KR940021515A - 2, 4-디아미노-3-하이드록시카복실산 유도체 - Google Patents

2, 4-디아미노-3-하이드록시카복실산 유도체 Download PDF

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KR940021515A
KR940021515A KR1019940004724A KR19940004724A KR940021515A KR 940021515 A KR940021515 A KR 940021515A KR 1019940004724 A KR1019940004724 A KR 1019940004724A KR 19940004724 A KR19940004724 A KR 19940004724A KR 940021515 A KR940021515 A KR 940021515A
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빌리히 안드레아스
샤르삐오 브리지뜨
에트마이어 페터
그스타흐 후베르트
레르 필립
숄츠 디터
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죠오지 그렐리니, 한스 루돌프 하우스
산도즈 리미티드
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Abstract

본 발명은 하기 일반식(Ⅰ)의 화합물에 관한 것이다 :
상기 식에서 치환체는 다양한 의미를 갖는다.
이들은 예를 들면, 커플링, 치환, 탈보호 또는 보호 반응과 같은 종래의 방법에 의해 제조될 수 있다.
이들은 흥미로운 약리학적 성질을 가지고 있으며, 이로 인해 레트로바이러스 감염의 치료에, 특히 HIV 프로테이나제 억제제로 사용될 수 있다.

Description

2, 4-디아미노-3-하이드록시카복실산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. 유리 형태 또는 염 형태의 하기 일반식(Ⅰ)의 화합물 :
    상기 식에서, A 및 B는 각기 독립적으로 결합 또는 임의로 치환된 아미노아실 부분을 나타내고; R1은 수소, 아미노 보호기, 또는 일반식 R5Y-의 기(이때, R5는 수소 또는 임의로 치환된 알킬, 알케닐, 알키닐, 아릴, 아릴알킬, 헤테로아릴, 헤테로아릴알킬, 헤테로사이클릴, 또는 헤테로사이클릴알킬기를 나타내고, Y는 -CO-, -NHCO-, -NHCS-, -SO2-, -O-CO-, 또는 -O-CS-를 나타낸다)를 나타내고; R2는 천연 아미노산의 측쇄, 알킬, 아릴알킬, 헤테로아릴알킬, 또는 사이클로알킬알킬기 또는 트리메틸실릴메틸, 2-티에닐메틸, 또는 스티릴메틸을 나타내고; R3는 할로겐, 알킬, 알콕시 또는 하이드록시알콕시를 나타내고; R4는 2(R)-하이드록시인단-1(S)-일, (S)-2-하이드록시-1-페닐에틸, 또는 4번 위치에서 메톡시에 의해 임의로 치환된 2-하이드록시벤질을 나타낸다.
  2. 제1항에 있어서, 유리 형태 또는 염 형태의 하기 일반식(Ⅰs)의 화합물 :
    상기 식에서, As는 결합; (5-메틸-1, 3, 4-티아디아졸-2-일)-SCH2CO-, (벤즈티아졸-2-일)SCH2CO-또는 (1-메틸-1, 3, 4-트리아졸-2-일)SCH2CO-에 의해 질소 원자에 임의로 치환된 L-t-류시노일; (2-피리딜메틸)N(메틸)-CO- 또는 (벤즈이미다졸-2-일메틸)N(메틸)-CO-에 의해 질소원자에 임의로 치환된 L-발리노일; L-이소류시노일; 탄소원자수 1 내지 4의 알킬에 의해 유리 카복실 부분에 임의로 치환된 L-아스파틸; L-아스파라기노일; 또는 (5-메틸-1, 3, 4-티아디아졸-2-일)SCH2CO-에 의해 질소원자에 임의로 치환된 시스-1-아미노사이클로펜트-2-일카보닐 또는 시스-아미노사이클로헥스-2-일카보닐 부분이고; Bs는 결합 또는 L-발리노일이고; R1s는 수소; t-부톡시카보닐 또는 벤질옥시카보닐; 또는 일반식 R5sYs-의 기(이때, R5s는 이소부틸, 2-하이드록시-4-메톡시페닐, 이미다조[1, 2-a]피리미딘-2-일, 이미다조[1, 2-a]테트라하이드로피리미딘-2-일, 이미다조[1, 2-a]피리미딘-2-일메틸, 또는 2-(벤즈이미다졸-2-일)에틸이고, Ys는 -CO-, -NHCO-, 또는 -O-CO-이다)이고; R2s는 벤질이고; R3s는 염소, 브롬, 메틸, 메톡시, 에톡시 또는 2-하이드록시에톡시이고; R4는 제1항에서 정의한 바와 같다.
  3. 유리 형태 또는 염 형태의 4(S)-(벤질옥시카보닐-L-t-류시노일)아미노-3(S) 하이드록시-2(R)-(4-메톡시벤질아미노)-5-페닐-펜타노산 1(S)-아미노 -2(R)-하이드록시인단-아미드.
  4. a) 하기 일반식(Ⅱ)의 화합물을 하기 일반식(A)의 화합물과 반응시키거나, 또는 b) R1이 수소 또는 HY-가 아닌 제1항에 따른 화합물을 제조하기 위해서, R1이 수소 또는 HY-인, 대응되는 일반식(Ⅰ)의 화합물을 적절히 치환하고; 경우에 따라, 보호된 형태의 일반식(Ⅰ)의 생성 화합물을 탈보호시키거나, 또는 보호되지 않은 형태의 일반식(Ⅰ)의 생성 화합물을 적절히 보호하고; 유리 형태 또는 염 형태의 일반식(Ⅰ)의 생성 화합물을 회수함을 포함하는 제1항에 따른 화합물의 제조방법 :
    상기 식에서, A 및 B는 각기 독립적으로 결합 또는 임의로 치환된 아미노아실 부분을 나타내고; R1은 수소, 아미노 보호기, 또는 일반식 R5Y-의 기(이때, R5는 수소 또는 임의로 치환된 알킬, 알케닐, 알키닐, 아릴, 아릴알킬, 헤테로아릴, 헤테로아릴알킬, 헤테로사이클릴, 또는 헤테로사이클릴알킬기를 나타내고, Y는 -CO-, -NHCO-, -NHCS-, SO2-, -O-CO-, 또는 -O-CS-를 나타낸다)를 나타내고; R2는 천연 아미노산의 측쇄, 알킬, 아릴알킬, 헤테로아릴알킬, 또는 사이클로알킬알킬기 또는 트리메틸실릴메틸, 2-티에닐메틸, 또는 스티릴메틸을 나타내고; R3는 할로겐, 알킬, 알콕시 또는 하이드록시알콕시를 나타내고; R4는 2(R)-하이드록시인단-1(S)-일, (S)-2-하이드록시-1-페닐에틸, 또는 4번 위치에서 메톡시에 의해 임의로 치환된 2-하이드록시벤질을 나타낸다.
  5. 적어도 하나의 약학적으로 허용가능한 담체 또는 희석제와 함께 유리 형태 또는 약학적으로 허용가능한 염 형태의 제1항에서 정의한 바와 같은 일반식(Ⅰ)의 화합물을 포함하는 약학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940004724A 1993-03-12 1994-03-11 2, 4-디아미노-3-하이드록시카복실산 유도체 KR940021515A (ko)

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GB939319667A GB9319667D0 (en) 1993-09-23 1993-09-23 Organic compounds
GB9319667.3 1993-09-23

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US6017887A (en) * 1995-01-06 2000-01-25 Sibia Neurosciences, Inc. Peptide, peptide analog and amino acid analog protease inhibitors
US5804560A (en) * 1995-01-06 1998-09-08 Sibia Neurosciences, Inc. Peptide and peptide analog protease inhibitors
US6008228A (en) * 1995-06-06 1999-12-28 Hoffman-La Roche Inc. Pharmaceutical compositions containing proteinase inhibitors
JPH11514996A (ja) * 1995-11-21 1999-12-21 ノバルティス アクチエンゲゼルシャフト レトロウイルスアスパラギン酸プロテアーゼの置換同配体としてのアザヘキサン誘導体
EP1173413B1 (en) * 1999-04-27 2004-06-30 Novartis AG Use of 2,4-diamino-3-hydroxycarboxylic acid derivatives as proteasome inhibitors
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Publication number Priority date Publication date Assignee Title
US4661473A (en) * 1984-03-27 1987-04-28 Merck & Co., Inc. Renin inhibitors containing peptide isosteres
IL89900A0 (en) * 1988-04-12 1989-12-15 Merck & Co Inc Hiv protease inhibitors useful for the treatment of aids and pharmaceutical compositions containing them
CA2032259A1 (en) * 1989-12-18 1991-06-19 Wayne J. Thompson Hiv protease inhibitors useful for the treatment of aids
CA2052892A1 (en) * 1990-10-11 1992-04-12 Suresh K. Balani Inhibitors of hiv protease
CA2109326A1 (en) * 1991-07-02 1993-01-03 Andreas Billich 4-amino-3-hydroxycarboxylic acid derivatives
GB9210744D0 (en) * 1992-05-20 1992-07-08 Pfizer Ltd Antiviral peptides

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JP3987586B2 (ja) 2007-10-10
PE15695A1 (es) 1995-06-13
CZ55394A3 (en) 1995-04-12
CN1104209A (zh) 1995-06-28
EP0615969A1 (en) 1994-09-21
NZ260063A (en) 1996-02-27
FI941149A (fi) 1994-12-22
IL108930A0 (en) 1994-06-24
JPH0789919A (ja) 1995-04-04
CA2118876A1 (en) 1994-09-13
HUT71793A (en) 1996-02-28
SK30394A3 (en) 1995-03-08
NO940844D0 (no) 1994-03-10
US5538997A (en) 1996-07-23
AU5773794A (en) 1994-09-15
TW260662B (ko) 1995-10-21
HU9400745D0 (en) 1994-06-28
NO940844L (no) 1994-09-13
AU672867B2 (en) 1996-10-17

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