KR830007618A - 1,5-비스-(1,4-벤조디옥신-2-일)-3-아자펜탄-1,5-디올의 제조방법 - Google Patents
1,5-비스-(1,4-벤조디옥신-2-일)-3-아자펜탄-1,5-디올의 제조방법 Download PDFInfo
- Publication number
- KR830007618A KR830007618A KR1019810003878A KR810003878A KR830007618A KR 830007618 A KR830007618 A KR 830007618A KR 1019810003878 A KR1019810003878 A KR 1019810003878A KR 810003878 A KR810003878 A KR 810003878A KR 830007618 A KR830007618 A KR 830007618A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- acid addition
- reaction
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- KACQVUFYYXTRDA-UHFFFAOYSA-N 1-(1,4-benzodioxin-3-yl)-2-[[2-(1,4-benzodioxin-3-yl)-2-hydroxyethyl]amino]ethanol Chemical compound C1=CC=C2OC(C(CNCC(O)C=3OC4=CC=CC=C4OC=3)O)=COC2=C1 KACQVUFYYXTRDA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 6
- 239000007858 starting material Substances 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 4
- 229910021529 ammonia Inorganic materials 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000005868 electrolysis reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- -1 salt salt Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기 일반식(Ⅲ)과 일반식(Ⅳ)의 화합물 또는 이화합물 각각의 대칭체, 또는 이 화합물의 라세미체를 반응시키며 필요하다면, 생성 이성체 혼합물을 분리시키며(반응1); 또는 Y가 α-알지방족 또는 아실기인 일반식(Ⅴ) 화합물 또는 일반식(Ⅴ) 함유이성체 혼합물을 가수소화시키거나 또는 가수분해시키며 또는 Y가 아실이며 하이드록시 그룹중 한그룹이 아실기로 보호되는 일반식(Ⅴ) 화합물을 가수분해시키며 필요하다면, 생성 이성체 혼합물을 분리시키며(반응 2); 또는 일반식(Ⅲ)의 화합물 또는 이 화합물의 라세미체와 암모니아를 가열시키며 필요하다면 생성 이성체 혼합물을 분리시키며, 원한다면 생성 유리화합물을 산부가염으로 전환시키거나 또는 산부가염을 유리 화합물 또는 또다른 산부가염으로 전환시킴(반응 3)을 특징으로하여 하기 일반식(Ⅱ)의 1-(2,3-디하이드로-1,4-벤조디옥신-2S-일)-5-(2,3-디하이드로-1,4-벤조디옥신-2R-일)-3-아자펜탄-1R, 5S-디올 및 이들의 산부가염을 제조하는 방법.
- 제1항에 있어서, 반응(1)이 반응혼합물의 환류온도에서 수행됨을 특징으로 하는 상기 방법.
- 제1항에 있어서, 반응(2)의 α-알지방족기 Y를 갖는 일반식(Ⅴ)의 출발물질을 촉매적으로 활성화된 수소 또는 발생기 수소로 또는 전기분해로 생성시킨 수소로 가수소화시킴을 특징으로 하는 상기 방법.
- 제1항에 있어서, 반응(2)의 아실기 Y를 갖는 일반식(Ⅴ)의 출발물질에서 아실기를 수용산이나 염기로 또는 복합 경금속 하이드라이드로 분해시킴을 특징으로 하는 상기 방법.
- 제1항에 있어서, 반응(3)이 ½몰랄당량의 암모니아로 수행됨을 특징으로하는 상기 방법.
- 제1항에 있어서, 이성체 또는 이성체염의 생성혼합물을 크로마토그라피시키거나 각각 결정화시켜 분리시킴을 특징으로하는 상기 방법.
- 제1항, 제2항, 제3항, 제4항, 제5항 또는 제6항에 있어서, 각 단계에서 수득된 중간생성물을 출발물질로 사용하며 모든 잔존단계를 수행하거나 또는 이 단계중 어느 단계를 중단시키거나 또는 상기 출발물질을 반응조건하에서 형성시키거나 또는 반응성분을 광학적으로 순수한 대칭체의 형태로 사용함을 특징으로 하는 상기 방법.
- 일반식(Ⅲ)의 화합물 및 이의 대칭제를 벤질아민과 반응시키며, 필요하다면 생성 유리화합물을 이들의 산부가염으로 또는 생성 산부가염을 유리화합물 또는 다른 산부가염으로 전환시킴을 특징으로하여 에리트로 연속물인 메소-및 d, 1-이성체의 혼합물인 일반식(Ⅴa)의 출발물질 및 이들의 산부가염을 제조하는 방법.
- 제1항에 있어서, 일반식(Ⅲ)의 화합물을 라세미 에리트로 형태내에서 벤질아민과 반응시키며, 이성체 생성혼합물을 이의 산 부가염으로 전환시키며, 결정화시켜 원하는 일반식(Ⅴ)의 화합물을 분리시키며 필요하다면 생성 산부가염을 유리화합물 또는 다른 산부가염으로 전환시킴을 특징으로하여 Y가 벤질인 일반식(Ⅴ)의 출발물질 및 이들의 산부가염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/196,503 US4313955A (en) | 1980-10-14 | 1980-10-14 | 1,5-Bis(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols |
| US196.503 | 1980-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007618A true KR830007618A (ko) | 1983-11-04 |
Family
ID=22725667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810003878A KR830007618A (ko) | 1980-10-14 | 1981-10-14 | 1,5-비스-(1,4-벤조디옥신-2-일)-3-아자펜탄-1,5-디올의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4313955A (ko) |
| EP (1) | EP0050585B1 (ko) |
| JP (1) | JPS5795982A (ko) |
| KR (1) | KR830007618A (ko) |
| AR (1) | AR227441A1 (ko) |
| AT (1) | ATE9694T1 (ko) |
| AU (1) | AU548164B2 (ko) |
| DD (1) | DD201678A5 (ko) |
| DE (1) | DE3166503D1 (ko) |
| DK (1) | DK454181A (ko) |
| ES (3) | ES506212A0 (ko) |
| FI (1) | FI813154L (ko) |
| GB (1) | GB2085008B (ko) |
| GR (1) | GR75089B (ko) |
| HU (1) | HU187378B (ko) |
| IE (1) | IE51645B1 (ko) |
| IL (1) | IL64033A (ko) |
| NO (1) | NO813446L (ko) |
| NZ (1) | NZ198619A (ko) |
| PT (1) | PT73812B (ko) |
| ZA (1) | ZA817048B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380653A (en) * | 1980-10-14 | 1983-04-19 | Ciba-Geigy Corporation | 1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols |
| US4471128A (en) * | 1981-09-08 | 1984-09-11 | Ciba-Geigy Corporation | 1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols |
| US4654362A (en) * | 1983-12-05 | 1987-03-31 | Janssen Pharmaceutica, N.V. | Derivatives of 2,2'-iminobisethanol |
| CA1337429C (en) * | 1983-12-05 | 1995-10-24 | Guy Rosalia Eugene Van Lommen | Derivatives of 2,2'-iminobisethanol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1038333A (en) * | 1963-02-13 | 1966-08-10 | Ici Ltd | Pharmaceutical compositions |
| US4187313A (en) * | 1978-01-30 | 1980-02-05 | Ciba-Geigy Corporation | 2-Aminoethyl-1,4-benzodioxans |
| US4261907A (en) * | 1978-01-30 | 1981-04-14 | Ciba-Geigy Corporation | Stereospecific process |
| DE2827801A1 (de) * | 1978-06-24 | 1980-01-10 | Kali Chemie Pharma Gmbh | Neue n tief 1 -benzoyl-n tief 2 -phenyl-1,3-diaminopropan-2-ole, verfahren zu deren herstellung und arzneimittel |
| US4212808A (en) * | 1979-03-09 | 1980-07-15 | Ciba-Geigy Corporation | 2-Oxiranyl-1,4-benzodioxans |
-
1980
- 1980-10-14 US US06/196,503 patent/US4313955A/en not_active Expired - Lifetime
-
1981
- 1981-10-08 AT AT81810403T patent/ATE9694T1/de not_active IP Right Cessation
- 1981-10-08 DE DE8181810403T patent/DE3166503D1/de not_active Expired
- 1981-10-08 EP EP81810403A patent/EP0050585B1/de not_active Expired
- 1981-10-09 GR GR66245A patent/GR75089B/el unknown
- 1981-10-12 GB GB8130712A patent/GB2085008B/en not_active Expired
- 1981-10-12 IL IL64033A patent/IL64033A/xx unknown
- 1981-10-12 FI FI813154A patent/FI813154L/fi not_active Application Discontinuation
- 1981-10-13 AR AR287078A patent/AR227441A1/es active
- 1981-10-13 IE IE2399/81A patent/IE51645B1/en unknown
- 1981-10-13 NZ NZ198619A patent/NZ198619A/en unknown
- 1981-10-13 NO NO813446A patent/NO813446L/no unknown
- 1981-10-13 ZA ZA817048A patent/ZA817048B/xx unknown
- 1981-10-13 ES ES506212A patent/ES506212A0/es active Granted
- 1981-10-13 PT PT73812A patent/PT73812B/pt unknown
- 1981-10-13 AU AU76290/81A patent/AU548164B2/en not_active Ceased
- 1981-10-13 DK DK454181A patent/DK454181A/da not_active Application Discontinuation
- 1981-10-13 HU HU812953A patent/HU187378B/hu unknown
- 1981-10-14 DD DD81234081A patent/DD201678A5/de unknown
- 1981-10-14 JP JP56162905A patent/JPS5795982A/ja active Pending
- 1981-10-14 KR KR1019810003878A patent/KR830007618A/ko unknown
-
1982
- 1982-10-06 ES ES516272A patent/ES8502437A1/es not_active Expired
-
1983
- 1983-11-30 ES ES527677A patent/ES8600282A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL64033A0 (en) | 1982-01-31 |
| GB2085008B (en) | 1984-04-18 |
| EP0050585B1 (de) | 1984-10-03 |
| PT73812A (en) | 1981-11-01 |
| ES8303403A1 (es) | 1983-02-01 |
| PT73812B (en) | 1983-06-20 |
| ES516272A0 (es) | 1985-01-01 |
| AU548164B2 (en) | 1985-11-28 |
| GR75089B (ko) | 1984-07-13 |
| ATE9694T1 (de) | 1984-10-15 |
| AR227441A1 (es) | 1982-10-29 |
| AU7629081A (en) | 1982-04-22 |
| DK454181A (da) | 1982-04-15 |
| EP0050585A1 (de) | 1982-04-28 |
| FI813154L (fi) | 1982-04-15 |
| ES506212A0 (es) | 1983-02-01 |
| HU187378B (en) | 1985-12-28 |
| IE51645B1 (en) | 1987-01-21 |
| ES527677A0 (es) | 1985-10-01 |
| GB2085008A (en) | 1982-04-21 |
| IE812399L (en) | 1982-04-14 |
| NO813446L (no) | 1982-04-15 |
| ES8502437A1 (es) | 1985-01-01 |
| ES8600282A1 (es) | 1985-10-01 |
| DD201678A5 (de) | 1983-08-03 |
| NZ198619A (en) | 1985-07-31 |
| US4313955A (en) | 1982-02-02 |
| ZA817048B (en) | 1982-09-29 |
| DE3166503D1 (en) | 1984-11-08 |
| IL64033A (en) | 1984-08-31 |
| JPS5795982A (en) | 1982-06-15 |
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