KR920019766A - 3-아릴 옥사졸리디논 유도체, 그의 제조방법 및 치료학적 용도 - Google Patents
3-아릴 옥사졸리디논 유도체, 그의 제조방법 및 치료학적 용도 Download PDFInfo
- Publication number
- KR920019766A KR920019766A KR1019920005842A KR920005842A KR920019766A KR 920019766 A KR920019766 A KR 920019766A KR 1019920005842 A KR1019920005842 A KR 1019920005842A KR 920005842 A KR920005842 A KR 920005842A KR 920019766 A KR920019766 A KR 920019766A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- pyridyl
- oxygen
- compound
- derivative
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 239000001301 oxygen Substances 0.000 claims 11
- -1 piperidino, pyrroli Dino, morpholino Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241000125205 Anethum Species 0.000 claims 1
- 238000010934 O-alkylation reaction Methods 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940001470 psychoactive drug Drugs 0.000 claims 1
- 239000004089 psychotropic agent Substances 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic 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
- A61P25/20—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 하기식을 가지며, 라세믹 형태를 비롯한 각종 입체이성질체 형태 또는 이들 형태들의 혼합물 형태를 취하는 유도체(I) 및 이들의 N-산화물과 이들 유도체 및 N-산화물의 산부가염.상기식중, R1C1-C4알킬 또는 CF3를 나타내고, R3는 CH2R4기로서, R4는 (i) 1 또는 2개의 질소원자를 갖는 5원 또는 6원 방향족 복소환기, (ii) 1또는 2개의 질소원자를 벤젠고리와 융합된 5원 또는 6원 방향족 복소환기, 또는 (iii)하기식을 갖는 기이다.(식중, n=0 또는 1이고, R5및 R6는 독립적으로 C1-C4알킬 또는 벤질을 나타내고, 또한 R5및 R6는 그들의 결합되어 있는 질소원자와 함께 피페리디노, 피롤리디노, 모로폴리노 또는 N-메틸 피페라지노 라디칼을 형성할 수 도 있다).
- 제1항에 있어서, 식중 R4가 이미다졸릴, 피라졸릴, 피리딜, 피리미디닐, 피라지닐, 피리다지닐, 퀴놀릴, 이소퀴놀릴, 퀴녹살리닐, 퀴나졸리닐 및 신놀리닐을 포함하는 군으로부터 선택된 것인 화합물.
- 제1항 또는 제2항에 있어서, 식중 R4=이미다졸릴, 피리딜, 퀴놀릴, 피리딜 N-산화물 또는 퀴놀릴 N-산화물인 화합물.
- 제1항에 있어서, 이하의 (a)-(1)을 포함하는 군으로부터 선택된 화합물, (a) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜인 유도체, b) 식중 R1=C1-C4알킬이고, X는 산소이며, R2CF3이고, R4=피리딜 N-산화물인 유도체, (c) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜이며, 또한 옥사졸리디논 고리내의 비대칭 탄소가 (R) 배위를 갖는 유도체, (d) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜 N-산화물이며, 또한 옥사졸리디논 고리내의 비대칭 탄소가 (R)배위를 갖는 유도체, (e) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜이며, 또한 R2-*CH(OR3)-의 비대칭 탄소가 (R)배위를 갖는 유도체, (f) 식중 R1=C1-C4알킬이고, X는 산소이며, R4=피리딜 N-산화물이고, 또한 R2-*CH(OR3)-비대칭 탄소가 (R)배위를 갖는 유도체, (g) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜이며, 또한 R2-*CH(OR3)-비대칭 탄소가 (S)배위를 갖는 유도체, (h) 식중 R1=C1-C4알킬이고, X는 산소이며, R4=피리딜 N-산화물이고, 또한 R2-*CH(OR3)-비대칭 탄소가 (S)배위를 갖는 유도체, (i) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜이며, 또한 배위가 (R, P)인 유도체, (j) 식중 R1=C1-C4알킬이고, X는 산소이며, R2=CF3이고, R4=피리딜이며, 또한 배위가 (R, P)인 유도체, (k) 앞서 열거한 (a)-(j)항에서 X가 산소대신 CH2기인 유도체, 및 (I)앞서 열거한 (a)-(k)항에서 산부가염 형태를 갖는 유도체.
- 제1항에 있어서, 하기식을 갖는 것들로부터 선택된 화합물.
- 제5항에 있어서, N-산화물 형태인 화합물.
- 제1항 내지 제6항중 어느 한 항에 있어서, 정의한 바있는 적어도 1종의 화합물과 함께 생리학적으로 허용되는 부형제를 함유하는 특징으로 하는 약학 조성물.
- 제1항 내지 제6항에서 정의한 화합물들의 향정신성약제 제조에 사용되는 용도.
- 하기식(II)를 갖는 화합물에 대하여 하기식(III)을 갖는 각각의 화합물을 사용하여 O-알킬화반응을 수행하고, 이어서 임의로 생성된 유도체의 N-산화반응 및/또는 염화반응을 수행하는 것을 특징으로 하는 하기식(I)을 갖는 유도체의 제조방법.[상기식들 중, R1은 C1-C4알킬을 나타내고, X는 산소원자 또는 메틸렌기를 나타내며, R2는 C1-C4알킬 또는 CF3를 나타내고, R3는 CH2R4기로서, R4는 (i) 1또는 2개의 질소원자를 갖는 5원 또는 6원 방향족 복소환기, (ii) 1 또는 2개의 질소원자를 가지며 벤젠고리와 융합된 5원 또는 6원 방향족 복소환기, 또는 (iii) 하기식을 갖는 기이며,(식중, n=0 또는 1이고, R5및 R6는 독립적으로 C1-C4알킬 또는 벤질을 나타내고, 또한 R5는 그들이 결합되어 있는 질소원자와 함께 피페리디노, 피롤리디노, 모르폴리노 또는 N-메틸 피페라지노 라디칼을 형성할 수 도 있다), 및 Y는 할로겐이다.]※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9104641 | 1991-04-16 | ||
FR9104641A FR2675504B1 (fr) | 1991-04-16 | 1991-04-16 | Derives d'aryl-3 oxazolidinone, leur procede de preparation et leur application en therapeutique. |
Publications (1)
Publication Number | Publication Date |
---|---|
KR920019766A true KR920019766A (ko) | 1992-11-19 |
Family
ID=9411887
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920005842A KR920019766A (ko) | 1991-04-16 | 1992-04-08 | 3-아릴 옥사졸리디논 유도체, 그의 제조방법 및 치료학적 용도 |
Country Status (13)
Country | Link |
---|---|
US (1) | US5264443A (ko) |
EP (1) | EP0511031B1 (ko) |
JP (1) | JPH05112542A (ko) |
KR (1) | KR920019766A (ko) |
AT (1) | ATE138059T1 (ko) |
AU (1) | AU647909B2 (ko) |
CA (1) | CA2065962A1 (ko) |
DE (1) | DE69210675T2 (ko) |
DK (1) | DK0511031T3 (ko) |
ES (1) | ES2087474T3 (ko) |
FR (1) | FR2675504B1 (ko) |
GR (1) | GR3020546T3 (ko) |
NZ (1) | NZ242351A (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2715155B1 (fr) * | 1994-01-19 | 1996-07-26 | Mayoly Spindler | Inhibiteurs de la monoamine oxydase B et leurs procédés de préparation. |
ATE170179T1 (de) * | 1994-11-02 | 1998-09-15 | Merck Patent Gmbh | Adhäsionsrezeptor-antagonisten |
US6455554B1 (en) | 1999-06-07 | 2002-09-24 | Targacept, Inc. | Oxopyridinyl pharmaceutical compositions and methods for use |
JPWO2004105753A1 (ja) * | 2003-05-29 | 2006-07-20 | 協和メデックス株式会社 | 抗うつ剤または抗うつ用飲食品 |
MX2010014461A (es) * | 2008-06-24 | 2011-04-28 | Valeant Pharmaceuticals Int | Derivados de benciloxi anilida utiles como moduladores de canales de potasio. |
GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
KR20220008824A (ko) | 2019-04-17 | 2022-01-21 | 컴퍼스 패쓰파인더 리미티드 | 실로시빈으로 불안 장애, 두통 장애 및 섭식 장애를 치료하는 방법 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2954381A (en) * | 1958-12-03 | 1960-09-27 | Us Vitamin Pharm Corp | Heteroaryloxazolidinediones |
US3290326A (en) * | 1963-09-20 | 1966-12-06 | Hoffmann La Roche | Esters of 4-lower alkyl-5-oxazole-car-bamic acid and intermediates therefor |
US4133675A (en) * | 1976-07-23 | 1979-01-09 | Ciba-Geigy Corporation | Pyridyloxy-phenoxy-alkanecarboxylic acid derivatives which are effective as herbicides and as agents regulating plant growth |
US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
FR2506769A2 (fr) * | 1978-06-09 | 1982-12-03 | Delalande Sa | Para-((cyano-5 n pentyl-1) phenyl)-3 methoxymethyl-5 oxazolidinone-2, son procede de preparation et ses applications en therapeutique |
CA1171865A (en) * | 1980-06-04 | 1984-07-31 | Alain Lacour | N-aryl azolone derivatives, the process for preparing the same and their application in therapeutics |
FR2608604B1 (fr) * | 1986-12-19 | 1989-04-28 | Delalande Sa | Derives 5-hydroxyethyles de l'oxazolidinone-2, leurs procedes de preparation et leurs applications en therapeutique |
FR2653017B1 (fr) * | 1989-10-17 | 1995-05-05 | Delalande Sa | Derives d'aryl-3 oxazolidinone-2, leur procede de preparation et leur application en therapeutique. |
-
1991
- 1991-04-16 FR FR9104641A patent/FR2675504B1/fr not_active Expired - Fee Related
-
1992
- 1992-03-18 ES ES92400721T patent/ES2087474T3/es not_active Expired - Lifetime
- 1992-03-18 DK DK92400721.4T patent/DK0511031T3/da active
- 1992-03-18 EP EP92400721A patent/EP0511031B1/fr not_active Expired - Lifetime
- 1992-03-18 DE DE69210675T patent/DE69210675T2/de not_active Expired - Fee Related
- 1992-03-18 AT AT92400721T patent/ATE138059T1/de not_active IP Right Cessation
- 1992-04-08 KR KR1019920005842A patent/KR920019766A/ko not_active Application Discontinuation
- 1992-04-09 US US07/865,885 patent/US5264443A/en not_active Expired - Fee Related
- 1992-04-14 CA CA002065962A patent/CA2065962A1/en not_active Abandoned
- 1992-04-14 NZ NZ242351A patent/NZ242351A/xx unknown
- 1992-04-15 AU AU14910/92A patent/AU647909B2/en not_active Ceased
- 1992-04-15 JP JP4095189A patent/JPH05112542A/ja active Pending
-
1996
- 1996-07-16 GR GR960401914T patent/GR3020546T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
DK0511031T3 (da) | 1996-09-30 |
ES2087474T3 (es) | 1996-07-16 |
JPH05112542A (ja) | 1993-05-07 |
GR3020546T3 (en) | 1996-10-31 |
FR2675504B1 (fr) | 1995-01-27 |
US5264443A (en) | 1993-11-23 |
FR2675504A1 (fr) | 1992-10-23 |
ATE138059T1 (de) | 1996-06-15 |
NZ242351A (en) | 1993-08-26 |
AU647909B2 (en) | 1994-03-31 |
EP0511031A1 (fr) | 1992-10-28 |
CA2065962A1 (en) | 1992-10-17 |
EP0511031B1 (fr) | 1996-05-15 |
DE69210675T2 (de) | 1996-11-28 |
AU1491092A (en) | 1992-10-22 |
DE69210675D1 (de) | 1996-06-20 |
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