SU420169A3 - METHOD FOR OBTAINING TRICYCLIC DERIVATIVES OF AAMINOSPIRATES 12 The invention relates to the preparation of new T'rAcclimate amino alcohol alcohols of the general formula IC-CCNgHgCHN ^ OI10 where A, X and Y have the indicated values, and Hal - chlorine or bromine interacts with the interactions of the interactions of the groups, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions that have the specified values; P1HoN— (CH2) “—CH20H in which p is as defined above. The reaction is carried out in an appropriate organic solvent, such as nitro methane, acetonitrile or dimethylformamide. In the presence of a hydrogen halide acceptor formed during p actions This acceptor may be an excess of co-amino alcohol (III), a tertiary amine, a pyridine base, an alkali or alkaline earth metal carbonate or bicarbonate. The reaction is exothermic and takes place at a temperature between 20 and 100 ° C. Producers of general formula I can be isolated in free form or in the form of salts with mineral or organic acids. - Google Patents

METHOD FOR OBTAINING TRICYCLIC DERIVATIVES OF AAMINOSPIRATES 12 The invention relates to the preparation of new T'rAcclimate amino alcohol alcohols of the general formula IC-CCNgHgCHN ^ OI10 where A, X and Y have the indicated values, and Hal - chlorine or bromine interacts with the interactions of the interactions of the groups, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions that have the specified values; P1HoN— (CH2) “—CH20H in which p is as defined above. The reaction is carried out in an appropriate organic solvent, such as nitro methane, acetonitrile or dimethylformamide. In the presence of a hydrogen halide acceptor formed during p actions This acceptor may be an excess of co-amino alcohol (III), a tertiary amine, a pyridine base, an alkali or alkaline earth metal carbonate or bicarbonate. The reaction is exothermic and takes place at a temperature between 20 and 100 ° C. Producers of general formula I can be isolated in free form or in the form of salts with mineral or organic acids.

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Publication number
SU420169A3
SU420169A3 SU1713118A SU1713118A SU420169A3 SU 420169 A3 SU420169 A3 SU 420169A3 SU 1713118 A SU1713118 A SU 1713118A SU 1713118 A SU1713118 A SU 1713118A SU 420169 A3 SU420169 A3 SU 420169A3
Authority
SU
USSR - Soviet Union
Prior art keywords
interactions
hal
chlorine
bromine
general formula
Prior art date
Application number
SU1713118A
Other languages
Russian (ru)
Inventor
бретени йзо
Original Assignee
Иностранцы Шарль Мален, Моник Денос , Жан Клод Пуан
Иностранна фирма Юньон Сосьете Франсэз Решерш Медикальх
где радикал
которых число или
число или низший алкил, содержащий атомов углерода,
целое число включн тельно,
, водород или галоген Предлагаемый способ основан известной реакции галоидалкила амином Использу известную реакцию, получают новые три циклические производные аминоопиртов, торые обладают физиологической активностью , могут иайти шримененне фармацевтической промышленности
Предложенный способ заключаетс том, что галоидное производное общей формулы
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 Иностранцы Шарль Мален, Моник Денос , Жан Клод Пуан, Иностранна фирма Юньон Сосьете Франсэз Решерш Медикальх, где радикал, которых число или, число или низший алкил, содержащий атомов углерода,, целое число включн тельно,, , водород или галоген Предлагаемый способ основан известной реакции галоидалкила амином Использу известную реакцию, получают новые три циклические производные аминоопиртов, торые обладают физиологической активностью , могут иайти шримененне фармацевтической промышленности, Предложенный способ заключаетс том, что галоидное производное общей формулы filed Critical Иностранцы Шарль Мален, Моник Денос , Жан Клод Пуан
Application granted granted Critical
Publication of SU420169A3 publication Critical patent/SU420169A3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D281/00Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02Seven-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

Mill, такими как сол на , бромистоводородна , сарна , фосфор-на , уксусна , пропионова , малеинова , фумарова , метансульфокислота , BiHHFiaH, лшюнна , щавелева  и бензойна  кислота.Mill, such as hydrochloric acid, hydrobromic acid, sarna, phosphorus, acetic acid, propionic acid, maleic acid, fumaric acid, methanesulfonic acid, BiHHFiaH, lushunna, oxalic acid and benzoic acid.

Кроме того, производные общей формулы I, в которой X и Y различные или А  вл етс  асимметричным мостиком, могут существовать в форме оптических изомеров.In addition, derivatives of general formula I, in which X and Y are different or A is an asymmetric bridge, may exist in the form of optical isomers.

Пример 1. Добавл ют при перемешивании раствор 30,6 г (0,133 моль) 5- хлордибелзо - (а, d) - циклогептадиена в 300 Л1Л нитрометана в теплый раствор 35 г (0,267 моль) 7-амнногептанола в 30 мл иитрометаиола. Реакци  слабо экзотермическа . В результате .выпадает хлоргидрат 7 - аминогептанола.Example 1. A solution of 30.6 g (0.133 mol) of 5-chloro-dibelzo-a (d, d) -cycloheptadiene in 300 L1L of nitromethane is added with stirring to a warm solution of 35 g (0.267 mol) of 7-amnepheptanol in 30 ml of nitromethiol. The reaction is slightly exothermic. As a result, 7-aminoheptanol hydrochloride falls out.

Реакционную смесь оставл ют «а ночь, зате-м фильтруют, фильтрат выпаривают досуха в вакууме. В осадок добавл ют воду и эфир. Органическа  фаза декантируетс , промываетс  до нейтрального состо ни , сушитс  сульфатом натри , зате.м выпариваетс  в вакууме.The reaction mixture is left overnight, then filtered, the filtrate is evaporated to dryness in vacuo. Water and ether are added to the precipitate. The organic phase is decanted, washed to neutrality, dried with sodium sulfate, then evaporated in vacuo.

Получают 35 г дибензо - (а, d) -циклогептадиенил - 5 - амино -7 - гептанола, содержание в котором чистого продукта, определенное титрованием с хлорной кислотой, составл ет 95%.35 g of dibenzo - (a, d) -cycloheptadienyl - 5 - amino-7 - heptanol are obtained, the content of which in the pure product determined by titration with perchloric acid is 95%.

Это сырое основание после обработки раствором газообразного хлористого водорода в эфире и перекристаллизации из воды дает 23,4 г хлоргйдрата дибензо - (а, d) - циклогептадиенил - 5 - 7 - аминогептанола, который плавитс  при 210°С.This crude base after treatment with a solution of hydrogen chloride gas in ether and recrystallization from water gives 23.4 g of dibenzo - (a, d) chlorohydrate cycloheptadienyl - 5-7 aminoheptanol, which melts at 210 ° C.

Примеры 2-4. Следующие производные получают способом, описанным в примере 1:Examples 2-4. The following derivatives are obtained by the method described in example 1:

дибензо - (а, d) - циклогептадиенил - 5 - 4 - амннобутанол, т. пл. соответствующего хлоргидрата 185°С, получали из 5-хлорд1Ябензо- (а, d)-циклогептадмена и 4-а.минобутанола;dibenzo - (a, d) - cycloheptadienyl - 5 - 4 - amnnobutanol, so pl. the corresponding hydrochloride, 185 ° C, was obtained from 5-chloro-1-benzo (a, d) -cycloheptadmen and 4-a. minobutanol;

дибензо- (а, d) - циклогептадиенил - 5 -5-амииопентанол , т. кип. при 0,05 мм рт. ст. 168-170°С, n22i) 1,5836, получали из 5-хлордибензо - (а, d) - циклогептадиена и 5 - аминопентанола;Dibenzo- (a, d) - cycloheptadienyl - 5 -5-amyiopentanol, t. Kip. with 0.05 mm Hg. Art. 168-170 ° C, n22i) 1.5836, obtained from 5-chlorodibenzo - (a, d) - cycloheptadiene and 5 - aminopentanol;

дибензо - (а, d) - циклогептадиенил - 5 - 11 - аминоундеканол, т. пл. соответствующего хлоргидрата 120°С (ацето-нитрил), получают из 5 - хлордибеизо - (а, d) - циклогептадиена и 11 - аминоундекаиола.dibenzo - (a, d) - cycloheptadiene - 5 - 11 - aminoundecanol, t. Pl. the corresponding hydrochloride 120 ° C (aceto-nitrile) is obtained from 5 - chlordibeiso - (a, d) - cycloheptadiene and 11 - aminoundecaiol.

Предмет 1И з о б р е т е н и  Subject 1 and sbretien

Способ получени  трнциклических производных аминоспиртов общей формулы IThe method of obtaining trcyclic derivatives of amino alcohols of general formula I

СН Ш-()-СН20НСН Ш - () - СН20Н

где А - радикал - (СНг) « ,- СН СП -, - (СП2)/,О -,-(CH2)pS-,S02 или NR в которых т - число 1, 2 нли 3, р - число 1 или 2, R - низший алкил, содержащий от 1 до 5 атомов углерода,where A is the radical - (CHg) ", - CH CH SP -, - (SP2) /, O -, - (CH2) pS-, S02 or NR in which t is the number 1, 2 nli 3, p is the number 1 or 2, R is lower alkyl containing from 1 to 5 carbon atoms,

п - целое число от 3 до 10 включительно ,n is an integer from 3 to 10 inclusive,

X и Y - водород или галоген, или их солей, отличающийс  тем, что галолдное производное общей формулы ИX and Y are hydrogen or halogen, or their salts, characterized in that the halide derivative of the general formula I

где А, X и Y имеют указан ое значение, и Па1 - хлор или брО:М,where A, X and Y have the specified value, and Pa1 is chlorine or brO: M,

подвергают взаимодействию с « - аминоспиртом общей формулы 1Пsubjected to interaction with "- amino alcohol of General formula 1P

ПаМ- (СП2),г -СИгОНPaM- (SP2), g - SIGON

где п - имеет указанное значение, с последующим выделением целевого продукта в свободном виде или в виде соли.where p - has the specified value, followed by separation of the target product in free form or in the form of salt.

SU1713118A 1970-11-04 1971-11-04 METHOD FOR OBTAINING TRICYCLIC DERIVATIVES OF AAMINOSPIRATES 12 The invention relates to the preparation of new T'rAcclimate amino alcohol alcohols of the general formula IC-CCNgHgCHN ^ OI10 where A, X and Y have the indicated values, and Hal - chlorine or bromine interacts with the interactions of the interactions of the groups, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions that have the specified values; P1HoN— (CH2) “—CH20H in which p is as defined above. The reaction is carried out in an appropriate organic solvent, such as nitro methane, acetonitrile or dimethylformamide. In the presence of a hydrogen halide acceptor formed during p actions This acceptor may be an excess of co-amino alcohol (III), a tertiary amine, a pyridine base, an alkali or alkaline earth metal carbonate or bicarbonate. The reaction is exothermic and takes place at a temperature between 20 and 100 ° C. Producers of general formula I can be isolated in free form or in the form of salts with mineral or organic acids. SU420169A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5246970 1970-11-04

Publications (1)

Publication Number Publication Date
SU420169A3 true SU420169A3 (en) 1974-03-15

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ID=10464037

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Application Number Title Priority Date Filing Date
SU1713118A SU420169A3 (en) 1970-11-04 1971-11-04 METHOD FOR OBTAINING TRICYCLIC DERIVATIVES OF AAMINOSPIRATES 12 The invention relates to the preparation of new T'rAcclimate amino alcohol alcohols of the general formula IC-CCNgHgCHN ^ OI10 where A, X and Y have the indicated values, and Hal - chlorine or bromine interacts with the interactions of the interactions of the groups, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions, and the Hal - chlorine or bromine has interactions that have interactions that have the specified values; P1HoN— (CH2) “—CH20H in which p is as defined above. The reaction is carried out in an appropriate organic solvent, such as nitro methane, acetonitrile or dimethylformamide. In the presence of a hydrogen halide acceptor formed during p actions This acceptor may be an excess of co-amino alcohol (III), a tertiary amine, a pyridine base, an alkali or alkaline earth metal carbonate or bicarbonate. The reaction is exothermic and takes place at a temperature between 20 and 100 ° C. Producers of general formula I can be isolated in free form or in the form of salts with mineral or organic acids.

Country Status (10)

Country Link
JP (1) JPS535294B1 (en)
AU (1) AU472765B2 (en)
BE (1) BE774861R (en)
CH (1) CH546732A (en)
DE (2) DE2166662C3 (en)
FR (1) FR2112436B2 (en)
GB (1) GB1347977A (en)
NL (1) NL7115092A (en)
SE (2) SE383148B (en)
SU (1) SU420169A3 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH629667A5 (en) * 1978-03-28 1982-05-14 Science Union & Cie PHARMACEUTICAL COMPOSITION ACTING ON GASTROINTESTINAL MOTORITY.
JPS55103369U (en) * 1979-01-16 1980-07-18
JPS55123572U (en) * 1979-02-26 1980-09-02
AU2015229258B2 (en) * 2014-03-12 2020-01-30 The Trustees Of Columbia University In The City Of New York A new class of Mu-Opioid receptor agonists

Also Published As

Publication number Publication date
JPS535294B1 (en) 1978-02-25
NL7115092A (en) 1972-05-08
FR2112436A2 (en) 1972-06-16
DE2166662B2 (en) 1978-07-13
DE2154867A1 (en) 1972-06-08
SE7409512L (en) 1974-07-22
SE407406B (en) 1979-03-26
FR2112436B2 (en) 1975-08-01
CH546732A (en) 1974-03-15
SE383148B (en) 1976-03-01
DE2166662A1 (en) 1975-01-23
DE2166662C3 (en) 1979-03-15
AU3464571A (en) 1973-04-19
GB1347977A (en) 1974-02-27
BE774861R (en) 1972-05-03
AU472765B2 (en) 1976-06-03

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