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 productionInfo
- 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
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- general formula
- above mentioned
- mentioned meaning
- origination
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000004702 methyl esters Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- ZHNMDZOUDCSDJS-UHFFFAOYSA-N 2-(1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid Chemical class N1C2=CC=CC=C2C2=C1C(CC(=O)O)OCC2 ZHNMDZOUDCSDJS-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- -1 α-substituted indol-3-acetic acid Chemical class 0.000 abstract 1
Landscapes
- Indole Compounds (AREA)
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>
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 |
Family
ID=25745377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS646489A CS274854B2 (en) | 1986-03-11 | 1987-02-18 | Method of substituted 1,3,4,9-tetrahydropyrano (3,4-b) iniole-acetic acids production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS274854B2 (en) |
-
1987
- 1987-02-18 CS CS646489A patent/CS274854B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS646489A2 (en) | 1990-11-14 |
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