GB1476262A - 11,12-secoprostaglandins - Google Patents

11,12-secoprostaglandins

Info

Publication number
GB1476262A
GB1476262A GB2579775A GB2579775A GB1476262A GB 1476262 A GB1476262 A GB 1476262A GB 2579775 A GB2579775 A GB 2579775A GB 2579775 A GB2579775 A GB 2579775A GB 1476262 A GB1476262 A GB 1476262A
Authority
GB
United Kingdom
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
GB2579775A
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 GB1476262A publication Critical patent/GB1476262A/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

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.
GB2579775A 1974-06-25 1975-06-17 11,12-secoprostaglandins Expired GB1476262A (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
GB1476262A true GB1476262A (en) 1977-06-10

Family

ID=27047557

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2579775A Expired GB1476262A (en) 1974-06-25 1975-06-17 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
US9383364B2 (en) 2011-03-07 2016-07-05 University Of Louisville Research Foundation, Inc. Predictive marker of DNMT1 inhibitor therapeutic efficacy and methods of using the marker
WO2014039860A2 (en) 2012-09-07 2014-03-13 University Of Louisville Research Foundation, Inc. Compositions and methods for modulating dnmt1 inhibitor activity

Also Published As

Publication number Publication date
DK263775A (en) 1975-12-26
NZ177843A (en) 1978-04-03
CA1064961A (en) 1979-10-23
IE41258B1 (en) 1979-11-21
NL7507020A (en) 1975-12-30
IE41258L (en) 1975-12-25
IL47487A (en) 1979-05-31
DE2528070A1 (en) 1976-01-08
IL47487A0 (en) 1975-08-31
LU72797A1 (en) 1976-04-13
NO142219B (en) 1980-04-08
NO142219C (en) 1980-07-16
ES438765A1 (en) 1977-07-01
SE7506804L (en) 1975-12-29
CH614935A5 (en) 1979-12-28
FI751730A (en) 1975-12-26
FR2276037B1 (en) 1979-03-02
JPS51125020A (en) 1976-11-01
AU8221675A (en) 1976-12-23
FR2276037A1 (en) 1976-01-23
NO752091L (en) 1975-12-30

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Legal Events

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