KR950703544A - 아미드 유도체(Amide derivatives) - Google Patents
아미드 유도체(Amide derivatives) Download PDFInfo
- 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
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- amide
- general formula
- carbon atoms
- group
- Prior art date
Links
Classifications
-
- 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
Landscapes
- 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
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 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.
- 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.
- 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.
- 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.
- 제1항 내지 제4항중 어느 한 항에 있어서, X가인 방법.
- 제1항 내지 제5항중 어느 한 항에 있어서, R이 o-메톡시페닐인 방법.
- 제1항 내지 제6항중 어느 한 항에 있어서, R1이 페닐인 방법.
- 제1항 내지 제7항중 어느 한 항에 있어서, R2및 R3가, 이들에 결합된 질소 원자와 함께 헥사하이드로아제피노를 나타내는 방법.
- 일반식(D)의 디에스테르.상기식에서, R1, R2및 R3는 제1항에서 정의한 바와 같고, R4및 R5는 각각 탄소수 3 내지 6의 저급 알킬 그룹이다.
- 제9항에 있어서, 일반식(IV)의 디에스테르.상기식에서, R4및 R5는 제9항에서 정의한 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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 |
Family
ID=10723688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019950701459A KR950703544A (ko) | 1992-10-17 | 1993-10-08 | 아미드 유도체(Amide derivatives) |
Country Status (17)
Country | Link |
---|---|
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)
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)
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 |
-
1992
- 1992-10-17 GB GB929221931A patent/GB9221931D0/en active Pending
-
1993
- 1993-10-08 DE DE69325660T patent/DE69325660T2/de not_active Expired - Fee Related
- 1993-10-08 DK DK93922576T patent/DK0664799T3/da active
- 1993-10-08 US US08/411,601 patent/US5637701A/en not_active Expired - Lifetime
- 1993-10-08 WO PCT/GB1993/002090 patent/WO1994008983A1/en active IP Right Grant
- 1993-10-08 KR KR1019950701459A patent/KR950703544A/ko active IP Right Grant
- 1993-10-08 AU AU51524/93A patent/AU5152493A/en not_active Abandoned
- 1993-10-08 JP JP50974494A patent/JP3478827B2/ja not_active Expired - Fee Related
- 1993-10-08 EP EP93922576A patent/EP0664799B1/en not_active Expired - Lifetime
- 1993-10-08 GB GB9320819A patent/GB2272436B/en not_active Expired - Fee Related
- 1993-10-08 CA CA002147155A patent/CA2147155C/en not_active Expired - Fee Related
- 1993-10-08 ES ES93922576T patent/ES2133414T3/es not_active Expired - Lifetime
- 1993-10-08 AT AT93922576T patent/ATE182144T1/de not_active IP Right Cessation
- 1993-10-11 ZA ZA937516A patent/ZA937516B/xx unknown
- 1993-10-15 PH PH47088A patent/PH31583A/en unknown
- 1993-10-15 MX MX9306421A patent/MX9306421A/es not_active IP Right Cessation
- 1993-10-15 TW TW082108553A patent/TW340844B/zh active
-
1999
- 1999-08-31 GR GR990402205T patent/GR3031123T3/el unknown
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NL300396I1 (nl) | Nieuwe derivaten met naftalinestructuren, werkwijze voor de bereiding ervan en de farmaceutische preparaten die deze bevatten | |
ATE135709T1 (de) | Erythromycinderivate, ihr verfahren zur herstellung und ihre verwendung als arzneimitteln | |
ES2095081T3 (es) | Procedimiento para la preparacion de derivados de taxano. | |
DE69406538T2 (de) | Dihalotriazolopyrimidinderivate als fugizide | |
TW234116B (en) | 2-Cyano-3-hydroxy-enamides and their preparation process | |
ES2115600T3 (es) | Derivados de 1-metilcarbapenem y procedimiento para su preparacion. | |
DE60316672D1 (de) | Polycyclische verbindungen als potenten alpha2-adrenoceptor antagonisten | |
KR910015546A (ko) | 복소환식 화합물 | |
KR950703544A (ko) | 아미드 유도체(Amide derivatives) | |
NO20042109L (no) | Fremgangsmate for fremstilling av 7-isoindolinkinolonkarboksylsyre-derivater og mellomprodukter for disse, salter av 7-isoindolinkinolonkarboksylsyrer, hydrater derav, og | |
AT397654B (de) | Neue pleuromutilinderivate, ihre verwendung und verfahren zu ihrer herstellung | |
ES8609212A1 (es) | Un procedimiento para la preparacion de derivados de etanolamina. | |
PT71125A (fr) | Procede de preparation d'esters de derives de l'allethrolone et d'acides carboxyliques | |
KR960703119A (ko) | 합성적 용도로 사용하기 위한 신규한 중간체 및 아미노피페라진 유도체를 제조하는 방법(Novel intermediate for synthetic use and process for producing amino-piperazine derivative) | |
ATE40117T1 (de) | O-substituierte 3-oxypyridiniumsalze, verfahren zu ihrer herstellung und ihre verwendung als fungizide fuer den pflanzenschutz. | |
MY105379A (en) | Diastereoselective process for preparing n-substituted amino acids and derivatives. | |
DK0756593T3 (da) | Fremgangsmåde til fremstilling af 2-piperazincarboxylsyrederivater | |
KR920703577A (ko) | 치환된 이환식 화합물의 이미다졸-2-일 유도체 및 이의 제조방법 | |
ES2148206T3 (es) | Procedimiento para preparar compuestos y productos intermedios antifolato basados en 4-hidroxipirrolo(2,3-d)pirimidina. | |
KR970027089A (ko) | 신규 세팔로스포린 유도체 및 그 중간체 | |
TH4616B (th) | อนุพันธ์ของควิโนลีน-3-คาร์บอกซิลิค แอซิตการเตรียมและการใช้สารเหล่านี้ | |
TH43782B (th) | ผลึกของอนุพันธ์ของเบนซิมิเดโซลและการผลิตของมัน | |
DK0519140T3 (da) | Fremgangsmåde til fremstilling af substituerede 1,4-dihydro-4-oxo-cinnolin-3-carboxylsyrer, estere og salte deraf og mellem | |
TH4773A (th) | อนุพันธ์ของควิโนลีน-3-คาร์บอกซิลิค แอซิตการเตรียมและการใช้สารเหล่านี้ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
AMND | Amendment | ||
E902 | Notification of reason for refusal | ||
A107 | Divisional application of patent | ||
AMND | Amendment | ||
E601 | Decision to refuse application | ||
AMND | Amendment | ||
J201 | Request for trial against refusal decision | ||
B701 | Decision to grant | ||
NORF | Unpaid initial registration fee |