KR950011466A - 선형 결합 억제제 - Google Patents

선형 결합 억제제 Download PDF

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KR950011466A
KR950011466A KR1019940027613A KR19940027613A KR950011466A KR 950011466 A KR950011466 A KR 950011466A KR 1019940027613 A KR1019940027613 A KR 1019940027613A KR 19940027613 A KR19940027613 A KR 19940027613A KR 950011466 A KR950011466 A KR 950011466A
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cys
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asn
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욘크지크 알프레드
펠딩-하베르만 브룬힐데
디펜바흐 베아테
리프만 프리드리히
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위르겐 호이만, 라인하르트 슈틀러
메르크 파텐트 게젤샤프트 미트 베쉬랭크터 하프퉁
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Abstract

하기 일반식(I)의 선헝 펩티드는 중성 리간드에 혈소판 인테그린 GP ⅡbⅢa(αⅡbβ3)의 결합을 억제하는 매우 높은 활성의 억제제이며 특히 순환계 질환, 혈전증, 실근 경색, 관상 심장 질환, 동맥경화증, 죽상동맥경화증, 종양 및 골용해성 질환의 치료 및 예방에 적합하며 상처의 치료 과정에 보조 효과를 가진다.

Description

선형 결합 억제제
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(I)의 선형 펩티드 및 이들의 약학적으로 허용가능한 염 ;
    X-A-Cys(R1)-B-Z (I)
    상기 식에서, X는 H또는 Ac 이고; A는 존재하지 않거나 Asp이거나또는 Ala-Asp, Thr-Ala-Asp, Lys-Thr-Ala-Asp, Lys-Thr-Ala-Asn, Lys-Thr-Gly-Asp, Lys-Ala-Ala-Asp, Arg-Thr-Ala-Asp,Ser-Ala-Asp, Gln-Ser-Ala-Asp, Gly-Lys-Thr-Ala-Asp, Asn- Gly-Lys-Thr-Ala-Asp, Ile-ser-Ala-Gly, Arg-Ser-Ala-Gly, Cys-Asn-Gly-Lys -Thr-Ala-Asp, Tyr-Cys-Asn-Gly-Lys-Thr-Ala-Asp, Asp-Tyr-Cys-Asn-Gly-Lys-Thr- Ala-Asp, Gly-Lys-Thr-Cys-Asp, Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Ala-Asp, Gly- Lys-Thr-Cys(Trt)-Asp, Met-Asp-Asp-Thr-Cys-Asn-Gly-Lys-Thr-Ala-AsP 및 Asp-Met-Asp-Asp-Tyr-Cys-Asn-Gly-Thr-Ala-Asp로 구성되는 군으로 부터 선택되는 펩티드 단편이고; B는 존재하지 않거나 또는 Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Orn, Phe, 4-Hal-Phe, Pro, Ser, Thr, Trp, Tyr 또는 Val 이거나, 또는 상기 아미노산 잔기의 N-메틸화된 유도체이거나. 또는 Pro-Arg, Pre-Arg-Asn. Pro-Arg-Asn-Pro, Pro-Arg-Asn-Pro-His, Pro-Arg-Asn-Pro-His-Lys, Pro-Arg-Asn-Pro-His-Lys-Gly,Pro-Arg-Asn-Pro-His-Lys-Gly-Pro, Pro-Arg-Asn-Pro-His-Lys- Gly-Pro-Ala 및 Pro-Arg-Asn-Pro-His-Lys-Gly-Pro-Ala-Thr로 구성되는 군으로 부터 선택되는 펩티드 단편이고 : 잔기 A 또는 B 중의 하나는 존재하지 않을 수 있고 Z는 OH, OR2, NH2, NHR2또는 N(R2)2이고: R1은 H, R2, Trt, Dpm 또는 Bz1이고: R2는 탄소 원자수 1 내지 6의 알킬이고: Ha1은 F, C1, Br또는 1이고: Ac는 탄소 원자수 1 내지10의 알카노일, 탄소 원자수 8 내지 10의 아르알카노일 또는 탄소 원자수 7 내지 11의 아로일이다.
  2. 제1항에 따른 일반식 (I)의 화합물의 거울상 이성질체 또는 부분입체 이성질체.
  3. (a) H-Ala-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-Lys-Gly-Pro-Ala-Thr-OH; (b) H-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-Lys-Gly-Pro-Ala-Thr-OH; (c) H-Gly-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-Lys-Gly-OH; (d) H-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-OH; (e) H-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-Lys-Gly-OH: (f) H-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-Arg-OH : (g) H-Lys-Thr-Ala-Asp-Cys(Trt)-Pro-OH: 및 (h) H3C-CO-Asp-Cys(Trt)-Pro-Arg-Asn-Pro-His-Lys-OH.
  4. 가용매분해제 또는 가수소분해제로 처리함으로써 그의 작용성 유도체중의 하나로부터 유리시키거나 또는 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 아미노 화합물과 반응시키거나 및/또는 유리 메르캅토, 하이드록시 또는 아미노 그룹을 알킬화시키거나 및/또는 제 1항에 따른 일반식( I )의 화합물을 산 또는 염기로 처리함으로써 그의 염중의 하나로 전환시킴을 특징으로 하는, 제1항에 따른 일반식 (Ⅰ)의 화합물 또는 그의 염을 제조하는 방법 :
    X-M-OH Ⅱ
    H-Q-Z Ⅲ
    상기 식에서, M온 A, A-Cys(R1), Ala, Thr, Thr-Ala, Lys, Lys-Thr, Lys-Thr-Ala-Gly, Lys-Thr-Ala-Gly, Gly-Lys, Gly-Lys-Thr, Gly-Lys-Thr-Ala, Gly-Lys-Thr-Cys(R1), Asn, Asn-Gly, Asn-Gly-Lys,Lys-Ala, Lys-Ala-Ala, Asn-Gly-Lys-Thr, Asn-Gly-Lys-Thr-Ala, Cys, Cys-Asn, Cys-Asn-Gly, Arg, Arg-Thr, Arg-Thr-Ala, Ser, Cys-Asn-Gly-Lys, Cys-Ans-Gly-Lys-Thr, Cys-Asn-Gly-Lys-Thr-Ala, Ser-Ala, Tyr, Tyr-Cys, Tyr-Cys-Asn, Tyr-Cys-Asn-Gly, Tyr-cys-Asn-Gly-Lys, Gln, Gln-Ser, Gln-Ser-Ala, Tyr-Cys-Asn-Cly-Lys-Thr, Tyr-Cys-Asn-Gly-Lys-Thr-Ala, Asp, Asp-Tyr, Asp-Tyr-Cys, Asp-Tyr-Cys-Asn, Asp-Tyr-Cys-Asn-Gly, Ile, Ile-Ser, Ile-Ser-Ala, Asp-Tyr-Cys-Asn-Gly-Lys, Asp-Thr-Cys-Asn-Gly-Thr, Arg-Ser, Arg- Ser-Ala, Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Ala, Asp-Asp, Asp-Asp-Tyr, Asp-Asp-Tyr-Cys, Asp-Asp-Tyr-Cys-Asn, Asp-Asp-Tyr-Cys-Asn-Gly, Asp-Asp-Tyr-Cys-Asn-Gly-Lys, Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr, Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Ala, Met, Met-Asp, Met-Asp-Asp, Met-Asp-Asp-Tyr, Met-Asp-Asp-Tyr-Cys, Met-Asp-Asp- Tyr-Cys-Asn, Met-Asp-Asp-Tyr-Cys-Asn-Gly, Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys, Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr, Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Ala, Asp-Met, Asp-Met-Asp, Asp-Met-Asp-Asp, Asp-Met-Asp-Asp-Tyr, Asp-Met-Asp-Asp- Tyr-Cys, Asp-Met-Asp-Asp-Tyr-Cys-Asn, Asp-Met-Asp-Asp-Tyr-Cys-Asn-Gly, Asp-Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys, Asp-Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Asp-Met-Asp-Asp-Tyr-Cys-Asn-Gly-Lys-Thr-Ala, A-Cys(R1)-Pro, A-Cys(R1)-Pro-Arg, A-Cys(R1)-Pro-Arg-Asn, A-Cys(R1)-Pro-Arg-Asn-Pro, A-Cys(R1)-Pro-Arg-Asn-Pro-HIs, A-Cys(R1)-Pro-Arg-Asn-Pro-HIs-Lys, A-Cys(R1)-Pro-Arg-Asn-Pro-His-Lys-Gly,A- Cys(R1)-Pro-Arg-Asn-Pro-His-Lys-Gly-Pro, A-Cys(R1)-Pro-Arg-Asn-Pro-His-Lys-Gly-Pro- Ala로 구성되는 군으로 부터 선택되는 아미노산 잔기 또는 펩티드 라디칼(여기서, A 및 R1은 제1항에서 정의한 바와 같다)이고: X는 제1항에서 정의한 바와 같으나 A및 따라서 M이 존재하지 않을 경우 수소는 아니고; Z는 제1항에서 정의한 바와 같고; Q는 B, Cys(R1)-B, Arg-Asn, Arg-Asn-Pro, Asn-Pro, Arg-Asn-Pro-His, Asn-Pro-His, Pro-His, Arg-Asn-Pro-His-Lys, Asn-Pro-His-Lys,Pro- His-Lys, His-Lys, Arg-Asn-Pro-His-Lys-G1y, Asn-Pro-His-1ys-G1y, Pro-His-Lys-G1y, His-Lys-G1y, 1ys-G1y, Arg-Asn-Pro-His- Lys-G1y-Pro, Asn-Pro-His- Lys-G1y-Pro, Pro-His-Lys-G1y-Pro, His-1ys-G1y-Pro, Lys-G1y-Pro, G1y-Pro, Arg-Asn-Pro-His-Lys-G1y-Pro-A1a, Asn-Pro-His-Lys-G1y-Pro-A1a, Pro-His-Lys-G1y-Pro-A1a, His-Lys-G1y-Pro-A1a, Lys-G1y-Pro-A1a, G1y-Pro-A1a, Pro-A7a, Arg-Asn-Pro-His-Lys-G1y-Pro-A1a-Thr, Asn-Pro-His-Lys-G1y-Pre-A1a-Thr, Pro-His-Lys-G1y-Pro-A1a-Thr, His-1ys-G1y-Pro-A1a-Thr, Lys-G1y-Pro-A1a-Thr, G1y-Pro-A1a-Thr, Pro-A1a-Thr, A1a-Thr, G1y-Asp-Cys(R1)-B, Thr-G1y-Asp-Cys(R1)-B, Asp-Cys(R1)-B, A1a-Asp-Cys(R1)-B, Thr-A1a-Asp-Cys(R1)-B, Lys-Thr-A1a-Asp-Cys(R1)-B, G1y-Lys-Thr-A1a-Asp-Cys(R1)-B, Asn-G1y-1ys-Thr-A1a- Asp-Cys(R1)-B, Asn-Cys(R1)-B, A1a- Asn-Cys(R1)-B, Thr-A1a-Asn-Cys(R1)-B, Cys-Asn-G1y-Lys-Thr-A1a-Asp-Cys(R1)-B, A1a-A1a-Asp-Cys(R1)-B, Ser-A1a-Asp-Cys(R1)-B, Tyr-Cys-Asn-G1y-Lys-Thr-A1a-Asp-Cys(R1)-B, G1y-Cys(R1)-B, A1a-G1y-Cys(R1)-B, Ser-A1a-G1y-Cys(R1)-B, Cys (Trt) -Asp-Cys(R1)-B, Thr-Cys(Trt)-Asp-Cys(R1)-B,Lys-Thr-Cys(Trt)-Asp-Cys(R1)-B, Asp-Tyr-Cys-Asn-G1y-Lys-Thr-A1a-Asp-Cys(R1)-B, Asp-Asp-Tyr-Cys-Asn-G1y-Lys-Thr-A1a-Asp-Cys(R1)-B 및 Met-Asp-Asp-Tyr-Cys-Asn-Gty-Lys-Thr-Ata-Asp-Cys(R1)-B로 구성되는 군으로 부터 선택되는 아미노산 잔기 또는 펩티드 라디칼(여기서, R1은 상기에서 정의된 바와 같다)이다.
  5. 적어도 하나의 고체, 액체 또는 반고체 부형제 또는 보조제와 함께 제 1항에 따른 일반식(I)의 화합물 및/또는 그의 생리학적으로 허용가능한 염을 적당한 투여 제형으로 제조함을 특징으로 하는, 약제의 제조 방법.
  6. 적어도 하나의 제1헝에 따른 일반식(I)의 화합물 및/또는 그의 생리학적으로 허용가능한 염중의 하나를 함유함을 특징으로 하는 약제.
  7. 질환 치료용 약제률 제조하기 위한 제1항에 따른 일반식(I)의 화합물 또는 그의 생리학적으로 허용가능한 염의 용도.
  8. 질환의 치료를 위한 제1항에 따른 일반식(I) 화합물 또는 그의 생리학적으로 허용가능한 염의 용도.
  9. 친화성 컬럼 크로마토그래피용 고정화된 리간드를 제조하기 위한 제1항에 따른 일반식(I)화합물의 용도.
  10. 친화성 크로마토그래피로 인테그린을 정제하기 위한 제1항에 따른 일반식 (I)화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940027613A 1993-10-28 1994-10-27 선형 결합 억제제 KR950011466A (ko)

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US6100423A (en) * 1995-08-30 2000-08-08 G. D. Searle & Co. Amino benzenepropanoic acid compounds and derivatives thereof
CN1085980C (zh) * 1995-08-30 2002-06-05 G·D·瑟尔公司 间－胍基、脲基、硫脲基或氮杂环氨基苯甲酸衍生物用作整合素拮抗剂
DE19534016A1 (de) * 1995-09-14 1997-03-20 Merck Patent Gmbh Biotinderivate
WO2000038730A2 (en) 1998-12-23 2000-07-06 G.D. Searle & Co. Use of a cyclooxygenase-2 inhibitor and one or more antineoplastic agents for combination therapy in neoplasia
MXPA06006319A (es) * 2003-12-03 2006-08-23 Scripps Research Inst Peptidos y anticuerpos especificos para integrina aiib??3.
CN108203465B (zh) * 2016-12-20 2022-09-02 山西医科大学 一种双重靶向抑制肿瘤细胞和肿瘤血管且性质稳定的多肽

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US2799670A (en) * 1954-04-13 1957-07-16 Laufer Louis Method of preparing cysteinylglycine
US4177277A (en) * 1977-01-17 1979-12-04 E. R. Squibb & Sons, Inc. Method for alleviating hypertension
JP2945680B2 (ja) * 1988-09-09 1999-09-06 旭硝子株式会社 ペプチド誘導体およびその用途
CA2009613A1 (en) * 1989-02-09 1990-08-09 Victor M. Garsky Polypeptide synthesis
AU5939890A (en) * 1989-06-07 1991-01-07 Genentech Inc. Platelet aggregation inhibitors and related molecules

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EP0655462A1 (de) 1995-05-31
ATE165837T1 (de) 1998-05-15
US5747457A (en) 1998-05-05
DE59405893D1 (de) 1998-06-10
NO944093D0 (no) 1994-10-27
SK130094A3 (en) 1995-05-10
ZA948479B (en) 1995-06-20
AU690923B2 (en) 1998-05-07
NO944093L (no) 1995-05-02
HU9403100D0 (en) 1994-12-28
AU7750194A (en) 1995-05-18
RU94039288A (ru) 1996-09-10
JPH07149794A (ja) 1995-06-13
CN1107159A (zh) 1995-08-23
CA2134418A1 (en) 1995-04-29
HUT69179A (en) 1995-08-28
CZ265594A3 (en) 1995-07-12
EP0655462B1 (de) 1998-05-06
PL305632A1 (en) 1995-05-02
DE4336758A1 (de) 1995-05-04

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