SU1378782A3 - Способ получени производных 1,4-дигидропиридина - Google Patents

Способ получени производных 1,4-дигидропиридина Download PDF

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SU1378782A3
SU1378782A3 SU843750492A SU3750492A SU1378782A3 SU 1378782 A3 SU1378782 A3 SU 1378782A3 SU 843750492 A SU843750492 A SU 843750492A SU 3750492 A SU3750492 A SU 3750492A SU 1378782 A3 SU1378782 A3 SU 1378782A3
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Фразер Кемпбэлл Симон
Эдвард Кросс Питер
Кендрик Стаббс Джон
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Пфайзер Корпорейшн (Фирма)
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

Изобретение относитс  к гетероциклическим соединени м, в частности ;К способу получени  производных 1,4- дигидропиридина (ДП)общей формулы R -CHj-O- CH -CHa-Ra, где R, Гер) ОСгНчТ-CHR: -С (СООСНА ) С(СНО-Ш; Rj -N -(CHg)2 -NH-((5H2)i ; R - моно- или дихлорзамещенный фенил, которые  вл ютс  промежуточными продуктами в синтезе I,4-дигидропиридинов, обладающих биологически активными свойствами . Цель изобретени  - получение новых производных указанного класса. Получение ДП ведут гидрированием соединен ий общей формулы R -CH -0-CH CHj-R -CHg- -Z, где R и Rj имеют указанные значени ; Z - С1 или Н, в присутствии Pd/C-катализатора, при давлении 50 фунт, на I кв. дюйм, при 20-40 €

Description

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41
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см
Изобретение относитс  к способу получени  новых производных 1,4-ди- гидропиридина общей форьтулы
HI Н НзСООСн: СООС2Н0
HjC о -CHgCHi Н
где R - моно- или дихлорзамещенный
фенил,
которые  вл ютс  промежуточными продуктами в синтезе 1 ,4-дигидропириди-- нов, обладающих биологически активными свойствами.
Цель изобретени  - разработка на основе известного метода способа получени  новых производных 154-дигид- ропиридинов,  вл ющихс  промежуточ ными продуктами в синтезе производных 1,4-дигидропиридинов обладающих ценными фармакологическими свой™ ствами,
Пример 1. Получение 4 (2 хлорфенил)-3-этоксикарбонил 5 метоксикарбонил-6-метил- 2 /2 « (пиперазин-1 -ил) этоксиметил)- ,4 дигидропиридина и его бисоксалат- ной соли,
а) Раствор бисоксалатной соли 4 хлорбензилзащищенного пиперазина (П, ) 51 в метаноле (1500 мл) перемешивают и подвергают гидрированию на палладиевом на подложке из древесного угл  катализаторе (Oj5 г) при давлении 50 фунт, на 1 кв. дюйм и комнатной температуре в течение ночи. Катализатор от фильтровывают, растворитель выпаривают и остаток раздел ют между метиленхлоридом (100 мл) и разбав- лен:ным водным раствором аммиака (100 мл). Органическую фазу сушат (NagCO), профильтровывают, выпаривают до сухости и получают предлагаемое соединение в виде свободного основани , масла (3 г). Образец, превращенный в бисоксапатную соль в ацетоне, имел т. пл, 170 (разлагалс ) .
Вычислено, %: С 51,03; Н 5,66; N 6,38.
Найдено, %: С 51,72; Н 5,58; N 6,54.
,,(C.,,}, б) Раствор бензилзащищенного пиперазина (П, Z Н) 42 г в смеси метанола (1500 мл) и уксусной кислоты (9 мл) подвергают гидрированию при 0°С и давлении 50 фунт, на 1 кв. дюйм на 5%-ном палладиевом катализаторе с подложкой из древесного угл  (2 г) в течение ночи. После та- кой же обработки, как описано в примере 1а, получают предлагаемое соединение в виде бисоксалатной соли (19 г), идентичной соли, полученной по примеру 1а.
Примеры 2-3. Следующие соединени  получили аналогично способу , описанному в примере 16, из соответствующих исходных материалов. Характеристика соединений приве- дена в таблице.

Claims (1)

  1. Формула изобретени 
    Способ получени  производных 1,4- дигидропиридина общей формулы
    Hi Н HsCOOCx5 r COOCtHs
    НзС CH2-0-CHseif,
    Н
    где R - моно- или дихлорзамещенный
    фенил,
    отличающийс  тем, что 40 соединение общей формулы
    Hi S
    йэ осд О еооС|Н5
    ;пЛш,-«
    Нзс;П Ш8-в-Ш|Ш8-:
    Н
    где R, имеет указанные значени ;
    Z - хлор или водород, подвергают гидрогенолизу.
    CI С1
    Свободное основание
    Продолжение таблицы
    1,21 (t) ЗН,. 2,38 (S) ЗН, 2,60 (т) ПН, 3,60 (S) ЗН, 3,60 (t) 2Н, 4,05 (q) 2Н, 4,68 (S) 2Н, 4,95 (S) 1Н, 7,16 (т) ЗН, также ИК (Nujol) NH 3300 см- 1685 см
SU843750492A 1982-09-04 1984-06-11 Способ получени производных 1,4-дигидропиридина SU1378782A3 (ru)

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GB8225246 1982-09-04

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SU833641411A SU1364237A3 (ru) 1982-09-04 1983-09-02 Способ получени производных 1,4-дигидропиридина или их гидрохлоридов
SU843750492A SU1378782A3 (ru) 1982-09-04 1984-06-11 Способ получени производных 1,4-дигидропиридина

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EP (1) EP0106462B1 (ru)
JP (1) JPS5980663A (ru)
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DE4410822A1 (de) * 1994-03-24 1995-09-28 Schering Ag Neue Piperidin-Derivate

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GB8527698D0 (en) * 1985-11-09 1985-12-11 Pfizer Ltd Dihydropyridine antiischaemic & antihypertensive agents
JP2513197B2 (ja) * 1986-01-21 1996-07-03 日本新薬株式会社 ピログルタミド誘導体
DE3621104A1 (de) * 1986-06-24 1988-01-07 Heumann Pharma Gmbh & Co 1,4-dihydropyridinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
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IT1197012B (it) * 1986-07-29 1988-11-25 Boehringer Biochemia Srl 2-(aciltio) metil diidropiridine, un processo per la loro preparazione e composizioni farmaceutiche che le contengono
US4855001A (en) * 1987-02-10 1989-08-08 Lord Corporation Structural adhesive formulations and bonding method employing same
GB8712747D0 (en) * 1987-05-30 1987-07-01 Pfizer Ltd Therapeutic agents
KR0177894B1 (ko) * 1993-07-28 1999-03-20 아만 히데아키 항우울제
US5700801A (en) * 1994-12-23 1997-12-23 Karl Thomae, Gmbh Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them
EP0799202A1 (de) * 1994-12-23 1997-10-08 Dr. Karl Thomae GmbH Piperazinderivate, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung
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FR2829766A1 (fr) * 2001-09-14 2003-03-21 Lipha Derives d'oxamates comportant un heterocycle azote diversement substitue
WO2022175384A1 (en) * 2021-02-17 2022-08-25 Fundación Universidad Católica De Valencia San Vicente Mártir Small-molecule agents with antiviral activity against rna viruses

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4410822A1 (de) * 1994-03-24 1995-09-28 Schering Ag Neue Piperidin-Derivate

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EP0106462A3 (en) 1984-05-30
FI80262B (fi) 1990-01-31
ATE39112T1 (de) 1988-12-15
KR880000180B1 (ko) 1988-03-12
CS242881B2 (en) 1986-05-15
DK161700B (da) 1991-08-05
YU43598B (en) 1989-08-31
ES8602760A1 (es) 1985-12-01
YU43659B (en) 1989-10-31
ES525241A0 (es) 1986-01-16
KR840006236A (ko) 1984-11-22
PL243621A1 (en) 1985-05-07
HU191092B (en) 1987-01-28
EP0106462A2 (en) 1984-04-25
SU1364237A3 (ru) 1987-12-30
AU542454B2 (en) 1985-02-21
FI833117A (fi) 1984-03-05
DD215544A5 (de) 1984-11-14
CA1205470A (en) 1986-06-03
DK398383A (da) 1984-03-05
PT77283A (en) 1983-10-01
PL250618A1 (en) 1985-07-30
IE55904B1 (en) 1991-02-14
DK161700C (da) 1992-01-06
ES8604200A1 (es) 1986-01-16
YU179985A (en) 1986-10-31
CS639583A2 (en) 1985-08-15
IE832058L (en) 1984-03-04
AU1865883A (en) 1984-03-08
PH19166A (en) 1986-01-16
JPS5980663A (ja) 1984-05-10
DK398383D0 (da) 1983-09-01
FI833117A0 (fi) 1983-09-01
NZ205472A (en) 1985-08-16
IL69627A (en) 1986-08-31
NO833159L (no) 1984-03-05
EP0106462B1 (en) 1988-12-07
ES532038A0 (es) 1985-12-01
GR78985B (ru) 1984-10-02
US4539322A (en) 1985-09-03
PL143900B1 (en) 1988-03-31
JPS6222985B2 (ru) 1987-05-20
IL69627A0 (en) 1983-12-30
DE3378632D1 (en) 1989-01-12
PT77283B (en) 1986-05-19
ZA836514B (en) 1984-07-25
PL139499B1 (en) 1987-01-31
YU178583A (en) 1986-10-31
NO160259C (no) 1989-03-29
NO160259B (no) 1988-12-19

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