KR860006489A - 지방족-방향족 케톤 측쇄를 함유하는 펩티드의 제법 - Google Patents

지방족-방향족 케톤 측쇄를 함유하는 펩티드의 제법 Download PDF

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KR860006489A
KR860006489A KR1019860001235A KR860001235A KR860006489A KR 860006489 A KR860006489 A KR 860006489A KR 1019860001235 A KR1019860001235 A KR 1019860001235A KR 860001235 A KR860001235 A KR 860001235A KR 860006489 A KR860006489 A KR 860006489A
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phe
peptide
pro
arg
trp
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KR1019860001235A
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KR900007865B1 (ko
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에드워어드 프레드릭 리비어 지인
에드워어드 프레드릭 리비어 외 2 지인
알렉 앤더슨 해리
베일 쥬니어 와일리워어커
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더 솔크 인스티튜티 훠 바이올로지칼 스터디이즈
델버어트 어니스트그랜즈
더 솔크 인스티튜트 훠 바이올로지칼 스터디이즈
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S930/00—Peptide or protein sequence
    • Y10S930/01—Peptide or protein sequence
    • Y10S930/13—Luteinizing hormone-releasing hormone; related peptides

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Endocrinology (AREA)
  • Genetics & Genomics (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음

Description

지방족－방향족 케톤 측쇄를 함유하는 펩티드의 제법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 그 기본쇄중 비말단 위치에 글루타민산, 호모글루타민산 또는 아스파르틴산을 갖고 있으며 그 잔기의 측쇄가 방향족 기에서 끝나는 혼합알킬케톤으로 구성되어 있는 50개 이하의 잔기로 된 펩티드 호르몬을 제조하는데 있어서, 그 방법이 상기 기본 펩티드쇄가 원하는 위치에 글루타민산, 호모글루타민산 또는 아스파트틴산 잔기를 함유하며 그 측쇄카복실기가 벤질에스테르, 2,6－디클로로벤질, 디니트로페닐, 1－하이드록시－벤조트리아졸벤질에스테르, 8－하이드록시퀴놀린에스테르, p－니트로벤질옥시, 페닐아조페닐 및 t－부톡시로 구성된 부류로 부터 선택된 보호기에 의해 보호된 펩티드 중간체를 형성한 다음 ; 상기 펩티드 중간체를 상기 보호기가 제거되고 그 이온이 상기 방향족 화합물과 반응하여 그와 혼합 알킬케톤을 형성하는 아크릴늄 이온 중간체가 형성될 수 있는 조건하에서 HF 및 앞서 정의한 Z'부류로 부터 선택된 방향족 화합물로 처리하고 ; 상기 HF를 제거하고 ; 상기 방향족 케톤측쇄를 포함한 결과로서 문제의 수용체에 대한 결합친화력이 증가된 상기한 바라는 펩티드 호르몬을 회수하는 것으로 구성되어 있는 펩티드의 제법.
  2. 제 1 항에 있어서 하기 구조를 가진 GnRH 길항제 펩티드를 제조하는 방법.
    X－R1－(W)D－Phe－R3－R4－R5－R6(V)－R7－Arg－Pro－R|10
    상기구조에서,
    X는 수소 또는 C1－7의 아실기이며 ; R1은 대하이드로－Pro,Pro,D－pGlu,D－Phe,D－Trp 또는 β－D－NAL이며 ; W는 F,Cl,Cl2Br,NO2또는 CaMe/Cl이며 ; R3는 D－Trp,D－3PAL,(NinFor)D－Trp 또는 5－ 또는 6－위치가 NO2,NH2,OCH3,F,Cl,Br 또는 CH3에 의해 치환된 D－Trp이며 ; R4는 Ser,Orn,AAL 또는 aBu이며 ; R5는 Tyr,Arg,(2F)Phe,(2F)Phe,(3I)Tyr,(3CH3)Phe,(2CH3)Phe,(3Cl)Phe 또는 (2Cl)Phe이며 ; R6는 D－Glu,D－Hgl 또는 D－Asp이며 ; R7는 Leu,NML,NIe 또는 Nva이며 ; R10은 Gly－NH2,D－Ala－NH2또는 NH－Y이며 여기서 Y는 저급알킬, 사이클로알킬, 플루오로저급알킬 또는 NHCONHQ이며 (Q는 H 또는 저급알킬임) ; V는 R6의 카복실기측쇄와 Z'로 부터 선택된 화합물로 부터 생성된 케톤의 방향족 부분이다.
  3. 제 2 항에 있어서 R6가 D－Glu인 방법.
  4. 제 2 항 또는 제 3 항에 있어서 V가 C6H4OCH3인 방법.
  5. 제 2 항에 있어서 R6가 D－Hgl이며 V가 C6H4OCH3인 방법.
  6. 제 2 항에 있어서 하기 구조를 가진 펩티드를 제조하는 방법.
    Ac－β－D－2NAL－(4Cl)D－Phe－D－3PAL－Ser－Arg－D－Glu(C6H4OCH3)－Leu－Arg－Pro－D－Ala－HN2.
  7. 제 2 항에 있어서 하기 구조를 가진 펩티드를 제조하는 방법.
    Ac－데하이드로Pro－(4F)D－Phe－β－D－2NAL－Ser－Tyr－D－Glu(C6H4OCH3)－Leu－Arg－Pro－Gly－HN2.
  8. 제 1 항에 있어서 하기 구조를 가진 GnRH 길항제 펩티드를 제조하는 방법.
    R1－His－Trp－Ser－Tyr－R6(V)－Leu－Arg－Pro－R10
    상기구조에서,
    R1은 pGlu 또는 포르밀 Pro이며 R6는 D－Glu,D－Hgl 또는 D－Asp이며 ; R10은 Gly－NH2,D-Ala-NH2또는 NH－Y이며, 여기서 Y는 저급알킬 또는 플루오르 저급알킬이며 ; V는 상기 정의된 Z'로 부터 선택된 화합물로부터 생성된 케톤의 방향족 부분이다.
  9. 제 1 항에 있어서 상기 펩티드가 하기 구조식을 갖는 방법.
    pGlu－His－Trp－Ser－Tyr－D－Glu(C6H4OCH3)－Leu－Arg－Pro－Gly－NHCH2CH3.
  10. 제 1 항에 있어서, 상기 처리가 약 20℃ 또는 그 이상의 온도에서 수행되는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019860001235A 1985-02-22 1986-02-21 지방족-방향족 케톤 측쇄를 함유하는 펩티드 및 그의 제법 KR900007865B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/704,299 US4677193A (en) 1985-02-22 1985-02-22 Peptides containing an aliphatic-aromatic ketone side chain
US704,299 1985-02-22

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KR860006489A true KR860006489A (ko) 1986-09-11
KR900007865B1 KR900007865B1 (ko) 1990-10-22

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US (1) US4677193A (ko)
EP (1) EP0192492B1 (ko)
JP (1) JPH0631315B2 (ko)
KR (1) KR900007865B1 (ko)
AT (1) ATE71112T1 (ko)
AU (1) AU585583B2 (ko)
CA (1) CA1307374C (ko)
DD (1) DD247009A5 (ko)
DE (1) DE3683169D1 (ko)
DK (1) DK79686A (ko)
ES (1) ES8707973A1 (ko)
GR (1) GR860456B (ko)
HU (1) HU204849B (ko)
IE (1) IE58815B1 (ko)
MX (1) MX162099A (ko)
PH (1) PH22616A (ko)
PT (1) PT82069B (ko)
ZA (1) ZA86569B (ko)

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ATE81255T1 (de) * 1985-07-05 1992-10-15 United Biscuits Ltd Backwaren mit lagerstabiler textur.
HU194280B (en) * 1985-10-22 1988-01-28 Richter Gedeon Vegyeszet Process for producing new gonadoliberin analogues of high effectivity and pharmaceutical compositions containing them
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HU194913B (en) * 1986-01-03 1988-03-28 Innofinance Altalanos Innovaci Process for producing novel gonadoliberin derivatives containing in the sixth position aromatic amino carboxylic acid and medical preparations containing these compounds
US4914189A (en) * 1987-02-05 1990-04-03 The Adminstrators Of The Tulane Educational Fund Synthetic GHRH analogs
US4800191A (en) * 1987-07-17 1989-01-24 Schally Andrew Victor LHRH antagonists
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HU208158B (en) * 1990-02-20 1993-08-30 Syntex Inc Process for the synthesis of 1h-rh analogs by temporary protection
ATE127476T1 (de) * 1990-04-06 1995-09-15 Univ Tulane Lhrh-analoge.
US5869605A (en) * 1992-10-30 1999-02-09 Rhone-Poulencchimie Protected compound comprising a protective group removably attached to a compound to be protected
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US5843901A (en) 1995-06-07 1998-12-01 Advanced Research & Technology Institute LHRH antagonist peptides
US6521641B1 (en) 1998-10-08 2003-02-18 Allergan, Inc. Male anti-fertility agents
US6455499B1 (en) 1999-02-23 2002-09-24 Indiana University Foundation Methods for treating disorders associated with LHRH activity
US6598784B2 (en) * 2000-12-20 2003-07-29 Meadwestvaco Packaging Syatens, Llc Beverage carton with strap type carrying handle
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IL70888A0 (en) * 1983-03-10 1984-05-31 Salk Inst For Biological Studi Gn rh antagonist peptides and pharmaceutical compositions containing them
HU187503B (en) * 1983-03-29 1986-01-28 Magyar Tudomanyos Akademia,Hu Process for preparing gonadoliberine derivatives containing beta-aspartyl group
US4547370A (en) * 1983-11-29 1985-10-15 The Salk Institute For Biological Studies GnRH Antagonists

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AU585583B2 (en) 1989-06-22
EP0192492A3 (en) 1988-03-02
GR860456B (en) 1986-06-18
PH22616A (en) 1988-10-17
IE58815B1 (en) 1993-11-17
DK79686D0 (da) 1986-02-20
KR900007865B1 (ko) 1990-10-22
US4677193A (en) 1987-06-30
CA1307374C (en) 1992-09-08
ATE71112T1 (de) 1992-01-15
HU204849B (en) 1992-02-28
PT82069B (pt) 1988-01-22
PT82069A (en) 1986-03-01
DD247009A5 (de) 1987-06-24
JPS61194098A (ja) 1986-08-28
DE3683169D1 (de) 1992-02-13
JPH0631315B2 (ja) 1994-04-27
ES552266A0 (es) 1987-09-01
IE860385L (en) 1986-08-22
AU5348986A (en) 1986-08-28
DK79686A (da) 1986-08-23
EP0192492A2 (en) 1986-08-27
ES8707973A1 (es) 1987-09-01
EP0192492B1 (en) 1992-01-02
ZA86569B (en) 1986-11-26
MX162099A (es) 1991-03-27
HUT40146A (en) 1986-11-28

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