KR870002145A - 아미노산 유도체의 제조방법 - Google Patents
아미노산 유도체의 제조방법 Download PDFInfo
- Publication number
- KR870002145A KR870002145A KR1019860006897A KR860006897A KR870002145A KR 870002145 A KR870002145 A KR 870002145A KR 1019860006897 A KR1019860006897 A KR 1019860006897A KR 860006897 A KR860006897 A KR 860006897A KR 870002145 A KR870002145 A KR 870002145A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- group
- hydrogen
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- 150000003862 amino acid derivatives Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- -1 (S) -carboxy-3-phenylpropyl Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- a) 일반식(II)의 화합물을 일반식(III)의 화합물과 반응시키거나; b) 일반식(IV)의 α-옥소카복실산유도체를 T를 NH2인 일반식(II)의 아미노산과 반응시켜 상응하는 이민을 수득한 후 이이민을 환원시키거나; 또는 c) 일반식(V)의 화합물을 일반식(VI)의 아미노산 드는 일반식(VI)화합물의 에스테르(즉, 일반식(VI)화합물에서 수소 대신 R7을 갖는 화합물)와 축합시키며, W가 NH또는 W가 S이며 R3가 H일 경우, 수소 원자는 보호그룹 R8중 하나로 치환시켜야 하고, 필요할 경우, 수득된 일반식(I)의 최종 생성물을 통상적인 방법으로 염으로 전환시킴을 특징으로하여, 일반식(I)의 아미노산 유도체 및 그의 염을 제조하는 방법상기식에서 R1은 수소 또는, 임의로 페닐치환된 탄소수 1 내지 6의 알킬그룹이고; R2는 수소 또는, 임의로 페닐-치환된 탄소수 1내지6의 알킬그룹이고; R3는 수소, 말단 위치에 아미노 그룹 또는 페닐환을 가질 수 있는 탄소수 1 내지 7의 알킬 그룹: 또는 R4-CO-그룹이고; R4는, W가 NH일 경우, α위치에 아미노 그룹을 가질 수 있는 탄소수 1 내지 5의 알킬 그룹이며: W는 산소, 황 또는 NH그룹이고; n은 m은 각각 0.1 또는 2인, n+m은 1 또는 2이며; k는 1,2,3 또는 4이고 X,Y 및 Z는 산소, 황, NR5, CR6, CHR6, -인데, 단, X,Y 및 Z그룹중의 하나만이 O,S,일수 있고 X,Y 및 Z그룹중 하나 또는 두개가 NR5일수 있으며; R5은 수소 또는 탄소수 1내지 4의 알킬그룹이고: R6은 수소이거나, 인접 그룹과 함께 페닐환을 형성하며: R7은 수소, 탄소수 1 내지 4의 알킬 그룹, 벤질그룹 또는 트리메틸실릴 그룹이고; R8은 R3와 같거나, W가 -NH 또는 -S이고 R3가 H일 경우, R8은 보호그룹인 3급 부틸옥시카보닐, 벤질옥시카보닐, 플루오레닐메틸옥시카보닐, 벤질 또는 트리틸중의 하나일 수 있고; T는 친핵적 치환가능 그룹이고 U는 아미노그룹이거나, 역으로 T는 아미노그룹이고 U는 친핵적 치환가능 그룹이다.
- 제1항에 있어서, 일반식(Ia)의 화합물을 제조하는 방법.상기식에서, R2,R3및 R5는 상술한 바와 같고; m은 1 또는 2이며, n은 0또, 1인데, m+n은 2이고; A는그룹중의 하나이고, A1, A3및 A3그룹은 B환에 어떤 방법으로도 연결될 수 있다.
- 제1항에 있어서, 일반식(Ib)의 화합물을 제조하는 방법.상기식에서, R2' 는 H 또는, 탄소수 1 내지 4의 알킬그룹이고; R3'는 H또는 COR4이며; R4는 상술한 바와같고; m은 1 또는 2이며, n은 0 또는 1인데, m+n은 2이고; A'는,그룹중의 하나이고, A1·A2' 및 A3'그룹은 B환에 어떤 방법으로도 연결될 수 있다.
- 제1항 내지 3항중 어느 하나에 있어서, 모든 비대칭 중심이 L-형태로 존재하는 화합물을 제조하는 방법.
- 제1항에 있어서, N-[N-(1S)-에톡시카보닐-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[3,2-C]피리딘-4(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[N-(1S)-에톡시카보닐-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[2,3-C]피리딘-7(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[N-(1S)-카복시-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[2,3-C]피리딘-5(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[N-(1S)-카복시-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[3,2-C]피리딘-6(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[N-(1S)-카브에톡시-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[3,2-C]피리딘-5(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[1-(S-카브에톡시-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[3,2-C]피리딘-6(S)-카복실산을 제조하는 방법
- 제1항에 있어서, N-[N-(1(S)-카복시-3-페닐프로필)-L-리실]-4,5,6,7-테트라하이드로-티에노[3,2-C]피리딘-6(R)-카복실산을 제조하는 방법※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529960 DE3529960A1 (de) | 1985-08-22 | 1985-08-22 | Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung |
| DEP3529960.6 | 1985-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR870002145A true KR870002145A (ko) | 1987-03-30 |
Family
ID=6279053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860006897A KR870002145A (ko) | 1985-08-22 | 1986-08-21 | 아미노산 유도체의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5008273A (ko) |
| EP (1) | EP0213499A3 (ko) |
| JP (1) | JPS6245598A (ko) |
| KR (1) | KR870002145A (ko) |
| AU (1) | AU594969B2 (ko) |
| DD (1) | DD258609A5 (ko) |
| DE (1) | DE3529960A1 (ko) |
| DK (1) | DK398986A (ko) |
| ES (1) | ES2001875A6 (ko) |
| FI (1) | FI863358A (ko) |
| GR (1) | GR862183B (ko) |
| HU (1) | HU196434B (ko) |
| IL (1) | IL79792A (ko) |
| NO (1) | NO164982C (ko) |
| NZ (1) | NZ217310A (ko) |
| PL (1) | PL148493B1 (ko) |
| PT (1) | PT83239B (ko) |
| SU (1) | SU1544188A3 (ko) |
| YU (1) | YU146686A (ko) |
| ZA (1) | ZA866311B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3801587A1 (de) * | 1988-01-21 | 1989-08-03 | Hoechst Ag | Neue aminosaeureglyceride, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und deren verwendung |
| CA1340588C (en) * | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Amino acid derivatives |
| US5162336A (en) * | 1990-06-21 | 1992-11-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Tetrahydro-pyrido-indoles as cholecystokinin and gastrin antagonists |
| US5688762A (en) * | 1995-09-06 | 1997-11-18 | Steiner; Zoltan W. | Method of treating hypertension using animal stomach mucosa extract and endogenous protease-inhibitor peptides |
| US5922839A (en) * | 1995-09-06 | 1999-07-13 | Steiner; Zoltan W. | Method of treating hypertension using a composition containing a dried animal stomach mucosa and endogenous protease-inhibitor peptides |
| WO2001004090A2 (en) * | 1999-07-09 | 2001-01-18 | Ortho-Mcneil Pharmaceutical, Inc. | Neurotrophic tetrahydroisoquinolines and tetrahydrothienopyridines, and related compositions and methods |
| CA2609812C (en) * | 2005-05-27 | 2013-12-24 | University Of Cape Town | Angiotensin i-converting enzyme (ace) inhibitors |
| US7632796B2 (en) | 2005-10-28 | 2009-12-15 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| US8263539B2 (en) * | 2005-10-28 | 2012-09-11 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and methods for its use |
| US9329486B2 (en) | 2005-10-28 | 2016-05-03 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| TWI450052B (zh) * | 2008-06-24 | 2014-08-21 | Dynaloy Llc | 用於後段製程操作有效之剝離溶液 |
| US8987181B2 (en) | 2011-11-08 | 2015-03-24 | Dynaloy, Llc | Photoresist and post etch residue cleaning solution |
| US9158202B2 (en) | 2012-11-21 | 2015-10-13 | Dynaloy, Llc | Process and composition for removing substances from substrates |
| US9029268B2 (en) | 2012-11-21 | 2015-05-12 | Dynaloy, Llc | Process for etching metals |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2487829A2 (fr) * | 1979-12-07 | 1982-02-05 | Science Union & Cie | Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| DE3174844D1 (en) * | 1980-10-23 | 1986-07-24 | Schering Corp | Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them |
| DE3302125A1 (de) * | 1983-01-22 | 1984-07-26 | Boehringer Ingelheim KG, 6507 Ingelheim | Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung |
-
1985
- 1985-08-22 DE DE19853529960 patent/DE3529960A1/de not_active Withdrawn
-
1986
- 1986-08-04 SU SU864027899A patent/SU1544188A3/ru active
- 1986-08-14 EP EP86111239A patent/EP0213499A3/de not_active Withdrawn
- 1986-08-20 DD DD86293752A patent/DD258609A5/de not_active IP Right Cessation
- 1986-08-20 PL PL1986261087A patent/PL148493B1/pl unknown
- 1986-08-20 FI FI863358A patent/FI863358A/fi not_active Application Discontinuation
- 1986-08-21 YU YU01466/86A patent/YU146686A/xx unknown
- 1986-08-21 ZA ZA866311A patent/ZA866311B/xx unknown
- 1986-08-21 DK DK398986A patent/DK398986A/da not_active Application Discontinuation
- 1986-08-21 IL IL79792A patent/IL79792A/xx unknown
- 1986-08-21 JP JP61194129A patent/JPS6245598A/ja active Pending
- 1986-08-21 NZ NZ217310A patent/NZ217310A/en unknown
- 1986-08-21 HU HU863645A patent/HU196434B/hu not_active IP Right Cessation
- 1986-08-21 NO NO863373A patent/NO164982C/no unknown
- 1986-08-21 ES ES8601245A patent/ES2001875A6/es not_active Expired
- 1986-08-21 AU AU61691/86A patent/AU594969B2/en not_active Ceased
- 1986-08-21 KR KR1019860006897A patent/KR870002145A/ko not_active Application Discontinuation
- 1986-08-22 GR GR862183A patent/GR862183B/el unknown
- 1986-08-22 PT PT83239A patent/PT83239B/pt not_active IP Right Cessation
-
1989
- 1989-09-06 US US07/403,628 patent/US5008273A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0213499A2 (de) | 1987-03-11 |
| US5008273A (en) | 1991-04-16 |
| DK398986D0 (da) | 1986-08-21 |
| GR862183B (en) | 1986-12-23 |
| NO164982C (no) | 1990-12-05 |
| SU1544188A3 (ru) | 1990-02-15 |
| NO863373D0 (no) | 1986-08-21 |
| DK398986A (da) | 1987-02-23 |
| EP0213499A3 (de) | 1989-08-23 |
| NO863373L (no) | 1987-02-23 |
| JPS6245598A (ja) | 1987-02-27 |
| ZA866311B (en) | 1988-04-27 |
| PL261087A1 (en) | 1988-04-14 |
| NO164982B (no) | 1990-08-27 |
| PT83239B (pt) | 1989-03-30 |
| DE3529960A1 (de) | 1987-03-05 |
| FI863358A (fi) | 1987-02-23 |
| DD258609A5 (de) | 1988-07-27 |
| PL148493B1 (en) | 1989-10-31 |
| IL79792A0 (en) | 1986-11-30 |
| HU196434B (en) | 1988-11-28 |
| NZ217310A (en) | 1990-01-29 |
| HUT42505A (en) | 1987-07-28 |
| AU594969B2 (en) | 1990-03-22 |
| ES2001875A6 (es) | 1988-07-01 |
| FI863358A0 (fi) | 1986-08-20 |
| IL79792A (en) | 1990-11-05 |
| AU6169186A (en) | 1987-02-26 |
| PT83239A (de) | 1986-09-01 |
| YU146686A (en) | 1988-02-29 |
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