KR960029331A - 3-알콕시카르보닐-티아디아지논 유도체 - Google Patents
3-알콕시카르보닐-티아디아지논 유도체 Download PDFInfo
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- KR960029331A KR960029331A KR1019960000414A KR19960000414A KR960029331A KR 960029331 A KR960029331 A KR 960029331A KR 1019960000414 A KR1019960000414 A KR 1019960000414A KR 19960000414 A KR19960000414 A KR 19960000414A KR 960029331 A KR960029331 A KR 960029331A
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- Prior art keywords
- methyl
- general formula
- compound
- thiadiazin
- tetrahydro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- -1 N, N-diethylamino Chemical group 0.000 claims 14
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 4
- 238000007796 conventional method Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 abstract 1
- 230000004118 muscle contraction Effects 0.000 abstract 1
Classifications
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- C07D417/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
본 발명은 일반식(Ⅰ)으로 표시되는 3-알콕시카르보닐티아디아지논 유도체 및 이의 생리학적으로 허용 가능한 염을 제공한다.
(Ⅰ)
(단, 상기 식에서, R1, R2및 R3는 각기 독립적으로 H 또는 A이고, R4는 탄소수가 1 내지 15인 아실기이며, R5는 NH2, NHA, NA2, 또는 A로 치환될 수 있는 하나 이상의 질소원자를 갖는 3원 내지 8원의 포화 이종원자 고리형 라디칼이고, 여기에서 상기 고리중에 존재하는 CH2기는 NH 또는 NA기나 산소 또는 황원자로 대체될 수 있으며, Q는 부재이거나 또는 탄소수가 1내지 10인 측쇄 또는 직쇄 알킬렌이고, n은 1,2 또는 3이며, A는 탄소수가 1 내지 6인 알킬기이다).
본 발명의 화합물은 양성의 근수축성 작용을 나타내고, 심부전중의 치료에 사용할 수 있다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 일반식(Ⅰ)으로 표시되는 3-알콕시카르보닐티아디아지논 유도체 및 이의 생리학적으로 허용가능한 염.(Ⅰ)(단, 상기 식에서, R1, R2및 R3는 각기 독립적으로 H 또는 A이고, R4는 탄소수가 1 내지 15인 아실기이며, R5는 NH2, NHA, NA2, 또는 A로 치환될 수 있는 하나 이상의 질소원자를 갖는 3원 내지 8원의 포화 이종원자 고리형 라디칼이고, 여기에서 상기 고리중에 존재하는 CH2기는 NH 또는 NA기나 산소 또는 황원자로 대체될 수 있으며, Q는 부재이거나 또는 탄소수가 1 내지 10인 측쇄 또는 직쇄 알킬렌이고, n은 1,2 또는 3이며, A는 탄소수가 1 내지 6인 알킬기이다).
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물의 거울상 이성질체.
- 제1항에 있어서, 상기한 일반식(Ⅰ)으로 표시되는 화합물이 다음 화합물 (a) 내지 (i)인 것을 특징으로 하는 화합물 및 이들 화합물의 거울상 이성질체:(a) 3-〔2-(N,N-디에틸아미노)에톡시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (b) 3-〔2-(N,N-디에틸아미노)프로폭시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (c) 3-〔6-(N,N-디에틸아미노)헥실옥시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (d) 3-〔1-메틸-2-(N,N-디에틸아미노)에톡시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (e)3-〔1-메틸-4-피페리딜옥시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (f) 3-〔2-(N,N-디에틸아미노)에톡시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-4,4-메틸-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (g) 3-〔2-(N,N-디에틸아미노)헥실옥시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-4,4-디메틸-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (h) 3-〔1-메틸-4-피페리딜옥시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-4,4-메틸-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온; (i) 3-〔1-메틸-2-(N,N-디에틸아미노)에톡시카르보닐〕-5-〔1,2,3,4-테트라히드로-1-(3,4-디메톡시벤조일)-4,4-디메틸-6-퀴놀릴〕-6-메틸-2H-3,6-디히드로-1,3,4-티아디아진-2-온.
- 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시키거나 또는 일반식(Ⅴ)의 화합물을 일반식 (V)의 화합물과 반응시키거나 또는 라디칼 R5대신에 일차 또는 이차 아미노기를 갖는 일반식(Ⅰ)의 화합물을 통상의 방법으로 알킬화시키거나 또는 라디칼 R4대신에 수소원자를 갖는 일반식(Ⅰ)의 화합물을 통상의 방법으로 아실화시키거나 또는 일반식(Ⅰ)의 라디칼 R4중 하나가 라디칼 R4중 다른 하나로 전환시키거나 및/또는 일반식(Ⅰ)의 염기를 산으로 처리하여 이의 염중 하나로 전화키는 것을 특징으로 하는 제1항에 따른 일반식(Ⅰ)의 화합물 및 이들의 염의 제조방법.(Ⅱ)(단, 상기 식에서, R1, R2, R3, R4및 n은 상기에서 정의한 바와 같다.)X-CO2-Q-R5(Ⅲ)(단, 상기 식에서, Q 및 R5는 상기에서 정의한 바와 같고, X는 Cl, Br, OH 또는 반응적으로 에스테르화된 OH기이다.)(Ⅳ)(단, 상기 식에서, R1, R2, R3, R4, Q, n 및 X는 상기에서 정의한 바와 같다.)R5-H (Ⅴ)(단, 상기 식에서, R는 상기에서 정의한 바와 같다.)
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물 및/또는 이의 생리학적으로 허용가능한 염중 하나를 1종 이상의 고체, 액체 또는 반액체 부형제 또는 보조제와 함께 적합한 투여 형태로 만드는 것을 특징으로 하는 약제학적 제형의 제조방법.
- 제1항에 따른 일반식(Ⅰ)으로 표시되는 화합물 1종이상 및/또는 이의 생리학적으로 허용가능한 염중 하나를 함유하는 것을 특징으로 하는 약제학적 제형.
- 질병 치료용 약물 제조에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 이의 생리학적으로 허용가능한 염.
- 질병 치료에 사용되는 일반식(Ⅰ)의 화합물 및/또는 이의 생리학적으로 허용가능한 염.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP19500558.9 | 1995-01-11 | ||
DE19500558A DE19500558A1 (de) | 1995-01-11 | 1995-01-11 | 3-Alkoxycarbonyl-thiadiazinone |
Publications (2)
Publication Number | Publication Date |
---|---|
KR960029331A true KR960029331A (ko) | 1996-08-17 |
KR100399541B1 KR100399541B1 (ko) | 2003-12-31 |
Family
ID=7751240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960000414A KR100399541B1 (ko) | 1995-01-11 | 1996-01-11 | 3-알콕시카르보닐-티아디아지논유도체 |
Country Status (24)
Country | Link |
---|---|
US (1) | US5705497A (ko) |
EP (1) | EP0721950B1 (ko) |
JP (1) | JP4025377B2 (ko) |
KR (1) | KR100399541B1 (ko) |
CN (1) | CN1055691C (ko) |
AT (1) | ATE165828T1 (ko) |
AU (1) | AU704493B2 (ko) |
CA (1) | CA2166854A1 (ko) |
CZ (1) | CZ292094B6 (ko) |
DE (2) | DE19500558A1 (ko) |
DK (1) | DK0721950T3 (ko) |
ES (1) | ES2120251T3 (ko) |
GR (1) | GR3027566T3 (ko) |
HK (1) | HK1010194A1 (ko) |
HU (1) | HUP9600061A3 (ko) |
MX (1) | MX9600165A (ko) |
NO (1) | NO306300B1 (ko) |
PL (1) | PL183011B1 (ko) |
RU (1) | RU2162087C2 (ko) |
SI (1) | SI0721950T1 (ko) |
SK (1) | SK280532B6 (ko) |
TW (1) | TW407157B (ko) |
UA (1) | UA44249C2 (ko) |
ZA (1) | ZA96177B (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
DE19929785A1 (de) | 1999-06-29 | 2001-01-04 | Bayer Ag | Tetrahydrochinolinyl-6-methyldihydrothiadiazinon-Derivate und ihre Verwendung |
RU2692102C2 (ru) * | 2014-08-15 | 2019-06-21 | Ф. Хоффманн-Ля Рош Аг | 2,2,2-трифторэтил-тиадиазины |
CN112500353B (zh) * | 2020-12-08 | 2022-11-25 | 北京晨光同创医药研究院有限公司 | 一种左西孟旦的前药化合物、制备方法及其应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU614965B2 (en) * | 1987-06-06 | 1991-09-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Thiadiazinones |
DE4041074A1 (de) * | 1990-12-21 | 1992-06-25 | Merck Patent Gmbh | Thiadiazinonderivate |
DE4129062A1 (de) * | 1991-09-02 | 1993-03-04 | Merck Patent Gmbh | Verfahren zur enantiomerentrennung von 5-hetaryl-1,3,4-thiadiazinonen |
DE4134893A1 (de) * | 1991-10-23 | 1993-04-29 | Merck Patent Gmbh | Thiadiazinone |
DE4223537A1 (de) * | 1992-07-17 | 1994-01-20 | Merck Patent Gmbh | Thiadiazinone |
DE4310699A1 (de) * | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Thiadiazinone |
-
1995
- 1995-01-11 DE DE19500558A patent/DE19500558A1/de not_active Withdrawn
- 1995-12-27 SK SK1652-95A patent/SK280532B6/sk unknown
-
1996
- 1996-01-04 AU AU40826/96A patent/AU704493B2/en not_active Ceased
- 1996-01-05 ES ES96100093T patent/ES2120251T3/es not_active Expired - Lifetime
- 1996-01-05 DE DE59600173T patent/DE59600173D1/de not_active Expired - Fee Related
- 1996-01-05 AT AT96100093T patent/ATE165828T1/de not_active IP Right Cessation
- 1996-01-05 EP EP96100093A patent/EP0721950B1/de not_active Expired - Lifetime
- 1996-01-05 DK DK96100093T patent/DK0721950T3/da active
- 1996-01-05 SI SI9630017T patent/SI0721950T1/xx not_active IP Right Cessation
- 1996-01-09 CN CN96100838A patent/CN1055691C/zh not_active Expired - Fee Related
- 1996-01-09 MX MX9600165A patent/MX9600165A/es unknown
- 1996-01-09 CA CA002166854A patent/CA2166854A1/en not_active Abandoned
- 1996-01-10 CZ CZ199680A patent/CZ292094B6/cs not_active IP Right Cessation
- 1996-01-10 PL PL96312240A patent/PL183011B1/pl not_active IP Right Cessation
- 1996-01-10 TW TW085100251A patent/TW407157B/zh not_active IP Right Cessation
- 1996-01-10 HU HU9600061A patent/HUP9600061A3/hu unknown
- 1996-01-10 ZA ZA96177A patent/ZA96177B/xx unknown
- 1996-01-10 NO NO960112A patent/NO306300B1/no not_active IP Right Cessation
- 1996-01-10 RU RU96100853/04A patent/RU2162087C2/ru not_active IP Right Cessation
- 1996-01-10 UA UA96010108A patent/UA44249C2/uk unknown
- 1996-01-11 JP JP01924796A patent/JP4025377B2/ja not_active Expired - Fee Related
- 1996-01-11 KR KR1019960000414A patent/KR100399541B1/ko not_active IP Right Cessation
- 1996-01-11 US US08/584,127 patent/US5705497A/en not_active Expired - Fee Related
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1998
- 1998-08-04 GR GR980401750T patent/GR3027566T3/el unknown
- 1998-09-29 HK HK98111044A patent/HK1010194A1/xx not_active IP Right Cessation
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