KR930004234A - 메타노안트라센 화합물 - Google Patents
메타노안트라센 화합물 Download PDFInfo
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- KR930004234A KR930004234A KR1019920014635A KR920014635A KR930004234A KR 930004234 A KR930004234 A KR 930004234A KR 1019920014635 A KR1019920014635 A KR 1019920014635A KR 920014635 A KR920014635 A KR 920014635A KR 930004234 A KR930004234 A KR 930004234A
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- pyridyl
- chloro
- hydrogen
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- -1 cyano, nitro, benzoyl Chemical group 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- RUGKKMPAGMRECE-HOFKKMOUSA-N 1-((9s,10s)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(2-hydroxy-3-pyridylmethyl)piperidine Chemical compound C([C@]12C[C@@H](C3=CC=CC=C32)C2=CC=C(C=C21)Cl)N(CC1)CCC1CC1=CC=CNC1=O RUGKKMPAGMRECE-HOFKKMOUSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- RUGKKMPAGMRECE-UHFFFAOYSA-N l008412 Chemical compound C12=CC(Cl)=CC=C2C(C2=CC=CC=C22)CC12CN(CC1)CCC1CC1=CC=CNC1=O RUGKKMPAGMRECE-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- FAIDZDOWNFSXLC-RNJDCESWSA-N (R)-[1-[[(1S,8S)-4-chloro-1-tetracyclo[6.6.1.02,7.09,14]pentadeca-2(7),3,5,9,11,13-hexaenyl]methyl]piperidin-4-yl]-pyridin-3-ylmethanol Chemical compound C1([C@@H](C2CCN(C[C@]34C5=CC=CC=C5[C@H](C3)C=3C4=CC(Cl)=CC=3)CC2)O)=CC=CN=C1 FAIDZDOWNFSXLC-RNJDCESWSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004407 fluoroaryl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
-
- 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
- C07D401/06—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (10)
- 하기 일반식(Ⅰ)의 화합물 또는 이의 약학적으로 허용 가능한 염:상기식에서, X 및 Y는 수소 및 할로로부터 독립적으로 선택되고;R2는 하기 일반식 (Ia)-(Ic)로 나타낸 구조로 부터 선택된다.상기식에서, R3는 (3-6C)시클로 알킬;(1-6C)알킬;(1-6C)알킬, (1-6C)알콕시, 히드록시, 할로, 시아노, 니트로, 벤조일, 일반식 SO2NRaRb을 갖는 디(1-6C)알킬아미노(1-6C)알킬 아미노설포닐 및 일반식 CONRcRd를 갖는 아미노카르보닐로 구성된 군으로부터 독립적으로 선택된 0-3개의 치환체를 각각 함유하는 페닐 및 나프틸(이때, Ra, Rb, Rc및 Rd는 수소 및(1-6C)알킬로부터 독립적으로 선택되거나, 또는 Ra, Rb, Rc및 Rd각각이 결합되어 있는 질소원자와 함께 5-원 또는 6-원 헤테로시클릭 고리를 형성하며, 상기의 질소는 유일한 이종원자이다);질소, 산소 및 황으로부터 선택된 1-3개의 이종원자를 함유하고, 히드록시, (1-6C)알킬, (1-6C)알콕시, (1-6C)히드록시알킬, 페닐, 클로로 및 플루오로로부터 선택된 0-2개의 치환체를 함유할 수 있는 5-원 및 6-원 헤테로아릴고리 및 이의 벤즈 유도체로부터 선택되고;R4는 수소 및 (1-6C)알킬로부터 선택된다.
- 제1항에 있어서, X 및 Y는 수소 및 클로로로부터 독립적으로 선택되며, (a) R2가 상기 일반식 (Ia)일때, R3는 2-피리딜 및 3-피리딜로부터 선택되고, R4는 수소 및 메틸로부터 선택되며;(b) R2가 상기 일반식(Ib)일때, R3는 3-피리딜이며;(c) R2가 상기 일반식(Ic)일때, R3는 2-히드록시-3-피리딜이고, R4는 수소인 화합물.
- 하기로 구성된 군으로부터 선택된 화합물:R-1-〔((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;S-1-〔1-((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;(R,S)-1-〔1-9RS,10RS)-(2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;1-((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-(2-히드록시-3-피리딜메틸)피페리딘;1-((9RS,10RS)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-(2-히드록시-3-피리딜메틸)피페리딘.
- 하기 일반식(Ⅰ)의 화합물 또는 이의 약학적으로 허용 가능한 염을 포함하는 약학적 조성물:상기식에서, X 및 Y는 수소 및 할로로부터 독립적으로 선택되고;R2는 하기 일반식 (Ia)-(Ic)로 나타낸 구조로 부터 선택된다:식에서, R3는 (3-6C)시클로알킬;(1-6C)알킬;(1-6C)알킬, (1-6C)알콕시, 히드록시, 할로, 시아노, 니트로, 벤조일, 일반식 SO2NRaRb을 갖는 디(1-6C)알킬아미노(1-6C)알킬 아미노설포닐 및 일반식 CONRcRd를 갖는 아미노카르보닐로 구성된 군으로부터 독립적으로 선택된 0-3개의 치환체를 각각 함유하는 페닐 및 나프틸(이때, Ra, Rb, Rc및 Rd는 수소 및(1-6C)알킬로부터 독립적으로 선택되거나, 또는 Ra, Rb, Rc및 Rd각각이 결합되어 있는 질소원자와 함께 5-원 또는 6-원 헤테로시클릭 고리를 형성하며, 상기의 질소는 유일한 이종원자이다);질소, 산소 및 황으로부터 선택된 1-3개의 이종원자를 함유하고, 히드록시, (1-6C)알킬, (1-6C)알콕시, (1-6C)히드록시알킬, 페닐, 클로로 및 플루오로로부터 선택된 0-2개의 치환체를 함유할 수 있는 5-원 및 6-웬 헤테로아릴고리 및 이의 벤즈 유도체로부터 선택되고;R4는 수소 및 (1-6C)알킬로부터 선택된다.
- 제4항에 있어서, X 및 Y는 수소 및 클로로로부터 독립적으로 선택되며, (a) R2가 상기 일반식 (Ia)일때, R3는 2-피리딜 및 3-피리딜로부터 선택되고, R4는 수소 및 메틸로부터 선택되며;(b) R2가 상기 일반식 (Ib)일때, R3는 3-피리딜이며;(c) R2가 상기 일반식 (Ic)일때, R3는 2-히드록시-3-피리딜이고, R4는 수소이다.
- 제5항에 있어서, 상기 화합물이 하기로 부터 선택된 조성물:R-1-〔1-((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;S-1-〔1-((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;(R,S)-1-〔1-9RS,10RS)-(2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-피페리딜〕-1-(3-피리딜)메탄올;1-((9S,10S)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-(2-히드록시-3-피리딜메틸)피페리딘;1-((9RS,10RS)-2-클로로-9,10-디히드로-9,10-메타노안트라센-9-일메틸)-4-(2-히드록시-3-피리딜메틸)피페리딘.
- (a) R2가 하기 일반식 (Ia)일대, 일반식(II)의 상응하는 아미드를 환원시키고;(b) R2가 하기 일반식(Ia)이고, R4가 수소일때, 하기 일반식(III)의 상응하는 알데히드를 일반식 R3Li의 사용하는 알킬리튬 화합물로 처리하고;(c) R2가 하기 일반식(Ia)이고, R4가 수소일때, 하기 일반식(III)의 상응하는 알데히드를 Z가 할로기인 일반식R3MgZ의 마그네슘 할리이드로 처리하고;(d) R2가 하기 일반식(Ia)이고, R4가 (1-6C) 알킬일때, 하기 일반식(IV)의 케톤을 Z가 할로기인 일반식R4MgZ의 상응하는 알킬마그네슘 할라이드로 처리하고;(e) R2가 하기 일반식(Ia) 이고, R4가 (1-6C)알킬일때, 하기 일반식(IV)의 케톤을 일반식 R4Li의 상응하는 알킬리튬 화합물로 처리하고;(f) R2가 하기 일반식(Ib)일때, 하기 일반식(V)의 상응하는 알콜을 산화시키고;(g) R2가 하기 일반식(Ic)일때, 하기 일반식(VI)의 상응하는 알콜을 환원시키고, 이후에, 약학적으로 허용가능한 염의 요구될때, 통상적인 방법으로 상기 화합물을 적당한 산과 반응시키는 것을 특징으로 하는 제1항 내지 제3항중 어느 한 항에서 정의된 화합물을 제조하는 방법:식중, X, Y, R3및 R4는 제2항에서 주어진 의미를 갖는다.
- X, Y, R3및 R4가 제1항에서 주어진 의미를 갖는 하기 일반식(II)의 화합물.
- X, Y, R3가 제1항에서 주어진 의미를 갖는 하기 일반식(V)의 화합물.
- X, Y, R3및 R4가 제1항에서 주어진 의미를 갖는 하기 일반식(VI)의 화합물:※참고사항:최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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GB919117644A GB9117644D0 (en) | 1991-08-15 | 1991-08-15 | Amine derivatives |
GB9117644.6 | 1991-08-15 | ||
GB9207539.9 | 1992-04-07 | ||
GB929207539A GB9207539D0 (en) | 1992-04-07 | 1992-04-07 | Therapeutic agents |
Publications (2)
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KR930004234A true KR930004234A (ko) | 1993-03-22 |
KR100233209B1 KR100233209B1 (ko) | 1999-12-01 |
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KR1019920014635A Expired - Fee Related KR100233209B1 (ko) | 1991-08-15 | 1992-08-14 | 메타노안트라센 화합물 |
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US (3) | US5399568A (ko) |
EP (1) | EP0532177B1 (ko) |
JP (1) | JP3281047B2 (ko) |
KR (1) | KR100233209B1 (ko) |
AT (1) | ATE144252T1 (ko) |
AU (1) | AU652653B2 (ko) |
CA (1) | CA2076168A1 (ko) |
CZ (1) | CZ251892A3 (ko) |
DE (1) | DE69214586T2 (ko) |
DK (1) | DK0532177T3 (ko) |
ES (1) | ES2092645T3 (ko) |
FI (1) | FI923662L (ko) |
GB (1) | GB9216297D0 (ko) |
GR (1) | GR3021399T3 (ko) |
HU (1) | HUT66623A (ko) |
IE (1) | IE922587A1 (ko) |
IL (1) | IL102806A0 (ko) |
NO (1) | NO923198L (ko) |
NZ (1) | NZ243954A (ko) |
TW (1) | TW222622B (ko) |
Families Citing this family (7)
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GB9216298D0 (en) * | 1991-08-15 | 1992-09-16 | Ici Plc | Piperidine derivatives |
US5514683A (en) * | 1992-02-20 | 1996-05-07 | James Black Foundation Limited | Bicyclo 2,2,2!octane derivatives |
US5530012A (en) * | 1994-12-22 | 1996-06-25 | Bristol-Myers Squibb Co. | 3-alkoxybenzylpiperidine derivatives as melatonergic agents |
AU5772196A (en) * | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
GB9517062D0 (en) * | 1995-08-18 | 1995-10-25 | Scherer Ltd R P | Pharmaceutical compositions |
MX2008006076A (es) | 2005-11-09 | 2008-12-16 | Combinatorx Inc | Metodos, composiciones y kits para el tratamiento de condiciones medicas. |
CN101679357A (zh) * | 2007-05-09 | 2010-03-24 | 辉瑞大药厂 | 取代的杂环衍生物及其组合物和作为抗菌剂的药物用途 |
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BE610863A (fr) * | 1960-11-29 | 1962-05-28 | Ciba Geigy | Procédé de préparation de nouvelles amines, entre autres de 9-amino-alcoyl-9,10-dihydro-9,10-éthano-(1,2)-anthracènes |
US3632653A (en) * | 1960-11-29 | 1972-01-04 | Ciba Geigy Corp | Ethano-anthracenes |
BE674185A (ko) * | 1961-10-10 | |||
FR176F (ko) * | 1965-05-19 | |||
US3489799A (en) * | 1967-09-26 | 1970-01-13 | Ciba Geigy Corp | Ethano-anthracenes |
ES367292A1 (es) * | 1968-05-16 | 1971-05-01 | Ciba Geigy | Procedimiento para la obtencion de 9-(aminoalquilo)-9,10- dihidro - 9,10-etanoantracenos sustituidos. |
US3706765A (en) * | 1969-01-03 | 1972-12-19 | Ciba Geigy Corp | Hydroxyethano-anthracenes |
CH532553A (de) * | 1969-03-25 | 1973-01-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen N-substituierten 9-NAminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthano-anthrazenen |
DE2021668A1 (de) * | 1969-05-10 | 1970-11-19 | Ciba Geigy | Neue Amine und Verfahren zu ihrer Herstellung |
US3870796A (en) * | 1970-11-27 | 1975-03-11 | Ciba Geigy Corp | Pharmaceutical preparation |
US4045580A (en) * | 1971-02-23 | 1977-08-30 | Ciba-Geigy Corporation | Pharmaceutical preparation using 9-(2-hydroxy-3-amino-propyl)-9,10-dihydro-9,10-ethano-anthracenes as antidepressants |
US4017542A (en) * | 1971-02-23 | 1977-04-12 | Ciba-Geigy Corporation | 9-(2-Hydroxy-3-amino-propyl)-9,10-dihydro-9,10-ethano-anthracenes and salts thereof |
JPS5911576B2 (ja) * | 1975-07-07 | 1984-03-16 | 住友化学工業株式会社 | 新規なメタノ−アントラセン誘導体の製造法 |
US4224344A (en) * | 1974-12-13 | 1980-09-23 | Sumitomo Chemical Company, Limited | Organic tricyclic compounds |
US4358620A (en) * | 1974-12-13 | 1982-11-09 | Sumitomo Chemical Company, Limited | 9-Formyl-9,10-dihydro-9,10-methanoanthracene |
JPS527972A (en) * | 1975-07-07 | 1977-01-21 | Sumitomo Chem Co Ltd | Process for preparing novel morpholine derivatives |
JPS5268170A (en) * | 1975-12-03 | 1977-06-06 | Sumitomo Chem Co Ltd | Preparation of novel methano-anthracene derivatives |
GB1531278A (en) * | 1975-12-15 | 1978-11-08 | Shionogi & Co | 9,10-dihydro-9,10-methanoanthracene n-oxide derivatives and the production thereof |
JPS5910654B2 (ja) * | 1976-04-07 | 1984-03-10 | 住友化学工業株式会社 | 新規なメタノ−アントラセン誘導体 |
JPS5936621B2 (ja) * | 1976-05-19 | 1984-09-05 | 大塚製薬株式会社 | 新規なカルボスチリル誘導体 |
US4318926A (en) * | 1979-08-14 | 1982-03-09 | Ciba-Geigy Corporation | Method of curing or alleviating herpes infections and pharmaceutical compositions suitable therefor |
US5226570A (en) * | 1991-07-16 | 1993-07-13 | Fabio Pedrini | Self-centering roof rack |
GB9216298D0 (en) * | 1991-08-15 | 1992-09-16 | Ici Plc | Piperidine derivatives |
GB9117639D0 (en) * | 1991-08-15 | 1991-10-02 | Ici Plc | Therapeutic compounds |
JP3005175U (ja) | 1993-08-23 | 1994-12-13 | 有限会社サンエイ | レンタルショップ用ビデオケース |
-
1992
- 1992-07-31 GB GB929216297A patent/GB9216297D0/en active Pending
- 1992-08-06 US US07/927,685 patent/US5399568A/en not_active Expired - Lifetime
- 1992-08-11 DK DK92307352.2T patent/DK0532177T3/da active
- 1992-08-11 ES ES92307352T patent/ES2092645T3/es not_active Expired - Lifetime
- 1992-08-11 AT AT92307352T patent/ATE144252T1/de not_active IP Right Cessation
- 1992-08-11 DE DE69214586T patent/DE69214586T2/de not_active Expired - Lifetime
- 1992-08-11 EP EP92307352A patent/EP0532177B1/en not_active Expired - Lifetime
- 1992-08-14 JP JP21699592A patent/JP3281047B2/ja not_active Expired - Lifetime
- 1992-08-14 NZ NZ243954A patent/NZ243954A/en unknown
- 1992-08-14 KR KR1019920014635A patent/KR100233209B1/ko not_active Expired - Fee Related
- 1992-08-14 AU AU21017/92A patent/AU652653B2/en not_active Ceased
- 1992-08-14 IE IE258792A patent/IE922587A1/en unknown
- 1992-08-14 NO NO92923198A patent/NO923198L/no unknown
- 1992-08-14 IL IL102806A patent/IL102806A0/xx unknown
- 1992-08-14 CZ CS922518A patent/CZ251892A3/cs unknown
- 1992-08-14 CA CA002076168A patent/CA2076168A1/en not_active Abandoned
- 1992-08-14 HU HU9202641A patent/HUT66623A/hu unknown
- 1992-08-14 FI FI923662A patent/FI923662L/fi unknown
- 1992-08-19 TW TW081106563A patent/TW222622B/zh active
-
1995
- 1995-01-19 US US08/374,053 patent/US5550136A/en not_active Expired - Lifetime
-
1996
- 1996-04-15 US US08/632,705 patent/US5719166A/en not_active Expired - Lifetime
- 1996-10-17 GR GR960402635T patent/GR3021399T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
US5550136A (en) | 1996-08-27 |
GR3021399T3 (en) | 1997-01-31 |
DE69214586D1 (de) | 1996-11-21 |
HU9202641D0 (en) | 1992-10-28 |
IE922587A1 (en) | 1993-02-24 |
AU652653B2 (en) | 1994-09-01 |
ES2092645T3 (es) | 1996-12-01 |
CZ251892A3 (en) | 1993-02-17 |
EP0532177A1 (en) | 1993-03-17 |
JP3281047B2 (ja) | 2002-05-13 |
NO923198D0 (no) | 1992-08-14 |
JPH05246988A (ja) | 1993-09-24 |
FI923662L (fi) | 1993-02-16 |
IL102806A0 (en) | 1993-01-31 |
FI923662A0 (fi) | 1992-08-14 |
HUT66623A (en) | 1994-12-28 |
KR100233209B1 (ko) | 1999-12-01 |
EP0532177B1 (en) | 1996-10-16 |
DK0532177T3 (da) | 1997-03-24 |
AU2101792A (en) | 1993-02-18 |
NO923198L (no) | 1993-02-16 |
NZ243954A (en) | 1995-09-26 |
TW222622B (ko) | 1994-04-21 |
ATE144252T1 (de) | 1996-11-15 |
GB9216297D0 (en) | 1992-09-16 |
US5719166A (en) | 1998-02-17 |
DE69214586T2 (de) | 1997-03-20 |
US5399568A (en) | 1995-03-21 |
CA2076168A1 (en) | 1993-02-16 |
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