KR950032176A - 3-인돌릴피페리딘 - Google Patents
3-인돌릴피페리딘 Download PDFInfo
- Publication number
- KR950032176A KR950032176A KR1019950009554A KR19950009554A KR950032176A KR 950032176 A KR950032176 A KR 950032176A KR 1019950009554 A KR1019950009554 A KR 1019950009554A KR 19950009554 A KR19950009554 A KR 19950009554A KR 950032176 A KR950032176 A KR 950032176A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- indolyl
- physiologically acceptable
- general formula
- Prior art date
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- XKJJOWGAKBYIQV-UHFFFAOYSA-N 2-piperidin-3-yl-1h-indole Chemical compound C1CCNCC1C1=CC2=CC=CC=C2N1 XKJJOWGAKBYIQV-UHFFFAOYSA-N 0.000 title claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 7
- -1 methylenedioxy Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ASMNHUUVNJNLGM-UHFFFAOYSA-N 3-[3-[4-(5-cyano-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-5-carboxamide Chemical compound C1=C(C#N)C=C2C(C3CCN(CC3)CCCC3=CNC4=CC=C(C=C43)C(=O)N)=CNC2=C1 ASMNHUUVNJNLGM-UHFFFAOYSA-N 0.000 claims 1
- DKXPYZFROKUHIN-UHFFFAOYSA-N 3-[4-[4-(5-cyanoindol-1-yl)piperidin-1-yl]butyl]-1H-indole-5-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCCCN3CCC(CC3)N3C4=CC=C(C=C4C=C3)C#N)=CNC2=C1 DKXPYZFROKUHIN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000005661 deetherification reaction Methods 0.000 claims 1
- 230000000593 degrading effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 238000006266 etherification reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract 2
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 229960003638 dopamine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Hydrogenated Pyridines (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Abstract
일반식(I)의 3-인돌릴피페리딘:
(상기 식에서, R1, R2, R3그리고 R4는 각각 상호 독립적으로 H, A, OH, OA, F, Cl, Br, I, CN, CF3, COOH, CONH2, CONHA, CONA2또는 COOA, 또는 R1그리고 R2또한 R3그리고 R4는 각 경우 함께 또는 메틸렌디옥시이고, R5는 H 또는 OH이고, R6는 H 또는 R5그리고 R6함께는 또한 결합이고, A는 탄소수 1 내지 6을 가지는 알킬기이고, 그리고 n은 2,3,4,5또는 6이다) 및 이들 생리학적으로 허용되는 염은 중추신경계, 특히 도파민 효능 또는 도파민-길항작용을 나타낸다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 일반식(I)의 3-인돌릴피페리딘 및 이들의 생리학적으로 허용되는 염:(상기 식에서, R1, R2, R3및 R4는 각각 상호 독립적으로 H, A, OH, OA, F, Cl, Br, I, CN, CF3, COOH, CONH2, CONHA, CONA2또는 COOA, 또는 R1및 R2또한 R3및 R4는 각 경우 함께 또는 메틸렌디옥시이고, R5는 H 또는 OH이고, R6는 H 또는 R5및 R6는 함께 또한 결합이고, A는 탄소수 1 내지 6인 알킬기이고, 그리고 n은 2,3,4,5 또는 6이다)
- 제1항에 있어서, 상기한 3-인돌릴피페리딘이 (a)3-(1-(3-(5-카르바모일-3-인돌릴)프로필)-피페리드-4-일)인돌-5-카르복스아미드; (b)3-(1-(3-(5-카르바모일-3-인돌릴)프로필)-피페리드-4-일)인돌-5-카르보니트릴; (c)3-(1-(4-(5-메톡시카르보닐-3-인돌릴)부틸)-피페리드-4-일)인돌-5-메톡시인돌; (d)3-(1-(3-(5-에톡시카르보닐-3-인돌릴)프로필)-피페리드-4-일)인돌-5-카르복스아미드; (e)3-(1-(4-(5-시아노-3-인돌릴)부틸피페리드-4-일)인돌-5-카르보니트릴 중의 어느 하나 또는 이들의 생리학적으로 허용되는 염들인 것을 특징으로 하는 3-인돌릴피페리딘.
- 제1항에 따른 일반식(I)의 3-인돌릴피페리딘 유도체 및 이들 염의 제조방법에 있어서, 다음 일반식(Ⅱ)의 화합물:(상기 식에서, X1은 X 또는 NH2이고, X는 Cl, Br, I, OH 또는 반응기를 형성하기 위해 기능적으로 변형된 OH기이고, R1, R2및 n은 상기한 바와 같다)을 다음 일반식(Ⅲ)의 화합물과 반응시키거나,(상기 식에서, X2및 X3는 같거나 또는 상이할 수 있으며, 그리고 X1=NH2인 경우 각각 X이거나 또는 다른 경우에는 함께 NH이고, R3및 R4는 상기한 바와 같다), 또는 다음 일반식(Ⅳ)의 화합물:(상기 식에서, R1, R2그리고 n은 상기한 바와 같다)을 다음 일반식(Ⅴ)의 인돌과 반응시키거나,(상기 식에서, R3및 R4는 상기한 바와 같다) 또는 R5가 OH이고, R6가 수소인 일반식(I)의 화합물을 탈수에 의해 일반식(I)의 다른 화합물로 전화시키거나, 또는 하나 이상의 수소원자가 하나 이상의 환원성기 및/또는 하나 이상의 부가적 C-C 및/또는 C-N결합으로 치환된 것 이외의 일반식(I)을 가지는 화합물을 환원제로 처리하거나, 또는 하나 이상의 수소원자가 하나 이상의 가용매분해성기로 치환된 것 이외의 일반식(I)을 가지는 화합물을 가용매분해제로 처리하거나, 및/또는 R1, R2, R3및/또는 R4가 에스테르화, 가수분해, 에테르화, 에테르 절단, 완전 또는 부분가수분해 또는 알킬화에 의해 다른 라디칼(들) R1, R2, R3및/또는 R4로 전환시키거나, 및/또는 생성된 일반식(I)의 염기 또는 산을 산 또는 염기로 처리하여 이들 염증의 하나로 전환시키는 것을 특징으로 하는 일반식(I)의 3-인돌릴피페리딘 유도체 및 이들 염의 제조방법.
- 제1항에 의한 일반식(I)의 화합물 및/또는 이들의 생리학적으로 허용되는 염을 하나 이상의 고체, 액체 또는 반액체 부형제 또는 보조제와 함께 적합한 투여형태로 전환하는 것을 특징으로 하는 약학적 제형의 제조방법.
- 제1항에 따른 일반식(I)의 화합물 1종 이상 및/또는 이들의 생리학적으로 허용되는 염증 하나를 함유하는 것을 특징으로 하는 약학적제형.
- 제1항에 따른 일반식(I)의 화합물 또는 이들의 생리학적으로 허용되는 들을 약물의 제조에 사용하는 용도.
- 제1항에 따른 일반식(I)의 화합물 또는 이들의 생리학적으로 허용되는 염들을 질병의 치료에 사용하는 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4414113A DE4414113A1 (de) | 1994-04-22 | 1994-04-22 | 3-Indolylpiperidine |
| DEP4414113.0 | 1994-04-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR950032176A true KR950032176A (ko) | 1995-12-20 |
| KR100361950B1 KR100361950B1 (ko) | 2003-02-05 |
Family
ID=6516183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950009554A KR100361950B1 (ko) | 1994-04-22 | 1995-04-22 | 3-인돌릴피페리딘 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5693655A (ko) |
| EP (1) | EP0683166B1 (ko) |
| JP (1) | JPH07291969A (ko) |
| KR (1) | KR100361950B1 (ko) |
| CN (1) | CN1047385C (ko) |
| AT (1) | ATE172730T1 (ko) |
| AU (1) | AU697749B2 (ko) |
| CA (1) | CA2147451C (ko) |
| CZ (1) | CZ285369B6 (ko) |
| DE (2) | DE4414113A1 (ko) |
| DK (1) | DK0683166T3 (ko) |
| ES (1) | ES2125508T3 (ko) |
| HU (1) | HUT74096A (ko) |
| NO (1) | NO307831B1 (ko) |
| PL (1) | PL180781B1 (ko) |
| RU (1) | RU2151148C1 (ko) |
| SK (1) | SK280881B6 (ko) |
| TW (1) | TW401416B (ko) |
| UA (1) | UA41333C2 (ko) |
| ZA (1) | ZA953260B (ko) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
| GB9523462D0 (en) * | 1995-11-16 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
| ZA9711376B (en) | 1996-12-20 | 1998-07-21 | Lundbeck & Co As H | Indole or dihydroindole derivatives |
| DE19707628A1 (de) * | 1997-02-26 | 1998-08-27 | Merck Patent Gmbh | Oxazolidinone |
| AU736596B2 (en) * | 1997-07-25 | 2001-08-02 | H. Lundbeck A/S | Indole and 2,3-dihydroindole derivatives, their preparation and use |
| BR9811557A (pt) * | 1997-08-15 | 2000-08-22 | Pfizer Prod Inc | Derivados do 2-)4-aril ou heteroaril-piperazin-1-ilmetil)-1h-indol |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| EP1065205B1 (en) | 1998-03-18 | 2003-05-28 | Taisho Pharmaceutical Co., Ltd | Heteroaromatic derivatives |
| AU747508B2 (en) | 1998-03-19 | 2002-05-16 | Nihon Nohyaku Co., Ltd. | Arylpiperidine derivatives and use thereof |
| US6204274B1 (en) | 1998-04-29 | 2001-03-20 | American Home Products Corporation | Indolyl derivatives as serotonergic agents |
| US6310066B1 (en) | 1998-04-29 | 2001-10-30 | American Home Products Corp. | Antipsychotic indolyl derivatives |
| US6066637A (en) * | 1998-06-19 | 2000-05-23 | American Home Products Corporation | Indolyl derivatives as serotonergic agents |
| ID27976A (id) | 1998-06-19 | 2001-05-03 | Lundbeck & Co As H | 4,5,6 dan 7-indol dan turunan-turunan indolin, pembuatan dan penggunaannya |
| CA2335711A1 (en) * | 1998-06-19 | 1999-12-29 | Ivan Mikkelsen | 4,5,6 and 7-indole and indoline derivatives, their preparation and use |
| AR020773A1 (es) | 1998-10-16 | 2002-05-29 | Duphar Int Res | Compuesto derivados de 3-(tetrahidropiridin-4-il)indol, metodo para prepararlo, una composicion farmaceutica que los contiene, metodo para preparar dicha composicion y uso del compuesto |
| WO2000069424A2 (en) * | 1999-05-12 | 2000-11-23 | Solvay Pharmaceuticals B.V. | Method of treating psychotic disorders |
| PL201178B1 (pl) | 1999-08-23 | 2009-03-31 | Solvay Pharm Bv | Nowe pochodne fenylopiperazyny, sposób ich wytwarzania, kompozycja farmaceutyczna oraz zastosowanie |
| US6806275B2 (en) | 2000-09-13 | 2004-10-19 | Nihon Nohyaku Co., Ltd. | Arylpiperidine derivatives and use thereof |
| AR032712A1 (es) | 2001-02-21 | 2003-11-19 | Solvay Pharm Bv | Un mesilato de derivados de fenilpiperazina y composiciones farmaceuticas que lo contienen |
| US6903110B2 (en) | 2001-07-25 | 2005-06-07 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of 7,8-dihydro-6H-5-oxa-1-aza-phenanthrene |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| US7235569B2 (en) * | 2003-05-02 | 2007-06-26 | Wyeth | Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use |
| CN106243088B (zh) | 2015-06-03 | 2019-01-04 | 广东东阳光药业有限公司 | 取代的哌嗪化合物及其使用方法和用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2675801A (en) * | 1954-04-20 | Intramedbllary nail | ||
| FR2349331A1 (fr) * | 1976-04-30 | 1977-11-25 | Roussel Uclaf | Nouveaux derives de 2,3 dihydro a/4-(3-indolyl) 1-piperidinyl/methyl 1,4-benzodioxin-2-methanol, un procede pour leur preparation et leur application comme medicaments |
| GB2044254B (en) | 1979-01-26 | 1983-01-26 | Wyeth John & Brother Ltd | Piperidine derivatives |
| US4359468A (en) * | 1981-02-25 | 1982-11-16 | Boehringer Ingelheim Ltd. | Antiallergic N-[4-(indolyl)-piperidino-alkyl]-benzimidazolones |
| HU198036B (en) * | 1983-08-22 | 1989-07-28 | Hoechst Roussel Pharma | Process for production of derivatives of 3-piperidil-/1h/-indasole and medical preparatives containing them |
| US5256673A (en) * | 1983-11-25 | 1993-10-26 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Indole-3-yl-A-tetrahydropyridyl or piperidyl compounds |
| US4548939A (en) * | 1984-10-01 | 1985-10-22 | Janssen Pharmaceutica N. V. | 1H-Indol-3-yl containing 1,3-dimethyl-1H-purine-2,6-diones |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
| GB8531665D0 (en) * | 1985-12-23 | 1986-02-05 | Wyeth John & Brother Ltd | Indole derivatives |
| JP2860688B2 (ja) * | 1990-03-14 | 1999-02-24 | 第一製薬株式会社 | インドール誘導体 |
| FR2675801A1 (fr) | 1991-04-24 | 1992-10-30 | Rhone Poulenc Rorer Sa | Piperidines, leur preparation et les medicaments les contenant. |
| DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
| KR102044254B1 (ko) * | 2018-01-18 | 2019-11-13 | (주)우신에이펙 | 배광제어가 가능한 led 탐조등 |
-
1994
- 1994-04-22 DE DE4414113A patent/DE4414113A1/de not_active Withdrawn
-
1995
- 1995-03-22 UA UA95038268A patent/UA41333C2/uk unknown
- 1995-04-07 ES ES95105227T patent/ES2125508T3/es not_active Expired - Lifetime
- 1995-04-07 AT AT95105227T patent/ATE172730T1/de not_active IP Right Cessation
- 1995-04-07 DE DE59504032T patent/DE59504032D1/de not_active Expired - Lifetime
- 1995-04-07 DK DK95105227T patent/DK0683166T3/da active
- 1995-04-07 EP EP95105227A patent/EP0683166B1/de not_active Expired - Lifetime
- 1995-04-13 AU AU16488/95A patent/AU697749B2/en not_active Ceased
- 1995-04-17 JP JP7091077A patent/JPH07291969A/ja active Pending
- 1995-04-19 SK SK508-95A patent/SK280881B6/sk unknown
- 1995-04-20 CN CN95104705A patent/CN1047385C/zh not_active Expired - Fee Related
- 1995-04-20 CA CA002147451A patent/CA2147451C/en not_active Expired - Fee Related
- 1995-04-20 TW TW084103916A patent/TW401416B/zh active
- 1995-04-21 PL PL95308287A patent/PL180781B1/pl not_active IP Right Cessation
- 1995-04-21 NO NO951529A patent/NO307831B1/no not_active IP Right Cessation
- 1995-04-21 HU HU9501139A patent/HUT74096A/hu unknown
- 1995-04-21 CZ CZ951035A patent/CZ285369B6/cs not_active IP Right Cessation
- 1995-04-21 ZA ZA953260A patent/ZA953260B/xx unknown
- 1995-04-21 RU RU95106675/04A patent/RU2151148C1/ru not_active IP Right Cessation
- 1995-04-21 US US08/426,405 patent/US5693655A/en not_active Expired - Lifetime
- 1995-04-22 KR KR1019950009554A patent/KR100361950B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO951529L (no) | 1995-10-23 |
| DE59504032D1 (de) | 1998-12-03 |
| HU9501139D0 (en) | 1995-06-28 |
| CN1114651A (zh) | 1996-01-10 |
| AU1648895A (en) | 1995-11-02 |
| DE4414113A1 (de) | 1995-10-26 |
| PL308287A1 (en) | 1995-10-30 |
| ATE172730T1 (de) | 1998-11-15 |
| DK0683166T3 (da) | 1999-07-12 |
| ES2125508T3 (es) | 1999-03-01 |
| CA2147451C (en) | 2006-03-28 |
| CZ103595A3 (en) | 1995-12-13 |
| CZ285369B6 (cs) | 1999-07-14 |
| EP0683166B1 (de) | 1998-10-28 |
| JPH07291969A (ja) | 1995-11-07 |
| EP0683166A1 (de) | 1995-11-22 |
| CN1047385C (zh) | 1999-12-15 |
| NO307831B1 (no) | 2000-06-05 |
| HUT74096A (en) | 1996-11-28 |
| KR100361950B1 (ko) | 2003-02-05 |
| CA2147451A1 (en) | 1995-10-23 |
| UA41333C2 (uk) | 2001-09-17 |
| SK280881B6 (sk) | 2000-08-14 |
| US5693655A (en) | 1997-12-02 |
| RU2151148C1 (ru) | 2000-06-20 |
| ZA953260B (en) | 1996-01-09 |
| TW401416B (en) | 2000-08-11 |
| SK50895A3 (en) | 1995-11-08 |
| NO951529D0 (no) | 1995-04-21 |
| AU697749B2 (en) | 1998-10-15 |
| RU95106675A (ru) | 1997-03-20 |
| PL180781B1 (pl) | 2001-04-30 |
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| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |