CS274854B2 - Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) iniole-acetic acids production - Google Patents

Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) iniole-acetic acids production

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Publication number
CS274854B2
CS274854B2 CS646489A CS646489A CS274854B2 CS 274854 B2 CS274854 B2 CS 274854B2 CS 646489 A CS646489 A CS 646489A CS 646489 A CS646489 A CS 646489A CS 274854 B2 CS274854 B2 CS 274854B2
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Czechoslovakia
Prior art keywords
general formula
above mentioned
mentioned meaning
origination
compound
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CS646489A
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Czech (cs)
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CS646489A2 (en
Inventor
Alan Howard Katz
Christopher Alexander Demerson
Leslie George Humber
Original Assignee
American Home Prod
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Priority claimed from US06/838,510 external-priority patent/US4670462A/en
Application filed by American Home Prod filed Critical American Home Prod
Publication of CS646489A2 publication Critical patent/CS646489A2/en
Publication of CS274854B2 publication Critical patent/CS274854B2/en

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Abstract

The solution concerns a method of production of substituted 1,3,4,9-tetrahydropyrano-[3,4-b]-indol-1-acetic acids of general formula I, where R<1> means alkyl residuum with 1 to 4 carbon atoms, R<2> and R<3> mean atoms of hydrogen or they form together the group -CH=CH-CH=CH- at origination of benzene nucleus, R<4> and R<5> mean hydrogen atom, alkyl residuum with 1 to 6 carbon atoms are halogen atom, as well as of slats of these compounds, acceptable from the pharmaceutical point of view by 1) condensation of the substituted methyl ester of indol-3-acetic acid of general formula VIII, where R<4> and R<5> are of the above mentioned meaning, with halogenide of general formula IX, where R<2> and R<3> are of the above mentioned meaning and X means atom of halogen from the group consisting of chlorine, brome, or iodine, resulting in origination of ester of α-substituted indol-3-acetic acid of general formula X, where R<2>, R<3>, R<4> and R<5> are of the above mentioned meaning, 2) by reduction compound of general formula X, resulting in origination of compound of general formula VI, where R<2>, R<3>, R<4> and R<5> are of the above mentioned meaning, 3) by introduction of the obtained compound of general formula VI into reaction with methyl ester of 3-methoxy-2-alkan acid of general formula VII, where R<1> is of the above mentioned meaning, resulting in origination of methyl ester of compound of general formula I, where R<1>, R<2>, R<3>, R<4> and R<5> are of the above mentioned meaning with subsequent hydrolysis of the ester obtained in this manner resulting in origination of a compound of general formula I.<IMAGE>
CS646489A 1986-03-11 1987-02-18 Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) iniole-acetic acids production CS274854B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/838,510 US4670462A (en) 1986-03-11 1986-03-11 Substituted 1,3,4,9-tetrahydropyrano(3,4-B)indole-1-acetic acids
CS107487A CS274612B2 (en) 1986-03-11 1987-02-18 Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) indol-1-acetic acids production

Publications (2)

Publication Number Publication Date
CS646489A2 CS646489A2 (en) 1990-11-14
CS274854B2 true CS274854B2 (en) 1991-11-12

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CS646489A CS274854B2 (en) 1986-03-11 1987-02-18 Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) iniole-acetic acids production

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CS646489A2 (en) 1990-11-14

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