KR950703544A - 아미드 유도체(Amide derivatives) - Google Patents

아미드 유도체(Amide derivatives) Download PDF

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Publication number
KR950703544A
KR950703544A KR1019950701459A KR19950701459A KR950703544A KR 950703544 A KR950703544 A KR 950703544A KR 1019950701459 A KR1019950701459 A KR 1019950701459A KR 19950701459 A KR19950701459 A KR 19950701459A KR 950703544 A KR950703544 A KR 950703544A
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KR
South Korea
Prior art keywords
formula
amide
general formula
carbon atoms
group
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KR1019950701459A
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English (en)
Inventor
안토니 애쉬웰 마크
Original Assignee
폴 에이. 리터
존 와이어쓰 앤드 브라더 리미티드
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Application filed by 폴 에이. 리터, 존 와이어쓰 앤드 브라더 리미티드 filed Critical 폴 에이. 리터
Publication of KR950703544A publication Critical patent/KR950703544A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—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
    • C07D295/04—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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

본 발명은 광학적으로 활성인 일반식(A)의 아미드 및 이의 염의 제조를 위한 신규한 비대칭적 합성법에 관한 것이다.
상기 일반식에서, X는 -N-(a) 또는 -CH-(b)를 나타내고, R은 모노 또는 바이사이클릭 아릴 또는 헤테로아릴 그룹을 나타내며, R1은 아릴 또는 헤테로아릴 라디칼을 나타내고, R2및 R3본원에서 정의한 의미를 갖는다. 당해 생성물은 5-HT1A길항제로서 유용하다. 본 발명의 방법에 유용한 중간체인 신규한 디에스테르도 기술되어 있다.

Description

아미드 유도체(Amide derivatives)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(B)의 알데하이드를 일반식(C)의 아민과 축합시킴을 포함하여, 광학적으로 활성인 일반식(A)의 아미드 또는 약제학적으로 허용되는 이의 염을 포함하는 방법.
    상기식에서, X는 -N- 또는 -CH-이고, R은 모노 또는 바이사이클릭 아릴 또는 헤테로아릴 그룹이며, R1은 아릴 또는 헤테로아릴 라디칼이고, R2은 수소 또는 저급 알킬이며, R3은 수소, 탄소수 1 내지 10의 알킬 그룹, 탄소수 3 내지 12의 사이클로알킬, 사이클로알킬(저급)알킬, 아릴 또는 아릴(저급)알킬이거나, R2와 R3는 이들 모두와 결합한 질소원자와 함께, 추가의 헤테로원자를 함유할 수 있는 포화 헤테로사이클릭 환을 나타낸다.
  2. 제1항에 있어서, 일반식(B)의 알데하이드가, 일반식(D)의 디에스테르를 가수분해시켜 일반식(E)의 이산(diacid) 아미드를 수득하고, 이러한 일반식(E)의 이산 아미드를 탈카복실화시켜 일반식(F)의 일산(monoacid)아미드를 수득한 다음, 일반식(F)의 일산 아미드를 환원시킴으로써 수득되는 방법.
    상기식에서, R1, R2및 R3는 제1항에서 정의한 바와 같고, R4및 R5는 각각 탄소수 3 내지 6의 저급 알킬 그룹이다.
  3. 일반식(H)의 활성화된 α-하이드록시 아미드를 일반식(J)의 디알킬말로네이트와 반응시킴을 포함하여, 일반식(D)의 디에스테르를 제조하는 방법.
    상기식에서, R1, R2및 R3는 제1항에서 정의한 바와 같고, R4및 R5는 각각 탄소수 3 내지 6의 저급 알킬 그룹이며, R6는 키랄성을 유지시키는 활성화 그룹이다.
  4. 제3항에 있어서, R1이 페닐인 일반식(H)의 활성화된 α-하이드록시 아미드가, 구조식(V)의 S-(+)-만델산의 하이드록시 그룹을 보호시켜 일반식(VI)의 보호된 유도체를 수득하고, 이와 같이 보호된 유도체(VI)를 할로겐화시켜 일반식(VII)의 아실 할라이드를 수득하며, 이 아실 할라이드(VII)를 일반식 NHR2R3의 아민(여기서, R2및 R3은 제1항에서 정의된 바와 같다)과 반응시켜 일반식(VIII)의 보호된 하이드록시 아미드를 수득하며, 보호시킨 하이드록시 아미드(VIII)로부터 보호 그룹은 제거시켜 일반식(I X)의 하이드록시아미드를 수득한 다음, 하이드록시 아미드(I X)를 활성화시킴으로써 제조되는 방법.
    상기식에서, R2및 R3는 제1항의 정의와 같고, R7은 보호 그룹이며, Z는 염소 또는 브롬이다.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, X가인 방법.
  6. 제1항 내지 제5항중 어느 한 항에 있어서, R이 o-메톡시페닐인 방법.
  7. 제1항 내지 제6항중 어느 한 항에 있어서, R1이 페닐인 방법.
  8. 제1항 내지 제7항중 어느 한 항에 있어서, R2및 R3가, 이들에 결합된 질소 원자와 함께 헥사하이드로아제피노를 나타내는 방법.
  9. 일반식(D)의 디에스테르.
    상기식에서, R1, R2및 R3는 제1항에서 정의한 바와 같고, R4및 R5는 각각 탄소수 3 내지 6의 저급 알킬 그룹이다.
  10. 제9항에 있어서, 일반식(IV)의 디에스테르.
    상기식에서, R4및 R5는 제9항에서 정의한 바와 같다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950701459A 1992-10-17 1993-10-08 아미드 유도체(Amide derivatives) KR950703544A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB929221931A GB9221931D0 (en) 1992-10-17 1992-10-17 Piperazine derivatives
GB9221931.0 1992-10-17
PCT/GB1993/002090 WO1994008983A1 (en) 1992-10-17 1993-10-08 Amide derivatives

Publications (1)

Publication Number Publication Date
KR950703544A true KR950703544A (ko) 1995-09-20

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Application Number Title Priority Date Filing Date
KR1019950701459A KR950703544A (ko) 1992-10-17 1993-10-08 아미드 유도체(Amide derivatives)

Country Status (17)

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US (1) US5637701A (ko)
EP (1) EP0664799B1 (ko)
JP (1) JP3478827B2 (ko)
KR (1) KR950703544A (ko)
AT (1) ATE182144T1 (ko)
AU (1) AU5152493A (ko)
CA (1) CA2147155C (ko)
DE (1) DE69325660T2 (ko)
DK (1) DK0664799T3 (ko)
ES (1) ES2133414T3 (ko)
GB (2) GB9221931D0 (ko)
GR (1) GR3031123T3 (ko)
MX (1) MX9306421A (ko)
PH (1) PH31583A (ko)
TW (1) TW340844B (ko)
WO (1) WO1994008983A1 (ko)
ZA (1) ZA937516B (ko)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5607936A (en) * 1994-09-30 1997-03-04 Merck & Co., Inc. Substituted aryl piperazines as neurokinin antagonists
US5525600A (en) * 1994-11-28 1996-06-11 American Home Products Corporation (Thiophen-2-yl)-piperidin or tetrahydropyridin carboxamides
DE19519245C2 (de) * 1995-04-14 2003-04-30 Boehringer Ingelheim Kg Neue Arylglycinamidderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
FR2744448B1 (fr) * 1996-02-02 1998-04-24 Pf Medicament Nouvelles piperidines derivees d'aryl piperazine, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments
FR2757158B1 (fr) * 1996-12-18 1999-04-02 Lipha Nouveaux derives d'acide 4-(1-piperazinyl) benzoique, leur procede de preparation et leurs applications therapeutiques
US6900228B1 (en) * 1998-03-10 2005-05-31 Research Triangle Institute Opiate compounds, methods of making and methods of use
US20040072839A1 (en) * 2002-06-14 2004-04-15 Amedeo Leonardi 1-Phenylalkylpiperazines

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2776282A (en) * 1954-05-04 1957-01-01 Searle & Co Cyclic amides of alpha-toluic acids and derivatives thereof
GB8909209D0 (en) * 1989-04-22 1989-06-07 Wyeth John & Brother Ltd Piperazine derivatives
ES2130116T3 (es) * 1989-04-22 1999-07-01 Wyeth John & Brother Ltd Derivados de piperazina.
DE69033393T2 (de) * 1989-04-22 2000-05-25 Wyeth John & Brother Ltd Tertiäre alkyl funktionalisierte Piperazin-Derivate
GB9022820D0 (en) * 1990-10-19 1990-12-05 Wyeth John & Brother Ltd Piperazine derivatives

Also Published As

Publication number Publication date
MX9306421A (es) 1994-04-29
TW340844B (en) 1998-09-21
EP0664799B1 (en) 1999-07-14
ES2133414T3 (es) 1999-09-16
GB9320819D0 (en) 1993-12-01
GB9221931D0 (en) 1992-12-02
DE69325660D1 (de) 1999-08-19
GR3031123T3 (en) 1999-12-31
GB2272436B (en) 1997-06-18
DK0664799T3 (da) 1999-11-29
JPH08502738A (ja) 1996-03-26
GB2272436A (en) 1994-05-18
DE69325660T2 (de) 2000-03-09
US5637701A (en) 1997-06-10
EP0664799A1 (en) 1995-08-02
CA2147155C (en) 2005-01-04
WO1994008983A1 (en) 1994-04-28
AU5152493A (en) 1994-05-09
CA2147155A1 (en) 1994-04-28
JP3478827B2 (ja) 2003-12-15
ATE182144T1 (de) 1999-07-15
ZA937516B (en) 1995-04-21
PH31583A (en) 1998-11-03

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