KR840009088A - 광학 활성 카바졸 유도체의 제조방법 - Google Patents
광학 활성 카바졸 유도체의 제조방법 Download PDFInfo
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- KR840009088A KR840009088A KR1019840002847A KR840002847A KR840009088A KR 840009088 A KR840009088 A KR 840009088A KR 1019840002847 A KR1019840002847 A KR 1019840002847A KR 840002847 A KR840002847 A KR 840002847A KR 840009088 A KR840009088 A KR 840009088A
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- KR
- South Korea
- Prior art keywords
- group
- pharmacologically acceptable
- formula
- carbazole
- general formula
- Prior art date
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- 238000000034 method Methods 0.000 title claims 5
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 8
- 210000001072 colon Anatomy 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- -1 methoxyphenoxyethyl Chemical group 0.000 claims 4
- 230000003287 optical effect Effects 0.000 claims 4
- 239000012876 carrier material Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BRLQWZUYTZBJKN-VKHMYHEASA-N (-)-Epichlorohydrin Chemical compound ClC[C@H]1CO1 BRLQWZUYTZBJKN-VKHMYHEASA-N 0.000 claims 1
- SVWKIGRDISDRLO-SNVBAGLBSA-N 4-[[(2r)-oxiran-2-yl]methoxy]-9h-carbazole Chemical compound C=1C=CC=2NC3=CC=CC=C3C=2C=1OC[C@H]1CO1 SVWKIGRDISDRLO-SNVBAGLBSA-N 0.000 claims 1
- UEOHATPGKDSULR-UHFFFAOYSA-N 9h-carbazol-4-ol Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2O UEOHATPGKDSULR-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000208202 Linaceae Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 다음 일반식(Ⅱ)의 S-에포시드 유도체를 유기용매의 존재하에 알칼리성 매질 중에서 4-히드록시카졸과 반응시키고 얻어진 R-4-(2,3-에폭시프로폭시)-카바졸을 암모니아 또는 RH , 일반식의 치환 아민과 반응시키고 그 다음 필요하다면 얻어진 화합물을 약물학적으로 수용 가능한 염으로 전환시킴을 특징으로하는 다음 일반식(I)의R -카바졸 유도체 뿐만 아니라 그것의 약물학적으로 수용 가능한 염의 제조방법.상기식에서, R은 불치환 또는 치환된 아미노 기이고, R1은 치환된 술폰 산 유도체의 잔사이다.
- 상기 1항에 있어 R은 이소프로필아민, tert-부틸아만 또는0-메톡시펜옥시 에틸아민기이고 R1은 메실기를 나타내는 상기의 방법.
- 상기 1항에 있어 실제적으로 상기한 바와 같이 기재되고 예시된 일반식(I)의 R-카바졸 유도체의 제조방법.
- 상기 1내지 3항에 따른 방법에 의해 제조된 일반식(Ⅰ)의 -카바졸 유도체.
- R-(-)-에피클로르히드린을 알칼리성 매질중에서 유기용매의 존재하에 4-히드록시카바졸과 반응시키고 얻어진 S-4-(2,3-에폭시프로폭시)카바졸을 암모니아 또는RH , 일반식의 치환된 아민과 반응시켜 그 후 얻어진 화합물을 필요하다면 약물학적으로 수용 가능한 염으로 전환시킴을 특징으로 하는 다음 일반식(I)의 S-카바졸 유도체 뿐만 아니라 약물학적으로 수용 가능한 염들의 제조방법.상기 식에서 R은 불치환된 또는 치환된 아미노기이다.
- 상기 5항에 있어 R은 이소프로필아마, tert-무틸아만 또는-메톡시펜옥시에틸 아민기를 나타내는 상기의 방법.
- 상기 5항에 있어 실제적으로 상기한 바와 같이 기재되고 예시된 일반식(I)의S -카바족 유도체의 제조방법.
- 상기 5내지 7항에 따른 방법에 의해 제조된 일반식(I)의 S-카바졸 유도체.
- 다음 일반식(I)의 R-(+)-및 S-(-)-카바졸 유도체.상기 식에서 R은 저급 알킬기로 치환된 아미노기이거나 다음 일반식의 기이고,여기서 R2는 수소원자, 저급 알킬기 또는 벤질, 페닐에틸 또는 페닐프로필기이고, R3는 수소원자 또는 저급 알킬기이고 R4는 수소원자 또는 저급 알킬기이고 X는 일원자가 결합으로 -CH2-그룸 또는 산소 또는 황원자이고, Ar은 패니, 나프틸, 인다닐, 테트라히드로나프틸 또는 피리딜기이고, R5및 R6는 같거나 다를수 있으며 수소 또는 할로겐 원자, 저급 알킬기, 아미노카보닐그룹, 히드록실그룹,히드록실그룹, 저급 알콕시기, 벤질옥시기, 저급 알킬티오기, 저급 알킬술피닐기 또는 저급 알킬술포닐기 또는 다 같이 메틸렌디옥시기를 나타낸다.
- R-(+)-및S-(-)-(1-카바졸-4-일옥시)-3-2-(2-메톡시펜옥시)-에틸아미노프로핀-2-올 뿐만 아니라 그것의 약물학적으로 수용 가능한 염돌.
- R-(-)-및S-(+)-4-(2,3-에폭시프로폭시)-카바졸.
- 상기 9항에 따른 화합물과 알려진 약물학적으로 수용 가능한 담체물질을 함유하는 약제 조성물.
- 상기 10항에 따른 화합물과 알려진 약물학적으로 수용 가능한 담체물질을 함유하는 약제 조성물.
- 다른 광학 대장체와 적당한 비율로 함유되나 대장체 R:S비가 50:50으로 함유되는 것을 제외하여 상기 9항에 따른 광학적으로 순수한 광학대장체에 덧붙여 알려진 약물학적으로 수용 가능한 담체물질을 함유하는 약제 조성물.
- 다른 광학 대장체와 적당한 비율로 함유되나 대장체 R:S비가 50:50으로 함유되는 것을 제회하여 상기 10항에 따른 광학적으로 순수한 광학대장체에 덧붙여 알려진 약물학적으로 수용 가능한 담체물질을 함유하는 약제 조성물.
- 약제 조성물의 제조를 위해 상기 9 또는 10항에 따른 화합물의 사용.
- 상기 1 또는 5항에 따른 일반식(I)의 화합물의 제조를 위한 상기 11항에 따른 화합물의 사용.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3319027.5 | 1983-05-26 | ||
| DEP3319027.5 | 1983-05-26 | ||
| DE19833319027 DE3319027A1 (de) | 1983-05-26 | 1983-05-26 | Verfahren zur herstellung von optisch aktiven carbazol-derivaten, neue r- und s-carbazol-derivate, sowie arzneimittel, die diese verbindungen enthalten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840009088A true KR840009088A (ko) | 1984-12-24 |
| KR860001761B1 KR860001761B1 (ko) | 1986-10-21 |
Family
ID=6199873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840002847A KR860001761B1 (ko) | 1983-05-26 | 1984-05-24 | 광학활성 카바졸 유도체의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US4697022A (ko) |
| EP (1) | EP0127099B1 (ko) |
| JP (2) | JPS59222473A (ko) |
| KR (1) | KR860001761B1 (ko) |
| AT (1) | ATE27273T1 (ko) |
| AU (1) | AU551116B2 (ko) |
| CA (1) | CA1259071A (ko) |
| DE (2) | DE3319027A1 (ko) |
| DK (2) | DK169331B1 (ko) |
| ES (1) | ES532838A0 (ko) |
| FI (1) | FI80018C (ko) |
| GR (1) | GR81577B (ko) |
| HU (1) | HU193011B (ko) |
| IE (1) | IE57533B1 (ko) |
| IL (1) | IL71876A (ko) |
| NO (1) | NO164537C (ko) |
| NZ (1) | NZ208254A (ko) |
| PH (1) | PH22749A (ko) |
| PT (1) | PT78633B (ko) |
| ZA (1) | ZA843976B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10749118B2 (en) | 2014-06-26 | 2020-08-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4657929A (en) * | 1983-10-25 | 1987-04-14 | Fisons Plc | Compounds |
| DE3540149A1 (de) * | 1985-11-13 | 1987-05-14 | Boehringer Mannheim Gmbh | Verwendung von 1-(benztriazol-4-yloxy)3-(2-(2-methoxyphenoxy) -ethylamino)-2-propanol als antiglaukommittel, optisch aktive r und s isomere dieser substanz, verfahren zur herstellung derselben sowie arzneimittel, die diese substanzen enthalten |
| DE68913965T2 (de) * | 1988-12-26 | 1994-08-04 | Kowa Co | Herstellung von glycidyläther. |
| US5308862A (en) * | 1993-03-05 | 1994-05-03 | Boehringer Mannheim Pharmaceuticals Corporation - Smithkline Beecham Corp., Ltd. Partnership No. 1 | Use of, and method of treatment using, carbazolyl-(4)-oxypropanolamine compounds for inhibition of smooth muscle cell proliferation |
| WO1994020096A1 (en) * | 1993-03-05 | 1994-09-15 | Boehringer Mannheim Pharmaceuticals Corporation - Smithkline Beckman Corporation Limited | Method of employing carbazolyl-(4)-oxypropanolamine compounds for inhibition of smooth muscle cell proliferation |
| US5629345A (en) * | 1993-07-23 | 1997-05-13 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| US5965620A (en) * | 1993-07-23 | 1999-10-12 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| US5760069A (en) | 1995-02-08 | 1998-06-02 | Boehringer Mannheim Pharmaceuticals Corporation-Smithkline Beecham Corporation Limited Partnership #1 | Method of treatment for decreasing mortality resulting from congestive heart failure |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| AU3542697A (en) * | 1996-07-13 | 1998-02-09 | Boehringer Mannheim Gmbh | Pharmaceutical formulations for topical application containing as an active ingredient carbazolyl-(4)-oxy-propanol amine derivate |
| ES2171839T3 (es) | 1996-09-05 | 2002-09-16 | Lilly Co Eli | Analogos de carbazol como agonistas adrenergicos selectivos de beta3. |
| US5808080A (en) * | 1996-09-05 | 1998-09-15 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| EP0893440A1 (en) * | 1997-07-22 | 1999-01-27 | Roche Diagnostics GmbH | Thermodynamically stable modification of 1-(4-carbazolyloxy)-3-[2-(2-methoxyphenoxy)ethylamino]-2-propanole, process for its preparation and pharmaceutical compositions containing it |
| US6730326B2 (en) | 1997-07-22 | 2004-05-04 | Roche Diagnostics Gmbh | Thermodynamically stable modification of 1-(4-carbazolyl-oxy-3[2-(2-methoxyphenoxy)-ethylamino]-2-propanol process for its preparation and pharmaceutical compositions containing it |
| ZA989365B (en) * | 1997-10-15 | 1999-04-15 | Boehringer Mannheim Pharm Corp | Preparation for treating alzheimer's disease |
| HU227441B1 (en) * | 1997-11-24 | 2011-06-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Process for producing carvedilol, enantiomers and salts thereof |
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1983
- 1983-05-26 DE DE19833319027 patent/DE3319027A1/de not_active Withdrawn
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1984
- 1984-05-19 EP EP84105747A patent/EP0127099B1/de not_active Expired
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- 1984-05-23 JP JP59102778A patent/JPS59222473A/ja active Granted
- 1984-05-23 CA CA000454948A patent/CA1259071A/en not_active Expired
- 1984-05-23 NZ NZ208254A patent/NZ208254A/xx unknown
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- 1984-05-24 IE IE1295/84A patent/IE57533B1/en not_active IP Right Cessation
- 1984-05-24 PT PT78633A patent/PT78633B/pt unknown
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- 1984-05-25 ES ES532838A patent/ES532838A0/es active Granted
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1987
- 1987-05-13 US US07/049,673 patent/US4824963A/en not_active Expired - Lifetime
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1989
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10749118B2 (en) | 2014-06-26 | 2020-08-18 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
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