KR830009028A - 피르부테롤, 그 유사체 및 이들 중간체의 제조방법 - Google Patents
피르부테롤, 그 유사체 및 이들 중간체의 제조방법 Download PDFInfo
- Publication number
- KR830009028A KR830009028A KR1019820000528A KR820000528A KR830009028A KR 830009028 A KR830009028 A KR 830009028A KR 1019820000528 A KR1019820000528 A KR 1019820000528A KR 820000528 A KR820000528 A KR 820000528A KR 830009028 A KR830009028 A KR 830009028A
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- KR
- South Korea
- Prior art keywords
- represented
- general formula
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- following general
- hydrocracking
- Prior art date
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- 239000000543 intermediate Substances 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 6
- -1 methylphosphonium halogen compound Chemical class 0.000 claims 5
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 238000004517 catalytic hydrocracking Methods 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000003797 solvolysis reaction Methods 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims 1
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 229960005414 pirbuterol Drugs 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 하기 일반식(II)로 표시되는 피리딘카르발데히드를 제4급 메틸포스포늄 할로겐화합물과 반응시켜 하기 일반식(III)으로 표시되는 비닐피리딘(III)을 생성시키고, 비닐피리딘(III)을 과산으로 산화시켜 하기 일반식(IV)로 표시되는 에폭시드 N-옥사이드(IV)를 생성시킨 다음, 에폭시드 N-옥사이드(IV)를 제3급-부틸아민에 의해 에폭시드 개환시켜 하기 일반식(VI)로 표시되는 아민을 생성시키고, 아민(VI)을 수소 첨가 분해를 행하거나 또는 가용매 분해 및 수소첨가 분해를 병용하여 하기 일반식(I)로 표시되는 화합물을 생성시킴을 특징으로 하는 피르부테롤, 그 유사체 및 이들 중간체의 제조방법.상기 식들에 있어서,R은 수소원자, 메틸기 또는 히드록시메틸기이고,R1은 벤질기이며,R2는 수소원자 또는 메틸기이거나, 또는 R1과 R2는 함께 취하여 형성되는 " T-2-1" 기이다.
- 하기 구조식으로 표시되는 화합물을 약 염기 존재하의 포름알데히드의 수용액 중에서 가열시킴을 특징으로 하는 피르부테롤의 제조방법.
- 제2항에 있어서, 약 염기가 트리메틸아민임을 특징으로 하는 방법.
- 다음 일반식(Y는 벤질기 또는 아세틸기임)으로 표시되는 제1의 화합물을 초산 무수물 중에서 가열시켜 다음 일반식으로 표시되는 제2의 화합물을 생성시킨 다음, 제2의 화합물을 가용매 분해시키거나 또는 가용매 분해 및 수소첨가 분해를 병용하여 피르부테롤을 생성시킴을 특징으로 하는 피르부테롤의 제조방법.
- N-제3-부틸벤질아민을 하기 일반식(VII)로 표시되는 에폭시드와 반응시켜 하기 일반식(VIII)으로 표시되는 아민을 생성시킨 다음, 아민(VIII)을 수소첨가 분해시키거나 또는 가용매 분해 수소첨가 분해를 병용하여 하기 일반식(I)로 표시되는 화합물을 생성시킴을 특징으로 하는 피르부테롤, 그 유사체 및 이들 중간체의 제조방법.상기 식들에 있어서,R는 수소원자, 메틸기 또는 히드록시메틸기이고,R1는 벤질기이며,R2는 수소원자 또는 메틸기이거나, 또는 R1과 R2는 함께 취하여 형성되는 " T-7 " 기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019860002099A KR860000625B1 (ko) | 1981-02-09 | 1986-03-21 | 피르부테롤 및 그의 유도체의 제조 방법 |
| KR1019860002098A KR860000624B1 (ko) | 1981-02-09 | 1986-03-21 | 피르부테롤의 제조 방법 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23292381A | 1981-02-09 | 1981-02-09 | |
| US232923 | 1988-08-18 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860002098A Division KR860000624B1 (ko) | 1981-02-09 | 1986-03-21 | 피르부테롤의 제조 방법 |
| KR1019860002099A Division KR860000625B1 (ko) | 1981-02-09 | 1986-03-21 | 피르부테롤 및 그의 유도체의 제조 방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009028A true KR830009028A (ko) | 1983-12-17 |
| KR860000623B1 KR860000623B1 (ko) | 1986-05-24 |
Family
ID=22875140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200528A KR860000623B1 (ko) | 1981-02-09 | 1982-02-08 | 피르부테롤 및 그의 유도체의 제조 방법 |
Country Status (26)
| Country | Link |
|---|---|
| EP (4) | EP0058069B1 (ko) |
| JP (4) | JPS57150665A (ko) |
| KR (1) | KR860000623B1 (ko) |
| AR (4) | AR231439A1 (ko) |
| AT (2) | ATE20882T1 (ko) |
| AU (1) | AU530826B2 (ko) |
| CA (1) | CA1179677A (ko) |
| CS (1) | CS229678B2 (ko) |
| DD (2) | DD210034A5 (ko) |
| DE (2) | DE3272061D1 (ko) |
| DK (1) | DK157541C (ko) |
| EG (1) | EG16242A (ko) |
| ES (4) | ES8305721A1 (ko) |
| FI (1) | FI820396L (ko) |
| GR (1) | GR75867B (ko) |
| GT (1) | GT198273686A (ko) |
| IE (2) | IE52325B1 (ko) |
| IL (1) | IL64954A (ko) |
| NO (4) | NO820371L (ko) |
| NZ (1) | NZ199646A (ko) |
| PH (4) | PH20622A (ko) |
| PL (4) | PL130917B1 (ko) |
| PT (1) | PT74397B (ko) |
| SU (4) | SU1194273A3 (ko) |
| YU (3) | YU42756B (ko) |
| ZA (1) | ZA82778B (ko) |
Families Citing this family (1)
| 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 |
Family Cites Families (5)
| 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 |
-
1982
- 1982-02-03 SU SU823392299A patent/SU1194273A3/ru active
- 1982-02-04 NZ NZ199646A patent/NZ199646A/en unknown
- 1982-02-04 CS CS82781A patent/CS229678B2/cs unknown
- 1982-02-05 GR GR67223A patent/GR75867B/el unknown
- 1982-02-05 AR AR288347A patent/AR231439A1/es active
- 1982-02-05 GT GT198273686A patent/GT198273686A/es unknown
- 1982-02-08 EP EP82300602A patent/EP0058069B1/en not_active Expired
- 1982-02-08 DE DE8282300604T patent/DE3272061D1/de not_active Expired
- 1982-02-08 DD DD82253605A patent/DD210034A5/de unknown
- 1982-02-08 DD DD82237264A patent/DD202544A5/de not_active IP Right Cessation
- 1982-02-08 IE IE273/82A patent/IE52325B1/en not_active IP Right Cessation
- 1982-02-08 AT AT82300604T patent/ATE20882T1/de active
- 1982-02-08 EP EP82300604A patent/EP0058071B1/en not_active Expired
- 1982-02-08 NO NO820371A patent/NO820371L/no unknown
- 1982-02-08 EP EP82300605A patent/EP0058072A3/en not_active Withdrawn
- 1982-02-08 JP JP57018693A patent/JPS57150665A/ja active Granted
- 1982-02-08 EP EP82300603A patent/EP0058070A3/en not_active Withdrawn
- 1982-02-08 FI FI820396A patent/FI820396L/fi not_active Application Discontinuation
- 1982-02-08 DK DK052182A patent/DK157541C/da not_active IP Right Cessation
- 1982-02-08 ES ES509430A patent/ES8305721A1/es not_active Expired
- 1982-02-08 DE DE8282300602T patent/DE3272793D1/de not_active Expired
- 1982-02-08 PT PT74397A patent/PT74397B/pt unknown
- 1982-02-08 KR KR8200528A patent/KR860000623B1/ko active
- 1982-02-08 CA CA000395768A patent/CA1179677A/en not_active Expired
- 1982-02-08 AU AU80271/82A patent/AU530826B2/en not_active Expired
- 1982-02-08 YU YU266/82A patent/YU42756B/xx unknown
- 1982-02-08 AT AT82300602T patent/ATE21691T1/de active
- 1982-02-08 ZA ZA82778A patent/ZA82778B/xx unknown
- 1982-02-08 IE IE275/82A patent/IE52326B1/en not_active IP Right Cessation
- 1982-02-09 IL IL64954A patent/IL64954A/xx active IP Right Revival
- 1982-02-09 PL PL1982239427A patent/PL130917B1/pl unknown
- 1982-02-09 PL PL1982239428A patent/PL130918B1/pl unknown
- 1982-02-09 PH PH26843A patent/PH20622A/en unknown
- 1982-02-09 EG EG60/82A patent/EG16242A/xx active
- 1982-02-09 PL PL1982235000A patent/PL130580B1/pl unknown
- 1982-02-09 PL PL1982239426A patent/PL130678B1/pl unknown
- 1982-11-17 AR AR291327A patent/AR229373A1/es active
- 1982-11-17 AR AR291328A patent/AR229374A1/es active
- 1982-11-17 AR AR291329A patent/AR229712A1/es active
- 1982-12-20 NO NO824273A patent/NO824273L/no unknown
- 1982-12-20 NO NO824275A patent/NO824275L/no unknown
- 1982-12-20 NO NO824274A patent/NO824274L/no unknown
-
1983
- 1983-01-05 SU SU833535711A patent/SU1217253A3/ru active
- 1983-01-05 SU SU833534854A patent/SU1250170A3/ru active
- 1983-01-05 SU SU833534107A patent/SU1240354A3/ru active
- 1983-01-13 ES ES518973A patent/ES8403112A1/es not_active Expired
- 1983-01-13 ES ES518972A patent/ES8403111A1/es not_active Expired
- 1983-01-13 ES ES518971A patent/ES518971A0/es active Granted
- 1983-10-19 PH PH29713A patent/PH19167A/en unknown
- 1983-10-19 PH PH29714A patent/PH19164A/en unknown
- 1983-10-19 PH PH29712A patent/PH20292A/en unknown
-
1984
- 1984-11-28 YU YU2019/84A patent/YU42908B/xx unknown
- 1984-11-28 YU YU2018/84A patent/YU43389B/xx unknown
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1985
- 1985-01-23 JP JP60010724A patent/JPS6059231B2/ja not_active Expired
- 1985-01-23 JP JP60010723A patent/JPS6059911B2/ja not_active Expired
- 1985-10-09 JP JP60225922A patent/JPS6193164A/ja active Granted
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