SU1240354A3 - Способ получени дигидрохлорида пирбутерола - Google Patents

Способ получени дигидрохлорида пирбутерола Download PDF

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Publication number
SU1240354A3
SU1240354A3 SU833534107A SU3534107A SU1240354A3 SU 1240354 A3 SU1240354 A3 SU 1240354A3 SU 833534107 A SU833534107 A SU 833534107A SU 3534107 A SU3534107 A SU 3534107A SU 1240354 A3 SU1240354 A3 SU 1240354A3
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USSR - Soviet Union
Prior art keywords
formula
hydrogen
compound
pyrbuterol
dihydrochloride
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SU833534107A
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English (en)
Inventor
Венделл Кью Беркели (Младший)
Сарджент Массетт Стефен
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Пфайзер Инк (Фирма)
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Publication of SU1240354A3 publication Critical patent/SU1240354A3/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Изобретение относитс  к усовершенствованному способу получени  дигид- рохлорида пирбутерола, про вл ющего. брюхорасшир ющую ак тивность, а также примен емого дл  лечени  застойной сердечной недостаточности.
Цель изобретени  - упрощение способа получени  дигидрохлорида пирбутерола
-Пример 1. 6- 1-ГидроЛси-2- -(К-трет-бут11пбензиламино) . -фенш1-4Н-1,3-диоКсино(5,4-Ь)пиридин (III). .
Раствор 33,0 г (0,13 моль) 6-(1,2- -этоксиэтш1)-2-фенш1-4Н-1,3-диокси- но(5,4-Ь)пиридина и 22,0 г (0,135 мол ) N-трет-бутилбензиламйна в 200 мл метанола нагревают в течение 16 ч при температуре кипени  с обратным холодильником. После охлаждени  осаж- даетс  целевой продукт, который пере- кристаллизовываетс  из изопропанола с получением 29,4 г (54%) аминоспир- та (IJI), т,п, 126-130 с. . Найдено, %: С 75,04, Н 7,21, N7,15,
С 74,61, Н 7,23,
Вычислено,
N 6,69
ПРИ м е р 2, 2-Гидроксиметил- -3- гидрокси-6- 1-гидрокси-2-(Н-трет- бутилбензиламино)-этил пиридина ди- гидрохлорид.
Раствор 8,40 г (0,02 моль) 6-fl- -гидpoкcи-2-(N-тpeт-бyтилбeнзилaмиРедактор Н,Данкулич Заказ 3416/60
Составитель М,Борин
Техред В.Кадар Корректор М,Шароши
Тираж 379 Подписное ВНИИПИ Государственного комитета СССР
по делам изобретений и открытий 113035, Москва, Ж-35, Раушска  наб,, д, 4/5
Производственно-полиграфическое предпри тие, г, Ужгород, ул. Проектна , 4
5 0 5
0
но) этил |-2-фенил-4Н-1,3-диоксинр(5,4- -Ь)пиркдина в 75 мл метанола, содер- жап(его 10 мл концентрированной хдот ристоводородной кислоты, перемешивают при комнатной температуре в тече ние 4ч, затем растворитель упаривают в вакууме с получением твердого вещества. Перекристаллизаци  из изо- пропанола/метанола дает 6,30 г (74%) 2- ГИДроксиэтил-3-гищ)окси-6-С1-гид- рокси-2-(Н-трет-бутш1бензш1амино)- этил пиридина дигидрохлорида, т,ш1, 173-175 с (с разложением), Найдено, %: С 55,73, Н 7,28, N 6,90,
,j03, 2НС1 1/2Н20 Вычислено, % С 55,34, Н 7,09,
N 6,80.;.
Пример 3, Пирбутерола дигид-т рохпорид,
В сосуд Парра (250 мл) помещают 0,50 г (0,0012 моль) 6- 1-гидрокси- -2-(Ы-трет-бутилбензиламино)этил2-2- -фенил-4Л-1,3-диоксино(5,4-Ь) пири- дина и 500 мг 5%-ного паллади  на угле в 20 мл метанола. При давлении водорода 345 кПа смесь подвергают реагированию при комнатной температуре в течение 2 ч. Катализатор удал ют фильтрованием в атмосфере азота и растворители насыщают сухим хлористым водородом с получением пирбутерола 250 мг (67%), т.пл, 174-176 0 (с разложением),

Claims (1)

  1. СПОСОБ ПОЛУЧЕНИЯ ДИГИДРОХЛОРИДА ПИРБУТЕРОЛА формулы путем взаимодействия эпоксида формулы с органическим амином с последующим отщеплением защитных групп сольволизом в кислой среде,'о т л и чающийся тем, что с целью упрощения процесса, в качестве органического амина используют N-трет-бутилбензиламин и полученный промежуточный продукт формулы подвергают гидрогенолизу над Pd/C, а затем сольволизу.
    1240354 АЗ
    1 1240
SU833534107A 1981-02-09 1983-01-05 Способ получени дигидрохлорида пирбутерола SU1240354A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US23292381A 1981-02-09 1981-02-09

Publications (1)

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SU1240354A3 true SU1240354A3 (ru) 1986-06-23

Family

ID=22875140

Family Applications (4)

Application Number Title Priority Date Filing Date
SU823392299A SU1194273A3 (ru) 1981-02-09 1982-02-03 Способ получени пирбутерола или его аналогов
SU833535711A SU1217253A3 (ru) 1981-02-09 1983-01-05 Способ получени пирбутерола дигидрохлорида
SU833534854A SU1250170A3 (ru) 1981-02-09 1983-01-05 Способ получени дихлоргидрата пирбутерола
SU833534107A SU1240354A3 (ru) 1981-02-09 1983-01-05 Способ получени дигидрохлорида пирбутерола

Family Applications Before (3)

Application Number Title Priority Date Filing Date
SU823392299A SU1194273A3 (ru) 1981-02-09 1982-02-03 Способ получени пирбутерола или его аналогов
SU833535711A SU1217253A3 (ru) 1981-02-09 1983-01-05 Способ получени пирбутерола дигидрохлорида
SU833534854A SU1250170A3 (ru) 1981-02-09 1983-01-05 Способ получени дихлоргидрата пирбутерола

Country Status (26)

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EP (4) EP0058069B1 (ru)
JP (4) JPS57150665A (ru)
KR (1) KR860000623B1 (ru)
AR (4) AR231439A1 (ru)
AT (2) ATE20882T1 (ru)
AU (1) AU530826B2 (ru)
CA (1) CA1179677A (ru)
CS (1) CS229678B2 (ru)
DD (2) DD210034A5 (ru)
DE (2) DE3272061D1 (ru)
DK (1) DK157541C (ru)
EG (1) EG16242A (ru)
ES (4) ES8305721A1 (ru)
FI (1) FI820396L (ru)
GR (1) GR75867B (ru)
GT (1) GT198273686A (ru)
IE (2) IE52325B1 (ru)
IL (1) IL64954A (ru)
NO (4) NO820371L (ru)
NZ (1) NZ199646A (ru)
PH (4) PH20622A (ru)
PL (4) PL130917B1 (ru)
PT (1) PT74397B (ru)
SU (4) SU1194273A3 (ru)
YU (3) YU42756B (ru)
ZA (1) ZA82778B (ru)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3615293A1 (de) * 1986-05-06 1987-11-12 Bayer Ag Verwendung von heteroarylethylaminen zur leistungsfoerderung bei tieren, heteroarylethylamine und verfahren zu ihrer herstellung

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3700681A (en) * 1971-02-16 1972-10-24 Pfizer 2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)pyridines
BE795937A (fr) * 1972-03-01 1973-08-27 Pepro Procede d'hydroxymethylation d'une 3-hydroxy-pyridine substituee
AR207639A1 (es) * 1973-12-26 1976-10-22 Pfizer Un procedimiento para preparar pirido (3,2-d)1,3-dioxin-6-epoxietanos y compuestos intermediarios desprovistos de actividad terapeutica
US4031108A (en) * 1974-10-09 1977-06-21 Pfizer Inc. 2-Hydroxymethyl-3-benzyloxypyridine-6-epoxyethane
US3952101A (en) * 1975-04-14 1976-04-20 Smithkline Corporation α-Amino methyl-5-hydroxy-2-pyridinemethanols

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EP0058072A3 (en) 1982-08-25
ES509430A0 (es) 1983-04-16
EP0058069A3 (en) 1982-09-01
EP0058072A2 (en) 1982-08-18
NO824274L (no) 1982-08-10
ES8403110A1 (es) 1984-03-01
DE3272061D1 (en) 1986-08-28
JPS6059231B2 (ja) 1985-12-24
CS229678B2 (en) 1984-06-18
IE52326B1 (en) 1987-09-16
SU1217253A3 (ru) 1986-03-07
AU530826B2 (en) 1983-07-28
YU26682A (en) 1985-04-30
ES8305721A1 (es) 1983-04-16
PL130918B1 (en) 1984-09-29
DD210034A5 (de) 1984-05-30
NZ199646A (en) 1985-11-08
ES518972A0 (es) 1984-03-01
YU201984A (en) 1985-04-30
EP0058070A2 (en) 1982-08-18
PL239426A1 (en) 1983-04-25
ES8403111A1 (es) 1984-03-01
IL64954A (en) 1986-03-31
KR830009028A (ko) 1983-12-17
FI820396L (fi) 1982-08-10
AR229373A1 (es) 1983-07-29
PL130678B1 (en) 1984-08-31
PL239428A1 (en) 1983-04-25
SU1250170A3 (ru) 1986-08-07
AU8027182A (en) 1982-08-19
IE52325B1 (en) 1987-09-16
PH19164A (en) 1986-01-16
PL130580B1 (en) 1984-08-31
DE3272793D1 (en) 1986-10-02
JPS60208962A (ja) 1985-10-21
JPS6193164A (ja) 1986-05-12
PH20622A (en) 1987-03-06
NO824273L (no) 1982-08-10
PL235000A1 (en) 1983-04-11
SU1194273A3 (ru) 1985-11-23
EP0058071A2 (en) 1982-08-18
JPS6119624B2 (ru) 1986-05-17
EP0058069B1 (en) 1986-08-27
NO824275L (no) 1982-08-10
EP0058071A3 (en) 1982-08-25
ES518971A0 (es) 1984-03-01
GT198273686A (es) 1983-07-30
JPS57150665A (en) 1982-09-17
IE820273L (en) 1982-08-09
JPS6059911B2 (ja) 1985-12-27
EP0058070A3 (en) 1982-08-25
DK157541C (da) 1990-06-11
YU42908B (en) 1988-12-31
YU43389B (en) 1989-06-30
ES518973A0 (es) 1984-03-01
CA1179677A (en) 1984-12-18
PT74397B (en) 1984-10-09
YU201884A (en) 1985-04-30
EP0058069A2 (en) 1982-08-18
AR229712A1 (es) 1983-10-31
ZA82778B (en) 1983-01-26
EP0058071B1 (en) 1986-07-23
IE820275L (en) 1982-08-09
ATE20882T1 (de) 1986-08-15
KR860000623B1 (ko) 1986-05-24
DK52182A (da) 1982-09-17
EG16242A (en) 1989-01-30
NO820371L (no) 1982-08-10
PT74397A (en) 1982-03-01
JPS6135184B2 (ru) 1986-08-12
AR229374A1 (es) 1983-07-29
ES8403112A1 (es) 1984-03-01
JPS60208964A (ja) 1985-10-21
GR75867B (ru) 1984-08-02
PH20292A (en) 1986-11-18
PL239427A1 (en) 1983-04-25
PH19167A (en) 1986-01-16
PL130917B1 (en) 1984-09-29
DK157541B (da) 1990-01-22
AR231439A1 (es) 1984-11-30
ATE21691T1 (de) 1986-09-15
YU42756B (en) 1988-12-31
IL64954A0 (en) 1982-04-30
DD202544A5 (de) 1983-09-21

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