RU2000109633A - METHOD FOR PRODUCING PYRLINDOL HYDROCHLORIDE - Google Patents

METHOD FOR PRODUCING PYRLINDOL HYDROCHLORIDE

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Publication number
RU2000109633A
RU2000109633A RU2000109633/04A RU2000109633A RU2000109633A RU 2000109633 A RU2000109633 A RU 2000109633A RU 2000109633/04 A RU2000109633/04 A RU 2000109633/04A RU 2000109633 A RU2000109633 A RU 2000109633A RU 2000109633 A RU2000109633 A RU 2000109633A
Authority
RU
Russia
Prior art keywords
formula
hydrochloride
alkaline agent
methyl
pyrlindol
Prior art date
Application number
RU2000109633/04A
Other languages
Russian (ru)
Other versions
RU2249592C2 (en
Inventor
Массимо Феррари
Марчелло ГЕЦЦИ
Паоло БЕЛОТТИ
Фабрицио ДЗИНЕТТИ
Original Assignee
ЭРРЕДЖИЕРРЕ С.п.А.
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
Priority claimed from IT1999MI000802A external-priority patent/IT1312539B1/en
Application filed by ЭРРЕДЖИЕРРЕ С.п.А. filed Critical ЭРРЕДЖИЕРРЕ С.п.А.
Publication of RU2000109633A publication Critical patent/RU2000109633A/en
Application granted granted Critical
Publication of RU2249592C2 publication Critical patent/RU2249592C2/en

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Claims (7)

1. Способ синтеза гидрохлорида пирлиндола формулы I
Figure 00000001

с использованием гидрохлорида 6-метил-1-(2-хлорлэтил-имино)-1,2,3,4-тетрагидрокарбазола, отличающийся тем, что гидрохлорид 6-метил-1-(2-хлорэтил-имино)-1,2,3,4-тетрагидрокарбазола формулы IV
Figure 00000002

циклизуют с помощью щелочного агента в присутствии катализатора переноса фаз с получением 1,2,5,6-тетрагидро-8-метил-пиразин[3,2,1-j, k] -4Н-карбазола формулы VI
Figure 00000003

который подвергают восстановлению.1. The method of synthesis of pirlindole hydrochloride of the formula I
Figure 00000001

using 6-methyl-1- (2-chloroethyl-imino) -1,2,3,4-tetrahydrocarbazole hydrochloride, characterized in that 6-methyl-1- (2-chloroethyl-imino) -1,2 hydrochloride, 3,4-tetrahydrocarbazole formula IV
Figure 00000002

cyclized using an alkaline agent in the presence of a phase transfer catalyst to give 1,2,5,6-tetrahydro-8-methyl-pyrazine [3,2,1-j, k] -4H-carbazole of formula VI
Figure 00000003

which is being restored. 2. Способ по п. 1, в котором щелочной агент присутствует в молярном отношении от 1,5: 1 до 3: 1 по отношению к соединению формулы IV, катализатор переноса фаз в количестве 3 мас. %. 2. The method according to p. 1, in which the alkaline agent is present in a molar ratio of from 1.5: 1 to 3: 1 with respect to the compound of formula IV, the phase transfer catalyst in an amount of 3 wt. % 3. Способ по п. 2, в котором щелочным агентом является щелочной карбонат, выбранный из группы, включающей карбонат калия и карбонат натрия. 3. The method of claim 2, wherein the alkaline agent is an alkaline carbonate selected from the group consisting of potassium carbonate and sodium carbonate. 4. Способ по п. 2, в котором щелочной агент используют в соотношении 2,4: 1,1 по отношению к соединению формулы IV. 4. The method according to p. 2, in which the alkaline agent is used in a ratio of 2.4: 1.1 with respect to the compound of formula IV. 5. Способ по п. 1, в котором продукт формулы VI восстанавливают боргидридом натрия. 5. The method of claim 1, wherein the product of formula VI is reduced with sodium borohydride. 6. Способ по п. 1, который проводят в растворителе, выбранном из группы, состоящей из диметилформамида, диметилацетамида и монометилового эфира этиленгликоля. 6. The method according to p. 1, which is carried out in a solvent selected from the group consisting of dimethylformamide, dimethylacetamide and ethylene glycol monomethyl ether. 7. Способ по п. 6, в котором растворителем является диметилформамид. 7. The method of claim 6, wherein the solvent is dimethylformamide.
RU2000109633/04A 1999-04-16 2000-04-14 Method for production of pyrlindone hydrochloride RU2249592C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI99A000802 1999-04-16
IT1999MI000802A IT1312539B1 (en) 1999-04-16 1999-04-16 PROCESS FOR THE PREPARATION OF HYDROCHLORIDE PYRINDOL.

Publications (2)

Publication Number Publication Date
RU2000109633A true RU2000109633A (en) 2002-02-27
RU2249592C2 RU2249592C2 (en) 2005-04-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
RU2000109633/04A RU2249592C2 (en) 1999-04-16 2000-04-14 Method for production of pyrlindone hydrochloride

Country Status (9)

Country Link
EP (1) EP1044976B1 (en)
AT (1) ATE221070T1 (en)
DE (1) DE60000274T2 (en)
ES (1) ES2180483T3 (en)
HU (1) HUP0001558A3 (en)
IT (1) IT1312539B1 (en)
PL (1) PL339641A1 (en)
PT (1) PT1044976E (en)
RU (1) RU2249592C2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012150707A1 (en) 2011-05-02 2012-11-08 国立大学法人熊本大学 Low molecular weight compound which promotes induction of differentiation of stem cells into insulin-producing cells and method for inducing differentiation of stem cells into insulin-producing cells using low molecular weight compound
CN102952089B (en) * 2012-10-19 2015-07-08 江苏省农用激素工程技术研究中心有限公司 Preparation method of metamitron
CN104774208A (en) * 2015-04-24 2015-07-15 南京靖龙药物研发有限公司 Preparation method of deuterium-labeled pirlindole hydrochloride
EP3392251A1 (en) * 2017-04-21 2018-10-24 Tecnimede-Sociedade Tecnico-Medicinal, S.A. Process for the preparation of pirlindole enantiomers and its salts
EP3392250A1 (en) * 2017-04-21 2018-10-24 Tecnimede-Sociedade Tecnico-Medicinal, S.A. Process for the preparation of piperazine ring for the synthesis of pyrazinocarbazole derivatives
CN110950873A (en) * 2019-12-10 2020-04-03 河南大学 New synthesis method of paludidole

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