KR920701136A - 아릴-및 헤테로아릴에테닐렌 유도체 및 이의 제조방법 - Google Patents
아릴-및 헤테로아릴에테닐렌 유도체 및 이의 제조방법Info
- Publication number
- KR920701136A KR920701136A KR1019910701435A KR910701435A KR920701136A KR 920701136 A KR920701136 A KR 920701136A KR 1019910701435 A KR1019910701435 A KR 1019910701435A KR 910701435 A KR910701435 A KR 910701435A KR 920701136 A KR920701136 A KR 920701136A
- Authority
- KR
- South Korea
- Prior art keywords
- cyano
- acrylamide
- tetrahydronaphth
- hydroxy
- hydroxyquinolin
- Prior art date
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- C07—ORGANIC CHEMISTRY
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/44—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 일반식(I)의 화합물 및 약제학적으로 허용되는 이의 염.상기식에서, Y는 (A), (B),(c), (D), (E), (F) 및 (G)중에서 선택된 모노-또는 비사이클릭 환 시스템이고,R은 (a), (b), (c), (d), (e), (f), (g), (h), (i) 또는 (j)의 그룹이고,R3은 -OH 또는 -NH2이고, Ph는 페닐이고, R1은 수소, C1-C6알킬 또는 C2-C6알카노일이고, R2는 수소, 할로겐, 시아노 또는 C1-C6알킬이고, n은 0 또는 1 내지 3의 정수이고, Y가 환 시스템(A)인 경우 n은 0 또는 1 내지 3의 정수이고; Y가 환 시스템(B), (E), (F) 또는 (G)인 경우 n은 0, 1 또는 2이고; Y가 환 시스템(C) 또는 (D)인 경우 n은 0 또는 1이고, 치환체 R, OR1및 R2의 각각은 독립적으로 비사이클릭 환 시스템(A), (E), (F) 및 (G)의 아릴이거나 헤테로아릴 잔기일 수 있으며, 벤젠 잔기만이 비사이클릭 환시스템(B)에서 치환될 수 있다.
- 제1항에 있어서, Y가 모모사이클릭 또는 비사이클릭 환 시스템(A) 내지 (G) 중에서 선택되며; R이 (a), (b), (c), (d), (e), (i) 또는 (j)의 그룹이고; R1이 수소, C1-C4알킬 또는 C2-C4알카노일이고; R2가 수소이고; n이 제1항에서 정의한 바와 같은 일반식(I)의 화합물 및 약제학적으로 허용되는 이의 염.
- 제1항에 있어서, Y가 일반식(A), (B) 또는 (E)의 비사이클릭 환 시스템이고; R이 (a), (d), (e), (i) 또는 (j)의 그룹이고, R1및 R2가 수소이고; n이 0 또는 1인 일반식(I)의 화합물 및 약제학적으로 허용되는 이의 염.
- Z- 또는 E-부분입체이성체 또는 부분입체이성체의 혼합물일 수 있는, 2-시아노-3-(2-하이드록시나프트-1-일)아크릴아미드; 2-시아노-3-(3-하이드록시나프트-1-일)아크릴아미드; 2-시아노-3-(4-하이드록시나프트-1-일)아크릴아미드; 2-시아노-3-(1-하이드록시나프트-1-일)아크릴아미드; 2-시아노-3-(3-하이드록시나프트-2-일)아크릴아미드; 2-시아노-3-(4-하이드록시나프트-2-일)아크릴아미드; 2-시아노-3-(2-하이드록시나프트-1-일)아크릴산; 2-시아노-3-(3-하이드록시나프트-1-일)아크릴산; 2-시아노-3-(4-하이드록시나프트-1-일)아크릴산; 2-시아노-3-(1-하이드록시나프트-2-일)아크릴산; 2-시아노-3-(3-하이드록시나프트-2-일)아크릴산; 2-시아노-3-(4-하이드록시나프트-2-일)아크릴산; 2-시아노-3-(2-하이드록시나프트-1-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시나프트-1-일)티오아크릴아미드; 2-시아노-3-(4-하이드록시나프트-1-일)티오아크릴아미드; 2-시아노-3-(1-하이드록시나프트-2-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시나프트-2-일)티오아크릴아미드; 2-시아노-3-(4-하이드록시나프트-2-일)티오아크릴아미드; 2-(4-하이드록시페닐)-3-(나프트-1-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(나프트-2-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(나프트-1-일)아크릴산; 2-(4-하이드록시페닐)-3-(나프트-2-일)아크릴산; 2-시아노-3-(2-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴아미드; 2-시아노-3-(3-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴아미드; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴아미드; 2-시아노-3-(1-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)아크릴아미드; 2-시아노-3-(3-하이드록시나프트-5,6,7,8-테트라하이드로나프트-2-일)아크릴아미드; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)아크릴아미드; 2-시아노-3-(2-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴산; 2-시아노-3-(3-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴산; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)아크릴산; 2-시아노-3-(1-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)아크릴산; 2-시아노-3-(3-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)아크릴산; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)아크릴산; 2-시아노-3-(2-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)티오아크릴아미드; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)티오아크릴아미드; 2-시아노-3-(1-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)티오아크릴아미드; 2-시아노-3-(4-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)티오아크릴아미드; 2-(4-하이드록시페닐)-3-(5,6,7,8-테트라하이드로나프트-1-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(5,6,7,8-테트라하이드로나프트-2-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(5,6,7,8-테트라하이드로나프트-1-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(5,6,7,8-테트라하이드로나프트-2-일)아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-2-일)아크릴아미드; 2-시아노-3-(4-하이드록시퀴놀린-2-일)아크릴아미드; 2-시아노-3-(2-하이드록시퀴놀린-3-일)아크릴아미드; 2-시아노-3-(4-하이드록시퀴놀린-3-일)아크릴아미드; 2-시아노-3-(2-하이드록시퀴놀린-4-일)아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-4-일)아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-2-일)아크릴산; 2-시아노-3-(4-하이드록시퀴놀린-2-일)아크릴산; 2-시아노-3-(2-하이드록시퀴놀린-3-일)아크릴산; 2-시아노-3-(4-하이드록시퀴놀린-3-일)아크릴산; 2-시아노-3-(2-하이드록시퀴놀린-4-일)아크릴산; 2-시아노-3-(3-하이드록시퀴놀린-4-일)아크릴산; 2-시아노-3-(3-하이드록시퀴놀린-2-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-2-일)티오아크릴아미드; 2-시아노-3-(2-하이드록시퀴놀린-3-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-2-일)티오아크릴아미드; 2-시아노-3-(4-하이드록시퀴놀린-3-일)티오아크릴아미드; 2-시아노-3-(2-하이드록시퀴놀린-4-일)티오아크릴아미드; 2-시아노-3-(3-하이드록시퀴놀린-4-일)티오아크릴아미드; 2-(4-하이드록시페닐)-3-(퀴놀린-2-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(퀴놀린-3-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(퀴놀린-4-일)아크릴아미드; 2-(4-하이드록시페닐)-3-(퀴놀린-2-일)아크릴산; 2-(4-하이드록시페닐)-3-(퀴놀린-3-일)아크릴산; 2-(4-하이드록시페닐)-3-(퀴놀린-4-일)아크릴산; 3-[(3-하이드록시-1-나프틸)메틸렌]-2-옥스인돌; 3-[(4-하이드록시-1-나프틸)메틸렌]-2-옥스인돌; 3-[(1-하이드록시-2-나프틸)메틸렌]-2-옥스인돌; 3-[(4-하이드록시-2-나프틸)메틸렌]-2-옥스인돌; 3-[(3-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)메틸렌]-2-옥스인돌; 3-[(4-하이드록시-5,6,7,8-테트라하이드로나프트-1-일)메틸렌]-2-옥스인돌; 3-[(1-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)메틸렌]-2-옥스인돌; 3-[(4-하이드록시-5,6,7,8-테트라하이드로나프트-2-일)메틸렌]-2-옥스인돌; 3-[(7-하이드록시퀴놀린-5-일)메틸렌]-2-옥스인돌; 3-[(8-하이드록시퀴놀린-5-일)메틸렌]-2-옥스인돌; 3-[(7-하이드록시퀴놀린-6-일)메틸렌]-2-옥스인돌; 3-[(8-하이드록시퀴놀린-6-일)메틸렌]-2-옥스인돌, 및 약제학적으로 허용되는 이의 염중에서 선택되는 화합물.
- 일반식(Ⅱ)의 알데이드를 각각 일반식(a'), (b'), (c'), (d'), (e'), (f'), (g'), (h') (i') 또는 (j')와 축합시키고, 필요한 경우 일반식(I)의 화합물을 다른 일반식(I)의 화합물로 전환시키고/시키거나, 필요한 경우 일반식(I)의 화합물을 약제학적으로 허용되는 이의 염으로 전환시키고/시키거나, 필요한 경우 일반식(I)의 화합물의 이성체 혼합물을 단일 이성체로 분리시킴을 특징으로 하여 일반식(I)의 화합물 또는 약제학적으로 허용되는 이의 염을 제조하는 방법.상기식에서, R1, R2, R3, Y 및 Ph는 제1항에서 정의한 바와 같다.
- 활성성분으로서 제1항에 따른 일반식(I)의 화합물 또는 약제학적으로 허용되는 이의 염과 적당한 담체 및/또는 희석제를 함유하는 약제학적 조성물.
- 타이로신 키나제 억제제로서 사용하기 위한, 제1항에 따른 일반식(I)의 화합물 또는 약제학적으로 허용되는 이의 염.
- 약제의 제조에서 타이로신 커나제 억제제로서 사용하기 위한, 제1항에서 정의한 일반식(I)의 화합물 또는 약제학적으로 허용되는 이의 염의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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US3056790A (en) * | 1960-01-08 | 1962-10-02 | Wisconsin Alumni Res Found | 8-ro-2-quinoline acrylic acid and lower alkyl esters thereof |
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GB9226855D0 (en) * | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
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1990
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1991
- 1991-01-25 IL IL9704991A patent/IL97049A/en active IP Right Grant
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- 1991-02-26 EP EP95102495A patent/EP0662473B1/en not_active Expired - Lifetime
- 1991-02-26 DE DE69115379T patent/DE69115379T2/de not_active Expired - Fee Related
- 1991-02-26 KR KR1019910701435A patent/KR920701136A/ko not_active Application Discontinuation
- 1991-02-26 HU HU913626A patent/HU210791B/hu not_active IP Right Cessation
- 1991-02-26 RU SU915010251A patent/RU2091369C1/ru active
- 1991-02-26 WO PCT/EP1991/000350 patent/WO1991013055A2/en active IP Right Grant
- 1991-02-26 DE DE69131581T patent/DE69131581T2/de not_active Expired - Fee Related
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- 1991-02-26 AT AT91904125T patent/ATE131470T1/de not_active IP Right Cessation
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- 1991-02-26 JP JP50422291A patent/JP3152434B2/ja not_active Expired - Fee Related
- 1991-02-26 ES ES95102495T patent/ES2137386T3/es not_active Expired - Lifetime
- 1991-02-27 PT PT96897A patent/PT96897B/pt not_active IP Right Cessation
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- 1991-10-23 FI FI915010A patent/FI915010A0/fi not_active Application Discontinuation
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1995
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