KR900009603A - 광학 활성 2-옥소이미다졸리딘 유도체의 제조 방법 - Google Patents
광학 활성 2-옥소이미다졸리딘 유도체의 제조 방법 Download PDFInfo
- Publication number
- KR900009603A KR900009603A KR1019890018658A KR890018658A KR900009603A KR 900009603 A KR900009603 A KR 900009603A KR 1019890018658 A KR1019890018658 A KR 1019890018658A KR 890018658 A KR890018658 A KR 890018658A KR 900009603 A KR900009603 A KR 900009603A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- group
- iii
- general formula
- configuration
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical class O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 238000006482 condensation reaction Methods 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- -1 propionic acid compound Chemical class 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- KZKRPYCBSZIQKN-UHFFFAOYSA-N 2-Imidazolidone-4-carboxylic acid Chemical compound OC(=O)C1CNC(=O)N1 KZKRPYCBSZIQKN-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- 229940086542 triethylamine Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(Ⅱ)의 (S)배열을 갖는 2-옥소이미다 졸리딘-4-카르복실산 에스테르를 하기 일반식(Ⅲ)의 (R)배열을 갖는 프로피온산 화합물의 카르복실기에서의 반응성 유도체와 반응시켜 하기 일반식(Ⅳ)의 (S,R)배열을 갖는 3-아실-2-옥소이미다졸리딘-4-카르복실산 에스테르 유도체를 형성하고, 이 화합물(Ⅳ)를 하기 일반식(Ⅴ)의 (S)배열을 갖는 아미노산 에스테르와 반응시켜 하기 일반식(Ⅵ)의 (S,S,S)배열을 갖는 2-옥소이미다졸리딘 디에스테르 유도체를 형성하고, 계속해서 이 화합물로부터 R2를 제거하고, 또한 R4가 벤질기인 경우 추가로 이 벤질기로 제거하는 것을 특징으로 하는 하기 일반식(Ⅰ)의 광학 활성 2-옥소이미다졸리딘 유도체의 제조방법.상기 각 식에서, R1은 수소 원자 또는 저급 알킬기이고, R2는 tert.-부틸기 또는 벤질기이며, R3는 저급 알킬기 또는 아릴기이고, R4는 저급 알킬기 또는 벤질기를 나타낸다.
- 제1항에 있어서, 상기 화합물(Ⅲ)에서 R3가 메틸기, 에틸기, 페닐기 또는 p-메틸페닐기인 것을 특징으로 하는 방법.
- 제1항에 있어서, 상기 화합물(Ⅲ)의 카르복실기에서의 반응성 유도체가 N-히드록시숙신산 이미드, 산염화물 또는 산 브롬화물과 반응성인 에스테르인 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅱ)와 화합물(Ⅲ)의 축합 반응을 t-부톡시화칼륨, 수산화나트륨 또는 수산화칼륨 중에서 선택된 탈산제의 존재하에서 실시하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅱ)와 화합물(Ⅲ)의 축합 반응을 테트라히드로푸란, 디옥산 또는 디메틸포름아미드 중에서 선택된 용매 존재하에서 실시하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅱ)와 화합물(Ⅲ)의 축합 반응을 실온으로 냉각시키면서 실시하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅳ)와 화합물(Ⅴ)의 축합 반응을 탄산 칼륨, 탄산 나트륨, 트리에틸 아민, 트리부틸 아민, 또는 N-메틸모르폴린 중에서 선택된 탈산제 존재하에서 실시하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅳ)과 화합물(Ⅴ)의 축합 반응을 술폭시화디메틸, 헥사메틸포스포릴아미드 또는 디메틸포름아미드 중에서 선택된 용매 존재하에서 실시하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 화합물(Ⅳ)와 화합물(Ⅴ)의 축합 반응을 실온 내지 가열하에 실시하는 것을 특징으로 하는 방법.
- 하기 일반식의 (S,R)배열을 갖는 3-아실-2-옥소 이미다졸리딘-4-카르복실산 에스테르 유도체.상기 식에서, R2는 tert-부틸기 또는 벤질기이고, R3은 저급 알킬기 또는 아릴기를 나타낸다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63-318745 | 1988-12-16 | ||
| JP63318745A JPH0645603B2 (ja) | 1988-12-16 | 1988-12-16 | 光学活性２‐オキソイミダゾリジン誘導体の製法 |
| JP88-318745 | 1988-12-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900009603A true KR900009603A (ko) | 1990-07-05 |
| KR950009364B1 KR950009364B1 (ko) | 1995-08-21 |
Family
ID=18102470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890018658A KR950009364B1 (ko) | 1988-12-16 | 1989-12-15 | 광학 활성 2-옥소이미다졸리딘 유도체의 제조 방법 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5013845A (ko) |
| EP (1) | EP0373881B1 (ko) |
| JP (1) | JPH0645603B2 (ko) |
| KR (1) | KR950009364B1 (ko) |
| CN (1) | CN1032308C (ko) |
| AT (1) | ATE100817T1 (ko) |
| AU (1) | AU622959B2 (ko) |
| CA (1) | CA2004606C (ko) |
| DE (1) | DE68912745T2 (ko) |
| DK (1) | DK174701B1 (ko) |
| ES (1) | ES2062044T3 (ko) |
| FI (1) | FI97133C (ko) |
| HK (1) | HK34195A (ko) |
| HU (1) | HU203730B (ko) |
| IE (1) | IE64315B1 (ko) |
| IL (1) | IL92456A0 (ko) |
| SG (1) | SG4795G (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104513292A (zh) * | 2013-09-29 | 2015-04-15 | 山东新时代药业有限公司 | 一种雷米普利的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5788165A (en) * | 1980-11-21 | 1982-06-01 | Tanabe Seiyaku Co Ltd | 2-oxoimidazolidine-4-carboxylic acid derivative and its preparation |
| JPS6058233B2 (ja) * | 1982-05-24 | 1985-12-19 | 田辺製薬株式会社 | ２−オキソイミダゾリジン誘導体及びその製法 |
| JPS6058233A (ja) * | 1983-08-11 | 1985-04-04 | ザ・アプジヨン・カンパニー | 滅菌懸濁液及び溶液の保持及び混合装置 |
-
1988
- 1988-12-16 JP JP63318745A patent/JPH0645603B2/ja not_active Expired - Lifetime
-
1989
- 1989-11-27 IL IL92456A patent/IL92456A0/xx unknown
- 1989-12-04 FI FI895795A patent/FI97133C/fi active IP Right Grant
- 1989-12-04 US US07/445,060 patent/US5013845A/en not_active Expired - Lifetime
- 1989-12-05 CN CN89109175A patent/CN1032308C/zh not_active Expired - Lifetime
- 1989-12-05 CA CA002004606A patent/CA2004606C/en not_active Expired - Lifetime
- 1989-12-12 EP EP89312965A patent/EP0373881B1/en not_active Expired - Lifetime
- 1989-12-12 DE DE89312965T patent/DE68912745T2/de not_active Expired - Lifetime
- 1989-12-12 AT AT89312965T patent/ATE100817T1/de not_active IP Right Cessation
- 1989-12-12 ES ES89312965T patent/ES2062044T3/es not_active Expired - Lifetime
- 1989-12-12 AU AU46195/89A patent/AU622959B2/en not_active Expired
- 1989-12-14 IE IE400489A patent/IE64315B1/en not_active IP Right Cessation
- 1989-12-15 KR KR1019890018658A patent/KR950009364B1/ko not_active IP Right Cessation
- 1989-12-15 DK DK198906382A patent/DK174701B1/da not_active IP Right Cessation
- 1989-12-15 HU HU896640A patent/HU203730B/hu unknown
-
1995
- 1995-01-13 SG SG4795A patent/SG4795G/en unknown
- 1995-03-09 HK HK34195A patent/HK34195A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0645603B2 (ja) | 1994-06-15 |
| CN1032308C (zh) | 1996-07-17 |
| AU4619589A (en) | 1990-06-21 |
| KR950009364B1 (ko) | 1995-08-21 |
| DK174701B1 (da) | 2003-09-29 |
| DE68912745T2 (de) | 1994-05-11 |
| EP0373881A3 (en) | 1990-08-16 |
| ES2062044T3 (es) | 1994-12-16 |
| IL92456A0 (en) | 1990-08-31 |
| AU622959B2 (en) | 1992-04-30 |
| JPH02164869A (ja) | 1990-06-25 |
| DK638289D0 (da) | 1989-12-15 |
| ATE100817T1 (de) | 1994-02-15 |
| SG4795G (en) | 1995-06-16 |
| CA2004606C (en) | 1997-01-07 |
| HU203730B (en) | 1991-09-30 |
| US5013845A (en) | 1991-05-07 |
| CA2004606A1 (en) | 1990-06-16 |
| HU896640D0 (en) | 1990-02-28 |
| FI895795A0 (fi) | 1989-12-04 |
| HK34195A (en) | 1995-03-17 |
| FI97133C (fi) | 1996-10-25 |
| EP0373881A2 (en) | 1990-06-20 |
| IE64315B1 (en) | 1995-07-26 |
| EP0373881B1 (en) | 1994-01-26 |
| FI97133B (fi) | 1996-07-15 |
| CN1043705A (zh) | 1990-07-11 |
| DK638289A (da) | 1990-06-17 |
| IE894004L (en) | 1990-06-16 |
| HUT52064A (en) | 1990-06-28 |
| DE68912745D1 (de) | 1994-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR870004019A (ko) | 퀴놀린 유도체의 제조방법 | |
| KR870010005A (ko) | 퀴놀린 유도체 및 그의 에스테르 또는 염의 제조법 | |
| KR840001156A (ko) | 벤지미다졸 유도체의 제조방법 | |
| KR850001905A (ko) | 벤조시클로 알칸 유도체의 제조방법 | |
| KR840000463A (ko) | 광학적으로 활성인 1-방향족 그룹으로 치환된-1- 알카논의 제조방법 | |
| KR860006462A (ko) | 1,8-나프틸리딘 유도체, 그 에스테르 또는 그 염의 제조방법 | |
| KR850004754A (ko) | 3-인돌 카르복사미드 화합물류의 제조방법 | |
| KR840000565A (ko) | 세펨 화합물의 제조방법 | |
| KR830005090A (ko) | 3,7,11,15-테트라메틸-2,4,6,10,14-헥사데카펜타엔 산(酸) | |
| KR850002459A (ko) | 디히드록시벤즈아미드 유도체 및 그 제조방법 | |
| KR840004415A (ko) | 옥사졸 유도체의 제조방법 | |
| KR850004959A (ko) | 아릴옥시-n-(아미노알킬)-1-피롤리딘 및 피페리딘 카복스 아미드 및 카보티오 아미드의 제조방법 | |
| KR850006411A (ko) | 이속사졸 유도체의 제조방법 | |
| KR900009603A (ko) | 광학 활성 2-옥소이미다졸리딘 유도체의 제조 방법 | |
| KR860001097A (ko) | 4-아미노-2-페닐퀴놀린의 제조방법 | |
| KR850004743A (ko) | 티아졸일 아세트산 유도체의 제조방법 | |
| KR840002821A (ko) | N-(2,3-에폭시프로필렌)-n-아르알킬술폰아미드 유도체의 제조방법 | |
| KR880011120A (ko) | 1- 프로파르길-2,4-디옥소이미다졸리딘의 제조방법 | |
| KR860004051A (ko) | 치환된 페닐피페라진 유도체의 제조방법 | |
| KR950032107A (ko) | 헤테로치환된 아세탈의 제조방법 | |
| KR840000578A (ko) | 포스포리피드 유도체의 제조방법 | |
| KR860002474A (ko) | 치환된 페닐술포닐아졸의 제조방법 | |
| KR870002118A (ko) | 벤질아민 유도체 및 그 제조방법 | |
| KR890006613A (ko) | 디벤조티에핀 유도체의 제조방법 | |
| KR880001666A (ko) | 1-히드록시-옥소-5H-피리도 [3,2-a]페녹사진-3-카르복실산에스테르 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20090807 Year of fee payment: 15 |
|
| EXPY | Expiration of term |