KR960703110A - 길항 펩티드의 GnRH 제조를 위해 유용한 구아니디노 또는 변형된 구아니디노기를 함유하는 페닐알라닌 유도체 또는 동족체의 제조 방법(PROCESS FOR THE PREPA-RATION OF PHENYLALANINE DERIVATIVES OR HOMOLOGUES CONTAIN-ING A GUANIDINO OR MODIFIED GUANIDINO GROUP USEFUL FOR THE PREPARATION GnRH OF ANTAGONISTIC PEPTIDES) - Google Patents

길항 펩티드의 GnRH 제조를 위해 유용한 구아니디노 또는 변형된 구아니디노기를 함유하는 페닐알라닌 유도체 또는 동족체의 제조 방법(PROCESS FOR THE PREPA-RATION OF PHENYLALANINE DERIVATIVES OR HOMOLOGUES CONTAIN-ING A GUANIDINO OR MODIFIED GUANIDINO GROUP USEFUL FOR THE PREPARATION GnRH OF ANTAGONISTIC PEPTIDES) Download PDF

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KR960703110A
KR960703110A KR1019950705738A KR19950705738A KR960703110A KR 960703110 A KR960703110 A KR 960703110A KR 1019950705738 A KR1019950705738 A KR 1019950705738A KR 19950705738 A KR19950705738 A KR 19950705738A KR 960703110 A KR960703110 A KR 960703110A
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에이. 호거 카알
이.에프. 리비에르 진
에스. 포터 존
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더글라스 리이 버쉬
더 솔크 인스티튜트 포오 바이오로지칼 스터디이즈
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    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
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Abstract

본 발명은 건조 전뇌하수체에 의해 고나도트로핀의 분비물을 억제하거나 촉진하고, 생식선에 의해 스테로이드의 방출을 억제하는 펩티드내로 혼입될 수 있는 인공 아미노산을 제조하는 방법에 관한 것으로 이 방법은, 식(i)를 갖는 α-아미노산을 :(CH2)j-CHNH2COOH(여기서, j는 1, 2, 또는 3) α-아미노산의 각 몰에 대해 적어도 약 2몰의 HNO3를 갖는 진한 질산, 진한 황산, 및 상기 아미노산을 포함하는 반응 혼합물을 형성하고, 약 5℃이하의 온도에서 이 반응 혼합물을 유지시키므로써 니트로화 조건에 적용시켜, 이 니트로화가 4-위치에서 주로 일어나게 하고, 적당한 약제와 상기 4NO2-치환 생성물을 반응시켜 상기 α-아미노산에 아미노-보호기를 첨가시키고, 상기 보호된 아미노산을 처리하여, 상기 치환된 니트로 부분을 수소첨가시키고, 그를 아미노 부분으로 변형시키며, 적합한 용매내에 상기 수소첨가된 아미노산을 용해시키고, 그를 디페닐시아노카르본이미데이트와 반응시켜, 친핵성 부분과 반응성 시아노구아니디노 중간체를 형성하여, 구조식(a) 또는 구조식(b)를 갖는 원하를 인공 아미노산을 생성하는 것으로 구성된다.

Description

길항 펩티드의 GnRH 제조를 위해 유용한 구아니디노 또는 변형된 구아니디노기를 함유하는 페닐알라닌 유도체 또는 동족체의 제조 방법(PROCESS FOR THE PREPARATION OF PHENYLALANINE DERIVATIVES OR HOMOLOGUES CONTAINING A GUANIDINO OR MODIFIED GUANIDINO GROUP USEFUL FOR THE PREPARATION GnRH OF ANTAGONISTIC PEPTIDES)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 사슬 연장 방법에 의해 펩티드의 합성에 유용한 인공 아미노산을 제조하는 방법으로서, 하기 식을 갖는 α-아미노산을 :(CH2)j-CHNH2COOH(여기서, j는 1, 2, 또는 3) α-아미노산을 각 몰에 대해 적어도 약 2몰의 HNO3를 갖는 진한 질산, 진한 황상, 및 상기 아미노산을 포함하는 반응 혼합물을 형성하고, 약 5℃이하의 온도에서 이 반응 혼합물을 유지시키므로써 니트로화 조건에 적용시켜, 이 니트로화가 4-위치에서 주로 일어나게 하고, 적당한 약제와 상기 4NO2-치환 생성물을 반응시켜 상기 α-아미노산에 아미노-보호기를 첨가시키고, 상기 보호된 아미노산을 처리하여, 상기 치환된 니트로 부분을 수소첨가시키고, 그를 아미노 부분으로 변형시키며 적합한 용매내에 상기 수소첨가된 아미노산을 용해시키고, 그를 디페닐시아노카르본이미데이트와 반응시켜, 친핵성 부분과 반응성 시아노구아니디노 중간체를 형성하여, 원하는 인공 아미노산을 생성하는 것으로 구성되는 방법.
  2. 제1항에 있어서, 진한 질산이 α-아미노산의 몰당 약 2∼약3.5몰 HNO3양으로 상기 니트로화 단계에서 사용되는 방법.
  3. 제2항에 있어서, 상기 진한 황산이 NHO3의 각 당량당 약 2∼약 3당량의 양으로 사용되는 방법.
  4. 제1항에 있어서, 상기 4NO2-치환 생성물이 지방족 우레탄 보호기에 의해 α-아미노기를 보호하는 약제와 반응되는 방법.
  5. 제4항에 있어서, 상기 보호기가 터트-부틸옥시카르보닐(Boc)인 방법.
  6. 제5항에 있어서, 상기 약제가 디-터트-부틸디카르보네이트인 방법.
  7. 제1항에 있어서, 상기 보호된 α-아미노산이 알콜내에 용해되고, 팔라듐/탄소 촉매를 사용하여 수소첨가되는 방법.
  8. 제1항에 있어서, 상기 수소첨가된 화합물이 상기 반응을 위해 디클로메탄 및 N-메틸피롤리딘의 혼합물 내 용해되어 상기 시아노구아니디노 중간체를 생성하는 방법.
  9. 제8항에 있어서, 히드라진 수화물 형태의 히드라진이 상기 중간체가 용해되는 용액에 첨가되는 방법.
  10. 제9항에 있어서, j가 1인 방법.
  11. 제1∼10항중 어느 한 항에 있어서, 상기 중간체가 히드라진과 반응되어, 상기 아미노산의 측쇄가 페닐고리의 4-위치에 부착된 3-아미노, 1,24 트리아졸 부분을 생성하는 방법.
  12. 펩티드 중간체 α-아미노기의 보호를 제거하고, 이것을 아미드 결합을 형성하기 위해 제1항의 방법에 의해 제조된 α-아미노산과 반응시키는 것으로 구성되는, 펩티드의 C-말단으로부터 사슬 연장에 의해 펩티드를 합성하는 방법.
  13. 아미노산이 하기 일반 구조식을 갖는, 제1항의 방법에 의해 제조된 아미노산:
    상기 식에, X1은 α-아미노-보호기이고, j는 1, 2, 또는 3이고, R2는 알킬, 변형된 알킬, 알케닐, 알키닐, 아릴 또는 메틸피리딜이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950705738A 1993-06-17 1994-06-13 길항 펩티드의 gnrh 제조를 위해 유용한 구아니디노또는변형된구아니디노기를함유하는페닐알라닌유도체또는동족체의제조방법 KR100308361B1 (ko)

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US08/078965 1993-06-17
US08/078,965 1993-06-17
US08/078,965 US5352796A (en) 1989-10-30 1993-06-17 Amino acids useful in making GnRH analogs
PCT/US1994/006726 WO1995000474A1 (en) 1993-06-17 1994-06-13 PROCESS FOR THE PREPARATION OF PHENYLALANINE DERIVATIVES OR HOMOLOGUES CONTAINING A GUANIDINO OR MODIFIED GUANIDINO GROUP USEFUL FOR THE PREPARATION GnRH OF ANTAGONISTIC PEPTIDES

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AU (1) AU682702B2 (ko)
CA (1) CA2165469A1 (ko)
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Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5352796A (en) * 1989-10-30 1994-10-04 The Salk Institute For Biological Studies Amino acids useful in making GnRH analogs
US6469158B1 (en) * 1992-05-14 2002-10-22 Ribozyme Pharmaceuticals, Incorporated Synthesis, deprotection, analysis and purification of RNA and ribozymes
GB9312761D0 (en) * 1993-06-21 1993-08-04 Wellcome Found Amino acid derivatives
US5843901A (en) * 1995-06-07 1998-12-01 Advanced Research & Technology Institute LHRH antagonist peptides
JPH11514380A (ja) * 1995-10-27 1999-12-07 メルク エンド カンパニー インコーポレーテッド ＧｎＲＨ／シュードモナス還元型菌体外毒素結合体
US5912872A (en) * 1996-09-27 1999-06-15 Digital Optics Corporation Integrated optical apparatus providing separated beams on a detector and associated methods
US5928727A (en) * 1997-06-02 1999-07-27 Lacks Industries, Inc. Method for electroplating elastomer-modified polyphthalamide articles
WO1999026964A1 (en) * 1997-11-20 1999-06-03 Ortho-Mcneil Pharmaceutical, Inc. LIQUID PHASE PROCESS FOR THE PREPARATION OF GnRH PEPTIDES
SI20424A (sl) * 1998-03-05 2001-06-30 Agouron Pharmaceuticals, Inc. Nepeptidna GnRH sredstva
US6455499B1 (en) 1999-02-23 2002-09-24 Indiana University Foundation Methods for treating disorders associated with LHRH activity
AU2001268607A1 (en) * 2000-06-21 2002-01-02 Bristol-Myers Squibb Company Piperidine amides as modulators of chemokine receptor activity
PL361027A1 (en) * 2000-07-14 2004-09-20 Allergan,Inc. Compositions containing therapeutically active components having enhanced solubility
US20040214829A1 (en) * 2000-07-14 2004-10-28 Allergan, Inc. Compositions containing alpha-2-adrenergic agonist components
US8858961B2 (en) 2000-07-14 2014-10-14 Allergan, Inc. Compositions containing alpha-2-adrenergic agonist components
JP4927298B2 (ja) 2000-07-14 2012-05-09 アラーガン、インコーポレイテッド α−２−アドレナリンアゴニスト成分を含有する組成物
US20050026924A1 (en) * 2000-07-14 2005-02-03 Allergan, Inc. Compositions containing alpha-2-adrenergic agonist components
US6598784B2 (en) * 2000-12-20 2003-07-29 Meadwestvaco Packaging Syatens, Llc Beverage carton with strap type carrying handle
CA2587444C (en) * 2004-11-12 2013-09-10 Ucl Business Plc Guanidine derivatives as inhibitors of ddah
JP5649825B2 (ja) 2007-01-31 2015-01-07 デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド 安定化させたｐ５３ペプチドおよびその使用法
ES2430067T3 (es) 2007-03-28 2013-11-18 President And Fellows Of Harvard College Polipéptidos cosidos
KR20170058446A (ko) 2010-08-13 2017-05-26 에일러론 테라퓨틱스 인코포레이티드 펩티도미메틱 거대고리
RU2639523C2 (ru) 2011-10-18 2017-12-21 Эйлерон Терапьютикс, Инк. Пептидомиметические макроциклы и их применение
CA2864120A1 (en) 2012-02-15 2013-08-22 Aileron Therapeutics, Inc. Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles
CA2862038C (en) 2012-02-15 2021-05-25 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
JP6526563B2 (ja) 2012-11-01 2019-06-05 エイルロン セラピューティクス，インコーポレイテッド 二置換アミノ酸ならびにその調製および使用の方法
MX365465B (es) 2013-03-21 2019-06-04 Sanofi Aventis Deutschland Sintesis de productos peptidicos que contienen imida ciclica.
SG11201506804VA (en) 2013-03-21 2015-09-29 Sanofi Aventis Deutschland Synthesis of hydantoin containing peptide products
MX2017003797A (es) 2014-09-24 2017-06-15 Aileron Therapeutics Inc Macrociclos peptidomimeticos y usos de los mismos.
CN107614003A (zh) 2015-03-20 2018-01-19 艾瑞朗医疗公司 拟肽大环化合物及其用途

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK558181A (da) * 1981-01-30 1982-07-31 Smithkline Corp Fremgangsmaade til fremstilling af 3,5-diamino-1,2,4-triazoler
EP0079522B1 (en) * 1981-11-09 1986-05-07 Merck & Co. Inc. N-carboxymethyl(amidino)lysyl-proline antihypertensive agents
US4935491A (en) * 1987-08-24 1990-06-19 Board Of Regents, The University Of Texas System Effective antagonists of the luteinizing hormone releasing hormone which release negligible histamine
US5110904A (en) * 1989-08-07 1992-05-05 Abbott Laboratories Lhrh analogs
US5352796A (en) * 1989-10-30 1994-10-04 The Salk Institute For Biological Studies Amino acids useful in making GnRH analogs
IL101074A (en) * 1991-03-14 1997-09-30 Salk Inst For Biological Studi GnRH ANALOGS AND THEIR PREPARATION

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CA2165469A1 (en) 1995-01-05
WO1995000474A1 (en) 1995-01-05
ZA944345B (en) 1995-04-03
PH31215A (en) 1998-05-05
EP0703900A1 (en) 1996-04-03
DE69416676T2 (de) 1999-09-16
KR100308361B1 (ko) 2001-11-30
US5710249A (en) 1998-01-20
DE69416676D1 (de) 1999-04-01
IL110032A (en) 1999-09-22
EP0703900B1 (en) 1999-02-24
US5352796A (en) 1994-10-04
JPH09500110A (ja) 1997-01-07
AU7061194A (en) 1995-01-17
US5565574A (en) 1996-10-15
AU682702B2 (en) 1997-10-16
IL110032A0 (en) 1994-10-07
ATE176904T1 (de) 1999-03-15
NZ267921A (en) 1997-12-19

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