KR930702980A - 인단 유도체 - Google Patents
인단 유도체Info
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- KR930702980A KR930702980A KR1019930701680A KR930701680A KR930702980A KR 930702980 A KR930702980 A KR 930702980A KR 1019930701680 A KR1019930701680 A KR 1019930701680A KR 930701680 A KR930701680 A KR 930701680A KR 930702980 A KR930702980 A KR 930702980A
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- lower alkyl
- hydrogen
- optionally substituted
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- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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Abstract
Description
Claims (41)
- 하기의 일반식 I을 갖는 5-치환 트랜스-1-피페라지노인단 유도체 또는 약제학적으로 허용가능한 이것의 산부가염 또는 이것의 프로드러그
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- [상기식에서 Ar이 선택적으로 치환된 페닐일때, R은 히드록시로 선택적으로 치환된 알켄일 또는 저급 알킬 또는 수소일 수 없다는 조건부로; X는 할로겐, 트리플루오로메틸, 저급알킬, 저급알킬티오, 저급알킬옥시, 히드록시, 저급 알킬술포닐, 저급알킬-또는 디알킬아니노, 트리플루오로메틸티오 또는 시아노기 이고, R은 선택적으로 1또는 2의 히드록시기로 치환되고, 존재하는 모든 히드록시기는 2내지 24탄소수를 갖는 지방족 카르복실산으로 선택적으로 에스테르화되어 있는 수소, 저급알킬, 또는 알켄일, 시클로알킬, 또는 시클로 알킬 저급알킬이거나 또는 R은 치환체
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- 이며, {상기 식에서 n은 정수 1내지 6; U는 CH 또는 N;Y는 CH2, O, S또는 N-R′(여기서 R1은 1 또는 2의 히드록시기로 선택적으로 치환된 저급 알킬 또는 알켄일 또는 시클로알킬메틸 또는 시클로알킬 또는 수소이거나 또는 할로겐, 트리플루오로메틸 또는 저급 알킬로 선택적으로 치환된 페닐기이다. ); W는 O 또는 S; Z는
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- (여기서, R2및 R3는 할로겐 또는 트리플루오로메틸로 선택적으로 치환된 1,2-페닐렌, 수소 또는 저급알킬, -CH=CH-CH2-, -CH=CH-이다)이거나, 또는 U가 질소이고 Y가 NR1인 경우 Z는 또한 1,2-C6H4CH2-(퀴나졸리딘온 또는 -티온고리계를 형성하는 것) 또는 1,2-C6H4CO-(퀴나졸리딘디온 또는 티옥소퀴나졸리딘온 고리구조를 형성하는 것)일 수 있다); 그리고 Ar은 할로겐, 트리플루오로메틸 또는 저급 알킬로 선택적으로 치환된 페닐고리이거나 또는 Ar은 저급 알킬로 선택적으로 치환된 티오펜 또는 푸란 고리이다.〕
- 제1항에 있어서, Ar은 할로겐 또는 메틸로 선택적으로 치환된 페닐기, 바람직하게는 5-플루오로페닐이고, 및/또는 X는 Cl또는F인 것을 특징으로 하는 5-치환 트랜스-1-피페라지노인단 유도체.
- 제 1항 또는 제 2항에 있어서, R이 식
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- 기인 것을 특징으로 하는 5-치환 트랜스-1-피페라지노인단 유도체.
- (여기에서 n은 2; U는 N;W는 O는 S;Z는 -CH2-CH2-, 또는 -CH2-CH2-CH2-; 그리고 Y는 R1이 수소 또는 저급 알킬인 NR1기이다. )
- 제 1항에 있어서, (-)-트랜스-1-[2-[4-[클로로-3-(4-플루오로페닐)-2,3-디히드로-1H-인덴-1-일]피페라진-1-일]-에틸]-3-이소프로필-2-이미다졸리디논, 디말레산염;(+)-트랜스-1-[2-[4-[5-플루오르-3-(4-플루오로페닐)-2,3-디히드로-1H-인덴-1-일]피페라진-1-일]에틸]-테트라히드로-2(1H)-피리미딘티온, 이염산염; (-)-트랜스-1-[2-[4-[5-클로로-3-(4-플루오로페닐)-2,3-디히드로-1H-인덴-1-일]피페라진-1-일]-에틸]-테트라히드로-2(1H)-피리미딘티온, 이염산염; (+)-트랜스-1-[2-[4-[5-플루오르-3-(4-플루오로페닐)-2,3-디히드로-1H-인덴-1-일]피페라진-1-일]에틸]-테트라히드로-2(1H)-피리미딘티온, 디말레산염; 및 (-)-트랜스-1-[2-[4-[5-클로로-3-(4-플루오로페닐)-2,3-디히드로-1H-인덴-1-일]피페라진-1-일]-에틸]-테트라히드로-2(1H)-피리미딘티온, 디말레산염; 및 이것들의 산부가염의 군으로부터 선택되는 것을 특징으로 하는 5-치환 트랜스-1-피페라지노인단 유도체.
- 산 또는 활성산과, 알콜이나 아민의 존재하에서 또는 단독으로의 포름알데히드와, 또는 할로겐화아실옥시 메틸렌과의 반응생성물이고, 결국 이생성물은 W은 0이고, Y는 NR1'〔여기에서 R1'은 -A-B기를 나타내고 여기에서 A는 CO,CS 또는 CH2로부터 선택되며, A가 CO 또는 CS이면, B는 i)1또는 2의 히드록시기로 선택적으로 치환된 수소, 알킬, 알켄일, 시클로알킬, 시클로 알켄일 또는 시클로알킬(알켄일)알킬(알켄일)이거나 또는 할로겐, 트리플루오로메틸, 저급알킬, 저급알콕시, 저급 알킬티오, 아실옥시 또는 시아노로 구성된 군으로부터 선택되는 하나이상의 치환체로 선택적으로 치환된 페닐 또는 ⅱ)QB1[여기에서 Q는 O 또는 S이고, B1은 수소를 제외한 상기 i)에서 B로 정의된 치환체로 부터 선택된다); 그리고 ⅲ)NB2B3(여기에서B2및 B3은 각각 상기 ⅱ)에서 B′으로서 정의된 치환체들로부터 선택되거나 또는 B2와 B3는 결합하여 1 내지 3의 질소원자와 0내지 3의 산소 또는 황원자를 함유하는 4내지 8원 헤테로고리의 고리를 형성한다); 으로 구성된 군으로 부터 선택되고; 또는 A가 CH2인 경우 B는 ⅳ)ⅱ)에서 정의한 QB1기; ⅴ)ⅲ)에서 정의한 NB2B3기; 또는 ⅵ)OC(O)B4(여기에서 B4는 B1의 정의와 같다.);으로 구성된 군으로부터 선택된다]인 제 1항에서 정의한 일반식 I에 유사한 식으로서 나타낸 것인 것을 특징으로 하는, R이 하기식의 기인 제 1항의 화합물의 프로드러그
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- {여기에서 W는 O이고 Y는 NR1이며, 여기에서 R1은 수소이고, n,Z및 U는 제 1항에서 정의한 것과 같다)
- 약제학적으로 허용가능한 담체 또는 희석제와 함께 제 1항에 따른 적어도 하나의 화합물을 포함하는 것을 특징으로 하는 약제학적 제제.
- 제6항에 있어서, 약제학적으로 수용가능한 오일상태로 제5항에 따른 프로드러그를 포함하는 것을 특징으로 하는 약제학적 체제
- 불안, 우울, 수면장애, 정신불열의 부증상 또는 편두통의 치료를 위한 약물을 제조하기 위한, 제 1항에 있는 단서를 적용하지 않는 것을 제외하고 제 1항에서 정의한 것과 같은 일반식 I을 갖는 5-치환 트랜스-1-피페라지노인단 유도체 또는 이것의 약제학적으로 허용가능한 산부가염 또는 프로드러그의 용도.
- 제 1항의 단서를 적용하지 않는다는 것을 제외하고 제 1항에서 정의한 것과 같은 식I의 화합물 또는 약제학적으로 허용가능한 이것의 산부가염 또는 이것에 대한 프로드러그를 치료적으로 유효한 양으로 치료를 필요로하는 환자에게 투여하는 것으로 구성된, 불안, 우울, 수면장애, 정신불열의 부증상 또는 편두통을 치료하는 방법
- a)하기식 Ⅱ의 화합물을, 식
-
- 을 갖는 피페라진 유도체로 처리하는 단계 (여기서, X,Ar및R는 제1항에서 정의한 것과 같고, X1은 할로겐 또는 -OSO2R4이며, 여기에서 R4는 CH3와 같은 알킬 또는 p-툴루일과 같은 아릴이다. );
- b)X 및 Ar이 앞에서 정의한 것과 같은 하기식 Ⅲ의 화합물을,
-
- R이 수소일 수 없다는 것을 제외하고 R와 X1이 앞에서 정의한 것과 같은 식 X1-R의 화합물로 처리하는 단계;
- c)Pt또는 Pd와 같은 적당한 촉매의 존재하에서 NaCNBH3또는 수소와 같은 환원제의 존재하에서, 화합물 R'-CHO(여기에서 R'는 앞서 정의한 R을 R'-CH2-로서 나타낼때의 R'와 같은 기이다)로 식Ⅲ의 화합물을 처리하는 단계;
- d)X,Ar,R1,Z및 n이 앞서 정의한 것과 같은 하기식 Ⅳ의 화합물을,
-
- CS2, 티오프스겐, 요소 또는 포스겐으로 처리하는 단계;
- e)X,Ar,n 및 Z가 앞서 정의한 바와 같고, Alk는 나트륨 또는 칼륨과 같은 알카리급속인 하기식Ⅴ의 화합물을
-
- R5는 저급 알킬기이고, X1은 앞서 정의한 것과 같은식 R5-X1의 화합물로 처리하는 단계;
- f)X,AR,n,U,Z및 W는 앞서 정의한 바와 같고R1″은 하나이상의 에스테르, 케톤 또는 알데히드기를 갖는 시클로알킬 또는 저급알킬기인 하기식 Ⅵ의 화합물을,
-
- 적당한 환원제를 사용하여, R1이 하나이상의 히드록시기를 갖는 시클로알킬기 또는 저급 알킬기인 대응하는 화합물로 환원시키는 단계;
- g)n,U,Z및 Y는 앞서 정의한 바와 같고 W는 O인 하기식
-
- 기가 R인 식 I의 화합물을, P2S5또는Lawessons시약과 반응시켜 W가 S인 대응하는 화합물을 얻는 단계;
- 및 필요하다면, 획득한 이 유도체를 계속적으로 대응하는 산부가염으로 전화시키는 단계;로 구성된 것을 특징으로 하는 제1항에 따른 5-치환 트랜스-1-피페라지노인단 유도체의 제조 방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK286990A DK286990D0 (da) | 1990-12-04 | 1990-12-04 | Indanderivater |
DK2869/90 | 1990-12-04 | ||
PCT/DK1991/000358 WO1992010192A1 (en) | 1990-12-04 | 1991-11-28 | Indan derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
KR930702980A true KR930702980A (ko) | 1993-11-29 |
Family
ID=8116621
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019930701680A KR930702980A (ko) | 1990-12-04 | 1991-11-28 | 인단 유도체 |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0560868B1 (ko) |
JP (1) | JP3245418B2 (ko) |
KR (1) | KR930702980A (ko) |
AT (1) | ATE121294T1 (ko) |
AU (1) | AU653375B2 (ko) |
CA (1) | CA2097715C (ko) |
DE (1) | DE69109132T2 (ko) |
DK (2) | DK286990D0 (ko) |
ES (1) | ES2071479T3 (ko) |
FI (1) | FI105685B (ko) |
HK (1) | HK122995A (ko) |
IE (1) | IE914076A1 (ko) |
IL (1) | IL100164A (ko) |
NO (1) | NO179947C (ko) |
NZ (1) | NZ240734A (ko) |
PT (1) | PT99673B (ko) |
WO (1) | WO1992010192A1 (ko) |
ZA (1) | ZA919563B (ko) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
DK55192D0 (da) * | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
DK78692D0 (da) * | 1992-06-12 | 1992-06-12 | Lundbeck & Co As H | Dimere piperidin- og piperazinderivater |
SK94393A3 (en) * | 1992-09-11 | 1994-08-10 | Thomae Gmbh Dr K | Cyclic derivatives of urea, process for their production and their pharmaceutical agents with the content of those |
US5935958A (en) * | 1996-07-01 | 1999-08-10 | Schering Corporation | Muscarinic antagonists |
KR20000022380A (ko) * | 1996-07-01 | 2000-04-25 | 둘락 노먼 씨. | 무스카린 길항제 |
TWI242011B (en) | 1997-03-31 | 2005-10-21 | Eisai Co Ltd | 1,4-substituted cyclic amine derivatives |
MXPA04006119A (es) | 2001-12-21 | 2004-11-01 | Lundbeck & Co As H | Derivados aminoindano como inhibidores de la absorcion de la serotonina y de la norepinefrina. |
IS7282A (is) * | 2001-12-21 | 2004-05-21 | H. Lundbeck A/S | Amínóindan afleiður sem serótónín og noradrenalínupptökuhindrar |
FR2883876B1 (fr) * | 2005-03-30 | 2007-05-04 | Servier Lab | Derives d'indanyl-piperazines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
TW200819426A (en) | 2006-08-31 | 2008-05-01 | Lundbeck & Co As H | Novel indane compounds |
LT2720989T (lt) | 2011-06-20 | 2016-11-25 | H. Lundbeck A/S | Deuterinti 1-piperazin-3-fenilindanai, skirti šizofrenijos gydymui |
WO2020114853A1 (en) * | 2018-12-03 | 2020-06-11 | H. Lundbeck A/S | Prodrugs of 4-((1r,3s)-6-chloro-3-phenyl-2,3-dihydro-1h-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE50867B1 (en) * | 1980-02-29 | 1986-08-06 | Kefalas As | Indane derivatives |
GB8427125D0 (en) * | 1984-10-26 | 1984-12-05 | Lundbeck & Co As H | Organic compounds |
-
1990
- 1990-12-04 DK DK286990A patent/DK286990D0/da not_active Application Discontinuation
-
1991
- 1991-11-22 IE IE407691A patent/IE914076A1/en not_active IP Right Cessation
- 1991-11-26 NZ NZ240734A patent/NZ240734A/en not_active IP Right Cessation
- 1991-11-27 IL IL10016491A patent/IL100164A/en not_active IP Right Cessation
- 1991-11-28 DK DK92900941.3T patent/DK0560868T3/da active
- 1991-11-28 AT AT92900941T patent/ATE121294T1/de not_active IP Right Cessation
- 1991-11-28 ES ES92900941T patent/ES2071479T3/es not_active Expired - Lifetime
- 1991-11-28 DE DE69109132T patent/DE69109132T2/de not_active Expired - Fee Related
- 1991-11-28 AU AU89599/91A patent/AU653375B2/en not_active Ceased
- 1991-11-28 WO PCT/DK1991/000358 patent/WO1992010192A1/en active IP Right Grant
- 1991-11-28 KR KR1019930701680A patent/KR930702980A/ko not_active Application Discontinuation
- 1991-11-28 EP EP92900941A patent/EP0560868B1/en not_active Expired - Lifetime
- 1991-11-28 CA CA002097715A patent/CA2097715C/en not_active Expired - Fee Related
- 1991-11-28 JP JP50028192A patent/JP3245418B2/ja not_active Expired - Fee Related
- 1991-12-03 PT PT99673A patent/PT99673B/pt not_active IP Right Cessation
- 1991-12-04 ZA ZA919563A patent/ZA919563B/xx unknown
-
1993
- 1993-06-03 FI FI932541A patent/FI105685B/fi active
- 1993-06-03 NO NO932024A patent/NO179947C/no not_active IP Right Cessation
-
1995
- 1995-07-27 HK HK122995A patent/HK122995A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CA2097715A1 (en) | 1992-06-05 |
JP3245418B2 (ja) | 2002-01-15 |
JPH06503073A (ja) | 1994-04-07 |
HK122995A (en) | 1995-08-04 |
DK0560868T3 (da) | 1995-10-02 |
EP0560868B1 (en) | 1995-04-19 |
FI105685B (fi) | 2000-09-29 |
FI932541A (fi) | 1993-07-23 |
CA2097715C (en) | 2003-04-15 |
NO179947B (no) | 1996-10-07 |
IL100164A0 (en) | 1992-08-18 |
PT99673A (pt) | 1992-10-30 |
PT99673B (pt) | 1999-05-31 |
NZ240734A (en) | 1994-02-25 |
NO179947C (no) | 1997-01-15 |
ES2071479T3 (es) | 1995-06-16 |
NO932024L (no) | 1993-07-30 |
EP0560868A1 (en) | 1993-09-22 |
ATE121294T1 (de) | 1995-05-15 |
DE69109132T2 (de) | 1995-08-31 |
NO932024D0 (no) | 1993-06-03 |
WO1992010192A1 (en) | 1992-06-25 |
ZA919563B (en) | 1992-08-26 |
FI932541A0 (fi) | 1993-06-03 |
AU8959991A (en) | 1992-07-08 |
IL100164A (en) | 1996-06-18 |
DK286990D0 (da) | 1990-12-04 |
AU653375B2 (en) | 1994-09-29 |
DE69109132D1 (de) | 1995-05-24 |
IE914076A1 (en) | 1992-06-17 |
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