KR900018070A - N-(아릴옥시알킬)헤테로아릴피페리딘 및 -헤테로아릴피페라진, 이의 제조방법 및 약제로서의 이의 용도 - Google Patents
N-(아릴옥시알킬)헤테로아릴피페리딘 및 -헤테로아릴피페라진, 이의 제조방법 및 약제로서의 이의 용도 Download PDFInfo
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- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
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- 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
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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
- C07D401/04—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
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (19)
- 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 이의 산 부가염.
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- 상기식에서, X는 -O-, -S-, -NH- 또는이고, P는 1 또는 2이며, Y는 P가 1인 경우 수소, C1-C6-알킬, -OH, C1, F, Br, I, C1-C6-알콕시, -CF3, -NO2또는 -NH2이고, P가 2이고 X가 -O-인 경우, 저급 알콕시이며, R2는 저급 알킬, 아릴저급 알킬, 아릴, 사이클로알킬, 아로일, 알카노일 및 페닐설포닐 그룹으로 이루어진 그룹 중에서 선택되고, Z는또는이며, n은 2,3,4 또는 5이고, R은 수소, 알킬, C1-C6-알콕시, 하이드록실, 카복실, CI, F, Br, I, 아미노, C1-C6모노 또는 디알킬 아미노, -NO2, 저급알킬티오, -OCF3, 시아노, 아실아미노, -CF3, 트리플루오로아세틸, 아미노 카보닐,알킬,O-알킬,아릴,헤테로 아릴 또는알킬 [여기서, 알킬은 저급 알킬이고, 아릴은 페닐 또는 일반식의 그룹(여기서, R1은 수소, 저급 알킬, C1-C6-알콕시, 하이드록시, CI, F, Br, I, C1-C6알킬 아미노, -NO2, -CN, -CF3또는 -OCF3이다)이며, 헤테로아릴은 일반식의 그룹(여기서, Q는 -O-, -S-,또는 -CH=N 이다)이고, R3은 수소, 저급 알킬 또는 아실이다]이며, m은 1.2 또는 3이다.
- 제1항에 있어서, X는 -O-, -S- 또는 -NH인 화합물.
- 제2항에 있어서, n은 2,3 또느 ㄴ4이고 Y는 수소이거나 6위치에서 염소 또는 불소이며 p는 1인 화합물.
- 제3항에 있어서, R은 수소, 알킬, C1-C6-알콕시, C1-C6-알킬티오, 할로겐, C1-C6-알킬아미노,알킬,페닐 또는 -CH(OR3)-C1-C6-알킬이고 m은 2 또는 3인 화합물.
- 제3항에 있어서, n은 3 또는 4이고, m은 2이며 R은 -OCH3또는인 화합물.
- 제1항에 있어서, 1-[4-[3-[4-(1H-인다졸-3-일)-1-피페라지닐]프로폭시]-3-메톡시페닐]에탄온 또는 약제학적으로 허용되는 이의 산 부가염.
- 제1항에 있어서, 1-[4-[3-[4-(1,2-베느이속사졸-3-일)-1-피페라디닐]프로폭시]-3-메톡시페닐]에탄온 또는 약제학적으로 허용되는 이의 산 부가염.
- 제1항에 있어서, 1-[4-[3-[4-(6-플루오로-1,2-벤즈이속사졸-3-일)-1-피페라지닐]프로폭시]-3-메톡시페닐]에탈온 또는 약제학적으로 허용되는 이의 산 부가염.
- 제1항에있어서,1-[4-[4-[4-(1,2-벤즈이속사졸-3-일)-1-피페라지닐]부록시]-3-메톡시페닐]에탈온 또는 약제학적으로 허용되는 이의 산 부가염.
- 제1항에 있어서, 1-[4-[4-[4-(6-플루오로-1,2-벤즈이속사졸-3-일)-1-피페라지닐]부록시]-3-메톡시페닐]에탈온 또는 약제학적으로 허용되는 이의 산 부가염.
- 활성성분으로 제1항에서 청구한 화합물과 이에 적합한 담체를 포함하는 약제학적 조성물.
- 정신병 치료 활성 및/또는 진통 활성이 있는 약제를 제조하기 위한, 제1항에서 청구한 화합물의 용도.
- a)일반식(Ⅱ)의 화합물을 알킬화 조건하에 일반식(Ⅲ)의 화합물과 반응시키고, b)임의로 R이-C6-알킬인 일반식(Ⅰ)의 화합물을 환원시켜 R이 CH2(OH)-C1-C6-알킬인 일반식(Ⅰ)의 화합물을 수득하고, c)임의로 R이 -CH(OR3)-C1-C6-알킬이고, R3은 수소인 일반식(Ⅰ)의 화합물을 알카노산 무수물과 반응시켜 R이 C1-C6-알카노일인 일반식(Ⅰ)의 화합물을 수득하고, d)임의로 R이 하이드록시인 일반식(Ⅰ)의 화합물을 우선 강염기와 반응시키고, 이어서 일반식 Hal-C1-C6알킬의 화합물(여기서, Hal은 염소 또는 브롬이다)과 반응시켜 R이 C1-C6-알콕시인 일반식(Ⅰ)의 화합물을 수득하고, e)임의로 X가 N-R2이고, R2는 수소인 일반식(Ⅰ)의 화합물을 C1-C6-알카노일 또는 아로일 할라이드와 반응시켜 X가 NR2이고 R2는 C1-C6-알카노일 또는 아로일인 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, 제1항에서 청구한 화합물을 제조하는 방법.
-
- 상기식에서, X,Y,X,R,m,n 및 p는 제1항에서 정의한 바와 같고, Hal은 염소 또는 브롬이다.
- 제13항에 있어서, 단계a)으 반응을 불활성 용매 중에서 50℃ 내지 용매의 환류온도에서 산 수용체의 존재하에 수행하는 방법.
- ※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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US35441189A | 1989-05-19 | 1989-05-19 | |
US354411 | 1989-05-19 | ||
US354,411 | 1989-05-19 | ||
US45679089A | 1989-12-29 | 1989-12-29 | |
US456790 | 1989-12-29 | ||
US456,790 | 1989-12-29 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1019910008308A Division KR930009238B1 (ko) | 1990-05-24 | 1991-05-23 | 콘버젼스 보정장치 |
Publications (2)
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KR900018070A true KR900018070A (ko) | 1990-12-20 |
KR0157308B1 KR0157308B1 (ko) | 1998-11-16 |
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Application Number | Title | Priority Date | Filing Date |
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KR1019900007102A KR0157308B1 (ko) | 1989-05-19 | 1990-05-18 | N-(아릴옥시알킬)헤테로아릴피페리딘 및 -헤테로아릴피페라진, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
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EP (1) | EP0402644B1 (ko) |
JP (1) | JPH0662580B2 (ko) |
KR (1) | KR0157308B1 (ko) |
CN (2) | CN1086387C (ko) |
AT (1) | ATE126512T1 (ko) |
AU (1) | AU640653B2 (ko) |
CA (1) | CA2017193C (ko) |
CZ (1) | CZ282385B6 (ko) |
DD (1) | DD300433A5 (ko) |
DE (1) | DE69021645T2 (ko) |
DK (1) | DK0402644T3 (ko) |
ES (1) | ES2076253T3 (ko) |
FI (2) | FI104072B (ko) |
GR (1) | GR3017447T3 (ko) |
HK (2) | HK1006710A1 (ko) |
HU (2) | HU218200B (ko) |
IE (1) | IE68431B1 (ko) |
IL (1) | IL94425A (ko) |
NO (1) | NO177301C (ko) |
NZ (1) | NZ233710A (ko) |
PL (1) | PL163965B1 (ko) |
PT (1) | PT94084B (ko) |
RU (3) | RU2147583C1 (ko) |
SK (1) | SK279474B6 (ko) |
Families Citing this family (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
DK203990D0 (da) * | 1990-08-24 | 1990-08-24 | Novo Nordisk As | Piperazinylderivater |
US5328920A (en) * | 1991-04-17 | 1994-07-12 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted (pyridinylamino)-indoles |
US5177088A (en) * | 1991-04-17 | 1993-01-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Substituted 3-(pyridinylamino)-indoles |
TW241263B (ko) * | 1991-08-22 | 1995-02-21 | Hoechst Roussel Pharma | |
NZ240863A (en) * | 1991-09-11 | 1995-04-27 | Mcneilab Inc | Substituted 4-aryl piperidine and 4-aryl piperazine derivatives, preparation and pharmaceutical compositions thereof |
US5378714A (en) * | 1991-11-27 | 1995-01-03 | Novo Nordisk A/S | Antipsychotic piperidine derivatives |
NZ245260A (en) * | 1991-11-27 | 1995-06-27 | Novo Nordisk As | Piperidine derivatives, preparation and pharmaceutical compositions thereof |
AU3170793A (en) * | 1991-12-25 | 1993-07-28 | Zeria Pharmaceutical Co., Ltd. | Tricyclic compound and medicine containing the same |
US5631269A (en) * | 1992-10-23 | 1997-05-20 | Merck Sharp & Dohme Limited | Dopamine receptor subtype ligands |
AU5341394A (en) * | 1992-10-23 | 1994-05-24 | Merck Sharp & Dohme Limited | Dopamine receptor subtype ligands |
DK60593D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
DK60793D0 (da) * | 1993-05-26 | 1993-05-26 | Novo Nordisk As | Kemiske forbindelser, deres fremstilling og anvendelse |
GB9318691D0 (en) * | 1993-09-09 | 1993-10-27 | Merck Sharp & Dohme | Therapeutic agents |
EP0724572B1 (en) * | 1993-09-15 | 1998-12-16 | MERCK SHARP & DOHME LTD. | Fused tricyclic heteroaromatic derivatives as dopamine receptor subtype ligands |
JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
ES2101646B1 (es) * | 1995-04-12 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
US5668148A (en) * | 1995-04-20 | 1997-09-16 | Merck & Co., Inc. | Alpha1a adrenergic receptor antagonists |
ATE199147T1 (de) * | 1995-06-06 | 2001-02-15 | Aventis Pharma Inc | Benzisoxazol- und indazol- derivate als antipsychotika |
BR9612578A (pt) * | 1996-01-05 | 1999-07-27 | Hoechst Marion Roussel Inc | 4,5 DidronaftÚ1,2-c¾ isoxazóis e seus derivedos tendo atividade no scn |
US5880121A (en) * | 1996-01-05 | 1999-03-09 | Hoechst Marion Roussel Inc. | 4,5-dihydronaphth (1,2-c) isoxazoles and derivatives thereof |
ES2144355B1 (es) * | 1997-12-30 | 2001-01-01 | Ferrer Int | Compuestos derivados del cromeno. |
WO2001017993A1 (en) * | 1999-09-09 | 2001-03-15 | EGIS Gyógyszergyár Rt. | Alkylpiperidi nylbenzo [d] isoxazole derivatives having psychotropic activity, pharmaceutical compositions containing the same, and a process for the preparation of the active ingredient |
GB0102841D0 (en) * | 2001-02-05 | 2001-03-21 | Novartis Ag | Organic compounds |
AU2006201188B2 (en) * | 2001-02-05 | 2007-11-15 | Novartis Ag | New use of iloperidone |
WO2003020707A1 (en) | 2001-08-31 | 2003-03-13 | Novartis Ag | Optical isomers of an iloperidone metabolite |
WO2003037337A1 (en) | 2001-10-30 | 2003-05-08 | Novartis Ag | Depot formulations of iloperidone and a star polymer |
US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
GB0216416D0 (en) * | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
EA200500342A1 (ru) * | 2002-09-17 | 2005-08-25 | УОРНЕР-ЛАМБЕРТ КОМПАНИ Эл-Эл-Си | Гетероциклические замещённые пиперазины для лечения шизофрении |
WO2004041793A1 (en) * | 2002-11-08 | 2004-05-21 | Warner-Lambert Company Llc | Phenylalkyl and pyridylalkyl piperazine derivatives |
US7160888B2 (en) * | 2003-08-22 | 2007-01-09 | Warner Lambert Company Llc | [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia |
GB0322994D0 (en) * | 2003-10-01 | 2003-11-05 | Novartis Ag | Organic compounds |
AU2007217040A1 (en) | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-HT6 receptor affinity |
PL2083811T3 (pl) | 2006-11-22 | 2017-05-31 | Clinical Research Associates, Llc | Sposoby leczenia zespołu downa, zespołu łamliwego chromosomu x oraz autyzmu |
WO2008128166A1 (en) * | 2007-04-13 | 2008-10-23 | Concert Pharmaceuticals Inc. | Deuterated derivatives of 4-(6-fluoro-1, 2-benzisoxazol-3-yl) piperidine compounds |
CN101824030B (zh) * | 2009-03-04 | 2014-06-18 | 北京德众万全药物技术开发有限公司 | 一种伊潘立酮的制备方法 |
NZ597107A (en) | 2009-06-25 | 2013-12-20 | Alkermes Pharma Ireland Ltd | Heterocyclic compounds for the treatment of neurological and psychological disorders |
US8802855B2 (en) | 2009-09-19 | 2014-08-12 | Zhejiang Huahai Pharmaceutical Co., Ltd. | Method for preparation of iloperidone and crystallization method thereof |
CN102030744B (zh) * | 2009-09-30 | 2013-04-17 | 天津药物研究院 | 伊潘立酮晶体、其制备方法及药物组合物 |
WO2011061750A2 (en) * | 2009-11-19 | 2011-05-26 | Symed Labs Limited | Process for the preparation of iloperidone using a novel intermediate |
WO2011154860A1 (en) * | 2010-06-08 | 2011-12-15 | Alembic Pharmaceuticals Limited | An improved process for preparing iloperidone |
CN102311430A (zh) * | 2010-06-29 | 2012-01-11 | 大道隆达(北京)医药科技发展有限公司 | 伊潘立酮的新晶态及其制备方法 |
ITMI20101294A1 (it) * | 2010-07-14 | 2012-01-15 | Dipharma Francis Srl | Procedimento per la preparazione di iloperidone |
WO2012032532A1 (en) * | 2010-09-07 | 2012-03-15 | Symed Labs Limited | "processes for the preparation of 4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone and intermediates thereof" |
WO2012063269A2 (en) | 2010-11-12 | 2012-05-18 | Cadila Healthcare Limited | Process for preparing iloperidone |
EP2640391B1 (en) | 2010-11-15 | 2015-11-11 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
WO2012123963A2 (en) | 2011-02-24 | 2012-09-20 | Megafine Pharma (P) Ltd. | A process for preparation of iloperidone and amorphous co- precipitate of iloperidone with pharmaceutically acceptable excipient |
WO2012153341A1 (en) | 2011-05-12 | 2012-11-15 | Arch Pharmalabs Limited | A process for the preparation of iloperidone and pharmaceutically acceptable salts thereof |
WO2012164516A1 (en) | 2011-06-03 | 2012-12-06 | Lupin Limited | Process for the preparation of iloperidone |
ITMI20120511A1 (it) * | 2012-03-29 | 2013-09-30 | Procos Spa | Processo one-pot per la sintesi di iloperidone |
WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
EP4032889A1 (en) | 2013-12-20 | 2022-07-27 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
US10815242B2 (en) | 2015-06-19 | 2020-10-27 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
BR112019012821A2 (pt) | 2016-12-19 | 2019-11-26 | Agenebio Inc | derivados de benzodiazepina, composições e métodos para o tratamento do comprometimento cognitivo |
US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
EP3810611A4 (en) | 2018-06-19 | 2022-03-30 | Agenebio, Inc. | BENZODIAZEPINE DERIVATIVES, COMPOSITIONS, AND METHODS OF TREATING COGNITIVE IMPAIRMENT |
WO2024039886A1 (en) | 2022-08-19 | 2024-02-22 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
US4458076A (en) * | 1983-05-31 | 1984-07-03 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
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 |
US4590196A (en) * | 1984-08-23 | 1986-05-20 | Bristol-Myers Company | Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives |
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1990
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