalkenyl-cyclopentane-1-heptanoic acids methods for preparation thereof and their use
GB1508170A (en) Substituted cyclopentane compounds useful as intermediates in the synthesis of prostaglandin analogues
GB1434620A (en) Prostaglandins and the preparation thereof
IE40571B1 (en) Cyclopentane derivatives
GB1431561A (en) Cyclopentane derivatives
EP0059756A1 (en) 7-oxoprostacyclin derivatives and process for the preparation thereof.
GB1462716A (en) Prosta-5-cis,11,13-trnas-trienoic acids and derivatives thereof
US4191822A (en) 5-Hydroxy-PGI1 compounds
CA1040195A (en) Cyclopentane derivatives
IE42966L (en) 8-azaprostaglandins and process for the preparation thereof.
GB1494321A (en) Prostanoic acid derivatives
GB1398346A (en) Prostaglandins and the preparation thereof