KR950701935A - 항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체(Conformationally restrained peptide analogs as antiplatelet agents) - Google Patents
항혈소판제로서의 입체배좌적으로 억제된 펩타이드 동족체(Conformationally restrained peptide analogs as antiplatelet agents)Info
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
- C07K14/75—Fibrinogen
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- C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
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- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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Abstract
본 발명은 혈소판 응집 억제제로서의 입테배좌적으로 억제된 (coformationally restrained) 펩타이드 동족체에 관한 것이다. 이들 화합물은 혈소판 응집을 억재하는 혈소판 GPⅡb-Ⅲa 인테그린(integrin) 수용체에 대한 피브리노겐의 결합을 억제하여 이들 화합물은 강력한 항혈전제로서 작용한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염.상기식에서, Y는 단편 -A1-A2-A3-NR1R2(여기서, A1은 결합이거나 Ser, Asp, Met, Trp, Phe 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, A2는 결합이거나 Pro, Nle, Met, Leu, Asn, Asp, Val, Arg 및 Leu로 이루어진 그룹에서 선택된 아미노산이며, A3는 결합이거나 Ala, Asp, Pro 및 Asn으로 이루어진 그룹에서 선택된 아미노산이고, R1및 R2는 각각 독립적으로 수소, C1-C10알킬, 벤질, 인돌릴, 피리디닐이거나 또는 Cl, Br, NO2, NH2, OH 및 OCH3로 이루어진 그룹에서 선택된 1 내지 3개의 치환cp로 임의 치환된 페닐이다)이며, Z는 단편 W-A6-A5-A4-(여기서, A4는 결합이거나 Gly및 βAla로 이루어진 그룹에서 선택된 아미노산이고, A5는 결합이거나 Arg, Lys, Thr, Ile, Leu, Asp, Asn 및 Val로 이루어진 그룹에서 선택된 아미노산이며, A6은 결합이거나 Val, Lys, Arg, Asp, Asn 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, W는 수소, 석시닐, C1-C10아실, C1-C10알킬, -(CH2)mC6H5(여기서, m은 정수 1 내지 3이다) 또는 -(CH2)pCO2H(여기서, p는 정수 1 내지 4이다)이다〕이며, X는 CONH, CH2NH, COCH2, CH2CH2, -CH20- 또는 -CH=CH-이고; R은 수소, C-C10알킬, 벤질 인돌릴, 나프틸, 티에닐, p-HO-벤질, p-NO2-벤질, p-Cl-벤질; 및 p-NH2-벤질이며, n은 정수 1 내지 3이고, 단 A6, A5및 A4중 하나가 아미노산인 경우 W는 C1-C10알킬, -(CH2)mC6H5또는 -(CH2)pCO2H가 아니다.
- 제1항에 있어서, X가 CONH, COCH2또는 CH2CH2인 화합물.
- 제1항에 있어서, Y가 벤질아민 또는 Asp-NH2인 화합물.
- 제1항에 있어서, n이 2인 화합물.
- 제1항에 있어서, R이 CH3, 벤질 또는 p-0H-벤질인 화합물.
- 제1항에 일어서, Z가 석시닐, -(CH2)3Co2H 또는 CH3CO-Asp-Gly인 화합물.
- 제1항에 있어서, X가 CONH, COCH2또는 CH2CH2이고; Y가 벤질아민 또는 Asp-NH2이며; n이 2이고; R이 CH3, 벤질 또는 p-OH-벤질이며; Z가 석시닐, -(CH2)3C02H 또는 CH3CO-Asp-Gly인 화합물.
- 제1항에 있어서, 사이클로〔Ala〔CH2NH〕-Arg-Gly-Asp-δ-Glu〕(NHBn) CF3CO2H인 화합물.
- 제1항에 있어서, 사이클로〔Ala〔CH2N(CO(CH2)2CO2H)-Arg-Gly-Asp-δ-Glu〕 (NHBn) ·CF3CO2H인 화합물.
- 제1항에 있어서, 사이클〔Ala〔CH2N(CO(CH2)3Ph)-Arg-Gly-Asp-δ-Glu〕 (NHBn)·CF3CO2H인 화합물.
- 제1항에 있어서, 사이클로〔Ala〔CH2N(CO(CH2)3CO2H)-Arg-Gly-Asp-δ-Glu〕 (NHBn) ·CF3CO2H인 화합물.
- 혈전 상태의 치료를 필요로 하는 환자에 대한 혈전 상태치료용 약제로서의, 제1항 내지 제11항중 어느 한 항에 따른 화합물의 용도.
- 약제로서의 제1항 내지 제11항중 어느 한 항에 따른 화합물의 용도.
- 제1항 내지 제11항중 어느 한 항에 따른 화합물을 불활성 담체와의 혼합물 형태로서 포함하는 조성물.
- 제14항에 있어서, 불활성 담체가 약제학적 담체인 조성물.
- 일반식(Ⅰ)화합물 또는 이의 약제학적으로 허용되는 염의 항혈소판 유효 투여량을 환자에게 투여함을 포함하여 혈전 상태의 치료를 필요로 하는 환자의 혈전 상태를 치료하는 방법.상기식에서, Y는 단편 -A1-A2-A3-NR1R2(여기서, A1은 결합이거나 Ser, Asp, Met, Trp, Phe 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, A2는 결합이거나 Pro, Nle, Met, Leu, Asn, Asp, Val, Arg 및 Leu로 이루어진 그룹에서 선택된 아미노산이며, A3는 결합이거나 Ala, Asp, Pro 및 Asn으로 이루어진 그룹에서 선택된 아미노산이고, R1및 R2는 각각 독립적으로 수소, C1-C10알킬, 벤질, 인돌릴, 피리디닐이거나 또는 Cl, Br, NO2, NH2, OH 및 OCH3로 이루어진 그룹에서 선택된 1 내지 3개의 치환체로 임의 치환된 페닐이다)이며, Z는 단편 W-A6-A5-A4-〔여기서, A4는 결합이거나 Gly및 βAla로 이루어진 그룹에서 선택된 아미노산이고, A5는 결합이거나 Arg, Lys, Thr, Ile, Leu, Asp, Asn 및 Val로 이루어진 그룹에서 선택된 아미노산이며, A6은 결합이거나 Val, Lys, Arg, Asp, Asn 및 Ala로 이루어진 그룹에서 선택된 아미노산이고, W는 수소, 석시닐, C1-C10아실, C1-C10알킬, -(CH2)mC6H5(여기서, m은 정수 1 내지 3이다) 또는 -(CH2)pCO2H(여기서, p는 정수 1 내지 4이다)이다〕이며, X는 CONH, CH2NH, COCH2, CH2CH2, -CH20- 또는 -CH=CH-이고; R은 수소, C-C10알킬, 벤질 인돌릴, 나프틸, 티에닐, p-HO-벤질, p-NO2-벤질, p-Cl-벤질; 및 P-NH2-벤질이며, n은 정수 1 내지 3이고, 단 A6, A5및 A4중 하나가 아미노산인 경우 W는 C1-C10알킬, -(CH2)mC6H5또는 -(CH2)PCO2H가 아니다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89421492A | 1992-06-04 | 1992-06-04 | |
US07/894214 | 1992-06-04 | ||
US07/894,214 | 1992-06-04 | ||
US5611193A | 1993-05-07 | 1993-05-07 | |
US08/056,111 | 1993-05-07 | ||
US08/056111 | 1993-05-07 | ||
PCT/US1993/004660 WO1993024520A1 (en) | 1992-06-04 | 1993-05-14 | Conformationally restrained peptide analogs as antiplatelet agents |
Publications (2)
Publication Number | Publication Date |
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KR950701935A true KR950701935A (ko) | 1995-05-17 |
KR100297184B1 KR100297184B1 (ko) | 2001-10-22 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1019940704404A KR100297184B1 (ko) | 1992-06-04 | 1993-05-14 | 항혈소판제로서의입체배좌적으로억제된펩타이드동족체및이를포함하는약제학적조성물 |
Country Status (16)
Country | Link |
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US (1) | US6107275A (ko) |
EP (1) | EP0648224B1 (ko) |
JP (1) | JP3398747B2 (ko) |
KR (1) | KR100297184B1 (ko) |
AT (1) | ATE168380T1 (ko) |
AU (1) | AU672010B2 (ko) |
CA (1) | CA2137072C (ko) |
DE (1) | DE69319733T2 (ko) |
DK (1) | DK0648224T3 (ko) |
ES (1) | ES2121088T3 (ko) |
GR (1) | GR3027738T3 (ko) |
IL (1) | IL105885A (ko) |
MX (1) | MX9303332A (ko) |
NZ (1) | NZ253452A (ko) |
TW (1) | TW274085B (ko) |
WO (1) | WO1993024520A1 (ko) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US5843156A (en) * | 1988-08-24 | 1998-12-01 | Endoluminal Therapeutics, Inc. | Local polymeric gel cellular therapy |
US6117974A (en) * | 1991-10-02 | 2000-09-12 | Peptor Limited | Libraries of backbone-cyclized peptidomimetics |
EP0729362B1 (en) * | 1993-11-19 | 2000-01-12 | G.D. SEARLE & CO. | TRANSDERMAL COMPOSITION OF N- N- 5- 4-(AMINOIMINOMETHYL)PHENYL]-1-OXOPENTYL]-L-alpha-ASPARTYL]-L-PHENYLALANINE OR ITS ESTERS AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS |
US6387880B1 (en) | 1994-10-24 | 2002-05-14 | G.D. Searle & Co. | Transdermal N-[N-[5-[4-(aminoiminomethly)phenyl]-1-oxopentyl]-L-α-aspartyl]-L-phenylalainine or its esters and their pharmaceutically acceptable salts |
DE19653036A1 (de) * | 1996-12-19 | 1998-06-25 | Merck Patent Gmbh | Cyclopeptidderivate |
DE19728524A1 (de) * | 1997-07-04 | 1999-01-07 | Merck Patent Gmbh | Cyclische Azapeptide |
CA2284459C (en) | 1999-10-04 | 2012-12-11 | Neokimia Inc. | Combinatorial synthesis of libraries of macrocyclic compounds useful in drug discovery |
CA2793838C (en) | 2010-03-19 | 2019-09-17 | H. Lee Moffitt Cancer Center & Research Institute, Inc. | Integrin interaction inhibitors for the treatment of cancer |
US10011635B2 (en) | 2013-09-27 | 2018-07-03 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Cyclic peptide conjugates and methods of use |
Family Cites Families (9)
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GB1585061A (en) * | 1977-03-15 | 1981-02-25 | Nat Res Dev | Synthesis of peptides |
US5041380A (en) * | 1982-08-04 | 1991-08-20 | La Jolla Cancer Research Foundation | Tetrapeptide |
US5318899A (en) * | 1989-06-16 | 1994-06-07 | Cor Therapeutics, Inc. | Platelet aggregation inhibitors |
FI84025C (fi) * | 1989-06-30 | 1991-10-10 | Jukka Elias Saarikettu | Filter som taol hoega temperaturer och foerfarande foer framstaellning daerav. |
US5384309A (en) * | 1989-07-17 | 1995-01-24 | Genentech, Inc. | Cyclized peptides and their use as platelet aggregation inhibitors |
CA2021951A1 (en) * | 1989-07-28 | 1991-01-29 | Ruth F. Nutt | Fibrinogen receptor antagonists |
US5023233A (en) * | 1989-07-28 | 1991-06-11 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
EP0410541A1 (en) * | 1989-07-28 | 1991-01-30 | Merck & Co. Inc. | Fibrinogen receptor antagonists |
US5192746A (en) * | 1990-07-09 | 1993-03-09 | Tanabe Seiyaku Co., Ltd. | Cyclic cell adhesion modulation compounds |
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1993
- 1993-05-14 AT AT93913930T patent/ATE168380T1/de not_active IP Right Cessation
- 1993-05-14 KR KR1019940704404A patent/KR100297184B1/ko not_active IP Right Cessation
- 1993-05-14 NZ NZ253452A patent/NZ253452A/en unknown
- 1993-05-14 AU AU43783/93A patent/AU672010B2/en not_active Ceased
- 1993-05-14 JP JP50059594A patent/JP3398747B2/ja not_active Expired - Fee Related
- 1993-05-14 DK DK93913930T patent/DK0648224T3/da active
- 1993-05-14 DE DE69319733T patent/DE69319733T2/de not_active Expired - Fee Related
- 1993-05-14 ES ES93913930T patent/ES2121088T3/es not_active Expired - Lifetime
- 1993-05-14 WO PCT/US1993/004660 patent/WO1993024520A1/en active IP Right Grant
- 1993-05-14 EP EP93913930A patent/EP0648224B1/en not_active Expired - Lifetime
- 1993-05-14 CA CA002137072A patent/CA2137072C/en not_active Expired - Fee Related
- 1993-06-01 TW TW082104342A patent/TW274085B/zh active
- 1993-06-02 IL IL10588593A patent/IL105885A/en not_active IP Right Cessation
- 1993-06-03 MX MX9303332A patent/MX9303332A/es unknown
-
1997
- 1997-04-09 US US08/835,274 patent/US6107275A/en not_active Expired - Fee Related
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1998
- 1998-08-26 GR GR980401921T patent/GR3027738T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
WO1993024520A1 (en) | 1993-12-09 |
CA2137072C (en) | 2000-06-13 |
MX9303332A (es) | 1994-06-30 |
TW274085B (ko) | 1996-04-11 |
DK0648224T3 (da) | 1998-10-26 |
US6107275A (en) | 2000-08-22 |
JPH07507310A (ja) | 1995-08-10 |
ES2121088T3 (es) | 1998-11-16 |
CA2137072A1 (en) | 1993-12-09 |
EP0648224A1 (en) | 1995-04-19 |
GR3027738T3 (en) | 1998-11-30 |
AU4378393A (en) | 1993-12-30 |
IL105885A0 (en) | 1993-10-20 |
DE69319733T2 (de) | 1999-01-14 |
NZ253452A (en) | 1996-06-25 |
JP3398747B2 (ja) | 2003-04-21 |
EP0648224B1 (en) | 1998-07-15 |
AU672010B2 (en) | 1996-09-19 |
ATE168380T1 (de) | 1998-08-15 |
DE69319733D1 (de) | 1998-08-20 |
KR100297184B1 (ko) | 2001-10-22 |
IL105885A (en) | 1999-06-20 |
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