GB1431100A - 11,12-secoprostaglandins - Google Patents

11,12-secoprostaglandins

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Publication number
GB1431100A
GB1431100A GB4904073A GB4904073A GB1431100A GB 1431100 A GB1431100 A GB 1431100A GB 4904073 A GB4904073 A GB 4904073A GB 4904073 A GB4904073 A GB 4904073A GB 1431100 A GB1431100 A GB 1431100A
Authority
GB
United Kingdom
Prior art keywords
acetoxy
acid
alkyl
methyl
benzyloxyheptadecanoic
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB4904073A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and 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 and Co Inc filed Critical Merck and Co Inc
Publication of GB1431100A publication Critical patent/GB1431100A/en
Expired legal-status Critical Current

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    • 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
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
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    • 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
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    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
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    • 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

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  • 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.
GB4904073A 1972-10-30 1973-10-22 11,12-secoprostaglandins Expired GB1431100A (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 (1)

Publication Number Publication Date
GB1431100A true GB1431100A (en) 1976-04-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB4904073A Expired GB1431100A (en) 1972-10-30 1973-10-22 11,12-secoprostaglandins

Country Status (10)

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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
FR2204423B1 (en) 1977-07-08
NL7314109A (en) 1974-05-02
FR2204423A1 (en) 1974-05-24
AU472337B2 (en) 1976-05-20
IE38390L (en) 1974-04-30
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

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PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee