KR830008998A - N-치환된-아미노-아미노산의 제조방법 - Google Patents
N-치환된-아미노-아미노산의 제조방법 Download PDFInfo
- Publication number
- KR830008998A KR830008998A KR1019820001387A KR820001387A KR830008998A KR 830008998 A KR830008998 A KR 830008998A KR 1019820001387 A KR1019820001387 A KR 1019820001387A KR 820001387 A KR820001387 A KR 820001387A KR 830008998 A KR830008998 A KR 830008998A
- Authority
- KR
- South Korea
- Prior art keywords
- lower alkyl
- amino
- formula
- alkyl
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- -1 N-substituted-amino-amino Chemical group 0.000 title claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 1
- 108010016626 Dipeptides Proteins 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 150000004716 alpha keto acids Chemical class 0.000 claims 1
- 238000010640 amide synthesis reaction Methods 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (14)
- 아미드 생성 반응 조건하에서 일반식(II)의 아미노화합물을 일반식(III)의 단 아실화유도체와 반응시키거나, 일반식(IV)의 디펩티드를 일반식(V)의 α-케토산과 또는 에스테르와 반응시켜 수득되는 이민을 환원시키거나 또는 일반식(VI)의 혼합물을 일반식(VII)의 할로 화합물과 반응시켜 일반식(I)의 화합물을 얻은 후 치환 또는 전환반응에 의해 수득된 일반식(I)의 화합물중에 여러 치환체를 도입시키고 임의로 그 염을 형성시킴을 특징으로 하는 일반식(I)의 N-치환-아미도-아미노산 및 그 약제학적으로 가능한 산 및 염기와의 염의 제조방법.상기식에서R 및 R9는 독립적으로 하이드록시, 저급알콕시, 저급알케녹시, 디(저급알킬)아미노-저급알콕시, 하이드록시-저급알콕시, 아실아미노-저급알콕시, 아실옥시-저급알콕시, 아릴옥시, 아릴옥실-저급알콕시, 아미노, 저급알킬아미노, 디-저급알킬아미노, 하이드록시아미노, 또는 아릴-저급알킬아미노이고;R1,R2,R3,R4,R5,R7및 R8은 독립적으로 수소, 탄소수 20까지인 알킬, 알케닐 또는 알키닐, 탄소수 12까지의 아릴 또는 아릴-저급알킬, 탄소수 6 내지 12의 사이클릭 또는 헤테로 사이클릭 저급알킬 또는 탄소수 20까지인 사이클로알킬 또는 사이클로알킬 알킬이고;R6은 헤테로사이클릭 및 헤테로사이클릭 알킬이고;R2및 R3은 이들이 각각 결합된 탄소 및 질소와 함께, R3및 R5는 이들이 각각 결합된 질소 및 탄소와 함께, 3 내지 5 또는 2 내지 4개의 탄소원자 및 황원자 하나를 함유하는 N-헤테로사이클을 생성하고,상기 알킬, 알케닐 및 알키닐그룹은 하이드록시, 저급알콕시, 티오, 저급알킬멀캅토, 아미노, 저급알킬 아미노, 디(저급알킬)아미노, 할로겐 및 니트로에 의해 치환될 수 있다.
- 제1항에 있어서, R 및 R9는 각각 독립적으로 하이드록시 및 저급알콕시이고 R1및 R2는 각각 독립적으로 수소, 저급알킬, 탄소수 7 내지 12의 아릴-저급알킬, 또는 탄소수 6 내지 12의 헤테로사이클릭 저급알킬이고,R3,R4,R5,R7및 R8은 수소 또는 저급알킬이고,R6는 헤테로사이클릭 또는 헤테로사이클릭 알킬인 일반식(I)화합물 및 그 약제학적으로 가능한 산 및 염기와의 염을 제조하는 방법.
- 제1항 또는 2항에 있어서, R6는 피롤, 피롤린, 피콜리딘, 피리딘, 디-하이드로피리딘, 피페리딘, 모르폴린, 티아모르폴린, 이미다졸, 이미다졸린, 이미다졸리딘, 푸란, 풀푸릴, 티오펜, 벤즈이미다졸, 티아졸, 티아졸린, 티아졸리딘, 인돌, 퀴놀린, 이소퀴놀린, 테트라하이드로, 퀴놀린, 테트라하이드로이소퀴놀린인 방법.
- 제1항 내지 3항에 있어서, 헤테로사이클 그룹은 저급알킬, 저급알케닐, 저급알키닐, 하이드록시, 저급알콕시, 아미노, 저급알킬아미노, 디(저급알킬)아미노, 티올, 저급알킬멀캅, 하이드록시-저급알킬, 아미노-저급알킬, 티오-저급알킬, 니트로, 할로겐, 트리플루오로메틸, 메틸렌디옥시, 우레이도, 구아니디노로부터 선택된 하나 이상의 치환체를 지니는 방법.
- 제1항 내지 3항에 있어서, R1이 저급알킬 또는 페닐-저급알킬이고, R4는 저급알킬이고, R2,R3,R5,R7및 R8은 수소인 방법.
- 제1항 내지 3항에 있어서, R 및 R9는 하이드록시인 방법.
- 제1항 내지 3항에 있어서, R은 에톡시이고, R9는 하이드록시인 방법.
- 제1항 내지 3항에 있어서, R1및 R4는 각각 메틸인 방법.
- 제1항 내지 3항에 있어서, R1은 벤질 또는 페네틸이고 R4는 메틸인 방법.
- 제1항 내지 3항에 있어서, R6는 인돌릴에틸인 방법.
- 제1항 내지 3항에 있어서, R1은 벤질인 방법.
- 제1항 내지 3항에 있어서, R1은 페네틸인 방법.
- 제1항 내지 3항에 있어서, R은 에톡시이고 R1은 펜에틸이고, R4는 메틸이고, R6는 2-(3-인돌릴 메틸)이고 R9는 하이드록시인 방법.
- 제13항에 있어서, R2, R3, R5, R7및 R8는 각각 수소인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24905381A | 1981-03-30 | 1981-03-30 | |
| US249053 | 1981-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830008998A true KR830008998A (ko) | 1983-12-16 |
Family
ID=22941861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019820001387A KR830008998A (ko) | 1981-03-30 | 1982-03-30 | N-치환된-아미노-아미노산의 제조방법 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0061768B1 (ko) |
| JP (1) | JPS57175152A (ko) |
| KR (1) | KR830008998A (ko) |
| AT (1) | ATE19782T1 (ko) |
| AU (1) | AU556932B2 (ko) |
| DE (1) | DE3271116D1 (ko) |
| IL (1) | IL65347A (ko) |
| NZ (1) | NZ200162A (ko) |
| PH (3) | PH20083A (ko) |
| ZA (1) | ZA822083B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820729A (en) * | 1981-03-30 | 1989-04-11 | Rorer Pharmaceutical Corporation | N-substituted-amido-amino acids |
| US4686295A (en) * | 1982-03-10 | 1987-08-11 | Usv Pharmaceutical Corporation | N-carboxy anhydride intermediates |
| US4482544A (en) * | 1982-11-29 | 1984-11-13 | Usv Pharmaceutical Corporation | Compounds for treating hypertension |
| JPS6248696A (ja) * | 1985-08-27 | 1987-03-03 | Kanegafuchi Chem Ind Co Ltd | Ｎ−〔１（ｓ）−エトキシカルボニル−３−フエニルプロピル〕−ｌ−アラニル−ｌ−プロリンの製造法 |
| US4888427A (en) * | 1987-04-07 | 1989-12-19 | University Of Florida | Amino acids containing dihydropyridine ring systems for site-specific delivery of peptides to the brain |
| US5079366A (en) * | 1987-04-07 | 1992-01-07 | University Of Florida | Quarternary pyridinium salts |
| FR2626279B1 (fr) * | 1988-01-26 | 1990-07-13 | Roussel Uclaf | Nouveaux derives de l'indolo(3,2,1-de)(1,4)-oxazino(2,3,4-ij)(1,5) naphthyridine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions les renfermant |
| JP2008545006A (ja) | 2005-07-05 | 2008-12-11 | シプラ・リミテッド | Ａｃｅ阻害剤の合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL58849A (en) * | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
| US4256761A (en) * | 1979-07-13 | 1981-03-17 | Usv Pharmaceutical Corporation | Antihypertensive amides |
-
1982
- 1982-03-19 AU AU81706/82A patent/AU556932B2/en not_active Ceased
- 1982-03-25 IL IL65347A patent/IL65347A/xx unknown
- 1982-03-25 PH PH27057A patent/PH20083A/en unknown
- 1982-03-26 ZA ZA822083A patent/ZA822083B/xx unknown
- 1982-03-29 NZ NZ200162A patent/NZ200162A/xx unknown
- 1982-03-29 DE DE8282102653T patent/DE3271116D1/de not_active Expired
- 1982-03-29 EP EP82102653A patent/EP0061768B1/en not_active Expired
- 1982-03-29 AT AT82102653T patent/ATE19782T1/de active
- 1982-03-29 JP JP57049245A patent/JPS57175152A/ja active Granted
- 1982-03-30 KR KR1019820001387A patent/KR830008998A/ko unknown
-
1983
- 1983-07-11 PH PH29200A patent/PH21449A/en unknown
- 1983-07-11 PH PH29201A patent/PH21632A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL65347A0 (en) | 1982-05-31 |
| PH20083A (en) | 1986-09-24 |
| NZ200162A (en) | 1985-08-16 |
| AU556932B2 (en) | 1986-11-27 |
| ZA822083B (en) | 1983-02-23 |
| EP0061768A1 (en) | 1982-10-06 |
| JPH0448800B2 (ko) | 1992-08-07 |
| PH21449A (en) | 1987-10-28 |
| EP0061768B1 (en) | 1986-05-14 |
| PH21632A (en) | 1988-01-13 |
| IL65347A (en) | 1987-12-31 |
| ATE19782T1 (de) | 1986-05-15 |
| AU8170682A (en) | 1982-10-07 |
| DE3271116D1 (de) | 1986-06-19 |
| JPS57175152A (en) | 1982-10-28 |
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