ES438765A1 - 11,12-secoprostaglandins - Google Patents

11,12-secoprostaglandins

Info

Publication number
ES438765A1
ES438765A1 ES438765A ES438765A ES438765A1 ES 438765 A1 ES438765 A1 ES 438765A1 ES 438765 A ES438765 A ES 438765A ES 438765 A ES438765 A ES 438765A ES 438765 A1 ES438765 A1 ES 438765A1
Authority
ES
Spain
Prior art keywords
ester
secoprostaglandins
dioxothia
oxothia
thia
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
ES438765A
Other languages
Spanish (es)
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 ES438765A1 publication Critical patent/ES438765A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • 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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

9-Thia-, 9-oxothia- and 9-dioxothia-11,12-secoprostaglandins of the formula II < IMAGE > are prepared, wherein A, R<4>, R<9> and R<10> are defined in Claim 1 and m is 0, 1 or 2. If n = 0, these compounds are obtained by reacting, in optional sequence, di-tert.-butyl malonate with two different appropriate halogeno-esters in order to introduce the two side chains. The reaction product obtained is a disubstituted malonic ester. By heating this ester in the presence of a strong acid, the corresponding substituted decarboxylated malonic acid derivative is obtained. This derivative is then reacted with bromine in the presence of mercury(II) oxide, whereby the carboxyl group is replaced by bromine. The resulting substituted bromo-ester is then reacted with the alkali metal salt of a mercaptan of the formula R<9>SH, and finally the ester group is hydrolysed. To prepare 9-oxothia- and 9-dioxothia-11,12-secoprostaglandins, the 9-thia-11,12-secoprostaglandins are oxidised. The compounds exhibit a prostaglandin-like activity and may be used for the treatment of skin diseases.
ES438765A 1974-06-25 1975-06-20 11,12-secoprostaglandins Expired ES438765A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48317874A 1974-06-25 1974-06-25
US56656675A 1975-04-09 1975-04-09

Publications (1)

Publication Number Publication Date
ES438765A1 true ES438765A1 (en) 1977-07-01

Family

ID=27047557

Family Applications (1)

Application Number Title Priority Date Filing Date
ES438765A Expired ES438765A1 (en) 1974-06-25 1975-06-20 11,12-secoprostaglandins

Country Status (16)

Country Link
JP (1) JPS51125020A (en)
CA (1) CA1064961A (en)
CH (1) CH614935A5 (en)
DE (1) DE2528070A1 (en)
DK (1) DK263775A (en)
ES (1) ES438765A1 (en)
FI (1) FI751730A (en)
FR (1) FR2276037A1 (en)
GB (1) GB1476262A (en)
IE (1) IE41258B1 (en)
IL (1) IL47487A (en)
LU (1) LU72797A1 (en)
NL (1) NL7507020A (en)
NO (1) NO142219C (en)
NZ (1) NZ177843A (en)
SE (1) SE7506804L (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2111385B1 (en) 2007-02-06 2014-11-12 University Of Louisville Research Foundation, Inc. Substituted alkine derivatives as anti-cancer agents
AU2012225574A1 (en) 2011-03-07 2013-09-26 University Of Louisville Research Foundation, Inc. Predictive marker of DNMT1 inhibitor therapeutic efficacy and methods of using the marker
US9737493B2 (en) 2012-09-07 2017-08-22 University Of Louisville Research Foundation, Inc. Compositions and methods for modulating DNMT1 inhibitor activity

Also Published As

Publication number Publication date
LU72797A1 (en) 1976-04-13
DE2528070A1 (en) 1976-01-08
SE7506804L (en) 1975-12-29
IL47487A0 (en) 1975-08-31
CA1064961A (en) 1979-10-23
NO142219B (en) 1980-04-08
NO142219C (en) 1980-07-16
AU8221675A (en) 1976-12-23
NL7507020A (en) 1975-12-30
FR2276037B1 (en) 1979-03-02
JPS51125020A (en) 1976-11-01
IE41258B1 (en) 1979-11-21
FI751730A (en) 1975-12-26
DK263775A (en) 1975-12-26
NZ177843A (en) 1978-04-03
GB1476262A (en) 1977-06-10
CH614935A5 (en) 1979-12-28
IE41258L (en) 1975-12-25
IL47487A (en) 1979-05-31
NO752091L (en) 1975-12-30
FR2276037A1 (en) 1976-01-23

Similar Documents

Publication Publication Date Title
ES426574A1 (en) Preparation of arylalkanoic acids
IL48637A (en) 2-(tetrazol-5-yl)-9-oxo(hydroxy)-11-desoxy-15wpentanorprosstanoic acid derivatives and pharmaceutical compositions containing them
GB1415412A (en) Perfluoroalkyl compounds process for their manufacture and their use
GB1461184A (en) Process for the manufacture of 5-fluorocytosine
ES438765A1 (en) 11,12-secoprostaglandins
GB1363597A (en) 2-acyloxy-benzoic acid anilides process for their preparation and their insecticidal and acaricidal use
GB1480671A (en) Process for the preparation of 1,1-dihalo-4-methyl pentadienes
ES438496A1 (en) Process for making 2-cyano-2-hydroxyiminoacetamide salts
JPS53147026A (en) Continuous preparation of thioglycolic acid
SE7509339L (en) PROCEDURE FOR THE PREPARATION OF 7BETA-ACYLAMINO-7ALFA-ALCOXIC PHALOSPHORINS.
SE7509107L (en) ARYLOXY OR ARYLTIO CONTAINING SECOPROSTAGLANDINS
IE42933L (en) Glyoxylic acid derivatives.
GB1515614A (en) Preparation of m-benzoylhydratropic acid and an intermediate therefor
ES409237A1 (en) Process for the preparation of 3-benzoylphenyl alkanoic acids
GB999252A (en) A novel ester and a process for the preparation thereof
ES450688A1 (en) Production of n,n-diethyl 2(&#39; -naphthoxy)propionamide
CH609669A5 (en) Process for the preparation of metformin clofibrate
GB1240987A (en) Sulfur-containing hydroxybenzophenone ethers
ES445336A1 (en) Oxoindanylpropionic acids and process for the preparation thereof
GB1382438A (en) Adamantane and substituted adamantane carboxylic acid esters of chloramphenicol
CH609024A5 (en) Process for the preparation of new sulphur-containing diaryl and oxygen-containing diaryl compounds
GB1464418A (en) Production of 2-hydroxynaphthalene-3-carboxylic acid
ES336788A1 (en) 5-halosalicylic acid derivatives
GB1425159A (en) Phenylacetone compounds and their bisulphite adducts
GB1382469A (en) Cyclohexanepentol derivatives and process for preparing the same