SU743580A3 - Method of producing bis-(2-aminocyclopentene-1-yl-1 thyocarbonyl) disulfides - Google Patents

Method of producing bis-(2-aminocyclopentene-1-yl-1 thyocarbonyl) disulfides Download PDF

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Publication number
SU743580A3
SU743580A3 SU772559902A SU2559902A SU743580A3 SU 743580 A3 SU743580 A3 SU 743580A3 SU 772559902 A SU772559902 A SU 772559902A SU 2559902 A SU2559902 A SU 2559902A SU 743580 A3 SU743580 A3 SU 743580A3
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USSR - Soviet Union
Prior art keywords
carbon atoms
ene
general formula
disulfides
group
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SU772559902A
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Russian (ru)
Inventor
Матолчи Дьердь
Барток Пирошка
Кишш Бела
Палоши Ева
Карпати Эгон
Спорни Ласло
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Рихтер Гедеон Ведьесети Дьяр Рт (Фирма)
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Publication of SU743580A3 publication Critical patent/SU743580A3/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

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  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

Novel N-substituted 2-amino-cyclopent-1-ene-1-dithiocarboxylic acids of the general formula <IMAGE> in which R denotes an unsubstituted straight or branched alkyl group having 5 or 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, which is substituted by alkoxy groups having 1 to 4 carbon atoms, or by hydroxyl, carboxyl and/or amino groups, an alkenyl group having 2 to 4 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or a phenyl group, are prepared by reacting 2-amino-cyclopent-1-ene-1-dithiocarboxylic acid with amines of the general formula NH2-R. The novel compounds have a dopamine- beta -hydroxylase-inhibiting effect.

Description

1one

Изобретение относитс  к способу получени  2-аминоциклопент-1-ен-1-тиокарбонилдисульфидов общей формулы IThis invention relates to a process for the preparation of 2-aminocyclopent-1-ene-1-thiocarbonyl disulfides of the general formula I

NHHNHH

HHRHhr

C-S-S-C S SC-S-S S S

хуhu

где R - алкил-С -С, незамещенный или замещенный гидроксильной группой , низшей алкоксигруппой, карбоксильной и/или аминогруппой, алкенил-Cg -Cj, , циклоалкил-С5 -С, , которые обладают биологической активностью и могут поэтому найти применение в медицине.where R is alkyl-C-C, unsubstituted or substituted by hydroxyl group, lower alkoxy group, carboxyl and / or amino group, alkenyl-Cg-Cj,, cycloalkyl-C5-C, which have biological activity and can therefore be used in medicine.

Известен способ получени  тиурамдисулвфидов , заключающийс  в окислении дитиокарбаминовых кислот известными методами, например, с помощью перекиси водррола или перманганата натри  Щ .A known method for the preparation of thiuram disulphides, which involves the oxidation of dithiocarbamic acids by known methods, for example, with the aid of aqdrol peroxide or sodium permanganate.

Цель изобретени  - разработка способа получени  новых биологически активных 2-аминоциклопент-1-ен-1-тиокарбонилдисульфидов овщей формулы 1, обладающих высокой биологической активностью.The purpose of the invention is to develop a method for the preparation of novel biologically active 2-aminocyclopent-1-ene-1-thiocarbonyl disulfides of formula 1 with high biological activity.

Это достигаетс  тем, что 2-аминоциклопент-1-ен-1-тиокарбонилди2This is achieved by the fact that 2-aminocyclopent-1-ene-1-thiocarbonyldi2

сульфидов 2-аминоциклопент-1-ен-1дитиокарбоновую кислоту общей формулы I I :sulfides 2-aminocyclopent-1-ene-1dithiocarboxylic acid of the general formula I I:

NHHNHH

CSHCSH

где R - имеет указанные значени , окисл ют с последук цим выделениемwhere R - has the indicated values, is oxidized with the subsequent release

10 целевого продукта в свободном виде.10 target product in free form.

Окисление провод т с помощью окислителей, обычно использующихс  дл  получени  дисульфидов, например, перекиси водорода или перманганатаThe oxidation is carried out using oxidizing agents commonly used to produce disulfides, such as hydrogen peroxide or permanganate.

16 кали . В качестве растворител  предпочтительно используют воду.16 potassium. Water is preferably used as a solvent.

Пример 1. 2-Аллиламиноциклопент-1-ен-1-тиокарбонилдисульфид . 2,98 г (0,015 мол ) 2-аллиламиноаО циклопент-1-ен-1-дитиокарбоновой кислоты суспендируют в 30 мл воды, затем добавл ют 6 г (0,015 мол ) гидроокиси натри  в виде 10%-ного раствора едкого натра и смесь встр хи-,Example 1. 2-Allylaminocyclopent-1-ene-1-thiocarbonyl disulfide. 2.98 g (0.015 mol) of 2-allylamino-O cyclopent-1-ene-1-dithiocarboxylic acid is suspended in 30 ml of water, then 6 g (0.015 mol) of sodium hydroxide is added in the form of a 10% sodium hydroxide solution and mixed in him-

25 вают 10 мин. При комнатной температуре добавл ют смесь 3 мл воды, 0,9 г (0,0075 мол ) концентрированной серной кислоты и 0,9 г (0,0075 мол ) 30%-ной перекиси водорода и смесь встр хивгиот 3 ч. Вы25 is 10 minutes. At room temperature, add a mixture of 3 ml of water, 0.9 g (0.0075 mol) of concentrated sulfuric acid and 0.9 g (0.0075 mol) of 30% hydrogen peroxide and a mixture of shakes 3 hours. You

Claims (1)

Формула изобретенияClaim Способ получения 2-аминоциклопент-1-ен-1-тиокарбонилдисульфидов общей формулы I так такThe method for producing 2-aminocyclopent-1-en-1-thiocarbonyldisulfides of the general formula I is as follows S S 1—1 где Я — алкил-С(_б , незамещенный или замещенный гидроксильной группой,низ35 шей алкоксигруппой, карбоксильной и/или аминогруппой, алкенил^Сг-С4, циклоалкил-С5-С6, отличающийся тем, что 2-аминоциклопент-1-ен-1-дитиокарбоновую кислоту об40 щей формулы I I:SS 1 - 1 where I is alkyl-C ( _b, unsubstituted or substituted by a hydroxyl group, a lower alkoxy group, a carboxyl and / or amino group, alkenyl ^ C g -C 4 , cycloalkyl-C 5 -C 6 , characterized in that 2 aminocyclopent-1-en-1-dithiocarboxylic acid of the general formula II: NHK 0ггн где R — имеет вышеуказанные значения, окисляют с последующим выделением целевого продукта в свободном виде.NHK 0gg n where R - has the above values, oxidize, followed by isolation of the target product in free form.
SU772559902A 1976-12-30 1977-12-28 Method of producing bis-(2-aminocyclopentene-1-yl-1 thyocarbonyl) disulfides SU743580A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU76RI610A HU175526B (en) 1976-12-30 1976-12-30 Process for producing 2-amino-cyclopent-1-2n2-1-dithiocarboxylic acid -disulfides

Publications (1)

Publication Number Publication Date
SU743580A3 true SU743580A3 (en) 1980-06-25

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JP (1) JPS5384949A (en)
AR (1) AR216308A1 (en)
AT (1) AT351501B (en)
AU (1) AU516353B2 (en)
BE (1) BE862408A (en)
CH (1) CH631701A5 (en)
DE (1) DE2758809A1 (en)
ES (1) ES465567A1 (en)
FI (1) FI66595C (en)
FR (1) FR2376132A1 (en)
GB (1) GB1582716A (en)
HU (1) HU175526B (en)
IL (1) IL53646A (en)
IN (1) IN146470B (en)
NL (1) NL7714514A (en)
NO (1) NO145237C (en)
PT (1) PT67482B (en)
SE (1) SE7714526L (en)
SU (1) SU743580A3 (en)
YU (1) YU309677A (en)
ZA (1) ZA777573B (en)

Also Published As

Publication number Publication date
JPS5384949A (en) 1978-07-26
ATA912077A (en) 1979-01-15
IL53646A (en) 1982-03-31
AU516353B2 (en) 1981-05-28
AU3197977A (en) 1979-06-28
PT67482A (en) 1978-01-01
AT351501B (en) 1979-07-25
GB1582716A (en) 1981-01-14
BE862408A (en) 1978-04-14
NO145237C (en) 1982-02-10
NL7714514A (en) 1978-07-04
YU309677A (en) 1983-01-21
HU175526B (en) 1980-08-28
PT67482B (en) 1979-05-30
FR2376132A1 (en) 1978-07-28
ZA777573B (en) 1978-10-25
FI66595B (en) 1984-07-31
IL53646A0 (en) 1978-03-10
SE7714526L (en) 1978-07-01
FR2376132B1 (en) 1979-10-19
FI773967A (en) 1978-07-01
FI66595C (en) 1984-11-12
AR216308A1 (en) 1979-12-14
DE2758809A1 (en) 1978-07-06
CH631701A5 (en) 1982-08-31
IN146470B (en) 1979-06-09
NO774502L (en) 1978-07-03
ES465567A1 (en) 1979-01-01
NO145237B (en) 1981-11-02

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