IE41258B1 - 11,12-secoprostaglandins - Google Patents

11,12-secoprostaglandins

Info

Publication number
IE41258B1
IE41258B1 IE1371/75A IE137175A IE41258B1 IE 41258 B1 IE41258 B1 IE 41258B1 IE 1371/75 A IE1371/75 A IE 1371/75A IE 137175 A IE137175 A IE 137175A IE 41258 B1 IE41258 B1 IE 41258B1
Authority
IE
Ireland
Prior art keywords
ester
secoprostaglandins
dioxothia
oxothia
thia
Prior art date
Application number
IE1371/75A
Other versions
IE41258L (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 IE41258L publication Critical patent/IE41258L/en
Publication of IE41258B1 publication Critical patent/IE41258B1/en

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. [GB1476262A]
IE1371/75A 1974-06-25 1975-06-19 11,12-secoprostaglandins IE41258B1 (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 (2)

Publication Number Publication Date
IE41258L IE41258L (en) 1975-12-25
IE41258B1 true IE41258B1 (en) 1979-11-21

Family

ID=27047557

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1371/75A IE41258B1 (en) 1974-06-25 1975-06-19 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
JP2010518108A (en) * 2007-02-06 2010-05-27 ユニバーシティ オブ ルーイビル リサーチ ファウンデーション，インコーポレーテッド Therapeutic compound
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
SE7506804L (en) 1975-12-29
AU8221675A (en) 1976-12-23
DE2528070A1 (en) 1976-01-08
CA1064961A (en) 1979-10-23
ES438765A1 (en) 1977-07-01
JPS51125020A (en) 1976-11-01
NO752091L (en) 1975-12-30
NO142219B (en) 1980-04-08
DK263775A (en) 1975-12-26
IE41258L (en) 1975-12-25
NO142219C (en) 1980-07-16
FR2276037B1 (en) 1979-03-02
IL47487A (en) 1979-05-31
IL47487A0 (en) 1975-08-31
FR2276037A1 (en) 1976-01-23
CH614935A5 (en) 1979-12-28
NL7507020A (en) 1975-12-30
FI751730A (en) 1975-12-26
NZ177843A (en) 1978-04-03
GB1476262A (en) 1977-06-10
LU72797A1 (en) 1976-04-13

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